CN1896066B - 制备杀虫剂的方法 - Google Patents

制备杀虫剂的方法 Download PDF

Info

Publication number: CN1896066B
Authority: CN; China
Prior art keywords: amino; trifluoromethyl; formula; mixture; dichlor
Prior art date: 1999-10-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CN2004101300014A

Other languages

English (en)

Chinese (zh)

Other versions

CN1896066A (zh

Inventor

J·-L·克拉弗

I·佩拉

S·勒巴尔斯

P·沙罗

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer LLC

Original Assignee

Bayer CropScience SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-10-22

Filing date

1999-10-22

Publication date

2011-06-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8167491&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN1896066(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1999-10-22 Application filed by Bayer CropScience SA filed Critical Bayer CropScience SA

1999-10-22 Priority to CN2004101300014A priority Critical patent/CN1896066B/zh

2007-01-17 Publication of CN1896066A publication Critical patent/CN1896066A/zh

2011-06-15 Application granted granted Critical

2011-06-15 Publication of CN1896066B publication Critical patent/CN1896066B/zh

2019-10-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
239000000575 pesticide Substances 0.000 title description 7
238000000034 method Methods 0.000 claims abstract description 62
239000000203 mixture Substances 0.000 claims abstract description 30
RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 claims abstract description 11
239000002798 polar solvent Substances 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 9
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 6
238000005304 joining Methods 0.000 claims description 2
125000006414 CCl Chemical group ClC* 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 28
229910052736 halogen Inorganic materials 0.000 abstract description 7
150000002367 halogens Chemical class 0.000 abstract description 7
125000001188 haloalkyl group Chemical group 0.000 abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 abstract 1
150000004675 formic acid derivatives Chemical class 0.000 abstract 1
125000004438 haloalkoxy group Chemical group 0.000 abstract 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 29
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 26
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000007789 gas Substances 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 12
RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 12
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 11
239000000543 intermediate Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
230000007797 corrosion Effects 0.000 description 7
238000005260 corrosion Methods 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000006365 thiocyanation reaction Methods 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
239000004327 boric acid Substances 0.000 description 4
230000006837 decompression Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000001291 vacuum drying Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical group OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
-1 thiocyanic acid basic metal Chemical class 0.000 description 3
XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000005899 Fipronil Substances 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052728 basic metal Inorganic materials 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000007872 degassing Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000002360 explosive Substances 0.000 description 2
229940013764 fipronil Drugs 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000009776 industrial production Methods 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000012423 maintenance Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
0 *c1cc(*)c(N(C(C2)N)NC*=C2C#N)nc1 Chemical compound *c1cc(*)c(N(C(C2)N)NC*=C2C#N)nc1 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YMJLEPMVGQBLHL-UHFFFAOYSA-N 1h-pyrazole-5-carbonitrile Chemical compound N#CC1=CC=NN1 YMJLEPMVGQBLHL-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
WZCTXSUTPWUZHE-UHFFFAOYSA-N FC(C(=O)OO)(F)F.OO Chemical compound FC(C(=O)OO)(F)F.OO WZCTXSUTPWUZHE-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
150000003818 basic metals Chemical class 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000002288 cocrystallisation Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000004434 industrial solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
238000012805 post-processing Methods 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229960001866 silicon dioxide Drugs 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000007704 transition Effects 0.000 description 1
OFHCXWMZXQBQMH-UHFFFAOYSA-N trifluoro(trifluoromethylsulfanyl)methane Chemical compound FC(F)(F)SC(F)(F)F OFHCXWMZXQBQMH-UHFFFAOYSA-N 0.000 description 1
WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CN2004101300014A 1999-10-22 1999-10-22 制备杀虫剂的方法 Expired - Lifetime CN1896066B (zh)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CN2004101300014A CN1896066B (zh)	1999-10-22	1999-10-22	制备杀虫剂的方法

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/EP1999/008687 WO2001030760A1 (en)	1999-10-22	1999-10-22	Process for preparing 4-trifluoromethylsulphinylpyrazole derivative
CN2004101300014A CN1896066B (zh)	1999-10-22	1999-10-22	制备杀虫剂的方法

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CNB998060828A Division CN1163488C (zh)	1999-10-22	1999-10-22	制备杀虫剂的新方法

Publications (2)

Publication Number	Publication Date
CN1896066A CN1896066A (zh)	2007-01-17
CN1896066B true CN1896066B (zh)	2011-06-15

Family

ID=8167491

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CN2004101300014A Expired - Lifetime CN1896066B (zh)	1999-10-22	1999-10-22	制备杀虫剂的方法
CNB998060828A Expired - Lifetime CN1163488C (zh)	1999-10-22	1999-10-22	制备杀虫剂的新方法
CN2008101863366A Expired - Lifetime CN101445483B (zh)	1999-10-22	1999-10-22	制备杀虫剂的方法

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CNB998060828A Expired - Lifetime CN1163488C (zh)	1999-10-22	1999-10-22	制备杀虫剂的新方法
CN2008101863366A Expired - Lifetime CN101445483B (zh)	1999-10-22	1999-10-22	制备杀虫剂的方法

Country Status (30)

Country	Link
US (2)	US6620943B1 (2)
EP (1)	EP1222173B1 (2)
JP (1)	JP4666863B2 (2)
KR (2)	KR100665599B1 (2)
CN (3)	CN1896066B (2)
AT (1)	ATE273961T1 (2)
AU (1)	AU783139B2 (2)
BG (1)	BG65483B1 (2)
BR (1)	BR9917518B1 (2)
CA (1)	CA2384283C (2)
CZ (1)	CZ299822B6 (2)
DE (1)	DE69919599T2 (2)
DK (1)	DK1222173T3 (2)
EA (1)	EA005077B1 (2)
ES (1)	ES2222743T3 (2)
HR (1)	HRP20020438B1 (2)
HU (1)	HU229393B1 (2)
IL (2)	IL149152A0 (2)
IN (2)	IN2005MU00818A (2)
ME (1)	MEP7808A (2)
MX (1)	MX229662B (2)
NZ (2)	NZ527896A (2)
PL (1)	PL206482B1 (2)
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PT1222173E (pt)	2004-11-30
RO121209B1 (ro)	2007-01-30
HUP0203206A2 (hu)	2003-03-28
CA2384283A1 (en)	2001-05-03
CN1332730A (zh)	2002-01-23
MX229662B (es)	2005-08-04
BR9917518B1 (pt)	2009-08-11
IN2005MU00818A (2)	2005-11-11
NZ527896A (en)	2004-07-30
EP1222173B1 (en)	2004-08-18
CA2384283C (en)	2009-02-03
KR100665598B1 (ko)	2007-01-10
CZ299822B6 (cs)	2008-12-03
ZA200201961B (en)	2003-05-28
HU229393B1 (en)	2013-11-28
BR9917518A (pt)	2002-06-18
TR200201072T2 (tr)	2002-07-22
MEP7808A (en)	2010-06-10
US6620943B1 (en)	2003-09-16
NZ517770A (en)	2003-11-28
MXPA02003944A (es)	2003-10-15
JP4666863B2 (ja)	2011-04-06
TR200202806T2 (tr)	2003-03-21
HRP20020438B1 (en)	2011-01-31
IN192712B (2)	2004-05-15
CN1163488C (zh)	2004-08-25
ATE273961T1 (de)	2004-09-15
HRP20020438A2 (en)	2004-08-31
JP2003512456A (ja)	2003-04-02
ES2222743T3 (es)	2005-02-01
DE69919599T2 (de)	2005-08-11
DE69919599D1 (de)	2004-09-23
KR20020040899A (ko)	2002-05-30
PL354611A1 (en)	2004-02-09
WO2001030760A1 (en)	2001-05-03
EA200200481A1 (ru)	2002-10-31
BG106622A (en)	2002-12-29
CN101445483A (zh)	2009-06-03
EP1222173A1 (en)	2002-07-17
KR20060097747A (ko)	2006-09-14
CN101445483B (zh)	2011-03-30
AU783139B2 (en)	2005-09-29
IL149152A (en)	2008-08-07
PL206482B1 (pl)	2010-08-31
UA73752C2 (en)	2005-09-15
AU1270700A (en)	2001-05-08
HUP0203206A3 (en)	2005-11-28
US20040034234A1 (en)	2004-02-19
IL149152A0 (en)	2002-11-10
BG65483B1 (bg)	2008-09-30
DK1222173T3 (da)	2004-09-20
CZ20021384A3 (cs)	2002-08-14
KR100665599B1 (ko)	2007-01-10
EA005077B1 (ru)	2004-10-28
US6881848B2 (en)	2005-04-19
IN2002MU00312A (2)	2007-06-29
CN1896066A (zh)	2007-01-17

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