DE2743416A1 - 2-(halogenalkoxyphenyl)-alkansaeure- m-phenoxybenzylester, verfahren zu ihrer herstellung und deren verwendung - Google Patents
2-(halogenalkoxyphenyl)-alkansaeure- m-phenoxybenzylester, verfahren zu ihrer herstellung und deren verwendungInfo
- Publication number
- DE2743416A1 DE2743416A1 DE19772743416 DE2743416A DE2743416A1 DE 2743416 A1 DE2743416 A1 DE 2743416A1 DE 19772743416 DE19772743416 DE 19772743416 DE 2743416 A DE2743416 A DE 2743416A DE 2743416 A1 DE2743416 A1 DE 2743416A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- atom
- isopropyl
- acid
- compounds
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 85
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 37
- -1 m-phenoxybenzyl ester Chemical class 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 32
- 241000238876 Acari Species 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 23
- 241000238631 Hexapoda Species 0.000 claims description 20
- 241001465754 Metazoa Species 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 19
- 125000006485 halo alkoxy phenyl group Chemical group 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
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- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- 125000001424 substituent group Chemical group 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
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- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 3
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- 238000009395 breeding Methods 0.000 claims description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004434 sulfur atom Chemical group 0.000 claims 8
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- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
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- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229930040373 Paraformaldehyde Natural products 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 150000005524 benzylchlorides Chemical class 0.000 claims 1
- 210000001124 body fluid Anatomy 0.000 claims 1
- 239000010839 body fluid Substances 0.000 claims 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 1
- 238000007265 chloromethylation reaction Methods 0.000 claims 1
- 229960003750 ethyl chloride Drugs 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 239000004459 forage Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 0.000 claims 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 claims 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims 1
- 229920002866 paraformaldehyde Polymers 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
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- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 57
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- FTSWXBGPLRXJMZ-UHFFFAOYSA-N 1-chloro-2-propan-2-yl-4-(trifluoromethoxy)benzene Chemical compound CC(C)C1=CC(OC(F)(F)F)=CC=C1Cl FTSWXBGPLRXJMZ-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- LXKNAUOWEJWGTE-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetonitrile Chemical compound COC1=CC=CC(CC#N)=C1 LXKNAUOWEJWGTE-UHFFFAOYSA-N 0.000 description 1
- IGPAZROMUKCCRP-UHFFFAOYSA-N 2-phenyl-2-(trifluoromethoxy)acetonitrile Chemical compound FC(F)(F)OC(C#N)C1=CC=CC=C1 IGPAZROMUKCCRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241000933851 Cochliomyia Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 1
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 1
- 241000832202 Diaphania indica Species 0.000 description 1
- 241000995023 Empoasca Species 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241001313288 Labia Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000819999 Nymphes Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- 241000256626 Pterygota <winged insects> Species 0.000 description 1
- WABPPBHOPMUJHV-UHFFFAOYSA-N Sesamex Chemical compound CCOCCOCCOC(C)OC1=CC=C2OCOC2=C1 WABPPBHOPMUJHV-UHFFFAOYSA-N 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 240000001260 Tropaeolum majus Species 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229940074076 glycerol formal Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 201000001064 tick infestation Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 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
- 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
- C07C317/00—Sulfones; Sulfoxides
-
