TH96546A - Ketone and oxidative inhibitors that kill pests and animals. - Google Patents

Abstract

DC60 (16/09/47) A compound of the formula (chemical formula) (I), in which A0, A1 and A2, which are independent of each other, are C1-C6 alkylene bonds or linkers; A3 is the C1-C6 alkylene linker which has no substituents or is replaced by one to six identical or different substituents chosen from halogens and C3-C8 cycloalkyl; Y is, for example, O, S, SO or SO2; M is O or NOR6, X1 and X2, each independent of each other, is fluorine, chlorine, or bromine; R1, R2, and R3 are, for example, H, halogen, OH, SH, CN, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C2-C6 alkenyl, C2-C6 haloalkenyl, or C2-C6 alkinyl; Q is, for example, O, S, SO, or SO2; W is, for example, O, S, SO, SO2, -C(=O)-O-, or -O-C(=O)-; T is, for example, bond, O, S, SO, SO2, -C(=O)-O-, or -O-C(=O)-; D is CH or N; R4 is, for example, H, halogen, OH, SH, CN, nitro, C1-C6 alkyl, or C1-C6 haloalkyl. R5 is, for example, C1-C12 alkyl, C3-C8 cycloalkyl or -N(R7)2; R7 is H, C1-C6 alkyl, C1-C3 haloalkyl, C1-C6 alkylcarbonyl, C1-C3 haloalkyl carbonyl, C1-C6 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylcarbonyl or formyl; K is 0, 1, 2, 3 or 4; m is 1 or 2; and q is 0, 1 or 2; and, where applicable, its possible E/Z isomers, mixtures of E/Z isomers and/or totomers, in each case in free form or in salt form, methods for the preparation of such compounds and their use, pesticide mixtures in which the active component has been selected from those compounds. and its salts that are accepted in agrochemicals, and the methods for the preparation of those mixtures and their use, on plant propagation material treated with those mixtures, and methods for controlling pests and animals. Compounds of the formula (chemical formula) (I), in which A0, A1 and A2, which are independent of each other, are C1-C6 alkylene bonds or linkers; A3 is the C1-C6 alkylene linker which has no substituents or is replaced by one to six identical or different substituents selected from halogens and C3-C8 cycloalkyl; Y is, for example, O, S, SO or SO2; M is O or NOR6, X1 and X2, each independent of each other, is fluorine, chlorine, or bromine; R1, R2, and R3 are, for example, H, halogen, OH, SH, CN, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C2-C6 alkenyl, C2-C6 haloalkenyl, or C2-C6 alkinyl; Q is, for example, O, S, SO, or SO2; W is, for example, O, S, SO, SO2, -C(=O)-O-, or -O-C(=O)-; T is, for example, bond, O, S, SO, SO2, -C(=O)-O-, or -O-C(=O)-; D is CH or N; R4 is, for example, H, halogen, OH, SH, CN, nitro, C1-C6 alkyl, or C1-C6 haloalkyl. R5 is, for example, C1-C12 alkyl, C3-C8 cycloalkyl or -N(R7)2; R7 is H, C1-C6 alkyl, C1-C3 haloalkyl, C1-C6 alkylcarbonyl, C1-C3 haloalkyl carbonyl, C1-C6 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylcarbonyl or formyl; K is 0, 1, 2, 3 or 4; m is 1 or 2; and q is 0, 1 or 2; and, where applicable, its possible E/Z isomers, mixtures of E/Z isomers and/or totomers, in each case in free form or in salt form, methods for the preparation of such compounds and their use, pesticide mixtures in which the active component has been selected from those compounds. and its salts that are accepted in agrochemicals, and the methods for preparing those mixtures and their use, on plant propagation material treated with those mixtures, and methods for controlling pests and animals.

Claims (11)

1. A compound of the formula (chemical formula) (I), in which independent A0, A1 and A2 are C1-C6 alkylene bonds or are replaced by one to six identical or differential substituents chosen from halogens and C3-C8 cycloalkyl bonds; A3 is a C1-C6 alkylene bridge which is either unsubstituted or replaced by one to six identical or differential substituents chosen from halogens and C3-C8 cycloalkyl bonds; Y is O, NR11, S, SO or SO2; M is O or NOR6, X1 and X2 each independent of each other is fluorine, chlorine, or bromine; R1, R2, and R3 are, each independent of the other, H, halogen, OH, SH, CN, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl; C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C1-C6 alkynyloxy, -S(=O)-C1-C6 alkyl, -S(=O)2-C1-C6 alkyl, C1-C6 alkoxycarbonyl, or C3-C6 haloalkinyloxy; The substituent groups R3 are independent of each other when m is 2; Q is, O, NR11, S, SO, or SO2; W is, O, NR11, S, SO, SO2, -C(=O)-O-, -O-C(=O)-; -C(=O)-NR11- or -NR11-C(=O)-; T is the bond, O, NR11, S, SO, SO2, -C(=O)-O-, -O-C(=O)-, -C(=O)-NR11- or -NR11C(=O)-; D is CH or N; R4 is H, halogen, OH, SH, CN, nitro, C1-C6 alkyl, C1-C6 haloalkyl; C1-C6 alkyl carbonyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkynyl oxy, C1-C6 haloalkenyl oxy, C2-C6 alkynyl oxy, -S(=O)-C1-C6 alkyl. -S(=O)2-C1-C6 alkyl, C1-C6-alkoxycarbonyl, C3-C6 haloalkinyloxy, NH2,NH(C1-C6 alkyl) or N(C1-C6 alkyl)2, where the two alkyl groups are independent of each other; The R4 substituents are independent of each other when K is greater than 1; R5 is a C1-C12 alkyl, replaced by one to five substituents selected from the groups that comprise -N3, NO2, OH, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkinyl, C3-C6 haloalkinyl-oxy, C3-C8 cycloalkyl-C1-C6 alkoxy, C1-C6 alkyl carbonyl, C1-C6 haloalkyl carbonyl, C1-C6 alkoxy-C1-C6 alkoxy, -P(=O)(OC1-C6). The C3-C8 cycloalkyl substituents are replaced by one to five identical or different substituents selected from groups comprising C1-C6 alkyl, halogen, CN, NO2, OH, C1-C6 alkoxy, C1-C6 haloalkoxy, NH2, NH(C1-C6 alkyl) and N(C1-C6 alkyl)2, where the two alkyl groups are independent of each other; -N(R7)2; where the two R7s are independent of each other; and -NR14S(O)qR15; C3-C8 cycloalkyl substituents are replaced by one to five identical or different substituents selected from groups comprising C1-C6 alkyl, halogen, CN, NO2, OH, C1-C6 alkoxy, C1-C6 haloalkoxy, NH2, NH(C1-C6 alkyl) and N(C1-C6 alkyl)2, where the two alkyl groups are independent of each other; -N(R7)2; where the two R7s are independent of each other; -C(=O)-O-R8; -C(=O)-R9; -C(=O)-NH-R39; -C(=N-O-R9)R10; -C(=N-NH-R9)R10; C2-C6 alkenyl; C2-C6 alkinyl; heterocyclyl; or -NR14S(O)qR15, where alkenyl and alkinyl radicals are not substituted or, depending on the possibility of substitution, are substituted by one to five identical or different substituents selected from groups comprising halogens, -N3, CN, NO2, OH, C3-C8 cycloalkyl, C1-C6-alkoxy, C1-C6 halo-alkoxy, C2-C6 alkenyl oxyl. C2-C6 haloalkinyloxy, C3-C6 alkynyloxy, C3-C6 halo-alkinyloxy, C3-C8 cycloalkyl-C1-C6 alkoxy, C1-C6 alkyl carbonyl, C1-C6 haloalkyl carbonyl, C1-C6-alkoxycarbonyl, C1-C6 alkyl carbonyl-C1-C6 alkyl, C1-C6 alkoxy Carbonyl-C1-C6 alkyl, C3-C6 halo alkynyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 halo alkoxy-C1-C6 alkyl, C2-C6 alkynyl oxy-C1-C6 alkyl, C2-C6 halo alkynyl oxy-C1-C6 alkyl, C3-C6 alkynyl oxy-C1-C6 alkyl, -P(=O)(OC1-C6 alkyl)2,-S(O)q-R13, NH2, NH(C1-C6 alkyl) and N(C1-C6 alkyl)2, where the two alkyl groups are independent of each other; and where the heterocyclyl radicals mentioned under R5 have no substituents or, depending on the likelihood. Substitution is achieved by replacing one to five selected substituents from the halogens: CN, NO2, OH, SH, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6-haloalkenyl, C3-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6. Alkenyloxy, C2-C6 haloalkenyloxy, C3-C6, alkynyloxy, C3-C6 haloalkinyloxy, C3-C8 cycloalkyl-C1-C6 alkoxy, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl, C1-C6 alkylthio, C2-C6 alkenylthio, C3-C6 alkynylthio, C3-C6 cycloalkyl-C1-C6 alkylthio, C3-C6 haloalkinyl. C2-C6 haloalkenylthio, C1-C6 haloalkylthio, C1-C6 alkoxy,-C1-C6 alkyl, C1-C6 haloalkoxy -C1-C6 alkyl, C2-C6 alkinyloxy-C1-C6 alkyl, C2-C6 haloalkenyloxy, -C1-C6 alkyl, C3-C6 alkynyloxy-C1-C6 alkyl, NH2, NH(C1-C6 alkyl), N(C1-C6 alkyl)2 in which the two alkyl groups are independent, C1-C6 alkyl carbonyl amino, C1-C6 haloalkyl carbonyl amino, C1-C6 alkoxy carbonyl amino, and C1-C6 alkyl amino carbonyl amino; Or, when A0 is the C1-C6 alkyl linker, R5 is the C2-C6 alkyl linker bonded to one of the carbon atoms of A0; or, when R4 and the -C(=NOR6)R5 are orthodependent, R4 and R5 together form a C2-C6 alkyl linker in which one or two independent CH2 groups may be replaced by O, NR12, S, or SO, and in which the CH2 group is unsubstituted or mono- or di-substituted by halogen, OH, SH, CN, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; R6 is H, C1-C12 alkyls, C3-C8 cycloalkyls, C1-C6 alkylcarbonyls, C2-C6 alkenyls, C2-C6 alkinyls, aryls, heterocyclyls, or benzyls, where alkyls, cycloalkyls, alkenyls, and alkinyl radicals are either unsubstituted or, depending on the possibility of substitution, are substituted by one to five identical or different substituents. Selected from groups containing halogens, -N3, CN, NO2, OH, SH, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkinyloxy, C3-C6 akinyloxy, C3-C6 haloalkinyloxy, C3-C8 cycloalkyl-C1-C6 alkoxy, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 alkyl, C1-C6 alkoxycarbonyl -C1-C6 alkyl, C1-C6 alkylthio, C2-C6 alkenilthio, C3-C6 alkinilthio, C3-C6 cycloalkyl-C1-C6 alkylthio, C1-C6 halo alkinil, C2-C6 halo alkenilthio, C1-C6 halo alkylthio, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 halo alkoxy-C1-C6 alkyl, C2-C6 alkenyloxy-C1-C6 alkyl, C2-C6 halo alkenyloxy-C1-C6 alkyl, C3-C6 alkinyloxy-C1-C6 alkyl, NH2, NH(C1-C6 alkyl), N(C1-C6 alkyl)2, in which the two alkyl groups are independent of each other, C1-C6 alkyl carbonylamino, C1-C6 haloalkyl carbonylamino, C1-C6 alkoxycarbonylamino, and C1-C6 alkylaminocarbonylamino; and aryl, heterocyclyl, and benzyl radicals are either unsubstituted or, depending on the possibility of substitution, are substituted by one to five identical or different substituents selected from the groups which Contains halogens, CN, NO2, OH, SH, C1-C6 alkyls, C1-C6 haloalkyls, C2-C6 alkenyls, C2-C6 haloalkenyls, C3-C6 alkinyls, C3-C8 cycloalkyls, C3-C8 cycloalkyl-C1-C6 alkyls, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkinyloxy, C3-C6 alkinyloxy, C3-C8. Haloalkyl-C1-C6alkoxy, C1-C6alkyl carbonyl, C1-C6 haloalkyl carbonyl, C1-C6alkoxycarbonyl, C1-C6alkyl carbonyl-C1-C6 Alkyl-C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkylthio, C2-C6 alkenylthio, C3-C6 alkynylthio, C3-C6 cycloalkyl-C1-C6 alkylthio, C3-C6 haloalkinyl, C2-C6 haloalkinylthio, C1-C6 haloalkylthio, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 haloalkoxy-C1-C6 alkyl, C2-C6 alkenyloxy-C1-C6 alkyl, C2-C6 haloalkinyloxy-C1-C6 alkyl, C3-C6 alkynyloxy-C1-C6 alkyl, NH2, NH(C1-C6 alkyl), N(C1-C6 alkyl)2, where the two alkyl groups are independent of each other, C1-C6 alkyl carbonylamino, C1-C6 haloalkyl carbonylamino, C1-C6 alkoxycarbonylamino, and C1-C6 alkylaminocarbonylamino; R7 is H, C1-C6 alkyl, C1-C3 haloalkyl, C1-C6 alkyl carbonyl, C1-C3 haloalkyl carbonyl, C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C8 cycloalkyl carbonyl or formil; R8 is H, C1-C12 alkyls are replaced by one to five identical or different substituents. Selected from halogens, -N3, CN, NO2, OH, C1-C6 alkoxy, C1-C6 alkylthio, NH2,NH(C1-C6 alkyl), N(C1-C6 alkyl)2, where the two alkyl groups are independent of each other, and C1-C6 alkyl carbonyl amino; C3-C8 cycloalkyl, C1-C6 alkyl carbonyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkinyl, C2-C6 haloalkinyl, aryl, heterocyclyl or benzyl, where aryl, heterocyclyl and benzyl radicals are not substituted or, depending on the possibility of substitution, are substituted by one to two. Five substituent groups selected from the group composition include halogens, CN, NO2, OH, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6-alkinyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6. Haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkinyloxy, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C2-C6 alkenylthio, C3-C6 alkynylthio, C1-C6 alkylthio, C3-C6 haloalkinyl, C1-C6 haloalkylthio, C1-C6 alkoxy-C1-C6 alkyl, NH2, NH(C1-C6 alkyl), N(C1-C6 alkyl)2, C1-C6 alkylcarbonylamino, C1-C6 haloalkylcarbonylamino, C1-C6 alkoxycarbonylamino, and C1-C6 alkylaminocarbonylamino; R9 is H, C1-C12 alkyls are either unsubstituted or substituted by one to five identical or different substituents selected from halogens, CN, NO2, OH, C1-C6 alkoxy, C1-C6 alkylthio, NH2, NH(C1-C6 alkyl), N(C1-C6 alkyl)2 where the two alkyl groups are independent of each other, and C1-C6 alkylcarbonylamino; C3-C8 cycloalkyl, C1-C6 alkylcarbonyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkinyl, C2-C6 haloalkinyl, aryl, heterocyclyl, or benzyl, where aryl, heterocyclyl, and benzyl radicals are not substituted or, depending on the possibility of substitution, are substituted by one to five substituents selected from groups containing halogens, CN, NO2, OH, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkinyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkinyloxy, C1-C6 alkylcarbonyl, C1-C6 haloalkyl carbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C2-C6 alkenylthio, C3-C6 alkynylthio, C1-C6 alkylthio, C3-C6 haloalkinyl, C1-C6 Haloalkylthio, C1-C6 alkoxy-C1-C6 alkyl, NH2,NH(C1-C6 alkyl), N(C1-C6 alkyl)2 in which the two alkyl groups are independent, C1-C6 alkylcarbonylamino, C1-C6 haloalkylcarbonylamino, C1-C6 alkoxycarbonylamino, and C1-C6 alkylaminocarbonylamino; R10 is H, C1-C12 alkyls that are unsubstituted or substituted by one to five identical or different substituents. Selected from halogens, CN, NO2, OH, C1-C6 alkoxy, C1-C6 alkylthio, NH2, NH(C1-C6 alkyl), N(C1-C6 alkyl)2 and C1-C6 alkylcarbonylamino; C3-C8 cycloalkyl, C2-C6 alkinyl, C2-C6 haloalkenyl, C2-C6 alkynyl, aryl, heterocyclyl or benzyl, where aryl, heterocyclyl and benzyl radicals are not substituted or, depending on the possibility of substitution, are substituted by one to five identical or different substituents selected from the constituent groups. Including halogens, CN, NO2, OH, SH, C1-C6 alkyls, C1-C6 haloalkyls, C3-C8 cycloalkyls, C1-C6-alkoxy, C1-C6 haloalkoxy, C1-C6 alkylcarbonyls, C1-C6 haloalkylcarbonyls, C1-C6 alkoxycarbonyls, C1-C6 alkylcarbonyl-C1-C6 alkyls, C1-C6 alkoxy-C1-C6 alkyls, NH2, NH(C1-C6 alkyls), N(C1-C6 alkyls)2 The two alkyl groups are independent of each other: C1-C6 alkyl carbonylamino, C1-C6 haloalkyl carbonylamino, C1-C6 alkoxycarbonylamino, and C1-C6 alkylaminocarbonylamino; R11 and R12 each have independent groups: H, C1-C6 alkyl, C1-C3 haloalkyl, C1-C6 alkyl carbonyl, C1-C3 haloalkyl carbonyl, C1-C6 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C6 alkyl, or C3-C8 cycloalkyl carbonyl; R13 is H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C1-C6 haloalkyl; R14 is H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C1-C6 haloalkyl; R15 is H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C1-C6 haloalkyl; k is 0, 1, 2, 3, or 4; m is 1 or 2; and q is 0, 1, or 2; or, where applicable, possible E/Z isomers, mixtures of E/Z isomers and/or their totomers, in each case in free form or in salt form. 2. The compound according to claim 1, where M is NOR6, 3. The compound according to claim 1, where M is O. 4. Any compound under any of the claims in Claims 1 through 3 in its free form. 5. Any compound under any of the claims in Claims 1 through 4, where X1 and X2 are chlorine or bromine. 6. A compound according to any one of the claims in Claims 1 through 5, where D is CH. 7. A compound according to any one of the claims in claims 1 through 6, where A3 is a straight-chain alkylene linker. 8. A compound according to any of the claims in claims 1 through 7, where R5 is C1-C12 alkoxy-C1-C12 alkyl. 9. Any compound under any of the claims in Claims 1 through 7, where R5 is heterocyclic. 10. A pesticide mixture containing at least one active ingredient defined in any of the claims in Claims 1 through 9, in its free form or in an agrochemically acceptable salt form, and at least one auxiliary. 11. Methods of pest and animal control which include the use of pesticide mixtures as defined in Claim 10 against pests and animals or against points of their outbreak.