CH616313A5 - Process for the preparation of novel phenoxybenzyl esters of spirocarboxylic acids and their optical and geometric isomers - Google Patents
Process for the preparation of novel phenoxybenzyl esters of spirocarboxylic acids and their optical and geometric isomers Download PDFInfo
- Publication number
- CH616313A5 CH616313A5 CH180776A CH180776A CH616313A5 CH 616313 A5 CH616313 A5 CH 616313A5 CH 180776 A CH180776 A CH 180776A CH 180776 A CH180776 A CH 180776A CH 616313 A5 CH616313 A5 CH 616313A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethylspiro
- carboxylic acid
- phenoxybenzyl ester
- formula
- cyclopropan
- Prior art date
Links
- -1 phenoxybenzyl esters Chemical class 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 19
- 239000002253 acid Substances 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 11
- 230000003287 optical effect Effects 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 6
- 150000007513 acids Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 64
- 230000000749 insecticidal effect Effects 0.000 claims description 29
- 241000238631 Hexapoda Species 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 25
- 241000238876 Acari Species 0.000 claims description 16
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 11
- 239000002689 soil Substances 0.000 claims description 10
- QGBPTYVAIGFIPL-UHFFFAOYSA-N 2,2-dimethylspiro[2.4]hepta-4,6-diene-1-carboxylic acid Chemical compound CC1(C)C(C(O)=O)C11C=CC=C1 QGBPTYVAIGFIPL-UHFFFAOYSA-N 0.000 claims description 6
- NKIXSBGTDVMHAI-UHFFFAOYSA-N 2,2-dimethylspiro[2.4]heptane-1-carboxylic acid Chemical compound CC1(C)C(C(O)=O)C11CCCC1 NKIXSBGTDVMHAI-UHFFFAOYSA-N 0.000 claims description 6
- 230000000895 acaricidal effect Effects 0.000 claims description 6
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 206010061217 Infestation Diseases 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
- 239000004480 active ingredient Substances 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 238000012360 testing method Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 241000254173 Coleoptera Species 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 241000255925 Diptera Species 0.000 description 12
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 241000256244 Heliothis virescens Species 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 235000013601 eggs Nutrition 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 241001521235 Spodoptera eridania Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002917 insecticide Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 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 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- TXORZOOFFDVXQY-UHFFFAOYSA-N octa-5,7-dienoic acid Chemical compound OC(=O)CCCC=CC=C TXORZOOFFDVXQY-UHFFFAOYSA-N 0.000 description 7
- 239000002728 pyrethroid Substances 0.000 description 7
- 230000009885 systemic effect Effects 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 6
- ZQTQPYJGMWHXMO-UHFFFAOYSA-N OOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOO ZQTQPYJGMWHXMO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000012447 hatching Effects 0.000 description 6
- 230000017448 oviposition Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- 241000238657 Blattella germanica Species 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 241000219146 Gossypium Species 0.000 description 5
- 240000002024 Gossypium herbaceum Species 0.000 description 5
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 5
- 241000238889 Ixodidae Species 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 4
- 241001425390 Aphis fabae Species 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 4
- RTYZCUMXOXNVSI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOO RTYZCUMXOXNVSI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229950011148 cyclopropane Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000035558 fertility Effects 0.000 description 4
- 229960000490 permethrin Drugs 0.000 description 4
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 4
- 229960003536 phenothrin Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- GBFUISVVTYNAKO-UHFFFAOYSA-N 1-(3-phenoxyphenyl)prop-2-yn-1-ol Chemical compound C#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GBFUISVVTYNAKO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 244000045232 Canavalia ensiformis Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000462639 Epilachna varivestis Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 3
- VMORCWYWLVLMDG-YZGWKJHDSA-N Pyrethrin-II Natural products CC(=O)OC(=C[C@@H]1[C@H](C(=O)O[C@H]2CC(=O)C(=C2C)CC=CC=C)C1(C)C)C VMORCWYWLVLMDG-YZGWKJHDSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004166 bioassay Methods 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000003559 chemosterilizing effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 230000001418 larval effect Effects 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 3
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- 241001524388 Abrupta Species 0.000 description 2
- 241000254175 Anthonomus grandis Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FMTFEIJHMMQUJI-UHFFFAOYSA-N Cinerin I Natural products C1C(=O)C(CC=CC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C FMTFEIJHMMQUJI-UHFFFAOYSA-N 0.000 description 2
- LTNDZDRYUXNFCU-NEWSRXKRSA-N Cinerin II Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]2[C@@H](C=C(C)OC(=O)C)C2(C)C LTNDZDRYUXNFCU-NEWSRXKRSA-N 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 2
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000238680 Rhipicephalus microplus Species 0.000 description 2
- 241001494115 Stomoxys calcitrans Species 0.000 description 2
- 241000254112 Tribolium confusum Species 0.000 description 2
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- FMTFEIJHMMQUJI-DFKXKMKHSA-N cinerin I Chemical compound C1C(=O)C(C\C=C/C)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1C=C(C)C FMTFEIJHMMQUJI-DFKXKMKHSA-N 0.000 description 2
- SHCRDCOTRILILT-WOBDGSLYSA-N cinerin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C)C(=O)C1 SHCRDCOTRILILT-WOBDGSLYSA-N 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000009189 diving Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 2
- 229940070846 pyrethrins Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- MHDBJGQZKNBLKT-UHFFFAOYSA-N (3-phenoxyphenyl)methyl 2,2-dimethylspiro[cyclopropane-3,1'-indene]-1-carboxylate Chemical compound C1=CC2=CC=CC=C2C11C(C)(C)C1C(=O)OCC(C=1)=CC=CC=1OC1=CC=CC=C1 MHDBJGQZKNBLKT-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 241001388466 Bruchus rufimanus Species 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
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- 241000995023 Empoasca Species 0.000 description 1
- 241000995027 Empoasca fabae Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001177117 Lasioderma serricorne Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000403354 Microplus Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000819999 Nymphes Species 0.000 description 1
- JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 1
- UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241001481703 Rhipicephalus <genus> Species 0.000 description 1
- WABPPBHOPMUJHV-UHFFFAOYSA-N Sesamex Chemical compound CCOCCOCCOC(C)OC1=CC=C2OCOC2=C1 WABPPBHOPMUJHV-UHFFFAOYSA-N 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 240000001260 Tropaeolum majus Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- BZKFMUIJRXWWQK-UHFFFAOYSA-N cyclopenten-2-one Natural products O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 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
- 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
- A01N37/08—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 carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
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 |
---|---|---|---|
US05/550,106 US3962458A (en) | 1975-02-13 | 1975-02-13 | Systemic control of ectoparasites with pyrethroids |
US05/550,105 US3966959A (en) | 1975-02-13 | 1975-02-13 | Insecticidal and acaricidal, pyrethroid compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
CH616313A5 true CH616313A5 (en) | 1980-03-31 |
Family
ID=27069344
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH180776A CH616313A5 (en) | 1975-02-13 | 1976-02-13 | Process for the preparation of novel phenoxybenzyl esters of spirocarboxylic acids and their optical and geometric isomers |
Country Status (26)
Country | Link |
---|---|
JP (1) | JPS51105040A (pt) |
AR (1) | AR221026A1 (pt) |
AT (1) | AT343413B (pt) |
AU (1) | AU500011B2 (pt) |
BR (1) | BR7600925A (pt) |
CH (1) | CH616313A5 (pt) |
DD (1) | DD127001A5 (pt) |
DE (1) | DE2605828A1 (pt) |
DK (1) | DK58076A (pt) |
EG (1) | EG12151A (pt) |
ES (1) | ES445129A1 (pt) |
FR (1) | FR2300559A1 (pt) |
GB (1) | GB1490672A (pt) |
GR (1) | GR59845B (pt) |
IE (1) | IE43348B1 (pt) |
IL (1) | IL49029A (pt) |
IT (1) | IT1066095B (pt) |
KE (1) | KE2882A (pt) |
MY (1) | MY7800449A (pt) |
NL (1) | NL7601502A (pt) |
NZ (1) | NZ180004A (pt) |
PT (1) | PT64800B (pt) |
SE (1) | SE426062B (pt) |
TR (1) | TR19001A (pt) |
YU (1) | YU40132B (pt) |
ZM (1) | ZM2176A1 (pt) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51148024A (en) * | 1975-06-11 | 1976-12-18 | Sumitomo Chem Co Ltd | Insecticide compositions containing cyclopropanecarboxylic acid esters and their preparation |
US4078080A (en) * | 1976-12-13 | 1978-03-07 | American Cyanamid Company | Oral administration of pyrethroids to warm-blooded animals to prevent fly development in their droppings |
DE2825314A1 (de) * | 1978-06-09 | 1979-12-20 | Bayer Ag | Substituierte spiropentancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
JPS5683412A (en) * | 1979-11-14 | 1981-07-08 | Shell Int Research | Insecticidal composition |
DE3044010A1 (de) | 1980-11-22 | 1982-06-24 | Hoechst Ag, 6000 Frankfurt | Phenoxybenzylester, ihre herstellung und ihre verwendung als pflanzenschutzmittel und im veterinaermedizinischen bereich |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3823177A (en) * | 1971-06-25 | 1974-07-09 | Procter & Gamble | Insecticidal esters of spiro carboxylic acids |
GB1437987A (pt) * | 1973-10-08 | 1976-06-03 |
-
1976
- 1976-02-12 FR FR7603879A patent/FR2300559A1/fr active Granted
- 1976-02-13 CH CH180776A patent/CH616313A5/de not_active IP Right Cessation
- 1976-02-13 AT AT105676A patent/AT343413B/de not_active IP Right Cessation
- 1976-02-13 SE SE7601656A patent/SE426062B/xx unknown
- 1976-02-13 NL NL7601502A patent/NL7601502A/xx not_active Application Discontinuation
- 1976-02-13 GB GB5842/76A patent/GB1490672A/en not_active Expired
- 1976-02-13 IT IT48098/76A patent/IT1066095B/it active
- 1976-02-13 NZ NZ180004A patent/NZ180004A/xx unknown
- 1976-02-13 JP JP51014110A patent/JPS51105040A/ja active Pending
- 1976-02-13 AU AU11117/76A patent/AU500011B2/en not_active Expired
- 1976-02-13 DD DD191239A patent/DD127001A5/xx unknown
- 1976-02-13 AR AR262252A patent/AR221026A1/es active
- 1976-02-13 YU YU342/76A patent/YU40132B/xx unknown
- 1976-02-13 DK DK58076*#A patent/DK58076A/da not_active Application Discontinuation
- 1976-02-13 ZM ZM21/76A patent/ZM2176A1/xx unknown
- 1976-02-13 DE DE19762605828 patent/DE2605828A1/de not_active Withdrawn
- 1976-02-13 TR TR19001A patent/TR19001A/xx unknown
- 1976-02-13 IL IL49029A patent/IL49029A/xx unknown
- 1976-02-13 GR GR50045A patent/GR59845B/el unknown
- 1976-02-13 ES ES445129A patent/ES445129A1/es not_active Expired
