WO1998000009A1 - Pesticidal compositions - Google Patents

Pesticidal compositions Download PDF

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Publication number
WO1998000009A1
WO1998000009A1 PCT/EP1997/003195 EP9703195W WO9800009A1 WO 1998000009 A1 WO1998000009 A1 WO 1998000009A1 EP 9703195 W EP9703195 W EP 9703195W WO 9800009 A1 WO9800009 A1 WO 9800009A1
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WO
WIPO (PCT)
Prior art keywords
composition according
ethoxylate
mol
composition
propoxylate
Prior art date
Application number
PCT/EP1997/003195
Other languages
French (fr)
Inventor
Manfred Vogt
William Baettig
Original Assignee
Novartis Ag
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 Novartis Ag filed Critical Novartis Ag
Priority to JP10503804A priority Critical patent/JP2000514793A/en
Priority to NZ333283A priority patent/NZ333283A/en
Priority to US09/202,886 priority patent/US6071857A/en
Priority to BR9710090A priority patent/BR9710090A/en
Priority to PL97330710A priority patent/PL330710A1/en
Priority to IL12730897A priority patent/IL127308A0/en
Priority to EP97930372A priority patent/EP0907316A1/en
Priority to AU34350/97A priority patent/AU719494B2/en
Publication of WO1998000009A1 publication Critical patent/WO1998000009A1/en

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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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N25/02—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 liquids as carriers, diluents or solvents
    • 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
    • A01N25/30—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 characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals

Definitions

  • the present invention relates to storage stable, liquid, pesticidal compositions, the preparation of such compositions and a method of using such compositions to combat pests or as plant growth regulators.
  • Alkylphenol ethoxylates for example nonylphenol ethoxylates
  • alkylbenzene sulfonates and its salts for example dodecylbenzene sulfonate calcium salt
  • Fatty alcohol ethoxylates e.g. C ⁇ 0 -C ⁇ 4 alcohol ethoxylates (EP-A-400,585) and tristyrenephenol-ethoxylates (EP-A-102,003) have been proposed, both in combination with alkylbenzene sulfonates, as surfactants in water-emulsifiable pesticidal compositions.
  • C 1 -C 10 Alkyl ethoxylate/propoxylate-blockcopolymers and tristyrenephenol-ethoxylates have been disclosed as surfactants in aqueous suspensions (EP-A-261 ,492).
  • the present invention provides a water-emulsifiable or water-soluble, storage stable, liquid, pesticidal composition, which is substantially free of water, comprising a hydrophobic pesticide or mixture of pesticides dissolved in an organic solvent and comprising as surfactants
  • Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, for example sodium, potassium calcium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower aikylamine, for example ethyl-, diethyl-, triethyl- or dimethyl-propylamine, or a mono-, di- or tri-hydroxy-lower aikylamine, for example mono-, di- or tri-ethanolamine.
  • metal salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium calcium or magnesium salts
  • salts with ammonia or an organic amine such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower aikylamine, for example ethyl-, diethyl-, triethyl- or
  • compositions also include gels having a viscosity of 500 to 20O00 mPas and comprising additionally a gelling agent.
  • compositions according to the invention are stable for at least 12 months at 25°C. They are very well miscible with water, even at higher concentrations.
  • the surfactants can be combined, depending for example on the kind of pesticide and the preferred solvents, as follows:
  • surfactants mentioned above can be prepared by methods known per se; they are also commercially available. Preferred are surfactants, wherein
  • the butanole-ethoxylate/propoxyiate-blockcopolymer has 20-24 mol, preferably 22 mol ethoxylate, and 30-36 mol, most preferably 34 mol propoxylate;
  • the branched C 8 -C ⁇ alcohol ethoxylate is isotridecanol ethoxylate having 5-10 mol, most preferably 6-8 mol ethoxylate;
  • composition of the invention is substantially free of water, i.e. the amount of water is less that 0.5%.
  • Some commercially available materials may contain a small amount of water, which, when more than about 0.1% can be removed for example in a separator.
  • the composition is a gel with a viscosity of 500 - 20O00 mPas; preferably 800 to 10OOO mPas and particularly 1000-5000 mPas.
  • the viscosity of the composition can be measured using for example a BROOKFIELD viscosimeter with spindles 1 to 3 at 30 rpm.
  • the composition additionally has to contain a gelling agent, for example oxypropylated cellulose, precipitated or fused silica (hydrophobizised or non- hydrophobizised), gelatine, polysaccharides, tetramethyl decyne diol, ethoxylated dialkyl phenol, methylated clay, propylene carbonate, hydrogenated castor oil, ethoxylated vegetable oil, sodium benzoate and hexanediol.
  • a gelling agent for example oxypropylated cellulose, precipitated or fused silica (hydrophobizised or non- hydrophobizised), gelatine, polysaccharides, tetramethyl decyne diol, ethoxylated dialkyl phenol, methylated clay, propylene carbonate, hydrogenated castor oil, ethoxylated vegetable oil, sodium benzoate and hexanediol.
  • Preferred gelling agent is oxypropylated
  • Gels are particularly suitable for pesticides packing into water soluble bags or sachets, which quickly dissolve when put into the water.
  • the organic solvents wherein the pesticide has to be dissolved may be water-immiscible or water miscible or a mixture thereof.
  • Suitable water-immiscible solvents in which the pesticides may be dissolved are aliphatic and aromatic hydrocarbons such as hexane, cyclohexane, benzene, toluene, xylene, mineral oil or kerosin, mixtures or substituted naphthalenes, mixtures of mono- and polyalkylated aromatics commercially available under the registered trademarks SOLVESSO and SHELLSOL and PETROL SPEZIAL, halogenated hydroarbons such as methylene chloride, chloroform and o-dichlorobenzene; phthalates, such as dibutyl phthalate or dioctyl phthalate; ethers and esters, such as ethylene glycol monomethyl or monoethyl ether, fatty acid esters; lactones such as butyrolactone, ketones, such as cyclohexanone; plant oils such as castor oil, soybean oil, cottonseed oil and possible methyl esters thereof;
  • Preferred water-immiscible solvents are aliphatic and aromatic hydrocarbons, fatty acid esters ⁇ e.g. WITCONOL 2309), dipropyleneglycol monomethylether (e.g. DOWANOL DPM) and castor oil.
  • Suitable water-miscible solvents in which the pesticides may be dissolved are alcohols and glycols, such as ethanol, ethylene glycol, strongly polar solvents, such as N-methyl-2- pyrrolidone, tetramethylurea, gamma-butyrolacone.dimethyl sulfoxide, N,N- dimethylacetamid and dimethylformamide; preferred are N-methyl-2-pyrrolidone and gamma-butyrolacone.
  • Suitable pesticides are those which are substantially insoluble in water (hydrophobic), but soluble in the organic solvent.
  • pesticide is understood to encompass herbicides, insecticides, acaricides, nemati- cides, ectoparasiticides, fungicides and plant growth regulators.
  • these pesticides may belong to a very wide range of compound classes.
  • compound classes to which the suitable pesticide may belong are: acylalanines, haloacetanilides, triazole derivatives, phosphoric acid esters, pyrethroids, benzilic acid esters, polycyclic halogenated hydrocarbons, diphenyl ether derivates, formamidines, strobilurines, aryloxyphenoxy-alkanoic acid derivatives.
  • suitable individual compounds of the above mentioned compound classes are listed below. Where known, the common name is used to designate the individual compounds
  • Haloacetanilides Dimethachlor, Metolachlor, Pretilachlor, 2-chloro-N-(1-methyl-2-methoxy- ethyl)-acet-2,6-xylidide, Alachlor, Butachlor, Propachlor, Dimethenamid.
  • Diphenyl ether derivates: Bifenox, 4-(4-Pentyn-1-yloxy)diphenylether, Acifluorfen, Oxyfluor- fen, Fluoroglycofen-ethyl, Fomesafen, cis-trans- ( ⁇ )2-ethyl-5-(4-phenoxy-phenoxymethy!)-
  • Phenoxypropionic acid derivatives Fluazifop-butyl, Haloxyf op-methyl, Haloxyfop-(2-ethoxy- ethyl), Fluorotopic, Fenoxapropethyl, Quizalofop-ethyl, Propaquizafop, Diclofop-methyl.
  • Triazole derivatives Difenoconazole, Etaconazol, Propiconazole, Penconazole,
  • Phosphoric acid esters Piperophos, Anilofos, Butamifos, Azamethiphos, Chlorfenvinphos,
  • Prothiophos Quinalphos, Sulprofos, Phemephos, Terbufos, Triazophos, Trichloronate,
  • Fenamipos Isazophos, s-benzyl-o,o-diisopropylphosphorothioate, Edinphos, Pyrazophos.
  • Pyrethroids Allethrin, Bioallethrin, Bioresmethrin, Cyhalotrin, Cypermethrin, ⁇ -Cypermethrin, ⁇ -Cypermethrin, Deltamethrin, Fenpropathrin, Fenvalerate, s-Fenvalerate, Flucythrinate,
  • Cyfluthrin Cycloprothrin, Tefluthrin, Flufenprox, Silafluofen, Bifenthrin, Fenfluthrin,
  • Benzilic acid esters Brompropylate, Chlorbenzylate, Chlorpropylate.
  • Polvcvclic halogenated hydrocarbons Aldrin, Endosulfan.
  • Strobilurines Kresoxim-methyl, Azoxystrobin (BAS 490F), Methoxyimino- ⁇ 2-[1-(3- trifluoromethyl-phenyl)- ethylideneaminooxymethyl]-phenyl ⁇ -acetic acid methyl ester.
  • Fenpiclonil Fenpropimorph, Fenpropidin, Fludioxonil, Pymetrozine, Pyrifenox, Pyriproxyfen,
  • Preferred pesticides are herbicides, as Propaquizafop, Piperophos and Propanil; fungicides, as Methoxyimino- ⁇ 2-[1-(3-trifluoromethyl-phenyl)- ethylideneaminooxymethyl]- phenyl ⁇ -acetic acid methyl ester, Propiconazole, Cyproconazole, Fluazinam, Metalaxyl or R-
  • Metalaxyl (enantiomer of Metalaxyl), or a mixture thereof; insecticides, as Diazinon; plant growth regulators, as Trinexapac-ethyl.
  • Suitable concentrations in relation to the composition are (% weight per volume of the total composition; 1000 g per liter correspond to 100%) a) of the hydrophobic pesticide or mixture of pesticides: 1 to 99 %, preferably 10 to 90% and 20 to 50%; b) of the organic solvent: 1 to 96%, preferably 10 to 80% and 20 to 70%; c) of the surfactants: 3 to 80%, preferably 10 to 40% and 20 to 30%; wherein of surfactant (1): 2 to 25%, preferably 5 to 20%, surfactant (2): 2 to 40%, preferably 5 to 25%, surfactant (3): 2 to 20%, preferably 5 to 15%; d) of the gelling agent: 0.1 to 10 % preferably 0.5 to 5%.
  • an alkylbenzene sulfonate or its salt preferably dodecylbenzene sulfonate calcium salt in an amount of 1 to 10%, preferably 2 to 4 % by weight in relation to the volume of the composition. It may be advantageous to combine the pesticide or mixture of pesticides with a safener.
  • Another object of the invention is a process for preparing a liquid pesticidal composition as herein described, by intimateley mixing, optionally by warming, until a homogeneous phase is achieved.
  • composition is an aqueous spray mixture.
  • composition of the invention may be diluted with water by simple mixing at ambient temperature in order to get a ready for use spray mixture.
  • This spray mixture may be an aqueous emulsion or a solution or a suspension, depending on the kind of composition.
  • the resulting spray mixtures are stable, i.e. they remain as a homogeneously emulsified phase, as a solution or as a homogeneously distributed suspension on standing without agitation for at least one hour to 12 hours or even more.
  • Preferred concentrations of the spray mixture are 0.1 to 5 %, more preferred 0.5 to 2% pesticide in relation to the spray mixture.
  • Further aspects of the invention include a method of preventing or combatting infestation of plants or animals by pests and regulating plant growth by diluting the composition with water and applying a pesticidally effective amount to the plant, animal or locus as desired.
  • compositions After diluting with water the compositions form an emulsion or, depending on the pesticide, solvent and concentration, a clear solution. Both the emulsions and solutions are stable without agitation for at least one to 12 hours or even more.

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  • 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

A liquid pesticidal composition, which is substantially free of water, comprising a hydrophobic pesticide or mixture of pesticides dissolved in an organic solvent and comprising as surfactants (1) a butanole-ethoxylate/propoxylate-blockcopolymer having 12-30 mol ethoxylate and 16-48 mol propoxylate, in combination with (2) a branched C8-C18 alcohol ethoxylate having 5-10 mol ethoxylate, and/or (3) a tristyrenephenol-ethoxylate having 8-30 mol ethoxylate, or its phosphate or salt thereof. The compositions include also gels having a viscosity of 500 to 20'000 mPas and comprising additionally a gelling agent.

Description

Pesticidal Compositions
The present invention relates to storage stable, liquid, pesticidal compositions, the preparation of such compositions and a method of using such compositions to combat pests or as plant growth regulators.
Alkylphenol ethoxylates, for example nonylphenol ethoxylates, and alkylbenzene sulfonates and its salts, for example dodecylbenzene sulfonate calcium salt, are commonly used and well known surfactants in water-emulsifiable pesticidal compositions.
Some of these surfactants are not entirely satisfactory; in particular with respect to their ecological and toxicological properties.
There is still a need for further water-emulsifiable or water soluble, liquid, homogeneous pesticidal compositions which are storage stable, ecological and toxicological favourable and which have good pesticidal efficacy.
Fatty alcohol ethoxylates, e.g. Cι0-Cι4alcohol ethoxylates (EP-A-400,585) and tristyrenephenol-ethoxylates (EP-A-102,003) have been proposed, both in combination with alkylbenzene sulfonates, as surfactants in water-emulsifiable pesticidal compositions. C1-C10 Alkyl ethoxylate/propoxylate-blockcopolymers and tristyrenephenol-ethoxylates have been disclosed as surfactants in aqueous suspensions (EP-A-261 ,492).
A novel combination of surfactants for water-emulsifiable or water-soluble pesticidal compositions has now been found; the novel compositions are storage stable, easy to apply, ecological and toxicological favourable and have good pesticidal efficacy.
Accordingly, the present invention provides a water-emulsifiable or water-soluble, storage stable, liquid, pesticidal composition, which is substantially free of water, comprising a hydrophobic pesticide or mixture of pesticides dissolved in an organic solvent and comprising as surfactants
(1) a butanole-ethoxylate/propoxylate-blockcopolymer having 12-30 mol ethoxylate and 16-48 mol propoxylate, in combination with
(2) a branched C8-C β alcohol ethoxylate having 5-10 mol ethoxylate, and/or
(3) a tristyrenephenol-ethoxylate having 8-30 mol ethoxylate, or its phosphate or salt thereof. Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, for example sodium, potassium calcium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower aikylamine, for example ethyl-, diethyl-, triethyl- or dimethyl-propylamine, or a mono-, di- or tri-hydroxy-lower aikylamine, for example mono-, di- or tri-ethanolamine.
The compositions also include gels having a viscosity of 500 to 20O00 mPas and comprising additionally a gelling agent.
The compositions according to the invention are stable for at least 12 months at 25°C. They are very well miscible with water, even at higher concentrations.
The surfactants can be combined, depending for example on the kind of pesticide and the preferred solvents, as follows:
(1 ) in combination with (2) and (3); (1) in combination with (2); (1 ) in combination with (3).
The surfactants mentioned above can be prepared by methods known per se; they are also commercially available. Preferred are surfactants, wherein
(1 ) the butanole-ethoxylate/propoxyiate-blockcopolymer has 20-24 mol, preferably 22 mol ethoxylate, and 30-36 mol, most preferably 34 mol propoxylate;
(2) the branched C8-Cιβ alcohol ethoxylate is isotridecanol ethoxylate having 5-10 mol, most preferably 6-8 mol ethoxylate; and
(3) the tristyrenephenol-ethoxylate has 16-18 mol ethoxylate.
The composition of the invention is substantially free of water, i.e. the amount of water is less that 0.5%. Some commercially available materials may contain a small amount of water, which, when more than about 0.1% can be removed for example in a separator.
In another aspect of the invention the composition is a gel with a viscosity of 500 - 20O00 mPas; preferably 800 to 10OOO mPas and particularly 1000-5000 mPas.
The viscosity of the composition can be measured using for example a BROOKFIELD viscosimeter with spindles 1 to 3 at 30 rpm.
In this case the composition additionally has to contain a gelling agent, for example oxypropylated cellulose, precipitated or fused silica (hydrophobizised or non- hydrophobizised), gelatine, polysaccharides, tetramethyl decyne diol, ethoxylated dialkyl phenol, methylated clay, propylene carbonate, hydrogenated castor oil, ethoxylated vegetable oil, sodium benzoate and hexanediol. Preferred gelling agent is oxypropylated cellulose.
Gels are particularly suitable for pesticides packing into water soluble bags or sachets, which quickly dissolve when put into the water.
The organic solvents wherein the pesticide has to be dissolved may be water-immiscible or water miscible or a mixture thereof.
Suitable water-immiscible solvents in which the pesticides may be dissolved are aliphatic and aromatic hydrocarbons such as hexane, cyclohexane, benzene, toluene, xylene, mineral oil or kerosin, mixtures or substituted naphthalenes, mixtures of mono- and polyalkylated aromatics commercially available under the registered trademarks SOLVESSO and SHELLSOL and PETROL SPEZIAL, halogenated hydroarbons such as methylene chloride, chloroform and o-dichlorobenzene; phthalates, such as dibutyl phthalate or dioctyl phthalate; ethers and esters, such as ethylene glycol monomethyl or monoethyl ether, fatty acid esters; lactones such as butyrolactone, ketones, such as cyclohexanone; plant oils such as castor oil, soybean oil, cottonseed oil and possible methyl esters thereof; as well as epoxidised coconut oil or soybean oil. Preferred water-immiscible solvents are aliphatic and aromatic hydrocarbons, fatty acid esters {e.g. WITCONOL 2309), dipropyleneglycol monomethylether (e.g. DOWANOL DPM) and castor oil. Suitable water-miscible solvents in which the pesticides may be dissolved are alcohols and glycols, such as ethanol, ethylene glycol, strongly polar solvents, such as N-methyl-2- pyrrolidone, tetramethylurea, gamma-butyrolacone.dimethyl sulfoxide, N,N- dimethylacetamid and dimethylformamide; preferred are N-methyl-2-pyrrolidone and gamma-butyrolacone.
Suitable pesticides are those which are substantially insoluble in water (hydrophobic), but soluble in the organic solvent.
The term pesticide is understood to encompass herbicides, insecticides, acaricides, nemati- cides, ectoparasiticides, fungicides and plant growth regulators.
With respect to their chemical constitution, these pesticides may belong to a very wide range of compound classes. Examples of compound classes to which the suitable pesticide may belong are: acylalanines, haloacetanilides, triazole derivatives, phosphoric acid esters, pyrethroids, benzilic acid esters, polycyclic halogenated hydrocarbons, diphenyl ether derivates, formamidines, strobilurines, aryloxyphenoxy-alkanoic acid derivatives. Examples of suitable individual compounds of the above mentioned compound classes are listed below. Where known, the common name is used to designate the individual compounds
(q.v. the Pesticide Manual, 10th edition, 1994,British Crop Protection Council).
Haloacetanilides: Dimethachlor, Metolachlor, Pretilachlor, 2-chloro-N-(1-methyl-2-methoxy- ethyl)-acet-2,6-xylidide, Alachlor, Butachlor, Propachlor, Dimethenamid.
Diphenyl ether derivates: Bifenox, 4-(4-Pentyn-1-yloxy)diphenylether, Acifluorfen, Oxyfluor- fen, Fluoroglycofen-ethyl, Fomesafen, cis-trans- (±)2-ethyl-5-(4-phenoxy-phenoxymethy!)-
1 ,3-dioxolane ("diofenolan").
Phenoxypropionic acid derivatives: Fluazifop-butyl, Haloxyf op-methyl, Haloxyfop-(2-ethoxy- ethyl), Fluorotopic, Fenoxapropethyl, Quizalofop-ethyl, Propaquizafop, Diclofop-methyl.
Acylalanines: Furalaxyl, etalaxyl, R- Metalaxyl, Benzoylprop ethyl, Benalaxyl, Oxadixyl,
Flamprop methyl.
Triazole derivatives: Difenoconazole, Etaconazol, Propiconazole, Penconazole,
Triadimefon, Epoxiconazole, Tebuconazole, Bromuconazole, Fenbuconazole,
Cyproconazole.
Phosphoric acid esters: Piperophos, Anilofos, Butamifos, Azamethiphos, Chlorfenvinphos,
Dichlorvos, Diazinon, Methidathion, Azinphos ethyl, Azinphos methyl, Chlorpyrifos, Chlor- thiofos, Crotoxyphos, Cyanophos, Demeton, Dialifos, Dimethoate, Disulfoton, Etrimfos,
Famphur, Flusulfothion, Fluthion, Fonofos, Formothion, Heptenophos, Isofenphos,
Isoxathion, Malathion, Mephospholan, Mevinphos, Naled, Oxydemeton methyl, Oxy- deprofos, Parathion, Phoxim, Pyrimiphos methyl, Profenofos, Propaphos, Propetamphos,
Prothiophos, Quinalphos, Sulprofos, Phemephos, Terbufos, Triazophos, Trichloronate,
Fenamipos, Isazophos, s-benzyl-o,o-diisopropylphosphorothioate, Edinphos, Pyrazophos.
Pyrethroids: Allethrin, Bioallethrin, Bioresmethrin, Cyhalotrin, Cypermethrin, α-Cypermethrin, φ-Cypermethrin, Deltamethrin, Fenpropathrin, Fenvalerate, s-Fenvalerate, Flucythrinate,
Fluvalinate, Permethrin, Pyrethrine, Resmethrin, Tetramethrin, Tralomethrin, Ethophenprox,
Cyfluthrin, Cycloprothrin, Tefluthrin, Flufenprox, Silafluofen, Bifenthrin, Fenfluthrin,
Bromfenprox.
Benzilic acid esters: Brompropylate, Chlorbenzylate, Chlorpropylate.
Polvcvclic halogenated hydrocarbons: Aldrin, Endosulfan.
Strobilurines: Kresoxim-methyl, Azoxystrobin (BAS 490F), Methoxyimino-{2-[1-(3- trifluoromethyl-phenyl)- ethylideneaminooxymethyl]-phenyl}-acetic acid methyl ester.
Miscellaneous: Tridemorph, Bromoxynil, Carboxin, Prochloraz, Propargite, Dicamba,
Fenpiclonil, Fenpropimorph, Fenpropidin, Fludioxonil, Pymetrozine, Pyrifenox, Pyriproxyfen,
Trinexapac-ethyl, Fluazinam.
Preferred pesticides are herbicides, as Propaquizafop, Piperophos and Propanil; fungicides, as Methoxyimino-{2-[1-(3-trifluoromethyl-phenyl)- ethylideneaminooxymethyl]- phenyl}-acetic acid methyl ester, Propiconazole, Cyproconazole, Fluazinam, Metalaxyl or R-
Metalaxyl (enantiomer of Metalaxyl), or a mixture thereof; insecticides, as Diazinon; plant growth regulators, as Trinexapac-ethyl.
Suitable concentrations in relation to the composition are (% weight per volume of the total composition; 1000 g per liter correspond to 100%) a) of the hydrophobic pesticide or mixture of pesticides: 1 to 99 %, preferably 10 to 90% and 20 to 50%; b) of the organic solvent: 1 to 96%, preferably 10 to 80% and 20 to 70%; c) of the surfactants: 3 to 80%, preferably 10 to 40% and 20 to 30%; wherein of surfactant (1): 2 to 25%, preferably 5 to 20%, surfactant (2): 2 to 40%, preferably 5 to 25%, surfactant (3): 2 to 20%, preferably 5 to 15%; d) of the gelling agent: 0.1 to 10 % preferably 0.5 to 5%.
It may be advantageous to add additionally an alkylbenzene sulfonate or its salt, preferably dodecylbenzene sulfonate calcium salt in an amount of 1 to 10%, preferably 2 to 4 % by weight in relation to the volume of the composition. It may be advantageous to combine the pesticide or mixture of pesticides with a safener.
Another object of the invention is a process for preparing a liquid pesticidal composition as herein described, by intimateley mixing, optionally by warming, until a homogeneous phase is achieved.
In another aspect of the invention the composition is an aqueous spray mixture.
Before the application, the composition of the invention may be diluted with water by simple mixing at ambient temperature in order to get a ready for use spray mixture.
This spray mixture may be an aqueous emulsion or a solution or a suspension, depending on the kind of composition. The resulting spray mixtures are stable, i.e. they remain as a homogeneously emulsified phase, as a solution or as a homogeneously distributed suspension on standing without agitation for at least one hour to 12 hours or even more.
Preferred concentrations of the spray mixture are 0.1 to 5 %, more preferred 0.5 to 2% pesticide in relation to the spray mixture.
Further aspects of the invention include a method of preventing or combatting infestation of plants or animals by pests and regulating plant growth by diluting the composition with water and applying a pesticidally effective amount to the plant, animal or locus as desired.
Preparation examples
The following Examples illustrate the invention in more detail. The registered trademarks and other designations denote the following products:
(1 ) WITCONOL NS 500 K® (WITCO) Copolymer of butanol-34 PO/22 EO,
(2) GENAPOL X-080® (HOECHST) lsotridecanol-8 EO GENAPOL X-060® (HOECHST) lsotridecanol-6 EO
(3) SOPROPHOR BSU® (RHONE-P) Tristyrenephenole-16 EO
,®
SOPROPHOR 3D331* (RHONE-P) Tristyrenephenol-poly-EO-phosphate
WITCONOL 2309^ Fatty acid methylester EMULSOGEN EL® castor oil-36 EO PETROL SPEZIAL 200* Mixture of aromatic hydrocarbons KLUCEL M® Oxypropylated cellulose (gelling agent) DOWANOL DPM ® Dipropyleneglycol monomethylether (mixture of isomers) EO = ethyleneoxid PO = propyleneoxid
% in weight per volume of the total composition (i.e.1000 g per liter correspond to 100%) The components are intimateley mixed, optionally by warming, until a homogeneous phase is achieved. ExamD e 1
% component type
10 0 Propaquizafop herbicide
5.0 WITCONOL NS 500 K® surfactant (1)
35.0 GENAPOL X-060® surfactant (2)
10.0 1 -Methyl-2-pyrrolidone solvent
40.0 PETROL SPEZIAL 200 solvent
Density: 1.02 g/cπT
ExamD e 2
% component type
14.5 Piperophos herbicide
25.0 Propanil herbicide
8.0 WITCONOL NS 500 K® surfactant (1 )
12.0 GENAPOL X-060® surfactant (2)
40.5 Dipropyleneqlycol monomethyl ether solvent
Density: 1.065 g/crτr
Exam pie 3
Figure imgf000009_0001
Density: 1.11 g/cm"
Figure imgf000010_0001
Density: 1.07 g/cm
Exam pie 5
Figure imgf000010_0002
Density: 1.095 g/cm3
Figure imgf000010_0003
Density: 1.1 g/cm xam pie 7
Figure imgf000011_0001
Density: 1.073 g/cπr
Exam pie 8
Figure imgf000011_0002
Density: 1.07 g/crrf
Exam pie 9
Figure imgf000011_0003
Density: 1.09 g/cm' Example 10
% component type
15.0 Methoxyimino-{2-[1 -(3-trifluoromethyl-phenyl)- ethylidene- fungicide aminooxvmethyl]-phenyl}-acetic acid methyl ester
7.0 R-Metalaxyl funqicide
12.5 WITCONOL NS 500 K surfactant (1 )
12.5 SOPROPHOR BSU® surfactant (3)
53.0 1 -Methyl-2-pyrrolidone solvent
Density: 1.081 g/crτr
Example 11
% component type
12.5 Methoxyimino-{2-[1 -(3-trifluoromethyl-phenyl)- ethylidene- fungicide aminooxymethγl]-phenyl}-acetic acid methyl ester
7.5 R-Metalaxyl fungicide
3.0 WITCONOL NS 500 K surfactant (1)
3.0 GENAPOL X-080® surfactant (2)
45.5 1 -Methyl-2-pvrrolidone solvent
27.5 Aromatic solvent 230 solvent
Density: 1.081 g/cm3
Example 12
% component type
9.3 R-Metalaxyl fungicide
4.0 WITCONOL NS 500 K surfactant (1 )
16.0 GENAPOL X-080® surfactant (2)
5.0 Gamma-Butyrolactone solvent
27.0 Fatty acid methyl ester Me C 6-10 solvent
Density: 1.035 g/cm ExamD e 13
% component tvpe
17.7 R-Metalaxyl funqicide
26.0q Fluazinam funqicide
5.0 WITCONOL NS 500 K surfactant (1)
5.0 GENAPOL X-060® surfactant (2)
5.0 SOPROPHOR BSU® surfactant (3)
16.0 PETROL SPEZIAL 200® solvent
25.3 Gamma-Butyrolactone solvent
Density: 1.184 g/cm2
Figure imgf000013_0001
Density: 1.073 g/crrf
Examp e 15 (Gel)
% component type
26 Trinexapac-ethyl plant growth regulator
21.0 WITCONOL NS 500 K surfactant (1)
7.0 GENAPOL X-060® surfactant (2)
0.8 KLUCEL M® gelling agent
45.2 DOWANOL DPM ® solvent
Density: 1.027 g/cm3 ; Viscosity: ca. 2700 mPas (Spindle 3 / 30 rpm)
ExamDl e 16
% component type
26.3 Trinexapac-ethyl plant growth requlator
21.4 WITCONOL NS 500 K surfactant (1)
7.1 GENAPOL X-060® surfactant (2)
45.2 WITCONOL 2309® solvent
Density: 0.98 g/cm" All the compositions according to the examples are stable for at least 12 months at 25°C.
After diluting with water the compositions form an emulsion or, depending on the pesticide, solvent and concentration, a clear solution. Both the emulsions and solutions are stable without agitation for at least one to 12 hours or even more.

Claims

Claims
1. A liquid pesticidal composition, which is substantially free of water, comprising a hydrophobic pesticide or mixture of pesticides dissolved in an organic solvent and comprising as surfactants
(1 ) a butanole-ethoxylate/propoxylate-blockcopolymer having 12-30 mol ethoxylate and 16-48 mol propoxylate, in combination with
(2) a branched C8-C18 alcohol ethoxylate having 5-10 mol ethoxylate, and/or
(3) a tristyrenephenol-ethoxylate having 8-30 mol ethoxylate, or its phosphate or salt thereof.
2. A composition according to claim 1 , wherein the butanole-ethoxylate/propoxylate- blockcopolymer (1) has 20-24 mol, preferably 22 mol ethoxylate, and 30-36 mol, preferably 34 mol propoxylate.
3. A composition according to claim 1 , wherein the branched C8-Cι8 alcohol ethoxylate (2) is isotridecanol ethoxylate having 5-10 mol, preferably 6-8 mol ethoxylate.
4. A composition according to claim 1 , wherein the tristyrenephenol-ethoxylate (3) has 16- 18 mol ethoxylate.
5. A composition according to claim 1 which is a gel having a viscosity of 500 to 20O00 mPas and comprising additionally a gelling agent.
6. A composition according to claim 5 having a viscosity of 800 to 10O00 mPas, preferably 1000-5000 mPas.
7. A composition according to claim 6, wherein the gelling agent is selected from the group consisting of oxypropylated cellulose, precipitated or fused silica (hydrophobizised or non- hydrophobizised), gelatine, polysaccharides, tetramethyl decyne diol, ethoxylated dialkyl phenol, methylated clay, propylene carbonate, hydrogenated castor oil, ethoxylated vegetable oil, sodium benzoate and hexanediol.
8. A composition according to claim 7, wherein the gelling agent is oxypropylated cellulose.
9. A composition according to claim 1 , wherein the surfactants are (1) a butanole-ethoxylate/propoxylate-blockcopolymer having 12-30 mol ethoxylate and 16- 48 mol propoxylate, in combination with
(2) a branched C8-Cιβ alcohol ethoxylate having 5-10 mol ethoxylate.
10. A composition according to claim 1 , wherein the surfactants are
(1) a butanole-ethoxylate/propoxylate-blockcopolymer having 12-30 mol ethoxylate and 16- 48 mol propoxylate, in combination with
(3) a tristyrenephenol-ethoxylate having 8-30 mol ethoxylate, or its phosphate or salt thereof.
11. A composition according to claim 1 , wherein the organic solvent is water-immiscible.
12. A composition according to claim 11 , wherein the organic solvent is selected from aliphatic and aromatic hydrocarbons, phthalates, ethers and esters, fatty acid esters, lactones, ketones, castor oil, soybean oil, cottonseed oil and possible methyl esters thereof, and epoxidised coconut oil or soybean oil.
13. A composition according to claim 12, wherein the organic solvent is selected from aliphatic and aromatic hydrocarbons, fatty acid esters, dipropyleneglycol monomethylether and castor oil.
14. A composition according to claim 1 , wherein the organic solvent is water-miscible.
15. A composition according to claim 14, wherein the organic solvent is selected from alcohols, glycols, N-methyl-2-pyrrolidone, tetramethylurea, gamma-butyrolacone, dimethyl sulfoxide N,N-dimethylacetamid and dimethylformamide.
16. A composition according to claim 15, wherein the organic solvent is N-methyl-2- pyrrolidone or gamma-butyrolacone or a mixture thereof.
17. A composition according to claim 1 , wherein the pesticide is a herbicide, preferably Propaquizafop, Piperophos or Propanil.
18. A composition according to claim 1 , wherein the pesticide is a fungicide, preferably Methoxyimino-{2-[1-(3-trifluoromethyl-phenyl)- ethylideneaminooxymethyl]-phenyl}-acetic acid methyl ester, Propiconazole, Cyproconazole, Fluazinam, Metalaxyl or R- Metalaxyl, or a mixture thereof.
19. A composition according to claim 1 , wherein the pesticide is an insecticide, preferably Diazinon.
20. A composition according to claim 1 , wherein the pesticide is a plant growth regulator, preferably Trinexapac-ethyl.
21. A composition according to claim 1, wherein the concentration of the pesticide or mixture of pesticides is 1 to 99 % by weight in relation to the volume of the composition.
22. A composition according to claim 21 , wherein the concentration of the pesticide or mixture of pesticides is 10 to 90%, preferably 20 to 50% in relation to the volume of the composition.
23. A composition according to claim 1 , wherein the concentration of the organic solvent is 1 to 96% by weight in relation to the volume of the composition.
24. A composition according to claim 23, wherein the concentration of the organic solvent is 10 to 80%, preferably 20 to 70% by weight in relation to the volume of the composition.
25. A composition according to claim 1 , wherein the concentration of the surfactants (1), (2) and/or (3) is 3 to 80% by weight in relation to the volume of the composition.
26. A composition according to claim 25, wherein the concentration of the surfactants is 10 to 40%, preferably 20 to 30% by weight in relation to the volume of the composition.
27. A composition according to claim 5, wherein the concentration of the gelling agent is 0.1 to 10 %, preferably 0.5 to 5% by weight in relation to the volume of the composition.
28. A process for preparing a liquid pesticidal composition according to claim 1 by intimateley mixing, optionally by warming, until a homogeneous phase is achieved.
29. An aqueous microemulsion or solution prepared by mixing the composition according to claim 1 with water.
30. A method of preventing or combatting infestation of plants or animals by pests and regulating plant growth by diluting the composition according to claim 1 with water and applying a pesticidally effective amount to the plant, animal or locus.
PCT/EP1997/003195 1996-06-28 1997-06-19 Pesticidal compositions WO1998000009A1 (en)

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US09/202,886 US6071857A (en) 1996-06-28 1997-06-19 Pesticidal compositions
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IL12730897A IL127308A0 (en) 1996-06-28 1997-06-19 Pesticidal compositions
EP97930372A EP0907316A1 (en) 1996-06-28 1997-06-19 Pesticidal compositions
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