CA2311382A1 - Use of narrow range ethoxylates of fatty alcohols in agricultural pesticide and adjuvant formulations - Google Patents
Use of narrow range ethoxylates of fatty alcohols in agricultural pesticide and adjuvant formulations Download PDFInfo
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- CA2311382A1 CA2311382A1 CA002311382A CA2311382A CA2311382A1 CA 2311382 A1 CA2311382 A1 CA 2311382A1 CA 002311382 A CA002311382 A CA 002311382A CA 2311382 A CA2311382 A CA 2311382A CA 2311382 A1 CA2311382 A1 CA 2311382A1
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- 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
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- 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
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- 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
- A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
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Abstract
An adjuvant containing: (a) a narrow range ethoxylate of fatty alcohol; and (b) a component selected from the group consisting of nonoionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty acid dialkyl ethers, fatty acid dialkyl carbonates, vegetable oils, and mixtures thereof.
Description
2 PGTNS98/23252 _ USE OF NARROW RANGE ETHOXYLATES OF FATTY ALCOHOLS IN
AGRICULTURAL PESTICIDE AND ADJUVANT FORMULATIONS
BACKGROUND OF THE INVENTION
The present invention generally relates to the use of narrow range ethoxylates of fatty alcohols as emuls~ers, dispersants, wetting agents and solvents for adjuvant concentrates, pesticide compositions, and aqueous pesticide compositions.
Insecticides, insect repellents, fungicides, bactericides, bacteriostats, herbicides, and plant growth regulators are normally formulated into various products for use on crops, for insect control, weed control and the like.
Alternatively, the products may be formulated as liquids or powders or granules. Solvents, emulsifiers, dispersing agents and wetting agents are normally incorporated into such compositions to ensure the preparation of a uniform pesticide formulation.
These formulation components are also selected to ensure that the pesticide composition will disperse or emulsify evenly in a tank mix at the point of application. They afso have a third purpose which is to ensure optimum delivery of the tank mix preparation to the targeted pest or substrate.
Sometimes these surfactants incorporated in pesticide formulations are not sufficient to fully ensure stable tank mixes when such tank mixes contain multiple components. Similarly, it may be necessary to add adjuvants to the tank mix for full stability. It is widely known that adding adjuvants which contain surfactants to the tank mix will realize the desired stabilization.
Moreover, additional quantities of surfactants have been shown to potentiate pesticidal activity of many pesticide and there are many adjuvant formulations that have been developed for this purpose. Surfactants are nearly always components of these adjuvants ranging from minor components to the sole component.
BRIEF SUMMARY OF THE INVENTION
The present invention is directed to an adjuvant composition containing:
(a) a narrow range ethoxylate of fatty alcohol; and (b) a component selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty dialkyl ethers, fatty dialkyl carbonates, vegetable oils, and mixtures thereof.
The present invention is also directed to a pesticide concentrate containing:
(a) an adjuvant containing:
(i) a narrow range ethoxylate of fatty alcohol; and (ii) a component selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty dialkyl ethers, fatty dialkyl carbonates, vegetable oils, and mixtures thereof; and (b) a biologically-active ingredient.
The present invention is also directed to a process for treating a target substrate involving contacting the target substrate with the above-disclosed pesticide concentrate.
BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING
Not Applicable.
DETAILED DESCRIPTION OF THE INVENTION
Other than in the claims and in the operating examples, or where othec~nrase.indicated,.Jall aumbersExpressing.quant~ies_.o~ingredieats.ac reaction conditions used herein are to be understood as being modified in all instances by the term "about".
WO 99/26472 PCT/US98/23252 _ The term target substrate as used herein means a plant, a plant pest, or a combination of a plant and a plant pest. A plant pest is defined as any living stage of any weed, insects, mites, nematodes, slugs, snails, protozoa, or other invertebrate animals, bacteria, fungi, other parasitic plants or reproductive parts thereof, viruses, or any organisms similar to or allied with any of the foregoing, or any infectious substances which can directly or indirectly injure or cause disease or damage in any plants or parts thereof, or any processed, manufactured, or other products of plants.
The narrow range ethoxylates of fatty alcohols of the present invention can provide a variety of functions in agricultural applications. They can serve as emulsifiers and wetting agents in a variety of pesticide and adjuvant compositions. Specifically, they may be used in emulsifiable concentrates, microemulsions, aqueous flowable and oil-based flowables. They can also be used as emulsifiers in crop oil concentrate adjuvants based on both synthetic and vegetable oils.
Suitable narrow range ethoxylates of fatty alcohols which may be employed in the present invention include, but are not limited to, those derived from Cs C~ fatty alcohols. A more detailed explanation of the types of narrow range ethoxylates that may be employed is found in U.S. Patent No. 5,292,910, the entire contents of which are incorporated herein by reference.
Examples of suitable co-surfactants/solvents include, for example, other nonionic surfactants such as ethoxylated castor oils, alcohol ethoxylates, alkyl polyglycosides, glucamides and the like, anionic surfactants such as fatty alcohol ether sulfates, phosphate esters, sulfonates, and the like, cationic surfactants such as ethoxylated fatty amines, and the like, alkyl esters such as methyl oleate, ethyl canolate, and methyl soyate, phytobland mineral oils, water-soluble silicone surfactants, fatty dialkyl ethers, fatty dialkyl carbonates, vegetable oils such as canola oil, soybean oil and the like, and mixtures thereof, typically employed in adjuvant and pesticide compositions.
The co-surfactant/solvent of the present invention will typically be present in the adjuvant composition in an amount of from about 1 to about 99% by weight, preferably from about 10 to about 95% by weight, and most preferably from about 25 to about 90% by weight, based on the weight of the adjuvant composition.
According to another embodiment of the present invention, there is provided a pesticide concentrate containing a mixture of the above-disclosed adjuvant composition and a biologically active ingredient.
Suitable biologically-active ingredients for use in the pesticide concentrates of the present invention are generally selected from the group consisting of insecticides, insect repellents, fungicides, bactericides, bacteriostats, herbicides, and plant growth regulators, all of which are based on biologically-active ingredients. Suitable insecticides include, for example, O,O-diethyl O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, O,O-diethyl S-2-[(ethylthio)ethyl]phosphorodithioate, O,O-dimethyl O-(3-methyl-4-nitrophenyl)thiophosphate, O,O-dimethyl S-(N-methylcarbamoylmethyl)phosphorodithioate, O,O-dimethyl S-(N-methyl-N-formyicarbamoylmethyl)phosphorodithioate, O,O-dimethyl S-2-[(ethylthio)ethyl]phosphorodithioate, O,O-diethyl S-2-[(ethylthio)ethylJphosphorodithioate, O,O-dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate, O,O-diethyl-O-(5-phenyl-3-isooxazolyl)phosphorothioate, O,O-dimethyi O-(2,5-dichloro-4-bromophenyl)phosphorothioate, O,O-dimethyl-O-)3-methyl-4-methylmercaptophenyl)thiophosphate, O-ethyl O-p-cyanophenyl-O-phenylphosphorothioate, O,O-dimethyl-S-(1,2-dicarboethoxyethyl)phosphorodithioate, 2-chloro-(2,4,5-trichlorophenyl)vinyldimethyl phosphate, 2-chloro-1-(2,4-dichlorophenyl)vinyldimethyi phosphate, O,O-dimethyl O-p-cyanophenyl phosphorothioate, 2,2-dichlorovinyl dimethyl phosphate, O,O-diethyl O-2,4-dichlorophenyl phosphorothioate, ethyl mercaptophenylacetate O,O-dimethyl phosphorodithioate, S-[(6-chloro-2-oxo-3-benzooxazolinyl)methyl]O,O-diethyl phosphorodithioate, 2-chloro-1-(2,4-dichlorophenyl)vinyl diethylphosphate O,O-diethyl WO 99/26472 PCTNS98/23252 _ O-(3-oxo-2-phenyl-2H-pyridazine-6-yl)phosphorothioate, O,O-dimethyl S-(1-methyl-2-ethylsulfinyl)-ethyl phosphorothioate, O,O-dimethyl S-phthalimidomethyl phosphorodithioate, O,O-diethyl 2,2,2-trichioroethanol, 2-(p-tert-butyl-phenoxy)isopropyl-2'-chloroethylsulfite, azoxybenzene, 5 di-(p-chlorophenyl)-cyclopropyl carbinol, di[tri(2,2-dimethyl-2-phenylethyl)tin]oxide, 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea and S-tricyclohexyltin O,O-diisopropylphosphorodithioate; 2-methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime; ethyl [2-(4-phenoxyphenoxy)ethyl] carbamate;
butyl-2,3-dihydro-2,2-dimethylbenzofuran-7-yl N,N'-dimethyl-N,N'-thiodicarbamate; 1-naphthyl methyl carbamate; 2-(ethylthiomethyl)phenyl methylcarbamate; 5-(4-phenoxybutyl)dimethylthiocarbamate;
dimethyl N,N'-(thiobis(methylimino)carbonyloxy)-bis(ethanimidothioate); (RS) a-cyano-3-phenoxybenzyl-(RS)-2-{4-chlorophenyl)-3-methyibutyrate; {RS)-a cyano-3-phenoxyphenyl-(RS)-2,2-dichloro-1-(4 ethoxyphenyl)cyclopropanecarboxylate; (RS)-a-cyano-3-phenoxybenzyl-N-(2-chloro-a,a,a-trifluoro-p-tolyl-D-valinate;
3-phenoxybenzyl-(1 RS)-cis,traps-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanedicarboxylate.
Insect repellents which may be employed include but are not limited to 2-ethyl-1,3-hexanediol; N-octyl bicycloheptene dicarboximide;
N,N-diethyl-M-toluamide; 2,3:4,5-Bis (2-butylene) tetrahydro-2-furaldehyde;
Di-n-propyl isocinchomeronate; and 2-hydroxyethyl-n-octyl sulfide.
Fungicides which may be employed include but are not limited to 3,3'-ethylenebis (tetrahydro-4,6-dimethyl-2H-1,3,5-thiadiazine-2-thione), zinc or manganese ethylenebis(dithiocarbamate), bis-(dimethyldithiocarbamoyl)disulfide, zinc propylenebis (dithiocarbamate), bis(dimethyldithiocarbamoyl) ethylenediamine; nickel dimethyldithiocarbamate, methyl-1 (butylcarbamoyl)-2-benzimidazolecarbamate, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, 1-isopropylcarbamoyl-3-(3,5-dichlorophenyl)hydantoin, potassium WO 99/26472 PGTNS98/Z3252 _ N-hydroxymethyl-N-methyldithiocarbamate and 5-methyl-10-butoxycarbonylamino-10, 11-dehydrodibenzo (b,f)azepine;
pyridine fungicides such as zinc bis(1-hydroxy-2(1 H)pyridinethionate and 2-pyridinethiol-1-oxide sodium salt;
O,O-diisopropyl S-benzylphosphorothioate and O-ethyl S,S-diphenyldithiophosphate; phthalimide fungicides such as N-(2,6-p-diethylphenyl)phthalimide and N-(2,6-diethy!phenyl)-4-methylphthalimide; dicarboxyimide fungicides such as N-trichloromethylthio 4-cyclohexene-1,2-dicarboxyimide and N-tetrachloroethylthin-4-cyclohexene-1,2-dicarboxyimide;
5,6-dihydro-2-methyl-1,4-oxathine-3-carboxanifido-4,4-dioxide and 5,6-dihydro-2-methyl-1, 4-oxathine-3-carboxanilide; naphthoquinone fungicides such as 2,3-dichloro-1,4-naphthoquinone, 2-oxy-3-chloro-1,4-naphthoquinone copper sulfate, pentachloronitrobenzene; 1,4-dichloro-2,5-dimethoxybenzene;
5-methyl-s-triazol-(3,4-b)benzthiazole; 2-(thiocyanomethylthio)benzothiazole;
3-hydroxy-5-methylisooxazole; N-2,3-dichlorophenyltetrachlorophthalamic acid;
5-ethoxy-3-trichloromethyl-1,2,4-thiazole;
2,4-dichloro-6-(0-chloroanilino)-1,3,5-triazine;
2,3-dicyano-1,4-dithioanthraquinone; copper 8-quinolinate; polyoxine;
validamycin; cycloheximide; iron methanearsonate; diisopropyl 1,3-dithiolane-2-iridene malonate; 3-allyloxy-1,2-benzoisothiazol-1,1-dioxide;
kasugamycin; Blasticidin S; 4,5,6,7-tetrachlorophthalide;
3-(3,5-dichlorophenyl)5-ethenyl5-methyloxazoline-2,4-dione;
N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboxyimide;
S-n-butyl-5'-pa ra-t-b utylbenzyl-N-3-pyridyld ith ioca rbonyl i m id ate;
4-chlorophenoxy-3,3-dimethyl-1-(1 H,1,3,4-triazol-1-yl)-2-butanone;
methyl-D,L-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alaninate;
N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazol-1-carboxamide;
N-(3,5-dichiorophenyl)succinamide; tetrachloroisophthalonitrile;
2-d imethyla m i no-4-methyl-5-n-butyl-6-hyd roxypyrim id ine;
WO 99/26472 PCT/US98/23252 _ 2,6-dichloro-4-nitroaniline; 3-methyl-4-chlorobenzthiazol-2-one;
1,2,5,6-tetrahydro-4H-pyrrolol-[3,2,1-i,j]quinoline-2-one;
3'-isopropoxy-2-methylbenzanilide;
1-(2-(2,4-dichiorophenyl)-4-ethyl-1,3-dioxorane-2-ylmethyl]-1 H,1,2,4-triazot;
1,2-benzisothiazoline-3-one; basic copper chloride; basic copper sulfate;
N'-dichlorofluoromethylthio-N,N-dimethyl-N-phenyl sulfamide;
ethyl-N-(3-dimethylaminopropyl)thiocarbamate hydrochloride; piomycin;
S,S-6-methylquinoxaline-2,3-diyldithiocarbonate; complex of zinc and manneb; di-zinc bis(dimethyldithiocarbamate)ethylenebis (dithiocarbamate).
Plant growth regulators which may be employed include but are not limited to N-methoxycarbonyl-N'-4-methylphenylcarbamoylethylisourea and 1-(4-chlorophenylcarbamoyl)-3-ethoxycarbonyl-2-methylisourea; another type of plant growth regulators such as sodium naphthaleneacetate, 1,2-dihydropyridazine-3,6-dione and gibberellins; triazine herbicides such as 2-methylthio-4,6-bisethylamino-1,3,5-triazine, 2-chloro-4,6-bisethylamino-1,3,5 triazine, 2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-s-triazine, 2-methylthio-4,6-bis(isopropylamino)-S-triazine and 2-methylthio-4-ethylamino-6-isopropylamino-s-triazine; phenoxy herbicides such as 2,4-dichlorophenoxyacetic acid and methyl, ethyl, and butyl esters thereof.
2-chloro-4-methylphenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid and ethyl 2-methyl-4.-chlorophenoxybutylate; diphenylether herbicides such as 2,4,6-trichlorophenyl-4'-nitrophenylether,2,4-dichlorophenyl-4'-nitrophenylether and 3,5-dimethylphenyl-4'-nitrophenylether; urea herbicides such as 3-(3,4-dichlorophenyl)-1-methoxy-1-methyl urea, 3-(3,4-dichlorophenyl}-1,1-dimethylurea and 3-(4-chlorophenyl)-1,1-dimethyl urea; carbamate herbicides such as 3-methoxycarbonylaminophenyl-N-(3-methylphenyl)carbamate, WO 99/26472 PCTNS98/23252 _ isopropyl-N-(3-chlorophenyl)carbamate and methyl-N-(3,4'-dichlorophenyl)carbamate; uracil herbicides such as 5-bromo-3-sec-butyl-6-methyluracil and 1-cyclohexyl-3,5-propyleneuracil;
thiolcarbamate herbicides such as S-(4-chlorobenzyl)-N,N-diethylthiolcarbamate,S-ethyl-N-cyclohexyl-N-ethylthiolcarbamate and S-ethyl-hexahydro-1 H-azepine-1-carbothioate and S-ethyl-N,N-di-n-propyl-thiocarbamate; pyridinium herbicides such as 1,1'-di-methyl-4,4'-bispyridinium dichloride; phosphoric herbicides such as N-(phosphonomethyl)glycine; aniline herbicides such as alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine, 4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline and N[3], N[3]-diethyl-2,4-dinitro-6 trifluoromethyl-1,3-phenylene diamine; acid anilide herbicides such as 2-chloro-2',6'-diethyl-N-{butoxymethyl)acetoanilide, 2-chloro-2',6'-diethyl-N-(methoxymethyl)acetoanilide, and 3,4-dichloropropionanilide; pyrazole herbicides such as 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole and 1,3-di-methyl-4-(2,4-dichlorobenzoyl)-5-(p-toluenesulfonyloxy) pyrazole;
5-tert-butyl-3-(2,4-dichloro-5- isopropoxyphenyl)-1,3,4-oxadiazoline-2-one;
2-[N-isopropyl,N-(4-chlorophenyl)carbamoyl]-4-chloro-5-methyl-4 -isooxazoline-3-one; 3-isopropylbenzo-2- thia-1,3-diazinone-(4)-2,4-dioxide and 3-(2-methyl- phenoxy)pyridazine.
According to another embodiment of the present invention, there is thus provided a pesticide concentrate containing: (a) from about 99.9 to about 5% by weight, preferably from about 95 to about 15% by weight, and most preferably from about 90 to about 20% by weight, of the above-disclosed adjuvant; and (b) from about 0.1 to about 95% by weight, preferably from about 5 to about 85% by weight, and most preferably from about 10 to about 80% by weight, of a biologically active ingredient.
The precise amount of biologically active ingredient contained in the pesticide concentrate will oftentimes depend upon the specific end-use application, i.e., the target substrate to be treated, the area to be treated, etc.
Thus, it is within the skill of the applicator to determine the speck amount of WO 99/264'12 PCT/US98/23252 _ biologically active ingredient to be used for a particular application.
In order to formulate the pesticide concentrate into a ready-to-use form, it is typically diluted with water to form an aqueous pesticide composition. The ready-to-use aqueous pesticide composition will typically contain from about 0.1 % to about 10% by weight, and preferably from about 0.5 to about 5% by weight, based on the weight of the composition, of the above-disclosed pesticide concentrate, the remainder of which will typically be water.
The precise amount of dilution of the pesticide concentrate necessary to form a ready-to-use aqueous pesticide composition will again depend upon the specific application itself, i.e., the target substrate to be treated, the area to be treated, etc. Thus, it is once again within the skill of the applicator to determine the specific amount of water needed to dilute the pesticide concentrate.
Finally, the present invention also provides for a process for treating a target substrate involving contacting the target substrate with the above-disclosed aqueous pesticide composition.
AGRICULTURAL PESTICIDE AND ADJUVANT FORMULATIONS
BACKGROUND OF THE INVENTION
The present invention generally relates to the use of narrow range ethoxylates of fatty alcohols as emuls~ers, dispersants, wetting agents and solvents for adjuvant concentrates, pesticide compositions, and aqueous pesticide compositions.
Insecticides, insect repellents, fungicides, bactericides, bacteriostats, herbicides, and plant growth regulators are normally formulated into various products for use on crops, for insect control, weed control and the like.
Alternatively, the products may be formulated as liquids or powders or granules. Solvents, emulsifiers, dispersing agents and wetting agents are normally incorporated into such compositions to ensure the preparation of a uniform pesticide formulation.
These formulation components are also selected to ensure that the pesticide composition will disperse or emulsify evenly in a tank mix at the point of application. They afso have a third purpose which is to ensure optimum delivery of the tank mix preparation to the targeted pest or substrate.
Sometimes these surfactants incorporated in pesticide formulations are not sufficient to fully ensure stable tank mixes when such tank mixes contain multiple components. Similarly, it may be necessary to add adjuvants to the tank mix for full stability. It is widely known that adding adjuvants which contain surfactants to the tank mix will realize the desired stabilization.
Moreover, additional quantities of surfactants have been shown to potentiate pesticidal activity of many pesticide and there are many adjuvant formulations that have been developed for this purpose. Surfactants are nearly always components of these adjuvants ranging from minor components to the sole component.
BRIEF SUMMARY OF THE INVENTION
The present invention is directed to an adjuvant composition containing:
(a) a narrow range ethoxylate of fatty alcohol; and (b) a component selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty dialkyl ethers, fatty dialkyl carbonates, vegetable oils, and mixtures thereof.
The present invention is also directed to a pesticide concentrate containing:
(a) an adjuvant containing:
(i) a narrow range ethoxylate of fatty alcohol; and (ii) a component selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty dialkyl ethers, fatty dialkyl carbonates, vegetable oils, and mixtures thereof; and (b) a biologically-active ingredient.
The present invention is also directed to a process for treating a target substrate involving contacting the target substrate with the above-disclosed pesticide concentrate.
BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING
Not Applicable.
DETAILED DESCRIPTION OF THE INVENTION
Other than in the claims and in the operating examples, or where othec~nrase.indicated,.Jall aumbersExpressing.quant~ies_.o~ingredieats.ac reaction conditions used herein are to be understood as being modified in all instances by the term "about".
WO 99/26472 PCT/US98/23252 _ The term target substrate as used herein means a plant, a plant pest, or a combination of a plant and a plant pest. A plant pest is defined as any living stage of any weed, insects, mites, nematodes, slugs, snails, protozoa, or other invertebrate animals, bacteria, fungi, other parasitic plants or reproductive parts thereof, viruses, or any organisms similar to or allied with any of the foregoing, or any infectious substances which can directly or indirectly injure or cause disease or damage in any plants or parts thereof, or any processed, manufactured, or other products of plants.
The narrow range ethoxylates of fatty alcohols of the present invention can provide a variety of functions in agricultural applications. They can serve as emulsifiers and wetting agents in a variety of pesticide and adjuvant compositions. Specifically, they may be used in emulsifiable concentrates, microemulsions, aqueous flowable and oil-based flowables. They can also be used as emulsifiers in crop oil concentrate adjuvants based on both synthetic and vegetable oils.
Suitable narrow range ethoxylates of fatty alcohols which may be employed in the present invention include, but are not limited to, those derived from Cs C~ fatty alcohols. A more detailed explanation of the types of narrow range ethoxylates that may be employed is found in U.S. Patent No. 5,292,910, the entire contents of which are incorporated herein by reference.
Examples of suitable co-surfactants/solvents include, for example, other nonionic surfactants such as ethoxylated castor oils, alcohol ethoxylates, alkyl polyglycosides, glucamides and the like, anionic surfactants such as fatty alcohol ether sulfates, phosphate esters, sulfonates, and the like, cationic surfactants such as ethoxylated fatty amines, and the like, alkyl esters such as methyl oleate, ethyl canolate, and methyl soyate, phytobland mineral oils, water-soluble silicone surfactants, fatty dialkyl ethers, fatty dialkyl carbonates, vegetable oils such as canola oil, soybean oil and the like, and mixtures thereof, typically employed in adjuvant and pesticide compositions.
The co-surfactant/solvent of the present invention will typically be present in the adjuvant composition in an amount of from about 1 to about 99% by weight, preferably from about 10 to about 95% by weight, and most preferably from about 25 to about 90% by weight, based on the weight of the adjuvant composition.
According to another embodiment of the present invention, there is provided a pesticide concentrate containing a mixture of the above-disclosed adjuvant composition and a biologically active ingredient.
Suitable biologically-active ingredients for use in the pesticide concentrates of the present invention are generally selected from the group consisting of insecticides, insect repellents, fungicides, bactericides, bacteriostats, herbicides, and plant growth regulators, all of which are based on biologically-active ingredients. Suitable insecticides include, for example, O,O-diethyl O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, O,O-diethyl S-2-[(ethylthio)ethyl]phosphorodithioate, O,O-dimethyl O-(3-methyl-4-nitrophenyl)thiophosphate, O,O-dimethyl S-(N-methylcarbamoylmethyl)phosphorodithioate, O,O-dimethyl S-(N-methyl-N-formyicarbamoylmethyl)phosphorodithioate, O,O-dimethyl S-2-[(ethylthio)ethyl]phosphorodithioate, O,O-diethyl S-2-[(ethylthio)ethylJphosphorodithioate, O,O-dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate, O,O-diethyl-O-(5-phenyl-3-isooxazolyl)phosphorothioate, O,O-dimethyi O-(2,5-dichloro-4-bromophenyl)phosphorothioate, O,O-dimethyl-O-)3-methyl-4-methylmercaptophenyl)thiophosphate, O-ethyl O-p-cyanophenyl-O-phenylphosphorothioate, O,O-dimethyl-S-(1,2-dicarboethoxyethyl)phosphorodithioate, 2-chloro-(2,4,5-trichlorophenyl)vinyldimethyl phosphate, 2-chloro-1-(2,4-dichlorophenyl)vinyldimethyi phosphate, O,O-dimethyl O-p-cyanophenyl phosphorothioate, 2,2-dichlorovinyl dimethyl phosphate, O,O-diethyl O-2,4-dichlorophenyl phosphorothioate, ethyl mercaptophenylacetate O,O-dimethyl phosphorodithioate, S-[(6-chloro-2-oxo-3-benzooxazolinyl)methyl]O,O-diethyl phosphorodithioate, 2-chloro-1-(2,4-dichlorophenyl)vinyl diethylphosphate O,O-diethyl WO 99/26472 PCTNS98/23252 _ O-(3-oxo-2-phenyl-2H-pyridazine-6-yl)phosphorothioate, O,O-dimethyl S-(1-methyl-2-ethylsulfinyl)-ethyl phosphorothioate, O,O-dimethyl S-phthalimidomethyl phosphorodithioate, O,O-diethyl 2,2,2-trichioroethanol, 2-(p-tert-butyl-phenoxy)isopropyl-2'-chloroethylsulfite, azoxybenzene, 5 di-(p-chlorophenyl)-cyclopropyl carbinol, di[tri(2,2-dimethyl-2-phenylethyl)tin]oxide, 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea and S-tricyclohexyltin O,O-diisopropylphosphorodithioate; 2-methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime; ethyl [2-(4-phenoxyphenoxy)ethyl] carbamate;
butyl-2,3-dihydro-2,2-dimethylbenzofuran-7-yl N,N'-dimethyl-N,N'-thiodicarbamate; 1-naphthyl methyl carbamate; 2-(ethylthiomethyl)phenyl methylcarbamate; 5-(4-phenoxybutyl)dimethylthiocarbamate;
dimethyl N,N'-(thiobis(methylimino)carbonyloxy)-bis(ethanimidothioate); (RS) a-cyano-3-phenoxybenzyl-(RS)-2-{4-chlorophenyl)-3-methyibutyrate; {RS)-a cyano-3-phenoxyphenyl-(RS)-2,2-dichloro-1-(4 ethoxyphenyl)cyclopropanecarboxylate; (RS)-a-cyano-3-phenoxybenzyl-N-(2-chloro-a,a,a-trifluoro-p-tolyl-D-valinate;
3-phenoxybenzyl-(1 RS)-cis,traps-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanedicarboxylate.
Insect repellents which may be employed include but are not limited to 2-ethyl-1,3-hexanediol; N-octyl bicycloheptene dicarboximide;
N,N-diethyl-M-toluamide; 2,3:4,5-Bis (2-butylene) tetrahydro-2-furaldehyde;
Di-n-propyl isocinchomeronate; and 2-hydroxyethyl-n-octyl sulfide.