- 1976-02-13 PT PT64800A patent/PT64800B/pt unknown
- 1976-02-13 BR BR7600925A patent/BR7600925A/pt unknown
- 1976-02-13 IE IE296/76A patent/IE43348B1/en unknown
- 1976-02-14 EG EG7679A patent/EG12151A/xx active
-
1978
- 1978-09-15 KE KE2882A patent/KE2882A/xx unknown
- 1978-12-31 MY MY1978449A patent/MY7800449A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
NZ180004A (en) | 1978-04-28 |
ZM2176A1 (en) | 1977-08-22 |
GR59845B (en) | 1978-03-07 |
AR221026A1 (es) | 1980-12-30 |
SE426062B (sv) | 1982-12-06 |
NL7601502A (nl) | 1976-08-17 |
YU34276A (en) | 1982-10-31 |
MY7800449A (en) | 1978-12-31 |
FR2300559B1 (pt) | 1980-06-27 |
IL49029A0 (en) | 1976-04-30 |
DK58076A (da) | 1976-08-14 |
ES445129A1 (es) | 1977-09-01 |
EG12151A (en) | 1978-12-31 |
PT64800B (en) | 1977-07-07 |
GB1490672A (en) | 1977-11-02 |
AT343413B (de) | 1978-05-26 |
SE7601656L (sv) | 1976-08-14 |
IE43348B1 (en) | 1981-02-11 |
BR7600925A (pt) | 1976-09-14 |
PT64800A (en) | 1976-03-01 |
DD127001A5 (pt) | 1977-08-31 |
JPS51105040A (pt) | 1976-09-17 |
AU500011B2 (en) | 1979-05-10 |
IL49029A (en) | 1979-10-31 |
TR19001A (tr) | 1978-03-01 |
DE2605828A1 (de) | 1976-08-26 |
YU40132B (en) | 1985-08-31 |
IT1066095B (it) | 1985-03-04 |
FR2300559A1 (fr) | 1976-09-10 |
AU1111776A (en) | 1977-08-18 |
IE43348L (en) | 1976-08-13 |
ATA105676A (de) | 1977-09-15 |
KE2882A (en) | 1978-09-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2633732C (en) | Insecticidal and miticidal compositions of bifenthrin and cyano-pyrethroids | |
DE2653189C2 (de) | Cyclopropanverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Insektizide | |
DE2449546C2 (de) | Insektizide Mittel | |
DE2231312A1 (de) | Cyclopropancarbonsaeure-alpha-cyanbenzylester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2737297A1 (de) | Insektizide mittel und verwendung von optisch aktiven 2-(4-chlorphenyl)- isovaleriansaeure-alpha-cyan-3-phenoxybenzylestern als insektizide | |
DE2357826B2 (de) | Stabilisiertes Insektizides und acarizides Mittel auf Pyrethroid-Basis | |
DD211473A5 (de) | Zusammensetzung zur bekaempfung von parasiten | |
DE2843760A1 (de) | Benzylpyrrolylmethylcarbonsaeureester und verfahren zu ihrer herstellung | |
DD206731A5 (de) | Zusammensetzungen zum kampf gegen parasiten | |
DE2348930C3 (de) | Insektizide Mittel auf Basis von Chrysanthemumsäureestern | |
CA1084943A (en) | Pesticidal m-phenoxybenzyl esters of 2,2- dimethylspiro 2,4 heptane-1-carboxylic acid derivatives | |
DE2757066C2 (pt) | ||
DE2448872A1 (de) | Insektizide mittel | |
IE47446B1 (en) | Insecticidal and acaricidal compositions | |
DE2250085C3 (de) | Insektizides Mittel auf der Basis einer Mischung aus parasitären Mikroorganismen und Insektiziden | |
DE2647366A1 (de) | Substituierte arylessigsaeureester, verfahren zu ihrer herstellung und insektizide und acarizide mittel | |
CH616313A5 (en) | Process for the preparation of novel phenoxybenzyl esters of spirocarboxylic acids and their optical and geometric isomers | |
DE2554634C3 (de) | Cyclopropancarbonsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Pestizide | |
DE2432951A1 (de) | (+)-cis-chrysanthemumsaeureester und insektizide und akarizide mittel | |
DE68924786T2 (de) | (Trifluormethyl)vinylpyrethroidderivate, ihre Verwendung als Pestizide, Verfahren zu ihrer Herstellung und Zwischenprodukte dieses Verfahrens. | |
CH639532A5 (de) | Insektizide carbonsaeureester von alpha-trifluormethyl-3-phenoxybenzylalkohol. | |
DE69210639T2 (de) | 3-(3,3,3-Trifluor-2-Chlorpropenyl)-2,2-Dimethylcyclopropancarbonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestitzide | |
DE1966823C3 (de) | Insecticide und acaricide Zubereitung auf Basis von Benzimidazolderivaten | |
DE69104394T2 (de) | Pyrrol-Derivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Pestizide. | |
DE2850795A1 (de) | Insektizide, nematizide und akarizide |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |