IE35157L - Chrysanthemic acid esters - Google Patents
Chrysanthemic acid estersInfo
- Publication number
- IE35157L IE35157L IE710186A IE18671A IE35157L IE 35157 L IE35157 L IE 35157L IE 710186 A IE710186 A IE 710186A IE 18671 A IE18671 A IE 18671A IE 35157 L IE35157 L IE 35157L
- Authority
- IE
- Ireland
- Prior art keywords
- general formula
- reacting
- acid esters
- chrysanthemic acid
- chloro
- Prior art date
Links
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical class CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 title abstract 5
- -1 alkali metal salt Chemical class 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- LNJXZKBHJZAIKQ-UHFFFAOYSA-N 1,1,1,2-tetrachloro-3-(2,3,3,3-tetrachloropropoxy)propane Chemical compound ClC(Cl)(Cl)C(Cl)COCC(Cl)C(Cl)(Cl)Cl LNJXZKBHJZAIKQ-UHFFFAOYSA-N 0.000 abstract 1
- VNTCVNLNEOVBEE-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carbonyl chloride Chemical compound CC(C)=CC1C(C(Cl)=O)C1(C)C VNTCVNLNEOVBEE-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- RPUJAOFSZSEVPC-UHFFFAOYSA-N 4-chlorobut-2-yn-1-ol Chemical compound OCC#CCCl RPUJAOFSZSEVPC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 229960005235 piperonyl butoxide Drugs 0.000 abstract 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1290226 Chrysanthemic acid esters ROCHE PRODUCTS Ltd 19 April 1971 [3 March 1970] 10034/70 Heading C2C The invention comprises Chrysanthemic acid esters of formula in which R represents hydrogen or a C 1 -C 4 alkyl group and X represents an oxygen atom, a sulphur atom or a methylene group. They may be prepared (a) by reacting an acid chloride or bromide of the general formula with an alcohol of the general formula or (b) by reacting an alkali metal salt, a silver salt or tri-(C 1 -C 4 alkyl) amine salt of a chrysanthemum monocarboxylic acid with a halide of general formula in which hal stands for halogen, or (c) to obtain compounds in which X is oxygen or sulphur by reacting a compound (Z) of the general formula with an alkali metal salt of a phenol or thiophenol of general formula 4 - Chloro - 2 - butynyl() - cis/trans - 2,2- dimethyl - 3 - (2 - methyl - propenyl) - cyclopropane carboxylate (compound Z above) used as a starting material, is prepared by reacting chrysanthemic acid chloride with 4-chloro-2- butyn-1-ol in the presence of pyridine. The chrysanthemic acid esters may be used as active agents in insecticides optionally in conjunction with compatible carriers and/or pyrethrin synergists, e.g. piperonyl butoxide; (1,2- methylene dioxy) - 4 - [2 - (octylsulphinyl)- propyl]-benzene; and bis-(2,3,3,3-tetrachloropropyl)-ether.
[GB1290226A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1003470 | 1970-03-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35157L true IE35157L (en) | 1971-09-03 |
| IE35157B1 IE35157B1 (en) | 1975-11-26 |
Family
ID=9960244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE186/71A IE35157B1 (en) | 1970-03-03 | 1971-02-17 | Chrysanthemic acid esters and a process for the manufacture thereof |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT309891B (en) |
| BE (1) | BE763665A (en) |
| CH (1) | CH566710A5 (en) |
| CS (1) | CS171695B2 (en) |
| DE (1) | DE2108779A1 (en) |
| DK (1) | DK131458B (en) |
| ES (1) | ES388773A1 (en) |
| FR (1) | FR2084122A5 (en) |
| GB (1) | GB1290226A (en) |
| IE (1) | IE35157B1 (en) |
| IL (1) | IL36151A (en) |
| NL (1) | NL7102103A (en) |
| NO (1) | NO127968B (en) |
| SE (1) | SE371813B (en) |
| ZA (1) | ZA71743B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4118505A (en) * | 1973-04-20 | 1978-10-03 | Sumitomo Chemical Company, Limited | Novel cyclopropanecarboxylates |
| FR2426673A1 (en) * | 1978-05-25 | 1979-12-21 | Nat Res Dev | PYRETHRINE TYPE PESTICIDES |
-
1970
- 1970-03-03 GB GB1003470A patent/GB1290226A/en not_active Expired
-
1971
- 1971-02-03 CH CH162771A patent/CH566710A5/xx not_active IP Right Cessation
- 1971-02-05 ZA ZA710743A patent/ZA71743B/en unknown
- 1971-02-08 IL IL36151A patent/IL36151A/en unknown
- 1971-02-17 NL NL7102103A patent/NL7102103A/xx unknown
- 1971-02-17 IE IE186/71A patent/IE35157B1/en unknown
- 1971-02-19 CS CS1281A patent/CS171695B2/cs unknown
- 1971-02-24 DE DE19712108779 patent/DE2108779A1/en active Pending
- 1971-03-02 SE SE7102657A patent/SE371813B/xx unknown
- 1971-03-02 NO NO00793/71*[A patent/NO127968B/no unknown
- 1971-03-02 AT AT175671A patent/AT309891B/en not_active IP Right Cessation
- 1971-03-02 ES ES388773A patent/ES388773A1/en not_active Expired
- 1971-03-02 BE BE763665A patent/BE763665A/en unknown
- 1971-03-03 FR FR7107262A patent/FR2084122A5/fr not_active Expired
- 1971-03-03 DK DK97471AA patent/DK131458B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7102103A (en) | 1971-09-07 |
| IE35157B1 (en) | 1975-11-26 |
| GB1290226A (en) | 1972-09-20 |
| IL36151A (en) | 1974-10-22 |
| DE2108779A1 (en) | 1971-09-16 |
| CH566710A5 (en) | 1975-09-30 |
| IL36151A0 (en) | 1971-04-28 |
| ZA71743B (en) | 1971-10-27 |
| DK131458B (en) | 1975-07-21 |
| DK131458C (en) | 1975-12-08 |
| CS171695B2 (en) | 1976-10-29 |
| AT309891B (en) | 1973-09-10 |
| FR2084122A5 (en) | 1971-12-17 |
| NO127968B (en) | 1973-09-10 |
| ES388773A1 (en) | 1974-02-16 |
| BE763665A (en) | 1971-09-02 |
| SE371813B (en) | 1974-12-02 |
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