DE2757066C2 - - Google Patents
Info
- Publication number
- DE2757066C2 DE2757066C2 DE2757066A DE2757066A DE2757066C2 DE 2757066 C2 DE2757066 C2 DE 2757066C2 DE 2757066 A DE2757066 A DE 2757066A DE 2757066 A DE2757066 A DE 2757066A DE 2757066 C2 DE2757066 C2 DE 2757066C2
- Authority
- DE
- Germany
- Prior art keywords
- isopropyl
- acid
- group
- cyano
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 70
- -1 m-phenoxybenzyl ester Chemical class 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 15
- 230000000749 insecticidal effect Effects 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 6
- 230000000895 acaricidal effect Effects 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- PYQWVKPCMUFCRW-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoate Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 PYQWVKPCMUFCRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- GBIHOLCMZGAKNG-UHFFFAOYSA-N flucythrinate Chemical compound C=1C=C(OC(F)F)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
- 230000001804 emulsifying effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 79
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
- 238000006243 chemical reaction Methods 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000003921 oil Substances 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 241000238876 Acari Species 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 21
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000011161 development Methods 0.000 description 14
- 230000018109 developmental process Effects 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 241000255925 Diptera Species 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 241000985245 Spodoptera litura Species 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 241000238631 Hexapoda Species 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 238000011835 investigation Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 240000002024 Gossypium herbaceum Species 0.000 description 8
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 241000238680 Rhipicephalus microplus Species 0.000 description 7
- 241000258242 Siphonaptera Species 0.000 description 7
- 235000013601 eggs Nutrition 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 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 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 210000003608 fece Anatomy 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- QIMUYXGVXHABQI-UHFFFAOYSA-N 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(OC(F)(F)F)C=C1 QIMUYXGVXHABQI-UHFFFAOYSA-N 0.000 description 4
- 241000256190 Anopheles quadrimaculatus Species 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
- 241001480793 Dermacentor variabilis Species 0.000 description 4
- 241000256244 Heliothis virescens Species 0.000 description 4
- 241000238745 Musca autumnalis Species 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241001481696 Rhipicephalus sanguineus Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 3
- MZTLKRLBGMLXEL-UHFFFAOYSA-N 1-(bromomethyl)-4-(1,1,2,2-tetrafluoroethoxy)benzene Chemical compound FC(F)C(F)(F)OC1=CC=C(CBr)C=C1 MZTLKRLBGMLXEL-UHFFFAOYSA-N 0.000 description 3
- VACIXOPZIXUAKS-UHFFFAOYSA-N 1-methyl-4-(1,1,2,2-tetrafluoroethoxy)benzene Chemical compound CC1=CC=C(OC(F)(F)C(F)F)C=C1 VACIXOPZIXUAKS-UHFFFAOYSA-N 0.000 description 3
- UMYCEVQRDMCARW-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methylbutanenitrile Chemical compound CC(C)C(C#N)C1=CC=C(O)C=C1 UMYCEVQRDMCARW-UHFFFAOYSA-N 0.000 description 3
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 3
- OYGCWHSVOCRIMA-UHFFFAOYSA-N 3,3-dimethyl-2-[4-(trifluoromethoxy)phenyl]butanoic acid Chemical compound CC(C)(C)C(C(O)=O)C1=CC=C(OC(F)(F)F)C=C1 OYGCWHSVOCRIMA-UHFFFAOYSA-N 0.000 description 3
- DTUWPQOYMPLYSM-UHFFFAOYSA-N 3-methyl-2-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]butanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(OC(F)(F)C(F)F)C=C1 DTUWPQOYMPLYSM-UHFFFAOYSA-N 0.000 description 3
- ZJXJJFSDURDZRP-UHFFFAOYSA-N 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanenitrile Chemical compound CC(C)C(C#N)C1=CC=C(OC(F)(F)F)C=C1 ZJXJJFSDURDZRP-UHFFFAOYSA-N 0.000 description 3
- 241001425390 Aphis fabae Species 0.000 description 3
- 241000995027 Empoasca fabae Species 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- 150000003983 crown ethers Chemical class 0.000 description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000010871 livestock manure Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- JBAKZVLANWWXLJ-UHFFFAOYSA-N (3-phenoxyphenyl)methyl 3-methyl-2-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]butanoate Chemical compound C=1C=C(OC(F)(F)C(F)F)C=CC=1C(C(C)C)C(=O)OCC(C=1)=CC=CC=1OC1=CC=CC=C1 JBAKZVLANWWXLJ-UHFFFAOYSA-N 0.000 description 2
- FRHAFNRTNWOQIL-UHFFFAOYSA-N (3-phenoxyphenyl)methyl 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoate Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C(C)C)C(=O)OCC(C=1)=CC=CC=1OC1=CC=CC=C1 FRHAFNRTNWOQIL-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- VAYGJBCOCRVROJ-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethylsulfanyl)benzene Chemical compound FC(F)(F)SC1=CC=C(CBr)C=C1 VAYGJBCOCRVROJ-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- GDBITPXOESTAML-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(O)C=C1 GDBITPXOESTAML-UHFFFAOYSA-N 0.000 description 2
- GEQWCUVIQMRCAZ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(O)C=C1 GEQWCUVIQMRCAZ-UHFFFAOYSA-N 0.000 description 2
- FEVVTKCAZXCXEQ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)pentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=C(O)C=C1 FEVVTKCAZXCXEQ-UHFFFAOYSA-N 0.000 description 2
- CNBUXJALZYSKQJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-methylbutanenitrile Chemical compound COC1=CC=C(C(C#N)C(C)C)C=C1 CNBUXJALZYSKQJ-UHFFFAOYSA-N 0.000 description 2
- PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 description 2
- URYMRVDLIBKXNB-UHFFFAOYSA-N 2-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]acetonitrile Chemical compound FC(F)C(F)(F)OC1=CC=C(CC#N)C=C1 URYMRVDLIBKXNB-UHFFFAOYSA-N 0.000 description 2
- LXJRCJQNKRXQLY-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]pentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=C(OC(F)F)C=C1 LXJRCJQNKRXQLY-UHFFFAOYSA-N 0.000 description 2
- MAJFSFIOQKLTQH-UHFFFAOYSA-N 2-[4-(difluoromethylsulfanyl)phenyl]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(SC(F)F)C=C1 MAJFSFIOQKLTQH-UHFFFAOYSA-N 0.000 description 2
- LYFCAROXYJTUQF-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]acetonitrile Chemical compound FC(F)(F)OC1=CC=C(CC#N)C=C1 LYFCAROXYJTUQF-UHFFFAOYSA-N 0.000 description 2
- ULMVDTBZVARXOJ-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]pentanoic acid Chemical class CCCC(C(O)=O)C1=CC=C(OC(F)(F)F)C=C1 ULMVDTBZVARXOJ-UHFFFAOYSA-N 0.000 description 2
- HZIDFDPCOAUCGK-UHFFFAOYSA-N 2-[4-(trifluoromethylsulfanyl)phenyl]acetonitrile Chemical compound FC(F)(F)SC1=CC=C(CC#N)C=C1 HZIDFDPCOAUCGK-UHFFFAOYSA-N 0.000 description 2
- PTBIVRMXTMPHBJ-UHFFFAOYSA-N 2-[4-(trifluoromethylsulfanyl)phenyl]butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(SC(F)(F)F)C=C1 PTBIVRMXTMPHBJ-UHFFFAOYSA-N 0.000 description 2
- HCZZJXUAGKRTAP-UHFFFAOYSA-N 2-[4-(trifluoromethylsulfanyl)phenyl]pentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=C(SC(F)(F)F)C=C1 HCZZJXUAGKRTAP-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- PVUXOAXXXXGDFN-UHFFFAOYSA-N 3-methyl-2-(4-sulfanylphenyl)butanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(S)C=C1 PVUXOAXXXXGDFN-UHFFFAOYSA-N 0.000 description 2
- YAGKXWOCKMLECL-UHFFFAOYSA-N 3-methyl-2-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]butanenitrile Chemical compound CC(C)C(C#N)C1=CC=C(OC(F)(F)C(F)F)C=C1 YAGKXWOCKMLECL-UHFFFAOYSA-N 0.000 description 2
- GQKBVWCWRLXTPJ-UHFFFAOYSA-N 3-methyl-2-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]butanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(OC(F)(F)C(F)F)C=C1 GQKBVWCWRLXTPJ-UHFFFAOYSA-N 0.000 description 2
- KPZFKIYGSAJNLQ-UHFFFAOYSA-N 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(OC(F)(F)F)C=C1 KPZFKIYGSAJNLQ-UHFFFAOYSA-N 0.000 description 2
- KUIVQIHLLUMGLX-UHFFFAOYSA-N 3-methyl-2-[4-(trifluoromethylsulfanyl)phenyl]butanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(SC(F)(F)F)C=C1 KUIVQIHLLUMGLX-UHFFFAOYSA-N 0.000 description 2
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WSWMGHRLUYADNA-UHFFFAOYSA-N 7-nitro-1,2,3,4-tetrahydroquinoline Chemical compound C1CCNC2=CC([N+](=O)[O-])=CC=C21 WSWMGHRLUYADNA-UHFFFAOYSA-N 0.000 description 2
