BG63007B1 - Пестицидни флуороолефини - Google Patents
Пестицидни флуороолефини Download PDFInfo
- Publication number
- BG63007B1 BG63007B1 BG100934A BG10093496A BG63007B1 BG 63007 B1 BG63007 B1 BG 63007B1 BG 100934 A BG100934 A BG 100934A BG 10093496 A BG10093496 A BG 10093496A BG 63007 B1 BG63007 B1 BG 63007B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- compound
- formula
- group
- substituted
- phenyl
- Prior art date
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- 230000000361 pesticidal effect Effects 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 33
- -1 phenoxy, phenyl Chemical group 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 25
- 150000004795 grignard reagents Chemical class 0.000 claims description 12
- 239000007818 Grignard reagent Substances 0.000 claims description 11
- 239000002689 soil Substances 0.000 claims description 11
- 244000045947 parasite Species 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- 241000894007 species Species 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002917 insecticide Substances 0.000 description 11
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 10
- 229910052749 magnesium Inorganic materials 0.000 description 10
- 238000012746 preparative thin layer chromatography Methods 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 241001674044 Blattodea Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000255925 Diptera Species 0.000 description 6
- FKYPOKTXODYBME-UHFFFAOYSA-N [4-(4-chlorophenyl)-2-fluoro-4-methylpent-2-enyl] acetate Chemical compound CC(=O)OCC(F)=CC(C)(C)C1=CC=C(Cl)C=C1 FKYPOKTXODYBME-UHFFFAOYSA-N 0.000 description 6
- CZGLLUVCCUAKAF-UHFFFAOYSA-N [4-(4-chlorophenyl)-4-cyclopropyl-2-fluorobut-2-enyl] acetate Chemical compound C=1C=C(Cl)C=CC=1C(C=C(F)COC(=O)C)C1CC1 CZGLLUVCCUAKAF-UHFFFAOYSA-N 0.000 description 6
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 6
- IZFINJJZPCOAGD-UHFFFAOYSA-N methyl 4-cyclopropyl-4-(4-ethoxyphenyl)-2-fluorobut-2-enoate Chemical compound C1=CC(OCC)=CC=C1C(C=C(F)C(=O)OC)C1CC1 IZFINJJZPCOAGD-UHFFFAOYSA-N 0.000 description 6
- GREWZYRZMVYLBQ-UHFFFAOYSA-N 4-bromo-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(Br)C=C1OC1=CC=CC=C1 GREWZYRZMVYLBQ-UHFFFAOYSA-N 0.000 description 5
- 241000257226 Muscidae Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- VMAOIZSJPPRWJI-UHFFFAOYSA-N [2-fluoro-4-methyl-4-[4-(trifluoromethoxy)phenyl]pent-2-enyl] acetate Chemical compound CC(=O)OCC(F)=CC(C)(C)C1=CC=C(OC(F)(F)F)C=C1 VMAOIZSJPPRWJI-UHFFFAOYSA-N 0.000 description 5
- BJCZERJFLFNOPP-UHFFFAOYSA-N [4-cyclopropyl-4-(4-ethoxyphenyl)-2-fluorobut-2-enyl] acetate Chemical compound C1=CC(OCC)=CC=C1C(C=C(F)COC(C)=O)C1CC1 BJCZERJFLFNOPP-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- CXTXQBGWWMWLCK-UHFFFAOYSA-N methyl 2,2-dichloro-2-fluoroacetate Chemical compound COC(=O)C(F)(Cl)Cl CXTXQBGWWMWLCK-UHFFFAOYSA-N 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- AHDAKFFMKLQPTD-UHFFFAOYSA-N 1-bromo-3-phenoxybenzene Chemical compound BrC1=CC=CC(OC=2C=CC=CC=2)=C1 AHDAKFFMKLQPTD-UHFFFAOYSA-N 0.000 description 4
- FPEBBCAZUBYMIH-UHFFFAOYSA-N 2-fluoro-4-methyl-4-[4-(trifluoromethoxy)phenyl]pent-2-en-1-ol Chemical compound OCC(F)=CC(C)(C)C1=CC=C(OC(F)(F)F)C=C1 FPEBBCAZUBYMIH-UHFFFAOYSA-N 0.000 description 4
- FBVYEKTWRXGZLJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-fluoro-4-methylpent-2-en-1-ol Chemical compound OCC(F)=CC(C)(C)C1=CC=C(Cl)C=C1 FBVYEKTWRXGZLJ-UHFFFAOYSA-N 0.000 description 4
- NXOSLHPKBLVCGB-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-cyclopropyl-2-fluorobut-2-en-1-ol Chemical compound C=1C=C(Cl)C=CC=1C(C=C(F)CO)C1CC1 NXOSLHPKBLVCGB-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- WUJJZAWLOGKQJQ-UHFFFAOYSA-N [5-(4-ethoxyphenyl)-3-fluorohex-3-en-2-yl] acetate Chemical compound CCOC1=CC=C(C(C)C=C(F)C(C)OC(C)=O)C=C1 WUJJZAWLOGKQJQ-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NLMFTBDEVMMEID-UHFFFAOYSA-N 4-cyclopropyl-4-(4-ethoxyphenyl)-2-fluorobut-2-en-1-ol Chemical compound C1=CC(OCC)=CC=C1C(C=C(F)CO)C1CC1 NLMFTBDEVMMEID-UHFFFAOYSA-N 0.000 description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- OOQVVLQHVPZDNA-UHFFFAOYSA-N methyl 4-(4-chlorophenyl)-2-fluoro-4-methylpent-2-enoate Chemical compound COC(=O)C(F)=CC(C)(C)C1=CC=C(Cl)C=C1 OOQVVLQHVPZDNA-UHFFFAOYSA-N 0.000 description 3
- PIXKSEHATLAMAV-UHFFFAOYSA-N methyl 4-(4-ethoxyphenyl)-2-fluoro-4-methylpent-2-enoate Chemical compound CCOC1=CC=C(C(C)(C)C=C(F)C(=O)OC)C=C1 PIXKSEHATLAMAV-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- SGWLLHXNRGNUPJ-UHFFFAOYSA-N [4-(4-ethoxyphenyl)-2-fluoro-4-methylpent-2-enyl] acetate Chemical compound CCOC1=CC=C(C(C)(C)C=C(F)COC(C)=O)C=C1 SGWLLHXNRGNUPJ-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
- 229950002373 bioresmethrin Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RVJXXLGNIHDTAG-UHFFFAOYSA-N methyl 4-(4-chlorophenyl)-4-cyclopropyl-2-fluorobut-2-enoate Chemical compound C=1C=C(Cl)C=CC=1C(C=C(F)C(=O)OC)C1CC1 RVJXXLGNIHDTAG-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- NWVPLWUGKVMRIZ-UHFFFAOYSA-N 1-[4-fluoro-2-methyl-5-(3-phenoxyphenyl)pent-3-en-2-yl]-4-(trifluoromethoxy)benzene Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C)(C)C=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 NWVPLWUGKVMRIZ-UHFFFAOYSA-N 0.000 description 1
- ITXWCHFNRPTERZ-UHFFFAOYSA-N 1-chloro-4-[4-fluoro-2-methyl-5-(3-phenoxyphenyl)pent-3-en-2-yl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)C=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 ITXWCHFNRPTERZ-UHFFFAOYSA-N 0.000 description 1
- JDXBXUXJWJADCO-UHFFFAOYSA-N 1-ethoxy-4-[4-fluoro-2-methyl-5-(3-phenoxyphenyl)pent-3-en-2-yl]benzene Chemical compound C1=CC(OCC)=CC=C1C(C)(C)C=C(F)CC1=CC=CC(OC=2C=CC=CC=2)=C1 JDXBXUXJWJADCO-UHFFFAOYSA-N 0.000 description 1
- KOISKHDDGOERRH-UHFFFAOYSA-N 1-fluoro-4-[2-fluoro-4-methyl-4-[4-(trifluoromethoxy)phenyl]pent-2-enyl]-2-phenoxybenzene Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C)(C)C=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 KOISKHDDGOERRH-UHFFFAOYSA-N 0.000 description 1
- CFFUTUSXYUPKSJ-UHFFFAOYSA-N 2-(4-ethoxyphenyl)acetaldehyde Chemical compound CCOC1=CC=C(CC=O)C=C1 CFFUTUSXYUPKSJ-UHFFFAOYSA-N 0.000 description 1
- CYDKMUWRBIHVRW-UHFFFAOYSA-N 2-methyl-2-[4-(trifluoromethoxy)phenyl]propanal Chemical compound O=CC(C)(C)C1=CC=C(OC(F)(F)F)C=C1 CYDKMUWRBIHVRW-UHFFFAOYSA-N 0.000 description 1
- BNZFBOWDVKHGSP-UHFFFAOYSA-N 4-(4-ethoxyphenyl)-2-fluoro-4-methylpent-2-en-1-ol Chemical compound CCOC1=CC=C(C(C)(C)C=C(F)CO)C=C1 BNZFBOWDVKHGSP-UHFFFAOYSA-N 0.000 description 1
- IMPFTKSHLMLGGW-UHFFFAOYSA-N 4-[4-(4-ethoxyphenyl)-2-fluoro-4-methylpent-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C)(C)C=C(F)CC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 IMPFTKSHLMLGGW-UHFFFAOYSA-N 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000258920 Chilopoda Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- 241001529600 Diabrotica balteata Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- HFWBELFXCMGIGS-UHFFFAOYSA-N but-2-enylcyclopropane Chemical compound CC=CCC1CC1 HFWBELFXCMGIGS-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- GLZVGOOXNYUJMW-UHFFFAOYSA-N cyclopropyl-(4-ethoxyphenyl)methanone Chemical compound C1=CC(OCC)=CC=C1C(=O)C1CC1 GLZVGOOXNYUJMW-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ZRVYLYVXPQTHAD-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-4-cyclopropyl-2-fluorobut-2-enoate Chemical compound C=1C=C(Cl)C=CC=1C(C=C(F)C(=O)OCC)C1CC1 ZRVYLYVXPQTHAD-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ANJYSOJXCIIKCM-UHFFFAOYSA-N methyl 2-fluoro-4-methyl-4-[4-(trifluoromethoxy)phenyl]pent-2-enoate Chemical compound COC(=O)C(F)=CC(C)(C)C1=CC=C(OC(F)(F)F)C=C1 ANJYSOJXCIIKCM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- WGGJTPQHVFOGPN-UHFFFAOYSA-N pent-2-enyl acetate Chemical compound CCC=CCOC(C)=O WGGJTPQHVFOGPN-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9408605A GB9408605D0 (en) | 1994-04-29 | 1994-04-29 | Pesticidal fluoroolefins |
| PCT/GB1995/000954 WO1995029887A1 (en) | 1994-04-29 | 1995-04-26 | Pesticidal fluoroolefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG100934A BG100934A (en) | 1997-12-30 |
| BG63007B1 true BG63007B1 (bg) | 2001-01-31 |
Family
ID=10754382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG100934A BG63007B1 (bg) | 1994-04-29 | 1996-10-23 | Пестицидни флуороолефини |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5880162A (fi) |
| EP (1) | EP0757668A1 (fi) |
| JP (1) | JPH09512543A (fi) |
| KR (1) | KR970702836A (fi) |
| CN (1) | CN1147242A (fi) |
| AU (1) | AU2264995A (fi) |
| BG (1) | BG63007B1 (fi) |
| BR (1) | BR9507508A (fi) |
| CA (1) | CA2187918A1 (fi) |
| CZ (1) | CZ310796A3 (fi) |
| FI (1) | FI964343A0 (fi) |
| GB (3) | GB9408605D0 (fi) |
| HU (1) | HU215403B (fi) |
| NO (1) | NO307297B1 (fi) |
| PL (1) | PL179373B1 (fi) |
| RU (1) | RU2154625C2 (fi) |
| SK (1) | SK281501B6 (fi) |
| TR (1) | TR28774A (fi) |
| TW (1) | TW398956B (fi) |
| WO (1) | WO1995029887A1 (fi) |
| ZA (1) | ZA953119B (fi) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT811593E (pt) * | 1996-06-03 | 2002-11-29 | Basf Ag | Agentes insecticidas e acaricidas 1,4-diaril-2-fluor-2-buteno |
| US5849958A (en) * | 1997-03-17 | 1998-12-15 | American Cyanamid Company | 1,4,diaryl-2-fluoro-2-butene insecticidal and acaricidal agents |
| ZA974582B (en) * | 1996-06-03 | 1998-11-26 | American Cyanamid Co | Process and intermediate compounds for the preparation of pesticidal fluoroolefin compounds |
| US5892131A (en) * | 1997-05-29 | 1999-04-06 | American Cyanamid Company | Process for the preparation of pesticidal fluoroolefin compounds |
| US5998673A (en) * | 1996-06-03 | 1999-12-07 | American Cyanamid Company | 1, 4-diaryl-2-fluoro-2-butene insecticidal and acaricidal agents |
| US5962742A (en) * | 1996-06-14 | 1999-10-05 | American Cyanamid Company | Process for the preparation of 5-bromo-2 fluorobenzeneboronic acid |
| US6198008B1 (en) | 1997-06-06 | 2001-03-06 | American Cyanamid Company | Process for the preparation of 5-bromo-2-fluorobenzeneboronic acid |
| GEP20022795B (en) * | 1997-06-19 | 2002-09-25 | American Cyanamid Co | Process and Intermediate Compounds for Preparation of Pesticidal Fluoroolefin Compounds |
| TW467889B (en) * | 1997-11-12 | 2001-12-11 | American Cyanamid Co | 1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents |
| IL127856A0 (en) * | 1998-01-30 | 1999-10-28 | American Cyanamid Co | 1,4-Diaryl-3-fluoro-2-butene compounds for protecting animals and humans against attack and infestation by anthropod parasites |
| IL127852A0 (en) * | 1998-01-30 | 1999-10-28 | American Cyanamid Co | Methods and compositions for protecting animals and humans against attack and infestation by arthropod and helminth parasites |
| US6235754B1 (en) | 1998-01-30 | 2001-05-22 | American Cyanamid Company | Methods and compositions for protecting animals and humans against attack and infestation by arthropod and helminth parasites |
| US6646166B1 (en) * | 1998-11-16 | 2003-11-11 | Basf Aktiengesellschaft | Processes for the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene and 1,4-diaryl-2-fluoro 2 butene compounds |
| DE60109914T2 (de) | 2000-05-04 | 2006-02-09 | Basf Ag | 1,4-diaryl-2-fluoro-4-cyano-2-buten-derivate, verfahren zu ihrer herstellung und zwischenprodukte für dieses verfahren |
| CA2421861A1 (en) | 2000-09-12 | 2002-03-21 | Basf Aktiengesellschaft | 1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents |
| DE60110123T2 (de) | 2000-09-12 | 2006-03-02 | Basf Ag | Verfahren und zwischenverbindungen zur herstellung von pestiziden fluorolefinverbindungen |
| TWI780112B (zh) * | 2017-03-31 | 2022-10-11 | 美商科迪華農業科技有限責任公司 | 具有殺蟲效用之分子，及其相關之中間物、組成物暨方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60115545A (ja) * | 1983-11-25 | 1985-06-22 | Sumitomo Chem Co Ltd | 炭化水素系化合物を有効成分とする殺虫剤 |
| GB8409195D0 (en) * | 1984-04-09 | 1984-05-16 | Elliott M | Pesticides |
| US4975451A (en) * | 1989-03-02 | 1990-12-04 | Fmc Corporation | Insecticidal cyclopropyl di(aryl) 2-butenes |
| GB9219612D0 (en) * | 1992-09-16 | 1992-10-28 | Khambay Bhupinder P S | Pesticidal fluoroolefins |
-
1994
- 1994-04-29 GB GB9408605A patent/GB9408605D0/en active Pending
-
1995
- 1995-04-18 ZA ZA953119A patent/ZA953119B/xx unknown
- 1995-04-26 HU HU9602967A patent/HU215403B/hu not_active IP Right Cessation
- 1995-04-26 CA CA002187918A patent/CA2187918A1/en not_active Abandoned
- 1995-04-26 AU AU22649/95A patent/AU2264995A/en not_active Abandoned
- 1995-04-26 RU RU96122872/04A patent/RU2154625C2/ru active
- 1995-04-26 CZ CZ963107A patent/CZ310796A3/cs unknown
- 1995-04-26 GB GB9620352A patent/GB2301360A/en not_active Withdrawn
- 1995-04-26 EP EP95915964A patent/EP0757668A1/en not_active Withdrawn
- 1995-04-26 US US08/732,305 patent/US5880162A/en not_active Expired - Fee Related
- 1995-04-26 WO PCT/GB1995/000954 patent/WO1995029887A1/en not_active Application Discontinuation
- 1995-04-26 CN CN95192851A patent/CN1147242A/zh active Pending
- 1995-04-26 BR BR9507508A patent/BR9507508A/pt not_active IP Right Cessation
- 1995-04-26 PL PL95317027A patent/PL179373B1/pl unknown
- 1995-04-26 JP JP7528060A patent/JPH09512543A/ja active Pending
- 1995-04-26 GB GB9508449A patent/GB2288803B/en not_active Expired - Fee Related
- 1995-04-26 SK SK1289-96A patent/SK281501B6/sk unknown
- 1995-04-28 TW TW084104220A patent/TW398956B/zh not_active IP Right Cessation
- 1995-04-28 TR TR00488/95A patent/TR28774A/xx unknown
-
1996
- 1996-10-23 BG BG100934A patent/BG63007B1/bg unknown
- 1996-10-28 NO NO964563A patent/NO307297B1/no not_active IP Right Cessation
- 1996-10-28 FI FI964343A patent/FI964343A0/fi unknown
- 1996-10-29 KR KR1019960706098A patent/KR970702836A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2264995A (en) | 1995-11-29 |
| GB9408605D0 (en) | 1994-06-22 |
| FI964343L (fi) | 1996-10-28 |
| HUT76430A (en) | 1997-08-28 |
| HU215403B (hu) | 1998-12-28 |
| GB2288803A (en) | 1995-11-01 |
| SK128996A3 (en) | 1997-06-04 |
| KR970702836A (ko) | 1997-06-10 |
| JPH09512543A (ja) | 1997-12-16 |
| CZ310796A3 (en) | 1997-08-13 |
| GB9508449D0 (en) | 1995-06-14 |
| PL317027A1 (en) | 1997-03-03 |
| US5880162A (en) | 1999-03-09 |
| HU9602967D0 (en) | 1996-12-30 |
| GB2301360A (en) | 1996-12-04 |
| NO964563L (no) | 1996-10-28 |
| EP0757668A1 (en) | 1997-02-12 |
| TR28774A (tr) | 1997-02-20 |
| BR9507508A (pt) | 1997-09-02 |
| GB2288803B (en) | 1998-09-16 |
| BG100934A (en) | 1997-12-30 |
| PL179373B1 (en) | 2000-08-31 |
| TW398956B (en) | 2000-07-21 |
| CN1147242A (zh) | 1997-04-09 |
| RU2154625C2 (ru) | 2000-08-20 |
| CA2187918A1 (en) | 1995-11-09 |
| ZA953119B (en) | 1996-01-09 |
| GB9620352D0 (en) | 1996-11-13 |
| NO964563D0 (no) | 1996-10-28 |
| FI964343A0 (fi) | 1996-10-28 |
| WO1995029887A1 (en) | 1995-11-09 |
| SK281501B6 (sk) | 2001-04-09 |
| NO307297B1 (no) | 2000-03-13 |
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