HU218383B - Inszekticid hatású fluor-olefinek, előállításuk, ezeket tartalmazó inszekticid készítmények és ezekkel végzett rovarirtási eljárás - Google Patents
Inszekticid hatású fluor-olefinek, előállításuk, ezeket tartalmazó inszekticid készítmények és ezekkel végzett rovarirtási eljárás Download PDFInfo
- Publication number
- HU218383B HU218383B HU9500773A HU9500773A HU218383B HU 218383 B HU218383 B HU 218383B HU 9500773 A HU9500773 A HU 9500773A HU 9500773 A HU9500773 A HU 9500773A HU 218383 B HU218383 B HU 218383B
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- fluoro
- formula
- cyclopropane
- propenyl
- Prior art date
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- 241000238631 Hexapoda Species 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 48
- 239000000203 mixture Substances 0.000 title claims description 37
- 230000000749 insecticidal effect Effects 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- -1 methylenedioxy Chemical group 0.000 claims abstract description 39
- 239000002689 soil Substances 0.000 claims abstract description 24
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 3
- 239000004480 active ingredient Substances 0.000 claims description 15
- 150000004795 grignard reagents Chemical group 0.000 claims description 15
- 239000007818 Grignard reagent Substances 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000008187 granular material Substances 0.000 claims description 10
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000000575 pesticide Substances 0.000 claims description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 208000015181 infectious disease Diseases 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
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000010410 dusting Methods 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000002458 infectious effect Effects 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 claims 1
- 238000006578 reductive coupling reaction Methods 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 230000000361 pesticidal effect Effects 0.000 abstract description 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 238000012746 preparative thin layer chromatography Methods 0.000 description 15
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 12
- 238000002953 preparative HPLC Methods 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 9
- AHDAKFFMKLQPTD-UHFFFAOYSA-N 1-bromo-3-phenoxybenzene Chemical compound BrC1=CC=CC(OC=2C=CC=CC=2)=C1 AHDAKFFMKLQPTD-UHFFFAOYSA-N 0.000 description 8
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 8
- 239000012346 acetyl chloride Substances 0.000 description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 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 7
- CXTXQBGWWMWLCK-UHFFFAOYSA-N methyl 2,2-dichloro-2-fluoroacetate Chemical compound COC(=O)C(F)(Cl)Cl CXTXQBGWWMWLCK-UHFFFAOYSA-N 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 description 3
- UIMDIRFSLFHWCR-UHFFFAOYSA-N 3-[1-(4-chlorophenyl)cyclopropyl]-2-fluoroprop-2-en-1-ol Chemical compound C=1C=C(Cl)C=CC=1C1(C=C(F)CO)CC1 UIMDIRFSLFHWCR-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- AJHAJKLUTGHFLT-UHFFFAOYSA-N [2-fluoro-3-[1-(4-fluorophenyl)cyclopropyl]prop-2-enyl] acetate Chemical compound C=1C=C(F)C=CC=1C1(C=C(F)COC(=O)C)CC1 AJHAJKLUTGHFLT-UHFFFAOYSA-N 0.000 description 3
- QVQASYJXVVYVPS-UHFFFAOYSA-N [3-[1-(2,4-difluorophenyl)cyclopropyl]-2-fluoroprop-2-enyl] acetate Chemical compound C=1C=C(F)C=C(F)C=1C1(C=C(F)COC(=O)C)CC1 QVQASYJXVVYVPS-UHFFFAOYSA-N 0.000 description 3
- VFAGEPVSLXRUNM-UHFFFAOYSA-N [3-[1-(4-ethoxyphenyl)cyclopropyl]-2-fluoroprop-2-enyl] acetate Chemical compound C1=CC(OCC)=CC=C1C1(C=C(F)COC(C)=O)CC1 VFAGEPVSLXRUNM-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- OBKLRYRACIFYTL-UHFFFAOYSA-N methyl 3-[1-(4-chlorophenyl)cyclopropyl]-2-fluoroprop-2-enoate Chemical compound C=1C=C(Cl)C=CC=1C1(C=C(F)C(=O)OC)CC1 OBKLRYRACIFYTL-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
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- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
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- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- YADWWNQHVYZLLU-UHFFFAOYSA-N 1-[1-[2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl]cyclopropyl]-4-(trifluoromethoxy)benzene Chemical compound C1CC1(C=1C=CC(OC(F)(F)F)=CC=1)C=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 YADWWNQHVYZLLU-UHFFFAOYSA-N 0.000 description 2
- TZIKUTDKYOVUJJ-UHFFFAOYSA-N 1-ethoxy-4-[1-[2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl]cyclopropyl]benzene Chemical compound C1=CC(OCC)=CC=C1C1(C=C(F)CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CC1 TZIKUTDKYOVUJJ-UHFFFAOYSA-N 0.000 description 2
- GMCIVBMWHOJJTR-UHFFFAOYSA-N 1-fluoro-4-[1-[2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl]cyclopropyl]benzene Chemical compound C1CC1(C=1C=CC(F)=CC=1)C=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 GMCIVBMWHOJJTR-UHFFFAOYSA-N 0.000 description 2
- OPPCWNKMZVGJEX-UHFFFAOYSA-N 1-fluoro-4-[2-fluoro-3-[1-(4-fluorophenyl)cyclopropyl]prop-2-enyl]-2-phenoxybenzene Chemical compound C1CC1(C=1C=CC(F)=CC=1)C=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 OPPCWNKMZVGJEX-UHFFFAOYSA-N 0.000 description 2
- VBZUENJQUNCHHT-UHFFFAOYSA-N 1-fluoro-4-[2-fluoro-3-[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]prop-2-enyl]-2-phenoxybenzene Chemical compound C1CC1(C=1C(=CC(=CC=1)C(F)(F)F)F)C=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 VBZUENJQUNCHHT-UHFFFAOYSA-N 0.000 description 2
- LOMQGYLDHIXMFP-UHFFFAOYSA-N 2,4-difluoro-1-[1-[2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl]cyclopropyl]benzene Chemical compound C1CC1(C=1C(=CC(F)=CC=1)F)C=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 LOMQGYLDHIXMFP-UHFFFAOYSA-N 0.000 description 2
- GCYAPDWBFYUIOQ-UHFFFAOYSA-N 2,4-difluoro-1-[1-[2-fluoro-3-(4-fluoro-3-phenoxyphenyl)prop-1-enyl]cyclopropyl]benzene Chemical compound C1CC1(C=1C(=CC(F)=CC=1)F)C=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 GCYAPDWBFYUIOQ-UHFFFAOYSA-N 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- KQUZFCTUDFVQOW-UHFFFAOYSA-N 2-fluoro-1-[1-[2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl]cyclopropyl]-4-(trifluoromethyl)benzene Chemical compound C1CC1(C=1C(=CC(=CC=1)C(F)(F)F)F)C=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 KQUZFCTUDFVQOW-UHFFFAOYSA-N 0.000 description 2
- ZYQPZLLMOAXOSI-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)cyclopropyl]-2-fluoroprop-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1CC1(C=1C=CC(Cl)=CC=1)C=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 ZYQPZLLMOAXOSI-UHFFFAOYSA-N 0.000 description 2
- PYNWISUSXSLQAJ-UHFFFAOYSA-N 4-[3-[1-[4-(difluoromethoxy)phenyl]cyclopropyl]-2-fluoroprop-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OC(F)F)=CC=C1C1(C=C(F)CC=2C=C(OC=3C=CC=CC=3)C(F)=CC=2)CC1 PYNWISUSXSLQAJ-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- AXNPFQGOEBWOAR-UHFFFAOYSA-N [2-fluoro-3-[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]prop-2-enyl] acetate Chemical compound C=1C=C(C(F)(F)F)C=C(F)C=1C1(C=C(F)COC(=O)C)CC1 AXNPFQGOEBWOAR-UHFFFAOYSA-N 0.000 description 2
- QQQZWQCNGSNTSV-UHFFFAOYSA-N [2-fluoro-3-[1-[4-(trifluoromethoxy)phenyl]cyclopropyl]prop-2-enyl] acetate Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C1(C=C(F)COC(=O)C)CC1 QQQZWQCNGSNTSV-UHFFFAOYSA-N 0.000 description 2
- WLRLSUUFSVAATO-UHFFFAOYSA-N [3-[1-[4-(difluoromethoxy)phenyl]cyclopropyl]-2-fluoroprop-2-enyl] acetate Chemical compound C=1C=C(OC(F)F)C=CC=1C1(C=C(F)COC(=O)C)CC1 WLRLSUUFSVAATO-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- FSRAZHNJMPEBRL-UHFFFAOYSA-N methyl 2-fluoro-3-[1-(4-fluorophenyl)cyclopropyl]prop-2-enoate Chemical compound C=1C=C(F)C=CC=1C1(C=C(F)C(=O)OC)CC1 FSRAZHNJMPEBRL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VVVQGZOWNHDLAL-UHFFFAOYSA-N 1-(2,4-difluorophenyl)cyclopropane-1-carbaldehyde Chemical compound FC1=CC(F)=CC=C1C1(C=O)CC1 VVVQGZOWNHDLAL-UHFFFAOYSA-N 0.000 description 1
- HEGXENQCLACJQG-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopropane-1-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1C1(C=O)CC1 HEGXENQCLACJQG-UHFFFAOYSA-N 0.000 description 1
- ZMRBCVCKMGFOBI-UHFFFAOYSA-N 1-(difluoromethoxy)-4-[1-[2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl]cyclopropyl]benzene Chemical compound C1=CC(OC(F)F)=CC=C1C1(C=C(F)CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CC1 ZMRBCVCKMGFOBI-UHFFFAOYSA-N 0.000 description 1
- BRAPKQJMJZTYFH-UHFFFAOYSA-N 1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropane-1-carbaldehyde Chemical compound FC1=CC(C(F)(F)F)=CC=C1C1(C=O)CC1 BRAPKQJMJZTYFH-UHFFFAOYSA-N 0.000 description 1
- QJROFKQLDSKHOL-UHFFFAOYSA-N 1-[4-(trifluoromethoxy)phenyl]cyclopropane-1-carbaldehyde Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1(C=O)CC1 QJROFKQLDSKHOL-UHFFFAOYSA-N 0.000 description 1
- XZBIDJGLZNWDTL-UHFFFAOYSA-N 1-chloro-4-[1-[2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl]cyclopropyl]benzene Chemical compound C1CC1(C=1C=CC(Cl)=CC=1)C=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 XZBIDJGLZNWDTL-UHFFFAOYSA-N 0.000 description 1
- HXBOFIGSLNDZRW-UHFFFAOYSA-N 1-chloro-4-cyclopropylbenzene Chemical compound C1=CC(Cl)=CC=C1C1CC1 HXBOFIGSLNDZRW-UHFFFAOYSA-N 0.000 description 1
- FQYPAYFQUDJGFI-LNKIKWGQSA-N 1-fluoro-4-[(e)-3-[1-(4-fluorophenyl)cyclopropyl]prop-2-enyl]-2-phenoxybenzene Chemical compound C1=CC(F)=CC=C1C1(\C=C\CC=2C=C(OC=3C=CC=CC=3)C(F)=CC=2)CC1 FQYPAYFQUDJGFI-LNKIKWGQSA-N 0.000 description 1
- OBVSTBUYNZGZHQ-UHFFFAOYSA-N 1-fluoro-4-[2-fluoro-3-[1-[4-(trifluoromethoxy)phenyl]cyclopropyl]prop-2-enyl]-2-phenoxybenzene Chemical compound C1CC1(C=1C=CC(OC(F)(F)F)=CC=1)C=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 OBVSTBUYNZGZHQ-UHFFFAOYSA-N 0.000 description 1
- DUFYIWIXVQWODR-UHFFFAOYSA-N 2-fluoro-3-[1-(4-fluorophenyl)cyclopropyl]prop-2-en-1-ol Chemical compound C=1C=C(F)C=CC=1C1(C=C(F)CO)CC1 DUFYIWIXVQWODR-UHFFFAOYSA-N 0.000 description 1
- NIZIYLVJSPDNGV-UHFFFAOYSA-N 2-fluoro-3-[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]prop-2-en-1-ol Chemical compound C=1C=C(C(F)(F)F)C=C(F)C=1C1(C=C(F)CO)CC1 NIZIYLVJSPDNGV-UHFFFAOYSA-N 0.000 description 1
