The present invention relates to an emulsifiable agrochemical composition
having high emulsion stability.
BACKGROUND ART
[0002] A patticular isoxazoline-substituted benzamide compound is known to
have control activity against pests (insects, mites, crustaceans, and nematodes, for
15 example) in the agricultural and horticultural field or the animal husbandry and sanitary
field (see Patent Document 1).
A liquid agrochemical composition containing the compound, a surfactant, an ester
solvent corresponding to a polar solvent, and water as needed is also known (see Patent
Document 2).
20 Prior Art Documents
Patent Documents
25
[0003]
Patent Document 1: WO 2007/026965 Pamphlet
PatentDocument2: WO 2009/031621 Pamphlet
SUMMARY OF THE INVENTION
Problem to be Solved by Invention
[0004] An object of the present invention is to provide an emulsifiable
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2
agrochemical composition containing an isoxazoline-substituted benzamide compound
and having an excellent effect to control pests.
Solution to Problem
[0005] The inventors of the present invention conducted intensive research and,
5 as a result, found that, by adjusting the content of a polar solvent to fall within a specific
range, the emulsion stability is improved in the following emulsifiable agrochemical
composition containing an isoxazoline-substituted benzamide compound as an active
agrochemical component.
In other words, the present invention relates to emulsifiable agrochemical
10 compositions according to [I] to [22] below (hereinafter, each of them is also called a
composition of the present invention).
[1] An emulsifiable agrochemical composition including
(Z)-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yi]-N-(methoxyimi
nomethyl)-2-methylbenzoic acid amide (hereinafter, abbreviated as a compound A), a
15 polar solvent, a nonpolar solvent, and a surfactant.
[2] The emulsifiable agrochemical composition according to [1] in which the
content of the polar solvent is 7.5 to 67.5% by mass relative to the mass of the
emulsifiable agrochemical composition.
[3] The emulsifiable agrochemical composition according to [1] or [2] in
20 which the polar solvent is at least one or more selected from the group consisting of a
ketone, a N-alkylpyrrolidone, a cyclic urea, a carboxylic acid amide, a lactone, a
nitrogen-containirig aromatic compound, a cyclic amine, dimethyl sulfoxide, and a
carbonic acid ester.
[ 4] The emulsifiable agrochemical composition according to [I] or [2] in
25 which the polar solvent is at least one or more selected from the group consisting of a 5-
to ?-membered cyclic ketone, a N-C1-12 alkylpyrrolidone, a 5- or 6-membered cyclic urea,
a CJ.12 carboxylic acid amide, a 4- to ?-membered cyclic lactone, a 5- or 6-membered
cyclic aromatic compound containing one or more nitrogen atoms, a 5- or 6-membered
saturated cyclic amine containing one or more nitrogen atoms, dimethyl sulfoxide, and a
5
3
c2-4 alkylene carbonate.
[5] The emulsifiable agrochemical composition according to [4] in which the
5- or 6-membered saturated cyclic amine containing one or more nitrogen atoms is a
4-acylmorpholine.
[6] The emulsifiable agrochemical composition according to [I] or [2] in
which the polar solvent is at least one or more selected from the group consisting of
cyclohexanone, N-methyl-pyrrolidone, N-ethyl-2-pyrrolidone,
I ,3-dimethyl-2-imidazolidinone, N,N'-dimethylpropylene urea, N ,N-dimethylfonnamide,
N,N-dimethylacetamide, s-caprolactone, 1-methylimidazole, 4-acetylmorpholine,
10 4-formylmorpholine, dimethyl sulfoxide, and propylene carbonate.
[7] The emulsifiable agrochemical composition according to [I] in which the
polar solvent is cyclohexanone and the content of the polar solvent is 22.5 to 67.5% by
mass relative to the mass of the emulsifiable agrochemical composition.
[8] The emulsifiable agrochemical composition according to [I] in which the
15 polar solvent is N-methyl-2-pyrrolidone and the content of the polar solvent is 7.5 to
62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
[9] The emulsifiable agrochemical composition according to [I] in which the
polar solvent is N-ethyl-2-pyrrolidone and the content of the polar solvent is 7.5 to 62.5%
by mass relative to the mass of the emulsifiable agrochemical composition.
20 [I 0] The emulsifiable agrochemical composition according to [I] in which the
polar solvent is 1,3-dimethyl-2-imidazolidinone and the content of the polar solvent is 7.5
to 62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
[11] The emulsifiable agrochemical composition according to [1] in which the
polar solvent is N,N'-dimethylpropylene urea and the content of the polar solvent is 7.5 to
25 62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
[12] The emulsifiable agrochemical composition according to [I] in which the
polar solvent is N,N-dimethylformamide and the content of the polar solvent is 12.5 to
62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
[13] The emulsifiable agrochemical composition according to [1] in which the
4
polar solvent is N,N-dimethylacetamide and the content of the polar solvent is 7.S to
62.S% by mass relative to the mass of the emulsifiable agrochemical composition.
[14] The emulsifiable agrochemical composition according to [I] in which the
polar solvent is s-caprolactone and the content of the polar solvent is 42.S to S7.S% by
S mass relative to the mass of the emulsifiable agrochemical composition.
[IS] The emulsifiable agrochemical composition according to [I] in which the
polar solvent is 1-methylimidazole and the content of the polar solvent is 17.S to 62.5%
by mass relative to the mass of the emulsifiable agrochemical composition.
[16] The emulsifiable agrochemical composition according to [I] in which the
I 0 polar solvent is 4-acetylmorpholine and the content of the polar solvent is 22.S to 62.S%
by mass relative to the mass of the emulsifiable agrochemical composition.
[17] The emulsifiable agrochemical composition according to [I] in which the
polar solvent is 4-fmmylmorpholine and the content of the polar solvent is 12.S to 67.S%
by mass relative to the mass of the emulsifiable agrochemical composition.
IS [18] The emulsifiable agrochemical composition according to [I] in which the
20
2S
polar solvent is dimethyl sulfoxide and the content of the polar solvent is 17.5 to 67.S%
by mass relative to the mass of the emulsifiable agrochemical composition.
[19] The emulsifiable agrochemical composition according to any one of[!] to
(18] in which the nonpolar solvent is an aromatic hydrocarbon.
[20] The emulsifiable agrochemical composition according to any one of [I] to
[19] in which the surfactant is one or more selected from the group consisting of a
polyoxyalkylene arylphenyl ether, a polyoxyalkylene aryl phenyl ether formalin
condensate, a polyoxyalkylene vegetable oil, and a polyoxyethylene polyoxypropylene
block copolymer.
[21] The emulsifiable agrochemical composition according to [20] in which the
surfactant is at least one or more selected from the group consisting of a polyoxyalkylene
aryl phenyl ether and a polyoxyalkylene vegetable oil.
[22] The emulsifiable agrochemical composition according to [20] in which the
surfactant is at least one or more selected from the group consisting of polyoxyethylene
""
5
monostyrylphenyl ether, polyoxyethylene distyrylphenyl ether, polyoxyethylene
tristyrylphenyl ether, polyoxyethylene castor oil ether, and polyoxyethylene hydrogenated
castor oil ether.
Effects of the Invention
5 [0006] The composition of the present invention has an excellent effect to control
pests in the agricultural and hotiicultural field or the animal husbandry and sanitary field.
When the content of the polar solvent in the composition of the present invention is 7.5 to
67.5% by mass, the composition of the present invention is transparent, clear, and
uniform and the liquid prepared by diluting the composition of the present invention with
10 water has high emulsion stability.
MODES FOR CARRYING OUT THE INVENTION
[0007] An emulsifiable agrochemical composition of the present invention is
15 usually a solution or a suspension itself and, when diluted with water, becomes a fine
liquid drop and emulsified in watet:
The content of the compound A in the composition of the present invention is
usually 0.05 to 25% by mass. The lower limit of the content is preferably 0.1% by mass
or more, 1% by mass or more, 3% by mass or more, 4% by mass or more, or 5% by mass
20 or more. The upper limit of the content is preferably 20% by mass or less or 15% by
mass or less.
