ZA200509284B - Insecticidal composition - Google Patents

Description

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DESCRIPTION

INSECTICIDAL COMPOSITION

TECHNICAL FIELD

The present invention relates to a water-soluble solution which evenly dissolves in water and exhibites excellent insecticidal activity, and particularly relates to a water-soluble solution containing as its active ingredient a chloronicotinyl compound such as acetamiprid.

BACKGROUND ART

Although emulsions, wettable powders, flowable agents, or the like can be raised among agricultural chemical formulations as examples of formulations that are to be diluted with water before spraying, a method for formulation of a water-soluble agent in which an active ingredient is dissolved in a polar solvent which readily dissolves in water is preferred due to easy handling thereof. As a water-soluble agent containing a chloronicotinyl compound as a bioactive ingredient, Japanese

Laid-Open Patent Application No. Hei 8-92091, for example, discloses a formulation in which a chloronicotinyl insecticide such as imidacloprid is formulated with a solvent such as ethanol, butanol, glycerol, hydrocarbons, polyethylene glycol,

N-methylpyrrolidone, or the like in a concentrated solution which is to be diluted before application, and more specifically discloses a water-soluble concentrated (SL) formulation using imidacloprid with a natural emulsifier based on an alkylaryl polyglycol ether or sodium diisooctyl sulfosuccinate as a surfactant, and dimethyl sulfoxide and isopropanol as polar solvents.

Moreover, Published Japanese Translation No. 2001-50665 of PCT International Publication discloses as a formulation of a compound having insecticidal activity a water-soluble agent using a nonyl phenol ethylene oxide concentrated solution, and a concentrated solution of N-methylpyrrolidone or tristyryl phenol ethylene oxide, 70% W/W solution of calcium dodecylbenzene sulfonate, N-methylpyrrolidone, and Solvesso.

However, the above-mentioned compositions are insufficiently stable at low temperature and have problems with the handling thereof in a state of concentrated solution, and the activity thereof is also insufficient.

DISCLOSURE OF THE INVENTION

The present invention has as its object to provide a water-soluble solution of chloronicotinyl insecticide which puts less burden on the environment and has excellent effects.

As a result of conducting extensive studies to solve the aforementioned problems, the inventors of the present invention found that the aforementioned problems could be solved by using an organic solvent which is a mixed solvent containing dimethyl sulfoxide and either dimethylacetamide or y-butyrolactone, and additionally by combining a particular surfactant, thereby leading to completion of the present invention.

Specifically, the present invention relates to the following:

[1] a liquid insecticidal composition characterized by comprising: (1) a chloronicotinyl compound; (2) a solvent comprsing dimethyl sulfoxide and either dimethylacetamide or y-butyrolactone; and (3) a surfactant;

[2] a liquid insecticidal composition according to [1] characterized in that the surfactant is a castor oil surfactant or a propylene oxide / ethylene oxide block copolymer surfactant;

[3] a liquid insecticidal composition according to [1] or [2] characterized in that the chloronicotinyl compound is acetamiprid;

[4] a liquid insecticidal composition according to any one of

[1] to [3] characterized in that the chloronicotinyl compound (1) is contained in an amount of 1.5 to 40% by weight, the solvent (2) is contained in an amount of 59.9 to 98.4% by weight, and the surfactant (3) is contained in an amount of 0.1 to 10% by weight;

[5] a liquid insecticidal composition according to any one of

[1] to [4] characterized in that the weight ratio of dimethyl sulfoxide to either dimethylacetamide or y-butyrolactone in the solvent is in the range of 10:90 to 90:10; and

[6] a liquid insecticidal composition according to any one of

[1] to [5] characterized in that the solvent comprises 2 to 40% by weight of N-methylpyrrolidone relative to the whole solvent.

The chloronicotinyl compound to be used in the present invention is not particularly limited, provided that it has a chloronicotinyl group or exhibits similar bioactivity, and the following compounds can be specifically raised as examples.

— CH, 7 \ _ 7 / lo] CH7—N__-NH Ci CH—N_ NH,

SA GE

~N

NO, N—NO,

CH, a a Hon SS = CH, cl NO

Sno, 2 » I

OC. H o— crn i A ee

N= S—CH—CH,

N

Neen ~

NO, CH,

C.Hs 7 \ A. TR /

Cl CH;—N.__NH cl CH; ——N NHCH,

CTL TTY

~

CN N—NO,

o—0 Hon S oi Hon s

SAEs SEER Sa

Nen N—NO, ( re o— Hone NH a— Horn N(CH,),

N= hy N=

CH_

NO, CH—NO, cr a—{ Hn NH o— Horn N(CH;), = " \

CH

“No, N——NO, re

Gt MN eo Hcnni—c—on, o— cnn N—CH,

I TTY fa SY

CN ~

NO,

i ro oi H—ctn—g—non, c— NN cH—n N—CH

N= 1 _ 2 Ne” 3

CH_ N I

NC,

Ss NH S HENNA

Y a

CH N N

NO,

NO,

H,C N._ NH S CH —N._ _NH 4

NO,

Among them, acetamiprid is particularly preferable.

The solvent usable in the present invention is a mixed solvent containing dimethyl sulfoxide and at least one selected from the group consisting of dimethylacetamide and y-butyrolactone. Although the mixing ratio thereof is not particularly limited, provided that it is within a range which enables the chloronicotinyl compound to be dissolved, it is specifically preferable that the ratio by weight of dimethyl sulfoxide to at least one selected from the group consisting of dimethylacetamide and y-butyrolactone be in a range of 10:90 to 90:10. Although other solvents such as ethanol, butanol, benzyl alcohol, glycerol, hydrocarbons, propylene glycol, polyethylene glycol, N-methylpyrrolidone, or the like may be optionally added, if needed, N-methylpyrrolidone is preferably used to improve the stability of the chloronicotinyl compound at low temperature. Although the content of

N-methylpyrrolidone is not particularly limited, it is preferably within a range of 2 to 40% by weight of the whole solvent in view of handling convenience.

Specific examples of the surfactant usable in the present invention include ionic or nonionic emulsions, dispersants, wetting agents, and mixtures thereof. Particular examples thereof include salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, condensed polymers of ethylene oxide and fatty alcohol or fatty acid, fatty acid ester, or fatty acid amino, substituted phenols (particularly alkylphenol or arylphenol), sulfosuccinate ester, taurine derivatives (particularly alkyltaurate), phosphoric esters of condensed polymers of alcohol or phenol and ethylene oxide, esters of fatty acid and polyol, sulfates, derivatives having a functional group of sulfonate or phosphate of the above-mentioned compound, and the like. Preferable examples thereof include castor oil surfactants, and propylene oxide / ethylene oxide block copolymer surfactants.

Although the mixing ratio of the chloronicotinyl compound, the solvent and the surfactant in the liquid insecticidal composition of the present invention is not particularly limited, it is specifically preferable that the chloronicotinyl compound be contained in an amount of 1.5 to 40% by weight, the solvent be contained in an amount of 59.9 to 98.4% by weight, and the surfactant be contained in an amount of 0.1 to 10% by weight.

BEST MODE FOR CARRYING OUT THE INVENTION

Although the following provides a specific explanation of effects of the present invention through examples, the present invention is not limited to these examples.

Example 1 g of acetamiprid was dissolved in a mixed solvent containing 37.5 g of dimethylacetamide and 37.5 g of dimethyl sulfoxide, and 5 g of polyoxyethylene castor oil (HLB 11.7) was further dissolved in the mixture as a surfactant to obtain a uniform solution.

Example 2

20 g of acetamiprid was dissolved in a mixed solvent containing 37.5 g of y-butyrolactone and 37.5 g of dimethyl sulfoxide, and 5 g of polyoxyethylene hydrogenated castor oil (HLB 10.8) was further dissolved in the mixture as a surfactant to obtain a uniform solution.

Example 3 20 g of acetamiprid was dissolved in a mixed solvent containing 37.5 g of y-butyrolactone and 41.5 g of dimethyl sulfoxide, and 1 g of PO/EO block copolymer (HLB 12 to 18: manufactured by BASF under the name of Pluronic PE 6400) was further dissolved in the mixture as a surfactant to obtain a uniform solution.

Example 4 20 g of imidacloprid was dissolved in a mixed solvent containing 37.5 g of dimethylacetamide and 37.5 g of dimethyl sulfoxide, and 5 g of polyoxyethylene castor oil was further dissolved in the mixture as a surfactant to obtain a uniform solution.

Example 5 20 g of acetamiprid was dissolved in a mixed solvent containing 27.5 g of dimethylacetamide, 37.5 g of dimethyl

Claims (6)

1. A liquid insecticidal composition comprising: (1) a chloronicotinyl compound; (2) a solvent comprising dimethyl sulfoxide and either dimethylacetamide or y-butyrolactone; and (3) a surfactant.

2. A liquid insecticidal composition according to claim 1, wherein the surfactant is a castor oil surfactant or a propylene oxide / ethylene oxide block copolymer surfactant.

3. A liquid insecticidal composition according to claim 1 or 2, wherein the chloronicotinyl compound is acetamiprid.

4. A liquid insecticidal composition according to any one of claims 1 to 3, wherein the chloronicotinyl compound (1) is contained in an amount of 1.5 to 40% by weight, the solvent (2) is contained in an amount of 59.9 to 98.4% by weight, and the surfactant (3) is contained in an amount of 0.1 to 10% by weight.

5. A liquid insecticidal composition according to any one of claims 1 to 4, wherein the ratio of dimethyl sulfoxide to either dimethylacetamide or y-butyrolactone in the solvent is in a range of 10:90 to 90:10.

6. A liquid insecticidal composition according to any one of claims 1 to 5, wherein the solvent comprises 2 to 40% by weight of N-methylpyrrolidone relative to the whole solvent.