EP1435783A1 - Insecticide composition - Google Patents

Insecticide composition

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Publication number
EP1435783A1
EP1435783A1 EP02783061A EP02783061A EP1435783A1 EP 1435783 A1 EP1435783 A1 EP 1435783A1 EP 02783061 A EP02783061 A EP 02783061A EP 02783061 A EP02783061 A EP 02783061A EP 1435783 A1 EP1435783 A1 EP 1435783A1
Authority
EP
European Patent Office
Prior art keywords
radical
chosen
alkyl
haloalkyl
oil
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.)
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Application number
EP02783061A
Other languages
German (de)
French (fr)
Inventor
François DARCHY
Elmar Rump
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.)
Bayer CropScience SA
Original Assignee
Bayer CropScience SA
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Filing date
Publication date
Application filed by Bayer CropScience SA filed Critical Bayer CropScience SA
Publication of EP1435783A1 publication Critical patent/EP1435783A1/en
Withdrawn legal-status Critical Current

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to an insecticide composition useful for controlling ravaging or pest arthropods, and in particular to an insecticide composition comprising a phenyl pyrazole compound as the active material in combination with an oil adjuvant.
  • Insecticide compositions comprising phenyl pyrazole • compounds are known and in particular EP 029511 discloses an insecticide composition comprising the compound 5-amino-3-cyano-l- (2, 6-dichloro-4- trifluoromethylphenyl) -4- trifluoromethylsulphinylpyrazole, generally known as and is known as fipronil.
  • a more recently known phenyl pyrazole compound which can also be used as the active ingredient in an insecticide composition is 5-amino-3- cyano-1,- (2, 6-dichloro-4-trifluoromethylphenyl) -4- ethylsulphinylpyrazole . This compound is generally known as ethiprole and is disclosed in US Patent 5814652.
  • the present invention provides an insecticide composition
  • a compound of general formula (I) and an oil said oil being of plant origin and possessing high drying power
  • R 2 represents -S(0) n R 3 or the 4 , 5-dicyanoimidazol- 2-yl radical or a haloalkyl group;
  • R 3 represents an alkyl or haloalkyl radical
  • R 5 and R 6 are independently chosen from a hydrogen atom, an alkyl, haloalkyl, -C(O) alkyl, alkoxycarbonyl, alkoxyalkyl-C(O) - or -S(0) r CF 3 radical; or R 5 and R 6 form together a divalent radical which may be interrupted by one or more heteroatoms, such as oxygen or sulphur;
  • R is chosen from an alkyl radical and a haloalkyl radical
  • R 8 is chosen from an alkyl radical, a haloalkyl radical and a hydrogen atom
  • R 9 is chosen from a hydrogen atom and an alkyl radical; Rio is chosen from a phenyl radical and a heteroaryl radical optionally substituted with one or more hydroxyl radicals, halogen atoms, -O-alkyls, -S-alkyls, cyano or alkyl or a combination thereof;
  • X is chosen from a nitrogen atom and the C-R ⁇ 2 radical
  • Y is chosen from hydroxyl, amino, aminocarbonyl, alkoxy, arylcarbonyl, alkylcarbonyl, alkoxycarbonyl, carbamoyl, arylcarbamoyl, alkylcarbamoyl and pyrazole groups, which may be substituted or otherwise;
  • Z is chosen from hydroxyl, amino, aminocarbonyl, alkoxy, arylcarbonyl, alkylcarbonyl, alkoxycarbonyl, carbamoyl, arylcarbamoyl and alkylcarbamoyl groups;
  • Rix and R i2 are independently chosen from a halogen atom or a hydrogen atom or alternatively -CN or -N0 2 ;
  • R i3 is chosen from a halogen atom, a haloalkyl, haloalkoxy, -S(0) q CF 3 and -SF 5 radical;
  • m, n, q, r are independently chosen from 0, 1 and 2; with the proviso that when R x represents the methyl radical, then R 3 represents a haloalkyl radical, R 4 represents -NH 2 , n represents CI, R ⁇ 3 represents -CF 3 , and X represents N;
  • the present invention is an insecticide composition useful for protecting crops, based on a phenyl pyrazole compound and an adjuvant of the plant- derived oil type possessing a high drying power.
  • a phenyl pyrazole compound and an adjuvant of the plant- derived oil type possessing a high drying power.
  • Numerous examples of the use of vegetable oils in formulations of pesticide, and in particular insecticide, compounds are known, for example from US 6149913.
  • no use of vegetable oil possessing high drying power in insecticide compositions has ever been reported.
  • such a use in the insecticide compositions according to the invention have made it possible to obtain very advantageous results.
  • composition of the formulation provided makes it possible to obtain an excellent physical quality of the plant-protection mixture for application and thus allows its use with various other commercial combinations with no risk of physicochemical incompatibility.
  • Such a stability of the plant- protection mixture for application of the insecticide composition according to the invention also makes it possible to be able to formulate certain active ingredients which are otherwise difficult or even impossible to apply.
  • the insecticide of the present invention comprises a compound of general formula 1 and an oil of the plant origin.
  • the alkyl and alkoxy radicals of formula (I) are preferably lower alkyl and alkoxy radicals, that is to say radicals possessing from 1 to 4 carbon atoms; the haloalkyl and haloalkoxy radicals likewise preferably possess from 1 to 4 carbon atoms; the haloalkyl and haloalkoxy radicals may carry one or more halogen atoms; the preferred radicals of this type comprise -CF 3 and -OCF 3 .
  • the preferred compound of general formula 1 is when Ri represents -CN; R 2 represents -S(0) n R 3 ; R 3 is alkyl or haloalkyl; R 4 represents -NR 5 R6; R5 and R 6 are independently chosen from a hydrogen atom, an alkyl, haloalkyl, -C(O) alkyl and C(0)OR 7 radical; R 7 is an alkyl or haloalkyl radical; X represents -C-R ⁇ 2 ; R i3 is a haloalkyl; Ru and R i2 are independently chosen from a halogen atom or a hydrogen atom or alternatively -CN or -N0 2 .
  • a first particularly preferred compound according to general formula 1 are (1) when R 3. represents -CN; R 2 represents -S(0) 2 CF 3 ; R 4 represents -NH 2 ; X represents -C-Cl; Rn is chloride and R 13 is a methylchloride .
  • This compound has the chemical name 5-amino-3-cyano-l- (2, 6- dichloro-4-trifluoromethylphenyl) -4- trifluoromethylsulphinylpyrazole and is known as fipronil.
  • a second particularly preferred compound is when Ri represents -CN; R 2 represents -S(0) 2 C 2 Hs; R 4 represents -NH 2 ; X represents -C-Cl; Rn is chloride and Ri 3 is methyl chloride.
  • This compound has the chemical name 5-amino-3-cyano-l- (2, 6-dichloro-4- trifluoromethylphenyl) -4-ethylsulphinylpyrazole and is also known as ethiprole.
  • the second component of the composition is an oil of plant origin.
  • the advantages attached to the use of vegetable oil according to the present invention are their nontoxicity or at the very least a lower toxicity, compared with oils of mineral origin, a lower phytotoxicity, a higher biodegradability.
  • the oil is suitably an unsaturated vegetable oil, an isomerised oil, a vegetable oil ester, of a plant polymer or a mixture, of these various organic phases.
  • the oil may be of various origins, but those derived from linseed, sunflower, soyabean, maize, cottonseed, safflower and rapeseed is preferred.
  • oils are available in different grades, namely crude, refined or isomerised.
  • the oil is a polyunsaturated vegetable oil which naturally contains a large number of unsaturated bonds.
  • the expression polyunsaturated oil is understood to mean a triglyceride in which the majority of linear fatty chains possess two or three double bonds per chain, noted C18:2 or C18:3, that is to say chains consisting of 18 carbon atoms with 2 or 3 double bonds.
  • polyunsaturated oils there may be mentioned triglycerides which predominantly contain so-called linoleic fatty acid chains (C18:3) such as linseed oil.
  • the composition by weight of this oil may be in the following range: 50 to 60% of C18:3 - 10 to 17% of C18:2 - 15 to 25% of C18:l - 2 to 4% of C18:0 - 5 to 8% of C16:0.
  • polyunsaturated oils there may also be mentioned the triglycerides predominantly containing linoleic type fatty acid chains (C18:2) such as sunflower, maize, soyabean, safflower, cottonseed and rapeseed oil.
  • the composition of these oils may be in the following range: 45 to 70% of C18:2 - 0.1 to 10% of C18:3 - 10 to 40% of C18:l - 0.1 to 10% of C18:0 - 1 to 26% of C16:0.
  • the oil falling within the scope of the present invention is said to be a drying oil.
  • The- drying power is either natural (drying or semidrying oils) or obtained by chemically treating an oil which has little or no drying power (so-called semidrying or nondrying oils) ; this oil is then said to be isomerised.
  • isomerized oil isomerized sunflower oil with a percentage of conjugated dienes of between 16 and 18%, but also isomerized linseed oil containing 11 to 13% of conjugated dienes.
  • composition according to the invention it is preferable to use vegetable oils whose iodine value linked to their drying power is greater than 70, preferably greater than 90, more preferably still greater than 130, and in a most preferred manner greater than 150.
  • the oil is preferably refined and/or isomerised sunflower oil.
  • the weight ratio of oil to compound of general formula 1 in the composition according to the present invention is suitably from 0.15 to 1.6, preferably from 0.2 to 1.35, more preferably from 0.25 to 1.
  • the composition according to the present invention is a liquid and may be in the form of a concentrated composition, that is to say commercial product combining both substances. It may also be dilute composition ready to be sprayed on the crop to be treated. In the latter case, the dilution with water may be carried out either using a commercial concentrated composition containing both substances (this mixture is called ready mix) or by means of the tank mix of both commercial concentrated compositions each containing one substance.
  • the liquid composition according to the present invention may be in the form of a solution, suspension or emulsion or emulsifiable concentrate.
  • the oil- aqueous liquid compositions are preferred both because of their ease of use and because of the simplicity of their manufacture.
  • an aqueous suspension concentrate using vegetable oil in the form of an oil-in-water emulsion.
  • the composition according to the present invention may further comprise solid or liquid additives corresponding to the customary techniques for the fo mulation of plant-protection products.
  • the composition may also comprise, , all the usual additives or adjuvants for plant-protection compositions, in particular carriers, surfactants, adhesion promoters and flow-enhancing agents, antifreezing agents.
  • composition may also contain additional ingredients such as protective colloids, adhesives, thickeners, thixotropic agents, penetration-enhancing agents, stabilizers, sequestrants, pigments, colourings, polymers, antifoams.
  • carrier in the present disclosure, designates a natural or synthetic, organic or inorganic substance with which the active ingredients are combined to facilitate their application to the plant. This carrier is therefore generally inert and should be agriculturally acceptable, in particular on the treated plant.
  • the carrier may be solid (clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, and the like) or liquid (water, alcohols, ketones, petroleum fractions, aromatic or paraffin hydrocarbons, chlorinated hydrocarbons, liquefied gases, and the like) .
  • the surfactant may be an emulsifying, dispersing or wetting agent of the ionic or nonionic type.
  • ionic or nonionic type there may be mentioned, for example, salts of polyacrylic acids, salts of lignosulphonic acids, salts of phenolsulphonic or naphthalenesulphonic acids, polycondensates of ethyleneoxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols) , salts of sulphosuccinic acid esters, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated phenols or alcohols.
  • oil-aqueous suspension concentrate is understood to mean an aqueous suspension in which the solid active ingredients are in the form of crystals in suspension in water and the oily organic phase, here the vegetable oil plus an emulsive substance, in the form of an oil-in-water emulsion.
  • the suspension concentrates which can also be applied by spraying, are prepared so as to obtain a stable fluid product which does not give rise to thickening or to the formation of a sediment after storage or to phase separation, and they contain from 10 to 75% of active ingredients, from 0.5 to 15% of surfactants, from 0.1 to 10% of thixotropic agents, from 0 to 10% of appropriate additives, such as pigments, colourings, antifoams, corrosion inhibitors, stabilizers, penetration-enhancing agents, adhesives and, as carrier, water or an organic liquid in which the active ingredients are scarcely soluble or are insoluble.
  • Some organic solid substances or inorganic salts may be dissolved or dispersed in the carrier to prevent sedimentation or as antifreeze for water.
  • the insecticide composition of the present invention may be applied to crops means of various known methods of treatment such as spraying, over the aerial parts of the crops to be treated, of a liquid comprising the said composition, sprinkling, injection into trees or daubing. Spraying a liquid over the aerial parts of the crops to be treated is the preferred method of treatment.
  • the invention also relates to a method of treatment for controlling crop-ravaging arthropods, characterized in that an effective and nonphytotoxic dose of the insecticidal composition as hereinbefore defined is applied over the aerial parts of plants.
  • an effective and nonphytotoxic quantity is understood to mean a quantity of composition according to the invention which is sufficient to allow the arthropods present or likely to appear ,on the crops to be controlled or destroyed, and causing no symptom of phytotoxicity for the said crops.
  • Such a quantity is likely to vary within broad limits depending on the pest to be controlled, the type of crop, the climatic conditions, and the compounds contained in the composition according to the invention; this quantity may, for example, be determined by systematic field trials, within the capability of persons skilled in the art.
  • the insecticide composition according to the invention is advantageously used so that the dose of insecticidal compound applied is from 5 to 1000 g/ha, preferably from 10 to 250 g/ha for compound of general formula 1.
  • the oil component there is suitably required an amount from 0.25 to 0.45 times the dose of compound of general formula 1.
  • the actual dose will of course depend upon various factors such as the plant to be treated, the degree of infestation, the climatic conditions and the like.
  • cereal grain in particular barley, protein- rich and oil-rich plants, such as peas, rapeseed, sunflower, maize, grapevine, potato, tomato, vegetable crops (lettuce, curcurbitaceous plants and the like) , rice, arboriculture (apple tree, pear tree, cherry tree and the like), citrus fruits, turf.
  • protein- rich and oil-rich plants such as peas, rapeseed, sunflower, maize, grapevine, potato, tomato, vegetable crops (lettuce, curcurbitaceous plants and the like) , rice, arboriculture (apple tree, pear tree, cherry tree and the like), citrus fruits, turf.
  • the two components of the insecticide composition according to the invention are applied simultaneously, by means of a composition according to the invention prepared from a ready-mix concentrate or from a tank mix.
  • Another aspect of the invention relates to a product for the simultaneous, sequential or alternate application of compound of general formula 1 and the oil of the insecticidal composition according to the invention.
  • Example 1 Preparation of Insecticide Composition
  • An insecticide composition according to the present invention comprising the following components:
  • Monopropylene glycol, isotridecanol, ethoxylated polyararylphenol phosphate potassium salt, dioctyl sulphosuccinate sodium salt, and citric acid monohydrate are simultaneously added to water, with stirring. The stirring is continued so as to disperse and dissolve the constituents.
  • the active ingredient is then added, with stirring.
  • the suspension is preground using a colloid mill and then ground to the final particle size using a ball mill.
  • a solution containing 2% of polysaccharide and 1% of 1,2- benzisothiazolin-3-one is added, with stirring, to the ground suspension.
  • the oily phase consisting of the homogeneous mixture of vegetable oil and ethoxylated oleic acid, is added, with stirring, so as to form the oil-in-water emulsion.
  • compositions according to the present invention were prepared as detailed in Example 1 containing rapeseed oil and soyabean oil.
  • Table 1 details the components present in each formulation.
  • Rice plants of approximately 16 to 17 cm in height infested by the insect small brown planthopper (Laodelphax striatellus) were treated by foliar application of compositions 1 and 2 according to the present invention at a concentration of 50g/ha.
  • the insecticide composition was applied with a spray gun.
  • Rice plants of approximately 16 to 17 cm in height infested by the insect brown planthopper (Nilaoarvara lugens) were treated by foliar application of compositions 1 and 2 according to the present invention at two dose rates 25 and 50 g/ha.
  • the insecticide composition was applied with a spray gun.
  • oil-containing composition of the present invention provide a better knock-down activity that the corresponding composition without the oil.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The subject of the present invention is an insecticidal composition useful for controlling ravaging or pest arthropods, in particular insects, and more especially those which attack crops, the said composition combining at least one insecticidal compound of general formula (I) as in the description with an oil of plant origin possessing high drying power.

Description

INSECTICIDE COMPOSITION
The present invention relates to an insecticide composition useful for controlling ravaging or pest arthropods, and in particular to an insecticide composition comprising a phenyl pyrazole compound as the active material in combination with an oil adjuvant.
Insecticide compositions comprising phenyl pyrazole • compounds are known and in particular EP 029511 discloses an insecticide composition comprising the compound 5-amino-3-cyano-l- (2, 6-dichloro-4- trifluoromethylphenyl) -4- trifluoromethylsulphinylpyrazole, generally known as and is known as fipronil. A more recently known phenyl pyrazole compound which can also be used as the active ingredient in an insecticide composition is 5-amino-3- cyano-1,- (2, 6-dichloro-4-trifluoromethylphenyl) -4- ethylsulphinylpyrazole . This compound is generally known as ethiprole and is disclosed in US Patent 5814652.
It is desirable to reduce the doses of chemical products spread in the environment, in order to control crop ravagers, in particular by reducing the doses for application. To do this, certain adjuvants, termed biological activators, such as mineral oils, wetting agents, penetrating agents, are combined with commercial proprietary products and now make it possible, for example, to combine an adjuvant of the mineral oil type with insecticidal compounds, which has the advantage of reducing the dose of compounds which is applied. This thus widens the possibilities of choice which are offered to farmers, so that they can find the solution best suited to their particular problem. On the other hand, the use of some of these proprietary products is restricted when cases of phytotoxicity are observed on certain crops.
We have found that when a specific adjuvant is combined with the phenyl pyrazole compound, the resulting insecticide composition is selective even on so-called sensitive crops, while preserving an equivalent biological activity against the ravagers targeted.
Accordingly, the present invention provides an insecticide composition comprising a compound of general formula (I) and an oil, said oil being of plant origin and possessing high drying power
0)
in which
Rx represents a halogen atom, the -CN radical or the methyl radical or the radical -C(S)NH2, the radical -C(=N-Y)Z or the radical C(0)CH3; R2 represents -S(0)nR3 or the 4 , 5-dicyanoimidazol- 2-yl radical or a haloalkyl group;
R3 represents an alkyl or haloalkyl radical;
R4 is chosen from the group comprising a hydrogen atom, a halogen atom, a hydroxyl or alkoxy group, and a radical which may be -NR5R6, C (O) R7-C (0) OR7, -S(0)mR7, alkyl, haloalkyl, -OR8 or -N=C (R9) (R10) ;
R5 and R6 are independently chosen from a hydrogen atom, an alkyl, haloalkyl, -C(O) alkyl, alkoxycarbonyl, alkoxyalkyl-C(O) - or -S(0)rCF3 radical; or R5 and R6 form together a divalent radical which may be interrupted by one or more heteroatoms, such as oxygen or sulphur;
R is chosen from an alkyl radical and a haloalkyl radical; R8 is chosen from an alkyl radical, a haloalkyl radical and a hydrogen atom;
R9 is chosen from a hydrogen atom and an alkyl radical; Rio is chosen from a phenyl radical and a heteroaryl radical optionally substituted with one or more hydroxyl radicals, halogen atoms, -O-alkyls, -S-alkyls, cyano or alkyl or a combination thereof;
X is chosen from a nitrogen atom and the C-Rι2 radical;
Y is chosen from hydroxyl, amino, aminocarbonyl, alkoxy, arylcarbonyl, alkylcarbonyl, alkoxycarbonyl, carbamoyl, arylcarbamoyl, alkylcarbamoyl and pyrazole groups, which may be substituted or otherwise; Z is chosen from hydroxyl, amino, aminocarbonyl, alkoxy, arylcarbonyl, alkylcarbonyl, alkoxycarbonyl, carbamoyl, arylcarbamoyl and alkylcarbamoyl groups;
Rix and Ri2 are independently chosen from a halogen atom or a hydrogen atom or alternatively -CN or -N02; Ri3 is chosen from a halogen atom, a haloalkyl, haloalkoxy, -S(0)qCF3 and -SF5 radical; m, n, q, r are independently chosen from 0, 1 and 2; with the proviso that when Rx represents the methyl radical, then R3 represents a haloalkyl radical, R4 represents -NH2, n represents CI, Rχ3 represents -CF3, and X represents N;
The present invention is an insecticide composition useful for protecting crops, based on a phenyl pyrazole compound and an adjuvant of the plant- derived oil type possessing a high drying power. Numerous examples of the use of vegetable oils in formulations of pesticide, and in particular insecticide, compounds are known, for example from US 6149913. However, no use of vegetable oil possessing high drying power in insecticide compositions has ever been reported. Thus and most surprisingly, such a use in the insecticide compositions according to the invention have made it possible to obtain very advantageous results.
Furthermore, the composition of the formulation provided makes it possible to obtain an excellent physical quality of the plant-protection mixture for application and thus allows its use with various other commercial combinations with no risk of physicochemical incompatibility. Such a stability of the plant- protection mixture for application of the insecticide composition according to the invention also makes it possible to be able to formulate certain active ingredients which are otherwise difficult or even impossible to apply.
The insecticide of the present invention comprises a compound of general formula 1 and an oil of the plant origin. As regards the compound of general formula 1, the alkyl and alkoxy radicals of formula (I) are preferably lower alkyl and alkoxy radicals, that is to say radicals possessing from 1 to 4 carbon atoms; the haloalkyl and haloalkoxy radicals likewise preferably possess from 1 to 4 carbon atoms; the haloalkyl and haloalkoxy radicals may carry one or more halogen atoms; the preferred radicals of this type comprise -CF3 and -OCF3. The preferred compound of general formula 1 is when Ri represents -CN; R2 represents -S(0)nR3; R3 is alkyl or haloalkyl; R4 represents -NR5R6; R5 and R6 are independently chosen from a hydrogen atom, an alkyl, haloalkyl, -C(O) alkyl and C(0)OR7 radical; R7 is an alkyl or haloalkyl radical; X represents -C-Rι2; Ri3 is a haloalkyl; Ru and Ri2 are independently chosen from a halogen atom or a hydrogen atom or alternatively -CN or -N02.
A first particularly preferred compound according to general formula 1 are (1) when R3. represents -CN; R2 represents -S(0)2CF3; R4 represents -NH2 ; X represents -C-Cl; Rn is chloride and R13 is a methylchloride . This compound has the chemical name 5-amino-3-cyano-l- (2, 6- dichloro-4-trifluoromethylphenyl) -4- trifluoromethylsulphinylpyrazole and is known as fipronil.
A second particularly preferred compound is when Ri represents -CN; R2 represents -S(0)2C2Hs; R4 represents -NH2 ; X represents -C-Cl; Rn is chloride and Ri3 is methyl chloride. This compound has the chemical name 5-amino-3-cyano-l- (2, 6-dichloro-4- trifluoromethylphenyl) -4-ethylsulphinylpyrazole and is also known as ethiprole. The second component of the composition is an oil of plant origin. The advantages attached to the use of vegetable oil according to the present invention are their nontoxicity or at the very least a lower toxicity, compared with oils of mineral origin, a lower phytotoxicity, a higher biodegradability. The oil is suitably an unsaturated vegetable oil, an isomerised oil, a vegetable oil ester, of a plant polymer or a mixture, of these various organic phases.
The oil may be of various origins, but those derived from linseed, sunflower, soyabean, maize, cottonseed, safflower and rapeseed is preferred.
These oils are available in different grades, namely crude, refined or isomerised. Preferably, the oil is a polyunsaturated vegetable oil which naturally contains a large number of unsaturated bonds. The expression polyunsaturated oil is understood to mean a triglyceride in which the majority of linear fatty chains possess two or three double bonds per chain, noted C18:2 or C18:3, that is to say chains consisting of 18 carbon atoms with 2 or 3 double bonds. By way of example of polyunsaturated oils, there may be mentioned triglycerides which predominantly contain so-called linoleic fatty acid chains (C18:3) such as linseed oil. As a guide, the composition by weight of this oil, characterized as fatty acids, may be in the following range: 50 to 60% of C18:3 - 10 to 17% of C18:2 - 15 to 25% of C18:l - 2 to 4% of C18:0 - 5 to 8% of C16:0. By way of example of polyunsaturated oils, there may also be mentioned the triglycerides predominantly containing linoleic type fatty acid chains (C18:2) such as sunflower, maize, soyabean, safflower, cottonseed and rapeseed oil. As a guide, the composition of these oils, characterized as fatty acids, may be in the following range: 45 to 70% of C18:2 - 0.1 to 10% of C18:3 - 10 to 40% of C18:l - 0.1 to 10% of C18:0 - 1 to 26% of C16:0. In other words, the oil falling within the scope of the present invention is said to be a drying oil. The- drying power is either natural (drying or semidrying oils) or obtained by chemically treating an oil which has little or no drying power (so-called semidrying or nondrying oils) ; this oil is then said to be isomerised. The isomerisation reaction consists in conjugating the double bonds of the fatty acid chain - C=CH-CH2-CH=CH-, in order to obtain conjugated dienes as follows -CH=CH-CH=CH-CH2-, thus increasing their drying ,power (reactivity with air) . Thus there may be mentioned, as isomerized oil, isomerized sunflower oil with a percentage of conjugated dienes of between 16 and 18%, but also isomerized linseed oil containing 11 to 13% of conjugated dienes.
For the composition according to the invention, it is preferable to use vegetable oils whose iodine value linked to their drying power is greater than 70, preferably greater than 90, more preferably still greater than 130, and in a most preferred manner greater than 150.
The oil is preferably refined and/or isomerised sunflower oil.
The weight ratio of oil to compound of general formula 1 in the composition according to the present invention, is suitably from 0.15 to 1.6, preferably from 0.2 to 1.35, more preferably from 0.25 to 1. The composition according to the present invention is a liquid and may be in the form of a concentrated composition, that is to say commercial product combining both substances. It may also be dilute composition ready to be sprayed on the crop to be treated. In the latter case, the dilution with water may be carried out either using a commercial concentrated composition containing both substances (this mixture is called ready mix) or by means of the tank mix of both commercial concentrated compositions each containing one substance.
The liquid composition according to the present invention may be in the form of a solution, suspension or emulsion or emulsifiable concentrate. The oil- aqueous liquid compositions are preferred both because of their ease of use and because of the simplicity of their manufacture. Preferably, there is available an aqueous suspension concentrate using vegetable oil in the form of an oil-in-water emulsion. The composition according to the present invention may further comprise solid or liquid additives corresponding to the customary techniques for the fo mulation of plant-protection products. The composition may also comprise, , all the usual additives or adjuvants for plant-protection compositions, in particular carriers, surfactants, adhesion promoters and flow-enhancing agents, antifreezing agents.
This composition may also contain additional ingredients such as protective colloids, adhesives, thickeners, thixotropic agents, penetration-enhancing agents, stabilizers, sequestrants, pigments, colourings, polymers, antifoams. The term "carrier", in the present disclosure, designates a natural or synthetic, organic or inorganic substance with which the active ingredients are combined to facilitate their application to the plant. This carrier is therefore generally inert and should be agriculturally acceptable, in particular on the treated plant. The carrier may be solid (clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, and the like) or liquid (water, alcohols, ketones, petroleum fractions, aromatic or paraffin hydrocarbons, chlorinated hydrocarbons, liquefied gases, and the like) .
The surfactant may be an emulsifying, dispersing or wetting agent of the ionic or nonionic type. There may be mentioned, for example, salts of polyacrylic acids, salts of lignosulphonic acids, salts of phenolsulphonic or naphthalenesulphonic acids, polycondensates of ethyleneoxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols) , salts of sulphosuccinic acid esters, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated phenols or alcohols. The presence of at least one surfactant is desirable in order to promote the dispersion of the active ingredients in water and their good application to plants. The expression oil-aqueous suspension concentrate is understood to mean an aqueous suspension in which the solid active ingredients are in the form of crystals in suspension in water and the oily organic phase, here the vegetable oil plus an emulsive substance, in the form of an oil-in-water emulsion.
The suspension concentrates, which can also be applied by spraying, are prepared so as to obtain a stable fluid product which does not give rise to thickening or to the formation of a sediment after storage or to phase separation, and they contain from 10 to 75% of active ingredients, from 0.5 to 15% of surfactants, from 0.1 to 10% of thixotropic agents, from 0 to 10% of appropriate additives, such as pigments, colourings, antifoams, corrosion inhibitors, stabilizers, penetration-enhancing agents, adhesives and, as carrier, water or an organic liquid in which the active ingredients are scarcely soluble or are insoluble. Some organic solid substances or inorganic salts may be dissolved or dispersed in the carrier to prevent sedimentation or as antifreeze for water.
The insecticide composition of the present invention may be applied to crops means of various known methods of treatment such as spraying, over the aerial parts of the crops to be treated, of a liquid comprising the said composition, sprinkling, injection into trees or daubing. Spraying a liquid over the aerial parts of the crops to be treated is the preferred method of treatment.
According to a further aspect of the resent invention there is provided The invention also relates to a method of treatment for controlling crop-ravaging arthropods, characterized in that an effective and nonphytotoxic dose of the insecticidal composition as hereinbefore defined is applied over the aerial parts of plants.
The expression "effective and nonphytotoxic quantity" is understood to mean a quantity of composition according to the invention which is sufficient to allow the arthropods present or likely to appear ,on the crops to be controlled or destroyed, and causing no symptom of phytotoxicity for the said crops. Such a quantity is likely to vary within broad limits depending on the pest to be controlled, the type of crop, the climatic conditions, and the compounds contained in the composition according to the invention; this quantity may, for example, be determined by systematic field trials, within the capability of persons skilled in the art.
The insecticide composition according to the invention is advantageously used so that the dose of insecticidal compound applied is from 5 to 1000 g/ha, preferably from 10 to 250 g/ha for compound of general formula 1. For the oil component, there is suitably required an amount from 0.25 to 0.45 times the dose of compound of general formula 1. The actual dose will of course depend upon various factors such as the plant to be treated, the degree of infestation, the climatic conditions and the like.
Among the crops suitable for the method of treatment according to the invention, there may be mentioned cereal grain, in particular barley, protein- rich and oil-rich plants, such as peas, rapeseed, sunflower, maize, grapevine, potato, tomato, vegetable crops (lettuce, curcurbitaceous plants and the like) , rice, arboriculture (apple tree, pear tree, cherry tree and the like), citrus fruits, turf.
In the method of treatment according to the invention, the two components of the insecticide composition according to the invention are applied simultaneously, by means of a composition according to the invention prepared from a ready-mix concentrate or from a tank mix.
Another aspect of the invention relates to a product for the simultaneous, sequential or alternate application of compound of general formula 1 and the oil of the insecticidal composition according to the invention.
The following example is given without limiting the advantageous properties of the compositions according to the invention.
Example 1 : Preparation of Insecticide Composition
An insecticide composition according to the present invention comprising the following components:
- insecticidal active ingredient of formula (I) 375
- ethoxylated polyararylphenol phosphate potassium 60 salt
- dioctyl sulphosuccinate sodium salt 10
- ethoxylated oleic acid 8.5
- polyunsaturated vegetable oil 170
- monopropylene glycol 50
- polysaccharide 1.4
- 1, 2-benzisothiazolin-3-one 0.7
- isotridecanol 10
- citric acid monohydrate 1
- water (qs 1 litre) is prepared according to known methods and as detailed as follows :
Monopropylene glycol, isotridecanol, ethoxylated polyararylphenol phosphate potassium salt, dioctyl sulphosuccinate sodium salt, and citric acid monohydrate are simultaneously added to water, with stirring. The stirring is continued so as to disperse and dissolve the constituents. The active ingredient is then added, with stirring. The suspension is preground using a colloid mill and then ground to the final particle size using a ball mill. A solution containing 2% of polysaccharide and 1% of 1,2- benzisothiazolin-3-one is added, with stirring, to the ground suspension. The oily phase, consisting of the homogeneous mixture of vegetable oil and ethoxylated oleic acid, is added, with stirring, so as to form the oil-in-water emulsion.
Example 2
Two compositions according to the present invention were prepared as detailed in Example 1 containing rapeseed oil and soyabean oil. The following Table 1 details the components present in each formulation.
Example 3: Treatment of Rice Crops
Rice plants of approximately 16 to 17 cm in height infested by the insect small brown planthopper (Laodelphax striatellus) were treated by foliar application of compositions 1 and 2 according to the present invention at a concentration of 50g/ha. The insecticide composition was applied with a spray gun.
The insect mortality was observed over a 2-days period. The results are given in Table 2 below:
Example 4 Treatment of Rice Crops
Rice plants of approximately 16 to 17 cm in height infested by the insect brown planthopper (Nilaoarvara lugens) were treated by foliar application of compositions 1 and 2 according to the present invention at two dose rates 25 and 50 g/ha. The insecticide composition was applied with a spray gun.
As a comparative exercise, a similar suspension composition comprising the same active ingredient but with no oil component was also applied to the rice plants .
The number of insects per square metre of plant was observed over a 14-days period. The results are given in Table 3 below: Table 3
It can be seen from the above results that the oil-containing composition of the present invention provide a better knock-down activity that the corresponding composition without the oil.

Claims

1. Insecticidal composition characterized in that it comprises at least one insecticidal compound A of formula (I) and an oil of plant origin and possessing high drying power,
in which
Ri represents a halogen atom, the -CN radical or the methyl radical or the radical -C(S)NH2, the radical -C(=N-Y)Z or the radical C(0)CH3;
R2 represents -S(0)nR3 or the 4, 5-dicyanoimidazol- 2-yl radical or a haloalkyl group;
R3 represents an alkyl or haloalkyl radical; R4 is chosen from the group comprising a hydrogen atom, a halogen atom, a hydroxyl or alkoxy group, and a radical which may be -NR5R6f C (O) R7-C (0) OR7, -S(0)mR7, alkyl, haloalkyl, -0R8 or -N=C (R9) (R10) ;
R5 and R_ are independently chosen from a hydrogen atom, an alkyl, haloalkyl, -C(O) alkyl, alkoxycarbonyl, alkoxyalkyl-C(O) - or -S(0)rCF3 radical; or R5 and R6 form together a divalent radical which may be interrupted by one or more heteroatoms, such as oxygen or sulphur;
R is chosen from an alkyl radical and a haloalkyl radical;
Rs is chosen from an alkyl radical, a haloalkyl radical and a hydrogen atom; Rg is chosen from a hydrogen atom and an alkyl radical;
R10 is chosen from a phenyl radical and a heteroaryl radical optionally substituted with one or more hydroxyl radicals, halogen atoms, -0-alkyls, -S-alkyls, cyano or alkyl or a combination thereof;
X is chosen from a nitrogen atom and the C-Rχ2 radical; Y is chosen from hydroxyl, amino, aminocarbonyl, alkoxy, arylcarbonyl, alkylcarbonyl, alkoxycarbonyl, carbamoyl, arylcarbamoyl, alkylcarbamoyl and pyrazole groups, which may be substituted or otherwise;
Z is chosen from hydroxyl, amino, aminocarbonyl, alkoxy, arylcarbonyl, alkylcarbonyl, alkoxycarbonyl, carbamoyl, arylcarbamoyl and alkylcarbamoyl groups;
Rn and R12 are independently chosen from a halogen atom or, a hydrogen atom or alternatively -CN or -N02;
Rι3 is chosen from a halogen atom, a haloalkyl, haloalkoxy, -S(0)qCF3 and -SF5 radical; m, n, q, r are independently chosen from 0, 1 and 2; with the restriction that when Ri represents the methyl radical, then R3 represents a haloalkyl radical, R4 represents -NH2, Rι represents Cl, Ri3 represents -CF3, and X represents N;
2. Insecticide composition according to claim 1 in which for compound of formula (I) : Ri represents -CN;
R2 represents -S(0)nR3; R3 is alkyl or haloalkyl or alkyl; R4 represents -NR5R6;
R5 and R6 are independently chosen from a hydrogen atom, an alkyl, haloalkyl, -C(O) alkyl and C(0)0R7 radical;
R7 is chosen from an alkyl radical and a haloalkyl radical; X represents -C-Rχ2; R13 is a haloalkyl;
Rn and Ri2 are independently chosen from a halogen atom or a hydrogen atom or alternatively -CN or -N02; n is 1
3. Insecticide composition according to either of the preceding claims, such that the insecticidal compound of general formula 1 is fipronil having the chemical name 5-amino-3-cyano-l- (2, 6-dichloro-4-trifluoromethyl- phenyl) -4-trifluoromethylsulphinylpyrazole
4. Insecticide composition according to claim 2 or claim 3 , such that the insecticide compound of general formula 1 is ethiprole having the chemical name 5-amino-3-cyano-l- (2, 6-dichloro-4- trifluoromethylphenyl) -4-ethylsulphinylpyrazole.
5. Insecticide composition according to any one of the preceding claims, such that the vegetable oil possesses an iodine value greater than 70,
6 Insecticide composition according to claim 4 the in which such that the vegetable oil possesses an iodine value greater than 150,
7. Insecticide composition according to any one of the preceding claims, such that the vegetable oil is chosen from linseed, sunflower, soybean, maize, cottonseed, safflower and rapeseed oils .
8. Insecticide composition according to any one of the preceding claims, such that the oil/compound of general formula 1 weight ratio is from 0.15 to 1.6,
9. Method of treatment for controlling crop-ravaging arthropods, characterized in that an effective and nonphytotoxic dose of an insecticide composition according to any one of the preceding claims is applied to the aerial parts of plants.
10. Method as claimed in claim 9 characterized in that the dose of insecticidal compound applied is from 5 to 1000 g/ha for compound of general formula 1 and from 0.25 to 0.45 times the dose for compound of general formula 1 for the oil.
11. Product for simultaneous, sequential or alternate application of compounds of general formula 1 and the oil of the insecticidal composition according to the invention.
EP02783061A 2001-09-24 2002-09-23 Insecticide composition Withdrawn EP1435783A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0112273 2001-09-24
FR0112273 2001-09-24
PCT/EP2002/012188 WO2003028465A1 (en) 2001-09-24 2002-09-23 Insecticide composition

Publications (1)

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EP1435783A1 true EP1435783A1 (en) 2004-07-14

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TWI484910B (en) 2006-12-01 2015-05-21 Du Pont Liquid formulations of carboxamide arthropodicides
CN102669190B (en) * 2012-05-11 2013-10-02 浙江农林大学 Botanical pesticide special for landscape plants and preparation method and use thereof

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US6117854A (en) * 1997-08-20 2000-09-12 The Clorox Company Enhanced performance insecticide compositions containing plant derived oil carriers and methods of using the same
US6149913A (en) * 1998-11-16 2000-11-21 Rhone-Poulenc Ag Company, Inc. Compositions and methods for controlling insects

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JP2005504107A (en) 2005-02-10
TWI335208B (en) 2011-01-01
WO2003028465A1 (en) 2003-04-10
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KR20040033318A (en) 2004-04-21
CO5570636A2 (en) 2005-10-31
KR100952092B1 (en) 2010-04-13

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