Patent EA-001313-B1 (EA)
Title: Pesticides
Inventor: FAROOQ SALEM
IPC: C07C255/54
Filed: 1996-11-25
Abstract: 1. A compound of the formula   in which (A) either X is CH or N, Y is OR1 and Z is O; or X is N; Y is NHR8 and Z is O, S or S(=O); R1 is C1-C4alkyl; R2 is H, C1-C4alkyl, haloidC1-C4alkyl, C3-C6cycloalkyl, C1-C4alkoxymethyl, C1-C4alkoxy, haloidC1-C4alkoxy, C1-C4alkylthio, haloidC1-C4alkylthio or CN; R3 and R4 independently of one another are H, C1-C4alkyl, C1-C4alkoxy, OH, CN, NO2, a (C1-C4alkyl)3-Si group, where the alkyl groups can be identical or different, halogen, (C1-C4alkyl)S(=O)m, (haloidC1-C4alkyl)S(=O)m, haloidC1-C4alkyl or haloidC1-C4alkoxy; R8 is H or C1-C4alkyl; R9 is methyl, fluoromethyl or difluoromethyl; m is 0, 1 or 2; G is O or S; and A is a direct bond, C1-C10alkylene, -C(=O)-, -C(=S)- or haloidC1-C10alkylene and R7 is a radical R10; or A is C1-C10alkylene, -C(=O)-, -C(=S)- or haloidC1-C10alkylene and R7 is -CN, OR10, N(R10)2, where the radicals R10 can be identical or different, or  -S(=O)pR10; R is an unsubstituted or mono- or polysubstituted C1-C4alkyl-, C2-C4alkenyl-, C2-C4alkynyl-, C3-C6cycloalkyl-, benzyl-, aryl or heteroaryl-group, where the substituents of the groups independently of one another are chosen from the group consisting of halogen, C1-C6alkyl, haloidC1-C6alkyl, C3-C6cycloalkyl, haloidC3-C6cycloalkyl, C1-C6alkoxy, haloidC1-C6alkoxy, C1-C6alkylthio, haloidC1-C6alkylthio, phenoxy, CN and nitro, or a phenyl radical which is monosubstituted on two adjacent C atoms by an unsubstituted or mono- to tetrasubstituted C1-C4alkylenedioxy group, where the substituents are selected from the group consisting of C1-C4alkyl and halogen; or CH2Si(C1-C4alkyl)3, where the alkyl groups can be identical or different; and R5 is C1-C6alkyl, haloidC1-C6alkyl, C3-C6cycloalkyl, haloidC3-C6cycloalkyl, C1-C6alkoxy, haloidC1-C6alkoxy, C1-C6alkylthio, haloidC1-C6alkylthio, C1-C6alkylsulfinyl, haloidC1-C6alkylsulfinyl, C1-C6alkylsulfonyl, haloidC1-C6alkylsulfonyl, C1-C6alkylsulfonyloxy, haloidC1-C6alkylsulfonyloxy, C1-C6alkoxy-C1-C6alkyl, haloidC1-C6alkoxy-C1-C6alkyl, C1-C6alkylthio-C1-C6alkyl, haloidC1-C6alkylthio-C1-C6alkyl, C1-C6alkylsulfinyl-C1-C6alkyl, haloidC1-C6alkylsulfinyl-C1-C6alkyl, C1-C6alkylsulfonyl-C1-C6alkyl, haloidC1-C6alkylsulfonyl-C1-C6alkyl, C1-C6alkylcarbonyl, haloidC1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, haloidC1-C6alkoxycarbonyl, C1-C6alkylaminocarbonyl, C1-C4alkoxyiminomethyl, di(C1-C6alkyl)aminocarbonyl, where the alkyl groups can be identical or different; C1-C6alkylaminothiocarbonyl, di(C1-C6alkyl)aminothiocarbonyl, where the alkyl groups can be identical or different; C1-C6alkylamino, di(C1-C6alkyl)amino, where the alkyl groups can be identical or different; halogen, NO2, CN, SF5, thioamido, thiocyanatomethyl, trimethylsilyl; an unsubstituted or mono-to tetrasubstituted C1-C4alkylenedioxy group, where the substituents are chosen from the group consisting of C1-C4alkyl and halogen; aryl-Q-(C1-C6)alkyl, aryl-Q-(C2-C6)alkenyl, heterocyclyl-Q-(C1-C6)alkyl, heterocyclyl-Q-(C2-C6)alkenyl, or aryl-Q-(C1-C6)alkyl, aryl-Q-(C2-C6)alkenyl, heterocyclyl-Q-(C1-C6)alkyl or heterocyclyl-Q-(C2-C6)alkenyl which are mono- to pentasubstituted in the aryl or heterocyclyl ring, depending on the possibility of substitution, where the substituents independently of one another are chosen from the group consisting of halogen, C1-C6alkyl, haloidC1-C6alkyl, C3-C6cycloalkyl, haloidC3-C6cycloalkyl, C1-C6alkoxy, haloidC1-C6alkoxy, CN, nitro, OC(=O)-C1-C6alkyl, OH, NH2 and C1-C6alkoxycarbonyl; where, if q is greater than 1, the radicals R5 can be identical or different; Q is a direct bond, -CH(OH)-, -C(=O)- or -S(=O)v-; v is 0, 1 or 2; R10 is H, C1-C6alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6cycloalkyl; or C1-C6alkyl , C2-C8alkenyl, C2-C8alkynyl or C3-C6cycloalkyl, which are mono- or polysubstituted by substituents from the group consisting of halogen; -Si(C1-C4alkyl)3, where the alkyl groups can be identical or different; C1-C6alkoxycarbonyl, or an aryl or heterocyclyl group which are unsubstituted or mono- or polysubstituted by substituents from the group consisting of halogen, C1-C4alkyl and haloidC1-C4alkyl, and p is 0, 1 or 2; and (B) either (I) n is 1 or 2 and q is 1, 2, 3 or, when n is 1, is 4; and A, G, X, Y, Z, R, R2, R3, R4, R5, R7 and R9 are as defined above under (A); or (II) n is 0; q is 2, 3, 4 or 5; and A, X, Y, Z, R2, R3, R4, R5, R7 and R9 are as defined above under (A); and the radicals R5 can be identical or different; with the proviso that if q is 2, (R5)2 is not dichloro or dimethyl, and with the further proviso that R2 is not CH3, if AR7 is CH3 and (R5)2 is 3-fluoro, 5-CF3 or, together, 3,4-methylenedioxy and R3 and R4 are H; or (III) n is 0; q is 1; A, X, Y, Z, R2, R3, R4, R7 and R9 are as defined above under (A); and R5 is tert-butyl, C5-C6alkyl, haloidC1-C6alkyl, with the exeption of CF3; C3-C6cycloalkyl, haloidC3-C6cycloalkyl, C5-C6alkoxy, haloidC3-C6alkoxy, C2-C6alkylthio, haloidC1-C6alkylthio, C1-C6alkylsulfinyl, haloidC1-C6alkylsulfinyl, C2-C6alkylsulfonyl, haloidC1-C6alkylsulfonyl, C1-C6alkylsulfonyloxy, haloidC1-C6alkylsulfonyloxy, C1-C6alkoxy-C1-C6alkyl, haloidC1-C6alkoxy-C1-C6alkyl, C1-C6alkylthio-C1-C6alkyl, haloidC1-C6alkylthio-C1-C6alkyl, C1-C6alkylsulfinyl-C1-C6alkyl, haloidC1-C6alkylsulfinyl-C1-C6alkyl, C1-C6alkylsulfonyl-C1-C6alkyl, haloidC1-C6alkylsulfonyl-C1-C6alkyl, C1-C6alkylcarbonyl, haloidC1-C6alkylcarbonyl, C2-C6alkoxycarbonyl, haloidC1-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C1-C4alkoxyiminomethyl, di(C2-C6alkyl)aminocarbonyl, where the alkyl groups can be identical or different; C1-C6alkylaminothiocarbonyl, di(C1-C6alkyl)aminothiocarbonyl, where the alkyl groups can be identical or different; C2-C6alkylamino, di(C2-C6alkyl)amino, where the alkyl groups can be identical or different; SF5, thiocyanatomethyl, trimethylsilyl, aryl-Q-(C1-C6)alkyl, aryl-Q-(C2-C6)alkenyl, heterocyclyl-Q-(C1-C6)alkyl, heterocyclyl-Q-(C2-C6)alkenyl; or aryl-Q-(C1-C6)alkyl, aryl-Q-(C2-C6)alkenyl, heterocyclyl-Q-(C1-C6)alkyl or heterocyclyl-Q-(C2-C6)alkenyl which are mono- to pentasubstituted in the aryl or heterocyclyl ring, depending on the possibility of substitution, where the substituents independently of one another are chosen from the group consisting of halogen, C1-C6alkyl, haloidC1-C6alkyl, C3-C6cycloalkyl, haloidC3-C6cycloalkyl, C1-C6alkoxy, haloidC1-C6alkoxy, CN, nitro and C1-C6alkoxycarbonyl; Q is a direct bond, -CH(OH)-, -C(=O)- or-S(=O)v-; v is 0, 1 or 2; or (IV) n is 1 and q is 0; A, X, Y, Z, R2, R3, R4, R7 and R9 are as defined above under (A); G is O; and R is n-propyl, n-butyl, sec-butyl, isobutyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C4alkyl, haloidC4-C6cycloalkyl-C1-C4alkyl, C1-C4alkylenyl-C3-C6cycloalkyl, C1-C4alkylenyl-haloidC3-C6cycloalkyl, CH2Si(C1-C4alkyl)3, where the alkyl groups can be identical or different; a substituted aryl or benzyl, where the substituents of the aryl or benzyl independently of one another are chosen from the group consisting of C1-C6alkyl, haloidC1-C6alkyl, C3-C6cycloalkyl, haloidC3-C6-cycloalkyl, C1-C6alkoxy, haloidC1-C6alkoxy, C1-C6alkylthio, haloidC1-C6alkylthio, phenoxy, CN and nitro; or a phenyl radical which is monosubstituted on two adjacent C atoms by an unsubstituted or mono- to tetrasubstituted C1-C4alkylenedioxy group, where the substituents are selected from the group consisting of C1-C4alkyl and halogen; with the proviso that OR is not n-propyloxy or -OCH2Si(CH3)3 in the 4-position, if X is CH, Y is OCH3, Z is O, AR7 is CH3, R2 is CH3 and R3 and R4 are H; and with the further proviso that R is not phenyl group which is substituted by fluorine or chlorine in the 4-position or benzyl group which is substituted by methyl or methoxy in the 4-position or monosubstituted by fluorine, chlorine, bromine or CF3 in the 2-, 3- or 4-position if OR is in the p-position, AR7 is CH3, R2 is CH3 and R3 and R4 are H ; or (V) n is 1; q is 0; A, X, Y, Z, R, R2, R3, R4, R7 and R9 are as defined above under (A); and G is S; with the proviso that R is not methyl if R2 is methyl; or (VI) n is 1; q is 0;  A, G, X, Y, Z, R2, R3, R4 and R9 are as defined above under (A); A is a direct bond, C7-C10alkylene, -C(=O)-, -C(=S)- or haloidC1-C10alkylene and R7 is a radical R10; or A is C1-C10alkylene, -C(=O)-, -C(=S)- or haloidC1-C10alkylene; and R7 is CN, O(C1-C4alkyl)2, or N(C1-C4alkyl)2, in which the two alkyl radicals can be identical or different, OR10, N(R10)2, where the radicals R10 can be identical or different, or -S(=O)pR10; R10 is H; or C5-C8alkenyl, C4-C8alkynyl, C3-C6cycloalkyl; or C1-C6alkyl, C2-C8alkenyl, C2-C8alkynyl or C3-C6cycloalkyl which are mono- or polysubsbtituted by substituents from the group consisting of halogen; -Si(C1-C4alkyl)3, where the alkyl groups can be identical or different; C1-C6alkoxycarbonyl, or an aryl or heterocyclyl group which are unsubstituted or mono- or polysubstituted by substituents from the group consisting of halogen, C1-C4alkyl and haloidC1-C4alkyl; and R is methyl, ethyl, t-butyl, or mono- or polysubstituted methyl, ethyl or t-butyl, where the substituents independently of one another are chosen from the group consisting of halogen, C1-C6alkyl, haloidC1-C6alkyl, C3-C6cycloalkyl, haloidC3-C6cycloalkyl, C1-C6alkoxy, haloidC1-C6alkoxy, C1-C6alkylthio, haloidC1-C6alkylthio, phenoxy, CN and nitro; or a phenyl radical which is monosubstituted on two adjacent C atoms by an unsubstituted or mono- to tetrasubstituted C1-C4alkylenedioxy group, where the substituents are selected from the group consisting of C1-C4alkyl and halogen; or CH2Si(C1-C4alkyl)3, where the alkyl groups can be identical or different; or (VII) n is 1; q is 0; A, G, X, Y, Z, R2, R3, R4, R7 and R9 are as defined above under (A); and R is C2-C4alkenyl or C2-C4alkynyl which are substituted or unsubstituted, and where the substituents independently of one another are chosen from the group consisting of halogen, C1-C6alkyl, haloidC1-C6alkyl, C3-C6cycloalkyl, haloidC3-C6cycloalkyl, C1-C6alkoxy, haloidC1-C6alkoxy, C1-C6alkylthio, haloidC1-C6alkylthio, ph