IE43348B1 - Pyrethroids as insecticides - Google Patents
Pyrethroids as insecticidesInfo
- Publication number
- IE43348B1 IE43348B1 IE296/76A IE29676A IE43348B1 IE 43348 B1 IE43348 B1 IE 43348B1 IE 296/76 A IE296/76 A IE 296/76A IE 29676 A IE29676 A IE 29676A IE 43348 B1 IE43348 B1 IE 43348B1
- Authority
- IE
- Ireland
- Prior art keywords
- carboxylic acid
- dimethylspiro
- compound
- compound according
- phenoxybenzyl ester
- Prior art date
Links
- 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 title description 10
- 239000002917 insecticide Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- -1 phenoxybenzyl esters Chemical class 0.000 claims abstract description 35
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- 239000002253 acid Substances 0.000 claims abstract description 15
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims abstract description 9
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- MAHFUOSRSHBAFO-UHFFFAOYSA-N 2',2'-dimethylspiro[1,2-dihydroindene-3,3'-cyclopropane]-1'-carboxylic acid Chemical compound CC1(C)C(C(O)=O)C11C2=CC=CC=C2CC1 MAHFUOSRSHBAFO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 8
- 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 7
- 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
- RXTAQAPVUFGHOU-UHFFFAOYSA-N 2,2-dimethylspiro[cyclopropane-3,1'-indene]-1-carboxylic acid Chemical compound CC1(C)C(C(O)=O)C11C2=CC=CC=C2C=C1 RXTAQAPVUFGHOU-UHFFFAOYSA-N 0.000 claims description 6
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- 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 claims description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
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- 230000001418 larval effect Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 244000144972 livestock Species 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
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- TXORZOOFFDVXQY-UHFFFAOYSA-N octa-5,7-dienoic acid Chemical compound OC(=O)CCCC=CC=C TXORZOOFFDVXQY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000004382 potting Methods 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
- 229940070846 pyrethrins Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 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
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- 231100000167 toxic agent Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (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 |
|---|---|---|---|
| US05/550,105 US3966959A (en) | 1975-02-13 | 1975-02-13 | Insecticidal and acaricidal, pyrethroid compounds |
| US05/550,106 US3962458A (en) | 1975-02-13 | 1975-02-13 | Systemic control of ectoparasites with pyrethroids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43348L IE43348L (en) | 1976-08-13 |
| IE43348B1 true IE43348B1 (en) | 1981-02-11 |
Family
ID=27069344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE296/76A IE43348B1 (en) | 1975-02-13 | 1976-02-13 | Pyrethroids as insecticides |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS51105040A (xx) |
| AR (1) | AR221026A1 (xx) |
| AT (1) | AT343413B (xx) |
| AU (1) | AU500011B2 (xx) |
| BR (1) | BR7600925A (xx) |
| CH (1) | CH616313A5 (xx) |
| DD (1) | DD127001A5 (xx) |
| DE (1) | DE2605828A1 (xx) |
| DK (1) | DK58076A (xx) |
| EG (1) | EG12151A (xx) |
| ES (1) | ES445129A1 (xx) |
| FR (1) | FR2300559A1 (xx) |
| GB (1) | GB1490672A (xx) |
| GR (1) | GR59845B (xx) |
| IE (1) | IE43348B1 (xx) |
| IL (1) | IL49029A (xx) |
| IT (1) | IT1066095B (xx) |
| KE (1) | KE2882A (xx) |
| MY (1) | MY7800449A (xx) |
| NL (1) | NL7601502A (xx) |
| NZ (1) | NZ180004A (xx) |
| PT (1) | PT64800B (xx) |
| SE (1) | SE426062B (xx) |
| TR (1) | TR19001A (xx) |
| YU (1) | YU40132B (xx) |
| ZM (1) | ZM2176A1 (xx) |
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 |
| ZA806984B (en) * | 1979-11-14 | 1981-11-25 | Shell Res Ltd | Pesticidal compositions |
| 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 (xx) * | 1973-10-08 | 1976-06-03 |
-
1976
- 1976-02-12 FR FR7603879A patent/FR2300559A1/fr active Granted
- 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 BR BR7600925A patent/BR7600925A/pt unknown
- 1976-02-13 PT PT64800A patent/PT64800B/pt unknown
- 1976-02-13 TR TR19001A patent/TR19001A/xx unknown
- 1976-02-13 CH CH180776A patent/CH616313A5/de not_active IP Right Cessation
- 1976-02-13 GR GR50045A patent/GR59845B/el unknown
- 1976-02-13 SE SE7601656A patent/SE426062B/xx unknown
- 1976-02-13 AT AT105676A patent/AT343413B/de not_active IP Right Cessation
- 1976-02-13 IE IE296/76A patent/IE43348B1/en unknown
- 1976-02-13 IL IL49029A patent/IL49029A/xx unknown
- 1976-02-13 AR AR262252A patent/AR221026A1/es active
- 1976-02-13 IT IT48098/76A patent/IT1066095B/it active
- 1976-02-13 ES ES445129A patent/ES445129A1/es not_active Expired
- 1976-02-13 NZ NZ180004A patent/NZ180004A/xx unknown
- 1976-02-13 AU AU11117/76A patent/AU500011B2/en not_active Expired
- 1976-02-13 ZM ZM21/76A patent/ZM2176A1/xx unknown
- 1976-02-13 GB GB5842/76A patent/GB1490672A/en not_active Expired
- 1976-02-13 JP JP51014110A patent/JPS51105040A/ja active Pending
- 1976-02-13 DD DD191239A patent/DD127001A5/xx unknown
- 1976-02-13 DE DE19762605828 patent/DE2605828A1/de not_active Withdrawn
- 1976-02-13 NL NL7601502A patent/NL7601502A/xx not_active Application Discontinuation
- 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 |
|---|---|
| MY7800449A (en) | 1978-12-31 |
| BR7600925A (pt) | 1976-09-14 |
| JPS51105040A (xx) | 1976-09-17 |
| KE2882A (en) | 1978-09-29 |
| DD127001A5 (xx) | 1977-08-31 |
| CH616313A5 (en) | 1980-03-31 |
| TR19001A (tr) | 1978-03-01 |
| AR221026A1 (es) | 1980-12-30 |
| IE43348L (en) | 1976-08-13 |
| AT343413B (de) | 1978-05-26 |
| PT64800B (en) | 1977-07-07 |
| IL49029A0 (en) | 1976-04-30 |
| ZM2176A1 (en) | 1977-08-22 |
| NZ180004A (en) | 1978-04-28 |
| AU1111776A (en) | 1977-08-18 |
| NL7601502A (nl) | 1976-08-17 |
| SE7601656L (sv) | 1976-08-14 |
| ATA105676A (de) | 1977-09-15 |
| FR2300559A1 (fr) | 1976-09-10 |
| EG12151A (en) | 1978-12-31 |
| IL49029A (en) | 1979-10-31 |
| GR59845B (en) | 1978-03-07 |
| SE426062B (sv) | 1982-12-06 |
| ES445129A1 (es) | 1977-09-01 |
| DK58076A (da) | 1976-08-14 |
| FR2300559B1 (xx) | 1980-06-27 |
| IT1066095B (it) | 1985-03-04 |
| DE2605828A1 (de) | 1976-08-26 |
| AU500011B2 (en) | 1979-05-10 |
| YU34276A (en) | 1982-10-31 |
| GB1490672A (en) | 1977-11-02 |
| PT64800A (en) | 1976-03-01 |
| YU40132B (en) | 1985-08-31 |
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