- QJHAMLIMUGYVGX-UHFFFAOYSA-N 2-fluoro-3-[1-[4-(trifluoromethoxy)phenyl]cyclopropyl]prop-2-en-1-ol Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C1(C=C(F)CO)CC1 QJHAMLIMUGYVGX-UHFFFAOYSA-N 0.000 description 1
- NGIHJDCCUNTCKY-UHFFFAOYSA-N 3-[1-(1,3-benzodioxol-5-yl)cyclopropyl]-2-fluoroprop-2-en-1-ol Chemical compound C=1C=C2OCOC2=CC=1C1(C=C(F)CO)CC1 NGIHJDCCUNTCKY-UHFFFAOYSA-N 0.000 description 1
- QJXBVPCKFBYBBP-UHFFFAOYSA-N 3-[1-(2,4-difluorophenyl)cyclopropyl]-2-fluoroprop-2-en-1-ol Chemical compound C=1C=C(F)C=C(F)C=1C1(C=C(F)CO)CC1 QJXBVPCKFBYBBP-UHFFFAOYSA-N 0.000 description 1
- PPPDAWKYEYUYNO-UHFFFAOYSA-N 3-[1-(4-ethoxyphenyl)cyclopropyl]-2-fluoroprop-2-en-1-ol Chemical compound C1=CC(OCC)=CC=C1C1(C=C(F)CO)CC1 PPPDAWKYEYUYNO-UHFFFAOYSA-N 0.000 description 1
- NFCFFXKBGVCRLW-UHFFFAOYSA-N 3-[1-[4-(difluoromethoxy)phenyl]cyclopropyl]-2-fluoroprop-2-en-1-ol Chemical compound C=1C=C(OC(F)F)C=CC=1C1(C=C(F)CO)CC1 NFCFFXKBGVCRLW-UHFFFAOYSA-N 0.000 description 1
- ONUMMKXSGIGZQL-OMCISZLKSA-N 4-[(e)-3-[1-(4-ethoxyphenyl)cyclopropyl]prop-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C1(\C=C\CC=2C=C(OC=3C=CC=CC=3)C(F)=CC=2)CC1 ONUMMKXSGIGZQL-OMCISZLKSA-N 0.000 description 1
- WUKXNQXZQFIJLY-UHFFFAOYSA-N 4-[3-[1-(4-ethoxyphenyl)cyclopropyl]-2-fluoroprop-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C1(C=C(F)CC=2C=C(OC=3C=CC=CC=3)C(F)=CC=2)CC1 WUKXNQXZQFIJLY-UHFFFAOYSA-N 0.000 description 1
- PGWKEGTYTNDEPU-UHFFFAOYSA-N 5-[1-[2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl]cyclopropyl]-1,3-benzodioxole Chemical compound C1CC1(C=1C=C2OCOC2=CC=1)C=C(F)CC(C=1)=CC=CC=1OC1=CC=CC=C1 PGWKEGTYTNDEPU-UHFFFAOYSA-N 0.000 description 1
- IUZBVHJLUZYBEL-UHFFFAOYSA-N 5-[1-[2-fluoro-3-(4-fluoro-3-phenoxyphenyl)prop-1-enyl]cyclopropyl]-1,3-benzodioxole Chemical compound C1CC1(C=1C=C2OCOC2=CC=1)C=C(F)CC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 IUZBVHJLUZYBEL-UHFFFAOYSA-N 0.000 description 1
- HQKFWAYVOSZCJS-UHFFFAOYSA-N 5-cyclopropyl-1,3-benzodioxole Chemical compound C1CC1C1=CC=C(OCO2)C2=C1 HQKFWAYVOSZCJS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 229940126062 Compound A Drugs 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 241001585354 Delia coarctata Species 0.000 description 1
- 241001529600 Diabrotica balteata Species 0.000 description 1
- 244000299507 Gossypium hirsutum Species 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
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 238000006680 Reformatsky reaction Methods 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
- OGUXLWAUGMHVOR-UHFFFAOYSA-N [3-[1-(1,3-benzodioxol-5-yl)cyclopropyl]-2-fluoroprop-2-enyl] acetate Chemical compound C=1C=C2OCOC2=CC=1C1(C=C(F)COC(=O)C)CC1 OGUXLWAUGMHVOR-UHFFFAOYSA-N 0.000 description 1
- SKYREHZCAJIRQS-UHFFFAOYSA-N [3-[1-(4-chlorophenyl)cyclopropyl]-2-fluoroprop-2-enyl] acetate Chemical compound C=1C=C(Cl)C=CC=1C1(C=C(F)COC(=O)C)CC1 SKYREHZCAJIRQS-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229960000892 attapulgite Drugs 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
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- RWNVDUGKSPLHAO-UHFFFAOYSA-N cyclopropyl-[4-(difluoromethoxy)phenyl]methanone Chemical compound C1=CC(OC(F)F)=CC=C1C(=O)C1CC1 RWNVDUGKSPLHAO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine 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
- 239000012669 liquid formulation Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- SSYPASYDAHBJNR-UHFFFAOYSA-N methyl 3-[1-(2,4-difluorophenyl)cyclopropyl]-2-fluoroprop-2-enoate Chemical compound C=1C=C(F)C=C(F)C=1C1(C=C(F)C(=O)OC)CC1 SSYPASYDAHBJNR-UHFFFAOYSA-N 0.000 description 1
- RVTOMEGVBWFJKK-UHFFFAOYSA-N methyl 3-[1-(4-ethoxyphenyl)cyclopropyl]-2-fluoroprop-2-enoate Chemical compound C1=CC(OCC)=CC=C1C1(C=C(F)C(=O)OC)CC1 RVTOMEGVBWFJKK-UHFFFAOYSA-N 0.000 description 1
- HXJIMHPTKURASF-UHFFFAOYSA-N methyl 3-[1-[4-(difluoromethoxy)phenyl]cyclopropyl]-2-fluoroprop-2-enoate Chemical compound C=1C=C(OC(F)F)C=CC=1C1(C=C(F)C(=O)OC)CC1 HXJIMHPTKURASF-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929219612A GB9219612D0 (en) | 1992-09-16 | 1992-09-16 | Pesticidal fluoroolefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9500773D0 HU9500773D0 (en) | 1995-05-29 |
| HUT71731A HUT71731A (en) | 1996-01-29 |
| HU218383B true HU218383B (hu) | 2000-08-28 |
Family
ID=10722016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9500773A HU218383B (hu) | 1992-09-16 | 1993-09-16 | Inszekticid hatású fluor-olefinek, előállításuk, ezeket tartalmazó inszekticid készítmények és ezekkel végzett rovarirtási eljárás |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5763700A (enExample) |
| EP (1) | EP0660815B1 (enExample) |
| JP (1) | JP3286323B2 (enExample) |
| KR (1) | KR950703504A (enExample) |
| CN (1) | CN1037098C (enExample) |
| AT (1) | ATE151737T1 (enExample) |
| BR (1) | BR1100212A (enExample) |
| CA (1) | CA2142714A1 (enExample) |
| DE (1) | DE69309940T2 (enExample) |
| DK (1) | DK0660815T3 (enExample) |
| ES (1) | ES2101343T3 (enExample) |
| GB (2) | GB9219612D0 (enExample) |
| GR (1) | GR3024029T3 (enExample) |
| HU (1) | HU218383B (enExample) |
| IN (1) | IN182328B (enExample) |
| TR (1) | TR27236A (enExample) |
| TW (1) | TW239834B (enExample) |
| WO (1) | WO1994006741A1 (enExample) |
| ZA (1) | ZA936834B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9408605D0 (en) * | 1994-04-29 | 1994-06-22 | British Tech Group | Pesticidal fluoroolefins |
| 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 |
| ATE221037T1 (de) * | 1996-06-03 | 2002-08-15 | Basf Ag | 1,4-diaryl-2-fluoro-2-butene als insectizide und akarizide mittel |
| US5849958A (en) * | 1997-03-17 | 1998-12-15 | American Cyanamid Company | 1,4,diaryl-2-fluoro-2-butene insecticidal and acaricidal agents |
| 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 |
| US6288011B1 (en) | 1997-11-12 | 2001-09-11 | American Cyanamid Co. | 1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents |
| 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 |
| 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 |
| 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 |
| HUP0303198A3 (en) * | 2000-09-12 | 2005-11-28 | Basf Ag | Process and intermediate compounds for the preparation of pesticidal fluoroolefin compounds |
| CA2421861A1 (en) | 2000-09-12 | 2002-03-21 | Basf Aktiengesellschaft | 1,4-diaryl-2,3-difluoro-2-butene insecticidal and acaricidal agents |
| KR101926833B1 (ko) | 2015-06-05 | 2019-03-07 | 주식회사 엘지화학 | 메탈로센 화합물 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562213A (en) * | 1982-05-12 | 1985-12-31 | Sumitomo Chemical Company, Limited | Certain phenoxy-benzyloxy ether derivatives and an insecticidal and/or acaricidal composition containing the same and methods of use |
