The present invention relates to phenylacetic acid derivatives of the formula I ##STR1## and their salts. The invention additionally relates to processes and intermediates for preparing these compounds and compositions containing them for controlling animal pests and harmful fungi.

Claims

9 · 3 independent · depth 2

9 granted claims

›1.independentA phenylacetic acid derivative of the formula ##STR26## where the substituents and the index have the following meanings: X is NOCH.sub.3, CHOCH.sub.3…+6

A phenylacetic acid derivative of the formula ##STR26## where the substituents and the index have the following meanings: X is NOCH.sub.3, CHOCH.sub.3, CHCH.sub.3, or CHCH.sub.2 CH.sub.3 ; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl; R.sup.2 is cyano, nitro, trifluoromethyl, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy; m is 0, 1 or 2, it being possible for the R.sup.2 radicals to be different if m is 2; R.sup.3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino; R.sup.4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkenylamino, N--C.sub.2 -C.sub.6 -alkenyl-N--C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -alkynyloxy, C.sub.2 -C.sub.6 -alkynylthio, C.sub.2 -C.sub.6 -alkynylamino, N--C.sub.2 -C.sub.6 -alkynyl-N--C.sub.1 -C.sub.6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely hydrogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C.sub.1 -C.sub.4 -alkoxy, arylthio, aryl-C.sub.1 -C.sub.4 -alkylthio, hetaryl, hetaryloxy, hetaryl-C.sub.1 -C.sub.4 -alkoxy, hetarylthio, hetaryl-C.sub.1 -C.sub.4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, C.sub.3 -C.sub.6 -cycloalkylthio, C.sub.3 -C.sub.6 -cycloalkylamino, N--C.sub.3 -C.sub.6 -cycloalkyl-N--C.sub.1 -C.sub.6 -alkylamino, C.sub.3 -C.sub.6 -cycloalkenyl, C.sub.3 -C.sub.6 -cycloalkenyloxy, C.sub.3 -C.sub.6 -cycloalkenylthio, C.sub.3 -C.sub.6 -cycloalkenylamino, N--C.sub.3 -C.sub.6 -cycloalkenyl-N--C.sub.3 -C.sub.6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C.sub.1 -C.sub.6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C.sub.1 -C.sub.6 -alkylamino hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N--C.sub.1 -C.sub.6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R.sup.5 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkynyl, C.sub.1 -C.sub.10 -alkylcarbonyl, C.sub.2 -C.sub.10 -alkenylcarbonyl, C.sub.3 -C.sub.10 -alkynylcarbonyl or C.sub.1 -C.sub.10 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C2.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; where A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C.sub.1 -C.sub.6 -alkyl; n is 0 or 1; R.sup.6 is hydrogen or C.sub.1 -C.sub.6 -alkyl and R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl, wherein heterocyclyl is a member selected from the group consisting of three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur; aryl is a member selected from the group consisting of aromatic mono- or polycyclic hydrocarbon radicals; and hetaryl is a member selected from the group consisting of aromatic mono- or polycyclic radicals which, in addition to carbon ring members, contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom, where X is not CHOCH.sub.3 if R.sup.3 is hydrogen and R.sup.5 is C.sub.1 -C.sub.10 -alkyl, and its salts.

›2.↳ 1A compound of the formula I as claimed in claim 1, in which R.sup.3, R.sup.4 and R.sup.5 have the following meanings: R.sup.3 is hydrogen, hydroxyl, c…d2

A compound of the formula I as claimed in claim 1, in which R.sup.3, R.sup.4 and R.sup.5 have the following meanings: R.sup.3 is hydrogen, hydroxyl, cyclopropyl, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, R.sup.4 is hydrogen, hydroxyl, halogen, cyclopropyl, cyclohexyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, aryl or hetaryl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R.sup.5 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkynyl, C.sub.1 -C.sub.10 -alkylcarbonyl, C.sub.2 -C.sub.10 -alkenylcarbonyl, C.sub.3 -C.sub.10 -alkynylcarbonyl or C.sub.1 -C.sub.10 -alkylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the aromatic and heteroaromatic radicals, in turn, to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7, where X is not CHOCH.sub.3 if R.sup.3 is hydrogen and R.sup.5 is C.sub.1 -C.sub.10 -alkyl.

›3.↳ 1A compound of the formula I as claimed in claim 1, in which m is 0.d2

›4.↳ 1A compound of the formula I as claimed in claim 1, in which R.sup.1 is methyl.d2

›5.↳ 1A process for preparing the compounds of the formula I as claimed in claim 1, in which R.sup.3 is not halogen, which comprises reacting a benzyl deriv…d2

›6.↳ 1A composition against harmful fungi, containing additives and an effective amount of a compound of the formula I as claimed in claim 1.d2

›8.↳ 1A method for controlling harmful fungi, which comprises treating harmful fungi, their environment or the plants, surfaces, materials or spaces to be k…d2

›7.independentA composition against animal pests or harmful fungi, containing additives and an effective amount of a compound of a phenylacetic acid derivative of t…

A composition against animal pests or harmful fungi, containing additives and an effective amount of a compound of a phenylacetic acid derivative of the formula I ##STR28## where the substituents and the index have the following meanings: X is NOCH.sub.3, CHOCH.sub.3, CHCH.sub.3, and CHCH.sub.2 CH.sub.3 ; R.sup.1 is hydrogen and C.sub.1 -C.sub.4 -alkyl; R.sup.2 is cyano, nitro, trifluoromethyl, halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy; m is 0, 1 or 2, it being possible for the R.sup.2 radicals to be different if m is 2; R.sup.3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino; R.sup.4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkenylamino, N--C.sub.2 -C.sub.6 -alkenyl-N--C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkynyl,C.sub.2 -C.sub.6 -alkynyloxy, C.sub.2 -C.sub.6 -alkynylthio, C.sub.2 -C.sub.6 -alkynylamino, N--C.sub.2 -C.sub.6 -alkynyl-N--C.sub.1 -C.sub.6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely hydrogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C.sub.1 -C.sub.4 -alkoxy, arylthio, aryl-C.sub.1 C.sub.4 -alkylthio, hetaryl, hetaryloxy, hetaryl-C.sub.1 -C.sub.4 -alkoxy, hetarylthio, hetaryl-C.sub.1 -C.sub.4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, C.sub.3 -C.sub.6 -cycloalkylthio, C.sub.3 -C.sub.6 -cycloalkylamino, N--C.sub.3 -C.sub.6 -cycloalkyl-N--C.sub.1 C.sub.6 -alkylamino, C.sub.3 -C.sub.6 -cycloalkenyl, C.sub.3 -C.sub.6 -cycloalkenyloxy, C.sub.3 -C.sub.6 -cycloalkenylthio, C.sub.3 -C.sub.6 -cycloalkenylamino, N--C.sub.3 -C.sub.6 -cycloalkenyl-N--C.sub.1 -C.sub.6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C.sub.1 -C.sub.6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C.sub.1 -C.sub.6 -alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N--C.sub.1 -C.sub.6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R.sup.5 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkynyl, C.sub.1 -C.sub.10 -alkylcarbonyl, C.sub.2 -C.sub.10 -alkenylcarbonyl, C.sub.3 -C.sub.10 -alkynylcarbonyl or C.sub.1 -C.sub.10 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.3 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C2.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; where A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C.sub.1 -C.sub.6 -alkyl; n is 0 or 1; R.sup.6 is hydrogen or C.sub.1 -C.sub.6 -alkyl and R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl, wherein heterocyclyl is a member selected from the group consisting of three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur; aryl is a member selected from the group consisting of aromatic mono- or polycyclic hydrocarbon radicals; and hetaryl is a member selected from the group consisting of aromatic mono- or polycyclic radicals which, in addition to carbon ring members, contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom.

›9.independentA method for controlling animal pests, which comprises treating the pests, their environment or the plants, surfaces, materials or spaces to be kept f…

A method for controlling animal pests, which comprises treating the pests, their environment or the plants, surfaces, materials or spaces to be kept free from them with an effective amount of a compound of the formula I, where the substituents and the index have the following meanings: X is NOCH.sub.3, CHOCH.sub.3, CHCH.sub.3, and CHCH.sub.2 CH.sub.3 ; R.sup.1 is hydrogen and C.sub.1 -C.sub.4 -alkyl; R.sup.2 is cyano, nitro, trifluoromethyl, halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy; m is 0, 1 or 2, it being possible for the R.sup.2 radicals to be different if m is 2; R.sup.3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino; R.sup.4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkenylamino, N--C.sub.2 -C.sub.6 -alkenyl-N--C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -alkynyloxy, C.sub.2 -C.sub.6 -alkynylthio, C.sub.2 -C.sub.6 -alkynylamino, N--C.sub.2 -C.sub.6 -alkynyl-N--C.sub.1 -C.sub.6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely hydrogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C.sub.1 -C.sub.4 -alkoxy, arylthio, aryl-C.sub.1 -C.sub.4 -alkylthio, hetaryl, hetaryloxy, hetaryl-C.sub.1 -C.sub.4 -alkoxy, hetarylthio, hetaryl-C.sub.1 -C.sub.4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C1.sub.-- C6-alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, C.sub.3 -C.sub.6 -cycloalkylthio, C.sub.3 -C.sub.6 -cycloalkylamino, N--C.sub.3 -C.sub.6 -cycloalkyl-N--C.sub.1 -C.sub.6 -alkylamino, C.sub.3 -C.sub.6 -cycloalkenyl, C.sub.3 -C.sub.6 -cycloalkenyloxy, C.sub.3 -C.sub.6 -cycloalkenylthio, C.sub.3 -C.sub.6 -cycloalkenylamino, N--C.sub.3 -C.sub.6 -cycloalkenyl-N--C.sub.1 -C.sub.6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C.sub.1 -C.sub.6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C.sub.1 -C.sub.6 -alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N--C.sub.1 -C.sub.6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R.sup.5 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkynyl, C.sub.1 -C.sub.10 -alkylcarbonyl, C.sub.2 -C.sub.10 -alkenylcarbonyl, C.sub.3 -C.sub.10 -alkynylcarbonyl or C.sub.1 -C.sub.10 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylaminothiocarbonyl, C2.sub.2 -C.sub.6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(.dbd.NOR.sup.6)--A.sub.n --R.sup.7 ; where A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C.sub.1 -C.sub.6 -alkyl; n is 0 or 1; R.sup.6 is hydrogen or C.sub.1 -C.sub.6 -alkyl and R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl, wherein heterocyclyl is a member selected from the group consisting of three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur; aryl is a member selected from the group consisting of aromatic mono- or polycyclic hydrocarbon radicals; and hetaryl is a member selected from the group consisting of aromatic mono- or polycyclic radicals which, in addition to carbon ring members, contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom, and its salts.

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USPC · US Patent Classification

514/538514/359546/366.1558/414514/274560/35544/319544/316562/451514/406544/309514/344546/373.1514/640514/369514/567

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Yogendra N. Gupta

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