- 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
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72881776A | 1976-10-01 | 1976-10-01 | |
| US72881876A | 1976-10-01 | 1976-10-01 | |
| US81460077A | 1977-07-11 | 1977-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2743416A1 true DE2743416A1 (de) | 1978-04-06 |
Family
ID=27419119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772743416 Pending DE2743416A1 (de) | 1976-10-01 | 1977-09-27 | 2-(halogenalkoxyphenyl)-alkansaeure- m-phenoxybenzylester, verfahren zu ihrer herstellung und deren verwendung |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5344540A (enExample) |
| BG (2) | BG28238A3 (enExample) |
| BR (1) | BR7706474A (enExample) |
| CH (1) | CH638774A5 (enExample) |
| DE (1) | DE2743416A1 (enExample) |
| DK (1) | DK434777A (enExample) |
| GB (3) | GB1582775A (enExample) |
| GR (1) | GR72107B (enExample) |
| IL (1) | IL52973A (enExample) |
| PL (1) | PL114067B1 (enExample) |
| SU (1) | SU1082782A1 (enExample) |
| TR (1) | TR22094A (enExample) |
| YU (1) | YU40906B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008732A3 (de) * | 1978-08-28 | 1980-10-15 | Bayer Ag | Fluorhaltige Phenylessigsäureester, Verfahren zu deren Herstellung, deren Verwendung als Insektizide und Akarizide; Zwischenprodukte zu deren Herstellung |
| EP0036774B1 (en) * | 1980-03-24 | 1984-05-02 | Sumitomo Chemical Company, Limited | Preparation of insecticidal optically active alpha-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR74446B (enExample) * | 1978-03-20 | 1984-06-28 | American Cyanamid Co | |
| 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 |
| JPS60174599U (ja) * | 1984-04-27 | 1985-11-19 | 横河電機株式会社 | 結晶缶自動煎糖装置 |
| JPH04720Y2 (enExample) * | 1984-10-24 | 1992-01-10 | ||
| JPS6174399U (enExample) * | 1984-10-24 | 1986-05-20 | ||
| DE102006023413A1 (de) * | 2006-05-17 | 2007-11-22 | Bayer Cropscience Ag | Mit insektiziden Wirkstoffen getränktes Papier |
-
1977
- 1977-09-21 IL IL5297377A patent/IL52973A/xx unknown
- 1977-09-26 GB GB4004377A patent/GB1582775A/en not_active Expired
- 1977-09-26 GB GB2486678A patent/GB1604875A/en not_active Expired
- 1977-09-27 DE DE19772743416 patent/DE2743416A1/de active Pending
- 1977-09-27 TR TR2209477A patent/TR22094A/xx unknown
- 1977-09-28 BR BR7706474A patent/BR7706474A/pt unknown
- 1977-09-28 GR GR54449A patent/GR72107B/el unknown
- 1977-09-30 BG BG037467A patent/BG28238A3/xx unknown
- 1977-09-30 BG BG7741086A patent/BG28695A4/xx unknown
- 1977-09-30 DK DK434777A patent/DK434777A/da unknown
- 1977-09-30 CH CH1199877A patent/CH638774A5/de not_active IP Right Cessation
- 1977-09-30 YU YU233577A patent/YU40906B/xx unknown
- 1977-10-01 PL PL20119877A patent/PL114067B1/pl unknown
- 1977-10-01 JP JP11733977A patent/JPS5344540A/ja active Pending
-
1978
- 1978-05-23 GB GB2166078A patent/GB1596903A/en not_active Expired
- 1978-10-12 SU SU782672702A patent/SU1082782A1/ru active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008732A3 (de) * | 1978-08-28 | 1980-10-15 | Bayer Ag | Fluorhaltige Phenylessigsäureester, Verfahren zu deren Herstellung, deren Verwendung als Insektizide und Akarizide; Zwischenprodukte zu deren Herstellung |
| US4284643A (en) | 1978-08-28 | 1981-08-18 | Bayer Aktiengesellschaft | Combating arthropods with novel fluorine-containing phenylacetic acid esters |
| US4405639A (en) | 1978-08-28 | 1983-09-20 | Bayer Aktiengesellschaft | Combating arthropods with fluorine-containing phenylacetic acid esters |
| EP0036774B1 (en) * | 1980-03-24 | 1984-05-02 | Sumitomo Chemical Company, Limited | Preparation of insecticidal optically active alpha-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates |
Also Published As
| Publication number | Publication date |
|---|---|
| DK434777A (da) | 1978-04-02 |
| PL114067B1 (en) | 1981-01-31 |
| BG28238A3 (en) | 1980-03-25 |
| JPS5344540A (en) | 1978-04-21 |
| TR22094A (tr) | 1986-04-02 |
| BG28695A4 (en) | 1980-06-16 |
| BR7706474A (pt) | 1978-06-06 |
| GB1582775A (en) | 1981-01-14 |
| SU1082782A1 (ru) | 1984-03-30 |
| IL52973A (en) | 1983-10-31 |
| CH638774A5 (en) | 1983-10-14 |
| GR72107B (enExample) | 1983-09-14 |
| GB1596903A (en) | 1981-09-03 |
| GB1604875A (en) | 1981-12-16 |
| PL201198A1 (enExample) | 1980-02-11 |
| YU233577A (en) | 1983-02-28 |
| YU40906B (en) | 1986-08-31 |
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| DE3908486A1 (de) | Schaedlingsbekaempfungsmittel |
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