| EP0120037A1 (en) * | 1982-09-24 | 1984-10-03 | Commonwealth Scientific And Industrial Research Organisation | Arthropodicidal compounds |
| EP0125204A1 (de) * | 1983-04-12 | 1984-11-14 | Ciba-Geigy Ag | 3-Phenoxybenzyl-(2-phenyl-2,2-alkylen-äthyl)-äther und -thioäther, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
| DE3333239A1 (de) * | 1983-09-12 | 1985-03-28 | Schering AG, 1000 Berlin und 4709 Bergkamen | Arylmethylaetherderivate, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| GB8409195D0 (en) | 1984-04-09 | 1984-05-16 | Elliott M | Pesticides |
| JPS62500238A (ja) * | 1984-08-30 | 1987-01-29 | コモンウエルス・サイエンテイフイツク・アンド・インダストリアル・リサ−チ・オ−ガニゼイシヨン | 節足動物駆除剤 |
| DE3513041A1 (de) * | 1985-04-09 | 1986-10-16 | Schering AG, Berlin und Bergkamen, 1000 Berlin | Difluorcyclopropanderivate, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
-
1992
- 1992-09-16 GB GB929219612A patent/GB9219612D0/en active Pending
-
1993
- 1993-09-10 IN IN1017DE1993 patent/IN182328B/en unknown
- 1993-09-13 TR TR00829/93A patent/TR27236A/xx unknown
- 1993-09-14 TW TW082107549A patent/TW239834B/zh active
- 1993-09-16 KR KR1019950701062A patent/KR950703504A/ko not_active Ceased
- 1993-09-16 US US08/403,795 patent/US5763700A/en not_active Expired - Fee Related
- 1993-09-16 CA CA002142714A patent/CA2142714A1/en not_active Abandoned
- 1993-09-16 HU HU9500773A patent/HU218383B/hu not_active IP Right Cessation
- 1993-09-16 DE DE69309940T patent/DE69309940T2/de not_active Expired - Fee Related
- 1993-09-16 ES ES93920956T patent/ES2101343T3/es not_active Expired - Lifetime
- 1993-09-16 JP JP50792394A patent/JP3286323B2/ja not_active Expired - Fee Related
- 1993-09-16 EP EP93920956A patent/EP0660815B1/en not_active Expired - Lifetime
- 1993-09-16 AT AT93920956T patent/ATE151737T1/de not_active IP Right Cessation
- 1993-09-16 CN CN93119025A patent/CN1037098C/zh not_active Expired - Fee Related
- 1993-09-16 GB GB9319153A patent/GB2270693B/en not_active Revoked
- 1993-09-16 WO PCT/GB1993/001959 patent/WO1994006741A1/en not_active Ceased
- 1993-09-16 DK DK93920956.5T patent/DK0660815T3/da active
- 1993-09-16 ZA ZA936834A patent/ZA936834B/xx unknown
-
1997
- 1997-04-02 BR BR1100212-3A patent/BR1100212A/pt active IP Right Grant
- 1997-07-09 GR GR970401684T patent/GR3024029T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1037098C (zh) | 1998-01-21 |
| HUT71731A (en) | 1996-01-29 |
| DE69309940T2 (de) | 1997-09-04 |
| GB9219612D0 (en) | 1992-10-28 |
| EP0660815B1 (en) | 1997-04-16 |
| CN1087895A (zh) | 1994-06-15 |
| GB2270693B (en) | 1995-11-15 |
| EP0660815A1 (en) | 1995-07-05 |
| JPH08504186A (ja) | 1996-05-07 |
| BR1100212A (pt) | 1999-10-05 |
| ES2101343T3 (es) | 1997-07-01 |
| GR3024029T3 (en) | 1997-10-31 |
| ATE151737T1 (de) | 1997-05-15 |
| JP3286323B2 (ja) | 2002-05-27 |
| DK0660815T3 (da) | 1997-05-26 |
| WO1994006741A1 (en) | 1994-03-31 |
| IN182328B (enExample) | 1999-03-20 |
| DE69309940D1 (de) | 1997-05-22 |
| KR950703504A (ko) | 1995-09-20 |
| HU9500773D0 (en) | 1995-05-29 |
| TR27236A (tr) | 1994-12-20 |
| TW239834B (enExample) | 1995-02-01 |
| GB2270693A (en) | 1994-03-23 |
| ZA936834B (en) | 1995-03-16 |
| US5763700A (en) | 1998-06-09 |
| CA2142714A1 (en) | 1994-03-31 |
| GB9319153D0 (en) | 1993-11-03 |
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Legal Events
| Date | Code | Title | Description |
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| HMM4 | Cancellation of final prot. due to non-payment of fee |