Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, [structure] X is CH or N; Y is C(O) or S(O) 2 ; provided that when Y is S(O) 2 , then X is CH; A is a radical selected from the group consisting of [structure] and B 1 , B 2 , B 3 , T, R 1 , R 2 R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

Description

78 parts

›FIELD OF THE INVENTION

This invention relates to certain bis-nitrogen heterocycles, their salts and compositions, and methods of their use for controlling undesirable vegetation. This invention also relates to certain intermediates and a method useful for preparing these bis-nitrogen heterocycles and their salts. This invention also relates to certain bis-nitrogen oxo or sulfono heterocycles, their salts and compositions, and methods of their use for controlling undesirable vegetation.

›BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.

International patent application publication WO 2007/088876 discloses pyridone compounds of Formula i

wherein inter alia R 1 is C 1 -C 6 alkyl; R 2 and R 3 are each independently hydrogen, cyano, or nitro; and A is a A-1 through A-5 as defined therein as herbicides.

The bis-nitrogen containing oxo and sulfono heterocycles of the present invention are not disclosed in this publication.

›SUMMARY OF THE INVENTION · 1 of 6

This invention is directed to compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:

wherein

X is CH; Y is C(O); A is a radical selected from the group consisting of

B 1 and B 3 are each independently a radical selected from the group consisting of

B 2 is a radical selected from the group consisting of

R 1 is phenyl, phenylsulfonyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —NHCHO, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 haloalkyl, C 2 -C 10 haloalkenyl, C 2 -C 12 haloalkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 halocycloalkyl, C 4 -C 14 alkylcycloalkyl, C 4 -C 14 cycloalkylalkyl, C 6 -C 18 cycloalkylcycloalkyl, C 4 -C 14 halocycloalkylalkyl, C 5 -C 16 alkylcycloalkylalkyl, C 3 -C 12 cycloalkenyl, C 3 -C 12 halocycloalkenyl, C 2 -C 12 alkoxyalkyl, C 3 -C 12 alkoxyalkenyl, C 4 -C 14 alkylcycloalkyl, C 4 -C 14 alkoxycycloalkyl, C 4 -C 14 cycloalkoxyalkyl, C 5 -C 14 cycloalkoxyalkoxyalkyl, C 3 -C 14 alkoxyalkoxyalkyl, C 2 -C 12 alkylthioalkyl, C 2 -C 12 alkylsulfinylalkyl, C 2 -C 12 alkylsulfonylalkyl, C 2 -C 12 alkylaminoalkyl, C 3 -C 14 dialkylaminoalkyl, C 2 -C 12 haloalkylaminoalkyl, C 4 -C 14 cycloalkylaminoalkyl, C 2 -C 12 alkylcarbonyl, C 2 -C 12 haloalkylcarbonyl, C 4 -C 14 cycloalkylcarbonyl, C 2 -C 12 alkoxycarbonyl, C 4 -C 16 cycloalkoxycarbonyl, C 5 -C 14 cycloalkylalkoxycarbonyl, C 2 -C 12 alkylaminocarbonyl, C 3 -C 14 dialkylaminocarbonyl, C 4 -C 14 cycloalkylaminocarbonyl, C 2 -C 9 cyanoalkyl, C 1 -C 10 hydroxyalkyl, C 4 -C 14 cycloalkenylalkyl, C 2 -C 12 haloalkoxyalkyl, C 2 -C 12 alkoxyhaloalkyl, C 2 -C 12 haloalkoxyhaloalkyl, C 4 -C 14 halocycloalkoxyalkyl, C 4 -C 14 cycloalkenyloxyalkyl, C 4 -C 14 halocycloalkenyloxyalkyl, C 3 -C 14 dialkoxyalkyl, C 3 -C 14 alkoxyalkylcarbonyl, C 3 -C 14 alkoxycarbonylalkyl, C 2 -C 12 haloalkoxycarbonyl, C 1 -C 10 alkoxy, C 1 -C 10 haloalkoxy, C 3 -C 12 cycloalkoxy, C 3 -C 12 halocycloalkoxy, C 4 -C 14 cycloalkylalkoxy, C 2 -C 10 alkenyloxy, C 2 -C 10 haloalkenyloxy, C 2 -C 10 alkynyloxy, C 3 -C 10 haloalkynyloxy, C 2 -C 12 alkoxyalkoxy, C 2 -C 12 alkylcarbonyloxy, C 2 -C 12 haloalkylcarbonyloxy, C 4 -C 14 cycloalkylcarbonyloxy, C 3 -C 14 alkylcarbonylalkoxy, C 1 -C 10 alkylthio, C 1 -C 10 haloalkylthio, C 3 -C 12 cycloalkylthio, C 1 -C 10 alkylsulfinyl, C 1 -C 10 haloalkylsulfinyl, C 1 -C 10 alkylsulfonyl, C 1 -C 10 haloalkylsulfonyl, C 3 -C 12 cycloalkylsulfonyl, C 2 -C 12 alkylcarbonylthio, C 2 -C 12 alkyl(thiocarbonyl)thio, C 3 -C 12 cycloalkylsulfinyl, C 1 -C 10 alkylaminosulfonyl, C 2 -C 12 dialkylaminosulfonyl, C 1 -C 10 alkylamino, C 2 -C 12 dialkylamino, C 1 -C 10 haloalkylamino, C 2 -C 12 halodialkylamino, C 3 -C 12 cycloalkylamino, C 2 -C 12 alkylcarbonylamino, C 2 -C 12 haloalkylcarbonylamino, C 1 -C 10 alkylsulfonylamino, C 1 -C 10 haloalkylsulfonylamino or C 4 -C 14 cycloalkyl(alkyl)amino;

W 1 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;

W 2 is C 1 -C 6 alkylene;

R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 4 G; or H, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═S)NH 2 , —C(═O)NHCN, —C(═O)NHOH, —SH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —SF 5 , —NHCHO, —NHNH 2 , —NHOH, —NHCN, —NHC(═O)NH 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -C 10 dialkylaminoalkyl, C 2 -C 8 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkylcarbonyl, C 3 -C 10 alkoxycarbonylalkyl, C 2 -C 8 haloalkoxycarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 8 trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 halocycloalkenyloxy, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyhaloalkoxy, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -C 8 alkyl(thiocarbonyl)oxy, C 2 -C 8 alkylcarbonylthio, C 2 -C 8 alkyl(thiocarbonyl)thio, C 3 -C 8 cycloalkylsulfinyl, C 1 -C 6 alkylaminosulfonyl, C 2 -C 8 dialkylaminosulfonyl, C 3 -C 10 halotrialkylsilyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino or C 4 -C 10 cycloalkyl(alkyl)amino; or

›SUMMARY OF THE INVENTION · 2 of 6

R 1 and R 2 are taken together along with the atoms to which they are attached to make a 5-, 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O) 2 —, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy; and optionally substituted on nitrogen ring members selected from H and C 1 -C 6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy;

W 3 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;

W 4 is C 1 -C 6 alkylene;

R 3 is H, halogen, cyano, hydroxy, —O − M + , amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═S)NH 2 , —SH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —OCN, —SCN, —SF 5 , —NHNH 2 , —NHOH, —N═C═O, —N═C═S, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -C 6 alkylsulfonylamino or C 1 -C 6 haloalkylsulfonylamino; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or benzylsulfonyl, each optionally substituted on ring members with up to five substituents selected from R 21 ;

M + is an alkali metal cation or an ammonium cation;

R 4 , R 5 , R 6 and R 7 are each independently H, halogen, hydroxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy or C 3 -C 8 halocycloalkoxy; or phenyl or benzyl, each optionally substituted on ring members with up to five substituents selected from R 21 ;

R 8 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl or C 3 -C 8 halocycloalkyl; or benzyl optionally substituted on ring members with up to five substituents selected from R 21 ;

R 9 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl or C 2 -C 8 alkylthioalkyl;

R 10 is H, halogen, cyano, hydroxy, amino, nitro, SH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —OCN, —SCN, —SF 5 , —NHCHO, —NHNH 2 , —N 3 , —NHOH, —NHCN, —NHC(═O)NH 2 , —N═C═O, —N═C═S, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl or C 2 -C 8 alkylthioalkyl;

R 11 is H, halogen, cyano, hydroxy, amino, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl or C 2 -C 8 alkylsulfonylalkyl; or phenyl optionally substituted with up to five substituents selected from R 21 ;

R 12 is H, halogen, cyano, hydroxy, amino, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl or C 2 -C 8 alkoxycarbonylamino;

R 13 is H, halogen, cyano, hydroxy, amino, nitro or C 2 -C 8 alkoxycarbonyl;

n is 0, 1, or 2;

each R 14 , R 15 , R 18 and R 19 is independently H, halogen, cyano, hydroxy or C 1 -C 6 alkyl; or

a pair of R 14 and R 18 is taken together as C 2 -C 6 alkylene or C 2 -C 6 alkenylene;

R 20 is H, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 8 cycloalkyl;

T is C 1 -C 6 alkylene or C 2 -C 6 alkenylene;

each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally substituted with up to five substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members;

each R 21 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═S)NH 2 , —C(═O)NHCN, —C(═O)NHOH, —SH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —OCN, —SCN, —SF 5 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 halodialkylamino or C 3 -C 8 cycloalkylamino; and

›SUMMARY OF THE INVENTION · 3 of 6

each R 22 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 2 -C 8 alkoxyalkyl.

More particularly, this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide, or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein)

This invention also relates to a herbicidal mixture of (a) a compound of Formula 1 and (b) at least one additional active ingredient.

This invention is also directed to an intermediate compound of Formula 1Q (including all stereoisomers), N-oxides, and salts thereof:

wherein A′ is a radical selected from the group consisting of

and

R 1 , R 2 , B 1 , B 2 , B 3 , T, R 9 and R 10 are as defined above for a compound of Formula 1 which is useful for preparing a compound of Formula 1.

This invention is also directed to a compound of Formula 1R (including all stereoisomers), N-oxides, and salts thereof:

wherein

R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl or C 2 -C 8 alkylsulfonylalkyl;

W 1 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;

W 2 is C 1 -C 6 alkylene;

R 2 is phenyl or —W 3 (phenyl), each substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl;

W 3 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;

each R 22 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 2 -C 8 alkoxyalkyl

which is useful for preparing a compound of Formula 1.

This invention is also directed to a compound of Formula 1S (including all stereoisomers), N-oxides, and salts thereof:

wherein

R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 alkoxycycloalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl or C 2 -C 8 alkylsulfonylalkyl;

W 1 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;

W 2 is C 1 -C 6 alkylene;

R 2 is phenyl or —W 3 (phenyl), each substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl;

W 3 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;

›SUMMARY OF THE INVENTION · 4 of 6

each R 22 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 2 -C 8 alkoxyalkyl; and

R 23 is an optionally substituted carbon moiety

which is useful for preparing a compound of Formula 1.

This invention is also directed to a process for preparing a compound of Formula 1 from a compound of formula 1Q in the presence of cesium fluoride:

wherein A′ is a radical selected from A′-1, A′-2, A′-3 and A′-5 as defined above for a compound of Formula 1Q; and A is radical selected from A-1, A-2, A-3 and A-5 as defined above for a compound of Formula 1; and R 1 and R 2 are as defined above for a compound of Formula 1 which is useful for preparing a compound of Formula 1.

This invention is also directed to compounds of Formula 1P (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:

wherein

X is CH or N; Y is C(O) or S(O) 2 ; provided that when Y is S(O) 2 , then X is CH; A is a radical selected from the group consisting of

B 1 and B 3 are each independently a radical selected from the group consisting of

B 2 is a radical selected from the group consisting of

R 1 is phenyl, phenylsulfonyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —NHCHO, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 5 -C 10 cycloalkoxyalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -C 10 dialkylaminoalkyl, C 2 -C 8 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkylcarbonyl, C 3 -C 10 alkoxycarbonylalkyl, C 2 -C 8 haloalkoxycarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 2 -C 8 alkylcarbonylthio, C 2 -C 8 alkyl(thiocarbonyl)thio, C 3 -C 8 cycloalkylsulfinyl, C 1 -C 6 alkylaminosulfonyl, C 2 -C 8 dialkylaminosulfonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino or C 4 -C 10 cycloalkyl(alkyl)amino;

W 1 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;

W 2 is C 1 -C 6 alkylene;

R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 4 G; or H, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═S)NH 2 , —C(═O)NHCN, —C(═O)NHOH, —SH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —SF 5 , —NHCHO, —NHNH 2 , —NHOH, —NHCN, —NHC(═O)NH 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -C 10 dialkylaminoalkyl, C 2 -C 8 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkylcarbonyl, C 3 -C 10 alkoxycarbonylalkyl, C 2 -C 8 haloalkoxycarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 8 trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 halocycloalkenyloxy, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyhaloalkoxy, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -C 8 alkyl(thiocarbonyl)oxy, C 2 -C 8 alkylcarbonylthio, C 2 -C 8 alkyl(thiocarbonyl)thio, C 3 -C 8 cycloalkylsulfinyl, C 1 -C 6 alkylaminosulfonyl, C 2 -C 8 dialkylaminosulfonyl, C 3 -C 10 halotrialkylsilyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino or C 4 -C 10 cycloalkyl(alkyl)amino;

›SUMMARY OF THE INVENTION · 5 of 6

W 3 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;

W 4 is C 1 -C 6 alkylene;

M + is an alkali metal cation or an ammonium cation;

R 13 is H, halogen, cyano, hydroxy, amino, nitro or C 2 -C 8 alkoxycarbonyl;

n is 0, 1, or 2;

each R 14 , R 15 , R 18 and R 19 is independently H, halogen, cyano, hydroxy or C 1 -C 6 alkyl; or

a pair of R 14 and R 18 is taken together as C 2 -C 6 alkylene or C 2 -C 6 alkenylene;

R 20 is H, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 8 cycloalkyl;

T is C 1 -C 6 alkylene or C 2 -C 6 alkenylene;

›SUMMARY OF THE INVENTION · 6 of 6

each R 22 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 2 -C 8 alkoxyalkyl.

More particularly, this invention pertains to a compound of Formula 1P (including all stereoisomers), an N-oxide, or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).

This invention also includes a herbicidal mixture of (a) a compound of Formula 1P and (b) an active ingredient selected from a photosystem II inhibitor.

›DETAILS OF THE INVENTION · 1 of 7

As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.

Where applicants have defined an invention or a portion thereof with an open-ended term such as “comprising,” it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms “consisting essentially of” or “consisting of.”

Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive “or”. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

As referred to herein, the term “seedling”, used either alone or in a combination of words means a young plant developing from the embryo of a seed.

As referred to herein, the term “broadleaf” used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.

As used herein, the term “alkylating agent” refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to a leaving group such as halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term “alkylating” does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R 1 , R 2 and R 3 .

In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkylene” denotes a straight-chain or branched alkanediyl. Examples of “alkylene” include CH 2 , CH 2 CH 2 , CH(CH 3 ), CH 2 CH 2 CH 2 , CH 2 CH(CH 3 ) and the different butylene isomers. “Alkenylene” denotes a straight-chain or branched alkenediyl containing one olefinic bond. Examples of “alkenylene” include CH═CH, CH 2 CH═CH, CH═C(CH 3 ) and the different butenylene isomers. “Alkynylene” denotes a straight-chain or branched alkynediyl containing one triple bond. Examples of “alkynylene” include C≡C, CH 2 C≡C, C≡CCH 2 and the different butynylene isomers.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy. “Alkenyloxy” includes straight-chain or branched alkenyloxy moieties. Examples of “alkenyloxy” include H 2 C═CHCH 2 O, (CH 3 ) 2 C═CHCH 2 O, (CH 3 )CH═CHCH 2 O, (CH 3 )CH═C(CH 3 )CH 2 O and CH 2 ═CHCH 2 CH 2 O. “Alkynyloxy” includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC≡CCH 2 O, CH 3 C≡CCH 2 O and CH 3 C≡CCH 2 CH 2 O. “Alkoxyalkenyl” includes straight-chain or branched alkenyl substituted by an alkoxy group. Examples of “alkoxyalkenyl” include CH 3 OCH═CH, CH 3 C(OCH 3 )═CH and CH 3 CH 2 OCH═CHCH 2 . “Alkoxyalkoxyalkyl” denotes alkoxyalkoxy substitution on alkyl. Examples of “alkoxyalkoxyalkyl” include CH 3 OCH 2 OCH 2 , CH 3 OCH 2 OCH 2 CH 2 , CH 3 CH 2 OCH 2 OCH 2 and CH 3 OCH 3 CH 2 OCH 2 CH 2 . “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH 3 S(O)—, CH 3 CH 2 S(O)—, CH 3 CH 2 CH 2 S(O)—, (CH 3 ) 2 CHS(O)— and the different butylsulfonyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH 3 S(O) 2 —, CH 3 CH 2 S(O) 2 —, CH 3 CH 2 CH 2 S(O) 2 —, (CH 3 ) 2 CHS(O) 2 —, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. The terms “cycloalkylsulfinyl” and “cycloalkylsulfonyl” are defined analogously to the terms “alkylsulfinyl” and “alkylsulfonyl” above.

›DETAILS OF THE INVENTION · 2 of 7

“Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 ; “alkylsulfinylalkyl” and “alkylsulfonylalkyl” include the corresponding sulfoxides and sulfones, respectively. “Alkylamino” includes an NH radical substituted with straight-chain or branched alkyl. Examples of “alkylamino” include CH 3 CH 2 NH, CH 3 CH 2 CH 2 NH, and (CH 3 ) 2 CHCH 2 NH. Examples of “dialkylamino” include (CH 3 ) 2 N, (CH 3 CH 2 CH 2 ) 2 N and CH 3 CH 2 (CH 3 )N. “Alkylaminoalkyl” denotes alkylamino substitution on alkyl. Examples of “alkylaminoalkyl” include CH 3 NHCH 2 , CH 3 NHCH 2 CH 2 , CH 3 CH 2 NHCH 2 , CH 3 CH 2 CH 2 CH 2 NHCH 2 and CH 3 CH 2 NHCH 2 CH 2 . Examples of “dialkylaminoalkyl” include ((CH 3 ) 2 CH) 2 NCH 2 , (CH 3 CH 2 CH 2 ) 2 NCH 2 and CH 3 CH 2 (CH 3 )NCH 2 CH 2 . The term “alkylcarbonylamino” denotes alkyl bonded to a C(═O)NH moiety. Examples of “alkylcarbonylamino” include CH 3 CH 2 C(═O)NH and CH 3 CH 2 CH 2 C(═O)NH.

“Alkylcarbonylthio” denotes a straight-chain or branched alkylcarbonyl attached to and linked through a sulfur atom. Examples of “alkylcarbonylthio” include CH 3 C(═O)S, CH 3 CH 2 CH 2 C(═O)S and (CH 3 ) 2 CHC(═O)S. The term “alkyl(thiocarbonyl)oxy” refers to an alkylsulfinyl moiety group bonded to an oxygen atom. Examples of “alkyl(thiocarbonyl)oxy”, include CH 3 CH 2 OS(O) and CH 3 CH 2 CH 2 OS(O). The term “alkyl(thiocarbonyl)thio” refers to an alkylsulfinyl moiety bonded to a sulfur atom. Examples “alkyl(thiocarbonyl)thio” include CH 3 CH 2 S(O)S.

“Trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom, such as trimethylsilyl, triethylsilyl and tert-butyldimethylsilyl. Examples of “halotrialkylsilyl” include CF 3 (CH 3 ) 2 Si—, (CF 3 ) 3 Si—, and CH 2 Cl(CH 3 ) 2 Si—. “Hydroxyalkyl” denotes an alkyl group substituted with one hydroxy group. Examples of “hydroxyalkyl” include HOCH 2 CH 2 , CH 3 CH 2 (OH)CH and HOCH 2 CH 2 CH 2 CH 2 . “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH 2 , NCCH 2 CH 2 and CH 3 CH(CN)CH 2 .

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkoxy” denotes cycloalkyl linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety. Examples of “alkylcycloalkyl” include methylcyclopropyl, ethylcyclopentyl, and other straight-chain or branched alkyl groups bonded to cycloalkyl moiety. The term “alkoxycycloalkyl” denotes alkoxy substitution on a cycloalkyl moiety. Examples of “alkoxycycloalkyl” include methoxycyclopropyl, ethoxycyclopentyl, and other straight-chain or branched alkoxy groups bonded to a cycloalkyl moiety. “Cycloalkylalkoxy” denotes cycloalkylalkyl linked through an oxygen atom attached to the alkyl chain. Examples of “cycloalkylalkoxy” include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to straight-chain or branched alkoxy groups. Examples of “cyanocycloalkyl” include 4-cyanocyclohexyl and 3-cyanocyclopentyl. “Cycloalkenyl” includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl.

The term “halogen”, either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F 3 C—, ClCH 2 —, CF 3 CH 2 — and CF 3 CCl 2 —. The terms “halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, haloalkylsulfinyl, haloalkylsulfonyl, “haloalkenyloxy”, “haloalkynyloxy” “haloalkenyl”, “haloalkynyl”, “haloalkoxyalkyl”, “haloalkoxyalkoxy” “haloalkoxyhaloalkoxy”, “haloalkoxyhaloalkyl”, “halo alkylamino”, “haloalkylaminoalkyl” “halocycloalkoxy”, “halocycloalkoxyalkyl”, “halocycloalkylalkyl”, “halocycloalkenyl”, “halocycloalkenyloxy”, “halocycloalkenyloxy”, “halocycloalkenyloxyalkyl”, “alkoxyhaloalkoxy”, alkoxyhaloalkyl, haloalkylcarbonyloxy, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF 3 O—, CCl 3 CH 2 O—, HCF 2 CH 2 CH 2 O— and CF 3 CH 2 O—. Examples of “haloalkylthio” include CCl 3 S—, CF 3 S—, CCl 3 CH 2 S— and ClCH 2 CH 2 CH 2 S—. Examples of “haloalkylsulfinyl” include CF 3 S(O)—, CCl 3 S(O)—, CF 3 CH 2 S(O)— and CF 3 CF 2 S(O)—. Examples of “haloalkylsulfonyl” include CF 3 S(O) 2 —, CCl 3 S(O) 2 —, CF 3 CH 2 S(O) 2 — and CF 3 CF 2 S(O) 2 —. Examples of “haloalkenyl” include (Cl) 2 C═CHCH 2 — and CF 3 CH 2 CH═CHCH 2 —. Examples of “haloalkynyl” include HC≡CCHCl—, CF 3 C≡C—, CCl 3 C≡C— and FCH 2 C≡CCH 2 —. Examples of “haloalkoxyalkoxy” include CF 3 OCH 2 O—, ClCH 2 CH 2 OCH 2 CH 2 O—, Cl 3 CCH 2 OCH 2 O— as well as branched alkyl derivatives. Examples of “haloalkylamino” include CF 3 (CH 3 )CHNH, (CF 3 ) 2 CHNH and CH 2 ClCH 2 NH. The term “halodialkyl”, either alone or in compound words such as “halodialkylamino”, means at least one of the two alkyl groups is substituted with at least one halogen atom, and independently each halogenated alkyl group may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “halodialkylamino” include (BrCH 2 CH 2 ) 2 N and BrCH 2 CH 2 (ClCH 2 CH 2 )N.

›DETAILS OF THE INVENTION · 3 of 7

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moieties bonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH 3 C(═O)—, CH 3 CH 2 CH 2 C(═O)— and (CH 3 ) 2 CHC(═O)—. Examples of “alkoxycarbonyl” include CH 3 OC(═O)—, CH 3 CH 2 OC(═O)—, CH 3 CH 2 CH 2 OC(═O)—, (CH 3 ) 2 CHOC(═O)— and the different butoxy- or pentoxycarbonyl isomers. The terms “haloalkylcarbonyl” “haloalkoxycarbonyl”, “alkoxyalkylcarbonyl”, “cycloalkoxycarbonyl”, “cycloalkylalkoxycarbonyl”, “cycloalkylaminocarbonyl” are defined analogously.

The term “alkoxycarbonylamino” denotes a straight-chain or branched alkoxy moieties bonded to a C(═O) moiety of carbonylamino group. Examples of “alkoxycarbonylamino” include CH 3 OC(═O)NH— and CH 3 CH 2 OC(═O)NH—. Examples of “alkylaminocarbonyl” include CH 3 NHC(═O), CH 3 CH 2 NHC(═O), CH 3 CH 2 CH 2 NHC(═O), (CH 3 ) 2 CHNHC(═O) and the different butylamino- or pentylaminocarbonyl isomers. Examples of “dialkylaminocarbonyl” include (CH 3 ) 2 NC(═O), (CH 3 CH 2 ) 2 NC(═O), CH 3 CH 2 (CH 3 )NC(═O), (CH 3 ) 2 CH(CH 3 )NC(═O) and CH 3 CH 2 CH 2 (CH 3 )NC(═O). The term “alkylcarbonyloxy” denotes straight-chain or branched alkyl bonded to a C(═O)O moiety. Examples of “alkylcarbonyloxy” include CH 3 CH 2 C(═O)O and (CH 3 ) 2 CHC(═O)O. The term “alkylcarbonylalkoxy” denotes alkylcarbonyl bonded to an alkoxy moiety. Examples of “alkylcarbonylalkoxy” include CH 3 C(═O)CH 2 CH 2 O and CH 3 CH 2 C(═O)CH 2 O. Examples of “alkoxycarbonyloxy” include CH 3 CH 2 CH 2 OC(═O)O and (CH 3 ) 2 CHOC(═O)O. The term “cycloalkylcarbonyloxy” denotes a cycloalkylcarbonyl group bonded to oxygen. Examples of “cycloalkylcarbonyloxy” include c-Pr—C(O)O— and c-hexyl-C(O)O—.

“Alkylsulfonylamino” denotes an NH radical substituted with alkylsulfonyl. Examples of “alkylsulfonylamino” include CH 3 CH 2 S(═O) 2 NH— and (CH 3 ) 2 CHS(═O) 2 NH—. The term “alkylsulfonyloxy” denotes an alkylsulfonyl group bonded to an oxygen atom. Examples of “alkylsulfonyloxy” include CH 3 S(═O) 2 O —, CH 3 CH 2 S(═O) 2 O—, CH 3 CH 2 CH 2 S(═O) 2 O—, (CH 3 ) 2 CHS(═O) 2 O—, and the different butylsulfonyloxy, pentylsulfonyloxy and hexylsulfonyloxy isomers.

The term “cycloalkoxyalkyl” denotes cycloalkoxy substitution on an alkyl moiety. Examples of “cycloalkoxyalkyl” include cyclopropyloxymethyl, cyclopentyloxyethyl, and other cycloalkoxy moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkylthio” denotes cycloalkyl attached to and linked through a sulfur atom such as cyclopropylthio and cyclopentylthio; “cycloalkylsulfonyl” includes the corresponding sulfones. “Alkylcycloalkylalkyl” denotes an alkyl group substituted with alkylcycloalkyl. Examples of “alkylcycloalkylalkyl” include 1-, 2-, 3- or 4-methyl or -ethyl cyclohexylmethyl. The term “cycloalkoxyalkoxyalkyl” denotes a cycloalkoxy moiety attached to an alkoxyalkyl group. Examples of the term “cycloalkoxyalkoxyalkyl” include (tetrahydrofuran-2-yl)CH 2 OCH 2 —, (tetrahydrofuran-3-yl)CH 2 CH 2 O CH 2 — or (oxiran-2-yl)CH 2 OCH 2 CH 2 —. The term “cycloalkylcycloalkyl” denotes cycloalkyl substitution on another cycloalkyl ring, wherein each cycloalkyl ring independently has from 3 to 7 carbon atom ring members. Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (such as 1,1′-bicyclopropyl-1-yl, 1,1′-bicyclopropyl-2-yl), cyclohexylcyclopentyl (such as 4-cyclopentylcyclohexyl) and cyclohexylcyclohexyl (such as 1,1′-bicyclohexyl-1-yl), and the different cis- and trans-cycloalkylcycloalkyl isomers, (such as (1R,2S)-1,1′-bicyclopropyl-2-yl and (1R,2R)-1,1′-bicyclopropyl-2-yl).

“Dialkoxyalkyl” denotes two independent alkoxy groups substituted on same carbon of the alkyl group. Examples of “dialkoxyalkyl” include (CH 3 O) 2 CH— and CH 3 CH 2 O(CH 3 O)CH—. “Cycloalkylamino” denotes an NH radical substituted with cycloalkyl. Examples of “cycloalkylamino” include cyclopropylamino and cyclohexylamino. “Cycloalkyl(alkyl)amino” means a cycloalkylamino group where the hydrogen atom is replaced by an alkyl radical. Examples of “cycloalkyl(alkyl)amino” include groups such as cyclopropyl(methyl)amino, cyclobutyl(butyl)amino, cyclopentyl(propyl)amino, cyclohexyl(methyl)amino and the like. The term “cycloalkylaminoalkyl” denotes cycloalkylamino substitution on an alkyl group. Examples of “cycloalkylaminoalkyl” include cyclopropylaminomethyl, cyclopentylaminoethyl, and other cycloalkylamino moieties bonded to straight-chain or branched alkyl groups.

“Cycloalkylcarbonyl” denotes cycloalkyl bonded to a C(═O) group including, for example, cyclopropylcarbonyl and cyclopentylcarbonyl. The term “cycloalkoxycarbonyl” means cycloalkoxy bonded to a C(═O) group, for example, cyclopropyloxycarbonyl and cyclopentyloxycarbonyl. “Cycloalkylaminocarbonyl” denotes cycloalkylamino bonded to a C(═O) group, for example, cyclopentylaminocarbonyl and cyclohexylaminocarbonyl. “Cycloalkylalkoxycarbonyl” denotes cycloalkylalkoxy bonded to a C(═O) group. Examples of “cycloalkylalkoxycarbonyl” include cyclopropylethoxycarbonyl and cyclopentylmethoxycarbonyl. “Cycloalkylcarbonyloxy” denotes cycloalkylcarbonyl attached to and linked through an oxygen atom. Examples of “cycloalkylcarbonyloxy” include cyclohexylcarbonyloxy and cyclopentylcarbonyloxy.

The term “cycloalkenylalkyl” denotes cycloalkenyl substitution on an alkyl moiety. Examples of “cycloalkenylalkyl” include cyclobutenylmethyl, cyclopentenylethyl, and other cycloalkenyl moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkenyloxy” denotes cycloalkenyl linked through an oxygen atom such as cyclopentenyloxy and cyclohexenyloxy. The term “cycloalkenyloxyalkyl” denotes cycloalkenyloxy substitution on an alkyl moiety. Examples of “cycloalkenyloxyalkyl” include cyclobutenyloxymethyl, cyclopentenyloxyethyl, and other cycloalkenyloxy moieties bonded to straight-chain or branched alkyl groups.

The term “alkylaminosulfonyl” denotes a straight-chain or branched alkylamino moiety bonded to a sulfonyl group. Examples of an “alkylaminosulfonyl” group include CH 3 NHS(O) 2 — or CH 3 CH 2 CH 2 NHS(O) 2 —. The term “dialkylaminosulfonyl” denotes a straight-chain or branched dialkylamino moiety bonded to a sulfonyl group. Examples of a “dialkylaminosulfonyl” group include (CH 3 ) 2 NS(O) 2 — or (CH 3 CH 2 CH 2 ) 2 NS(O) 2 —.

›DETAILS OF THE INVENTION · 4 of 7

The total number of carbon atoms in a substituent group is indicated by the “C i -C j ” prefix where i and j are numbers from 1 to 14. For example, C 1 -C 4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C 2 alkoxyalkyl designates CH 3 OCH 2 —; C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 )—, CH 3 OCH 2 CH 2 — or CH 3 CH 2 OCH 2 —; and C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 — and CH 3 CH 2 OCH 2 CH 2 —.

When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., (R v ) r , r is 1, 2, 3, 4 or 5 in U-1 of Exhibit 2. When a group contains a substituent which can be hydrogen, for example R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 18 , R 19 or R 20 , then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R v ) r in Q-29 of Exhibit 1 then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component of Formula 1 (e.g., substituent G) is carbocyclic or heterocyclic. The term “ring system” denotes two or more fused rings. The terms “bicyclic ring system” and “fused bicyclic ring system” denote a ring system consisting of two fused rings, in which either ring can be saturated, partially unsaturated, or fully unsaturated unless otherwise indicated. The term “ring member” refers to an atom or other moiety (e.g., C(═O), C(═S), S(O) or S(O) 2 ) forming the backbone of a ring or ring system.

The terms “carbocyclic ring”, “carbocycle” or “carbocyclic ring system” denote a ring or ring system wherein the atoms forming the ring backbone are selected only from carbon. Unless otherwise indicated, a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated carbocyclic ring satisfies Hückel's rule, then said ring is also called an “aromatic ring”. “Saturated carbocyclic” refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.

The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ring system” denote a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Hückel's rule, then said ring is also called a “heteroaromatic ring” or “aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and that (4n+2) π electrons, where n is a positive integer, are associated with the ring to comply with Hückel's rule. The term “aromatic ring system” denotes a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. The term “aromatic carbocyclic ring system” denotes a carbocyclic ring system in which at least one ring of the ring system is aromatic. The term “aromatic heterocyclic ring system” denotes a heterocyclic ring system in which at least one ring of the ring system is aromatic. The term “nonaromatic ring system” denotes a carbocyclic or heterocyclic ring system that may be fully saturated, as well as partially or fully unsaturated, provided that none of the rings in the ring system are aromatic. The term “nonaromatic carbocyclic ring system” denotes a carbocylcic ring system in which no ring in the ring system is aromatic. The term “nonaromatic heterocyclic ring system” denotes a heterocyclic ring system in which no ring in the ring system is aromatic.

As used herein, the following definitions shall apply unless otherwise indicated. The term “optionally substituted” is used interchangeably with the phrase “substituted or unsubstituted” or with the term “(un)substituted.” Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.

When G is a 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom, unless otherwise described. When G is (among others) a 5- or 6-membered heterocyclic ring it may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. Examples of a 5- or 6-membered unsaturated aromatic heterocyclic ring optionally substituted with from one or more substituents include the rings Q-1 through Q-60 illustrated in Exhibit 1 wherein R v is any substituent as defined in the Summary of the Invention for R 21 on carbon ring members or R 22 on nitrogen ring members, and r is an integer from 0 to 4, limited by the number of available positions on each Q group. As Q-29, Q-30, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42 and Q-43 have only one available position, for these Q groups r is limited to the integers 0 or 1, and r being 0 means that the Q group is unsubstituted and a hydrogen is present at the position indicated by (R v ) r .

›DETAILS OF THE INVENTION · 5 of 7

Note that when G is a 5- or 6-membered saturated or unsaturated non-aromatic heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents as defined in the Summary of the Invention for R 21 one or two carbon ring members of the heterocycle can optionally be in the oxidized form of a carbonyl moiety.

Examples of a 5- or 6-membered saturated or non-aromatic unsaturated heterocyclic ring include the rings U-1 through U-36 as illustrated in Exhibit 2. Note that when the attachment point on the U group is illustrated as floating, the U group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the U group by replacement of a hydrogen atom. The optional substituents corresponding to R v can be attached to any available carbon or nitrogen by replacing a hydrogen atom. For these U rings, r is typically an integer from 0 to 4, limited by the number of available positions on each U group.

Note that when G comprises a ring selected from U-29 through U-36, U 2 is selected from O, S or N. Note that when U 2 is N, the nitrogen atom can complete its valence by substitution with either H or the substituents corresponding to R v as defined in the Summary of the Invention for U (i.e. R 22 ).

As noted above, G can be (among others) an 8-, 9- or 10-membered fused bicyclic ring system optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention (i.e. R 21 ). Examples of 8-, 9- or 10-membered fused bicyclic ring system optionally substituted with from one or more substituents include the rings Q-81 through Q-123 illustrated in Exhibit 3 wherein R v is any substituent as defined in the Summary of the Invention for G (i.e. R 21 or R 22 ), and r is typically an integer from 0 to 4.

Although R v groups are shown in the structures Q-1 through Q-60 and Q-81 through Q-123, it is noted that they do not need to be present since they are optional substituents. The nitrogen atoms that require substitution to fill their valence are substituted with H or R v . Note that when the attachment point between (R v ) r and the Q group is illustrated as floating, (R v ) r can be attached to any available carbon atom or nitrogen atom of the Q group. Note that when the attachment point on the Q group is illustrated as floating, the Q group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the Q group by replacement of a hydrogen atom. Note that some Q groups can only be substituted with less than 4 R v groups (e.g., Q-1 through Q-5, Q-7 through Q-48, and Q-52 through Q-60).

As noted in the Summary of the Invention, R 1 and R 2 are taken together along with the atoms to which they are attached to make a 5-, 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O) 2 —, —C(O)— groups. Besides the possibility of R 1 and R 2 being separate substituents, they may also be connected to form a ring fused to the ring to which they are attached. The fused ring can be a 5-, 6- or 7-membered ring including as ring members the two atoms shared with the ring to which the substituents are attached. The other 3, 4 or 5 ring members of the fused ring are provided by R 1 and R 2 substituents taken together. These other ring members can include up to 5 carbon atoms (as allowed by the ring size) and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 3 N. The fused ring is optionally substituted with up to 3 substituents as noted in the Summary of the Invention. Exhibit 4 provides, as illustrative examples, rings formed by R 1 and R 2 taken together. As these rings are fused with a ring of Formula 1, a portion of the Formula 1 ring is shown and the truncated lines represent the ring bonds of the Formula 1 ring. The rings depicted are fused to the two adjacent atoms of a ring as shown in Formula 1. The optional substituents (R v ) r , are independently selected from the group consisting of halogen, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy; on carbon atom ring members. The optional substituents (R v ) r , are independently selected from the group consisting of H and C 1 -C 6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy; on nitrogen ring members. Substituents are limited by the number of available positions on each T-ring. When the attachment point between (R v ) r and the T-ring is illustrated as floating, R v may be bonded to any available T-ring carbon or nitrogen atom (as applicable). One skilled in the art recognizes that while r is nominally an integer from 0 to 3, some of the rings shown in Exhibit 4 have less than 3 available positions, and for these groups r is limited to the number of available positions. When “r” is 0 this means the ring is unsubstituted and hydrogen atoms are present at all available positions. If r is 0 and (R v ) r is shown attached to a particular atom, then hydrogen is attached to that atom. The nitrogen atoms that require substitution to fill their valence are substituted with H or R v . Furthermore, one skilled in the art recognizes that some of the rings shown in Exhibit 4 can form tautomers, and the particular tautomer depicted is representative of all the possible tautomers.

A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry , A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II , A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

›DETAILS OF THE INVENTION · 6 of 7

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.

One skilled in the art will recognize that when A is A-1, A-2 or A-3, and the R 3 variable is hydroxy or O − M + , then the resulting compound of Formula 1 can exist in either the “triketone” tautomer or the “di-keto enol” tautomer. Likewise, when A is A-1, A-2 or A-3, and the R 3 variable is —SH, the resulting compound of Formula 1 can exist in either the the “di-keto thioketo” tautomer or the “di-keto thioenol” tautomer. In any of these cases and for the purposes of this invention both tautomeric combinations represent fully functional species of the present invention. For example, named species using the phrase “2-(1,3-cyclohexanedione)” is synonymous with the term “3-oxo-1-cyclohexen-1-yl”.

Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term “polymorph” refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.

One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis , vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry , vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry , vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry , vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry , vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus a wide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof):

Embodiment 1. A compound of Formula 1 wherein A is A-1, A-3, A-4, A-5 or A-6. Embodiment 2. A compound of Embodiment 1 wherein A is A-1, A-3, A-5 or A-6. Embodiment 3. A compound of Embodiment 2 wherein A is A-1, A-3 or A-5. Embodiment 4. A compound of Embodiment 3 wherein A is A-1 or A-3. Embodiment 5. A compound of Embodiment 4 wherein A is A-1. Embodiment 6. A compound of Embodiment 4 wherein A is A-3. Embodiment 7. A compound of Formula 1 or any one of Embodiments 1 through 5 wherein A is other than A-1. Embodiment 8. A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B 1 is C-1. Embodiment 9. A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B 1 is C-2. Embodiment 10. A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B 2 is C-3. Embodiment 11. A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B 2 is C-4. Embodiment 12. A compound of Formula 1 or any one of Embodiments 1 through 11 wherein B 3 is C-1. Embodiment 13. A compound of Formula 1 or any one of Embodiments 1 through 11 wherein B 3 is C-2. Embodiment 14. A compound of Formula 1 or any one of Embodiments 1 through 13 wherein R 1 is phenyl, phenylsulfonyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —NHCHO, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 haloalkyl, C 2 -C 10 haloalkenyl, C 2 -C 12 haloalkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 halocycloalkyl, C 4 -C 14 alkylcycloalkyl, C 4 -C 14 cycloalkylalkyl, C 6 -C 18 cycloalkylcycloalkyl, C 4 -C 14 halocycloalkylalkyl, C 5 -C 16 alkylcycloalkylalkyl, C 3 -C 12 cycloalkenyl, C 3 -C 12 halocycloalkenyl, C 2 -C 12 alkoxyalkyl, C 3 -C 12 alkoxyalkenyl, C 4 -C 14 alkylcycloalkyl, C 4 -C 14 alkoxycycloalkyl, C 4 -C 14 cycloalkoxyalkyl, C 5 -C 14 cycloalkoxyalkoxyalkyl, C 3 -C 14 alkoxyalkoxyalkyl, C 2 -C 12 alkylthioalkyl, C 2 -C 12 alkylsulfinylalkyl, C 2 -C 12 alkylsulfonylalkyl, C 2 -C 12 alkylaminoalkyl, C 3 -C 14 dialkylaminoalkyl, C 2 -C 12 haloalkylaminoalkyl, C 4 -C 14 cycloalkylaminoalkyl, C 2 -C 12 alkylcarbonyl, C 2 -C 12 haloalkylcarbonyl, C 4 -C 14 cycloalkylcarbonyl, C 2 -C 12 alkoxycarbonyl, C 4 -C 16 cycloalkoxycarbonyl, C 5 -C 14 cycloalkylalkoxycarbonyl, C 2 -C 12 alkylaminocarbonyl, C 3 -C 14 dialkylaminocarbonyl, C 4 -C 14 cycloalkylaminocarbonyl, C 2 -C 9 cyanoalkyl, C 1 -C 10 hydroxyalkyl, C 4 -C 14 cycloalkenylalkyl, C 2 -C 12 haloalkoxyalkyl, C 2 -C 12 alkoxyhaloalkyl, C 2 -C 12 haloalkoxyhaloalkyl, C 4 -C 14 halocycloalkoxyalkyl, C 4 -C 14 cycloalkenyloxyalkyl, C 4 -C 14 halocycloalkenyloxyalkyl, C 3 -C 14 dialkoxyalkyl, C 3 -C 14 alkoxyalkylcarbonyl, C 3 -C 14 alkoxycarbonylalkyl or C 2 -C 12 haloalkoxycarbonyl. Embodiment 15. A compound of Formula 1 or any one of Embodiments 1 through 14 wherein R 1 is phenyl, phenylsulfonyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —NHCHO, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 alkoxycycloalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -C 10 dialkylaminoalkyl, C 2 -C 8 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkylcarbonyl, C 3 -C 10 alkoxycarbonylalkyl or C 2 -C 8 haloalkoxycarbonyl. Embodiment 16. A compound of Embodiment 15 wherein R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 alkoxycycloalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl or C 2 -C 8 alkylsulfonylalkyl. Embodiment 17. A compound of Embodiment 16 wherein R 1 is phenyl or —W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl or C 4 -C 10 alkoxycycloalkyl. Embodiment 18. A compound of Embodiment 17 wherein R 1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 19. A compound of Embodiment 18 wherein R 1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 20. A compound of Embodiment 19 wherein R 1 is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl. Embodiment 21. A compound of Embodiment 20 wherein R 1 is phenyl. Embodiment 22. A compound of Embodiment 19 wherein R 1 is 3,4-dimethoxyphenyl. Embodiment 23. A compound of Embodiment 19 wherein R 1 is 5-chloro-2-methylphenyl. Embodiment 24. A compound of Formula 1 or any one of Embodiments 1 through 21 wherein R 1 is other than phenyl. Embodiment 25. A compound of Embodiment 17 wherein R 1 is -G or —W 2 G; C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl. Embodiment 26. A compound of Embodiment 25 wherein R 1 is -G or —W 2 G. Embodiment 27. A compound of Embodiment 26 wherein R 1 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl. Embodiment 28. A compound of Embodiment 27 wherein R 1 is n-Pr, i-Pr, n-Bu, c-hexyl, c-heptyl, —CH 2 CH 2 OCH 3 , —CH 2 CH 2 CH 2 OCH 3 or —CH 2 CH 2 OCH 2 CH 3 . Embodiment 29. A compound of Embodiment 28 wherein R 1 is n-Pr, c-hexyl, —CH 2 CH 2 OCH 3 or —CH 2 CH 2 CH 2 OCH 3 . Embodiment 29a. A compound of Embodiment 29 wherein R 1 is n-Pr or —CH 2 CH 2 OCH 3 . Embodiment 29b. A compound of Embodiment 29 wherein R 1 is c-hexyl. Embodiment 30. A compound of Formula 1 or any one of Embodiments 1 through 17 wherein W 1 is C 1 -C 6 alkylene. Embodiment 31. A compound of Embodiment 30 wherein W 1 is —CH 2 —. Embodiment 32. A compound of Formula 1 or any one of Embodiments 1 through 17, 25 or 26 wherein W 2 is —CH 2 —. Embodiment 33. A compound of Formula 1 or any one of Embodiments 1 through 32 wherein R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G; C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 cycloalkoxyalkyl, C 4 -C 10 cycloalkoxylalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylcarbonyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 8 trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 halocycloalkenyloxy, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyhaloalkoxy, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -C 8 alkyl(thiocarbonyl)oxy, C 3 -C 8 cycloalkylsulfinyl or C 3 -C 10 halotrialkylsilyl. Embodiment 34. A compound of Embodiment 33 wherein R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment 35. A compound of Embodiment 34 wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl. Embodiment 36. A compound of Embodiment 35 wherein R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl. Embodiment 36a. A compound of Embodiment 35 wherein R 2 is phenyl, 3-bromophenyl, 3-chlorophenyl, or 2-methylphenyl. Embodiment 37. A compound of Embodiment 35 wherein R 2 is phenyl. Embodiment 38. A compound of Formula 1 or any one of Embodiments 1 through 36 wherein R 2 is other than phenyl. Embodiment 39. A compound of Embodiment 35 wherein R 2 is 3-thienyl or 2-thienyl. Embodiment 40. A compound of Embodiment 35 wherein R 2 is n-propyl, n-butyl, or cyclopropyl. Embodiment 41. A compound of Formula 1 or any one of Embodiments 1 through 13 wherein R 1 and R 2 are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O) 2 —, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy; and optionally substituted on nitrogen ring members selected from H and C 1 -C 6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy. Embodiment 42. A compound of Embodiment 41 wherein R 1 and R 2 are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 1 oxygen atoms, 1 nitrogen atoms or 1 sulfur atoms or up to one —S(O)—, —S(O) 2 —, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and optionally substituted on nitrogen ring members selected from H and C 1 -C 6 alkyl. Embodiment 43. A compound of Embodiment 42 wherein R 1 and R 2 are taken together along with the atoms to which they are attached to make a 7-membered partially unsaturated ring optionally substituted with halogen, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 2 -C 8 alkoxyalkyl on carbon atom ring members. Embodiment 44. A compound of Embodiment 43 wherein R 1 and R 2 are taken together along with the atoms to which they are attached to make an unsubstituted 7-membered partially unsaturated ring. Embodiment 45. A compound of Formula 1 or any one of Embodiments 1 through 34 wherein W 3 is —CH 2 —. Embodiment 46. A compound of Formula 1 or any one of Embodiments 1 through 32 wherein W 4 is —CH 2 —. Embodiment 47. A compound of Formula 1 or any one of Embodiments 1 through 46 wherein R 3 is hydroxy, —O − M + , C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy or C 3 -C 10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R 21 . Embodiment 48. A compound of Embodiment 47 wherein R 3 is hydroxy, —O − M + or C 2 -C 8 alkylcarbonyloxy; or phenylsulfonyloxy optionally substituted with up to two substituents selected from R 21 . Embodiment 49. A compound of Embodiment 48 wherein M + is a sodium or potassium metal cation. Embodiment 50. A compound of Embodiment 49 wherein R 3 is hydroxy or C 2 -C 8 alkylcarbonyloxy. Embodiment 51. A compound of Embodiment 50 wherein R 3 is hydroxy or —OC(═O)CH 2 CH(CH 3 ) 2 . Embodiment 52. A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 51 wherein R 4 , R 5 , R 6 and R 7 are each independently H, or C 1 -C 6 alkyl. Embodiment 53. A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 52 wherein R 8 is C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment 54. A compound of Embodiment 53 wherein R 8 is CH 3 , CH 2 CH 3 or cyclopropyl. Embodiment 55. A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14 through 51 wherein R 9 is C 1 -C 6 alkyl. Embodiment 56. A compound of Embodiment 55 wherein R 9 is CH 2 CH 3 . Embodiment 57. A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14 through 51 wherein R 10 is H, halogen or C 1 -C 6 alkyl. Embodiment 58. A compound of Embodiment 57 wherein R 10 is H or CH 3 . Embodiment 59. A compound of Formula 1 or any one of Embodiments 1, 2, 8, 10 and 12 through 51 wherein R 11 is H or C 1 -C 6 alkyl. Embodiment 60. A compound of Embodiment 59 wherein R 11 is H. Embodiment 61. A compound of Formula 1 or any one of Embodiments 1, 2, 8, 10 and 12 through 51 wherein R 12 is H, halogen, cyano, hydroxy, amino or C 1 -C 6 alkyl. Embodiment 62. A compound of Embodiment 61 wherein R 12 is H, halogen, cyano, C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment 63. A compound of Embodiment 62 wherein R 12 is CH 3 , CH 2 CH 3 or cyclopropyl. Embodiment 64. A compound of Formula 1 or any one of Embodiments 7 and 15 through 51 wherein R 13 is H, halogen, cyano or nitro. Embodiment 65. A compound of Embodiment 64 wherein R 13 is cyano or nitro. Embodiment 66. A compound of Formula 1 or any one of Embodiments 1 through 65 wherein when instances of R 14 and R 18 are taken alone (i.e. R 14 and R 18 are not taken together as alkylene or alkenylene), then independently said instances of R 14 and R 18 are H or C 1 -C 6 alkyl. Embodiment 67. A compound of Embodiment 66 wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H or CH 3 . Embodiment 68. A compound of Embodiment 68 wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H. Embodiment 69. A compound of Formula 1 or any one of Embodiments 1 through 68 wherein when instances of R 14 and R 18 are taken together, then said instances of R 14 and R 18 are taken together as —CH 2 CH 2 CH 2 — or —CH═CHCH 2 —. Embodiment 70. A compound of Formula 1 or any one of Embodiments 1 through 68 wherein all instances of R 14 and R 18 are taken alone. Embodiment 71. A compound of Formula 1 or any one of Embodiments 1 through 70 wherein independently each R 15 and R 19 is H or C 1 -C 6 alkyl. Embodiment 72. A compound of Embodiment 71 wherein independently each R 15 and R 19 is H or CH 3 . Embodiment 73. A compound of Embodiment 72 wherein independently each R 15 and R 19 is H. Embodiment 73a. A compound of Embodiments 67 and 72 wherein each R 14 , R 15 , R 18 and R 19 is H or CH 3 . Embodiment 73b. A compound of Embodiment 73 wherein each R 14 , R 15 , R 18 and R 19 is H. Embodiment 74. A compound of Formula 1 or any one of Embodiments 1 through 73 wherein R 20 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 8 cycloalkyl. Embodiment 75. A compound of Embodiment 74 wherein R 20 is H or CH 3 . Embodiment 76. A compound of Formula 1 or any one of Embodiments 1 through 4, 6, 10, 11 and 14 through 51 wherein T is —CH 2 CH 2 — or —CH═CH—. Embodiment 77. A compound of Embodiment 76 wherein T is —CH 2 CH 2 —. Embodiment 78. A compound of Formula 1 or any one of Embodiments 1 through 17 wherein each G is independently a 5- or 6-membered heterocyclic ring optionally substituted with up to five substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members. Embodiment 79. A compound of Embodiment 78 wherein G is

›DETAILS OF THE INVENTION · 7 of 7

This invention also includes a herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) AHAS inhibitors, (b3) ACCase inhibitors, (b4) auxin mimics and (b5) EPSP inhibitors.

Embodiment 94. A herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1), (b2) and (b3). Embodiment 95. A herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1). Embodiment 96. A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1 and (b) one additional active ingredient selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, dimethametryn, diuron, hexazinone, isoproturon, metribuzin, pyridate, simazine and terbutryn. Embodiment 97. A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1; and (b) bromoxynil. Embodiment 98. A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1; and (b) dimethametryn. Embodiment 99. A herbicidal mixture comprising (a) a compound of Formula 1 and (b) diuron and hexazinone.

Combinations of Embodiments 1-93 are illustrated by:

›Embodiment A. A compound of Formula 1 wherein

A is A-1, A-3, A-4, A-5 or A-6; R 1 is phenyl, phenylsulfonyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —NHCHO, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, haloalkyl, C 2 -C 10 haloalkenyl, C 2 -C 12 haloalkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 halocycloalkyl, C 4 -C 14 alkylcycloalkyl, C 4 -C 14 cycloalkylalkyl, C 6 -C 18 cycloalkylcycloalkyl, C 4 -C 14 halocycloalkylalkyl, C 5 -C 16 alkylcycloalkylalkyl, C 3 -C 12 cycloalkenyl, C 3 -C 12 halocycloalkenyl, C 2 -C 12 alkoxyalkyl, C 3 -C 12 alkoxyalkenyl, C 4 -C 14 alkylcycloalkyl, C 4 -C 14 alkoxycycloalkyl, C 4 -C 14 cycloalkoxyalkyl, C 5 -C 14 cycloalkoxyalkoxyalkyl, C 3 -C 14 alkoxyalkoxyalkyl, C 2 -C 12 alkylthioalkyl, C 2 -C 12 alkylsulfinylalkyl, C 2 -C 12 alkylsulfonylalkyl, C 2 -C 12 alkylaminoalkyl, C 3 -C 14 dialkylaminoalkyl, C 2 -C 12 haloalkylaminoalkyl, C 4 -C 14 cycloalkylaminoalkyl, C 2 -C 12 alkylcarbonyl, C 2 -C 12 haloalkylcarbonyl, C 4 -C 14 cycloalkylcarbonyl, C 2 -C 12 alkoxycarbonyl, C 4 -C 16 cycloalkoxycarbonyl, C 5 -C 14 cycloalkylalkoxycarbonyl, C 2 -C 12 alkylaminocarbonyl, C 3 -C 14 dialkylaminocarbonyl, C 4 -C 14 cycloalkylaminocarbonyl, C 2 -C 9 cyanoalkyl, C 1 -C 10 hydroxyalkyl, C 4 -C 14 cycloalkenylalkyl, C 2 -C 12 haloalkoxyalkyl, C 2 -C 12 alkoxyhaloalkyl, C 2 -C 12 haloalkoxyhaloalkyl, C 4 -C 14 halocycloalkoxyalkyl, C 4 -C 14 cycloalkenyloxyalkyl, C 4 -C 14 halocycloalkenyloxyalkyl, C 3 -C 14 dialkoxyalkyl, C 3 -C 14 alkoxyalkylcarbonyl, C 3 -C 14 alkoxycarbonylalkyl or C 2 -C 12 haloalkoxycarbonyl; W 1 is C 1 -C 6 alkylene; W 2 is —CH 2 —; R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G; C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 cycloalkoxyalkyl, C 4 -C 10 cycloalkoxylalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylcarbonyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 8 trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 halocycloalkenyloxy, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyhaloalkoxy, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -C 8 alkyl(thiocarbonyl)oxy, C 3 -C 8 cycloalkylsulfinyl or C 3 -C 10 halotrialkylsilyl; W 3 is —CH 2 —; W 4 is —CH 2 —; R 1 and R 2 are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O) 2 —, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy; and optionally substituted on nitrogen ring members selected from H and C 1 -C 6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy; R 3 is hydroxy, —O − M + , C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy or C 3 -C 10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R 21 ; M + is a sodium or potassium metal cation; R 9 is C 1 -C 6 alkyl; R 10 is H, halogen or C 1 -C 6 alkyl; R 11 is H or C 1 -C 6 alkyl; R 12 is H, halogen, cyano, hydroxy, amino or C 1 -C 6 alkyl; R 13 is cyano or nitro; each R 14 , R 15 , R 18 and R 19 is H or CH 3 ; R 14 and R 18 are taken together as —CH 2 CH 2 CH 2 — or —CH═CHCH 2 —; R 20 is H or CH 3 ; T is —CH 2 CH 2 — or —CH═CH—; each G is G-1 through G-20 (as depicted in Embodiment 79); r is 0, 1, 2 or 3; each R 21 is independently halogen, cyano, hydroxy, nitro, —CHO, —SH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl or C 3 -C 8 cycloalkylsulfonyl; and each R 22 is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl.

›Embodiment B. A compound of Embodiment A wherein

X is CH; A is A-3 or A-5; B 2 is C-3; R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl or C 2 -C 8 alkylsulfonylalkyl; R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl; R 3 is hydroxy or —O − M + ; or phenylsulfonyloxy optionally substituted on ring members with up to two substituents selected from R 21 ; R 9 is CH 2 CH 3 ; R 10 is H or CH 3 ; W 1 is —CH 2 —; W 3 is —CH 2 —; G is G-13, G-14, G-15, G-16 or G-17; and each R 21 is independently halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio.

›Embodiment C. A compound of Embodiment A wherein

A is A-1, A-3 or A-5; B 1 is C-1; B 2 is C-3; B 3 is C-1; R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 alkoxycycloalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 12 alkylsulfonylalkyl or C 2 -C 8 alkylsulfonylalkyl; W 1 is —CH 2 —; R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl; R 1 and R 2 are taken together along with the atoms to which they are attached to make an unsubstituted 7-membered partially unsaturated ring; R 3 is hydroxy or C 2 -C 8 alkylcarbonyloxy; R 9 is CH 2 CH 3 ; R 10 is H or CH 3 ; G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20; and R 21 is independently halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio.

›Embodiment D. A compound of Embodiment C wherein

A is A-1 or A-3; R 1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl; R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl; R 3 is hydroxy or —OC(═O)CH 2 CH(CH 3 ) 2 ; each R 14 , R 15 , R 18 and R 19 is H or CH 3 ; and T is —CH 2 CH 2 —.

›Embodiment E. A compound of Embodiment D wherein

A is A-1; R 1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl; R 2 is phenyl, 3-chlorophenyl, or 2-methylphenyl; R 3 is hydroxy or —OC(═O)CH 2 CH(CH 3 ) 2 ; and each R 14 , R 15 , R 18 and R 19 is H.

›Embodiment F. A compound of Embodiment C wherein

A is A-3; R 1 is n-Pr or —CH 2 CH 2 OCH 3 ; R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl; R 3 is hydroxy; and each R 14 , R 15 , R 18 and R 19 is H.

›Embodiment G. A compound of Embodiment C wherein

A is A-1; R 1 is -G or —W 2 G; C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl; G is G-19 or G-20; R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl; R 3 is hydroxy; and each R 14 , R 15 , R 18 and R 19 is H.

›Embodiment H. A compound of Embodiment C wherein · 1 of 5

A is A-1; R 1 is n-Pr, c-hexyl, —CH 2 CH 2 OCH 3 or —CH 2 CH 2 CH 2 OCH 3 ; R 2 is 3-thienyl or 2-thienyl; R 3 is hydroxy; and each R 14 , R 15 , R 18 and R 19 is H.

Specific embodiments include a compound of Formula 1 selected from:

5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 2), 5-[(2-hydroxy-6-oxo-1-cyclohexane-1-yl)carbonyl]-3-(3-methoxypropyl)-2-(3-methylphenyl)-4(3H)-pyrimidinone (Compound 118), 5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone (Compound 97), 5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(4-methoxyphenyl)-2-phenyl-4(3H)-pyrimidinone (Compound 4), 5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(3-methoxypropyl)-2-phenyl-4(3H)-pyrimidinone (Compound 81) and 3-cyclohexyl-5-[(2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone (Compound 128).

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1Q from the Summary of the Invention as used in the following Embodiments includes N-oxides and salts thereof):

Embodiment 1Q. A compound of Formula 1Q wherein A′ is A′-1, A′-3 or A′-5. Embodiment 2Q. A compound of Embodiment 2Q wherein A′ is A′-1 or A′-3. Embodiment 3Q. A compound of Embodiment 3Q wherein A′ is A′-1. Embodiment 4Q. A compound of Embodiment 4Q wherein A′ is A′-3. Embodiment 5Q. A compound of Formula 1Q or any one of Embodiments 1Q through 4Q wherein B 1 is C-1. Embodiment 6Q. A compound of Formula 1Q or any one of Embodiments 1Q through 4Q wherein B 1 is C-2. Embodiment 7Q. A compound of Formula 1Q or any one of Embodiments 1Q through 6Q wherein B 2 is C-3. Embodiment 8Q. A compound of Formula 1Q or any one of Embodiments 1Q through 9Q wherein B 2 is C-4. Embodiment 9Q. A compound of Formula 1Q or any one of Embodiments 1Q through 8Q wherein B 3 is C-1. Embodiment 10Q. A compound of Formula 1Q or any one of Embodiments 1Q through 8Q wherein B 3 is C-2. Embodiment 11Q. A compound of Formula 1Q or any one of Embodiments 1Q through 10Q wherein R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 alkoxycycloalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 12 alkylsulfinylalkyl or C 2 -C 8 alkylsulfonylalkyl. Embodiment 12Q. A compound of Embodiment 11Q wherein R 1 is phenyl or —W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl or C 4 -C 10 alkoxycycloalkyl. Embodiment 13Q. A compound of Embodiment 12Q wherein R 1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 14Q. A compound of Embodiment 13Q wherein R 1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 15Q. A compound of Embodiment 14Q wherein R 1 is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl. Embodiment 16Q. A compound of Embodiment 15Q wherein R 1 is phenyl. Embodiment 17Q. A compound of Embodiment 14Q wherein R 1 is 3,4-dimethoxyphenyl. Embodiment 18Q. A compound of Embodiment 14Q wherein R 1 is 5-chloro-2-methylphenyl. Embodiment 19Q. A compound of Formula 1Q or any one of Embodiments 1 through 16Q wherein R 1 is other than phenyl. Embodiment 20Q. A compound of Embodiment 11Q wherein R 1 is -G or —W 2 G; C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl. Embodiment 21Q. A compound of Embodiment 20Q wherein R 1 is -G or —W 2 G. Embodiment 22Q. A compound of Embodiment 20Q wherein R 1 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or C 2 -C 8 alkoxyalkyl. Embodiment 23Q. A compound of Embodiment 22Q wherein R 1 is n-Pr, i-Pr, n-Bu, c-hexyl, —CH 2 CH 2 OCH 3 , —CH 2 CH 2 CH 2 OCH 3 or —CH 2 CH 2 OCH 2 CH 3 . Embodiment 24Q. A compound of Embodiment 23Q wherein R 1 is n-Pr, c-hexyl, —CH 2 CH 2 OCH 3 or —CH 2 CH 2 CH 2 OCH 3 . Embodiment 25Q. A compound of Formula 1Q or any one of Embodiments 1Q through 12Q wherein W 1 is C 1 -C 6 alkylene. Embodiment 26Q. A compound of Embodiment 25Q wherein W 1 is —CH 2 —. Embodiment 27Q. A compound of Formula 1Q or any one of Embodiments 1Q through 12Q, 20Q or 21Q wherein W 2 is —CH 2 —. Embodiment 28Q. A compound of Formula 1Q or any one of Embodiments Embodiment 1Q through 27Q wherein R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment 29Q. A compound of Embodiment 28Q wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl. Embodiment 30Q. A compound of Embodiment 29Q wherein R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl. Embodiment 31Q. A compound of Embodiment 30Q wherein R 2 is phenyl. Embodiment 32Q. A compound of Formula 1Q or any one of Embodiments 1Q through 30Q wherein R 2 is other than phenyl. Embodiment 33Q. A compound of Embodiment 32Q wherein R 2 is 3-thienyl or 2-thienyl. Embodiment 34Q. A compound of Embodiment 33Q wherein R 2 is n-propyl, n-butyl, or cyclopropyl. Embodiment 35Q. A compound of Formula 1Q or any one of Embodiments 1Q through 28Q wherein W 3 is —CH 2 —. Embodiment 36Q. A compound of Formula 1Q or any one of Embodiments 1Q through 3Q, 7Q and 14Q through 51Q wherein R 9 is C 1 -C 6 alkyl. Embodiment 37Q. A compound of Formula 1Q or any one of Embodiments 1Q or 11Q through 36Q wherein R 9 is CH 2 CH 3 . Embodiment 38Q. A compound of Formula 1Q or any one of Embodiments 1Q or 11Q through 36Q wherein R 10 is H, halogen or C 1 -C 6 alkyl. Embodiment 39Q. A compound of Embodiment 38Q wherein R 10 is H or CH 3 . Embodiment 40Q. A compound of Formula 1Q or any one of Embodiments 1Q through 39Q wherein when instances of R 14 and R 18 are taken alone (i.e. R 14 and R 18 are not taken together as alkylene or alkenylene), then independently said instances of R 14 and R 18 are H or C 1 -C 6 alkyl. Embodiment 41Q. A compound of Embodiment 40Q wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H or CH 3 . Embodiment 42Q. A compound of Embodiment 41Q wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H. Embodiment 43Q. A compound of Formula 1Q or any one of Embodiments 1Q through 42Q wherein independently each R 15 and R 19 is H or CH 3 . Embodiment 44Q. A compound of Embodiment 43Q wherein independently each R 15 and R 19 is H. Embodiment 45Q. A compound of Formula 1Q or any one of Embodiments 1Q through 44Q wherein R 20 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 8 cycloalkyl. Embodiment 46Q. A compound of Embodiment 45Q wherein R 20 is H or CH 3 . Embodiment 47Q. A compound of Formula 1Q or any one of Embodiments 1Q, 2Q, 4Q, 7Q, 8Q and 11Q through 46Q wherein T is —CH 2 CH 2 — or —CH═CH—. Embodiment 48Q. A compound of Embodiment 47Q wherein T is —CH 2 CH 2 —. Embodiment 49Q. A compound of Formula 1Q or any one of Embodiments 1Q through 48Q wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79). Embodiment 50Q. A compound of Embodiment 49Q wherein when R 1 is G, then G is G-19 or G-20. Embodiment 51Q. A compound of Embodiment 50Q wherein when R 1 is G, then G is G-19. Embodiment 52Q. A compound of Embodiment 50Q wherein when R 1 is G, then G is G-20. Embodiment 53Q. A compound of Embodiment 49Q wherein when R 2 is G, then G is G-2, G-3 or G-15. Embodiment 54Q. A compound of Embodiment 53Q wherein when R 2 is G, then G is G-2. Embodiment 55Q. A compound of Embodiment 53Q wherein when R 2 is G, then G is G-3. Embodiment 56Q. A compound of Formula 1Q or any one of Embodiments 1Q through 55Q wherein each R 21 is independently halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio. Embodiment 57Q. A compound of Embodiment 56Q wherein each R 21 is independently fluorine, chlorine, bromine, CH 3 , CF 3 , OCH 3 , OCF 3 or SCH 3 . Embodiment 58Q. A compound of Formula 1Q or any one of Embodiments 1Q through 57Q wherein each R 22 is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl. Embodiment 59Q. A compound of Embodiment 58Q wherein each R 22 is independently CH 3 or CH 2 CF 3 .

›Embodiment H. A compound of Embodiment C wherein · 2 of 5

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1R from the Summary of the Invention as used in the following Embodiments include N-oxides and salts thereof):

Embodiment 1R. A compound of Formula 1R wherein R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 alkoxycycloalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 12 alkylsulfinylalkyl or C 2 -C 8 alkylsulfonylalkyl. Embodiment 2R. A compound of Embodiment 1R wherein R 1 is phenyl or —W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl or C 4 -C 10 alkoxycycloalkyl. Embodiment 3R. A compound of Embodiment 2R wherein R 1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 4R. A compound of Embodiment 3R wherein R 1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 5R. A compound of Embodiment 4R wherein R 1 is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl. Embodiment 6R. A compound of Embodiment 5R wherein R 1 is phenyl. Embodiment 7R. A compound of Embodiment 4R wherein R 1 is 3,4-dimethoxyphenyl. Embodiment 8R. A compound of Embodiment 4R wherein R 1 is 5-chloro-2-methylphenyl. Embodiment 9R. A compound of Formula 1R or any one of Embodiments 1R through 8R wherein R 1 is other than phenyl. Embodiment 10R. A compound of Formula 1R or any one of Embodiments 1R and 2R R wherein R 1 is -G or —W 2 G; C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl. Embodiment 11R. A compound of Embodiment 10R wherein R 1 is -G or —W 2 G. Embodiment 12R. A compound of Embodiment 10R wherein R 1 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl. Embodiment 13R. A compound of Embodiment 12R wherein R 1 is n-Pr, i-Pr, n-Bu, c-hexyl, —CH 2 CH 2 OCH 3 , —CH 2 CH 2 CH 2 OCH 3 or —CH 2 CH 2 OCH 2 CH 3 . Embodiment 14R. A compound of Embodiment 13R wherein R 1 is n-Pr, c-hexyl, —CH 2 CH 2 OCH 3 or —CH 2 CH 2 CH 2 OCH 3 . Embodiment 15R. A compound of Formula 1R or any one of Embodiments 1R and 2R wherein W 1 is C 1 -C 6 alkylene. Embodiment 16R. A compound of Embodiment 15R wherein W 1 is —CH 2 —. Embodiment 17R. A compound of Formula 1R or any one of Embodiments 1R, 2R 10R and 11R wherein W 2 is —CH 2 —. Embodiment 18R. A compound of Formula 1R or any one of Embodiments Embodiment 1R through 17R wherein R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment 19R. A compound of Embodiment 18R wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment 20R. A compound of Embodiment 19R wherein R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl. Embodiment 21R. A compound of Embodiment 20R wherein R 2 is phenyl. Embodiment 22R. A compound of Formula 1R or any one of Embodiments 1R through 21R wherein R 2 is other than phenyl. Embodiment 23R. A compound of Embodiment 22R wherein R 2 is 3-thienyl or 2-thienyl. Embodiment 24R. A compound of Embodiment 23R wherein R 2 is n-propyl, n-butyl, or cyclopropyl. Embodiment 25R. A compound of Formula 1R or any one of Embodiments 1R through 18R wherein W 3 is —CH 2 —. Embodiment 26R. A compound of Formula 1R or any one of Embodiments 1R through 25R wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79). Embodiment 27R. A compound of Embodiment 26R wherein when R 1 is G, then G is G-19 or G-20. Embodiment 28R. A compound of Embodiment 27R wherein when R 1 is G, then G is G-19. Embodiment 29R. A compound of Embodiment 28R wherein when R 1 is G, then G is G-20. Embodiment 30R. A compound of Embodiment 26R wherein when R 2 is G, then G is G-2, G-3 or G-15. Embodiment 31R. A compound of Embodiment 30R wherein when R 2 is G, then G is G-2. Embodiment 32R. A compound of Embodiment 31R wherein when R 2 is G, then G is G-3. Embodiment 33R. A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R 21 is independently halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio. Embodiment 34R. A compound of Embodiment 33R wherein each R 21 is independently fluorine, chlorine, bromine, CH 3 , CF 3 , OCH 3 , OCF 3 or SCH 3 . Embodiment 35R. A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R 22 is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl. Embodiment 36R. A compound of Embodiment 35R wherein each R 22 is independently CH 3 or CH 2 CF 3 .

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1S from the Summary of the Invention as used in the following Embodiments includes N-oxides and salts thereof):

›Embodiment H. A compound of Embodiment C wherein · 3 of 5

Embodiment 1S. A compound of Formula 1S wherein R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 alkoxycycloalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 12 alkylsulfinylalkyl or C 2 -C 8 alkylsulfonylalkyl. Embodiment 2S. A compound of Embodiment 1S wherein R 1 is phenyl or —W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 alkoxycycloalkyl. Embodiment 3S. A compound of Embodiment 2S wherein R 1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 4S. A compound of Embodiment 3S wherein R 1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 5S. A compound of Embodiment 4S wherein R 1 is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl. Embodiment 6S. A compound of Embodiment 5S wherein R 1 is phenyl. Embodiment 7S. A compound of Embodiment 4S wherein R 1 is 3,4-dimethoxyphenyl. Embodiment 8S. A compound of Embodiment 4S wherein R 1 is 5-chloro-2-methylphenyl. Embodiment 9S. A compound of Formula 1S or any one of Embodiments 1S through 8S wherein R 1 is other than phenyl. Embodiment 10S. A compound of Formula 1S or any one of Embodiments 1S and 2S wherein R 1 is -G or —W 2 G; C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl. Embodiment 11S. A compound of Embodiment 10S wherein R 1 is -G or —W 2 G. Embodiment 12S. A compound of Embodiment 10S wherein R 1 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl. Embodiment 13S. A compound of Embodiment 12S wherein R 1 is n-Pr, i-Pr, n-Bu, c-hexyl, —CH 2 CH 2 OCH 3 , —CH 2 CH 2 CH 2 OCH 3 or —CH 2 CH 2 OCH 2 CH 3 . Embodiment 14S. A compound of Embodiment 13S wherein R 1 is n-Pr, c-hexyl, —CH 2 CH 2 OCH 3 or —CH 2 CH 2 CH 2 OCH 3 . Embodiment 15S. A compound of Formula 1S or any one of Embodiments 1S and 2S wherein W 1 is C 1 -C 6 alkylene. Embodiment 16S. A compound of Embodiment 15S wherein W 1 is —CH 2 —. Embodiment 17S. A compound of Formula 15 or any one of Embodiments 1S, 2S 10S and 11S wherein W 2 is —CH 2 —. Embodiment 18S. A compound of Formula 1s or any one of Embodiments Embodiment 1S through 17S wherein R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment 19S. A compound of Embodiment 18S wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl. Embodiment 20S. A compound of Embodiment 19S wherein R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl. Embodiment 21S. A compound of Embodiment 20S wherein R 2 is phenyl. Embodiment 22S. A compound of Formula 1S or any one of Embodiments 1S through 21S wherein R 2 is other than phenyl. Embodiment 23S. A compound of Embodiment 22S wherein R 2 is 3-thienyl or 2-thienyl. Embodiment 24S. A compound of Embodiment 23S wherein R 2 is n-propyl, n-butyl, or cyclopropyl. Embodiment 25S. A compound of Formula 1S or any one of Embodiments 1S through 18S wherein W 3 is —CH 2 —. Embodiment 26S. A compound of Formula 1S or any one of Embodiments 1S through 25S wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79). Embodiment 27S. A compound of Embodiment 26S wherein when R 1 is G, then G is G-19 or G-20. Embodiment 28S. A compound of Embodiment 27S wherein when R 1 is G, then G is G-19. Embodiment 29S. A compound of Embodiment 28S wherein when R 1 is G, then G is G-20. Embodiment 30S. A compound of Embodiment 26S wherein when R 2 is G, then G is G-2, G-3 or G-15. Embodiment 31S. A compound of Embodiment 30R wherein when R 2 is G, then G is G-2. Embodiment 32S. A compound of Embodiment 31R wherein when R 2 is G, then G is G-3. Embodiment 33S. A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R 21 is independently halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio. Embodiment 34S. A compound of Embodiment 33R wherein each R 21 is independently fluorine, chlorine, bromine, CH 3 , CF 3 , OCH 3 , OCF 3 or SCH 3 . Embodiment 35S. A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R 22 is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl. Embodiment 36S. A compound of Embodiment 58Q wherein each R 22 is independently CH 3 or CH 2 CF 3 . Embodiment 37S. A compound of Formula 1S or any on of Embodiments 1S through 36S wherein when R 23 is an optionally substituted carbon moiety, R 23 is C 1 -C 16 alkyl; or phenyl or benzyl optionally substituted with halogen, nitro, cyano or hydroxy on ring members. Embodiment 38S. A compound of Embodiment 37S wherein when R 23 is an optionally substituted carbon moiety, R 23 is C 1 -C 10 alkyl; or phenyl or benzyl optionally substituted with halogen or nitro on ring members. Embodiment 39S. A compound of Embodiment 38S wherein when R 23 is an optionally substituted carbon moiety, R 23 is C 1 -C 6 alkyl; or benzyl optionally substituted with halogen or nitro on ring members. Embodiment 40S. A compound of Embodiment 39S wherein when R 23 is an optionally substituted carbon moiety, R 23 is C 1 -C 6 alkyl; or unsubstituted benzyl. Embodiment 41S. A compound of Embodiment 40S wherein when R 23 is an optionally substituted carbon moiety, R 23 is C 1 -C 6 alkyl. Embodiment 42S. A compound of Embodiment 41S wherein when R 23 is an optionally substituted carbon moiety, R 23 is unsubstituted benzyl. Embodiment 43S. A compound of Embodiment 42S wherein when R 23 is an optionally substituted carbon moiety, R 23 is ethyl, n-propyl, n-butyl or i-propyl. Embodiment 44S. A compound of Embodiment 43S wherein when R 23 is an optionally substituted carbon moiety, R 23 is ethyl, n-propyl or i-propyl. Embodiment 45S. A compound of Embodiment 44S wherein when R 23 is an optionally substituted carbon moiety, R 23 is ethyl.

›Embodiment H. A compound of Embodiment C wherein · 4 of 5

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1P as used in the following Embodiments includes N-oxides and salts thereof):

Embodiment P1. A compound of Formula 1P wherein X is N. Embodiment P2. A compound of Formula 1P wherein X is CH. Embodiment P3. A compound of Formula 1P or any one of Embodiments P1 through P2 wherein Y is C(O). Embodiment P4. A compound of Formula 1P or Embodiment P2 wherein Y is S(O) 2 . Embodiment P5. A compound of Formula 1P or any one of Embodiments P1 through P4 wherein A is A-1, A-3, A-4, A-5 or A-6. Embodiment P6. A compound of Embodiment P5 wherein A is A-1, A-3, A-5 or A-6. Embodiment P7. A compound of Embodiment P6 wherein A is A-3 or A-5. Embodiment P8. A compound of Embodiment P7 wherein A is A-3. Embodiment P9. A compound of Embodiment P6 wherein A is A-1 or A-6. Embodiment P10. A compound of Embodiment P9 wherein A is A-1. Embodiment P11. A compound of Formula 1P or any one of Embodiments P1 through P9 wherein A is other than A-1. Embodiment P12. A compound of Formula 1P or any one of Embodiments P1 through P11 wherein B 1 is C-1. Embodiment P13. A compound of Formula 1P or any one of Embodiments P1 through P11 wherein B 1 is C-2. Embodiment P14. A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B 2 is C-3. Embodiment P15. A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B 2 is C-4. Embodiment P16. A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B 2 is C-6 Embodiment P17. A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B 2 is C-7. Embodiment P18. A compound of Formula 1P or any one of Embodiments P1 through P17 wherein B 3 is C-1. Embodiment P19. A compound of Formula 1P or any one of Embodiments P1 through P17 wherein B 3 is C-2. Embodiment P20. A compound of Formula 1P or any one of Embodiments P1 through P19 wherein R 1 is phenyl, phenylsulfonyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —NHCHO, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -C 10 dialkylaminoalkyl, C 2 -C 8 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkylcarbonyl, C 3 -C 10 alkoxycarbonylalkyl or C 2 -C 8 haloalkoxycarbonyl. Embodiment P21. A compound of Embodiment P20 wherein R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl or C 2 -C 8 alkylsulfonylalkyl. Embodiment P22. A compound of Embodiment P21 wherein R 1 is phenyl or —W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or C 1 -C 6 alkyl or C 2 -C 6 alkenyl. Embodiment P23. A compound of Embodiment P22 wherein R 1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 2-methylphenyl, 4-methoxyphenyl, 2,3-dimethylphenyl, CH 2 (phenyl), CH 3 or CH 2 CH 3 . Embodiment P24. A compound of Embodiment P23 wherein R 1 is phenyl. Embodiment P25. A compound of Formula 1P or any one of Embodiments P1 through P22 wherein W 1 is C 1 -C 6 alkylene. Embodiment P26. A compound of Embodiment P25 wherein W 1 is —CH 2 —. Embodiment P27. A compound of Formula 1P or any one of Embodiments P1 through P21 or P25 or P26 wherein W 2 is —CH 2 —. Embodiment P28. A compound of Formula 1P or any one of Embodiments P1 through P27 wherein R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 4 -C 10 cycloalkoxylalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylcarbonyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 8 trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 halocycloalkenyloxy, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyhaloalkoxy, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -C 8 alkyl(thiocarbonyl)oxy, C 3 -C 8 cycloalkylsulfinyl or C 3 -C 10 halotrialkylsilyl. Embodiment P29. A compound of Embodiment P28 wherein R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl. Embodiment P30. A compound of Embodiment P29 wherein R 2 is phenyl or CH 2 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or C 1 -C 6 alkylthio. Embodiment P31. A compound of Embodiment P30 wherein R 2 is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, CH 2 CH 3 , cyclopropyl or SCH 3 . Embodiment P32. A compound of Formula 1P or any one of Embodiments P1 through P29 wherein W 3 is C 1 -C 6 alkylene. Embodiment P33. A compound of Embodiment P32 wherein W 3 is —CH 2 —. Embodiment P34. A compound of Formula 1P or any one of Embodiments P1 through P27 or P32 or P33 wherein W 4 is —CH 2 —. Embodiment P35. A compound of Formula 1P or any one of Embodiments P1 through P34 wherein R 3 is hydroxy, —O − M + , C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy or C 3 -C 10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R 21 . Embodiment P36. A compound of Embodiment P35 wherein R 3 is hydroxy or —O − M + ; or phenylsulfonyloxy optionally substituted with up to two substituents selected from R 21 . Embodiment P37. A compound of Embodiment P36 wherein R 3 is hydroxy; or phenylsulfonyloxy substituted with CH 3 at the 4-position. Embodiment P38. A compound of Formula 1P or any one of Embodiments P1 through P36 wherein M + is a sodium or potassium metal cation. Embodiment P39. A compound of Formula 1P or any of Embodiments P1 through P7 and P12 through P38 wherein R 4 , R 5 , R 6 and R 7 are each independently H, or C 1 -C 6 alkyl. Embodiment P40. A compound of Formula 1P or any one of Embodiments P1 through P7 and 12 through 39 wherein R 8 is C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment P41. A compound of Embodiment P40 wherein R 8 is CH 3 , CH 2 CH 3 or cyclopropyl. Embodiment P42. A compound of Formula 1P or any one of Embodiments P1 through P9 and 12 through 41 wherein R 9 is C 1 -C 6 alkyl. Embodiment P43. A compound of Embodiment P42 wherein R 9 is CH 2 CH 3 . Embodiment P44. A compound of Formula 1P or any one of Embodiments P1 through P9 and 12 through 41 wherein R 10 is H, halogen or C 1 -C 6 alkyl. Embodiment P45. A compound of Embodiment P44 wherein R 10 is H or CH 3 . Embodiment P46. A compound of Formula 1P or any one of Embodiments P1 through P8, P10, and P12 through P45 wherein R 11 is H or C 1 -C 6 alkyl. Embodiment P47. A compound of Embodiment P46 wherein R 11 is H. Embodiment P48. A compound of Formula 1P or any one of Embodiments P1 through P8, P10, and P12 through P47 wherein R 12 is H, halogen, cyano, hydroxy, amino or C 1 -C 6 alkyl. Embodiment P49. A compound of Embodiment P48 wherein R 12 is H, halogen, cyano, C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl. Embodiment P50. A compound of Embodiment P49 wherein R 12 is CH 3 , CH 2 CH 3 or cyclopropyl. Embodiment P51. A compound of Formula 1P or any one of Embodiments P1 through P6 and P12 through P50 wherein R 13 is H, halogen, cyano or nitro. Embodiment P52. A compound of Embodiment P51 wherein R 13 is cyano or nitro. Embodiment P53. A compound of Formula 1P or any one of Embodiments P1 through P52 wherein when instances of R 14 and R 18 are taken alone (i.e. R 14 and R 18 are not taken together as alkylene or alkenylene), then independently said instances of R 14 and R 18 are H or C 1 -C 6 alkyl. Embodiment P53a. A compound of Embodiment P53 wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H or CH 3 . Embodiment P53b. A compound of Embodiment P53a wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H. Embodiment P53c. A compound of Formula 1P or any one of Embodiments P1 through P53b wherein when instances of R 14 and R 18 are taken together, then said instances of R 14 and R 18 are taken together as —CH 2 CH 2 CH 2 — or —CH═CH—CH 2 —. Embodiment P53d. A compound of Formula 1P or any one of Embodiments P1 through P53b wherein all instances of R 14 and R 18 are taken alone. Embodiment P54. A compound of Formula 1P or any one of Embodiments P1 through P53d wherein independently each R 15 and R 19 is H or C 1 -C 6 alkyl. Embodiment P54a. A compound of Embodiment P54 wherein independently each R 15 and R 19 is H or CH 3 . Embodiment P55. A compound of Embodiment P54a wherein independently each R 15 and R 19 is H. Embodiment P56. A compound of Formula 1P or any one of Embodiments P1 through P55 wherein R 20 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 8 cycloalkyl. Embodiment P57. A compound of Embodiment P56 wherein R 20 is H or CH 3 . Embodiment P58. A compound of Formula 1P or any one of Embodiments P1 through P57 wherein T is —CH 2 CH 2 — or —CH═CH—. Embodiment P59. A compound of Formula 1P or any one of Embodiments P1 through P58 wherein each G is independently a 5- or 6-membered heterocyclic ring optionally substituted with up to five substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members. Embodiment P60. A compound of Embodiment P59 wherein G is selected from

›Embodiment H. A compound of Embodiment C wherein · 5 of 5

This invention also includes a herbicidal mixture of (a) a compound of Formula 1P and (b) an active ingredient selected from photosystem II inhibitors.

Embodiment P67. A herbicidal mixture comprising (a) a compound of Formula 1P and (b) an additional herbicidal ingredient selected from photosystem II inhibitors. Embodiment P68. A herbicidal mixture of Embodiment P67 comprising (a) a compound of Formula 1P and (b) an additional herbicidal compound selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, diuron, hexazinone, isoproturon, metribuzin, pyridate, simazine and terbutryn. Embodiment P69. A herbicidal mixture of Embodiment P68 comprising (a) a compound of Formula 1P; and (b) bromoxynil.

Embodiments of this invention, including Embodiments P1-P69 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1P but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1P. In addition, embodiments of this invention, including Embodiments 1-66 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.

Combinations of Embodiments 1-66 are illustrated by:

›Embodiment PA. A compound of Formula 1P wherein

Y is C(O); A is A-1, A-3, A-5 or A-6; R 1 is phenyl, phenylsulfonyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —NHCHO, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -C 10 dialkylaminoalkyl, C 2 -C 8 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkylcarbonyl, C 3 -C 10 alkoxycarbonylalkyl or C 2 -C 8 haloalkoxycarbonyl; W 1 is C 1 -C 6 alkylene W 2 is —CH 2 —; R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 4 -C 10 cycloalkoxylalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylcarbonyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 8 trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 halocycloalkenyloxy, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyhaloalkoxy, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -C 8 alkyl(thiocarbonyl)oxy, C 3 -C 8 cycloalkylsulfinyl or C 3 -C 10 halotrialkylsilyl; W 3 is C 1 -C 6 alkylene; W 4 is —CH 2 —; R 3 is hydroxy, —O − M + , C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy or C 3 -C 10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R 21 ; M + is a sodium or potassium metal cation; R 9 is C 1 -C 6 alkyl; R 10 is H, halogen or C 1 -C 6 alkyl; R 11 is H or C 1 -C 6 alkyl; R 12 is H, halogen, cyano, hydroxy, amino or C 1 -C 6 alkyl; R 13 is cyano or nitro; each R 14 , R 15 , R 18 and R 19 is independently H or CH 3 ; or a pair of R 14 and R 18 is taken together as —CH 2 CH 2 CH 2 — or —CH═CH—CH 2 —; R 20 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 8 cycloalkyl; T is —CH 2 CH 2 — or —CH═CH—; each G is selected from G-1 through G-23 (as depicted in Embodiment 79); r is 0, 1, 2 or 3; each R 21 is independently halogen, cyano, hydroxy, nitro, —CHO, —SH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl or C 3 -C 8 cycloalkylsulfonyl; and R 22 is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl.

›Embodiment PB. A compound of Embodiment PA wherein

›Embodiment PC. A compound of Embodiment PA wherein

X is CH; A is A-1 or A-6; B 1 is C-1, B 2 is C-3 and B 3 is C-1; R 1 is phenyl, —W 1 (phenyl), —W 1 (S-phenyl), —W 1 (SO 2 -phenyl), —W 2 (SO 2 CH 2 -phenyl) or —W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or —W 2 G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl or C 2 -C 8 alkylsulfonylalkyl; R 2 is phenyl or —W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl; R 3 is hydroxy or —O − M + ; or phenylsulfonyloxy optionally substituted on ring members with up to two substituents selected from R 21 ; R 11 is H; each R 14 , R 15 , R 18 and R 19 is independently H or CH 3 ; R 12 is H, halogen, cyano, C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl; W 1 is —CH 2 —; W 3 is —CH 2 —; G is G-13, G-14, G-15, G-16 or G-17; and each R 21 is independently halogen, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio.

›Embodiment PD. A compound of Embodiment PC wherein

A is A-1; R 1 is phenyl or —W 1 (phenyl) each optionally substituted on ring members with up to two substituents selected from R 21 ; or C 1 -C 6 alkyl or C 2 -C 6 alkenyl; R 2 is phenyl or CH 2 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or C 1 -C 6 alkylthio; R 3 is hydroxy; or phenylsulfonyloxy substituted with CH 3 at the 4-position; and each R 21 is independently fluorine, chlorine, CH 3 , CF 3 , OCH 3 , OCF 3 or SCH 3 .

›Embodiment PE. A compound of Embodiment PD wherein · 1 of 4

R 1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 2-methylphenyl, 4-methoxyphenyl, 2,3-dimethylphenyl, CH 2 (phenyl), CH 3 or CH 2 CH 3 ; R 2 is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, CH 2 CH 3 , c-Pr or SCH 3 .

Specific embodiments include the compound of Formula 1P which is:

5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone.

This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above.

This invention also includes herbicidal mixture comprising (a) a compound of Formula 1P and (b) an additional herbicidal ingredient selected from a photosystem II inhibitor. Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.

“Photosystem II inhibitors” (b1) are chemical compounds that bind to the D-1 protein at the Q B -binding niche and thus block electron transport from Q A to Q B in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction. The Q B -binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate. Examples of photosystem II inhibitors include, but are not limited to ametryn, atrazine, cyanazine, desmetryne, dimethametryn, prometon, prometryne, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryne, trietazine, hexazinone, metamitron, metribuzin, amicarbazone, bromacil, lenacil, terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, propanil, pentanochlor, bromofenoxim, bromoxynil, ioxynil, bentazon, pyridate and pyridafol.

“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for DNA synthesis and cell growth. Examples of AHAS inhibitors include but are not limited to amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl (including sodium salt), foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl (including sodium salt), mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl, tritosulfuron, imazapic, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, imazethapyr, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrithiobac-sodium, pyriminobac-methyl, thiencarbazone, flucarbazone-sodium and propoxycarbazone-sodium.

“ACCase inhibitors” (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back. Examples of ACCase inhibitors include but are not limited to clodinafop, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, propaquizafop, quizalofop, alloxydim, butroxydim, clethodim, cycloxydim, pinoxaden, profoxydim, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.

Auxin is a plant hormone that regulates growth in many plant tissues. “Auxin mimics” (b4) are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include but are not limited to aminocyclopyrachlor, aminopyralid benazolin-ethyl, chloramben, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, mecoprop, MCPA, MCPB, 2,3,6-TBA, picloram, triclopyr, quinclorac, quinmerac.

“EPSP (5-enol-pyruvylshikimate-3-phosphate) synthase inhibitors” (b5) are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).

›Embodiment PE. A compound of Embodiment PD wherein · 2 of 4

One or more of the following methods and variations as described in Schemes 1-18 can be used to prepare the compounds of Formula 1. The definitions of A, B 1 , B 2 , B 3 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 12 and R 13 in the compounds of Formulae 1-34 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae 1a-1h are various subsets of the compounds of Formula 1, and all substituents for Formulae 1a-1h are as defined above for Formula 1.

Compounds of Formula 1a, 1b or 1c (where R 3 is hydroxy) can be prepared via the two-step process shown in Schemes 1a, 1b and 1c respectively. Intermediate 4a, 4b or 4c can be prepared by reacting dione 2 with intermediate 3 where G is a nucleophilic reaction leaving group (e.g., G 1 is a halogen, alkoxycarbonyl, haloalkylcarbonyloxy, haloalkoxycarbonyloxy, pyridinyl or imidazoyl group). Reaction of intermediate 4a, 4b or 4c with the appropriate cyano compound (e.g., acetone cyanohydrin, potassium cyanide, sodium cyanide) in the presence of a base such as triethylamine or pyridine leads to a compound of Formula 1a, 1b or 1c. Alternatively a fluoride anion source such as potassium fluoride or cesium fluoride and optionally in the presence of a phase transfer catalyst (e.g. tetrabutyl ammonium bromide, etc.) can be used in this transformation. A solvent such as dimethylsulfoxide, N,N-dimethylformamide, acetonitrile or dichloromethane at ambient temperature to the reflux temperature of the solvent can lead to a compound of Formula 1a, 1b or 1c. (Formula 1a is Formula 1 wherein A is A-1; Formula 1b is Formula 1 wherein A is A-2; Formula 1c is Formula 1 wherein A is A-3.) Alternatively, compounds of Formula 1a, 1b or 1c can be prepared by Process 2 (in Schemes 1a, 1b and 1c respectively) by reacting dione 2a, 2b or 2c with intermediate 3 in the presence of a cyano compound or a fluoride anion source along with a base. For additional reaction conditions for this general coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.

Compounds of Formula 1a, 1b or 1c can also be prepared as shown in Scheme 2, by reacting dione 2a, 2b or 2c with intermediate 3a in the presence of a base or Lewis acid. For reaction conditions for this general coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.

As shown in Scheme 3, intermediate 4a, 4b or 4c can also be prepared by allowing dione 2a, 2b or 2c to react with acid 6 in the presence of a dehydrating condensation agent such as 2-chloro-1-pyridinium iodide (known as the Mukaiyama coupling agent), dicyclohexyl carbodiimide (DCC) or the like and optionally in the presence of a base. For additional reaction conditions for this general enol ester coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.

Intermediate 4a, 4b or 4c can also be made by the palladium-catalyzed carbonylation reaction of a compound of Formula 7 in the presence of dione 2a, 2b or 2c (Scheme 4). For reaction conditions for this general enol ester forming methodology, see Edmunds, A. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.

Compounds of Formula 1a, 1b or 1c (where R 3 is bonded through oxygen) are prepared by reacting compounds of Formula 1a, 1b or 1c with intermediate 8 where X is a nucleophilic reaction leaving group, also known as a nucleofuge in the presence of a base as shown in Scheme 5. Alternatively, compounds of Formula 1a, 1b and 1c (where R 3 is bonded through nitrogen, sulfur or carbon) can be prepared using the appropriate halogenating agent followed by nucleophilic addition. For reaction conditions for this general functionalization method, see Edmunds, A. or Almisick A. V. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 or Chapter 4.4, and references cited therein.

As shown in Scheme 6, compounds of Formula 1d (i.e. Formula 1 wherein A is A-4 and R 3 is OH) can be prepared by the reaction of intermediate 9 with intermediate 3 in the presence of a Lewis base, for example n-butyllithium or lithium diisopropylamide in an appropriate solvent such as tetrahydrofuran or diethyl ether. For reaction conditions for this type of transformation, see JP 2003327580.

Compounds of Formula 1e (i.e. Formula 1 wherein A is A-5 and R 3 is OH) can be prepared via a two-step process as shown in Scheme 7. Intermediate 12 can be prepared by reacting pyrazole 11 with intermediate 3 where G 1 is a nucleophilic reaction leaving group (i.e. G 1 is a halogen atom, alkoxycarbonyl, haloalkylcarbonyloxy, benzoyloxy, pyridinyl or imidazoyl group). Reaction of intermediate 12 with the appropriate cyano compound in the presence of a base leads to a compound of Formula 1e. Alternatively, a compound of Formula 1e can be prepared directly by reacting intermediate 11 with intermediate 3 (Process 2, Scheme 7) in the presence of a cyano compound or a fluoride anion source with a base. For reaction conditions for this general coupling methodology, see Almisick A. V. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

Compounds of Formula 1f (i.e. Formula 1 wherein A is A-5) wherein R 3 is bonded through oxygen can be prepared by reacting a compound of Formula 1e with intermediate 8 (where X is a nucleophilic reaction leaving group, also known as a nucleofuge) in the presence of a base as shown in Scheme 8. Alternatively compounds of Formula 1f wherein R 3 is bonded through nitrogen, sulfur or carbon can be prepared using the appropriate halogenating agent followed by nucleophilic displacement. For reaction conditions for these general functionalization methods, see Almisick A. V. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

›Embodiment PE. A compound of Embodiment PD wherein · 3 of 4

Compounds of Formula 17 can be prepared by reacting intermediate 3 with a compound Formula 16 in an appropriate solvent in the presence of a base. Thereafter intermediate 17 can be rearranged into the compound of Formula 1g (i.e. Formula 1 wherein A is A-7) in the presence of a cyano compound and a base as shown in Scheme 9. For reaction conditions for this general coupling methodology, see Almisick A. V. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

Compounds of Formula 19 can be prepared from corresponding compounds of Formula 1g wherein R 13 is an alkoxycarbonyl in the presence of an acid such as hydrogen chloride, sulfuric or acetic acid and optionally in the presence of a solvent such as tetrahydrofuran, diethyl ether or dichloromethane as shown in Scheme 10. Intermediate 19 is then reacted with an orthoformate ester or N,N-dimethylformamide dimethylacetal (DMF-DMA) in the presence of an acid to obtain intermediate 20. Reaction of intermediate 20 with hydroxylamine hydrochloride salt in a solvent such as ethanol, acetonitrile, water or acetic acid provides isoxazole compounds of Formula 1h (i.e. Formula 1 wherein A is A-6 and R 11 is H). For reaction conditions for this general cyclization methodology, see Almisick A. V. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

As illustrated in Scheme 11, sulfoxides and sulfones of Formula 1 wherein R 2 is a substituent bonded through a sulfoxide or sulfone radical can be prepared by oxidation of the compounds of Formula 1 wherein R 2 is a substituent bonded through a sulfide radical. In a typical procedure, an oxidizing agent in an amount from 1 to 4 equivalents depending on the oxidation state of the product desired is added to a solution of the compound of Formula 1 in a solvent. Useful oxidizing agents include Oxone® (potassium peroxymonosulfate), hydrogen peroxide, sodium periodate, peracetic acid and 3-chloroperbenzoic acid. The solvent is selected with regard to the oxidizing agent employed. Aqueous ethanol or aqueous acetone is preferably used with potassium peroxymonosulfate, and dichloromethane is generally preferable with 3-chloroperbenzoic acid. Useful reaction temperatures typically range from 0 to 90° C. Particular procedures useful for oxidizing sulfides to sulfoxides and sulfones are described by Brand et al., J. Agric. Food Chem. 1984, 32, 221-226 and references cited therein.

One skilled in the art will realize that acid chlorides of Formula 3d (i.e. Formula 3 wherein G 1 is Cl) are easily prepared from the acid of Formula 6 (Scheme 12) by numerous well-known methods. For example reacting the acid with a chlorinating reagent such as oxalyl chloride or thionyl chloride in a solvent such as dichloromethane or toluene and optionally in the presence of a catalytic amount of N,N-dimethylformamide can provide the corresponding acid chloride of Formula 3d.

Compounds of Formula 6 can be prepared from esters of Formula 23 by numerous well-known methods, for example standard saponification procedures using aqueous bases such as LiOH, NaOH or KOH in a solvent such methanol or ethanol as described in Scheme 13. Alternatively, a dealkylating agent such as lithium iodide or trimethylsilyl iodide can be used in the presence of a base in a solvent such as pyridine or ethyl acetate. Additional reaction procedures for deesterification can be found in PCT Patent Publication WO 2006/133242. Boron tribromide (BBr 3 ) can alternatively be used to prepare a compound of Formula 6 from a compound of Formula 23 in a solovent such as dichloromethane. Procedures using boron tribromide can be found in Bioorg . & Med. Chem. Lett . 2009, 19(16), 4733-4739.

Pyrimidinone esters of Formula 23a (i.e. Formula 23 whererin Alk is ethyl, X is CH and Y is C(O)) are prepared as illustrated in Scheme 14 by N-alkylation of pyridones of Formula 26 with agents such as alkyl halides in the presence of a base such as sodium hydride or potassium carbonate in a solvent such as N,N-dimethylformamide, tetrahydrofuran or diethyl ether.

Pyrimidinone esters of Formula 23a can be made by the method of Scheme 15. In this method an methylene malonate of Formula 28 is cyclized with an amidine salt of Formula 29 wherein X is a halogen or sulfonate counter ion in the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as ethanol (generally at the reflux temperature of the solvent) to give the corresponding pyrimidinone of Formula 3f. Examples of this synthetic method are reported in PCT Patent Publication WO 2006/133242 or Tetrahedron 2001, 57, 2689.

Pyrimidinone esters of Formula 26 can be prepared by the method of Scheme 16. In this method, an ethylene malonate of Formula 28 is cyclized with an amidine salt Formula 29a wherein X is a halogen or sulfonate counter ion in the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as methanol (generally at the reflux temperature of the solvent) to give the corresponding pyrimidinone of Formula 26. Examples of this synthetic procedure are reported in PCT Patent Publication WO 2006/133242 , Tetrahedron 2001, 57, 2689.

Thiones of Formula 23b (i.e. Formula 23 wherein Alk is ethyl, X is CH and Y is S(O) 2 ) can be made by the method of Scheme 17. In this method amidines of Formula 29 is reacted with acetal 30 in the presence of a base such as triethylamine, pyridine or potassium carbonate to give the corresponding azabutadiene 31. Reacting this compound with the sulfonic acid chloride 32 as shown in Scheme 17 in the presence of a base such as triethylamine, pyridine or potassium carbonate in an appropriate solvent results in the corresponding compound of Formula 33. The corresponding thiones of formula 23b can be obtained by reacting the compound of Formula 33 with iodomethane and subsequent treatment with a base such as triethylamine. Examples of this synthetic methodology are reported in Synthesis 2000, 5, 695.

›Embodiment PE. A compound of Embodiment PD wherein · 4 of 4

Triazines of Formula 23c (i.e. Formula 23 wherein Alk is ethyl, X is N and Y is C(O)) can be made by the method of Scheme 18. In this method a ketomalonate of Formula 34 is cyclized with a semicarbazide of Formula 29c wherein X is a halogen or sulfonate counter ion with or without the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as ethanol or t-butanol (generally at the reflux temperature of the solvent) to the corresponding triazine of Formula 23c. Examples of this synthetic methodology are found in Eur. J. Med. Chem. 2008, 43(5), 1085 , Bull. Soc. Chim. Fr. 1976, (11-12, Pt. 2), 1825 and J. Org. Chem. 1962, 27, 976.

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.

One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. 1 H NMR spectra are reported in ppm downfield from tetramethylsilane at 400 MHz unless otherwise noted; “s” means singlet, “m” means multiplet, “br s” means broad singlet, “d” means doublet, “t” means triplet, “dt” means doublet of triplets, “q” means quartet and “sep” means septet.

›EXAMPLE 1

Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 2)

›Step A: Preparation of N-phenylbenzenecarboximidamide sodium salt

To a stirred solution of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 21.5 mL, 21.5 mmol) in tetrahydrofuran (10 mL) was added aniline (2.0 g, 21.5 mmol) and allowed to stir for 10 min at room temperature. Benzonitrile (2.21 g, 21.5 mmol) was added, and the reaction mixture was stirred for 1 h at room temperature. The solid that precipitated was filtered, washed with diethyl ether and dried under reduced pressure to afford the title product as an off-white solid (4.0 g), which was used without further purification in the next step.

Step B: Preparation of (A) 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid ethyl ester and (B) 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid

To a stirred solution of N-phenylbenzenecarboximidamide sodium salt (i.e. the product from Step A) (6.0 g, 27.5 mmol) in acetonitrile (30 mL) was added ammonium chloride (1.47 g, 27.5 mmol) followed by diethyl ethoxymethylenemalonate (5.94 g, 27.5 mmol). The reaction mixture was heated and stirred at reflux for 2 h. The reaction mixture was concentrated under reduced pressure to give a residue. Water (30 mL) was added to the residue, followed by a saturated solution of sodium bicarbonate (30 mL), and the mixture was extracted with ethyl acetate. The aqueous layer was separated and retained. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure. The resulting residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford the title product (A) as a white solid (2.80 g).

1 H NMR (CDCl 3 ) δ 8.81 (s, 1H), 7.11-7.33 (m, 10H), 4.41 (m, 2H), 1.39 (m, 3H).

The above retained aqueous layer was acidified with 1 N hydrochloric acid until the pH was 1-2, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure to provide a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product (B) as a white solid (680 mg).

1 H NMR (DMSO-d 6 ) δ 13.03 (s, 1H), 8.79 (s, 1H), 7.22-7.36 (m, 10H).

Step B1: Preparation of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (alternate preparation to Step B, product (B))

To a stirred solution of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid ethyl ester (i.e. Step B product (A)) (2.30 g, 7.18 mmol) in pyridine (15 mL) was added lithium iodide (2.46 g, 18.0 mmol). The reaction mixture was heated to reflux with stirring for 24 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL) followed by 1 N hydrochloric acid until the pH was 7. The solution was filtered though Celite® diatomaceous filter aid. The filtrate was acidified with 1 N hydrochloric acid until the pH was 1, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (1.40 g).

1 H NMR (DMSO-d 6 ) δ 13.03 (s, 1H), 8.79 (s, 1H), 7.22-7.36 (m, 10H).

Step C: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (i.e. Step B product (B) or the product from Step B1) (1.40 g, 4.8 mmol) in dichloromethane (30 mL) was added oxalyl chloride (1.21 g, 9.61 mmol) at 0° C. followed by catalytic amount (2 drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. Then the reaction mixture was concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL), 1,3-cyclohexanedione (646 mg, 5.76 mmol), followed by triethylamine (976 mg, 9.60 mmol), and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (1.1 g).

1 H NMR (CDCl 3 ) δ 8.89 (s, 1H), 7.31-7.36 (m, 5H), 7.24-7.26 (m, 3H), 7.12-7.15 (m, 2H), 6.04 (m, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.11 (m, 2H).

Step D: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 2)

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylate (i.e. the product from Step C) (640 mg, 1.65 mmol) in acetonitrile (20 mL) was added triethylamine (401 mg, 3.97 mmol), followed by a catalytic amount of acetone cyanohydrin (3 drops). The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the resulting residue was added dichloromethane and 1 N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried (MgSO 4 ) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 100% ethyl acetate to afford the title product, a compound of the present invention, as a white solid (150 mg).

1 H NMR (CDCl 3 ) δ 8.24 (s, 1H), 7.12-7.34 (m, 10H), 2.70 (m, 2H), 2.48 (m, 2H), 2.03 (m, 2H).

›EXAMPLE 2

Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 17)

›Step A: Preparation of N-(phenylmethyl)-benzenecarboximidamide

To a stirred solution of ethylbenzimidate hydrochloride (3.0 g, 16.2 mmol) in N,N-dimethylformamide (10 mL) was added triethylamine (1.60 g, 16.2 mmol). The reaction mixture was allowed to stir at room temperature for 1 h and then filtered to remove triethylamine salts, which were rinsed with N,N-dimethylformamide (5 mL). Benzylamine (1.23 g, 11.5 mmol) was added to the filtrate, and the mixture was heated to 65° C. for 24 h. To the cooled mixture was added water (80 mL) and ethyl acetate. The organic layer was washed with water and brine, then dried (MgSO 4 ) and concentrated under reduced pressure to afford the title product as a clear oil (2.80 g).

1 H NMR (CDCl 3 ) δ 7.61 (m, 2H), 7.26-4.43 (m, 8H), 4.57 (m, 2H), 4.37 (m, 1H), 1.42 (m, 1H).

›Step B: Preparation of ethyl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of N-(phenylmethyl)-benzenecarboximidamide (i.e. the product from Step A) (2.54 g, 12.1 mmol) in ethanol (15 mL) was added diethyl ethoxymethylenemalonate (2.61 g, 12.1 mmol), and the reaction mixture was heated to reflux for 24 h. The reaction mixture was then allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford the title product as a white solid (2.9 g).

1 H NMR (CDCl 3 ) δ 8.71 (s, 1H), 7.51 (m, 1H), 7.42 (m, 2H), 7.33 (m, 2H), 7.23 (m, 3H), 6.93 (m, 2H), 5.28 (s, 2H), 4.42 (m, 2H), 1.40 (m, 3H).

›Step C: Preparation of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid

To a stirred solution of ethyl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step B) (2.9 g, 8.6 mmol) in pyridine (15 mL) was added lithium iodide (3.01 g, 21.7 mmol). The reaction mixture was heated to reflux for 4 h, cooled, and then stirred at room temperature for 72 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL), followed by 1 N hydrochloric acid until the pH was 7. The solution was filtered through Celite® diatomaceous filter aid, and the filtrate was acidified with 1 N hydrochloric acid until the pH was 1. The mixture was extracted with dichloromethane, and the organic layer was dried (MgSO 4 ) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (2.2 g).

Step D: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid (i.e. the product from Step C) (1.00 g, 3.26 mmol) in dichloromethane (30 mL) at 0° C., was added oxalyl chloride (823 mg, 6.53 mmol) followed by a catalytic amount of N,N-dimethylformamide (2 drops). The reaction mixture was allowed to warm to room temperature and stir for 1 h. Then the reaction mixture was concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL) and 1,3-cyclohexanedione (440 mg, 3.90 mmol), followed by triethylamine (990 mg, 9.80 mmol), and the reaction mixture was stirred at room temperature for 30 min Saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (500 mg).

1 H NMR (CDCl 3 ) δ 8.81 (s, 1H), 7.55 (m, 1H), 7.45 (m, 2H), 7.37 (m, 2H), 7.25 (m, 3H), 6.95 (m, 2H), 6.03 (s, 1H), 5.30 (s, 2H), 2.69 (m, 2H), 2.46 (m, 2H), 2.12 (m, 2H).

Step E: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 17)

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step D) (450 mg, 1.12 mmol) in acetonitrile (15 mL) was added triethylamine (272 mg, 2.69 mmol), followed by a catalytic amount (3 drops) of acetone cyanohydrin. The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the resulting residue were added dichloromethane and 1 N hydrochloric acid, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate to afford the title product, a compound of the present invention, as a white solid (160 mg).

1 H NMR (CDCl 3 ) δ 16.44 (br s, 1H), 8.17 (s, 1H), 7.47 (m, 1H), 7.37 (m, 2H), 7.21-7.30 (m, 5H), 6.95 (m, 2H), 5.20 (s, 2H), 2.72 (m, 2H), 2.51 (m, 2H), 2.06 (m, 2H).

›Examples3

›Example 3

Preparation of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 20)

Step A: Preparation of 1-ethyl-1H-pyrazol-5-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 2, Step C) (1.20 g, 3.92 mmol) in dichloromethane (30 mL) was added oxalyl chloride (998 mg, 7.84 mmol) at 0° C. followed by a catalytic amount (4-drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. The reaction mixture was then concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL) and 5-hydroxy-1-ethyl-1H-pyrazole, (572 mg, 4.7 mmol), followed by triethylamine (1.18 g, 11.8 mmol), and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 70% ethyl acetate in hexanes to afford the title product as a white solid (700 mg).

1 H NMR (CDCl 3 ) δ 8.90 (s, 1H), 7.56 (m, 1H), 7.46 (m, 3H), 7.38 (m, 2H), 7.26 (m, 3H), 6.95 (m, 2H), 6.29 (m, 1H), 5.34 (s, 2H), 4.19 (m, 2H), 1.45 (m, 3H).

Step B: Preparation of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 20)

To a stirred solution of 1-ethyl-1H-pyrazol-5-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step A) (650 mg, 1.62 mmol) in acetonitrile (15 mL) was added triethylamine (393 mg, 3.70 mmol), followed by a catalytic amount (5 drops) of acetone cyanohydrin. The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the residue were added dichloromethane and 1 N hydrochloric acid, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 10% methanol in ethyl acetate to afford the title product, a compound of the present invention, as a white solid (150 mg).

1 H NMR (CDCl 3 ) δ 8.56 (s, 1H), 7.86 (s, 1H), 7.53 (m, 1H), 7.39-7.46 (m, 4H), 7.24 (m, 3H), 6.97 (m, 2H), 5.33 (s, 2H), 4.04 (m, 2H), 1.42 (m, 3H).

›EXAMPLE 4

Step A: Preparation of 5-[[1-ethyl-5-[[(4-methylphenyl)sulfonyl]oxy]-1H-pyrazol-4-yl]carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 21)

To a stirred solution of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (i.e. the product from Example 3, Step B) (300 mg, 0.75 mmol) in acetonitrile (10 mL) was added triethylamine (116 mg, 1.12 mmol), followed by p-toluenesulfonyl chloride (171 mg, 0.90 mmol), and the reaction mixture was stirred at room temperature for 72 h. Saturated aqueous ammonium chloride solution was added to the mixture, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product, a compound of the present invention, as a white solid (160 mg).

1 H NMR (CDCl 3 ) δ 8.07 (s, 1H), 7.84 (s, 1H), 7.74 (m, 2H), 7.44 (m, 2H), 7.25-7.35 (m, 8H), 6.95 (m, 2H), 5.23 (s, 2H), 4.00 (m, 2H), 2.41 (s, 3H), 1.42 (m, 3H).

›EXAMPLE 5

Preparation of 3-(3-fluoro-2-methylphenyl)-5-[2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone (Compound 47)

›Step A: Preparation of N-(3-fluro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1)

To a stirred solution of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 200.0 mL, 200.0 mmol) was added 3-fluoro-2-methylaniline (25.0 g, 200.0 mmol) and allowed to stir for 10 min at room temperature. Benzonitrile (20.6 g, 200.0 mmol) was added, and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was concentrated and the solid that formed was filtered, washed with diethyl ether and dried under reduced pressure to afford the title product as a grey solid (51.0 g), which was used without further purification in the next step.

Step B: Preparation of 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid

To a stirred solution of N-(3-fluro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1) (i.e. the product from Example 5, Step A) (51.0 g, 200 mmol) in acetonitrile (300 mL) was added diethyl ethoxymethylenemalonate (44.04 g, 200 mmol). The reaction was stirred at room temperature for 30 min followed by the addition of water (3.6 mL, 200 mmol). The reaction was then stirred for another 30 min Water (100 mL) was added to the residue, followed by a saturated solution of sodium bicarbonate (300 mL), and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid until the pH was 1-2, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO 4 ) and concentrated under reduced pressure to provide a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a off-white solid (18 g).

1 H NMR (CDCl 3 ) δ 12.68 (s, 1H), 9.15 (s, 1H), 7.43 (m, 1H), 7.19-7.38 (m, 5H), 7.12 (m, 1H), 6.88 (m, 1H), 2.03 (s, 3H).

Step C: Preparation of 3-oxo-1-cyclohexen-1-yl 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate

To a stirred solution of 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 5, Step B) (41.0 g, 126 mmol) in dichloromethane (400 mL) was added oxalyl chloride (31.05 g, 252.0 mmol) at 0° C. followed by a catalytic amount (7 drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. The reaction mixture was then concentrated under reduced pressure. To the resulting residue was added dichloromethane (400 mL), 1,3-cyclohexanedione (17.03 g, 152 mmol), followed by triethylamine (38.30 g, 379 mmol) and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with dichloromethane. The organic layer was washed once with water. Then the organic layer was dried (MgSO 4 ) and concentrated under reduced pressure. The resulting solid was washed with chlorobutane to afford the title product pure as an off-white solid (37.6 g).

1 H NMR (CDCl 3 ) δ 8.92 (s, 1H), 7.24-7.40 (m, 5H), 7.18 (m, 1H), 7.05 (m, 1H), 6.87 (m, 1H), 6.05 (s, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.11 (m, 2H), 2.03 (s, 3H).

Step D: Preparation of 3-(3-fluoro-2-methylphenyl)-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate (i.e. the product from Example 5, Step C) (42 g, 100.4 mmol) in acetonitrile (200 mL) was added cesium fluoride (30.5 g, 200.8 mmol). The reaction mixture was stirred for 24 h at room temperature. Water and ethyl acetate was added to the reaction mixture and the water layer was extracted several times with ethyl acetate. The combined organic layers were dried (MgSO 4 ) and concentrated under reduced pressure. The resulting solid was washed several times with ether and filtered, followed by the addition 60 mL of ethyl acetate and let stir for 2 h. The resulting solid was then washed again with ether and dried under reduced pressure to afford the title product, a compound of the present invention, as a yellow solid (26 g).

1 H NMR (CDCl 3 ) δ 16.38 (s, 1H), 8.28 (s, 1H), 7.21-7.34 (m, 5H), 7.11 (m, 1H), 7.00 (m, 1H), 6.86 (m, 1H), 2.70 (m, 2H), 2.47 (m, 2H), 2.10 (m, 3H), 2.03 (m, 2H).

›EXAMPLE 6

Preparation of 5-[5-cyclopropyl-4-isoxazolyl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 223)

Step A: Preparation of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione

To a mixture of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 1, step B) (1.84 g, 6.3 mmol) and toluene (6.3 mL) was added phosphorus pentachloride (1.31 g, 6.3 mmol) at ambient temperature. The resulting mixture was heated at reflux under a nitrogen atmosphere for 6 h. The resulting yellow solution was concentrated to give 1.53 g of the acid chloride as a yellow solid.

n-Butyllithium (2.5M solution in hexanes, 2.2 mL, 5.6 mmol) was added dropwise to a solution of N,N-diisopropylamine (0.82 mL, 5.8 mmol) and anhydrous tetrahydrofuran (8 mL) at −78° C. under a nitrogen atmosphere. The resulting solution was warmed to 0° C., stirred for 30 min, and then cooled to −78° C. Cyclopropyl methyl ketone (0.55 mL, 5.6 mmol) was added dropwise at below −65° C. The resulting solution was stirred at −78° C. for 30 min and was then treated with a slurry of the acid chloride as prepared above (823 mg, 2.7 mmol) in anhydrous tetrahydrofuran (5 mL) added dropwise via syringe at below 60° C. Additional anhydrous tetrahydrofuran (5 mL) was used to complete the transfer of the acid chloride. The resulting mixture was stirred at −78° C. for 1 h and was then treated with saturated aqueous ammonium chloride (7 mL) at below −50° C. The resulting mixture was stirred at ambient temperature for 15 min and was partitioned between ethyl acetate (100 mL) and saturated aqueous ammonium chloride (50 mL). The organic layer was dried over MgSO 4 , filtered, and concentrated onto silica gel (2.5 g). The residue was purified by medium pressure liquid chromatography using a 24 g silica column and eluting with a gradient of 0 to 100% ethyl acetate in hexanes to provide the title compound as a pale yellow glassy solid (250 mg).

1 HNMR (400 MHz, CDCl 3 ) δ 15.88 (s, 1H), 8.93 (s, 1H), 7.40-7.33 (m, 3H), 7.33-7.26 (m, 3H), 7.24-7.19 (m, 3H), 7.14 (apparent d, 2H), 1.81 (sep, 1H), 1.20-1.15 (m, 2H), 0.99-0.92 (m, 2H).

Step B: Preparation of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione

A suspension of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione (i.e. the product from Example 6, Step A) (165 mg, 0.46 mmol), triethyl orthoformate (0.23 mL, 1.4 mmol), and acetic anhydride (0.92 mL) was heated at 110° C. under a nitrogen atmosphere for 4 h. The residue was dissolved in toluene (5 mL) and the resulting solution was concentrated under reduced pressure at 50° C. The residue was re-dissolved in toluene (5 mL) and the resulting solution was concentrated at 50° C. to give 181 mg of the title compound as a brown oil that was used in the next step without further purification. 1 H NMR analysis showed the product to contain a mixture of Z- and E-olefin isomers.

1 HNMR (400 MHz, CDCl 3 ) 8.63 and 8.47 (2s, 1H total), 7.68 and 7.62 (2s, 1H total), 7.33-7.16 (m, 8H), 7.10-7.02 (m, 2H), 4.27 and 4.16 (2q, 2H total), 2.64-2.57 (m, <1H), 1.42 and 1.33 (3t, 3H total), 1.11-1.06 and 1.04-0.98 (2m, 2H total), 0.91-0.82 (m, 2H).

›Step C: Preparation of 5-[(5-cyclopropyl-4-isoxazolyl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone

Anhydrous sodium acetate (68 mg, 0.83 mmol) was added to a solution of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione (i.e. the product from Example 6, Step B) (171 mg, 0.41 mmol) in ethanol (4 mL) at 0° C. Hydroxylamine hydrochloride (29 mg, 0.42 mmol) was added and the resulting suspension was stirred at 0° C. for 30 min and then at ambient temperature for 2 h. The resulting mixture was diluted with ethyl acetate (20 mL) and ethanol (20 mL), concentrated onto 0.8 g silica gel, and the residue purified by medium pressure liquid chromatography using a 12 g silica gel column and eluting with 0 to 100% ethyl acetate in hexanes to obtain 14 mg of the title compound, a compound of the present invention as a yellow glassy solid.

1 HNMR (400 MHz, CDCl 3 ) 8.56 (s, 1H), 8.45 (s, 1H), 7.40-7.30 (m, 6H), 7.25-7.20 (m, 2H), 7.16-7.12 (m, 2H), 3.02-2.93 (m, 1H), 1.37-1.32 (m, 2H), 1.27-1.22 (m, 2H).

›EXAMPLE 7

Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-phenyl-2-(3-pyridinyl)-4(3H)-pyrimidone (Compound 113)

›Step A: Preparation of N-phenyl-3-pyridinecarboximidamide

Sodium hydride (60% in mineral oil, 11.52 g, 288 mmol) was added portion-wise over 30 min to a stirred solution of 3-pyridinecarbonitrile (30 g, 288 mmol) and aniline (26 g, 290 mmol) in dimethylsulfoxide (150 mL) at 10° C. The reaction mixture was allowed to warm to ambient temperature with stirring for 18 h. The reaction mixture was slowly and cautiously poured into water containing crushed ice. The solid that precipitated was filtered, washed with petroleum ether, dissolved in dichloromethane and dried over anhydrous Na 2 SO 4 . The volatiles were removed under reduced pressure (high vacuum) and the residue was dried to afford 36.5 g of the title compound as a yellow solid.

1 H NMR (CDCl 3 , 500 MHz) δ 9.06 (s, 1H), 8.68 (d, 1H), 8.22 (d, 1H), 7.38-7.35 (m, 3H), 7.08 (t, 1H), 6.97 (d, 2H), 5.00 (s, 2H).

›Step B: Preparation of ethyl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate

A suspension of the N-phenyl-3-pyridinecarboximidamide (i.e. the product from Example 7, Step A) (36.5 g, 185 mmol) in diethyl ethoxymethylenemalonate (60 g, 280 mmol) was heated to 160° C. for 8 h. Ethanol formed in the reaction was collected using a distillation head attached to the flask containing the heated reaction mixture. The reaction mixture was then cooled to ambient temperature when the formation of a solid was observed. A mixture of diethyl ether/petroleum ether (8:2) was added to the reaction mixture was filtered. The collected solid was washed with additional ether/petroleum ether (4:1) followed by n-chlorobutane/petroleum ether (1:1) to obtain 51 g of the title compound as a light brown powder.

1 H NMR (CDCl 3 , 500 MHz) δ 8.79 (s, 1H), 8.57 (dd, 1H), 8.52 (dd, 1H), 7.58 (dt, 1H), 7.38-7.35 (m, 3H), 7.16-7.13 (m, 3H), 4.41 (q, 2H), 1.39 (t, 3H).

›Step C: Preparation of 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid

A suspension of ethyl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e. the product from Example 7, Step B) (5.0 g, 15.5 mmol) and lithium iodide (powder, 5.2 g, 38.8 mmol) in pyridine (15 mL) was heated to 125-130° C. for 12 h. After cooling to ambient temperature, excess solvent was removed under reduced pressure. The resulting residue was dissolved in water (100 mL) and acidified with hydrochloric acid (6 N) to pH 7. The resulting dark brown solution was extracted with ethyl acetate (1×100 mL) to remove the non polar impurities. The aqueous layer was again extracted with dichloromethane/methanol (95:5) (2×50 mL). After initial extractions, the aqueous layer was slowly acidified to pH 4 and further extracted with dichloromethane/methanol (95:5) (3×50 mL). The combined neutral and acidic extracts were washed with brine and dried over anhydrous Na 2 SO 4 . The residue obtained after removal of the solvent was dried under high-vacuum to obtain 3.4 g of the title compound as a light brown solid.

1 H NMR (CDCl 3 , 500 MHz) δ 12.67 (br s, 1H), 9.12 (s, 1H), 8.60-8.57 (m, 2H), 7.65 (dt, 1H), 7.47-7.46 (m, 3H), 7.22-7.19 (m, 3H).

Step D: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate

To a stirred suspension of 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 7, Step C) (10.7 g, 36.3 mmol) in dichloromethane (150 mL) at ambient temperature was added 2-chloro-N-methyl pyridinium iodide (also known as the Mukaiyama reagent) (14.8 g, 57.9 mmol) followed by cyclohexanedione (6.5 g, 58 mmol) and triethylamine (9.2 g, 91 mmol). The reaction mixture was left stirring at ambient temperature overnight, then diluted with dichloromethane, washed with water, brine and dried over anhydrous Na 2 SO 4 . The residue obtained after removal of the solvent under vacuum was purified by tituration with n-chlorobutane/petroleum ether mixtures to obtain 9.8 g of the title compound as a light brown solid.

1 H NMR (CDCl 3 , 500 MHz) δ 8.89 (s, 1H), 8.60 (d, 1H) 8.54 (dd, 1H), 7.61 (dt, 1H), 7.42-7.37 (m, 3H), 7.19-7.14 (m, 3H), 6.04 (s, 1H), 2.69-2.66 (m, 2H), 2.45-2.42 (m, 2H), 2.10 (q, 2H).

Step E: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-phenyl-2-(3-pyridinyl)-4(3H)-pyrimidone

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e. the product from Example 7, Step D) (11.1 g, 28.6 mmol) in acetonitrile (166 mL) was added cesium fluoride (8.71 g, 57.3 mmol) followed by catalytic amount (˜50 mg) of tetrabutylammonium bromide at ambient temperature. After stirring for 3 h at ambient temperature, the reaction mixture was diluted with ethyl acetate, washed with water, brine and dried over anhydrous Na 2 SO 4 . The volatile components were removed under reduced pressure and the residue was subjected to silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:1) to ethyl acetate to dichloromethane/methanol (95:5). The product obtained was washed with minimum amount of methanol to afford 1.4 g of the title compound, a compound of the present invention as a light yellow solid.

1 H NMR (CDCl 3 , 500 MHz) mixture of tautomers δ 16.45 (s, 0.8H), 8.57-8.50 (m, 2H), 8.21 (s, 1H), 7.57 (d, 1H), 7.35 (d, 3H), 7.16-7.13 (m, 3H), 5.29 (s, 0.2H,), 2.71 (br s, 2H), 2.47 (br s, 2H), 2.04-2.02 (m, 2H).

›EXAMPLE 8

Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (Compound 168) and 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (Compound 169)

Step A: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone and 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone

To 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(tetrahydro-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (the tautomer known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(tetrahydro-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) (0.15 g, 0.37 mmol) in a mixture of 5.0 mL water and 5.0 mL methanol at room temperature was added NaIO 4 (0.074 g, 0.35 mmol). After approximately 45 min, additional NaIO 4 (0.011 g, 0.05 mmol) was added and stirring was continued for an additional 2 h. The reaction mixture was extracted with dichloromethane and the combined organics were dried over MgSO 4 concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.07 g of Compound 168 (alternatively known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) and and 0.03 g of Compound 169 (alternatively known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) both as solids.

1 H NMR of Compound 168 (CDCl 3 ) δ 16.58 (br s, 1H), 7.99 (s, 1H), 7.58 (m, 3H), 7.47 (m, 2H), 4.14 (m, 1H), 3.39 (m, 2H), 3.12 (m, 2H), 2.74 (t, 2H), 2.49 (t, 2H), 2.37 (t, 2H), 2.05 (m, 4H).

1 H NMR Compound 169 (CDCl 3 ) δ 16.42 (br s, 1H), 8.00 (s, 1H), 7.54 (m, 5H), 4.06 (m, 1H), 3.65 (m, 2H), 3.07 (m, 2H), 2.60 (br s, 4H), 2.17 (m, 2H), 2.07 (m, 2H), 1.80 (d, 2H).

›EXAMPLE 9

Preparation of 2-(3,5-difluorophenyl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-3-(2-methoxyethyl)-4(3H)-pyrimidinone (Compound 243)

›Step A: Preparation of 3,5-difluorobenzenecarboxamidic acid ethyl ester hydrochloride (1:1)

To a stirred solution of 3,5-difluorobenzonitirile (25 g, 180 mmol) in ethanol (336 mL) and dichloromethane (180 mL) at 0° C., was added acetyl chloride (128 mL, 1800 mmol) drop wise via addition funnel. The reaction mixture was allowed to warm to room temperature and stir for 24 h. The reaction mixture was then concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (21.5 g) which was carried forward to the next step without further purification.

›Step B: Preparation of 3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1)

To a stirred solution of 3,5-difluorobenzenecarboxamidic acid ethyl ester hydrochloride (5.39 g, 24.3 mmol) (i.e. the product from Example 9, Step A) in methanol (25 mL) at 0° C., was added 2-methoxy-1-ethylamine (2.2 mL, 25.5 mmol). The reaction mixture was allowed to warm to room temperature and stir for 24 h. The reaction mixture was concentrated under reduced pressure to afford the title product as a gummy oil, which was used without further purification in the next step.

Step C: Preparation of ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxyate

To a stirred solution of 3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1 (i.e. the product from Example 9, Step B) (24.3 mmol) in ethanol (25 mL) was added diethyl ethoxymethylenemalonate (5.25 g, 24.3 mmol) followed by sodium ethoxide (21% soln) (9.1 mL, 24.3 mmol). The reaction mixture was heated and stirred at reflux for 24 h. The reaction mixture was cooled to room temperature concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (6.1 g).

1 H NMR (CDCl 3 ) δ 8.65 (s, 1H), 7.14 (m, 2H), 6.98 (m, 1H), 4.41 (m, 2H), 4.21 (m, 2H), 3.67 (m, 2H), 3.22 (s, 3H), 1.40 (m, 3H).

Step D: Preparation of 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylic acid

To a stirred solution of ethyl ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxyate (i.e. the product from Example 9, Step C) (1.14 g, 3.37 mmol) in ethyl acetate (10 mL) was added lithium iodide powder (1.35 g, 10.0 mmol). The reaction mixture was heated to reflux for 24 h, cooled, and then stirred at room temperature for 72 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL), followed by 6 N hydrochloric acid until the pH was 2. The mixture was extracted with dichloromethane, and the organic layer was dried (MgSO 4 ) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (700 mg).

1 H NMR (CDCl 3 ) δ 12.88 (s, 1H), 8.99 (s, 1H), 7.20 (m, 2H), 7.03 (m, 1H), 4.32 (m, 2H), 3.69 (m, 2H), 3.25 (s, 3H).

Step E: Preparation of 2-(3,5-difluorophenyl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-3-(2-methoxyethyl)-4(3H)-pyrimidinone

To 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylic acid (i.e. the product from Example 9, Step D) (0.25 g, 0.81 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.21 g, 1.6 mmol) and one drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The remaining crude oil was re-dissolved in dichloromethane (10 mL) and then treated with bicycle[3.2.1]octane-2,4-dione (0.12 g, 0.88 mmol) (prepared according to U.S. Pat. No. 6,815,563) and triethylamine (0.16 g, 1.6 mmol). After 30 min at room temperature, a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.0075 g, 0.088 mmol) and triethylamine (0.16 g, 1.6 mmol) were added and the reaction mixture was stirred at ambient temperature over night. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.180 g of the title compound (also known as 3-[[2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinyl]carbonyl]biciclo[3.2.1]octane-2,4-dione), a compound of the present invention, as a solid.

1 H NMR (CDCl 3 ) δ 16.58 (br s, 1H), 8.05 (s, 1H), 7.17 (m, 2H), 6.96 (m, 1H), 4.18 (br s, 2H), 3.61 (t, 2H), 3.26 (br s, 3H), 3.09 (br s, 1H), 2.96 (br s, 1H), 2.26 (d, 1H), 2.17 (br s, 2H), 2.02 (br s, 1H), 1.88 (br s, 1H), 1.73 (m, 1H).

›EXAMPLE 10

Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone (Compound 97)

›Step A: Preparation of 3-thiophenecarboximidic acid ethyl ester hydrochloride

To a solution of thiophene-3-carbonitrile (10 g, 9.2 mmol) in dichloromethane (100 mL) and ethanol (170 mL) at 0° C. was added acetyl chloride (114 g, 145 mmol). The reaction was allowed to slowly warm to ambient temperature and stir 16 h. The reaction mixture was then concentrated under reduced pressure to yield a solid which was triturated with diethyl ether resulting in 17.1 g of 3-thiophenecarboximidic acid ethyl ester hydrochloride as a white solid.

1 H NMR (DMSO-d 6 ) δ 11.77 (br s, 2H), 8.92 (m, 1H), 7.90 (m, 1H), 7.83 (m, 1H), 4.60 (q, 2H), 1.46 (t, 3H).

Step B: Preparation of ethyl 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate

2-Methoxy-1-ethylamine (0.86 g, 11.4 mmol) was added to a solution of 3-thiophenecarboximidic acid ethyl ester hydrochloride (2.0 g, 10.4 mmol) in methanol (10 mL), which was then stirred at ambient temperature for 1.5 h. The reaction mixture was then concentrated under reduced pressure and redissolved in ethanol (10 mL). Sodium ethoxide solution (21% w/w in ethanol, 3.4 g, 10 mmol) and diethyl ethoxymethylenemalonate (2.2 g, 10 mmol) were added and the mixture was heated to reflux for 2 h before being concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to provide 1.82 g of the title compound as an oil.

1 H NMR (CDCl 3 ) δ 8.68 (s, 1H), 8.06 (m, 1H), 7.48 (m, 1H), 7.43 (m, 1H), 4.38 (m, 4H), 3.81 (t, 2H), 3.29 (s, 3H), 1.40 (t, 3H).

›Step C: 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylic acid

Ethyl 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate a (1.82 g, 5.90 mmol) (i.e. the product from Example 10, Step B) was dissolved in ethyl acetate and treated with lithium iodide (powder, 2.36 g, 17.6 mmol) and heated to reflux for 16 h. The crude reaction mixture was concentrated under reduced pressure and then aqueous sodium bicarbonate solution was added and the resulting solution was extracted with ethyl acetate which was then discarded. The aqueous layer was made acidic with hydrochloric acid (1 N) and then extracted with dichloromethane (2×40 mL). The combined organics were dried over MgSO 4 and concentrated under reduced pressure to provide the title compound as a solid.

1 H NMR (CDCl 3 ) δ 12.96 (br s, 1H), 8.99 (s, 1H), 8.17 (m, 1H), 7.53 (m, 1H), 7.48 (m, 1H), 4.47 (t, 2H), 3.83 (t, 2H), 3.32 (s, 3H).

Step D: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone

To 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 10, Step C) (0.5 g, 1.8 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.45 g, 3.6 mmol) and one drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The crude oil was redissolved in 10 mL of dichloromethane and treated with 1,3-cyclohexanedione (0.22 g, 2.0 mmol) and triethylamine (0.18 g, 1.8 mmol). The reaction mixture was stirred for 30 min then treated with a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.18 mmol) and triethylamine (0.182 g, 1.8 mmol) and stirred at ambient temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.160 g of the title compound (also known as 2-[[1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione), a compound of the invention, as a solid.

1 H NMR (CDCl 3 ) δ 16.51 (s, 1H), 8.14 (s, 1H), 7.97 (m, 1H), 7.43 (m, 2H), 4.29 (t, 2H), 3.70 (t, 2H), 3.29 (s, 3H), 2.73 (t, 2H), 2.50 (t, 2H), 2.08 (m, 2H).

›EXAMPLE 11

Preparation of 3-cyclohexyl-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone (Compound 128)

›Step A: Preparation of ethyl 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate

Cyclohexylamine (0.58 g, 5.8 mmol) was added to a solution of ethyl benzenecarboximidic acid ethyl ester (1.0 g, 5.4 mmol) in methanol (10 mL), which was then stirred at room temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and then redissolved in ethanol (10 mL). Sodium ethoxide solution (21% w/w in ethanol, 1.8 g, 5.5 mmol) and diethyl ethoxymethylenemalonate (1.2 g, 5.5 mmol) were added and the mixture was heated to reflux for 16 h before being concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to provide 1.41 g of the title compound as a yellow oil.

1 H NMR (CDCl 3 ) δ 8.58 (s, 1H), 7.53 (m, 3H), 7.45 (m, 2H), 4.41 (m, 2H), 3.94 (m, 1H), 2.76 (m, 2H), 1.78 (d, 2H), 1.67 (d, 2H), 1.53 (d, 1H), 1.42 (m, 3H), 1.21 (m, 1H), 0.96 (m, 2H).

›Step B: Preparation of 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid · 1 of 4

Ethyl 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate (1.41 g, 4.32 mmol) (i.e. the product from Example 11, Step A) was dissolved in ethyl acetate and treated with lithium iodide (powder, 1.72 g, 12.8 mmol) and heated to reflux for 16 h. The crude reaction mixture was concentrated under reduced pressure and then aqueous sodium bicarbonate was added and the resulting solution was extracted with ethyl acetate which was then discarded. The aqueous layer was made acidic with hydrochloric acid (1 N) and then extracted with dichloromethane (2×40 mL). The combined organic extracts were dried over MgSO 4 and concentrated under reduced pressure resulting in 0.58 g of the title product as a solid.

1 H NMR (CDCl 3 ) δ 13.30 (br. s., 1 H), 8.94 (s, 1 H), 7.59 (m, 3 H), 7.48 (m, 2 H), 4.12 (m, 1 H), 2.68 (m, 2 H), 1.84 (d, 2 H), 1.74 (d, 2 H), 1.60 (d, 1 H), 1.22 (m, 1 H), 1.03 (m, 2 H).

Step C: Preparation of 2-[(1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinyl)carbonyl]-1,3-cyclohexanedione

To 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 11, Step B) (0.58 g, 1.5 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.490 g, 3.9 mmol) and one drop of N,N-dimethylformamide. The reaction was stirred at ambient temperature for 2 h and then concentrated under reduced pressure. The crude oil was then redissolved in 10 mL of dichloromethane and then treated with 1,3-cyclohexanedione (0.24 g, 2.1 mmol) and triethylamine (0.39 g, 3.8 mmol) stirred for 30 min, then treated with a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.15 mmol) and triethylamine (0.393 g, 3.8 mmol) and stirred at ambient temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.570 g of the title compound, a compound of the invention, as a solid.

1 H NMR (CDCl 3 ) δ 16.61 (s, 1H), 8.02 (s, 1H), 7.50 (m, 5H), 3.93 (m, 1H), 2.73 (t, 2H), 2.61 (m, 2H), 2.51 (t, 2H), 2.08 (m, 2H), 1.74 (m, 4H), 1.51 (d, 1H), 1.19 (m, 1H), 0.97 (m, 2H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 32 can be prepared. The following abbreviations are used in the Tables which follow: Me means methyl, Et means ethyl, n-Pr means normal propyl, i-Pr means isopropyl, c-Pr means cyclopropyl, n-Bu means normal butyl, i-Bu means isobutyl, s-Bu means secondary butyl, c-Bu means cyclobutyl, t-Bu means tertiary butyl, n-pent means normal pentyl, c-Pent means cyclopentyl, n-Hex means normal hexyl, hept means hetpyl, c-Hex means cyclohexyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, thp means tetrahydropyran, thtp means tetrahydrothiopyran, thf means tetrahydrofuran, —CN means cyano, —NO 2 means nitro, S(O)Me means methylsulfinyl, SO 2 means sulfonyl and S(O) 2 Me means methylsulfonyl.

The present disclosure also includes Tables 1A through 57A, each of which is constructed the same as Table 1 above except that the row heading in Table 1 (i.e. “R 2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1A the row heading is “R 2 is Me”, and R 1 is as defined in Table 1 above. Thus, the first entry in Table 1A specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is Me; R 2 is Me; R 3 is OH; A is A-1; B 1 is C-1; B 2 is C-3; B 3 is C-1; and each R 14 , R 15 , R 18 and R 19 is H. Tables 2A through 57A are constructed similarly.

The present disclosure also includes Tables 1B through 38B, each of which is constructed the same as Table 2 above except that the row heading in Table 2 (i.e. “R 1 is Me”) is replaced with the respective row headings shown below. For example, in Table 1B the row heading is “R 1 is Et”, and R 2 , R 3 , R 14a , R 15a , R 18 , R 19 , R 14b and R 15b are as defined in Table 2 above. Thus, the first entry in Table 1B specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is Et; R 2 is Et, R 3 is OH; A is A-1; B 1 is C-1, B 2 is C-3 and B 3 is C-1; R 14a is Me; R 15a is H; R 18 is H; R 19 is H; R 14b is H; and R 15b is H. Tables 2B through 38B are constructed similarly.

The present disclosure also includes Tables 1C through 37C, each of which is constructed the same as Table 3 above except that the row heading in Table 3 (i.e. “R 1 is CH 3 , R 9 is CH 3 ”) is replaced with the respective row headings shown below. For example, in Table 1C the row heading is “R 1 is CH 2 CH 3 , R 9 is CH 3 ”, and R 2 is as defined in Table 3 above. Thus, the first entry in Table 1C specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is CH 2 CH 3 ; R 2 is Et; A is A-5; R 3 is OH; R 9 is CH 3 ; and R 10 is H. Tables 2C through 27C are constructed similarly.

The present disclosure also includes Tables 1D through 37D, each of which is constructed the same as Table 4 above except that the row heading in Table 4 (i.e. “R 1 is CH 3 , R 9 is CH 3 ”) is replaced with the respective row headings shown below. For example, in Table 1D the row heading is “R 1 is CH 2 CH 3 , R 9 is CH 3 ”, and R 2 is as defined in Table 4 above. Thus, the first entry in Table 1D specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is CH 2 CH 3 ; R 2 is Et; A is A-5; R 3 is OH; R 9 is CH 3 ; and R 10 is CH 3 . Tables 2D through 37D are constructed similarly.

The present disclosure also includes Tables 1E through 57E, each of which is constructed the same as Table 1 above except that the row heading in Table 1 (i.e. “R 2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1E the row heading is “R 2 is Me”, and R 1 is as defined in Table 5 above. Thus, the first entry in Table 1E specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is Me; R 2 is Me; R 3 is OH; A is A-1; B 1 is C-1; B 2 is C-3; B 3 is C-1; and each R 14 , R 15 , R 18 and R 19 is H. Tables 2E through 57E are constructed similarly.

›Step B: Preparation of 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid · 2 of 4

The present disclosure also includes Tables 1F through 11F, each of which is constructed the same as Table 6 above except that the row heading in Table 6 (i.e. “R 1 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1F the row heading is “R 1 is n-Pr”, and R 2 is as defined in Table 6 above. Thus, the first entry in Table 1F specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is phenyl; R 2 n-Pr; R 3 is OMe; A is A-3; B 2 is C-3; T is —CH 2 CH 2 —; R 18 and R 19 are both H. Tables 2F through 11F are constructed similarly.

The present disclosure also includes Tables 1H through 2H, each of which is constructed the same as Table 8 above except that the row heading in Table 8 (i.e. “R 12 is c-Pr”) is replaced with the respective row headings shown below. For example, in Table 1H the row heading is “R 12 is CH 3 ”, and R 1 and R 2 are as defined in Table 8 above. Thus, the first entry in Table 1H specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is CH 3 ; R 2 is Et; A is A-6; R 11 is H; and R 12 is CH 3 . Table 2H is constructed similarly.

The present disclosure also includes Tables 1J through 2J, each of which is constructed the same as Table 9 above except that the row heading in Table 9 (i.e. “R 12 is c-Pr”) is replaced with the respective row headings shown below. For example, in Table 1J the row heading is “R 12 is CH 3 ”, and R 1 and R 2 are as defined in Table 9 above. Thus, the first entry in Table 1J specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is CH 3 ; R 2 is Et; A is A-7; R 12 is CH 3 ; and R 13 is cyano. Table 2J is constructed similarly.

The present disclosure also includes Tables 1K through 10K, each of which is constructed the same as Table 9 above except that the row heading in Table 10 (i.e. “R 1 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1K the row heading is “R 1 is n-Bu”, and R 2 is as defined in Table 10 above. Thus, the first entry in Table 1K specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is n-Bu; R 2 is Ph; A is A-7; R 12 is hydroxy; and R 13 is nitro. Table 2K through 10K are constructed similarly.

The present disclosure also includes Tables 1U through 57U, each of which is constructed the same as Table 19 above except that the row heading in Table 19 (i.e. “R 2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1U the row heading is “R 2 is Me”, and R 1 is as defined in Table 19 above. Thus, the first entry in Table 1U specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is Me; R 2 is Me; R 3 is OH; A is A-1; B 1 is C-1; B 2 is C-3; B 3 is C-1; and each R 14 , R 15 , R 18 and R 19 is H. Tables 2U through 57U are constructed similarly.

The present disclosure also includes Tables 1BB through 57BB, each of which is constructed the same as Table 27 above except that the row heading in Table 27 (i.e. “R 2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1BB the row heading is “R 2 is Me”, and R 1 is as defined in Table 27 above. Thus, the first entry in Table 1BB specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R 1 is Me; R 2 is Me; R 3 is OH; A is A-1; B 1 is C-1; B 2 is C-3; B 3 is C-1; and each R 14 , R 15 , R 18 and R 19 is H. Tables 2BB through 57BB are constructed similarly.

The present disclosure also includes Tables 1K through 4K, each of which is constructed the same as Table 11 above except that the row heading in Table 11 (i.e. “R 2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1K the row heading is “R 2 is Ph”, and R 1 is as defined in Table 11 above. Thus, the first entry in Table 1K specifically discloses a compound of Formula 1P wherein X is N, Y is C(O), R 1 is Me; R 2 is c-Pr; R 3 is OH; A is A-1; B 1 is C-1; B 2 is C-3; B 3 is C-1; and each R 14 , R 15 , R 18 and R 19 is H. Tables 2K through 4K are constructed similarly.

The present disclosure also includes Tables 1L through 11L, each of which is constructed the same as Table 12 above except that the row heading in Table 12 (i.e. “R 2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1L the row heading is “R 2 is Ph”, and R 1 is as defined in Table 12 above. Thus, the first entry in Table 1L specifically discloses a compound of Formula 1P wherein X is CH; Y is S(O) 2 ; R 1 is Me and R 2 is c-Pr; R 3 is OH; A is A-1; B 1 is C-1; B 2 is C-3; B 3 is C-1; and each R 14 , R 15 , R 18 and R 19 is H. Tables 2L through 11L are constructed similarly.

A compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.

Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.

›Step B: Preparation of 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid · 3 of 4

Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.

Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. .

Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C 6 -C 22 ), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as “surface-active agents”) generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides.

Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.

›Step B: Preparation of 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid · 4 of 4

Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon's Emulsifiers and Detergents , annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents , Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents , Seventh Edition, John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon's Volume 2 . Functional Materials , annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μm can be wet milled using media mills to obtain particles with average diameters below 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 μm range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering , Dec. 4, 1967, pp 147-48 , Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. Nos. 4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food - Environment Challenge , T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science , John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology , PJB Publications, Richmond, U K, 2000.

In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-B. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.

›EXAMPLE A

High Strength Concentrate

›EXAMPLE B

Wettable Powder

›EXAMPLE C

Granule

›EXAMPLE D

Extruded Pellet

›EXAMPLE E

Emulsifiable Concentrate

›EXAMPLE F · 1 of 3

Microemulsion

These compounds generally show highest activity for early postemergence weed control (i.e. applied when the emerged weed seedlings are still young) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum , soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of the invention are particularly useful for selective control of weeds in wheat, barley, and particularly maize, soybean, cotton and perennial plantation crops such as sugarcane and citrus. Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have both postemergent and preemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.

A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of a compound of this invention is about 0.001 to 20 kg/ha with a typical range of about 0.004 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.

Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.

A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halo sulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron and vernolate. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.

›EXAMPLE F · 2 of 3

Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides, herbicide safeners, insecticides, fungicides, nematocides, acaricides and biological agents) include The Pesticide Manual, 13 th Edition , C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2003 and The BioPesticide Manual, 2 nd Edition , L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2001.

For embodiments where one or more of these various mixing partners are used, the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30:1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.

In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.

Of note is a combination of a compound of the invention with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of the invention. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.

Compounds of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, BCS (1-bromo-4-[(chloromethyl)sulfonyl]benzene), cloquintocet-mexyl, cyometrinil, cyprosulfonamide, dichlormid, 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone ((4-methoxy-3-methylphenyl)(3-methylphenyl)methanone), naphthalic anhydride (1,8-naphthalic anhydride) and oxabetrinil to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.

Of note is a composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

Preferred for better control of undesired vegetation (e.g., lower use rate such as from synergism, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of 2,4-D, ametryne, aminocyclopyrachlor, aminopyralid, atrazine, bromacil, bromoxynil, bromoxynil octanoate, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron, clopyralid, clopyralid-olamine, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, diflufenican, dimethenamid, dimethenamid-P, diuron, florasulam, flufenacet, flumetsulam, flumioxazin, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluroxypyr, glyphosate (particularly glyphosate-isopropylammonium, glyphosate-sodium, glyphosate-potassium, glyphosate-trimesium), hexazinone, imazamethabenz-methyl, imazaquin, imazethapyr, iodosulfuron-methyl, lactofen, lenacil, linuron, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, MCPA-thioethyl, mesosulfuron-methyl, S-metolachlor, metribuzin, metsulfuron-methyl, nicosulfuron, oxyfluorfen, pendimethalin, pinoxaden, pronamide, prosulfuron, pyroxasulfone, pyroxsulam, quinclorac, rimsulfuron, saflufenacil, sulfentrazone, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, and triclopyr-triethylammonium. Specifically preferred mixtures (compound numbers refer to compounds in Index Table A) are selected from the group: compound 2 and 2,4-D; compound 4 and 2,4-D; compound 8 and 2,4-D; compound 12 and 2,4-D; compound 2 and ametryne; compound 4 and ametryne; compound 8 and ametryne; compound 12 and ametryne; compound 2 and aminocyclopyrachlor; compound 4 and aminocyclopyrachlor; compound 8 and aminocyclopyrachlor; compound 12 and aminocyclopyrachlor; compound 2 and aminopyralid; compound 4 and aminopyralid; compound 8 and aminopyralid; compound 12 and aminopyralid; compound 2 and atrazine; compound 4 and atrazine; compound 8 and atrazine; compound 12 and atrazine; compound 2 and bromacil; compound 4 and bromacil; compound 8 and bromacil; compound 12 and bromacil; compound 2 and bromoxynil; compound 4 and bromoxynil; compound 8 and bromoxynil; compound 12 and bromoxynil; compound 2 and bromoxynil octanoate; compound 4 and bromoxynil octanoate; compound 8 and bromoxynil octanoate; compound 12 and bromoxynil octanoate; compound 2 and carfentrazone-ethyl; compound 4 and carfentrazone-ethyl; compound 8 and carfentrazone-ethyl; compound 12 and carfentrazone-ethyl; compound 2 and chlorimuron-ethyl; compound 4 and chlorimuron-ethyl; compound 8 and chlorimuron-ethyl; compound 12 and chlorimuron-ethyl; compound 2 and chlorsulfuron; compound 4 and chlorsulfuron; compound 8 and chlorsulfuron; compound 12 and chlorsulfuron; compound 2 and clopyralid; compound 4 and clopyralid; compound 8 and clopyralid; compound 12 and clopyralid; compound 2 and clopyralid-olamine; compound 4 and clopyralid-olamine; compound 8 and clopyralid-olamine; compound 12 and clopyralid-olamine; compound 2 and dicamba; compound 4 and dicamba; compound 8 and dicamba; compound 12 and dicamba; compound 2 and diflufenican; compound 4 and diflufenican; compound 8 and diflufenican; compound 12 and diflufenican; compound 2 and dimethenamid; compound 4 and dimethenamid; compound 8 and dimethenamid; compound 12 and dimethenamid; compound 2 and dimethenamid-P; compound 4 and dimethenamid-P; compound 8 and dimethenamid-P; compound 12 and dimethenamid-P; compound 2 and diuron; compound 4 and diuron; compound 8 and diuron; compound 12 and diuron; compound 2 and florasulam; compound 4 and florasulam; compound 8 and florasulam; compound 12 and florasulam; compound 2 and flufenacet; compound 4 and flufenacet; compound 8 and flufenacet; compound 12 and flufenacet; compound 2 and flumetsulam; compound 4 and flumetsulam; compound 8 and flumetsulam; compound 12 and flumetsulam; compound 2 and flumioxazin; compound 4 and flumioxazin; compound 8 and flumioxazin; compound 12 and flumioxazin; compound 2 and flupyrsulfuron-methyl; compound 4 and flupyrsulfuron-methyl; compound 8 and flupyrsulfuron-methyl; compound 12 and flupyrsulfuron-methyl; compound 2 and flupyrsulfuron-methyl-sodium; compound 4 and flupyrsulfuron-methyl-sodium; compound 8 and flupyrsulfuron-methyl-sodium; compound 12 and flupyrsulfuron-methyl-sodium; compound 2 and fluroxypyr; compound 4 and fluroxypyr; compound 8 and fluroxypyr; compound 12 and fluroxypyr; compound 2 and glyphosate; compound 4 and glyphosate; compound 8 and glyphosate; compound 12 and glyphosate; compound 2 and hexazinone; compound 4 and hexazinone; compound 8 and hexazinone; compound 12 and hexazinone; compound 2 and imazamethabenz-methyl; compound 4 and imazamethabenz-methyl; compound 8 and imazamethabenz-methyl; compound 12 and imazamethabenz-methyl; compound 2 and imazaquin; compound 4 and imazaquin; compound 8 and imazaquin; compound 12 and imazaquin; compound 2 and imazethapyr; compound 4 and imazethapyr; compound 8 and imazethapyr; compound 12 and imazethapyr; compound 2 and iodosulfuron-methyl; compound 4 and iodosulfuron-methyl; compound 8 and iodosulfuron-methyl; compound 12 and iodosulfuron-methyl; compound 2 and lactofen; compound 4 and lactofen; compound 8 and lactofen; compound 12 and lactofen; compound 2 and lenacil; compound 4 and lenacil; compound 8 and lenacil; compound 12 and lenacil; compound 2 and linuron; compound 4 and linuron; compound 8 and linuron; compound 12 and linuron; compound 2 and MCPA; compound 4 and MCPA; compound 8 and MCPA; compound 12 and MCPA; compound 2 and MCPA-isoctyl; compound 4 and MCPA-isoctyl; compound 8 and MCPA-isoctyl; compound 12 and MCPA-isoctyl; compound 2 and MCPA-thioethyl; compound 4 and MCPA-thioethyl; compound 8 and MCPA-thioethyl; compound 12 and MCPA-thioethyl; compound 2 and mesosulfuron-methyl; compound 4 and mesosulfuron-methyl; compound 8 and mesosulfuron-methyl; compound 12 and mesosulfuron-methyl; compound 2 and S-metolachlor; compound 4 and S-metolachlor; compound 8 and S-metolachlor; compound 12 and S-metolachlor; compound 2 and metribuzin; compound 4 and metribuzin; compound 8 and metribuzin; compound 12 and metribuzin; compound 2 and metsulfuron-methyl; compound 4 and metsulfuron-methyl; compound 8 and metsulfuron-methyl; compound 12 and metsulfuron-methyl; compound 2 and nicosulfuron; compound 4 and nicosulfuron; compound 8 and nicosulfuron; compound 12 and nicosulfuron; compound 2 and oxyfluorfen; compound 4 and oxyfluorfen; compound 8 and oxyfluorfen; compound 12 and oxyfluorfen; compound 2 and pendimethalin; compound 4 and pendimethalin; compound 8 and pendimethalin; compound 12 and pendimethalin; compound 2 and pinoxaden; compound 4 and pinoxaden; compound 8 and pinoxaden; compound 12 and pinoxaden; compound 2 and pronamide; compound 4 and pronamide; compound 8 and pronamide; compound 12 and pronamide; compound 2 and prosulfuron; compound 4 and prosulfuron; compound 8 and prosulfuron; compound 12 and prosulfuron; compound 2 and pyroxasulfone; compound 4 and pyroxasulfone; compound 8 and pyroxasulfone; compound 12 and pyroxasulfone; compound 2 and pyroxsulam; compound 4 and pyroxsulam; compound 8 and pyroxsulam; compound 12 and pyroxsulam; compound 2 and quinclorac; compound 4 and quinclorac; compound 8 and quinclorac; compound 12 and quinclorac; compound 2 and rimsulfuron; compound 4 and rimsulfuron; compound 8 and rimsulfuron; compound 12 and rimsulfuron; compound 2 and saflufenacil; compound 4 and saflufenacil; compound 8 and saflufenacil; compound 12 and saflufenacil; compound 2 and sulfentrazone; compound 4 and sulfentrazone; compound 8 and sulfentrazone; compound 12 and sulfentrazone; compound 2 and thifensulfuron-methyl; compound 4 and thifensulfuron-methyl; compound 8 and thifensulfuron-methyl; compound 12 and thifensulfuron-methyl; compound 2 and triasulfuron; compound 4 and triasulfuron; compound 8 and triasulfuron; compound 12 and triasulfuron; compound 2 and tribenuron-methyl; compound 4 and tribenuron-methyl; compound 8 and tribenuron-methyl; compound 12 and tribenuron-methyl; compound 2 and triclopyr; compound 4 and triclopyr; compound 8 and triclopyr; compound 12 and triclopyr; compound 2 and triclopyr-butotyl; compound 4 and triclopyr-butotyl; compound 8 and triclopyr-butotyl; compound 12 and triclopyr-butotyl; compound 2 and triclopyr-triethylammonium; compound 4 and triclopyr-triethylammonium; compound 8 and triclopyr-triethylammonium; compound 12 and triclopyr-triethylammonium.

›EXAMPLE F · 3 of 3

Table A1 lists specific combinations of a compound of Formula 1 (i.e. Component (a)) with an additional active ingredient (i.e. Component (b)) illustrative of the mixtures, compositions and methods of the present invention. The first column of Table A1 lists compound 45 as the illustrative compound of Formula 1. The second column of Table A1 lists the specific Component (b) compound (e.g., “2,4-D” in the first line). The third, fourth and fifth columns of Table A1 lists ranges of weight ratios for rates at which the Component (b) compound is typically applied to a field-grown crop relative to Component (a). Thus, for example, the first line of Table A1 specifically discloses the combination of Component (a) with 2,4-D is typically applied in a weight ratio between 1:192 to 6:1. The remaining lines of Table A1 are to be construed similarly.

The present disclosure also includes Tables A2 through A22 which are each constructed the same as Table A1 above except that entries below the “Component (a)” column heading are replaced with the respective Component (a) Column Entry shown below. Thus, for example, in Table A2 the entries below the “Component (a)” column heading all recite “Compound 50”, and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 50 with 2,4-D. Tables A3 through A22 are constructed similarly.

The following Tests demonstrate the herbicidal effect of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to the plant species tested. See Index Tables A-I for compound descriptions. The following abbreviations are used in the Index Tables which follow: “Cmpd” means Compound, Me is methyl, Et is ethyl, c-Pr is cyclopropyl, i-Bu is isobutyl (i.e. —CH 2 CH(CH 3 ) 2 ), Ph is phenyl, OMe is methoxy, c-hex is cyclohexyl, n-hex is normal hexyl Bn in benzyl, acetylene means —C≡CH, and SMe is methylthio. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared. Substitution is noted in parentheses following the listed ring, for example Ph(4-OMe) indicates that the phenyl group is substituted by methoxy at the 4-position (relative to the point of attachment of the phenyl group to the remainder of the Formula 1 compound).

Biological Examples of the Invention

›Test A

Seeds of barnyardgrass ( Echinochloa crus - galli ), large crabgrass ( Digitaria sanguinalis ), giant foxtail ( Setaria faberii ), morningglory ( Ipomoea spp.), pigweed ( Amaranthus retroflexus ), velvetleaf ( Abutilon theophrasti ), wheat ( Triticum aestivum ) and corn ( Zea mays ) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time these species were also treated with postemergence applications of test compounds formulated in the same manner.

Plants ranged in height from two to ten cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately ten days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

›Test B

Seeds of plant species selected from blackgrass ( Alopecurus myosuroides ), downy bromegrass ( Bromus tectorum ), green foxtail ( Setaria viridis ), Italian ryegrass ( Lolium multiflorum ), wheat ( Triticum aestivum ), wild oat ( Avena fatua ), deadnettle (henbit deadnettle, Lamium amplexicaule ), galium (catchweed bedstraw, Galium aparine ), bermudagrass ( Cynodon dactylon ), Surinam grass ( Brachiaria decumbens ), cocklebur ( Xanthium strumarium ), corn ( Zea mays ), large crabgrass ( Digitaria sanguinalis ), woolly cupgrass ( Eriochloa villosa ), giant foxtail ( Setaria faberii ), goosegrass ( Eleusine indica ), johnsongrass ( Sorghum halepense ), kochia ( Kochia scoparia ), lambsquarters ( Chenopodium album ), morningglory ( Ipomoea coccinea ), nightshade (eastern black nightshade, Solanum ptycanthum ), yellow nutsedge ( Cyperus esculentus ), pigweed ( Amaranthus retroflexus ), ragweed (common ragweed, Ambrosia elatior ), Russian thistle ( Salsola kali ), soybean ( Glycine max ), sunflower (common oilseed sunflower, Helianthus annuus ) and velvetleaf ( Abutilon theophrasti ) were planted into a blend of loam soil and sand and treated preemergence with test compounds formulated in a non-phytotoxic solvent mixture which included a surfactant.

At the same time, plants selected from these crop and weed species and also winter barley ( Hordeum vulgare ), canarygrass ( Phalaris minor ), chickweed ( Stellaria media ) and windgrass ( Apera spica - venti ) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients and treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.

Plant species in the flooded paddy test consisted of rice ( Oryza sativa ), umbrella sedge ( Cyperus difformis ), ducksalad ( Heteranthera limosa ) and barnyardgrass ( Echinochloa crus - galli ) grown to the 2-leaf stage for testing. At the time of treatment, test pots were flooded with water to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test.

Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all treated plants were visually evaluated and compared to controls. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE B Flood 250 g ai/ha Compounds 1 2 3 4 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 Barnyardgrass 0 0 0 20 0 45 50 0 25 0 35 0 35 10 25 50 15 0 0 0 0 20 0 0 40 20 30 0 0 40 40 0 0 15 0 0 30 40 30 0 Ducksalad 0 78 70 85 0 90 75 80 80 55 95 40 60 75 45 90 90 75 75 60 45 75 0 85 85 85 85 50 75 95 95 65 0 40 60 65 90 90 75 50 Rice 0 8 0 0 0 50 0 0 25 0 25 0 0 10 15 25 0 15 0 0 15 0 0 0 0 0 0 0 0 30 50 0 — 35 20 0 15 25 0 20 Sedge, Umbrella 0 75 60 90 0 95 75 55 85 65 85 40 30 50 80 85 95 60 65 65 45 75 0 85 85 80 80 50 75 90 85 40 0 20 40 40 90 85 80 30 250 g ai/ha Compounds 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 Barnyardgrass 20 30 30 0 20 35 0 60 55 55 75 0 20 35 25 0 45 40 20 0 10 0 0 45 0 20 30 20 0 30 0 40 60 0 65 0 30 30 60 Ducksalad 80 90 90 20 95 85 70 85 95 70 75 40 50 50 60 0 40 60 0 30 40 60 0 20 0 40 20 0 0 0 0 0 50 0 40 20 40 30 40 Rice 40 40 20 10 25 65 15 20 60 60 85 0 25 20 25 0 15 15 0 0 10 0 0 20 0 30 0 20 0 20 0 0 45 0 15 20 20 15 15 Sedge, Umbrella 80 90 85 65 85 75 85 95 90 40 90 40 60 75 75 0 75 85 0 0 0 40 0 50 0 0 40 20 25 30 0 60 50 0 40 40 30 40 40 250 g ai/ha Compounds 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 Barnyardgrass 20 40 0 65 60 60 60 40 30 65 45 85 60 70 85 75 50 55 75 40 70 0 0 0 15 60 30 20 40 60 40 Ducksalad 20 50 20 65 65 20 80 100 90 100 85 80 30 20 75 70 0 80 85 30 85 0 0 0 0 40 70 100 75 75 95 Rice 20 30 0 20 40 70 50 15 0 15 40 45 35 30 15 40 40 60 — 20 35 0 0 0 20 45 10 25 30 30 15 Sedge, Umbrella 50 50 50 80 85 70 65 85 80 100 85 90 85 75 90 80 75 85 85 65 75 0 0 0 0 85 95 80 75 85 90 250 g ai/ha Compounds 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 138 139 Barnyardgrass 15 40 65 75 75 70 50 65 70 40 70 30 60 75 75 40 60 85 50 30 0 0 0 25 25 35 Ducksalad 70 75 85 85 100 100 70 85 80 0 95 0 70 85 80 100 100 100 85 100 100 0 40 75 80 90 Rice 0 20 20 0 15 15 35 40 55 15 40 20 0 15 35 35 30 25 55 0 0 0 0 20 15 30 Sedge, Umbrella 70 40 90 90 95 85 75 75 70 45 85 40 90 85 80 75 60 100 85 100 100 0 0 50 80 85 250 g ai/ha Compounds 140 141 142 143 144 145 146 147 148 151 152 153 154 155 156 158 161 162 164 178 179 183 184 185 186 187 Barnyardgrass 45 50 10 20 20 25 30 75 50 55 75 45 40 45 60 60 30 55 0 80 30 35 25 0 30 80 Ducksalad 85 85 80 90 100 80 100 100 100 100 100 100 100 95 100 100 80 100 85 100 100 95 100 75 100 100 Rice 40 35 0 0 25 0 35 15 50 50 60 65 75 45 35 85 50 90 35 70 65 0 15 0 65 70 Sedge, Umbrella 85 85 80 65 100 80 90 80 95 100 100 95 100 100 100 100 60 100 90 95 95 90 95 60 90 100 250 g ai/ha Compounds 188 189 190 191 192 193 194 195 196 197 198 199 200 203 204 206 207 208 209 210 211 212 213 214 215 216 Barnyardgrass 0 70 30 25 0 50 15 20 30 30 35 25 38 20 60 0 20 25 20 40 35 50 30 20 40 0 Ducksalad 85 100 100 100 75 100 80 85 95 85 95 90 85 95 100 90 50 75 85 90 85 95 100 95 85 95 Rice 15 60 15 0 20 65 0 15 65 45 50 0 23 0 60 20 15 0 20 25 15 10 20 15 15 0 Sedge, Umbrella 85 100 95 85 60 90 65 65 80 85 80 85 70 85 95 85 70 70 80 80 80 95 90 85 90 100 250 g ai/ha Compounds 217 218 219 220 221 222 223 224 226 227 228 229 230 231 232 233 234 235 236 237 238 239 243 244 245 246 Barnyardgrass 0 40 60 40 20 0 0 30 95 60 80 30 40 40 50 65 0 75 20 30 40 15 85 75 65 60 Ducksalad 40 95 90 100 70 65 0 75 40 80 80 40 0 0 85 100 70 100 70 100 100 80 100 100 100 100 Rice 20 15 75 70 15 0 0 60 65 55 60 20 45 0 0 50 0 55 0 45 0 0 75 85 90 65 Sedge, Umbrella 40 85 85 85 75 40 0 75 60 85 85 70 75 75 80 85 40 80 40 100 80 75 100 100 100 100 250 g ai/ha 125 g ai/ha Compounds Compounds 248 249 250 251 252 253 254 255 256 1 2 3 4 7 8 9 10 11 12 13 14 16 17 18 19 20 21 22 23 33 34 35 36 37 Barnyardgrass 40 0 10 20 0 20 15 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 25 20 0 0 0 0 0 30 0 0 0 0 Ducksalad 90 90 75 80 0 90 100 80 85 0 58 70 75 0 85 60 75 65 35 0 30 75 30 65 85 65 70 30 45 80 30 0 0 50 Rice 0 15 0 10 0 20 0 0 0 0 0 0 0 0 15 0 0 20 0 0 0 0 0 25 0 0 0 0 0 20 0 0 20 0 Sedge, Umbrella 85 90 70 75 0 85 80 60 75 0 45 60 80 0 85 70 55 40 50 60 0 40 70 50 85 50 60 40 40 50 0 0 0 30 125 g ai/ha Compounds 38 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 76 79 80 81 82 83 84 85 86 87 88 89 90 Barnyardgrass 0 0 35 40 40 55 0 20 20 20 0 20 30 0 0 0 0 0 0 0 0 20 0 0 0 0 20 25 40 15 15 0 55 50 55 40 30 15 Ducksalad 60 40 85 85 40 75 30 0 40 40 0 0 40 0 0 40 50 0 0 0 30 0 0 0 0 0 15 30 15 0 40 0 60 55 20 75 100 80 Rice 0 10 15 25 50 60 0 15 15 15 0 15 0 0 0 0 0 0 0 0 20 0 0 0 20 0 15 0 15 15 0 0 15 20 60 40 0 0 Sedge, Umbrella 30 0 85 85 30 90 0 40 60 50 0 50 75 0 0 0 0 0 30 0 0 0 20 0 0 0 0 30 30 40 40 30 80 70 50 40 85 75 125 g ai/ha Compounds 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 108 109 110 111 123 124 125 126 127 128 129 130 132 Barnyardgrass 60 20 75 40 65 80 60 30 20 60 40 60 0 0 0 0 15 20 20 50 55 0 40 60 65 15 10 0 0 Ducksalad 90 70 80 25 0 50 30 0 75 85 30 80 0 0 0 0 60 65 75 75 90 0 60 85 60 95 90 80 80 Rice 15 25 20 20 30 15 0 0 0 35 0 20 0 0 0 20 0 20 30 0 30 20 0 0 25 10 0 0 0 Sedge, Umbrella 100 70 80 85 50 85 70 75 65 80 30 65 0 0 0 0 60 75 50 80 75 20 90 80 60 60 60 75 60 125 g ai/ha Compounds 133 142 143 144 145 146 147 148 151 152 153 154 155 156 157 158 161 162 163 164 166 167 168 170 171 172 Barnyardgrass 0 0 0 0 0 0 45 15 30 50 35 0 20 40 0 20 0 40 0 0 20 20 0 30 20 20 Ducksalad 100 80 80 75 80 80 80 90 100 100 100 70 85 80 70 100 0 100 60 0 60 70 30 45 70 60 Rice 0 0 0 20 0 0 10 20 15 30 55 60 25 20 0 40 45 90 20 20 0 0 0 20 0 0 Sedge, Umbrella 95 65 0 95 60 80 40 85 100 85 80 95 85 100 75 100 0 100 70 0 70 60 20 35 80 75 125 g ai/ha Compounds 173 174 175 176 177 178 179 180 181 182 183 184 185 186 190 191 192 193 194 195 196 197 198 199 200 203 Barnyardgrass 15 0 20 0 15 60 20 15 70 0 0 20 0 30 20 0 0 45 10 0 20 20 30 15 23 0 Ducksalad 75 95 95 75 70 100 95 75 90 85 80 100 75 90 40 75 75 85 50 70 95 80 85 85 85 95 Rice 15 0 0 20 20 70 25 30 65 0 0 15 0 45 15 0 0 30 0 0 40 30 20 0 10 0 Sedge, Umbrella 85 95 85 85 75 95 85 65 85 75 65 80 65 80 30 80 50 70 0 50 75 75 80 75 43 75 125 g ai/ha Compounds 204 207 208 209 210 211 212 213 215 216 218 219 220 221 223 224 226 227 228 229 230 235 236 237 238 239 Barnyardgrass 25 0 15 0 20 25 0 0 30 0 30 20 30 0 0 0 95 50 75 0 20 50 0 0 30 0 Ducksalad 90 0 40 85 90 85 90 90 85 90 85 65 85 70 0 0 30 75 75 0 0 100 60 90 80 70 Rice 0 15 0 10 20 0 0 0 0 0 10 70 50 0 0 0 60 45 35 0 30 45 0 0 0 0 Sedge, Umbrella 90 60 40 70 75 70 90 85 75 80 85 60 20 75 0 0 50 85 75 50 40 80 0 55 65 40 125 g ai/ha 62 g ai/ha Compounds Compounds 243 244 245 246 248 249 250 251 253 254 255 256 1 2 3 4 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 Barnyardgrass 75 40 40 20 0 0 10 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 20 20 0 0 0 0 0 Ducksalad 100 100 100 100 80 80 70 50 85 85 60 80 0 40 0 40 0 85 30 20 0 25 0 20 0 40 30 50 75 60 70 20 35 Rice 95 60 50 65 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 15 0 0 0 0 0 Sedge, Umbrella 100 100 100 100 75 85 65 65 75 75 50 75 0 0 50 65 0 65 30 40 0 40 0 0 0 0 70 30 70 40 50 30 30 62 g ai/ha Compounds 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 Barnyardgrass 0 0 0 0 10 0 0 0 10 20 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 20 0 40 0 20 15 0 0 0 0 0 Ducksalad 20 0 75 75 70 70 20 60 75 75 0 0 0 30 20 80 0 70 30 70 80 20 20 65 0 0 75 30 0 65 0 0 20 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 15 10 15 0 0 10 15 0 20 0 10 0 0 0 15 0 0 Sedge, Umbrella 0 0 75 75 70 70 20 60 75 30 0 0 0 20 0 90 70 70 30 30 80 70 45 70 40 0 75 40 30 85 0 30 40 0 0 40 30 0 62 g ai/ha Compounds 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 30 0 0 20 0 0 0 0 25 40 45 20 20 0 20 0 60 0 35 65 40 30 20 45 Ducksalad 0 20 30 0 0 0 0 0 0 0 0 0 0 30 0 30 0 0 20 0 0 30 0 50 55 30 40 90 65 90 30 55 20 0 0 30 0 40 75 Rice 0 0 0 0 0 0 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 15 0 15 0 20 15 0 0 0 30 Sedge, Umbrella 0 0 0 0 0 0 0 0 0 0 0 0 30 0 0 40 30 0 20 0 0 30 0 75 30 20 30 85 60 95 65 75 70 20 75 40 65 50 75 62 g ai/ha Compounds 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 Barnyardgrass 40 60 0 0 0 0 40 0 0 0 40 35 10 20 50 65 65 50 30 20 30 20 40 0 25 45 Ducksalad 30 40 0 0 0 0 0 50 60 40 30 85 25 65 85 80 — 100 30 30 45 0 80 0 40 80 Rice 0 15 0 0 0 0 20 0 0 0 0 0 0 0 20 0 0 0 20 0 0 0 20 15 0 0 Sedge, Umbrella 20 40 0 0 0 0 60 40 60 35 75 85 40 30 70 75 95 70 25 40 30 20 70 0 35 70 62 g ai/ha Compounds 127 128 129 130 131 132 133 134 135 136 138 139 140 141 142 143 144 145 146 147 148 151 152 153 154 155 Barnyardgrass 40 10 0 0 20 0 0 0 0 20 0 10 20 20 0 0 0 0 0 10 0 15 25 0 0 0 Ducksalad 30 95 90 80 40 50 60 0 30 55 70 75 50 75 0 80 60 80 60 60 90 80 90 65 50 60 Rice 15 0 0 0 25 0 0 0 0 15 0 10 0 0 0 0 20 0 0 0 10 0 20 35 0 0 Sedge, Umbrella 20 30 0 60 20 0 60 0 0 45 70 70 75 80 0 0 65 0 50 40 80 85 0 0 95 60 62 g ai/ha Compounds 156 158 161 162 164 178 179 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 203 Barnyardgrass 20 20 0 25 0 20 10 0 0 0 20 45 0 30 0 0 0 20 0 0 0 0 0 0 0 0 Ducksalad 65 75 0 100 0 75 90 65 100 70 90 95 70 100 20 85 60 50 50 50 60 65 50 85 83 75 Rice 30 30 50 25 0 20 0 0 15 0 20 15 0 20 15 0 0 15 0 0 0 0 20 0 0 0 Sedge, Umbrella 95 85 0 100 0 85 80 50 80 75 80 95 80 95 0 75 40 30 0 0 30 70 20 70 33 65 62 g ai/ha Compounds 204 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 226 227 228 229 230 231 Barnyardgrass 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 60 40 40 0 0 40 Ducksalad 70 70 0 30 50 85 — 85 85 0 75 90 0 80 20 40 65 50 0 0 0 — 50 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 15 0 0 0 0 40 30 20 0 20 0 Sedge, Umbrella 75 60 40 40 50 75 0 85 80 0 0 65 40 80 40 0 60 30 0 0 40 85 75 0 30 0 62 g ai/ha 31 g ai/ha Compounds Compounds 232 233 234 235 236 237 238 239 243 244 245 246 248 249 250 251 252 253 254 255 256 1 2 3 4 7 8 9 Barnyardgrass 30 20 0 20 0 0 0 0 30 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 85 100 20 95 0 65 40 0 85 80 100 100 80 65 30 0 0 75 85 50 40 0 15 0 20 0 30 0 Rice 0 25 0 0 0 0 0 0 60 0 50 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 80 70 0 70 0 45 0 0 90 0 100 85 65 60 65 50 0 65 50 20 40 0 0 40 50 0 30 0 31 g ai/ha Compounds 10 11 12 13 14 16 17 18 19 20 21 22 23 33 34 35 36 37 38 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 Barnyardgrass 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 15 0 20 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 20 0 60 60 0 20 60 0 0 0 0 0 0 70 0 0 40 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 Rice 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 0 0 20 0 0 0 0 0 0 0 40 0 20 20 0 0 0 0 0 0 75 30 20 40 0 0 30 0 0 30 0 0 0 0 0 0 0 0 0 31 g ai/ha Compounds 69 70 71 72 76 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 108 109 Barnyardgrass 0 0 0 0 0 0 15 0 0 0 0 25 30 20 0 20 0 15 0 30 0 20 60 30 0 0 20 20 15 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 0 0 20 0 40 0 20 30 45 50 65 20 40 0 0 0 30 0 30 35 20 30 0 0 0 0 40 50 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 10 0 0 0 0 0 0 Sedge, Umbrella 0 0 0 0 0 0 0 0 0 0 0 50 20 0 0 30 50 75 65 70 20 0 50 30 40 50 40 0 30 0 0 0 0 0 50 31 g ai/ha Compounds 110 111 123 124 125 126 127 128 129 130 132 133 142 143 144 145 146 147 148 151 152 153 154 155 156 157 Barnyardgrass 0 0 30 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 15 0 0 0 0 0 Ducksalad 0 30 30 0 20 75 0 90 0 60 0 60 0 80 50 80 0 60 90 80 0 0 0 0 0 50 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 15 0 0 0 20 20 20 35 0 0 30 0 Sedge, Umbrella 30 0 40 0 25 50 0 0 0 40 0 0 0 0 50 0 0 0 80 85 0 0 0 60 0 40 31 g ai/ha Compounds 158 161 162 163 164 166 167 168 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 190 Barnyardgrass 20 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 Ducksalad 50 0 98 30 0 0 0 0 0 40 20 30 80 75 40 30 75 90 60 85 60 30 95 75 90 20 Rice 20 25 0 10 0 0 0 0 15 0 0 0 0 0 15 15 0 0 15 0 0 0 15 0 10 15 Sedge, Umbrella 70 0 95 70 0 50 20 0 0 70 0 0 85 75 70 60 55 40 20 75 50 0 65 65 70 0 31 g ai/ha Compounds 191 192 193 194 195 196 197 198 199 200 203 204 207 208 209 210 211 212 213 215 216 218 219 220 221 223 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 65 60 40 40 0 40 65 40 85 38 40 50 0 0 0 75 50 85 75 70 50 75 0 30 20 0 Rice 0 0 0 0 0 0 0 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 60 0 0 0 0 20 65 20 60 30 0 70 0 0 0 50 0 80 65 0 0 75 20 0 0 0 31 g ai/ha Compounds 224 226 227 228 229 230 235 236 237 238 239 243 244 245 246 248 249 250 251 253 254 255 256 Barnyardgrass 0 50 20 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 — 40 0 0 95 0 0 0 0 0 35 100 85 75 0 30 0 60 45 0 30 Rice 0 20 20 0 0 0 0 0 0 0 0 45 0 50 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 0 30 80 65 0 0 0 0 0 0 0 0 0 60 0 50 0 0 0 60 30 0 30 Postemergence 250 g ai/ha Compounds 1 3 4 7 8 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 Barley 0 0 10 0 20 35 5 10 0 40 70 0 20 0 0 30 — 0 35 10 10 5 15 5 0 35 Bermudagrass 65 80 100 70 100 98 95 100 100 80 100 75 100 100 98 98 100 100 100 100 100 98 98 100 90 — Blackgrass 5 5 50 5 20 70 50 40 20 5 50 40 50 50 30 40 15 30 40 20 15 20 30 25 10 30 Bromegrass, Downy 10 45 55 5 10 50 20 45 20 70 75 40 30 45 20 50 65 45 85 0 85 25 85 50 25 55 Canarygrass 0 5 80 0 85 60 40 90 40 50 60 60 50 40 5 50 50 30 45 20 35 0 40 30 0 40 Chickweed 90 100 100 100 100 98 98 100 100 80 100 85 80 85 100 100 100 100 100 100 100 95 100 100 98 100 Cocklebur 85 100 100 70 100 45 98 100 100 98 100 100 98 98 95 95 — — — 98 — 95 98 95 90 100 Corn 0 15 85 10 80 80 65 85 75 70 85 50 70 60 15 50 85 75 90 65 90 45 85 80 75 — Crabgrass, Large 65 90 100 60 100 95 80 100 90 85 100 80 60 80 98 98 98 90 100 90 100 90 98 85 75 100 Cupgrass, Woolly 20 55 100 65 100 85 75 95 80 80 95 85 80 85 90 95 98 100 100 90 98 55 95 80 45 100 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 50 65 100 60 100 100 95 100 98 95 95 95 90 95 95 95 98 100 100 95 100 85 98 98 85 98 Foxtail, Green 40 50 60 40 95 95 70 98 70 85 95 95 90 90 90 95 90 95 95 90 95 85 90 95 85 95 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 80 95 98 35 100 100 98 98 100 85 98 95 98 95 85 95 95 95 95 75 98 95 95 90 80 98 Johnsongrass 20 15 98 0 100 95 75 98 75 80 80 70 80 45 40 100 100 85 100 98 100 65 95 100 75 — Kochia 45 95 100 50 100 85 20 98 65 — 100 — 100 — 98 100 65 65 100 95 75 100 95 98 30 100 Lambsquarters 90 100 100 75 100 95 95 98 98 85 100 98 98 98 100 100 100 100 100 100 100 100 98 100 95 100 Morningglory 65 70 95 20 100 75 55 80 95 95 90 75 90 98 85 95 75 95 100 95 85 98 80 90 80 95 Nutsedge, Yellow 45 80 80 0 85 70 75 60 80 50 70 35 55 70 80 65 60 65 55 45 — 70 55 60 75 70 Oat, Wild 10 50 50 10 35 55 40 70 20 50 80 60 65 80 55 70 85 80 85 40 90 25 85 70 30 60 Pigweed 90 100 100 98 100 100 100 98 100 98 80 98 100 85 100 98 98 100 100 100 100 100 100 100 80 100 Ragweed 75 100 100 85 100 100 98 100 100 98 98 100 100 100 98 98 95 98 95 98 98 85 98 98 80 95 Ryegrass, Italian 0 5 20 20 50 45 20 40 5 50 50 45 10 45 45 40 15 30 65 20 10 15 35 35 10 50 Soybean 80 90 100 85 100 98 98 100 100 90 100 98 100 98 100 100 100 100 100 100 100 95 95 98 90 98 Surinam Grass 20 65 90 25 80 85 80 85 85 55 80 60 80 85 90 85 95 95 95 70 100 65 95 95 90 100 Velvetleaf 90 100 100 98 100 98 85 100 100 100 98 98 90 98 100 100 100 100 100 95 100 98 100 95 90 100 Wheat 5 30 70 15 35 30 5 45 0 20 50 30 30 40 5 55 5 5 60 20 35 10 30 30 0 15 Windgrass 5 5 75 5 40 80 40 98 50 50 80 60 60 50 60 80 85 70 90 — 90 — — — 50 — 250 g ai/ha Compounds 48 49 50 51 52 53 55 56 58 59 61 62 63 64 66 67 68 70 71 72 73 74 75 77 79 80 Barley 10 0 5 50 25 70 0 — 10 10 0 30 0 35 0 30 30 90 5 0 10 0 0 0 55 75 Bermudagrass 100 98 100 98 100 98 90 100 100 100 90 90 95 98 95 85 98 98 98 85 90 98 98 95 85 55 Blackgrass 30 30 15 55 30 50 10 20 40 60 5 50 50 15 15 10 20 50 5 0 30 45 20 5 45 10 Bromegrass, Downy 70 5 20 60 70 60 0 60 50 45 5 50 40 85 25 5 40 70 30 20 60 35 50 5 65 80 Canarygrass 45 0 5 98 85 90 0 40 85 70 0 5 0 60 0 5 35 98 20 0 40 0 0 0 50 70 Chickweed 100 90 98 95 98 100 90 98 90 100 98 80 95 100 98 100 100 100 98 90 100 100 100 98 98 100 Cocklebur 98 85 90 90 85 90 75 95 90 100 85 75 95 95 45 90 90 40 95 95 80 95 95 85 98 65 Corn 85 15 25 85 80 85 10 70 80 75 15 80 45 90 75 75 80 75 15 10 85 60 55 75 75 65 Crabgrass, Large 95 85 98 90 98 100 85 95 90 100 75 85 90 98 70 95 98 100 95 90 95 95 100 85 95 95 Cupgrass, Woolly 95 55 85 90 95 98 20 85 95 95 60 65 65 98 75 75 75 90 100 50 65 75 80 40 75 75 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 98 75 95 85 90 95 75 95 98 95 75 80 80 100 95 90 90 98 95 80 90 85 95 80 95 95 Foxtail, Green 95 90 95 100 100 100 80 100 100 70 80 85 90 100 98 95 95 98 98 90 95 85 90 80 98 98 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 98 70 90 85 85 85 75 90 90 95 80 75 75 90 95 80 95 95 90 70 80 85 98 85 80 85 Johnsongrass 95 10 70 98 95 100 20 100 100 100 10 10 15 100 65 10 100 98 100 45 75 85 75 10 75 45 Kochia 100 90 100 35 65 80 85 100 25 75 85 80 65 80 98 85 98 98 65 90 90 98 100 95 80 60 Lambsquarters 100 98 100 98 95 98 98 100 100 100 98 100 98 100 100 100 100 100 98 100 100 98 100 98 100 100 Morningglory 80 85 80 100 85 98 85 100 90 80 80 75 75 90 100 100 100 100 80 90 95 100 95 90 100 100 Nutsedge, Yellow 70 70 75 80 65 75 65 75 75 75 65 55 60 25 70 70 80 60 25 75 70 70 75 80 80 75 Oat, Wild 85 40 30 90 95 85 5 45 85 80 5 40 20 98 10 10 70 95 5 40 95 80 60 5 75 50 Pigweed 100 98 100 100 98 100 95 100 100 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 98 90 98 95 85 98 98 75 98 95 90 80 80 90 60 90 95 80 95 95 85 90 95 85 98 75 Ryegrass, Italian 30 0 0 30 60 45 0 50 70 80 0 50 10 30 10 5 50 70 5 30 70 35 60 10 55 5 Soybean 98 85 95 95 98 95 75 98 95 95 50 95 85 98 98 98 98 98 98 95 95 95 98 70 98 95 Surinam Grass 98 70 85 90 98 98 60 100 98 90 75 70 75 98 98 25 90 100 85 100 85 75 85 80 90 65 Velvetleaf 100 98 100 95 100 98 100 98 95 98 98 100 98 100 100 100 100 100 95 100 100 100 100 100 100 100 Wheat 30 30 15 30 35 50 10 0 0 60 10 30 10 55 0 25 10 35 5 10 50 50 25 10 40 35 Windgrass — 30 80 85 100 95 5 85 70 70 20 50 60 100 80 5 85 100 60 65 98 95 90 25 90 80 250 g ai/ha Compounds 81 82 83 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 102 107 108 109 111 113 117 Barley 5 5 5 20 65 5 80 20 20 40 0 5 5 0 5 5 15 30 50 60 30 0 5 30 20 0 Bermudagrass 95 95 90 90 95 100 85 95 85 95 85 85 98 90 98 98 98 98 85 100 98 100 95 100 95 100 Blackgrass 30 15 0 50 55 40 10 30 30 50 5 30 20 5 40 50 50 15 40 45 20 30 50 40 5 40 Bromegrass, Downy 50 30 60 30 50 80 60 5 10 30 20 0 0 0 10 10 40 25 35 30 30 5 5 10 90 45 Canarygrass 20 35 25 60 85 35 90 60 30 75 0 10 35 0 45 30 50 70 10 50 80 5 45 15 90 5 Chickweed 100 100 100 98 98 100 95 98 90 100 100 98 100 100 100 100 100 98 100 100 100 100 100 100 100 100 Cocklebur 90 100 90 98 98 100 95 70 100 95 98 98 90 100 100 100 100 100 98 100 100 100 100 100 98 100 Corn 65 15 25 85 85 75 80 98 75 60 60 60 80 35 80 75 70 80 45 70 85 65 60 60 85 25 Crabgrass, Large 98 90 98 95 98 98 98 98 80 100 100 90 90 80 90 95 95 95 80 90 95 85 85 85 95 95 Cupgrass, Woolly 90 75 95 90 95 90 95 75 55 98 70 70 70 65 85 75 95 85 75 85 80 75 75 75 95 98 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 98 95 98 98 98 95 95 98 85 98 98 85 98 85 85 90 85 95 85 95 95 80 90 70 95 95 Foxtail, Green 95 90 98 98 100 95 100 80 90 98 98 90 80 90 85 95 95 98 85 95 98 80 98 70 95 95 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 80 85 95 85 95 98 70 80 75 85 90 75 85 90 85 98 90 80 75 90 85 85 85 85 90 85 Johnsongrass 100 95 100 98 100 45 100 100 65 100 100 70 45 45 80 85 98 95 25 75 90 60 75 40 95 25 Kochia 100 75 95 90 98 100 85 100 98 95 100 98 90 100 100 100 98 100 100 100 100 100 98 100 100 85 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 100 100 98 100 100 100 100 100 98 100 Morningglory 100 100 100 100 100 65 95 100 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Nutsedge, Yellow 80 55 85 85 85 75 75 75 75 75 75 70 65 85 85 80 75 75 40 80 85 85 80 85 75 35 Oat, Wild 55 10 10 60 80 90 80 50 20 50 10 5 30 0 30 10 50 80 30 80 40 0 40 10 85 35 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 98 100 100 100 100 100 100 Ragweed 100 95 98 98 98 98 98 100 95 98 75 98 80 95 95 100 90 95 80 95 98 98 98 98 98 98 Ryegrass, Italian 55 10 5 45 60 60 80 30 0 20 30 0 10 0 10 5 15 20 50 10 5 0 40 5 85 50 Soybean 98 98 95 95 98 100 98 98 100 98 98 98 95 98 98 100 100 100 100 100 100 85 100 98 98 95 Surinam Grass 100 80 90 85 100 85 98 95 75 98 75 70 80 70 85 85 90 80 75 85 85 80 80 80 90 85 Velvetleaf 100 95 100 98 100 100 98 100 100 100 100 98 80 100 100 100 98 100 85 100 100 100 100 100 98 100 Wheat 25 5 0 35 45 50 5 10 35 50 0 5 5 0 15 5 20 5 35 30 15 5 15 30 50 25 Windgrass 70 50 30 95 95 95 70 50 50 65 90 55 50 0 45 85 70 60 60 70 85 40 80 70 80 65 250 g ai/ha Compounds 118 119 120 121 123 126 127 128 129 130 140 141 146 147 152 155 156 157 160 162 164 173 181 184 186 187 Barley 0 5 5 10 50 40 60 5 0 0 0 5 30 0 90 85 85 30 50 85 35 50 55 60 5 40 Bermudagrass 98 98 98 100 98 95 98 100 98 95 90 90 100 98 98 100 98 100 95 100 100 100 100 100 98 100 Blackgrass 40 50 60 60 80 45 40 15 5 5 5 25 50 55 70 65 50 40 25 65 35 50 15 50 20 5 Bromegrass, Downy 35 85 80 90 45 40 40 50 35 40 20 45 35 10 85 50 40 65 55 50 95 70 85 60 50 40 Canarygrass 15 30 55 30 85 90 60 30 0 25 5 5 10 5 85 65 60 90 35 90 98 80 90 95 40 60 Chickweed 100 100 100 100 100 98 98 100 100 100 75 95 98 98 95 100 100 100 100 100 100 100 100 100 100 100 Cocklebur 98 95 80 100 100 98 100 100 100 100 95 100 — 100 100 100 98 100 100 100 100 100 100 100 100 100 Corn 25 70 75 85 80 80 75 60 60 80 45 45 35 40 80 65 60 100 60 85 70 85 95 98 65 80 Crabgrass, Large 95 95 98 98 90 90 95 100 85 100 90 85 98 90 95 90 80 100 95 98 100 100 100 100 95 100 Cupgrass, Woolly 95 100 100 100 90 90 85 95 85 90 65 70 75 80 100 75 65 98 95 100 100 100 100 100 85 95 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — 100 100 100 Foxtail, Giant 95 95 98 98 85 90 90 98 98 98 90 85 98 90 98 95 90 100 85 98 100 100 100 100 95 100 Foxtail, Green 95 100 100 100 90 95 95 98 95 98 95 90 90 90 100 80 85 95 98 100 100 90 98 98 95 98 Galium — — — — — — — — — — — — — — — — — — — — — — — 60 70 85 Goosegrass 90 95 98 98 85 85 85 98 95 95 85 80 95 95 98 98 80 100 90 98 98 100 100 100 100 100 Johnsongrass 35 80 80 85 90 90 95 85 85 80 45 65 95 60 100 70 65 100 75 100 98 — 100 100 100 100 Kochia 98 100 98 100 100 85 100 98 98 100 35 90 90 100 100 100 25 45 100 80 100 100 100 10 100 80 Lambsquarters 100 100 100 100 98 98 95 100 98 100 80 100 100 100 100 100 100 100 98 100 100 100 100 100 100 100 Morningglory 80 95 90 45 100 100 98 90 90 100 65 65 95 100 95 100 100 100 100 100 100 95 100 100 100 100 Nutsedge, Yellow 65 75 75 50 80 80 80 60 85 40 75 60 40 75 80 75 75 45 80 80 75 75 85 75 80 75 Oat, Wild 40 95 95 98 60 50 60 80 30 60 40 40 70 45 85 70 50 70 60 55 90 85 100 98 45 45 Pigweed 100 100 100 100 100 98 100 100 98 100 98 98 100 100 100 100 100 98 100 100 100 100 100 100 100 100 Ragweed 98 98 80 95 98 90 98 98 95 98 75 95 98 98 98 95 90 100 98 100 100 98 100 — 100 100 Ryegrass, Italian 60 85 80 75 50 50 30 30 0 5 5 5 15 40 80 60 40 35 35 90 40 30 65 60 30 30 Soybean 100 80 98 100 90 98 98 98 98 100 80 90 100 85 100 100 98 100 98 100 100 100 100 100 100 100 Surinam Grass 90 98 100 100 85 98 90 85 85 90 65 75 75 75 95 75 70 100 75 85 98 — 100 100 — — Velvetleaf 100 100 100 100 100 98 100 100 100 100 85 98 100 100 100 100 100 100 100 100 95 100 100 100 100 100 Wheat 10 60 80 80 50 50 40 5 0 10 15 10 45 10 90 70 45 30 45 40 50 50 70 60 5 5 Windgrass 80 100 90 100 90 60 70 85 85 85 30 50 60 70 98 85 60 80 80 80 85 75 65 100 65 80 250 g ai/ha 125 g ai/ha Compounds Compounds 189 190 191 193 197 217 218 219 220 226 227 228 229 233 235 236 237 238 239 240 243 244 245 255 1 2 Barley 40 70 70 50 40 10 35 30 15 60 30 40 25 10 — 0 40 40 5 15 95 98 95 50 0 30 Bermudagrass 70 100 100 100 100 100 100 100 100 98 90 95 90 100 100 — 100 100 100 100 100 100 100 100 60 90 Blackgrass 5 40 60 60 45 30 5 90 40 60 20 55 30 50 — 40 80 70 50 65 98 85 80 60 5 45 Bromegrass, Downy 10 35 75 85 30 65 30 80 30 30 25 10 30 60 85 25 95 85 10 50 100 80 95 85 0 80 Canarygrass 10 55 85 25 60 20 5 55 30 60 10 10 60 20 30 10 50 30 0 40 100 100 100 60 0 80 Chickweed 100 100 100 100 100 100 100 100 100 95 90 100 98 100 100 100 100 100 100 100 100 100 100 100 65 95 Cocklebur 100 100 100 100 100 100 — — — 100 95 100 100 100 — 100 — — 100 — — — — — 70 95 Corn 45 65 85 60 65 35 80 80 75 98 85 90 85 85 100 — 100 95 75 100 100 100 100 85 0 35 Crabgrass, Large 100 90 100 100 100 98 90 98 90 98 90 98 90 100 100 100 100 98 98 100 100 100 100 95 55 90 Cupgrass, Woolly 80 85 98 98 98 55 80 98 65 95 95 98 90 100 100 — 100 100 95 100 100 100 100 98 0 85 Deadnettle 100 100 100 100 100 — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 98 95 100 100 100 90 85 95 95 95 98 95 95 98 100 98 100 100 98 100 98 100 100 100 20 85 Foxtail, Green 95 70 98 80 70 90 90 90 90 90 90 100 95 100 98 98 95 98 95 98 100 100 100 90 30 100 Galium 85 85 60 90 80 — — — — — — — — — — — — — — — — — — — — — Goosegrass 90 98 100 100 100 95 35 95 90 85 80 90 80 98 100 100 98 98 100 98 98 98 100 98 65 95 Johnsongrass 70 80 100 80 100 65 80 100 90 100 65 100 100 25 100 55 100 100 — 100 100 100 100 95 0 98 Kochia 100 98 35 100 98 100 100 100 100 100 100 100 100 — 100 100 100 100 98 100 100 100 100 65 25 80 Lambsquarters 100 100 100 100 100 100 100 100 100 98 98 100 98 100 100 100 100 100 100 100 100 100 100 100 90 95 Morningglory 100 100 100 90 100 80 98 100 100 100 100 100 100 100 100 — 100 100 100 — 100 100 100 100 45 95 Nutsedge, Yellow 65 75 70 75 75 70 60 85 55 75 65 70 55 25 60 65 45 25 70 45 85 75 75 60 20 75 Oat, Wild 25 50 80 75 85 85 60 85 50 50 30 40 35 60 95 60 90 60 30 60 100 98 100 90 10 55 Pigweed 100 100 100 100 100 100 100 100 100 98 100 100 100 — 100 — 100 100 100 100 100 100 100 100 85 95 Ragweed 80 — — — — 98 100 100 98 90 85 98 95 98 100 98 100 100 100 100 100 100 100 95 70 90 Ryegrass, Italian 5 30 50 45 35 40 70 40 60 20 10 0 10 60 60 5 60 70 0 40 95 95 85 80 0 40 Soybean 100 98 100 100 100 98 100 100 100 100 98 100 98 100 100 100 100 100 98 100 100 100 100 100 70 95 Surinam Grass 85 90 98 95 70 95 90 65 75 85 95 98 90 100 100 — 100 100 75 100 100 100 100 90 10 85 Velvetleaf 100 100 100 100 100 100 100 98 100 98 98 100 85 100 100 100 100 100 100 100 100 100 100 100 85 90 Wheat 0 30 65 60 40 50 0 50 15 30 20 35 35 65 80 60 85 80 30 50 100 95 98 80 0 20 Windgrass 80 65 100 75 98 85 45 85 60 85 50 90 65 60 98 85 100 95 70 98 100 95 98 95 0 50 125 g ai/ha Compounds 3 4 7 8 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 Barley 0 0 0 5 20 0 10 0 5 50 0 10 0 0 30 20 0 0 0 10 0 5 5 0 10 10 0 5 Bermudagrass 70 85 65 95 98 90 100 98 80 100 60 100 90 98 95 100 98 100 85 100 95 95 95 90 98 98 95 100 Blackgrass 0 30 0 10 40 50 40 10 5 40 10 45 40 30 10 15 5 15 0 10 15 30 10 10 25 20 0 5 Bromegrass, Downy 0 50 5 10 40 10 45 20 50 70 20 20 40 10 50 45 15 85 0 70 15 80 45 10 50 50 0 20 Canarygrass 0 75 0 70 50 5 90 5 20 — 50 30 40 5 50 50 10 10 0 30 0 30 30 0 40 45 0 5 Chickweed 98 100 90 100 95 95 100 100 80 95 85 50 50 100 98 100 85 100 100 100 80 98 98 95 100 95 80 98 Cocklebur 85 100 65 100 35 95 100 100 90 98 95 95 95 95 85 — — — 95 — 85 90 70 80 95 98 80 90 Corn 10 50 0 75 75 45 80 45 45 85 40 50 50 10 45 65 60 75 45 85 20 80 60 60 80 85 5 25 Crabgrass, Large 80 100 45 90 85 75 100 80 85 95 50 60 55 90 95 95 85 98 85 100 85 95 75 75 90 95 80 95 Cupgrass, Woolly 20 100 50 90 80 70 90 70 80 95 85 70 85 70 90 95 75 95 85 98 25 85 75 25 90 90 55 80 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 60 98 55 100 95 80 98 98 80 90 70 90 90 85 95 98 95 100 95 100 75 95 95 80 98 95 70 95 Foxtail, Green 35 60 30 85 80 70 85 70 50 90 85 80 75 90 90 90 85 95 90 95 60 90 85 85 95 95 75 95 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 70 85 35 95 90 95 95 98 80 85 95 98 85 85 90 90 85 90 65 95 90 90 80 80 95 95 70 90 Johnsongrass — 95 0 98 85 60 90 60 80 70 50 45 40 35 95 85 60 95 90 75 40 90 98 70 98 80 10 65 Kochia 85 100 45 100 25 15 75 60 — 80 — 100 — 95 100 60 15 100 60 10 100 75 15 20 98 100 80 100 Lambsquarters 98 100 65 100 80 90 95 98 85 90 90 95 90 98 100 100 98 100 100 100 100 95 100 90 98 100 90 100 Morningglory 55 90 15 100 70 45 70 70 80 60 75 80 80 80 85 75 75 75 75 75 75 75 80 45 90 80 80 70 Nutsedge, Yellow 65 75 0 80 60 60 50 65 30 30 35 50 70 75 55 25 25 15 15 55 70 50 45 70 70 60 70 70 Oat, Wild 5 50 0 35 40 20 70 20 50 60 45 50 60 40 60 75 40 80 30 90 10 80 60 20 60 85 5 10 Pigweed 100 100 90 100 100 95 85 98 80 80 85 100 80 98 98 90 98 98 100 100 100 98 100 80 100 100 95 100 Ragweed 98 100 80 100 75 90 100 100 85 90 98 100 100 98 95 95 95 80 95 98 85 95 95 80 95 90 80 98 Ryegrass, Italian 5 15 0 30 30 0 40 5 5 40 10 5 40 40 20 10 5 60 5 0 10 10 35 5 30 30 0 0 Soybean 80 100 75 98 85 95 100 100 90 95 95 95 98 98 95 100 95 90 98 100 95 95 98 90 98 98 85 95 Surinam Grass 40 75 20 75 75 70 85 65 50 60 60 80 70 75 80 85 75 90 65 98 45 95 95 80 98 95 55 80 Velvetleaf 100 90 90 95 90 75 100 98 90 98 95 80 80 98 98 100 95 100 80 100 95 100 90 85 98 98 98 98 Wheat 10 50 10 35 30 0 40 0 0 30 5 10 10 5 35 5 0 40 5 30 5 30 15 0 5 10 15 5 Windgrass 0 60 5 30 60 30 85 45 30 60 40 50 30 30 50 80 50 85 5 80 70 85 70 15 80 90 5 60 125 g ai/ha Compounds 51 52 53 55 56 58 59 61 62 63 64 66 67 68 69 70 71 72 73 74 75 77 79 80 81 82 83 85 Barley 30 25 70 0 30 5 10 0 5 0 — 0 20 25 15 90 0 0 0 0 0 0 35 30 0 0 5 20 Bermudagrass 90 95 98 85 100 98 98 90 85 85 98 95 70 95 98 95 80 85 90 95 98 95 85 45 95 85 85 90 Blackgrass 50 25 40 5 20 20 40 0 30 35 5 10 5 0 0 35 0 0 10 25 0 0 30 5 30 5 0 35 Bromegrass, Downy 55 60 55 0 50 45 35 0 50 20 60 20 0 25 70 70 10 0 50 5 35 5 30 60 30 5 45 25 Canarygrass 60 65 90 0 40 80 50 0 0 0 40 0 0 35 25 85 5 0 5 0 0 0 35 50 10 15 25 55 Chickweed 85 95 98 80 98 90 98 95 75 80 98 95 95 98 98 98 95 90 95 95 98 95 95 100 98 98 98 95 Cocklebur 90 85 85 65 75 85 90 70 55 90 95 25 90 90 20 40 95 90 65 90 95 60 98 45 65 95 80 98 Corn 80 65 80 5 65 65 75 10 75 25 85 70 65 80 25 60 0 5 80 15 20 60 60 65 15 5 15 85 Crabgrass, Large 85 90 95 80 90 90 95 75 80 80 98 65 90 90 98 95 80 85 90 95 100 75 90 90 95 80 95 90 Cupgrass, Woolly 80 85 95 15 65 70 90 60 60 65 98 60 70 55 95 90 85 50 65 55 55 35 65 70 90 65 90 90 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 85 90 90 55 85 90 95 65 75 65 98 80 85 85 98 95 80 75 80 70 85 75 95 95 95 95 95 90 Foxtail, Green 95 98 100 80 98 98 70 60 80 70 100 90 80 85 100 98 70 90 90 80 90 80 80 95 95 85 98 95 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 85 85 80 65 75 85 95 65 65 70 85 70 65 85 85 85 90 65 75 80 95 75 70 80 70 80 80 80 Johnsongrass 85 90 95 10 85 98 100 10 0 10 100 65 5 75 100 80 98 40 70 10 20 10 70 10 75 80 100 95 Kochia 25 55 75 75 100 25 45 70 60 25 80 90 85 95 80 75 25 90 90 95 100 95 75 20 90 65 80 85 Lambsquarters 95 90 98 95 100 100 100 95 98 98 100 95 98 100 100 100 90 100 100 95 100 98 100 98 100 100 100 98 Morningglory 90 75 80 75 100 90 80 70 75 75 85 100 95 98 75 100 75 90 75 95 95 80 100 100 100 100 85 100 Nutsedge, Yellow 75 45 75 55 75 55 70 60 35 50 10 65 65 70 40 40 10 65 50 70 70 70 70 55 80 45 70 85 Oat, Wild 60 95 85 0 40 60 55 0 25 5 95 5 10 50 85 90 0 30 80 60 50 5 60 40 50 5 10 25 Pigweed 98 95 100 90 100 98 100 90 100 95 100 100 98 100 100 98 98 100 100 100 100 100 100 100 100 100 100 100 Ragweed 90 80 95 95 75 90 90 85 75 80 90 25 85 80 100 75 80 90 85 85 90 80 95 65 98 95 85 85 Ryegrass, Italian 10 55 40 0 50 30 70 0 50 0 0 5 5 15 50 50 0 10 60 20 40 5 50 5 45 5 0 35 Soybean 95 95 95 60 95 95 95 10 90 85 98 98 98 98 98 95 95 85 90 95 98 70 95 90 95 95 90 90 Surinam Grass 90 90 98 45 85 95 90 75 65 35 98 85 20 70 100 95 65 80 85 65 70 75 75 60 98 75 85 85 Velvetleaf 90 98 95 98 98 85 95 95 95 98 98 98 98 100 98 100 90 100 100 100 100 98 98 100 100 90 95 98 Wheat 10 35 30 5 0 0 10 0 5 0 30 0 25 5 10 35 0 10 40 30 10 10 35 20 25 0 0 20 Windgrass 60 90 85 0 60 60 60 0 35 40 95 70 5 65 80 90 45 60 90 80 70 20 65 70 60 20 15 80 125 g ai/ha Compounds 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 102 107 108 109 111 113 117 118 119 120 121 Barley 60 0 40 10 10 30 0 5 5 0 0 0 10 10 30 30 25 0 5 5 5 0 0 5 5 5 Bermudagrass 95 98 80 95 85 95 85 85 98 75 95 95 85 80 75 85 95 100 90 100 95 95 98 98 98 100 Blackgrass 45 20 5 20 5 30 5 30 10 0 30 30 20 5 10 30 15 20 40 25 5 40 35 50 60 40 Bromegrass, Downy 35 60 45 5 10 5 20 0 0 0 5 5 5 25 15 10 10 5 5 5 80 15 30 60 60 80 Canarygrass 80 35 80 50 30 65 0 5 30 0 30 10 35 60 5 30 60 5 30 0 — 5 10 30 55 5 Chickweed 95 100 95 98 85 98 98 95 100 98 98 100 98 98 95 95 100 100 98 100 100 98 95 100 85 100 Cocklebur 95 100 95 65 100 95 98 95 60 100 98 100 100 100 95 100 100 100 100 100 98 98 85 80 25 85 Corn 80 75 65 98 45 45 45 50 70 25 65 60 55 65 20 65 75 50 60 55 80 25 20 60 50 55 Crabgrass, Large 98 95 98 95 75 98 98 80 90 75 85 85 80 95 75 85 90 75 75 80 95 95 80 95 95 95 Cupgrass, Woolly 95 75 90 65 50 98 65 65 65 65 85 70 75 80 70 75 75 70 60 75 95 95 75 98 100 100 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 98 85 95 90 75 98 90 80 85 75 80 85 85 95 80 80 85 75 80 65 90 80 85 95 85 98 Foxtail, Green 100 90 100 70 80 98 98 80 70 65 70 85 85 95 80 90 90 80 85 65 80 80 95 95 95 100 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 85 95 70 75 75 85 75 65 75 75 85 80 80 75 75 80 75 75 80 85 85 75 80 85 85 98 Johnsongrass 100 35 100 100 30 95 98 50 45 15 70 75 75 80 10 60 70 20 50 20 90 — 20 75 75 — Kochia 98 100 80 85 85 85 95 95 80 100 95 98 80 100 98 100 100 98 85 100 100 — 70 95 80 — Lambsquarters 100 100 100 98 100 100 100 95 100 98 100 100 100 100 98 100 100 100 100 100 98 100 100 100 98 100 Morningglory 90 65 95 90 100 98 100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 80 70 95 80 25 Nutsedge, Yellow 75 70 70 70 70 75 70 70 60 85 85 80 70 70 15 75 75 80 75 80 75 25 65 65 65 45 Oat, Wild 60 65 70 20 10 45 5 0 5 0 25 5 20 40 30 40 20 0 30 0 45 30 10 95 80 98 Pigweed 100 — 100 100 100 100 100 98 100 100 98 100 100 100 98 95 100 100 100 100 100 — 100 100 100 100 Ragweed 95 98 95 95 85 95 75 85 65 95 95 100 80 80 75 85 95 95 95 98 98 90 95 95 75 90 Ryegrass, Italian 50 40 30 20 0 10 5 0 0 0 10 0 15 20 10 5 5 0 5 0 50 15 5 60 60 70 Soybean 98 100 98 98 98 95 98 95 95 98 75 95 98 100 100 95 100 65 98 95 98 95 95 60 95 95 Surinam Grass 98 — 95 80 70 98 70 70 65 45 75 80 85 75 65 75 80 65 65 70 90 — 75 95 100 100 Velvetleaf 100 100 95 98 100 100 100 95 75 100 98 100 95 100 70 100 100 100 100 100 98 95 98 100 98 100 Wheat 40 50 5 5 15 35 0 0 0 0 10 0 5 5 15 20 5 0 5 5 40 20 5 60 60 45 Windgrass 85 85 65 30 5 50 80 50 45 0 45 60 50 10 45 60 80 30 60 35 35 65 70 100 90 100 125 g ai/ha Compounds 122 123 126 127 128 129 130 131 140 141 146 147 152 155 156 157 160 162 164 169 173 181 184 186 187 189 Barley 50 25 15 35 0 0 0 0 0 5 15 0 85 45 60 30 35 50 30 0 35 50 60 5 40 15 Bermudagrass 85 90 90 98 98 95 90 85 85 85 100 95 98 98 95 100 90 100 98 100 100 100 100 95 100 65 Blackgrass 15 40 30 25 10 5 5 0 5 10 35 45 55 60 35 10 20 55 10 10 30 15 40 5 5 5 Bromegrass, Downy 50 10 30 20 40 15 35 0 5 10 10 5 60 35 35 60 50 45 85 90 40 60 50 30 35 5 Canarygrass 45 55 60 35 30 0 20 0 5 5 5 5 80 50 40 80 20 90 90 80 40 85 80 40 55 5 Chickweed 80 95 98 98 95 90 100 90 45 90 98 98 90 100 100 100 95 100 98 100 100 100 100 100 100 100 Cocklebur 85 100 80 95 100 98 95 100 65 95 — 90 98 98 75 100 100 100 100 100 100 100 100 100 100 100 Corn 25 75 55 25 60 60 80 20 25 45 20 25 65 40 45 95 50 80 45 55 60 95 85 30 75 35 Crabgrass, Large 85 85 85 90 95 85 95 80 80 80 85 85 95 80 65 98 95 98 98 100 95 100 100 85 100 95 Cupgrass, Woolly 75 75 85 85 90 85 85 65 65 65 65 80 98 65 55 98 85 100 98 100 100 100 100 80 85 75 Deadnettle — — — — — — — — — — — — — — — — — — — — — — 100 100 — 100 Foxtail, Giant 80 80 85 85 98 90 98 80 80 80 95 85 95 90 85 100 75 98 98 100 100 100 100 95 100 90 Foxtail, Green 85 85 90 90 95 90 95 95 85 90 80 80 98 80 85 85 70 98 98 95 90 95 85 85 98 90 Galium — — — — — — — — — — — — — — — — — — — — — — 60 70 55 85 Goosegrass 70 80 75 75 98 90 95 75 70 75 95 80 95 85 70 98 90 90 98 100 95 100 100 98 100 90 Johnsongrass 75 75 85 80 85 70 80 50 35 50 70 60 95 65 45 100 65 100 95 65 95 100 100 75 100 65 Kochia 45 80 25 100 95 95 100 75 10 85 85 80 95 100 20 10 100 75 100 100 98 100 5 100 70 98 Lambsquarters 90 98 85 90 100 95 100 98 75 98 100 98 98 100 95 100 98 98 100 100 100 100 100 100 100 100 Morningglory 85 100 100 90 90 90 100 75 65 60 85 65 75 100 100 95 100 90 98 100 80 100 100 100 100 100 Nutsedge, Yellow 75 75 80 75 60 60 35 45 65 60 20 70 80 70 70 40 80 75 70 55 60 80 45 75 65 55 Oat, Wild 35 30 35 25 60 20 40 0 10 15 50 20 80 60 35 60 50 45 85 85 70 90 80 20 45 10 Pigweed 98 100 98 95 98 98 100 100 75 95 100 100 100 100 98 90 100 100 100 100 100 100 75 100 100 100 Ragweed 75 95 85 98 95 95 98 95 65 85 98 90 95 90 75 100 98 100 98 100 90 100 — 100 100 75 Ryegrass, Italian 40 5 5 5 5 0 0 0 0 0 10 30 45 40 20 30 35 80 20 10 30 60 45 0 10 5 Soybean 80 85 85 98 98 98 98 98 75 75 98 65 98 100 98 100 98 100 100 95 95 100 100 100 100 98 Surinam Grass 90 85 85 85 85 85 80 65 55 70 75 75 90 65 60 98 60 75 95 — — 95 100 — — 80 Velvetleaf 98 95 95 100 95 95 98 98 80 98 98 95 100 100 95 100 100 95 80 100 100 100 100 100 100 100 Wheat 50 15 35 25 0 0 5 0 10 5 15 5 85 40 35 20 40 35 35 5 40 50 55 0 5 0 Windgrass 50 80 40 55 70 80 75 5 5 40 60 55 85 70 55 70 60 60 75 55 70 60 90 50 65 60 125 g ai/ha 62 g ai/ha Compounds Compounds 190 191 193 197 217 218 219 220 225 226 227 228 229 233 235 236 237 238 239 240 243 244 245 255 1 2 Barley 40 50 50 10 10 35 30 10 40 30 5 40 5 10 40 0 40 35 5 15 95 90 85 35 0 20 Bermudagrass 100 100 100 100 98 95 100 98 85 85 85 90 85 100 100 98 100 100 100 100 100 100 100 95 50 85 Blackgrass 35 50 40 10 30 5 55 30 15 40 5 50 5 30 70 30 70 60 30 65 85 65 80 10 0 30 Bromegrass, Downy 35 50 40 30 40 20 80 15 85 5 0 10 20 50 50 10 90 50 5 25 95 75 95 80 0 60 Canarygrass 25 60 25 40 20 0 55 10 85 50 5 5 50 10 30 0 50 30 0 30 100 98 100 50 0 50 Chickweed 100 98 100 100 100 100 100 98 95 85 80 100 90 100 100 100 100 100 98 100 100 98 100 100 60 90 Cocklebur 95 98 100 100 98 — — — 100 100 95 100 100 100 — 100 — — 100 — — — — — 65 90 Corn 40 75 40 45 25 75 75 55 70 98 75 85 85 85 100 70 100 95 45 100 100 95 100 85 0 25 Crabgrass, Large 80 100 98 98 90 70 95 85 95 95 85 98 90 98 98 98 100 98 95 100 100 100 100 90 50 85 Cupgrass, Woolly 80 90 95 90 45 60 95 65 85 85 90 95 80 100 100 95 100 100 95 100 100 100 100 95 0 80 Deadnettle 100 100 100 100 — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 90 100 95 98 85 65 80 55 85 95 90 95 80 98 100 95 98 100 90 100 98 95 100 98 15 85 Foxtail, Green 45 80 60 50 85 90 90 80 98 90 90 98 80 95 95 98 95 98 90 95 100 98 100 90 10 90 Galium 60 60 90 — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 80 100 98 100 85 15 95 85 95 85 75 85 70 98 98 95 98 98 98 98 98 98 100 95 60 90 Johnsongrass 75 100 70 95 60 55 98 80 75 100 60 95 100 25 100 20 100 98 60 100 100 100 100 90 0 90 Kochia 98 25 100 95 100 100 98 75 15 100 85 100 80 — 100 100 100 100 98 100 100 100 100 15 20 75 Lambsquarters 100 98 98 100 100 100 100 100 98 95 98 100 95 100 100 100 100 100 100 100 100 100 100 98 75 90 Morningglory 85 90 65 100 80 80 100 98 95 100 100 100 100 98 100 95 100 100 100 — 100 100 100 85 20 80 Nutsedge, Yellow 65 55 75 65 70 15 70 25 25 70 65 60 40 25 55 15 45 20 65 20 70 65 70 15 20 60 Oat, Wild 40 70 70 70 50 60 80 30 85 50 10 15 10 45 85 20 60 50 5 45 85 95 85 85 5 45 Pigweed 100 98 100 98 100 100 100 100 98 98 100 100 95 — 100 98 100 100 98 100 100 100 100 98 80 90 Ragweed — — — — 85 98 98 98 90 85 70 95 80 98 100 98 100 100 100 100 98 98 100 95 70 80 Ryegrass, Italian 20 50 40 30 40 60 40 30 40 5 5 0 0 50 55 0 60 25 0 40 85 80 70 30 0 40 Soybean 95 100 98 100 95 100 100 90 98 100 95 100 98 100 100 98 100 100 98 95 100 100 100 100 65 90 Surinam Grass 75 90 80 65 80 85 35 60 85 80 80 95 80 100 100 75 100 100 45 100 100 100 100 90 0 75 Velvetleaf 100 90 100 100 100 100 95 95 90 90 98 100 85 95 100 100 100 100 100 85 100 100 100 98 75 85 Wheat 30 55 60 5 50 0 50 0 55 25 10 20 5 60 80 30 85 80 5 50 95 85 95 50 0 10 Windgrass 65 85 70 50 80 45 60 40 80 70 40 80 50 60 95 70 98 85 30 98 98 80 95 80 0 15 62 g ai/ha Compounds 3 4 7 8 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 51 52 53 55 56 Barley 0 0 0 0 0 0 10 0 0 5 0 0 0 0 30 10 0 0 0 0 0 0 5 0 10 5 0 0 25 0 50 0 10 Bermudagrass 25 85 45 85 95 75 100 85 70 95 50 90 90 95 95 98 90 100 60 100 75 95 85 85 — 95 85 100 90 95 95 80 85 Blackgrass 0 20 0 10 0 0 5 10 0 10 0 5 20 15 5 5 0 15 0 10 10 10 5 5 20 5 0 5 30 5 30 0 10 Bromegrass, Downy 0 15 0 5 30 0 35 10 30 50 15 5 10 5 50 30 10 70 0 50 5 70 20 5 40 25 0 5 50 55 50 0 45 Canarygrass 0 20 0 50 25 0 50 5 20 40 30 10 20 0 50 45 5 10 0 20 0 20 10 0 30 30 0 0 60 50 80 0 30 Chickweed 98 100 80 100 85 95 98 100 — 90 50 45 50 98 75 98 80 90 100 100 70 95 85 95 98 90 75 80 80 95 98 75 95 Cocklebur 80 100 45 100 0 90 100 98 90 98 80 95 95 90 25 — — — 75 — 45 80 50 80 — 95 80 85 85 85 85 60 55 Corn 0 25 0 65 45 15 75 30 40 50 35 40 35 10 0 55 15 70 45 80 10 80 45 35 — 70 5 10 80 45 80 5 65 Crabgrass, Large 70 85 45 85 80 70 85 75 55 75 50 50 50 85 85 95 75 90 80 98 75 90 75 65 85 85 75 85 85 90 95 75 85 Cupgrass, Woolly 15 95 50 80 75 70 75 60 80 80 40 60 85 65 80 90 65 90 85 95 20 80 75 20 90 80 50 75 75 75 90 10 45 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 45 98 55 100 85 75 85 90 70 85 60 85 90 80 90 95 85 98 85 100 65 95 90 80 98 85 60 85 80 80 85 30 80 Foxtail, Green 10 40 20 70 40 25 60 60 45 40 40 80 75 85 90 90 65 90 80 95 55 90 80 60 90 95 50 80 95 98 100 40 85 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 50 75 25 85 85 75 85 85 80 85 90 90 85 75 80 85 85 85 55 90 85 90 75 75 95 85 70 80 80 80 80 60 75 Johnsongrass 0 80 0 98 70 55 70 60 80 60 50 45 20 35 90 75 40 75 65 — 0 70 90 50 — 80 0 10 75 85 95 0 80 Kochia 80 100 45 100 15 15 25 20 — 70 — — — 80 95 0 0 80 45 0 100 75 0 0 95 98 65 100 20 25 65 65 95 Lambsquarters 95 100 65 100 80 80 70 85 85 90 90 95 85 98 98 100 98 95 95 100 95 95 98 85 98 95 80 98 90 85 95 80 98 Morningglory 20 85 15 90 45 45 15 60 70 60 50 80 70 60 80 70 70 70 75 — 70 70 75 30 80 70 80 25 80 45 75 60 — Nutsedge, Yellow 45 65 0 70 25 55 35 55 30 30 30 40 50 50 25 20 15 0 0 35 60 50 10 70 65 45 65 70 65 25 65 10 70 Oat, Wild 0 50 0 15 5 5 50 5 40 50 40 50 50 15 50 75 10 75 20 85 10 80 55 5 60 50 5 5 60 90 70 0 20 Pigweed 90 100 75 100 85 85 80 95 80 80 80 98 65 95 90 85 85 98 100 98 95 95 98 75 98 85 90 98 95 90 95 85 98 Ragweed 85 100 65 100 75 80 100 100 80 80 85 98 85 95 85 90 80 80 85 98 75 95 85 75 90 85 80 90 80 80 85 80 55 Ryegrass, Italian 0 10 0 20 0 0 10 0 5 5 0 5 20 10 10 5 0 50 5 0 5 5 30 5 30 5 0 0 0 45 5 0 0 Soybean 70 100 65 98 75 95 100 100 85 95 95 95 95 98 95 98 80 85 95 100 90 95 95 80 95 95 65 85 90 95 95 60 85 Surinam Grass 25 70 10 65 65 70 70 55 50 55 40 70 50 65 75 85 70 85 65 95 40 95 75 75 95 85 30 75 85 85 95 15 80 Velvetleaf 100 75 80 80 85 70 95 85 90 90 70 60 55 90 95 100 80 100 80 100 80 98 80 80 85 85 95 98 85 98 85 98 90 Wheat 0 5 0 30 5 0 35 0 0 10 0 5 0 0 10 5 0 20 5 20 0 10 15 0 0 0 5 5 10 25 25 0 0 Windgrass 0 55 5 20 55 10 85 40 30 30 30 10 10 25 40 70 30 80 0 70 60 70 60 10 — 80 0 50 60 80 80 0 40 62 g ai/ha Compounds 58 59 61 62 63 64 66 67 68 69 70 71 72 73 74 75 77 79 80 81 82 83 85 86 87 88 89 90 91 Barley 5 0 0 5 0 — 0 5 0 5 30 0 0 0 0 0 0 30 30 0 0 5 10 40 0 30 5 5 30 Bermudagrass 85 90 90 80 85 95 70 70 75 98 85 75 80 80 80 98 90 80 40 85 85 75 85 90 90 80 85 80 95 Blackgrass 10 35 0 30 35 0 10 0 0 0 35 0 0 10 0 0 0 15 0 10 0 0 35 30 5 5 15 5 20 Bromegrass, Downy 40 30 0 45 20 45 10 0 5 55 50 5 0 45 5 20 5 10 60 5 0 45 5 10 50 45 0 5 5 Canarygrass 60 5 0 0 0 40 0 0 0 0 80 5 0 0 0 0 0 30 50 5 0 20 40 20 30 70 35 10 55 Chickweed 80 98 80 70 65 98 85 95 90 98 90 90 85 80 85 90 85 95 98 98 90 90 95 95 100 85 80 80 95 Cocklebur 85 85 65 55 80 95 10 75 75 0 0 65 80 45 85 80 0 98 10 55 90 80 95 95 100 90 60 90 65 Corn 45 0 0 70 20 85 55 10 15 10 35 0 0 80 0 0 5 45 35 10 5 5 70 60 55 65 95 25 35 Crabgrass, Large 80 85 65 75 75 90 55 80 90 95 90 75 80 85 80 98 60 85 80 95 75 85 90 98 85 98 95 75 95 Cupgrass, Woolly 65 75 55 55 60 95 40 70 10 95 65 45 45 65 10 55 20 40 70 75 55 85 85 85 75 80 50 45 85 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 85 90 65 65 65 95 75 80 80 98 85 75 70 75 55 80 75 75 90 85 80 95 80 95 80 95 85 70 98 Foxtail, Green 90 70 55 70 70 85 85 80 85 98 85 60 70 90 20 85 80 60 95 85 60 95 95 95 80 98 70 65 85 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 75 80 50 65 70 80 65 55 70 80 85 75 65 75 75 80 75 65 75 70 75 80 70 75 80 70 65 60 75 Johnsongrass 85 75 0 0 10 98 60 0 10 100 70 75 10 65 0 10 0 65 0 10 80 100 95 98 25 100 90 25 90 Kochia 10 10 25 25 25 55 85 80 90 70 65 0 85 80 75 95 80 75 20 80 60 75 85 85 100 75 75 85 80 Lambsquarters 95 98 95 95 95 100 95 95 98 100 98 85 100 98 95 100 98 98 95 98 95 98 98 100 98 98 98 95 100 Morningglory 80 50 70 15 70 80 100 90 85 70 100 65 85 50 85 90 75 95 100 90 100 75 100 80 45 90 85 95 90 Nutsedge, Yellow 40 60 60 25 20 10 45 65 10 10 15 10 65 20 20 65 60 60 15 80 15 20 85 70 60 65 55 65 65 Oat, Wild 60 40 0 10 0 90 0 5 20 80 70 0 — 80 20 20 5 45 30 35 0 10 25 50 60 55 10 5 30 Pigweed 95 100 85 98 95 100 98 98 95 100 98 85 100 98 98 100 98 100 100 100 98 90 100 100 98 100 98 98 100 Ragweed 85 80 80 75 75 85 10 80 80 90 70 80 80 80 75 85 75 85 60 80 80 80 85 90 95 80 85 75 85 Ryegrass, Italian 0 50 0 5 0 0 0 5 5 50 10 0 0 45 20 15 5 20 0 5 0 0 10 30 10 5 5 0 5 Soybean 85 95 0 80 75 98 95 90 95 90 75 70 80 85 75 95 50 90 80 95 90 90 85 95 98 90 90 98 85 Surinam Grass 80 80 65 45 25 95 70 20 55 90 65 55 80 85 45 50 65 45 45 90 65 75 85 95 75 95 75 65 98 Velvetleaf 75 90 80 95 98 98 90 95 100 98 80 85 100 100 100 100 98 98 100 100 90 90 98 100 100 90 95 98 100 Wheat 0 5 0 0 0 15 — 5 5 5 20 0 5 35 5 0 5 25 10 20 0 0 5 35 35 5 5 10 10 Windgrass 50 60 0 35 30 90 60 0 50 60 85 10 20 80 60 50 10 65 60 50 5 10 70 60 60 60 5 5 40 62 g ai/ha Compounds 92 93 94 95 96 97 98 99 100 102 107 108 109 111 113 117 118 119 120 121 122 123 126 127 128 129 Barley 0 0 0 0 0 0 5 5 20 10 5 0 0 0 5 0 0 0 5 5 10 10 5 20 0 0 Bermudagrass 80 75 80 75 95 95 80 75 70 85 80 90 85 100 90 90 95 98 95 98 80 85 85 95 85 80 Blackgrass 0 5 10 0 20 20 5 0 5 5 5 5 5 5 0 10 10 20 30 40 5 20 25 20 5 5 Bromegrass, Downy 5 0 0 0 0 0 5 5 10 10 5 0 0 0 60 10 5 30 60 50 5 5 15 10 35 10 Canarygrass 0 0 5 0 5 10 20 60 5 20 15 5 0 0 90 0 0 5 30 5 35 40 40 10 10 0 Chickweed 95 80 100 85 95 100 80 98 75 80 100 100 98 100 98 95 95 80 75 100 70 75 80 75 90 85 Cocklebur 80 90 45 95 95 100 100 100 85 95 100 95 98 98 95 75 40 10 15 45 45 80 65 95 98 98 Corn 35 45 55 0 60 40 35 65 10 15 65 35 15 45 60 15 0 45 20 55 15 70 30 25 50 35 Crabgrass, Large 90 80 75 65 80 80 75 85 60 80 85 70 75 75 90 80 75 85 85 90 75 80 80 85 85 80 Cupgrass, Woolly 25 45 65 55 75 60 70 75 65 75 65 60 60 50 85 85 70 98 75 100 70 45 75 75 90 85 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 75 80 75 65 70 75 75 80 75 75 80 60 75 65 85 75 80 85 80 98 75 75 80 85 95 85 Foxtail, Green 80 60 60 50 65 85 85 90 70 90 75 30 80 60 80 70 85 90 95 90 85 60 80 85 95 90 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 70 65 70 75 70 70 75 75 70 70 75 70 75 70 75 75 65 75 80 98 65 65 70 75 95 85 Johnsongrass 85 10 15 10 45 55 70 75 5 25 70 20 30 15 85 20 10 40 25 70 65 65 65 70 70 45 Kochia 90 85 55 100 85 90 70 80 95 70 98 95 75 100 100 50 65 75 40 100 0 65 25 98 85 95 Lambsquarters 98 95 95 98 98 100 98 100 98 98 100 98 98 98 98 98 98 100 85 100 65 95 85 85 98 95 Morningglory 95 80 75 100 95 100 85 100 100 100 100 90 98 100 100 75 60 60 50 20 75 98 85 80 80 90 Nutsedge, Yellow 65 60 20 75 70 75 60 70 5 65 75 75 65 75 75 0 45 50 35 45 70 75 75 70 35 35 Oat, Wild 5 0 5 0 5 5 20 20 10 15 5 0 0 0 40 10 5 60 80 90 30 5 10 10 50 5 Pigweed 100 95 100 98 95 100 100 100 98 70 100 98 100 100 100 98 100 98 98 100 90 98 95 95 98 95 Ragweed 60 75 45 80 80 98 75 80 70 80 85 85 95 95 95 75 85 75 75 85 60 85 75 85 85 95 Ryegrass, Italian 0 0 0 0 5 0 5 0 5 0 0 0 0 0 45 10 5 30 40 40 10 5 5 5 0 0 Soybean 98 80 80 98 75 80 98 100 98 85 98 55 95 80 98 80 90 50 80 90 75 75 75 98 98 98 Surinam Grass 65 65 60 45 75 75 75 70 65 75 75 60 65 — 85 75 — 85 85 100 75 75 80 75 80 85 Velvetleaf 100 90 70 95 98 100 95 100 70 100 100 100 98 98 95 85 75 80 95 98 90 90 90 95 95 95 Wheat 0 0 0 0 5 0 5 5 5 10 5 0 5 0 15 5 5 40 40 45 30 15 15 10 0 0 Windgrass 50 10 40 0 10 50 20 5 40 10 40 10 40 30 30 45 60 85 80 98 30 60 10 50 65 60 62 g ai/ha Compounds 130 131 140 141 146 147 152 155 156 157 159 160 162 164 169 173 181 184 186 187 189 190 191 193 197 217 Barley 0 0 0 0 0 0 45 30 45 15 50 30 35 5 0 20 40 40 5 5 5 5 50 0 5 5 Bermudagrass 90 75 75 85 90 90 95 98 90 90 100 75 95 98 75 98 100 100 80 85 15 100 100 100 100 85 Blackgrass 5 0 0 5 30 40 35 35 5 5 25 10 40 5 5 10 5 35 0 0 0 30 45 15 10 5 Bromegrass, Downy 15 0 5 5 5 5 55 30 10 40 50 5 30 80 40 25 50 50 25 30 5 30 40 30 15 15 Canarygrass 20 0 0 0 0 0 45 35 30 70 90 20 50 85 80 35 80 50 25 35 0 5 50 5 30 20 Chickweed 98 80 10 85 95 90 65 100 98 100 100 95 100 90 100 95 100 100 98 100 100 100 98 98 100 95 Cocklebur 95 98 15 65 25 75 80 55 40 100 100 100 100 100 100 65 100 100 100 100 70 90 98 95 100 98 Corn 60 10 5 45 5 15 45 25 10 80 75 40 75 25 55 25 85 80 10 65 20 0 75 15 35 10 Crabgrass, Large 85 75 65 75 75 75 85 75 55 95 95 90 90 98 95 80 100 100 85 98 75 65 100 90 85 85 Cupgrass, Woolly 85 60 50 65 65 70 98 45 50 85 85 65 100 85 98 95 85 100 75 85 70 80 90 85 85 45 Deadnettle — — — — — — — — — — — — — — — — — 100 98 95 98 98 100 100 100 — Foxtail, Giant 90 75 75 75 85 80 85 80 80 98 95 75 95 98 98 98 98 100 80 98 75 85 100 85 95 75 Foxtail, Green 90 90 60 75 55 65 75 50 60 85 98 55 98 98 85 70 85 60 80 95 80 40 55 50 30 60 Galium — — — — — — — — — — — — — — — — — 50 40 50 60 50 40 — 75 — Goosegrass 85 65 65 75 90 70 85 80 70 95 90 85 70 98 95 90 98 100 95 98 80 75 98 95 98 80 Johnsongrass 60 25 15 15 45 40 90 40 45 100 60 55 98 85 65 80 100 100 70 100 55 65 100 65 85 60 Kochia 85 60 10 65 45 75 65 100 10 0 45 100 45 100 100 65 95 0 85 50 90 10 10 80 80 98 Lambsquarters 100 95 60 80 98 95 95 100 85 98 100 98 95 98 100 98 100 100 98 100 98 98 80 98 100 100 Morningglory 95 70 60 60 15 50 75 85 80 95 65 98 80 95 95 80 100 95 100 95 100 40 65 60 100 75 Nutsedge, Yellow 20 25 45 10 10 60 75 45 60 40 60 75 60 45 20 45 65 40 65 55 40 45 40 65 55 60 Oat, Wild 30 0 5 10 20 10 45 40 35 50 80 30 40 40 30 50 75 80 5 30 10 0 60 50 40 40 Pigweed 98 95 70 75 98 95 98 100 95 75 98 100 100 98 100 90 100 70 100 100 100 75 85 95 90 100 Ragweed 90 85 45 75 80 75 80 70 65 100 90 95 95 98 100 70 100 — 90 98 70 — — — — 80 Ryegrass, Italian 0 0 0 0 5 5 30 30 5 20 40 5 45 5 0 10 40 40 0 0 0 0 40 40 0 30 Soybean 98 95 60 70 85 60 70 95 90 98 95 98 100 95 95 95 100 100 95 100 98 80 95 98 100 85 Surinam Grass 80 60 50 65 65 65 85 55 60 90 75 55 70 95 — — 80 90 — 85 70 60 85 65 55 80 Velvetleaf 95 85 65 95 85 80 95 100 80 100 100 100 85 70 100 100 100 98 70 95 90 100 80 100 80 98 Wheat 5 0 5 5 0 5 50 30 30 10 55 30 30 15 0 35 45 45 0 0 0 5 40 35 0 45 Windgrass 65 0 5 35 50 50 70 55 50 65 60 30 45 40 30 65 50 80 30 50 40 50 85 70 50 50 62 g ai/ha 31 g ai/ha Compounds Compounds 218 219 220 225 226 227 228 229 233 235 236 237 238 239 240 243 244 245 255 1 2 3 4 7 8 9 10 11 Barley 30 25 10 35 30 5 5 0 0 30 0 15 30 0 5 90 65 85 35 0 10 0 0 0 0 0 0 0 Bermudagrass 80 98 95 85 80 75 85 80 95 98 98 98 98 100 100 98 100 100 95 40 80 15 15 35 60 90 70 80 Blackgrass 0 55 20 5 30 0 35 0 30 60 5 70 60 5 50 80 60 70 5 0 10 0 10 0 5 0 0 5 Bromegrass, Downy 15 50 10 70 0 0 5 15 40 30 5 45 40 5 20 70 50 95 60 0 35 0 10 0 5 5 0 20 Canarygrass 0 55 10 85 30 0 0 15 5 30 0 40 25 0 5 98 95 95 50 0 40 0 10 0 20 5 0 50 Chickweed 100 100 95 40 75 75 100 85 95 100 100 98 90 98 98 100 95 85 98 55 75 90 100 60 98 20 90 80 Cocklebur — — — 100 98 80 98 90 100 — 100 — — 100 — — — — — 65 80 65 100 45 100 0 70 90 Corn 10 60 50 50 80 75 85 80 50 100 60 98 80 45 95 95 90 100 75 0 15 0 10 0 15 15 15 70 Crabgrass, Large 45 95 75 85 85 80 98 90 90 98 90 98 98 90 98 100 100 100 85 40 80 60 70 30 70 70 65 80 Cupgrass, Woolly 45 85 60 75 80 75 95 75 85 100 85 100 100 95 100 95 100 100 95 0 75 0 75 0 75 70 60 55 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 55 70 50 80 90 80 85 80 95 100 80 98 100 85 100 95 95 100 98 0 85 15 80 20 98 75 70 75 Foxtail, Green 85 80 65 98 80 90 90 80 90 90 95 90 95 85 90 98 98 98 90 5 75 5 40 5 40 35 10 60 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 10 95 85 90 80 75 80 70 95 98 90 98 98 98 98 95 95 98 90 60 80 15 25 20 80 60 45 65 Johnsongrass — 60 65 75 85 60 75 100 5 80 15 100 — 20 100 100 95 100 85 0 85 0 45 0 80 60 0 65 Kochia 85 98 65 10 85 75 100 70 85 100 98 80 98 98 98 95 90 100 15 15 60 65 80 0 85 10 10 25 Lambsquarters 98 100 100 85 90 98 98 95 98 100 100 100 100 98 100 100 100 100 95 70 90 85 98 0 95 75 80 50 Morningglory 70 85 65 95 98 100 100 100 80 98 95 95 — — — 100 95 100 85 0 70 15 60 15 75 45 0 15 Nutsedge, Yellow 15 55 25 25 65 45 45 20 5 45 15 35 20 30 15 65 50 45 15 15 45 15 55 0 65 20 15 25 Oat, Wild 45 70 20 50 30 0 5 5 35 50 0 55 35 5 40 85 70 85 80 5 30 0 30 0 10 0 0 50 Pigweed 100 100 100 95 85 90 100 95 98 100 85 98 100 98 100 100 100 98 98 65 85 75 100 75 98 80 85 65 Ragweed 95 98 95 80 85 70 80 80 85 100 95 98 100 98 98 95 98 98 90 60 70 80 100 50 90 70 75 100 Ryegrass, Italian 40 25 5 35 0 0 0 0 45 30 0 50 25 0 15 85 60 50 30 0 0 0 10 0 20 0 0 10 Soybean 100 98 85 95 98 65 98 98 98 100 98 100 100 95 95 98 100 98 95 50 80 65 95 60 98 70 95 100 Surinam Grass 80 25 60 75 75 70 85 70 85 90 70 98 100 35 98 95 95 100 80 0 70 15 60 0 60 55 60 60 Velvetleaf 100 90 90 90 85 80 100 75 85 100 100 90 90 100 85 100 100 100 98 55 85 95 70 70 75 85 70 80 Wheat 0 50 0 40 15 0 5 0 30 80 10 70 45 0 35 95 80 95 40 0 5 0 5 0 25 0 0 30 Windgrass 20 40 40 55 50 30 50 40 55 95 50 90 70 30 80 90 70 70 80 0 10 0 50 5 5 50 5 40 31 g ai/ha Compounds 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 51 52 53 55 56 58 59 61 62 63 64 66 67 68 69 70 Barley 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 5 0 5 5 0 0 5 0 0 0 0 5 0 0 0 0 15 0 0 0 5 10 Bermudagrass 65 70 85 40 70 85 75 75 90 85 98 50 — 70 80 80 80 85 85 75 90 80 85 90 80 75 85 — 75 — — 95 70 35 75 98 75 Blackgrass 10 0 5 0 0 10 10 0 5 0 5 0 0 5 0 5 0 5 0 0 5 0 5 20 0 0 5 10 0 15 30 0 5 0 0 0 30 Bromegrass, Downy 5 10 25 10 5 5 5 40 30 0 50 0 45 0 40 10 0 35 10 0 0 50 50 35 0 35 40 5 0 30 10 25 5 0 5 40 10 Canarygrass 0 10 40 20 10 10 0 5 40 0 10 0 20 0 20 10 0 20 30 0 0 60 0 40 0 0 60 5 0 0 0 40 0 0 0 0 50 Chickweed 100 — 80 40 40 50 80 50 85 80 85 98 100 60 90 75 80 85 85 75 80 80 95 85 65 90 70 85 80 70 60 98 80 90 85 98 80 Cocklebur 70 80 90 80 90 85 85 0 — — — 75 — 0 80 10 75 95 95 65 85 85 75 80 45 5 85 85 0 25 65 90 10 75 25 0 0 Corn 25 10 30 35 35 20 0 0 50 0 55 25 80 0 75 10 20 65 65 5 5 75 30 55 0 45 0 — 0 70 — 80 25 5 0 5 15 Crabgrass, Large 65 50 70 40 50 45 75 80 90 70 90 75 85 70 85 65 60 85 85 75 75 80 85 85 60 75 75 80 65 55 70 85 50 75 75 95 80 Cupgrass, Woolly 55 50 80 40 60 80 65 80 85 55 80 65 90 15 80 70 10 85 80 50 70 75 70 65 10 15 65 75 55 55 50 75 40 60 10 90 45 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 75 50 70 60 65 80 75 85 95 70 95 75 100 45 95 75 70 90 85 45 75 80 80 80 25 75 75 75 55 55 60 90 65 75 65 95 75 Foxtail, Green 40 45 40 35 80 60 50 70 85 60 85 80 90 50 90 50 45 80 85 50 80 85 95 95 30 80 75 50 50 40 60 70 80 10 40 95 80 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 70 80 85 60 90 80 70 75 85 80 80 40 85 70 85 75 75 90 85 65 75 75 75 75 45 65 70 75 40 65 70 80 65 55 65 75 75 Johnsongrass 55 45 60 35 40 20 15 75 65 0 70 65 — 0 70 60 40 85 45 0 0 75 75 55 0 55 50 — 0 0 — 90 45 0 10 98 65 Kochia 20 — 70 — — — 10 85 0 0 65 20 0 80 75 0 0 95 98 55 95 20 20 45 20 90 0 — 5 10 10 50 80 75 70 60 65 Lambsquarters 80 85 90 80 90 85 95 95 98 95 90 95 100 90 90 95 80 98 85 70 98 75 85 90 80 98 95 95 85 85 — 95 95 80 95 100 85 Morningglory 15 70 50 50 50 60 60 60 60 60 65 65 70 45 60 75 30 75 70 65 10 75 10 55 55 — 65 — 45 — — 80 98 80 80 70 98 Nutsedge, Yellow 15 20 20 30 30 40 40 5 10 10 0 0 20 55 40 10 65 65 40 65 70 60 20 20 10 20 25 45 20 15 20 0 25 60 0 5 10 Oat, Wild 0 30 40 40 45 40 10 40 60 0 55 10 85 5 50 35 0 40 40 0 5 60 90 50 0 5 45 30 0 5 0 60 0 0 5 60 55 Pigweed 95 80 70 50 98 60 90 70 85 80 95 98 90 85 75 85 75 98 85 80 80 85 85 85 80 98 80 — 80 98 85 98 98 98 85 98 85 Ragweed 100 80 70 70 85 80 90 75 90 80 75 85 98 70 85 80 70 85 85 75 80 80 75 80 70 55 80 75 75 70 70 85 0 75 75 90 60 Ryegrass, Italian 0 0 0 0 0 5 5 10 0 0 35 0 0 0 5 30 0 0 0 0 0 0 40 0 0 0 0 5 0 0 0 0 0 0 5 30 10 Soybean 98 80 85 95 95 85 95 85 90 75 85 95 100 70 95 80 75 95 95 55 85 85 80 90 25 85 85 90 0 75 75 85 95 80 80 80 75 Surinam Grass 25 40 50 30 50 50 45 70 75 60 70 60 85 40 85 70 45 85 70 15 65 80 75 85 10 75 70 75 20 20 10 85 65 10 25 85 65 Velvetleaf 80 85 75 70 50 50 80 80 98 75 95 75 98 80 95 70 75 80 85 90 90 80 95 85 90 85 75 85 80 85 95 85 85 90 95 95 75 Wheat 0 0 5 0 0 0 0 0 5 0 0 5 0 0 5 10 0 0 0 0 0 5 15 20 0 0 0 0 0 0 0 10 0 5 5 5 5 Windgrass 10 5 20 10 10 5 10 10 50 5 70 0 70 10 65 30 10 60 70 0 10 50 60 60 0 30 35 20 0 30 10 70 60 0 40 60 80 31 g ai/ha Compounds 71 72 73 74 75 77 79 80 81 82 83 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 102 107 108 Barley 0 0 0 0 0 0 5 15 0 0 0 5 30 0 30 0 0 0 0 0 0 0 0 0 0 5 5 0 0 0 Bermudagrass 65 75 65 75 90 90 80 20 85 80 75 85 85 90 80 75 70 75 20 60 80 45 80 95 75 75 70 80 75 85 Blackgrass 0 0 0 0 0 0 5 0 5 0 0 5 15 5 0 10 5 10 0 0 5 0 5 5 0 0 0 0 0 0 Bromegrass, Downy 0 0 20 0 5 0 5 45 5 0 40 0 10 20 40 0 5 0 0 0 0 0 0 0 5 5 5 0 0 0 Canarygrass 0 0 0 0 0 0 15 45 0 0 20 35 20 0 60 10 5 25 0 0 0 0 0 0 5 40 0 5 5 0 Chickweed 75 70 80 75 85 80 80 90 95 90 90 85 80 100 75 75 70 85 90 80 95 75 75 95 80 80 75 60 98 85 Cocklebur 65 75 0 20 40 0 95 0 5 85 75 95 85 98 90 10 75 20 25 70 45 70 75 95 98 95 40 90 98 75 Corn 0 0 20 0 0 0 5 5 5 0 0 50 10 20 15 80 15 25 20 0 0 0 45 20 35 40 0 — 65 15 Crabgrass, Large 65 75 80 80 95 55 80 75 85 70 85 90 85 85 95 85 65 80 80 70 70 45 75 75 75 85 55 70 75 60 Cupgrass, Woolly 10 45 60 10 10 20 10 65 65 55 70 75 75 50 75 35 45 70 10 45 — 45 70 55 65 70 — 70 65 40 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 20 65 70 25 75 65 70 75 75 75 80 75 90 75 95 70 65 85 65 70 65 45 65 60 65 75 70 70 75 45 Foxtail, Green 60 10 70 20 65 40 60 90 5 60 90 80 70 75 95 60 65 70 75 50 10 20 50 40 30 50 20 80 70 5 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 75 60 65 65 75 65 45 70 65 75 75 70 70 75 65 55 60 30 60 60 45 65 70 60 60 75 70 55 75 60 Johnsongrass 65 0 10 0 0 0 0 0 5 65 95 80 95 5 95 25 10 65 20 10 — 5 20 15 55 70 0 20 60 10 Kochia 0 75 75 75 75 75 75 0 75 10 65 75 75 100 75 65 65 20 75 65 — 80 65 65 65 80 — 65 98 70 Lambsquarters 75 90 85 95 98 95 95 95 95 80 95 98 100 98 95 95 85 85 90 85 80 80 90 90 95 98 95 95 90 98 Morningglory 65 20 0 60 20 75 80 85 75 65 70 95 70 45 90 70 65 75 80 70 55 100 65 100 70 100 60 65 100 75 Nutsedge, Yellow 10 35 20 20 10 45 25 10 65 10 10 75 65 10 25 35 60 50 45 45 20 75 70 75 50 45 — 45 75 50 Oat, Wild 0 0 55 20 0 0 40 20 25 0 10 5 20 50 50 10 0 30 0 0 0 0 0 0 10 10 0 5 0 0 Pigweed 85 80 80 90 100 98 100 100 98 75 80 100 98 98 98 80 85 100 90 90 100 85 90 95 100 100 90 70 95 95 Ragweed 75 75 75 75 80 75 80 50 75 75 75 80 80 85 75 70 60 85 40 65 40 75 80 85 70 65 70 70 75 80 Ryegrass, Italian 0 0 35 5 0 0 20 0 0 0 0 0 25 5 5 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 Soybean 65 80 80 75 80 25 75 75 85 75 75 80 80 98 75 90 98 75 90 55 65 95 65 70 90 98 95 75 95 45 Surinam Grass 50 75 80 20 50 65 20 45 75 65 75 75 80 75 95 55 65 85 25 50 — 45 75 65 65 70 — 60 75 55 Velvetleaf 75 98 95 98 100 90 95 85 100 85 85 90 98 100 80 90 85 98 95 85 — 85 95 100 95 95 — 98 90 100 Wheat 0 0 0 5 0 0 10 5 5 0 0 0 5 35 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Windgrass 5 5 70 5 30 10 50 50 10 5 5 40 30 55 40 0 0 10 0 5 0 0 5 5 0 5 0 5 5 0 31 g ai/ha Compounds 109 111 113 117 118 119 120 121 122 123 126 127 128 129 130 131 140 141 146 147 152 155 156 157 159 160 Barley 0 0 0 0 0 0 — 0 0 5 5 0 0 0 0 0 0 0 0 0 10 30 30 5 20 5 Bermudagrass 70 95 80 75 75 75 80 95 75 80 75 95 75 80 75 65 60 80 85 75 95 85 80 75 95 65 Blackgrass 0 5 0 0 5 5 30 5 5 20 5 5 5 0 0 0 0 5 5 10 20 10 5 0 20 5 Bromegrass, Downy 0 0 5 5 0 10 20 25 5 0 5 5 30 5 10 0 0 0 0 0 30 5 10 40 50 0 Canarygrass 0 0 65 0 0 5 0 0 10 25 15 5 10 0 5 0 0 0 0 0 35 10 15 40 80 5 Chickweed 90 95 98 85 90 70 60 100 70 70 65 65 90 85 98 65 0 60 70 70 10 100 80 100 100 85 Cocklebur 75 98 95 75 40 0 10 40 20 65 15 75 98 95 85 95 0 40 10 50 70 15 20 100 95 98 Corn 0 10 25 10 0 20 15 25 0 35 10 5 40 20 55 0 0 0 0 0 25 5 10 70 60 15 Crabgrass, Large 65 70 85 75 70 75 80 85 75 70 75 80 85 80 85 75 50 70 65 60 75 60 45 80 80 80 Cupgrass, Woolly — 40 85 65 65 75 70 95 65 25 65 75 85 80 80 50 50 65 60 65 95 20 40 85 70 65 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 70 60 80 65 75 75 75 95 70 65 70 80 95 70 90 75 65 75 75 65 80 65 75 98 85 70 Foxtail, Green 20 40 80 50 50 85 90 80 80 50 50 75 85 80 90 70 45 50 50 40 75 25 45 70 85 55 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 65 70 70 45 55 75 75 95 40 65 65 65 90 85 85 65 45 65 75 35 80 65 65 85 85 80 Johnsongrass 5 10 65 5 10 10 15 20 45 35 65 65 70 40 60 5 10 15 45 15 70 10 15 70 45 45 Kochia 70 80 98 45 45 40 10 95 0 60 10 45 60 80 85 35 0 20 40 40 10 35 10 0 40 90 Lambsquarters 98 98 95 95 85 85 80 95 60 80 70 75 95 90 98 85 45 80 95 85 85 98 80 98 100 95 Morningglory 70 100 98 10 10 10 15 5 60 70 75 65 80 90 95 70 0 60 0 50 45 55 80 20 60 75 Nutsedge, Yellow — 65 65 0 35 10 5 5 55 65 65 65 20 35 10 15 10 0 5 50 65 20 45 30 40 65 Oat, Wild 0 0 20 5 5 50 50 60 5 0 5 5 40 0 20 0 0 10 0 5 30 10 5 30 60 10 Pigweed 100 95 95 95 85 95 95 100 85 80 75 80 95 85 95 90 55 60 95 85 95 98 60 65 95 90 Ragweed 75 75 80 70 70 70 50 65 60 70 55 70 85 90 85 80 25 65 65 20 60 45 65 90 90 80 Ryegrass, Italian 0 0 40 0 5 5 10 40 5 0 0 0 0 0 0 0 0 0 5 5 5 5 0 10 30 0 Soybean 95 70 98 65 75 0 40 90 45 60 70 95 98 95 98 75 10 70 70 15 70 95 80 95 95 85 Surinam Grass 65 60 85 65 50 75 20 95 75 25 70 75 50 80 80 20 50 40 65 50 75 40 40 75 75 40 Velvetleaf 90 80 85 70 75 75 75 98 80 80 80 90 90 95 95 80 50 75 80 60 85 100 60 100 100 90 Wheat 0 0 0 0 0 10 20 5 15 10 5 5 0 0 5 0 5 0 0 0 35 15 15 0 40 10 Windgrass 30 0 5 40 50 60 60 80 5 30 10 25 50 45 60 0 0 25 45 10 50 50 40 60 45 20 31 g ai/ha Compounds 162 164 169 173 181 184 186 187 189 190 191 193 197 217 218 219 220 225 226 227 228 229 233 235 236 237 Barley 30 5 0 5 5 5 0 0 0 0 5 0 0 0 30 0 10 20 10 0 0 0 0 0 0 5 Bermudagrass 85 70 70 98 100 98 80 75 10 98 100 95 95 70 70 95 80 80 80 75 80 75 95 98 95 98 Blackgrass 30 5 5 5 0 30 0 0 0 5 30 10 0 0 0 50 10 0 5 0 5 0 5 45 0 50 Bromegrass, Downy 20 40 10 5 40 40 5 5 0 5 35 10 15 10 5 45 10 35 0 0 5 5 40 10 0 30 Canarygrass 40 40 40 10 50 45 5 10 0 0 20 5 5 0 0 35 10 60 5 0 0 5 0 20 0 30 Chickweed 90 80 100 65 100 100 95 100 98 — 98 95 100 75 100 100 95 25 75 65 98 70 90 98 75 90 Cocklebur 100 98 100 60 100 100 90 100 60 40 90 95 80 80 — — — 98 98 75 98 85 90 — — — Corn 50 15 45 5 70 80 10 50 20 0 65 0 15 0 0 10 25 40 75 20 80 70 30 95 15 85 Crabgrass, Large 80 95 85 70 98 100 80 85 75 60 85 75 75 80 40 90 70 75 85 80 80 80 80 98 75 95 Cupgrass, Woolly 90 75 85 85 80 75 70 80 70 75 85 75 70 25 40 85 60 75 80 55 75 70 80 95 70 100 Deadnettle — — — — — 100 90 80 85 65 90 100 100 — — — — — — — — — — — — — Foxtail, Giant 85 90 95 95 98 98 75 98 75 70 100 75 85 70 40 70 30 75 85 75 85 75 90 98 75 98 Foxtail, Green 98 70 60 55 70 30 50 65 65 25 40 40 5 55 60 70 60 85 70 50 85 40 85 90 80 80 Galium — — — — — 50 40 20 20 50 20 75 75 — — — — — — — — — — — — — Goosegrass 60 85 95 80 95 100 85 85 60 70 95 85 85 80 0 90 80 85 80 75 80 70 85 95 80 95 Johnsongrass 98 45 60 65 100 100 65 90 50 60 70 50 70 0 — — 60 60 85 45 75 70 0 70 0 100 Kochia 20 98 100 65 65 0 75 40 85 0 5 20 65 75 35 80 45 5 80 70 90 55 70 98 80 65 Lambsquarters 80 98 100 98 100 80 98 98 98 80 75 98 95 90 98 100 100 85 90 90 98 85 98 98 98 95 Morningglory 75 90 95 75 95 40 95 80 100 40 40 40 98 70 70 60 65 95 98 100 100 98 65 95 60 85 Nutsedge, Yellow 25 40 0 45 60 35 65 45 20 35 40 60 45 10 10 10 10 10 55 10 40 0 0 45 0 20 Oat, Wild 35 25 0 50 65 40 0 10 5 0 50 0 40 30 40 50 10 45 25 0 0 0 30 35 0 40 Pigweed 100 98 100 85 100 70 85 100 80 65 80 90 80 85 100 100 95 90 75 80 98 80 85 100 85 80 Ragweed 90 85 100 55 98 — 85 95 10 — — — — 80 95 80 90 75 80 60 70 80 80 98 80 95 Ryegrass, Italian 40 5 0 0 10 20 0 0 0 0 40 5 0 0 30 20 5 0 0 0 0 0 30 30 0 50 Soybean 98 80 90 60 100 98 85 98 90 80 90 80 98 75 85 95 80 85 95 55 95 95 98 98 90 95 Surinam Grass 65 60 — — 70 80 — 65 65 60 70 65 50 70 75 10 50 75 75 55 75 65 80 80 60 85 Velvetleaf 80 70 100 100 100 85 70 90 85 100 75 90 80 98 85 85 80 80 85 80 80 75 80 95 98 85 Wheat 10 0 0 10 40 30 0 0 0 0 35 30 0 30 0 40 0 30 10 0 0 0 10 45 0 50 Windgrass 40 5 15 30 40 60 10 10 25 15 55 50 10 50 10 35 5 50 10 0 5 0 50 85 30 60 31 g ai/ha Compounds 238 239 240 243 244 245 255 Barley 10 0 5 60 50 45 30 Bermudagrass 95 95 98 98 80 80 90 Blackgrass 40 5 40 60 50 40 5 Bromegrass, Downy 10 0 10 50 40 60 50 Canarygrass 20 0 5 90 80 80 50 Chickweed 80 90 90 80 80 80 95 Cocklebur — 90 — — — — — Corn 80 5 90 90 85 100 60 Crabgrass, Large 95 75 80 95 80 80 85 Cupgrass, Woolly 95 75 98 95 100 100 85 Deadnettle — — — — — — — Foxtail, Giant 100 75 100 95 95 98 95 Foxtail, Green 85 80 90 98 85 85 85 Galium — — — — — — — Goosegrass 95 80 95 95 85 98 90 Johnsongrass 60 0 — 100 85 100 80 Kochia 90 90 80 85 85 85 10 Lambsquarters 100 98 98 100 100 98 90 Morningglory — 95 — 95 90 90 75 Nutsedge, Yellow 20 30 10 65 45 40 10 Oat, Wild 30 0 25 80 50 70 65 Pigweed 100 95 — 85 95 80 80 Ragweed 100 95 98 90 98 95 50 Ryegrass, Italian 20 0 10 60 35 40 10 Soybean 98 70 95 95 85 95 95 Surinam Grass 95 25 95 90 90 100 80 Velvetleaf 80 100 75 100 100 100 95 Wheat 40 0 30 85 60 75 35 Windgrass 45 20 60 80 50 65 50 16 g ai/ha 8 g ai/ha Compounds Compound 2 69 122 131 159 169 225 159 Barley 0 0 0 0 20 0 5 0 Bermudagrass 40 85 65 60 80 70 40 70 Blackgrass 0 0 0 0 5 0 0 0 Bromegrass, Downy 20 30 5 0 15 0 30 15 Canarygrass 20 0 0 0 40 5 55 25 Chickweed 70 95 65 45 100 90 15 80 Cocklebur 75 0 0 80 80 100 85 75 Corn 15 0 0 0 25 20 10 15 Crabgrass, Large 70 95 65 65 75 75 70 65 Cupgrass, Woolly 75 75 65 10 65 75 70 60 Foxtail, Giant 70 80 65 65 80 75 75 75 Foxtail, Green 50 75 40 40 80 45 85 50 Goosegrass 80 75 10 65 80 80 80 70 Johnsongrass 75 75 20 0 45 40 20 10 Kochia 55 60 0 20 20 100 5 20 Lambsquarters 80 100 55 75 95 95 85 90 Morningglory 55 65 55 5 10 95 80 0 Nutsedge, Yellow 40 5 35 0 20 0 5 10 Oat, Wild 5 50 5 0 35 0 25 0 Pigweed 70 95 75 60 75 90 80 55 Ragweed 65 75 55 65 80 98 70 65 Ryegrass, Italian 0 0 5 0 0 0 0 0 Soybean 75 45 20 75 85 55 65 80 Surinam Grass 70 75 25 15 65 — 35 65 Velvetleaf — 75 75 70 100 75 80 98 Wheat 0 0 5 0 35 0 20 10 Windgrass 10 40 5 0 40 5 5 10 Preemergence 250 g ai/ha Compounds 3 7 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 Bermudagrass 90 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 Blackgrass 0 0 40 20 60 10 0 10 10 30 50 30 50 25 10 40 0 5 5 60 5 0 5 5 0 5 Bromegrass, Downy 0 0 10 0 5 0 0 20 10 30 5 30 80 10 0 40 0 10 0 5 5 0 10 45 — 0 Cocklebur 100 75 100 98 100 100 95 95 98 90 90 90 85 80 45 90 45 100 — 45 — 15 — 85 55 — Corn 5 0 10 0 35 75 10 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100 95 100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 Cupgrass, Woolly 10 45 60 40 75 85 70 90 85 80 90 85 100 65 70 80 10 85 5 85 75 60 90 95 20 70 Foxtail, Giant 0 25 98 45 100 100 90 100 90 95 100 98 100 80 75 95 75 98 10 98 75 25 100 98 45 90 Foxtail, Green 0 0 — 30 65 80 60 100 70 80 100 100 100 85 90 100 100 100 85 100 100 10 98 98 30 100 Galium 50 0 95 85 75 95 80 80 98 95 100 90 98 95 100 85 85 90 50 98 85 70 95 70 95 98 Goosegrass 98 60 100 98 100 100 100 100 100 100 100 98 100 100 100 100 100 100 100 100 100 98 100 100 100 100 Johnsongrass 10 0 98 75 98 98 95 90 90 85 90 20 100 85 90 95 75 90 65 95 85 70 100 98 10 95 Kochia 100 100 100 100 100 100 100 100 100 100 100 — — — — — — — — — — — — — — — Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 100 Morningglory 100 20 98 40 100 100 100 100 100 100 100 90 98 20 0 100 100 65 0 95 0 0 55 100 85 55 Nightshade 100 100 100 100 100 100 100 100 100 100 100 100 100 98 85 100 100 100 100 100 100 98 100 100 98 100 Nutsedge, Yellow 50 55 95 75 90 90 85 90 85 90 85 90 90 75 90 80 10 85 85 90 70 90 90 90 90 90 Oat, Wild 0 0 60 10 40 5 0 80 5 50 50 50 60 0 10 20 0 30 0 30 5 0 10 15 0 0 Pigweed 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 90 90 100 100 100 100 90 100 100 100 100 100 90 90 98 95 95 95 80 95 95 100 95 95 95 100 Russian Thistle — — — — — — — — — — — — — — — — — — — — — — — — — — Ryegrass, Italian 0 0 40 0 0 0 0 10 0 0 40 5 10 0 0 40 0 5 0 0 0 0 0 0 5 0 Soybean 50 30 80 75 95 95 85 85 90 90 95 75 80 40 35 75 0 70 0 0 0 25 0 20 85 0 Sunflower 85 25 98 98 98 100 98 98 95 100 100 90 90 85 90 75 65 80 75 80 75 60 85 80 75 85 Surinam Grass 5 10 95 80 75 100 80 100 90 95 95 100 90 100 100 80 15 90 75 100 98 90 100 100 85 100 Velvetleaf 100 100 100 100 100 100 100 100 100 95 100 100 100 100 98 100 98 100 90 100 95 65 100 100 100 100 Wheat 0 0 5 5 5 0 0 0 0 5 0 5 0 0 0 5 0 — 0 0 0 0 0 0 0 0 250 g ai/ha Compounds 51 52 53 55 56 58 59 61 62 63 64 66 67 68 72 73 74 75 77 81 113 119 120 193 217 218 Bermudagrass 100 100 100 100 100 100 98 98 100 98 98 98 100 100 100 100 100 100 100 100 100 100 100 98 100 100 Blackgrass 20 10 60 30 5 30 40 0 0 40 0 5 5 5 5 10 10 10 0 35 20 70 50 70 0 20 Bromegrass, Downy 40 5 30 0 5 0 0 0 0 0 0 0 0 5 0 20 0 0 0 0 10 55 85 50 0 0 Cocklebur 75 75 70 15 0 65 75 65 10 10 70 0 20 80 80 65 80 90 65 85 100 85 98 95 85 100 Corn 0 0 20 0 0 0 0 0 — 0 0 0 0 0 0 10 0 0 0 55 0 50 55 5 0 0 Crabgrass, Large 100 100 100 98 98 100 98 98 98 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 Cupgrass, Woolly 85 80 95 55 70 85 85 0 10 10 10 75 10 85 65 80 5 75 0 85 95 100 90 90 80 85 Foxtail, Giant 75 75 100 10 80 75 75 45 20 10 65 80 65 75 65 80 45 80 45 98 85 100 100 80 85 85 Foxtail, Green 100 100 98 0 100 100 98 75 10 30 50 75 40 85 90 80 0 98 15 100 100 100 100 98 90 100 Galium 95 95 90 85 85 80 98 98 0 20 70 0 90 85 85 85 98 98 90 100 95 100 98 100 90 100 Goosegrass 100 100 100 98 100 100 100 98 98 100 100 98 98 98 100 100 100 100 98 100 100 100 100 100 100 98 Johnsongrass 80 95 75 0 80 85 90 20 — 60 75 98 0 95 10 98 0 70 0 90 70 95 90 60 55 45 Kochia — — — — — — 98 — 100 100 95 85 85 95 85 90 85 95 95 70 90 98 75 90 — — Lambsquarters 98 100 100 100 98 98 100 — 100 100 98 100 98 100 100 100 100 100 100 98 100 100 100 100 100 100 Morningglory 70 55 65 65 65 75 60 65 20 55 0 80 80 85 75 70 80 90 90 95 — 95 100 95 0 65 Nightshade 100 100 100 100 100 100 100 — 98 98 98 98 98 100 100 100 100 100 100 100 100 100 98 100 100 100 Nutsedge, Yellow 90 90 90 65 90 90 90 90 — 90 10 95 75 90 90 85 90 90 90 95 90 98 98 90 90 90 Oat, Wild 0 60 70 0 0 30 0 0 0 0 5 40 0 5 0 65 5 0 0 0 40 80 65 60 0 0 Pigweed 100 100 100 100 100 100 100 — 100 100 98 98 98 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 90 95 90 90 80 90 95 90 60 85 85 55 50 90 85 85 100 95 95 90 98 95 95 100 95 100 Russian Thistle — — — — — — — — — — — — 90 98 80 — 98 — — 100 — 100 — 100 — — Ryegrass, Italian 5 0 50 0 0 0 20 5 20 0 0 5 0 0 0 5 0 0 0 0 40 100 100 45 10 5 Soybean 85 80 85 65 90 95 80 20 — 15 — — — — — — — — — — 90 80 80 80 0 90 Sunflower 75 75 65 70 75 75 80 70 55 70 55 10 55 85 80 75 85 85 85 90 95 85 95 95 85 95 Surinam Grass 100 98 100 45 98 95 95 35 60 85 90 100 75 85 98 100 95 75 100 100 98 100 100 45 90 100 Velvetleaf 100 100 100 100 98 95 100 100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 10 0 10 0 10 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 10 50 30 25 0 0 250 g ai/ha 125 g ai/ha Compounds Compounds 219 220 243 244 245 255 2 3 7 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 Bermudagrass 100 100 100 100 100 100 100 80 85 100 100 100 100 100 100 98 100 100 100 100 100 98 100 100 100 100 Blackgrass 60 35 95 70 45 60 50 0 0 20 0 30 5 0 0 0 10 50 10 50 25 5 30 0 0 0 Bromegrass, Downy 20 5 70 30 15 40 5 0 0 5 0 0 0 0 0 0 0 0 5 10 0 0 5 0 5 0 Cocklebur 85 0 98 100 100 — 80 70 0 65 65 95 98 85 95 85 85 90 85 75 — 0 25 — 85 — Corn 0 0 95 85 65 0 0 0 0 0 0 0 15 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100 100 100 100 100 100 100 85 45 100 70 100 100 100 100 100 100 100 100 100 100 10 100 100 100 95 Cupgrass, Woolly 80 25 100 100 100 90 20 0 0 45 35 15 75 50 85 50 60 55 60 100 10 10 60 0 70 0 Foxtail, Giant 80 75 95 100 100 98 70 0 0 60 0 75 70 75 90 45 85 100 95 90 65 0 80 70 80 10 Foxtail, Green 100 100 100 90 100 100 60 0 0 5 0 65 40 10 100 30 50 100 100 90 85 0 85 75 85 85 Galium 100 100 100 98 95 100 — 30 0 60 85 50 90 40 10 90 85 98 50 90 80 30 85 85 85 10 Goosegrass 100 100 100 100 100 100 100 85 45 100 95 100 100 98 100 95 100 100 90 100 95 80 100 100 100 100 Johnsongrass 80 80 100 100 100 98 80 0 0 90 60 85 75 80 90 60 50 30 0 98 80 45 85 65 85 10 Kochia — — 100 100 100 — 100 100 100 100 100 100 100 100 100 100 100 100 — — — — — — — — Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 100 90 100 100 100 90 75 100 0 70 0 35 85 100 100 100 100 100 70 75 0 0 0 15 0 0 Nightshade 100 100 98 100 100 100 100 98 95 100 100 100 100 100 100 100 100 100 100 100 95 80 98 100 98 100 Nutsedge, Yellow 90 90 95 95 80 90 70 40 15 80 55 85 75 40 85 50 30 60 70 75 40 20 70 0 65 75 Oat, Wild 40 60 90 40 30 90 50 0 0 0 0 10 0 0 0 0 30 45 30 30 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 98 95 98 100 100 100 98 90 15 100 100 100 100 90 98 95 100 100 100 90 85 65 80 75 90 25 Russian Thistle — — 100 — — — — — — — — — — — — — — — — — — — — — — — Ryegrass, Italian 10 0 70 45 40 30 5 0 0 0 0 0 0 0 10 0 0 10 5 5 0 0 5 0 5 0 Soybean 75 75 95 95 75 80 70 35 20 — 65 65 80 50 80 80 80 90 65 65 0 0 0 0 20 0 Sunflower 85 90 95 100 95 90 90 70 0 95 95 95 98 85 95 90 90 90 75 80 55 45 25 25 75 55 Surinam Grass 100 65 100 100 100 100 60 0 0 95 15 35 95 60 95 90 60 90 95 65 100 55 65 10 85 10 Velvetleaf 95 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 90 100 100 95 100 20 98 75 100 85 Wheat 0 5 70 45 15 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 125 g ai/ha Compounds 44 45 46 47 48 49 50 51 52 53 55 56 58 59 61 62 63 64 66 67 68 69 72 73 74 75 77 Bermudagrass 100 100 — 100 100 98 100 100 98 100 100 100 100 98 75 95 98 98 98 95 98 100 98 98 100 100 100 Blackgrass 40 0 0 5 0 0 0 10 0 5 0 0 5 30 0 0 5 0 5 0 0 0 0 0 0 5 0 Bromegrass, Downy 0 0 0 5 0 0 0 5 5 5 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 Cocklebur — — 0 — 0 45 75 20 10 65 10 0 10 10 20 0 0 10 0 15 — 10 70 60 70 75 10 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100 100 85 100 100 98 100 100 100 100 95 98 98 98 98 80 100 98 95 98 98 100 100 100 100 100 98 Cupgrass, Woolly 80 60 50 75 75 0 15 75 65 85 0 50 20 65 0 5 0 0 60 0 55 45 45 55 0 55 0 Foxtail, Giant 75 45 15 85 85 20 90 50 25 100 0 75 75 60 15 20 0 35 75 45 55 90 10 75 5 80 5 Foxtail, Green 98 80 5 98 98 5 95 98 45 98 0 20 70 90 40 10 — 0 30 — 25 85 50 30 0 50 0 Galium 65 50 0 50 60 90 95 80 70 0 20 60 30 95 98 0 0 30 0 85 70 0 85 80 40 95 85 Goosegrass 100 100 98 100 100 98 100 100 100 100 98 95 100 100 98 98 100 98 90 90 98 100 100 100 100 100 98 Johnsongrass 90 75 45 80 90 0 90 75 90 60 0 55 80 80 10 0 55 55 85 0 75 85 0 98 0 65 0 Kochia — — — — — — — — — — — — — 60 85 100 100 45 85 80 95 45 85 80 85 90 90 Lambsquarters 100 100 95 100 100 98 100 98 100 100 98 98 98 100 98 100 100 98 98 98 98 100 98 100 98 100 100 Morningglory 50 — 0 0 100 80 — 20 45 25 45 45 55 55 45 0 0 0 25 15 65 0 65 45 75 75 75 Nightshade 100 100 98 100 100 98 100 98 98 100 100 98 98 100 98 98 98 95 98 95 100 98 98 98 98 98 98 Nutsedge, Yellow 75 20 80 80 85 85 90 85 80 90 45 85 75 85 90 45 25 0 85 65 85 0 75 65 65 90 90 Oat, Wild 5 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 Pigweed 100 100 95 100 100 100 100 100 100 100 98 100 100 100 100 100 100 85 98 98 100 100 100 100 100 100 100 Ragweed 95 80 100 90 90 80 95 80 85 85 85 70 85 90 75 45 70 75 45 35 80 65 80 75 98 95 90 Russian Thistle — — — — — — — — — — — — — — — — — — — — 80 100 80 — 90 — — Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 20 5 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 0 0 15 0 0 85 — 80 55 80 15 80 85 0 0 80 5 — — — — — — — — — — Sunflower 75 10 0 80 80 75 85 75 70 65 60 65 65 70 60 10 20 0 0 35 75 5 65 70 70 75 75 Surinam Grass 90 98 75 100 100 75 98 98 95 100 0 98 85 85 0 25 55 85 90 15 55 100 75 100 85 60 75 Velvetleaf 100 85 55 90 100 100 100 98 98 98 100 98 95 100 98 95 100 95 95 90 100 85 100 100 100 100 100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 125 g ai/ha 62 g ai/ha Compounds Compounds 81 113 119 120 193 217 218 219 220 243 244 245 255 2 3 7 9 10 11 12 14 24 26 27 29 33 Bermudagrass 100 100 100 100 95 100 100 100 98 100 100 100 100 100 70 0 100 80 100 100 75 100 70 98 100 100 Blackgrass 35 0 50 50 30 0 0 40 20 70 60 30 40 0 0 0 0 0 5 0 0 0 0 0 5 0 Bromegrass, Downy 0 10 55 30 5 0 0 10 0 60 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 75 90 70 60 — 85 90 — — 95 100 98 — 65 10 0 25 15 75 80 85 — 40 85 80 80 Corn 50 0 50 25 5 0 0 0 0 85 60 25 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100 100 100 100 100 100 65 100 80 100 100 100 100 100 70 0 90 0 100 90 50 98 40 80 100 98 Cupgrass, Woolly 75 85 95 75 80 65 65 20 10 95 95 80 75 15 0 0 15 10 0 10 5 70 5 0 10 50 Foxtail, Giant 85 60 95 98 70 75 20 10 0 95 100 90 55 20 0 0 15 0 35 20 10 85 10 5 50 45 Foxtail, Green 100 60 100 100 50 0 80 90 — 100 90 75 80 5 0 0 0 0 25 0 0 40 0 30 40 45 Galium 100 85 90 95 100 70 95 98 90 98 98 95 60 — 5 0 40 10 50 50 0 0 50 50 80 10 Goosegrass 100 100 100 100 100 100 98 100 98 100 100 100 100 100 70 25 98 75 95 95 85 98 80 98 100 85 Johnsongrass 90 60 95 80 15 20 20 65 0 95 100 80 75 65 0 0 85 10 55 0 30 85 10 5 5 0 Kochia 65 85 55 50 80 — — — — 90 95 98 — 100 — 100 100 50 100 100 100 100 100 100 100 — Lambsquarters 98 100 100 100 100 100 100 100 100 100 100 100 100 100 — 100 100 100 100 100 100 100 100 100 100 100 Morningglory 80 — 95 90 95 0 15 15 0 98 98 65 65 20 100 0 40 0 0 55 100 100 100 100 100 15 Nightshade 98 100 98 95 100 100 100 100 98 98 100 100 100 100 — 90 100 100 100 100 98 98 100 98 90 100 Nutsedge, Yellow 95 90 98 98 70 70 90 85 60 90 80 65 40 40 10 10 45 0 55 60 30 50 50 20 30 45 Oat, Wild 0 20 50 65 30 0 0 5 0 85 10 30 60 5 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 — 100 100 100 100 100 98 100 100 100 100 100 Ragweed 90 95 95 95 100 90 98 85 80 98 100 100 85 85 65 0 90 100 100 98 90 90 85 85 90 85 Russian Thistle 100 — 100 80 100 — — — — 100 — — — — — — — — — — — — — — — — Ryegrass, Italian 0 5 100 100 25 5 5 5 0 45 5 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean — 85 80 80 60 0 80 65 0 85 90 55 15 60 30 0 10 60 45 65 — 60 60 70 85 60 Sunflower 85 90 70 85 80 85 90 80 70 95 85 80 75 70 70 0 85 80 85 98 85 90 90 75 85 75 Surinam Grass 100 95 100 100 30 85 98 45 45 100 100 100 95 20 0 0 45 10 25 60 5 75 5 20 20 65 Velvetleaf 100 100 100 100 100 100 90 90 90 100 100 100 98 90 90 85 100 100 100 100 98 100 90 85 90 90 Wheat 0 10 30 25 10 0 0 0 0 70 5 5 0 0 0 0 0 — 0 0 0 0 0 0 0 0 62 g ai/ha Compounds 34 36 37 38 39 40 42 44 45 46 47 48 49 50 51 52 53 55 56 58 59 61 62 63 64 66 67 Bermudagrass 100 100 80 100 100 100 100 100 100 — 100 100 — 100 98 98 100 98 100 98 98 75 75 98 85 80 90 Blackgrass 5 25 0 5 0 0 0 30 0 0 5 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 Bromegrass, Downy 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 55 — — 10 — — 0 — — 0 0 0 20 75 0 0 20 10 0 0 0 10 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 0 0 Crabgrass, Large 100 90 0 90 95 98 85 75 95 75 95 90 95 100 98 98 100 60 85 98 95 85 50 85 75 85 65 Cupgrass, Woolly 100 0 0 10 0 50 0 45 45 45 45 10 0 5 35 10 55 0 20 10 65 0 0 0 0 40 0 Foxtail, Giant 55 20 0 40 45 65 0 45 0 0 70 75 0 75 45 15 85 0 40 20 0 0 0 0 25 20 0 Foxtail, Green 70 80 0 30 — 85 65 98 80 0 80 60 0 50 50 30 60 0 20 5 70 0 0 — 0 5 30 Galium 50 80 10 40 80 70 0 65 40 0 50 60 80 95 75 0 0 0 0 0 90 70 0 0 0 0 35 Goosegrass 100 90 0 100 100 98 95 98 100 95 100 100 95 98 100 100 100 95 95 98 98 98 95 98 40 75 85 Johnsongrass 75 65 0 80 60 80 0 75 45 10 75 45 0 20 5 75 55 0 45 20 — 0 0 0 0 55 0 Kochia — — — — — — — — — — — — — — — — — — — — 45 70 100 100 0 80 70 Lambsquarters 100 100 98 98 100 100 100 100 100 90 100 100 95 100 98 100 100 98 98 98 100 98 98 98 98 98 98 Morningglory 0 0 0 0 0 0 0 0 — 0 — 100 80 0 20 0 20 0 0 0 0 0 0 0 0 20 15 Nightshade 95 95 40 95 100 98 100 98 100 95 100 100 98 100 98 95 98 98 98 98 98 95 95 95 85 95 95 Nutsedge, Yellow 45 0 0 60 0 45 35 60 10 55 45 20 60 85 70 25 80 45 80 75 65 70 25 15 0 30 65 Oat, Wild 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 98 95 85 100 100 100 100 100 100 98 95 100 98 100 100 98 98 75 98 98 Ragweed 80 75 10 70 45 75 20 90 80 100 80 85 75 95 70 80 75 65 65 75 90 75 20 65 50 0 25 Russian Thistle — — — — — — — — — — — — — — — — — — — — — — — — 0 0 — Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 45 0 0 0 0 0 0 0 0 0 0 0 80 0 0 0 70 0 — — 0 0 80 0 — — — Sunflower 70 0 0 0 5 55 0 70 0 0 65 75 75 75 70 10 55 60 60 55 65 45 10 15 0 0 20 Surinam Grass 60 95 45 60 10 75 5 85 60 5 98 90 — 95 98 25 85 0 95 65 75 0 20 0 85 80 10 Velvetleaf 85 85 0 60 45 85 80 90 65 45 90 95 100 85 85 98 98 98 90 80 90 85 75 90 75 80 85 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 62 g ai/ha 31 g ai/ha Compounds Compounds 68 69 72 73 74 75 77 81 113 119 120 193 217 218 219 220 243 244 245 255 2 3 7 9 10 11 Bermudagrass 98 100 98 98 98 100 100 100 95 100 100 95 100 100 100 98 100 100 100 100 98 10 0 98 45 98 Blackgrass 0 0 0 0 0 0 0 0 0 30 50 0 0 0 35 20 10 35 5 20 0 0 0 0 0 0 Bromegrass, Downy 0 0 0 5 0 0 0 0 10 50 30 5 0 0 0 0 40 0 0 0 0 0 0 0 0 0 Cocklebur 10 0 50 0 45 20 0 10 75 — 35 75 — 0 75 0 75 90 0 — 0 10 0 0 0 35 Corn 0 0 0 0 0 0 0 40 0 40 — 0 0 0 0 0 75 25 5 0 0 0 0 0 0 0 Crabgrass, Large 95 100 100 98 98 100 98 100 98 100 100 100 100 20 98 75 100 100 100 95 15 0 0 0 0 60 Cupgrass, Woolly 20 0 0 20 0 — 0 55 50 75 70 70 5 0 10 0 95 55 70 10 0 0 0 0 0 0 Foxtail, Giant 20 75 5 70 0 25 0 75 40 85 98 65 40 0 0 0 85 80 10 45 15 0 0 0 0 0 Foxtail, Green 5 70 0 30 0 50 0 90 40 100 98 50 0 30 70 90 100 45 0 80 0 0 0 0 0 0 Galium 70 — 85 30 30 85 20 100 70 85 90 100 10 80 85 50 90 65 60 50 — 0 0 0 0 5 Goosegrass 95 100 98 98 98 100 95 98 90 100 100 100 98 60 100 95 100 100 100 98 85 30 10 75 0 70 Johnsongrass 5 45 0 0 0 10 0 80 5 85 70 0 5 0 15 0 95 85 75 60 60 0 0 0 0 0 Kochia 80 20 75 — — 90 90 55 80 0 20 70 — — — — 20 90 45 — 100 98 15 15 0 15 Lambsquarters 98 100 98 98 98 100 98 98 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 55 0 55 0 60 60 65 65 — 95 90 90 0 0 0 0 — 90 0 55 0 100 — 0 0 0 Nightshade 98 98 95 95 98 98 98 98 98 98 95 100 100 98 98 90 98 100 100 90 98 50 80 100 100 85 Nutsedge, Yellow 70 0 70 65 55 80 80 75 80 95 90 65 65 75 45 0 80 60 0 25 15 5 0 0 0 0 Oat, Wild 0 0 0 0 0 0 0 0 5 45 10 5 0 0 0 0 85 5 0 0 — 0 0 0 0 0 Pigweed 98 100 98 100 98 100 100 100 98 90 100 100 100 100 100 100 98 100 95 100 100 85 100 50 100 100 Ragweed 75 65 70 60 98 75 75 85 90 80 80 100 60 95 75 60 95 95 85 75 60 65 0 55 98 65 Russian Thistle — 100 30 — 80 — — 100 — 100 80 98 — — — — 100 — — — — — — — — — Ryegrass, Italian 0 0 0 0 0 0 0 0 5 100 100 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 Soybean — — — — — — — — 65 55 70 60 0 65 0 0 75 80 10 0 15 0 0 0 10 25 Sunflower 60 0 25 20 55 55 75 75 80 60 — 80 75 80 45 45 85 80 70 60 50 50 0 45 0 75 Surinam Grass 50 100 75 100 80 60 20 100 80 98 100 15 75 65 10 20 98 100 100 85 15 0 0 0 0 0 Velvetleaf 100 70 100 100 100 100 100 100 100 80 100 100 100 85 75 70 100 100 100 95 75 50 40 98 55 100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 0 0 0 0 0 0 0 31 g ai/ha Compounds 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 51 52 53 55 56 58 59 Bermudagrass 100 70 95 5 70 98 98 100 95 10 98 85 98 90 100 98 0 100 100 — 100 95 98 — 95 98 98 10 Blackgrass 0 0 0 0 0 5 0 0 20 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Bromegrass, Downy 0 0 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 25 0 10 10 0 5 25 0 — 0 0 0 65 0 — — 0 — — 0 — 0 0 10 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 0 5 90 0 5 98 85 55 20 0 60 55 70 45 65 45 45 75 75 75 98 75 60 75 10 80 95 55 Cupgrass, Woolly 0 0 5 0 0 5 10 100 0 0 0 0 0 0 0 45 10 0 10 0 0 10 0 0 0 0 10 10 Foxtail, Giant 0 0 30 5 0 10 10 15 10 0 0 0 10 0 20 0 0 45 20 0 45 0 0 5 0 0 10 0 Foxtail, Green 0 0 0 0 0 0 0 50 35 0 20 — 0 65 0 0 0 65 60 0 50 50 0 60 0 0 0 — Galium 0 0 0 0 0 50 0 10 10 0 0 70 50 0 0 40 0 50 0 0 70 0 0 0 0 0 0 0 Goosegrass 85 70 85 5 80 95 80 95 0 0 95 85 80 50 90 80 85 95 98 20 95 98 98 98 45 90 95 98 Johnsongrass 0 5 20 0 0 0 0 20 0 0 10 0 10 0 10 0 0 65 20 0 0 0 10 10 0 10 10 — Kochia 15 85 100 80 100 98 — — — — — — — — — — — — — — — — — — — — — 0 Lambsquarters 100 100 98 98 100 100 98 100 98 95 98 100 100 100 100 100 90 100 100 95 100 95 98 98 95 95 85 98 Morningglory 40 100 100 100 100 100 0 0 0 0 0 0 0 0 0 0 0 0 0 45 0 0 0 0 0 0 0 — Nightshade 100 85 90 85 80 90 80 55 80 0 90 50 65 100 95 98 95 100 100 98 100 98 90 98 60 85 90 95 Nutsedge, Yellow 25 0 30 10 0 0 0 10 0 0 10 0 10 10 45 0 25 45 20 60 80 55 0 65 0 20 20 55 Oat, Wild 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 90 98 98 100 100 100 100 100 100 100 90 98 100 98 85 85 98 100 100 90 100 90 95 45 98 85 90 Ragweed 90 70 85 65 85 80 80 75 35 0 40 0 75 0 20 45 100 45 65 70 75 65 80 65 55 20 20 75 Russian Thistle — — — — — — — — — — — — — — — — — — — — — — — — — — — — Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 60 25 45 50 70 20 60 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 10 — Sunflower 95 50 85 60 75 75 65 55 0 0 0 0 20 0 10 0 0 65 0 60 55 20 10 15 10 0 0 55 Surinam Grass 35 0 65 0 0 0 0 5 70 0 40 0 40 0 65 45 0 85 80 0 75 95 10 75 0 55 40 5 Velvetleaf 90 70 98 50 55 10 80 75 65 0 55 15 80 75 75 0 0 80 75 95 85 75 80 80 75 85 75 75 Wheat 0 0 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 31 g ai/ha Compounds 61 62 63 64 66 67 68 69 72 73 74 75 77 81 113 119 120 193 217 218 219 220 243 244 245 255 Bermudagrass 20 20 75 50 20 45 95 98 95 50 — 98 55 100 95 100 100 75 98 98 98 80 100 100 98 100 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 5 0 0 0 30 10 0 35 0 0 Bromegrass, Downy 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 10 0 10 10 0 0 45 0 0 — — — — 0 — — 0 — Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 0 0 0 0 0 0 65 5 0 0 Crabgrass, Large 70 0 50 50 70 40 65 98 95 85 98 98 70 100 70 100 98 100 95 0 10 0 100 98 60 80 Cupgrass, Woolly 0 0 0 0 25 0 5 0 0 10 0 5 0 40 5 65 50 10 0 0 0 0 75 45 50 0 Foxtail, Giant 0 0 0 20 15 0 0 5 0 0 0 0 0 60 5 55 75 0 5 0 0 0 55 60 0 15 Foxtail, Green 0 0 0 0 0 0 0 — 0 0 0 5 0 80 10 95 95 5 0 0 20 80 35 0 0 0 Galium 70 0 0 0 0 0 0 — 0 — 20 60 0 85 50 65 80 75 0 60 75 0 85 55 20 0 Goosegrass 80 15 90 30 35 85 80 95 60 85 98 95 55 98 75 100 100 98 95 10 98 65 98 98 95 80 Johnsongrass 0 0 0 0 0 0 0 5 0 0 0 0 0 10 0 50 35 0 0 0 0 0 70 70 65 0 Kochia 0 98 0 0 80 70 80 0 45 0 80 80 85 45 80 0 0 20 — — — — 15 85 0 — Lambsquarters 90 98 98 95 98 98 98 98 98 95 98 98 98 98 98 95 100 100 95 100 100 100 100 100 100 98 Morningglory 0 0 0 0 0 0 0 0 0 0 10 0 0 — — 60 0 75 0 0 0 0 — 85 0 40 Nightshade 90 10 80 55 80 70 98 95 95 75 85 95 98 98 98 90 90 100 95 98 90 65 90 98 98 75 Nutsedge, Yellow 25 15 10 0 10 0 0 0 40 20 20 60 75 10 65 75 70 10 60 45 0 0 65 20 0 10 Oat, Wild 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 — 30 0 0 0 Pigweed 0 45 95 55 98 98 95 98 98 95 98 98 100 100 98 80 95 98 95 100 100 100 75 100 80 100 Ragweed 50 0 65 0 0 25 10 65 55 45 10 75 50 60 55 80 80 100 60 85 45 15 85 70 75 65 Russian Thistle — — — — — 85 — 100 0 0 0 — — 100 — 100 — 90 — — — — 100 — — — Ryegrass, Italian — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 100 0 0 0 0 0 0 0 0 0 Soybean — 0 0 — — — — — — — — — — — 0 10 15 40 0 0 0 — 65 70 0 0 Sunflower 0 0 5 0 0 0 0 0 25 0 0 30 60 60 75 40 45 70 70 75 0 0 80 80 45 45 Surinam Grass 0 5 0 0 35 0 45 80 45 85 0 40 0 98 0 90 100 0 45 10 10 10 80 75 95 65 Velvetleaf 80 75 75 65 80 75 95 70 98 100 98 100 95 100 80 75 80 85 95 80 0 45 100 100 95 80 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 16 g ai/ha Compounds 2 69 Bermudagrass 25 90 Blackgrass 0 0 Bromegrass, Downy 0 0 Cocklebur 0 0 Corn 0 0 Crabgrass, Large 0 75 Cupgrass, Woolly 0 0 Foxtail, Giant 0 0 Foxtail, Green 0 — Goosegrass 0 55 Johnsongrass 0 0 Kochia 0 — Lambsquarters 100 95 Morningglory 0 0 Nightshade 55 80 Nutsedge, Yellow 0 0 Oat, Wild 0 0 Pigweed 98 95 Ragweed 25 40 Russian Thistle — 100 Ryegrass, Italian 0 — Soybean 0 — Sunflower 0 0 Surinam Grass 0 75 Velvetleaf 0 0 Wheat 0 0

›Test C

Seeds of plant species selected from bluegrass (annual bluegrass, Poa annua ), blackgrass ( Alopecurus myosuroides ), canarygrass ( Phalaris minor ), chickweed (common chickweed, Stellaria media ), galium (catchweed bedstraw, Galium aparine ), bromegrass (downy bromegrass, Bromus tectorum ), field poppy ( Papaver rhoeas ), field violet (Viola arvensis ), green foxtail ( Setaria viridis ), deadnettle (henbit deadnettle, Lamium amplexicaule ), Italian ryegrass ( Lolium multiflorum ), kochia ( Kochia scoparia ), lambsquarters ( Chenopodium album ), oilseed rape ( Brassica napus ), pigweed ( Amaranthus retroflexus ), Russian thistle ( Salsola iberica ), spring barley ( Hordeum vulgare ), spring wheat ( Triticum aestivum ), buckwheat (wild buckwheat, Polygonum convolvulus ), wild mustard ( Sinapis arvensis ), wild oat ( Avena fatua ), wild radish ( Raphanus raphanistrum ), windgrass ( Apera spica - venti ), winter barley ( Hordeum vulgare ), and winter wheat ( Triticum aestivum ) were planted and treated postemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage).

Treated plants and controls were maintained in a controlled growth environment for 14 days after which time all test plants were visually evaluated and compared to controls. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

›Test D

Seeds of plant species selected from bermudagrass ( Cynodon dactylon ), Surinam grass ( Brachiaria decumbens ), large crabgrass ( Digitaria sanguinalis ), green foxtail ( Setaria viridis ), goosegrass ( Eleusine indica ), j ohnsongrass ( Sorghum halepense ), kochia ( Kochia scoparia ), morningglory (pitted morningglory, Ipomoea lacunosa ), nutsedge (purple nutsedge, Cyperus rotundus ), ragweed (common ragweed, Ambrosia elatior ), black mustard ( Brassica nigra ), guineagrass ( Panicum maximum ), dallisgrass ( Paspalum dilatatum ), barnyardgrass ( Echinochloa crus - galli ), sandbur (southern sandbur, Cenchrus echinatus ), sowthistle (common sowthistle, Sonchus oleraceous ), prickly sida ( Sida spinosa ), Italian ryegrass ( Lolium multiflorum ), purslane (common purslane, Portulaca oleracea ), signalgrass (broadleaf signalgrass, Brachiaria platyphylla ), groundsel (common groundsel, Senecio vulgaris ), chickweed (common chickweed, Stellaria media ), dayflower (Virginia (VA) dayflower, Commelina virginica ), bluegrass (annual bluegrass, Poa annua ), naked crabgrass ( Digitaria nuda ), itchgrass ( Rottboellia cochinchinensis ), quackgrass ( Elytrigia repens ), field bindweed ( Convolvulus arvensis ), spanishneedles ( Bidens bipinnata ), mallow (common mallow, Malva sylvestris ) and Russian thistle ( Salsola kali ), were planted into a blend of loam soil and sand and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants from these weed species were treated with postemergence applications of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse for 14 to 21 days, after which time all species were visually evaluated and compared to controls. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE D Postemergence 250 g ai/ha Compounds 226 235 238 240 243 244 245 Barnyardgrass 95 95 95 95 90 90 90 Bermudagrass 98 95 95 95 95 95 80 Black Mustard 85 98 98 98 98 98 98 Bluegrass 30 50 40 35 35 20 35 Chickweed 85 70 50 70 70 60 50 Crabgrass, Large 85 80 80 70 85 75 75 Crabgrass, Naked 75 — — — — — — Dallisgrass 35 80 75 75 90 80 85 Dayflower, VA 65 75 75 75 75 70 75 Field Bindweed 80 70 50 70 70 70 70 Foxtail, Green 98 98 95 98 98 100 95 Goosegrass 75 75 75 80 75 70 75 Groundsel 100 100 100 100 100 100 100 Guineagrass 80 75 75 80 85 75 85 Itchgrass 90 90 80 80 85 75 75 Johnsongrass 90 85 80 95 75 75 75 Kochia 70 85 75 70 75 65 75 Mallow 65 70 60 60 70 70 70 Morningglory 80 95 90 95 85 75 80 Nutsedge, Purple 5 40 20 20 50 35 20 Prickly Sida 75 75 65 75 80 60 70 Purslane 70 70 60 50 50 50 30 Quackgrass 35 70 40 50 75 65 65 Ragweed 98 80 75 90 75 85 75 Russian Thistle 70 60 50 35 60 65 70 Ryegrass, Italian 15 35 5 35 65 60 50 Sandbur 75 75 85 90 80 75 75 Signalgrass 65 95 65 85 95 35 75 Sowthistle 98 98 95 98 98 100 95 Spanishneedles 80 85 75 75 70 75 75 Surinam Grass 90 85 85 95 85 80 75 125 g ai/ha Compounds 47 51 52 59 66 85 87 113 128 226 228 233 235 238 Barnyardgrass 70 70 80 75 75 70 70 80 90 95 80 85 95 85 Bermudagrass 90 85 80 80 65 90 85 80 90 95 70 70 95 95 Black Mustard 100 100 98 98 98 85 100 100 95 80 50 100 98 98 Bluegrass 0 0 35 5 0 5 0 0 0 10 5 0 35 20 Chickweed 65 70 100 — 95 100 100 — 70 35 75 60 60 40 Crabgrass, Large 65 35 70 70 35 75 75 70 70 75 75 60 75 75 Crabgrass, Naked 65 65 95 70 70 80 75 75 75 70 — 70 — — Dallisgrass 15 70 75 50 60 80 75 70 60 30 5 35 80 70 Dayflower, VA 30 20 60 — 30 80 70 60 70 — 85 60 75 70 Field Bindweed 65 60 70 60 0 75 40 — 65 70 70 70 65 — Foxtail, Green 95 65 95 35 80 65 60 90 70 80 80 35 98 80 Goosegrass 65 65 80 65 75 75 65 65 70 70 70 65 75 75 Groundsel 100 100 100 100 80 100 100 100 100 95 100 100 100 100 Guineagrass 30 50 75 20 30 60 30 70 35 80 15 50 75 65 Itchgrass 10 80 65 75 40 70 30 70 65 70 65 80 80 75 Johnsongrass 65 70 — 60 60 80 60 75 65 80 70 50 85 75 Kochia 30 20 40 50 40 60 60 50 40 70 75 35 70 65 Mallow 65 20 75 40 60 75 70 20 40 50 65 0 70 50 Morningglory 50 65 70 50 90 90 50 90 70 70 50 70 95 80 Nutsedge, Purple 20 20 40 25 30 65 50 50 50 0 15 0 30 20 Prickly Sida 90 75 90 70 98 98 95 70 80 70 65 60 70 50 Purslane 30 35 75 50 75 90 35 75 50 65 35 40 60 60 Quackgrass 5 0 20 0 5 20 5 30 5 20 5 25 40 30 Ragweed 95 85 95 80 5 100 98 80 90 90 75 98 80 75 Russian Thistle — — — 65 — — 35 20 — 40 65 10 50 50 Ryegrass, Italian 30 0 35 5 15 20 5 50 5 0 5 5 5 5 Sandbur 35 60 80 25 90 95 35 60 35 75 5 75 75 75 Signalgrass 20 50 90 20 30 75 60 75 35 65 20 35 90 60 Sowthistle 100 100 100 100 90 100 100 100 100 98 98 100 98 95 Spanishneedles 70 70 80 70 80 95 70 60 65 75 70 60 80 70 Surinam Grass 70 80 90 60 90 85 40 — 50 90 70 60 75 75 25 g ai/ha Compounds 240 243 244 245 Barnyardgrass 95 80 85 85 Bermudagrass 95 95 95 80 Black Mustard 98 98 95 98 Bluegrass 35 35 10 35 Chickweed 60 60 40 50 Crabgrass, Large 65 85 75 75 Crabgrass, Naked — — — — Dallisgrass 75 90 75 80 Dayflower, VA 70 70 65 65 Field Bindweed 70 70 65 60 Foxtail, Green 98 90 95 95 Goosegrass 80 70 70 70 Groundsel 100 100 100 100 Guineagrass 80 75 75 75 Itchgrass 80 75 75 75 Johnsongrass 95 70 75 75 Kochia 65 70 50 70 Mallow 60 70 60 50 Morningglory 90 85 75 80 Nutsedge, Purple 5 25 10 5 Prickly Sida 75 70 40 50 Purslane — 50 50 30 Quackgrass 35 70 50 40 Ragweed 80 75 80 75 Russian Thistle — 30 60 60 Ryegrass, Italian 35 30 35 20 Sandbur 90 75 75 75 Signalgrass 75 75 25 50 Sowthistle 98 95 100 95 Spanishneedles 75 70 75 70 Surinam Grass 95 75 80 75 62 g ai/ha Compounds 47 51 52 59 66 85 87 113 128 226 233 235 238 240 Barnyardgrass 70 70 75 60 70 65 60 80 70 85 85 80 80 95 Bermudagrass 70 80 75 70 65 80 70 80 80 95 70 95 90 95 Black Mustard 100 — 98 65 50 75 100 100 95 80 50 80 95 80 Bluegrass 0 0 35 0 0 5 0 0 0 10 0 20 5 35 Chickweed — — 98 70 35 100 75 — 65 35 — 30 35 50 Crabgrass, Large 60 35 70 50 25 75 70 70 60 75 50 75 70 65 Crabgrass, Naked 35 — 95 50 65 75 70 70 70 65 60 — — — Dallisgrass 15 30 70 20 35 65 50 60 30 20 10 75 65 70 Dayflower, VA 20 10 30 60 0 60 60 60 60 50 35 70 65 60 Field Bindweed 50 20 70 30 0 75 25 65 65 70 50 65 50 70 Foxtail, Green 50 40 85 20 65 35 35 70 65 70 30 95 80 98 Goosegrass 65 65 75 50 65 75 65 65 65 70 60 75 70 70 Groundsel 100 100 100 100 80 100 100 100 100 90 90 100 100 100 Guineagrass 20 30 75 20 10 35 20 50 30 80 40 75 50 65 Itchgrass 5 40 65 15 35 65 30 65 40 70 70 75 70 75 Johnsongrass 35 60 85 40 50 80 40 65 50 80 50 70 70 90 Kochia 20 5 0 20 25 20 35 50 30 60 30 60 50 65 Mallow 65 0 65 5 60 70 70 0 40 50 0 50 35 40 Morningglory — 20 70 50 90 75 40 90 70 70 70 75 80 80 Nutsedge, Purple 10 15 35 20 20 50 20 35 35 0 0 5 10 5 Prickly Sida 80 65 80 70 98 95 80 70 65 65 50 65 30 65 Purslane 30 35 65 35 75 90 35 50 30 50 30 60 60 35 Quackgrass 0 0 15 0 5 15 0 20 0 0 10 30 5 30 Ragweed 80 80 95 — 0 80 95 75 90 90 75 70 75 75 Russian Thistle 20 — — — — — — 20 20 — — 30 40 35 Ryegrass, Italian 20 0 15 5 0 15 0 35 0 0 5 5 5 35 Sandbur 20 25 75 5 35 65 20 60 5 75 70 75 75 70 Signalgrass 15 50 80 10 30 60 60 60 35 40 25 90 35 75 Sowthistle 100 100 98 100 70 100 98 100 100 98 — 98 95 98 Spanishneedles 65 60 80 70 80 90 60 50 50 75 50 70 70 65 Surinam Grass 60 70 80 50 90 75 40 80 30 70 50 75 75 70 62 g ai/ha Compounds 243 244 245 Barnyardgrass 80 80 85 Bermudagrass 85 80 80 Black Mustard 75 75 95 Bluegrass 5 10 20 Chickweed 50 20 25 Crabgrass, Large 80 75 70 Crabgrass, Naked — — — Dallisgrass 80 75 75 Dayflower, VA 65 50 35 Field Bindweed 70 35 50 Foxtail, Green 85 90 90 Goosegrass 70 60 70 Groundsel 100 100 100 Guineagrass 75 75 75 Itchgrass 75 70 70 Johnsongrass 70 70 75 Kochia 60 50 65 Mallow 60 50 50 Morningglory 85 70 75 Nutsedge, Purple 25 0 5 Prickly Sida 65 35 50 Purslane 50 50 5 Quackgrass 40 40 35 Ragweed 70 70 75 Russian Thistle 30 40 60 Ryegrass, Italian 20 15 5 Sandbur 75 70 70 Signalgrass 75 20 40 Sowthistle 90 95 95 Spanishneedles 65 65 70 Surinam Grass 75 75 75 31 g ai/ha Compounds 47 51 52 59 66 85 87 113 128 226 228 233 235 238 Barnyardgrass 70 70 75 60 65 50 50 75 70 85 20 75 80 75 Bermudagrass 50 75 75 40 50 75 65 70 70 90 70 70 80 80 Black Mustard 100 95 90 40 20 60 65 — 95 65 20 50 80 80 Bluegrass 0 0 25 0 0 0 0 0 0 0 0 0 5 0 Chickweed 65 — 90 70 — 80 75 70 — 20 35 50 5 30 Crabgrass, Large 50 35 70 35 25 60 65 60 50 65 65 40 70 50 Crabgrass, Naked 35 50 75 30 50 50 60 65 65 60 — 50 — — Dallisgrass 10 20 65 10 35 25 25 10 20 15 0 10 70 10 Dayflower, VA 15 10 5 — 0 30 35 40 50 50 35 35 60 35 Field Bindweed 40 5 70 5 0 75 15 65 50 70 65 50 60 35 Foxtail, Green 35 20 70 5 35 25 30 60 40 65 70 10 70 75 Goosegrass 65 65 75 20 50 65 35 50 40 70 50 50 75 50 Groundsel 100 98 100 90 60 100 98 90 100 80 100 50 100 100 Guineagrass 20 30 70 10 5 20 20 25 30 80 0 30 75 25 Itchgrass 5 20 50 15 15 35 0 10 40 50 40 65 70 70 Johnsongrass 15 35 75 35 20 50 30 40 40 50 65 35 70 60 Kochia 10 5 0 5 25 10 35 40 30 60 65 20 20 20 Mallow 50 0 65 5 30 65 60 0 5 35 40 0 10 25 Morningglory 5 20 65 40 70 70 40 60 65 50 50 60 75 70 Nutsedge, Purple 0 0 20 0 5 30 10 10 10 0 5 0 5 5 Prickly Sida 70 50 65 40 98 95 80 60 60 40 40 50 65 30 Purslane 20 20 65 35 50 80 25 30 30 50 — 30 60 60 Quackgrass 0 0 10 0 5 0 0 0 0 0 0 0 5 5 Ragweed 75 75 95 70 0 80 80 70 75 80 75 75 70 70 Russian Thistle — — — — — — — 0 0 — 20 — 30 30 Ryegrass, Italian 10 0 0 0 0 0 0 20 0 0 0 0 5 5 Sandbur 5 25 65 5 35 50 5 10 5 60 5 65 75 50 Signalgrass 5 35 60 5 10 35 30 40 30 35 15 5 65 20 Sowthistle 100 98 95 100 65 100 98 95 100 90 95 100 98 95 Spanishneedles 40 50 75 50 70 75 60 35 50 70 65 35 65 65 Surinam Grass 50 60 65 35 60 75 40 75 25 65 5 — 75 75 31 g ai/ha Compounds 240 243 244 245 Barnyardgrass 80 75 80 80 Bermudagrass 85 75 80 80 Black Mustard 70 50 50 75 Bluegrass 5 5 0 5 Chickweed 25 35 15 5 Crabgrass, Large 40 75 70 70 Crabgrass, Naked — — — — Dallisgrass 5 75 40 65 Dayflower, VA 35 35 30 20 Field Bindweed 60 65 20 50 Foxtail, Green 95 80 75 85 Goosegrass 70 65 50 70 Groundsel 100 98 100 95 Guineagrass 40 70 70 75 Itchgrass 75 75 60 70 Johnsongrass 70 70 70 70 Kochia 20 50 25 50 Mallow 10 50 50 35 Morningglory 65 75 65 70 Nutsedge, Purple 0 20 0 5 Prickly Sida 35 60 25 30 Purslane 0 35 25 0 Quackgrass 25 35 20 20 Ragweed 70 65 65 70 Russian Thistle 35 20 20 25 Ryegrass, Italian 0 0 5 5 Sandbur 70 75 70 65 Signalgrass 20 50 20 10 Sowthistle 98 90 75 95 Spanishneedles 65 60 65 65 Surinam Grass 70 75 75 75 16 g ai/ha Compounds 47 51 52 59 66 85 87 113 128 233 Barnyardgrass 70 65 75 40 35 30 35 65 35 65 Bermudagrass 50 65 75 35 5 65 65 65 70 70 Black Mustard 95 70 65 10 0 35 40 100 95 20 Bluegrass 0 0 15 0 0 0 0 0 0 0 Chickweed 50 — 75 — — — 75 — 60 — Crabgrass, Large 20 25 65 35 20 60 40 60 40 20 Crabgrass, Naked 20 35 70 20 — — 50 50 35 30 Dallisgrass 5 20 60 10 35 15 25 10 10 0 Dayflower, VA 10 10 5 25 0 20 10 20 50 15 Field Bindweed 35 5 50 5 0 65 0 50 50 10 Foxtail, Green 5 10 70 0 20 20 5 25 25 5 Goosegrass 40 35 65 20 50 40 30 40 35 40 Groundsel 100 85 100 70 — 100 98 90 100 30 Guineagrass 10 20 50 10 5 10 10 25 20 20 Itchgrass 0 0 25 0 10 30 0 0 0 50 Johnsongrass 5 20 65 30 0 35 20 40 35 20 Kochia 0 5 0 5 — 0 25 25 20 10 Mallow 35 0 50 0 25 60 40 0 5 0 Morningglory 5 0 50 0 65 70 40 50 65 50 Nutsedge, Purple 0 0 0 0 0 5 0 0 0 0 Prickly Sida 60 50 65 40 — — 70 50 50 30 Purslane 20 10 65 35 — 75 10 30 30 30 Quackgrass 0 0 5 0 0 0 0 0 0 0 Ragweed 75 60 90 70 0 80 70 70 — 65 Russian Thistle 20 0 — — — — — 0 0 0 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 Sandbur 5 5 65 5 — 10 5 5 5 30 Signalgrass 0 5 50 5 0 20 20 5 0 0 Sowthistle 90 95 80 70 35 100 90 90 100 90 Spanishneedles 35 35 75 30 65 75 60 35 35 35 Surinam Grass 35 50 — 30 — — 30 60 — 30 Preemergence 250 g ai/ha Compound 243 Barnyardgrass 100 Bermudagrass 100 Black Mustard 100 Bluegrass 100 Crabgrass, Large 100 Crabgrass, Naked 100 Dallisgrass 100 Dayflower, VA 100 Field Bindweed 100 Foxtail, Green 100 Goosegrass 100 Guineagrass 100 Itchgrass 100 Johnsongrass 100 Kochia 100 Mallow 98 Morningglory 100 Nutsedge, Purple 100 Prickly Sida 100 Purslane 100 Quackgrass 98 Ragweed 100 Russian Thistle 100 Ryegrass, Italian 100 Sandbur 100 Signalgrass 100 Spanishneedles 100 Surinam Grass 100 Compounds 47 51 52 59 66 85 87 113 128 233 243 125 g ai/ha Barnyardgrass 5 10 10 10 75 98 95 35 15 40 100 Bermudagrass 100 30 100 90 5 100 98 85 75 85 100 Black Mustard 100 100 100 100 80 100 100 100 95 65 100 Bluegrass 35 0 20 30 0 15 35 0 25 40 95 Chickweed — — 95 — 98 100 — — — — — Crabgrass, Large 95 5 98 65 98 100 100 95 — 90 100 Crabgrass, Naked 98 0 80 95 25 98 100 100 75 65 100 Dallisgrass 75 90 95 75 95 98 98 100 98 35 100 Dayflower, VA 50 0 40 35 5 95 65 65 25 100 100 Field Bindweed 35 0 50 60 20 98 70 90 98 85 100 Foxtail, Green 0 0 15 0 5 70 10 20 0 0 100 Goosegrass 75 40 98 80 50 98 100 95 90 100 100 Guineagrass 0 75 — 0 65 75 75 100 0 0 100 Itchgrass 0 0 5 20 0 50 20 0 20 20 50 Johnsongrass 75 70 95 35 30 95 70 10 65 65 100 Kochia 100 50 35 0 90 95 100 100 50 80 100 Mallow 98 65 — 65 75 98 100 90 100 60 80 Morningglory 65 100 100 80 95 100 95 90 90 95 98 Nutsedge, Purple 35 5 40 80 70 95 75 80 70 5 100 Prickly Sida 100 35 100 65 90 100 100 90 30 70 100 Purslane 100 100 100 100 100 100 100 100 100 100 100 Quackgrass 0 0 20 0 0 20 0 0 0 0 85 Ragweed 100 95 98 100 0 100 98 98 100 98 100 Russian Thistle 100 75 — 100 — — 100 100 100 100 100 Ryegrass, Italian 0 0 15 20 0 20 30 20 0 20 98 Sandbur 90 75 98 0 80 98 95 90 20 85 100 Signalgrass 90 10 90 5 5 95 75 90 5 35 95 Sowthistle 100 100 100 100 0 100 100 100 100 100 — Spanishneedles 95 98 98 90 95 100 98 95 100 95 100 Surinam Grass — — 98 100 98 100 100 95 90 100 100 62 g ai/ha Barnyardgrass 5 0 0 0 5 95 50 0 5 5 100 Bermudagrass 50 0 90 40 5 100 98 70 65 85 100 Black Mustard 80 75 80 60 35 98 100 80 85 20 100 Bluegrass 0 0 0 15 0 0 25 0 25 25 40 Chickweed — — — — 90 100 — — — — — Crabgrass, Large 5 5 75 35 50 100 95 95 60 25 100 Crabgrass, Naked 60 0 20 65 10 95 100 90 0 65 100 Dallisgrass 65 10 50 65 5 95 80 50 65 0 100 Dayflower, VA 50 — 0 35 0 90 65 50 10 100 100 Field Bindweed 0 0 20 20 0 70 40 65 35 85 100 Foxtail, Green 0 0 0 0 0 40 0 0 0 0 35 Goosegrass 5 40 80 20 30 75 95 75 65 98 100 Guineagrass 0 0 50 0 0 70 50 100 0 0 100 Itchgrass 0 0 0 0 0 35 20 0 0 0 25 Johnsongrass 0 20 75 10 0 80 20 10 15 20 100 Kochia 100 0 25 0 65 75 100 100 50 20 80 Mallow 65 0 — 65 5 95 80 5 70 0 50 Morningglory 20 30 0 0 90 90 80 60 0 95 — Nutsedge, Purple 10 5 30 20 35 95 50 20 0 0 20 Prickly Sida 65 20 50 5 5 100 100 70 25 0 100 Purslane 95 65 90 100 60 100 100 100 100 100 95 Quackgrass 0 0 0 0 0 15 0 0 0 0 35 Ragweed 100 65 70 90 0 100 98 80 90 95 100 Russian Thistle 50 75 — 90 — — 90 100 95 75 100 Ryegrass, Italian 0 0 0 0 0 10 0 0 0 0 60 Sandbur 5 5 5 0 10 60 50 65 20 50 100 Signalgrass 10 0 50 0 5 75 75 0 0 10 75 Sowthistle 100 98 80 100 0 100 100 100 100 100 — Spanishneedles 95 90 95 0 85 98 85 — 90 85 100 Surinam Grass 0 100 98 100 95 100 95 — 80 65 100 31 g ai/ha Barnyardgrass 0 0 0 0 0 75 5 0 0 0 60 Bermudagrass 25 0 70 0 0 100 65 50 0 5 75 Black Mustard 65 50 20 40 5 60 75 0 60 0 80 Bluegrass 0 0 0 0 0 0 20 0 0 0 10 Chickweed — — — — 20 100 — — — — — Crabgrass, Large 0 5 20 35 30 98 75 30 25 5 100 Crabgrass, Naked 0 0 0 0 0 95 80 0 0 0 100 Dallisgrass 25 10 10 0 5 80 50 50 20 0 75 Dayflower, VA 35 0 0 0 0 10 0 50 0 80 90 Field Bindweed 0 0 — 0 0 70 0 20 0 0 100 Foxtail, Green 0 0 0 0 0 5 0 0 0 0 20 Goosegrass 0 20 60 5 0 75 35 25 5 95 100 Guineagrass 0 0 — 0 0 10 0 65 0 0 100 Itchgrass 0 0 0 0 0 15 20 0 0 0 10 Johnsongrass 0 0 0 0 0 65 5 0 0 0 95 Kochia 50 — 25 0 65 20 98 70 0 0 — Mallow 0 0 — 65 0 — — 5 70 0 0 Morningglory 0 0 0 0 0 70 — 60 0 80 90 Nutsedge, Purple 0 0 5 20 0 75 5 10 0 0 5 Prickly Sida 50 20 0 0 0 100 60 35 0 0 85 Purslane 0 50 60 100 0 100 100 100 0 0 75 Quackgrass 0 0 0 0 0 0 0 0 0 0 0 Ragweed 50 50 50 50 0 95 98 50 75 70 100 Russian Thistle — — — 90 — — 75 65 0 65 100 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 50 Sandbur 0 0 0 0 5 5 25 0 0 0 75 Signalgrass 0 0 0 0 5 60 0 0 0 0 — Sowthistle 65 75 80 95 0 100 100 75 80 50 — Spanishneedles 95 0 70 0 60 98 65 0 0 50 100 Surinam Grass — 98 98 90 80 100 50 40 35 5 100 16 g ai/ha Compounds 47 51 52 59 66 85 87 113 128 233 Barnyardgrass 0 0 0 0 0 60 0 0 0 0 Bermudagrass 10 0 30 0 0 80 65 50 0 5 Black Mustard 0 0 0 20 0 50 75 0 60 0 Bluegrass 0 0 0 0 0 0 20 0 0 0 Chickweed — — — — 0 90 — — — — Crabgrass, Large 0 0 0 0 15 95 50 20 0 0 Crabgrass, Naked 0 0 0 0 0 0 — 0 0 0 Dallisgrass 0 0 5 0 0 50 50 5 0 0 Dayflower, VA 35 0 0 — 0 5 0 50 — 0 Field Bindweed 0 0 20 0 0 50 0 0 0 0 Foxtail, Green 0 0 0 0 0 0 0 0 0 0 Goosegrass 0 20 5 0 0 65 35 25 0 70 Guineagrass 0 0 0 0 0 0 0 0 0 0 Itchgrass 0 0 0 0 0 10 0 0 0 0 Johnsongrass 0 0 0 0 0 50 0 0 0 0 Kochia 0 0 — 0 0 5 65 — 0 0 Mallow 0 0 — 0 0 80 — 0 — 0 Morningglory 0 0 0 0 0 — 10 60 — 0 Nutsedge, Purple 0 0 0 0 0 70 0 0 0 0 Prickly Sida 0 0 0 0 0 90 50 0 0 0 Purslane 0 0 0 65 0 80 70 90 0 0 Quackgrass 0 0 0 0 0 0 0 0 0 0 Ragweed 0 35 30 0 0 90 30 0 0 50 Russian Thistle 0 — 0 — — — 50 0 — 50 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 Sandbur 0 0 0 0 0 5 0 0 0 0 Signalgrass 0 0 0 0 0 5 0 0 0 0 Sowthistle 65 40 0 0 0 100 98 50 80 0 Spanishneedles 0 0 35 0 0 90 0 0 0 0 Surinam Grass 0 90 0 5 0 98 0 — 0 0

›Test E

Three plastic pots (ca. 16-cm diameter) for each application were partially filled with sterilized Tama silt loam soil comprising a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separate plantings for each of the three pots were as follows. Seeds from the U.S. of ducksalad ( Heteranthera limosa ), sedge (smallflower umbrella sedge, Cyperus difformis ), ricefield bulrush ( Scirpus mucronatus ) and redstem (purple redstem, Ammannia coccinea ), were planted into one 16-cm pot for each rate. Seeds from the U.S. of flatsedge (rice flatsedge, Cyperus iria ), sprangletop (bearded (i.e. Brdd.) sprangletop, Leptochloa fascicularis ), one stand of 9 or 10 water seeded rice seedlings ( Oryza sativa cv. ‘ Japonica -M202’), and two stands of 3 or 4 transplanted rice seedlings ( Oryza sativa cv. ‘ Japonica -M202’) were planted into one 16-cm pot for each rate. Seeds from the U.S. of barnyardgrass ( Echinochloa crus - galli ), late watergrass ( Echinochloa oryzicola ), early watergrass ( Echinochloa oryzoides ) and junglerice ( Echinochloa colona ) were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5-leaf stage at time of treatment.

Potted plants were grown in a greenhouse with day/night temperature settings of 30/27° C., and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. Test pots were maintained in the greenhouse until test completion.

At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 days. Plant response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE E Flood 500 g ai/ha Compounds 4 19 Barnyardgrass 60 85 Bulrush, Ricefield 80 75 Ducksalad 100 100 Flatsedge, Rice 90 100 Junglerice 50 80 Redstem 85 85 Rice, Transplanted 15 65 Rice, Water Seeded 50 95 Sedge, Umbrella 100 100 Sprangletop, Brdd. — 100 Watergrass, Early 65 85 Watergrass, Late 60 55 Compounds 4 19 28 218 250 g ai/ha Barnyardgrass 60 70 0 95 Bulrush, Ricefield 80 70 65 100 Ducksalad 100 100 100 100 Flatsedge, Rice 40 95 45 75 Junglerice 25 65 0 100 Redstem 80 90 90 80 Rice, Transplanted 0 40 15 10 Rice, Water Seeded 20 70 85 35 Sedge, Umbrella 95 100 100 100 Sprangletop, Brdd. — 100 — 95 Watergrass, Early 60 65 20 60 Watergrass, Late 15 60 0 70 125 g ai/ha Barnyardgrass 0 60 0 30 Bulrush, Ricefield 40 70 35 90 Ducksalad 90 95 80 95 Flatsedge, Rice 0 40 0 70 Junglerice 0 50 0 65 Redstem 80 90 50 75 Rice, Transplanted 0 35 15 0 Rice, Water Seeded 10 40 65 20 Sedge, Umbrella 90 100 90 100 Sprangletop, Brdd. — 95 — 70 Watergrass, Early 0 45 0 20 Watergrass, Late 0 45 0 40 64 g ai/ha Compounds 19 28 218 Barnyardgrass 60 0 0 Bulrush, Ricefield 50 30 80 Ducksalad 85 0 85 Flatsedge, Rice 40 0 70 Junglerice 0 0 0 Redstem 0 40 65 Rice, Transplanted 0 15 0 Rice, Water Seeded 0 60 0 Sedge, Umbrella 90 85 95 Sprangletop, Brdd. 75 — 70 Watergrass, Early 20 0 20 Watergrass, Late 0 0 40 32 g ai/ha Compounds 28 218 Barnyardgrass 0 0 Bulrush, Ricefield 20 80 Ducksalad 0 80 Flatsedge, Rice 0 75 Junglerice 0 0 Redstem 0 65 Rice, Transplanted 0 0 Rice, Water Seeded 45 15 Sedge, Umbrella 0 85 Sprangletop, Brdd. — 65 Watergrass, Early 0 0 Watergrass, Late 0 20

›Test F

Test F evaluated the effect of combining compound 2 with bromoxynil. The test species for this experiment was Russian thistle ( Salsola iberica ), which was prepared by sowing seeds into a blend of loam soil and sand. Test chemicals were formulated in a non-phytotoxic solvent mixture that included a surfactant and applied postemergence to plants ranging in height from 12 to 20 cm.

Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of 16 hours; day and night temperatures ranged between 24-30° C. and 19-21° C., respectively. Treatments consisted of Compound 2, bromoxynil, or their combination, using a spray volume of 457 L/ha. Each treatment was replicated three times. Treated plants and untreated controls were maintained in a greenhouse for 15 days, after which time all plants were visually evaluated and compared to the untreated controls. Plant responses were calculated as the mean of the three replicates and summarized in Table F. Visual evaluations were based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. Colby's Equation was used to determine the herbicidal effects expected from the mixtures. Colby's Equation (Colby, S. R. “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds , 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form:

P a+b =P a +P b −( P a P b /100)

wherein P a+b is the percentage effect of the mixture expected from additive contribution of the individual components:

P a is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and P b is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.

The results and additive effects expected from Colby's Equation are listed in Table F1.

The results in Table D1 suggest the combination of Compound 2 and bromoxynil have a synergistic action based on the observed injury being greater than the expected values as calculated by the Colby Equation for an additive effect.

›Tables in the description — 25

Table	Row Heading
1A	R 2 is Me
2A	R 2 is Et
3A	R 2 is n-Pr
4A	R 2 is c-Pr
5A	R 2 is SMe
6A	R 2 is SO 2 Me
7A	R 2 is CF 3
8A	R 2 is Ph(2-Cl)
9A	R 2 is Ph(3-Cl)
10A	R 2 is Ph(4-Cl)
11A	R 2 is Ph(2-Me)
12A	R 2 is Ph(3-Me)
13A	R 2 is Ph(4-Me)
14A	R 2 is Ph(2-OMe)
15A	R 2 is Ph(3-OMe)
16A	R 2 is Ph(4-OMe)
17A	R 2 is Ph(2-F)
18A	R 2 is Ph(3-F)
19A	R 2 is Ph(4-F)
20A	R 2 is OMe
21A	R 2 is OEt
22A	R 2 is CH 2 Ph
23A	R 2 is 2-pyridinyl
24A	R 2 is 3-pyridinyl
25A	R 2 is 4-pyridinyl
26A	R 2 is H
27A	R 2 is Ph(3,5-di-F)
28A	R 2 is Ph(3,4-di-F)
29A	R 2 is Ph(3,4,5-tri-F)
30A	R 2 is Ph(2,3-di-F)
31A	R 2 is Ph(3-CF 3 )
32A	R 2 is Ph(4-CF 3 )
33A	R 2 is Ph(3,5-di-CF 3 )
34A	R 2 is n-Bu
35A	R 2 is CH 2 OCH 3 ,
36A	R 2 is CH 2 CH 2 OCH 3
37A	R 2 is CH 2 CH 2 CF 3
38A	R 2 is CH 2 CF 3
39A	R 2 is n-pent
40A	R 2 is c-pent
41A	R 2 is c-Hex
42A	R 2 is n-Hex
43A	R 2 is thp-4-yl
44A	R 2 is Ph(2-CN)
45A	R 2 is Ph(3-CN)
46A	R 2 is Ph(4-CN)
47A	R 2 is Ph(2-C≡CH)
48A	R 2 is Ph(3-C≡CH)
49A	R 2 is Ph(4-C≡CH)
50A	R 2 is Ph(3-Me, 2-F)
51A	R 2 is Ph(3-Me-4-F)
52A	R 2 is Ph(3-Me, 5-F)
53A	R 2 is Ph(3-Me, 6-F)
54A	R 2 is Ph(3-F, 2-Me)
55A	R 2 is Ph(3-F-4-Me)
56A	R 2 is Ph(3-F-5-Me)
57A	R 2 is Ph(3-F, 6-Me)

Table	Row Heading
1B	R 1 is Et
2B	R 1 is CH 2 CF 3
3B	R 1 is CH 2 CH═CH 2
4B	R 1 is CH 2 C≡CH
5B	R 1 is Ph
6B	R 1 is Ph(2-Me)
7B	R 1 is Ph(4-Me)
8B	R 1 is Ph(2-Cl)
9B	R 1 is Ph(3-Cl)
10B	R 1 is n-Pr
11B	R 1 is c-Pr
12B	R 1 is n-Bu
13B	R 1 is i-Bu
14B	R 1 is n-pent
15B	R 1 is n-Hex
16B	R 1 is thp-4-yl
17B	R 1 is thtp-4yl
18B	R 1 is c-Hex
19B	R 1 is CH 2 CH 2 OCH 3
20B	R 1 is CH 2 CH 2 OCH 2 CH 3
21B	R 1 is CH 2 CH 2 CH 2 OCH 3
22B	R 1 is CH 2 CH 2 CH 2 OCH 2 CH 3
23B	R 1 is Ph(3-OMe)
24B	R 1 is Ph(4-OMe)
25B	R 1 is Ph(3,4-di-OMe)
26B	R 1 is Ph(2-F)
27B	R 1 is Ph(3-F)
28B	R 1 is Ph(4-F)
29B	R 1 is Ph(3-Me)
30B	R 1 is Ph(2-Me-3-F)
31B	R 1 is Ph(2-Me-4-F)
32B	R 1 is Ph(2-Me-5-F)
33B	R 1 is Ph(2-F-3-Me)
34B	R 1 is Ph(2-F-4-Me)
35B	R 1 is Ph(2-F-5-Me)
36B	R 1 is Ph(3-F-4-Me)
37B	R 1 is Ph(3-F-5-Me)
38B	R 1 is Ph(3-Me-4-F)

Table	Row Heading
1C	R 1 is CH 2 CH 3 , R 9 is CH 3
2C	R 1 is CH 2 CH═CH 2 , R 9 is CH 3
3C	R 1 is CH 2 C≡CH, R 9 is CH 3
4C	R 1 is Ph, R 9 is CH 3
5C	R 1 is Ph(2-Me), R 9 is CH 3
6C	R 1 is Ph(4-Me), R 9 is CH 3
7C	R 1 is Ph(2-Me), R 9 is CH 3
8C	R 1 is Ph(3-Cl), R 9 is CH 3
9C	R 1 is CH 3 , R 9 is CH 2 CH 3
10C	R 1 is CH 2 CH 3 , R 9 is CH 2 CH 3
11C	R 1 is CH 2 CH═CH 2, R 9 is CH 2 CH 3
12C	R 1 is CH 2 C≡CH, R 9 is CH 2 CH 3
13C	R 1 is Ph, R 9 is CH 2 CH 3
14C	R 1 is Ph(2-Me), R 9 is CH 2 CH 3
15C	R 1 is Ph(4-Me), R 9 is CH 2 CH 3
16C	R 1 is Ph(2-Cl), R 9 is CH 2 CH 3
17C	R 1 is Ph(3-Cl), R 9 is CH 2 CH 3
18C	R 1 is n-Bu, R 9 is CH 3
19C	R 1 is n-pent, R 9 is CH 3
20C	R 1 is n-Hex, R 9 is CH 3
21C	R 1 is thp-4-yl, R 9 is CH 3
22C	R 1 is thtp-4-yl, R 9 is CH 3
23C	R 1 is c-Hex, R 9 is CH 3
24C	R 1 is CH 2 CH 2 OCH 3 , R 9 is CH 3
25C	R 1 is CH 2 CH 2 OCH 2 CH 3 , R 9 is CH 3
26C	R 1 is CH 2 CH 2 CH 2 OCH 3 , R 9 is CH 3
27C	R 1 is CH 2 CH 2 CH 2 OEt, R 9 is CH 3
28C	R 1 is n-Bu, R 9 is CH 2 CH 3
29C	R 1 is n-pent, R 9 is CH 2 CH 3
30C	R 1 is n-Hex, R 9 is CH 2 CH 3
31C	R 1 is thp-4-yl, R 9 is CH 2 CH 3
32C	R 1 is thtp-4-yl, R 9 is CH 2 CH 3
33C	R 1 is c-Hex, R 9 is CH 2 CH 3
34C	R 1 is CH 2 CH 2 OCH 3 , R 9 is CH 2 CH 3
35C	R 1 is CH 2 CH 2 OCH 2 CH 3 , R 9 is CH 2 CH 3
36C	R 1 is CH 2 CH 2 CH 2 OCH 3 , R 9 is CH 2 CH 3
37C	R 1 is CH 2 CH 2 CH 2 OEt, R 9 is CH 2 CH 3

Table	Row Heading
1D	R 1 is CH 2 CH 3 , R 9 is CH 3
2D	R 1 is CH 2 CH═CH 2 , R 9 is CH 3
3D	R 1 is CH 2 C≡CH, R 9 is CH 3
4D	R 1 is Ph, R 9 is CH 3
5D	R 1 is Ph(2-Me), R 9 is CH 3
6D	R 1 is Ph(4-Me), R 9 is CH 3
7D	R 1 is Ph(2-Me), R 9 is CH 3 R 5 is CH 3
8D	R 1 is Ph(3-Cl), R 9 is CH3
9D	R 1 is CH 3 , R 9 is CH 2 CH 3
10D	R 1 is CH 2 CH 3 , R 9 is CH 2 CH 3
11D	R 1 is CH 2 CH═CH 2 , R 9 is CH 2 CH 3
12D	R 1 is CH 2 C≡CH, R 9 is CH 2 CH 3
13D	R 1 is Ph, R 9 is CH 2 CH 3
14D	R 1 is Ph(2-Me), R 9 is CH 2 CH 3
15D	R 1 is Ph(4-Me), R 9 is CH 2 CH 3
16D	R 1 is Ph(2-Cl), R 9 is CH 2 CH 3
17D	R 1 is Ph(3-Cl), R 9 is CH 2 CH 3
18D	R 1 is n-Bu, R 9 is CH 3
19D	R 1 is n-pent, R 9 is CH 3
20D	R 1 is n-Hex, R 9 is CH 3
21D	R 1 is thp-4-yl, R 9 is CH 3
22D	R 1 is thtp-4-yl, R 9 is CH 3
23D	R 1 is c-Hex, R 9 is CH 3
24D	R 1 is CH 2 CH 2 OCH 3 , R 9 is CH 3
25D	R 1 is CH 2 CH 2 OCH 2 CH 3 , R 9 is CH 3
26D	R 1 is CH 2 CH 2 CH 2 OCH 3 , R 9 is CH 3
27D	R 1 is CH 2 CH 2 CH 2 OEt, R 9 is CH 3
28D	R 1 is n-Bu, R 9 is CH 2 CH 3
29D	R 1 is n-pent, R 9 is CH 2 CH 3
30D	R 1 is n-Hex, R 9 is CH 2 CH 3
31D	R 1 is thp-4-yl, R 9 is CH 2 CH 3
32D	R 1 is thtp-4-yl, R 9 is CH 2 CH 3
33D	R 1 is c-Hex, R 9 is CH 2 CH 3
34D	R 1 is CH 2 CH 2 OCH 3 , R 9 is CH 2 CH 3
35D	R 1 is CH 2 CH 2 OCH 2 CH 3 , R 9 is CH 2 CH 3
36D	R 1 is CH 2 CH 2 CH 2 OCH 3 , R 9 is CH 2 CH 3
37D	R 1 is CH 2 CH 2 CH 2 OEt, R 9 is CH 2 CH 3

