TH46450A - The organic compound 1-aryl-hydrazono-2-nitrilo-aryl - Google Patents

Abstract

DC60 (26/02/42) The compound formula (chemical formula) (I), where A1 and A2, which are independent of each other, represent either aryl or heteroaryl radicals, and where A1 is appropriately substituted by the substitute (R3a)n1 and A2, where it is appropriately substituted by the substitute (R3b)n2, n1 and n2 are 1, 2, 3, or 4, which are independent of each other. And either R3a or R3b, which are independent of each other, would be, for example, halogen, C1-C6 alkyl, C2-C4 alkinil, halogen-C1-C6 alkyl, halogen-C2-C4 alkinil, C1-C6 alkoxy, halogen-C1-C6 alkoxy, C2-C6 alkiniloxy, C2-C6 alkiniloxy, or halogen-C2-C6 alkiniloxy, and R2 is R2a; R2a, for example, is -C1-C6 alkyl-NR11R12, -COC9-C20 alkyl, -C1-C6 alkyl-O-C1-C6. Alkyl-O-C1-C6 alkyl or -CH2O(C=O)C1-C6 alkyl or at least one of the R3a or R3b radicals, namely -CR5=CR5R14, -NR11R12, C(=O)CN, -C(=O)C(=O)O-C1-C6 alkyl, -CR7=NOR10, or a heteroeryl ring with five or six members. This bond is formed by carbon atoms R2, which is either R2a or R2b, where R2a is as previously defined and R2b, for example, is hydrogen, -OH, C1-C6 alkyl, or C1-C6 alkoxy. R14, for example, is hydrogen, halogen, C1-C6 alkyl, or halogen-C1-C6 alkyl. X is O or S; p is 0, 1, or 2; R5 is H or independent C1-C8 alkyls; R6, for example, is H, C1-C8 alkyl, or C3-C6 cycloalkyl. Independent R7 is, for example, H, C1-C8 alkyl, or C2-C8 alkenyl, or halogen-C1-C8 alkyl. R8 is, for example, C1-C8 alkyl, C1-C8 alkenyl, or halogen-C1-C8 alkyl. R9 is C1-C6 alkyl, halogen-C1-C4 alkyl, or aryl. R10 is H, C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, or benzyl. R11 and R12 are, for example, H, C1-C6 alkyl, or phenyl. Where appropriate, possible E/Z isomers, E/Z isomer mixtures, and/or their totomers, in their free form or in agriculturally acceptable forms, can be used as active agricultural components and may be prepared using known methods. A compound formula (chemical formula) where independent A1 and A2 represent aryl or heteroaryl radicals, and A1 is appropriately replaced by (R3a)n1 and A2 is appropriately replaced by (R3b)n2, n1 and n2 are independent 1, 2, 3, or 4, and either independent R3 and R3b are, for example, halogen, C1-C6 alkoxy, halogen-C1-C6 alkoxy, C2-C6 alkinyloxy, C2-C6 alkinyloxy, or halogen-C2-C6 alkinyloxy, and R2 is R2a:R2a. For example, -C1-C6 alkyl-NR11R12, -COC9-C20. Alkyl,-C1-C6 alkyl-O-C1-6 alkyl-O-C-1-C6 alkyl or -CH2O(O=O)C1-C6 alkyl or at least one of the radicals R3 or R2b is -CR5=CR5R14,-NR11R12,-C(=O)CN,-C(=O)C(=O)O=C-1-C6 alkyl,-CR7=NOR10 or a heteroeryl ring with five or six members bonded by a carbon atom R2 is R2a or R2b, where R2a is as previously defined here and R2b, for example, is hydrogen,-OH,C1-C6 alkyl or C1-C6 alkoxy. R14, for example, is hydrogen, halogen,C1-C6 alkyl or halo. R5 is H or C1-C8 alkyl; X is O or S; p is 0, 1, or 2; R5 is H or C1-C8 independent alkyls; R6, for example, is H, C1-C8 alkyls or C3-C6 independent cycloalkyls; R7, for example, is H, C1-C8 alkyls, C2-C8 alkenyls, or halogen-C1-C8 alkyls; R8, for example, is C1-C8 alkyls, C1-C8 alkenyls, or halogen-C1-C8 alkyls; R9 is C1-C6 alkyls, halogen-C1-C4 alkyls, or aryls; R10 is H, C1-C6 alkyls, C3-C6 cycloalkyls, phenyls, or benzyls; R11 and R12, for example, are H, C1-C6 alkyls or phenyls, and where appropriate, E/Z. Possible isomers, E/Z mixtures, and/or their totomers, in free form or in agriculturally acceptable forms, can be used as active agricultural components and may be prepared using known methods.

