HRP931427A2 - Insecticidal n'-substituted-n, n'.diacylhydrazines - Google Patents
Insecticidal n'-substituted-n, n'.diacylhydrazines Download PDFInfo
- Publication number
- HRP931427A2 HRP931427A2 HR931427A HRP931427A HRP931427A2 HR P931427 A2 HRP931427 A2 HR P931427A2 HR 931427 A HR931427 A HR 931427A HR P931427 A HRP931427 A HR P931427A HR P931427 A2 HRP931427 A2 HR P931427A2
- Authority
- HR
- Croatia
- Prior art keywords
- tert
- butylhydrazine
- methylbenzoyl
- methoxy
- methoxybenzoyl
- Prior art date
Links
- 230000000749 insecticidal effect Effects 0.000 title claims description 39
- 150000008037 diacylhydrazines Chemical class 0.000 title 1
- -1 alkyl lithium Chemical compound 0.000 claims abstract description 115
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 55
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 41
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 19
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 76
- 239000001257 hydrogen Substances 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 65
- 239000000460 chlorine Substances 0.000 claims description 60
- 229910052801 chlorine Inorganic materials 0.000 claims description 60
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 45
- 229910052794 bromium Inorganic materials 0.000 claims description 45
- 150000002431 hydrogen Chemical group 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 44
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 40
- 229910052702 rhenium Inorganic materials 0.000 claims description 40
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- 239000011737 fluorine Substances 0.000 claims description 39
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 37
- 229910021481 rutherfordium Inorganic materials 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 241000238631 Hexapoda Species 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 claims description 12
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 125000006530 (C4-C6) alkyl group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- FFDQGQKRNVKUDK-UHFFFAOYSA-N n'-tert-butyl-2-chloro-n'-(3,5-dimethylbenzoyl)-3-methoxybenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1Cl FFDQGQKRNVKUDK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- MQDKOSHYSWPOBM-UHFFFAOYSA-N n'-tert-butyl-2-ethyl-3-methoxy-n'-(3-methoxybenzoyl)benzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC=CC(OC)=C1 MQDKOSHYSWPOBM-UHFFFAOYSA-N 0.000 claims description 6
- MAKHCMHVQLYJHX-UHFFFAOYSA-N n'-tert-butyl-2-ethyl-3-methoxy-n'-(3-methylbenzoyl)benzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC=CC(C)=C1 MAKHCMHVQLYJHX-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- VDVJGIYXDVPQLP-UHFFFAOYSA-N piperonylic acid Chemical compound OC(=O)C1=CC=C2OCOC2=C1 VDVJGIYXDVPQLP-UHFFFAOYSA-N 0.000 claims description 6
- 235000010344 sodium nitrate Nutrition 0.000 claims description 6
- 239000004317 sodium nitrate Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 241000255777 Lepidoptera Species 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- CDUYORZAQRQNFH-UHFFFAOYSA-N n'-tert-butyl-3-methoxy-2-methyl-n'-(3-methylbenzoyl)benzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=CC=2)C(C)(C)C)=C1C CDUYORZAQRQNFH-UHFFFAOYSA-N 0.000 claims description 5
- XIBWXIXIEGUWCX-UHFFFAOYSA-N n'-tert-butyl-3-methoxy-2-methyl-n'-(4-methylbenzoyl)benzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=CC(C)=CC=2)C(C)(C)C)=C1C XIBWXIXIEGUWCX-UHFFFAOYSA-N 0.000 claims description 5
- UHMHZASNMONJPJ-UHFFFAOYSA-N n'-tert-butyl-n'-(3-chloro-5-methylbenzoyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(Cl)=C1 UHMHZASNMONJPJ-UHFFFAOYSA-N 0.000 claims description 5
- MUQNAPSBHXFMHT-UHFFFAOYSA-N tert-butylhydrazine Chemical compound CC(C)(C)NN MUQNAPSBHXFMHT-UHFFFAOYSA-N 0.000 claims description 5
- UFNRVOJYQUIQHJ-UHFFFAOYSA-N 2-bromo-n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-3-methoxybenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1Br UFNRVOJYQUIQHJ-UHFFFAOYSA-N 0.000 claims description 4
- ZKYDPPPQBCAAQG-UHFFFAOYSA-N 4-bromo-n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-1,3-benzodioxole-5-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3OCOC3=CC=2)Br)C(C)(C)C)=C1 ZKYDPPPQBCAAQG-UHFFFAOYSA-N 0.000 claims description 4
- 241000258937 Hemiptera Species 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 4
- WGDATBCAWVSEDC-UHFFFAOYSA-N n'-(3-bromo-4-fluorobenzoyl)-n'-tert-butyl-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Br)C(F)=CC=2)C(C)(C)C)=C1C WGDATBCAWVSEDC-UHFFFAOYSA-N 0.000 claims description 4
- ZNXGJIUPRDPGSY-UHFFFAOYSA-N n'-(3-bromo-5-chlorobenzoyl)-n'-tert-butyl-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Br)C=C(Cl)C=2)C(C)(C)C)=C1C ZNXGJIUPRDPGSY-UHFFFAOYSA-N 0.000 claims description 4
- YQEGYKXKWSHEBO-UHFFFAOYSA-N n'-tert-butyl-n'-(3,4-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C(C)=CC=2)C(C)(C)C)=C1C YQEGYKXKWSHEBO-UHFFFAOYSA-N 0.000 claims description 4
- OHJCURYZNGMLAC-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dichlorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Cl)C=C(Cl)C=2)C(C)(C)C)=C1C OHJCURYZNGMLAC-UHFFFAOYSA-N 0.000 claims description 4
- ASIUTMRRCYGOAV-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-difluorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(F)C=C(F)C=2)C(C)(C)C)=C1C ASIUTMRRCYGOAV-UHFFFAOYSA-N 0.000 claims description 4
- QYYXITIZXRMPSZ-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYYXITIZXRMPSZ-UHFFFAOYSA-N 0.000 claims description 4
- CUEUYBWEBYJLCW-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-4-ethyl-1,3-benzodioxole-5-carbohydrazide Chemical compound CCC1=C2OCOC2=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 CUEUYBWEBYJLCW-UHFFFAOYSA-N 0.000 claims description 4
- VQLOUZNRXGJFGR-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-4-methyl-1,3-benzodioxole-5-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3OCOC3=CC=2)C)C(C)(C)C)=C1 VQLOUZNRXGJFGR-UHFFFAOYSA-N 0.000 claims description 4
- WHZJAKGSNKXLIN-UHFFFAOYSA-N n'-tert-butyl-n'-(3-chloro-4-methylbenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Cl)C(C)=CC=2)C(C)(C)C)=C1C WHZJAKGSNKXLIN-UHFFFAOYSA-N 0.000 claims description 4
- KUPSFYNLNDGHBH-UHFFFAOYSA-N n'-tert-butyl-n'-(3-chloro-5-methylbenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Cl)C=C(C)C=2)C(C)(C)C)=C1C KUPSFYNLNDGHBH-UHFFFAOYSA-N 0.000 claims description 4
- TZMOITBSBROIEZ-UHFFFAOYSA-N n'-tert-butyl-n'-(3-chlorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Cl)C=CC=2)C(C)(C)C)=C1C TZMOITBSBROIEZ-UHFFFAOYSA-N 0.000 claims description 4
- VDZVXQNZMFLBAK-UHFFFAOYSA-N n'-tert-butyl-n'-(3-ethylbenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound CCC1=CC=CC(C(=O)N(NC(=O)C=2C(=C(OC)C=CC=2)C)C(C)(C)C)=C1 VDZVXQNZMFLBAK-UHFFFAOYSA-N 0.000 claims description 4
- DAGQRBAFGTUEIA-UHFFFAOYSA-N n'-tert-butyl-n'-(4-chloro-3-methylbenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C(Cl)=CC=2)C(C)(C)C)=C1C DAGQRBAFGTUEIA-UHFFFAOYSA-N 0.000 claims description 4
- ZMCLMZWLLDYVAX-UHFFFAOYSA-N n'-tert-butyl-n'-(4-fluorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=CC(F)=CC=2)C(C)(C)C)=C1C ZMCLMZWLLDYVAX-UHFFFAOYSA-N 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- UAFCOEKNMQYUQM-UHFFFAOYSA-N n'-(3-bromo-5-methylbenzoyl)-n'-tert-butyl-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Br)C=C(C)C=2)C(C)(C)C)=C1C UAFCOEKNMQYUQM-UHFFFAOYSA-N 0.000 claims description 3
- RWMNZJYZSLFWJU-UHFFFAOYSA-N n'-tert-butyl-3-methoxy-n'-(2-methoxy-4-methylbenzoyl)-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C(=CC(C)=CC=2)OC)C(C)(C)C)=C1C RWMNZJYZSLFWJU-UHFFFAOYSA-N 0.000 claims description 3
- VFPVUELTFFXJAO-UHFFFAOYSA-N n'-tert-butyl-3-methoxy-n'-(3-methoxy-5-methylbenzoyl)-2-methylbenzohydrazide Chemical compound COC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(OC)C=CC=2)C)C(C)(C)C)=C1 VFPVUELTFFXJAO-UHFFFAOYSA-N 0.000 claims description 3
- RFHHXBKWJHQBMB-UHFFFAOYSA-N n'-tert-butyl-3-methoxy-n'-(3-methoxybenzoyl)-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)N(NC(=O)C=2C(=C(OC)C=CC=2)C)C(C)(C)C)=C1 RFHHXBKWJHQBMB-UHFFFAOYSA-N 0.000 claims description 3
- VZWAHPCUOACJMH-UHFFFAOYSA-N n'-tert-butyl-4-chloro-n'-(3,5-dimethylbenzoyl)-1,3-benzodioxole-5-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3OCOC3=CC=2)Cl)C(C)(C)C)=C1 VZWAHPCUOACJMH-UHFFFAOYSA-N 0.000 claims description 3
- PDBHWZQIBTZDGS-UHFFFAOYSA-N n'-tert-butyl-n'-(2,4-dichlorobenzoyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC=C(Cl)C=C1Cl PDBHWZQIBTZDGS-UHFFFAOYSA-N 0.000 claims description 3
- JRGGNDKKHFPIIH-UHFFFAOYSA-N n'-tert-butyl-n'-(2-chloro-5-methylbenzoyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC=C1Cl JRGGNDKKHFPIIH-UHFFFAOYSA-N 0.000 claims description 3
- HPCSRTXBVRDLCU-UHFFFAOYSA-N n'-tert-butyl-n'-(3,4-dichlorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)C(C)(C)C)=C1C HPCSRTXBVRDLCU-UHFFFAOYSA-N 0.000 claims description 3
- INTYDMWHWMEZHK-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dichlorobenzoyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(Cl)=CC(Cl)=C1 INTYDMWHWMEZHK-UHFFFAOYSA-N 0.000 claims description 3
- RCXMMUYYDGEVKJ-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-2-methyl-3-(trifluoromethoxy)benzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(OC(F)(F)F)C=CC=2)C)C(C)(C)C)=C1 RCXMMUYYDGEVKJ-UHFFFAOYSA-N 0.000 claims description 3
- LIGUZCXJYXFKRY-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-3-ethoxy-2-ethylbenzohydrazide Chemical compound CCOC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1CC LIGUZCXJYXFKRY-UHFFFAOYSA-N 0.000 claims description 3
- HCSCXFLFNHVPEM-UHFFFAOYSA-N n'-tert-butyl-n'-(3-chloro-4-fluorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Cl)C(F)=CC=2)C(C)(C)C)=C1C HCSCXFLFNHVPEM-UHFFFAOYSA-N 0.000 claims description 3
- LRIGVXWRWWLTRZ-UHFFFAOYSA-N n'-tert-butyl-n'-(3-chloro-4-methoxybenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)N(C(C)(C)C)NC(=O)C1=CC=CC(OC)=C1C LRIGVXWRWWLTRZ-UHFFFAOYSA-N 0.000 claims description 3
- DFLXBWQPHGUIRR-UHFFFAOYSA-N n'-tert-butyl-n'-(3-fluorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(F)C=CC=2)C(C)(C)C)=C1C DFLXBWQPHGUIRR-UHFFFAOYSA-N 0.000 claims description 3
- IBSGDNWBLTXOGH-UHFFFAOYSA-N n'-tert-butyl-n'-(4-chloro-2-methoxybenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C(=CC(Cl)=CC=2)OC)C(C)(C)C)=C1C IBSGDNWBLTXOGH-UHFFFAOYSA-N 0.000 claims description 3
- JEOZYBZMYFQZPV-UHFFFAOYSA-N n-tert-butyl-3,4,5-trichloro-n'-(3-methoxy-2-methylbenzoyl)benzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(C)(C)C)=C1C JEOZYBZMYFQZPV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- UNQKCTXKHGIRKS-UHFFFAOYSA-N 2-bromo-n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-3-methylbenzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(C)C=CC=2)Br)C(C)(C)C)=C1 UNQKCTXKHGIRKS-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- ZYHYHCKVKFEXRV-UHFFFAOYSA-N 4-ethyl-1,3-benzodioxole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C(CC)=C2OCOC2=C1 ZYHYHCKVKFEXRV-UHFFFAOYSA-N 0.000 claims description 2
- UOVBAZLLBRLOTA-UHFFFAOYSA-N 4-methyl-1,3-benzodioxole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=C2OCOC2=C1 UOVBAZLLBRLOTA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- FRBTYVCLBZZLBC-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(2,2-dimethylpropyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(CC(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 FRBTYVCLBZZLBC-UHFFFAOYSA-N 0.000 claims description 2
- YNMJKNTVZHTMQW-UHFFFAOYSA-N n'-tert-butyl-3-methoxy-n'-(3-methoxy-4-methylbenzoyl)-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(OC)C(C)=CC=2)C(C)(C)C)=C1C YNMJKNTVZHTMQW-UHFFFAOYSA-N 0.000 claims description 2
- DQSVISMUIAVOSN-UHFFFAOYSA-N n'-tert-butyl-n'-(2,4-dichlorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C(=CC(Cl)=CC=2)Cl)C(C)(C)C)=C1C DQSVISMUIAVOSN-UHFFFAOYSA-N 0.000 claims description 2
- LKTMKKZEWWHBGB-UHFFFAOYSA-N n'-tert-butyl-n'-(2,5-difluorobenzoyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(F)=CC=C1F LKTMKKZEWWHBGB-UHFFFAOYSA-N 0.000 claims description 2
- LJQGJXJONMMOMA-UHFFFAOYSA-N n'-tert-butyl-n'-(2-chloro-5-methylbenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C(=CC=C(C)C=2)Cl)C(C)(C)C)=C1C LJQGJXJONMMOMA-UHFFFAOYSA-N 0.000 claims description 2
- BSLRFIKNVWCUER-UHFFFAOYSA-N n'-tert-butyl-n'-(4-fluoro-3-methylbenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C(F)=CC=2)C(C)(C)C)=C1C BSLRFIKNVWCUER-UHFFFAOYSA-N 0.000 claims description 2
- KIBMXOXOLLBZEO-UHFFFAOYSA-N n-tert-butyl-2,5-dichloro-4-fluoro-n'-(3-methoxy-2-methylbenzoyl)benzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C(=CC(F)=C(Cl)C=2)Cl)C(C)(C)C)=C1C KIBMXOXOLLBZEO-UHFFFAOYSA-N 0.000 claims description 2
- GFJQVAFEOQQZPO-UHFFFAOYSA-N n-tert-butyl-3,5-dichloro-4-fluoro-n'-(3-methoxy-2-methylbenzoyl)benzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(Cl)C(F)=C(Cl)C=2)C(C)(C)C)=C1C GFJQVAFEOQQZPO-UHFFFAOYSA-N 0.000 claims description 2
- HXVRNOQKOJZXDV-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(2,2-dimethylpropyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(CC(C)(C)C)C(=O)C=2C=C(C)C=C(C)C=2)=C1C HXVRNOQKOJZXDV-UHFFFAOYSA-N 0.000 claims 2
- MRCRSVRRRZKROZ-UHFFFAOYSA-N n'-tert-butyl-2-ethyl-3-methoxy-n'-(2-methoxybenzoyl)benzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC=CC=C1OC MRCRSVRRRZKROZ-UHFFFAOYSA-N 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical compound CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- IIQADYWOHJECCO-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(3,3-dimethylbutan-2-yl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 IIQADYWOHJECCO-UHFFFAOYSA-N 0.000 claims 1
- LEEBAGPGNIOYMP-UHFFFAOYSA-N n'-benzoyl-n'-tert-butyl-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=CC=CC=2)C(C)(C)C)=C1C LEEBAGPGNIOYMP-UHFFFAOYSA-N 0.000 claims 1
- DBOUTKKSYHQTFE-UHFFFAOYSA-N n'-tert-butyl-n'-(2-chlorobenzoyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC=CC=C1Cl DBOUTKKSYHQTFE-UHFFFAOYSA-N 0.000 claims 1
- VPMNLVHJMGFBET-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-difluorobenzoyl)-2-ethyl-3-methoxybenzohydrazide Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(F)=CC(F)=C1 VPMNLVHJMGFBET-UHFFFAOYSA-N 0.000 claims 1
- PWJQXNCIMVWGQX-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-3-ethoxy-2-methylbenzohydrazide Chemical compound CCOC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C PWJQXNCIMVWGQX-UHFFFAOYSA-N 0.000 claims 1
- BNCHZMFWJSVFIO-UHFFFAOYSA-N n'-tert-butyl-n'-(4-chlorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=CC(Cl)=CC=2)C(C)(C)C)=C1C BNCHZMFWJSVFIO-UHFFFAOYSA-N 0.000 claims 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 18
- 238000007792 addition Methods 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 230000002349 favourable effect Effects 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 241001521235 Spodoptera eridania Species 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 241000995027 Empoasca fabae Species 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- JPCISVSOTKMFPG-UHFFFAOYSA-N 3-methoxy-2-methylbenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1C JPCISVSOTKMFPG-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical class COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- JWZQJTGQFHIRFQ-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6-carboxylic acid Chemical compound O1CCOC2=CC(C(=O)O)=CC=C21 JWZQJTGQFHIRFQ-UHFFFAOYSA-N 0.000 description 4
- BYHMLZGICSEKIY-UHFFFAOYSA-N 3-amino-2-methylbenzoic acid Chemical compound CC1=C(N)C=CC=C1C(O)=O BYHMLZGICSEKIY-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 description 3
- BXKZGIVKHPCDFO-UHFFFAOYSA-N 3-methoxy-2-methylbenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1C BXKZGIVKHPCDFO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- ZLHGTUBOTOKPQP-UHFFFAOYSA-N n-tert-butyl-3,5-dimethylbenzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(N)C(C)(C)C)=C1 ZLHGTUBOTOKPQP-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- OFBFTCNIRSRGGG-UHFFFAOYSA-N 2-(3-methoxyphenyl)-5,5-dimethyl-4h-1,3-oxazole Chemical compound COC1=CC=CC(C=2OC(C)(C)CN=2)=C1 OFBFTCNIRSRGGG-UHFFFAOYSA-N 0.000 description 2
- RXCOEMMGBRUEEG-UHFFFAOYSA-N 2-ethyl-3-methoxybenzoic acid Chemical compound CCC1=C(OC)C=CC=C1C(O)=O RXCOEMMGBRUEEG-UHFFFAOYSA-N 0.000 description 2
- LLPAULVDRSLFBZ-UHFFFAOYSA-N 2-ethyl-3-methoxybenzoyl chloride Chemical compound CCC1=C(OC)C=CC=C1C(Cl)=O LLPAULVDRSLFBZ-UHFFFAOYSA-N 0.000 description 2
- ZJIOBDJEKDUUCI-UHFFFAOYSA-N 3,5-dimethylbenzoyl chloride Chemical compound CC1=CC(C)=CC(C(Cl)=O)=C1 ZJIOBDJEKDUUCI-UHFFFAOYSA-N 0.000 description 2
- MZUIOLZHUUHESU-UHFFFAOYSA-N 3-chloro-5-methylbenzoic acid Chemical compound CC1=CC(Cl)=CC(C(O)=O)=C1 MZUIOLZHUUHESU-UHFFFAOYSA-N 0.000 description 2
- OPIVSAZDWOWATK-UHFFFAOYSA-N 5-ethyl-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid Chemical compound O1CCOC2=CC=C(C(O)=O)C(CC)=C21 OPIVSAZDWOWATK-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 244000100170 Phaseolus lunatus Species 0.000 description 2
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 239000012022 methylating agents Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- LECIHFPXHCYQCP-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(3,3-dimethylbutan-2-yl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(C)C(C)(C)C)C(=O)C=2C=C(C)C=C(C)C=2)=C1C LECIHFPXHCYQCP-UHFFFAOYSA-N 0.000 description 2
- JPHNWUMYNZVUFT-UHFFFAOYSA-N n'-tert-butyl-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NNC(C)(C)C)=C1C JPHNWUMYNZVUFT-UHFFFAOYSA-N 0.000 description 2
- URMBXDMUIBFIEP-UHFFFAOYSA-N n'-tert-butyl-n'-(3,4-difluorobenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(F)C(F)=CC=2)C(C)(C)C)=C1C URMBXDMUIBFIEP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FKKLHLZFSZGXBN-UHFFFAOYSA-N 1-chloro-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(Cl)=C1 FKKLHLZFSZGXBN-UHFFFAOYSA-N 0.000 description 1
- YPQAFWHSMWWPLX-UHFFFAOYSA-N 1975-50-4 Chemical compound CC1=C(C(O)=O)C=CC=C1[N+]([O-])=O YPQAFWHSMWWPLX-UHFFFAOYSA-N 0.000 description 1
- ADMTUGZFHLWYAU-UHFFFAOYSA-N 2,2-dimethylpropylhydrazine Chemical compound CC(C)(C)CNN ADMTUGZFHLWYAU-UHFFFAOYSA-N 0.000 description 1
- CWKXDPPQCVWXAG-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6-carbaldehyde Chemical compound O1CCOC2=CC(C=O)=CC=C21 CWKXDPPQCVWXAG-UHFFFAOYSA-N 0.000 description 1
- UUTKEFGMHCMDDT-UHFFFAOYSA-N 2-(2,3-dimethoxyphenyl)-5,5-dimethyl-4h-1,3-oxazole Chemical compound COC1=CC=CC(C=2OC(C)(C)CN=2)=C1OC UUTKEFGMHCMDDT-UHFFFAOYSA-N 0.000 description 1
- WUPXALABZXSNMV-UHFFFAOYSA-N 2-(2-ethyl-3-methoxy-4-methylphenyl)-5,5-dimethyl-4h-1,3-oxazole Chemical compound CCC1=C(OC)C(C)=CC=C1C1=NCC(C)(C)O1 WUPXALABZXSNMV-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IMCURGNYGGRUCQ-UHFFFAOYSA-N 2-ethyl-3-methoxy-4-methylbenzoic acid Chemical compound CCC1=C(C(O)=O)C=CC(C)=C1OC IMCURGNYGGRUCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- UMIIZOBDBBNULH-UHFFFAOYSA-N 3-amino-2-ethylbenzoic acid Chemical compound CCC1=C(N)C=CC=C1C(O)=O UMIIZOBDBBNULH-UHFFFAOYSA-N 0.000 description 1
- JQULINCXIWRQML-UHFFFAOYSA-N 3-ethyl-1,4-dioxane-2-carboxylic acid Chemical compound CCC1OCCOC1C(O)=O JQULINCXIWRQML-UHFFFAOYSA-N 0.000 description 1
- RIERSGULWXEJKL-UHFFFAOYSA-N 3-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(O)C=CC=C1C(O)=O RIERSGULWXEJKL-UHFFFAOYSA-N 0.000 description 1
- QYHMPRAUVJVVEH-UHFFFAOYSA-N 3-methoxy-2-propan-2-ylbenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1C(C)C QYHMPRAUVJVVEH-UHFFFAOYSA-N 0.000 description 1
- RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- WCAFQVZALMRDAP-UHFFFAOYSA-N n'-tert-butyl-n'-(3-fluoro-4-methylbenzoyl)-3-methoxy-2-methylbenzohydrazide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(F)C(C)=CC=2)C(C)(C)C)=C1C WCAFQVZALMRDAP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- DDPWVABNMBRBFI-UHFFFAOYSA-N tert-butylhydrazine;hydron;chloride Chemical compound Cl.CC(C)(C)NN DDPWVABNMBRBFI-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/48—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/56—Amides of thiocarboxylic acids having nitrogen atoms of thiocarboxamide groups further bound to another hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
- C07D213/87—Hydrazides; Thio or imino analogues thereof in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/984,189 US5344958A (en) | 1992-11-23 | 1992-11-23 | Insecticidal N'-substituted-N,N'-diacylhydrazines |
US08/129,549 US5530028A (en) | 1992-11-23 | 1993-09-29 | Insecticidal N'-substituted-N,N'-diacylhydrazines |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP931427A2 true HRP931427A2 (en) | 1996-06-30 |
Family
ID=26827677
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR931427A HRP931427A2 (en) | 1992-11-23 | 1993-11-22 | Insecticidal n'-substituted-n, n'.diacylhydrazines |
Country Status (19)
Country | Link |
---|---|
US (1) | US5530028A (fr) |
EP (3) | EP0729934A3 (fr) |
KR (1) | KR100317793B1 (fr) |
CN (4) | CN1038673C (fr) |
AT (1) | ATE179166T1 (fr) |
AU (1) | AU683224B2 (fr) |
BG (1) | BG98232A (fr) |
BR (1) | BR9304789A (fr) |
CA (1) | CA2103110C (fr) |
DE (2) | DE69324552T4 (fr) |
DK (1) | DK0602794T3 (fr) |
ES (1) | ES2130232T3 (fr) |
GR (1) | GR3030029T3 (fr) |
HR (1) | HRP931427A2 (fr) |
HU (1) | HUT75039A (fr) |
IL (1) | IL107533A (fr) |
MY (1) | MY111887A (fr) |
NZ (2) | NZ250170A (fr) |
PH (1) | PH31254A (fr) |
Families Citing this family (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6013836A (en) * | 1992-02-28 | 2000-01-11 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-disubstitutedhydrazines |
US5369127A (en) * | 1993-04-21 | 1994-11-29 | Allergan, Inc. | 1,3-benzodioxole and 1,2-dialkoxybenzene derivatives as ocular hypotensive agents |
US5948406A (en) * | 1996-08-12 | 1999-09-07 | Rohm And Haas Company | Immunogens, antibodies formed therefrom, and coating antigens useful in a diacylhydrazine immunoassay method |
US5917079A (en) * | 1996-09-24 | 1999-06-29 | Rohm And Haas Company | Process for synthesizing benzoic acids |
DE19730848A1 (de) | 1997-07-18 | 1999-01-21 | Bayer Ag | Verfahren zur Herstellung von 3-Hydroxy-2-methylbenzoesäure |
US6013671A (en) * | 1998-02-03 | 2000-01-11 | Rohm And Haas Company | Synergistic insecticidal compositions |
US6124500A (en) * | 1998-03-09 | 2000-09-26 | Rohm And Haas Company | Process for synthesizing benzoic acids |
US6258603B1 (en) * | 1998-06-17 | 2001-07-10 | Rohm And Haas Company | Ligands for modulating the expression of exogenous genes via an ecdysone receptor complex |
DE19831710A1 (de) * | 1998-07-15 | 2000-01-20 | Merck Patent Gmbh | Diacylhydrazinderivate |
IL133121A (en) | 1998-12-08 | 2004-06-20 | Dow Agrosciences Llc | Process for the preparation of benzoic acids-2-alkyl-3-hydroxy |
US20040033600A1 (en) | 2001-03-21 | 2004-02-19 | Palli Subba Reddy | Ecdysone receptor-based inducible gene expression system |
US8105825B2 (en) | 2000-10-03 | 2012-01-31 | Intrexon Corporation | Multiple inducible gene regulation system |
US6576422B1 (en) | 2000-10-17 | 2003-06-10 | Rohm And Haas Company | Method for identifying products employing gene expression |
DK1534738T3 (da) | 2001-02-20 | 2012-10-01 | Intrexon Corp | Nye substitutionsmutantreceptorer og anvendelse heraf i et inducérbart genekpressionssystem på basis af en nuklear receptor |
WO2002066614A2 (fr) * | 2001-02-20 | 2002-08-29 | Rheogene Holdings, Inc. | Recepteurs x de retinoides chimeriques et utilisations de ceux-ci dans un nouveau systeme d'expression de gene inductible fonde sur un recepteur d'ecdysone |
ES2385598T3 (es) | 2001-02-20 | 2012-07-27 | Intrexon Corporation | Sistema novedoso de expresión génica inducible basado en el receptor de ecdisona/receptor X retinoide de invertebrado |
EP1373470B1 (fr) | 2001-02-20 | 2013-04-24 | Intrexon Corporation | Nouveaux recepteurs de mutants de substitution et utilisation de ceux-ci dans un systeme d'expression genique inductible a base de recepteurs nucleaires |
DE10244149A1 (de) * | 2001-09-25 | 2003-04-30 | Werner Keber | Verfahren und Einrichtung zum Verhindern einer unzulässigen Flugannäherung von Flugzeugen an zu schützende Bodenobjeke |
US7919269B2 (en) | 2001-09-26 | 2011-04-05 | Intrexon Corporation | Whitefly ecdysone receptor nucleic acids, polypeptides, and uses thereof |
JP2005532781A (ja) * | 2001-09-26 | 2005-11-04 | レオジーン・ホールディングス,インコーポレーテッド | ヨコバイエクジソン受容体核酸、ポリペプチド、およびそれらの使用 |
US7375093B2 (en) | 2002-07-05 | 2008-05-20 | Intrexon Corporation | Ketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex |
US7304161B2 (en) | 2003-02-10 | 2007-12-04 | Intrexon Corporation | Diaclhydrazine ligands for modulating the expression of exogenous genes in mammalian systems via an ecdysone receptor complex |
US7304162B2 (en) * | 2003-02-21 | 2007-12-04 | Intrexon Corporation | Oxadiazoline ligands for modulating the expression of exogenous genes via an ecdysone receptor complex |
US7456315B2 (en) | 2003-02-28 | 2008-11-25 | Intrexon Corporation | Bioavailable diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex |
US7935510B2 (en) | 2004-04-30 | 2011-05-03 | Intrexon Corporation | Mutant receptors and their use in a nuclear receptor-based inducible gene expression system |
US20070212716A1 (en) * | 2006-02-10 | 2007-09-13 | Commonwealth Scientific & Industrial Research Org. | Nezara viridula Ecdysone Receptor |
RU2490253C2 (ru) | 2007-05-29 | 2013-08-20 | Интрексон Корпорейшн | Хиральные диацилгидразиновые лиганды для модуляции экспрессии экзогенных генов с помощью экдизон-рецепторного комплекса |
NZ583430A (en) | 2007-08-23 | 2012-06-29 | Intrexon Corp | Methods and compositions for diagnosing disease via detecting reporter gene expression |
EP2183355B1 (fr) * | 2007-09-17 | 2016-01-27 | Rohm and Haas Company | Compositions et procedes pour la modification de reponses physiologiques chez les plantes |
CA2715080C (fr) | 2007-09-28 | 2021-09-28 | Intrexon Corporation | Constructions et bioreacteurs de commutation de gene theapeutique destines a l'expression de molecules biotherapeutiques, et utilisation de ceux-ci |
HUE024479T2 (en) * | 2007-10-08 | 2016-01-28 | Intrexon Corp | Genetically altered dendritic cells and uses for cancer treatment |
RU2612788C2 (ru) | 2010-03-23 | 2017-03-13 | Интрексон Корпорейшн | Векторы, условно экспрессирующие терапевтические белки, клетки-хозяева, содержащие указанные векторы, и их применение |
EP2681327B1 (fr) | 2011-03-04 | 2018-11-21 | Intrexon Corporation | Vecteurs exprimant une protéine de façon conditionnelle |
EP3461810B1 (fr) | 2011-09-08 | 2020-06-17 | Precigen, Inc. | Diacylhydrazine cristalline et utilisation associée |
CN103563953A (zh) * | 2012-08-05 | 2014-02-12 | 南京华洲药业有限公司 | 一种含甲氧虫酰肼和氟啶脲的复合杀虫组合物及其用途 |
CN102863355B (zh) * | 2012-09-24 | 2014-05-21 | 浙江禾田化工有限公司 | 一种n-(3-甲氧基-2-甲基苯甲酰基)-n’-叔丁基肼的提纯方法 |
CN102960356A (zh) * | 2012-12-12 | 2013-03-13 | 海利尔药业集团股份有限公司 | 一种含有双三氟虫脲与甲氧虫酰肼的杀虫组合物 |
CN103416409A (zh) * | 2012-12-15 | 2013-12-04 | 海利尔药业集团股份有限公司 | 一种含有氟螨嗪与甲氧虫酰肼的杀虫组合物 |
US9127024B2 (en) | 2013-03-15 | 2015-09-08 | Intrexon Corporation | Boron-containing diacylhydrazines |
CN103222466A (zh) * | 2013-04-26 | 2013-07-31 | 南通金陵农化有限公司 | 一种吡蚜酮和甲氧虫酰肼的复配农药 |
CN104072383A (zh) * | 2014-07-10 | 2014-10-01 | 四川北方红光特种化工有限公司 | 制备3-氨基-2-甲基苯甲酸的方法 |
US9944659B2 (en) | 2014-09-17 | 2018-04-17 | Intrexon Corporation | Boron-containing diacylhydrazine compounds |
EP3247702B1 (fr) | 2015-01-23 | 2020-04-22 | Syngenta Participations AG | Dérivés de semi-carbazones et de thiosemicarbazones ayant une activité pesticide |
AU2016334401A1 (en) | 2015-10-10 | 2018-04-26 | Intrexon Corporation | Improved therapeutic control of proteolytically sensitive, destabilized forms of interleukin-12 |
KR20180069081A (ko) | 2015-11-11 | 2018-06-22 | 인트렉손 코포레이션 | 심장 이상 및 기타 병리 이상의 치료를 위한 복수의 생물학적으로 활성화된 폴리펩티드를 단일 벡터로부터 발현하기 위한 조성물 및 방법 |
UY37343A (es) | 2016-07-25 | 2018-02-28 | Intrexon Corp | Control del fenotipo en plantas |
US11116852B2 (en) | 2016-11-09 | 2021-09-14 | Precigen, Inc. | Frataxin expression constructs |
JP7288401B2 (ja) | 2017-01-10 | 2023-06-07 | プレシゲン,インコーポレイテッド | 新規の遺伝子スイッチ発現系を介したポリペプチドの発現のモジュレーション |
CN108530297B (zh) * | 2017-03-03 | 2021-09-24 | 联化科技股份有限公司 | 2-氯-3-甲基苯甲酸及其中间体的制备方法 |
CN109384667A (zh) * | 2017-08-02 | 2019-02-26 | 江苏永安化工有限公司 | 一种2-甲基-3-甲氧基苯甲酰氯的合成工艺 |
CN112135622A (zh) | 2018-03-06 | 2020-12-25 | 普莱西根股份有限公司 | 乙型肝炎疫苗及其用途 |
CN109776464A (zh) * | 2019-03-26 | 2019-05-21 | 江苏省农药研究所股份有限公司 | 呋喃虫酰肼的制备方法、中间体及其制备方法 |
WO2020206056A1 (fr) | 2019-04-04 | 2020-10-08 | Greenvenus Llc | Peptides et procédés de protection de plantes |
CN113121339B (zh) * | 2021-04-19 | 2022-10-11 | 江苏永安化工有限公司 | 一种3-羟基-2-甲基苯甲酸甲酯与3-甲氧基-2-甲基苯甲酸甲酯的联产工艺 |
CN113511968A (zh) * | 2021-04-19 | 2021-10-19 | 江苏永安化工有限公司 | 一种2-甲基-3-甲氧基苯甲酸的合成工艺 |
CN117320551A (zh) | 2021-05-14 | 2023-12-29 | 先正达农作物保护股份公司 | 种子处理组合物 |
WO2022268815A1 (fr) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Lutte contre les insectes, les acariens et les nématodes nuisibles |
WO2022268813A1 (fr) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Lutte contre les insectes, les acariens et les nématodes nuisibles |
GB2612942A (en) * | 2021-09-16 | 2023-05-24 | Rotam Agrochem Int Co Ltd | A crystalline form of methoxyfenozide, a process for its preparation and use of the same |
WO2023105064A1 (fr) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Lutte contre les insectes, les acariens et les nématodes |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4161611A (en) * | 1976-02-23 | 1979-07-17 | Veesicol Chemical Corporation | Process for the production of 2-methoxy-3,6-dichlorobenzoic acid |
US4389401A (en) * | 1979-07-10 | 1983-06-21 | Rohm And Haas Company | Arthropod repellents |
DK483586A (da) * | 1985-10-21 | 1987-04-22 | Rohm & Haas | Insecticide n'-substituerede-n,n'-diacylhydraziner |
US4985461A (en) * | 1985-10-21 | 1991-01-15 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-diacylhydrazines |
US5117057A (en) * | 1985-10-21 | 1992-05-26 | Rohm And Haas Company | Insecticidal N' substituted-N-N'-disubstituted-hydrazines |
US5110986A (en) * | 1988-04-26 | 1992-05-05 | Rohm And Haas Company | Synthesis of n-t-alkyl-1,2-diacylhydrazines |
JPH0660142B2 (ja) * | 1989-06-02 | 1994-08-10 | 田辺製薬株式会社 | ビフェニル誘導体、その製法及びその合成中間体 |
NZ229555A (en) * | 1988-06-16 | 1992-03-26 | Rohm & Haas | Pharmaceutical compositions for combating helminths in animals |
US4954655A (en) * | 1989-03-31 | 1990-09-04 | Rohm And Haas Company | Preparation of alkylhydrazines |
NZ228936A (en) * | 1989-05-01 | 1992-04-28 | Rohm & Haas | Method for treating insect infestation in rice plants comprising applying diacylhydrazine derivatives |
JPH0539252A (ja) * | 1990-08-01 | 1993-02-19 | Nippon Kayaku Co Ltd | N,N’−ジベンゾイル−tert−ブチルヒドラジン誘導体およびそれを有効成分とする殺虫組成物 |
JP3068846B2 (ja) * | 1990-08-01 | 2000-07-24 | 日本化薬株式会社 | 新規ヒドラジン誘導体およびそれを有効成分とする殺虫組成物 |
US5110979A (en) * | 1991-01-15 | 1992-05-05 | Imperial Chemical Industries Plc | Trisubstituted benzoic acid intermediates |
IL100643A (en) * | 1991-01-25 | 1996-10-31 | Nippon Kayaku Kk | History of hydrazine and pesticides containing these histories as an active ingredient |
US5334753A (en) * | 1992-03-12 | 1994-08-02 | Rhone-Poulenc Agriculture Ltd | Processes for preparing ortho-substituted benzoic acids |
-
1993
- 1993-09-29 US US08/129,549 patent/US5530028A/en not_active Expired - Lifetime
- 1993-11-08 DE DE69324552T patent/DE69324552T4/de not_active Expired - Lifetime
- 1993-11-08 IL IL10753393A patent/IL107533A/en not_active IP Right Cessation
- 1993-11-08 ES ES93308902T patent/ES2130232T3/es not_active Expired - Lifetime
- 1993-11-08 AT AT93308902T patent/ATE179166T1/de active
- 1993-11-08 DK DK93308902T patent/DK0602794T3/da active
- 1993-11-08 EP EP96106726A patent/EP0729934A3/fr not_active Withdrawn
- 1993-11-08 EP EP93308902A patent/EP0602794B1/fr not_active Expired - Lifetime
- 1993-11-08 DE DE69324552A patent/DE69324552D1/de not_active Expired - Lifetime
- 1993-11-08 EP EP96106727A patent/EP0729953A3/fr not_active Withdrawn
- 1993-11-09 NZ NZ250170A patent/NZ250170A/xx not_active IP Right Cessation
- 1993-11-09 NZ NZ280487A patent/NZ280487A/en not_active IP Right Cessation
- 1993-11-11 AU AU50635/93A patent/AU683224B2/en not_active Expired
- 1993-11-15 CA CA002103110A patent/CA2103110C/fr not_active Expired - Lifetime
- 1993-11-19 BG BG98232A patent/BG98232A/xx unknown
- 1993-11-20 MY MYPI93002437A patent/MY111887A/en unknown
- 1993-11-22 HU HU9303312A patent/HUT75039A/hu unknown
- 1993-11-22 BR BR9304789A patent/BR9304789A/pt not_active IP Right Cessation
- 1993-11-22 HR HR931427A patent/HRP931427A2/hr not_active Application Discontinuation
- 1993-11-23 CN CN93114977A patent/CN1038673C/zh not_active Expired - Lifetime
- 1993-11-23 KR KR1019930025020A patent/KR100317793B1/ko not_active IP Right Cessation
- 1993-11-23 PH PH47307A patent/PH31254A/en unknown
-
1997
- 1997-09-10 CN CN97118445A patent/CN1116271C/zh not_active Expired - Lifetime
- 1997-09-10 CN CN97118446A patent/CN1072217C/zh not_active Expired - Lifetime
- 1997-09-10 CN CN97118447A patent/CN1067050C/zh not_active Expired - Lifetime
-
1999
- 1999-04-22 GR GR990401016T patent/GR3030029T3/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP931427A2 (en) | Insecticidal n'-substituted-n, n'.diacylhydrazines | |
AU761273B2 (en) | Heterocyclic dicarboxylic acid diamide derivatives, agricultural/horticultural insecticides and method of using the same | |
CA1268475A (fr) | Herbicides ayant des proprietes optiques | |
JP5149003B2 (ja) | アミド誘導体ならびに該化合物を含有する殺虫剤 | |
KR930004672B1 (ko) | 3-치환 페닐피라졸 유도체 또는 이의 염 및 이의 제조방법, 이의 용도 및 이의 사용 방법 | |
JPS6284054A (ja) | 新規のスルホニル―フェニルアルキルアミン、及びこれを含有する、高められた血小板凝集又は腎臓機能の病理学的変化に基づく疾病の治療剤 | |
CA2263399A1 (fr) | Composes de 1-alkyl-4-benzoyl-5-hydroxypyrazole et leur utilisation comme herbicides | |
SI9300607A (en) | Insecticidal n'-substituted-n,n'-diacylhydrazines | |
US4148625A (en) | Tetrahydroisophthalimide compounds | |
EP0493606B1 (fr) | Derive de benzene substitue par heterocycle, production de ce derive, et herbicide contenant ce derive comme ingredient actif | |
Liu et al. | Design, synthesis and insecticidal evaluation of novel pyrazolecarboxamides containing cyano substituted N‐pyridylpyrazole | |
JP4004555B2 (ja) | 殺虫化合物 | |
US4032649A (en) | 2,3-Dihydro-2,2-dimethyl-7-benzo[b]thienyl N-methylcarbamate and use as an insecticide | |
CA2434200A1 (fr) | Conjugues d'acides amines indanoyle 6-substitues utilises comme mimetiques pour l'activite biologique de la coronatine | |
RU2488575C1 (ru) | Способ получения 2,4-динитрофенола | |
US4377408A (en) | Herbicidal derivatives of 5-phenoxy-4(3H)-quinazolinone-1-oxide | |
US4977182A (en) | Fungicidal 3-cyano-4-phenyl-pyrroles | |
JP2726404B2 (ja) | 置換フェニルカーボナート誘導体 | |
RU2038351C1 (ru) | Производные бензола, содержащие гетероцикл, способы их получения и гербицидное средство | |
JPH01113388A (ja) | 除草剤組成物 | |
JP2673175B2 (ja) | ナフトキノン系化合物、それを含む殺ダニ剤およびダニ類を防除する方法 | |
JPS5851943B2 (ja) | エチニルシクロプロパンカルボンサンエステルノセイゾウホウホウ | |
JPH04164067A (ja) | N−置換フェニル−3、4、5、6−テトラヒドロフタルイミド誘導体及びそれを有効成分とする除草剤 | |
JPH1072414A (ja) | 置換ベンゼン誘導体 | |
JPS6023668B2 (ja) | テトラヒドロフタラミド誘導体,その製造法および製剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A1OB | Publication of a patent application | ||
OBST | Application withdrawn |