Table	Row Heading
1E	R 2 is Me
2E	R 2 is Et
3E	R 2 is n-Pr
4E	R 2 is c-Pr
5E	R 2 is SMe
6E	R 2 is SO 2 Me
7E	R 2 is CF 3
8E	R 2 is Ph(2-Cl)
9E	R 2 is Ph(3-Cl)
10E	R 2 is Ph(4-Cl)
11E	R 2 is Ph(2-Me)
12E	R 2 is Ph(3-Me)
13E	R 2 is Ph(4-Me)
14E	R 2 is Ph(2-OMe)
15E	R 2 is Ph(3-OMe)
16E	R 2 is Ph(4-OMe)
17E	R 2 is Ph(2-F)
18E	R 2 is Ph(3-F)
19E	R 2 is Ph(4-F)
20E	R 2 is OMe
21E	R 2 is OEt
22E	R 2 is CH 2 Ph
23E	R 2 is 2-pyridinyl
24E	R 2 is 3-pyridinyl
25E	R 2 is 4-pyridinyl
26E	R 2 is H
27E	R 2 is Ph(3,5-di-F)
28E	R 2 is Ph(3,4-di-F)
29E	R 2 is Ph(3,4,5-tri-F)
30E	R 2 is Ph(2,3-di-F)
31E	R 2 is Ph(3-CF 3 )
32E	R 2 is Ph(4-CF 3 )
33E	R 2 is Ph(3,5-di-CF 3 )
34E	R 2 is n-Bu
35E	R 2 is CH 2 OCH 3
36E	R 2 is CH 2 CH 2 OCH 3
37E	R 2 is CH 2 CH 2 CF 3
38E	R 2 is CH 2 CF 3
39E	R 2 is n-pent
40E	R 2 is c-pent
41E	R 2 is c-Hex
42E	R 2 is n-Hex
43E	R 2 is thp-4-yl
44E	R 2 is Ph(2-CN)
45E	R 2 is Ph(3-CN)
46E	R 2 is Ph(4-CN)
47E	R 2 is Ph(2-C≡CH)
48E	R 2 is Ph(3-C≡CH)
49E	R 2 is Ph(4-C≡CH)
50E	R 2 is Ph(3-Me, 2-F)
51E	R 2 is Ph(3-Me-4-F)
52E	R 2 is Ph(3-Me, 5-F)
53E	R 2 is Ph(3-Me, 6-F)
54E	R 2 is Ph(3-F, 2-Me)
55E	R 2 is Ph(3-F-4-Me)
56E	R 2 is Ph(3-F-5-Me)
57E	R 2 is Ph(3-F, 6-Me)

Table	Row Heading
1F	R 1 is n-Pr
2F	R 1 is n-Bu
3F	R 1 is n-pent
4F	R 1 is n-Hex
5F	R 1 is thp-4-yl
6F	R 1 is thtp-4-yl
7F	R 1 is c-Hex
8F	R 1 is CH 2 CH 2 OCH 3
9F	R 1 is CH 2 CH 2 OCH 2 CH 3
10F	R 1 is CH 2 CH 2 CH 2 OCH 3
11F	R 1 is CH 2 CH 2 CH 2 OCH 2 CH 3

Table	Row Heading
1H	R 12 is CH 3
2H	R 12 is CH 2 CH 3

Table	Row Heading
1J	R 12 is CH 3
2J	R 12 is CH 2 CH 3

Table	Row Heading
1K	R 1 is n-Bu
2K	R 1 is n-pent
3K	R 1 is n-Hex
4K	R 1 is thp-4-yl
5K	R 1 is thtp-4-yl
6K	R 1 is c-Hex
7K	R 1 is CH 2 CH 2 OCH 3
8K	R 1 is CH 2 CH 2 OCH 2 CH 3
9K	R 1 is CH 2 CH 2 CH 2 OCH 3
10K	R 1 is CH 2 CH 2 CH 2 OCH 2 CH 3

Table	Row Heading
1U	R 2 is Me
2U	R 2 is Et
3U	R 2 is n-Pr
4U	R 2 is c-Pr
5U	R 2 is SMe
6U	R 2 is SO 2 Me
7U	R 2 is CF 3
8U	R 2 is Ph(2-Cl)
9U	R 2 is Ph(3-Cl)
10U	R 2 is Ph(4-Cl)
11U	R 2 is Ph(2-Me)
12U	R 2 is Ph(3-Me)
13U	R 2 is Ph(4-Me)
14U	R 2 is Ph(2-OMe)
15U	R 2 is Ph(3-OMe)
16U	R 2 is Ph(4-OMe)
17U	R 2 is Ph(2-F)
18U	R 2 is Ph(3-F)
19U	R 2 is Ph(4-F)
20U	R 2 is OMe
21U	R 2 is OEt
22U	R 2 is CH 2 Ph
23U	R 2 is 2-pyridinyl
24U	R 2 is 3-pyridinyl
25U	R 2 is 4-pyridinyl
26U	R 2 is H
27U	R 2 is Ph(3,5-di-F)
28U	R 2 is Ph(3,4-di-F)
29U	R 2 is Ph(3,4,5-tri-F)
30U	R 2 is Ph(2,3-di-F)
31U	R 2 is Ph(3-CF 3 )
32U	R 2 is Ph(4-CF 3 )
33U	R 2 is Ph(3,5-di-CF 3 )
34U	R 2 is n-Bu
35U	R 2 is CH 2 OCH 3
36U	R 2 is CH 2 CH 2 OCH 3
37U	R 2 is CH 2 CH 2 CF 3
38U	R 2 is CH 2 CF 3
39U	R 2 is n-pent
40U	R 2 is c-pent
41U	R 2 is c-Hex
42U	R 2 is n-Hex
43U	R 2 is thp-4-yl
44U	R 2 is Ph(2-CN)
45U	R 2 is Ph(3-CN)
46U	R 2 is Ph(4-CN)
47U	R 2 is Ph(2-C≡CH)
48U	R 2 is Ph(3-C≡CH)
49U	R 2 is Ph(4-C≡CH)
50U	R 2 is Ph(3-Me, 2-F)
51U	R 2 is Ph(3-Me-4-F)
52U	R 2 is Ph(3-Me, 5-F)
53U	R 2 is Ph(3-Me, 6-F)
54U	R 2 is Ph(3-F, 2-Me)
55U	R 2 is Ph(3-F-4-Me)
56U	R 2 is Ph(3-F-5-Me)
57U	R 2 is Ph(3-F, 6-Me)

Table	Row Heading
1BB	R 2 is Me
2BB	R 2 is Et
3BB	R 2 is n-Pr
4BB	R 2 is c-Pr
5BB	R 2 is SMe
6BB	R 2 is SO 2 Me
7BB	R 2 is CF 3
8BB	R 2 is Ph(2-Cl)
9BB	R 2 is Ph(3-Cl)
10BB	R 2 is Ph(4-Cl)
11BB	R 2 is Ph(2-Me)
12BB	R 2 is Ph(3-Me)
13BB	R 2 is Ph(4-Me)
14BB	R 2 is Ph(2-OMe)
15BB	R 2 is Ph(3-OMe)
16BB	R 2 is Ph(4-OMe)
17BB	R 2 is Ph(2-F)
18BB	R 2 is Ph(3-F)
19BB	R 2 is Ph(4-F)
20BB	R 2 is OMe
21BB	R 2 is OEt
22BB	R 2 is CH 2 Ph
23BB	R 2 is 2-pyridinyl
24BB	R 2 is 3-pyridinyl
25BB	R 2 is 4-pyridinyl
26BB	H
27BB	Ph(3,5-di-F)
28BB	Ph(3,4-di-F)
29BB	Ph(3,4,5-tri-F)
30BB	Ph(2,3-di-F)
31BB	Ph(3-CF 3 )
32BB	Ph(4-CF 3 )
33BB	Ph(3,5-di-CF 3 )
34BB	n-Bu
35BB	CH 2 OCH 3
36BB	CH 2 CH 2 OCH 3
37BB	CH 2 CH 2 CF 3
38BB	CH 2 CF 3
39BB	n-pent
40BB	c-pent
41BB	c-Hex
42BB	n-Hex
43BB	thp-4-yl
44BB	Ph(2-CN)
45BB	Ph(3-CN)
46BB	Ph(4-CN)
47BB	Ph(2-C≡CH)
48BB	Ph(3-C≡CH)
49BB	Ph(4-C≡CH)
50BB	Ph(3-Me, 2-F)
51BB	Ph(3-Me-4-F)
52BB	Ph(3-Me, 5-F)
53BB	Ph(3-Me, 6-F)
54BB	Ph(3-F, 2-Me)
55BB	Ph(3-F-4-Me)
56BB	Ph(3-F-5-Me)
57BB	Ph(3-F, 6-Me)

Table	Row Heading
1K	R 2 is c-Pr
2K	R 2 is SMe
3K	R 2 is SO 2 Me
4K	R 2 is CF 3

Table	Row Heading
1L	R 2 is c-Pr
2L	R 2 is n-Pr
3L	R 2 is SMe
4L	R 2 is SO 2 Me
5L	R 2 is CF 3
6L	R 2 Ph(2-Cl)
7L	R 2 Ph(3-Cl)
8L	R 2 is Ph(4-Cl)
9L	R 2 is Ph(2-Me)
10L	R 2 is Ph(3-Me)
11L	R 2 is Ph(4-Me)

Weight Percent Active

	Ingredient	Diluent	Surfactant
Water-Dispersible and Water-	0.001-90	0-99.999	0-15
soluble Granules, Tablets and
Powders
Oil Dispersions, Suspensions,	1-50	40-99	0-50
Emulsions, Solutions
(including Emulsifiable
Concentrates)
Dusts	1-25	70-99	0-5
Granules and Pellets	0.001-99	5-99.999	0-15
High Strength Compositions	90-99	0-10	0-2

Compound 4	98.5%
silica aerogel	0.5%
synthetic amorphous fine silica	1.0%

Compound 2	65.0%
dodecylphenol polyethylene glycol ether	2.0%
sodium ligninsulfonate	4.0%
sodium silicoaluminate	6.0%
montmorillonite (calcined)	23.0%

Compound 12	10.0%
attapulgite granules (low volatile matter, 0.71/0.30 mm;	90.0%
U.S.S. No. 25-50 sieves)

Compound 8	25.0%
anhydrous sodium sulfate	10.0%
crude calcium ligninsulfonate	5.0%
sodium alkylnaphthalenesulfonate	1.0%
calcium/magnesium bentonite	59.0%

Compound 2	10.0%
polyoxyethylene sorbitol hexoleate	20.0%
C 6 -C 10 fatty acid methyl ester	70.0%

Compound 12	5.0%
polyvinylpyrrolidone-vinyl acetate copolymer	30.0%
alkylpolyglycoside	30.0%
glyceryl monooleate	15.0%
Water	20.0%

TABLE A1

			More	Most
		Typical	Typical	Typical
		Weight	Weight	Weight
Component (a)	Component (b)	Ratio	Ratio	Ratio
Compound 47	2,4-D	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	acetochlor	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	acifluorfen	1:96 to 12:1	1:32 to 4:1	1:12 to 1:2
Compound 47	aclonifen	1:857 to 2:1	1:285 to 1:3	1:107 to
				1:12
Compound 47	alachlor	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	ametryn	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	amicarbazone	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	amidosulfuron	1:6 to 168:1	1:2 to 56:1	1:1 to 11:1
Compound 47	amino-	1:48 to 24:1	1:16 to 8:1	1:6 to 2:1
	cyclopyrachlor
Compound 47	aminopyralid	1:20 to 56:1	1:6 to 19:1	1:2 to 4:1
Compound 47	amitrole	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	anilofos	1:96 to 12:1	1:32 to 4:1	1:12 to 1:2
Compound 47	asulam	1:960 to 2:1	1:320 to 1:3	1:120 to
				1:14
Compound 47	atrazine	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	azimsulfuron	1:6 to 168:1	1:2 to 56:1	1:1 to 11:1
Compound 47	beflubutamid	1:342 to 4:1	1:114 to 2:1	1:42 to 1:5
Compound 47	benfuresate	1:617 to 2:1	1:205 to 1:2	1:77 to 1:9
Compound 47	bensulfuron	1:25 to 45:1	1:8 to 15:1	1:3 to 3:1
Compound 47	bentazon	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	benzobicyclon	1:85 to 14:1	1:28 to 5:1	1:10 to 1:2
Compound 47	benzofenap	1:257 to 5:1	1:85 to 2:1	1:32 to 1:4
Compound 47	bicyclopyrone	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	bifenox	1:257 to 5:1	1:85 to 2:1	1:32 to 1:4
Compound 47	bispyribac-	1:10 to 112:1	1:3 to 38:1	1:1 to 7:1
	sodium
Compound 47	bromacil	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	bromobutide	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	bromoxynil	1:96 to 12:1	1:32 to 4:1	1:12 to 1:2
Compound 47	butachlor	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	butafenacil	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	butylate	1:1542 to 1:2	1:514 to 1:5	1:192 to
				1:22
Compound 47	carfenstrole	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	carfentrazone	1:128 to 9:1	1:42 to 3:1	1:16 to 1:2
Compound 47	chlorimuron	1:8 to 135:1	1:2 to 45:1	1:1 to 9:1
Compound 47	chlorotoluron	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	chlorsulfuron	1:6 to 168:1	1:2 to 56:1	1:1 to 11:1
Compound 47	cincosulfuron	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
Compound 47	cinidon-ethyl	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	cinmethylin	1:34 to 34:1	1:11 to 12:1	1:4 to 3:1
Compound 47	clethodim	1:48 to 24:1	1:16 to 8:1	1:6 to 2:1
Compound 47	clodinafop	1:20 to 56:1	1:6 to 19:1	1:2 to 4:1
Compound 47	clomazone	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	clomeprop	1:171 to 7:1	1:57 to 3:1	1:21 to 1:3
Compound 47	clopyralid	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	cloransulam	1:12 to 96:1	1:4 to 32:1	1:1 to 6:1
Compound 47	cumyluron	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	cyanazine	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	cyclosul-	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
	famuron
Compound 47	cycloxydim	1:96 to 12:1	1:32 to 4:1	1:12 to 1:2
Compound 47	cyhalofop	1:25 to 45:1	1:8 to 15:1	1:3 to 3:1
Compound 47	daimuron	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	desmedipham	1:322 to 4:1	1:107 to 2:1	1:40 to 1:5
Compound 47	dicamba	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	dichlobenil	1:1371 to 1:2	1:457 to 1:4	1:171 to
				1:20
Compound 47	dichlorprop	1:925 to 2:1	1:308 to 1:3	1:115 to
				1:13
Compound 47	diclofop	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	diclosulam	1:10 to 112:1	1:3 to 38:1	1:1 to 7:1
Compound 47	difenzoquat	1:288 to 4:1	1:96 to 2:1	1:36 to 1:4
Compound 47	diflufenican	1:857 to 2:1	1:285 to 1:3	1:107 to
				1:12
Compound 47	diflufenzopyr	1:12 to 96:1	1:4 to 32:1	1:1 to 6:1
Compound 47	dimethachlor	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	dimethametryn	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	dimethenamid	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	dithiopyr	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	diuron	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	EPTC	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	esprocarb	1:1371 to 1:2	1:457 to 1:4	1:171 to
				1:20
Compound 47	ethalfluralin	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	ethametsulfuron	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
Compound 47	ethoxyfen	1:8 to 135:1	1:2 to 45:1	1:1 to 9:1
Compound 47	ethoxysulfuron	1:20 to 56:1	1:6 to 19:1	1:2 to 4:1
Compound 47	etobenzanid	1:257 to 5:1	1:85 to 2:1	1:32 to 1:4
Compound 47	fenoxaprop	1:120 to 10:1	1:40 to 4:1	1:15 to 1:2
Compound 47	fenoxasulfone	1:85 to 14:1	1:28 to 5:1	1:10 to 1:2
Compound 47	fentrazamide	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
Compound 47	flazasulfuron	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
Compound 47	florasulam	1:2 to 420:1	1:1 to 140:1	2:1 to 27:1
Compound 47	fluazifop	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	flucarbazone	1:8 to 135:1	1:2 to 45:1	1:1 to 9:1
Compound 47	flucetosulfuron	1:8 to 135:1	1:2 to 45:1	1:1 to 9:1
Compound 47	flufenacet	1:257 to 5:1	1:85 to 2:1	1:32 to 1:4
Compound 47	flumetsulam	1:24 to 48:1	1:8 to 16:1	1:3 to 3:1
Compound 47	flumiclorac	1:10 to 112:1	1:3 to 38:1	1:1 to 7:1
Compound 47	flumioxazin	1:25 to 45:1	1:8 to 15:1	1:3 to 3:1
Compound 47	fluometuron	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	flupyrsulfuron	1:3 to 336:1	1:1 to 112:1	2:1 to 21:1
Compound 47	fluridone	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	fluroxypyr	1:96 to 12:1	1:32 to 4:1	1:12 to 1:2
Compound 47	flurtamone	1:857 to 2:1	1:285 to 1:3	1:107 to
				1:12
Compound 47	fomesafen	1:96 to 12:1	1:32 to 4:1	1:12 to 1:2
Compound 47	foramsulfuron	1:13 to 84:1	1:4 to 28:1	1:1 to 6:1
Compound 47	glufosinate	1:288 to 4:1	1:96 to 2:1	1:36 to 1:4
Compound 47	glyphosate	1:288 to 4:1	1:96 to 2:1	1:36 to 1:4
Compound 47	halosulfuron	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
Compound 47	haloxyfop	1:34 to 34:1	1:11 to 12:1	1:4 to 3:1
Compound 47	hexazinone	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	imazamox	1:13 to 84:1	1:4 to 28:1	1:1 to 6:1
Compound 47	imazapic	1:20 to 56:1	1:6 to 19:1	1:2 to 4:1
Compound 47	imazapyr	1:85 to 14:1	1:28 to 5:1	1:10 to 1:2
Compound 47	imazaquin	1:34 to 34:1	1:11 to 12:1	1:4 to 3:1
Compound 47	imazethabenz	1:171 to 7:1	1:57 to 3:1	1:21 to 1:3
Compound 47	imazethapyr	1:24 to 48:1	1:8 to 16:1	1:3 to 3:1
Compound 47	imazosulfuron	1:27 to 42:1	1:9 to 14:1	1:3 to 3:1
Compound 47	indanofan	1:342 to 4:1	1:114 to 2:1	1:42 to 1:5
Compound 47	indaziflam	1:25 to 45:1	1:8 to 15:1	1:3 to 3:1
Compound 47	iodosulfuron	1:3 to 336:1	1:1 to 112:1	2:1 to 21:1
Compound 47	ioxynil	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	ipfencarbazone	1:85 to 14:1	1:28 to 5:1	1:10 to 1:2
Compound 47	isoproturon	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	isoxaben	1:288 to 4:1	1:96 to 2:1	1:36 to 1:4
Compound 47	isoxaflutole	1:60 to 20:1	1:20 to 7:1	1:7 to 2:1
Compound 47	lactofen	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	lenacil	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	linuron	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	MCPA	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	MCPB	1:288 to 4:1	1:96 to 2:1	1:36 to 1:4
Compound 47	mecoprop	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	mefenacet	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	mefluidide	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	mesosulfuron	1:5 to 224:1	1:1 to 75:1	1:1 to 14:1
Compound 47	mesotrione	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	metamifop	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	metazachlor	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	metazosulfuron	1:25 to 45:1	1:8 to 15:1	1:3 to 3:1
Compound 47	metha-	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
	benzthiazuron
Compound 47	metolachlor	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	metosulam	1:8 to 135:1	1:2 to 45:1	1:1 to 9:1
Compound 47	metribuzin	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	metsulfuron	1:2 to 560:1	1:1 to 187:1	3:1 to 35:1
Compound 47	molinate	1:1028 to 2:1	1:342 to 1:3	1:128 to
				1:15
Compound 47	napropamide	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	naptalam	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	nicosulfuron	1:12 to 96:1	1:4 to 32:1	1:1 to 6:1
Compound 47	norflurazon	1:1152 to 1:1	1:384 to 1:3	1:144 to
				1:16
Compound 47	orbencarb	1:1371 to 1:2	1:457 to 1:4	1:171 to
				1:20
Compound 47	ortho-	1:20 to 56:1	1:6 to 19:1	1:2 to 4:1
	sulfamuron
Compound 47	oryzalin	1:514 to 3:1	1:171 to 1:2	1:64 to 1:8
Compound 47	oxadiargyl	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	oxadiazon	1:548 to 3:1	1:182 to 1:2	1:68 to 1:8
Compound 47	oxasulfuron	1:27 to 42:1	1:9 to 14:1	1:3 to 3:1
Compound 47	oxaziclomefone	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	oxyfluorfen	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	paraquat	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	pendimethalin	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	penoxsulam	1:10 to 112:1	1:3 to 38:1	1:1 to 7:1
Compound 47	penthoxamid	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	pentoxazone	1:102 to 12:1	1:34 to 4:1	1:12 to 1:2
Compound 47	phenmedipham	1:102 to 12:1	1:34 to 4:1	1:12 to 1:2
Compound 47	picloram	1:96 to 12:1	1:32 to 4:1	1:12 to 1:2
Compound 47	picolinafen	1:34 to 34:1	1:11 to 12:1	1:4 to 3:1
Compound 47	pinoxaden	1:25 to 45:1	1:8 to 15:1	1:3 to 3:1
Compound 47	pretilachlor	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	primisulfuron	1:8 to 135:1	1:2 to 45:1	1:1 to 9:1
Compound 47	prodiamine	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	profoxydim	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	prometryn	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	propachlor	1:1152 to 1:1	1:384 to 1:3	1:144 to
				1:16
Compound 47	propanil	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	propaquizafop	1:48 to 24:1	1:16 to 8:1	1:6 to 2:1
Compound 47	propoxy-	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
	carbazone
Compound 47	propyrisulfuron	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
Compound 47	propyzamide	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	prosulfocarb	1:1200 to 1:2	1:400 to 1:4	1:150 to
				1:17
Compound 47	prosulfuron	1:6 to 168:1	1:2 to 56:1	1:1 to 11:1
Compound 47	pyraclonil	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	pyraflufen	1:5 to 224:1	1:1 to 75:1	1:1 to 14:1
Compound 47	pyrasulfotole	1:13 to 84:1	1:4 to 28:1	1:1 to 6:1
Compound 47	pyrazolynate	1:857 to 2:1	1:285 to 1:3	1:107 to
				1:12
Compound 47	pyrazosulfuron	1:10 to 112:1	1:3 to 38:1	1:1 to 7:1
Compound 47	pyrazoxyfen	1:5 to 224:1	1:1 to 75:1	1:1 to 14:1
Compound 47	pyribenzoxim	1:10 to 112:1	1:3 to 38:1	1:1 to 7:1
Compound 47	pyributicarb	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	pyridate	1:288 to 4:1	1:96 to 2:1	1:36 to 1:4
Compound 47	pyriftalid	1:10 to 112:1	1:3 to 38:1	1:1 to 7:1
Compound 47	pyriminobac	1:20 to 56:1	1:6 to 19:1	1:2 to 4:1
Compound 47	pyrimisulfan	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
Compound 47	pyrithiobac	1:24 to 48:1	1:8 to 16:1	1:3 to 3:1
Compound 47	pyroxasulfone	1:85 to 14:1	1:28 to 5:1	1:10 to 1:2
Compound 47	pyroxsulam	1:5 to 224:1	1:1 to 75:1	1:1 to 14:1
Compound 47	quinclorac	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	quizalofop	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	rimsulfuron	1:13 to 84:1	1:4 to 28:1	1:1 to 6:1
Compound 47	saflufenacil	1:25 to 45:1	1:8 to 15:1	1:3 to 3:1
Compound 47	sethoxydim	1:96 to 12:1	1:32 to 4:1	1:12 to 1:2
Compound 47	simazine	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	sulcotrione	1:120 to 10:1	1:40 to 4:1	1:15 to 1:2
Compound 47	sulfentrazone	1:147 to 8:1	1:49 to 3:1	1:18 to 1:3
Compound 47	sulfometuron	1:34 to 34:1	1:11 to 12:1	1:4 to 3:1
Compound 47	sulfosulfuron	1:8 to 135:1	1:2 to 45:1	1:1 to 9:1
Compound 47	tebuthiuron	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	tefuryltrione	1:42 to 27:1	1:14 to 9:1	1:5 to 2:1
Compound 47	tembotrione	1:31 to 37:1	1:10 to 13:1	1:3 to 3:1
Compound 47	tepraloxydim	1:25 to 45:1	1:8 to 15:1	1:3 to 3:1
Compound 47	terbacil	1:288 to 4:1	1:96 to 2:1	1:36 to 1:4
Compound 47	terbuthyl-	1:857 to 2:1	1:285 to 1:3	1:107 to
	atrazine			1:12
Compound 47	terbutryn	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	thenylchlor	1:85 to 14:1	1:28 to 5:1	1:10 to 1:2
Compound 47	thiazopyr	1:384 to 3:1	1:128 to 1:1	1:48 to 1:6
Compound 47	thiencarbazone	1:3 to 336:1	1:1 to 112:1	2:1 to 21:1
Compound 47	thifensulfuron	1:5 to 224:1	1:1 to 75:1	1:1 to 14:1
Compound 47	thiobencarb	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	topramazone	1:6 to 168:1	1:2 to 56:1	1:1 to 11:1
Compound 47	tralkoxydim	1:68 to 17:1	1:22 to 6:1	1:8 to 2:1
Compound 47	triallate	1:768 to 2:1	1:256 to 1:2	1:96 to 1:11
Compound 47	triasulfuron	1:5 to 224:1	1:1 to 75:1	1:1 to 14:1
Compound 47	triaziflam	1:171 to 7:1	1:57 to 3:1	1:21 to 1:3
Compound 47	tribenuron	1:3 to 336:1	1:1 to 112:1	2:1 to 21:1
Compound 47	triclopyr	1:192 to 6:1	1:64 to 2:1	1:24 to 1:3
Compound 47	trifloxysulfuron	1:2 to 420:1	1:1 to 140:1	2:1 to 27:1
Compound 47	trifluralin	1:288 to 4:1	1:96 to 2:1	1:36 to 1:4
Compound 47	triflusulfuron	1:17 to 68:1	1:5 to 23:1	1:2 to 5:1
Compound 47	tritosulfuron	1:13 to 84:1	1:4 to 28:1	1:1 to 6:1

Table Number	Component (a) Column Entries
A2	Compound 50
A3	Compound 52
A4	Compound 59
A5	Compound 75
A6	Compound 81
A7	Compound 82
A8	Compound 83
A9	Compound 85
A10	Compound 87
A11	Compound 96
A12	Compound 97
A13	Compound 107
A14	Compound 118
A15	Compound 128
A16	Compound 133
A17	Compound 169
A18	Compound 175
A19	Compound 186
A20	Compound 218
A21	Compound 240
A22	Compound 243

INDEX TABLE A a Mass spectra are reported as the molecular weight of the highest isotopic abundance parent ion (M + 1) formed by addition of H + (molecular weight of 1) to the molecule, observed by mass spectrometry using atmospheric pressure chemical ionization (AP + ) unless otherwise noted. b1 H NMR data are reported in CDCl 3 at 400 MHz unless otherwise noted; s means singlet, br s means broad singlet, d means doublet, dd means doublet of doublet, ddd means doublet of double of doublets, ddt means doublet of doublet of triplets, t means triplet, td means triplet of doublets, q means quartet, quin means quintet and sxt means sextet.

Cmpd	R 1	R 2	R 3	m.p.(° C.)
1	CH 3	c-Pr	OH	*
2 (Ex. 1)	Ph	Ph	OH	* **
3	Et	c-Pr	OH	*
4	Ph(4-OMe)	Ph	OH	*
7	Ph	Et	OH	*
8	Ph(4-Me)	Ph	OH	*
9	Ph(3-Cl)	Ph	OH	101-102
10	Ph(2-Cl)	Ph	OH	142-143
11	Ph(4-Cl)	Ph	OH	83-85
12	Ph(2-Me)	Ph	OH	181-182
13	Ph(4-Cl)	Ph	O − K +	105-108
14	Ph	Ph	O − K +	128-130
15	Ph(2-OMe)	Ph	OH	178-179
17 (Ex. 2)	—CH 2 Ph	Ph	OH	57-58 **
18	Ph(3-Me)	Ph	OH	77-78
19	Ph(3-OMe)	Ph	OH	87-88
22	Ph(3-F)	Ph	OH	72-74
23	—CH 2 CH═CH 2	Ph	OH	38-40
24	Ph(4-F)	Ph	OH	131-132
25	Ph	Ph(4-Cl)	OH	*
26	Ph(2-F)	Ph	OH	142-144
27	Ph(2,3-di-Me)	Ph	OH	155-157
28	Ph(2,4-di-Me)	Ph	OH	186-187
29	Ph(2,5-di-Me)	Ph	OH	169-171
30	Ph	SMe	OH	92-94
31	Ph(2,6-di-Me)	Ph	OH	177-178
32	Ph(3,4-di-Me)	Ph	OH	165-166
33	Ph(3,5-di-Me)	Ph	OH	156-157
34	Ph	Ph(3-Cl)	OH	131-135
35	Ph	Ph(2-Cl)	OH	138-142
36	Ph(2-Me)	Ph(3-Cl)	OH	82-83
37	Ph(2-Br)	Ph	OH	170-171
38	Ph(3-Br)	Ph	OH	105-107
39	Ph(4-Me)	Ph(3-Cl)	OH	78-80
40	Ph(3-Cl-2-Me)	Ph	OH	170-171
41	Ph(2-Cl-4-Me)	Ph	OH	183-184
42	Ph	n-Bu	OH	145-147
43	Ph(4-Cl-2-Me)	Ph	OH	172-173
44	Ph(5-F-2-Me)	Ph	OH	169-170
45	Ph(3-Me)	Ph(3-Cl)	OH	69-70
46	Ph(2-Cl-6-Me)	Ph	OH	180-181
47 (Ex. 5)	Ph(3-F-2-Me)	Ph	OH	168-169
48	Ph(4-F-2-Me)	Ph	OH	153-155
49	Et	Ph	OH	62-66
50	n-Pr	Ph	OH	106-108
51	Ph(2-F-5-Me)	Ph	OH	159-161
52	Ph(5-Cl-2-Me)	Ph	OH	165-166
53	Ph(4-F-3-Me)	Ph	OH	152-153
54	Ph	n-hex	OH	138-140
55	Me	Ph	OH	152-154
56	Ph	3-thienyl	OH	*
57	Ph(2,4-di-F)	Ph	OH	153-154
58	Ph(2-F,3-Me)	Ph	OH	161-162
59	—CH 2 (tetrahydrofuran-2yl)	Ph	OH	155-156
60	Ph	i-Pr	OH	*
61	—CH 2 C≡CH	Ph		151-153
62	Ph(2-Me)	n-Bu	OH	100-101
63	Ph(3-Me)	n-Bu	OH	136-137
64	Ph(4-Cl)	Ph(3-Cl)	OH	140-142
65	Ph	2-thienyl(5-Cl)	OH	*
66	Ph	2-thienyl	OH	*
67	Ph(4-Me)	n-Bu	OH	143-144
68	Ph	i-Bu	OH	*
69	Ph	Ph(3-Br)	OH	*
70	Ph	Ph(4-Br)	OH	*
71	Ph	Ph(2-Br)	OH	*
72	n-Pr	n-Pr	OH	95-97
73	Ph(2-Me)	n-Pr	OH	127-128
74	—CH 2 (tetrahydrofuran-2-yl)	n-Pr	OH	95-96
75	n-Bu	n-Pr	OH	88-89
76	Ph	furan-2-yl	OH	*
77	n-Pr	2-thienyl	OH	*
78	Ph	n-pentyl	OH	*
79	Ph(3-Me)	n-Pr	OH	140-142
80	Ph	Ph(4-Me)	OH	164-169
81	—CH 2 CH 2 CH 2 OCH 3	Ph	OH	121-122
82	Ph	Ph(2-Me)	OH	165-167
83	Ph	Ph	OC(═O)-i-Bu	175-176
84	—CH 2 (Ph(3,4-di-OMe))	n-Pr	OH	*
85	—CH 2 CH 2 OCH 3	Ph	OH	135-137
86	n-Bu	Ph	OH	*
87	Ph	c-Pr	OH	*
88	Ph	Ph	OC(═O)-c-Pr	167-168
89	n-pentyl	Ph	OH	100-102
90	c-Pr	Ph	OH	172-174
91	—CH 2 CH 2 OCH 2 CH 2 OCH 3	Ph	OH	138-139
92	Ph	c-pentyl	OH	*
93	n-Pr	3-thienyl	OH	*
94	n-hex	Ph	OH	95-97
95	i-Pr	Ph	OH	163-165
96	—CH 2 CH 2 OCH 2 CH 3	Ph	OH	129-131
97 (Ex. 10)	—CH 2 CH 2 OCH 3	3-thienyl	OH	103-105
98	—CH 2 (tetrahydrofuran-2-yl)	3-thienyl	OH	*
99	c-hex	3-thienyl	OH	*
100	n-Pr	Ph(3-OMe)	OH	*
101	n-Pr	Ph(2-F)	OH	136-138
102	n-Pr	Ph(4-F)	OH	100-103
103	Bn	n-Pr	OH	*
104	—CH 2 (Ph(3-OMe))	n-Pr	OH	*
105	—CH 2 (Ph(3-OCF 3 ))	n-Pr	OH	*
106	Ph	c-hex	OH	*
107	—CH(CH 3 )CH 2 OCH 3	Ph	OH	122-123
108	—CH 2 CH 2 OCH 3	2-thienyl	OH	*
109	—CH 2 (tetrahydrofuran-2-yl)	2-thienyl	OH	*
110	n-Pr	furan-2-yl	OH	*
111	—CH 2 CH 2 OCH 3	furan-2-yl	OH	*
112	n-Pr	Ph(4-OMe)	OH	*
113 (Ex. 7)	Ph	3-pyridinyl	OH	**
114	Ph	c-Bu	OH	*
115	Et	Ph(3-Me)	OH	*
116	n-Bu	Ph(3-Me)	OH	*
117	—CH 2 CH 2 OCH 3	Ph(3-Me)	OH	*
118	—CH 2 CH 2 CH 2 OCH 3	Ph(3-Me)	OH	*
119	—CH 2 CH 2 OCH 3	Ph(3,5-di-F)	OH	154-178
120	—CH 2 CH 2 CH 2 OCH 3	Ph(3,5-di-F)	OH	139-140
121	n-Bu	Ph(3,5-di-F)	OH	144-145
122	Et	Ph(3,5-di-F)	OH	162-165
123	—CH 2 CH 2 OCH 3	Ph(3-F)	OH	*
124	Et	Ph(3-F)	OH	*
125	n-Bu	Ph(3-F)	OH	*
126	—CH 2 CH 2 CH 2 OCH 3	Ph(3-F)	OH	*
127	n-Pr	Ph(3-F)	OH	*
128 (Ex. 11)	c-hex	Ph	OH	160-163
				**
129	tetrahydropyran-4-yl	Ph	OH	*
130	c-heptyl	Ph	OH	*
131	c-pentyl	Ph	OH	*
132	Ph(4-F-3-Me)	Ph(3-Br)	OH	*
133	Ph(4-F-3-Me)	Ph(3-Cl)	OH	*
134	n-Pr	Ph(4-Br)	OH	*
135	n-Pr	1-Me-pyrazol-3-yl	OH	*
136	—CH 2 CH 2 OCH 3	1-Me-pyrazol-3-yl	OH	*
137	Et	Ph(3-Br)	OH	141-145
138	n-Bu	Ph(3-Br)	OH	112-113
139	—CH 2 CH 2 OCH 3	Ph(3-Br)	OH	115-116
140	—CH 2 CH 2 CH 2 OCH 3	Ph(3-Br)	OH	118-119
141	n-Pr	Ph(3-Br)	OH	134-137
142	—CH 2 (tetrahydrofuran-2-yl)	Ph(3-Cl)	OH	*
143	—CH 2 CH 2 CH 2 OCH 3	Ph(3-Cl)	OH	*
144	Ph(5-Cl-2-Me)	Ph(3-Br)	OH	*
145	Et	Ph(3-Cl)	OH	114-115
146	n-Bu	Ph(3-Cl)	OH	104-112
147	—CH 2 CH 2 OCH 3	Ph(3-Cl)	OH	124-125
148	Ph(5-Cl-2-Me)	Ph(3-Cl)	OH	*
149	n-Pr	1,4-benzodioxan-6-yl	OH	*
150	n-Pr	naphthalen-2-yl	OH	*
151	Ph(4-OMe)	Ph(3-Cl)	OH	154-156
152	n-Pr	Ph(3,5-di-F)	OH	*
153	n-Pr	c-Pr	OH	163-165
154	Ph(5-F-2-Me)	Ph(3-Br)	OH	*
155	n-Pr	Ph(3-CF 3 )	OH	129-131
156	n-Pr	Ph(3,5-di-Me)	OH	161-163
157	Ph(5-F-2-Me)	Ph(3-Cl)	OH	*
158	Ph(4-Et)	Ph(3,5-di-F)	OH	181-182
159	Ph(2-Me)	Ph(3,5-di-F)	OH	166-168
160	c-hex	c-Pr	OH	173-175
161	Ph	Ph(3,5-di-F)	OH	147-148
162	Ph(4-Me)	Ph(3,5-di-F)	OH	191-192
163	—CH 2 -c-hex	Ph(3,5-di-F)	OH	*
164	tetrahydrothiopyran-4-yl	Ph	OH	*
165	c-dodecahexyl	Ph	OH	*
166	Ph(4-F-2-Me)	Ph(3-Br)	OH	*
167	Ph(4-F-2-Me)	Ph(3-Cl)	OH	*
168 (Ex. 8)	(cis/trans)-tetrahydro-1-oxido-2H-	Ph	OH	**
	thiopyran-4-yl
169 (Ex. 8)	(trans/cis)-tetrahydro-1-oxido-2H-	Ph	OH	**
	thiopyran-4-yl
170	—CH 2 C≡CH	Ph(3,5-di-F)	OH	*
171	—CH 2 CH 2 OCH 2 CH 2 OCH 3	Ph(3,5-di-F)	OH	*
172	n-Pr	Ph(3-Me)	OH	116-117
173	n-Pr	Ph(3,5-di-Cl)	OH	97-100
174	Ph(4-Et)	Ph(3-Cl)	OH	146-148
175	Ph(4-Et)	Ph(3-Br)	OH	126-129
176	Ph(4-OMe)	Ph(3-Br)	OH	120-124
177	Ph(4-Et)	Ph(3-Br)	OH	139-142
178	Ph(5-F-2-Me)	Ph(3-Me)	OH	*
179	Ph(5-Cl-2-Me)	Ph(3,5-di-F)	OH	*
180	—CH 2 (tetrahydrofuran-2-yl)	Ph(3,5-di-F)	OH	*
181	c-hex	Ph(3,5-di-F)	OH	*
182	—CH 2 CH 2 OCH 2 CH 3	Ph(3,5-di-F)	OH	*
183	Ph(5-F-2-Me)	Ph(3,5-di-F)	OH	*
184	Ph(5-Cl-2-Me)	Ph(3-F)	OH	*
185	c-hex	Ph(3-Me)	OH	*
186	tetrahydropyran-4-yl	3-thienyl	OH	*
187	c-hex	Ph(3-F)	OH	*
188	c-hex	furan-2-yl	OH	*
189	c-hex	2-thienyl	OH	*
190	n-Pr	Ph(3-Cl)	OH	123-125
191	Ph(4-F-3-Me)	Ph(3-F)	OH	*
192	Ph(4-F-2-Me)	Ph(3-Me)	OH	*
193	n-Bu	c-Pr	OH	140-142
194	c-hex	Ph(3-Et)	OH	*
195	c-hex	Ph(3-CF 3 )	OH	*
196	c-hex	Ph(3-OMe)	OH	*
197	c-hex	Ph(4-F)	OH	*
198	c-hex	Ph(3,4-di-F)	OH	*
199	Ph	Ph(3-F)	OH	*
200	Et	Bn	OH	*
201	Ph(2-Me)	Ph(3-F)	OH	*
202	Ph(4-Me)	Ph(3-F)	OH	*
203	Ph(4-OMe)	Ph(3-F)	OH	*
204	Ph(4-Et)	Ph(3-F)	OH	*
205	c-hex	Ph(3,4,5-tri-F)	OH	*
206	c-hex	Ph(3-Br)	OH	*
207	—CH 2 CH 2 CF 3	Ph	OH	*
208	—CH 2 CH 2 CF 3	Ph(3-F)	OH	69-70
209	Ph(2-Me)	Ph(3-Br)	OH	144-146
210	Ph(2-Me)	Ph(3-Me)	OH	152-154
211	Ph(4-Me)	Ph(3-Me)	OH	146-148
212	Ph(4-OMe)	Ph(3-Me)	OH	156-158
213	Ph(4-Et)	Ph(3-Me)	OH	147-148
214	—CH 2 CH 2 CHCH 2	Ph	OH	124-127
215	c-octyl	Ph	OH	*
216	c-hex	Ph(4-acetylene)	OH	*
217	Ph	n-Pr	OH	145-147
218	Ph(3,4-di-OMe)	Ph	OH	164-165
219	Ph(4-Et)	Ph	OH	160-162
220	Ph(3-Et)	Ph	OH	126-127
255	Ph(2-Et)	Ph	OH	171-172
256	Ph(2,4-diOMe)	Ph	OH	182-183
257	—CH 2 CH 2 CH 2 CH 2 CH 2 —	OH	*
* See Index Table J for M.S. or 1 H NMR data.
** See synthesis examples for 1 H NMR data.
INDEX TABLE B
Cmpd	R 1	R 2	R 3	m.p. (° C.)
16	Ph	Ph	OS(O) 2 Ph(4-Me)	63-65
20 (Ex. 3)	—CH 2 Ph	Ph	OH	56-57 **
21 (Ex. 4)	—CH 2 Ph	Ph	OS(O) 2 Ph(4-Me)	52-53 **
221	n-Pr	2-thienyl	OH	*
* See Index Table J for M.S. or 1 H NMR data.
** See synthesis example for 1 H NMR data.
INDEX TABLE C
	Cmpd	R 1	R 2	m.p. (° C.)
	222	Ph(2,5-di-Me)	Ph	*
	223 (Ex. 6)	Ph	Ph	**
	* See Index Table J for M.S. or 1 H NMR data.
	** See synthesis examples for 1 H NMR data.
INDEX TABLE D
Cmpd	R 1	R 2	R 3	m.p. (° C.)
224	n-Pr	Ph(3,5-di-F)	OH	*
225	Ph	Ph	OH	125-127
* See Index Table J for M.S. or 1 H NMR data.
INDEX TABLE E
Cmpd	R 1	R 2	R 3	m.p.(° C.)
226	n-Pr	Ph	OH	*
227	n-Pr	3-thienyl	OH	*
228	—CH 2 CH 2 OCH 3	3-thienyl	OH	*
229	—CH 2 (tetrahydrofuran-	3-thienyl	OH	*
	2-yl)
230	n-Pr	furan-2-yl	OH	*
231	Et	Ph(3-Me)	OH	*
232	n-Bu	Ph(3-Me)	OH	*
233	—CH 2 CH 2 OCH 3	Ph(3-Me)	OH	*
234	Ph(3-F-2-Me)	Ph	OH	*
235	—CH 2 CH 2 OCH 3	Ph(3-F)	OH	*
236	Et	Ph(3-F)	OH	*
237	n-Bu	Ph(3-F)	OH	*
238	—CH 2 CH 2 CH 2 OCH 3	Ph(3-F)	OH	*
239	Et	Ph	OH	*
240	n-Bu	Ph	OH	*
241	n-Pr	1,4-benzodioxan-6-yl	OH	*
242	n-Pr	naphthalen-2-yl	OH	*
243 (Ex. 9)	—CH 2 CH 2 OCH 3	Ph(3,5-di-F)	OH	**
244	—CH 2 CH 2 CH 2 OCH 3	Ph(3,5-di-F)	OH	*
245	n-Bu	Ph(3,5-di-F)	OH	*
246	Ph	Ph(3,5-di-F)	OH	158-159
247	c-dodecahexyl	Ph	OH	*
248	c-hex	Ph	OH	*
249	tetrahydropyran-4-yl	Ph	OH	*
250	—CH 2 (tetrahydrofuran-	Ph	OH	*
	2-yl)
251	c-hex	Ph(3,4,5-tri-F)	OH	*
252	c-hex	Ph(3-Br)	OH	*
253	c-heptyl	Ph	OH	*
254	c-hex	Ph(4-acetylene)	OH	*
* See index table J for 1 H NMR.
** See synthesis example for 1 H NMR data.
INDEX TABLE F
Cmpd	R 1	R 2	m.p. (° C.)
2Q (Ex. 1)	Ph	Ph	**
17Q (Ex. 2)	—CH 2 Ph	Ph	**
23Q	—CH 2 CH═CH 2	Ph	*
47Q (Ex. 5)	Ph(3-F-2-Me)	Ph	**
59Q	—CH 2 (tetrahydrofuran-2yl)	Ph	*
61Q	—CH 2 C≡CH	Ph	*
76Q	Ph	2-furanyl	*
84Q	—CH 2 (Ph(3,4-di-OMe))	n-Pr	*
105Q	—CH 2 (Ph(3-OCF 3 ))	n-Pr	*
113Q (Ex. 7)	Ph	3-pyridinyl	**
153Q	n-Pr	c-Pr	*
163Q	—CH 2 -c-hex	Ph(3,5-di-F)	*
212Q	Ph(4-OMe)	Ph(3-Me)	*
257Q	—CH 2 CH 2 CH 2 CH 2 CH 2 —	*
* See Index Table J for MS or 1 H NMR data.
** See synthesis examples for 1 H NMR data.
INDEX TABLE G
	Cmpd	R 1	R 2	m.p. (° C.)
	20Q (Ex. 3)	—CH 2 Ph	Ph	**
	** See synthesis example for 1 H NMR data.
INDEX TABLE H
			m.p.
Cmpd	R 1	R 2	(° C.)
2R (Ex. 1)	Ph	Ph	**
17R (Ex. 2)	—CH 2 Ph	Ph	**
23R	—CH 2 CH═CH 2	Ph	*
47R (Ex. 5)	Ph(3-F-2-Me)	Ph	**
59R	—CH 2 (tetrahydrofuran-2-yl)	Ph	*
61R	—CH 2 C≡CH	Ph	*
76R	Ph	2-furanyl	*
84R	—CH 2 (Ph(3,4-di-OMe))	n-Pr	*
105R	—CH 2 (Ph(3-OCF 3 ))	n-Pr	*
97R (Ex. 10)	—CH 2 CH 2 OCH 3	3-thienyl	**
118R	—CH 2 CH 2 CH 2 OCH 3	Ph(3-Me)	*
113R (Ex. 7)	Ph	3-pyridinyl	**
135R	n-Pr	1-Me-pyrazol-3-yl	*
128R (Ex. 11)	c-hex	Ph	**
153R	n-Pr	c-Pr	*
163R	—CH 2 -c-hex	Ph(3,5-di-F)	*
164R	tetrahydrothiopyran-4-yl	Ph	*
186R	tetrahydropyran-4-yl	3-thienyl	*
212R	Ph(4-OMe)	Ph(3-Me)	*
216R	c-hex	Ph(4-acetylene)	*
242R	n-Pr	naphthalene-2-yl	*
247R	c-dodecahexyl	Ph	*
243R (Ex. 9)	—CH 2 CH 2 OCH 3	Ph(3,5-di-F)	**
257R	—CH 2 CH 2 CH 2 CH 2 CH 2 —	*
* See Index Table J for MS or 1 H NMR data.
** See synthesis examples for 1 H NMR data.
INDEX TABLE I
				m.p.
Cmpd	R 1	R 2	R 23	(° C.)
2S (Ex. 1)	Ph	Ph	Et	**
17S (Ex. 2)	—CH 2 Ph	Ph	Et	**
23S	—CH 2 CH═CH 2	Ph	Et	*
59S	—CH 2 (tetrahydrofuran-	Ph	Et	*
	2-yl)
61S	—CH 2 C≡CH	Ph	Et	*
84S	—CH 2 (Ph(3,4-di-OMe))	n-Pr	Et	*
105S	—CH 2 (Ph(3-OCF 3 ))	n-Pr	Et	*
97S (Ex. 10)	—CH 2 CH 2 OCH 3	3-thienyl	Et	**
118S	—CH 2 CH 2 CH 2 OCH 3	Ph(3-Me)	Et	*
113S (Ex. 7)	Ph	3-pyridinyl	Et	**
135S	n-Pr	1-Me-pyrazol-	Et	*
		3-yl
128S (Ex. 11)	c-hex	Ph	Et	**
153S	n-Pr	c-Pr	Me	*
163S	—CH 2 -c-hex	Ph(3,5-di-F)	Et	*
164S	tetrahydrothiopyran-4-yl	Ph	Et	*
186S	tetrahydropyran-4-yl	3-thienyl	Et	*
212S	Ph(4-OMe)	Ph(3-Me)	Et	*
216S	c-hex	Ph(4-acetylene)	Et	*
242S	n-Pr	naphthalene-2-yl	Et	*
247S	c-dodecahexyl	Ph	Et	*
243S (Ex. 9)	—CH 2 CH 2 OCH 3	Ph(3,5-di-F)	Et	**
257S	—CH 2 CH 2 CH 2 CH 2 CH 2 —	Et	*
* See Index Table J for MS or 1 H NMR data.
** See synthesis examples for 1 H NMR data.
INDEX TABLE J
Cmpd	Mass spectra data a or 1 H NMR data b
1	289
3	303
4	417
7	339
8	401
25	421
56	393
60	353 (ESI, M + 1)
65	427
66	393
68	367 (ESI, M + 1)
	(500 MHz) δ 16.38 (s, 1H), 8.14 (s, 1H), 7.45 (t, 1H), 7.34 (dd, 1H), 7.32-7.23 (m, 3H), 7.10-7.05 (m,
69	3H), 7.01-6.95 (m, 1H), 2.64 (t, 2H), 2.40 (t, 2H), 1.96 (dd, 2H).
70	465
71	463 (AP, M − H)
76	377
77	359
78	381 (ESI, M + H)
84	425 (AP, M − H)
86	367
87	351 (ESI, M + H)
92	379 (ESI, M + H)
93	359
98	401
99	399
100	381 (EST, M − H)
103	δ 16.41 (s, 1H), 8.09 (s, 1H), 7.42 (m, 3H), 7.21 (m, 2H), 5.29 (s, 2H), 2.79 (m, 2H), 2.77 (m, 2H),
	2.65 (m, 2H), 2.15 (m, 2H), 1.75 (m, 2H), 0.94 (t, 3H).
104	δ 16.22 (s, 1H), 8.07 (s, 1H), 7.25 (m, 1H), 6.77 (m, 3H), 5.29 (s, 2H), 3.81 (s, 3H), 2.79 (m, 2H), 2.64
	(m, 2H), 2.55 (m, 2H), 2.15 (m, 2H), 1.65 (m, 2H), 0.95 (t, 3H).
105	δ 16.41 (s, 1H), 8.06 (s, 1H), 7.41 (m, 1H), 7.14 (m, 3H), 5.32 (s, 2H), 2.81 (m, 2H), 2.62 (m, 2H),
	2.52 (m, 2H), 2.15 (m, 2H), 1.81 (m, 2H), 0.95 (t, 3H).
106	393 (ESI, M + H)
108	375
109	401
110	343
111	359
112	382
114	365 (ESI, M + H)
115	353
116	381
117	383
118	397
123	387
124	357
125	385
126	401
127	δ 8.09 (s, 1H), 7.55-7.46 (m, 1H), 7.33-7.20 (m, 3H), 3.94-3.83 (m, 2H), 2.74 (t, 2H), 2.51 (t, 2H),
	2.08 (quin, 2H), 1.63 (sxt, 2H), 0.78 (t, 3H).
129	395
130	407
131	379
132	495 (AP, M − H)
133	453
134	431 (ESI, M + H)
135	357
136	373
142	429
143	417
144	(500 MHz) δ 16.32 (br s, 1H), 8.22 (s, 1H), 7.55 (s, 1H), 7.46 (d, 1H), 7.25-7.06 (m, 5H), 2.70 (br s,
	2H), 2.46 (d, 2H), 2.14 (s, 3H), 2.08-2.00 (m, 2H)
148	469
149	411
150	403
152	389
154	497
157	453
163	443
164	411
165	477
166	495 (AP, M − H)
167	453
170	385
171	449
178	433
179	471
180	431
181	429
182	419
183	455
184	453
185	δ 16.65 (br s, 1H), 8.00 (s, 1H), 7.20-7.40 (m, 4H), 3.90-4.00 (m, 1H), 0.90-2.80 (m, 19H).
186	401
187	411
188	383
189	399
191	437
192	433
194	421
195	461
196	423
197	411
198	429
199	403 (AP, M − H)
200	353
201	417 (AP, M − H)
202	417 (AP, M − H)
203	433 (AP, M − H)
204	431 (AP, M − H)
205	447
206	471
207	405 (AP, M − H)
215	421
216	417
221	359
222	412
224	417
226	379
227	385
228	401
229	427
230	369
231	379
232	407
233	409
234	445
235	413
236	383
237	411
238	427
239	365
240	393
241	437
242	429
244	445
245	429
247	503
248	419
249	421
250	δ 16.75 (d, 1H), 8.09 (s, 1H), 7.53 (m, 2H), 7.49 (m, 3H), 4.35 (m, 3H), 3.85 (m, 1H), 3.61 (m, 1H),
	3.31 (m, 1H), 3.15 (m, 1H), 2.95 (m, 1H), 2.20-1.20 (m, 9H).
251	473
252	497
253	433
254	443
257	δ 16.60 (s, 1H), 7.94 (s, 1H), 4.32 (m, 2H), 3.02 (m, 2H), 2.74 (m, 2H), 2.45 (m, 2H), 2.06 (m, 2H),
	1.85 (m, 4H), 1.8 (m, 2H).
23Q	δ 8.80 (s, 1H), 7.46-7.66 (m, 5H), 6.04 (m, 1H), 5.86-5.98 (m, 1H), 5.26 (m, 1H), 5.02 (m, 1H), 4.62
	(m, 2H), 2.69 (m, 2H), 2.42 (m, 2H), 2.12 (m, 2H).
59Q	δ 8.78 (s, 1H), 7.49-7.57 (m, 5H), 6.03 (s, 1H), 4.28-4.39 (m, 2H), 3.94 (m, 1H), 3.59 (m, 1H), 3.33
	(m, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.12 (m, 2H), 1.99 (m, 1H), 1.76 (m, 1H), 1.57-1.66 (m, 1H),
	1.39 (m, 1H).
61Q	δ 8.81 (s, 1H), 7.77 (m, 2H), 7.57 (m, 3H), 6.04 (s, 1H), 4.69 (m, 2H), 2.69 (m, 2H), 2.46 (m, 3H),
	2.12 (m, 2H).
76Q	δ 8.91 (s, 1H), 7.60 (m, 3H), 7.56 (m, 1H), 7.28 (dd, 2H), 6.35 (dd, 1H), 6.03 (s, 1H), 5.75 (d, 1H),
	2.66 (t, 2H), 2.44 (m, 2H), 2.09 (m, 2H).
84Q	δ 8.71 (s, 1H), 6.80 (m, 2H), 6.78 (d, 1H), 6.01 (s, 1H), 5.34 (s, 2H), 3.86 (d, 6H), 2.8 (m, 2H), 2.75
	(m, 2H), 2.45 (m, 2H), 2.20 (m, 2H), 1.80 (m, 2H), 1.00 (t, 3H).
105Q	δ 8.74 (s, 1H), 7.40 (m, 1H), 7.20 (m, 1H), 7.15 (m. 1H), 7.00 (s, 1H), 6.00 (s, 1H), 5.40 (s, 2H), 2.78
	(m, 2H), 2.72 (m, 2H), 2.40 (m, 2H), 2.15 (m, 2H), 1.80 (m, 2H), 0.94 (m, 3H).
153Q	(300 MHz) δ 8.57 (s, 1H), 5.98 (s, 1H), 4.25-4.19 (m, 2H), 2.67-2.63 (m, 2H), 2.45-2.41 (m, 2H),
	2.13-1.92 (m, 3H), 1.86-1.78 (m, 2H), 1.42-1.37 (m, 2H), 1.26-1.20 (m, 2H), 1.07-1.02 (m, 3H).
163Q	(500 MHz) δ 8.72 (s, 1H), 7.13-6.95 (m, 3H), 6.03 (s, 1H), 3.98 (d, 2H), 2.69 (td, 2H), 2.53-2.39 (m,
	2H), 2.12 (quin, 2H), 1.75 (ddt, 1H), 1.66-1.57 (m, 3H), 1.50-1.43 (m, 2H), 1.19-0.99 (m, 3H), 0.77-
	0.66 (m, 2H).
212Q	δ 8.86 (s., 1H), 7.07-7.32 (m, 4H), 6.80-7.06 (m, 4H), 6.04 (s., 1H), 3.78 (s, 3H), 2.67 (m, 2H), 2.44
	(m, 2H), 2.27 (s, 3H), 2.11 (m, 2H).
257Q	δ 8.60 (s, 1H), 6.00 (s, 1H), 4.40 (m, 2H), 3.15 (m, 2H), 2.66 (m, 2H), 2.44 (m, 2H), 2.15 (m, 2H),
	1.85 (m, 6H).
23R	δ 9.03 (s, 1H), 7.42-7.76 (m, 5H), 5.82-6.04 (m, 1H), 5.42 (m, 1H), 5.04 (m, 1H), 4.72 (m, 2H).
59R	δ 9.00 (s, 1H), 7.48-7.60 (m, 5H), 4.35 (m, 1H), 4.24-4.32 (m, 1H), 4.06 (m, 1H), 3.53-3.65 (m, 1H),
	3.29-3.41 (m, 1H), 2.02 (m, 1H), 1.79 (m, 1H), 1.57-1.69 (m, 1H), 1.41 (m, 1H).
61R	δ 13.02 (br s, 1H), 8.65 (s, 1H), 7.73 (m, 2H), 7.62 (m, 3H), 4.58 (m, 2H), 3.44 (m, 1H).
76R	δ 12.64 (br s, 1H), 9.11 (s, 1H), 7.66 (m, 3H), 7.56 (d, 1H), 7.33 (m, 2H), 6.39 (dd, 1H), 5.93 (d, 1H).
84R	δ 13.00 (br s, 1H), 8.92 (s, 1H), 6.80 (d, 1H), 6.79 (s, 1H), 6.85 (d, 1H), 5.34 (s, 2H), 3.87 (d, 6H),
	2.80 (m, 2H), 1.80 (m, 2H), 1.01 (t, 3H).
105R	δ 12.8 (br s, 1H), 8.94 (s, 1H), 7.45 (m, 1H), 7.25 (m, 1H), 7.15 (m, 1H), 7.05 (s, 1H), 5.41 (s, 2H),
	2.77 (m, 2H), 1.88 (m, 2H), 0.99 (t, 3H).
118R	δ 8.98 (s, 1H), 7.42 (m, 2H), 7.33 (m, 2H), 4.26 (m, 2H), 3.31 (t, 3H), 3.16 (s, 3H), 2.45 (s, 3H), 1.95
	(m, 3H).
135R	δ 13.33 (s, 1H), 8.95 (s, 1H), 7.50 (d, 1H), 7.11 (d, 1H), 4.69 (m, 2H), 4.04 (s, 3H), 1.86 (m, 2H), 1.01
	(t, 3H).
153R	(300 MHz) δ 13.15 (br s, 1H), 8.76 (s, 1H), 4.31-4.25 (m, 2H), 2.04-1.99 (m, 1H), 1.90-1.80 (m, 2H),
	1.45-1.41 (m, 2H), 1.31-1.25 (m, 2H), 1.09 (t, 3H).
163R	(500 MHz) δ 12.77 (br s, 1H), 7.19-6.94 (m, 3H), 4.08 (d, 2H), 1.86-1.52 9m, 4H), 1.44 (d, 2H), 1.22-
	0.95 (m, 3H), 0.82-0.63 (m, 2H).
164R	δ 13.12 (br s, 1H), 8.95 (s, 1H), 7.59 (m, 3H), 7.46 (m, 2H), 4.09 (s, 1H), 3.08 (d, 2H), 2.69 (d, 2H),
	2.46 (m, 2H), 2.05 (m, 2H).
186R	δ 13.12 (br s, 1H), 8.93 (s, 1H), 7.83 (m, 1H), 7.58 (m, 1H), 7.29 (m, 1H), 4.56 (m, 1H), 4.09 (m, 2H),
	3.26 (m, 2H), 3.12 (m, 2H), 1.67 (m, 2H).
212R	δ 9.09 (s, 1H), 6.98-7.21 (m, 6H), 6.90 (d, 2H), 3.81 (s, 3H), 2.28 (s, 3H).
216R	δ 13.25 (br s, 1H), 8.93 (s, 1H), 7.67 (m, 2H), 7.48 (m, 2H), 4.06 (m, 1H), 3.28 (s, 1H), 2.68 (dd, 2H),
	1.85 (d, 2H), 1.73 (d, 2H), 1.63 (m, 1H), 1.24 (m, 1H), 1.05 (m, 2H).
242R	δ 13.14 (br s, 1H), 9.03 (s, 1H), 8.05 (m, 2H), 7.96 (d, 2H), 7.65 (ddd, 2H), 7.56 (dd, 1H), 4.14 (m,
	2H), 1.75 (m, 2H), 0.80 (t, 3H).
247R	δ 13.26 (br s, 1H), 8.96 (s, 1H), 7.57 (m, 3H), 7.46 (m, 2H), 4.45 (m, 1H), 2.32 (m, 2H), 1.99 (m, 2H),
	1.18 (m, 15H), 0.69 (m, 3H).
257R	δ 13.00 (br s, 1H), 8.75 (s, 1H), 4.42 (m, 2H), 3.10 (m, 2H), 1.82 (m, 6H)
23S	δ 8.70 (s, 1H), 7.49-7.53 (m, 5H), 5.85-5.97 (m, 1H), 5.25 (m, 1H), 4.95 (m, 1H), 4.59 (m, 2H), 4.41
	(m, 2H), 1.40 (m, 3H).
59S	δ 8.68 (s, 1H), 7.46-7.55 (m, 5H), 4.40 (m, 2H), 4.28-4.35 (m, 2H), 3.88 (m, 1H), 3.58 (m, 1H), 3.31
	(m, 1H), 1.91-2.02 (m, 1H), 1.52-1.81 (m, 4H), 1.39 (m, 3H).
61S	δ 8.72 (s, 1H), 7.76 (m, 2H), 7.55 (m, 3H), 4.66 (m, 2H), 4.42 (m, 2H), 2.41 (s, 1H), 1.42 (m, 3H).
84S	δ 8.62 (s, 1H), 6.81 (m, 2H), 6.70 (m, 1H), 5.29 (s, 2H), 4.39 (q, 2H), 3.86 (d, 6H), 2.76 (t, 2H), 1.73
	(m, 2H), 1.40 (t, 3H), 0.98 (t, 3H).
105S	δ 8.64 (s, 1H), 7.42 (m, 1H), 7.20 (m, 1H), 7.18 (m, 1H), 7.00 (s, 1H), 5.34 (s, 2H), 4.39 (m, 2H), 2.65
	(m, 2H), 1.75 (m, 2H), 1.40 (m, 3H), 0.95 (t, 3H).
118S	δ 8.66 (s, 1H), 7.38 (m, 2H), 7.29 (m, 2H), 4.40 (m, 2H), 4.11 (m, 2H), 3.30 (t, 2H), 3.15 (s, 3H), 2.43
	(s, 3H), 1.93 (m, 2H), 1.40 (t, 3H).
135S	δ 8.68 (s, 1H), 7.47 (d, 1H), 6.98 (d, 1H), 4.53 (m, 2H), 4.39 (q, 2H), 4.02 (s, 3H), 1.82 (m, 2H), 1.39
	(t, 3H), 0.96 (t, 3H).
153S	(300 MHz) δ 8.51 (s, 1H), 4.23-4.18 (m, 2H), 3.88 (s, 3H), 1.99-1.95 (m, 1H), 1.85-1.77 (m, 2H),
	1.36-1.32 (m, 2H), 1.21-1.17 (m, 2H), 1.03 (t, 3H).
163S	(500 MHz) δ 8.62 (s, 1H), 7.06-6.98 (m, 3H), 4.40 (q, 2H), 3.95 (d, 2H), 1.80-1.70 (m, 1H), 1.66-1.55
	(m, 3H), 1.46 (d, 2H), 1.40 (t, 3H), 1.17-0.96 (m, 3H), 0.70 (dd, 2H).
164S	δ 8.59 (s, 1H), 7.55 (m, 3H), 7.42 (m, 2H), 4.40 (q, 2H), 3.92 (m, 1H), 3.10 (d, 2H), 2.64 (d, 2H), 2.41
	(m, 2H), 1.98 (m, 2H), 1.40 (t, 3H).
186S	δ 8.57 (s, 1H), 7.71 (m, 1H), 7.52 (m, 1H), 7.24 (m, 1H), 4.39 (m, 3H), 4.04 (d, 2H), 3.17 (m, 4H),
	1.58 (m, 3H), 1.39 (t, 3H).
212S	δ 8.80 (s, 1H), 7.14-7.25 (m, 1H), 6.95-7.18 (m, 5 H), 6.82-6.92 (m, 2H), 3.94 (s, 3H), 3.78 (s, 3H),
	2.26 (s, 3H).
216S	δ 8.57 (s, 1H), 7.64 (m, 2H), 7.43 (m, 2H), 4.40 (q, 2H), 3.89 (m, 1H), 3.24 (s, 1H), 2.75 (dd, 2H),
	1.78 (d, 2H), 1.63 (m, 3H), 1.55 (d, 1H), 1.39 (t, 3H), 0.99 (m, 2H).
242S	δ 8.71 (s, 1H), 7.99 (m, 2H), 7.93 (d, 2H), 7.62 (m, 2H), 7.53 (dd, 1H), 4.42 (q, 2H), 4.01 (m, 2H),
	1.71 (m, 2H), 1.42 (t, 3H), 0.75 (t, 3H).
247S	δ 8.60 (s, 1H), 7.51 (m, 3H), 7.42 (m, 2H), 4.39 (q, 2H), 4.12 (m, 1H), 2.32 (m, 2H), 1.98 (m, 2H),
	1.39 (t, 3H), 1.18 (m, 12H), 1.02 (m, 3H), 0.66 (m, 3H).
257S	δ 8.47 (s, 1H), 4.34 (m, 4H), 3.02 (m, 2H), 1.82 (m, 6H), 1.36 (m, 3H).

TABLE A Postemergence

	1000 g ai/ha	500 g ai/ha
	Compound	Compounds
	217	1	2	3	4	7	8	9	10	11	12	13	14	15	16	17	18	19	20	21	22	23	24	25	26	27	28
Barnyardgrass	90	60	100	90	100	70	100	100	90	100	90	90	80	40	60	70	90	70	10	10	70	60	70	90	80	90	90
Corn	40	0	90	10	50	40	50	70	90	20	80	50	20	10	20	10	20	10	10	0	40	0	30	20	20	30	0
Crabgrass, Large	100	80	100	90	90	70	90	90	100	90	100	90	90	70	40	70	80	20	10	10	80	60	90	90	90	100	80
Foxtail, Giant	80	40	100	60	90	60	100	90	100	90	90	80	90	70	70	30	90	50	0	0	80	50	90	90	90	90	80
Morningglory	100	90	100	90	100	100	100	90	100	90	100	50	100	50	20	70	100	60	10	0	100	100	100	90	80	70	10
Pigweed	100	80	100	100	100	100	100	100	100	100	100	100	100	90	70	100	100	100	50	50	100	100	100	100	100	100	100
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	70	70	100	100	100	100	100	100	100
Wheat	40	20	20	10	60	40	50	40	60	0	0	60	0	20	10	10	50	0	0	0	0	0	30	0	0	0	0
	500 g ai/ha
	Compounds
	29	30	31	32	33	34	35	36	37	38	39	40	41	42	43	44	45	46	47	48	49	50	51	52	53	54
Barnyardgrass	90	30	80	80	100	100	60	100	90	90	90	90	90	90	90	100	100	90	100	90	90	100	90	90	100	60
Corn	10	0	20	10	20	30	10	60	40	60	40	50	10	30	50	40	20	20	70	30	20	30	80	70	80	10
Crabgrass, Large	90	60	90	90	100	100	80	100	100	100	90	100	70	80	90	90	90	90	100	100	90	90	100	100	100	70
Foxtail, Giant	90	40	90	90	100	100	80	100	90	90	90	100	80	70	80	90	90	90	100	100	80	90	90	100	90	60
Morningglory	90	50	70	100	90	100	80	100	100	100	90	100	70	80	80	90	100	70	100	100	100	80	100	100	100	100
Pigweed	100	80	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Velvetleaf	100	—	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Wheat	0	0	0	30	20	30	0	0	0	40	0	0	0	0	0	20	40	0	0	20	0	0	0	40	50	0
	500 g ai/ha
	Compounds
	55	56	57	58	59	60	61	62	63	64	65	66	67	68	69	70	71	72	73	74	75	76	77	78	79	80
Barnyardgrass	70	90	90	90	90	90	90	90	90	90	50	90	90	90	100	80	60	90	90	90	90	80	90	70	90	80
Corn	10	50	40	20	30	10	10	70	50	60	0	60	10	10	40	20	20	10	60	20	50	20	20	20	60	50
Crabgrass, Large	90	90	90	90	100	100	90	90	90	90	60	90	90	100	100	90	80	90	90	90	90	90	80	70	90	90
Foxtail, Giant	60	90	90	90	90	90	80	90	80	80	40	80	60	70	90	90	60	60	90	80	90	70	70	50	80	90
Morningglory	90	100	60	100	100	90	100	100	100	100	60	90	100	90	100	100	100	90	100	100	100	90	100	100	100	100
Pigweed	100	100	100	100	100	100	100	100	100	100	60	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Wheat	0	0	10	0	10	50	0	20	0	30	0	0	30	0	10	0	0	0	50	20	50	10	0	0	50	0
	500 g ai/ha
	Compounds
	81	82	83	84	85	86	87	88	89	90	91	92	93	94	95	96	97	98	99	100	101	102	103	104	105	106
Barnyardgrass	100	70	90	10	90	90	90	90	90	90	100	90	90	90	90	90	90	90	90	90	90	90	60	40	50	50
Corn	70	20	30	20	80	50	50	60	10	20	10	20	30	10	10	20	80	60	20	0	10	20	20	0	10	10
Crabgrass, Large	90	90	90	10	90	90	90	90	100	90	100	90	100	90	90	100	100	100	100	90	90	100	40	0	70	70
Foxtail, Giant	90	80	90	0	90	90	90	90	90	80	80	90	90	80	90	90	80	90	90	90	80	90	20	0	20	60
Morningglory	100	100	100	90	100	90	100	100	100	100	100	100	100	100	100	100	100	100	100	100	70	100	100	100	80	100
Pigweed	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	80	100	100
Wheat	30	0	0	0	40	50	60	0	20	40	50	0	0	0	0	20	20	20	0	30	0	10	0	0	0	0
	500 g ai/ha
	Compounds
	107	108	109	110	111	112	113	114	115	116	117	118	119	120	121	122	123	124	125	126	127	128	129	130	131	132
Barnyardgrass	90	90	90	90	90	90	90	90	90	100	90	90	90	90	100	80	90	90	90	90	90	100	100	100	90	90
Corn	50	40	30	10	30	20	60	50	20	10	50	30	70	50	40	30	70	20	20	60	20	60	50	50	30	40
Crabgrass, Large	90	90	100	90	90	90	100	90	90	80	100	90	90	100	100	90	90	90	90	90	90	90	90	100	90	70
Foxtail, Giant	90	90	90	50	90	80	100	80	80	90	80	90	90	90	90	80	80	70	90	80	80	90	90	90	90	70
Morningglory	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	80	100	100	100	100	100	100	90
Pigweed	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	90
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Wheat	10	0	0	0	0	10	60	0	0	0	30	10	60	70	60	50	20	0	10	20	0	20	20	30	0	30
	500 g ai/ha
	Compounds
	133	134	135	136	138	139	140	141	142	143	144	145	146	147	148	149	150	151	152	153	154	155	156	157	158	159
Barnyardgrass	90	60	30	80	90	80	90	90	90	90	100	100	100	90	100	90	80	90	100	90	90	100	90	100	90	100
Corn	40	20	0	0	20	40	20	30	20	20	30	40	30	30	60	30	0	10	50	20	10	40	20	30	50	70
Crabgrass, Large	100	80	70	90	90	80	90	90	90	90	90	90	90	90	90	70	50	70	100	90	100	90	80	100	100	90
Foxtail, Giant	90	70	0	50	90	80	90	90	80	80	90	80	90	80	90	80	70	70	100	80	90	90	90	100	90	100
Morningglory	70	60	90	100	100	100	100	100	100	100	70	90	90	100	100	100	100	100	100	60	70	100	100	30	100	100
Pigweed	100	80	90	100	100	100	100	100	100	90	90	100	100	100	100	100	60	100	100	100	100	100	100	100	100	100
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	90	100	100	100	100	100	100	100	100	100
Wheat	40	0	0	0	20	40	0	0	20	10	0	0	50	60	0	50	20	20	70	10	0	30	20	0	50	60
	500 g ai/ha
	Compounds
	160	161	162	163	164	165	166	167	168	169	170	171	172	173	174	175	176	177	178	179	180	181	182	183	184	185
Barnyardgrass	100	90	100	100	100	80	100	100	100	100	90	90	90	100	100	100	90	100	90	90	100	100	90	90	100	90
Corn	60	10	50	20	50	30	40	30	30	30	30	40	30	20	20	20	10	0	70	80	40	50	20	80	80	50
Crabgrass, Large	90	90	100	90	100	50	90	90	90	100	90	90	80	90	90	80	60	70	80	100	100	90	90	100	100	70
Foxtail, Giant	80	90	100	50	100	30	90	90	90	100	80	90	90	90	60	80	70	40	80	90	100	100	80	100	100	80
Morningglory	100	100	100	100	100	100	—	100	100	100	100	100	100	100	60	80	50	10	100	100	100	100	100	70	100	100
Pigweed	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	80	100	100	100	100	100	100	100
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	90	100	100	100	100	100	100	100	100	100
Wheat	50	0	50	0	20	0	0	0	50	20	20	50	20	60	0	0	0	0	30	80	30	60	50	80	50	0
	500 g ai/ha
	Compounds
	186	187	188	189	190	191	192	193	194	195	196	197	198	199	200	202	203	204	205	206	207	208	209	210	211	212
Barnyardgrass	90	100	90	90	100	100	90	100	100	90	90	100	100	100	10	100	100	100	100	100	90	90	100	90	100	100
Corn	60	50	10	40	0	50	40	40	10	20	40	50	30	50	0	30	30	10	20	0	30	20	40	0	20	0
Crabgrass, Large	90	100	90	90	90	100	80	100	90	90	90	100	100	100	10	100	70	100	90	100	90	80	100	30	80	30
Foxtail, Giant	90	90	80	90	90	100	70	100	50	70	100	100	90	100	10	100	80	100	90	90	90	80	100	70	80	40
Morningglory	100	100	100	100	100	100	70	100	100	—	100	100	100	100	60	100	100	100	100	100	80	100	100	100	100	100
Pigweed	100	100	100	100	100	90	80	100	100	100	100	100	100	100	80	100	100	100	100	100	100	90	100	100	90	100
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	70	70	70
Wheat	0	0	0	0	0	50	0	70	0	0	30	0	0	10	0	50	30	40	10	0	0	10	0	10	0	0
	500 g ai/ha
	Compounds
	213	214	215	216	218	219	220	221	222	223	224	225	226	227	228	229	230	231	232	233	234	235	236	237	238	239
Barnyardgrass	100	90	100	90	90	90	90	20	80	50	90	100	90	90	90	100	90	90	90	90	100	100	90	100	100	90
Corn	20	30	30	0	70	30	30	20	0	20	50	50	60	60	90	40	20	40	60	80	50	90	50	80	80	30
Crabgrass, Large	50	90	70	80	70	100	90	20	30	60	100	100	100	100	100	100	90	70	60	90	90	100	90	100	100	90
Foxtail, Giant	40	90	80	70	70	90	60	10	40	70	100	90	90	90	90	100	50	80	90	90	90	100	90	100	100	80
Morningglory	100	100	100	90	100	100	100	20	40	80	100	100	100	100	100	100	90	100	100	100	100	100	100	100	100	100
Pigweed	100	100	100	90	100	100	100	70	70	70	100	100	100	100	100	100	90	90	90	100	90	100	100	100	100	90
Velvetleaf	60	100	100	100	100	100	100	80	90	80	100	100	100	100	100	100	100	100	80	100	100	100	100	100	100	100
Wheat	0	20	0	30	0	30	20	0	0	0	60	40	50	0	20	20	0	0	50	60	20	80	40	70	80	0
	500 g ai/ha	125 g ai/ha
	Compounds	Compounds
	240	241	242	243	244	245	246	247	248	249	250	251	252	253	254	255	256	1	2	3	4	7	8	9	10	11
Barnyardgrass	100	90	90	100	100	100	100	80	100	100	100	100	90	100	90	100	90	20	100	50	90	30	90	80	90	40
Corn	80	50	20	90	80	90	90	30	30	20	70	20	10	40	10	70	10	0	30	0	10	0	10	10	30	0
Crabgrass, Large	100	70	60	90	90	90	100	70	80	100	100	90	60	100	70	100	80	50	90	90	70	50	80	70	90	50
Foxtail, Giant	100	90	80	100	90	100	100	30	100	90	100	90	60	100	50	90	70	10	90	30	80	40	90	80	90	70
Morningglory	100	100	100	100	100	100	100	100	100	100	100	100	100	100	50	100	80	70	90	80	100	100	90	80	100	90
Pigweed	100	80	30	100	100	100	100	90	90	100	100	80	90	100	90	100	100	70	100	100	100	80	100	100	100	90
Velvetleaf	100	100	90	100	100	100	100	100	100	100	100	100	90	100	90	100	100	100	100	100	100	100	100	100	100	100
Wheat	40	60	30	90	70	80	50	0	0	50	20	10	10	20	0	50	0	10	0	0	0	0	10	0	40	0
	125 g ai/ha
	Compounds
	12	13	14	15	16	17	18	19	20	21	22	23	24	25	26	27	28	29	30	31	32	33	34	35	36	37	38
Barnyardgrass	90	30	30	10	20	10	20	0	0	0	10	10	10	30	30	50	30	20	10	10	20	80	90	10	90	50	60
Corn	40	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
Crabgrass, Large	90	30	30	20	10	10	30	0	0	0	40	30	70	40	70	70	40	70	30	50	50	70	90	50	80	70	60
Foxtail, Giant	90	30	30	10	30	0	40	20	0	0	30	10	70	50	50	80	30	70	10	70	30	60	90	40	80	70	50
Morningglory	100	0	20	10	10	20	40	0	0	0	30	50	70	50	50	60	0	60	30	20	50	80	80	—	50	80	100
Pigweed	100	80	80	60	50	80	100	80	10	0	80	80	90	80	90	100	100	80	70	70	100	90	100	80	90	100	100
Velvetleaf	100	100	100	100	70	100	100	100	20	30	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Wheat	0	10	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	39	40	41	42	43	44	45	46	47	48	49	50	51	52	53	54	55	56	57	58	59	60	61	62	63	64
Barnyardgrass	60	90	50	60	70	90	90	80	90	80	60	90	90	90	90	10	50	90	70	50	90	60	70	80	70	50
Corn	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	10	0	0	10	0	0	30	10	0
Crabgrass, Large	80	90	20	60	70	80	60	70	90	90	90	90	90	90	90	40	70	80	80	80	90	90	80	70	80	80
Foxtail, Giant	80	90	20	40	60	80	50	60	90	90	50	90	90	90	90	10	20	80	80	70	80	80	50	70	60	60
Morningglory	80	50	10	80	20	80	80	60	80	90	100	80	100	100	100	40	90	90	50	80	100	60	100	100	100	90
Pigweed	100	100	100	100	100	100	90	80	90	100	100	100	100	90	100	100	90	90	90	100	100	100	100	90	90	90
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Wheat	0	0	0	0	0	0	0	0	0	0	0	0	0	0	30	0	0	0	0	0	0	20	0	0	0	0
	125 g ai/ha
	Compounds
	65	66	67	68	69	70	71	72	73	74	75	76	77	78	79	80	81	82	83	84	85	86	87	88	89	90
Barnyardgrass	10	80	70	80	90	50	0	80	70	80	80	50	80	50	80	30	100	10	70	0	90	90	80	80	90	80
Corn	0	—	—	0	20	0	0	0	30	0	0	0	0	0	10	0	10	0	0	0	10	0	10	0	0	0
Crabgrass, Large	30	70	60	80	80	50	30	80	90	90	90	70	60	30	80	70	90	40	80	0	90	90	90	90	90	80
Foxtail, Giant	10	70	30	50	80	50	20	40	80	40	80	40	50	20	50	70	80	10	70	0	70	80	70	60	60	70
Morningglory	50	90	100	90	100	100	80	90	100	90	90	90	90	70	100	100	90	90	100	90	100	90	90	90	100	100
Pigweed	20	100	100	100	100	100	70	80	100	100	100	90	100	100	100	100	100	90	90	100	100	100	100	100	100	100
Velvetleaf	90	100	100	100	100	100	100	100	100	90	100	100	100	100	100	100	100	100	100	70	100	100	100	100	100	100
Wheat	0	0	20	0	0	0	0	0	10	0	0	0	0	0	0	0	0	0	0	0	0	0	30	0	0	0
	125 g ai/ha
	Compounds
	91	92	93	94	95	96	97	98	99	100	101	102	103	104	105	106	107	108	109	110	111	112	113	114	115	116
Barnyardgrass	90	80	90	90	80	90	90	80	90	80	80	80	30	10	20	10	90	90	80	60	90	60	70	70	70	80
Corn	0	0	10	0	0	0	50	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	10	0	0
Crabgrass, Large	90	90	90	80	90	90	80	90	90	80	90	90	10	0	20	40	80	90	90	80	90	80	100	80	60	60
Foxtail, Giant	80	80	80	30	70	70	60	70	80	80	60	80	0	0	0	20	70	60	70	10	60	70	90	60	50	60
Morningglory	100	100	100	100	100	100	100	100	100	90	60	100	100	70	10	100	100	100	90	90	100	90	100	90	90	100
Pigweed	100	100	100	100	100	100	100	100	100	90	90	100	100	100	90	80	100	100	100	90	100	90	100	100	100	100
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	70	100	100	100	100	100	90	100	100	100	100	100	70
Wheat	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	117	118	119	120	121	122	123	124	125	126	127	128	129	130	131	132	133	134	135	136	138	139	140	141	142	143
Barnyardgrass	80	90	80	90	80	60	80	40	70	80	80	100	90	100	90	10	20	10	10	30	90	60	90	90	70	70
Corn	20	0	0	10	0	0	20	0	0	10	20	20	20	10	0	0	10	0	0	0	20	20	0	20	0	10
Crabgrass, Large	80	90	80	90	80	70	80	70	70	90	80	90	90	70	90	20	40	50	40	80	70	70	90	80	70	70
Foxtail, Giant	70	80	70	80	90	70	70	50	70	70	70	90	90	80	80	0	20	40	0	30	60	50	80	80	30	60
Morningglory	100	100	90	100	100	90	100	100	80	100	90	100	100	100	100	90	40	0	70	100	50	100	100	70	100	90
Pigweed	100	100	100	90	100	100	100	90	90	90	90	100	100	100	100	60	80	70	80	80	100	90	90	90	90	70
Velvetleaf	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Wheat	0	0	50	20	30	0	0	0	0	0	0	0	0	0	0	0	20	0	0	0	0	20	0	0	0	0
	125 g ai/ha
	Compounds
	144	145	146	147	148	149	150	151	152	153	154	155	156	157	158	159	160	161	162	163	164	165	166	167	168	169
Barnyardgrass	70	70	100	80	90	70	40	60	100	80	90	90	90	90	90	90	90	30	100	50	100	0	80	60	30	90
Corn	0	30	20	20	0	0	0	0	0	0	0	20	20	0	10	0	20	0	0	0	10	0	30	30	20	0
Crabgrass, Large	50	70	80	80	70	40	20	30	90	90	70	70	70	80	70	90	90	60	80	60	90	20	40	60	50	90
Foxtail, Giant	40	60	70	70	60	60	40	20	80	70	60	80	80	90	70	90	70	40	70	20	100	20	60	90	50	80
Morningglory	30	90	90	100	100	100	100	40	100	50	30	100	100	10	70	100	100	60	100	10	100	50	100	60	100	100
Pigweed	80	100	100	100	90	70	30	100	100	100	60	100	100	90	100	100	100	80	100	80	100	80	70	90	100	100
Velvetleaf	100	100	100	100	100	100	50	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100	100
Wheat	0	0	20	20	0	20	0	0	20	0	0	0	0	0	0	10	0	0	30	0	0	0	0	0	0	20
	125 g ai/ha
	Compounds
	170	171	172	173	174	175	176	177	178	179	180	181	182	183	184	185	186	187	188	189	190	191	192	193	194	195
Barnyardgrass	40	50	90	90	90	50	50	80	80	60	90	100	70	60	90	70	80	90	70	90	90	90	60	90	90	70
Corn	20	30	20	0	10	0	0	0	0	10	10	10	0	10	10	0	0	0	0	10	0	0	0	10	0	0
Crabgrass, Large	60	60	60	70	70	40	10	30	50	60	90	90	80	80	80	50	90	90	80	90	90	70	30	100	60	40
Foxtail, Giant	50	60	60	70	20	30	10	0	50	40	70	100	50	80	90	50	80	80	40	80	80	80	50	90	30	30
Morningglory	100	100	90	100	30	10	0	0	50	60	40	30	100	40	50	100	100	100	90	100	100	90	—	100	90	60
Pigweed	80	100	100	100	100	100	100	100	60	90	100	100	80	100	100	90	100	100	90	100	100	80	60	100	100	90
Velvetleaf	100	100	100	100	100	100	80	90	90	100	100	100	100	100	100	90	100	100	100	100	100	100	70	100	100	100
Wheat	0	20	0	0	0	0	0	0	0	40	0	30	0	50	0	0	0	0	0	0	0	0	0	40	0	0
	125 g ai/ha
	Compounds
	196	197	198	199	200	202	203	204	205	206	207	208	209	210	211	212	213	214	215	216	218	219	220	221	222	223
Barnyardgrass	80	80	70	90	0	90	80	100	90	90	60	30	80	40	50	50	20	80	90	10	80	90	90	10	10	0
Corn	10	20	0	0	0	10	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
Crabgrass, Large	50	70	70	70	10	70	30	60	60	60	60	30	50	10	40	10	20	80	40	40	20	80	50	10	0	0
Foxtail, Giant	70	80	60	100	0	80	30	30	40	50	60	30	60	10	50	0	10	50	40	30	40	50	20	0	0	0
Morningglory	100	100	100	100	50	100	100	30	100	100	40	50	30	50	70	50	60	80	100	70	80	100	100	10	30	60
Pigweed	80	100	90	100	60	100	100	100	90	90	100	80	60	90	70	100	80	90	90	90	100	100	100	40	40	50
Velvetleaf	100	100	100	100	100	100	90	100	100	100	100	100	100	70	60	70	70	100	100	90	100	100	100	80	60	50
Wheat	0	0	0	0	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0	20	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	224	225	226	227	228	229	230	231	232	233	234	235	236	237	238	239	240	241	242	243	244	245	246	247	248	249
Barnyardgrass	90	90	90	90	90	90	70	70	60	90	80	90	90	100	100	90	100	90	50	100	90	90	70	30	90	90
Corn	10	10	10	10	50	0	0	0	10	60	20	80	20	40	40	30	40	20	0	70	40	40	0	0	0	0
Crabgrass, Large	70	90	90	90	90	80	80	50	20	90	40	100	80	80	90	80	90	50	20	90	90	90	70	40	50	90
Foxtail, Giant	70	70	90	90	90	90	30	60	60	90	70	90	70	90	90	70	90	80	50	100	90	100	80	0	50	80
Morningglory	100	100	100	100	100	100	70	90	100	100	100	100	100	100	100	100	100	100	40	100	100	100	90	100	100	100
Pigweed	100	100	100	100	100	100	80	80	70	100	70	100	80	90	100	80	90	70	20	100	100	100	90	70	80	90
Velvetleaf	100	100	100	100	100	100	100	90	70	100	100	100	100	100	100	100	100	100	50	100	100	100	100	100	100	100
Wheat	0	0	0	0	0	0	0	0	20	20	0	50	0	20	50	0	20	40	0	70	40	40	0	0	0	10
		125 g ai/ha
		Compounds
		250	251	252	253	254	255	256
	Barnyardgrass	50	80	80	100	0	90	40
	Corn	0	0	0	10	0	30	0
	Crabgrass, Large	60	50	30	80	20	90	30
	Foxtail, Giant	90	50	40	60	10	90	20
	Morningglory	100	100	80	100	20	100	30
	Pigweed	100	70	70	90	60	90	90
	Velvetleaf	100	100	70	100	50	100	100
	Wheat	0	0	0	0	0	10	0
Preemergence
	1000 g ai/ha	500 g ai/ha
	Compound	Compounds
	217	1	2	3	4	7	8	9	10	11	12	13	14	15	16	17	18	19	20	21	22	23	24	25	26	27	28
Barnyardgrass	80	10	70	60	70	10	80	100	90	70	70	90	70	90	70	80	100	90	20	0	100	70	90	80	60	80	70
Corn	0	0	0	0	20	0	20	0	0	0	0	20	0	0	20	0	20	0	0	0	0	0	0	0	0	0	0
Crabgrass, Large	100	70	100	80	90	40	100	100	100	90	90	100	90	90	70	100	100	80	30	20	90	90	100	100	90	90	60
Foxtail, Giant	80	10	90	10	70	20	90	90	100	50	90	90	90	70	70	20	90	30	20	10	80	20	100	90	70	90	30
Morningglory	70	50	90	100	70	40	70	90	90	70	90	0	60	60	0	10	70	50	0	0	70	70	80	60	70	80	80
Pigweed	100	100	100	100	90	80	90	100	100	100	100	100	100	90	50	90	100	90	—	70	90	70	100	80	100	90	100
Velvetleaf	100	80	100	90	100	100	90	100	100	100	90	100	100	90	40	100	100	100	50	0	100	100	100	100	100	100	80
Wheat	30	0	0	0	20	0	20	0	50	0	0	40	0	20	0	0	40	0	0	0	0	0	20	20	0	0	0
	500 g ai/ha
	Compounds
	29	30	31	32	33	34	35	36	37	38	39	40	41	42	43	44	45	46	47	48	49	50	51	52	53	54	55	56
Barnyardgrass	100	40	40	90	90	100	0	50	30	90	90	100	80	60	80	100	80	50	90	100	60	90	90	100	100	10	10	90
Corn	0	0	0	0	30	0	0	0	0	30	0	0	0	0	0	0	0	0	0	0	0	0	0	10	0	0	0	0
Crabgrass, Large	100	60	90	90	100	100	60	80	50	100	90	100	80	90	100	90	100	80	100	100	90	100	100	100	100	30	50	90
Foxtail, Giant	100	10	40	90	90	100	10	60	50	80	90	90	30	40	70	90	80	60	90	90	50	80	100	100	100	0	0	90
Morningglory	80	60	50	80	50	60	20	30	30	70	60	80	20	50	10	70	90	70	90	80	80	80	90	90	90	0	60	90
Pigweed	100	80	80	100	90	100	100	80	100	100	90	90	90	100	100	90	100	90	100	100	90	100	100	100	100	90	100	100
Velvetleaf	100	70	70	70	80	100	70	100	90	100	90	100	80	100	100	100	100	70	100	100	90	90	90	100	90	70	60	100
Wheat	0	0	0	20	10	0	0	20	0	20	0	0	0	0	0	0	20	20	0	0	0	0	0	0	10	0	0	0
	500 g ai/ha
	Compounds
	57	58	59	60	61	62	63	64	65	66	67	68	69	70	71	72	73	74	75	76	77	78	79	80	81	82	83
Barnyardgrass	90	90	90	90	90	90	90	90	10	70	40	50	60	10	0	60	70	60	80	30	50	30	70	10	90	10	90
Corn	0	0	0	10	0	20	0	0	0	0	0	0	0	0	0	20	0	0	0	0	0	0	0	0	0	0	20
Crabgrass, Large	100	90	100	100	100	90	100	90	80	100	90	100	100	90	50	100	100	90	100	100	90	50	100	90	100	100	100
Foxtail, Giant	90	80	80	90	60	70	80	70	40	80	50	60	70	60	10	30	70	40	70	30	20	10	50	60	80	40	90
Morningglory	80	100	90	80	80	100	70	0	0	30	50	50	50	10	0	70	80	60	90	50	70	0	50	30	70	60	60
Pigweed	100	100	100	100	90	100	100	100	0	100	90	100	100	100	90	90	100	100	100	100	90	100	100	90	100	100	100
Velvetleaf	100	100	100	100	100	90	90	90	50	100	80	100	100	80	70	100	100	90	100	70	100	50	100	100	100	90	100
Wheat	0	0	0	40	0	10	0	0	0	0	0	0	10	0	0	0	30	0	0	20	0	0	30	0	20	0	30
	500 g ai/ha
	Compounds
	84	85	86	87	88	89	90	91	92	93	94	95	96	97	98	99	100	101	102	103	104	105	106	107	108	109
Barnyardgrass	0	100	100	90	90	80	70	100	100	100	30	80	100	100	60	90	90	70	90	20	0	0	50	90	90	70
Corn	0	10	—	0	0	0	0	0	0	0	0	0	10	0	0	0	0	0	0	0	0	0	0	—	0	0
Crabgrass, Large	0	100	—	100	—	90	100	100	100	100	90	90	100	100	100	100	90	90	100	80	0	50	80	100	90	90
Foxtail, Giant	0	90	100	80	100	70	60	70	80	80	40	60	80	90	80	80	80	50	100	60	0	50	70	90	40	30
Morningglory	10	80	60	80	70	70	70	80	80	90	40	90	80	80	80	80	80	80	80	60	0	—	80	100	90	70
Pigweed	100	—	—	—	—	100	100	90	100	100	100	100	100	100	100	100	100	80	100	100	90	90	90	100	100	100
Velvetleaf	40	—	100	100	100	100	100	100	100	100	70	100	100	100	100	100	80	100	100	90	40	70	60	100	90	100
Wheat	0	40	—	40	10	30	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	500 g ai/ha
	Compounds
	110	111	112	113	114	115	116	117	118	119	120	121	122	123	124	125	126	127	128	129	130	131	132	133	134	135
Barnyardgrass	60	90	80	90	90	80	70	90	90	100	100	100	100	100	60	90	100	100	100	100	90	100	100	100	10	0
Corn	0	0	0	—	0	0	0	20	0	30	30	30	0	30	0	0	20	0	0	0	30	0	20	20	0	0
Crabgrass, Large	80	100	100	100	100	80	70	100	90	100	100	100	100	100	90	100	100	100	100	90	100	100	100	100	30	40
Foxtail, Giant	10	70	60	90	80	70	60	70	50	100	100	100	100	100	40	80	90	90	90	80	90	80	90	80	30	0
Morningglory	70	80	80	80	80	80	40	90	70	90	90	70	80	—	80	0	90	80	—	90	80	80	30	0	30	50
Pigweed	90	100	100	100	100	100	100	100	100	100	100	100	100	100	100	90	100	100	100	100	100	100	80	100	60	80
Velvetleaf	70	100	70	100	100	90	60	90	80	100	100	100	100	100	100	100	100	100	100	90	90	100	80	100	70	70
Wheat	0	0	0	0	20	0	0	20	0	60	70	50	40	20	0	0	20	0	30	0	0	0	10	20	0	0
	500 g ai/ha
	Compounds
	136	138	139	140	141	142	143	144	145	146	147	148	149	150	151	152	153	154	155	156	157	158	159	160	161	162
Barnyardgrass	60	90	90	100	100	80	90	20	90	100	100	30	50	0	100	100	80	40	90	80	50	80	90	80	90	100
Corn	0	20	20	0	0	0	0	0	20	30	0	0	20	0	0	30	20	0	30	20	0	20	40	20	0	0
Crabgrass, Large	60	70	100	90	100	80	90	30	100	100	100	50	80	10	50	100	100	50	90	50	70	100	100	100	90	100
Foxtail, Giant	0	70	70	90	80	20	70	10	70	90	90	10	60	0	60	90	70	30	60	50	50	80	90	70	80	90
Morningglory	60	0	80	50	30	50	70	10	80	—	90	0	40	0	30	80	70	0	0	0	0	80	50	—	40	80
Pigweed	100	90	100	100	100	100	90	90	100	100	100	60	100	0	70	100	100	80	90	80	50	100	100	100	100	100
Velvetleaf	100	80	90	100	100	60	100	70	100	100	100	80	70	0	70	100	100	80	100	50	100	80	100	30	90	100
Wheat	0	20	10	0	0	0	0	0	20	40	20	0	20	0	20	50	20	0	0	0	0	10	20	20	0	50
	500 g ai/ha
	Compounds
	163	164	165	166	167	168	169	170	171	172	173	174	175	176	177	178	179	180	181	182	183	184	185	186	187	188
Barnyardgrass	20	80	0	20	30	20	50	60	70	80	60	40	30	30	10	50	70	80	100	90	100	90	50	60	90	30
Corn	0	0	0	0	0	0	20	0	20	0	10	20	0	0	20	0	0	0	0	20	0	20	0	0	0	0
Crabgrass, Large	10	90	0	70	90	80	40	70	100	90	100	60	50	20	10	70	100	100	100	100	100	100	30	80	90	70
Foxtail, Giant	10	70	0	20	50	70	50	70	80	60	40	40	50	50	20	50	90	70	80	80	90	90	50	60	90	40
Morningglory	0	50	0	0	0	70	20	70	60	50	—	0	10	20	—	40	40	—	30	80	50	60	30	90	90	80
Pigweed	60	100	0	40	90	50	50	50	80	100	90	90	100	100	50	40	90	100	100	100	100	90	70	100	70	80
Velvetleaf	50	70	0	100	100	60	50	80	100	80	100	70	50	50	40	60	100	100	100	100	100	100	50	100	100	80
Wheat	0	0	0	0	0	0	0	20	40	0	20	0	0	0	0	0	60	20	20	50	50	0	0	0	0	0
	500 g ai/ha
	Compounds
	189	190	191	192	193	194	195	196	197	198	199	200	202	203	204	205	206	207	208	209	210	211	212	213	214	215
Barnyardgrass	90	100	80	30	90	40	10	50	40	50	90	0	100	70	80	10	20	50	80	50	70	70	90	30	60	20
Corn	0	0	30	40	0	0	0	20	30	20	30	0	40	20	20	0	0	0	20	20	0	0	0	0	0	0
Crabgrass, Large	80	90	100	40	100	40	50	70	60	90	100	0	100	70	100	90	60	100	100	70	50	90	40	50	90	60
Foxtail, Giant	60	90	90	40	90	—	30	80	50	70	90	0	100	90	90	80	60	80	70	60	90	50	50	30	70	30
Morningglory	80	70	70	0	90	20	0	40	60	30	80	—	100	70	80	60	0	70	70	30	50	10	80	60	80	70
Pigweed	100	100	100	50	100	100	10	30	100	100	100	20	100	100	100	90	80	100	100	70	100	60	90	90	90	90
Velvetleaf	100	100	100	60	100	70	50	50	90	80	100	60	100	80	90	80	60	100	90	100	60	60	70	60	100	70
Wheat	0	0	20	20	50	0	20	20	20	20	20	0	40	30	40	0	0	0	20	0	0	0	0	0	30	0
	500 g ai/ha
	Compounds
	216	218	219	220	221	222	223	224	225	226	227	228	229	230	231	232	233	234	235	236	237	238	239	240	241	242
Barnyardgrass	20	100	100	90	0	60	70	90	90	100	100	100	70	80	60	50	100	80	100	90	90	100	80	—	90	0
Corn	20	0	0	10	0	0	0	20	20	0	10	50	0	0	20	0	0	20	70	10	50	50	0	40	20	0
Crabgrass, Large	80	80	100	90	10	20	80	100	100	100	100	100	100	90	90	40	100	90	100	100	100	100	100	100	90	10
Foxtail, Giant	60	50	80	40	10	60	90	70	80	90	80	90	60	50	60	70	80	60	90	70	90	90	70	80	70	0
Morningglory	30	80	80	70	0	40	—	30	80	80	80	80	80	20	80	40	90	10	90	80	80	90	50	0	30	0
Pigweed	50	90	100	100	60	0	90	100	100	100	100	100	100	80	80	90	100	60	90	90	100	100	100	100	50	0
Velvetleaf	30	90	90	100	30	60	60	80	100	100	100	100	100	80	60	60	80	90	100	100	100	100	100	80	60	0
Wheat	0	0	20	0	0	0	0	30	30	10	10	0	0	0	0	30	40	20	40	30	30	40	30	40	40	0
	500 g ai/ha	125 g ai/ha
	Compounds	Compounds
	243	244	245	246	247	248	249	250	251	252	253	254	255	256	1	2	3	4	7	8	9	10	11	12	13	14	15	16	17	18
Barnyardgrass	100	100	100	100	0	30	40	40	20	0	20	10	100	70	0	10	30	10	0	10	0	30	0	10	10	10	10	0	0	10
Corn	60	40	20	50	0	20	0	0	0	0	—	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
Crabgrass, Large	100	100	100	100	0	70	80	90	80	20	80	50	90	80	10	80	50	20	0	40	90	90	20	50	60	30	40	40	20	60
Foxtail, Giant	100	100	90	90	0	20	40	60	40	10	70	30	50	30	0	50	0	10	0	40	40	70	10	20	50	40	40	30	0	40
Morningglory	90	80	60	60	0	40	70	60	40	10	70	—	60	50	—	60	0	0	0	0	20	10	0	30	0	10	0	0	0	20
Pigweed	100	100	90	100	0	40	100	100	60	40	80	0	90	90	20	100	80	90	10	90	50	100	60	80	40	100	30	30	80	70
Velvetleaf	100	100	100	100	0	60	90	90	70	50	90	20	100	80	60	60	80	40	60	50	70	90	60	70	80	90	40	0	40	30
Wheat	70	40	20	50	0	20	0	10	0	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	19	20	21	22	23	24	25	26	27	28	29	30	31	32	33	34	35	36	37	38	39	40	41	42	43	44	45	46	47	48	49	50	51	52	53	54	55	56
Barnyardgrass	10	0	0	10	0	10	20	0	10	10	0	0	0	0	10	10	0	10	0	10	10	10	0	0	10	30	40	0	10	20	20	50	10	40	40	0	0	50
Corn	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
Crabgrass, Large	20	0	0	40	10	30	60	20	30	20	20	0	0	20	80	90	10	10	10	30	60	60	20	40	50	80	50	30	70	90	60	90	30	90	90	0	0	80
Foxtail, Giant	10	0	0	20	0	40	50	30	30	0	30	0	0	10	30	60	0	10	10	10	50	50	10	10	10	30	0	0	50	70	20	50	30	80	70	0	0	70
Morningglory	0	0	0	20	0	20	0	10	20	20	40	0	0	0	0	10	—	0	0	0	40	10	0	0	0	20	20	10	60	40	30	40	—	30	80	0	30	50
Pigweed	80	0	—	70	50	90	50	60	70	80	50	0	40	30	80	90	10	0	50	50	60	70	90	90	90	60	80	60	80	90	80	90	90	100	90	80	50	90
Velvetleaf	50	0	0	30	40	90	80	20	60	20	20	20	10	20	50	50	0	60	50	70	70	70	30	70	60	70	60	40	70	80	80	80	70	100	80	60	60	80
Wheat	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	57	58	59	60	61	62	63	64	65	66	67	68	69	70	71	72	73	74	75	76	77	78	79	80	81	82	83	84	85	86	87	88	89	90
Barnyardgrass	40	30	40	60	30	10	10	10	0	20	0	0	10	0	0	10	0	30	40	0	20	0	0	0	50	0	30	0	50	20	20	10	20	40
Corn	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	—	0	0	0	0
Crabgrass, Large	90	70	90	90	60	60	90	80	10	90	30	70	90	40	10	70	70	70	90	50	50	10	50	50	90	—	70	0	100	—	—	—	60	60
Foxtail, Giant	70	50	50	60	10	60	50	50	0	—	—	—	40	30	0	0	50	0	50	0	0	0	0	10	30	10	40	0	—	—	—	—	20	30
Morningglory	20	—	—	—	60	90	10	0	0	0	30	20	0	0	0	—	10	40	60	0	—	0	0	0	0	0	20	0	50	0	50	50	0	0
Pigweed	90	70	90	90	80	80	100	80	0	90	90	90	100	60	—	50	100	90	100	50	80	50	100	60	100	90	80	90	—	—	—	—	90	80
Velvetleaf	80	70	100	80	60	70	80	60	30	70	70	70	70	70	50	90	80	70	90	20	70	20	70	50	100	50	70	0	70	—	100	80	70	70
Wheat	0	0	0	0	0	0	—	0	0	0	0	0	0	0	0	0	10	0	0	0	0	0	0	0	0	0	0	0	0	—	10	0	0	0
	125 g ai/ha
	Compounds
	91	92	93	94	95	96	97	98	99	100	101	102	103	104	105	106	107	108	109	110	111	112	113	114	115	116	117
Barnyardgrass	60	60	80	0	40	90	60	0	10	40	20	40	0	0	0	10	40	30	10	20	30	0	10	30	0	10	50
Corn	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	20	0	0	0	0	0	0	0	0	0	0
Crabgrass, Large	90	90	90	30	50	100	100	90	60	80	70	80	40	0	30	70	90	70	40	40	90	60	70	90	20	30	60
Foxtail, Giant	40	70	60	0	30	50	60	40	40	50	30	80	0	0	30	40	60	30	0	0	—	20	70	40	20	10	20
Morningglory	20	0	80	10	70	80	70	70	—	70	80	80	20	0	0	50	70	80	40	40	50	0	30	0	60	0	40
Pigweed	90	100	100	70	90	100	100	100	90	80	70	60	90	80	80	80	100	90	90	80	100	20	100	100	70	60	90
Velvetleaf	100	90	90	40	90	100	100	90	80	60	80	80	60	0	0	40	100	80	70	60	90	40	100	70	60	30	70
Wheat	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	118	119	120	121	122	123	124	125	126	127	128	129	130	131	132	133	134	135	136	138	139	140	141	142	143	144
Barnyardgrass	30	70	70	20	30	50	20	10	70	40	10	30	20	50	10	10	0	0	0	20	40	60	60	10	40	0
Corn	0	20	20	0	0	0	0	0	0	0	0	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0
Crabgrass, Large	60	100	100	90	90	100	60	80	90	90	80	70	40	80	50	50	0	0	20	40	90	70	80	30	50	10
Foxtail, Giant	10	90	90	80	30	50	10	40	60	50	60	40	20	60	20	40	0	0	0	30	20	40	40	0	10	0
Morningglory	10	60	30	0	40	70	60	0	70	10	80	—	10	—	0	0	—	20	30	0	0	30	0	0	10	0
Pigweed	90	100	100	80	100	90	100	90	100	100	80	100	90	100	10	40	0	40	80	50	70	80	70	90	70	0
Velvetleaf	70	90	80	80	100	70	70	60	80	70	80	80	80	80	50	50	70	40	70	20	60	80	70	20	70	20
Wheat	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	145	146	147	148	149	150	151	152	153	154	155	156	157	158	159	160	161	162	163	164	165	166	167	168	169	170
Barnyardgrass	20	60	70	10	20	0	20	50	40	0	10	0	0	20	30	40	10	10	0	10	0	0	0	0	0	0
Corn	0	0	0	0	0	0	0	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
Crabgrass, Large	50	60	100	0	30	0	10	90	80	10	60	10	20	70	80	80	50	90	0	30	0	10	20	30	40	10
Foxtail, Giant	30	30	70	0	10	0	20	60	20	10	30	10	10	10	60	20	50	30	0	40	0	0	10	10	40	10
Morningglory	0	10	40	0	0	0	—	60	20	0	0	0	0	0	0	70	0	0	0	10	—	0	0	0	0	0
Pigweed	70	70	90	0	80	0	50	100	100	30	90	70	0	100	100	80	90	100	0	60	0	0	10	10	0	30
Velvetleaf	90	70	80	30	40	0	50	60	100	40	60	0	60	50	70	60	70	60	10	40	0	40	70	0	20	10
Wheat	0	0	0	0	0	0	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	171	172	173	174	175	176	177	178	179	180	181	182	183	184	185	186	187	188	189	190	191	192	193	194	195	196
Barnyardgrass	20	10	0	0	0	10	0	0	0	30	20	70	20	20	0	0	20	0	20	10	10	10	80	0	0	0
Corn	0	0	0	10	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	40	0	0	0	0
Crabgrass, Large	70	10	40	20	30	0	0	10	20	80	90	100	90	30	0	30	30	30	30	60	50	10	90	20	0	0
Foxtail, Giant	30	10	20	0	0	10	0	10	10	30	30	50	60	30	0	20	30	10	30	60	40	0	90	—	0	0
Morningglory	0	0	0	0	0	0	0	0	0	0	0	70	20	10	—	20	80	70	—	—	0	0	80	—	0	0
Pigweed	50	10	50	30	60	60	0	0	50	90	100	90	90	70	0	50	60	60	70	70	80	0	100	50	0	0
Velvetleaf	80	50	70	20	40	10	10	0	50	80	70	70	100	80	0	60	70	70	70	70	60	0	100	30	0	0
Wheat	20	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	197	198	199	200	202	203	204	205	206	207	208	209	210	211	212	213	214	215	216	218	219	220	221	222	223	224
Barnyardgrass	0	0	20	0	20	30	30	0	0	10	10	0	10	10	10	0	10	0	0	20	40	10	0	0	0	0
Corn	0	0	20	0	20	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	20
Crabgrass, Large	0	10	60	0	50	20	40	20	10	60	80	20	10	10	0	0	30	0	0	10	50	20	0	20	30	70
Foxtail, Giant	0	70	60	0	50	30	20	10	0	30	40	10	20	20	10	10	30	10	0	0	10	0	0	30	30	20
Morningglory	0	0	70	0	0	0	0	0	0	0	0	0	0	0	0	—	0	0	0	0	20	0	0	0	10	—
Pigweed	20	10	80	0	90	100	100	10	30	80	60	0	60	40	60	50	70	20	0	20	90	80	0	0	60	70
Velvetleaf	40	0	90	0	70	50	50	10	0	70	60	60	40	30	50	40	90	0	0	50	30	40	20	0	0	50
Wheat	0	0	0	0	0	0	20	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	125 g ai/ha
	Compounds
	225	226	227	228	229	230	231	232	233	234	235	236	237	238	239	240	241	242	243	244	245	246	247	248	249	250
Barnyardgrass	20	30	50	40	0	10	0	0	30	0	90	50	20	70	20	40	10	0	70	30	40	10	0	0	0	0
Corn	0	0	0	0	0	0	0	0	0	0	20	0	0	0	0	0	0	0	30	20	0	0	0	0	0	0
Crabgrass, Large	60	90	90	100	80	30	40	10	40	60	100	80	40	90	70	50	20	0	100	90	80	100	0	10	40	30
Foxtail, Giant	40	70	40	50	50	40	0	0	20	10	70	40	40	50	20	40	10	0	90	70	80	90	0	10	20	30
Morningglory	30	60	50	70	40	0	10	0	50	—	80	70	10	40	—	0	0	0	70	30	20	20	0	0	30	10
Pigweed	90	100	80	100	90	—	50	0	70	50	90	80	30	100	70	20	20	0	100	100	80	100	0	0	80	60
Velvetleaf	80	80	90	100	100	60	50	0	60	30	100	80	80	90	80	60	20	0	90	50	70	90	0	20	60	50
Wheat	0	0	0	0	0	0	0	0	0	0	10	0	0	0	0	0	0	0	30	0	0	0	0	0	0	0
		125 g ai/ha
		Compounds
		251	252	253	254	255	256
	Barnyardgrass	0	0	10	0	10	0
	Corn	0	0	0	0	0	0
	Crabgrass, Large	20	10	30	0	20	10
	Foxtail, Giant	10	0	20	0	0	0
	Morningglory	0	0	40	0	40	0
	Pigweed	0	0	20	0	70	0
	Velvetleaf	50	20	50	0	60	20
	Wheat	0	0	0	0	0	0

TABLE F1 Observed and Expected Results from Compound 2, Bromoxynil, or their combination. Postemergence Application Rate *Application rates are grams of active ingredient per hectare (g a.i./ha). “Obsd.” is observed effect. “Exp.” is expected effect calculated from Colby's Equation.

(g a.i./ha)*	Russian Thistle
Cmpd 2	Bromoxynil	Obsd.	Exp.
62	—	42	—
125	—	52	—
—	70	8	—
—	140	13	—
62	70	93	47
125	140	95	58

Claims as granted

5 claims

Classifications

33 codes

IPC · International Patent Classification

Section A — Human necessities

A01N43/56
A01N43/90
A01N43/54
A01N43/78
A01N43/80

Section C — Chemistry; metallurgy

C07D419/12
C07D409/04
C07D498/04
C07D401/04
C07D409/06
C07D405/06
C07D239/36
C07D417/04
C07D405/04
C07D471/04
C07D405/12
C07D409/12
C07D401/14
C07D413/14
C07D411/12
C07D403/14
C07D413/04
C07D409/14
C07D417/14
C07D413/12
C07D417/12
C07D413/06
C07D487/04
C07D403/06
C07D405/14
C07D493/08
C07D403/12
C07D407/12

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Alexander R Pagano

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