[0008] The composition of the present invention can further contain, in addition
to the compound A, an active agrochemical component, in patiicular, a microbicide, a
bactericide, a nematicide, a miticide, or an insecticide. The common names of specific
25 microbicides, bactericides, nematicides, miticides, and insecticides that can be further
contained are exemplified below.
Microbicedes: amisulbrom, acibenzolar, ampropyfos, anilazine, azaconazole,
azoxystrobin, benalaxyl, benodanil, benomyl, benzamacri!, binapacryl, biphenyl,
bitetianol, bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate,
---------------------
6
buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, carpropamid,
carbendazim, carboxin, chinomethionat, chlobenthiazone, chlorfenazol, chloroneb,
chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram,
debacarb, dichlorophen, diclobutrazol, dichlofluanid, diclomezine, dicloran,
5 diethofencarb, diclocymet, difenoconazole, diflumetorim, dimethirimol, dimethommph,
diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos,
dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole,
ethirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenfuram, fenpiclonil,
fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, flnazinam, fludioxonil,
10 fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet,
fosetyl-aluminium, fuberidazole, furalaxyl, fenamidone, fenhexamid, guazatine,
hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadine,
ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, isopyrazam, kasugamycin,
kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,
15 metconazole, metiram, metominostrobin, myclobutanil, nabam, nickel
bis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, octhilinone, ofurace,
oxadixyl, oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole, pencycuron,
phthalide, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb
hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
20 quinoxyfen, quintozene, sulfur, spiroxamine, tebuconazole, tecnazene, tetraconazole,
thiabendazole, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid,
triadimefon, toriadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, triforine,
triticonazole, validamycin, vinclozolin, zineb, ziram, and oxine-copper.
[0009] Bactericides: streptomycin, oxytetracycline, and oxolinic acid.
25 Nematicides: aldoxycarb, fosthiazate, fosthietan, oxamyl, and fenamiphos.
Miticides: amitraz, bromopropylate, chinomethionat, chlorobenzilate, clofentezine,
cyenopyrafen, cyhexatine, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide,
fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, propargite,
pyridaben, pyrimidifen, and tebufenpyrad.
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7
Insecticides: abamectin, acephate, acetamipirid, azinphos-methyl, bendiocarb,
benfuracarb, bensultap, bifenthrin, buprofezin, butocarboxim, carbaryl, carbofuran,
carbosulfan, cm·tap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, chlorfenvinphos,
chlorfluazuron, clothianidin, chromafenozide, chlorpyrifos-methyl, cyantraniliprole,
5 cyflutlu·in, beta-cyflutlu·in, cypermethrin, cyromazine, cyhalothrin, lambda-cyhalothrin,
deltametlu·in, diafenthiuron, diazinon, diacloden, diflubenzuron, dimethylvinphos,
diofenolan, disulfoton, dimethoate, EPN, esfenvalerate, ethiofencarb, ethiprole,
etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb, fenpropathrin, fenvalerate,
fipronil, flubendiamide, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos,
10 fonnetanate, formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon,
imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion,
metaldehyde, methamidophos, methidathion, methacrifos, metalcarb, methomyl,
methoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nitenpyram,
omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permetlu·in,
15 phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb,
pirimiphos-methyl, profenofos, pymetrozine, pyraclofos, pyriproxyfen, rotenone,
sulprofos, silafluofen, spinosad, sulfotep, sulfoxaflor, tebfenozide, teflubenzuron,
tefluthorin, terbufos, tetrachlorvinphos, thiodicarb, thiamethoxam, thiofanox, thiometon,
tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, and vamidothion.
20 The active agrochemical component other than the compound A may be used singly
or as a mixture of two or more of these. The total content of the active agrochemical
component other than the compound A in the composition of the present invention is
usually 0.05 to 25% by mass. The lower limit of the total content is preferably 0.1% by
mass or more or I% by mass or more. The upper limit of the total content is more
25 preferably 20% by mass or less or 15% by mass or less.
[0010] The polar solvent used in the composition of the present invention is not
patticularly limited, and the water solubility thereof at 20°C is usually I giL or more,
preferably 2 giL or more, and more preferably 4 giL or more. Examples of the polar
solvent include ketones, N-alkylpynolidones, cyclic ureas, carboxylic acid amides,
-------------------
8
lactones, nitrogen-containing aromatic compounds, cyclic amines, dimethyl sulfoxide,
and carbonic acid esters. The polar solvent may be used singly or as a mixture of two or
more of these. The total content of the polar solvent in the composition of the present
invention needs to be 7.5% by mass or more so as to dissolve the compound A. When
5 the content is too high, however, crystals may be deposited in the diluted liquid. From
the viewpoint of preventing crystal deposition, the total content of the polar solvent needs
to be 67.5% by mass or less. Therefore, the total content of the polar solvent is 7.5 to
67.5% by mass.
[0011] Examples of the ketones include C3.9 chain ketones such as acetone,
10 methyl ethyl ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl isobutyl
ketone, methyl-n-amyl ketone, methyl-n-hexyl ketone, methyl-n-heptyl ketone, diethyl
ketone, ethyl-n-butyl ketone, di-n-propyl ketone, diisopropyl ketone, diisobutyl ketone,
diacetone alcohol, acetylacetone, acetonylacetone, mesityl oxide, acetophenone, and
phorone; and 5- to 7 -membered cyclic ketones such as cyclopentanone, cyclohexanone,
15 methyl cyclohexanone, cycloheptanone, and isophorone.
[0012] Examples of the N-alkylpyrrolidones include N-C1-12
alkyl-2-pytmlidones such as N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone,
N-octyl-2-pyrrolidone, and N-dodecyl-2-pyrrolidone.
Examples of the cyclic ureas include 5- or 6-membered cyclic ureas such as
20 1,3-dimethyl-2-imidazolidinone and N,N'-dimethylpropylene urea.
Examples of the carboxylic acid amides include C1-12 carboxylic acid amides (the
number of carbon atoms in the carboxylic acid is preferably I to 12, and the carboxylic
acid is preferably an aliphatic carboxylic acid) such as N,N-dimethylfonnamide,
N,N-dimethylacetamide, N,N-dimethyllactamide, N,N-dimethyloctanamide,
25 N,N-dimethyldecanamide, and N,N-dimethyldodecanamide.
Examples of the lactones include 4- to 7 -membered cyclic lactones such as
~-propiolactone, ~-butyrolactone, y-butyrolactone, y-valerolactone, o-valerolactone,
y-caprolactone, o-caprolactone, s-caprolactone, y-enantholactone, y-octanolactone, and
o-octanolactone.
I
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9
[0013] Examples of the nitrogen-containing aromatic compounds include 5- or
6-membered cyclic aromatic compounds containing one or more nitrogen atoms, such as
pyrrole, !-methyl pyrrole, 3-methyl pyrrole, !-ethyl pyrrole, 2-ethyl pyrrole, 2,4-dimethyl
pyrrole, 2,5-dimethyl pyrrole, 1-methylpyrazole, 3-methylpyrazole, 1-methylimidazole,
5 1-ethylimidazole, 1-isopropylimidazole, pyridine, 2-methylpyridine, 3-methylpyridine,
4-methylpyridine, 2-ethylpyridine, 3-ethylpyridine, 4-ethylpyridine, 2,3-dimethylpyridine,
2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 3,4-dimethylpyridine,
3,5-dimethylpyridine, 2-fonnylpyridine, 3-formylpyridine, 4-formylpyridine,
2-acetylpyridine, 3-acetylpyridine, 4-acetylpyridine, pyridazine, 3-methylpyridazine,
10 4-methylpyridazine, pyrimidine, 4-methylpyrimidine, 2-methylpyrazine,
2,3-dimethylpyrazine, 2,5-dimethylpyrazine, and 2-ethylpyrazine.
[0014] Examples of the cyclic amines include 5- or 6-membered saturated cyclic
amines containing one or more nitrogen atoms, such as pyrrolidine, l-methy1pynolidine,
1-ethylpyrrolidine, 1-acetylpyrrolidine, piperidine, 1-methylpiperidine,
15 2,6-dimethylpiperidine, 3,5-dimethylpiperidine, 1-ethylpiperidine, 1-formylpiperidine,
1-acetylpiperidine, morpholine, 4-methylmorpholine, 2,6-dimethylmorpholine,
4-ethylmorpholine, 4-acylmorpholines (such as 4-formylmorpholine, 4-acetylmorpholine,
4-propionylmorpholine, 4-butanoylmorpholine, 4-pentanoylmorpholine,
4-hexanoylmorpholine, 4-heptanoylmorpholine, 4-octanoylmorpholine,
20 4-nonanoylmorpholine, 4-decanoylmorpholine, 4-undecanoylmorpholine, and
4-dodecanoylmorpholine ), 1-methylpiperazine, 1 ,4-dimethylpiperazine, 1-ethylpiperazine,
and 1-formylpiperazine.
Examples of the carbonic acid esters include C2.4 alkylene carbonates such as
ethylene carbonate, propylene carbonate, I ,2-butylene carbonate, and trimethylene
25 carbonate.
[0015] The nonpolar solvent used in the composition of the present invention is
not particularly limited, and the water solubility thereof at 20°C is usually less than 1 giL,
preferably less than 0.7 g/L, and more preferably less than 0.5 giL. Examples of the
nonpolar solvent include aromatic hydrocarbons such as xylene, alkyl (C9_13, for
-----------------------------
10
example) benzenes, phenylxylylethane, dimethylnaphthalene, alkyl (C~, C3, or Ct2-t4, for
example) naphthalenes, alkyl biphenyls, alkyl diphenyl alkanes, and aromatic
hydrocarbons having a boiling point of !50 to 350°C; aliphatic hydrocarbons such as
machine oil, normal paraffin, isoparaffin, and naphthenes; and mixtures of an aromatic
5 hydrocarbon and an aliphatic hydrocarbon, such as kerosine. The nonpolar solvent may
be used singly or as a mixture of two or more of these. The total content of the nonpolar
solvent in the composition of the present invention is usually 5 to 70% by mass. The
lower limit of the total content is preferably I 0% by mass or more and is more preferably
15% by mass or more. The upper limit of the total content is preferably 65% by mass or
10 less and is more preferably 60% by mass or less.
[00 16] Examples of a surfactant used in the composition of the present
invention include (A), (B), (C), (D), and (E) below.
(A) Nonionic surfactants:
(A-1) polyethylene glycol surfactants: polyoxyethylene alkyl (CI2-ts) ethers, alkyl
15 naphthol ethylene oxide adducts, polyoxyethylene (mono- or di-) alkyl (Cs.tz) phenyl
ethers, polyoxyethylene (mono- or di-) alkyl (Cs-12) phenyl ether formalin condensates,
polyoxyethylene (mono-, di-, or tri-) phenyl phenyl ethers, polyoxyethylene (mono-, di-,
or tri-) benzyl phenyl ethers, polyoxypropylene (mono-, di-, or tri-) benzylphenyl ethers,
polyoxyethylene (mono-, di-, or tri-) styrylphenyl ethers, polyoxypropylene (mono-, di-,
20 or tri-) phenylphenyl ethers, polyoxypropylene (mono-, di-, or tri-) benzylphenyl ethers,
polyoxypropylene (mono-, di-, or tri-) styrylphenyl ethers, polyoxyethylene (mono-, di-,
or tri-) styrylphenyl ether formalin condensates, polyoxypropylene (mono-, di-, or tri-)
styrylphenyl ether formaldehyde condensates, polyoxyethylene polyoxypropylene block
polymers, alkyl (CI2-t&) polyoxyethylene polyoxypropylene block polymer ethers, alkyl
25 (Cs-12) phenylpolyoxyethylene polyoxypropylene block polymer ethers, polyoxyethylene
bisphenyl ethers, polyoxyethylene resin acid esters, polyoxyethylene fatty acid (Ctz-ts)
monoesters, polyoxyethylene fatty acid (Ctz-ts) diesters, polyoxyethylene sorbitan fatty
acid (CI2-t&) esters, glycerol fatty acid ester ethylene oxide adducts, polyoxyethylene
castor oil ethers, polyoxyethylene hydrogenated castor oil ethers, polyoxypropylene
11
castor oil ethers, polyoxypropylene hydrogenated castor oil ethers, and polyoxyethylene
rape oil ethers, alkyl (Cl2-ts) amine ethylene oxide adducts, and fatty acid (Ct2-t&) amide
ethylene oxide adducts, for example;
(A-2) polyhydric alcohol surfactants: glycerol fatty acid esters, polyglycerin fatty
5 acid esters, pentaerythritol fatty acid esters, sorbitol fatty acid (Ct2-ts) esters, sorbitan
fatty acid (C12. 18) esters, sucrose fatty acid esters, polyhydric alcohol alkyl ethers, and
fatty acid alkanolamides, for example;
(A-3) acetylene surfactants: acetylene glycols, acetylene alcohols, acetylene glycol
ethylene oxide adducts, and acetylene alcohol ethylene oxide adducts, for example; and
10 (A-4) other surfactants: alkyl glycosides, for example.
[0017] (B) Anionic surfactants:
(B-1) carboxylic acid surfactants: carboxylic acids such as polyacrylic acid,
polymethacrylic acid, polymaleic acid, copolymers of maleic acid and an olefin
(isobutylene or diisobutylene, for example), copolymers of acrylic acid and itaconic acid,
15 copolymers of methacrylic acid and itaconic acid, copolymers of maleic acid and styrene,
copolymers of acrylic acid and methacrylic acid, copolymers of acrylic acid and acrylic
acid methyl ester, copolymers of acrylic acid and vinyl acetate, copolymers of acrylic
acid and maleic acid, N-methyl-fatty acid (Ct2-ts) sarcosinates, resin acids, and fatty acids
(Ct2-ts); and salts of these carboxylic acids, for example;
20 (B-2) sulfate surfactants: sulfates such as alkyl (C12.ts) sulfates, polyoxyethylene
alkyl (Ct2-t&) ether sulfates, polyoxyethylene (mono- or di-) alkyl (Cs.t2) phenyl ether
sulfates, sulfates of polyoxyethylene (mono- or di-) alkyl (Cs-t2) phenyl ether polymers,
polyoxyethylene (mono-, di-, or tri-) phenylphenyl ether sulfates, polyoxyethylene
(mono-, di-, or tri-) benzylphenyl ether sulfates, polyoxyethylene (mono-, di-, or tri-)
25 styrylphenyl ether sulfates, sulfates ofpolyoxyethylene (mono-, di-, or tri-) styrylphenyl
ether polymers, sulfates of polyoxyethylene polyoxypropylene block polymers, sulfated
oil, sulfated fatty acid esters, sulfated fatty acids, and sulfated olefins; and salts of these
sulfates, for example;
(B-3) sulfonic acid surfactants: sulfonic acids such as paraffin (Ct2-22) sulfonic acids,
12
alkyl (Cs-12) benzenesulfonic acids, alkyl (Cs-12) benzenesulfonic acid formalin
condensates, cresolsulfonic acid formalin condensates, a-olefin (C14.16) sulfonic acids,
dialkyl (C8•12) sulfosuccinic acids, ligninsulfonic acids, polyoxyethylene (mono- or di-)
alkyl (Cs-12) phenyl ether sulfonic acids, polyoxyethylene alkyl (C12-1s) ether
5 sulfosuccinic acid half esters, naphthalenesulfonic acids, (mono- or di-) alkyl (C1.6)
naphthalenesulfonic acids, naphthalenesulfonic acid fmmalin condensates, (mono- or di-)
alkyl (C1.6) naphthalenesulfonic acid formalin condensates, creosote oil sulfonate
formalin condensates, alkyl (Cs-12) diphenyl ether disulfonic acids, Igepon T (trade name),
polystyrene sulfonic acids, and copolymers of styrenesulfonic acid and methacrylic acid;
10 and salts of these sulfonic acids, for example; and
(B-4) phosphate surfactants: phosphates such as alkyl (C8.12) phosphates,
polyoxyethylene alkyl (C12-1s) ether phosphates, polyoxyethylene (mono- or di-) alkyl
(C8•12) phenyl ether phosphates, phosphates of polyoxyethylene (mono-, di-, or tri-) alkyl
(Cs.12) phenyl ether polymers, polyoxyethylene (mono-, di-, or tri-) phenylphenyl ether
15 phosphates, polyoxyethylene (mono-, di-, or tri-) benzylphenyl ether phosphates,
polyoxyethylene (mono-, di-, or tri-) styrylphenyl ether phosphates, phosphates of
polyoxyethylene (mono-, di-, or tri-) styrylphenyl ether polymers, phosphates of
polyoxyethylene polyoxypropylene block polymers, phosphatidylcholine,
phosphatidylethanolimine, and condensed phosphoric acids (such as tripolyphosphoric
20 acid); and salts of these phosphates, for example.
25
Examples of the salts in (B-1) to (B-4) include the salts of alkali metals (lithium,
sodium, and potassium, for example), the salts of alkaline-earth metals (calcium and
magnesium, for example), the salts of ammonium, and the salts of various amines
(alkylamines, cycloalkylamines, and alkanolamines, for example).
[00 I 8] (C) Cationic surfactants:
alkylamine salts and alkyl quaternary ammonium salts, for example.
(D) Amphoteric surfactants:
betaine surfactants and amino acid surfactants, for example.
(E) Other surfactants:
I
13
silicone surfactants and fluorine surfactants, for example.
[0019] Among these surfactants, the following surfactants (1) to (4) are
desirably used.
(1) Polyoxyalkylene arylphenyl ethers: polyoxyethylene (mono-, di-, or tri-)
5 phenylphenyl ether, polyoxyethylene (mono-, di-, or tri-) benzylphenyl ether,
polyoxyethylene (mono-, di-, or tri-) styrylphenyl ether, polyoxypropylene (mono-, di-, or
tri-) phenylphenyl ether, polyoxypropylene (mono-, di-, or tri-) benzyl phenyl ether, and
polyoxypropylene (mono-, di-, or tri-) styrylphenyl ether, for example.
(2) Polyoxyalkylene arylphenyl ether formalin condensates: polyoxyethylene
10 (mono-, di-, or tri-) styrylphenyl ether formalin condensate and polyoxypropylene (mono-,
di-, or tri-) styrylphenyl ether formaldehyde condensate, for example.
(3) Polyoxyalkylene vegetable oils: polyoxyethylene castor oil ether,
polyoxyethylene hydrogenated castor oil ethel~ polyoxypropylene castor oil ether,
polyoxypropylene hydrogenated castor oil ether, and polyoxyethylene rape oil ether, for
15 example.
( 4) Polyoxyethylene polyoxypropylene block polymers: for example,
polyoxyethylene polyoxypropylene block polymers having molecular weight of 1500 to
20000 and having ethylene oxide portion in content of 10 to 85% of the entire molecule.
Specific examples thereof include EPAN 410 (trade name, Dai-ichi Kogyo Seiyaku Co.,
20 Ltd.), EPAN 420 (trade name, Dai-ichi Kogyo Seiyaku Co., Ltd.), EPAN 450 (trade name,
Dai-ichi Kogyo Seiyaku Co., Ltd.), EPAN 485 (trade name, Dai-ichi Kogyo Seiyaku Co.,
Ltd.), EPAN 610 (trade name, Dai-ichi Kogyo Seiyaku Co., Ltd.), EPAN 680 (trade name,
Dai-ichi Kogyo Seiyaku Co., Ltd.), EPAN 710 (trade name, Dai-ichi Kogyo Seiyaku Co.,
Ltd.), EPAN 720 (trade name, Dai-ichi Kogyo Seiyaku Co., Ltd.), EPAN 740 (trade name,
25 Dai-ichi Kogyo Seiyaku Co., Ltd.), EPAN 750 (trade name, Dai-ichi Kogyo Seiyaku Co.,
Ltd.), EPAN 785 (trade name, Dai-ichi Kogyo Seiyaku Co., Ltd.), EPAN U103 (trade
name, Dai-ichi Kogyo Seiyaku Co., Ltd.), EPAN U105 (trade name, Dai-ichi Kogyo
Seiyaku Co., Ltd.), EPAN U108 (trade name, Dai-ichi Kogyo Seiyaku Co., Ltd.),
Toxanon PE-61 (trade name, Sanyo Chemical Industries, Ltd.), Toxanon PE-62 (trade
14
name, Sanyo Chemical Industries, Ltd.), Toxanon PE-64 (trade name, Sanyo Chemical
Industries, Ltd.), Toxanon PE-68 (trade name, San yo Chemical Industries, Ltd.), Toxanon
PE-71 (trade name, Sanyo Chemical Industries, Ltd.), Toxanon PE-74 (trade name, Sanyo
Chemical Industries, Ltd.), Toxanon PE-75 (trade name, Sanyo Chemical Industries, Ltd.),
5 Toxanon PE-78 (trade name, Sanyo Chemical Industries, Ltd.), Toxanon PE-108 (trade
name, Sanyo Chemical Industries, Ltd.), Toxanon PE-128 (trade name, Sanyo Chemical
Industries, Ltd.), Pluronic P£3100 (trade name, BASF Japan Ltd.), Pluronic P£4300
(trade name, BASF Japan Ltd.), Pluronic PE6100 (trade name, BASF Japan Ltd.)
Pluronic P£6200 (trade name, BASF Japan Ltd.), Pluronic P£6400 (trade name, BASF
10 Japan Ltd.), Pluronic P£6800 (trade name, BASF Japan Ltd.), Pluronic P£8100 (trade
name, BASF Japan Ltd.), Pluronic P£9200 (trade name, BASF Japan Ltd.), Pluronic
P£9400 (trade name, BASF Japan Ltd.), Pluronic PEl 0100 (trade name, BASF Japan
Ltd.), Pluronic P£10500 (trade name, BASF Japan Ltd.), Pluronic RP£2520 (trade name,
BASF Japan Ltd.), Pluronic RP£3110 (trade name, BASF Japan Ltd.), Newcalgen
15 5050PB (trade name, Takemoto Oil & Fat Co., Ltd.), Newcalgen 70100PB (trade name,
Takemoto Oil & Fat Co., Ltd.), Pepol B-182 (TOHO Chemical Industry Co., Ltd.), Pepol
B-184 (TOHO Chemical Industry Co., Ltd.), and Pepol B-188 (TOHO Chemical Industry
Co., Ltd.).
[0020] Among these surfactants (1) to ( 4), polyoxyalkylene arylphenyl ethers
20 and polyoxyalkylene vegetable oils are preferable, polyoxyethylene monostyrylphenyl
ether, polyoxyethylene distyrylphenyl ether, polyoxyethylene tristyrylphenyl ether,
polyoxyethylene castor oil ether, and polyoxyethylene hydrogenated castor oil ether are
more preferable.
The surfactant may be used singly or as a combination of two or more of these.
25 When two of these surfactants are used in combination, the following combinations (a) to
(d) are preferable and, in particular, the following combinations (e) to (i) are more
preferable:
[0021] (a) polyoxyalkylene arylphenyl ethers and alkyl (Cg.12)
benzenesulfonates;
15
(b) polyoxyalkylene aryl phenyl ether formalin condensates and alkyl (C8_12)
benzenesulfonates;
(c) polyoxyalkylene vegetable oils and alkyl (Cs-12) benzenesulfonates;
(d) polyoxyethylene polyoxypropylene block copolymers and alkyl (C8_12)
5 benzenesulfonates;
(e) polyoxyethylene (mono-, di-, or tri-) styrylphenyl ethers and calcium
dodecylbenzenesulfonate;
(f) polyoxyethylene (mono-, di-, or tri-) styrylphenyl ether formalin condensates
and calcium dodecylbenzenesulfonate;
I 0 (g) polyoxyethylene castor oil ethers and calcium dodecylbenzenesulfonate;
(h) polyoxyethylene hydrogenated castor oil ethers and calcium
dodecylbenzenesulfonate; and
(i) polyoxyethylene polyoxypropylene block copolymers and calcium
dodecylbenzenesulfonate.
15 [0022] The total content of the surfactant in the composition of the present
invention is usually 2 to 30% by mass. The lower limit of the total content is preferably
5% by mass or more and is more preferably I 0% by mass or more. The upper limit of
the total content is preferably 25% by mass or less and is more preferably 20% by mass
or less.
20 The surfactant can also be used as an adjuvant for the purpose of enhancing the
insecticidal and miticidal activity of the composition of the present invention. Examples
of other adjuvants include vegetable oils and mineral oils. These adjuvants may be
contained in advance in the emulsifiable agrochemical composition or may be mixed in
the diluted emulsifiable agrochemical composition.
25 Examples of an auxiliary component that can be additionally contained in the
composition of the present invention include an anti-freezing agent, a pH adjuster, a
stabilizing agent, an antifoaming agent, and a preservative.
The emulsifiable composition of the present invention can be produced by the
following method. The emulsifiable composition of the present invention can be
16
obtained, for example, by dissolving a compound A as an active ingredient and a
surfactant in a polar solvent and a nonpolar solvent.
Application of the composition of the present invention can be conducted by a
method of diluting the composition about 10 to 5000 times with water, for example, and
5 then spraying it on a crop, a tree, or the soil where a crop or a tree grows by using a
sprayer or the like, or by a method of diluting the composition about 2 to 100 times with
water and then spraying it from the air by a helicopter or the like.
Examples
[0023] In the following, the present invention is explained in more detail
10 referring to examples, comparative examples, and test examples. The scope of the
present invention, however, is not limited to these examples. Hereinafter, the tetm
"part(s)" refers to part(s) by mass.
[Example 1]
By mixing 5.02 patis of a compound A (purity: 99.6%) as a teclmical product, 5
15 patis ofpolyoxyethylene styrylphenyl ether (trade name: Sorpol T-20, manufactured by
TOHO Chemical Industry Co., Ltd.), 5 parts of calcium dodecylbenzenesulfonate (trade
name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 25 parts of
cyclohexanone, and 59.98 parts of aromatic hydrocarbon (trade name: Cactus Fine SF-02,
manufactured by JX Nippon Oil & Energy Corporation), an emulsifiable agrochemical
20 composition was obtained.
[Examples 2 to 30]
By mixing the components shown in Table No. 1 in the same manner as in Example
1, emulsifiable agrochemical compositions were obtained.
---------- ---------
17
[0024] [Table I]
Table I
Example Example Example Example Example
Components
I 2 3 4 5
(part(s) (pati(s) (part(s) (part(s) (patt(s)
by mass) by mass) by mass) by mass) by mass)
Compound A as a
Purity: 99.6% 5.02 5.02 10.04 5.02 5.02
technical product
Trade name, manufactured
by TOHO Chemical
Sorpol T-20 Industry Co., Ltd. 5 5 5
polyoxyethylene
styrylphenyl ether
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10 10
polyoxyethylene castor oil
ether
Trade name, manufactured
by TOHO Chemical
Sorpol EX-15 Industry Co., Ltd. 5 5 5 10 10
calcium
dodecylbenzenesulfonate
Cyclohexanone 25 65 55
N-methyl-2-pyrrolido
10 60
ne
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
59.98
Energy Corporation
19.98 24.96 64.98 14.98
aromatic hydrocarbon
[0025] [Table 2]
Table 1 (continued)
Example Example Example Example Example
Components
6 7 8 9 10
(pati(s) (patt(s) (part(s) (patt(s) (part(s)
by mass) by mass) by mass) by mass) by mass)
Compound A as a
Purity: 99.6% 5.02
technical product
5.02 5.02 5.02 5.02
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10 10 10 10 10
polyoxyethylene castor oil
ether
Trade name, manufactured
Sorpol EX-15 by TOHO Chemical 10 10 10 10 10
Industry Co., Ltd.
18
calcium
dodecylbenzenesulfonate
N-ethyl-2-pyrrolidone 10 60
I ,3-dimethyl-2-imida
10 60
zolidinone
N,N'-dimethylprop
10
ylene urea
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
64.98 14.98 64.98 14.98 64.98
Energy Corporation
aromatic hydrocarbon
[0026] [Table 3]
Table I (continued)
Example Example Example Example Example
Components
II 12 13 14 15
(patt(s) (patt(s) (patt(s) (patt(s) (part(s)
by mass) by mass) by mass) by mass) by mass)
Compound A as a
Pmity: 99.6% 5.02 5.02 5.02 5.02 5.02
technical product
Trade name, manufactmed
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10 10 10 10 10
polyoxyethylene castor oil
ether
Trade name, manufactured
by TOHO Chemical
Sorpol EX-15 Industry Co., Ltd. 10 10 10 10 10
calcium
dodecylbenzenesu1fonate
N,N'-dimethylprop
60
ylene urea
N ,N -dimethylform
15 60
amide
N,N-dimethylaceta ' 10 60
mide
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
14.98 59.98 14.98 64.98 14.98
Energy Corporation
aromatic hydrocarbon
[0027] [Table 4]
Table 1 (continued)
Example Example Example Example Example
Components 16 17 18 19 20
(patt(s) (part(s) (pmt(s) (patt(s) (part(s)
19
by mass) by mass) by mass) by mass) by mass)
Compound A as a
Purity: 99.6% 5.02 5.02 5.02 5.02 5.02
technical product
Trade name, manufactured
by TOHO Chemical
Industry Co., Ltd.
Sorpol355 mixtures of 20 20 20 20
polyoxyethylene
styrylphenyl ether and
dodecylbenzenesulfonate
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. lO
polyoxyethylene castor oil
ether
Trade name, manufactured
by TOHO Chemical
Sorpol EX-15 Industry Co., Ltd. 10
calcium
dodecylbenzenesulfonate
s-caprolactone 45 55
I -methylimidazole 20 60
4-acetylmorpholine 25
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
29.98 19.98 54.98 14.98 49.98
Energy Corporation
aromatic hydrocarbon
[0028] [Table 5]
Example Example Example
Components
21 22 23
(pati(s) (pari(s) (part(s)
by mass) by mass) by mass)
Compound A as a
Purity: 99.6% 5.02 5.02 5.02
technical product
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10 10 10
polyoxyethylene castor oil
ether,
Trade name, manufactured
by TOHO Chemical
Sorpol EX -15 Industry Co., Ltd. lO 10 10
calcium
dodecylbenzenesulfonate
4-acetylmorpholine 60
20
Dimethyl sulfoxide 20 65
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
14.98 54.98 9.98
Energy Corporation
aromatic hydrocarbon
[0029] [Table 6]
Table 1 (continued)
Example Example Example Example
Components
24 25 26 27
(part(s) (pati(s) (pati(s) (part(s)
by mass) by mass) by mass) by mass)
Compound A as a
Purity: 97.3% 5.14 5.14 5.14 5.14
technical product
Trade name, manufactured
by Nikko Chemicals Co.,
NIKKOL HC0-20
Ltd.
10 10 10 10
polyoxyethylene
hydrogenated castor oil
ether
Trade name, manufactured
by TOHO Chemical
Sorpol EX-15 Industry Co., Ltd. 5 5 5 5
calcium
dodecylbenzenesulfonate
4-formylmorpholine 15 65
Trade name, manufactured
by Akzo Nobel
AnnidFMPC mixture of morpho line 20 60
derivative and carbonic
ester
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
64.86 14.86 59.86 19.86
Energy Corporation
aromatic hydrocarbon
[0030] [Table 7]
Table 1 (continued)
Example Example Example
Components
28 29 30
(part(s) (pati(s) (part(s)
by mass) by mass) by mass)
Compound A as a
Purity: 97.3% 10.28 10.28 10.28
technical product
Trade name, manufactured
NIKKOL HC0-20 by Nikko Chemicals Co., 10 10 10
Ltd.
·--·-----------------------------
I
21
polyoxyethylene
hydrogenated castor oil
ether
Trade name, manufactured
by TOHO Chemical
Sorpol EX-15 Industry Co., Ltd. 5 5 5
calcium
dodecylbenzenesulfonate
4-acetylmorpholine 35
4-formylmorpholine 35
Trade name, manufactured
by Akzo Nobel
AnnidFMPC mixture of morpho line 40
derivative and carbonic
ester
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
39.72 39.72 34.72
Energy Corporation
aromatic hydrocarbon
22
[0031] [Example 31]
By mixing 10.04 parts of a compound A (purity: 99.6%) as a technical product, 5
parts ofpolyoxyethylene castor oil ether (trade name: Sorpol CA-42, manufactured by
TOHO Chemical Industry Co., Ltd.), 5 parts of calcium dodecylbenzenesulfonate (trade
5 name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 55 pmts of
cyclohexanone, and 24.96 pmts of aromatic hydrocarbon (trade name: Cactus Fine SF-02,
manufactured by JX Nippon Oil & Energy Corporation), an emulsifiable agrochemical
composition was obtained.
[0032] [Example 32]
10 An emulsifiable agrochemical composition was obtained in the same manner as in
Example 31 except that 5 parts of a polyoxyethylene polyoxypropylene block copolymer
(trade name: EPAN 740, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) was added
instead of 5 patts polyoxyethylene castor oil ether.
[0033] [Example 33]
15 By mixing 10.04 pmts of a compound A (purity: 99.6%) as a technical product, 10
parts of polyoxyethylene styrylphenyl ether (trade name: Sorpol T-20, manufactured by
TOHO Chemical Industry Co., Ltd.), 10 parts of calcium dodecylbenzenesulfonate (trade
name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 45 parts of
dimethyl sulfoxide, and 24.96 patts of aromatic hydrocarbon (trade name: Cactus Fine
20 SF-02, manufactured by JX Nippon Oil & Energy Corporation), an emulsifiable
agrochemical composition was obtained.
[0034] [Example 34]
An emulsifiable agrochemical composition was obtained in the same manner as in
Example 33 except that 10 parts of a polyoxyethylene styrylphenyl ether formalin
25 condensate (trade name: Sorpol F-24, manufactured by TOHO Chemical Industry Co.,
Ltd.) was added instead of I 0 parts of polyoxyethylene styrylphenyl ether.
[0035] [Example 35]
An emulsifiable agrochemical composition was obtained in the same manner as in
Example 33 except that 10 parts of polyoxyethylene castor oil ether (trade name: Sorpol
--------------------
23
CA-30, manufactured by TOHO Chemical Industry Co., Ltd.) was added instead of 10
parts of polyoxyethylene styrylphenyl ether.
[0036] [Example 36]
By mixing 10.04 parts of a compound A (purity: 99.6%) as a technical product, 10
5 parts ofpolyoxyethylene castor oil ether (trade name: Sorpol CA-30, manufactured by
TOHO Chemical Industry Co., Ltd.), 10 parts of calcium dodecylbenzenesulfonate (trade
name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 20 pmis of
N-methyl-2-pyrrolidone, and 49.96 pmis of aromatic hydrocarbon (trade name: Cactus
Fine SF-02, manufactured by JX Nippon Oil & Energy Corporation), an emulsifiable
10 agrochemical composition was obtained.
[0037] [Example 37]
An emulsifiable agrochemical composition was obtained in the same manner as in
Example 36 except that 20 parts ofN,N'-dimethylpropylene urea was added instead of20
parts ofN-methyl-2-pyrrolidone.
15 [0038] [Example 38]
By mixing 10.04 parts of a compound A (purity: 99.6%) as a technical product, I 0
patis of polyoxyethylene castor oil ether (trade name: Sorpol CA-30, manufactured by
TOHO Chemical Industry Co., Ltd.), 10 parts of calcium dodecylbenzenesulfonate (trade
name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 25 parts of
20 1 ,3-dimethyl-2-imidazolidinone, and 44.96 patis of aromatic hydrocarbon (trade name:
Cactus Fine SF-02, manufactured by JX Nippon Oil & Energy Corporation), an
emulsifiable agrochemical composition was obtained.
[0039] [Example 39]
An emulsifiable agrochemical composition was obtained in the same manner as in
25 Example 38 except that 25 patis ofN-ethyl-2-pyrrolidone was added instead of25 patts
of 1,3-dimethyl-2-imidazolidinone.
[0040] [Example 40]
By mixing 10.28 parts of a compound A (purity: 97.3%) as a teclmical product, 10
patis ofpolyoxyethylene castor oil ether (trade name: Sorpol CA-30, manufactured by
24
TOHO Chemical Industry Co., Ltd.), 5 pmts of calcium dodecylbenzenesulfonate (trade
name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 35 pmts of
4-acetylmorpholine, and 39.72 parts of aromatic hydrocarbon (trade name: Cactus Fine
SF-02, manufactured by JX Nippon Oil & Energy Corporation), an emulsifiable
5 agrochemical composition was obtained.
[0041) [Example 41]
An emulsifiable agrochemical composition was obtained in the same manner as in
Example 40 except that I 0 parts of polyoxyethylene hydrogenated castor oil ether (trade
name: NIKKOL HC0-20, manufactured by Nikko Chemicals Co., Ltd.) was added
I 0 instead of I 0 parts of polyoxyethylene castor oil ether.
[0042] [Example 42]
By mixing I 0.28 pmts of a compound A (purity: 97.3%) as a teclmical product, 10
pmts ofpolyoxyethylene castor oil ether (trade name: Sorpol CA-30, manufactured by
TOHO Chemical Industry Co., Ltd.), 5 parts of calcium dodecylbenzenesulfonate (trade
15 name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 35 parts of
4-fonnylmorpholine, and 39.72 patts of aromatic hydrocarbon (trade name: Cactus Fine
SF-02, manufactured by JX Nippon Oil & Energy Corporation), an emulsifiable
agrochemical composition was obtained.
[0043] [Example 43]
20 An emulsifiable agrochemical composition was obtained in the same manner as in
Exmnple 42 except that I 0 pmts of polyoxyethylene hydrogenated castor oil ether (trade
name: NIKKOL HC0-20, manufactured by Nikko Chemicals Co., Ltd.) was added
instead of I 0 pmts of polyoxyethylene castor oil ether.
[0044] [Example 44]
25 By mixing 10.28 parts of a compound A (purity: 97.3%) as a technical product, 10
parts of polyoxyethylene castor oil ether (trade name: Sorpol CA-30, manufactured by
TOHO Chemical Industry Co., Ltd.), 5 parts of calcium dodecylbenzenesulfonate (trade
name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 40 parts of a
mixture of morpholine derivatives and a carbonic acid esters (trade name: Armid FMPC,
i
25
manufactured by Akzo Nobel), and 34.72 parts of aromatic hydrocarbon (trade name:
Cactus Fine SF-02, manufactured by JX Nippon Oil & Energy Corporation), an
emulsifiable agrochemical composition was obtained.
[0045] [Example 45]
5 An emulsifiable agrochemical composition was obtained in the same manner as in
Example 44 except that I 0 parts of polyoxyethylene hydrogenated castor oil ether (trade
name: NIKKOL HC0-20, manufactured by Nikko Chemicals Co., Ltd.) was added
instead of I 0 pmis of polyoxyethylene castor oil ether.
[0046] [Example 46]
10 By mixing 5.02 parts of a compound A (purity: 99.6%) as a technical product, 5
parts of polyoxyethylene styrylphenyl ether (trade name: Sorpol T-20, manufactured by
TOHO Chemical Industry Co., Ltd.), 5 parts of calcium dodecylbenzenesulfonate (trade
name: Sorpol EX-15, manufactured by TOHO Chemical Industry Co., Ltd.), 5 pmts of
cyclohexanone, and 79.98 patis of aromatic hydrocarbon (trade name: Cactus Fine SF-02,
15 manufactured by JX Nippon Oil & Energy Corporation), an emulsifiable agrochemical
composition was obtained.
[0047] [Examples 47 to 70]
By mixing the components shown in Table No. 2 in the same manner as in Example
46, emulsifiable agrochemical compositions were obtained.
I
26
[0048] [Table 8]
Table 2
Example Example Example Example Example
Components
46 47 48 49 50
(part(s) (part(s) (part(s) (part(s) (part(s)
by mass) by mass) by mass) by mass) by mass)
Compound A as a
Purity: 99.6% 5.02 5.02 10.04 5.02 5.02
technical product
Trade name, manufactured
by TOHO Chemical
Sorpol T-20 Industry Co., Ltd. 5 5 5
polyoxyethylene
styrylphenyl ether
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10 10
polyoxyethylene castor oil
ether
Trade name, manufactured
by TOHO Chemical
Sorpol EX -15 Industry Co., Ltd. 5 5 5 10 10
calcium
dodecylbenzenesulfonate
Cyclohexanone 5 70 70
N-methyl-2-pyrrolido
5 70
ne
Trade name, manufactured
Cactus Fine SF -02
by JX Nippon Oil &
79.98 14.98 9.96 69.98 4.98
Energy Corporation
aromatic hydrocarbon,
[0049] [Table 9]
Table 2 (continued)
Example Example Example Example Example
Components
51 52 53 54 55
(part(s) (pati(s) by (part(s) (pati(s) by (pati(s)
by mass) mass) by mass) mass) by mass)
Compound A as a
Purity: 99.6% 5.02 5.02 5.02 5.02 5.02
technical product
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10 10 10 10 10
polyoxyethylene castor oil
ether
Trade name, manufactured
SorpolEX-15 by TOHO Chemical 10 10 10 10 10
Industry Co., Ltd.
27
calcium
dodecylbenzenesulfonate
N-ethyl-2-pyrrolidone 5 70
I ,3-dimethyl-2-imida
5 70
zolidinone
N,N'-dimethylprop
5
ylene urea
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
69.98 4.98 69.98 4.98 69.98
Energy Corporation
aromatic hydrocarbon
[0050] [Table 10]
Table 2 (continued)
Example Example Example Example Example
56 57 58 59 60
Components
(pmi(s) (part(s) by (pati(s) (part(s) by (part(s)
by mass) mass) by mass) mass) by mass)
Compound A as a
Purity: 99.6% 5.02 5.02 5.02 5.02 5.02
technical product
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10 10 10 10 10
polyoxyethylene castor oil
ether,
Trade name, manufactured
by TOHO Chemical
Sorpol EX-15 Industry Co., Ltd. 10 10 10 10 10
calcium
dodecylbenzenesulfonate
N,N'-dimethylprop
70
ylene urea
N,N-dimethylform
5 70
amide
N,N-dimethylaceta
5 70
mide
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
4.98 69.98 4.98 69.98 4.98
Energy Corporation
aromatic hydrocarbon
[0051] [Table 11]
Table 2 (continued)
Example Example Example Example Example
61 62 63 64 65
Components
(pati(s) (part(s) by (pmt(s) (part(s) by (patt(s)
by mass) mass) by mass) mass) by mass)
i
28
Compound A as a
Purity: 99.6% 5.02 5.02 5.02 5.02 5.02
technical product
Trade name, manufactured
by TOHO Chemical
Industry Co., Ltd.
Sorpol355 mixtures of 20 20 20 20
polyoxyethylene
styrylphenyl ether and
dodecylbenzenesulfonate
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10
polyoxyethylene castor oil
ether
Trade name, manufactured
by TOHO Chemical
Sorpol EX-15 Industry Co., Ltd. 10
calcium
dodecylbenzenesulfonate
, -caprolactone 5 70
1-methylimidazole 5 70
4-acetylmorpholine 5
Trade name, manufactured
Cactus FineSF-02
by JX Nippon Oil &
69.98 4.98 69.98 4.98 69.98
Energy Corporation
aromatic hydrocarbon
[0052] [Table 12]
Table 2 (continued)
Example Example Example Example Example
66 67 68 69 70
Components
(pati(s) (part(s) by (pati(s) (part(s) by (patt(s)
by mass) mass) by mass) mass) by mass)
Compound A as a
Purity: 99.6% 5.02 5.02 5.02 5.14 5.14
technical product
Trade name, manufactured
by TOHO Chemical
Sorpol CA-30 Industry Co., Ltd. 10 10 10 !0 !0
polyoxyethylene castor oil
ether
Trade name, manufactured
by TOHO Chemical
Sorpol EX-15 Industry Co., Ltd. 10 10 10 5 5
calcium
dodecylbenzenesulfonate
4-acetylmorpholine 70
Dimethyl sulfoxide 5 70
-----------------------------
29
4-formylmorpholine 5 70
Trade name, manufactured
Cactus Fine SF-02
by JX Nippon Oil &
4.98 69.98 4.98 74.86 9.86
Energy Corporation
aromatic hydrocarbon
I
30
[0053) [Comparative Example I]
In 56.86 parts of water, 3 patis of a mixture of polyoxyethylene styrylphenyl ether
and polyoxyalkylene glycol (trade name: Sorpol3353, manufactured by TOHO Chemical
Industry Co., Ltd.), 0.1 pmi of a silicone antifoaming agent (trade name: KM-73,
5 manufactured by Shin-Etsu Chemical Co., Ltd.), 10 parts of propylene glycol, and 10.04
pmts of a compound A (purity: 99.6%) as a technical product were dispersed, followed by
wet grinding with 200 g of 0.8-1.2 mm diameter glass beads in a sand grinder
(manufactured by AIMEX Co., Ltd.) to obtain 80 parts of a ground slurry. Separately, in
19.55 pmis ofwate1; 0.05 part of 1,2-benzoisothiazolin-3-one (trade name: PROXEL
10 GXL, manufactured by Avecia Inc.), 0.1 part ofxanthan gum (trade name: KELZAN
ASX, manufactured by CP Kelco ), and 0.3 part of smectite clay (trade name: VEEGUM
R, manufactured by R. T. Vanderbilt Company, Inc.) were dispersed in this order to obtain
20 parts of a dispersion medium. The ground slurry at an amount of 80 pmts and 20
parts of the dispersion medium were mixed together to obtain 100 parts of an
15 agrochemical composition as a uniform aqueous suspension.
[0054] [Test Example 1] Appearance of emulsifiable agrochemical
composition
The appearance of the emulsifiable agrochemical compositions obtained in the
examples was visually observed for evaluation according to the following criteria. The
20 results are shown in Table No. 3.
0: transparent and clear
x: cloudy and whitish
[0055] [Test Example 2] Emulsion stability of water-diluted liquid
In a I 00 mL measuring cylinder, 100 mL of hard water having water hardness of 3
25 degrees was added and, thereto, I mL of the emulsifiable agrochemical composition
obtained in each example was further added. The measuring cylinder was then inverted
for uniform emulsification. The resulting diluted liquid was left to stand at 30°C for 24
hours, followed by measurement of the amount (mL) of a deposit. The results are
shown in Table No.3 and Table No.4.
31
[0056] [Table 13]
Table 3
Test Example Test Example Test Example Test
1 2 1 Example2
Appearance Deposit Appearance Deposit
amount (mL) amount
(mL)
Example 1 0 0 Example46 X -
Example2 0 infinitesimal Example 47 0 0.2
quantity
Example 3 0 0 Example48 0 0.6
Example4 0 0 Example 49 X -
Example 5 0 0 Example 50 0 0.6
Example6 0 0 Example 51 X -
Example 7 0 0 Example 52 0 0.7
Example 8 0 0 Example 53 X -
Example9 0 0 Example 54 0 0.6
Example 10 0 0 Example 55 X -
Example 11 0 0 Example 56 0 0.6
Example 12 0 0 Example 57 X -
Example 13 0 0 Example 58 0 0.6
Example 14 0 0 Example 59 X -
Example 15 0 0 Example60 0 0.5
Example 16 0 0 Example61 X -
Example 17 0 0 Example 62 0 0.4
Example 18 0 infinitesimal Example 63 X -
quantity
Example 19 0 infinitesimal Example 64 0 0.4
quantity
Example20 0 0 Example 65 X -
Example21 0 0 Example66 0 0.5
Example22 0 0 Example67 X -
Example23 0 0 Example 68 0 0.5
Example 24 0 0 Example 69 X -
Example 25 0 infinitesimal Example 70 0 1.25
quantity
Example26 0 0
Example27 0 0
Example28 0 infinitesimal
quantity
Example29 0 infinitesimal
quantity
Example 30 0 infinitesimal
quantity
[0057] [Table 14]
Table 4
Example 31
Example 32
Example 33
Example 34
Example 35
Example 36
Example 37
Example 38
Example 39
Example40
Example4l
Example42
Example43
Example44
Example45
32
Deposit amount (mL)
infinitesimal quantity
infinitesimal quantity
0
0
0
0
0
0
infinitesimal quantity
infinitesimal quantity
infinitesimal quantity
0
infinitesimal quantity
infinitesimal quantity
infinitesimal quantity
[0058] [Test Example 3] Test for efficacy on Thrips palmi female adults
A polystyrene cup with a lid having a hole at the center (lid diameter: 7.5 em,
height: 4 em) was charged with tap water, and filter paper was placed so as to absorb the
tap water. Absorbent cotton ( 5 em x 5 em) was placed on the filter paper and was then
5 dampened, and on top of it, a leaf disc (diameter: 3 em) prepared of a cucumber leaf was
placed. On the leaf disc, I 0 Thrips palmi female adults were released and each of the
test containers was uniformly sprayed (2.5 mg/cm2
) with a chemical solution using a
rotating spray tower. As the chemical solution used, the emulsifiable agrochemical
composition obtained in one of the examples and the comparative examples was diluted
10 with water so as to achieve a concentration of the compound A of 12.5 ppm. Three days
later, evaluation was conducted to determine the mortality by the following math formula.
