NL8004278A - Nieuwe carbonzuurester, werkwijze voor het bereiden daarvan, alsmede daarop gebaseerde insecticidesamen- stelling. - Google Patents
Nieuwe carbonzuurester, werkwijze voor het bereiden daarvan, alsmede daarop gebaseerde insecticidesamen- stelling. Download PDFInfo
- Publication number
- NL8004278A NL8004278A NL8004278A NL8004278A NL8004278A NL 8004278 A NL8004278 A NL 8004278A NL 8004278 A NL8004278 A NL 8004278A NL 8004278 A NL8004278 A NL 8004278A NL 8004278 A NL8004278 A NL 8004278A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- carboxylic acid
- acid ester
- methyl
- dimethyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 8
- 239000002917 insecticide Substances 0.000 title description 18
- 150000004651 carbonic acid esters Chemical class 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 6
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 150000001875 compounds Chemical class 0.000 description 46
- 239000000243 solution Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- -1 alkali metal salts Chemical class 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241000255925 Diptera Species 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
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- 241000256059 Culex pipiens Species 0.000 description 4
- 241000144210 Culex pipiens pallens Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- ROVGZAWFACYCSP-MQBLHHJJSA-N [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 Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 4
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- 230000000895 acaricidal effect Effects 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
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- 238000011161 development Methods 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
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- SBNFWQZLDJGRLK-UHFFFAOYSA-N phenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-UHFFFAOYSA-N 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 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 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
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- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 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 2
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- 239000004009 herbicide Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000201 insect hormone Substances 0.000 description 1
- 239000003949 liquefied natural gas Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- WLLGXSLBOPFWQV-OTHKPKEBSA-N molport-035-783-878 Chemical compound C([C@H]1C=C2)[C@H]2C2C1C(=O)N(CC(CC)CCCC)C2=O WLLGXSLBOPFWQV-OTHKPKEBSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9650379A JPS5620546A (en) | 1979-07-27 | 1979-07-27 | Carboxylic acid ester |
| JP9650379 | 1979-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8004278A true NL8004278A (nl) | 1981-01-29 |
Family
ID=14166903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8004278A NL8004278A (nl) | 1979-07-27 | 1980-07-25 | Nieuwe carbonzuurester, werkwijze voor het bereiden daarvan, alsmede daarop gebaseerde insecticidesamen- stelling. |
Country Status (11)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4665174A (en) * | 1981-05-12 | 1987-05-12 | Sumitomo Chemical Company, Limited | Production of cyclopentenone derivatives |
| JP2570388B2 (ja) * | 1988-06-10 | 1997-01-08 | 住友化学工業株式会社 | カルボン酸エステルおよびその殺虫剤としての用途 |
| TW402485B (en) | 1998-05-26 | 2000-08-21 | Sumitomo Chemical Co | Pyrethroid compound and composition for controlling pest containing the same as an active ingredient |
| CN1115325C (zh) * | 1998-08-05 | 2003-07-23 | 中山市凯达精细化工股份有限公司 | 4－二甲氨基吡啶催化酯化合成菊酯类农药的方法 |
| JP2000053512A (ja) * | 1998-08-10 | 2000-02-22 | Sumitomo Chem Co Ltd | 殺虫組成物 |
| AU764352B2 (en) | 1999-04-22 | 2003-08-14 | Sumitomo Chemical Company, Limited | Cockroach controlling compositions |
| CN1115326C (zh) * | 1999-12-13 | 2003-07-23 | 江苏扬农化工集团有限公司 | 一种拟除虫菊酯类化合物及其制备方法和应用 |
| JP4231894B1 (ja) * | 2008-03-31 | 2009-03-04 | 大日本除蟲菊株式会社 | イエバエ防除用噴霧剤 |
| AR080647A1 (es) * | 2010-02-25 | 2012-04-25 | Sumitomo Chemical Co | Compuesto de ester y su uso |
| EP3106477B1 (en) * | 2014-02-14 | 2018-08-29 | Mitsubishi Gas Chemical Company, Inc. | (meth)acrylic acid ester compound and production method therefor |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5516402B2 (enrdf_load_stackoverflow) * | 1972-09-29 | 1980-05-01 |
-
1979
- 1979-07-27 JP JP9650379A patent/JPS5620546A/ja active Granted
-
1980
- 1980-07-10 AU AU60303/80A patent/AU6030380A/en not_active Abandoned
- 1980-07-17 GB GB8023464A patent/GB2055822A/en not_active Withdrawn
- 1980-07-21 ZA ZA00804391A patent/ZA804391B/xx unknown
- 1980-07-23 FR FR8016245A patent/FR2462419A1/fr active Pending
- 1980-07-23 IT IT8049310A patent/IT8049310A0/it unknown
- 1980-07-24 ES ES493676A patent/ES493676A0/es active Granted
- 1980-07-24 BR BR8004637A patent/BR8004637A/pt unknown
- 1980-07-25 NL NL8004278A patent/NL8004278A/nl not_active Application Discontinuation
- 1980-07-25 DK DK323680A patent/DK323680A/da unknown
- 1980-07-25 DE DE19803028290 patent/DE3028290A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6157820B2 (enrdf_load_stackoverflow) | 1986-12-09 |
| ZA804391B (en) | 1981-07-29 |
| DE3028290A1 (de) | 1981-02-19 |
| ES8106693A1 (es) | 1981-07-01 |
| DK323680A (da) | 1981-01-28 |
| JPS5620546A (en) | 1981-02-26 |
| FR2462419A1 (fr) | 1981-02-13 |
| IT8049310A0 (it) | 1980-07-23 |
| GB2055822A (en) | 1981-03-11 |
| AU6030380A (en) | 1981-01-29 |
| ES493676A0 (es) | 1981-07-01 |
| BR8004637A (pt) | 1981-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |