CA1123452A - Procede industriel d'obtention de composes du type carboxylate de cyclopropyle et emploi comme pesticides - Google Patents

Procede industriel d'obtention de composes du type carboxylate de cyclopropyle et emploi comme pesticides

Info

Publication number: CA1123452A
Authority: CA; Canada
Prior art keywords: compound; compounds; cis; formula; atom
Prior art date: 1977-06-30
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

Application number

CA304,269A

Other languages

English (en)

Inventor

John H. Davies

John S. Badmin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

Priority date (The priority date 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 date listed.)

1977-06-30

Filing date

1978-05-29

Publication date

1982-05-11

1978-05-29 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1982-05-11 Application granted granted Critical

1982-05-11 Publication of CA1123452A publication Critical patent/CA1123452A/fr

Status Expired legal-status Critical Current

Links

YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 13
238000004519 manufacturing process Methods 0.000 title claims description 3
239000000575 pesticide Substances 0.000 title description 4
239000000460 chlorine Substances 0.000 claims abstract description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052794 bromium Inorganic materials 0.000 claims abstract description 4
229910052740 iodine Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000004094 surface-active agent Substances 0.000 claims description 4
241000238631 Hexapoda Species 0.000 claims description 2
241000607479 Yersinia pestis Species 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 1
230000000895 acaricidal effect Effects 0.000 abstract description 8
230000000749 insecticidal effect Effects 0.000 abstract description 2
-1 3-phenoxybenzyl esters Chemical class 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000004364 calculation method Methods 0.000 description 7
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231100000167 toxic agent Toxicity 0.000 description 7
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229910052799 carbon Inorganic materials 0.000 description 5
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KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
229960000490 permethrin Drugs 0.000 description 5
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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239000000654 additive Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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239000003381 stabilizer Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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239000002917 insecticide Substances 0.000 description 3
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229910052708 sodium Inorganic materials 0.000 description 3
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IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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150000001299 aldehydes Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 2
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235000014113 dietary fatty acids Nutrition 0.000 description 2
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
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JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 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 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
241000487918 Acacia argyrodendron Species 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical class [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 description 1
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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 1
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LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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150000004760 silicates Chemical class 0.000 description 1
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HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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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)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (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)

CA304,269A 1977-06-30 1978-05-29 Procede industriel d'obtention de composes du type carboxylate de cyclopropyle et emploi comme pesticides Expired CA1123452A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB27409/77		1977-06-30
GB2740977		1977-06-30

Publications (1)

Publication Number	Publication Date
CA1123452A true CA1123452A (fr)	1982-05-11

Family

ID=10259107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA304,269A Expired CA1123452A (fr)	1977-06-30	1978-05-29	Procede industriel d'obtention de composes du type carboxylate de cyclopropyle et emploi comme pesticides

Country Status (15)

Country	Link
EP (1)	EP0000229B1 (fr)
JP (1)	JPS5412351A (fr)
AU (1)	AU525337B2 (fr)
BR (1)	BR7804122A (fr)
CA (1)	CA1123452A (fr)
DE (1)	DE2861395D1 (fr)
DK (1)	DK292478A (fr)
EG (1)	EG13418A (fr)
GR (1)	GR64837B (fr)
IL (1)	IL55027A (fr)
IT (1)	IT7825089A0 (fr)
MX (1)	MX5434E (fr)
NZ (1)	NZ187712A (fr)
TR (1)	TR20942A (fr)
ZA (1)	ZA783300B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4459305A (en) *	1980-04-10	1984-07-10	Dainippon Sochugiku Kabushiki Kaisha	Cyclopropanecarboxylic acid ester derivatives, a method of manufacturing them, and their uses
FR2601360B2 (fr) *	1986-07-09	1988-11-10	Roussel Uclaf	Nouveaux derives de l'acide cyclopropane carboxylique a substituant iode, leur preparation, leur application a la lutte contre les parasites des vegetaux et des animaux.
FR2591223B1 (fr) *	1985-12-10	1988-03-18	Roussel Uclaf	Nouveaux derives de l'acide cyclopropane carboxylique a substituant iode, leur preparation, leur application a la lutte contre les parasites des vegetaux et des animaux
EP0228942B1 (fr) *	1985-12-10	1990-05-23	Roussel-Uclaf	Nouveaux dérivés de l'acide cyclopropane carboxylique à substituant iodé, leur préparation, leur application à la lutte contre les parasites des végétaux et des animaux et les compositions les renfermant
GB2187385A (en) *	1986-03-07	1987-09-09	Shell Int Research	Method of combatting colorado beetles using chemical compounds and compositions containing the chemical compounds
JP2546339B2 (ja) *	1988-06-03	1996-10-23	住友化学工業株式会社	エステル化合物およびその殺虫、殺ダニ剤としての用途
FR2641275B1 (fr) *	1988-12-29	1991-10-11	Roussel Uclaf	Nouveaux derives fluores de l'acide 3-ethenyl 2,2-dimethyl cyclopropane carboxylique, leur procede de preparation et leur application comme pesticides
DE4404640C1 (de) *	1994-02-14	1995-02-09	Siemens Ag	Zahnärztliche Röntgendiagnostikeinrichtung zur Erstellung von Panorama-Röntgenaufnahmen vom Schädel eines Patienten

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1413491A (en) *	1972-05-25	1975-11-12	Nat Res Dev	3-substituted-2,2-dimethyl-cyclopropane carboxylic acid esters their preparation and their use in pesticidal compositions
IE41614B1 (en) *	1973-08-15	1980-02-13	Nat Res Dev	Substituted 2,2-dimethyl cylopropane carboxylic acid estersprocess for their preperation and their use as insecticides

1978
- 1978-05-29 CA CA304,269A patent/CA1123452A/fr not_active Expired
- 1978-06-08 ZA ZA00783300A patent/ZA783300B/xx unknown
- 1978-06-20 DE DE7878200056T patent/DE2861395D1/de not_active Expired
- 1978-06-20 EP EP78200056A patent/EP0000229B1/fr not_active Expired
- 1978-06-27 EG EG398/78A patent/EG13418A/xx active
- 1978-06-28 DK DK292478A patent/DK292478A/da not_active Application Discontinuation
- 1978-06-28 IT IT7825089A patent/IT7825089A0/it unknown
- 1978-06-28 IL IL55027A patent/IL55027A/xx unknown
- 1978-06-28 JP JP7755078A patent/JPS5412351A/ja active Pending
- 1978-06-28 TR TR20942A patent/TR20942A/xx unknown
- 1978-06-28 BR BR7804122A patent/BR7804122A/pt unknown
- 1978-06-28 MX MX787189U patent/MX5434E/es unknown
- 1978-06-28 GR GR56623A patent/GR64837B/el unknown
- 1978-06-28 AU AU37513/78A patent/AU525337B2/en not_active Expired
- 1978-06-28 NZ NZ187712A patent/NZ187712A/xx unknown

Also Published As

Publication number	Publication date
GR64837B (en)	1980-06-04
IL55027A0 (en)	1978-08-31
MX5434E (es)	1983-08-05
IT7825089A0 (it)	1978-06-28
AU3751378A (en)	1980-01-03
TR20942A (tr)	1983-01-24
ZA783300B (en)	1979-09-26
IL55027A (en)	1981-07-31
DE2861395D1 (en)	1982-01-28
DK292478A (da)	1978-12-31
BR7804122A (pt)	1979-02-28
JPS5412351A (en)	1979-01-30
NZ187712A (en)	1980-10-24
EP0000229B1 (fr)	1981-12-02
EG13418A (en)	1981-06-30
AU525337B2 (en)	1982-11-04
EP0000229A1 (fr)	1979-01-10

Legal Events

Date	Code	Title	Description
1999-05-11	MKEX	Expiry

Publication	Publication Date	Title
CA1087208A (fr)	1980-10-07	Benzylethers et thioethers substitues
US3927068A (en)	1975-12-16	Pesticidal cyclopropane derivatives
US4042710A (en)	1977-08-16	Alpha-cyano-phenoxybenzyl-isovalerates
CA1123452A (fr)	1982-05-11	Procede industriel d'obtention de composes du type carboxylate de cyclopropyle et emploi comme pesticides
CS219296B2 (en)	1983-03-25	Insecticide means and method of making the active substance
US4282249A (en)	1981-08-04	Oxyimino-substituted (1R, cis)-cyclopropanecarboxylate pesticides
US4305934A (en)	1981-12-15	Pyrethroid pesticidal compositions
US3993774A (en)	1976-11-23	Pesticidal cyclopropane derivatives
US4292325A (en)	1981-09-29	Oxyimino-substituted (1R,cis)cyclopropanecarboxylate pesticides
US4308262A (en)	1981-12-29	Pyrethroid pesticidal compositions
CA1178966A (fr)	1984-12-04	Compose de cyclopropane oxyimino-substitues, procede de production, composes pesticides et utilisation desdits composes dans la production de pesticides
IE840345L (en)	1984-08-17	2-nitromethylene-1-formyl tetrahydro 1,3-thiazine
US4188400A (en)	1980-02-12	Furylmethyloxime ethers
US4666925A (en)	1987-05-19	1-Isopropyl-2-indanol and -indanthiol ether insecticides
US4259349A (en)	1981-03-31	Halobenzyl ester pesticides
US4175134A (en)	1979-11-20	Phenoxybenzyl ester pesticides
CA1205484A (fr)	1986-06-03	Protection des cultures contre les insectes du sol grace a un cyclopropanecarboxylate d'alkylbenzyle; nouveaux cyclopropanecarboxylates et compositions qui en renferment
US4100298A (en)	1978-07-11	Dispirocyclopropane carboxylate pesticides
GB2035301A (en)	1980-06-18	2-Bromobenzyl esters of alkenyl cycloproprane carboxylic acids and their use as pesticides
US4346092A (en)	1982-08-24	Insecticidal combinations
US4211792A (en)	1980-07-08	Oxyimino-substituted (1R,trans)-cyclopropanecarboxylate pesticides
EP0002091B1 (fr)	1981-06-10	Méthode de lutte contre les organismes nuisibles de l'ordre des acariens au moyen d'esters d'acides cyclopropanecarboxyliques, l'utilisation de tels esters comme acaricides, et un de ces esters comme nouveau composé
US4219563A (en)	1980-08-26	Cyclopropanecarboxylate pesticides
US4439446A (en)	1984-03-27	Fluorine-containing oxyiminocyclopropanecarboxylates
US4100363A (en)	1978-07-11	2-Substituted isovaleric acid ester pesticides