An isoxazolin-5-one derivative represented by the following (1): [structure] wherein R 1 represents a C1-C6 haloalkyl group, and R 2 to R 4 and X each represents a certain substituent or the like; and n represents an integer of 1 to 4, wherein X's may be different from each other when n represents an integer of 2 to 4, and an herbicide containing the isoxazolin-5-one derivative as an active ingredient are provided.

Description

24 parts

›TECHNICAL FIELD

The present invention provides isoxazolin-5-one derivatives and herbicides which contain the isoxazolin-5-one derivatives as active ingredients and which have a particularly excellent control effect on a harmful weed in an agricultural or horticultural field or in a non-crop land.

›BACKGROUND ART

Use of herbicides is indispensable for protecting useful crops such as rice, wheat, corn, soybeans, cotton plant and beets from weeds and for increasing the yield. Recently, a selective herbicide which does not damage crops but which can selectively kill weeds only is desired in cultivated land where both such a useful crop and weeds grow. Moreover, an agent which exhibits a high herbicidal effect with a possible low agent amount is required in view of the prevention of environmental pollution, a decrease in the economic costs in transport and spraying and the like.

Here, although isoxazolin-5-one derivatives exhibiting a similar herbicidal activity to that of the invention are reported in Patent Literatures 1 and 2 and Non Patent Literature 1, the compounds of the invention in which the 4-position of the isoxazolin-5-one ring is substituted with a 2-(haloalkylsulfonylamino)benzyl group are not reported at all. It is known that heterocyclic compounds having a haloalkylsulfonylamino group at the 2-position of a benzyl group have a herbicidal activity (Patent Literatures 3 to 12). However, there is no report showing that compounds in which the heterocyclic moiety is isoxazolin-5-one, as in the invention, exhibit a herbicidal activity.

›BACKGROUND ART LITERATURE

Patent Literature

Patent Literature 1: U.S. Pat. No. 4,000,155

Patent Literature 2: German Published Patent No. 3541722

Patent Literature 3: WO2004/011429

Patent Literature 4: WO2006/090792

Patent Literature 5: WO2008/059948

Patent Literature 6: WO2008/102908

Patent Literature 7: WO2010/026989

Patent Literature 8: WO2010/119906

Patent Literature 9: WO2014/175206

Patent Literature 10: WO2016/056565

Patent Literature 11: WO2015/004282

Patent Literature 12: WO2015/097071

Non Patent Literature

Non Patent Literature 1: Journal of Heterocyclic Chemistry, Vol. 50, 2013, P. 1381-1385

›SUMMARY OF INVENTION · 1 of 2

Technical Problem

A problem to be solved by the invention is to provide an herbicide having an excellent herbicidal activity and crop selectivity.

Solution to Problem

As a result of intensive studies to solve the problem, the present inventors have found that isoxazolin-5-one derivatives represented by the following formula (1) below exhibit an excellent herbicidal activity and thus have completed the invention.

Accordingly, the first invention of the present application relates to isoxazolin-5-one derivatives represented by the following formula (1) (sometimes referred to as “the compounds of the invention” in this description).

The second invention of the application relates to herbicides characterized by containing an isoxazolin-5-one derivative represented by the following formula (1) as an active ingredient.

That is, the inventors have found that the following aspects can solve the problem.

[1]

An isoxazolin-5-one derivative represented by the following formula (1) below:

wherein in the formula (1),

R 1 represents a C1-C6 haloalkyl group;

R 2 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 haloalkoxy C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C1-C6 alkylcarbonyl C1-C6 alkyl group, a C7-C11 aralkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a phenoxy C1-C6 alkyl group, a C7-C11 aralkyloxy C1-C6 alkyl group, a phenylcarbonyl C1-C6 alkyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C2-C6 alkenylcarbonyl group, a C2-C6 alkynylcarbonyl group, a C3-C6 cycloalkylcarbonyl group, a C3-C6 cycloalkyl C1-C6 alkylcarbonyl group, a C1-C6 alkoxy C1-C6 alkylcarbonyl group, a C1-C6 haloalkoxy C1-C6 alkylcarbonyl group, a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkylcarbonyl group, a C1-C6 alkylthio C1-C6 alkylcarbonyl group, a C1-C6 haloalkylthio C1-C6 alkylcarbonyl group, a benzoyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C7-C11 aralkylcarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic carbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic C1-C6 alkylcarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C2-C6 alkenyloxycarbonyl group, a C2-C6 alkynyloxycarbonyl group, a C3-C6 cycloalkyloxycarbonyl group, a C3-C6 cycloalkyl C1-C6 alkoxycarbonyl group, a C1-C6 alkoxy C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxy C1-C6 alkoxycarbonyl group, a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkoxycarbonyl group, a C1-C6 alkylthio C1-C6 alkoxycarbonyl group, a C1-C6 haloalkylthio C1-C6 alkoxycarbonyl group, a phenoxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C7-C11 aralkyloxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a phenoxy C1-C6 alkoxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic oxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic C1-C6 alkoxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C1-C6 alkylthiocarbonyl group, a C1-C6 haloalkylthiocarbonyl group, a C1-C6 alkylaminocarbonyl group, a C1-C6 haloalkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfonyl group, a C3-C6 cycloalkylsulfonyl group, a C3-C6 cycloalkyl C1-C6 alkylsulfonyl group, a C1-C6 alkoxy C1-C6 alkylsulfonyl group, a phenylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C7-C11 aralkylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C1-C6 alkylaminosulfonyl group or a di-C1-C6 alkylaminosulfonyl group wherein the di-C1-C6 alkyl groups may be same or different;

R 3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, a phenyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), an amino group, a C1-C6 alkylamino group or a di-C1-C6 alkylamino group wherein the di-C1-C6 alkyl groups may be same or different;

R 4 represents a hydrogen atom, a C1-C15 alkyl group, a C1-C15 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 haloalkoxy C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C1-C6 haloalkylthio C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkyl group, a C1-C6 alkylamino C1-C6 alkyl group, a di-C1-C6 alkylamino C1-C6 alkyl group wherein the di-C1-C6 alkyl groups may be same or different, a C1-C6 alkylcarbonyl C1-C6 alkyl group, a phenyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C7-C11 aralkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, cyano, nitro, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group or a C1-C6 haloalkylthio group), an indanyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a tetrahydronaphthyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a heterocyclic C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a phenoxy C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C7-C11 aralkyloxy C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a phenylcarbonyl C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C1-C6 alkylcarbonyl group, a benzoyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C7-C11 aralkylcarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a phenylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group) or a C7-C11 aralkylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group);

›SUMMARY OF INVENTION · 2 of 2

X represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group; and

n represents an integer of 1 to 4, wherein X's may be different from each other when n represents an integer of 2 to 4.

[2] The isoxazolin-5-one derivative according to [1], wherein R 1 in the formula (1) is a C1-C6 fluoroalkyl group.

[3] The isoxazolin-5-one derivative according to [1] or [2], wherein R 1 in the formula (1) is a trifluoromethyl group.

[4] The isoxazolin-5-one derivative according to any one of [1] to [3],

wherein in the formula (1),

R 1 is a trifluoromethyl group;

R 2 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C7-C11 aralkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C3-C6 cycloalkylcarbonyl group, a C1-C6 alkoxy C1-C6 alkylcarbonyl group, a benzoyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C7-C11 aralkylcarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic carbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic C1-C6 alkylcarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C1-C6 alkoxycarbonyl group, a C2-C6 alkenyloxycarbonyl group, a C1-C6 alkoxy C1-C6 alkoxycarbonyl group, a phenoxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C7-C11 aralkyloxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic C1-C6 alkoxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C3-C6 cycloalkylsulfonyl group, a phenylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group) or a C7-C11 aralkylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group);

R 3 is a hydrogen atom, a C1-C6 alkyl group which may be substituted with a fluorine atom or a C3-C6 cycloalkyl group;

R 4 is a hydrogen atom, a C1-C15 alkyl group, a C1-C15 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a phenyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C7-C11 aralkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, cyano, nitro, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group or a C1-C6 haloalkylthio group), an indanyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a tetrahydronaphthyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a heterocyclic C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a phenoxy C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C7-C11 aralkyloxy C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C1-C6 alkylcarbonyl group, a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different, a C1-C6 alkylsulfonyl group or a phenylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group);

X is a hydrogen atom or a halogen atom; and

n is an integer of 1 to 4 wherein X's may be different from each other when n represents an integer of 2 to 4.

[5] A herbicide containing the isoxazolin-5-one derivative according to any one of [1] to [4] as an active ingredient.

Effects of Invention

The novel isoxazolin-5-one derivatives of the invention represented by the formula (1) above exhibit an excellent herbicide effect.

›DESCRIPTION OF EMBODIMENTS · 1 of 14

The isoxazolin-5-one derivatives related to the compounds of the invention, the production methods thereof and the herbicides containing the compounds as active ingredients are explained specifically.

The carbon atom number described in each of a group below does not include the carbon in the cyano group when the group has a cyano group. Moreover, the carbonyl carbon in a group containing carbonyl, such as a C1-C6 alkylcarbonyl group or a (C1-C6) alkoxycarbonyl group, is not included, either.

In the isoxazolin-5-one derivatives represented by the formula (1) of the invention, examples of the halogen atom or the halogen atom as a substituent include elements of fluorine, chlorine, bromine or iodine. The number of the halogen atom(s) as a substituent may be one, or two or more, and when the number is two or more, the halogen atoms may be the same or different from each other. The position of substitution with the halogen atom may be any position.

Examples of the C1-C6 haloalkyl group represented by R 1 , R 2 or R 3 or the C1-C6 haloalkyl group as a substituent include monochloromethyl group, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2-chloroethyl group, trichloromethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 6-fluorohexyl group and the like. The number of the C1-C6 haloalkyl group(s) as a substituent may be one, two or more, and when the number is two or more, the C1-C6 haloalkyl groups may be the same or different from each other. The position of substitution with the C1-C6 haloalkyl group may be any position.

Examples of the C1-C6 alkyl group represented by R 2 , R 3 or X or the C1-C6 alkyl group as a substituent include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, neopentyl group, 2-pentyl group, 3-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group and the like. The number of the C1-C6 alkyl group(s) as a substituent may be one, two or more, and when the number is two or more, the C1-C6 alkyl groups may be the same or different from each other. The position of substitution with the C1-C6 alkyl group may be any position.

Examples of the C2-C6 alkenyl group represented by R 2 or R 4 include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.

Examples of the C2-C6 alkynyl group represented by R 2 or R 4 include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like.

Examples of the C1-C6 alkoxy C1-C6 alkyl group represented by R 2 or R 4 include methoxymethyl group, ethoxymethyl group, n-propoxymethyl group, isopropoxymethyl group, n-butoxymethyl group, sec-butoxymethyl group, tert-butoxymethyl group, 1-pentyloxymethyl group, 1-hexyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-isopropoxyethyl group, 2-isobutoxyethyl group, 3-methoxypropyl group, 2-methoxypropyl group, 2-methoxy-1-methylethyl group, 2-methoxy-1-ethylethyl group, 2-ethoxy-1-methylethyl group, 2-ethoxy-propyl group, 3-methoxy-1-methylpropyl group and the like.

Examples of the C1-C6 haloalkoxy C1-C6 alkyl group represented by R 2 or R 4 include trifluoromethoxymethyl group, 2,2,2-trifluoroethoxymethyl group, 2-(2,2,2-trifluoroethoxy)ethyl group and the like.

Examples of the C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group represented by R 2 or R 4 include methoxyethoxymethyl group, ethoxyethoxymethyl group, methoxyethoxyethyl group, ethoxyethoxyethyl group and the like.

Examples of the C1-C6 alkylthio C1-C6 alkyl group represented by R 2 or R 4 include methylthiomethyl group, ethylthiomethyl group, n-propylthiomethyl group, isopropylthiomethyl group, n-butylthiomethyl group, sec-butylthiomethyl group, tert-butylthiomethyl group, 1-pentylthiomethyl group, 1-hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-isopropylthioethyl group, 2-isobutylthioethyl group, 3-methylthiopropyl group, 2-methylthiopropyl group, 2-methylthio-1-methylethyl group, 2-methylthio-1-methylpropyl group and the like.

Examples of the C1-C6 alkylcarbonyl C1-C6 alkyl group represented by R 2 or R 4 include 2-oxopropyl group, 2-oxobutyl group, 3-oxobutyl group and the like.

Examples of the C7-C11 aralkyl group moiety of the C7-C11 aralkyl group which may be substituted and is represented by R 2 or R 4 include benzyl group, 1-phenethyl group, 2-phenethyl group, 1-phenylpropyl group, 2-phenylpropyl group, 3-phenylpropyl group, 1-phenyl-2-methylpropyl group, 1-phenylbutyl group, 1-phenylpentyl group, 1-phenylhexyl group, 2-phenyl-1-methylethyl group and the like.

Examples of the phenoxy C1-C6 alkyl group moiety of the phenoxy C1-C6 alkyl group which may be substituted and is represented by R 2 or R 4 include 2-phenoxyethyl group, 2-phenoxypropyl group, 3-phenoxypropyl group, 2-phenoxybutyl group, 3-phenoxybutyl group, 4-phenoxybutyl group and the like.

Examples of the C7-C11 aralkyloxy C1-C6 alkyl group moiety of the C7-C11 aralkyloxy C1-C6 alkyl group which may be substituted and is represented by R 2 or R 4 include benzyloxymethyl group, 1-phenethyloxymethyl group, 2-phenethyloxymethyl group, 1-phenylpropoxymethyl group, 2-phenylpropoxymethyl group, 3-phenylpropoxymethyl group, benzyloxyethyl group and the like.

Examples of the phenylcarbonyl C1-C6 alkyl group moiety of the phenylcarbonyl C1-C6 alkyl group which may be substituted and is represented by R 2 or R 4 include phenacyl group, 1-phenyl-1-oxopropyl group, 1-phenyl-2-oxopropyl group and the like.

›DESCRIPTION OF EMBODIMENTS · 2 of 14

Examples of the C1-C6 alkylcarbonyl group represented by R 2 or R 4 include acetyl group, ethylcarbonyl group, n-propylcarbonyl group, isopropylcarbonyl group, n-butylcarbonyl group, isobutylcarbonyl group, sec-butylcarbonyl group, tert-butylcarbonyl group, 1-pentylcarbonyl group, 1-hexylcarbonyl group and the like.

Examples of the C1-C6 haloalkylcarbonyl group represented by R 2 include monofluoromethylcarbonyl group, difluoromethylcarbonyl group, trifluoromethylcarbonyl group, 2,2,2-trifluoroethylcarbonyl group, 2-chloroethylcarbonyl group, trichloromethylcarbonyl group, 1-fluoroethylcarbonyl group, 2-fluoroethylcarbonyl group, 6-fluorohexylcarbonyl group and the like.

Examples of the C2-C6 alkenylcarbonyl group represented by R 2 include acryloyl group, methacryloyl group and the like.

Examples of the C2-C6 alkynylcarbonyl group represented by R 2 include propiolyl group, methylpropiolyl group and the like.

Examples of the C3-C6 cycloalkylcarbonyl group represented by R 2 include cyclopropanecarbonyl group, 1-methylcyclopropanecarbonyl group, 2-methylcyclopropanecarbonyl group, 2,2-dimethylcyclopropanecarbonyl group, cyclobutanecarbonyl group, cyclopentanecarbonyl group, cyclohexanecarbonyl group and the like.

Examples of the C3-C6 cycloalkyl C1-C6 alkylcarbonyl group represented by R 2 include cyclopropylmethylcarbonyl group, cyclopropylethylcarbonyl group, 1-methylcyclopropylmethylcarbonyl group, 2-methylcyclopropylmethylcarbonyl group, 2,2-dimethylcyclopropylmethylcarbonyl group, cyclobutylmethylcarbonyl group, cyclopentylmethylcarbonyl group, cyclohexylmethylcarbonyl group and the like.

Examples of the C1-C6 alkoxy C1-C6 alkylcarbonyl group represented by R 2 include methoxymethylcarbonyl group, ethoxymethylcarbonyl group, n-propoxymethylcarbonyl group, isopropoxymethylcarbonyl group, n-butoxymethylcarbonyl group, sec-butoxymethylcarbonyl group, tert-butoxymethylcarbonyl group, 1-pentyloxymethylcarbonyl group, 1-hexyloxymethylcarbonyl group, 2-methoxyethylcarbonyl group, 2-ethoxyethylcarbonyl group, 2-isopropoxyethylcarbonyl group, 2-isobutoxyethylcarbonyl group, 3-methoxypropylcarbonyl group, 2-methoxypropylcarbonyl group, 2-methoxy-1-methylethylcarbonyl group and the like.

Examples of the C1-C6 haloalkoxy C1-C6 alkylcarbonyl group represented by R 2 include trifluoromethoxymethylcarbonyl group, 2,2,2-trifluoroethoxymethylcarbonyl group, 2-(2,2,2-trifluoroethoxy)ethylcarbonyl group and the like.

Examples of the C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkylcarbonyl group represented by R 2 include methoxyethoxymethylcarbonyl group, ethoxyethoxymethylcarbonyl group, methoxyethoxyethylcarbonyl group, ethoxyethoxyethylcarbonyl group and the like.

Examples of the C1-C6 alkylthio C1-C6 alkylcarbonyl group represented by R 2 include methylthiomethylcarbonyl group, ethylthiomethylcarbonyl group, n-propylthiomethylcarbonyl group, isopropylthiomethylcarbonyl group, n-butylthiomethylcarbonyl group, sec-butylthiomethylcarbonyl group, tert-butylthiomethylcarbonyl group, 1-pentylthiomethylcarbonyl group, 1-hexylthiomethylcarbonyl group, 2-methylthioethylcarbonyl group, 2-ethylthioethylcarbonyl group, 2-isopropylthioethylcarbonyl group, 2-isobutylthioethylcarbonyl group, 3-methylthiopropylcarbonyl group, 2-methylthiopropylcarbonyl group, 2-methylthio-1-methylethylcarbonyl group, 2-methylthio-1-methylpropylcarbonyl group and the like.

Examples of the C1-C6 haloalkylthio C1-C6 alkylcarbonyl group represented by R 2 include monofluoromethylthiomethylcarbonyl group, difluoromethylthiomethylcarbonyl group, trifluoromethylthiomethylcarbonyl group, 2,2,2-trifluoroethylthiomethylcarbonyl group, 2-chloroethylthiomethylcarbonyl group, trichloromethylthiomethylcarbonyl group, 1-fluoroethylthiomethylcarbonyl group, 2-fluoroethylthiomethylcarbonyl group, 6-fluorohexylthiomethylcarbonyl group and the like.

Examples of the C7-C11 aralkylcarbonyl group moiety of the C7-C11 aralkylcarbonyl group which may be substituted and is represented by R 2 or R 4 include benzylcarbonyl group, 1-phenethylcarbonyl group, 2-phenethylcarbonyl group, 1-phenylpropylcarbonyl group, 2-phenylpropylcarbonyl group, 3-phenylpropylcarbonyl group, 1-phenyl-2-methylpropylcarbonyl group, 1-phenylbutylcarbonyl group, 1-phenylpentylcarbonyl group and the like.

Examples of the heterocyclic carbonyl group moiety of the heterocyclic carbonyl group which may be substituted and is represented by R 2 include 2-pyridylcarbonyl group, 3-pyridylcarbonyl group, 4-pyridylcarbonyl group, 2-thienylcarbonyl group, 3-thienylcarbonyl group, 2-tetrahydrofurylcarbonyl group, 3-tetrahydrofurylcarbonyl group and the like.

Examples of the heterocyclic C1-C6 alkylcarbonyl group moiety of the heterocyclic C1-C6 alkylcarbonyl group which may be substituted and is represented by R 2 include 2-pyridylmethylcarbonyl group, 3-pyridylmethylcarbonyl group, 4-pyridylmethylcarbonyl group, 2-thienylmethylcarbonyl group, 3-thienylmethylcarbonyl group, 2-tetrahydrofurfurylcarbonyl group, 3-tetrahydrofurfurylcarbonyl group and the like.

Examples of the C1-C6 alkoxycarbonyl group represented by R 2 or R 4 include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentyloxycarbonyl group, neopentyloxycarbonyl group, 2-pentyloxycarbonyl group, 3-pentyloxycarbonyl group, n-hexyloxycarbonyl group and the like.

Examples of the C1-C6 haloalkoxycarbonyl group represented by R 2 include trifluoromethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group and the like.

Examples of the C2-C6 alkenyloxycarbonyl group represented by R 2 include vinyloxycarbonyl group, 1-propenyloxycarbonyl group, 2-propenyloxycarbonyl group, 1-butenyloxycarbonyl group, 2-butenyloxycarbonyl group, 3-butenyloxycarbonyl group and the like.

Examples of the C2-C6 alkynyloxycarbonyl group represented by R 2 include ethynyloxycarbonyl group, 1-propynyloxycarbonyl group, propargyloxycarbonyl group, 1-butynyloxycarbonyl group, 2-butynyloxycarbonyl group, 3-butynyloxycarbonyl group, 1-methyl-2-propynyloxycarbonyl group, 2-methyl-3-butynyloxycarbonyl group and the like.

›DESCRIPTION OF EMBODIMENTS · 3 of 14

Examples of the C3-C6 cycloalkyloxycarbonyl group represented by R 2 include cyclopropyloxycarbonyl group, 1-methylcyclopropyloxycarbonyl group, 2-methylcyclopropyloxycarbonyl group, 2,2-dimethylcyclopropyloxycarbonyl group, cyclobutyloxycarbonyl group, cyclopentyloxycarbonyl group, cyclohexyloxycarbonyl group and the like.

Examples of the C3-C6 cycloalkyl C1-C6 alkoxycarbonyl group represented by R 2 include cyclopropylmethoxycarbonyl group, 1-methylcyclopropylmethoxycarbonyl group, 2-methylcyclopropylmethoxycarbonyl group, 2,2-dimethylcyclopropylmethoxycarbonyl group, cyclobutylmethoxycarbonyl group, cyclopentylmethoxycarbonyl group, cyclohexylmethoxycarbonyl group and the like.

Examples of the C1-C6 alkoxy C1-C6 alkoxycarbonyl group represented by R 2 include methoxymethoxycarbonyl group, ethoxymethoxycarbonyl group, n-propoxymethoxycarbonyl group, isopropoxymethoxycarbonyl group, n-butoxymethoxycarbonyl group, sec-butoxymethoxycarbonyl group, tert-butoxymethoxycarbonyl group, 1-pentyloxymethoxycarbonyl group, 1-hexyloxymethoxycarbonyl group, 2-methoxyethoxycarbonyl group, 2-ethoxyethoxycarbonyl group, 2-isopropoxyethoxycarbonyl group, 2-isobutoxyethoxycarbonyl group, 3-methoxypropoxycarbonyl group, 2-methoxypropoxycarbonyl group, 2-methoxy-1-methylethoxycarbonyl group and the like.

Examples of the C1-C6 haloalkoxy C1-C6 alkoxycarbonyl group represented by R 2 include trifluoromethoxymethoxycarbonyl group, 2,2,2-trifluoroethoxymethoxycarbonyl group, 2-(2,2,2-trifluoroethoxy)ethoxycarbonyl group and the like.

Examples of the C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkoxycarbonyl group represented by R 2 include methoxyethoxymethoxycarbonyl group, ethoxyethoxymethoxycarbonyl group, methoxyethoxyethoxycarbonyl group, ethoxyethoxyethoxycarbonyl group and the like.

Examples of the C1-C6 alkylthio C1-C6 alkoxycarbonyl group represented by R 2 include methylthiomethoxycarbonyl group, ethylthiomethoxycarbonyl group, n-propylthiomethoxycarbonyl group, isopropylthiomethoxycarbonyl group, n-butylthiomethoxycarbonyl group, sec-butylthiomethoxycarbonyl group, tert-butylthiomethoxycarbonyl group, 1-pentylthiomethoxycarbonyl group, 1-hexylthiomethoxycarbonyl group, 2-methylthioethoxycarbonyl group, 2-ethylthioethoxycarbonyl group, 2-isopropylthioethoxycarbonyl group, 2-isobutylthioethoxycarbonyl group, 3-methylthiopropoxycarbonyl group, 2-methylthiopropoxycarbonyl group, 2-methylthio-1-methylethoxycarbonyl group, 2-methylthio-1-methylpropoxycarbonyl group and the like.

Examples of the C1-C6 haloalkylthio C1-C6 alkoxycarbonyl group represented by R 2 include monofluoromethylthiomethoxycarbonyl group, difluoromethylthiomethoxycarbonyl group, trifluoromethylthiomethoxycarbonyl group, 2,2,2-trifluoroethylthiomethoxycarbonyl group, 2-chloroethylthiomethoxycarbonyl group, trichloromethylthiomethoxycarbonyl group, 1-fluoroethylthiomethoxycarbonyl group, 2-fluoroethylthiomethoxycarbonyl group, 6-fluorohexylthiomethoxycarbonyl group, 2-(2,2,2-trifluoroethylthio)ethoxycarbonyl group and the like.

Examples of the C7-C11 aralkyloxycarbonyl group moiety of the C7-C11 aralkyloxycarbonyl group which may be substituted and is represented by R 2 include benzyloxycarbonyl group, 1-phenethyloxycarbonyl group, 2-phenethyloxycarbonyl group, 1-phenylpropoxycarbonyl group, 2-phenylpropoxycarbonyl group, 3-phenylpropoxycarbonyl group, 1-phenyl-2-methylpropoxycarbonyl group, 1-phenylbutoxycarbonyl group, 1-phenylpentyloxycarbonyl group and the like.

Examples of the phenoxy C1-C6 alkoxycarbonyl group moiety of the phenoxy C1-C6 alkoxycarbonyl group which may be substituted and is represented by R 2 include 2-phenoxyethoxycarbonyl group, 2-phenoxypropoxycarbonyl group, 3-phenoxypropoxycarbonyl group, 2-phenoxybutoxycarbonyl group, 3-phenoxybutoxycarbonyl group, 4-phenoxybutoxycarbonyl group and the like.

Examples of the heterocyclic oxycarbonyl group moiety of the heterocyclic oxycarbonyl group which may be substituted and is represented by R 2 include 2-pyridyloxycarbonyl group, 3-pyridyloxycarbonyl group, 4-pyridyloxycarbonyl group, 2-thienyloxycarbonyl group, 3-thienyloxycarbonyl group, 2-tetrahydrofuryloxycarbonyl group, 3-tetrahydrofuryloxycarbonyl group and the like.

Examples of the heterocyclic C1-C6 alkoxycarbonyl group moiety of the heterocyclic C1-C6 alkoxycarbonyl group which may be substituted and is represented by R 2 include 2-pyridylmethyloxycarbonyl group, 3-pyridylmethyloxycarbonyl group, 4-pyridylmethyloxycarbonyl group, 2-thienylmethyloxycarbonyl group, 3-thienylmethyloxycarbonyl group, 2-tetrahydrofurfuryloxycarbonyl group, 3-tetrahydrofurfuryloxycarbonyl group and the like.

Examples of the C1-C6 alkylthiocarbonyl group represented by R 2 include methylthiocarbonyl group, ethylthiocarbonyl group, n-propylthiocarbonyl group, isopropylthiocarbonyl group, n-butylthiocarbonyl group, isobutylthiocarbonyl group, sec-butylthiocarbonyl group, tert-butylthiocarbonyl group and the like.

Examples of the C1-C6 haloalkylthiocarbonyl group represented by R 2 include trifluoromethylthiocarbonyl group, 2,2,2-trifluoroethylthiocarbonyl group and the like.

Examples of the C1-C6 alkylaminocarbonyl group represented by R 2 or R 4 include methylaminocarbonyl group, ethylaminocarbonyl group, n-propylaminocarbonyl group, isopropylaminocarbonyl group, n-butylaminocarbonyl group, isobutylaminocarbonyl group, sec-butylaminocarbonyl group, tert-butylaminocarbonyl group and the like.

Examples of the C1-C6 haloalkylaminocarbonyl group represented by R 2 include trifluoromethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group and the like.

Examples of the di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different and the di-C1-C6 alkylaminocarbonyl group is represented by R 2 or R 4 include dimethylaminocarbonyl group, methylethylaminocarbonyl group, diethylaminocarbonyl group, di-n-propylaminocarbonyl group, methyl n-propylaminocarbonyl group, ethyl n-propylaminocarbonyl group, diisopropylaminocarbonyl group, di-n-butylaminocarbonyl group, diisobutylaminocarbonyl group, di-sec-butylaminocarbonyl group, di-tert-butylaminocarbonyl group and the like.

›DESCRIPTION OF EMBODIMENTS · 4 of 14

Examples of the C1-C6 alkylsulfonyl group represented by R 2 or R 4 include methanesulfonyl group, ethanesulfonyl group, n-propanesulfonyl group, isopropanesulfonyl group, n-butanesulfonyl group, isobutanesulfonyl group, sec-butanesulfonyl group, tert-butanesulfonyl group, n-pentanesulfonyl group and the like.

Examples of the C1-C6 haloalkylsulfonyl group represented by R 2 or R 4 include monofluoromethylsulfonyl group, difluoromethylsulfonyl group, trifluoromethylsulfonyl group, monochloromethylsulfonyl group, trichloromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group and the like.

Examples of the C2-C6 alkenylsulfonyl group represented by R 2 include vinylsulfonyl group, 1-propenylsulfonyl group, 2-propenylsulfonyl group, 1-butenylsulfonyl group, 2-butenylsulfonyl group, 3-butenylsulfonyl group and the like.

Examples of the C2-C6 alkynylsulfonyl group represented by R 2 include ethynylsulfonyl group, 1-propynylsulfonyl group, propargylsulfonyl group, 1-butynylsulfonyl group, 2-butynylsulfonyl group, 3-butynylsulfonyl group, 1-methyl-2-propynylsulfonyl group, 2-methyl-3-butynylsulfonyl group and the like.

Examples of the C3-C6 cycloalkylsulfonyl group represented by R 2 include cyclopropanesulfonyl group, 1-methylcyclopropanesulfonyl group, 2-methylcyclopropanesulfonyl group, 2,2-dimethylpropanesulfonyl group, cyclobutanesulfonyl group, cyclopentanesulfonyl group, cyclohexanesulfonyl group and the like.

Examples of the C3-C6 cycloalkyl C1-C6 alkylsulfonyl group represented by R 2 include cyclopropylmethylsulfonyl group, 1-methylcyclopropylmethylsulfonyl group, 2-methylcyclopropylmethylsulfonyl group, 2,2-dimethylpropylmethylsulfonyl group, cyclobutylmethylsulfonyl group, cyclopentylmethylsulfonyl group, cyclohexylmethylsulfonyl group and the like.

Examples of the C1-C6 alkoxy C1-C6 alkylsulfonyl group represented by R 2 include methoxymethylsulfonyl group, ethoxymethylsulfonyl group, n-propoxymethylsulfonyl group, isopropoxymethylsulfonyl group, n-butoxymethylsulfonyl group, sec-butoxymethylsulfonyl group, tert-butoxymethylsulfonyl group, 1-pentyloxymethylsulfonyl group, 1-hexyloxymethylsulfonyl group, 2-methoxyethylsulfonyl group, 2-ethoxyethylsulfonyl group, 2-isopropoxyethylsulfonyl group, 2-isobutoxyethylsulfonyl group, 3-methoxypropylsulfonyl group, 2-methoxypropylsulfonyl group, 2-methoxy-1-methylethylsulfonyl group and the like.

Examples of the C7-C11 aralkylsulfonyl group moiety of the C7-C11 aralkylsulfonyl group which may be substituted and is represented by R 2 or R 4 include benzylsulfonyl group, 1-phenethylsulfonyl group, 2-phenethylsulfonyl group, 1-phenylpropylsulfonyl group, 2-phenylpropylsulfonyl group, 3-phenylpropylsulfonyl group, 1-phenyl-2-methylpropylsulfonyl group, 1-phenylbutylsulfonyl group, 1-phenylpentylsulfonyl group and the like.

Examples of the C1-C6 alkylaminosulfonyl group represented by R 2 include methylaminosulfonyl group, ethylaminosulfonyl group, n-propylaminosulfonyl group, isopropylaminosulfonyl group, n-butylaminosulfonyl group, isobutylaminosulfonyl group, sec-butylaminosulfonyl group, tert-butylaminosulfonyl group and the like.

Examples of the di-C1-C6 alkylaminosulfonyl group wherein the di-C1-C6 alkyl groups may be same or different and the di-C1-C6 alkylaminosulfonyl group is represented by R 2 include dimethylaminosulfonyl group, methylethylaminosulfonyl group, diethylaminosulfonyl group, di-n-propylaminosulfonyl group, methyl n-propylaminosulfonyl group, ethyl n-propylaminosulfonyl group, diisopropylaminosulfonyl group, di-n-butylaminosulfonyl group, diisobutylaminosulfonyl group, di-sec-butylaminosulfonyl group, di-tert-butylaminosulfonyl group and the like.

Examples of the C3-C6 cycloalkyl group represented by R 3 or R 4 include cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylpropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.

Examples of the C1-C6 alkylamino group represented by R 3 include methylamino group, ethylamino group, n-propylamino group, isopropylamino group, n-butylamino group, isobutylamino group, sec-butylamino group, tert-butylamino group and the like.

Examples of the di-C1-C6 alkylamino group wherein the di-C1-C6 alkyl groups may be same or different and the di-C1-C6 alkylamino group is represented by R 3 include dimethylamino group, methylethylamino group, diethylamino group, di-n-propylamino group, methyl n-propylamino group, ethyl n-propylamino group, diisopropylamino group, di-n-butylamino group, diisobutylamino group, di-sec-butylamino group, di-tert-butylamino group and the like.

Examples of the C1-C15 alkyl group represented by R 4 include methyl group, ethyl group, n-propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group, 2-ethyl-2-methylbutyl group, n-pentyl group, neopentyl group, 2-pentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylpentyl group, 2-ethylpentyl group, n-hexyl group, 1-methylhexyl group, 2-methylhexyl group, 1-ethylhexyl group, 2-ethylhexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group and the like.

Examples of the C1-C15 haloalkyl group represented by R 4 include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2-chloroethyl group, trichloromethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 5,5,5-trifluoropentyl group, 6-fluorohexyl group, 6,6,6-trifluorohexyl group, 7,7,7-trifluoroheptyl group and the like.

Examples of the C2-C6 haloalkenyl group represented by R 4 include bromovinyl group, chlorovinyl group, 3,3-dichloro-2-propenyl group, 3,3,3-trifluoro-1-propenyl group, 4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl group and the like.

›DESCRIPTION OF EMBODIMENTS · 5 of 14

Examples of the C2-C6 haloalkynyl group represented by R 4 include fluoroethynyl group, 3-fluoro-2-propynyl group, 3-chloro-2-propynyl group, 3-chloro-1-propynyl group, 5-chloro-4-pentynyl group, 3,3,3-trifluoro-1-propynyl group, 3,3-difluoro-1-propynyl group, 4,4,4-trifluoro-2-butynyl group and the like.

Examples of the C3-C6 cycloalkyl C1-C6 alkyl group represented by R 4 include cyclopropylmethyl group, cyclopropylethyl group, 1-methylcyclopropylmethyl group, 2-methylcyclopropylmethyl group, 2,2-dimethylcyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group and the like.

Examples of the C1-C6 haloalkylthio C1-C6 alkyl group represented by R 4 include monofluoromethylthiomethyl group, difluoromethylthiomethyl group, trifluoromethylthiomethyl group, 2,2,2-trifluoroethylthiomethyl group, 2-(2,2,2-trifluoroethylthio)ethyl group, 2-chloroethylthiomethyl group, trichloromethylthiomethyl group, 1-fluoroethylthiomethyl group, 2-fluoroethylthiomethyl group, 6-fluorohexylthiomethyl group and the like.

Examples of the C1-C6 alkylsulfinyl C1-C6 alkyl group represented by R 4 include methylsulfinylmethyl group, ethylsulfinylmethyl group, n-propylsulfinylmethyl group, isopropylsulfinylmethyl group, n-butylsulfinylmethyl group, isobutylsulfinylmethyl group, sec-butylsulfinylmethyl group, tert-butylsulfinylmethyl group, methylsulfinylethyl group, ethylsulfinylethyl group, n-propyl sulfinylethyl group, isopropyl sulfinylethyl group, methylsulfinylpropyl group and the like.

Examples of the C1-C6 alkylsulfonyl C1-C6 alkyl group represented by R 4 include methylsulfonylmethyl group, ethylsulfonylmethyl group, n-propylsulfonylmethyl group, isopropylsulfonylmethyl group, n-butylsulfonylmethyl group, isobutylsulfonylmethyl group, sec-butylsulfonylmethyl group, tert-butylsulfonylmethyl group, methylsulfonylethyl group, ethylsulfonylethyl group, n-propylsulfonylethyl group, isopropyl sulfonylethyl group, methylsulfonylpropyl group and the like.

Examples of the C1-C6 alkylamino C1-C6 alkyl group represented by R 4 include methylaminomethyl group, methylaminoethyl group, ethylaminoethyl group, n-propylaminoethyl group, isopropylaminoethyl group, n-butylaminoethyl group, isobutylaminoethyl group, sec-butylaminoethyl group, tert-butylaminoethyl group and the like.

Examples of the di-C1-C6 alkylamino C1-C6 alkyl group wherein the di-C1-C6 alkyl groups may be same or different and the di-C1-C6 alkylamino C1-C6 alkyl group is represented by R 4 include dimethylaminomethyl group, dimethylaminoethyl group, methylethylaminoethyl group, diethylaminoethyl group, di-n-propylaminoethyl group, methyl n-propylaminoethyl group, ethyl n-propylaminoethyl group, diisopropylaminoethyl group, di-n-butylaminoethyl group, diisobutylaminoethyl group, di-sec-butylaminoethyl group, di-tert-butylaminoethyl group and the like.

Examples of the indanyl group moiety of the indanyl group which may be substituted and is represented by R 4 include 1-indanyl group, 2-indanyl group and the like.

Examples of the tetrahydronaphthyl group moiety of the tetrahydronaphthyl group which may be substituted and is represented by R 4 include 1-(1,2,3,4-tetrahydronaphthyl) group, 2-(1,2,3,4-tetrahydronaphthyl) group and the like.

Examples of the heterocyclic C1-C6 alkyl group moiety of the heterocyclic C1-C6 alkyl group which may be substituted and is represented by R 4 include (2-oxiranyl)methyl group, (3-oxetanyl)methyl group, (2-methyl-2-oxiranyl)methyl group, (3-methyl-3-oxetanyl)methyl group, (2-tetrahydrofuryl)methyl group, (3-tetrahydrofuryl)methyl group, (2-thienyl)methyl group, (3-thienyl)methyl group, (2-pyridyl)methyl group, (3-pyridyl)methyl group, (4-pyridyl)methyl group, 1-(2-thienyl)ethyl group, 2-(2-thienyl)ethyl group, 1-(3-thienyl)ethyl group, 2-(3-thienyl)ethyl group, 1-(2-pyridyl)ethyl group, 2-(2-pyridyl)ethyl group, 1-(3-pyridyl)ethyl group, 2-(3-pyridyl)ethyl group, 1-(4-pyridyl)ethyl group, 2-(4-pyridyl)ethyl group and the like.

Examples of the C1-C6 alkoxy group represented by X or the C1-C6 alkoxy group as a substituent include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group and the like. The number of the C1-C6 alkoxy group(s) as a substituent may be one, two or more, and when the number is two or more, the C1-C6 alkoxy groups may be the same or different from each other. The position of substitution with the C1-C6 alkoxy group may be any position.

Examples of the C1-C6 haloalkoxy group as a substituent include monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2-chloroethoxy group, trichloromethoxy group, 1-fluoroethoxy group, 2-fluoroethoxy group and the like. The number of the C1-C6 haloalkoxy group(s) as a substituent may be one, two or more, and when the number is two or more, the C1-C6 haloalkoxy groups may be the same or different from each other. The position of substitution with the C1-C6 haloalkoxy group may be any position.

Examples of the C1-C6 alkylthio group as a substituent include methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, tert-butylthio group and the like. The number of the C1-C6 alkylthio group(s) as a substituent may be one, or two or more, and when the number is two or more, the C1-C6 alkylthio groups may be the same or different from each other. The position of substitution with the C1-C6 alkylthio group may be any position.

Examples of the C1-C6 haloalkylthio group as a substituent include trifluoromethylthio group, 2,2,2-trifluoroethylthio group and the like.

The number of the C1-C6 haloalkylthio group(s) as a substituent may be one, or two or more, and when the number is two or more, the C1-C6 haloalkylthio groups may be the same or different from each other. The position of substitution with the C1-C6 haloalkylthio group may be any position.

In the isoxazolin-5-one derivatives represented by the formula (1), although the combination of R 1 to R 4 , X and n is not particularly limited, for example, an embodiment is as follows.

›DESCRIPTION OF EMBODIMENTS · 6 of 14

In the formula (1) above, R 1 is a trifluoromethyl group; R 2 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C7-C11 aralkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C3-C6 cycloalkylcarbonyl group, a C1-C6 alkoxy C1-C6 alkylcarbonyl group, a benzoyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C7-C11 aralkylcarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic carbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic C1-C6 alkylcarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C1-C6 alkoxycarbonyl group, a C2-C6 alkenyloxycarbonyl group, a C1-C6 alkoxy C1-C6 alkoxycarbonyl group, a phenoxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C7-C11 aralkyloxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a heterocyclic C1-C6 alkoxycarbonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group), a C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C3-C6 cycloalkylsulfonyl group, a phenylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group) or a C7-C11 aralkylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group); R 3 is a hydrogen atom, a C1-C6 alkyl group which may be substituted with a fluorine atom or a C3-C6 cycloalkyl group; R 4 is a hydrogen atom, a C1-C15 alkyl group, a C1-C15 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a phenyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C7-C11 aralkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, cyano, nitro, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group or a C1-C6 haloalkylthio group), an indanyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a tetrahydronaphthyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a heterocyclic C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a phenoxy C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C7-C11 aralkyloxy C1-C6 alkyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group), a C1-C6 alkylcarbonyl group, a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different, a C1-C6 alkylsulfonyl group or a phenylsulfonyl group which may be substituted (the group may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group); X is a hydrogen atom or a halogen atom; and n is an integer of 1 to 4 (wherein X's may be different from each other when n represents an integer of 2 to 4.)

Representative examples of the isoxazolin-5-one derivatives represented by the formula (1) are shown together in Table 1 below, but the isoxazolin-5-one derivatives are not limited to these compounds. These compounds include compounds including optical isomers, an E-form and a Z-form. The compound numbers are referred to in the following paragraphs.

The symbols below in the tables stand for the corresponding groups as follows: “H” stands for hydrogen atom; “Me” stands for methyl group; “Et” stands for ethyl group; “n-Pr” stands for normal propyl group; “i-Pr” stands for isopropyl group; “c-Pr” stands for cyclopropyl group; “n-Bu” stands for normal butyl group; “s-Bu” stands for sec-butyl group; “i-Bu” stands for isobutyl group; “t-Bu” stands for tert-butyl group; “c-Bu” stands for cyclobutyl group; “n-Pen” stands for normal pentyl group; “c-Pen” stands for cyclopentyl group; “n-Hex” stands for normal hexyl group; “c-Hex” stands for cyclohexyl group; “Ph” stands for phenyl group; “Bz” stands for benzoyl group; and “Np” stands for naphthyl group.

Next, although production methods of the isoxazolin-5-one derivatives represented by the formula (1) of the invention are explained in detail, the production methods are not limited to these methods. In this regard, regarding the reaction devices, reaction using a microwave synthesis device is also possible in addition to reaction using a magnetic stirrer or a mechanical stirrer.

(R 3 , X and n have the same meanings as those described above. Y represents a leaving group such as a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group or a toluenesulfonyloxy group. R 5 represents a C1-C6 alkyl group.)

›DESCRIPTION OF EMBODIMENTS · 7 of 14

The step-1 is a step of reacting a nitrobenzene derivative represented by the formula (2) and a β-ketoester derivative represented by the formula (3) in the presence of a base and thus producing a 2-(2-nitrobenzyl)-β-ketoester derivative (4). The nitrobenzene derivative represented by the formula (2) and the β-ketoester derivative represented by the formula (3) are sometimes known and can be obtained from Tokyo Chemical Industry Co., Ltd. or the like. Alternatively, the derivatives can also be easily produced from an available reagent according to a known method described in Courses in Experimental Chemistry, Organic Syntheses or the like.

It is necessary to conduct the reaction in the presence of a base, and as the base, an organic base such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, 4-tert-butyl-N,N-dimethylaniline, pyridine, picoline and lutidine, an alkali metal salt such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, sodium amide, butyllithium, tert-butyllithium, lithium diisopropylamide, trimethylsilyl lithium and lithium hexamethyldisilazide or the like can be used. Of these bases, a metal base such as sodium methoxide and sodium ethoxide is preferable in view of the high yield. By conducting the reaction using the base in an amount of 0.1 to 5 equivalents based on the substrates, the target material can be obtained with a high yield. The reaction substrate (3) is generally used in an amount of 1 to 5 equivalents based on the substrate (2).

The reaction is preferably conducted in the presence of a solvent. A solvent which does not adversely affect the reaction can be used as the solvent used, and an aromatic hydrocarbon-based solvent such as benzene, toluene, xylene and chlorobenzene, an aliphatic hydrocarbon-based solvent such as pentane, hexane and octane, an ether-based solvent such as diethyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, dimethoxyethane and 1,4-dioxane, a ketone such as acetone, methyl ethyl ketone and cyclohexanone, a halogen-based solvent such as chloroform and dichloromethane, a nitrile-based solvent such as acetonitrile and propionitrile, an ester-based solvent such as ethyl acetate, propyl acetate, butyl acetate and methyl propionate, an amide-based solvent such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, an alcohol-based solvent such as methanol, ethanol, 1-propanol, 2-propanol and tert-butanol, dimethyl sulfoxide, water or a mixed solvent thereof can be used. To promote the progress of the reaction, a phase-transfer catalyst such as a quaternary ammonium salt can also be added.

The reaction can be conducted at a temperature which is appropriately determined in the range of from −78° C. to 200° C., although the temperature varies with the reaction conditions. After the reaction, although the target material can be obtained by a general post-treatment operation, the target material can also be purified by column chromatography, recrystallization or the like if necessary.

(R 3 , X, n and R 5 have the same meanings as those described above.)

The step-2 is a step of reacting the 2-(2-nitrobenzyl)-3-ketoester derivative represented by the formula (4) and hydroxylamine represented by the formula (5) and thus producing an isoxazolin-5-one derivative (6). The hydroxylamine represented by the formula (5) may be a quaternary salt such as a hydrochloride or a sulfate.

The reaction may be conducted in the presence of a base, and as the base, an organic base such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, 4-tert-butyl-N,N-dimethylaniline, pyridine, picoline and lutidine, an alkali metal salt such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, sodium amide, butyllithium, tert-butyllithium, lithium diisopropylamide, trimethylsilyl lithium and lithium hexamethyldisilazide or the like can be used. By conducting the reaction using the base in an amount of 0.1 to 5 equivalents based on the substrates, the target material can be obtained with a high yield. The reaction substrate (5) is generally used in an amount of 1 to 5 equivalents based on the substrate (4).

The reaction is preferably conducted in a solvent. A solvent which does not adversely affect the reaction can be used as the solvent, and an aromatic hydrocarbon-based solvent such as benzene, toluene, xylene and chlorobenzene, an aliphatic hydrocarbon-based solvent such as pentane, hexane and octane, an ether-based solvent such as diethyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, dimethoxyethane and 1,4-dioxane, a ketone such as acetone, methyl ethyl ketone and cyclohexanone, a halogen-based solvent such as chloroform and dichloromethane, a nitrile-based solvent such as acetonitrile and propionitrile, an ester-based solvent such as ethyl acetate, propyl acetate, butyl acetate and methyl propionate, an amide-based solvent such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, an alcohol-based solvent such as methanol, ethanol, 1-propanol, 2-propanol and tert-butanol, dimethyl sulfoxide, water or a mixed solvent thereof can be used.

The reaction can be conducted at a temperature which is appropriately determined in the range of from −78° C. to 200° C., although the temperature varies with the base used and the reaction conditions. After the reaction, although the target material can be obtained by a general post-treatment operation, the target material can also be purified by column chromatography, recrystallization or the like if necessary.

›DESCRIPTION OF EMBODIMENTS · 8 of 14

(R 3 , R 4 , X, n and Y have the same meanings as those described above.)

The step-3 is a step of introducing R 4 to the nitrogen atom at the 2-position of the isoxazolin-5-one derivative represented by the formula (6) and thus producing an isoxazolin-5-one derivative represented by the formula (7).

It is necessary to conduct the reaction in the presence of a base, and as the base, an organic base such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, 4-tert-butyl-N,N-dimethylaniline, pyridine, picoline and lutidine, an alkali metal salt such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, sodium amide, butyllithium, tert-butyllithium, lithium diisopropylamide, trimethylsilyl lithium and lithium hexamethyldisilazide or the like can be used. Of these bases, a metal base such as potassium carbonate and sodium hydride is preferable in view of the high yield. By conducting the reaction using the base in an amount of 0.1 to 5 equivalents based on the substrates, the target material can be obtained with a high yield. The reaction substrate (8) is generally used in an amount of 1 to 5 equivalents based on the substrate (6).

(R 3 , R 4 , X and n have the same meanings as those described above.)

The step-4 is a step of reducing the nitro group of the isoxazolin-5-one derivative represented by the formula (7) and thus producing an isoxazolin-5-one derivative (9) having an amino group.

The method for reducing the nitro group in the step can be a method using a reducing agent such as zinc powder, reduced iron, tin powder, stannous chloride and titanium chloride, a method using a hydrogen donor such as hydrazine in the presence of Raney nickel, catalytic hydrogenation reduction or catalytic hydrogen transfer reduction in the presence of a catalyst such as Raney nickel, palladium on carbon, palladium hydroxide and platinum oxide or the like.

The reaction can be conducted at a temperature which is appropriately determined in the range of from 0° C. to 200° C., although the temperature varies with the base used and the reaction conditions. After the reaction, although the target material can be obtained by a general post-treatment operation, the target material can also be purified by column chromatography, recrystallization or the like if necessary.

(R 1 , R 3 , R 4 , X, n and Y have the same meanings as those described above. R 22 represents a hydrogen atom or R 1 SO 2 .)

The step-5 is a step of reacting the isoxazolin-5-one derivative having an amino group represented by the formula (9) and a compound represented by the formula (10) and thus producing an isoxazolin-5-one derivative (la).

The reaction may be conducted in the presence of a base, and as the base, an organic base such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, 4-tert-butyl-N,N-dimethylaniline, pyridine, picoline and lutidine, an alkali metal salt such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, sodium amide, butyllithium, tert-butyllithium, lithium diisopropylamide, trimethylsilyl lithium and lithium hexamethyldisilazide or the like can be used. Of these bases, an organic base such as triethylamine and diisopropylethylamine is preferable in view of the high yield. By conducting the reaction using the base in an amount of 0.1 to 5 equivalents based on the substrates, the target material can be obtained with a high yield.

›DESCRIPTION OF EMBODIMENTS · 9 of 14

(R 1 , R 3 , R 4 , X, n and Y have the same meanings as those described above. R 23 represents any of the groups in R 2 except for hydrogen atom.)

The step-6 is a step of reacting a compound represented by the formula (11) with an isoxazolin-5-one derivative represented by the formula (1b) and thus producing an isoxazolin-5-one derivative (1c).

It is necessary to conduct the reaction in the presence of a base depending on the kind of the compound (11), and as the base, an organic base such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, 4-tert-butyl-N,N-dimethylaniline, pyridine, picoline and lutidine, an alkali metal salt such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, sodium amide, butyllithium, tert-butyllithium, lithium diisopropylamide, trimethylsilyl lithium and lithium hexamethyldisilazide or the like can be used. By conducting the reaction using the base in an amount of 0.1 to 5 equivalents based on the substrates, the target material can be obtained with a high yield.

(R 1 , R 3 , R 4 , R 23 , X, n and Y have the same meanings as those described above.)

The step-7 is a step of reacting the sulfonyl compound represented by the formula (10) with an isoxazolin-5-one derivative represented by the formula (1d) and thus producing the isoxazolin-5-one derivative (1c).

›DESCRIPTION OF EMBODIMENTS · 10 of 14

(X, n, Y and R 5 have the same meanings as those described above.)

The step-8 is a step of reacting the nitrobenzene derivative represented by the formula (2) and a phosphonium ylide derivative represented by the formula (12) and thus producing a phosphonium salt derivative (13). The phosphonium ylide derivative represented by the formula (12) is sometimes known and can be obtained from Tokyo Chemical Industry Co., Ltd. or the like. Alternatively, the derivative can also be easily produced from an available reagent according to a known method described in Courses in Experimental Chemistry, Organic Syntheses or the like.

The reaction is preferably conducted in the presence of a solvent. A solvent which does not adversely affect the reaction can be used as the solvent used, and an aromatic hydrocarbon-based solvent such as benzene, toluene, xylene and chlorobenzene, an aliphatic hydrocarbon-based solvent such as pentane, hexane and octane, an ether-based solvent such as diethyl ether, diisopropyl ether, cyclopentyl methyl ether, tetrahydrofuran, dimethoxyethane and 1,4-dioxane, a halogen-based solvent such as chloroform, dichloromethane and 1,2-dichloroethane, an ester-based solvent such as ethyl acetate, propyl acetate, butyl acetate and methyl propionate, an amide-based solvent such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, dimethyl sulfoxide or a mixed solvent thereof can be used. To promote the progress of the reaction, a phase-transfer catalyst such as a quaternary ammonium salt can also be added.

(X, n, Y and R 5 have the same meanings as those described above. Z represents a halogen atom. R 6 represents a hydrogen atom or a C1-C6 alkyl group. R 7 represents a hydrogen atom or a C1-C6 alkyl group.)

The step-9 is a step of reacting the phosphonium salt derivative represented by the formula (13) and an acyl halide derivative represented by the formula (14) in the presence of a base and thus producing an allenoate derivative (15).

It is necessary to conduct the reaction in the presence of a base, and as the base, an organic base such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, 4-tert-butyl-N,N-dimethylaniline, pyridine, picoline and lutidine, an alkali metal salt such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, sodium amide, butyllithium, tert-butyllithium, lithium diisopropylamide, trimethylsilyl lithium and lithium hexamethyldisilazide or the like can be used. Of these bases, an organic base such as triethylamine and diisopropylethylamine is preferable in view of the high yield. By conducting the reaction using the base in an amount of 0.1 to 5 equivalents based on the substrates, the target material can be obtained with a high yield. The reaction substrate (14) is generally used in an amount of 1 to 5 equivalents based on the substrate (13).

(X, n, R 4 , R 5 , R 6 and R 7 have the same meanings as those described above.)

The step-10 is a step of reacting the allenoate derivative represented by the formula (15) and a hydroxylamine derivative represented by the formula (16) and thus producing an isoxazolin-5-one derivative (17). The hydroxylamine derivative represented by the formula (16) is sometimes known and can be obtained from Tokyo Chemical Industry Co., Ltd. or the like. Alternatively, the derivative can also be easily produced from an available reagent according to a known method described in Courses in Experimental Chemistry, Organic Syntheses or the like. The hydroxylamine derivative represented by the formula (16) may be a quaternary salt such as a hydrochloride or a sulfate.

The reaction may be conducted in the presence of a base, and as the base, an organic base such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, 4-tert-butyl-N,N-dimethylaniline, pyridine, picoline and lutidine, an alkali metal salt such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, sodium amide, butyllithium, tert-butyllithium, lithium diisopropylamide, trimethylsilyl lithium and lithium hexamethyldisilazide or the like can be used. Of these bases, an organic base such as triethylamine and diisopropylamine is preferable in view of the high yield. By conducting the reaction using the base in an amount of 0.1 to 5 equivalents based on the substrates, the target material can be obtained with a high yield. The reaction substrate (16) is generally used in an amount of 1 to 5 equivalents based on the substrate (15).

›DESCRIPTION OF EMBODIMENTS · 11 of 14

The compounds of the invention can be analyzed, confirmed or identified by the melting points, the infrared absorption spectra, 1 H-NMR, 13 C-NMR, mass spectrometry, X-ray structure analysis or the like, if necessary.

The production methods are not limited to those described above, and the compounds of the invention can be produced by any organic synthesis methods.

As also shown in Test Examples described below, the compounds of the invention exhibit an excellent herbicidal activity and exhibit an excellent selective weed killing activity distinguishing the weeds and the crops below. Thus, the compounds can be used for a wide range of targets such as weeds and the like in paddy rice fields and dry field. Specific examples of the weeds are as follows.

Specifically, for example, the following harmful weeds can be controlled: Gramineae weeds such as Echinochloa crus - galli, Echinochloa oryzicola , southern crabgrass ( Digitaria sanguinalis, Digitaria ischaem, Digitaria adscendens, Digitaria microbachne or Digitaria horizontalis ), Setaria viridis, Setaria faberi, Setaria lutescens, Eleusine indica, Avena fatua, Sorghum halepense, Aropyron repens, Brachiaria plantaginea, Panicum maximum, Panicum purpurascens, Panicum dichotomiflorum, Leptochloa chinensis, Leptochloa panicea, Poa annua, Alopecurus aequalis, Alopecurus myosuroides, Agropyron tsukushiense, Bracharia platyphylla, Cenchrus echinatus, Lolium multiflorum, Cynodon dactylon, Beckmannia syzigache, Bromus catharticus, Leersia japonica, Leersia sayanuka, Lolium rigidum, Paspalum distichum and Phleum pratense ; Cyperaceae weeds such as Cyperus iria, Cyperus rotundus, Cyperus esculentus, Scirpus hotarui, Cyperus serotinus, Cyperus serotinus, Eleocharis acicularis, Eleocharis kuroguwai, Cyperus flaccidus, Kyllinga brevifolia and Scirpus juncoides ; Alismataceae weeds such as Sagittaria pygmaea, Sagittaria trifolia and Alisma canaliculatum ; Pontderiaceae weeds such as Monochoria vaginalis, Heteranthera limosa and Monochoria kosakowii ; Linderniaceae weeds such as Lindernia pyxidaria ; Plantaginaceae weeds such as Plantago asiatica, Gratiola japonica, Dopatrium junceum and Veronica polita ; Lythraceae weeds such as Rotala india, Ammannia multifflora and Rotala indica ; Elatinaceae weeds such as Elatine triandra ; Malvaceae weeds such as Abutiol theophrsti and Sida spinosa ; Compositae weeds such as Xanthium strumarim, Ambrosia elatior, Breea serosa, Galinsoga ciliata, Matricaria chamomilla, Taraxacum officinale, Erigeron canadensis, Bidens frondosa, Bidens pilosa, Bidens tripartita, Gnaphalium affine and Senecio vulgaris ; Lamiaceae weeds such as Lamium amplexinale weber ; Solanaceae weeds such as Solanum nigrum and Datura stramonium ; Amaranthaceae weeds such as Amaranthus viridis, Chenopodium album, Kochia scoparia and Amaranthus hybridus ; Polygonaceeae weeds such as Polygonum lapathifolium, Polygonum persicaria, Polygonum convolvulus, Polygonum aviculare, Persicaria longiseta and Persicaria nepalensis ; Crpurea weeds such as Cardamine flexuosa, Capsella bursapastoris, Brassica juncea and Rorippa indica ; Convolvulaceae weeds such as Ipomoea purpurea, Convolvulus arvensis, Ipomoea hederacea, Calystegia pubescens and Ipomoea coccinea ; Portulacaceae weeds such as Portulaca oleracea ; Fabaceae weeds such as Cassia obtusifolia, Aeschynomene indica, Sesbania exaltata, Trifolium repens and Vicia sativa ; Caryophyllaceae weeds such as Stellaria media, Stellaria neglecta and Stellaria uliginosa ; Euphoribiaceae weeds such as Euphorbia helioscopia and Acalypha australis ; Commelinaceae weeds such as Commelina communis and Murdannia keisak ; Potamogetonaceae weeds such as Potamogeton distinctus ; Araceae weeds such as Spirodela polyrhiza ; Cucurbitaceae weeds such as Sicyos angulatus ; Rubiaceae weeds such as Galium spurium ; Apiaceae weeds such as Oenanthe javanica ; Violaceae weeds such as Viola mandshuria ; Onagraceae weeds such as Ludwigia epilobioides and Oenothera odorata ; Oxalidaceae weeds such as Oxalis corniculata ; Equisetaceae weeds such as Equisetum arvense ; Zygnemataceae weeds such as Spirogyra sp. and the like. Accordingly, the compounds are effectively used for a case of selectively controlling a harmful weed or a case of non-selectively controlling a harmful weed in culturing, for example, Zea mays, Glycine max, Gossypium spp., Triticum spp., Hordeum vulgare, Secale cereale, Avena sativa, Sorghum bicolor, Brassica napus, Helianthus annuus, Beta Vulgaris, Saccharum officinarum, Zoysia japonicaa, Arachis hypogaea, Linum usitatissmum, Nicotiana tabacum, Coffea spp. or the like, which are useful crops.

›DESCRIPTION OF EMBODIMENTS · 12 of 14

The applications of the herbicides of the invention are not limited to the weeds and the crops described above as examples.

If necessary, the compounds of the invention may be prepared as mixed formulations with another kind of herbicide, an insecticide, an acaricide, a nematicide, a germicide (a fungicide, a bactericide, an antiviral agent or a plant resistance inducer), a bird repellent, a plant growth regulator, a safener, a fertilizer, a soil conditioner, a synergist or the like during the formation or spraying or may be blended with such an agent in a tank mixer at spraying and applied.

In particular, when the compounds are blended and applied with another kind of herbicide, the amount of the used herbicide can be reduced, and the labor can be reduced. Moreover, the range of the targets of the herbicides (weed control spectrum) broadens due to the multiplier action of the agents, and a stronger effect can be expected due to the synergistic action of the agents. At this point, more than one kind of known herbicide or safener can also be combined and blended at the same time.

Of the optional components above, although representative examples of herbicides are shown below, the components are not limited to these examples only.

(1) Phenoxy-based compounds such as 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-sodium, 2,4-D-isopropanolammonium, 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium 2,4-D choline salt, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop-potassium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-potassium, dichlorprop-P-sodium, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-potassium, MCPA-sodium, MCPA-thioetyl, MCPB, MCPB-ethyl, MCPB-sodium, mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethyl ammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, naproanilide, clomeprop and HIA-1; aromatic carboxylic acid-based compounds such as 2,3,6-TBA, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, picloram, picloram-dimethylammonium, picloram-isooctyl, picloram-potassium, picloram-trii sopropanolammonium, picloram-trii sopropylammonium, picloram-trolamine, tricolopyr, tricolopyr-butotyl, tricolopyr-triethylammonium, clopyralid, clopyralid-olamine, clopyralid-potassium, clopyralid-triisopropanolammonium, aminopyralid, aminocyclopyrachlor, aminocyclopyrachlor, halauxifen, florpyrauxifen, halauxifen-methyl and DAS-534; and other compounds which are considered to exhibit a herbicidal efficacy by disturbing the hormone action of a plant, such as naptalam, naptalam-sodium, benazolin, benazolin-ethyl, quinclorac, quinmerac, diflufenzopyr, diflufenzopyr-sodium, fluroxypyr, fluroxypyr-2-butoxy-1-methylethyl, fluroxypyr-meptyl, chlorflurenol, chlorflurenol-methyl and clacyfos.

(2) Urea-based compounds such as chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, karbutilate, methabenztiazuron, metoxuron, metoburomuron, monolinuron, neburon, siduron, terbumeton and trietazine; triazine-based compounds such as simazine, atrazine, atratone, simetryn, prometryn, dimethametryn, hexazinone, metribuzin, terbuthylazine, cyanazine, ametryn, cybutryne, terbutryn, propazine, metamitron and prometon; uracil-based compounds such as bromacil, bromacyl-lithium, lenacil and terbacil; anilide-based compounds such as propanil and cypromid; carbamate-based compounds such as swep, desmedipham and phenmedipham; hydroxybenzonitrile-based compounds such as bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium; and other compounds which are considered to exhibit a herbicidal efficacy by inhibiting the photosynthesis of a plant, such as pyridate, bentazone, bentazone-sodium, amicarbazone, methazole, pentanochlor and phenmedipham.

(3) Quaternary ammonium salt-based compounds which become free radicals in the plant and which are considered to generate active oxygen and exhibit an immediate herbicidal efficacy, such as paraquat and diquat.

(4) Diphenyl ether-based compounds such as nitrofen, chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesafen-sodium, oxyfluorfen, lactofen, aclonifen, ethoxyfen-ethyl, fluoroglycofen-ethyl and fluoroglycofen; cyclic imide-based compounds such as chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, cinidon-ethyl, fluthiacet-methyl and EK-5385; and other compounds which are considered to exhibit a herbicidal efficacy by inhibiting chlorophyll biosynthesis of a plant and causing abnormal accumulation of a photosensitizing peroxide substance in the plant, such as oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone, azafenidin, isopropazole, pyraflufen-ethyl, benzfendizone, butafenacil, saflufenacil, fluazolate, profluazol, flufenpyr-ethyl, bencarbazone, tiafenacil, pyrachlonil, trifludimoxazin, HNPC-B4047, IR-6396, EK-5498, SYN-523 and the compound described in WO2008/008763 (FMC).

(5) Pyridazinone-based compounds such as norflurazon, chloridazon and metflurazon; pyrazole-based compounds such as pyrazolynate, pyrazoxyfen, benzofenap, topramezone, pyrasulfotole and tolpyralate; and other compounds which are considered to exhibit a herbicidal efficacy characterized by a bleaching effect by inhibiting biosynthesis of a pigment of a plant such as carotenoids, such as amitrole, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulcotrione, mesotrione, tembotrione, tefuryltrione, fenquinotrione, lancotrione, cyclopyrimorate, isoxaflutole, difenzoquat, difenzoquat-metilsulfate, isoxachlortole, benzobicyclon, bicyclopyron, picolinafen, beflubutamid, ketospiradox, ketospiradox-potassium and compounds described in JP2012/2571 (Sumitomo Chemical Company, Limited).

›DESCRIPTION OF EMBODIMENTS · 13 of 14

(6) Compounds which are considered to inhibit biosynthesis of fatty acids and exhibit a herbicidal efficacy on a plant including aryloxyphenoxypropionic acid-based compounds such as diclofop-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, haloxyfop-P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl, metamifop, clodinafop-propargyl, propaquizafop, HNPC-A8169 and SYP-1924; cyclohexanedione-based compounds such as alloxydim-sodium, alloxydim, clethodim, sethoxydim, tralkoxydim, butroxydim, tepraloxydim, profoxydim and cycloxydim; phenylpyrazoline-based compounds such as pinoxaden; and the like.

(7) Sulfonylurea compounds such as chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, chlorsulfuron, metsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl, pyrazosulfuron, flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron, flucetosulfuron, cyclosulfamuron, prosulfuron, flupyrsulfuron-methyl-sodium, flupyrsulfuron, triflusulfuron, flupyrsulfuron-methyl-sodium, flupyrsulfuron, triflusulfuron-methyl, triflusulfuron, halosulfuron-methyl, halosulfuron, thifensulfuron-methyl, thifensulfuron, ethoxysulfuron, oxasulfuron, ethametsulfuron, ethametsulfuron-methyl, iodosulfuron, iodosulfuron-methyl-sodium, sulfosulfuron, triasulfuron, tribenuron-methyl, tribenuron, tritosulfuron, foramsulfuron, trifloxysulfuron, trifloxysulfuron-sodium, mesosulfuron-methyl, mesosulfuron, orthosulfamuron, amidosulfuron, azimsulfuron, propyrisulfuron, metazosulfuron, methiopyrsulfuron, monosulfuron-methyl, orsosulfuron, iofensulfuron and iofensulfuron-sodium; triazolopyrimidinesulfonamide-based compounds such as flumetsulam, metosulam, diclosulam, cloransulam-methyl, florasulam, penoxsulam and pyroxsulam; imidazolinone-based compounds such as imazapyr, imazapyr-isopropylammonium, imazethapyr, imazethapyr-ammonium, imazaquin, imazaquin-ammonium, imazamox, imazamox-ammonium, imazamethabenz, imazamethabenz-methyl and imazapic; pyrimidinyl salicylic acid-based compounds such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid, pyrimisulfan and triafamone; sulfonylaminocarbonyltriazolinone-based compounds such as flucarbazone, flucarbazone-sodium, propoxycarbazone-sodium, propoxycarbazone and thiencarbazone-methyl; and other compounds which are considered to exhibit a herbicidal efficacy by inhibiting amino acid biosynthesis of a plant, such as glyphosate, glyphosate-sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-trimesium, glyphosate-sesquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, bilanafos, bilanafos-sodium and cinmethylin.

(8) Dinitroaniline-based compounds such as trifluralin, oryzalin, nitralin, pendimethalin, ethalfluralin, benfluralin, prodiamine, butralin and dinitramine; amide-based compounds such as bensulide, napropamide, napropamide-M, propyzamide and pronamide; organic phosphorus-based compounds such as amiprofos-methyl, butamifos, anilofos and piperophos; phenyl carbamate-based compounds such as propham, chlorpropham, barban and carbetamide; cumylamine-based compounds such as daimuron, cumyluron, bromobutide and methyldymron; and other compounds which are considered to exhibit a herbicidal efficacy by inhibiting cell mitosis of a plant, such as asulam, asulam-sodium, dithiopyr, thiazopyr, chlorthal-dimethyl, chlorthal, diphenamid, flamprop-M-methyl, flamprop-M and flamprop-M-isopropyl.

(9) Chloroacetamide-based compounds such as alachlor, metazachlor, butachlor, pretilachlor, metolachlor, S-metolachlor, thenylchlor, pethoxamid, acetochlor, propachlor, dimethenamide, dimethenamide-P, propisochlor and dimethachlor; thiocarbamate-based compounds such as molinate, dimepiperate, pyributicarb, EPTC, butylate, vernolate, cycloate, prosulfocarb, esprocarb, thiobencarb, diallate, tri-allate and orbencarb; and other compounds which are considered to exhibit a herbicidal efficacy by inhibiting protein biosynthesis or lipid biosynthesis of a plant, such as etobenzanid, mefenacet, flufenacet, tridiphane, cafenstrole, fentrazamide, ipfencarbazone, oxaziclomefone, indanofan, benfuresate, pyroxasulfone, fenoxasulfone, methiozolin, dalapon, dalapon-sodium, TCA-sodium and trichloracetic acid.

(10) Compounds which are considered to exhibit a herbicidal efficacy by inhibiting cellulose biosynthesis of a plant, such as dichlobenil, triaziflam, indaziflam, flupoxam and isoxaben.

(11) Other herbicides such as MSMA, DSMA, CMA, endothall, endothall-dipotassium, endothall-sodium, endothall-mono(N,N-dimethylalkylammonium), ethofumesate, sodium chlarate, pelargonic acid, nonanoic acid, fosamine, fosamine-ammonium, aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacetate, cyanamide, methylarsonic acid, dimethylarsonic acid, sodium dimethylarsonate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC, ferrous sulfate, flupropanate, flupropanate-sodium, mefluidide, mefluidide-diolamine, metam, metam-ammonium, metam-potassium, metam-sodium, methyl isothiocyanate, pentachlorophenol, sodium pentachlorophenoxide, pentachlorophenol laurate, quinoclamine, sulfuric acid, urea sulfate, zanthinosin, herbimycin, unguinol, metatyrosine, sarmentine, thaxtomin A, mevalocidin, alpha-limonene, pyribambenz-propyl, pyribambenz-isopropyl, JS-913, KHG-23844, H-9201, SIOC-0163, SIOC-0171, SIOC-0172, SIOC-0285, SIOC-0426, SIOC-H-057, ZJ-0166, ZJ-1835, ZJ-0453, ZJ-0777, ZJ-0862 and compounds described in WO2008/096398 (Kumiai Chemical Industry Co., Ltd.).

(12) Those which are considered to exhibit a herbicidal efficacy by parasitizing in a plant, such as Xanthomonas campestris, Epicoccosirus nematosorus, Epicoccosirus nematosperus, Exserohilum monoseras and Drechsrela monoceras.

›DESCRIPTION OF EMBODIMENTS · 14 of 14

When the compounds of the invention are used as herbicides, the compounds can be directly used but can also be used as formulations. To prepare the formulations, an appropriate carrier, an auxiliary agent, a surfactant, a binder, a stabilizer and the like described in Pesticide Formulation Guide (edited by Special Committee on Application of Pesticide Science Society of Japan, issued by Japan Plant Protection Association, 1997).

The herbicides containing the compounds of the invention can be formulated into any agent forms which are generally used as agent forms. For example, although the herbicides can be used in the forms of granules, microgranules, fine granules, water dispersible powder, a granulate water dispersible (dry flowable) agent, an emulsion, water soluble powder, a sol agent (flowable agent), a liquid, powder, rough powder, DL (driftless) powder, a flow dust agent, an oil, a microcapsule, a paste, a jumbo agent and the like, the forms are not limited to these examples.

As the carrier used for formulation, both solid and liquid can be used as long as the carrier is generally used for herbicide formulations. Although the carrier is not limited to a particular carrier, specific examples include the following carriers. Examples of the solid carrier include mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, quartz, calcium carbonate, apatite, white carbon, slaked lime, silica sand, Japanese acid clay, zeolite, sepiolite, expanded perlite powder, Shirasu-balloon, alumina balloon, a phenolic resin, an epoxy resin, polyacrylonitrile, microspheres of polyurethane or the like and the like), vegetable powders (soybean flour, wheat flour, wood flour, tobacco powder, starch, crystalline cellulose and the like), polymer compounds (a petroleum resin, polyvinyl chloride, a ketone resin and the like), alumina, silicate, glucose, sucrose, lactose, glycopolymers, ammonium sulfate, sodium chloride, potassium chloride, urea, highly dispersible silicic acid, waxes and the like.

Examples of the liquid carrier include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, butanol, ethylene glycol, benzyl alcohol and the like), aromatic hydrocarbons (toluene, benzene, xylene, ethyl benzene, methylnaphthalene and the like), ethers (ethyl ether, ethylene oxide, dioxane, tetrahydrofuran and the like), ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, isophorone and the like), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate and the like), acid amides (dimethylformamide, dimethylacetamide and the like), nitriles (acetonitrile, propionitrile, acrylonitrile and the like), sulfoxides (dimethyl sulfoxide and the like), alcoholethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and the like), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane and the like), industrial gasoline (petroleum ether, solvent naphtha and the like), petroleum fractions (paraffin, kerosene, light oil and the like) and the like.

When the herbicides are formulated into an emulsion, water dispersible powder, a flowable agent or the like, various kinds of surfactant are blended for the purpose of emulsification, dispersion, solubilization, wetting, foaming, lubrication, spreading or the like. Examples of such a surfactant include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, polyoxyethylenealkyl aryl ethers, polyoxyethylene-polyoxypropylene block polymers and polyoxyethylene styrylphenylethers, anionic surfactants such as alkylbenzene sulfonates, alkyl sulfosuccinates, alkyl sulfates, polyoxyethylene alkyl sulfates, aryl sulfonates, alkylnaphthalene sulfonates, polyoxyethylene styrylphenylether sulfates, lignin sulfonates, naphthalene sulfonate formaldehyde condensate and polycarboxylates, cationic surfactants such as alkylamines (lauryl amine, stearyltrimethyl ammonium chloride and the like), polyoxyethylene alkyl amines, alkyl pyridinium salts, alkyltrimethyl ammonium salts and alkyldimethyl ammonium salts, ampholytic surfactants such as carboxylic acid (betaine type) and sulfate esters and the like, but the surfactant is not limited to the examples.

In addition, various kinds of auxiliary agent and additive such as polyvinyl alcohol (PVA), carboxymethyl cellulose (CMC), gum arabic, polyvinyl acetate, sodium alginate, gelatin, tragacanth gum, dextrin, hydroxypropyl methylcellulose (HPMC) and methyl cellulose (MC) and the like can be used.

An appropriate amount of the compound of the invention in the herbicide is around 0.01 to 90% based on the mass.

Preferable methods for using the herbicides containing the compounds of the invention as active ingredients include soil treatment, water surface treatment, leave and stem treatment and the like, and the herbicides can exhibit a particularly excellent effect when applied before germination and during the plumule period of a weed to be controlled.

Although the amount of the compound of the invention to be applied as an herbicide differs with the situation of the application, the time of the application, the application method, the target weed, the cultivated crop and the like, an appropriate amount of the active ingredient is generally around 0.001 to 10 Kg, and preferably around 0.01 to 1 Kg per hectare (ha).

›EXAMPLES · 1 of 4

Although the invention is explained further specifically below using Synthesis Examples, Formulation Examples and Test Examples of the compounds of the invention, the invention is not limited to the examples.

Synthesis Example 1

Synthesis of 1,1,1-trifluoro-N-[2-[(2-isobutyl-3-methyl-5-oxoisoxazol-4-yl)methyl]phenyl]methanesulfonamide (1-105) and 1,1,1-trifluoro-N-[2-[(2-isobutyl-3-methyl-5-oxoisoxazol-4-yl)methyl]phenyl]-N-(trifluoromethylsulfonyl)methanesulfonamide (1-967

Triethylamine (200 mg, 2.00 mmol) and trifluoromethanesulfonic acid anhydride (400 mg, 1.40 mmol) were added at 0° C. to a chloroform solution (10 ml) of 4-[(2-aminophenyl)methyl]-2-isobutyl-3-methylisoxazolin-5-one (350 mg, 1.30 mmol), and the mixture was stirred at the same temperature for an hour. Water was poured into the reaction mixture, followed by extraction with chloroform. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3), and 1,1,1-trifluoro-N-[2-[(2-isobutyl-3-methyl-5-oxoisoxazol-4-yl)methyl]phenyl]methanesulfonamide (amount of 230 mg, yield of 59%) as a yellow oil and 1,1,1-trifluoro-N-[2-[(2-isobutyl-3-methyl-5-oxoisoxazol-4-yl)methyl]phenyl]-N-(trifluoromethylsulfonyl)methanesulfonamide (amount of 180 mg, yield of 34%) as a yellow solid were thus obtained.

Synthesis Example 2

Synthesis of 1,1,1-trifluoro-N-[2-[(3-methyl-5-oxo-2-sec-butyl-isoxazol-4-yl)methyl]phenyl]methanesulfonamide (1-102) and 1,1,1-trifluoro-N-[2-[(3-methyl-5-oxo-2-sec-butyl-isoxazol-4-yl)methyl]phenyl]-N-(trifluoromethyl sulfonyl)methanesulfonamide (1-964

Triethylamine (86.0 mg, 0.850 mmol) and trifluoromethanesulfonic anhydride (220 mg, 0.770 mmol) were added at 0° C. to a chloroform solution (3 ml) of 4-[(2-aminophenyl)methyl]-3-methyl-2-sec-butyl-isoxazolin-5-one (100 mg, 0.380 mmol), and the mixture was stirred at the same temperature for an hour. Water was poured into the reaction mixture, followed by extraction with chloroform. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3), and 1,1,1-trifluoro-N-[2-[(3-methyl-5-oxo-2-sec-butyl-isoxazol-4-yl)methyl]phenyl]methanesulfonamide (amount of 80.0 mg, yield of 50%) as a yellow oil and 1,1,1-trifluoro-N-[2-[(3-methyl-5-oxo-2-sec-butyl-isoxazol-4-yl)methyl]phenyl]-N-(trifluoromethylsulfonyl)methanesulfonamide (amount of 20.0 mg, yield of 10%) as a yellow gum were thus obtained.

Synthesis Example 3

Synthesis of 1,1,1-trifluoro-N-[2-[[2-(2-methoxy-1-methyl-ethyl)-3-methyl-5-oxo-isoxazol-4-yl]methyl]phenyl]methanesulfonamide (1-149) and 1,1,1-trifluoro-N-[2-[[2-(2-methoxy-1-methyl-ethyl)-3-methyl-5-oxo-isoxazol-4-yl]methyl]phenyl]-N-(trifluoromethyl sulfonyl)methanesulfonamide (1-997

The same reaction and treatment as those in Synthesis Example 2 were conducted using 4-[(2-aminophenyl)methyl]-2-(2-methoxy-1-methyl-ethyl)-3-methyl-isoxazolin-5-one instead of 4-[(2-aminophenyl)methyl]-3-methyl-2-sec-butyl-isoxazolin-5-one, and 1,1,1-trifluoro-N-[2-[[2-(2-methoxy-1-methyl-ethyl)-3-methyl-5-oxo-isoxazol-4-yl]methyl]phenyl]methanesulfonamide (yield of 47%) as a white solid and 1,1,1-trifluoro-N-[2-[[2-(2-methoxy-1-methyl-ethyl)-3-methyl-5-oxo-isoxazol-4-yl]methyl]phenyl]-N-(trifluoromethylsulfonyl)methanesulfonamide (yield of 14%) as a yellow solid were thus obtained.

Synthesis Example 4

Synthesis of N-[2-[(2-isobutyl-3-methyl-5-oxoisoxazol-4-yl)methyl]phenyl]-N-(trifluoromethyl sulfonyl)acetamide (1-297

Triethylamine (71.0 mg, 0.700 mmol) and acetyl chloride (51.0 mg, 0.640 mmol) were added at 0° C. to a chloroform solution (3 ml) of 1,1,1-trifluoro-N-[2-[(2-isobutyl-3-methyl-5-oxoisoxazol-4-yl)methyl]phenyl]methanesulfonamide (230 mg, 0.590 mmol), and the mixture was stirred at the same temperature for an hour. Water was poured into the reaction mixture, followed by extraction with chloroform. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1), and the title compound (amount of 240 mg, yield of 94%) as a yellow oil was thus obtained.

Synthesis Example 5

Synthesis of methyl N-[2-[(3-methyl-5-oxo-2-sec-butyl-isoxazol-4-yl)methyl]phenyl]-N-(trifluoromethyl sulfonyl)carbamate (1-577

Sodium hydrogen carbonate (161 mg, 1.91 mmol) and methyl chloroformate (181 mg, 1.91 mmol) were added to an acetonitrile solution (3 ml) of 1,1,1-trifluoro-N-[2-[(3-methyl-5-oxo-2-sec-butyl-isoxazol-4-yl)methyl]phenyl]methanesulfonamide (250 mg, 0.637 mmol), and the mixture was heated under reflux for an hour. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3), and the title compound (amount of 201 mg, yield of 70%) as a yellow solid was thus obtained.

Synthesis Example 6

Synthesis of N-[2-[(2-tert-butyl-3-methyl-5-oxo-isoxazol-4-yl)]methyl]phenyl]-1,1,1-trifluoromethanesulfonamide (1-101) and N-[2-[(2-tert-butyl-3-methyl-5-oxo-isoxazol-4-yl)methyl]phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide (1-963

Triethylamine (1.60 g, 16.0 mmol) and trifluoromethanesulfonic anhydride (4.10 g, 15.0 mmol) were added at 0° C. to a chloroform solution (100 ml) of 4-[(2-aminophenyl)methyl]-2-tert-butyl-3-methyl-isoxazolin-5-one (2.70 g, 10.0 mmol), and the mixture was stirred at the same temperature for an hour. Water was poured into the reaction mixture, followed by extraction with chloroform. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3), and N-[2-[(2-tert-butyl-3-methyl5-oxo-isoxazol-4-yl)]methyl]phenyl]-1,1,1-trifluoro-methanesulfonamide (amount of 1.40 g, yield of 34%) as a yellow oil and N-[2-[(2-tert-butyl-3-methyl-5-oxo-isoxazol-4-yl)methyl]phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide (amount of 0.95 g, yield of 17%) as a yellow amorphous material were thus obtained.

›EXAMPLES · 2 of 4

The 1 HNMR spectrum (CDCl 3 ) σ (ppm) values, the melting points (° C.) and the like of the compounds according to the invention produced based on the above Synthesis Examples and the above production methods are shown in Table 2. The 1 HNMR data were measured by JNM-ECS400 spectrometer (manufactured by JEOL Ltd.). The compound numbers in Table 2 are the same as those in Table 1 above.

Although the Reference Examples below show Synthesis Examples for synthesizing the starting substances of the syntheses above from commercial products, the syntheses are not limited to the examples.

Reference Example 1

Synthesis of 3-methyl-4-[(2-nitrophenyl)methyl]-2H-isoxazol-5-one

Ethyl acetoacetate (834 g, 641 mmol) was added at 0° C. to a dimethoxyethane solution (1000 ml) of 60% sodium hydride (25.6 g, 641 mmol), and the mixture was stirred at room temperature for 30 minutes. To the mixture solution, 2-Nitrobenzyl chloride (100 g, 583 mmol) (manufactured by Tokyo Chemical Industry Co., Ltd.) was added at 0° C., and the mixture solution was stirred at 80° C. for three hours. The reaction mixture was poured into an aqueous dilute hydrochloric acid solution, followed by extraction with ethyl acetate. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and ethyl 2-[(2-nitrophenyl)methyl]-3-oxo-butanoate (amount of 155 g, yield of 100%) as a yellow oil was thus obtained. Hydroxylamine chloride (60.7 g, 873 mmol) was added to a methanol solution (500 ml) of the obtained oil, and the mixture was stirred at 80° C. for an hour. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was washed with a mixed solvent (ethyl acetate/n-hexane=1/2), and the title compound (amount of 100 g, yield of 73%) as a white solid was thus obtained.

Melting point: 148 to 150° C.

1 HNMR spectrum (DMSO-d6) σ: 12.1 (1H, br.s), 7.89 (1H, d, J=7.6 Hz), 7.60 (1H, t, J=7.6 Hz), 7.44 (1H, t, J=7.6 Hz), 7.36 (1H, d, J=7.6 Hz), 2.00 (3H, s).

Reference Example 2

Synthesis of 2-isobutyl-3-methyl-4-[(2-nitrophenyl)methyl]isoxazol-5-one

Potassium carbonate (5.50 g, 40.0 mmol) and 1-iodo-2-methylpropane (5.80 g, 32.0 mmol) were added to a N,N-dimethylformamide solution (15 ml) of 3-methyl-4-[(2-nitrophenyl)methyl]-2H-isoxazol-5-one (6.20 g, 26.0 mmol), and the mixture was stirred at 80° C. for five hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5), and the title compound (amount of 3.50 g, yield of 46%) as a yellow gum was thus obtained. 1 HNMR spectrum (CDCl 3 ) σ: 7.89 (1H, d, J=7.8 Hz), 7.55-7.51 (2H, m), 7.38-7.34 (1H, m), 3.89 (2H, s), 3.37 (2H, d, J=6.4 Hz), 2.22-2.14 (1H, m), 2.13 (3H, s), 0.96 (6H, d, J=6.4 Hz).

Reference Example 3

Synthesis of 3-methyl-4-[(2-nitrophenyl)methyl]-2-sec-butyl-isoxazol-5-one

The same reaction and treatment as those in Reference Example 2 were conducted using 2-iodobutane instead of 1-iodo-2-methylpropane, and the title compound (yield of 47%) as a yellow gum was thus obtained. 1 HNMR spectrum (CDCl 3 ) σ: 7.89 (1H, d, J=7.8 Hz), 7.54-7.51 (2H, m), 7.38-7.34 (1H, m), 3.90 (2H, d, J=2.3 Hz), 3.88-3.72 (1H, m), 2.13 (3H, s), 1.86-1.79 (1H, m), 1.65-1.58 (1H, m), 1.19 (3H, d, J=7.0 Hz), 0.94 (3H, t, J=7.0 Hz).

Reference Example 4

Synthesis of 2-(2-methoxy-1-methyl-ethyl)-3-methyl-4-[(2-nitrophenyl)methyl]-isoxazol-5-one

The same reaction and treatment as those in Reference Example 2 were conducted using (2-methoxy-1-methyl-ethyl) 4-methylbenzenesulfonate instead of 1-iodo-2-methylpropane, and the title compound (yield of 40%) as a light red solid was thus obtained.

Melting point: 89 to 91° C.

1 HNMR spectrum (CDCl 3 ) σ: 7.91 (1H, d, J=8.0 Hz), 7.54-7.47 (2H, m), 7.38-7.34 (1H, m), 4.13-4.05 (1H, m), 3.92 (2H, m), 3.56 (1H, t, J=10.0 Hz), 3.36 (1H, dd, J=10.0, 4.0 Hz), 3.27 (3H, s), 2.14 (3H, s), 1.28 (3H, d, J=6.8 Hz).

Reference Example 5

Synthesis of 4-[(2-aminophenyl)methyl]-2-isobutyl-3-methylisoxazol-5-one

Reduced iron (3.00 g), ammonium chloride (1.81 g, 33.9 mmol) and water (10 ml) were added to an ethanol solution (30 ml) of 2-isobutyl-3-methyl-4-[(2-nitrophenyl)methyl]isoxazol-5-one (1.97 g, 6.79 mmol), and the mixture was stirred at 90° C. for an hour. The reaction mixture was filtered through Celite, and an aqueous saturated sodium hydrogen carbonate solution was poured, followed by extraction with ethyl acetate. The extraction liquid was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3), and the title compound (amount of 1.73 g, yield of 98%) as a yellow oil was thus obtained.

1 HNMR spectrum (CDCl 3 ) σ: 7.05-6.98 (2H, m), 6.67-6.63 (2H, m), 4.32 (2H, br.s), 3.43 (2H, s), 3.31 (2H, d, J=7.0 Hz), 2.22-2.12 (1H, m), 2.13 (3H, s), 0.94 (6H, d, J=7.0 Hz).

Reference Example 6

Synthesis of 4-[(2-aminophenyl)methyl]-3-methyl-2-sec-butylisoxazol-5-one

The same reaction and treatment as those in Reference Example 5 were conducted using 3-methyl-4-[(2-nitrophenyl)methyl]-2-sec-butyl-isoxazol-5-one instead of 2-isobutyl-3-methyl-4-[(2-nitrophenyl)methyl]isoxazol-5-one, and the title compound (yield of 97%) as a yellow oil was thus obtained.

1 HNMR spectrum (CDCl 3 ) σ: 7.05-6.99 (2H, m), 6.67-6.63 (2H, m), 4.28 (2H, br.s), 3.74-3.67 (1H, m), 3.40 (2H, s), 2.12 (3H, s), 1.86-1.75 (1H, m), 1.65-1.57 (1H, m), 1.17 (3H, d, J=7.0 Hz), 0.92 (3H, d, J=7.0 Hz).

Reference Example 7

Synthesis of 4-[(2-aminophenyl)methyl]-2-(2-methoxy-1-methyl-ethyl)-3-methyl-isoxazolin-5-one

›EXAMPLES · 3 of 4

The same reaction and treatment as those in Reference Example 5 were conducted using 2-(2-methoxy-1-methyl-ethyl)-3-methyl-4-[(2-nitrophenyl)methyl]-isoxazol-5-one instead of 2-isobutyl-3-methyl-4-[(2-nitrophenyl)methyl]isoxazol-5-one, and the title compound (yield of 99%) as a yellow oil was thus obtained.

1 HNMR spectrum (CDCl 3 ) σ: 7.03-6.99 (2H, m), 6.67-6.62 (2H, m), 4.22 (2H, br.s), 4.08-4.00 (1H, m), 3.48 (1H, t, J=10.0 Hz), 3.43 (2H, s), 3.35 (1H, dd, J=10.0, 4.0 Hz), 2.12 (3H, s), 3.18 (3H, s), 2.15 (3H, s), 1.25 (3H, d, J=6.8 Hz).

Reference Example 8

Synthesis of [2-ethoxy-1-[(2-nitrophenyl)methyl]2-oxo-ethyl]triphenyl-phosphonium bromide

Ethyl (triphenylphosphoranylidene)acetate (25.0 g, 71.8 mmol) was added at room temperature to a chloroform (500 ml) solution of 2-nitrobenzyl bromide (15.5 g, 71.8 mol), and the mixture was heated under reflux for five hours. The reaction mixture was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=9/1). The title compound (amount of 29.0 g, yield of 72%) as a brown gum was thus obtained.

1 HNMR spectrum (CDCl 3 ) σ: 8.00-7.38 (19H, m), 3.80 (2H, q, J=7.2 Hz), 3.69-3.55 (3H, m), 0.51 (3H, t, J=7.2 Hz).

Reference Example 9

Synthesis of ethyl 2-[(2-nitrophenyl)methyl]buta-2,3-dienoate

Diisopropylethylamine (2.98 g, 23.0 mmol) was added at room temperature to a chloroform (80 ml) solution of [2-ethoxy-1-[(2-nitrophenyl)methyl]2-oxo-ethyl]triphenyl-phosphonium bromide (13.0 g, 23.0 mmol), and the mixture was stirred at the same temperature for 30 minutes. Then, acetyl chloride (1.81 g, 23.0 mmol) was dropped using a dropping funnel, and the mixture was stirred at the same temperature for an hour. The reaction mixture was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1). The title compound (amount of 5.69 g, yield of 100%) as a light-yellow oil was thus obtained.

1 HNMR spectrum (CDCl 3 ) σ: 7.92-7.90 (1H, m), 7.51 (1H, m), 7.39-7.34 (2H, m), 5.02 (2H, t, J=3.2 Hz), 4.18 (2H, q, J=7.0 Hz), 3.92 (2H, t, J=3.2 Hz), 1.25 (3H, t, J=7.0 Hz).

Reference Example 10

Synthesis of 2-tert-butyl-3-methyl-[(2-nitrophenyl)methyl]isoxazol-5-one

N-(Tert-butyl)hydroxylamine hydrochloride (1.68 g, 13.4 mmol) and triethylamine (1.35 g, 13.4 mmol) were added to a toluene (15 ml) solution of ethyl 2-[(2-nitrophenyl)methyl]buta-2,3-dienoate (3.00 g, 12.1 mmol), and the mixture was stirred at 100° C. for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1). The title compound (amount of 3.5 g, yield of 100%) as a white solid was thus obtained.

Melting point: 86 to 88° C.

1 HNMR spectrum (CDCl 3 ) σ: 7.89 (1H, m), 7.53 (1H, m), 7.46 (1H, m), 7.37 (1H, m), 3.91 (2H, s), 2.23 (3H, s), 1.42 (9H, s).

Reference Example 11

Synthesis of 4-[(2-aminophenyl)methyl]-2-tert-butyl-isoxazol-5-one

The same reaction and treatment as those in Reference Example 5 were conducted using 2-tert-butyl-3-methyl-[(2-nitrophenyl)methyl]isoxazol-5-one instead of 2-isobutyl-3-methyl-4-[(2-nitrophenyl)methyl]isoxazol-5-one, and the title compound (yield of 86%) as a light-yellow solid was thus obtained.

Melting point: 98 to 100° C.

1 HNMR spectrum (CDCl 3 ) σ: 7.01 (2H, m), 6.65 (2H, m), 4.27 (2H, brs), 3.44 (2H, s), 2.25 (3H, s), 1.40 (9H, s)

Next, the methods for formulating the compounds of the invention as herbicides are explained specifically by the Formulation Examples below. In this regard, however, the herbicides are not limited to these Formulation Examples only and can be blended with various other additives at any ratios and formulated.

Formulation Example 1 (Granules

Fifteen parts of water was added to 1 part of the compound of Synthesis Example 1, 1 part of calcium lignin sulfonate, 1 part of lauryl sulfate, 30 parts of bentonite and 67 parts of talc, and the mixture was kneaded with a kneader and then granulated with an extrusion granulator. By drying the granules with a fluidized-bed dryer, granules containing 1% active herbicide ingredient can be obtained. Furthermore, granules can be obtained by the same method except that each compound in Table 1 is used instead of the compound of Synthesis Example 1.

Formulation Example 2 (Flowable Agent

By evenly mixing and pulverizing 20.0 parts of the compound of Synthesis Example 1, 2.0 parts of di-2-ethylhexyl sulfosuccinate sodium salt, 2.0 parts of polyoxyethylene nonylphenyl ether, 5.0 parts of propylene glycol, 0.5 parts of a defoaming agent and 70.5 parts of water in a wet type ball mill, a flowable agent containing 20% active herbicide ingredient can be obtained. Furthermore, a flowable agent can be obtained by the same method except that each compound in Table 1 is used instead of the compound of Synthesis Example 1.

Formulation Example 3 (Dry Flowable Agent

By evenly mixing and finely pulverizing 75 parts of the compound of Synthesis Example 1, 10 parts of naphthalene sulfonate formaldehyde condensate, 5 parts of sodium lauryl sulfate, 5 parts of white carbon and 5 parts of clay, a dry flowable (granulate water dispersible) agent containing 75% active herbicide ingredient can be obtained. Furthermore, a dry flowable (granulate water dispersible) agent can be obtained by the same method except that each compound in Table 1 is used instead of the compound of Synthesis Example 1.

Formulation Example 4 (Water Dispersible Powder

By evenly mixing 15 parts of the compound of Synthesis Example 1, 15 parts of white carbon, 3 parts of calcium lignin sulfonate, 2 parts of polyoxyethylene alkyl ether, 5 parts of diatomaceous earth and 60 parts of clay with a pulverizing mixer, water dispersible powder containing 15% active herbicide ingredient can be obtained. Furthermore, water dispersible powder can be obtained by the same method except that each compound in Table 1 is used instead of the compound of Synthesis Example 1.

›EXAMPLES · 4 of 4

Formulation Example 5 (Emulsion

By mixing 20 parts of the compound of Synthesis Example 1, 18 parts of polyoxyethylene styrylphenylether, 2 parts of calcium dodecylbenzene sulfonate and 60 parts of xylene, an emulsion containing 20% active herbicide ingredient can be obtained. Furthermore, an emulsion can be obtained by the same method except that each compound in Table 1 is used instead of the compound of Synthesis Example 1.

Formulation Example 6 (Powder

By evenly mixing and pulverizing 0.5 parts of the compound of Synthesis Example 1, 0.5 parts of white carbon, 0.5 parts of calcium stearate, 50.0 parts of clay and 48.5 parts of talc, powder containing 0.5% active herbicide ingredient can be obtained. Furthermore, powder can be obtained by the same method except that each compound in Table 1 is used instead of the compound of Synthesis Example 1.

Formulation Example 7 (Jumbo Agent

After mixing 15 parts of the compound of Synthesis Example 1, 2 parts of sodium lauryl sulfate, 5 parts of di-2-ethylhexyl sulfosuccinate sodium salt, 5 parts of carboxymethyl cellulose sodium salt, 35 parts of Shirasu-balloon, 10 parts of lactose and 28 parts of expanded perlite, 35 parts of water was added, and the mixture was kneaded with a kneader and then granulated with an extrusion granulator. By drying the granules with a fluidized-bed dryer, a jumbo agent containing 15% active herbicide ingredient can be obtained. Furthermore, a jumbo agent can be obtained by the same method except that each compound in Table 1 is used instead of the compound of Synthesis Example 1.

Next, Test Examples are shown in order to demonstrate the herbicidal effect of the isoxazolin-5-one derivatives of the invention.

Test Example 1

Herbicidal Effect Test by Treatment of Rice Paddy Soil

Wagner pots with an area of 1/10000 ares were filled with a paddy soil, and after adding water, a compound fertilizer (N:P:K=17:17:17) was added, followed by soil puddling. Then, Echinochloa crus - galli , broad leaf weeds ( Lindernia pyxidaria and Monochoria vaginalis ) and Scirpus juncoides, 30 seeds each, were sown in a depth of 0 to 1 cm. Water was poured immediately after seeding, and the water depth was kept at about 3 cm. The subsequent management was conducted in a glass greenhouse. Immediately after that, emulsions prepared using the compounds in Table 3 below according to Formulation Example 5 were diluted with water, and a certain amount of the water-diluted agent solutions were dropped. The converted amount of the applied active ingredient corresponded to 120 g per 10 ares.

This test was conducted in a double system per one agent solution concentration area, and the herbicidal rates (%) were determined by the following equation (Math. 1) on 14 days after the treatment with the agents.

Herbicidal Rate (%)={1-(Average Dry Weight (g) of Plant of Treated Area)/(Average Dry Weight (g) of Plant of Untreated Area)}×100 [Math. 1]

The results are shown in Table 3 below. In this regard, a herbicidal rate of 80% or more is the maximum effect, and it has been confirmed that the effect is exhibited also in a test at a low concentration. The compound numbers in Table 3 are the same as those in Table 1 and Table 2 above.

Test Example 2

Herbicidal Effect Test by Treatment During Growing Period in Paddy Rice Cultivation

Wagner pots with an area of 1/10000 ares were filled with a paddy soil, and after adding water, a compound fertilizer (N:P:K=17:17:17) was mixed, followed by soil puddling. Then, Echinochloa crus - galli , broad leaf weeds ( Lindernia pyxidaria and Monochoria vaginalis ) and Scirpus juncoides, 30 seeds each, were sown in a depth of 0 to 1 cm. Water was poured immediately after seeding, and the water depth was kept at about 3 cm. The subsequent management was conducted in a glass greenhouse. Emulsions prepared using the compounds in Table 4 below according to Formulation Example 5 were diluted with water seven days after seeding, and a certain amount of the water-diluted agent solutions were dropped. The converted amount of the applied active ingredient corresponded to 120 g per 10 ares. The test was conducted in a double system per one agent solution concentration area, and the herbicidal rates (%) were determined by the equation (Math. 1) on 14 days after the treatment with the agents. The results are shown in Table 4. In this regard, a herbicidal rate of 80% or more is the maximum effect, and it has been confirmed that the effect is exhibited also in a test at a low concentration. The compound numbers in Table 4 are the same as those in Table 1 and Table 2 above.

Test Example 3

Herbicidal Effect Test by Treatment of Dry Field Farming Soil

Pots with a size of 36 cm 2 were filled with a dry field farming soil (alluvium). The soil of the top layer of 1 cm and seeds of weeds, namely southern crabgrass, Echinochloa crus - galli, Chenopodium album and Amaranthus viridis, 20 seeds each, were evenly mixed, and the top layer was gently pressed. Emulsions prepared using the compounds in Table 5 below according to Formulation Example 5 were diluted with water one day after seeding, and the water-diluted agent solutions were sprayed to the soil surfaces at a ratio of 100 liters per 10 ares. The converted amount of the applied active ingredient corresponded to 120 g per 10 ares. The herbicidal effects were evaluated by the same standard as that in Test Example 1 on 14 days after the treatment with the agents. The results are shown in Table 5. In this regard, a herbicidal rate of 80% or more is the maximum effect, and it has been confirmed that the effect is exhibited also in a test at a low concentration. The compound numbers in Table 5 are the same as those in Table 1 and Table 2 above.

Test Example 4

Herbicidal Effect Test by Treatment of Leave and Stem in Dry Field Farming

Pots with a size of 36 cm 2 were filled with a dry field farming soil (alluvium). The soil of the top layer of 1 cm and seeds of weeds, namely southern crabgrass, Echinochloa crus - galli, Chenopodium album and Amaranthus viridis, 20 seeds each, were evenly mixed, and the top layer was gently pressed. Emulsions prepared using the compounds in Table 6 below according to Formulation Example 5 were diluted with water seven days after seeding, and the water-diluted agent solutions were sprayed to the soil surfaces at a ratio of 100 liters per 10 ares. The converted amount of the applied active ingredient corresponded to 120 g per 10 ares. The herbicidal effects were evaluated by the same standard as that in Test Example 1 on 14 days after the treatment with the agents. The results are shown in Table 6. In this regard, a herbicidal rate of 80% or more is the maximum effect, and it has been confirmed that the effect is exhibited also in a test at a low concentration. The compound numbers in Table 6 are the same as those in Table 1 and Table 2 above.

›INDUSTRIAL APPLICABILITY

According to the invention, novel isoxazolin-5-one derivatives having an excellent herbicidal activity and herbicides containing the isoxazolin-5-one derivatives can be provided.

Although the invention has been explained in detail referring to specific embodiments, it is obvious to one skilled in the art that various changes and modifications can be made without departing from the spirit and the scope of the invention.

The application is based on a Japanese patent application filed on Jan. 20, 2017 (patent application No. 2017-008553), which is hereby incorporated by reference.

›Tables in the description — 6

TABLE 1

No.	R 1	R 2	R 3	R 4	Xn
1-1	CH 2 Cl	H	Me	i-Pr	H
1-2	CH 2 Cl	H	Me	s-Bu	H
1-3	CH 2 Cl	COMe	Me	s-Bu	H
1-4	CH 2 Cl	CO 2 Me	Me	s-Bu	H
1-5	CH 2 Cl	CO 2 Et	Me	s-Bu	H
1-6	CH 2 Cl	SO 2 Me	Me	s-Bu	H
1-7	CH 2 Cl	SO 2 CH 2 Cl	Me	s-Bu	H
1-8	CH 2 Cl	SO 2 CF 3	Me	s-Bu	H
1-9	CH 2 Cl	H	Me	i-Bu	H
1-10	CCl 3	H	Me	i-Pr	H
1-11	CCl 3	H	Me	s-Bu	H
1-12	CCl 3	H	Me	i-Bu	H
1-13	CH 2 F	H	Me	i-Pr	H
1-14	CH 2 F	H	Me	s-Bu	H
1-15	CH 2 F	H	Me	i-Bu	H
1-16	CF 2 H	H	Me	i-Pr	H
1-17	CF 2 H	H	Me	s-Bu	Hz
1-18	CF 2 H	COMe	Me	s-Bu	H
1-19	CF 2 H	CO 2 Me	Me	s-Bu	H
1-20	CF 2 H	CO 2 Et	Me	s-Bu	H
1-21	CF 2 H	SO 2 Me	Me	s-Bu	H
1-22	CF 2 H	SO 2 CHF 2	Me	s-Bu	H
1-23	CF 2 H	SO 2 CF 3	Me	s-Bu	H
1-24	CF 2 H	H	Me	i-Bu	H
1-25	CF 2 H	H	Me	CH(Me)CH 2 OMe	H
1-26	CF 3	H	Me	i-Pr	4-F
1-27	CF 3	H	Me	s-Bu	4-F
1-28	CF 3	H	Me	i-Bu	4-F
1-29	CF 3	SO 2 CF 3	Me	i-Bu	4-F
1-30	CF 3	H	Me	CH(Me)CH 2 OMe	4-F
1-31	CF 3	H	Me	CH 2 Ph	4-F
1-32	CF 3	SO 2 CF 3	Me	CH 2 Ph	4-F
1-33	CF 3	H	Me	i-Pr	2-Cl
1-34	CF 3	H	Me	s-Bu	2-Cl
1-35	CF 3	H	Me	i-Bu	2-Cl
1-36	CF 3	H	Me	CH(Me)CH 2 OMe	2-Cl
1-37	CF 3	H	Me	i-Pr	3-Cl
1-38	CF 3	H	Me	s-Bu	3-Cl
1-39	CF 3	H	Me	i-Bu	3-Cl
1-40	CF 3	H	Me	CH(Me)CH 2 OMe	3-Cl
1-41	CF 3	H	Me	i-Pr	4-Cl
1-42	CF 3	H	Me	s-Bu	4-Cl
1-43	CF 3	H	Me	i-Bu	4-Cl
1-44	CF 3	H	Me	CH(Me)CH 2 OMe	4-Cl
1-45	CF 3	H	Me	CH 2 Ph	4-Cl
1-46	CF 3	H	Me	i-Pr	5-Cl
1-47	CF 3	SO 2 CF 3	Me	i-Pr	5-Cl
1-48	CF 3	H	Me	s-Bu	5-Cl
1-49	CF 3	H	Me	i-Bu	5-Cl
1-50	CF 3	H	Me	CH(Me)CH 2 OMe	5-Cl
1-51	CF 3	H	Me	s-Bu	3,4-Cl 2
1-52	CF 3	H	Me	s-Bu	4-Br
1-53	CF 3	H	Me	s-Bu	4-I
1-54	CF 3	H	Me	s-Bu	4-Me
1-55	CF 3	H	Me	CH(Me)CH 2 OMe	4-Me
1-56	CF 3	H	Me	s-Bu	4-MeO
1-57	CF 3	H	Me	CH(Me)CH 2 OMe	4-MeO
1-58	CF 3	H	H	s-Bu	H
1-59	CF 3	H	F	s-Bu	H
1-60	CF 3	H	Cl	s-Bu	H
1-61	CF 3	H	Br	s-Bu	H
1-62	CF 3	H	I	s-Bu	H
1-63	CF 3	H	Et	i-Pr	H
1-64	CF 3	H	Et	s-Bu	H
1-65	CF 3	H	Et	i-Bu	H
1-66	CF 3	H	Et	CH(Me)CH 2 OMe	H
1-67	CF 3	H	n-Pr	s-Bu	H
1-68	CF 3	H	i-Pr	i-Pr	H
1-69	CF 3	SO 2 CF 3	i-Pr	i-Pr	H
1-70	CF 3	H	i-Pr	s-Bu	H
1-71	CF 3	H	i-Pr	i-Bu	H
1-72	CF 3	H	i-Pr	CH(Me)CH 2 OMe	H
1-73	CF 3	H	n-Bu	s-Bu	H
1-74	CF 3	H	i-Bu	s-Bu	H
1-75	CF 3	H	s-Bu	s-Bu	H
1-76	CF 3	H	t-Bu	s-Bu	H
1-77	CF 3	H	CF 2 H	s-Bu	H
1-78	CF 3	H	CF 3	Me	H
1-79	CF 3	H	CF 3	i-Pr	H
1-80	CF 3	H	CF 3	s-Bu	H
1-81	CF 3	H	CF 3	i-Bu	H
1-82	CF 3	H	CF 3	CH(Me)CH 2 OMe	H
1-83	CF 3	H	c-Pr	i-Pr	H
1-84	CF 3	SO 2 CF 3	c-Pr	i-Pr	H
1-85	CF 3	H	c-Pr	s-Bu	H
1-86	CF 3	H	c-Pr	i-Bu	H
1-87	CF 3	H	c-Pr	CH(Me)CH 2 OMe	H
1-88	CF 3	H	c-Bu	s-Bu	H
1-89	CF 3	H	c-Hex	s-Bu	H
1-90	CF 3	H	Ph	s-Bu	H
1-91	CF 3	H	4-ClPh	s-Bu	H
1-92	CF 3	H	4-MePh	s-Bu	H
1-93	CF 3	H	NH 2	s-Bu	H
1-94	CF 3	H	NHMe	s-Bu	H
1-95	CF 3	H	NMe 2	s-Bu	H
1-96	CF 3	H	Me	H	H
1-97	CF 3	H	Me	Me	H
1-98	CF 3	H	Me	Et	H
1-99	CF 3	H	Me	n-Pr	H
1-100	CF 3	H	Me	i-Pr	H
1-101	CF 3	H	Me	t-Bu	H
1-102	CF 3	H	Me	s-Bu	H
1-103	CF 3	H	Me	CH(Et)CH 2 CH 3	H
1-104	CF 3	H	Me	C(Me) 2 CH 2 CH 3	H
1-105	CF 3	H	Me	i-Bu	H
1-106	CF 3	H	Me	CH 2 C(Me) 2 CH 3	H
1-107	CF 3	H	Me	CH(Me)CH(Me)CH 3	H
1-108	CF 3	H	Me	n-Bu	H
1-109	CF 3	H	Me	CH(Me)CH 2 CH 2 CH 3	H
1-110	CF 3	H	Me	CH(Et)CH 2 CH 2 CH 3	H
1-111	CF 3	H	Me	C(Me) 2 CH 2 CH 2 CH 3	H
1-112	CF 3	H	Me	CH 2 CH(Me)CH 2 CH 3	H
1-113	CF 3	H	Me	CH 2 CH(Et)CH 2 CH 3	H
1-114	CF 3	H	Me	CH 2 C(Me) 2 CH 2 CH 3	H
1-115	CF 3	H	Me	CH 2 CH 2 CH(Me)CH 3	H
1-116	CF 3	H	Me	CH 2 CH 2 C(Me) 2 CH 3	H
1-117	CF 3	H	Me	CH(Me)CH(Me)CH 2 CH 3	H
1-118	CF 3	H	Me	CH 2 CH(Me)CH(Me)CH 3	H
1-119	CF 3	H	Me	n-Pen	H
1-120	CF 3	H	Me	CH(Me)CH 2 CH 2 CH 2 CH 3	H
1-121	CF 3	H	Me	CH(Et)CH 2 CH 2 CH 2 CH 3	H
1-122	CF 3	H	Me	CH 2 CH(Me)CH 2 CH 2 CH 3	H
1-123	CF 3	H	Me	CH 2 CH(Et)CH 2 CH 2 CH 3	H
1-124	CF 3	H	Me	CH 2 CH 2 CH(Me)CH 2 CH 3	H
1-125	CF 3	H	Me	CH 2 CH 2 CH 2 CH(Me)CH 3	H
1-126	CF 3	H	Me	n-Hex	H
1-127	CF 3	H	Me	CH(Me)CH 2 CH 2 CH 2 CH 2 CH 3	H
1-128	CF 3	H	Me	CH(Et)CH 2 CH 2 CH 2 CH 2 CH 3	H
1-129	CF 3	H	Me	CH 2 CH(Me)CH 2 CH 2 CH 2 CH 3	H
1-130	CF 3	H	Me	CH 2 CH(Et)CH 2 CH 2 CH 2 CH 3	H
1-131	CF 3	H	Me	(CH 2 ) 7 CH 3	H
1-132	CF 3	H	Me	(CH 2 ) 13 CH 3	H
1-133	CF 3	H	Me	CH 2 CH 2 Cl	H
1-134	CF 3	H	Me	CH 2 CF 3	H
1-135	CF 3	H	Me	CH 2 CH═CH 2	H
1-136	CF 3	H	Me	CH(Me)CH═CH 2	H
1-137	CF 3	H	Me	CH 2 C(Me)═CH 2	H
1-138	CF 3	H	Me	CH 2 C≡CH	H
1-139	CF 3	H	Me	c-Pr	H
1-140	CF 3	H	Me	c-Bu	H
1-141	CF 3	H	Me	c-Pen	H
1-142	CF 3	H	Me	c-Hex	H
1-143	CF 3	H	Me	CH 2 c-Pr	H
1-144	CF 3	H	Me	CH(Me)c-Pr	H
1-145	CF 3	H	Me	CH 2 (1-Me-c-Pr)	H
1-146	CF 3	H	Me	CH 2 c-Hex	H
1-147	CF 3	H	Me	CH 2 OMe	H
1-148	CF 3	H	Me	CH 2 CH 2 OMe	H
1-149	CF 3	H	Me	CH(Me)CH 2 OMe	H
1-150	CF 3	H	Me	CH(Et)CH 2 OMe	H
1-151	CF 3	H	Me	CH 2 CH(Me)OMe	H
1-152	CF 3	H	Me	CH 2 CH 2 OEt	H
1-153	CF 3	H	Me	CH(Me)CH 2 OEt	H
1-154	CF 3	H	Me	CH 2 CH(Me)OEt	H
1-155	CF 3	H	Me	CH 2 CH 2 Oi-Pr	H
1-156	CF 3	H	Me	CH 2 CH 2 Oi-Bu	H
1-157	CF 3	H	Me	CH 2 CH 2 CH 2 OMe	H
1-158	CF 3	H	Me	CH(Me)CH 2 CH 2 OMe	H
1-159	CF 3	H	Me	CH 2 CH 2 OCH 2 CF 3	H
1-160	CF 3	H	Me	CH 2 CH 2 OCH 2 CH 2 OMe	H
1-161	CF 3	H	Me	CH 2 SMe	H
1-162	CF 3	H	Me	CH 2 CH 2 SMe	H
1-163	CF 3	H	Me	CH(Me)CH 2 SMe	H
1-164	CF 3	H	Me	CH 2 CH(Me)SMe	H
1-165	CF 3	H	Me	CH 2 CH 2 SEt	H
1-166	CF 3	H	Me	CH 2 CH 2 Si-Pr	H
1-167	CF 3	H	Me	CH 2 CH 2 CH 2 SMe	H
1-168	CF 3	H	Me	CH 2 CH 2 SCH 2 CF 3	H
1-169	CF 3	H	Me	CH 2 CH 2 SOMe	H
1-170	CF 3	H	Me	CH 2 CH 2 SO 2 Me	H
1-171	CF 3	H	Me	CH 2 CH 2 NHMe	H
1-172	CF 3	H	Me	CH 2 CH 2 NMe 2	H
1-173	CF 3	H	Me	CH 2 COMe	H
1-174	CF 3	H	Me	Ph	H
1-175	CF 3	H	Me	2-ClPh	H
1-176	CF 3	H	Me	3-ClPh	H
1-177	CF 3	H	Me	4-ClPh	H
1-178	CF 3	H	Me	4-MePh	H
1-179	CF 3	H	Me	4-MeOPh	H
1-180	CF 3	H	Me	CH 2 Ph	H
1-181	CF 3	H	Me	CH 2 (2-FPh)	H
1-182	CF 3	H	Me	CH 2 (3-FPh)	H
1-183	CF 3	H	Me	CH 2 (4-FPh)	H
1-184	CF 3	H	Me	CH 2 (2-ClPh)	H
1-185	CF 3	H	Me	CH 2 (3-ClPh)	H
1-186	CF 3	H	Me	CH 2 (4-ClPh)	H
1-187	CF 3	H	Me	CH 2 (4-BrPh)	H
1-188	CF 3	H	Me	CH 2 (4-IPh)	H
1-189	CF 3	H	Me	CH 2 (4-CNPh)	H
1-190	CF 3	H	Me	CH 2 (4-NO 2 Ph)	H
1-191	CF 3	H	Me	CH 2 (4-MePh)	H
1-192	CF 3	H	Me	CH 2 (4-t-BuPh)	H
1-193	CF 3	H	Me	CH 2 (3-CF 3 Ph)	H
1-194	CF 3	H	Me	CH 2 (4-CF 3 Ph)	H
1-195	CF 3	H	Me	CH 2 (4-MeOPh)	H
1-196	CF 3	H	Me	CH 2 (4-CF 3 OPh)	H
1-197	CF 3	H	Me	CH 2 (4-MeSPh)	H
1-198	CF 3	H	Me	CH 2 (4-CF 3 SPh)	H
1-199	CF 3	H	Me	CH 2 (2,4-F 2 Ph)	H
1-200	CF 3	H	Me	CH 2 (3,4-F 2 Ph)	H
1-201	CF 3	H	Me	CH 2 (2-Cl-4-FPh)	H
1-202	CF 3	H	Me	CH 2 (3-Cl-4-FPh)	H
1-203	CF 3	H	Me	CH(Me)Ph	H
1-204	CF 3	H	Me	CH(Me)(4-FPh)	H
1-205	CF 3	H	Me	CH(Me)(2-ClPh)	H
1-206	CF 3	H	Me	CH(Me)(3-ClPh)	H
1-207	CF 3	H	Me	CH(Me)(4-ClPh)	H
1-208	CF 3	H	Me	CH(Me)(4-MePh)	H
1-209	CF 3	H	Me	CH(Me)(4-CF 3 OPh)	H
1-210	CF 3	H	Me	CH(Me)(2,4-F 2 Ph)	H
1-211	CF 3	H	Me	CH(Et)Ph	H
1-212	CF 3	H	Me	CH(n-Pr)Ph	H
1-213	CF 3	H	Me	CH(i-Pr)Ph	H
1-214	CF 3	H	Me	CH(n-Bu)Ph	H
1-215	CF 3	H	Me	CH(n-Pen)Ph	H
1-216	CF 3	H	Me	CH 2 CH 2 Ph	H
1-217	CF 3	H	Me	CH 2 CH 2 (4-FPh)	H
1-218	CF 3	H	Me	CH(Me)CH 2 Ph	H
1-219	CF 3	H	Me	CH 2 CH(Me)Ph	H
1-220	CF 3	H	Me	CH 2 CF 2 Ph	H
1-221	CF 3	H	Me	CH 2 CH 2 CH 2 Ph	H
1-222	CF 3	H	Me	1-indanyl	H
1-223	CF 3	H	Me	2-indanyl	H
1-224	CF 3	H	Me	1-(1,2,3,4-tetrahydro-Np)	H
1-225	CF 3	H	Me	2-(1,2,3,4-tetrahydro-Np)	H
1-226	CF 3	H	Me	CH 2 (2-oxiranyl)	H
1-227	CF 3	H	Me	CH 2 (3-oxetanyl)	H
1-228	CF 3	H	Me	CH 2 (2-Me-2-oxiranyl)	H
1-229	CF 3	H	Me	CH 2 (3-Me-3-oxetanyl)	H
1-230	CF 3	H	Me	CH 2 (2-tetrahydrofuryl)	H
1-231	CF 3	H	Me	CH 2 (2-thienyl)	H
1-232	CF 3	H	Me	CH 2 (3-thienyl)	H
1-233	CF 3	H	Me	CH 2 (2-pyridyl)	H
1-234	CF 3	H	Me	CH(Me)(2-thienyl)	H
1-235	CF 3	H	Me	CH(Me)(3-thienyl)	H
1-236	CF 3	H	Me	CH(Me)(2-pyridyl)	H
1-237	CF 3	H	Me	CH 2 CH 2 OPh	H
1-238	CF 3	H	Me	CH 2 CH 2 OCH 2 Ph	H
1-239	CF 3	H	Me	CH 2 COPh	H
1-240	CF 3	H	Me	COMe	H
1-241	CF 3	H	Me	COEt	H
1-242	CF 3	H	Me	COi-Pr	H
1-243	CF 3	H	Me	Bz	H
1-244	CF 3	H	Me	COCH 2 Ph	H
1-245	CF 3	H	Me	CO 2 Me	H
1-246	CF 3	H	Me	CO 2 Et	H
1-247	CF 3	H	Me	CONHEt	H
1-248	CF 3	H	Me	CONEt 2	H
1-249	CF 3	H	Me	SO 2 Me	H
1-250	CF 3	H	Me	SO 2 Et	H
1-251	CF 3	H	Me	SO 2 i-Pr	H
1-252	CF 3	H	Me	SO 2 CF 3	H
1-253	CF 3	H	Me	SO 2 Ph	H
1-254	CF 3	H	Me	SO 2 (4-MePh)	H
1-255	CF 3	H	Me	SO 2 CH 2 Ph	H
1-256	CF 3	Me	Me	Me	H
1-257	CF 3	Me	Me	i-Pr	H
1-258	CF 3	Me	Me	s-Bu	H
1-259	CF 3	Me	Me	i-Bu	H
1-260	CF 3	Me	Me	CH 2 Ph	H
1-261	CF 3	Et	Me	i-Pr	H
1-262	CF 3	Et	Me	s-Bu	H
1-263	CF 3	Et	Me	i-Bu	H
1-264	CF 3	Et	Me	CH 2 CH(Et)CH 2 CH 3	H
1-265	CF 3	CH 2 CF 3	Me	s-Bu	H
1-266	CF 3	CH 2 CH═CH 2	Me	s-Bu	H
1-267	CF 3	CH 2 C≡CH	Me	s-Bu	H
1-268	CF 3	CH 2 OMe	Me	i-Pr	H
1-269	CF 3	CH 2 OMe	Me	s-Bu	H
1-270	CF 3	CH 2 OMe	Me	i-Bu	H
1-271	CF 3	CH 2 OMe	Me	CH 2 CH(Me)CH 2 CH 3	H
1-272	CF 3	CH 2 OCH 2 CF 3	Me	s-Bu	H
1-273	CF 3	CH 2 OCH 2 CH 2 OMe	Me	s-Bu	H
1-274	CF 3	CH 2 SMe	Me	s-Bu	H
1-275	CF 3	CH 2 COMe	Me	s-Bu	H
1-276	CF 3	CH 2 Ph	Me	i-Pr	H
1-277	CF 3	CH 2 Ph	Me	s-Bu	H
1-278	CF 3	CH 2 Ph	Me	i-Bu	H
1-279	CF 3	CH 2 Ph	Me	CH 2 CH(Me)CH 2 CH 3	H
1-280	CF 3	CH 2 (4-ClPh)	Me	s-Bu	H
1-281	CF 3	CH 2 (4-MePh)	Me	s-Bu	H
1-282	CF 3	CH 2 (4-MeOPh)	Me	H	H
1-283	CF 3	CH 2 (4-MeOPh)	Me	i-Pr	H
1-284	CF 3	CH 2 (4-MeOPh)	Me	s-Bu	H
1-285	CF 3	CH 2 (4-MeOPh)	Me	i-Bu	H
1-286	CF 3	CH 2 (4-MeOPh)	Me	CH(Me)CH 2 OMe	H
1-287	CF 3	CH 2 (4-MeOPh)	Me	CONEt 2	H
1-288	CF 3	CH 2 CH 2 OPh	Me	s-Bu	H
1-289	CF 3	CH 2 OCH 2 Ph	Me	s-Bu	H
1-290	CF 3	CH 2 COPh	Me	s-Bu	H
1-291	CF 3	COMe	Me	Me	H
1-292	CF 3	COMe	Me	i-Pr	H
1-293	CF 3	COMe	Me	t-Bu	H
1-294	CF 3	COMe	Me	s-Bu	H
1-295	CF 3	COMe	Me	CH(Et)CH 2 CH 3	H
1-296	CF 3	COMe	Me	C(Me) 2 CH 2 CH 3	H
1-297	CF 3	COMe	Me	i-Bu	H
1-298	CF 3	COMe	Me	CH 2 C(Me) 2 CH 3	H
1-299	CF 3	COMe	Me	CH(Me)CH 2 CH 2 CH 3	H
1-300	CF 3	COMe	Me	CH 2 CH(Me)CH 2 CH 3	H
1-301	CF 3	COMe	Me	CH 2 CH(Et)CH 2 CH 3	H
1-302	CF 3	COMe	Me	CH 2 c-Pr	H
1-303	CF 3	COMe	Me	CH 2 CH 2 OMe	H
1-304	CF 3	COMe	Me	CH(Me)CH 2 OMe	H
1-305	CF 3	COMe	Me	CH 2 CH 2 SMe	H
1-306	CF 3	COMe	Me	2-ClPh	H
1-307	CF 3	COMe	Me	3-ClPh	H
1-308	CF 3	COMe	Me	4-ClPh	H
1-309	CF 3	COMe	Me	CH 2 Ph	H
1-310	CF 3	COMe	Me	CH(Me)Ph	H
1-311	CF 3	COMe	Me	CH(Me)(4-FPh)	H
1-312	CF 3	COMe	Me	1-indanyl	H
1-313	CF 3	COMe	Me	1-(1,2,3,4-tetrahydro-Np)	H
1-314	CF 3	COEt	Me	i-Pr	H
1-315	CF 3	COEt	Me	t-Bu	H
1-316	CF 3	COEt	Me	s-Bu	H
1-317	CF 3	COEt	Me	i-Bu	H
1-318	CF 3	COEt	Me	CH 2 C(Me) 2 CH 3	H
1-319	CF 3	COEt	Me	CH(Me)CH 2 OMe	H
1-320	CF 3	COEt	Me	CH 2 CH 2 SMe	H
1-321	CF 3	COEt	Me	CH(Me)Ph	H
1-322	CF 3	COn-Pr	Me	i-Pr	H
1-323	CF 3	COn-Pr	Me	t-Bu	H
1-324	CF 3	COn-Pr	Me	s-Bu	H
1-325	CF 3	COn-Pr	Me	i-Bu	H
1-326	CF 3	COn-Pr	Me	CH(Me)CH 2 OMe	H
1-327	CF 3	COn-Pr	Me	CH(Me)Ph	H
1-328	CF 3	COi-Pr	Me	i-Pr	H
1-329	CF 3	COi-Pr	Me	t-Bu	H
1-330	CF 3	COi-Pr	Me	s-Bu	H
1-331	CF 3	COi-Pr	Me	CH(Et)CH 2 CH 3	H
1-332	CF 3	COi-Pr	Me	i-Bu	H
1-333	CF 3	COi-Pr	Me	CH 2 C(Me) 2 CH 3	H
1-334	CF 3	COi-Pr	Me	CH(Me)CH 2 CH 2 CH 3	H
1-335	CF 3	COi-Pr	Me	CH(Me)CH 2 OMe	H
1-336	CF 3	COi-Pr	Me	CH 2 CH 2 SMe	H
1-337	CF 3	COi-Pr	Me	CH(Me)Ph	H
1-338	CF 3	COn-Bu	Me	i-Pr	H
1-339	CF 3	COn-Bu	Me	t-Bu	H
1-340	CF 3	COn-Bu	Me	s-Bu	H
1-341	CF 3	COn-Bu	Me	i-Bu	H
1-342	CF 3	COn-Bu	Me	CH(Me)CH 2 OMe	H
1-343	CF 3	COn-Bu	Me	CH(Me)Ph	H
1-344	CF 3	COs-Bu	Me	i-Pr	H
1-345	CF 3	COs-Bu	Me	t-Bu	H
1-346	CF 3	COs-Bu	Me	s-Bu	H
1-347	CF 3	COs-Bu	Me	i-Bu	H
1-348	CF 3	COs-Bu	Me	CH(Me)CH 2 OMe	H
1-349	CF 3	COs-Bu	Me	CH(Me)Ph	H
1-350	CF 3	COi-Bu	Me	i-Pr	H
1-351	CF 3	COi-Bu	Me	t-Bu	H
1-352	CF 3	COi-Bu	Me	s-Bu	H
1-353	CF 3	COi-Bu	Me	CH(Et)CH 2 CH 3	H
1-354	CF 3	COi-Bu	Me	i-Bu	H
1-355	CF 3	COi-Bu	Me	CH 2 C(Me) 2 CH 3	H
1-356	CF 3	COi-Bu	Me	CH(Me)CH 2 CH 2 CH 3	H
1-357	CF 3	COi-Bu	Me	CH(Me)CH 2 OMe	H
1-358	CF 3	COi-Bu	Me	CH 2 CH 2 SMe	H
1-359	CF 3	COi-Bu	Me	CH(Me)Ph	H
1-360	CF 3	COt-Bu	Me	i-Pr	H
1-361	CF 3	COt-Bu	Me	t-Bu	H
1-362	CF 3	COt-Bu	Me	s-Bu	H
1-363	CF 3	COt-Bu	Me	i-Bu	H
1-364	CF 3	COt-Bu	Me	CH(Me)CH 2 OMe	H
1-365	CF 3	COt-Bu	Me	CH(Me)Ph	H
1-366	CF 3	COn-Pen	Me	i-Pr	H
1-367	CF 3	COn-Pen	Me	t-Bu	H
1-368	CF 3	COn-Pen	Me	s-Bu	H
1-369	CF 3	COn-Pen	Me	i-Bu	H
1-370	CF 3	COn-Pen	Me	CH(Me)CH 2 OMe	H
1-371	CF 3	COn-Pen	Me	CH(Me)Ph	H
1-372	CF 3	COn-Hex	Me	i-Pr	H
1-373	CF 3	COn-Hex	Me	t-Bu	H
1-374	CF 3	COn-Hex	Me	s-Bu	H
1-375	CF 3	COn-Hex	Me	i-Bu	H
1-376	CF 3	COn-Hex	Me	CH(Me)CH 2 OMe	H
1-377	CF 3	COn-Hex	Me	CH(Me)Ph	H
1-378	CF 3	COCF 3	Me	i-Pr	H
1-379	CF 3	COCF 3	Me	t-Bu	H
1-380	CF 3	COCF 3	Me	s-Bu	H
1-381	CF 3	COCF 3	Me	i-Bu	H
1-382	CF 3	COCF 3	Me	CH(Me)CH 2 OMe	H
1-383	CF 3	COCF 3	Me	CH(Me)Ph	H
1-384	CF 3	COCH 2 CF 3	Me	i-Pr	H
1-385	CF 3	COCH 2 CF 3	Me	t-Bu	H
1-386	CF 3	COCH 2 CF 3	Me	s-Bu	H
1-387	CF 3	COCH 2 CF 3	Me	i-Bu	H
1-388	CF 3	COCH 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-389	CF 3	COCH 2 CF 3	Me	CH(Me)Ph	H
1-390	CF 3	COCH═CH 2	Me	i-Pr	H
1-391	CF 3	COCH═CH 2	Me	t-Bu	H
1-392	CF 3	COCH═CH 2	Me	s-Bu	H
1-393	CF 3	COCH═CH 2	Me	i-Bu	H
1-394	CF 3	COCH═CH 2	Me	CH(Me)CH 2 OMe	H
1-395	CF 3	COCH═CH 2	Me	CH(Me)Ph	H
1-396	CF 3	COC≡CH	Me	i-Pr	H
1-397	CF 3	COC≡CH	Me	t-Bu	H
1-398	CF 3	COC≡CH	Me	s-Bu	H
1-399	CF 3	COC≡CH	Me	i-Bu	H
1-400	CF 3	COC≡CH	Me	CH(Me)CH 2 OMe	H
1-401	CF 3	COC≡CH	Me	CH(Me)Ph	H
1-402	CF 3	COc-Pr	Me	i-Pr	H
1-403	CF 3	COc-Pr	Me	t-Bu	H
1-404	CF 3	COc-Pr	Me	s-Bu	H
1-405	CF 3	COc-Pr	Me	CH(Et)CH 2 CH 3	H
1-406	CF 3	COc-Pr	Me	i-Bu	H
1-407	CF 3	COc-Pr	Me	CH 2 C(Me) 2 CH 3	H
1-408	CF 3	COc-Pr	Me	CH(Me)CH 2 CH 2 CH 3	H
1-409	CF 3	COc-Pr	Me	CH 2 CH(Me)CH 2 CH 3	H
1-410	CF 3	COc-Pr	Me	CH 2 CH(Et)CH 2 CH 3	H
1-411	CF 3	COc-Pr	Me	CH 2 c-Pr	H
1-412	CF 3	COc-Pr	Me	CH(Me)CH 2 OMe	H
1-413	CF 3	COc-Pr	Me	CH 2 CH 2 SMe	H
1-414	CF 3	COc-Pr	Me	3-ClPh	H
1-415	CF 3	COc-Pr	Me	CH 2 Ph	H
1-416	CF 3	COc-Pr	Me	CH(Me)Ph	H
1-417	CF 3	COc-Pr	Me	CH(Me)(4-FPh)	H
1-418	CF 3	COc-Bu	Me	i-Pr	H
1-419	CF 3	COc-Bu	Me	t-Bu	H
1-420	CF 3	COc-Bu	Me	s-Bu	H
1-421	CF 3	COc-Bu	Me	i-Bu	H
1-422	CF 3	COc-Bu	Me	CH(Me)CH 2 OMe	H
1-423	CF 3	COc-Bu	Me	CH(Me)Ph	H
1-424	CF 3	COc-Pen	Me	i-Pr	H
1-425	CF 3	COc-Pen	Me	t-Bu	H
1-426	CF 3	COc-Pen	Me	s-Bu	H
1-427	CF 3	COc-Pen	Me	i-Bu	H
1-428	CF 3	COc-Pen	Me	CH(Me)CH 2 OMe	H
1-429	CF 3	COc-Pen	Me	CH(Me)Ph	H
1-430	CF 3	COc-Hex	Me	i-Pr	H
1-431	CF 3	COc-Hex	Me	t-Bu	H
1-432	CF 3	COc-Hex	Me	s-Bu	H
1-433	CF 3	COc-Hex	Me	i-Bu	H
1-434	CF 3	COc-Hex	Me	CH(Me)CH 2 OMe	H
1-435	CF 3	COc-Hex	Me	CH(Me)Ph	H
1-436	CF 3	COCH 2 c-Pr	Me	i-Pr	H
1-437	CF 3	COCH 2 c-Pr	Me	t-Bu	H
1-438	CF 3	COCH 2 c-Pr	Me	s-Bu	H
1-439	CF 3	COCH 2 c-Pr	Me	i-Bu	H
1-440	CF 3	COCH 2 c-Pr	Me	CH(Me)CH 2 OMe	H
1-441	CF 3	COCH 2 c-Pr	Me	CH(Me)Ph	H
1-442	CF 3	COCH 2 OMe	Me	i-Pr	H
1-443	CF 3	COCH 2 OMe	Me	t-Bu	H
1-444	CF 3	COCH 2 OMe	Me	s-Bu	H
1-445	CF 3	COCH 2 OMe	Me	i-Bu	H
1-446	CF 3	COCH 2 OMe	Me	CH(Me)CH 2 OMe	H
1-447	CF 3	COCH 2 OMe	Me	CH(Me)Ph	H
1-448	CF 3	COCH 2 OCH 2 CF 3	Me	i-Pr	H
1-449	CF 3	COCH 2 OCH 2 CF 3	Me	t-Bu	H
1-450	CF 3	COCH 2 OCH 2 CF 3	Me	s-Bu	H
1-451	CF 3	COCH 2 OCH 2 CF 3	Me	i-Bu	H
1-452	CF 3	COCH 2 OCH 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-453	CF 3	COCH 2 OCH 2 CF 3	Me	CH(Me)Ph	H
1-454	CF 3	COCH 2 OCH 2 CH 2 OMe	Me	i-Pr	H
1-455	CF 3	COCH 2 OCH 2 CH 2 OMe	Me	t-Bu	H
1-456	CF 3	COCH 2 OCH 2 CH 2 OMe	Me	s-Bu	H
1-457	CF 3	COCH 2 OCH 2 CH 2 OMe	Me	i-Bu	H
1-458	CF 3	COCH 2 OCH 2 CH 2 OMe	Me	CH(Me)CH 2 OMe	H
1-459	CF 3	COCH 2 OCH 2 CH 2 OMe	Me	CH(Me)Ph	H
1-460	CF 3	COCH 2 SMe	Me	i-Pr	H
1-461	CF 3	COCH 2 SMe	Me	t-Bu	H
1-462	CF 3	COCH 2 SMe	Me	s-Bu	H
1-463	CF 3	COCH 2 SMe	Me	i-Bu	H
1-464	CF 3	COCH 2 SMe	Me	CH(Me)CH 2 OMe	H
1-465	CF 3	COCH 2 SMe	Me	CH(Me)Ph	H
1-466	CF 3	COCH 2 SCH 2 CF 3	Me	i-Pr	H
1-467	CF 3	COCH 2 SCH 2 CF 3	Me	t-Bu	H
1-468	CF 3	COCH 2 SCH 2 CF 3	Me	s-Bu	H
1-469	CF 3	COCH 2 SCH 2 CF 3	Me	i-Bu	H
1-470	CF 3	COCH 2 SCH 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-471	CF 3	COCH 2 SCH 2 CF 3	Me	CH(Me)Ph	H
1-472	CF 3	Bz	Me	i-Pr	H
1-473	CF 3	Bz	Me	t-Bu	H
1-474	CF 3	Bz	Me	s-Bu	H
1-475	CF 3	Bz	Me	CH(Et)CH 2 CH 3	H
1-476	CF 3	Bz	Me	i-Bu	H
1-477	CF 3	Bz	Me	CH 2 C(Me) 2 CH 3	H
1-478	CF 3	Bz	Me	CH(Me)CH 2 CH 2 CH 3	H
1-479	CF 3	Bz	Me	CH(Me)CH 2 OMe	H
1-480	CF 3	Bz	Me	CH 2 CH 2 SMe	H
1-481	CF 3	Bz	Me	CH(Me)Ph	H
1-482	CF 3	4-ClBz	Me	i-Pr	H
1-483	CF 3	4-ClBz	Me	t-Bu	H
1-484	CF 3	4-ClBz	Me	s-Bu	H
1-485	CF 3	4-ClBz	Me	CH(Et)CH 2 CH 3	H
1-486	CF 3	4-ClBz	Me	i-Bu	H
1-487	CF 3	4-ClBz	Me	CH 2 C(Me) 2 CH 3	H
1-488	CF 3	4-ClBz	Me	CH(Me)CH 2 CH 2 CH 3	H
1-489	CF 3	4-ClBz	Me	CH(Me)CH 2 OMe	H
1-490	CF 3	4-ClBz	Me	CH 2 CH 2 SMe	H
1-491	CF 3	4-ClBz	Me	CH(Me)Ph	H
1-492	CF 3	4-MeBz	Me	i-Pr	H
1-493	CF 3	4-MeBz	Me	t-Bu	H
1-494	CF 3	4-MeBz	Me	s-Bu	H
1-495	CF 3	4-MeBz	Me	CH(Et)CH 2 CH 3	H
1-496	CF 3	4-MeBz	Me	i-Bu	H
1-497	CF 3	4-MeBz	Me	CH 2 C(Me) 2 CH 3	H
1-498	CF 3	4-MeBz	Me	CH(Me)CH 2 CH 2 CH 3	H
1-499	CF 3	4-MeBz	Me	CH(Me)CH 2 OMe	H
1-500	CF 3	4-MeBz	Me	CH 2 CH 2 SMe	H
1-501	CF 3	4-MeBz	Me	CH(Me)Ph	H
1-502	CF 3	COCH 2 Ph	Me	i-Pr	H
1-503	CF 3	COCH 2 Ph	Me	t-Bu	H
1-504	CF 3	COCH 2 Ph	Me	s-Bu	H
1-505	CF 3	COCH 2 Ph	Me	i-Bu	H
1-506	CF 3	COCH 2 Ph	Me	CH(Me)CH 2 OMe	H
1-507	CF 3	COCH 2 Ph	Me	CH(Me)Ph	H
1-508	CF 3	COCH 2 (4-ClPh)	Me	i-Pr	H
1-509	CF 3	COCH 2 (4-ClPh)	Me	t-Bu	H
1-510	CF 3	COCH 2 (4-ClPh)	Me	s-Bu	H
1-511	CF 3	COCH 2 (4-ClPh)	Me	i-Bu	H
1-512	CF 3	COCH 2 (4-ClPh)	Me	CH(Me)CH 2 OMe	H
1-513	CF 3	COCH 2 (4-ClPh)	Me	CH(Me)Ph	H
1-514	CF 3	COCH 2 (4-MePh)	Me	i-Pr	H
1-515	CF 3	COCH 2 (4-MePh)	Me	t-Bu	H
1-516	CF 3	COCH 2 (4-MePh)	Me	s-Bu	H
1-517	CF 3	COCH 2 (4-MePh)	Me	i-Bu	H
1-518	CF 3	COCH 2 (4-MePh)	Me	CH(Me)CH 2 OMe	H
1-519	CF 3	COCH 2 (4-MePh)	Me	CH(Me)Ph	H
1-520	CF 3	CO(2-tetrahydrofuryl)	Me	i-Pr	H
1-521	CF 3	CO(2-tetrahydrofuryl)	Me	t-Bu	H
1-522	CF 3	CO(2-tetrahydrofuryl)	Me	s-Bu	H
1-523	CF 3	CO(2-tetrahydrofuryl)	Me	i-Bu	H
1-524	CF 3	CO(2-tetrahydrofuryl)	Me	CH(Me)CH 2 OMe	H
1-525	CF 3	CO(2-tetrahydrofuryl)	Me	CH(Me)Ph	H
1-526	CF 3	CO(2-pyridyl)	Me	i-Pr	H
1-527	CF 3	CO(2-pyridyl)	Me	t-Bu	H
1-528	CF 3	CO(2-pyridyl)	Me	s-Bu	H
1-529	CF 3	CO(2-pyridyl)	Me	i-Bu	H
1-530	CF 3	CO(2-pyridyl)	Me	CH(Me)CH 2 OMe	H
1-531	CF 3	CO(2-pyridyl)	Me	CH(Me)Ph	H
1-532	CF 3	CO(3-pyridyl)	Me	i-Pr	H
1-533	CF 3	CO(3-pyridyl)	Me	t-Bu	H
1-534	CF 3	CO(3-pyridyl)	Me	s-Bu	H
1-535	CF 3	CO(3-pyridyl)	Me	i-Bu	H
1-536	CF 3	CO(3-pyridyl)	Me	CH(Me)CH 2 OMe	H
1-537	CF 3	CO(3-pyridyl)	Me	CH(Me)Ph	H
1-538	CF 3	CO(4-pyridyl)	Me	i-Pr	H
1-539	CF 3	CO(4-pyridyl)	Me	t-Bu	H
1-540	CF 3	CO(4-pyridyl)	Me	s-Bu	H
1-541	CF 3	CO(4-pyridyl)	Me	i-Bu	H
1-542	CF 3	CO(4-pyridyl)	Me	CH(Me)CH 2 OMe	H
1-543	CF 3	CO(4-pyridyl)	Me	CH(Me)Ph	H
1-544	CF 3	CO(2-thienyl)	Me	i-Pr	H
1-545	CF 3	CO(2-thienyl)	Me	t-Bu	H
1-546	CF 3	CO(2-thienyl)	Me	s-Bu	H
1-547	CF 3	CO(2-thienyl)	Me	i-Bu	H
1-548	CF 3	CO(2-thienyl)	Me	CH(Me)CH 2 OMe	H
1-549	CF 3	CO(2-thienyl)	Me	CH(Me)Ph	H
1-550	CF 3	CO(3-thienyl)	Me	i-Pr	H
1-551	CF 3	CO(3-thienyl)	Me	t-Bu	H
1-552	CF 3	CO(3-thienyl)	Me	s-Bu	H
1-553	CF 3	CO(3-thienyl)	Me	i-Bu	H
1-554	CF 3	CO(3-thienyl)	Me	CH(Me)CH 2 OMe	H
1-555	CF 3	CO(3-thienyl)	Me	CH(Me)Ph	H
1-556	CF 3	CO(2-tetrahydrofurfuryl)	Me	i-Pr	H
1-557	CF 3	CO(2-tetrahydrofurfuryl)	Me	t-Bu	H
1-558	CF 3	CO(2-tetrahydrofurfuryl)	Me	s-Bu	H
1-559	CF 3	CO(2-tetrahydrofurfuryl)	Me	i-Bu	H
1-560	CF 3	CO(2-tetrahydrofurfuryl)	Me	CH(Me)CH 2 OMe	H
1-561	CF 3	CO(2-tetrahydrofurfuryl)	Me	CH(Me)Ph	H
1-562	CF 3	COCH 2 (2-pyridyl)	Me	i-Pr	H
1-563	CF 3	COCH 2 (2-pyridyl)	Me	t-Bu	H
1-564	CF 3	COCH 2 (2-pyridyl)	Me	s-Bu	H
1-565	CF 3	COCH 2 (2-pyridyl)	Me	i-Bu	H
1-566	CF 3	COCH 2 (2-pyridyl)	Me	CH(Me)CH 2 OMe	H
1-567	CF 3	COCH 2 (2-pyridyl)	Me	CH(Me)Ph	H
1-568	CF 3	COCH 2 (2-thienyl)	Me	i-Pr	H
1-569	CF 3	COCH 2 (2-thienyl)	Me	t-Bu	H
1-570	CF 3	COCH 2 (2-thienyl)	Me	s-Bu	H
1-571	CF 3	COCH 2 (2-thienyl)	Me	i-Bu	H
1-572	CF 3	COCH 2 (2-thienyl)	Me	CH(Me)CH 2 OMe	H
1-573	CF 3	COCH 2 (2-thienyl)	Me	CH(Me)Ph	H
1-574	CF 3	CO 2 Me	Me	Me	H
1-575	CF 3	CO 2 Me	Me	i-Pr	H
1-576	CF 3	CO 2 Me	Me	t-Bu	H
1-577	CF 3	CO 2 Me	Me	s-Bu	H
1-578	CF 3	CO 2 Me	Me	CH(Et)CH 2 CH 3	H
1-579	CF 3	CO 2 Me	Me	C(Me) 2 CH 2 CH 3	H
1-580	CF 3	CO 2 Me	Me	i-Bu	H
1-581	CF 3	CO 2 Me	Me	CH 2 C(Me) 2 CH 3	H
1-582	CF 3	CO 2 Me	Me	CH(Me)CH 2 CH 2 CH 3	H
1-583	CF 3	CO 2 Me	Me	CH 2 CH(Me)CH 2 CH 3	H
1-584	CF 3	CO 2 Me	Me	CH 2 CH(Et)CH 2 CH 3	H
1-585	CF 3	CO 2 Me	Me	CH 2 c-Pr	H
1-586	CF 3	CO 2 Me	Me	CH 2 CH 2 OMe	H
1-587	CF 3	CO 2 Me	Me	CH(Me)CH 2 OMe	H
1-588	CF 3	CO 2 Me	Me	CH(Et)CH 2 OMe	H
1-589	CF 3	CO 2 Me	Me	CH 2 CH(Me)OMe	H
1-590	CF 3	CO 2 Me	Me	CH(Me)CH 2 OEt	H
1-591	CF 3	CO 2 Me	Me	CH(Me)CH 2 CH 2 OMe	H
1-592	CF 3	CO 2 Me	Me	CH 2 CH 2 SMe	H
1-593	CF 3	CO 2 Me	Me	2-ClPh	H
1-594	CF 3	CO 2 Me	Me	3-ClPh	H
1-595	CF 3	CO 2 Me	Me	4-ClPh	H
1-596	CF 3	CO 2 Me	Me	CH 2 Ph	H
1-597	CF 3	CO 2 Me	Me	CH 2 (4-FPh)	H
1-598	CF 3	CO 2 Me	Me	CH(Me)Ph	H
1-599	CF 3	CO 2 Me	Me	CH(Me)(4-FPh)	H
1-600	CF 3	CO 2 Me	Me	1-indanyl	H
1-601	CF 3	CO 2 Me	Me	1-(1,2,3,4-tetrahydro-Np)	H
1-602	CF 3	CO 2 Et	Me	Me	H
1-603	CF 3	CO 2 Et	Me	i-Pr	H
1-604	CF 3	CO 2 Et	Me	t-Bu	H
1-605	CF 3	CO 2 Et	Me	s-Bu	H
1-606	CF 3	CO 2 Et	Me	CH(Et)CH 2 CH 3	H
1-607	CF 3	CO 2 Et	Me	C(Me) 2 CH 2 CH 3	H
1-608	CF 3	CO 2 Et	Me	i-Bu	H
1-609	CF 3	CO 2 Et	Me	CH 2 C(Me) 2 CH 3	H
1-610	CF 3	CO 2 Et	Me	CH(Me)CH 2 CH 2 CH 3	H
1-611	CF 3	CO 2 Et	Me	CH 2 CH(Me)CH 2 CH 3	H
1-612	CF 3	CO 2 Et	Me	CH 2 CH(Et)CH 2 CH 3	H
1-613	CF 3	CO 2 Et	Me	CH 2 c-Pr	H
1-614	CF 3	CO 2 Et	Me	CH 2 CH 2 OMe	H
1-615	CF 3	CO 2 Et	Me	CH(Me)CH 2 OMe	H
1-616	CF 3	CO 2 Et	Me	CH(Et)CH 2 OMe	H
1-617	CF 3	CO 2 Et	Me	CH 2 CH(Me)OMe	H
1-618	CF 3	CO 2 Et	Me	CH(Me)CH 2 OEt	H
1-619	CF 3	CO 2 Et	Me	CH(Me)CH 2 CH 2 OMe	H
1-620	CF 3	CO 2 Et	Me	CH 2 CH 2 SMe	H
1-621	CF 3	CO 2 Et	Me	2-ClPh	H
1-622	CF 3	CO 2 Et	Me	3-ClPh	H
1-623	CF 3	CO 2 Et	Me	4-ClPh	H
1-624	CF 3	CO 2 Et	Me	CH 2 Ph	H
1-625	CF 3	CO 2 Et	Me	CH 2 (4-FPh)	H
1-626	CF 3	CO 2 Et	Me	CH(Me)Ph	H
1-627	CF 3	CO 2 Et	Me	CH(Me)(4-FPh)	H
1-628	CF 3	CO 2 Et	Me	1-indanyl	H
1-629	CF 3	CO 2 Et	Me	1-(1,2,3,4-tetrahydro-Np)	H
1-630	CF 3	CO 2 n-Pr	Me	i-Pr	H
1-631	CF 3	CO 2 n-Pr	Me	t-Bu	H
1-632	CF 3	CO 2 n-Pr	Me	s-Bu	H
1-633	CF 3	CO 2 n-Pr	Me	i-Bu	H
1-634	CF 3	CO 2 n-Pr	Me	CH(Me)CH 2 OMe	H
1-635	CF 3	CO 2 n-Pr	Me	CH(Et)CH 2 OMe	H
1-636	CF 3	CO 2 n-Pr	Me	CH 2 CH(Me)OMe	H
1-637	CF 3	CO 2 n-Pr	Me	CH(Me)CH 2 OEt	H
1-638	CF 3	CO 2 n-Pr	Me	CH(Me)CH 2 CH 2 OMe	H
1-639	CF 3	CO 2 n-Pr	Me	CH(Me)Ph	H
1-640	CF 3	CO 2 i-Pr	Me	i-Pr	H
1-641	CF 3	CO 2 i-Pr	Me	t-Bu	H
1-642	CF 3	CO 2 i-Pr	Me	s-Bu	H
1-643	CF 3	CO 2 i-Pr	Me	CH(Et)CH 2 CH 3	H
1-644	CF 3	CO 2 i-Pr	Me	i-Bu	H
1-645	CF 3	CO 2 i-Pr	Me	CH 2 C(Me) 2 CH 3	H
1-646	CF 3	CO 2 i-Pr	Me	CH(Me)CH 2 CH 2 CH 3	H
1-647	CF 3	CO 2 i-Pr	Me	CH(Me)CH 2 OMe	H
1-648	CF 3	CO 2 i-Pr	Me	CH(Et)CH 2 OMe	H
1-649	CF 3	CO 2 i-Pr	Me	CH 2 CH(Me)OMe	H
1-650	CF 3	CO 2 i-Pr	Me	CH(Me)CH 2 OEt	H
1-651	CF 3	CO 2 i-Pr	Me	CH(Me)CH 2 CH 2 OMe	H
1-652	CF 3	CO 2 i-Pr	Me	CH 2 CH 2 SMe	H
1-653	CF 3	CO 2 i-Pr	Me	CH(Me)Ph	H
1-654	CF 3	CO 2 n-Bu	Me	i-Pr	H
1-655	CF 3	CO 2 n-Bu	Me	t-Bu	H
1-656	CF 3	CO 2 n-Bu	Me	s-Bu	H
1-657	CF 3	CO 2 n-Bu	Me	i-Bu	H
1-658	CF 3	CO 2 n-Bu	Me	CH(Me)CH 2 OMe	H
1-659	CF 3	CO 2 n-Bu	Me	CH(Me)Ph	H
1-660	CF 3	CO 2 s-Bu	Me	i-Pr	H
1-661	CF 3	CO 2 s-Bu	Me	t-Bu	H
1-662	CF 3	CO 2 s-Bu	Me	s-Bu	H
1-663	CF 3	CO 2 s-Bu	Me	i-Bu	H
1-664	CF 3	CO 2 s-Bu	Me	CH(Me)CH 2 OMe	H
1-665	CF 3	CO 2 s-Bu	Me	CH(Me)Ph	H
1-666	CF 3	CO 2 i-Bu	Me	Me	H
1-667	CF 3	CO 2 i-Bu	Me	i-Pr	H
1-668	CF 3	CO 2 i-Bu	Me	t-Bu	H
1-669	CF 3	CO 2 i-Bu	Me	s-Bu	H
1-670	CF 3	CO 2 i-Bu	Me	CH(Et)CH 2 CH 3	H
1-671	CF 3	CO 2 i-Bu	Me	i-Bu	H
1-672	CF 3	CO 2 i-Bu	Me	CH 2 C(Me) 2 CH 3	H
1-673	CF 3	CO 2 i-Bu	Me	CH(Me)CH 2 CH 2 CH 3	H
1-674	CF 3	CO 2 i-Bu	Me	CH 2 CH(Me)CH 2 CH 3	H
1-675	CF 3	CO 2 i-Bu	Me	CH(Me)CH 2 OMe	H
1-676	CF 3	CO 2 i-Bu	Me	CH 2 CH 2 SMe	H
1-677	CF 3	CO 2 i-Bu	Me	CH 2 Ph	H
1-678	CF 3	CO 2 i-Bu	Me	CH(Me)Ph	H
1-679	CF 3	CO 2 i-Bu	Me	CONEt 2	H
1-680	CF 3	CO 2 t-Bu	Me	i-Pr	H
1-681	CF 3	CO 2 t-Bu	Me	t-Bu	H
1-682	CF 3	CO 2 t-Bu	Me	s-Bu	H
1-683	CF 3	CO 2 t-Bu	Me	i-Bu	H
1-684	CF 3	CO 2 t-Bu	Me	CH(Me)CH 2 OMe	H
1-685	CF 3	CO 2 t-Bu	Me	CH(Me)Ph	H
1-686	CF 3	CO 2 n-Pen	Me	i-Pr	H
1-687	CF 3	CO 2 n-Pen	Me	t-Bu	H
1-688	CF 3	CO 2 n-Pen	Me	s-Bu	H
1-689	CF 3	CO 2 n-Pen	Me	i-Bu	H
1-690	CF 3	CO 2 n-Pen	Me	CH(Me)CH 2 OMe	H
1-691	CF 3	CO 2 n-Pen	Me	CH(Me)Ph	H
1-692	CF 3	CO 2 n-Hex	Me	i-Pr	H
1-693	CF 3	CO 2 n-Hex	Me	t-Bu	H
1-694	CF 3	CO 2 n-Hex	Me	s-Bu	H
1-695	CF 3	CO 2 n-Hex	Me	i-Bu	H
1-696	CF 3	CO 2 n-Hex	Me	CH(Me)CH 2 OMe	H
1-697	CF 3	CO 2 n-Hex	Me	CH(Me)Ph	H
1-698	CF 3	CO 2 CH 2 CF 3	Me	i-Pr	H
1-699	CF 3	CO 2 CH 2 CF 3	Me	t-Bu	H
1-700	CF 3	CO 2 CH 2 CF 3	Me	s-Bu	H
1-701	CF 3	CO 2 CH 2 CF 3	Me	i-Bu	H
1-702	CF 3	CO 2 CH 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-703	CF 3	CO 2 CH 2 CF 3	Me	CH(Me)Ph	H
1-704	CF 3	CO 2 CH 2 CH═CH 2	Me	i-Pr	H
1-705	CF 3	CO 2 CH 2 CH═CH 2	Me	t-Bu	H
1-706	CF 3	CO 2 CH 2 CH═CH 2	Me	s-Bu	H
1-707	CF 3	CO 2 CH 2 CH═CH 2	Me	i-Bu	H
1-708	CF 3	CO 2 CH 2 CH═CH 2	Me	CH(Me)CH 2 OMe	H
1-709	CF 3	CO 2 CH 2 CH═CH 2	Me	CH 2 CH 2 SMe	H
1-710	CF 3	CO 2 CH 2 CH═CH 2	Me	CH(Me)Ph	H
1-711	CF 3	CO 2 CH 2 C≡CH	Me	i-Pr	H
1-712	CF 3	CO 2 CH 2 C≡CH	Me	t-Bu	H
1-713	CF 3	CO 2 CH 2 C≡CH	Me	s-Bu	H
1-714	CF 3	CO 2 CH 2 C≡CH	Me	i-Bu	H
1-715	CF 3	CO 2 CH 2 C≡CH	Me	CH(Me)CH 2 OMe	H
1-716	CF 3	CO 2 CH 2 C≡CH	Me	CH(Me)Ph	H
1-717	CF 3	CO 2 c-Pr	Me	i-Pr	H
1-718	CF 3	CO 2 c-Pr	Me	t-Bu	H
1-719	CF 3	CO 2 c-Pr	Me	s-Bu	H
1-720	CF 3	CO 2 c-Pr	Me	i-Bu	H
1-721	CF 3	CO 2 c-Pr	Me	CH(Me)CH 2 OMe	H
1-722	CF 3	CO 2 c-Pr	Me	CH(Me)Ph	H
1-723	CF 3	CO 2 CH 2 c-Pr	Me	i-Pr	H
1-724	CF 3	CO 2 CH 2 c-Pr	Me	t-Bu	H
1-725	CF 3	CO 2 CH 2 c-Pr	Me	s-Bu	H
1-726	CF 3	CO 2 CH 2 c-Pr	Me	i-Bu	H
1-727	CF 3	CO 2 CH 2 c-Pr	Me	CH(Me)CH 2 OMe	H
1-728	CF 3	CO 2 CH 2 c-Pr	Me	CH(Me)Ph	H
1-729	CF 3	CO 2 CH 2 CH 2 OMe	Me	i-Pr	H
1-730	CF 3	CO 2 CH 2 CH 2 OMe	Me	t-Bu	H
1-731	CF 3	CO 2 CH 2 CH 2 OMe	Me	s-Bu	H
1-732	CF 3	CO 2 CH 2 CH 2 OMe	Me	i-Bu	H
1-733	CF 3	CO 2 CH 2 CH 2 OMe	Me	CH 2 CH(Me)CH 2 CH 3	H
1-734	CF 3	CO 2 CH 2 CH 2 OMe	Me	CH(Me)CH 2 OMe	H
1-735	CF 3	CO 2 CH 2 CH 2 OMe	Me	CH 2 CH 2 SMe	H
1-736	CF 3	CO 2 CH 2 CH 2 OMe	Me	CH(Me)Ph	H
1-737	CF 3	CO 2 CH 2 CH 2 OCH 2 CF 3	Me	i-Pr	H
1-738	CF 3	CO 2 CH 2 CH 2 OCH 2 CF 3	Me	t-Bu	H
1-739	CF 3	CO 2 CH 2 CH 2 OCH 2 CF 3	Me	s-Bu	H
1-740	CF 3	CO 2 CH 2 CH 2 OCH 2 CF 3	Me	i-Bu	H
1-741	CF 3	CO 2 CH 2 CH 2 OCH 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-742	CF 3	CO 2 CH 2 CH 2 OCH 2 CF 3	Me	CH(Me)Ph	H
1-743	CF 3	CO 2 CH 2 CH 2 OCH 2 CH 2 OMe	Me	i-Pr	H
1-744	CF 3	CO 2 CH 2 CH 2 OCH 2 CH 2 OMe	Me	t-Bu	H
1-745	CF 3	CO 2 CH 2 CH 2 OCH 2 CH 2 OMe	Me	s-Bu	H
1-746	CF 3	CO 2 CH 2 CH 2 OCH 2 CH 2 OMe	Me	i-Bu	H
1-747	CF 3	CO 2 CH 2 CH 2 OCH 2 CH 2 OMe	Me	CH(Me)CH 2 OMe	H
1-748	CF 3	CO 2 CH 2 CH 2 OCH 2 CH 2 OMe	Me	CH(Me)Ph	H
1-749	CF 3	CO 2 CH 2 CH 2 SMe	Me	i-Pr	H
1-750	CF 3	CO 2 CH 2 CH 2 SMe	Me	t-Bu	H
1-751	CF 3	CO 2 CH 2 CH 2 SMe	Me	s-Bu	H
1-752	CF 3	CO 2 CH 2 CH 2 SMe	Me	i-Bu	H
1-753	CF 3	CO 2 CH 2 CH 2 SMe	Me	CH(Me)CH 2 OMe	H
1-754	CF 3	CO 2 CH 2 CH 2 SMe	Me	CH(Me)Ph	H
1-755	CF 3	CO 2 CH 2 CH 2 SCH 2 CF 3	Me	i-Pr	H
1-756	CF 3	CO 2 CH 2 CH 2 SCH 2 CF 3	Me	t-Bu	H
1-757	CF 3	CO 2 CH 2 CH 2 SCH 2 CF 3	Me	s-Bu	H
1-758	CF 3	CO 2 CH 2 CH 2 SCH 2 CF 3	Me	i-Bu	H
1-759	CF 3	CO 2 CH 2 CH 2 SCH 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-760	CF 3	CO 2 CH 2 CH 2 SCH 2 CF 3	Me	CH(Me)Ph	H
1-761	CF 3	CO 2 Ph	Me	i-Pr	H
1-762	CF 3	CO 2 Ph	Me	t-Bu	H
1-763	CF 3	CO 2 Ph	Me	s-Bu	H
1-764	CF 3	CO 2 Ph	Me	i-Bu	H
1-765	CF 3	CO 2 Ph	Me	CH(Me)CH 2 OMe	H
1-766	CF 3	CO 2 Ph	Me	CH(Me)Ph	H
1-767	CF 3	CO 2 (4-ClPh)	Me	i-Pr	H
1-768	CF 3	CO 2 (4-ClPh)	Me	t-Bu	H
1-769	CF 3	CO 2 (4-ClPh)	Me	s-Bu	H
1-770	CF 3	CO 2 (4-ClPh)	Me	i-Bu	H
1-771	CF 3	CO 2 (4-ClPh)	Me	CH(Me)CH 2 OMe	H
1-772	CF 3	CO 2 (4-ClPh)	Me	CH(Me)Ph	H
1-773	CF 3	CO 2 (4-MePh)	Me	i-Pr	H
1-774	CF 3	CO 2 (4-MePh)	Me	t-Bu	H
1-775	CF 3	CO 2 (4-MePh)	Me	s-Bu	H
1-776	CF 3	CO 2 (4-MePh)	Me	i-Bu	H
1-777	CF 3	CO 2 (4-MePh)	Me	CH(Me)CH 2 OMe	H
1-778	CF 3	CO 2 (4-MePh)	Me	CH(Me)Ph	H
1-779	CF 3	CO 2 CH 2 Ph	Me	Me	H
1-780	CF 3	CO 2 CH 2 Ph	Me	i-Pr	H
1-781	CF 3	CO 2 CH 2 Ph	Me	t-Bu	H
1-782	CF 3	CO 2 CH 2 Ph	Me	s-Bu	H
(TLC top)
1-783	CF 3	CO 2 CH 2 Ph	Me	s-Bu	H
(TLC bottom)
1-784	CF 3	CO 2 CH 2 Ph	Me	CH(Et)CH 2 CH 3	H
1-785	CF 3	CO 2 CH 2 Ph	Me	i-Bu	H
1-786	CF 3	CO 2 CH 2 Ph	Me	CH 2 C(Me) 2 CH 3	H
1-787	CF 3	CO 2 CH 2 Ph	Me	CH(Me)CH 2 CH 2 CH 3	H
1-788	CF 3	CO 2 CH 2 Ph	Me	CH 2 CH(Me)CH 2 CH 3	H
(TLC top)
1-789	CF 3	CO 2 CH 2 Ph	Me	CH 2 CH(Me)CH 2 CH 3	H
(TLC bottom)
1-790	CF 3	CO 2 CH 2 Ph	Me	CH(Me)CH 2 OMe	H
1-791	CF 3	CO 2 CH 2 Ph	Me	CH 2 CH 2 SMe	H
1-792	CF 3	CO 2 CH 2 Ph	Me	2-ClPh	H
1-793	CF 3	CO 2 CH 2 Ph	Me	3-ClPh	H
1-794	CF 3	CO 2 CH 2 Ph	Me	4-ClPh	H
1-795	CF 3	CO 2 CH 2 Ph	Me	CH 2 Ph	H
1-796	CF 3	CO 2 CH 2 Ph	Me	CH(Me)Ph	H
1-797	CF 3	CO 2 CH 2 (4-ClPh)	Me	i-Pr	H
1-798	CF 3	CO 2 CH 2 (4-ClPh)	Me	t-Bu	H
1-799	CF 3	CO 2 CH 2 (4-ClPh)	Me	s-Bu	H
1-800	CF 3	CO 2 CH 2 (4-ClPh)	Me	i-Bu	H
1-801	CF 3	CO 2 CH 2 (4-ClPh)	Me	CH(Me)CH 2 OMe	H
1-802	CF 3	CO 2 CH 2 (4-ClPh)	Me	CH(Me)Ph	H
1-803	CF 3	CO 2 CH 2 (4-MePh)	Me	i-Pr	H
1-804	CF 3	CO 2 CH 2 (4-MePh)	Me	t-Bu	H
1-805	CF 3	CO 2 CH 2 (4-MePh)	Me	s-Bu	H
1-806	CF 3	CO 2 CH 2 (4-MePh)	Me	i-Bu	H
1-807	CF 3	CO 2 CH 2 (4-MePh)	Me	CH(Me)CH 2 OMe	H
1-808	CF 3	CO 2 CH 2 (4-MePh)	Me	CH(Me)Ph	H
1-809	CF 3	CO 2 (2-tetrahydrofuryl)	Me	i-Pr	H
1-810	CF 3	CO 2 (2-tetrahydrofuryl)	Me	t-Bu	H
1-811	CF 3	CO 2 (2-tetrahydrofuryl)	Me	s-Bu	H
1-812	CF 3	CO 2 (2-tetrahydrofuryl)	Me	i-Bu	H
1-813	CF 3	CO 2 (2-tetrahydrofuryl)	Me	CH(Me)CH 2 OMe	H
1-814	CF 3	CO 2 (2-tetrahydrofuryl)	Me	CH(Me)Ph	H
1-815	CF 3	CO 2 (2-pyridyl)	Me	i-Pr	H
1-816	CF 3	CO 2 (2-pyridyl)	Me	t-Bu	H
1-817	CF 3	CO 2 (2-pyridyl)	Me	s-Bu	H
1-818	CF 3	CO 2 (2-pyridyl)	Me	i-Bu	H
1-819	CF 3	CO 2 (2-pyridyl)	Me	CH(Me)CH 2 OMe	H
1-820	CF 3	CO 2 (2-pyridyl)	Me	CH(Me)Ph	H
1-821	CF 3	CO 2 (2-thienyl)	Me	i-Pr	H
1-822	CF 3	CO 2 (2-thienyl)	Me	t-Bu	H
1-823	CF 3	CO 2 (2-thienyl)	Me	s-Bu	H
1-824	CF 3	CO 2 (2-thienyl)	Me	i-Bu	H
1-825	CF 3	CO 2 (2-thienyl)	Me	CH(Me)CH 2 OMe	H
1-826	CF 3	CO 2 (2-thienyl)	Me	CH(Me)Ph	H
1-827	CF 3	CO 2 (2-tetrahydrofurfuryl)	Me	i-Pr	H
1-828	CF 3	CO 2 (2-tetrahydrofurfuryl)	Me	t-Bu	H
1-829	CF 3	CO 2 (2-tetrahydrofurfuryl)	Me	s-Bu	H
1-830	CF 3	CO 2 (2-tetrahydrofurfuryl)	Me	i-Bu	H
1-831	CF 3	CO 2 (2-tetrahydrofurfuryl)	Me	CH(Me)CH 2 OMe	H
1-832	CF 3	CO 2 (2-tetrahydrofurfuryl)	Me	CH(Me)Ph	H
1-833	CF 3	CO 2 CH 2 (2-pyridyl)	Me	i-Pr	H
1-834	CF 3	CO 2 CH 2 (2-pyridyl)	Me	t-Bu	H
1-835	CF 3	CO 2 CH 2 (2-pyridyl)	Me	s-Bu	H
1-836	CF 3	CO 2 CH 2 (2-pyridyl)	Me	i-Bu	H
1-837	CF 3	CO 2 CH 2 (2-pyridyl)	Me	CH(Me)CH 2 OMe	H
1-838	CF 3	CO 2 CH 2 (2-pyridyl)	Me	CH(Me)Ph	H
1-839	CF 3	CO 2 CH 2 (2-thienyl)	Me	i-Pr	H
1-840	CF 3	CO 2 CH 2 (2-thienyl)	Me	t-Bu	H
1-841	CF 3	CO 2 CH 2 (2-thienyl)	Me	s-Bu	H
1-842	CF 3	CO 2 CH 2 (2-thienyl)	Me	i-Bu	H
1-843	CF 3	CO 2 CH 2 (2-thienyl)	Me	CH(Me)CH 2 OMe	H
1-844	CF 3	CO 2 CH 2 (2-thienyl)	Me	CH(Me)Ph	H
1-845	CF 3	CO(SMe)	Me	i-Pr	H
1-846	CF 3	CO(SMe)	Me	t-Bu	H
1-847	CF 3	CO(SMe)	Me	s-Bu	H
1-848	CF 3	CO(SMe)	Me	i-Bu	H
1-849	CF 3	CO(SMe)	Me	CH(Me)CH 2 OMe	H
1-850	CF 3	CO(SMe)	Me	CH(Me)Ph	H
1-851	CF 3	CO(SEt)	Me	i-Pr	H
1-852	CF 3	CO(SEt)	Me	t-Bu	H
1-853	CF 3	CO(SEt)	Me	s-Bu	H
1-854	CF 3	CO(SEt)	Me	i-Bu	H
1-855	CF 3	CO(SEt)	Me	CH(Me)CH 2 OMe	H
1-856	CF 3	CO(SEt)	Me	CH(Me)Ph	H
1-857	CF 3	CO(SCF 3 )	Me	i-Pr	H
1-858	CF 3	CO(SCF 3 )	Me	t-Bu	H
1-859	CF 3	CO(SCF 3 )	Me	s-Bu	H
1-860	CF 3	CO(SCF 3 )	Me	i-Bu	H
1-861	CF 3	CO(SCF 3 )	Me	CH(Me)CH 2 OMe	H
1-862	CF 3	CO(SCF 3 )	Me	CH(Me)Ph	H
1-863	CF 3	CO(SCH 2 CF 3 )	Me	i-Pr	H
1-864	CF 3	CO(SCH 2 CF 3 )	Me	t-Bu	H
1-865	CF 3	CO(SCH 2 CF 3 )	Me	s-Bu	H
1-866	CF 3	CO(SCH 2 CF 3 )	Me	i-Bu	H
1-867	CF 3	CO(SCH 2 CF 3 )	Me	CH(Me)CH 2 OMe	H
1-868	CF 3	CO(SCH 2 CF 3 )	Me	CH(Me)Ph	H
1-869	CF 3	CONHEt	Me	i-Pr	H
1-870	CF 3	CONHEt	Me	t-Bu	H
1-871	CF 3	CONHEt	Me	s-Bu	H
1-872	CF 3	CONHEt	Me	i-Bu	H
1-873	CF 3	CONHEt	Me	CH(Me)CH 2 OMe	H
1-874	CF 3	CONHEt	Me	CH(Me)Ph	H
1-875	CF 3	CONHCH 2 CF 3	Me	i-Pr	H
1-876	CF 3	CONHCH 2 CF 3	Me	t-Bu	H
1-877	CF 3	CONHCH 2 CF 3	Me	s-Bu	H
1-878	CF 3	CONHCH 2 CF 3	Me	i-Bu	H
1-879	CF 3	CONHCH 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-880	CF 3	CONHCH 2 CF 3	Me	CH(Me)Ph	H
1-881	CF 3	CONEt 2	Me	i-Pr	H
1-882	CF 3	CONEt 2	Me	t-Bu	H
1-883	CF 3	CONEt 2	Me	s-Bu	H
1-884	CF 3	CONEt 2	Me	i-Bu	H
1-885	CF 3	CONEt 2	Me	CH(Me)CH 2 OMe	H
1-886	CF 3	CONEt 2	Me	CH(Me)Ph	H
1-887	CF 3	SO 2 Me	Me	Me	H
1-888	CF 3	SO 2 Me	Me	i-Pr	H
1-889	CF 3	SO 2 Me	Me	t-Bu	H
1-890	CF 3	SO 2 Me	Me	s-Bu	H
1-891	CF 3	SO 2 Me	Me	CH(Et)CH 2 CH 3	H
1-892	CF 3	SO 2 Me	Me	i-Bu	H
1-893	CF 3	SO 2 Me	Me	CH 2 C(Me) 2 CH 3	H
1-894	CF 3	SO 2 Me	Me	CH(Me)CH 2 CH 2 CH 3	H
1-895	CF 3	SO 2 Me	Me	CH 2 CH(Me)CH 2 CH 3	H
1-896	CF 3	SO 2 Me	Me	CH 2 CH(Et)CH 2 CH 3	H
1-897	CF 3	SO 2 Me	Me	CH 2 c-Pr	H
1-898	CF 3	SO 2 Me	Me	CH 2 CH 2 OMe	H
1-899	CF 3	SO 2 Me	Me	CH(Me)CH 2 OMe	H
1-900	CF 3	SO 2 Me	Me	CH 2 CH 2 SMe	H
1-901	CF 3	SO 2 Me	Me	Ph	H
1-902	CF 3	SO 2 Me	Me	2-ClPh	H
1-903	CF 3	SO 2 Me	Me	3-ClPh	H
1-904	CF 3	SO 2 Me	Me	4-ClPh	H
1-905	CF 3	SO 2 Me	Me	CH 2 Ph	H
1-906	CF 3	SO 2 Me	Me	CH 2 (4-FPh)	H
1-907	CF 3	SO 2 Me	Me	CH(Me)Ph	H
1-908	CF 3	SO 2 Me	Me	CH(Me)(4-FPh)	H
1-909	CF 3	SO 2 Me	Me	1-indanyl	H
1-910	CF 3	SO 2 Me	Me	1-(1,2,3,4-tetrahydro-Np)	H
1-911	CF 3	SO 2 Et	Me	i-Pr	H
1-912	CF 3	SO 2 Et	Me	t-Bu	H
1-913	CF 3	SO 2 Et	Me	s-Bu	H
1-914	CF 3	SO 2 Et	Me	i-Bu	H
1-915	CF 3	SO 2 Et	Me	CH(Me)CH 2 OMe	H
1-916	CF 3	SO 2 Et	Me	CH 2 CH 2 SMe	H
1-917	CF 3	SO 2 Et	Me	CH(Me)Ph	H
1-918	CF 3	SO 2 n-Pr	Me	i-Pr	H
1-919	CF 3	SO 2 n-Pr	Me	t-Bu	H
1-920	CF 3	SO 2 n-Pr	Me	s-Bu	H
1-921	CF 3	SO 2 n-Pr	Me	i-Bu	H
1-922	CF 3	SO 2 n-Pr	Me	CH(Me)CH 2 OMe	H
1-923	CF 3	SO 2 n-Pr	Me	CH(Me)Ph	H
1-924	CF 3	SO 2 i-Pr	Me	i-Pr	H
1-925	CF 3	SO 2 i-Pr	Me	t-Bu	H
1-926	CF 3	SO 2 i-Pr	Me	s-Bu	H
1-927	CF 3	SO 2 i-Pr	Me	i-Bu	H
1-928	CF 3	SO 2 i-Pr	Me	CH(Me)CH 2 OMe	H
1-929	CF 3	SO 2 i-Pr	Me	CH(Me)Ph	H
1-930	CF 3	SO 2 n-Bu	Me	i-Pr	H
1-931	CF 3	SO 2 n-Bu	Me	t-Bu	H
1-932	CF 3	SO 2 n-Bu	Me	s-Bu	H
1-933	CF 3	SO 2 n-Bu	Me	i-Bu	H
1-934	CF 3	SO 2 n-Bu	Me	CH(Me)CH 2 OMe	H
1-935	CF 3	SO 2 n-Bu	Me	CH(Me)Ph	H
1-936	CF 3	SO 2 i-Bu	Me	i-Pr	H
1-937	CF 3	SO 2 i-Bu	Me	t-Bu	H
1-938	CF 3	SO 2 i-Bu	Me	s-Bu	H
1-939	CF 3	SO 2 i-Bu	Me	i-Bu	H
1-940	CF 3	SO 2 i-Bu	Me	CH(Me)CH 2 OMe	H
1-941	CF 3	SO 2 i-Bu	Me	CH(Me)Ph	H
1-942	CF 3	SO 2 CH 2 Cl	Me	i-Pr	H
1-943	CF 3	SO 2 CH 2 Cl	Me	t-Bu	H
1-944	CF 3	SO 2 CH 2 Cl	Me	i-Bu	H
1-945	CF 3	SO 2 CH 2 Cl	Me	CH(Me)CH 2 OMe	H
1-946	CF 3	SO 2 CH 2 Cl	Me	CH(Me)Ph	H
1-947	CF 3	SO 2 CCl 3	Me	i-Pr	H
1-948	CF 3	SO 2 CCl 3	Me	t-Bu	H
1-949	CF 3	SO 2 CCl 3	Me	s-Bu	H
1-950	CF 3	SO 2 CCl 3	Me	i-Bu	H
1-951	CF 3	SO 2 CCl 3	Me	CH(Me)CH 2 OMe	H
1-952	CF 3	SO 2 CCl 3	Me	CH(Me)Ph	H
1-953	CF 3	SO 2 CHF 2	Me	i-Pr	H
1-954	CF 3	SO 2 CHF 2	Me	t-Bu	H
1-955	CF 3	SO 2 CHF 2	Me	i-Bu	H
1-956	CF 3	SO 2 CHF 2	Me	CH(Me)CH 2 OMe	H
1-957	CF 3	SO 2 CHF 2	Me	CH(Me)Ph	H
1-958	CF 3	SO 2 CF 3	Me	H	H
1-959	CF 3	SO 2 CF 3	Me	Me	H
1-960	CF 3	SO 2 CF 3	Me	Et	H
1-961	CF 3	SO 2 CF 3	Me	n-Pr	H
1-962	CF 3	SO 2 CF 3	Me	i-Pr	H
1-963	CF 3	SO 2 CF 3	Me	t-Bu	H
1-964	CF 3	SO 2 CF 3	Me	s-Bu	H
1-965	CF 3	SO 2 CF 3	Me	CH(Et)CH 2 CH 3	H
1-966	CF 3	SO 2 CF 3	Me	C(Me) 2 CH 2 CH 3	H
1-967	CF 3	SO 2 CF 3	Me	i-Bu	H
1-968	CF 3	SO 2 CF 3	Me	CH 2 C(Me) 2 CH 3	H
1-969	CF 3	SO 2 CF 3	Me	n-Bu	H
1-970	CF 3	SO 2 CF 3	Me	CH(Me)CH 2 CH 2 CH 3	H
1-971	CF 3	SO 2 CF 3	Me	CH(Et)CH 2 CH 2 CH 3	H
1-972	CF 3	SO 2 CF 3	Me	CH 2 CH(Me)CH 2 CH 3	H
1-973	CF 3	SO 2 CF 3	Me	CH 2 CH(Et)CH 2 CH 3	H
1-974	CF 3	SO 2 CF 3	Me	CH 2 CH 2 CH(Me)CH 3	H
1-975	CF 3	SO 2 CF 3	Me	CH 2 CH 2 C(Me) 2 CH 3	H
1-976	CF 3	SO 2 CF 3	Me	n-Pen	H
1-977	CF 3	SO 2 CF 3	Me	CH(Me)CH 2 CH 2 CH 2 CH 3	H
1-978	CF 3	SO 2 CF 3	Me	CH 2 CH 2 CH(Me)CH 2 CH 3	H
1-979	CF 3	SO 2 CF 3	Me	n-Hex	H
1-980	CF 3	SO 2 CF 3	Me	CH 2 CH(Et)CH 2 CH 2 CH 2 CH 3	H
1-981	CF 3	SO 2 CF 3	Me	(CH 2 ) 7 CH 3	H
1-982	CF 3	SO 2 CF 3	Me	(CH 2 ) 13 CH 3	H
1-983	CF 3	SO 2 CF 3	Me	CH 2 CH 2 Cl	H
1-984	CF 3	SO 2 CF 3	Me	CH 2 CF 3	H
1-985	CF 3	SO 2 CF 3	Me	CH 2 CH═CH 2	H
1-986	CF 3	SO 2 CF 3	Me	CH(Me)CH═CH 2	H
1-987	CF 3	SO 2 CF 3	Me	CH 2 C(Me)═CH 2	H
1-988	CF 3	SO 2 CF 3	Me	CH 2 C≡CH	H
1-989	CF 3	SO 2 CF 3	Me	c-Pr	H
1-990	CF 3	SO 2 CF 3	Me	c-Hex	H
1-991	CF 3	SO 2 CF 3	Me	CH 2 c-Pr	H
1-992	CF 3	SO 2 CF 3	Me	CH(Me)c-Pr	H
1-993	CF 3	SO 2 CF 3	Me	CH 2 (1-Me-c-Pr)	H
1-994	CF 3	SO 2 CF 3	Me	CH 2 c-Hex	H
1-995	CF 3	SO 2 CF 3	Me	CH 2 OMe	H
1-996	CF 3	SO 2 CF 3	Me	CH 2 CH 2 OMe	H
1-997	CF 3	SO 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-998	CF 3	SO 2 CF 3	Me	CH 2 CH(Me)OMe	H
1-999	CF 3	SO 2 CF 3	Me	CH 2 CH 2 Oi-Pr	H
1-1000	CF 3	SO 2 CF 3	Me	CH 2 CH 2 Oi-Bu	H
1-1001	CF 3	SO 2 CF 3	Me	CH 2 CH 2 CH 2 OMe	H
1-1002	CF 3	SO 2 CF 3	Me	CH 2 CH 2 SMe	H
1-1003	CF 3	SO 2 CF 3	Me	CH 2 CH 2 CH 2 SMe	H
1-1004	CF 3	SO 2 CF 3	Me	CH 2 CH 2 SCH 2 CF 3	H
1-1005	CF 3	SO 2 CF 3	Me	CH 2 CH 2 SOMe	H
1-1006	CF 3	SO 2 CF 3	Me	CH 2 CH 2 SO 2 Me	H
1-1007	CF 3	SO 2 CF 3	Me	Ph	H
1-1008	CF 3	SO 2 CF 3	Me	2-ClPh	H
1-1009	CF 3	SO 2 CF 3	Me	3-ClPh	H
1-1010	CF 3	SO 2 CF 3	Me	4-ClPh	H
1-1011	CF 3	SO 2 CF 3	Me	CH 2 Ph	H
1-1012	CF 3	SO 2 CF 3	Me	CH 2 (2-FPh)	H
1-1013	CF 3	SO 2 CF 3	Me	CH 2 (3-FPh)	H
1-1014	CF 3	SO 2 CF 3	Me	CH 2 (4-FPh)	H
1-1015	CF 3	SO 2 CF 3	Me	CH 2 (4-ClPh)	H
1-1016	CF 3	SO 2 CF 3	Me	CH 2 (4-BrPh)	H
1-1017	CF 3	SO 2 CF 3	Me	CH 2 (4-CNPh)	H
1-1018	CF 3	SO 2 CF 3	Me	CH 2 (4-MePh)	H
1-1019	CF 3	SO 2 CF 3	Me	CH 2 (4-t-BuPh)	H
1-1020	CF 3	SO 2 CF 3	Me	CH 2 (3-CF 3 Ph)	H
1-1021	CF 3	SO 2 CF 3	Me	CH 2 (4-CF 3 Ph)	H
1-1022	CF 3	SO 2 CF 3	Me	CH 2 (4-MeOPh)	H
1-1023	CF 3	SO 2 CF 3	Me	CH 2 (4-CF 3 OPh)	H
1-1024	CF 3	SO 2 CF 3	Me	CH 2 (4-MeSPh)	H
1-1025	CF 3	SO 2 CF 3	Me	CH 2 (4-CF 3 SPh)	H
1-1026	CF 3	SO 2 CF 3	Me	CH 2 (2,4-F 2 Ph)	H
1-1027	CF 3	SO 2 CF 3	Me	CH 2 (3,4-F 2 Ph)	H
1-1028	CF 3	SO 2 CF 3	Me	CH 2 (2-Cl-4-FPh)	H
1-1029	CF 3	SO 2 CF 3	Me	CH 2 (3-Cl-4-FPh)	H
1-1030	CF 3	SO 2 CF 3	Me	CH(Me)Ph	H
1-1031	CF 3	SO 2 CF 3	Me	CH(Me)(4-FPh)	H
1-1032	CF 3	SO 2 CF 3	Me	CH(Me)(2-ClPh)	H
1-1033	CF 3	SO 2 CF 3	Me	CH(Me)(3-ClPh)	H
1-1034	CF 3	SO 2 CF 3	Me	CH(Me)(4-ClPh)	H
1-1035	CF 3	SO 2 CF 3	Me	CH(Me)(4-MePh)	H
1-1036	CF 3	SO 2 CF 3	Me	CH(Me)(4-CF 3 OPh)	H
1-1037	CF 3	SO 2 CF 3	Me	CH(Me)(2,4-F 2 Ph)	H
1-1038	CF 3	SO 2 CF 3	Me	CH(Et)Ph	H
1-1039	CF 3	SO 2 CF 3	Me	CH(n-Pr)Ph	H
1-1040	CF 3	SO 2 CF 3	Me	CH(i-Pr)Ph	H
1-1041	CF 3	SO 2 CF 3	Me	CH(n-Bu)Ph	H
1-1042	CF 3	SO 2 CF 3	Me	CH(n-Pen)Ph	H
1-1043	CF 3	SO 2 CF 3	Me	CH 2 CH 2 Ph	H
1-1044	CF 3	SO 2 CF 3	Me	CH 2 CH 2 (4-FPh)	H
1-1045	CF 3	SO 2 CF 3	Me	CH(Me)CH 2 Ph	H
1-1046	CF 3	SO 2 CF 3	Me	CH 2 CH(Me)Ph	H
1-1047	CF 3	SO 2 CF 3	Me	CH 2 CF 2 Ph	H
1-1048	CF 3	SO 2 CF 3	Me	CH 2 CH 2 CH 2 Ph	H
1-1049	CF 3	SO 2 CF 3	Me	1-indanyl	H
1-1050	CF 3	SO 2 CF 3	Me	1-(1,2,3,4-tetrahydro-Np)	H
1-1051	CF 3	SO 2 CF 3	Me	CH 2 (2-Me-2-oxiranyl)	H
1-1052	CF 3	SO 2 CF 3	Me	CH 2 (3-Me-3-oxetanyl)	H
1-1053	CF 3	SO 2 CF 3	Me	CH 2 (2-tetrahydrofuryl)	H
1-1054	CF 3	SO 2 CF 3	Me	CH 2 (2-thienyl)	H
1-1055	CF 3	SO 2 CF 3	Me	CH 2 (3-thienyl)	H
1-1056	CF 3	SO 2 CF 3	Me	CH(Me)(2-thienyl)	H
1-1057	CF 3	SO 2 CF 3	Me	CH(Me)(3-thienyl)	H
1-1058	CF 3	SO 2 CF 3	Me	CH 2 CH 2 OPh	H
1-1059	CF 3	SO 2 CF 3	Me	CH 2 CH 2 OCH 2 Ph	H
1-1060	CF 3	SO 2 CF 3	Me	COMe	H
1-1061	CF 3	SO 2 CF 3	Me	COi-Pr	H
1-1062	CF 3	SO 2 CF 3	Me	Bz	H
1-1063	CF 3	SO 2 CF 3	Me	SO 2 Me	H
1-1064	CF 3	SO 2 CF 3	Me	SO 2 i-Pr	H
1-1065	CF 3	SO 2 CF 3	Me	SO 2 CF 3	H
1-1066	CF 3	SO 2 CF 3	Me	SO 2 (4-MePh)	H
1-1067	CF 3	SO 2 CH 2 CF 3	Me	i-Pr	H
1-1068	CF 3	SO 2 CH 2 CF 3	Me	t-Bu	H
1-1069	CF 3	SO 2 CH 2 CF 3	Me	s-Bu	H
1-1070	CF 3	SO 2 CH 2 CF 3	Me	i-Bu	H
1-1071	CF 3	SO 2 CH 2 CF 3	Me	CH(Me)CH 2 OMe	H
1-1072	CF 3	SO 2 CH 2 CF 3	Me	CH(Me)Ph	H
1-1073	CF 3	SO 2 CH═CH 2	Me	i-Pr	H
1-1074	CF 3	SO 2 CH═CH 2	Me	t-Bu	H
1-1075	CF 3	SO 2 CH═CH 2	Me	s-Bu	H
1-1076	CF 3	SO 2 CH═CH 2	Me	i-Bu	H
1-1077	CF 3	SO 2 CH═CH 2	Me	CH(Me)CH 2 OMe	H
1-1078	CF 3	SO 2 CH═CH 2	Me	CH(Me)Ph	H
1-1079	CF 3	SO 2 CH 2 CH═CH 2	Me	i-Pr	H
1-1080	CF 3	SO 2 CH 2 CH═CH 2	Me	t-Bu	H
1-1081	CF 3	SO 2 CH 2 CH═CH 2	Me	s-Bu	H
1-1082	CF 3	SO 2 CH 2 CH═CH 2	Me	i-Bu	H
1-1083	CF 3	SO 2 CH 2 CH═CH 2	Me	CH(Me)CH 2 OMe	H
1-1084	CF 3	SO 2 CH 2 CH═CH 2	Me	CH(Me)Ph	H
1-1085	CF 3	SO 2 CH 2 C≡CH	Me	i-Pr	H
1-1086	CF 3	SO 2 CH 2 C≡CH	Me	t-Bu	H
1-1087	CF 3	SO 2 CH 2 C≡CH	Me	s-Bu	H
1-1088	CF 3	SO 2 CH 2 C≡CH	Me	i-Bu	H
1-1089	CF 3	SO 2 CH 2 C≡CH	Me	CH(Me)CH 2 OMe	H
1-1090	CF 3	SO 2 CH 2 C≡CH	Me	CH(Me)Ph	H
1-1091	CF 3	SO 2 c-Pr	Me	i-Pr	H
1-1092	CF 3	SO 2 c-Pr	Me	t-Bu	H
1-1093	CF 3	SO 2 c-Pr	Me	s-Bu	H
1-1094	CF 3	SO 2 c-Pr	Me	i-Bu	H
1-1095	CF 3	SO 2 c-Pr	Me	CH(Me)CH 2 OMe	H
1-1096	CF 3	SO 2 c-Pr	Me	CH(Me)Ph	H
1-1097	CF 3	SO 2 c-Hex	Me	i-Pr	H
1-1098	CF 3	SO 2 c-Hex	Me	t-Bu	H
1-1099	CF 3	SO 2 c-Hex	Me	s-Bu	H
1-1100	CF 3	SO 2 c-Hex	Me	i-Bu	H
1-1101	CF 3	SO 2 c-Hex	Me	CH(Me)CH 2 OMe	H
1-1102	CF 3	SO 2 c-Hex	Me	CH(Me)Ph	H
1-1103	CF 3	SO 2 CH 2 c-Pr	Me	i-Pr	H
1-1104	CF 3	SO 2 CH 2 c-Pr	Me	t-Bu	H
1-1105	CF 3	SO 2 CH 2 c-Pr	Me	s-Bu	H
1-1106	CF 3	SO 2 CH 2 c-Pr	Me	i-Bu	H
1-1107	CF 3	SO 2 CH 2 c-Pr	Me	CH(Me)CH 2 OMe	H
1-1108	CF 3	SO 2 CH 2 c-Pr	Me	CH(Me)Ph	H
1-1109	CF 3	SO 2 CH 2 CH 2 OMe	Me	i-Pr	H
1-1110	CF 3	SO 2 CH 2 CH 2 OMe	Me	t-Bu	H
1-1111	CF 3	SO 2 CH 2 CH 2 OMe	Me	s-Bu	H
1-1112	CF 3	SO 2 CH 2 CH 2 OMe	Me	i-Bu	H
1-1113	CF 3	SO 2 CH 2 CH 2 OMe	Me	CH(Me)CH 2 OMe	H
1-1114	CF 3	SO 2 CH 2 CH 2 OMe	Me	CH(Me)Ph	H
1-1115	CF 3	SO 2 Ph	Me	i-Pr	H
1-1116	CF 3	SO 2 Ph	Me	t-Bu	H
1-1117	CF 3	SO 2 Ph	Me	s-Bu	H
1-1118	CF 3	SO 2 Ph	Me	i-Bu	H
1-1119	CF 3	SO 2 Ph	Me	CH(Me)CH 2 OMe	H
1-1120	CF 3	SO 2 Ph	Me	CH(Me)Ph	H
1-1121	CF 3	SO 2 (4-ClPh)	Me	i-Pr	H
1-1122	CF 3	SO 2 (4-ClPh)	Me	t-Bu	H
1-1123	CF 3	SO 2 (4-ClPh)	Me	s-Bu	H
1-1124	CF 3	SO 2 (4-ClPh)	Me	i-Bu	H
1-1125	CF 3	SO 2 (4-ClPh)	Me	CH(Me)CH 2 OMe	H
1-1126	CF 3	SO 2 (4-ClPh)	Me	CH(Me)Ph	H
1-1127	CF 3	SO 2 (4-MePh)	Me	i-Pr	H
1-1128	CF 3	SO 2 (4-MePh)	Me	t-Bu	H
1-1129	CF 3	SO 2 (4-MePh)	Me	s-Bu	H
1-1130	CF 3	SO 2 (4-MePh)	Me	i-Bu	H
1-1131	CF 3	SO 2 (4-MePh)	Me	CH(Me)CH 2 OMe	H
1-1132	CF 3	SO 2 (4-MePh)	Me	CH(Me)Ph	H
1-1133	CF 3	SO 2 CH 2 Ph	Me	i-Pr	H
1-1134	CF 3	SO 2 CH 2 Ph	Me	t-Bu	H
1-1135	CF 3	SO 2 CH 2 Ph	Me	s-Bu	H
1-1136	CF 3	SO 2 CH 2 Ph	Me	i-Bu	H
1-1137	CF 3	SO 2 CH 2 Ph	Me	CH(Me)CH 2 OMe	H
1-1138	CF 3	SO 2 CH 2 Ph	Me	CH(Me)Ph	H
1-1139	CF 3	SO 2 CH 2 (4-ClPh)	Me	i-Pr	H
1-1140	CF 3	SO 2 CH 2 (4-ClPh)	Me	t-Bu	H
1-1141	CF 3	SO 2 CH 2 (4-ClPh)	Me	s-Bu	H
1-1142	CF 3	SO 2 CH 2 (4-ClPh)	Me	i-Bu	H
1-1143	CF 3	SO 2 CH 2 (4-ClPh)	Me	CH(Me)CH 2 OMe	H
1-1144	CF 3	SO 2 CH 2 (4-ClPh)	Me	CH(Me)Ph	H
1-1145	CF 3	SO 2 CH 2 (4-MePh)	Me	i-Pr	H
1-1146	CF 3	SO 2 CH 2 (4-MePh)	Me	t-Bu	H
1-1147	CF 3	SO 2 CH 2 (4-MePh)	Me	s-Bu	H
1-1148	CF 3	SO 2 CH 2 (4-MePh)	Me	i-Bu	H
1-1149	CF 3	SO 2 CH 2 (4-MePh)	Me	CH(Me)CH 2 OMe	H
1-1150	CF 3	SO 2 CH 2 (4-MePh)	Me	CH(Me)Ph	H
1-1151	CF 3	SO 2 NHMe	Me	i-Pr	H
1-1152	CF 3	SO 2 NHMe	Me	t-Bu	H
1-1153	CF 3	SO 2 NHMe	Me	s-Bu	H
1-1154	CF 3	SO 2 NHMe	Me	i-Bu	H
1-1155	CF 3	SO 2 NHMe	Me	CH(Me)CH 2 OMe	H
1-1156	CF 3	SO 2 NHMe	Me	CH(Me)Ph	H
1-1157	CF 3	SO 2 NMe 2	Me	i-Pr	H
1-1158	CF 3	SO 2 NMe 2	Me	t-Bu	H
1-1159	CF 3	SO 2 NMe 2	Me	s-Bu	H
1-1160	CF 3	SO 2 NMe 2	Me	i-Bu	H
1-1161	CF 3	SO 2 NMe 2	Me	CH(Me)CH 2 OMe	H
1-1162	CF 3	SO 2 NMe 2	Me	CH(Me)Ph	H

TABLE 2 — Property

No.	(mp.° C.)	Form	1 HNMR spectrum σ ppm:
1-2		amorphous	9.65 (1H, brs), 7.57 (1H, d, J = 7.8 Hz), around7.24 (1H, m), 7.17-7.16 (2H, m), 4.58
			(2H, s), 3.77 (1H, m), 3.66 (2H, s), 2.28 (3H, s), 1.84-1.77 (1H, m), 1.65-1.58 (1H,
			m), 1.19 (3H, d, J = 6.6 Hz), 0.90 (3H, t, J = 7.3 Hz)
1-3		gum
1-4		amorphous
1-5		amorphous
1-6		amorphous
1-7		gum
1-17		gum	9.20 (1H, brs), 7.35 (1H, d, J = 7.8 Hz), 7.23 (1H, t, J = 7.8 Hz), 7.17 (1H, d, J = 7.8 Hz),
			7.07 (1H, t, J = 7.8 Hz), 6.12 (1H, t, J = 55.2 Hz 9, 3.82-3.76 (1H, m), 3.63 (1H, dd,
			J = 15.1, 3.2 Hz), 3.90 (1H, d, J = 15.1 Hz), 1.85-1.75 (1H, m), 1.67-1.56 (1H, m),
			1.20 (3H, dd, J = 6.4, 1.0 Hz), 0.90 (3H, td, J = 7.3, 2.3 Hz)
1-19		amorphous
1-20		amorphous
1-28		oil	10.7 (1H, br.s), 7.46 (1H, dd, J = 8.7, 5.0 Hz), 6.96 (1H, td, J = 8.4, 2.9 Hz), 6.84 (1H,
			dd, J = 8.5, 3.0 Hz), 3.54 (2H, s), 3.45 (2H, d, J = 6.9 Hz), 2.32 (3H, s), 2.20-2.12 (1H,
			m), 0.94 (6H, d, J = 6.9 Hz).
1-29		oil
1-31		oil
1-32	65.1	solid
1-33	125	solid
1-37		gum	10.70 (1H, brs), 7.50 (1H, d, J = 2.0 Hz), 7.16 (1H, dd, J = 8.4, 2.0 Hz), 7.05 (1H, d,
			J = 8.4 Hz), 4.15-4.04 (1H, m), 3.31 (2H, s), 2.29 (3H, s), 1.25 (6H, d, J = 6.4 Hz).
1-41		gum	10.87 (1H, brs), 7.42 (1H, d, J = 8.8 Hz), 7.22 (1H, dd, J = 8.8, 2.4 Hz), 7.10 (1H, d,
			J = 2.4 Hz), 4.14-4.06 (1H, m), 3.51 (2H, s), 2.31 (3H, s), 1.27 (6H, d, J = 6.8 Hz).
1-46		gum	11.10 (1H, brs), 7.43 (1H, dd, J = 7.6, 1.2 Hz), 7.30 (1H, dd, J = 7.6, 1.2 Hz), 7.21
			(1H, dd, J = 7.6, 7.6 Hz), 4.11 (1H, quint, J = 6.4 Hz), 3.71 (2H, s), 2.38 (3H, s), 1.26
			(6H, d, J = 6.4 Hz).
1-47		gum
1-63		gum	10.91 (1H, brs), 7.48 (1H, d, J = 8.4 Hz), 7.28-7.22 (1H, m), 7.22-7.16 (1H, m), 7.14
			(1H, dd, J = 7.2, 1.2 Hz), 4.07 (1H, quint, J = 6.8 Hz), 3.56 (2H, s), 2.67 (2H, q,
			J = 8.0 Hz), 1.32-1.23 (9H, m).
1-68		gum	10.93 (1H, brs), 7.48 (1H, dd, J = 7.6, 1.2 Hz), 7.28-7.22 (1H, m), 7.21-7.14 (2H, m),
			4.16 (1H, quint, J = 6.4 Hz), 3.61 (2H, s), 3.27 (1H, quint, J = 7.2 Hz), 1.40 (6H, d,
			J = 7.2 Hz), 1.27 (6H, d, J = 6.4 Hz).
1-69		gum
1-78		gum
1-81		oil	9.92 (1H, br.s), 7.51 (1H, dd, J = 7.8, 1.4 Hz), 7.33-7.23 (3H, m), 3.79 (2H, s), 3.50
			(2H, d, J = 7.3 Hz), 2.26-2.14 (1H, m), 2.17 (3H, s), 0.97 (6H, d, J = 6.9 Hz).
1-83		gum	10.79 (1H, brs), 7.52-7.48 (1H, m), 7.28-7.19 (3H, m), 4.44 (1H, quint, 6.4 Hz),
			3.67 (2H, s), 1.68 (2H, m), 1.25 (6H, d, J = 6.4 Hz), 0.96-0.92 (2H, m)
1-84	105	solid
1-96	135-137	solid	10.60 (2H, brs), 7.48 (1H, dd, J = 8.4, 1.6 Hz), 7.29-7.24 (1H, m), 7.21 (1H, ddd,
			J = 7.4, 7.4, 1.6 Hz), 7.17 (1H, dd, J = 8.4, 2.4 Hz), 3.56 (2H, s), 2.36 (3H, s).
1-97		oil
1-98		gum
1-100		gum
1-101		oil	10.9 (1H, br.s), 7.50-7.47 (1H, m), 7.27-7.23 (1H, m), 7.22-7.18 (1H, m), 7.16-7.14
			(1H, m), 3.56 (2H, s), 2.43 (3H, s), 1.42 (9H, s).
1-102		oil	7.50-7.48 (1H, d, J = 7.8 Hz), 7.28-7.15 (3H, m), 3.82 (1H, m), 3.57 (2H, s), 2.32
			(3H, s), 1.85-1.74 (1H, m), 1.67-1.56 (1H, m), 1.20 (3H, d, J = 6.9 Hz), 0.89 (3H, t,
			J = 7.3 Hz)
1-103		oil
1-105		oil	10.9 (1H, br.s), 7.50 (1H, d, J = 8.2 Hz), 7.28-7.24 (1H, m), 7.21 (1H, td, J = 7.3,
			1.4 Hz), , 7.15 (1H, dd, J = 7.8, 1.8 Hz), 3.56 (2H, s), 3.43 (2H, d, J = 6.9 Hz), 2.31
			(3H, s), 2.21-2.10 (1H, m), 0.94 (6H, d, J = 6.9 Hz).
1-106	146-148	solid
1-109		gum
1-110		oil
1-112		oil
1-113		gum
1-115	68.1-72.4	solid
1-116		gum
1-120		oil
1-124	68	solid
1-130		oil
1-133		oil
1-134		oil	10.0 (1H, br.s), 7.50 (1H, d, J = 7.8 Hz), 7.31-7.27 (1H, m), 7.26-7.22 (1H, m), 7.16-
			7.14 (1H, m), 4.20 (2H, d, J = 7.8 Hz), 3.61 (2H, s), 2.38 (3H, s).
1-135		oil	7.50-7.48 (1H, d, J = 6.9 Hz), 7.29-7.14 (3H, s), 5.77-5.70 (1H, m), 5.30-5.25 (2H,
			m), 4.24 (1H, brd, J = 6.0 Hz), 3.60 (2H, s), 2.17 (3H, s)
1-136		oil
1-137		oil
1-138		oil	10.2 (1H, br.s), 7.49 (1H, dd, J = 7.8, 1.4 Hz), 7.28 (1H, td, J = 7.3, 1.8 Hz), 7.23 (1H,
			td, J = 7.4, 1.5 Hz), 7.17 (1H, dd, J = 7.6, 1.6 Hz), 4.36 (2H, d, J = 2.3 Hz), 3.62 (2H, s),
			2.34 (3H, s), 2.25 (1H, d, J = 2.3 Hz).
1-142		oil	10.8 (1H, br.s), 7.49 (1H, dd, J = 7.8, 0.9 Hz), 7.28-7.13 (3H, m), 3.77-3.64 (1H, m),
			3.56 (2H, s), 2.36 (3H, s), 1.88-1.84 (2H, m), 1.74-1.64 (4H, m), 1.29-1.24 (2H,
			m).
1-143		oil	10.8 (1H, br.s), 7.50 (1H, d, J = 7.8 Hz), 7.27 (1H, td, J = 7.3, 1.4 Hz), 7.21 (1H, td,
			J = 7.3, 1.4 Hz), 7.16 (1H, dd, J = 7.6, 1.6 Hz), 3.58 (2H, s), 3.52 (2H, d, J = 6.9 Hz),
			2.33 (3H, s), 1.05-0.95 (1H, m), 0.65-0.53 (2H, m), 0.34-0.23 (2H, m).
1-144		oil
1-145		oil
1-146		gum
1-148	109.0-112.5	solid	10.72 (1H, brs), 7.47 (1H, dd, J = 7.6, 1.2 Hz), 7.26-7.21 (1H, m), 7.19 (1H, ddd,
			J = 7.6, 7.6, 1.6 Hz), 7.16-7.13 (1H, m), 3.82 (2H, dd, J = 4.8, 4.8 Hz), 3.55 (2H, s),
			3.48 (2H, dd, J = 4.8, 4.8 Hz), 3.15 (3H, s), 2.32 (3H, s).
1-149	107-109	solid	10.8 (1H, br.s), 7.48-7.46 (1H, m), 7.26-7.15 (3H, m), 4.17-4.08 (1H, m), 3.56 (2H,
			s), 3.43-3.32 (2H, m), 3.11 (3H, s), 2.33 (3H, s), 1.28-1.26 (3H, m).
1-155		oil	10.58 (1H, brs), 7.48-7.41 (1H, m), 7.37-7.31 (3H, m), 3.85 (2H, d, J = 4.8 Hz), 3.71
			(2H, s), 3.59 (2H, dd, J = 4.0, 4.0 Hz), 3.53-3.44 (1H, m), 2.02 (3H, s), 1.04 (6H, d,
			J = 6.0 Hz).
1-156		oil	7.51-7.40 (1H, m), 7.37-7.31 (1H, m), 7.27-7.21 (1H, m), 7.19-7.11 (1H, m), 3.89-
			3.85 (2H, m), 3.71 (1H, s), 3.60 (1H, dd, J = 4.0, 4.0 Hz), 3.54 (1H, s), 3.49 (1H, dd,
			J = 4.0, 4.0 Hz), 3.12 (1H, d, J = 6.8 Hz), 3.00 (1H, d, J = 6.8 Hz), 2.15 (3H, s), 1.64-
			1.54 (1H, m), 0.81 (3H, d, J = 6.8 Hz), 0.72 (3H, d, J = 6.8 Hz).
1-162		oil	10.6 (1H, br.s), 7.49 (1H, dd, J = 8.0, 1.1 Hz), 7.27 (1H, dd, J = 7.3, 1.8 Hz), 7.21 (1H,
			td, J = 7.6, 1.5 Hz), 7.16 (1H, dd, J = 7.8, 1.8 Hz), 3.83 (2H, t, J = 6.6 Hz), 3.58 (2H, s),
			2.75 (2H, t, J = 6.6 Hz), 2.37 (3H, s), 2.05 (3H, s).
1-166		oil
1-167		oil
1-174		oil	10.6 (1H, br.s), 7.54-7.41 (4H, m), 7.32-7.19 (5H, m), 3.67 (2H, s), 2.32 (3H, s).
1-175		oil
1-176		oil
1-177		amorphous
1-180		gum
1-181		oil
1-182		gum
1-183		gum
1-186		gum	10.4 (1H, br.s), 7.48 (1H, dd, J = 8.0, 1.1 Hz), 7.31 (2H, dt, J = 8.7, 2.2 Hz), 7.27-7.25
			(1H, m), 7.21 (1H, td, J = 7.3, 1.4 Hz), 7.16 (2H, dt, J = 8.7, 2.2 Hz), 7.10 (3H, dd,
			J = 7.6, 1.6 Hz), 4.73 (2H, s), 3.54 (2H, s), 2.35 (3H, s).
1-187	110-115	solid
1-189		oil
1-191	88-89	solid	10.58 (1H, brs), 7.46 (1H, dd, J = 8.0, 1.2 Hz), 7.27-7.22 (1H, m), 7.18 (1H, ddd,
			J = 7.6, 7.6, 1.2 Hz), 7.13-7.06 (5H, m), 4.74 (2H, s), 3.51 (2H, s), 2.33 (3H, s), 2.31
			(3H, s).
1-192		gum
1-193		gum
1-194		gum	10.28 (1H, brs), 7.57 (2H, d, J = 8.4 Hz), 7.45 (1H, dd, J = 8.4, 1.6 Hz), 7.33 (2H, d,
			J = 8.4 Hz), 7.27-7.22 (1H, m), 7.19 (1H, ddd, J = 7.6, 7.6, 1.6 Hz), 7.10 (1H, dd,
			J = 7.6, 1.6 Hz), 4.79 (2H, s), 3.53 (2H, s), 2.35 (3H, s).
1-195		oil	10.57 (1H, brs), 7.46 (1H, dd, J = 8.0, 1.2 Hz), 7.26-7.22 (1H, m), 7.18 (1H, ddd,
			J = 8.0, 8.0, 1.2 Hz), 7.12 (2H, d, J = 8.8 Hz), 7.09 (1H, dd, J = 1.6, 7.6 Hz), 6.83 (2H, d,
			J = 8.8 Hz), 4.71 (2H, s), 3.78 (3H, s), 3.51 (2H, s), 2.32 (3H, s).
1-198		gum	10.28 (1H, brs), 7.61 (2H, d, J = 8.0 Hz), 7.47 (1H, dd, J = 7.6, 0.8 Hz), 7.29-7.23 (3H,
			m), 7.19 (1H, ddd, J = 7.2, 7.2, 1.2 Hz), 7.10 (1H, dd, J = 7.2, 1.2 Hz), 4.77 (2H, s),
			3.55 (2H, s), 2.36 (3H, s).
1-199		oil
1-200		gum
1-201		gum
1-202		oil
1-203		gum	10.6 (1H, br.s), 7.47-7.44 (1H, m), 7.34-7.29 (3H, m), 7.26-7.21 (3H, m), 7.18-7.14
			(1H, m), 7.07-7.05 (1H, m), 5.03 (1H, q, J = 7.0 Hz), 3.50 (2H, q, J = 14.7 Hz), 2.28
			(3H, s), 1.70 (3H, d, J = 6.9 Hz).
1-204		oil	10.52 (1H, brs), 7.46 (1H, dd, J = 7.6, 0.8 Hz), 7.26-7.20 (3H, m), 7.16 (1H, ddd,
			J = 7.2, 7.2, 1.2 Hz), 7.04 (1H, dd, J = 7.2, 1.2 Hz), 6.99 (2H, dd, J = 8.8, 8.8 Hz), 4.98
			(1H, dd, J = 6.8, 6.8 Hz), 3.53 (1H, d, J = 15.2 Hz), 3.46 (1H, d, J = 15.2 Hz), 2.29 (3H,
			s), 1.67 (3H, d, J = 6.8 Hz).
1-205		oil
1-206		oil
1-207		oil
1-208		oil
1-209		gum	10.48 (1H, brs), 7.46 (1H, dd, J = 8.0, 0.8 Hz), 7.30-7.26 (2H, m), 7.25-7.21 (1H, m),
			7.18-7.14 (3H, m), 7.05 (1H, dd, J = 7.6, 1.6 Hz), 5.01 (1H, q, J = 6.8 Hz), 3.53 (1H, d,
			J = 15.2 Hz), 3.47 (1H, d, J = 15.2 Hz), 2.29 (3H, s), 1.66 (3H, d, J = 6.8 Hz).
1-211		oil	10.40 (1H, brs), 7.44 (1H, dd, J = 8.0, 1.2 Hz), 7.32-7.26 (3H, m), 7.22-7.16 (3H, m),
			7.12 (1H, ddd, J = 7.2, 7.2, 0.8 Hz), 7.02 (1H, dd, J = 8.0, 1.6 Hz), 4.65 (1H, dd,
			J = 8.0, 8.0 Hz), 3.52 (1H, d, J = 15.2 Hz), 3.41 (1H, d, J = 15.2 Hz), 2.31-2.23 (4H, m),
			2.08-1.96 (1H, m), 0.95 (3H, t, J = 7.2 Hz).
1-212		gum
1-213		gum
1-214		gum
1-215		gum
1-216		oil	10.58 (1H, brs), 7.49-7.43 (1H, m), 7.37-7.31 (2H, m), 7.30-7.25 (4H, m), 7.18-
			7.14 (2H, m), 3.88 (2H, dd, J = 6.8, 6.8 Hz), 3.66 (2H, s), 3.01 (2H, dd, J = 6.8,
			6.8 Hz), 2.15 (3H, s).
1-218		gum
1-219		gum
1-220		oil
1-221		gum
1-222		gum	10.61 (1H, brs), 7.51-7.46 (1H, m), 7.29-7.03 (7H, m), 5.45 (1H, dd, J = 8.5, 5.3 Hz),
			3.59 (2H, s), 3.16-3.08 (1H, m), 2.92-2.85 (1H, m), 2.41-2.314 (1H, m), 2.17-2.07
			(1H, m), 2.03 (3H, s)
1-224		gum	10.76 (1H, brs), 7.51-7.48 (1H, m), 7.29-7.06 (7H, m), 5.14 (1H, m), 3.60 (2H, s),
			2.88-2.71 (2H, m), 2.33 (3H, s), 2.02-1.87 (4H, m), 1.81-1.72 (2H, m)
1-229		oil
1-230		oil	10.66 (1H, brs), 7.42 (1H, dd, J = 8.0, 1.2 Hz), 7.27-7.22 (1H, m), 7.20-7.18 (1H, m),
			7.17-7.15 (1H, m), 4.09-4.03 (1H, m), 3.80-3.66 (4H, m), 3.60 (1H, d, J = 15.2 Hz),
			3.53 (1H, d, J = 15.2 Hz), 2.73 (3H, s), 2.06-1.98 (1H, m), 1.91-1.82 (2H, m), 1.61-
			1.54 (1H, m).
1-231		oil
1-232		oil	10.4 (1H, br.s), 7.48-7.46 (1H, m), 7.29-7.27 (1H, m), 7.26-7.16 (3H, m), 7.10-7.08
			(1H, m), 6.94-6.92 (1H, m), 4.79 (2H, s), 3.52 (2H, s), 2.33 (3H, s).
1-235		oil
1-237		oil	10.57 (1H, brs), 7.47 (1H, d, J = 6.9 Hz), 7.27-7.12 (5H, m), 6.95 (1H, t, J = 7.3 Hz),
			6.68 (1H, brd, J = 7.8 Hz), 4.13-4.09 (4H, m), 3.55 (2H, s), 2.24 (3H, s)
1-238		oil	7.49 (1H, d, J = 8.2 Hz), 7.31-7.27 (3H, m), 7.22 (1H, t, J = 8.2 Hz), around7.11 (4H,
			m), 4.34 (2H, s), 3.87 (2H, t, J = 4.8 Hz), 3.57 (2H, t, J = 4.8 Hz), 3.55 (2H, s), 2.30
			(3H, s)
1-242		oil	9.77 (1H, br.s), 7.51 (1H, d, J = 7.8 Hz), 7.31 (1H, td, J = 7.6, 1.8 Hz), 7.28-7.23 (1H,
			m), 7.19 (1H, dd, J = 7.8, 1.8 Hz), 3.64 (2H, s), 3.18-3.15 (1H, m), 2.75 (3H, s), 1.22
			(6H, d, J = 6.9 Hz).
1-248		oil
1-249		oil	9.95 (1H, br.s), 7.50 (1H, dd, J = 8.0, 1.6 Hz), 7.35-7.26 (2H, m), 7.18 (1H, dd,
			J = 7.6, 1.6 Hz), 3.68 (2H, s), 3.22 (3H, s), 2.60 (3H, s).
1-251		oil
1-254		amorphous	9.98 (1H, br.s), 7.61 (2H, d, J = 8.4 Hz), 7.40 (1H, dd, J = 8.0, 1.1 Hz), 7.30-7.28 (1H,
			m), 7.22-7.18 (1H, m), 7.20 (1H, d, J=8.4 Hz), 6.96 (1H, dd, J = 7.6,1.6 Hz), 3.46
			(2H, s), 2.60 (3H, s), 2.35 (3H, s).
1-256		gum
1-260		gum
1-263		oil
1-264		gum	7.34 (1H, dd, J = 7.3, 1.8 Hz), 7.29-7.19 (3H, m), 3.89 (2H, q, J = 7.2 Hz), 3.71 (2H,
			s), 3.47 (2H, d, J = 7.3 Hz), 2.09 (2H, s), 1.90-1.84 (1H, m), 1.46-1.36 (4H, m), 1.23
			(3H, t, J = 7.3 Hz), 0.92 (6H, td, J = 7.3, 1.4 Hz).
1-270		oil	7.36-7.32 (2H, m), 7.28-7.24 (1H, m), 7.21-7.19 (1H, m), 5.20 (1H, d, J = 10.1 Hz),
			4.97 (1H, d, J = 10.1 Hz), 3.71 (2H, s), 3.44 (3H, s), 3.39 (2H, d, J = 7.3 Hz), 2.22-
			2.16 (1H, m), 2.09 (3H, s), 0.98 (6H, dd, J = 6.9, 1.8 Hz).
1-271		oil
1-278		oil	7.37-7.29 (2H, m), 7.28-7.24 (2H, m), 7.17-7.14 (3H, m), 7.12-7.10 (1H, m), 6.99-
			6.96 (1H, m), 5.06 (1H, d, J = 14.2 Hz), 4.82 (1H, d, J = 14.2 Hz), 3.53 (1H, d,
			J = 16.9 Hz), 3.35 (2H, d, J = 7.3 Hz), 3.08 (1H, d, J = 16.9 Hz), 2.22-2.16 (1H, m), 1.93
			(3H, s), 0.96 (6H, dd, J = 6.9 Hz).
1-279		oil
1-293		oil
1-294	92-94	solid	7.45 (1H, t, J = 7.8 Hz), 7.36 (1H, t, J = 7.8 Hz), 7.32 (1H, d, _J = 7.8 Hz), 7.21 (1H, d,
			J = 7.8 Hz), 3.81 (1H, m), 3.69 (1H, d, J = 18.8 Hz), 3.60 (1H, d, J = 18.8 Hz), 2.16 (3H,
			s), 1.92-1.82 (1H, m), 1.72-1.60 (1H, m), 1.28-1.21 (3H, m), 0.98 (3H, dt, J = 9.6,
			7.3 Hz)
1-295		oil
1-297		oil	7.46-7.42 (1H, m), 7.37-7.33 (2H, m), 7.20 (1H, d, J = 8.2 Hz), 3.63 (2H, dd, J = 41.2,
			16.9 Hz), 3.41 (2H, d, J = 7.3 Hz), 2.28-2.17 (1H, m), 2.15 (3H, s), 2.14 (3H, s), 0.99
			(6H, dd, J = 6.6, 3.4 Hz).
1-298		oil
1-299		oil
1-300		oil
1-304		oil	7.46-7.40 (1H, m), 7.37-7.32 (1H, m), 7.31-7.28 (1H, m), 7.22-7.20 (1H, m), 4.20-
			4.09 (1H, m), 3.70-3.54 (3H, m), 3.39-3.36 (1H, m), 3.32 (3H, d, J = 19.7 Hz), 2.18-
			2.16 (6H, m), 1.34-1.32 (3H, m).
1-305		gum
1-306		oil
1-307		oil
1-308		oil
1-310		gum
1-315
1-316		oil
1-318		oil
1-319	122-124	solid	7.39 (1H, ddd, J = 7.2, 7.2, 0.8 Hz), 7.34-7.25 (2H, m), 7.18 (1H, d, J = 7.2 Hz), 4.18-
			4.07 (1H, m), 3.65-3.50 (3H, m), 3.39-3.33 (1H, m), 3.32 (1.5H, s), 3.27 (1.5H, s),
			2.50-2.30 (1H, m), 2.27-2.18 (1H, m), 2.16 (1.5H, s), 2.14 (1.5H, s), 1.31 (3H, d,
			J = 6.8 Hz), 1.08 (3H, t, J = 6.8 Hz).
1-320		gum
1-321		oil
1-329
1-330		oil
1-331		oil
1-333		oil
1-334		oil
1-335		oil	7.43-7.37 (1H, m), 7.35-7.30 (1H, m), 7.29-7.25 (1H, m), 7.23-7.19 (1H, m), 4.18-
			4.07 (1H, m), 3.66-3.53 (3H, m), 3.38-3.34 (1H, m), 3.32 (1.5H, s), 3.27 (1.5H, s),
			2.58-2.45 (1H, m), 2.12 (1.5H, s), 2.10 (1.5H, s), 1.33-1.27 (3H, m), 1.22-1.16 (3H,
			m), 1.08-1.03 (3H, m).
1-336		gum
1-337		oil
1-351	97-98	solid	7.43 (1H, ddd, J = 7.6, 7.6, 1.2 Hz), 7.34 (1H, ddd, J = 7.6, 7.6, 1.6 Hz), 7.21 (1H, d,
			J = 7.6 Hz), 7.17 (1H, d, J = 7.6 Hz), 3.64 (1H, d, J = 17.6 Hz), 3.55 (1H, d, J = 17.6 Hz),
			2.31-2.24 (1H, m), 2.23 (3H, s), 2.22-2.02 (2H, m), 1.45 (9H, s), 0.91 (3H, d,
			J = 6.4 Hz), 0.87 (3H, d, J = 6.4 Hz).
1-352	95-97	solid	7.44 (1H, t, J = 7.6 Hz), 7.34 (1H, t, J = 7.6 Hz), 7.28 (1H, dd, J = 8.2, 5.0 Hz), 7.16 (1H,
			d, J = 8.2 Hz), 3.83-3.74 (1H, m), 3.65 (1H, d, J = 16.9 Hz), 3.57 (1H, d, J = 16.9 Hz),
			2.28-2.02 (2H, m), 2.13 (3H, s), 1.92-1.79 (1H, m), 1.70-1.58 (2H, m), 1.29-0.85
			(12H, m)
1-353		oil
1-354		oil	7.47-7.43 (1H, m), 7.37-7.32 (2H, m), 7.18 (1H, d, J=7.8 Hz), 3.62 (2H, q,
			J=16.5 Hz), 3.41 (2H, d, J=7.3 Hz), 2.25-2.04 (4H, m), 2.13 (3H, s), 0.99 (6H, dd,
			J=6.9, 2.7 Hz), 0.90 (6H, dd, J=13.7, 6.4 Hz).
1-355		oil
1-356		oil
1-357	80-82	solid	7.45-7.37 (1H, m), 7.35-7.25 (2H, m), 7.17 (1H, d, J = 8.0 Hz), 4.18-4.07 (1H, m),
			3.67-3.51 (3H, m), 3.40-3.27 (4H, m), 2.34-2.24 (1H, m), 2.21-2.01 (5H, m), 1.32
			(3H, d, J = 10.0 Hz), 0.93-0.90 (3H, m), 0.89-0.86 (3H, m).
1-358		gum
1-359		oil
1-403		oil
1-404		oil	7.44 (1H, t, J = 7.3 Hz), 7.39-7.33- (2H, m), around7.24 (1H, m), 3.78 (1H, d,
			J = 16.9 Hz), 3.78 (1H, m), 3.64 (1H, d, J = 16.9 Hz), 2.15 (3H, s), 1.90-1.78 (1H, m),
			1.69-1.58 (2H, m), 1.47-1.36 (1H, m), around1.24 (1H, m), 1.21 (3H, dd, J = 6.9,
			1.4 Hz), 1.11-1.03 (1H, m), 0.95 (3H, dt, J = 7.3, 1.8 Hz)
1-405		oil
1-407		oil
1-408		oil
1-412		oil
1-413		gum
1-414		oil
1-416		oil
1-431		gum
1-432		oil	7.46 (1H, t, J = 7.6 Hz), 7.36-7.29 (2H, m), 7.21 (1H, d, J = 7.6 Hz), 3.79 (1H, m), 3.58
			(2H, s), 2.27-2.16 (1H, m), 2.12 (3H, s), 1.95-1.57 (8H, m), 1.46-1.37 (1H, m),
			1.25 (3H, dd, J = 8.0, 6.6 Hz), around1.18 (2H, m), 0.97 (3H, dt, J = 7.3, 6.4 Hz),
			around0.97 (1H, m)
1-434		gum
1-444		gum	7.48 (1H, t, J = 7.8 Hz), 7.36 (1H, t, J = 7.8 Hz), 7.31 (1H, d, J = 7.8 Hz), 7.22 (1H, d,
			J = 7.8 Hz), 4.12 (1H, dd, J = 16.9, 3.0 Hz), 3.81 (1H, m), 3.69 (1H, d, J = 17.9 Hz),
			3.57 (1H, d, J = 17.9 Hz), 3.40 (2H, s), 2.23 (3H, s), 1.92-1.81 (1H, m), 1.70-1.59
			(1H, m), 1.24 (3H, dd, J = 18.5, 6.6 Hz), 0.98 (3H, dt, J = 11.0, 7.3 hz)
1-472		gum
1-473		gum
1-474		oil	7.59 (2H, d, J = 7.3 Hz), 7.45 (1H, t, J = 7.8 Hz), 7.38 (1H, t, J = 7.8 Hz), 7.38 (1H, t,
			J = 7.6 Hz), around7.28 (3H, m), 7.19 (1H, d, J = 7.9 Hz), 7.12 (1H, t, J = 7.6 Hz), 7.02
			(1H, d, J = 7.8 Hz), 3.92-3.79 (3H, m), 2.12 (3H, s), 1.90-1.80 (1H, m), 1.67-1.64
			(1H, m), around1.22 (3H, m), 0.96 (3H, dt, J = 16.9, 7.3 Hz)
1-479		gum	7.46-7.38 (1H, m), 7.35-7.25 (3H, m), 7.24-7.15 (2H, m), 7.14-7.00 (3H, m), 4.19-
			4.08 (1H, m), 3.87-3.77 (1H, m), 3.74-3.51 (2H, m), 3.40-3.26 (4H, m), 2.18 (3H,
			d, J = 7.2 Hz), 1.33 (3H, d, J = 8.0 Hz).
1-484		amorphous
1-494		oil
1-503		gum
1-504		gum	7.44 (1H, t, J = 7.6 Hz), 7.32-7.21 (5H, m), 7.04 (2H, m), 3.82-3.54 (5H, m), 2.16
			(3H, s), 1.89-1.81 (1H, m), 1.70-1.63 (1H, m), 1.22 (3H, d, J = 6.9 Hz), 0.97 (3H, dt,
			J = 9.2, 7.3 Hz)
1-506		gum
1-522		gum	7.50 (1H, d, J = 7.8 Hz), around7.24 (1H, m), 7.21 (1H, t, J = 7.8 Hz), 7.15 (1H, d,
			J = 7.8 Hz), 4.01-3.94 (1H, m), 3.84-3.74 (2H, m), 3.57 (2H, s), 2.32 (3H, s), 1.91-
			1.75 (3H, m), 1.68-1.59 (2H, m), 1.20 (3H, d, J = 6.4 Hz), 0.90 (3H, t, J = 7.3 Hz)
1-528		gum	8.45 (1H, t, J = 5.7 Hz), 7.89 (1H, d, J = 7.8 Hz), around7.24 (4H, m), 7.06 (1H, t,
			J = 6.9 Hz), 7.01 (1H, t, J = 6.9 Hz), 7.01 (1H, t, J = 6.9 Hz), 4.30 (1H, dd, J = 17.4,
			6.0 Hz), 3.88 (1H, d, J = 17.4 Hz), 3.78 (1H, m)2.12 (3H, s), 1.87 (1H, m), 1.66 (1H,
			m), 1.23 (3H, dd, J = 15.3, 6.6 Hz), 0.97 (3H, dt, J = 13.6, 5.4 Hz)
1-575		gum
1-576		oil	7.41-7.38 (1H, m), 7.33-7.28 (1H, m), 7.26-7.24 (1H, m), 7.19-7.14 (1H, m), 3.87
			(3H, s), 3.57 (2H, s), 2.14 (3H, s), 1.44 (9H, s).
1-577	75-80	solid	7.43-7.39 (1H, m), 7.33-7.28 (2H, m), 7.18 (1H, d, J = 7.8 Hz), 3.87 (3H, d,
			J = 4.1 Hz), 3.79-3.73 (1H, m), 3.63 (2H, d, J = 1.8 Hz), 2.04 (3H, s), 1.90-1.81 (1H,
			m), 1.69-1.59 (1H, m), 1.22 (3H, d, J = 6.4 Hz), 0.96 (3H, td, J = 7.4, 2.0 Hz).
1-580		gum
1-583		oil
1-587	98-100	solid	7.41-7.36 (1H, m), 7.31-7.26 (2H, m), 7.20-7.16 (1H, m), 4.14-4.05 (1H, m), 3.88
			(3H, d, J = 3.2 Hz), 3.62-3.56 (3H, m), 3.40-3.34 (1H, m), 3.30 (3H, d, J = 5.0 Hz),
			2.06 (3H, d, J = 7.8 Hz), 1.31 (3H, dd, J = 7.8, 6.9 Hz).
1-592		oil
1-594		oil
1-597		gum
1-598		oil
1-604	98-100	solid	7.41-7.37 (1H, m), 7.32-7.27 (2H, m), 7.26-7.24 (1H, m), 7.18 (1H, d, J = 7.6 Hz),
			4.40-4.28 (2H, m), 3.63 (2H, s), 2.13 (3H, s), 1.44 (9H, s), 1.30 (3H, t, J = 7.6 Hz).
1-605	73-75	solid	7.42-7.38 (1H, m), 7.33-7.28 (2H, m), 7.18 (1H, d, J = 7.3 Hz), 4.36-4.27 (2H, m),
			3.78-3.63 (1H, m), 3.63 (2H, s), 2.03 (3H, d, J = 3.7 Hz), 1.90-1.82 (1H, m), 1.68-
			1.59 (1H, m), 1.35-1.26 (3H, m), 1.23-1.16 (3H, m), 0.96 (3H, t, J = 7.3 Hz).
1-608	88	solid
1-609		oil
1-611		oil
1-615	84-88	solid	7.39-7.35 (1H, m), 7.31-7.26 (2H, m), 7.18-7.16 (1H, m), 4.37-4.30 (2H, m), 4.14-
			4.07 (1H, m), 3.63-3.57 (3H, m), 3.41-3.35 (1H, m), 3.30 (3H, d, J = 5.0 Hz), 2.03
			(3H, d, J = 6.4 Hz), 1.32-1.24 (6H, m).
1-620		oil
1-622		oil
1-623		oil
1-626		oil	7.38-7.27 (5H, m), 7.26-7.22 (1H, m), 7.21-7.08 (2H, m), 6.93-6.88 (0.5H, m),
			6.55-6.50 (0.5H, m), 4.94 (1H, quint, J = 7.6 Hz), 4.35-4.23 (2H, m), 3.52 (2H, d,
			J = 5.6 Hz), 1.99 (1, 5H, s), 1.98 (1, 5H, s), 1.78 (1, 5H, d, J = 7.6 Hz), 1.75 (1, 5H, d,
			J = 7.6 Hz), 1.26 (3H, t, J = 6.8 Hz).
1-631	104-106	solid
1-632	84-86	solid
1-634		oil
1-641	144-146	solid
1-642	108-110	solid	7.41-7.37 (1H, m), 7.32-7.27 (2H, m), 7.17 (1H, d, J = 7.3 Hz), 5.13-5.06 (1H, m),
			3.78-3.73 (1H, m), 3.63 (2H, s), 2.01 (3H, d, J = 3.7 Hz), 1.90-1.82 (1H, m), 1.68-
			1.60 (1H, m), 1.34-1.27 (6H, m), 1.22 (3H, d, J = 6.4 Hz), 0.96 (3H, t, J = 7.3 Hz).
1-647		oil	7.39-7.35 (1H, m), 7.30-7.26 (2H, m), 7.18-7.14 (1H, m), 5.13-5.06 (1H, m), 4.13-
			4.04 (1H, m), 3.64-3.57 (3H, m), 3.39-3.33 (1H, m), 3.30 (3H, d, J = 4.6 Hz), 2.03
			(3H, d, J = 6.4 Hz), 1.34-1.28 (9H, m).
1-652		oil
1-653		oil
1-666		oil
1-667		amorphous
1-668		gum
1-669	78-80	solid	7.42-7.38 (1H, m), 7.34-7.28 (2H, m), 7.18 (1H, d, J = 7.8 Hz), 4.14-4.08 (1H, m),
			4.02-3.95 (1H, m), 3.78-3.72 (1H, m), 3.64 (2H, s), 2.03 (3H, d, J = 4.1 Hz), 1.97-
			1.82 (2H, m), 1.67-1.52 (1H, m), 1.24-1.20 (3H, m), 0.97-0.93 (3H, m), 0.86-0.82
			(6H, m).
1-671		gum
1-674		amorphous
1-675		oil	7.40-7.35 (1H, m), 7.31-7.27 (2H, m), 7.19-7.17 (1H, m), 4.14-4.06 (2H, m), 4.03-
			3.97 (1H, m), 3.64-3.56 (3H, m), 3.39-3.34 (1H, m), 3.30 (3H, d, J = 3.7 Hz), 2.04
			(3H, d, J = 6.4 Hz), 1.96-1.89 (1H, m), 1.31 (3H, t, J = 6.9 Hz), 0.85 (6H, dd, J = 12.4,
			6.4 Hz).
1-676		oil
1-677		amorphous
1-678		oil
1-679		oil
1-706		oil	7.42-7.38 (1H, m), 7.33-7.28 (2H, m), 7.19 (1H, d, J = 7.8 Hz), 5.91-5.80 (1H, m),
			5.30-5.24 (2H, m), 4.79-4.67 (2H, m), 3.79-3.72 (1H, m), 3.63 (2H, s), 2.02 (3H, d,
			J = 4.1 Hz), 1.89-1.81 (1H, m), 1.69-1.59 (1H, m), 1.23-1.20 (3H, m), 0.97-0.93 (3H,
			m).
1-707		gum
1-708		oil	7.39-7.33 (1H, m), 7.25-7.20 (2H, m), 7.16 (1H, d, J = 8.0 Hz), 5.91-5.78 (1H, m),
			5.36-5.21 (2H, m), 4.78-4.65 (2H, m), 4.13-4.03 (1H, m), 3.68-3.53 (3H, m), 3.39-
			3.30 (1H, m), 3.28 (1.5H, s), 3.27 (1.5H, s), 2.02 (1.5H, s), 2.00 (1.5H, s), 1.32-
			1.27 (3H, m).
1-709		oil
1-710		oil
1-731		oil	7.41-7.37 (1H, m), 7.32-7.28 (2H, m), 7.19 (1H, d, J = 7.3 Hz), 4.43-4.35 (2H, m),
			3.81-3.73 (1H, m), 3.65-3.64 (2H, m), 3.60-3.52 (2H, m), 3.27 (2H, d, J = 2.7 Hz),
			2.03 (3H, d, J = 2.7 Hz), 1.89-1.80 (1H, m), 1.69-1.59 (1H, m), 1.22 (3H, dd, J = 6.6,
			2.5 Hz), 0.96 (3H, t, J = 7.3 Hz).
1-733		oil
1-735		oil
1-736		oil
1-762		gum
1-763		amorphous	7.45-7.18 (9H, m), 3.75 (3H, m), 2.03 (3H, brs), 1.90-1.78 (1H, m), 1.67-1.57 (1H,
			m), 1.20 (3H, d, J = 6.4 Hz), 0.93 (3H, brdt, J = 7.3 Hz, 1.8 Hz)
1-765	117-121	solid	7.44-7.25 (7H, m), 7.23-7.15 (2H, m), 4.14-4.02 (1H, m), 3.73 (2H, dd, J = 5.6,
			5.6 Hz), 3.62-3.52 (1H, m), 3.35-3.31 (1H, m), 3.28 (1.5H, s), 3.27 (1.5H, s), 2.06
			(1.5H, s), 2.02 (1.5H, s), 1.30 (1.5H, d, J = 2.8 Hz), 1.28 (1.5H, d, J = 2.8 Hz).
1-766		gum
1-781		oil
1-782		oil
(TLC
top)
1-783		oil
(TLC
bottom)
1-785		gum
1-788		oil
(TLC
top)
1-789		oil
(TLC
bottom)
1-790		oil	7.39-7.32 (4H, m), 7.30-7.25 (4H, m), 7.15-7.13 (1H, m), 5.33-5.23 (2H, m), 4.14-
			4.03 (1H, m), 3.69-3.52 (3H, m), 3.38-3.32 (1H, m), 3.29 (3H, d, J = 5.0 Hz), 2.02
			(3H,d, J = 6.4 Hz), 1.31-1.25 (3H, m).
1-791		oil
1-793		oil
1-794		oil
1-796		oil
1-829		oil	7.40 (1H, t, J = 6.9 Hz), 7.35-7.28 (2H, m), 7.20 (1H, d, J = 7.8 Hz), 4.34-4.28 (1H, m),
			4.23-4.01 (2H, m), around3.74 (1H, m), 3.65 (2H, s), 2.04 (3H, m), 2.00-1.46 (8H,
			m), around1.23 (3H, m), 0.96 (3H, t, J = 7.3 Hz)
1-874		oil
1-886		oil
1-888	158-160	solid	7.42 (1H, m), 7.37-7.30 (2H, m), 7.16 (1H · m), 4.06 (1H, m), 3.69 (2H, m), 3.66
			(3H, s), 2.03 (3H, s), around1.25 (6H, m)
1-889		oil
1-890		oil	7.45-7.41 (1H, m), 7.37-7.29 (2H, m), 7.22-7.19 (1H, m), 3.84-3.75 (1H, m), 3.71
			(2H, d, J = 6.4 Hz), 3.63 (3H, s), 2.12 (3H, s), 1.91-1.82 (1H, m), 1.70-1.62 (1H, m),
			1.27-1.22 (3H, m), 1.00-0.95 (3Hm).
1-892		oil
1-893		oil
1-894		oil
1-895		oil
1-899		oil
1-900		oil
1-901		oil
1-903		oil
1-904		oil
1-906		gum
1-907		oil
1-913		oil
1-915		oil	7.49-7.33 (2H, m), 7.32-7.26 (1H, m), 7.22-7.14 (1H, m), 4.19-4.07 (1H, m), 3.89-
			3.76 (1H, m), 3.73-3.62 (3H, m), 3.61-3.53 (1H, m), 3.41-3.32 (1H, m), 3.31-3.28
			(3H, m), 2.17-2.08 (3H, m), 1.60 (3H, t, J = 7.2 Hz), 1.35-1.29 (3H, m).
1-916		oil
1-917		oil
1-960	135-137	solid
1-962	144-146	solid
1-963		amorphous	7.52-7.45 (1H, m), 7.38-7.34 (2H, m), 7.30-7.26 (1H, m), 3.71 (2H, s), 2.11 (3H, s),
			1.46 (9H, s).
1-964		gum	7.52-7.48 (1H, m), 7.36-7.35 (3H, m), 3.79 (1H, m), 3.75 (2H, s), 2.01 (3H, s), 1.89
			(1H, m), 1.67 (1H, m), 1.25 (3H, dJ = 6.9 Hz), 0.97 (3H, t, J = 7.3 Hz)
1-965		oil
1-967	120-122	solid	7.52-7.46 (1H, m), 7.39-7.34 (3H, m), 3.73 (2H, s), 3.43 (2H, d, J = 6.9 Hz), 2.31-
			2.16 (1H, m), 2.00 (3H, s), 0.99 (6H, d, J = 6.9 Hz).
1-968	113-115	solid
1-969		amorphous
1-970		gum
1-971		oil
1-972		amorphous
1-973		gum
1-974		oil
1-975		gum
1-977		oil
1-978		gum
1-980		oil
1-981		oil
1-982	60-62	solid
1-983	93.8-97.0	solid
1-985		oil
1-986		amorphous
1-988	106-112	solid
1-990	134-136	solid
1-991	96-97	solid
1-992		oil
1-993		oil
1-994	105	solid
1-996		amorphous
1-997	116-118	solid	7.48-7.42 (1H, m), 7.35-7.28 (3H, m), 4.15-4.07 (1H, m), 3.72 (2H, d, J = 2.0 Hz),
			3.61 (1H, dd, J = 9.6, 9.6 Hz), 3.37 (1H, dd, J = 9.6, 4.0 Hz), 3.30 (3H, s), 1.99 (3H,
			s), 1.32 (3H, d, J = 7.2 Hz).
1-1000		oil
1-1002		oil
1-1003		oil
1-1005		oil
1-1006		oil
1-1008		oil
1-1009	105-107	solid
1-1010		oil
1-1011		amorphous
1-1012	90-94	solid
1-1013		gum
1-1014		gum
1-1015		gum
1-1016	112-117	solid
1-1017	119.6	solid
1-1018	108	solid
1-1019		gum
1-1020	118	solid
1-1021		gum
1-1022		oil
1-1023		oil
1-1026		oil
1-1027		gum
1-1028		gum
1-1029	124-126	solid
1-1030	107-112	solid
1-1031		oil
1-1032	172-175	solid
1-1033	108.7-113.4	solid
1-1034		oil
1-1036		gum
1-1037		oil
1-1038		gum
1-1039		gum
1-1040		gum
1-1041		gum
1-1042		gum
1-1043		oil
1-1044		oil
1-1045		gum
1-1046		gum
1-1047		amorphous
1-1048		gum
1-1049		gum
1-1050		gum
1-1051		oil
1-1054		oil
1-1055		oil
1-1057		oil
1-1058		oil
1-1059	88-92	solid
1-1061		oil
1-1063	151-153	solid
1-1064		oil
1-1066		oil
1-1093		oil
1-1127		gum	7.80 (2H, d, J = 8.2 Hz), 7.39 (2H, d, J = 8.2 Hz), around7.39 (1H, m), around7.24
			(1H, m), 7.20 (1H, d, J = 7.8 Hz), 7.12 (1H, dJ = 7.8 Hz), 4.02 (1H, m), 3.46 (1H, d,
			J = 17.4 Hz), 3.12 (1H, d, J = 17.4 Hz), 2.49 (3H, s), 2.05 (3H, s), 1.29-1.26 (6H, m)

TABLE 3 — Concen- tration Echinochloa Monochoria Lindernia Scirpus

No.	(g/10a)	crus - galli
vaginalis
pyxidaria
juncoides
1-28	120	100	100	90	90
1-29	120	100	90	90	90
1-31	120	90	80	90	90
1-32	120	80	90	80	90
1-33	120	80	90	90	100
1-37	120	60	40	80	90
1-41	120	100	100	100	100
1-46	120	60	80	80	90
1-47	120	40	70	70	80
1-63	120	90	100	100	100
1-68	120	80	80	90	90
1-69	120	80	70	70	90
1-78	120	40	50	50	70
1-81	120	90	80	80	90
1-83	120	90	70	100	90
1-84	120	80	70	70	80
1-97	120	100	100	100	100
1-98	120	100	100	100	90
1-100	120	90	100	100	90
1-101	120	90	90	90	90
1-102	120	100	100	100	100
1-103	120	100	100	80	90
1-105	120	90	100	100	90
1-106	120	90	90	90	90
1-109	120	100	100	100	100
1-110	120	100	100	100	100
1-112	120	100	90	90	90
1-113	120	100	100	100	100
1-115	120	100	90	90	90
1-116	120	90	80	90	90
1-120	120	100	100	100	100
1-124	120	100	90	90	90
1-130	120	100	100	100	100
1-133	120	80	100	100	100
1-134	120	80	80	60	80
1-135	120	90	60	90	90
1-136	120	100	70	80	90
1-137	120	90	70	90	90
1-138	120	90	100	100	90
1-142	120	100	90	100	90
1-143	120	90	100	100	90
1-144	120	100	100	90	90
1-145	120	100	100	100	100
1-146	120	100	100	100	100
1-148	120	90	90	100	100
1-149	120	90	90	90	90
1-155	120	90	60	60	80
1-156	120	100	80	100	100
1-162	120	100	100	100	100
1-166	120	100	90	90	90
1-167	120	100	80	90	90
1-180	120	90	90	90	90
1-181	120	90	90	100	90
1-182	120	90	90	100	100
1-183	120	100	100	100	100
1-186	120	90	100	100	90
1-187	120	90	90	90	80
1-189	120	90	90	100	90
1-191	120	90	90	100	90
1-192	120	90	100	100	40
1-193	120	90	100	100	90
1-194	120	80	80	100	80
1-195	120	90	60	70	90
1-198	120	80	100	100	80
1-199	120	100	100	100	90
1-200	120	90	100	100	90
1-201	120	90	80	90	100
1-202	120	100	90	100	80
1-203	120	90	100	100	90
1-204	120	100	90	90	90
1-205	120	100	100	100	90
1-206	120	90	100	100	90
1-207	120	100	100	100	90
1-208	120	90	90	80	90
1-209	120	90	60	60	70
1-211	120	90	90	90	90
1-212	120	90	80	90	90
1-213	120	100	90	90	90
1-214	120	100	90	100	90
1-215	120	100	80	100	90
1-216	120	90	100	100	100
1-218	120	100	90	90	90
1-219	120	100	80	90	90
1-220	120	90	100	100	90
1-221	120	90	60	70	80
1-222	120	100	90	90	90
1-224	120	100	100	100	90
1-229	120	70	100	80	90
1-230	120	100	80	100	90
1-231	120	90	90	80	80
1-232	120	90	90	80	90
1-235	120	90	80	60	80
1-237	120	90	80	90	80
1-238	120	100	80	80	80
1-248	120	60	80	90	50
1-251	120	100	100	90	80
1-263	120	50	50	80	60
1-264	120	90	90	80	100
1-293	120	90	90	90	90
1-294	120	90	90	90	90
1-295	120	90	90	90	90
1-297	120	100	100	100	100
1-298	120	90	90	90	90
1-299	120	100	80	100	90
1-300	120	100	70	80	90
1-304	120	90	90	90	90
1-305	120	90	90	90	90
1-310	120	90	90	90	90
1-315	120	90	90	90	90
1-316	120	90	90	90	90
1-318	120	90	90	90	90
1-319	120	90	90	90	90
1-320	120	90	90	90	90
1-321	120	90	90	90	90
1-329	120	90	90	90	90
1-330	120	90	90	90	90
1-331	120	90	90	90	90
1-333	120	90	90	90	90
1-334	120	100	80	70	90
1-335	120	90	90	90	90
1-336	120	90	90	90	90
1-337	120	90	90	90	90
1-351	120	90	90	90	90
1-352	120	90	90	90	90
1-353	120	90	90	90	90
1-354	120	100	90	90	90
1-355	120	90	90	90	90
1-356	120	100	60	90	90
1-357	120	90	90	90	90
1-358	120	90	90	90	90
1-359	120	90	90	90	90
1-403	120	90	90	90	90
1-404	120	90	90	90	90
1-405	120	90	90	90	90
1-407	120	90	90	90	90
1-408	120	100	80	80	90
1-412	120	90	90	90	90
1-413	120	90	90	90	90
1-416	120	90	90	90	90
1-431	120	90	90	90	90
1-432	120	90	90	90	90
1-434	120	90	90	90	90
1-444	120	90	90	90	90
1-472	120	90	60	90	90
1-473	120	90	90	90	90
1-474	120	90	90	90	90
1-479	120	90	90	90	90
1-484	120	90	90	90	90
1-494	120	90	90	90	90
1-503	120	90	90	90	90
1-504	120	90	90	90	90
1-506	120	90	90	90	90
1-522	120	90	90	90	90
1-528	120	90	90	90	90
1-575	120	90	100	100	100
1-576	120	90	90	90	90
1-577	120	90	90	90	90
1-580	120	90	90	90	90
1-583	120	100	90	90	90
1-587	120	90	90	90	90
1-592	120	90	90	90	90
1-597	120	90	100	90	90
1-598	120	90	90	90	90
1-604	120	90	90	90	90
1-605	120	90	90	90	90
1-608	120	70	80	70	90
1-609	120	90	90	90	90
1-611	120	100	80	90	90
1-615	120	90	90	90	90
1-620	120	90	90	90	90
1-626	120	90	90	90	90
1-631	120	90	90	90	90
1-632	120	90	90	90	90
1-634	120	90	90	90	90
1-641	120	90	90	90	90
1-642	120	90	90	90	90
1-647	120	90	90	90	90
1-652	120	90	90	90	90
1-653	120	90	90	90	90
1-666	120	100	100	80	90
1-667	120	90	90	90	90
1-668	120	90	90	90	90
1-669	120	90	90	90	90
1-671	120	90	90	90	90
1-674	120	100	90	90	90
1-675	120	90	90	90	90
1-676	120	90	90	90	90
1-677	120	90	100	100	90
1-678	120	90	90	90	90
1-679	120	60	50	50	50
1-706	120	90	90	90	90
1-707	120	90	90	90	90
1-708	120	90	90	90	90
1-709	120	90	90	90	90
1-710	120	90	90	90	90
1-731	120	90	90	90	90
1-733	120	100	90	90	100
1-735	120	90	90	90	90
1-736	120	90	90	90	90
1-762	120	90	90	90	90
1-763	120	90	90	90	90
1-765	120	90	90	90	90
1-766	120	90	90	90	90
1-781	120	90	90	90	90
1-783	120	90	90	90	90
(TLC
bottom)
1-785	120	90	90	90	90
1-788	120	80	50	60	80
(TLC
top)
1-789	120	100	90	90	90
(TLC
bottom)
1-790	120	90	90	90	90
1-796	120	90	90	90	90
1-829	120	90	90	90	90
1-874	120	90	90	90	90
1-886	120	90	90	90	90
1-888	120	100	90	100	90
1-889	120	90	90	90	90
1-890	120	90	90	90	90
1-892	120	100	90	90	90
1-893	120	90	90	90	90
1-894	120	100	60	80	100
1-895	120	100	80	90	90
1-899	120	90	90	90	90
1-900	120	90	90	90	90
1-906	120	100	100	100	100
1-907	120	90	90	90	90
1-913	120	90	90	90	90
1-915	120	90	90	90	90
1-916	120	90	90	90	90
1-917	120	90	90	90	90
1-960	120	80	70	70	80
1-962	120	100	100	100	90
1-963	120	90	90	90	90
1-964	120	90	100	100	90
1-965	120	100	100	80	80
1-967	120	90	100	90	90
1-968	120	90	90	90	90
1-969	120	100	80	100	90
1-970	120	100	100	100	100
1-971	120	100	100	100	100
1-972	120	100	100	100	100
1-973	120	100	80	100	100
1-974	120	100	80	90	90
1-975	120	100	80	90	90
1-977	120	100	100	100	90
1-978	120	100	80	90	90
1-980	120	100	80	100	90
1-981	120	80	50	60	70
1-983	120	70	90	90	90
1-985	120	90	70	100	90
1-986	120	90	80	90	90
1-988	120	90	100	100	90
1-990	120	90	80	90	80
1-991	120	90	100	100	90
1-992	120	100	100	90	100
1-993	120	100	100	100	100
1-994	120	90	60	100	90
1-996	120	90	80	80	90
1-997	120	90	80	90	90
1-1000	120	100	90	80	100
1-1002	120	100	100	100	100
1-1003	120	100	90	90	90
1-1005	120	90	70	60	90
1-1006	120	70	60	70	90
1-1011	120	90	90	90	90
1-1012	120	90	100	100	100
1-1013	120	40	90	90	90
1-1014	120	90	100	90	90
1-1015	120	90	90	100	90
1-1016	120	90	60	90	80
1-1017	120	40	90	60	90
1-1018	120	90	90	100	90
1-1019	120	40	60	60	40
1-1020	120	50	40	80	40
1-1021	120	40	40	40	60
1-1022	120	90	100	100	90
1-1023	120	50	50	40	50
1-1026	120	100	100	100	90
1-1027	120	90	100	100	80
1-1028	120	80	90	80	40
1-1029	120	60	60	60	60
1-1030	120	90	100	100	90
1-1031	120	100	100	100	100
1-1032	120	80	90	90	90
1-1033	120	90	100	100	90
1-1034	120	100	100	100	90
1-1036	120	70	60	60	70
1-1037	120	90	60	70	90
1-1038	120	90	90	90	90
1-1039	120	90	80	90	90
1-1040	120	100	90	100	90
1-1041	120	100	90	90	90
1-1042	120	90	80	90	90
1-1043	120	100	100	100	90
1-1044	120	90	40	60	40
1-1045	120	100	80	90	90
1-1046	120	100	80	70	90
1-1047	120	90	80	100	90
1-1048	120	90	60	80	80
1-1049	120	90	80	90	90
1-1050	120	100	100	100	90
1-1051	120	80	80	60	100
1-1054	120	90	100	100	90
1-1055	120	60	100	100	90
1-1057	120	90	80	80	90
1-1058	120	90	70	80	90
1-1059	120	100	90	80	80
1-1064	120	90	90	90	90
1-1127	120	100	100	100	90

TABLE 4 — Concen- tration Echinochloa Monochoria Lindernia Scirpus

No.	(g/10a)	crus - galli
vaginalis
pyxidaria
juncoides
1-28	120	100	100	80	90
1-29	120	100	90	80	90
1-31	120	50	80	60	70
1-32	120	90	90	80	90
1-33	120	60	60	60	80
1-37	120	40	40	40	0
1-41	120	90	80	90	60
1-46	120	40	40	40	60
1-47	120	40	40	40	70
1-63	120	80	90	80	90
1-68	120	40	80	70	80
1-69	120	60	60	40	60
1-78	120	40	60	40	80
1-81	120	80	80	60	90
1-83	120	40	40	40	60
1-84	120	40	40	40	70
1-97	120	90	60	80	90
1-98	120	80	60	60	90
1-100	120	90	100	90	90
1-101	120	90	90	90	90
1-102	120	90	90	60	90
1-103	120	90	80	60	80
1-105	120	90	90	90	90
1-106	120	90	90	90	90
1-109	120	90	90	70	90
1-110	120	100	100	80	80
1-112	120	90	80	80	90
1-113	120	90	80	60	90
1-115	120	90	80	80	90
1-116	120	90	80	60	90
1-120	120	90	80	80	90
1-124	120	90	70	60	80
1-130	120	100	90	90	80
1-133	120	60	80	60	80
1-134	120	80	80	40	80
1-135	120	80	60	40	90
1-136	120	90	70	60	90
1-137	120	90	60	40	80
1-138	120	90	80	80	80
1-142	120	100	100	90	90
1-143	120	90	80	70	90
1-144	120	90	80	50	90
1-145	120	90	80	60	80
1-146	120	100	90	70	90
1-148	120	90	80	60	90
1-149	120	100	90	90	90
1-155	120	100	60	60	80
1-156	120	80	100	100	90
1-162	120	90	80	70	80
1-166	120	100	90	90	90
1-167	120	90	90	90	90
1-180	120	70	90	80	90
1-181	120	50	90	80	90
1-182	120	40	60	60	70
1-183	120	80	100	100	100
1-186	120	50	80	80	80
1-187	120	40	80	70	70
1-189	120	60	80	80	80
1-191	120	90	80	80	90
1-192	120	40	80	80	60
1-193	120	60	80	80	70
1-194	120	40	60	60	60
1-195	120	80	40	40	80
1-198	120	40	90	90	40
1-199	120	90	80	80	80
1-200	120	60	90	90	80
1-201	120	40	70	70	40
1-202	120	40	60	60	40
1-203	120	90	90	90	90
1-204	120	80	80	80	80
1-205	120	50	90	90	80
1-206	120	60	90	80	80
1-207	120	60	70	60	70
1-208	120	90	90	60	80
1-209	120	40	80	60	90
1-211	120	90	80	60	90
1-212	120	90	90	70	90
1-213	120	90	80	70	80
1-214	120	90	80	70	80
1-215	120	90	80	90	90
1-216	120	90	100	100	90
1-218	120	90	80	40	90
1-219	120	90	70	40	90
1-220	120	40	90	100	90
1-221	120	60	40	40	40
1-222	120	90	90	90	90
1-224	120	90	80	60	80
1-229	120	70	90	60	90
1-230	120	90	90	70	90
1-231	120	60	40	40	60
1-232	120	70	40	40	60
1-235	120	50	60	40	60
1-237	120	90	90	60	90
1-238	120	80	80	40	80
1-248	120	40	90	90	90
1-251	120	50	80	50	90
1-263	120	90	60	40	90
1-264	120	80	80	50	90
1-293	120	90	90	90	90
1-294	120	90	90	90	90
1-295	120	90	90	90	90
1-297	120	100	90	100	90
1-298	120	90	90	90	90
1-299	120	100	70	60	90
1-300	120	100	90	70	80
1-304	120	90	90	90	90
1-305	120	90	90	90	90
1-310	120	90	90	90	90
1-315	120	90	90	90	90
1-316	120	90	90	90	90
1-318	120	90	90	90	90
1-319	120	90	90	90	90
1-320	120	90	90	90	90
1-321	120	90	90	90	90
1-329	120	90	90	90	90
1-330	120	90	90	90	90
1-331	120	90	90	90	90
1-333	120	90	90	90	90
1-334	120	100	70	70	90
1-335	120	90	90	90	90
1-336	120	90	90	90	90
1-337	120	90	90	90	90
1-351	120	90	90	90	90
1-352	120	90	90	90	90
1-353	120	90	90	90	90
1-354	120	100	90	70	90
1-355	120	90	90	90	90
1-356	120	100	70	60	90
1-357	120	90	90	90	90
1-358	120	90	90	90	90
1-359	120	90	90	90	90
1-403	120	90	90	90	90
1-404	120	90	90	90	90
1-405	120	90	90	90	90
1-407	120	90	90	90	90
1-408	120	90	60	70	90
1-412	120	90	90	90	90
1-413	120	90	90	90	90
1-416	120	90	90	90	90
1-431	120	90	90	90	90
1-432	120	90	90	90	90
1-434	120	90	90	90	90
1-444	120	90	90	90	90
1-472	120	90	90	80	90
1-473	120	90	90	90	90
1-474	120	90	90	90	90
1-479	120	90	90	90	90
1-484	120	90	90	90	90
1-494	120	90	90	90	90
1-503	120	90	90	90	90
1-504	120	90	90	90	90
1-506	120	90	90	90	90
1-522	120	90	90	90	90
1-528	120	90	90	90	90
1-575	120	90	100	100	100
1-576	120	90	90	90	90
1-577	120	90	90	90	90
1-580	120	90	90	90	90
1-583	120	100	90	80	90
1-587	120	90	90	90	90
1-592	120	90	90	90	90
1-597	120	90	100	80	90
1-598	120	90	90	90	90
1-604	120	90	90	90	90
1-605	120	90	90	90	90
1-608	120	90	80	60	80
1-609	120	90	90	90	90
1-611	120	100	80	70	90
1-615	120	90	90	90	90
1-620	120	90	90	90	90
1-626	120	90	90	90	90
1-631	120	90	90	90	90
1-632	120	90	90	90	90
1-634	120	90	90	90	90
1-641	120	90	90	90	90
1-642	120	90	90	90	90
1-647	120	90	90	90	90
1-652	120	90	90	90	90
1-653	120	90	90	90	90
1-666	120	100	90	90	90
1-667	120	90	90	90	90
1-668	120	90	90	90	90
1-669	120	90	90	90	90
1-671	120	90	90	60	90
1-674	120	100	90	70	90
1-675	120	90	90	90	90
1-676	120	90	90	90	90
1-677	120	70	80	80	90
1-678	120	90	90	90	90
1-679	120	50	40	40	40
1-706	120	90	90	90	90
1-707	120	90	90	90	90
1-708	120	90	90	90	90
1-709	120	90	90	90	90
1-710	120	90	90	90	90
1-731	120	90	90	90	90
1-733	120	100	90	70	90
1-735	120	90	90	90	90
1-736	120	90	90	90	90
1-762	120	90	90	90	90
1-763	120	90	90	90	90
1-765	120	90	90	90	90
1-766	120	90	90	90	90
1-781	120	90	90	90	90
1-783	120	90	90	90	90
(TLC
bottom)
1-785	120	90	90	90	90
1-788	120	40	40	40	50
(TLC top)
1-789	120	100	90	60	90
(TLC
bottom)
1-790	120	90	90	90	90
1-796	120	90	90	90	90
1-829	120	90	90	90	90
1-874	120	90	90	90	90
1-886	120	90	90	90	90
1-888	120	90	100	80	90
1-889	120	90	90	90	90
1-890	120	90	90	90	90
1-892	120	90	80	80	90
1-893	120	90	90	90	90
1-894	120	90	70	70	80
1-895	120	90	80	70	90
1-899	120	90	90	90	90
1-900	120	90	90	90	90
1-906	120	90	100	100	100
1-907	120	90	90	90	90
1-913	120	90	90	90	90
1-915	120	90	90	90	90
1-916	120	90	90	90	90
1-917	120	90	90	90	90
1-960	120	70	70	70	70
1-962	120	90	80	60	80
1-963	120	90	90	90	90
1-964	120	90	90	90	90
1-965	120	100	80	50	80
1-967	120	90	90	100	80
1-968	120	90	90	90	90
1-969	120	100	90	60	90
1-970	120	100	90	70	90
1-971	120	100	90	80	90
1-972	120	100	100	80	90
1-973	120	100	90	60	90
1-974	120	100	90	90	90
1-975	120	100	80	70	80
1-977	120	100	90	80	90
1-978	120	100	60	50	60
1-980	120	100	80	80	80
1-981	120	90	40	50	40
1-983	120	40	80	80	80
1-985	120	90	60	60	60
1-986	120	90	70	40	90
1-988	120	90	100	100	90
1-990	120	100	80	100	80
1-991	120	90	80	70	90
1-992	120	90	90	50	80
1-993	120	90	60	50	90
1-994	120	90	80	60	80
1-996	120	70	80	70	90
1-997	120	90	90	70	90
1-1000	120	90	70	40	90
1-1002	120	90	80	60	80
1-1003	120	100	70	70	90
1-1005	120	90	90	70	90
1-1006	120	80	80	60	90
1-1011	120	40	90	90	90
1-1012	120	60	80	80	90
1-1014	120	90	80	80	90
1-1015	120	70	90	90	90
1-1016	120	40	80	70	60
1-1017	120	0	80	80	80
1-1018	120	40	80	80	80
1-1019	120	0	40	40	0
1-1020	120	60	40	40	40
1-1022	120	70	100	100	90
1-1023	120	40	40	40	40
1-1026	120	60	90	100	80
1-1027	120	40	40	40	40
1-1028	120	0	40	40	0
1-1030	120	90	90	90	90
1-1031	120	90	100	100	100
1-1032	120	40	40	40	40
1-1033	120	70	80	80	80
1-1034	120	90	80	80	90
1-1036	120	40	60	60	60
1-1037	120	90	50	60	60
1-1038	120	90	80	60	90
1-1039	120	100	80	70	80
1-1040	120	100	60	60	70
1-1041	120	90	70	70	70
1-1042	120	60	60	60	70
1-1043	120	90	100	100	90
1-1044	120	70	40	40	70
1-1045	120	90	90	60	90
1-1046	120	90	90	60	90
1-1047	120	80	80	90	80
1-1048	120	90	60	60	40
1-1049	120	80	70	60	70
1-1050	120	90	90	100	90
1-1051	120	90	80	40	90
1-1054	120	90	100	100	90
1-1055	120	80	60	40	80
1-1057	120	80	80	60	80
1-1058	120	90	90	80	80
1-1059	120	90	70	40	70
1-1064	120	70	80	50	90
1-1127	120	100	100	100	90

TABLE 5

	Concentration	southern
Echinochloa
Chenopodium
Amaranthus
No.	(g/10a)	crabgrass	crus - galli
album
viridis
1-28	120	80	90	100	100
1-29	120	70	70	40	40
1-33	120	70	90	40	0
1-37	120	40	70	40	0
1-41	120	90	90	50	0
1-63	120	90	90	40	40
1-83	120	40	50	40	40
1-97	120	90	90	0	0
1-98	120	90	90	0	0
1-100	120	100	100	100	100
1-101	120	90	90	90	90
1-102	120	90	90	80	80
1-103	120	100	100	100	100
1-105	120	90	60	50	70
1-106	120	90	90	90	90
1-109	120	90	90	60	60
1-110	120	90	90	80	80
1-112	120	90	90	80	60
1-113	120	90	90	100	80
1-115	120	90	90	100	100
1-116	120	90	90	50	80
1-120	120	90	90	50	50
1-124	120	80	100	50	40
1-130	120	70	90	50	40
1-136	120	100	100	60	100
1-137	120	50	70	40	40
1-138	120	90	90	0	0
1-142	120	90	100	90	70
1-143	120	40	50	0	60
1-144	120	80	70	0	0
1-145	120	80	90	40	40
1-146	120	100	100	90	90
1-148	120	100	100	80	80
1-149	120	90	90	40	40
1-156	120	80	80	60	60
1-166	120	90	90	60	60
1-180	120	80	80	30	30
1-183	120	90	90	60	50
1-203	120	90	60	40	40
1-208	120	50	100	40	40
1-211	120	90	90	0	0
1-212	120	90	90	0	0
1-213	120	100	100	100	100
1-214	120	70	80	90	90
1-215	120	50	50	40	40
1-216	120	70	60	0	40
1-218	120	40	80	40	40
1-219	120	80	90	40	90
1-221	120	50	70	40	50
1-222	120	100	100	100	100
1-224	120	100	100	90	100
1-229	120	60	40	40	60
1-230	120	100	100	60	60
1-237	120	50	50	40	80
1-248	120	80	70	60	50
1-251	120	80	100	80	80
1-293	120	90	90	90	90
1-294	120	90	90	90	90
1-295	120	90	90	90	90
1-297	120	90	100	90	90
1-298	120	90	90	90	90
1-299	120	80	90	40	70
1-300	120	100	90	60	80
1-304	120	90	90	90	90
1-305	120	90	90	90	90
1-310	120	90	90	90	90
1-315	120	90	90	90	90
1-316	120	90	90	90	90
1-318	120	90	90	90	90
1-319	120	90	90	90	90
1-320	120	90	90	90	90
1-321	120	90	90	90	90
1-329	120	90	90	90	90
1-330	120	90	90	90	90
1-331	120	90	90	90	90
1-333	120	90	90	90	90
1-334	120	70	90	40	50
1-335	120	90	90	90	90
1-336	120	90	90	90	90
1-337	120	90	90	90	90
1-351	120	90	90	90	90
1-352	120	90	90	90	90
1-353	120	90	90	90	90
1-354	120	80	90	90	90
1-355	120	90	90	90	90
1-356	120	90	90	60	90
1-357	120	90	90	90	90
1-358	120	90	90	90	90
1-359	120	90	90	90	90
1-403	120	90	90	90	90
1-404	120	90	90	90	90
1-405	120	90	90	90	90
1-407	120	90	90	90	90
1-408	120	100	100	60	80
1-412	120	90	90	90	90
1-413	120	90	90	90	90
1-416	120	90	90	90	90
1-431	120	90	90	90	90
1-432	120	90	90	90	90
1-434	120	90	90	90	90
1-444	120	90	90	90	90
1-472	120	70	90	50	0
1-473	120	90	90	90	90
1-474	120	90	90	90	90
1-479	120	90	90	90	90
1-484	120	90	90	90	90
1-494	120	90	90	90	90
1-503	120	90	90	90	90
1-504	120	90	90	90	90
1-506	120	90	90	90	90
1-522	120	90	90	90	90
1-528	120	90	90	90	90
1-575	120	90	90	40	40
1-576	120	90	90	90	90
1-577	120	90	90	90	90
1-580	120	90	90	90	90
1-583	120	90	100	50	60
1-587	120	90	90	90	90
1-592	120	90	90	90	90
1-597	120	90	90	0	0
1-598	120	90	90	90	90
1-604	120	90	90	90	90
1-605	120	90	90	90	90
1-609	120	90	90	90	90
1-611	120	70	70	40	40
1-615	120	90	90	90	90
1-620	120	90	90	90	90
1-626	120	90	90	90	90
1-631	120	90	90	90	90
1-641	120	90	90	90	90
1-642	120	90	90	90	90
1-647	120	90	90	90	90
1-652	120	90	90	90	90
1-653	120	90	90	90	90
1-666	120	100	90	40	0
1-667	120	80	90	90	80
1-668	120	90	90	90	90
1-669	120	90	90	90	90
1-674	120	50	80	40	40
1-675	120	90	90	90	90
1-676	120	90	90	90	90
1-678	120	90	90	90	90
1-706	120	90	90	90	90
1-707	120	90	90	90	90
1-708	120	90	90	90	90
1-709	120	90	90	90	90
1-710	120	90	90	90	90
1-731	120	90	90	90	90
1-733	120	100	100	60	80
1-735	120	90	90	90	90
1-736	120	90	90	90	90
1-762	120	90	90	90	90
1-763	120	90	90	90	90
1-765	120	90	90	90	90
1-766	120	90	90	90	90
1-781	120	90	90	90	90
1-783	120	90	90	90	90
(TLC bottom)
1-785	120	90	90	90	90
1-789	120	60	90	80	70
(TLC bottom)
1-790	120	90	90	90	90
1-796	120	90	90	90	90
1-829	120	90	90	90	90
1-874	120	90	90	90	90
1-886	120	90	90	90	90
1-888	120	70	90	60	40
1-889	120	90	90	90	90
1-890	120	90	90	90	90
1-892	120	90	90	80	90
1-893	120	90	90	90	90
1-894	120	90	90	60	70
1-895	120	100	100	50	80
1-899	120	90	90	90	90
1-900	120	90	90	90	90
1-906	120	90	100	70	50
1-907	120	90	90	90	90
1-913	120	90	90	90	90
1-915	120	90	90	90	90
1-916	120	90	90	90	90
1-917	120	90	90	90	90
1-960	120	80	100	0	0
1-962	120	90	90	70	80
1-963	120	90	90	90	90
1-964	120	90	90	90	90
1-965	120	100	100	100	100
1-967	120	90	50	40	80
1-968	120	90	90	90	90
1-969	120	80	90	40	40
1-970	120	90	90	40	60
1-971	120	80	90	60	80
1-972	120	90	90	100	100
1-973	120	100	100	90	90
1-974	120	90	90	100	100
1-975	120	90	80	90	90
1-977	120	80	80	50	70
1-978	120	90	80	90	90
1-980	120	60	40	40	40
1-985	120	70	70	80	80
1-986	120	80	100	60	60
1-990	120	50	50	50	0
1-992	120	90	90	40	40
1-993	120	80	90	40	40
1-997	120	90	90	50	50
1-1000	120	80	60	40	40
1-1005	120	40	60	40	40
1-1006	120	60	80	60	60
1-1011	120	80	90	40	40
1-1014	120	70	90	40	40
1-1038	120	90	90	0	0
1-1039	120	90	90	0	0
1-1040	120	100	100	80	100
1-1041	120	80	70	50	50
1-1045	120	50	90	40	40
1-1048	120	0	40	40	40
1-1049	120	80	90	50	50
1-1050	120	90	100	90	90
1-1051	120	80	80	60	80
1-1064	120	60	100	80	80
1-1127	120	70	90	60	40

TABLE 6

	Concentration	southern
Echinochloa
Chenopodium
Amaranthus
No.	(g/10a)	crabgrass	crus - galli
album
viridis
1-28	120	50	90	40	80
1-29	120	40	60	0	60
1-32	120	40	0	60	40
1-33	120	40	90	40	0
1-37	120	40	90	80	40
1-41	120	90	90	90	60
1-63	120	60	90	60	40
1-81	120	80	90	0	0
1-97	120	90	90	40	40
1-100	120	90	90	90	30
1-101	120	90	90	40	40
1-102	120	80	90	0	40
1-103	120	90	90	40	90
1-105	120	50	90	40	50
1-106	120	90	90	40	40
1-109	120	80	90	50	70
1-110	120	90	90	50	60
1-112	120	50	90	0	40
1-113	120	60	80	40	60
1-115	120	40	60	40	40
1-116	120	40	80	50	60
1-120	120	80	90	50	60
1-124	120	60	70	40	40
1-130	120	60	60	40	50
1-133	120	40	90	40	0
1-134	120	60	90	40	50
1-136	120	70	70	60	60
1-137	120	0	80	0	80
1-138	120	80	80	0	40
1-142	120	80	90	40	60
1-144	120	90	90	0	50
1-145	120	50	90	40	0
1-146	120	40	80	40	50
1-148	120	80	90	40	40
1-149	120	90	90	40	40
1-162	120	60	90	60	50
1-180	120	50	50	40	0
1-183	120	50	90	50	40
1-191	120	40	90	40	80
1-208	120	0	90	40	40
1-211	120	60	90	50	40
1-212	120	90	90	60	80
1-213	120	90	90	50	40
1-214	120	50	60	50	40
1-215	120	50	40	40	50
1-218	120	40	90	40	60
1-219	120	60	90	0	40
1-222	120	80	70	50	40
1-230	120	80	80	40	40
1-248	120	40	80	0	40
1-293	120	90	90	40	40
1-294	120	90	90	40	40
1-295	120	90	90	40	40
1-297	120	60	80	40	40
1-298	120	90	90	40	40
1-299	120	80	90	90	40
1-300	120	90	90	60	70
1-304	120	90	90	40	40
1-305	120	90	90	40	40
1-310	120	90	90	40	40
1-315	120	90	90	40	40
1-316	120	90	90	40	40
1-318	120	90	90	40	40
1-319	120	90	90	40	40
1-320	120	90	90	40	40
1-321	120	90	90	40	40
1-329	120	90	90	40	40
1-330	120	90	90	40	40
1-331	120	90	90	40	40
1-333	120	90	90	40	40
1-334	120	90	90	60	60
1-335	120	90	90	40	40
1-336	120	90	90	40	40
1-337	120	90	90	40	40
1-351	120	90	90	40	40
1-352	120	90	90	40	40
1-353	120	90	90	40	40
1-354	120	60	80	40	40
1-355	120	90	90	40	40
1-356	120	80	90	60	60
1-357	120	90	90	40	40
1-358	120	90	90	40	40
1-359	120	90	90	40	40
1-403	120	90	90	40	40
1-404	120	90	90	40	40
1-405	120	90	90	40	40
1-407	120	90	90	40	40
1-408	120	90	90	70	40
1-412	120	90	90	40	40
1-413	120	90	90	40	40
1-416	120	90	90	40	40
1-431	120	90	90	40	40
1-432	120	90	90	40	40
1-434	120	90	90	40	40
1-444	120	90	90	40	40
1-473	120	90	90	40	40
1-474	120	90	90	40	40
1-479	120	90	90	40	40
1-484	120	90	90	40	40
1-494	120	90	90	40	40
1-503	120	90	90	40	40
1-504	120	90	90	40	40
1-506	120	90	90	40	40
1-522	120	90	90	40	40
1-528	120	90	90	40	40
1-575	120	90	90	90	30
1-576	120	90	90	40	40
1-577	120	90	90	40	40
1-580	120	90	90	40	40
1-583	120	60	80	50	50
1-587	120	90	90	40	40
1-592	120	90	90	40	40
1-597	120	50	40	40	40
1-598	120	90	90	40	40
1-604	120	90	90	40	40
1-605	120	90	90	40	40
1-609	120	90	90	40	40
1-611	120	70	80	50	60
1-615	120	90	90	40	40
1-620	120	90	90	40	40
1-626	120	90	90	40	40
1-632	120	90	90	40	40
1-642	120	90	90	40	40
1-647	120	90	90	40	40
1-652	120	90	90	40	40
1-653	120	90	90	40	40
1-666	120	70	90	50	40
1-668	120	90	90	40	40
1-669	120	90	90	40	40
1-674	120	80	70	50	60
1-675	120	90	90	40	40
1-676	120	90	90	40	40
1-678	120	90	90	40	40
1-706	120	90	90	40	40
1-707	120	90	90	40	40
1-708	120	90	90	40	40
1-709	120	90	90	40	40
1-710	120	90	90	40	40
1-731	120	90	90	40	40
1-733	120	80	90	60	60
1-735	120	90	90	40	40
1-736	120	90	90	40	40
1-762	120	90	90	40	40
1-763	120	90	90	40	40
1-765	120	90	90	40	40
1-766	120	90	90	40	40
1-781	120	90	90	40	40
1-783	120	90	90	40	40
(TLC bottom)
1-785	120	90	90	40	40
1-789	120	50	50	40	60
(TLC bottom)
1-790	120	90	90	40	40
1-796	120	90	90	40	40
1-829	120	90	90	40	40
1-874	120	90	90	40	40
1-886	120	90	90	40	40
1-888	120	40	80	40	40
1-889	120	90	90	40	40
1-890	120	90	90	40	40
1-892	120	40	50	40	40
1-893	120	90	90	40	40
1-894	120	90	90	60	60
1-895	120	80	80	60	50
1-899	120	90	90	40	40
1-900	120	90	90	40	40
1-906	120	50	90	50	100
1-907	120	90	90	40	40
1-913	120	90	90	40	40
1-915	120	90	90	40	40
1-916	120	90	90	40	40
1-917	120	90	90	40	40
1-962	120	60	90	50	40
1-963	120	90	90	40	40
1-964	120	60	90	0	40
1-965	120	90	90	40	90
1-967	120	0	60	40	40
1-968	120	90	90	40	40
1-970	120	70	90	40	60
1-971	120	90	90	50	40
1-973	120	80	90	0	40
1-974	120	50	90	40	40
1-975	120	0	50	40	50
1-977	120	80	90	80	60
1-978	120	50	60	40	40
1-980	120	40	60	40	40
1-983	120	40	60	0	40
1-985	120	60	90	60	60
1-986	120	90	90	40	60
1-990	120	0	60	40	50
1-992	120	50	90	40	40
1-993	120	40	60	40	40
1-997	120	40	70	0	40
1-1000	120	40	60	0	40
1-1002	120	60	90	70	50
1-1003	120	40	60	0	40
1-1005	120	40	60	40	40
1-1006	120	40	40	40	40
1-1014	120	40	70	50	40
1-1030	120	40	90	40	40
1-1038	120	60	90	40	40
1-1039	120	90	90	40	40
1-1040	120	90	90	40	50
1-1041	120	50	40	40	60
1-1042	120	50	0	40	40
1-1045	120	40	90	0	60
1-1046	120	60	90	0	90
1-1050	120	40	50	50	40
1-1127	120	40	90	40	40

Claims as granted

11 claims

Classifications

3 codes

IPC · International Patent Classification

Section A — Human necessities

A01N43/80

Section C — Chemistry; metallurgy

C07D413/12
C07D261/12

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3.6 y

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Erin E Hirt

art unit 1616 · TC 1600

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