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- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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 |
|---|---|---|---|
| US81460077A | 1977-07-11 | 1977-07-11 | |
| US83051577A | 1977-09-06 | 1977-09-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2757066A1 DE2757066A1 (de) | 1979-02-01 |
| DE2757066C2 true DE2757066C2 (ja) | 1987-09-10 |
Family
ID=27123866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772757066 Granted DE2757066A1 (de) | 1977-07-11 | 1977-12-21 | Phenylalkansaeure-m-phenoxybenzylester, verfahren zu ihrer herstellung und deren verwendung |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5419933A (ja) |
| AR (1) | AR221329A1 (ja) |
| AT (2) | AT359058B (ja) |
| BE (1) | BE862133A (ja) |
| DD (2) | DD142961A5 (ja) |
| DE (1) | DE2757066A1 (ja) |
| IN (1) | IN147335B (ja) |
| IT (1) | IT1092245B (ja) |
| NL (1) | NL7800516A (ja) |
| RO (1) | RO74887A (ja) |
| SE (1) | SE7713322L (ja) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239777A (en) | 1976-10-01 | 1980-12-16 | American Cyanamid Company | (-)-α-Cyano-m-phenoxybenzyl(+)-α-isopropyl-4-difluoromethoxyphenylacetate |
| DE2819788A1 (de) * | 1978-05-05 | 1979-11-08 | Bayer Ag | Benzylester mit fluorsubstituierten aether- und/oder thioaethergruppen und ihre verwendung als insektizide |
| US4284643A (en) * | 1978-08-28 | 1981-08-18 | Bayer Aktiengesellschaft | Combating arthropods with novel fluorine-containing phenylacetic acid esters |
| DE2837524A1 (de) * | 1978-08-28 | 1980-03-20 | Bayer Ag | Substituierte alpha-phenyl-carbonsaeure- (4-fluoro-3-phenoxy-benzyl)-ester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| EP0015598B1 (en) | 1979-02-21 | 1983-04-13 | Shell Internationale Researchmaatschappij B.V. | Pesticidal compositions and their use |
| IL61348A (en) * | 1979-11-28 | 1984-05-31 | American Cyanamid Co | (-)-alpha-cyano-m-phenoxybenzyl(+)alpha-isopropyl-4-difluoromethoxy-phenylacetate,its preparation and its use as an insecticide |
| JPS588035A (ja) * | 1981-07-07 | 1983-01-18 | Nissan Chem Ind Ltd | ジフルオロメトキシフエニルケトン誘導体 |
| US4454344A (en) * | 1982-08-23 | 1984-06-12 | American Cyanamid Company | Method for the resolution of racemic 2-(p-difluoromethoxyphenyl)-3-methylbutyric acid |
| DE102004001271A1 (de) | 2004-01-08 | 2005-08-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| DE102004033796A1 (de) * | 2004-07-12 | 2006-06-29 | Uwe Schlitt | Anti-Allergische Pflanzanlagen:Milbenprotektionsschicht für Pflanzanlagen unterschiedlicher Substrate, insbesondere Hydrokulturen |
| DE102007045953B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102009028001A1 (de) | 2009-07-24 | 2011-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
-
1977
- 1977-11-24 SE SE7713322A patent/SE7713322L/xx unknown
- 1977-11-28 IN IN1654/CAL/77A patent/IN147335B/en unknown
- 1977-12-05 JP JP14597777A patent/JPS5419933A/ja active Granted
- 1977-12-05 AR AR270247A patent/AR221329A1/es active
- 1977-12-20 IT IT52291/77A patent/IT1092245B/it active
- 1977-12-21 DE DE19772757066 patent/DE2757066A1/de active Granted
- 1977-12-21 BE BE183695A patent/BE862133A/xx not_active IP Right Cessation
- 1977-12-21 AT AT919477A patent/AT359058B/de not_active IP Right Cessation
-
1978
- 1978-01-16 NL NL7800516A patent/NL7800516A/xx not_active Application Discontinuation
- 1978-02-22 DD DD78212571A patent/DD142961A5/de unknown
- 1978-02-22 DD DD78203805A patent/DD136689A5/xx unknown
- 1978-03-07 RO RO7893426A patent/RO74887A/ro unknown
-
1980
- 1980-02-18 AT AT0088280A patent/AT365405B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT359058B (de) | 1980-10-27 |
| RO74887A (ro) | 1980-10-30 |
| DD142961A5 (de) | 1980-07-23 |
| SE7713322L (sv) | 1979-01-12 |
| AR221329A1 (es) | 1981-01-30 |
| JPS62138B2 (ja) | 1987-01-06 |
| BE862133A (fr) | 1978-06-21 |
| IN147335B (ja) | 1980-02-02 |
| ATA88280A (de) | 1981-06-15 |
| DE2757066A1 (de) | 1979-02-01 |
| AT365405B (de) | 1982-01-11 |
| JPS5419933A (en) | 1979-02-15 |
| DD136689A5 (de) | 1979-07-25 |
| IT1092245B (it) | 1985-07-06 |
| NL7800516A (nl) | 1979-01-15 |
| ATA919477A (de) | 1980-03-15 |
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