Claims (14)

1. The compound formula (chemical formula) is given by A, and A2, which are independent of each other and in each case represent monocyclic or bicyclic aryl or heteroaryl radicals, and each independent heteroaryl radical has 1 to 4 heteroatoms selected from the N,O, and S groups, and A, is substituted where suitable by the substitute (R3a)n1 and A2 where suitable by the substitute (R3b)n2. n1 and n2 are 1, 2, 3, or 4, each independent of the other, depending on the possibilities for substitution on the A1 and A2 rings, and either of the independent (A)R3a and R3b will be hydrogen, halogen, C1-C6 alkyl, halogen-C1-C6 alkyl, C2-C4 alkenyl, C2-C4 alkyl, halogen-C2-C4. Alkinil, Halogen-C2-C4 Alkinil,C1-C6 Alkoxy, Halogen-C1-C6-Alkoxy,C2-C6 Alkiniloxy,C2-C6-Alkiniloxy, Halogen-C2-C6 Alkiniloxy, Halogen-C2-C6-Alkiniloxy,-OH,-SF5,-CHO,-C(=O)-C1-C6-Alkyl,-C(=O)-Halogen-C1-C6 Alkyl,-C(=O)-OC1-C6 Alkyl,-C(=O)-OC,Alkyl,-C(=O)-O-Halogen-C1-C6 Alkyd,O-C(=O)N(R5)2(where both representatives at R6 are independent of each other), -CN,-NO2,-S(=O)2N(R6)2 (where the two representatives at R6 are independent of each other),-S(=O)p-C1-C6 alkyl,-O-S(-O)p-C1-C6 alkyl,-OS(=O)2-halogen-C1-C6-alkyl,phenyl,benzyl,phenoxy or benzyloxy radicals, where each of the phenyl, benzyl, phenoxy or benzyloxy radicals is not replaced or is replaced in the aromatic ring independently one to five times by representatives selected from the halogen, cyano, NO2, C1-C6 groups. (B) R2a and R3b, which are independent of each other, shall be as defined under (A) and at least one of the radicals R3a or R3b, namely -CR5=CR5R14,-NR11R12,-C(=O)CN,-C(=O)-C1-C6 alkyl,-CR15=NOR10 or a heteroeryl ring with five or six complex units, shall be substituted where appropriate depending on the possibility of substitution on the ring with 1 to 3 substitutes selected from the groups consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, NO2 and CN and R2, which are R2a or (C) R3a shall be one of those defined herein. Before under (A) or (B), R3b is hydrogen, halogen, C1-C6 alkyl, halogen-C1-C4 alkyl, C2-C4 alkynyl, C2-C4 alkynyl, halogen-C2-alkynyl, halogen-C2-C4 altynyl, C1-C6 alkoxy, halogen-C1-C6-alkynyloxy, C2-C6 alkynyloxy, halogen-C2-C6 alkynyloxy, halogen-C2-C6 alkynyloxy, halogen-C2-C6 alkynyloxy,-OH,-SF5,-CHO,-C(=O)-halogen-C1-C6 alkyl,-C(=O)-OC1-C6 alkyl,-(C(=O)-O-halogen-C2-C6 Alkyl,-O-C(=O)N(R6)2 (where the two representatives at R6 are independent of each other),-CN,-NO2,phenyl,benzyl,phenoxy or benzyloxy such that each phenyl, benzyl,phenoxy or benzyloxy molecule is not independently replaced by one to five aromatic rings with representatives selected from the halogen, cyano, NO2,C1-C6 alkyl, halogen-C1-C6 alkyl,C1-C6 alkoxy and halogen-C1-C6 alkoxy,-S(=O),-C1-C6 alkyl at position 4 or -S(=O)p-halogen-C1-C6 alkyl at position 4, provided that one of the representatives at R3b is -S(=O)p-C1-C6. Alkyl or -S(=O)p-halogen-C1-C6 alkyl and R2 is R2a or R2b and in groups (A),(B) and (C) where appropriate R2a is -C1-C6 alkyl-NR11R12,-C(=X)-R12,-COC,9-C20 alkyl,-CH2O(C=O)C1-C6 alkyl,-C1-C6 alkyl-O-C1-C6 alkyl -O-C1-C6 alkyl,-CH2O(C=O)C2-C6 alkynyl,-CH2O(C=O)C2-C6 alkynyl,-C(=S)OC2-C6 alkynyl,- -C(=S)OC2-C6 alkynyl,-C(=S)SC1-C6 Alkyl,-C(=S)SC2-C6 Alkenil,-C(=S)SC2-C6 Alkinil,-C(=O)SC,-C6 Alkyl,-C(=O)SC2-C6 Alkinil,-C(=O)SC2-C6 Alkylthio-C1-C6 Alkyl,-C(=S)NR11R12,-C(=O)NR10OR13,-CH2OC2-C6 Alkenil,-CH2OC2-C6 Alkinil,-CH2OC2-C6 Haloalkenil or CH2OC2-C6 Haloalkinil R2b is hydrogen,-OH,C1-C6 Alkyl,C1-C6 Alkoxy, C3-C6 Cycloalkys,C3-C6 Alkenil,C3-C6 Alkinil, Halogen-C1-C6 Alkyl, halogen-C3-C6 alkynyl, halogen-C2-C6 altynyl, benzyl or benzoyl radicals, where the benzyl or benzoyl radicals are independently replaced in the aromatic ring one to three times by agents selected from the halogen, CN,NO2,C1-C6 alkoxy, halogen-C1-C6 alkyl and halogen-C1-C6 alkoxy;C1-C6 alkoxy-C1-C6 alkyl, cyano-C1-C6 alkyl,-C(=X)-R7a,-C(=X)-R7b,-OC(=O)-R2,-C(=O)-R2,-S(=O)pN(R6)2 (where the two agents at R6 are independent of each other), cyano,-C1-C6. Alkyl-N(R5)-C(=O)-R8,-C1-C6, alkyl-S-C(=S)-R8,C1-C6, alkyl-S(=O)p-R9,-S(=O)p-R9, or -CH2-N(R10)-SO2-R9. X is O or S, p is 0, 1, or 2, R5 is H or C1-C8 alkyl independently, R6 is H,C1-C8 alkyl,C3-C6. Cycloalkyl or phenyl or benzyl independently where the phenyl or benzyl group is replaced in the aromatic ring in a suitable and independent manner one to three times by a substitute selected from the halogen,-CN,NO2,C1-C6 alkyl,C1-C4 alkoxy, halogen-C1-C6 alkyl and halogen-C1-C6 groups. Alkoxy or two alkyl radicals R6, along with a nitrogen atom, are bonded to form a ring of five to seven members where the CH2 group is appropriately replaced by a heteroatom selected from groups containing O and S, or replaced by NH, and where the ring of five to seven members is appropriately replaced one or two times by C1-C4 alkyls. R7a is C1-C6 alkoxy-C1-C6 alkyl, CH2CH2CF2CI, C1-C6 alkylthio-C1-C6 alkyl, acyloxy-C1-C6 alkyl, halogen-C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, halogen-C3-C6 cycloalkyl-C1-C6 alkyl, aryloxy-C2-C6 alkyl or phenyl, benzyl, phenoxy. Or aryloxy-C1-C6 alkyls which are replaced by 1 to 3 substitutes which are selected from groups consisting of halogen, nitro, cyano, C1-C4 alkyls, halogen-C1-C4 alkyls and halogen-C1-C4 alkoxys. R7b is H, C1-C8 alkyls, C2-C8 alkynyls, halo-C1-C8 alkyls, halo-C2-C8 alkynyls, C1-C8 alkoxys, halo-C1-C8 alkoxys, C3-C6 cycloyalkyls, phenyls, benzyls, phenoxys, benzyloxys or -N(R6)2 (where two R6s are independent of each other). R8 is C1-C8 alkyls, C1-C8 alkoxys, halogen-C1-C8 alkyls, halogen-C1-C8. Alkoxy, C1-C8 alkylthio, phenyl, benzyl or -N(R6)2 (where the two R2 radicals are independent of each other). R9 is C1-C6 alkyl, halogen-C1-C4 alkyl or aryl which are not substituted or are substituted one to three times independently of each other by agents selected from the group consisting of C1-C6 alkyl, C2-C4 alkynyl, C2-C4 alkynyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen, cyano, halogen-C1-C4 alkyl, -C2-C4 alkynyl, halogen-C2-C4 alkynyl, halo R10 is composed of H,C1-C4 alkyl, C3-C6 alkyl, phenyl, oxytocin, and nitro radicals, where phenyl and benzyl radicals are either unsubstituted or independently substituted in the aromatic ring one to three times by representatives selected from groups consisting of C1-C4 alkyl, C1-C4 alkoxy, halogen, cyano, halogen-C1-C4 alkyl, halogen-C1-C4 alkoxy, and nitro radicals. R11 and R12 are independently composed of H,C1-C6 alkyl, phenyl, -COC1-C6 alkyl, -COC1-C6 haloalkyl-COphenyl, or in combination, forming five or six saturated or unsaturated ring units where, appropriately, one or more, particularly, one of the CH- or CH2 groups are replaced by a heterozygous radical. Selected atoms from groups containing O, N, and S, and where the ring has five or six members if suitable, are independently replaced by 1 to 3 substitutes selected from groups containing halogens, C1-C4 alkyls, C1-C4 haloalkyls, C1-C4 haloalxoxys, NO2, and CN, or two substitutes R11 and R12 together forming a ring (chemical formula) q is 2 or and R13 is H, C1-C6 alkyls, C2-C6 alkenyls, C2-C6 alkyls. R14 is hydrogen, C1-C6 alkyls, halogen-C3-C6 alkyls, C1-C6 alkoxys, halogen-C1-C6 alkoxys, C2-C6 alkenyloxys, -CHO, -C(=O)-C1-C6 alkyls, -C(=O)-halogens. Gen-C1-C6 alkyl,C(=O)-OC1-C6 alkyl,-C(=O)-halo Gen-C1-C6 alkyl,-CN.-NO2,-S(=O)2N(R6)2(where the two substitutes at R6 are independent of each other)-S(=O)p-C1-C6 alkyl,-S(=O)p-halo Gen-C1-C6 alkyl,-O-S(=O)p-C1-C6 alkyl-O-S(=O)p-halo Gen-C1-C6 alkyl,phenyl,benzyl or benzyloxywhere each substitute of phenyl,benzyl or benzyloxy is either unsubstituted or independently substituted in the aromatic ring. Up to five times with agents selected from groups consisting of halogens, cyanide, NO2, C1-C6 alkyls, halogen-C1-C6 alkyls, C1-C6 alkoxys, and halogen-C1-C6 alkoxys and R15 is hydrogen, C1-C6 alkyl or halogen-C1-C6 alkyls, and if suitable for E/Z isomers, the EZ isomer and/or totomer mixtures in each case are in free form or in salt form with methods for preparing and using these compounds. E/Z isomers and totomers can kill pests, where the active ingredient is selected from these compounds. E/Z isomers and totomers and methods for preparing and using these mixtures produce intermediates in free form or in salt form for the preparation of these compounds and in which suitable totomers of those substances are in free form or in salt form and with methods for preparing and using these intermediates and their totomers. 2. Compound formula (I) pursuant to claim 1 in free form. 3. Compound formula (I) according to claim 1, where A1 and A2 are phenyls. 4. Compound formula (I) according to any one of claims 1 through 3, where R2a is -C1-C6 alkyl-NR11-R12,-COC9-C20 alkyl,-C1-C6 alkyl-O-C1-C6 alkyl,(C=O)C1-C6 alkyl,-CH2O(C=O)C2-C6 alkynyl,-CH2O(C=O)C2-C6 alkynyl,-C(=S)OC2-C6 alkynyl,-C(=S)OC2-C6 alkynyl,-C(=S)SC1-C6 alkyl,-C(=S)SC2-C6 alkynyl,-C(=S)SC2-C6 alkynyl,-C(=O)SC1-C6 Alkyl,-(C(=O)SC2-C6 alkynil,-C(=O)SC2-C6 alkynil, -C1-C6 alkylthio-C1-C6 alkyl,-C(=S)NR11R12,-C(=O)NR10OR13-,CH2OC-C6 alkynil,-CH2OC2-C6 alkynil.-CH2OC2C6 haloaldenil or CH2OC2-C6 haloalkynil 5. A compound formula (I) according to any one of claims 1 through 4, where n, is 2,3 or and n2 is 1 or 2. 6. The pesticide mixture contains at least one of the formulation components (I) under Reputation 1 as the active ingredient in either free form or in the form of an agriculturally acceptable salt, and at least one adjuvant. 7. Methods for controlling pests or animals consisting of the application of a mixture of substances under claim 6 against the pests and animals or their habitats. 8. Method according to Article 7 for the control of insects and members of the Otter acarinae. 9. Method for preparing mixtures of claim 6 containing at least one adjuvant and consisting of thorough mixing and/or grinding of the active ingredient with the adjuvant. 10. The use of the compound formulated under Protection 1 in the form of one of the agriculturally acceptable salts for the preparation of the mixtures of Protection 6. 11. Use of the compounds under claim 6 for pest and animal control. 12. Application of Claim 11 for the protection of plant propagation materials. 13. The method of claim 7 for the protection of plant propagation material consists of the treatment of such propagation material or locus for the cultivation of such propagation material. 14. Propagation material treated in accordance with the methods described in Claim 13 (Claim 14, page 7, Figure).