The test was conducted in two replications.
Mortality(%)= {the number of dead insects/(the number of dead insects +the
number of live insects)} x I 00
15 The results are shown in Table No. 5.
[0059] [Table 15]
Table 5
33
concentration
Mortality of Thrips palmi female adults(%)
(ppm) Example 3 Example 28 Example 29 Example 30 Comparative
Example 1
12.5 100 100 100 100 5
[0060] [Test Example 4] Test for efficacy on Tetranychus urticae female
adults
A polystyrene cup with a lid having a hole at the center (lid diameter: 7.5 em,
height: 4 em) was charged with tap water, and filter paper was released so as to absorb
5 the tap water. On top of it, a leaf disc (2 em x 2 em) made of a common bean leaf was
placed. On the leaf disc, 10 Tetranychus urticae female adults were placed, and each of
the test containers was uniformly sprayed (2.5 mg/cm2
) with a chemical solution using a
rotating spray tower. As the chemical solution used, the emulsifiable agrochemical
composition obtained in one of the examples and the comparative examples was diluted
10 with water so as to achieve a concentration of the compound A of25 ppm. Two days
later, evaluation was conducted to determine the mottality by the math formula in Test
Example 3. The test was conducted in two replications. The results are shown in
Table No.6.
[0061] [Table 16]
15 Table 6
concentration
Mortality of Tetranychus urticae female adults (%)
(ppm) Example 3 Example28 Example 29 Example 30 Comparative
Example 1
25 100 100 100 100 5
INDUSTRIAL APPLICABILITY
[0062] The composition of the present invention can be used for controlling
20 harmful living organisms, in particular, pests and mites.

CLAIMS
I. An emulsifiable agrochemical composition comprising:
(Z)-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yi]-N-(methox
5 yiminomethyl)-2-methylbenzoic acid amide;
a polar solvent;
a nonpolar solvent; and
a surfactant.
I 0 2. The emulsifiable agrochemical composition according to claim I, wherein
the content of the polar solvent is 7.5 to 67.5% by mass relative to the mass of the
emulsifiable agrochemical composition.
3. The emulsifiable agrochemical composition according to claim 1 or 2, wherein
15 the polar solvent is at least one or more selected from the group consisting of a
ketone, a N-alkylpyrrolidone, a cyclic urea, a carboxylic acid amide, a lactone, a
nitrogen-containing aromatic compound, a cyclic amine, dimethyl sulfoxide, and a
carbonic acid ester.
20 4. The emulsifiable agrochemical composition according to claim 1 or 2, wherein
the polar solvent is at least one or more selected from the group consisting of a 5- to
7-membered cyclic ketone, a N-C1-12 alkylpyrrolidone, a 5- or 6-membered cyclic urea, a
C1.12 carboxylic acid amide, a 4- to 7-membered cyclic lactone, a 5- or 6-membered
cyclic aromatic compound containing one or more nitrogen atoms, a 5- or 6-membered
25 saturated cyclic amine containing one or more nitrogen atoms, dimethyl sulfoxide, and a
c2-4 alkylene carbonate.
5. TI1e emulsifiable agrochemical composition according to claim 4, wherein
the 5- or 6-membered saturated cyclic amine containing one or more nitrogen atoms
is a 4-acyhnorpholine.
6. The emulsifiable agrochemical composition according to claim 1 or 2, wherein
the polar solvent is at least one or more selected from the group consisting of
5 cyclohexanone, N-methyl-pyrrolidone, N-ethyl-2-pyrrolidone,
1,3-dimethyl-2-imidazolidinone, N,N'-dimethylpropylene urea, N,N-dimethylformamide,
N ,N-dimethylacetamide, s-caprolactone, 1-methylimidazole, 4-acetylmorpholine,
4-formylmorpholine, dimethyl sulfoxide, and propylene carbonate.
10 7. The emulsifiable agrochemical composition according to claim 1, wherein
the polar solvent is cyclohexanone and the content of the polar solvent is 22.5 to
67.5% by mass relative to the mass of the emulsifiable agrochemical composition.
8. The emulsifiable agrochemical composition according to claim 1, wherein
15 the polar solvent is N-methyl-2-pyrrolidone and the content of the polar solvent is
7.5 to 62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
9. The emulsifiable agrochemical composition according to claim 1, wherein
the polar solvent is N-ethyl-2-pyrrolidone and the content of the polar solvent is 7.5
20 to 62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
10. The emulsifiable agrochemical composition according to claim 1, wherein
the polar solvent is 1,3-dimethyl-2-imidazolidinone and the content of the polar
solvent is 7.5 to 62.5% by mass relative to the mass of the emulsifiable agrochemical
25 composition.
11. The emulsifiable agrochemical composition according to claim 1, wherein
the polar solvent is N,N'-din1ethylpropylene urea and the content of the polar
solvent is 7.5 to 62.5% by mass relative to the mass of the emulsifiable agrochemical
composition.
I 2. The emulsifiable agrochemical composition according to claim I, wherein
the polar solvent is N,N-dimethylfonnamide and the content of the polar solvent is
5 12.5 to 62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
13. The emulsifiable agrochemical composition according to claim I, wherein
the polar solvent is N,N-dimethylacetamide and the content of the polar solvent is
7.5 to 62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
I 4. The emulsifiable agrochemical composition according to claim I, wherein
the polar solvent is E-caprolactone and the content of the polar solvent is 42.5 to
57.5% by mass relative to the mass of the emulsifiable agrochemical composition.
15 I 5. The emulsifiable agrochemical composition according to claim 1, wherein
the polar solvent is 1-methylimidazole and the content of the polar solvent is I 7.5 to
62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
16. The emulsifiable agrochemical composition according to claim I, wherein
20 the polar solvent is 4-acetylmorpholine and the content of the polar solvent is 22.5
to 62.5% by mass relative to the mass of the emulsifiable agrochemical composition.
17. The emulsifiable agrochemical composition according to claim 1, wherein
the polar solvent is 4-formylmorpholine and the content of the polar solvent is 12.5
25 to 67.5% by mass relative to the mass of the emulsifiable agrochemical composition.
18. The emulsifiable agrochemical composition according to claim 1, wherein
the polar solvent is dimethyl sulfoxide and the cont~nt of the polar solvent is 17.5 to
67.5% by mass relative to the mass ofthe emulsifiable agrochemical composition.
19. The emulsifiable agrochemical composition according to any one of claims I to
18, wherein
the nonpolar solvent is an aromatic hydrocarbon.
20. The emulsifiable agrochemical composition according to any one of claims 1 to
19, wherein
the surfactant is one or more selected from the group consisting of a
polyoxyalkylene arylphenyl ether, a polyoxyalkylene arylphenyl ether formalin
10 condensate, a polyoxyalkylene vegetable oil, and a polyoxyethylene polyo~ypropylene
block copolymer.
21. The emulsifiable agrochemical composition according to claim 20, wherein
the surfactant is at least one or more selected from the group consisting of a
15 polyoxyalkylene arylphenyl ether and a polyoxyalkylene vegetable oil.
22. The emulsifiable agrochemical composition according to claim 20, wherein
the surfactant is at least one or more selected fiom the group consisting of
polyoxyethylene monostyrylphenyl ether, polyoxyethylene disiyrylphenyl ether,
20 polyoxyethylene tristyrylphenyl ether, polyoxyethylene castor oil ether, and
polyoxyethylene hydrogenated castor oil etheir.