Patent ID: 6723720
Filing Date: 2004-04-20
Classification: A01N,C07D

Abstract:
A compound of formula whereinR1 is unsubstituted or mono- to penta-substituted phenyl, unsubstituted or mono- to penta-substituted naphthyl or an unsubstituted or mono- to penta-substituted heteroaryl group comprising pyridyl, pyrimidyl, s-triazinyl, 1,3,4-triazinyl, thienyl, furanyl, pyrryl, pyrazolyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, benzothienyl, benzofuranyl, benzothiazolyl, indolyl or indazolyl, the substituents being selected from the group consisting of OH, halogen, CN, NO2, C1-C6alkyl, C3-C8cycloalkyl, optionally substituted C3-C8cycloalkenyl, C1-C6alkyl-C3-C8cycloalkyl, C3-C8cycloalkyl-C1-C6alkyl, C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6alkoxy, C3-C8cycloalkoxy, C1-C6haloalkoxy, C3-C8halocycloalkoxy, C1-C6alkylthio, C3-C8cycloalkylthio, C1-C6haloalkylthio, C3-C8halocycloalkylthio, C1-C6alkylsulfinyl, C3-C8cycloalkylsulfonyl, C1-C6haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, C1-C6alkylsulfonyl, C3-C8cycloalkylsulfonyl, C1-C6haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, optionally substituted C2-C8alkenyl, optionally substituted C2-C8alkynyl, C1-C6alkylcarbonyl, C1-C6alkyl-C(&boxH;NOR6), â€”P(&boxH;O)(OC1-C6alkyl)2, R7, unsubstituted or mono- to penta-substituted phenyl, an unsubstituted or mono- to penta-substituted heteroaryl group comprising pyridyl, pyrimidyl, s-triazinyl, thienyl, furanyl, pyrryl, pyrazolyl, imidazolyl, thiazoyl, oxazolyl, thiadiazolyl, oxadiazolyl, benzothienyl, benzofuranyl, benzothiazolyl, indolyl or indazolyl; wherein the substituents of the said phenyl and heteroaryl radicals are selected from the group consisting of OH, halogen, CN, NO2, C1-C6alkyl, optionally substituted C2-C8alkenyl, optionally substituted C2-C8alkynyl, C3-C8cycloalkyl, optionally substituted C3-C8cycloalkenyl, C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6alkoxy, C3-C8cycloalkoxy, C1-C6haloalkoxy, C3-C8halocycloalkoxy, C1-C6alkylthio, C3-C8cycloalkylthio, C1-C6haloalkylthio, C3-C8halocycloalkylthio, C1-C6alkylsulfinyl, C3-C8cycloalkylsulfonyl, C1-C6haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, C1-C6alkylsulfonyl, C3-C8cycloalkylsulfonyl, C1-C6haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, C2-C8alkenyl, which is unsubstituted or substituted, C2-C8alkynyl, which is unsubstituted or substituted, C1-C6alkylcarbonyl, â€”CH(&boxH;NOR6), â€”C(C1-C6alkyl)(NOR6), C1-C6alkyl-C(NOR6), â€”CHO, â€”C(&boxH;O)â€”C1-C6alkyl and R7; unsubstituted or mono- to penta-substituted phenoxy; unsubstituted or mono- to penta-substituted phenylthio; unsubstituted or mono- to penta-substituted phenylamino; and unsubstituted or mono- to penta-substituted phenyl-(C1-C6alkyl)-amino; the substituents of the phenoxy, phenylthio, phenylamino and phenyl-(C1-C6alkyl)-amino groups being selected from the group consisting of halogen, CN, NO2, C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C8cycloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C3-C8cycloalkylthio, C1-C6haloalkylthio and C3-C8halocycloalkylthio; R2 is H, OH, halogen, CN, NO2, optionally substituted C1-C6alkyl, C1-C6alkoxy, C1-C6alkoxy-C1-C6alkyl, C1-C6alkylthio, C1-C6alkylthio-C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl, C3-C8halocycloalkyl, â€”NHâ€”C1-C6-alkyl, SH or CH2-NO2; A is a single bond, C1-C12alkylene, O, O(C1-C12alkylene), S(O)n, S(O)n(C1-C12alkylene), C2-C8alkenylene, C2-C8alkynylene; NR3 or NR3(C1-C12alkylene); R3 is H, C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl, C2-C8alkenyl, C2-C8alkynyl, aryl-C1-C6alkyl, (CH2)pC(O)R4 or C1-C6alkoxy-C2-C6alkyl; R4 is H, C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl, C1-C6alkoxy, N(R5)2 or C1-C6alkoxyC2-C6alkyl; R5 is H, C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl or aryl-C1-C6alkyl; R6 is H, C1-C6alkyl, C3-C8cycloalkyl or â€”C(&boxH;O)â€”R5; R7 is R8 and R9 are each independently of the other H or C1-C6alkyl; X1 is R10; X2 and X3 are each independently of the other H or R10; R10 is halogen, CN, NO2, C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6alkoxy, C3-C8cycloalkoxy, C1-C6haloalkoxy, C3-C8halocycloalkoxy, C1-C6alkylthio, C3-C8cycloalkylthio, C1-C6haloalkylthio or C3-C8halocycloalkylthio; m is 1, 2, 3 or 4; n is 0, 1 or 2; and W is O or S; and the physiologically tolerable and agrochemically acceptable additional compounds thereof, and where appropriate to E/Z isomers, to mixtures of E/Z isomers and to tautomers, in each case in free form or in salt form, with the proviso that the radical Aâ€”R1 and the phenyl group substituted by X1, X2 and X3 are not in the vicinal position relative to one another on the triazine ring, with the further proviso, that X1 is not CH3, Cl or F, when X2 and X3 are H, A is a single bond, R1 is phenyl, 2-fluorophenyl, p-fluorophenyl or 3-chlorophenyl and R2 is H, Cl or NHC2â€”H5; and with the exception of 3,6-di-(2-chlorophenyl)-5-hydroxy-1,2,4-triazine and with the exception of 3-(2-methylphenyl)-6-(4-methylphenyl)-5-trifluoromethyl-1,2,4-triazine.