Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Biocides; animal or insect repellents or attractants
Reexamination Certificate
1997-10-30
2001-10-02
Levy, Neil S. (Department: 1616)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Biocides; animal or insect repellents or attractants
C514S113000, C514S345000, C514S531000
Reexamination Certificate
active
06296864
ABSTRACT:
The present invention relates to a pesticidal composition, in particular, a slightly irritant pesticidal emulsifiable concentrate which shows good emulsion stability when diluted with water.
A compound as a pesticidally active ingredient is usually used after being formulated into any of various conveniently usable forms. One of conventional formulations of a lipophilic compound used as a pesticidally active ingredient is an emulsifiable concentrate.
A pesticidal emulsifiable concentrate is usually composed of a lipophilic compound as a pesticidally active ingredient, a surfactant and an organic solvent and is used after being diluted with water. In order to enhance the emulsion stability of an emulsion obtained by dilution with water and reduce toxicity to human beings and animals and phytotoxicity to crops, depending on the kind of the compound as a pesticidally active ingredient, choice of the surfactant, choice of the organic solvent and their combination can be made variously.
The present invention was attained in order to provide a pesticidal composition which shows a good emulsion stability when diluted with water and is only slightly irritant.
The present invention provides a pesticidal composition comprising (a) 1 to 50% by weight of a lipophilic compound as a pesticidally active ingredient, (b) 0.1 to 10% by weight of at least one nonionic surfactant, (c) 0.3 to 4% by weight of at least one anionic surfactant selected from the group consisting of alkylarylsulfonic acid salts and alkylbiphenylsulfonic acid salts, (d) 15 to 40% by weight of a fatty acid ester represented by the formula:
RCOOR′ [1]
wherein R is an alkyl group having 2 to 21 carbon atoms or an alkenyl group having 2 to 21 carbon atoms, and R′ is an alkyl group having 1 to 6 carbon atoms, and (e) 20 to 80% by weight of an aromatic hydrocarbon solvent.
The pesticidal composition of the present invention shows a good emulsion stability when diluted with water. Furthermore, the pesticidal composition of the present invention is good also in low-temperature storage stability and is only slightly irritant.
The compound used in the present invention as a pesticidally active ingredient is not particularly limited so long as it is lipophilic and soluble in aromatic hydrocarbon solvents. The compound includes, for example, insecticides and insect growth regulators. Preferable examples thereof are Pyriproxyfen [4-phenoxy-phenyl 2-(2-pyridyloxy)propyl ether] and compounds represented by the formula:
wherein R
1
is a group represented by the formula:
[wherein X and Y, which may be the same or different, are methyl groups, trifluoromethyl groups, halogen atoms (e.g. fluorine, chlorine, bromine, iodine) or alkoxycarbonyl groups whose alkoxy group has 1 to 4 carbon atoms, and Z is a halogen atom (e.g. fluorine, chlorine, bromine, iodine) or a difluoromethoxy group], R
2
is a hydrogen atom or a cyano group, and R
3
is a hydrogen atom or a fluorine atom.
Specific examples of the compounds [2] are pyrethroid compounds such as Fenvalerate [&agr;-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate], Esfenvalerate [(S)-&agr;-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate], Fenpropathrine [&agr;-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], Permethrin [3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Cypermethrin [&agr;-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], d-Phenothrin [3-phenoxybenzyl (1R)-chrysanthemate], Cyphenothrin [&agr;-cyano-3-phenoxybenzyl (1R)-chrysanthemate], Cyhalothrin [&agr;-cyano-3-phenoxybenzyl (Z)-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate], Cyfluthrin [&agr;-cyano-4-fluoro-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Flucythrinate [&agr;-cyano-3-phenoxybenzyl (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyrate], etc.
In addition to these compounds, pyrethroid compounds such as Tralomethrin [(S)-&agr;-cyano-3-phenoxy-benzyl 2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclo-propanecarboxylate], Allethrin [3-allyl-2-methyl-4-oxo-2-cyclopentenyl crysanthemate], Cycloprothrin [&agr;-cyano-3-phenoxybenzyl 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], Fluvalinate [&agr;-cyano-3-phenoxybenzyl N-(2-chloro-&agr;,&agr;,&agr;-trifluoro-p-tolyl)valinate], Ethofenprox [2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether], etc.; organophosphorus compounds such as Fenitrothion, Cyanophos, Fenthion, Diazinon, etc.; and carbamate compounds such as Fenobucarb, Alanycarb, Carbosulfan, etc. are also preferable as the compound used as a pesticidally active ingredient in the pesticidal composition of the present invention.
The compound as a pesticidally active ingredient is contained in the pesticidal composition of the present invention in an amount of usually 1 to 50% by weight, preferably 1 to 30% by weight.
The surfactants used in the present invention are both the nonionic surfactant(s) and the anionic surfactant(s). As the nonionic surfactant(s), there are preferably used one or more nonionic surfactants selected from the group consisting of polyoxyethylene polyoxypropylene block polymers, polyoxyethylene polyoxypropylene alkyl aryl ethers, polyoxyethylene polyoxypropylene alkyl ethers, polyoxyethylene polyoxypropylene polyaryl ethers, and fatty acid esters of polyoxyethylene polyoxypropylene block polymers. As the anionic surfactant(s), there are used one or more anionic surfactants selected from the group consisting of alkylarylsulfonic acid salts and alkylbiphenylsulfonic acid salts.
Of the above-exemplified nonionic surfactants, those having a molecular weight of approximately 500-3,000 are preferable. More preferable are polyoxyethylene polyoxypropylene block polymers having a HLB of 10 to 14, polyoxyethylene polyoxypropylene alkyl aryl ethers (e.g. polyoxyethylene polyoxypropylene nonyl phenol ethers) having a HLB of 9 to 14, polyoxyethylene polyoxypropylene alkyl ethers (e.g. polyoxyethylene polyoxypropylene octyl ethers) having a HLB of 9 to 12, polyoxyethylene polyoxypropylene polyaryl ethers (e.g. tristyrylphenyl ethers of polyoxyethylene polyoxypropylenes, and distyrylphenyl ethers of polyoxyethylene polyoxypropylenes) having a HLB of 9 to 14, and fatty acid esters of polyoxyethylene polyoxypropylene block polymers (e.g. stearic acid esters of polyoxyethylene polyoxypropylene block polymers) having a HLB of 9 to 13.
It is also preferable to use other nonionic surfactants in combination with the above-exemplified nonionic surfactants. The other nonionic surfactants include polyoxyethylene alkylphenyl ethers, polyoxyethylene vegetable oils, polyoxyethylene hardened vegetable oils, polyoxyethylene tristyrylphenyl ethers, polyoxyethylene alkyl aryl ether polymers, polyoxyethylene fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene distyrylphenyl ether polymers, polyoxyethylene tristyrylphenylphosphate diesters, polyoxyalkylphenol ethers, fatty acid alcohol polyglycol ethers, glycerol fatty acid esters, etc.
The nonionic surfactant(s) is contained in the pesticidal composition of the present invention in an amount of usually 0.1 to 10% by weight, preferably 0.4 to 7% by weight.
The anionic surfactant(s) used in the present invention is at least one alkylarylsulfonic acid salt and/or at least one alkylbiphenylsulfonic acid salt. Although the alkyl group of the alkylarylsulfonic acid salt is not particularly limited so long as the alkylarylsulfonic acid salt has surface activity, it is usually an alkyl group having approximately 8-15 carbon atoms. The salt thereof is also not particularly limited so long as the alkylarylsulfonic acid salt has surface activity. Examples of the salt are alkaline earth metal salts such as calcium salt, magnesium salt, etc., and amine salts. The alkylarylsulfonic acid salts include alkyl
Levy Neil S.
Sughrue Mion Zinn Macpeak & Seas, PLLC
Sumitomo Chemical Company Limited
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