Patent ID: 6204221
Filing Date: 2001-03-20
Classification: A01N,C07D

Abstract:
A compound of the formula I ##STR286##in whichA is .dbd.N-- or ##STR287##n.sub.13 is 1, 2 or 3;R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 halogenoalkyl, cyano-C.sub.1 -C.sub.4 alkyl, C.sub.3 - or C.sub.4 alkenyl, C.sub.3 - or C.sub.4 halogenoalkenyl, C.sub.3 - or C.sub.4 alkynyl or C.sub.3 -C.sub.6 cycloalkyl;R.sub.2 is C.sub.1 -C.sub.4 halogenoalkyl;R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 halogenoalkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 -halogenoalkenyl, C.sub.2 -C.sub.6 alkynyl, halogen, cyano, NH.sub.2 C(S)--, nitro, OHC-- or R.sub.18 R.sub.19 N--;R.sub.18 and R.sub.19 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 halogenoalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 halogenoalkenyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.6 alkylcarbonyl, C.sub.1 -C.sub.6 halogenoalkylcarbonyl, C.sub.2 -C.sub.6 alkenylcarbonyl, C.sub.2 -C.sub.6 halogenoalkenylcarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl or C.sub.1 -C.sub.6 halogenoalkylsulfonyl;R.sub.11 is hydrogen, fluorine, chlorine, bromine or methyl;R.sub.13 is hydrogen, halogen, cyano, CIS(O).sub.2 --, CIC(O)--, nitro, amino, ##STR288##HS--, R.sub.20 NH-- orR.sub.20 R.sub.21 N--;R.sub.20 and R.sub.21 independently of one another are C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.8 halogenoalkyl, C.sub.3 -C.sub.8 halogenoalkenyl, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.4 -halogenoalkylcarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 halogenalkylsulfonyl, benzyl or benzyl which is substituted on the phenyl ring once to three times by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 -halogenoalkyl; orR.sub.13 is R.sub.30 O--;R.sub.30 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.3 -C.sub.8 halogenoalkenyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyloxy-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkynyloxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 alkoxycarbonyl, C.sub.3 -C.sub.8 alkenyloxycarbonyl, benzyloxycarbonyl, phenyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, where these aromatic and heteroaromatic rings mentioned can be unsubstituted or substituted once to three times by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl; orR.sub.30 is R.sub.31 X.sub.1 C(O)--C.sub.1 -C.sub.8 alkyl- or ##STR289##X.sub.1 is oxygen, sulfur or ##STR290##R.sub.31 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.3 -C.sub.8 halogenoalkenyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyloxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, phenyl, phenyl which is substituted once to three times by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl;R.sub.32 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.1 -C.sub.8 -halogenoalkyl; orR.sub.13 is R.sub.33 S(O).sub.n2 --;n.sub.2 is 0, 1 or 2;R.sub.33 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cyCloalkyl, C.sub.1 -C.sub.8 halogenoalkyl, C.sub.3 -C.sub.8 halogenoalkenyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyloxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 -alkyl, phenyl, phenyl which is substituted once to three times by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, and, if n.sub.2 is 0,R.sub.33 is hydrogen, C.sub.1 -C.sub.8 alkylcarbonyl or R.sub.34 X.sub.2 C(O)--;X.sub.2 is oxygen, sulfur or ##STR291##R.sub.34 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.3 -C.sub.8 halogenoalkenyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyloxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, phenyl, phenyl which is substituted once to three times by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl;R.sub.35 is hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.8 alkenyl; orR.sub.13 is R.sub.36 R.sub.37 NS(O).sub.2 --;R.sub.36 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl or C.sub.3 -C.sub.6 cycloalkyl;R.sub.37 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -CBalkynyl, C.sub.1 -C.sub.8 halogenoalkyl, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 halogenoalkylcarbonyl, benzoyl or benzoyl which is substituted once to three times on the phenyl ring by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl;R.sub.13 is R.sub.40 C(O)--;R.sub.40 is hydrogen, fluorine, chlorine, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.8 halogenoalkyl, cyano-C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.8 halogenoalkenyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyloxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, phenyl, phenyl which is substituted once to three times by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 -halogeno-alkyl; orR.sub.13 is R.sub.50 X.sub.3 C(O)--;X.sub.3 is oxygen, sulfur, ##STR292##R.sub.50 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.3 -C.sub.8 halogenoalkenyl, cyano-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyloxy-C.sub.1 -C.sub.4 alkyl, (oxiranyl)--CH.sub.2 --, oxetanyl-, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, phenyl, phenyl which is substituted once to three times by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, phenyl-C.sub.2 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyl-CO--C.sub.1 -C.sub.4 alkyl, ##STR293##R.sub.53 X.sub.4 C(O)--C.sub.1 --C.sub.6 alkyl, ##STR294##or R.sub.53 X.sub.4 C(O)--C.sub.3 -C.sub.6 cycloalkyl;X.sub.4 is oxygen, sulfur, ##STR295##R.sub.53 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.3 -C.sub.8 halogenoalkenyl, cyano-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 -alkenyloxy-C.sub.1 -C.sub.4 alkyl, (oxiranyl)--CH.sub.2 --, oxetanyl-, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, phenyl, phenyl which is substituted once to three times by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, benzyl, benzyl which is substituted once to three times on the phenyl ring by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl, or phenyl-C.sub.2 -C.sub.6 alkyl;R.sub.51, R.sub.52, R.sub.54 and R.sub.55 independently of one another are hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 halogenoalkyl or benzyl; orR.sub.13 is B.sub.1 -C.sub.1 -C.sub.8 alkyl, B.sub.1 -C.sub.2 -C.sub.8 alkenyl,B.sub.1 -C.sub.2 -C.sub.8 alkynyl, B.sub.1 -C.sub.1 -C.sub.8 halogenoalkyl,B.sub.1 -C.sub.2 -C.sub.8 halogenoalkenyl, B.sub.1 -C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, B.sub.1 -C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl orB.sub.1 -C.sub.3 -C.sub.6 cycloalkyl;B.sub.1 is hydrogen, cyano, hydroxyl, C.sub.1 -C.sub.8 alkoxy, C.sub.3 -C.sub.8 alkenyloxy, R.sub.60 X.sub.5 C(O)--, C.sub.1 -C.sub.4 -alkylcarbonyl or C.sub.1 -C.sub.4 halogenoalkylcarbonyl;X.sub.5 has the meaning of X.sub.4 ;R.sub.60 has the meaning of R.sub.53 ; orR.sub.13 is B.sub.2 -C(R.sub.70).dbd.CH--;B.sub.2 is nitro, cyano or R.sub.71 X.sub.6 C(O)--;R.sub.70 is cyano or R.sub.72 X.sub.7 C(O)--;X.sub.6 and X.sub.7 have the meaning of X.sub.4 ; andR.sub.71 and R.sub.72 have the meaning of R.sub.53,or a pyrazole N-oxide, agrochemically tolerated salt or stereoisomer of this compound of the formula I.