GB2127691A - Pesticide compositions containing a pyrethrinoid and a photostabilizer - Google Patents
Pesticide compositions containing a pyrethrinoid and a photostabilizer Download PDFInfo
- 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
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- phenoxybenzyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 239000000575 pesticide Substances 0.000 title claims abstract description 19
- 150000001412 amines Chemical class 0.000 claims abstract description 5
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000008366 benzophenones Chemical class 0.000 claims abstract description 4
- 150000001565 benzotriazoles Chemical class 0.000 claims abstract description 3
- -1 aliphatic hydrocarbyl radical Chemical class 0.000 claims description 12
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims description 8
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical group OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 claims description 8
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 claims description 3
- MJFOVRMNLQNDDS-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MJFOVRMNLQNDDS-UHFFFAOYSA-N 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 239000012964 benzotriazole Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 claims description 2
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical group C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- JWEQRJSCTFBRSI-PCLIKHOPSA-N rboxylate Chemical compound COC(=O)C1C(N2C3=O)C4=CC=CC=C4OC1(C)N=C2S\C3=C\C(C=1)=CC=C(OC)C=1COC1=CC=CC=C1C JWEQRJSCTFBRSI-PCLIKHOPSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 3
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000000473 propyl gallate Substances 0.000 description 2
- 229940075579 propyl gallate Drugs 0.000 description 2
- 235000010388 propyl gallate Nutrition 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940087291 tridecyl alcohol Drugs 0.000 description 2
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- VSBCUTLTLUSECJ-UHFFFAOYSA-N 2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(Br)C(Br)(Br)Br)C1C(O)=O VSBCUTLTLUSECJ-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229940113120 dipropylene glycol Drugs 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- ORECYURYFJYPKY-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;2,4,6-trichloro-1,3,5-triazine;2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.ClC1=NC(Cl)=NC(Cl)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 ORECYURYFJYPKY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 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
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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)
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.
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 (2)
| 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 |
| WO2024189563A1 (en) | 2023-03-14 | 2024-09-19 | Adama Makhteshim Ltd. | Liquid compositions containing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine-(1h)-one and derivatives thereof and a uv absorber |
Families Citing this family (8)
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1592691A (en) * | 1976-10-05 | 1981-07-08 | Ici Australia Ltd | Stabilised tickicidal compositions |
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| 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 | ||
| JPS55115859A (en) * | 1979-02-27 | 1980-09-06 | Sumitomo Chem Co Ltd | Carboxylic ester, its preparation, insecticide and acaricide with low toxicity to fish comprising it as active constituent |
| 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 |
-
1982
- 1982-09-29 FR FR8216373A patent/FR2533416B1/en not_active Expired
-
1983
- 1983-09-21 ZA ZA837022A patent/ZA837022B/en unknown
- 1983-09-27 JP JP58177152A patent/JPS59116202A/en active Pending
- 1983-09-28 IT IT8349062A patent/IT1212889B/en active
- 1983-09-28 AU AU19660/83A patent/AU563624B2/en not_active Ceased
- 1983-09-28 CH CH5259/83A patent/CH658772A5/en not_active IP Right Cessation
- 1983-09-28 CA CA000437768A patent/CA1208127A/en not_active Expired
- 1983-09-28 GB GB08325895A patent/GB2127691B/en not_active Expired
- 1983-09-29 DE DE19833335360 patent/DE3335360A1/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1592691A (en) * | 1976-10-05 | 1981-07-08 | Ici Australia Ltd | Stabilised tickicidal compositions |
Cited By (2)
| 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 |
| WO2024189563A1 (en) | 2023-03-14 | 2024-09-19 | Adama Makhteshim Ltd. | Liquid compositions containing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine-(1h)-one and derivatives thereof and a uv absorber |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2533416A1 (en) | 1984-03-30 |
| ZA837022B (en) | 1984-10-31 |
| JPS59116202A (en) | 1984-07-05 |
| DE3335360A1 (en) | 1984-03-29 |
| GB8325895D0 (en) | 1983-11-02 |
| AU563624B2 (en) | 1987-07-16 |
| IT1212889B (en) | 1989-11-30 |
| GB2127691B (en) | 1986-11-05 |
| AU1966083A (en) | 1984-04-05 |
| IT8349062A0 (en) | 1983-09-28 |
| CA1208127A (en) | 1986-07-22 |
| CH658772A5 (en) | 1986-12-15 |
| FR2533416B1 (en) | 1988-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19920928 |