CS209913B2 - Insecticide means and method of making the active substances - Google Patents
Insecticide means and method of making the active substances Download PDFInfo
- Publication number
- CS209913B2 CS209913B2 CS79407A CS40779A CS209913B2 CS 209913 B2 CS209913 B2 CS 209913B2 CS 79407 A CS79407 A CS 79407A CS 40779 A CS40779 A CS 40779A CS 209913 B2 CS209913 B2 CS 209913B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- carbon atoms
- group
- align
- compound
- Prior art date
Links
- 239000013543 active substance Substances 0.000 title description 7
- 239000002917 insecticide Substances 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 54
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 46
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 33
- 239000004480 active ingredient Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- USPVNSDVCUTNJN-UHFFFAOYSA-N ethenyl cyclopropanecarboxylate Chemical compound C=COC(=O)C1CC1 USPVNSDVCUTNJN-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000006506 3-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 7
- 125000003158 alcohol group Chemical group 0.000 abstract description 3
- XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 17
- 241000238631 Hexapoda Species 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 229960000490 permethrin Drugs 0.000 description 15
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 241001124076 Aphididae Species 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- SPVZAYWHHVLPBN-UJURSFKZSA-N (1s,3r)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)C(F)(F)F)[C@@H]1C(O)=O SPVZAYWHHVLPBN-UJURSFKZSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 230000003389 potentiating effect Effects 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 241001521235 Spodoptera eridania Species 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- ABALMDTULZCSTP-UJURSFKZSA-N (1s,3s)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@@H](C=C(Cl)C(F)(F)F)[C@@H]1C(Cl)=O ABALMDTULZCSTP-UJURSFKZSA-N 0.000 description 4
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 241000258913 Oncopeltus fasciatus Species 0.000 description 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- ZYINEYXPVKSTHR-NKWVEPMBSA-N (1S,3S)-2,2-dimethyl-3-(3,3,3-trifluoro-2-methylprop-1-enyl)cyclopropane-1-carboxylic acid Chemical compound CC(=C[C@H]1[C@@H](C1(C)C)C(=O)O)C(F)(F)F ZYINEYXPVKSTHR-NKWVEPMBSA-N 0.000 description 3
- SNLWRUNHDLFPFZ-UHFFFAOYSA-M 3-methylbut-2-enyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=C(C)C)C1=CC=CC=C1 SNLWRUNHDLFPFZ-UHFFFAOYSA-M 0.000 description 3
- 241000462639 Epilachna varivestis Species 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000256247 Spodoptera exigua Species 0.000 description 3
- 241000255993 Trichoplusia ni Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- HYPBCSOYFJREHZ-CRCLSJGQSA-N (1S,3S)-3-(2,2-dichloro-3,3,3-trifluoropropyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1([C@H]([C@@H]1CC(C(F)(F)F)(Cl)Cl)C(=O)O)C HYPBCSOYFJREHZ-CRCLSJGQSA-N 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 2
- XDXBCXDBFNODND-UHFFFAOYSA-N 1,1,1-trifluoro-2,5-dimethylhexa-2,4-diene Chemical compound CC(C)=CC=C(C)C(F)(F)F XDXBCXDBFNODND-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 241000253994 Acyrthosiphon pisum Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 241000255967 Helicoverpa zea Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000003466 anti-cipated effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- AMIBLBGLTDBYJJ-UHFFFAOYSA-N ethyl 4,6,6-trichloro-7,7,7-trifluoro-3,3-dimethylheptanoate Chemical compound CCOC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)C(F)(F)F AMIBLBGLTDBYJJ-UHFFFAOYSA-N 0.000 description 2
- YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RTRBHVOKZNZJDH-PKOBYXMFSA-N (3-phenoxyphenyl)methyl (1s,3r)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)C(F)(F)F)[C@@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RTRBHVOKZNZJDH-PKOBYXMFSA-N 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 1
- PCWLWQHNJVRNKZ-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-enyl cyclopropanecarboxylate Chemical class FC(F)(F)C=COC(=O)C1CC1 PCWLWQHNJVRNKZ-UHFFFAOYSA-N 0.000 description 1
- LGMPVUDVTHHFDR-UHFFFAOYSA-N 4-chloro-2-methylbut-1-ene Chemical compound CC(=C)CCCl LGMPVUDVTHHFDR-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 244000260524 Chrysanthemum balsamita Species 0.000 description 1
- 235000005633 Chrysanthemum balsamita Nutrition 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 101001108356 Homo sapiens Nardilysin Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 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
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 102100021850 Nardilysin Human genes 0.000 description 1
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical class OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- ZLDOMUPTDYCDBS-UHFFFAOYSA-N ethyl 3,3-dimethylpent-4-enoate Chemical compound CCOC(=O)CC(C)(C)C=C ZLDOMUPTDYCDBS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- BNTZFXLKSXUEBE-UHFFFAOYSA-N methyl 4,6,6-trichloro-7,7,7-trifluoro-3,3-dimethylheptanoate Chemical compound COC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)C(F)(F)F BNTZFXLKSXUEBE-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- ITDJKCJYYAQMRO-UHFFFAOYSA-L rhodium(2+);diacetate Chemical compound [Rh+2].CC([O-])=O.CC([O-])=O ITDJKCJYYAQMRO-UHFFFAOYSA-L 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000011273 tar residue Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- 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
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
- C07C29/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only in the presence of mineral boron compounds with, when necessary, hydrolysis of the intermediate formed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/32—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.3.0) system, e.g. indenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
-
- 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
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87097378A | 1978-01-20 | 1978-01-20 | |
| US92719878A | 1978-07-24 | 1978-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209913B2 true CS209913B2 (en) | 1981-12-31 |
Family
ID=27128180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS79407A CS209913B2 (en) | 1978-01-20 | 1979-01-18 | Insecticide means and method of making the active substances |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4263319A (fr) |
| EP (1) | EP0003336B1 (fr) |
| JP (1) | JPS54112820A (fr) |
| AR (1) | AR231431A1 (fr) |
| AT (1) | AT367391B (fr) |
| AU (1) | AU535346B2 (fr) |
| BR (1) | BR7900361A (fr) |
| CA (1) | CA1251801A (fr) |
| CS (1) | CS209913B2 (fr) |
| DD (2) | DD151444A5 (fr) |
| DE (1) | DE2966699D1 (fr) |
| DK (1) | DK159260C (fr) |
| DO (1) | DOP1979002732A (fr) |
| EG (1) | EG13725A (fr) |
| ES (1) | ES8205492A1 (fr) |
| GR (1) | GR67601B (fr) |
| HK (1) | HK43387A (fr) |
| IE (1) | IE48309B1 (fr) |
| IL (1) | IL56340A (fr) |
| IN (1) | IN150399B (fr) |
| IT (1) | IT1111011B (fr) |
| MX (1) | MX6173E (fr) |
| MY (1) | MY8800115A (fr) |
| NL (1) | NL971028I2 (fr) |
| NZ (1) | NZ189438A (fr) |
| PL (1) | PL125296B1 (fr) |
| SG (1) | SG15887G (fr) |
| SU (1) | SU1344244A3 (fr) |
| TR (1) | TR21071A (fr) |
| YU (1) | YU8679A (fr) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BG48333A3 (en) * | 1978-02-28 | 1991-01-15 | Montedison Spa | Method for preparing of 2, 2- dimethyl cyclopropane carbonic acid derivatives |
| DE2831193A1 (de) * | 1978-07-15 | 1980-01-24 | Bayer Ag | Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide |
| DE2842541A1 (de) * | 1978-09-29 | 1980-05-22 | Bayer Ag | Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide |
| US4333950A (en) * | 1979-05-24 | 1982-06-08 | Fmc Corporation | (+)-4-Substituted-2-indanol insecticidal ester derivatives |
| GB2093831B (en) * | 1981-02-24 | 1985-09-25 | Fmc Corp | 4-substituted-2-indanols and insecticidal ester derivatives |
| US4402973A (en) * | 1980-10-02 | 1983-09-06 | Fmc Corporation | Insecticidal (1,1'-biphenyl)-3-ylmethyl esters |
| IT1131883B (it) * | 1980-07-02 | 1986-06-25 | Montedison Spa | Processo per la sintesi stereoselettiva di ciclopropancarbossilati intermaedi per piretroidi |
| US4339457A (en) * | 1980-10-20 | 1982-07-13 | Fmc Corporation | 3-(Pyrrol-1-yl)phenylmethyl esters and intermediates |
| US4368205A (en) * | 1980-10-31 | 1983-01-11 | Fmc Corporation | 4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives |
| US4417078A (en) * | 1980-12-31 | 1983-11-22 | Fmc Corporation | Process for producing (+)-4-substituted-2-indanols |
| US4423255A (en) * | 1980-12-31 | 1983-12-27 | Fmc Corporation | (+)-4-Substituted-2-indanols |
| US4429149A (en) | 1980-12-31 | 1984-01-31 | Fmc Corporation | 4-Phenyl-2-indanyl esters of 1R,cis-3-(2-halo-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid |
| DE3171352D1 (en) * | 1981-01-21 | 1985-08-14 | Ici Plc | Halobenzyl esters of haloalkenylcyclopropane acids, their preparation, compositions and method of combating insect pests therewith |
| US4362744A (en) * | 1981-03-19 | 1982-12-07 | Fmc Corporation | Trans-3-substituted-1-indanol insecticidal ester derivatives |
| US4415748A (en) * | 1981-08-06 | 1983-11-15 | Fmc Corporation | Intermediates for insecticidal synthetic pyrethroids |
| EP0073566A1 (fr) * | 1981-08-27 | 1983-03-09 | Imperial Chemical Industries Plc | Procédés et compositions pour combattre les pestes dans la terre |
| FR2515176A1 (fr) * | 1981-10-23 | 1983-04-29 | Roussel Uclaf | Nouveaux esters d'alcools aromatiques ou heteroaromatiques, leur procede de preparation et leur application a la lutte contre les parasites |
| EP0091208B1 (fr) * | 1982-04-05 | 1986-06-18 | Imperial Chemical Industries Plc | Méthode pour la lutte contre les insectes et cyclopropanecarboxylates utilisables comme composés actifs dans celle-ci |
| FR2534918A2 (fr) * | 1982-10-26 | 1984-04-27 | Roussel Uclaf | Nouveaux esters d'alcools aromatiques et heteroaromatiques, leur procede de preparation et leur application a la lutte contre les parasites |
| USH49H (en) | 1983-01-10 | 1986-04-01 | Fmc Corporation | Process for producing 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates |
| DK113384A (da) * | 1983-03-11 | 1984-09-12 | Fmc Corp | Difluorethenylcyclopropancarboxylater, insecticide og acaricide midler og fremgangsmaade til bekaempelse af insekter og acarider |
| US4552892A (en) * | 1983-03-11 | 1985-11-12 | Fmc Corporation | Acaricidal difluoroethenylcyclopropanecarboxylates |
| FR2628103B1 (fr) * | 1988-03-03 | 1991-06-14 | Roussel Uclaf | Nouveaux esters pyrethrinoides portant un noyau indanyle, leur procede de preparation et leur application comme pesticides |
| IT1226546B (it) * | 1988-07-07 | 1991-01-24 | Mini Ricerca Scient Tecnolog | Esteri dell'acido 2,2-dimetil- ciclopropancarbossilico |
| DE3907069A1 (de) * | 1989-03-04 | 1990-09-06 | Basf Ag | Substituierte 2-phenyl-alk(en)yl-1-yl-cyclopropancarbonsaeurebenzylester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| GB9100654D0 (en) * | 1991-01-11 | 1991-02-27 | Ici Plc | Process for preparing halogenated compounds |
| FR2686602B1 (fr) * | 1992-01-28 | 1994-03-11 | Roussel Uclaf | Nouveaux derives de l'acide 2,2-dimethyl 3-[(2,2-difluorocyclopropylidene methyl] cyclopropane carboxylique, leur procede de preparation et leur application comme pesticides. |
| FR2708930B1 (fr) * | 1993-08-10 | 1995-09-08 | Roussel Uclaf | Nouveaux esters dérivés de l'acide 2,2-diméthyl 3-(3,3,3-trifluoro-1-propényl) cyclopropane carboxylique, leur procédé de préparation et leur application comme pesticides. |
| US6048892A (en) * | 1997-12-30 | 2000-04-11 | Sumitomo Chemical Company, Limited | Ester compound pesticide containing thereof |
| AU753585B2 (en) * | 1998-09-15 | 2002-10-24 | Sumitomo Chemical Company, Limited | Ester compound and pesticide containing thereof |
| GB0017617D0 (en) * | 2000-07-18 | 2000-09-06 | Zeneca Ltd | Chemical process |
| KR20140133601A (ko) * | 2012-03-13 | 2014-11-19 | 레드엑스 파마 리미티드 | 농약 |
| CN104326862B (zh) * | 2014-11-20 | 2016-08-17 | 西安近代化学研究所 | 一种2,4-二氯-1,1,1-三氟丁烷衍生物的制备方法 |
| CN109111373A (zh) * | 2018-10-09 | 2019-01-01 | 南通天泽化工有限公司 | 一种三氟氯氰菊酯的制备方法 |
| CN109912386A (zh) * | 2019-03-26 | 2019-06-21 | 江苏春江润田农化有限公司 | 一种可回收型功夫酸生产方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647857A (en) * | 1970-03-16 | 1972-03-07 | Procter & Gamble | Novel esters of chrysanthemic acid and alcohols related to 2-indanol |
| US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
| JPS51141844A (en) * | 1975-05-30 | 1976-12-07 | Kuraray Co Ltd | Process for preparing substituted cyclopropane-carboxylic acid esters |
| DE2638356A1 (de) | 1976-08-26 | 1978-03-02 | Bayer Ag | Verfahren zur herstellung vinylsubstituierter cyclopropancarbonsaeureester |
| US4160842A (en) * | 1976-08-27 | 1979-07-10 | Fmc Corporation | Insecticidal [β-(substituted-phenyl)vinyl]cyclopropanecarboxylates |
| US4157397A (en) * | 1976-08-27 | 1979-06-05 | Fmc Corporation | Insecticidal (β-phenylvinyl)cyclopropanecarboxylates |
| US4183948A (en) * | 1977-01-24 | 1980-01-15 | Imperial Chemical Industries Limited | Halogenated esters |
| GB1572669A (en) * | 1977-05-26 | 1980-08-28 | Ici Ltd | Manufacture of esters |
-
1978
- 1978-11-30 IN IN867/DEL/78A patent/IN150399B/en unknown
- 1978-12-28 CA CA000318687A patent/CA1251801A/fr not_active Expired
- 1978-12-28 DK DK585078A patent/DK159260C/da not_active IP Right Cessation
- 1978-12-29 IL IL56340A patent/IL56340A/xx unknown
-
1979
- 1979-01-02 IE IE9/79A patent/IE48309B1/en unknown
- 1979-01-04 GR GR58023A patent/GR67601B/el unknown
- 1979-01-16 YU YU00086/79A patent/YU8679A/xx unknown
- 1979-01-17 TR TR21071A patent/TR21071A/xx unknown
- 1979-01-17 MX MX797663U patent/MX6173E/es unknown
- 1979-01-18 AT AT0038279A patent/AT367391B/de not_active IP Right Cessation
- 1979-01-18 CS CS79407A patent/CS209913B2/cs unknown
- 1979-01-18 JP JP347779A patent/JPS54112820A/ja active Granted
- 1979-01-18 IT IT19418/79A patent/IT1111011B/it active Protection Beyond IP Right Term
- 1979-01-19 DE DE7979100163T patent/DE2966699D1/de not_active Expired
- 1979-01-19 NZ NZ189438A patent/NZ189438A/xx unknown
- 1979-01-19 DD DD79218544A patent/DD151444A5/de unknown
- 1979-01-19 DO DO1979002732A patent/DOP1979002732A/es unknown
- 1979-01-19 BR BRPI7900361-3A patent/BR7900361A/pt not_active IP Right Cessation
- 1979-01-19 PL PL1979212897A patent/PL125296B1/pl unknown
- 1979-01-19 ES ES476994A patent/ES8205492A1/es not_active Expired
- 1979-01-19 AU AU43507/79A patent/AU535346B2/en not_active Expired
- 1979-01-19 EP EP79100163A patent/EP0003336B1/fr not_active Expired
- 1979-01-19 DD DD79210563A patent/DD145996A5/de unknown
- 1979-01-20 EG EG38/79A patent/EG13725A/xx active
- 1979-05-24 US US06/042,372 patent/US4263319A/en not_active Expired - Lifetime
-
1980
- 1980-12-22 SU SU803220194A patent/SU1344244A3/ru active
-
1983
- 1983-11-02 AR AR294701A patent/AR231431A1/es active
-
1987
- 1987-02-19 SG SG158/87A patent/SG15887G/en unknown
- 1987-06-04 HK HK433/87A patent/HK43387A/xx not_active IP Right Cessation
-
1988
- 1988-12-30 MY MY115/88A patent/MY8800115A/xx unknown
-
1997
- 1997-08-07 NL NL971028C patent/NL971028I2/nl unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS209913B2 (en) | Insecticide means and method of making the active substances | |
| US4868209A (en) | Halogenated esters | |
| US4212879A (en) | Benzyl pyrrolyl methyl carboxylate insecticides and acaricides | |
| US4332815A (en) | Insecticidal perhaloalkylvinylcyclopropanecarboxylates | |
| JPH0112742B2 (fr) | ||
| EP0054360B1 (fr) | Esters fluorobenzyliques d'acides cyclopropanecarboxyliques, leur préparation, compositions les contenant et leur utilisation comme insecticides | |
| DD147665A5 (de) | Verfahren zur herstellung von substituierten 3-(2,2-dihalogenaethenyl)-2,2-dimethylcyclopropancarbonsaeure-eckige klammer auf 1,1'-biphenyl eckige klammer zu-3-ylmethylestern | |
| US4243677A (en) | Insecticidal perhaloalkylvinylcyclopropanecarboxylates | |
| CS197266B2 (en) | Insecticide and acaricide means | |
| US4341796A (en) | Control of acarids with biphenylmethyl perhaloalkylvinylcyclopropanecarboxylates | |
| JPH0231708B2 (fr) | ||
| EP0003420A1 (fr) | Insecticides à base d'arylthiovinylcyclopropanecarboxylates et intermédiaires | |
| US4235927A (en) | Insecticidal benzylfurylmethyl perhaloalkylvinylcyclopropanecarboxylates | |
| PL135350B1 (pl) | Method of obtaining novel pyretroides and insecticide and/or acaricide | |
| US4335252A (en) | Insecticidal pyrethroid enantiomer pair | |
| US4599358A (en) | Pyrethroids | |
| EP2186794A1 (fr) | Ester alpha-cyano-4-fluoro-3-phénoxybenzylique de l'acide pyréthrique monohalogéné, son procédé de préparation et son utilisation | |
| JPH0641015A (ja) | ６−（トリフルオルメチル）ベンジルアルコールから誘導される新規なピレスリノイドエステル、それらの製造法及びそれらの有害生物駆除剤としての用途 | |
| US4346251A (en) | 4-Substituted-2-indanols | |
| US4409238A (en) | Insecticides and insecticidal compositions | |
| JPS6030301B2 (ja) | シクロプロパンカルボン酸３−（２，２−ジクロロビニルオキシ）ベンジルエステル、その製造方法及び該化合物を含有する殺虫、殺ダニ剤 | |
| FR2527601A1 (fr) | Compose, composition et procede pour lutter contre les insectes | |
| US4239773A (en) | Insecticidal esters of certain substituted 7-oxabicyclo[2.2.1]2,5-heptadiene methanols | |
| KR820000654B1 (ko) | 퍼할로 알킬비닐싸이클로프로판 카르복시레이트의 제조방법 | |
| JP2823595B2 (ja) | ２，２―ジメチルシクロプロパンカルボン酸のエステル |