GB1260847A - Esters of cyclopropane carboxylic acids - Google Patents
Esters of cyclopropane carboxylic acidsInfo
- Publication number
- GB1260847A GB1260847A GB5814468A GB5814468A GB1260847A GB 1260847 A GB1260847 A GB 1260847A GB 5814468 A GB5814468 A GB 5814468A GB 5814468 A GB5814468 A GB 5814468A GB 1260847 A GB1260847 A GB 1260847A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- alkenyl
- group
- furylmethyl
- alkadienyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000257226 Muscidae Species 0.000 abstract 1
- 240000004460 Tanacetum coccineum Species 0.000 abstract 1
- 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 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- -1 alkadienyl Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229960005235 piperonyl butoxide Drugs 0.000 abstract 1
- 239000002728 pyrethroid Substances 0.000 abstract 1
- 229940015367 pyrethrum Drugs 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- 239000004563 wettable powder Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,260,847. Insecticides containing cyclopropane carboxylates. NATIONAL RESEARCH DEVELOPMENT CORP. 2 Dec., 1969 [6 Dec., 1968], No. 58144/68. Heading A5E. [Also in Division C2] An insecticidal composition contains as active ingredient a furylmethyl dialkyl-cyclopropane carboxylate of the formula (I):- wherein one of R 1 and R 2 is a C 1-4 alkyl group and the other is a hydrogen atom, each of R 3 and R 4 is a hydrogen atom or an alkyl, alkenyl or alkadienyl group and Y is an alkyl, alkenyl or alkadienyl group or an aryl or heterocyclic group optionally substituted by an alkyl, alkadienyl, alkenyl or alkoxy group or by halogen atoms. The composition may be in the form of a dust, granular solid, wettable powder, emulsion, emulsifiable concentrate, spray or aerosol or other solid or liquid preparation and may also contain a pyrethrum synergist, e.g. piperonyl butoxide. The active ingredient may be used in admixture with a synthetic pyrethroid having a greater toxicity to houseflies, e.g. furylmethyl esters with chrysanthemumic or pyrethric acids, and these mixtures may be obtained by esterifying a furylmethyl alcohol with a mixture of acids or their derivatives.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5814468A GB1260847A (en) | 1968-12-06 | 1968-12-06 | Esters of cyclopropane carboxylic acids |
| NL6918236A NL6918236A (en) | 1968-12-06 | 1969-12-04 | |
| CH1819669A CH519853A (en) | 1968-12-06 | 1969-12-05 | Use of a synthetic as an insecticide |
| FR6942054A FR2025534A1 (en) | 1968-12-06 | 1969-12-05 | |
| DE19691961155 DE1961155A1 (en) | 1968-12-06 | 1969-12-05 | Synthetic pyrethroids and their use as insecticides |
| BE742747D BE742747A (en) | 1968-12-06 | 1969-12-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5814468A GB1260847A (en) | 1968-12-06 | 1968-12-06 | Esters of cyclopropane carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1260847A true GB1260847A (en) | 1972-01-19 |
Family
ID=10480866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5814468A Expired GB1260847A (en) | 1968-12-06 | 1968-12-06 | Esters of cyclopropane carboxylic acids |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE742747A (en) |
| CH (1) | CH519853A (en) |
| DE (1) | DE1961155A1 (en) |
| FR (1) | FR2025534A1 (en) |
| GB (1) | GB1260847A (en) |
| NL (1) | NL6918236A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010573A1 (en) | 1978-07-24 | 1980-05-14 | Merck & Co. Inc. | Novel Z-2-acylamino-3-monosubstituted propenic acids and their esters and salts, and processes for preparing them |
| US4463188A (en) * | 1982-04-06 | 1984-07-31 | Sumitomo Chemical Company, Limited | Method for racemization of optically active 2,2-dimethylcyclopropane-1-carboxylic acid |
| US4487956A (en) * | 1983-07-20 | 1984-12-11 | Sumitomo Chemical Company, Limited | Menthyl 2,2-dimethylcyclopropanecarboxylate and resolution of the same |
| EP0155779A1 (en) * | 1984-02-28 | 1985-09-25 | Sumitomo Chemical Company, Limited | A method for the optical purification of an optically active 2,2-dimethylcyclopropanecarboxylic acid amide |
| US5166417A (en) * | 1990-09-04 | 1992-11-24 | Lonza Ltd. | Process for resolution of racemates of 2,2-dimethylcyclopropanecarboxylic acid |
| US5243070A (en) * | 1990-06-14 | 1993-09-07 | Lonza Ltd. | Process for resolution of racemates of 2,2-dimethylcyclopropanecarboxylic acid |
| WO2002022543A1 (en) * | 2000-09-05 | 2002-03-21 | Ajinomoto Co., Inc. | Process for preparing optically active carboxylic acid derivative |
| US7592480B2 (en) * | 2002-03-06 | 2009-09-22 | Ajinomoto Co., Inc. | Process for producing optically active carboxylic acid |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130655A (en) | 1976-07-12 | 1978-12-19 | Ciba-Geigy Corporation | Pesticidal 2,2-dimethyl-3-isobutyl-cyclopropionates |
-
1968
- 1968-12-06 GB GB5814468A patent/GB1260847A/en not_active Expired
-
1969
- 1969-12-04 NL NL6918236A patent/NL6918236A/xx unknown
- 1969-12-05 CH CH1819669A patent/CH519853A/en not_active IP Right Cessation
- 1969-12-05 FR FR6942054A patent/FR2025534A1/fr active Pending
- 1969-12-05 DE DE19691961155 patent/DE1961155A1/en active Pending
- 1969-12-05 BE BE742747D patent/BE742747A/xx unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010573A1 (en) | 1978-07-24 | 1980-05-14 | Merck & Co. Inc. | Novel Z-2-acylamino-3-monosubstituted propenic acids and their esters and salts, and processes for preparing them |
| US4463188A (en) * | 1982-04-06 | 1984-07-31 | Sumitomo Chemical Company, Limited | Method for racemization of optically active 2,2-dimethylcyclopropane-1-carboxylic acid |
| US4487956A (en) * | 1983-07-20 | 1984-12-11 | Sumitomo Chemical Company, Limited | Menthyl 2,2-dimethylcyclopropanecarboxylate and resolution of the same |
| EP0155779A1 (en) * | 1984-02-28 | 1985-09-25 | Sumitomo Chemical Company, Limited | A method for the optical purification of an optically active 2,2-dimethylcyclopropanecarboxylic acid amide |
| US5243070A (en) * | 1990-06-14 | 1993-09-07 | Lonza Ltd. | Process for resolution of racemates of 2,2-dimethylcyclopropanecarboxylic acid |
| US5166417A (en) * | 1990-09-04 | 1992-11-24 | Lonza Ltd. | Process for resolution of racemates of 2,2-dimethylcyclopropanecarboxylic acid |
| WO2002022543A1 (en) * | 2000-09-05 | 2002-03-21 | Ajinomoto Co., Inc. | Process for preparing optically active carboxylic acid derivative |
| US7592480B2 (en) * | 2002-03-06 | 2009-09-22 | Ajinomoto Co., Inc. | Process for producing optically active carboxylic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| CH519853A (en) | 1972-03-15 |
| NL6918236A (en) | 1970-06-09 |
| BE742747A (en) | 1970-05-14 |
| FR2025534A1 (en) | 1970-09-11 |
| DE1961155A1 (en) | 1970-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |