Patent EA-000786-B1 (EA)
Title: Phenylacetic acid derivatives, process and intermediate products for use in producing them and agents containing them
Inventor: GROTE THOMAS
IPC: C07C/
Filed: 1996-10-11
Abstract: 1. A phenylacetic acid derivative of the formula I   where the substituents and the index have the following meanings: X is NOCH3, CHOCH3, CHCH3; Y is O, NR; R1, R independently of one another are hydrogen and C1-C4-alkyl; R2 is cyano, nitro, trifluoromethyl, halogen, C1-C4-alkyl and C1-C4-alkoxy; m is 0, 1 or 2, it being possible for the radicals R2 to be different when m is 2; R3 is hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl; R4, R6 independently of one another are hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C10-alkylcarbonyl, C2-C10-alkenyl-carbonyl, C3-C10-alkynylcarbonyl or C1-C10-alkyl-sulfonyl, it being possible for these radicals to be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-carbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di- C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di- C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothio-carbonyl, di- C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups, in turn, to be partially or fully halo-genated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkyl-sulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di- C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di- C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di- C1-C6-alkylaminothio-carbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(=NOR<7>)-An-R<8>; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetaryl-carbonyl or hetarylsulfonyl, it being possible for these radicals to be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cyclo-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di- C1-C6-alkyl-aminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyl-oxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(=NOR<7>)-An-R<8>; R<5> is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, it being possible for the hydrocarbon radicals of these groups to be partially or fully halogenated or to have attached to them one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkylaminocarbonyl, di- C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di- C1-C6-alkylaminothio-carbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di- C1-C6-alkylamino, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl- C1-C4-alkoxy, arylthio, aryl- C1-C4-alkylthio, hetaryl, hetaryloxy, hetaryl- C1-C4-alkoxy, hetarylthio, hetaryl- C1-C4-alkylthio, it being possible for the cyclic radicals, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkyl-sulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di- C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di- C1-C6-alkylaminothio-carbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(=NOR<7>)-An-R<8>; C3-C6-cycloalkyl, C3-C6-cycloalkenyl, heterocyclyl, aryl, hetaryl, it being possible for the cyclic radicals to be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloa1koxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di- C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di- C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di- C1-C6-alkylaminothio-carbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; where  A is oxygen, sulfur or nitrogen and where the nitrogen has attached to it hydrogen or C1-C6-alkyl; n is 0 or 1; R<7> is hydrogen or C1-C6-alkyl and R<8> is hydrogen or C1-C6-alkyl, or a salt thereof. 2. A compound of the formula I as claimed in claim 1, where X is NOCH3. 3. A compound of the formula I as claimed in claim 1 or 2, where X is CHOCH3. 4. A compound of the formula I as claimed in any of claims 1 to 3 where X is CHCH3. 5. A compound of the formula I as claimed in any of claims 1 to 4 where m is 0. 6. A compound of the formula I as claimed in any of claims 1 to 5 where R<1> is methyl. 7. A compound of the formula I as claimed in any of claims 1 to 6 where R<3> is hydrogen, cyano, cyclopropyl, methyl, ethyl or 1-methylethyl. 8. A compound of the formula I as claimed in any of claims 1 to 7 where R<4> is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl. 9. A compound of the formula I as claimed in any of claims 1 to 8 where R<5> is hydrogen, cyclopropyl, methyl, ethyl, iso-propyl, unsubstituted or substituted aryl or hetaryl. 10. A compound of the formula I as claimed in any of claims 1 to 9 where R<6> is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, aryl-alkyl, hetarylalkyl, aryloxyalkyl or hetaryloxyalkyl. 11. A process for the preparation of the compounds of the formula I as claimed in claim 1, which comprises reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III   where L<1> is a nucleophilically exchangeable leaving group, and the rest radicals are given in claim 1. 12. A composition against animal pests or harmful fungi comprising customary additives and an effective amount of a compound of the formula I as claimed in claim 1. 13. A composition as claimed in claim 12 for controlling animal pests from the classes of the insects, arachnids or nematodes. 14. A method of controlling animals pests or harmful fungi which comprises treating the pests or harmful fungi, their environment, or the plants, areas, materials or spaces to be kept free from them with an effective amount of at least one compound of the formula I as claimed in claim 1. 15. The use of the compounds I as claimed in claim 1 for the preparation of compositions against animal pests or harmful fungi. 16. The use of the compounds I as claimed in claim 1 for controlling animal pests or harmful fungi. 17. Hydroxyimine of formula III'   in which substituents have the meanings as defined in claim 1 provided that R<4> and R<6> are not hydrogen. 18. Hydroxyimine of formula III   in which substituents have the meanings as defined in claim 1 provided that R<4> and R<6> are not hydrogen. 19. A process for the preparation of the compounds of the formula I, which comprises reacting a benzyl derivative of the formula II   in which Y is hydrogen, and L<1> is a nucleophilically exchangeable leaving group, with a hydroxyimine of the formula III   in which substituents have the meanings as defined in claim 1 and produced ester of formula I further reacts with amine of formula R<1>NH2, where R<1> has the meanings as defined in claim 1.