IE54587B1 - Fluorophenoxybenzyl esters, their preparation and use as pesticides - Google Patents
Fluorophenoxybenzyl esters, their preparation and use as pesticidesInfo
- Publication number
- IE54587B1 IE54587B1 IE2987/82A IE298782A IE54587B1 IE 54587 B1 IE54587 B1 IE 54587B1 IE 2987/82 A IE2987/82 A IE 2987/82A IE 298782 A IE298782 A IE 298782A IE 54587 B1 IE54587 B1 IE 54587B1
- Authority
- IE
- Ireland
- Prior art keywords
- group containing
- carbon atoms
- cis
- cycloalkyl
- alkyl
- Prior art date
Links
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- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000575 pesticide Substances 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
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- 238000000034 method Methods 0.000 claims description 12
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- 230000000361 pesticidal effect Effects 0.000 claims description 9
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
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- 125000000524 functional group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- -1 oxyiminomethylcyclopropane-carboxylic acids Chemical class 0.000 description 46
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- CKFBFQHBUCDOHL-UHFFFAOYSA-N phenoxy(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)OC1=CC=CC=C1 CKFBFQHBUCDOHL-UHFFFAOYSA-N 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 229940086065 potassium hydrogentartrate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/42—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33262181A | 1981-12-21 | 1981-12-21 | |
| US06/416,418 US4439446A (en) | 1981-12-21 | 1982-09-13 | Fluorine-containing oxyiminocyclopropanecarboxylates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE822987L IE822987L (en) | 1983-06-21 |
| IE54587B1 true IE54587B1 (en) | 1989-12-06 |
Family
ID=26988302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2987/82A IE54587B1 (en) | 1981-12-21 | 1982-12-16 | Fluorophenoxybenzyl esters, their preparation and use as pesticides |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4439446A (en, 2012) |
| EP (1) | EP0082573B1 (en, 2012) |
| KR (1) | KR880002622B1 (en, 2012) |
| AT (1) | ATE15184T1 (en, 2012) |
| AU (1) | AU558379B2 (en, 2012) |
| BR (1) | BR8207391A (en, 2012) |
| CA (1) | CA1192911A (en, 2012) |
| DE (1) | DE3265910D1 (en, 2012) |
| DK (1) | DK555882A (en, 2012) |
| EG (1) | EG15868A (en, 2012) |
| ES (1) | ES8403102A1 (en, 2012) |
| GR (1) | GR78092B (en, 2012) |
| IE (1) | IE54587B1 (en, 2012) |
| IL (1) | IL67526A (en, 2012) |
| MX (1) | MX156076A (en, 2012) |
| OA (1) | OA07283A (en, 2012) |
| PH (1) | PH18551A (en, 2012) |
| TR (1) | TR21738A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4584304A (en) * | 1984-06-08 | 1986-04-22 | Shell Oil Company | 2-pyridinylmethyl oxyiminocyclopropanecarboxylates as pesticides |
| FR2606014B1 (fr) * | 1986-10-30 | 1989-05-05 | Roussel Uclaf | Nouvelles oximes ethyleniques derives d'esters de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1410080A (en) * | 1972-12-21 | 1975-10-15 | Nat Res Dev | Oxime derivatives of 2,2-dimethyl-3-formyl cyclopropane carboxylic acid and their use as insecticides |
| DE2709264C3 (de) * | 1977-03-03 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | Substituierte Phenoxybenzyloxycarbonylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide sowie neue Zwischenprodukte |
| DE2739854A1 (de) * | 1977-09-03 | 1979-03-15 | Bayer Ag | Fluorsubstituierte phenoxybenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| US4211792A (en) * | 1978-06-02 | 1980-07-08 | Shell Oil Company | Oxyimino-substituted (1R,trans)-cyclopropanecarboxylate pesticides |
| DK158037C (da) * | 1978-06-02 | 1990-08-13 | Shell Int Research | Fremgangsmaade til bekaempelse af acari ved hjaelp af oxyimino-substituerede cyclopropancarboxylsyreestere og z-isomerer af visse af disse estere til brug ved fremgangsmaaden |
| US4282249A (en) * | 1978-06-02 | 1981-08-04 | Shell Oil Company | Oxyimino-substituted (1R, cis)-cyclopropanecarboxylate pesticides |
| US4292325A (en) * | 1979-02-21 | 1981-09-29 | Shell Oil Company | Oxyimino-substituted (1R,cis)cyclopropanecarboxylate pesticides |
-
1982
- 1982-09-13 US US06/416,418 patent/US4439446A/en not_active Expired - Fee Related
- 1982-12-14 DK DK555882A patent/DK555882A/da not_active Application Discontinuation
- 1982-12-16 IE IE2987/82A patent/IE54587B1/en not_active IP Right Cessation
- 1982-12-16 CA CA000417857A patent/CA1192911A/en not_active Expired
- 1982-12-17 DE DE8282201622T patent/DE3265910D1/de not_active Expired
- 1982-12-17 EP EP82201622A patent/EP0082573B1/en not_active Expired
- 1982-12-17 AT AT82201622T patent/ATE15184T1/de active
- 1982-12-20 BR BR8207391A patent/BR8207391A/pt not_active IP Right Cessation
- 1982-12-20 AU AU91662/82A patent/AU558379B2/en not_active Ceased
- 1982-12-20 IL IL67526A patent/IL67526A/xx not_active IP Right Cessation
- 1982-12-20 KR KR8205688A patent/KR880002622B1/ko not_active Expired
- 1982-12-21 EG EG745/82A patent/EG15868A/xx active
- 1982-12-21 GR GR70134A patent/GR78092B/el unknown
- 1982-12-21 TR TR21738A patent/TR21738A/xx unknown
- 1982-12-21 PH PH28304A patent/PH18551A/en unknown
- 1982-12-21 ES ES518417A patent/ES8403102A1/es not_active Expired
- 1982-12-21 OA OA57877A patent/OA07283A/xx unknown
-
1983
- 1983-01-03 MX MX195800A patent/MX156076A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE15184T1 (de) | 1985-09-15 |
| MX156076A (es) | 1988-06-29 |
| EP0082573A1 (en) | 1983-06-29 |
| TR21738A (tr) | 1985-05-22 |
| IE822987L (en) | 1983-06-21 |
| DK555882A (da) | 1983-06-22 |
| CA1192911A (en) | 1985-09-03 |
| DE3265910D1 (en) | 1985-10-03 |
| EG15868A (en) | 1992-12-30 |
| BR8207391A (pt) | 1983-10-18 |
| PH18551A (en) | 1985-08-09 |
| AU9166282A (en) | 1983-06-30 |
| ES518417A0 (es) | 1984-03-01 |
| AU558379B2 (en) | 1987-01-29 |
| GR78092B (en, 2012) | 1984-09-26 |
| IL67526A0 (en) | 1983-05-15 |
| OA07283A (en) | 1984-08-31 |
| KR880002622B1 (ko) | 1988-12-07 |
| KR840002774A (ko) | 1984-07-16 |
| IL67526A (en) | 1986-07-31 |
| ES8403102A1 (es) | 1984-03-01 |
| EP0082573B1 (en) | 1985-08-28 |
| US4439446A (en) | 1984-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |