GB2127691A - Pesticide compositions containing a pyrethrinoid and a photostabilizer - Google Patents

Pesticide compositions containing a pyrethrinoid and a photostabilizer Download PDF

Info

Publication number
GB2127691A
GB2127691A GB08325895A GB8325895A GB2127691A GB 2127691 A GB2127691 A GB 2127691A GB 08325895 A GB08325895 A GB 08325895A GB 8325895 A GB8325895 A GB 8325895A GB 2127691 A GB2127691 A GB 2127691A
Authority
GB
United Kingdom
Prior art keywords
product
formula
compositions
phenoxybenzyl
cis
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.)
Granted
Application number
GB08325895A
Other versions
GB2127691B (en
GB8325895D0 (en
Inventor
Colette Meinard
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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.)
Filing date
Publication date
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB8325895D0 publication Critical patent/GB8325895D0/en
Publication of GB2127691A publication Critical patent/GB2127691A/en
Application granted granted Critical
Publication of GB2127691B publication Critical patent/GB2127691B/en
Expired legal-status Critical Current

Links

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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • 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

Abstract

Pesticide compositions contain a pesticide of the pyrethrinoid series and a product serving to protect the composition from light chosen from derivatives of benzophenone, hindered amines, benzotriazoles and n- hexadecyl 3,5-ditert-butyl-4-hydroxy- benzoate.

Description

SPECIFICATION Pesticide compositions containing a pyrethrinoid and a photostabilizer The present invention concerns new pesticide compositions containing a photostabilizer.
The invention has as its subject pesticide compositions containing on the one hand a pesticide product of the pyrethrinoid series, chosen from the group constituted by: a) products corresponding to the formula (A1):
in which each of X1, X2 and X3, which may be identical or different, represents a halogen atom, and b) products corresponding to the formula (A2)::
in which X represents a hydrogen atom or a halogen atom, R' represents, either a linear, branched or cyclic, saturated or unsaturated, aliphatic hydrocarbyl radical containing 1-8 carbon atoms optionally substituted by one or more identical or different functional groups, or an aryl group containing 6-1 4 carbon atoms, optionally substituted by one or more identical or different functional groups, or a heterocyclic radical optionally substituted by one or more identical or different functional groups;B represents the residue of an alcohol used in the synthesis of esters of the pyrethrinoid series, the ethylene double bond having Z or E geometry, and, on the other hand: a product serving to protect the composition from light chosen from the group constituted by derivatives of benzophenone, hindered amines, benzotriazoles and n-hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate. The term "light" as used herein includes the sun's rays and in particular ultraviolet rays. The invention has particularly as its subject the compositions as previously defined, characterized in that they contain a compound with the formula (A1) in which X1, X2 and X3 each represents a bromine atom as well as the compositions characterized in that they contain a compound with the formula (A1) in which X1 and X2 each represents a chlorine atom, X3 representing a bromine atom.
The products with the formula (A1) are described and claimed in French Patent Specification No.
2.398.714. The invention also has particularly as its subject the compositions defined previously, characterized in that they contain a pesticide product corresponding to formula (A2) in which X represents a hydrogen atom, R' represents a methyl, ethyl or tert-butyl radical, and B represents the residue of an alcohol with the formula:
in which X' represents a hydrogen or fluorine atom and in which the geometry of the double bond is Z.
The products with the formula (A2) are known products, and are described and claimed in European Patent Specification Nos. 0038271, 0041021, 0048186, 0050534.
As a derivative of benzophenone serving to protect the composition from light there may be mentioned, for example 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy4-n-octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4-(,B- hydroxyethoxy)benzophenone, 2-hydroxy-4-methoxy-benzophenone and polymers thereof, phenyl-2 benzimidazolsulphonic-5' acid, dimethoxy-3,4-phenylglyoxylic acid and its sodium salt, (methyl-4benzylidene)-3-camphor, 2-hydroxy-4-methoxy-benzophenone, 2-ethyl-2-hexyl phenyl-4benzophenone carboxylate and 2,2'-dihydroxy-4-methoxybenzophenone.
As benzotriazole type products, 2-(2-hydroxy-3 , 5-ditert-butylphenyl)2H-benzotriazole, 2-(2hydroxy-3, 5-ditert-a mylphenyl)2 H-benzotriazole, 2-(2-hydroxy-5-methylphenyl)2 H-benzotriazole, 2 (2-hyd roxy-3 , 5-dimethylphenyl)2 H-benzotriazole a nd and 2-(2-hydroxy-5-t-octylphenyl)benzotriazole can be cited for example.
As hindered amines, the product corresponding to the formula:
(sold under the trade name Chimassorb 944(R)), the product corresponding to the formula:
(sold under the trade name Tinuvin 770(R)) and further, the product corresponding to the formula:
can be cited, for example.
The invention has more particularly as its subject the compositions as defined previously.
characterized in that the product serving to protect the composition from light is a benzotriazole chosen from the group constituted by the product with the formula:
OH C tert-butyl tert-butyl that is to say 2-(2-hydroxy-3,5-ditert-butylphenyl)2H-benzotriazole, the product with the formula:
OH CN/ -t tert-amyl tert-amyl that is to say 2-(2-hydroxy-3,5-ditert-amylphenyl)2H-benzotriazole, the product with the formula:
that is to say 2-(2-hydroxy-3,5-dimethylphenyl)2H-benzotriazole, and the product with the formula:
HO\ N uN/ \ < < t-oc tyl that is to say 2-(2-hydroxy-5-t-octylphenyl)2H-benzotriazole.
The invention also has more particularly as its subject the compositions as previously defined, characterized in that the product serving to protect the composition from light is 2-hydroxy-4-noctoxybenzophenone.
The invention has quite particularly as its subject the compositions as previously defined, characterized in that on the one hand they contain a pesticide product chosen from (S)a-cyano-3- phenoxybenzyl ( 1 R,cis)-2,2-dimethyl-3-( 1 ,2,2,2-tetrabromoethyl)cyclopropane-carboxylate, (S)acyano-3-phenoxybenzyl (1 R,cis)-2,2-dimethyl-3-(2,2-dichloro-1 ,2-dibromoethyl)cyclopropane carboxylate, (S)a-cyano-3-phenoxybenzyl ( 1 R,cI,s)-2,2-dimethyl-3-(Z)-2-methoxycarbonyl ethenyl cyclopropane-carboxylate, (S)a-cyano-3-phenoxybenzyl ( 1 R,cis)-2,2-di methyl-3-(Z)-2-ethoxyca rbo nyl- ethenyl-cyclopropane-carboxylate and (S)-cyano-3-phenoxybenzyl (1 R,cis)-2,2-dimethyl-3-(Z)-2 tert-butoxycarbonyl-ethenyl-cyclopropane-carboxylate and on the other hand 2-(2-hydroxy-3,5-ditert butyl-phenyl)2 H-benzotriazole or 2-hydroxy-4-n-octoxybenzophenone.
Among the compositions of the invention, there can also be cited those characterized in that they contain on the one hand a pesticide product chosen from (S)a-cyano-3-phenoxybenzyl (1 R,cis)-2,2 dimethyl-3-( 1 ,2,2,2-tetrabromoethyl)-cyclopropane-carboxylate, (S)a-cyano-3-phenoxybenzyl ( 1 R,cis)-2,2-dimethyl-3-(2,2-dichloro- 1 ,2-dibromoethyl)cyclopropane-carboxylate, (S)-cyano-3- phenoxybenzyl (1 R,cis)-2,2-dimethyl-3-(Z)-2-methoxy-carbonyl-ethenyl-cyclopropane-carboxylate, (S)a-cyano-3-phenoxybenzyl (1 R,cis)-2,2-di methyí-3-(Z)-2-ethoxy-ca rbonyí-ethenyí-cycíopropane- carboxylate and (S)-cyano-3-phenoxybenzyl (1 R,cis)-2,2-di methyl-3-(Z)-2 -tert-butoxy-ca rbonyl- ethenyl-cyclopropane-carboxylate and on the other hand, 2,2' -dihydroxy-4-methoxybe nzophenone, 2 (2-hydroxy-5-t-octyl-phenyl)benzotriazole or n-hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate.
The invention has more especially as its subject the compositions as previously defined containing 0.01 to 20 parts by weight of product serving to protect the composition from light and 5 to 50 parts by weight of pesticide product.
The compositions according to the invention may, in addition, contain an emulsifier, as well as a solvent if desired. As emulsifying product, tridecylic phosphates ethoxylated with 6-6.5 moles of ethylene oxide, oxyethylenated tridecylic alcohols, phenylsulphonates and polyglycol ethers of fatty alcohols can be cited. As a solvent, benzene, xylene, ethers such as methyl monopropyieneglycol ether, methyl dipropyleneglycol ether and methyl monoethyleneglycol ether can particularly be cited.
The compositions of the invention are quite remarkable because of their stability to light as is shown in the results of the following tests. This represents remarkable progress.
In fact it has been found that the pyrethrinoids contained as active materials in certain compositions and particularly in emulsifiable concentrates become degraded in light in such a way that practical usage of these compositions can become impossible.
By using the new stabilized compositions of the invention, the various classes of pyrethrinoids exhibit increased stability. These stabilized compounds are then suitable for agricultural use, particularly in the open without significant loss of activity and in the best economic conditions. Taking into account the intense insecticidal activity of the pyrethrinoids listed previously, the invention assumes a great practical importance.
According to a further feature of the invention there is provided a method of treating a site infested with or susceptible to infestation by pests which comprises applying to the said site an effective amount of a composition according to the invention.
It goes without saying that the compositions of the invention are not limited to agricultural use, they can also be used in all the other usages of pesticides, for example in domestic usages, treatment of stored grain and treatment of animals so as to rid them of pests (e.g. treatment by baths, by "sprays" or by painting of a small part of the animal's body according to the "pour-on" method).
The following examples illustrate the invention without however limiting it.
Examples of compositions A. Compositions were prepared containing: (emulsifiable concentrate) (1 R,cis)-2,2-dimethyl-3-(Z)-2-tert-butoxy carbonyl ethenyl cyclopropane carboxylate of (S)a-cyano-3-phenoxy benzyl 30 g Oxyethylenated tridecyl alcohol 100g Phosphoric acid ester of fatty alcohol, EMPHOS PS 40O 30 g Tinuvin 326 "R" or 2-(2-hydroxy-3,5-ditert-butylphenyl)2H-benzotriazole 5 g Xylene 300 g Methyl ether of monoethylene glycol q.s. for 11.
B. Compositions were prepared containing: (emulsifiable concentrate) (1 R,cis)-2,2-dimethyl-3-( 1 ,2,2,2-tetrabromoethyl cyclopropane carboxylate of (S)-cyano-3-phenoxybenzyl 36 g Oxyethylenated tridecyl alcohol 120 g Phosphoric acid ester of fatty alcohol, EMPHOS PS 4008 30 g Tinuvin 326 "R" or 2-(2-hydroxy-3,5-ditert-butylphenyl)2H-benzotriazole 5 9 Xylene 250 g Methyl ether of monoethyleneglycol q.s. for 11.
C. Compositions were prepared containing: (emulsifiable concentrate) (1 R,cis)-2,2-dimethyl-3-(Z)-2-tert-butoxy carbonyl ethenyl cyclopropane carboxylate of (S)a-cyano-3-phenoxybenzyl 25 g Phosphoric acid ester of ethoxylated tridecyl alcohol 30 g Hostavin VPR or 2-hydroxy-4-n-octoxybenzophenone 20 g Xylene 120 g Methyl ether of monoethylene glycol q.s. for 11.
D) Compositions were prepared containing: (emulsifiable concentrate) (1 R,cis)-2,2-dimethyl-3-( 1 ,2,2,2-tetrabromoethyl)cyclopropane carboxylate of (S)a-cyano-3-phenoxybenzyl 36 g Calcium salt of an alkyl aryl sulphonic acid 3g Polyglycol ethers of fatty alcohol 21 g Tinuvin 326 5g Propyl gallate 0.5 g Xylene q.s. for II.
E) Compositions were prepared containing: (emulsifiable concentrate) (1 R,cis)-2,2-dimethyl-3-(2,2-dichloro-1 ,2-dibromoethyl) cyclopropane carboxylate of (S)a-cyano-3-phenoxybenzyl 36 g Calcium salt of an alkyl aryl sulphonic acid 39 Polyglycol ethers of fatty alcohol 21 g Hostavin VP 20 g Propyl gallate 29 Xylene q.s. for 11.
Study of the stability of the compositions of the invention to light In order to measure the degradation kinetics under interior light, 200 ,ul of emulsifiable concentrate containing the active principle at the dosage of 25 g/l (that is 5 mg) is placed in 25 ml beakers (diameter=30 mm) while endeavouring to spread the deposit in the form of a ring at the base of the beaker. In this way an attempt is made to avoid inequalities of radiation surface for the various samples.
The organic solvent of the formulation is eliminated by a current of warm air for about 20 minutes. The beakers thus prepared are placed under interior lighting (1 50 k.lux, 1 hour of exposure corresponding to 14 hours of average sunlight) and are withdrawn at the times given. After light radiation, the contents of the beaker are taken up by 1-2 ml of methylene chloride and the compound under test is measured by high performance liquid chromatography.
The percentages of degradation in function of time are the following: - with the composition of example A, degradation is 0% after 20 hours.
- with the composition of example B, degradation is 4% after 20 hours.
- with the composition of example D, degradation is less than 10% after 10 hours.

Claims (12)

Claims
1. Pesticide compositions containing on the one hand a pesticide product of the pyrethrinoid series, chosen from the group constituted by: a) products corresponding to formula (A1):
in which each of X1,X2 and X3, which may be identical or different, represents a halogen atom, and b) products corresponding to formula (A2)::
in which X represents a hydrogen or halogen atom, R' represents either a linear, branched or cyclic, saturated or unsaturated, aliphatic hydrocarbyl radical containing 1-8 carbon atoms, optionally substituted by one or more identical or different functional groups, or an aryl group containing 6-14 carbon atoms, optionally substituted by one or more identical or different functional groups, or a heterocyclic radical optionally substituted by one or more identical or different functional groups;B represents the residue of an alcohol used in the synthesis of esters of the pyrethrinoid series, the ethylene double bond having Z or E geometry; and, on the other hand a product serving to protect the composition from light chosen from the group constituted by derivatives of benzophenone, hindered amines, benzotriazoles and n-hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate.
2. The compositions as defined in Claim 1, characterized in that they contain a compound with the formula (A,) in which X,, X2 and X3 each represent a bromine atom.
3. The compositions as defined in Claim 1, characterized in that they contain a compound with the formula (A1) in which X1 and X2 each represent a chlorine atom, X3 representing a bromine atom.
4. The compositions as defined in Claim 1, characterized in that they contain a compound with the formula (A2) in which X represents a hydrogen atom, R' represents a methyl, ethyl or tert-butyl radical and B represents the residue of an alcohol with the formula:
in which X' represents a hydrogen atom or a fluorine atom and in which the geometry of the double bond is Z.
5. The compositions as defined in any one of Claims 1-4, characterized in that the product serving to protect the composition from light is a benzotriazole chosen from the group constituted by the product with the formula:
OH N \N tert-butyl MWN\/NX\ te rt-butyl that is to say 2-(2-hydroxy-3,5-ditert-butylphenyl)2H-benzotriazole, the product with the formula:
OH OH "\ tert-amyl tert-amyl te rt-amyl that is to say 2-(2-hydroxy-3,5-ditert-amylphenyl)2H-benzotriazole, the product with the formula:
that is to say 2-(2-hydroxy-3,5-dimethylphenyl)2H-benzotriazole and the product with the formula::
HOs J \N < t-oc tyl that is to say 2-(2-hydroxy-5-t-octylphenyl)2H-benzotriazole.
6. The compositions as defined in any one of Claims 1--4, characterized in that the product serving to protect the composition from light is 2-hydroxy-4-n-octoxybenzophenone.
7. The compositions as defined in any one of Claims 1-4, characterized in that the product serving to protect the composition from light is a hindered amine chosen from the group constituted by the product with the formula:
the product corresponding to the formula:
and the product corresponding to the formula:
8.The compositions as defined in Claim 1, characterized in that they contain on the one hand a pesticide product chosen from (S)a-cyano-3-phenoxybenzyl (1 R,cis)-2,2-dimethyl-3-( 1,2,2,2 tetrabromoethyl)cyclopropane-carboxylate, (S)a-cyano-3-phenoxybenzyl (1 R,cis)-2,2-dimethyl-3-(2,2dichloro-1 ,2-dibromoethyl)cyclopropane-carboxylate, (S)a-cyano-3-phenoxybenzyl (1R,cis)-2,2- dimethyl-3-(Z)-2-methoxycarbonyl ethenyl-cyclopropane carboxylate, (S)a-cyano-3-phenoxybenzyl ( 1 R,cis)-2,2-dimethyl-3-(Z)-2-ethoxycarbonyl-ethenyl-cyclopropane-carboxylate and (S)a-cyano-3 phenoxybenzyl ( 1 R,cis)-2,2-dimethyl-3-(Z)-2-tert-butoxycarbonyl-ethenyl-cyclopropane-carboxylate and on the other hand 2-(2-hydroxy-3,5-ditert-butyl-phenyl)2H-benzotriazole or 2-hydroxy-4-noctoxybenzophenone.
9. The compositions as defined in Claim 1, characterized in that they contain on the one hand a pesticide product chosen from (S)a-cyano-3-phenoxybenzyl( 1 R,cis)-2,2-dimethyl-3-( 1,2,2,2tetrabromoethyl)cyclopropane-carboxylate, (S)c-cyano-3-phenoxybenzyl ( 1 R,cis)-2,2-di methyl-3-(2,2- dich loro- 1 ,2-dibromoethyl)cyclopropa ne-ca rboxylate, (S)a-cyano-3-phenoxybenzyl ( 1 R,cis)-2,2- dimethyl-3-(Z)-2-methoxy-carbonyl-ethenyl-cycíopropane-carboxylate, (S)a-cyano-3-phenoxybenzyl (1 R,cis)-2,2-dimethyl-3-(Z)-2-ethoxy-carbonyl-ethenyl-cyclopropane-carboxylate and (S)cz-cyano-3- phenoxybenzyl (1 R,cis)-2,2-dimethyl-3-(Z)-2-tert-butoxy-carbonyl-ethenyl-cyclopropane carboxylate and on the other hand, 2,2'-dihydroxy-4-methoxybenzophenone, 2-(2-hydroxy-5-t-octylphenyl)benzotriazole or n-hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate.
10. Compositions as claimed in any preceding claim containing 0.01 to 20 parts by weight of product serving to protect the composition from light and 5 to 50 parts by weight of pesticide product.
11. Pesticide compositions as defined in claim 1 substantially as herein described.
12. Pesticide compositions as defined in claim 1 substantially as herein described in any one of Examples A to E.
1 3. A method of treating a site infested with or susceptible to infestation by pests which comprises applying to the said site an effective amount of a composition as claimed in any one of claims 1 to 12.
1 4. Each and every novel method, process, composition and product herein disclosed.
GB08325895A 1982-09-29 1983-09-28 Pesticide compositions containing a pyrethrinoid and a photostabilizer Expired GB2127691B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8216373A FR2533416B1 (en) 1982-09-29 1982-09-29 NOVEL PESTICIDE COMPOSITIONS CONTAINING A PHOTOSTABILIZER

Publications (3)

Publication Number Publication Date
GB8325895D0 GB8325895D0 (en) 1983-11-02
GB2127691A true GB2127691A (en) 1984-04-18
GB2127691B GB2127691B (en) 1986-11-05

Family

ID=9277847

Family Applications (1)

Application Number Title Priority Date Filing Date
GB08325895A Expired GB2127691B (en) 1982-09-29 1983-09-28 Pesticide compositions containing a pyrethrinoid and a photostabilizer

Country Status (9)

Country Link
JP (1) JPS59116202A (en)
AU (1) AU563624B2 (en)
CA (1) CA1208127A (en)
CH (1) CH658772A5 (en)
DE (1) DE3335360A1 (en)
FR (1) FR2533416B1 (en)
GB (1) GB2127691B (en)
IT (1) IT1212889B (en)
ZA (1) ZA837022B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8017557B2 (en) * 2002-02-14 2011-09-13 Endura S.P.A. Benzodioxole derivatives as modulators of proteolytic activity in plants

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU188391B (en) * 1983-12-05 1986-04-28 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara,Hu Insecticide composition containing salicylic acid derivatives as activators
DE4009142A1 (en) * 1989-03-22 1990-09-27 Sumitomo Chemical Co New insecticidal compsns. - comprising a chrysanthemic acid ester, an odour-preventing cpd. and opt. an azole cpd. to prevent colour change
KR900013848A (en) * 1989-03-22 1990-10-22 모오리 히데오 Insect repellent composition
CA2038179A1 (en) * 1990-03-26 1991-09-27 Donald Frederick Anderson Stabilization of phenoxarsine microbiocides
US5427787A (en) * 1993-11-15 1995-06-27 Industrial Technology Research Institute Anti-ultraviolet biocidal composition
EP0713647A1 (en) * 1994-11-24 1996-05-29 Jaico N.V. Insect-repellent composition based on pyrethrum extract
US20080167374A1 (en) * 2007-01-09 2008-07-10 Loveland Products, Inc. Pesticide composition and method of use
JP4504454B2 (en) * 2009-03-11 2010-07-14 エステー株式会社 Insect repellent composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1592691A (en) * 1976-10-05 1981-07-08 Ici Australia Ltd Stabilised tickicidal compositions

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2011428A (en) * 1931-05-04 1935-08-13 Standard Oil Co Light stable insecticide
US2090109A (en) * 1933-11-15 1937-08-17 Mayne R Coe Stabilized insecticide of plant origin
US2772198A (en) * 1954-11-08 1956-11-27 Standard Oil Co Method of killing flies with composition comprising pyrethrins and p-aminoazobenzene
GB958956A (en) * 1959-11-24 1964-05-27 Kenya Pyrethrum Board Insecticidal compositions
US3560613A (en) * 1967-05-09 1971-02-02 Us Agriculture Stabilization of pyrethroid compositions
GB1256417A (en) * 1968-05-31 1971-12-08 Johnson & Son Inc S C Pyrethroid insecticide
US3839561A (en) * 1970-07-22 1974-10-01 Scm Corp Insecticidal compositions stabilized by certain diisophorone derivatives
JPS5017529B2 (en) * 1972-11-20 1975-06-21
JPS5124568B2 (en) * 1973-02-16 1976-07-24
JPS5030141B2 (en) * 1973-05-25 1975-09-29
PH15324A (en) * 1979-02-27 1982-11-18 Sumitomo Chemical Co Low mammalian toxic and/or low fish toxic cyclopropanecarboxylate insecticides and/or acaricides
IT1123122B (en) * 1979-09-12 1986-04-30 Montedison Spa INSECTICIDE LIQUID COMPOSITIONS CONTAINING SYNTHETIC PYRETROIDS
DE3004092A1 (en) * 1980-02-05 1981-08-13 Bayer Ag, 5090 Leverkusen SUBSTITUTED 3- (1,2-DIBROM-ALKYL) - 2,2-DIMETHYL-CYCLOPROPAN-1-CARBONIC ACID ESTERS, METHODS AND INTERMEDIATE PRODUCTS FOR THEIR PRODUCTION AND THEIR USE IN PEST CONTROL
OA06786A (en) * 1980-04-16 1982-12-31 Roussel Uclaf New derivatives of cyclopropane acid, their preparation, their application to the fight against parasites of plants and animals, the compositions containing them and the new intermediates obtained.
FR2482955A1 (en) * 1980-05-23 1981-11-27 Roussel Uclaf NOVEL DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID, PROCESS FOR PREPARING THEM AND THEIR APPLICATION TO THE FIGHT AGAINST PARASITES
FR2498201A2 (en) * 1980-06-11 1982-07-23 Roussel Uclaf LIGHT STABLE COMPOSITIONS CONTAINING PYRETHRINOID COMPOUNDS AND DYES
FR2484436A1 (en) * 1980-06-11 1981-12-18 Roussel Uclaf Pyrethroid compsn. stabilised against light - by incorporation of azo dye, and contg. liq. carrier and surfactant
FR2486073A1 (en) * 1980-07-02 1982-01-08 Roussel Uclaf NOVEL DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID, PROCESS FOR THEIR PREPARATION, AND THEIR APPLICATION TO THE FIGHT AGAINST PESTS
FR2491060A1 (en) * 1980-10-01 1982-04-02 Roussel Uclaf PYRETHRIC ACID-RELATED CARBOXYLIC CYCLOPROPANIC ACID ESTERS, METHOD FOR THE PREPARATION THEREOF AND THEIR USE IN THE FIGHT AGAINST PESTS
GB2102408A (en) * 1981-07-21 1983-02-02 Shell Int Research 3-phenoxybenzyl cyclopropanecarboxylate esters and their use as pesticides
JPS5939807A (en) * 1982-08-27 1984-03-05 Sumitomo Chem Co Ltd Insecticidal and miticidal composition having improved light stability

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1592691A (en) * 1976-10-05 1981-07-08 Ici Australia Ltd Stabilised tickicidal compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8017557B2 (en) * 2002-02-14 2011-09-13 Endura S.P.A. Benzodioxole derivatives as modulators of proteolytic activity in plants

Also Published As

Publication number Publication date
ZA837022B (en) 1984-10-31
FR2533416A1 (en) 1984-03-30
FR2533416B1 (en) 1988-09-02
IT1212889B (en) 1989-11-30
GB2127691B (en) 1986-11-05
DE3335360A1 (en) 1984-03-29
CA1208127A (en) 1986-07-22
GB8325895D0 (en) 1983-11-02
AU1966083A (en) 1984-04-05
CH658772A5 (en) 1986-12-15
AU563624B2 (en) 1987-07-16
JPS59116202A (en) 1984-07-05
IT8349062A0 (en) 1983-09-28

Similar Documents

Publication Publication Date Title
EP0543883B1 (en) Insect repellent
GB2127691A (en) Pesticide compositions containing a pyrethrinoid and a photostabilizer
JPH11501291A (en) Germicidal alcohol, its production and its use
KR100594551B1 (en) Composition for Keeping away Vermin
CA2091064C (en) Insecticidal composition
JPS60155105A (en) Insecticide
JPS5663950A (en) Cyclopropanecarboxylic ester
US2891889A (en) Insecticidal compositions containing cyclethrin
US4853217A (en) Methods and compositions for controlling the pear leaf blister moth, Leucoptera scitella
US5599848A (en) Preparation, intermediates for the preparation and the use of a mixture of dodecdienol isomers
US5401771A (en) Method of combatting household insects
JPH0688888B2 (en) β-branched chain alcohol mosquito control agent
EP0340971B1 (en) Attractants for the Mediterranean fruit fly
EP0147947A1 (en) Insecticidal composition
US3742052A (en) Diisophorone derivatives and compositions containing same
EP0609253B1 (en) Process for preparing a mixture of dodecadienol isomers, intermediates for preparing the same and its use
JPH07196411A (en) Method for controlling bacillus and mold
US4632827A (en) Pest control compositions
KR920016439A (en) Methyldioxolane derivatives and pesticide compositions containing the same
SK90597A3 (en) Pesticidal compounds
US3761421A (en) Dilsophorone derivatives and compositions containing same
JPS57109750A (en) Insecticidal and miticidal agent containing novel carboxylic acid ester derivative, and its preparation
RU94030238A (en) Esters, processes for preparation thereof, intermediates for preparation of said esters, processes for preparation thereof, composition, and method for controlling mites
JPS5799541A (en) Trihaloallyl derivative and injurious insect repellent containing the same as active constituent
JPH0122253B2 (en)

Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19920928