Fungicides which may be employed include but are not limited to 3,3'-ethylenebis (tetrahydro-4,6-dimethyl-2H-1,3,5-thiadiazine-2-thione), zinc or manganese ethylenebis(dithiocarbamate), bis-(dimethyldithiocarbamoyl)disulfide, zinc propylenebis (dithiocarbamate), bis(dimethyldithiocarbamoyl) ethylenediamine; nickel dimethyldithiocarbamate, methyl-1 (butylcarbamoyl)-2-benzimidazolecarbamate, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, 1-isopropylcarbamoyl-3-(3,5-dichlorophenyl)hydantoin, potassium WO 99/26472 PGTNS98/Z3252 _ N-hydroxymethyl-N-methyldithiocarbamate and 5-methyl-10-butoxycarbonylamino-10, 11-dehydrodibenzo (b,f)azepine;
pyridine fungicides such as zinc bis(1-hydroxy-2(1 H)pyridinethionate and 2-pyridinethiol-1-oxide sodium salt;
O,O-diisopropyl S-benzylphosphorothioate and O-ethyl S,S-diphenyldithiophosphate; phthalimide fungicides such as N-(2,6-p-diethylphenyl)phthalimide and N-(2,6-diethy!phenyl)-4-methylphthalimide; dicarboxyimide fungicides such as N-trichloromethylthio 4-cyclohexene-1,2-dicarboxyimide and N-tetrachloroethylthin-4-cyclohexene-1,2-dicarboxyimide;
5,6-dihydro-2-methyl-1,4-oxathine-3-carboxanifido-4,4-dioxide and 5,6-dihydro-2-methyl-1, 4-oxathine-3-carboxanilide; naphthoquinone fungicides such as 2,3-dichloro-1,4-naphthoquinone, 2-oxy-3-chloro-1,4-naphthoquinone copper sulfate, pentachloronitrobenzene; 1,4-dichloro-2,5-dimethoxybenzene;
5-methyl-s-triazol-(3,4-b)benzthiazole; 2-(thiocyanomethylthio)benzothiazole;
3-hydroxy-5-methylisooxazole; N-2,3-dichlorophenyltetrachlorophthalamic acid;
5-ethoxy-3-trichloromethyl-1,2,4-thiazole;
2,4-dichloro-6-(0-chloroanilino)-1,3,5-triazine;
2,3-dicyano-1,4-dithioanthraquinone; copper 8-quinolinate; polyoxine;
validamycin; cycloheximide; iron methanearsonate; diisopropyl 1,3-dithiolane-2-iridene malonate; 3-allyloxy-1,2-benzoisothiazol-1,1-dioxide;
kasugamycin; Blasticidin S; 4,5,6,7-tetrachlorophthalide;
3-(3,5-dichlorophenyl)5-ethenyl5-methyloxazoline-2,4-dione;
N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboxyimide;
S-n-butyl-5'-pa ra-t-b utylbenzyl-N-3-pyridyld ith ioca rbonyl i m id ate;
4-chlorophenoxy-3,3-dimethyl-1-(1 H,1,3,4-triazol-1-yl)-2-butanone;
methyl-D,L-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alaninate;
N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazol-1-carboxamide;
N-(3,5-dichiorophenyl)succinamide; tetrachloroisophthalonitrile;
2-d imethyla m i no-4-methyl-5-n-butyl-6-hyd roxypyrim id ine;
WO 99/26472 PCT/US98/23252 _ 2,6-dichloro-4-nitroaniline; 3-methyl-4-chlorobenzthiazol-2-one;
1,2,5,6-tetrahydro-4H-pyrrolol-[3,2,1-i,j]quinoline-2-one;
3'-isopropoxy-2-methylbenzanilide;
1-(2-(2,4-dichiorophenyl)-4-ethyl-1,3-dioxorane-2-ylmethyl]-1 H,1,2,4-triazot;
1,2-benzisothiazoline-3-one; basic copper chloride; basic copper sulfate;
N'-dichlorofluoromethylthio-N,N-dimethyl-N-phenyl sulfamide;
ethyl-N-(3-dimethylaminopropyl)thiocarbamate hydrochloride; piomycin;
S,S-6-methylquinoxaline-2,3-diyldithiocarbonate; complex of zinc and manneb; di-zinc bis(dimethyldithiocarbamate)ethylenebis (dithiocarbamate).
Plant growth regulators which may be employed include but are not limited to N-methoxycarbonyl-N'-4-methylphenylcarbamoylethylisourea and 1-(4-chlorophenylcarbamoyl)-3-ethoxycarbonyl-2-methylisourea; another type of plant growth regulators such as sodium naphthaleneacetate, 1,2-dihydropyridazine-3,6-dione and gibberellins; triazine herbicides such as 2-methylthio-4,6-bisethylamino-1,3,5-triazine, 2-chloro-4,6-bisethylamino-1,3,5 triazine, 2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-s-triazine, 2-methylthio-4,6-bis(isopropylamino)-S-triazine and 2-methylthio-4-ethylamino-6-isopropylamino-s-triazine; phenoxy herbicides such as 2,4-dichlorophenoxyacetic acid and methyl, ethyl, and butyl esters thereof.
2-chloro-4-methylphenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid and ethyl 2-methyl-4.-chlorophenoxybutylate; diphenylether herbicides such as 2,4,6-trichlorophenyl-4'-nitrophenylether,2,4-dichlorophenyl-4'-nitrophenylether and 3,5-dimethylphenyl-4'-nitrophenylether; urea herbicides such as 3-(3,4-dichlorophenyl)-1-methoxy-1-methyl urea, 3-(3,4-dichlorophenyl}-1,1-dimethylurea and 3-(4-chlorophenyl)-1,1-dimethyl urea; carbamate herbicides such as 3-methoxycarbonylaminophenyl-N-(3-methylphenyl)carbamate, WO 99/26472 PCTNS98/23252 _ isopropyl-N-(3-chlorophenyl)carbamate and methyl-N-(3,4'-dichlorophenyl)carbamate; uracil herbicides such as 5-bromo-3-sec-butyl-6-methyluracil and 1-cyclohexyl-3,5-propyleneuracil;
thiolcarbamate herbicides such as S-(4-chlorobenzyl)-N,N-diethylthiolcarbamate,S-ethyl-N-cyclohexyl-N-ethylthiolcarbamate and S-ethyl-hexahydro-1 H-azepine-1-carbothioate and S-ethyl-N,N-di-n-propyl-thiocarbamate; pyridinium herbicides such as 1,1'-di-methyl-4,4'-bispyridinium dichloride; phosphoric herbicides such as N-(phosphonomethyl)glycine; aniline herbicides such as alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine, 4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline and N[3], N[3]-diethyl-2,4-dinitro-6 trifluoromethyl-1,3-phenylene diamine; acid anilide herbicides such as 2-chloro-2',6'-diethyl-N-{butoxymethyl)acetoanilide, 2-chloro-2',6'-diethyl-N-(methoxymethyl)acetoanilide, and 3,4-dichloropropionanilide; pyrazole herbicides such as 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole and 1,3-di-methyl-4-(2,4-dichlorobenzoyl)-5-(p-toluenesulfonyloxy) pyrazole;
5-tert-butyl-3-(2,4-dichloro-5- isopropoxyphenyl)-1,3,4-oxadiazoline-2-one;
2-[N-isopropyl,N-(4-chlorophenyl)carbamoyl]-4-chloro-5-methyl-4 -isooxazoline-3-one; 3-isopropylbenzo-2- thia-1,3-diazinone-(4)-2,4-dioxide and 3-(2-methyl- phenoxy)pyridazine.
According to another embodiment of the present invention, there is thus provided a pesticide concentrate containing: (a) from about 99.9 to about 5% by weight, preferably from about 95 to about 15% by weight, and most preferably from about 90 to about 20% by weight, of the above-disclosed adjuvant; and (b) from about 0.1 to about 95% by weight, preferably from about 5 to about 85% by weight, and most preferably from about 10 to about 80% by weight, of a biologically active ingredient.
The precise amount of biologically active ingredient contained in the pesticide concentrate will oftentimes depend upon the specific end-use application, i.e., the target substrate to be treated, the area to be treated, etc.
Thus, it is within the skill of the applicator to determine the speck amount of WO 99/264'12 PCT/US98/23252 _ biologically active ingredient to be used for a particular application.
In order to formulate the pesticide concentrate into a ready-to-use form, it is typically diluted with water to form an aqueous pesticide composition. The ready-to-use aqueous pesticide composition will typically contain from about 0.1 % to about 10% by weight, and preferably from about 0.5 to about 5% by weight, based on the weight of the composition, of the above-disclosed pesticide concentrate, the remainder of which will typically be water.
The precise amount of dilution of the pesticide concentrate necessary to form a ready-to-use aqueous pesticide composition will again depend upon the specific application itself, i.e., the target substrate to be treated, the area to be treated, etc. Thus, it is once again within the skill of the applicator to determine the specific amount of water needed to dilute the pesticide concentrate.
Finally, the present invention also provides for a process for treating a target substrate involving contacting the target substrate with the above-disclosed aqueous pesticide composition.
Claims (6)
1. A composition comprising:
(a) a narrow range ethoxylate of a fatty alcohol; and (b) a component selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty acid dialkyl ethers, fatty acid dialkyl carbonates, vegetable oils, and mixtures thereof.
(a) a narrow range ethoxylate of a fatty alcohol; and (b) a component selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty acid dialkyl ethers, fatty acid dialkyl carbonates, vegetable oils, and mixtures thereof.
2. The composition of claim 1 wherein component (b) is present in the composition in an amount of from about 1 to about 99% by weight, based on the weight of the composition.
3. A pesticide concentrate comprising:
(a) an adjuvant containing:
(i) a narrow range ethoxylate of a fatty alcohol; and (ii) a component selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty acid dialkyl ethers, fatty acid dialkyl carbonates, vegetable oils, and mixtures thereof; and (b) a biologically active ingredient.
(a) an adjuvant containing:
(i) a narrow range ethoxylate of a fatty alcohol; and (ii) a component selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, alkyl esters, phytobland mineral oils, water soluble silicone surfactants, fatty acid dialkyl ethers, fatty acid dialkyl carbonates, vegetable oils, and mixtures thereof; and (b) a biologically active ingredient.
4. The concentrate of claim 3 wherein the adjuvant is present in the concentrate in an amount of from about 5 to about 99.9% by weight, based on the weight of the concentrate.
5. The concentrate of claim 3 wherein the biologically active ingredient is present in the concentrate in an amount of from about 0.1 to 95% by weight, based on the weight of the concentrate.
6. A process for treating a target substrate comprising contacting the substrate with the concentrate of claim 3.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US6689297P | 1997-11-25 | 1997-11-25 | |
US60/066,892 | 1997-11-25 | ||
US17970198A | 1998-10-27 | 1998-10-27 | |
US09/179,701 | 1998-10-27 | ||
PCT/US1998/023252 WO1999026472A1 (en) | 1997-11-25 | 1998-11-17 | Use of narrow range ethoxylates of fatty alcohols in agricultural pesticide and adjuvant formulations |
Publications (1)
Publication Number | Publication Date |
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CA2311382A1 true CA2311382A1 (en) | 1999-06-03 |
Family
ID=26747271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002311382A Abandoned CA2311382A1 (en) | 1997-11-25 | 1998-11-17 | Use of narrow range ethoxylates of fatty alcohols in agricultural pesticide and adjuvant formulations |
Country Status (11)
Country | Link |
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EP (1) | EP1033911A4 (en) |
JP (1) | JP2001523690A (en) |
KR (1) | KR20010032380A (en) |
AU (1) | AU1373999A (en) |
BR (1) | BR9815109A (en) |
CA (1) | CA2311382A1 (en) |
EA (1) | EA200000573A1 (en) |
PL (1) | PL340691A1 (en) |
SK (1) | SK7802000A3 (en) |
TR (1) | TR200001487T2 (en) |
WO (1) | WO1999026472A1 (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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US6235300B1 (en) | 1999-01-19 | 2001-05-22 | Amway Corporation | Plant protecting adjuvant containing topped or peaked alcohol alkoxylates and conventional alcohol alkoxylates |
AU2000278977A1 (en) * | 2000-11-01 | 2002-05-15 | Kemtek Ltda. | Emulsifiable colloid concentrate compositions |
DE10118076A1 (en) * | 2001-04-11 | 2002-10-17 | Bayer Ag | Using fatty alcohol ethoxylate as penetration enhancer for neonicotinyl insecticide, useful for plant protection, are effective at very low concentration |
GB0121580D0 (en) | 2001-09-06 | 2001-10-24 | Syngenta Ltd | Novel compounds |
GB0318448D0 (en) * | 2003-08-06 | 2003-09-10 | Syngenta Ltd | Formulation |
AR045376A1 (en) * | 2003-08-14 | 2005-10-26 | Basf Ag | USE OF ALCOHOL ALCOXYLATES AS ASSISTANTS FOR BENZAMIDOXIMA DERIVATIVES FUNGICIDES, AGENTS AND CORRESPONDING KITS |
US20060199739A1 (en) * | 2005-03-02 | 2006-09-07 | Olav Messerschmidt | Limonene-containing herbicide compositions, herbicide concentrate formulations and methods for making and using same |
WO2017094676A1 (en) * | 2015-11-30 | 2017-06-08 | クミアイ化学工業株式会社 | Aqueous suspension agrochemical composition |
US10624345B2 (en) * | 2017-08-24 | 2020-04-21 | Valent U.S.A., Llc | Protoporphyrinogen oxidase inhibitor mixtures |
BR112021024061A2 (en) * | 2019-05-31 | 2022-02-08 | Sumitomo Chemical Co | Liquid composition comprising mefentrifluconazole |
US11317629B2 (en) | 2019-05-31 | 2022-05-03 | Sumitomo Chemical Company, Limited | Liquid composition comprising mefentrifluconazole |
CA3171463A1 (en) * | 2020-02-19 | 2021-08-26 | Sasol Chemicals Gmbh | Crop husbandry composition and use thereof |
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HU199234B (en) * | 1987-05-18 | 1990-02-28 | Chinoin Gyogyszer Es Vegyeszet | Microemulsion composition comprising phosphoric acid ester or thiophosphoric acid ester as active ingredient |
AU616438B2 (en) * | 1987-10-27 | 1991-10-31 | Colgate-Palmolive Company, The | Antistatic and fabric softening liquid detergent composition |
GB9110720D0 (en) * | 1991-05-17 | 1991-07-10 | Unilever Plc | Detergent composition |
IL102433A (en) * | 1991-07-24 | 1996-08-04 | Colgate Palmolive Co | Liquid household cleaning composition with insect repellent |
US5651975A (en) * | 1991-09-27 | 1997-07-29 | Harju-Jeanty; Pontus | Method for the preparation of herbicidal granular products comprising two separate phases |
DE4227863A1 (en) * | 1992-08-22 | 1994-02-24 | Henkel Kgaa | Pourable liquid aqueous detergent concentrates |
DE4327327A1 (en) * | 1993-08-13 | 1995-02-16 | Henkel Kgaa | Detergent mixtures |
JP2888643B2 (en) * | 1993-12-17 | 1999-05-10 | モンサント・カンパニー | Surfactants that enhance the efficacy and / or rain resistance of pesticide formulations |
-
1998
- 1998-11-17 TR TR2000/01487T patent/TR200001487T2/en unknown
- 1998-11-17 KR KR1020007005619A patent/KR20010032380A/en not_active Application Discontinuation
- 1998-11-17 BR BR9815109-6A patent/BR9815109A/en not_active Application Discontinuation
- 1998-11-17 PL PL34069198A patent/PL340691A1/en unknown
- 1998-11-17 JP JP2000521693A patent/JP2001523690A/en active Pending
- 1998-11-17 SK SK780-2000A patent/SK7802000A3/en unknown
- 1998-11-17 EA EA200000573A patent/EA200000573A1/en unknown
- 1998-11-17 CA CA002311382A patent/CA2311382A1/en not_active Abandoned
- 1998-11-17 EP EP98957493A patent/EP1033911A4/en not_active Withdrawn
- 1998-11-17 AU AU13739/99A patent/AU1373999A/en not_active Abandoned
- 1998-11-17 WO PCT/US1998/023252 patent/WO1999026472A1/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
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JP2001523690A (en) | 2001-11-27 |
WO1999026472A1 (en) | 1999-06-03 |
AU1373999A (en) | 1999-06-15 |
KR20010032380A (en) | 2001-04-16 |
EP1033911A4 (en) | 2001-04-04 |
EP1033911A1 (en) | 2000-09-13 |
TR200001487T2 (en) | 2000-10-23 |
SK7802000A3 (en) | 2000-11-07 |
EA200000573A1 (en) | 2000-10-30 |
BR9815109A (en) | 2000-10-10 |
PL340691A1 (en) | 2001-02-26 |
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