TECIINICAL FIELD
[0001] The present inventio~rie lates to a liquid pesticide conipositioti in \vI~icha
spray solution thereof prepared by diluting the liquid pesticide composition with water
can maintain insecticidal efficacy for long periods.
10
BACKGROUND ART
[0002] It has been known that certain isoxazoline substituted benza~nide
compounds have pest control activities against harmful insects (for example, insects,
15 mites, crustaceans, nematodes, and the like) in the field of horticulture or of animal
l~usbandtylllygiene( see Patent Docunlcnt 1).
In addition, a pesticide e~nulsifierc olnposition containing the compound, a
surfactant, and an ester solvent that corresponds to a polar solvent has been known (see
Patent Document 2).
20
Prior Art Docr~~nents
Patent Documents
[0003] Patent Document 1 : International Publication WO 2007f026965
Patent Document 2: International Publicatio~Wi O 2009103 1621
25
SUMMAItaininigso xazoline substituteti
ben~amidec ompountls with water to preparc spray solutioas thcrcof, and storing then1 for
long periods, insecticidal efficacy is reduccd after storage.
5 Means for Solving the Problem
[0005] As a result of intensive study regarding the problen~sd escribed above,
the inventors of the present invention have founti that when a spray solution prepared by
diluting the later-described liquid pesticide composition, which contains an isoxazoline
substih~tedb enzarnide conlpound as a pesticide active component, with water is stored
10 for long periods, insecticidal efficacy of the liquid pesticide con~position is not reduced,
whereby the present invention has been completed.
That is, the present invention relates to a liquid pesticide co~lipositiond escribed in
[I] to [23] below (hereinafter, also referred to as a compositio~ol f the present invention).
[00061 [ll
15 A liquid pesticide composition containing: (a)
(2)-4-[5-(3,5-dic1~loropl1e1~yl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(metl1oxyi
minomethyl)-2-methyl benzoic acid amide (hereinafter, abbreviated as Con~poundA ) as a
pesticide active ingredient; (b) at least one selected from the group consisting of
surfactant and protective colloid; (c) a solvent; and (d) water.
20 [00071 PI
'l'he liquid pesticide composition described in [I], characterized in that (b) at least
one selected from the group consisting of surfactant and protective colloid is a surfactant,
that (c) the solvent is a llorlpolar solvent, and that (a) the pesticide active ingredient is
present as a solid dispersed in (d) water.
25 100081 [31
Tile liquid pesticide compositioll described in [2], in which (c) the nonpolar solvent
is at least one selected fio~nth e group consisting of aromatic carboxylic acid estct;
dibasic acid estel; fatty acid ester, and aromatic hydrocarbon.
[00091 [41
3
The liquid pesticidc co~lipositiond cscribcd in [2j, in which (c) tlie nonpolar solvcnt
is at least one selected from the group consisting of plithalic acid alkyl ester having a
Cg.13 alkyl gronp; trimellitic acid alkyl cstcr having a C8.10 alkyl group; dibasic acid ester
that is an cstcr of a C6.10 dicarboxylic acid and a C4.g alcohol; fatty acid ester derived
5 from a vegetable oil; fatty acid ester tliat is an ester of a CS.lg fatty acid and a c1.1~
alcohol; fatty acid triglyceride; and aromatic hydrocarboti.
[OOlOI [51
The liquid pesticidc cornposition described in [2], in wliicli (c) the nonpolar solvent
is at least one selected from the group consisting of ditridecyl plithalate, bis(2-ethylliexyl)
10 plithalate, dialkyl (Clo-l*) phthalate, trialkyl (Cg or Clo) trimellitate, tris(2-ethylhexpl)
trimellitate, triisodecyl trimellitate, diisobutyl adipate, bis(2-etliylhexyl) sebacate,
soybean oil fatty acid ester, methyl oleate, isobutyl oleate, cetyl2-ethylhexanoate,
2-ethyll~exanoica cid triglyceride, and phet~ylxylyle tlia~ie.
[00111 [61
15 The liquid pesticide composition described in any one of [2] to [5j, in which a
content of (c) the nonpolar solvent is 30% by mass to 50% by mass based on a total mass
of the liquid pesticide composition.
[00121 [71
The liquid pesticide composition described in any one of [2j to [6], in which (b) the
20 suifactant is at least one selected from the group consisting of polyoxyethylene
styrylphenyl ether, polyoxyethylene-polyoxypropylene block polymer, acetylene diol,
polyoxyethylene styrylplienyl ether sulfuric acid ester or a salt thereof, and
polyoxyethylene styrylphenyl ether pliospl~orica cid ester or a salt tliereof.
[00131 [81
25 The liquid pesticide composition described ia 171, in which (b) the surfactant is at
least one selected from the group consisting of polyoxyethyle~ie~ nonostytylphenyle tlier,
polyoxyetl~yle~dieis tyrylphenyl ether, polyoxyethylene tristyrylpl~enple ther,
polyoxpctliylene-polyoxypropyleneb lock poly~~iearc,e tylene diol, polyoxyethylene
styrylphenyl ether sulfuric acid ester salt, and polyoxyethylene styrylphenyl ether
pl~ospliorica cid ester.
I00141 I91
Thc liquid pesticide conlposition described in any one of [2] to [8], in which a total
content of (b) the surfactant is 0.1% by Inass to 10% by mass based on a total nlass of the
5 liquid pesticide composition.
[0015] [lo]
The liquid pesticide coinposition described in [I], characterized in that (a) the
pesticide active ingredient is dissolved in (c) the solvent, and the solvent is present as
being enlulsified in (d) water.
10 [0016] [ll]
The liquid pesticide composition describcd in [lo], in which (c) the solvent is at
least one sclcctcd fsom the group consisting of fatty acid dimethylamide,
N-alkyl-2-pyl-rolidone, arotnatic hydrocarboil, and ester solvent.
[0017] [12]
15 The liquid pesticide colnposition described in [lo], in which (c) the solvent is at
least one selected from the group consisting of fatty acid dimethylalnide,
N-alkyl-2-pyrl-olidone, aromatic hydrocarbon, dibasic acid ester, and fatty acid ester.
[0018] [13]
The liquid pesticide cotnposition described in [lo], characterized in that (c) the
20 solvent is a mixture of at least one selected fso~nth e group consisting of fatty acid
dimethylamide and N-alkyl-2-pyrolidone; and at least one selected from the group
consisting of aromatic hydrocarbon and ester solvent.
[0019] [14]
The liquid pesticide composition described in [lo], characterized in that (c) the
25 solvent is a mixture of at least one selected fsotn the group consisting of fatty acid
diinethylainide and N-alkyl-2-pyrrolidone; and at least onc selected fro111 the group
consisting of aromatic hydrocarbon, dibasic acid ester, and fatty acid esten
[0020] [I51
The liquid pesticide composition described in [lo], characterized in that (c) thc
5
solvent is a mixture of at least one sclcctcd from the group consisting of fatty acid
dirnethylaniidc co~nposedo f c8.1f0a tty acid and N-alkyl-2-pyrrolidone; and at least one
selected frolorn the group consisting of aron~atich ydrocarbon, dibasic acid ester that is an
ester of a C4~6d icarboxylic acid and a C1.4 alcohol, and fatty acid cster that is an cster of a
5 (23.8 fatty acid and a c1.8 alcohol.
[0021] 1161
The liquid pesticide composition described in [lo], characterized in that (c) the
solvent is a mixture of at least one selected fi.0111 the group consisting of dimethyl octane
amide, dimethyl decane a~nidea, nd N-octpl-2-pyrrolidone; and at least one selected from
10 the group consisting of aromatic hydrocarbon, diisobutyl succinate, diisobutyl glotarate,
dimethyl 2-methylglutarate, diisobutyl adipate, butyl lactate, lactic acid 2-ethylhexyl ester:
and tnethyl caprylate.
[0022] [17]
The liquid pesticide composition described in [13], in wllich a content of at least
15 one selected from the group consisting of aromatic hydrocarbon and ester solvent is 2.5%
by n~astso 17.5% by mass based on a total nlass of thc liquid pesticide composition.
[0023] [IS]
The liquid pesticide composition described in any one of 1101 to 1171, in which (b)
the surfactant is a nonionic surfactant or a sulfonic acid surfactant.
20 [0024] [I91
v
The liquid pesticide composition described in [I S], in which (b) the surfactant is
selected from the group consisting of polyoxyethylene styrylphenpl ethel;
polyoxyethylene-poIyoxyprop>fletlbe lock polymer, and dialkyl (C8.,2) s~~lfos~ccinate.
100251 [20]
25 The liquid pesticide composition described in [18], in which (b) the surfactant is
selected fiom the group consisting of polyoxyethylene styr)~Iphenyel ther,
polyoxyethylene-polyoxypropyle~~belo ck polymer, and dioctyl sulfosuccinate
6
The liquid pcsticide composition describcd in any one of [lo] to 1201, in wliich a
total content oC(b) the sul-Factant is 0.1% by mass to 10% by mass based on a total mass
of the liquid pesticide co~nposition.
[0027] [22]
5 The liquid pesticide composition tlescribed in any one of [lo] to [21], in which (b)
the protective colloid is a polyvinyl alcohol.
100281 1231
The liquid pesticide conlposition describcd in [22], in which a content of the
protective colloid is 0.1% by mass to 10% by mass based on a total mass of the liquid
10 pesticide composition.
Effects of tlie Invention
[0029] When diluting the composition of the present invention with water to
prepare a spray solution, decrease of insecticidal efficacy of the co~npositionc an be
15 suppressed even after storing tlie composition for long periods. Also, the conlposition
of the present invention shows an cxcellent pest control effect against harmful insects in
the field of horticulture or of ani~nahl usbandry/hygiene. Moreover, the co~npositiono f
the present invention in tlie fomi of tlie aqueous suspensioti described in [2] to [9]
(hereinafter, also referred to as an aqueous suspension pesticide composition) is excellent
20 for preservation stability. The coniposition of tlie present invention in the fomi of the
oil-in-water en~ulsiond escribed in 11 01 to [23] (hereinaftel; also refcued to as an
oil-in-water emulsion pesticide composition) can achieve superior preservation stability
at low temperatures by using a certain solvent.
25 MODES FOR CAKKYINCi OUT THE INVENTION
[0030] A liquid pesticide composition of tlie present invention contains:
(a)
(Z)-4-[5-(3,5-dicliloropl1enyl)-5-1t~ifluolu1iietl1yl-4,5-diliydroisoxazole-3-yl]-N-(1i~ellioxyi
mi1io1i1etliyl)-2-1nethylb cnzoic acitl atnide (Compound A) as a pesticide active
ingredient;
(b) at least one selected fiom the group co~lsistiligo f surfactant ant1 protective
colloid;
5 (c) a solvent; and
(d) water;
and contains otller ingredients that will be dcscribed later, if desired.
[003 11 [(a) Compound A:
(Z)-4-[5-(3,5-dichloroplienyl)-5-trifluorotnetl~yl-4,5-dihydroisoxazole-3-yl]-N-(1nethoxyi
10 niinomethy1)-2-niethyl benzoic acid aniide]
A content of Compound A in tlie conlposition of tile present invention is usually
0.05% by mass to 50% by tnass based on a total Inass of the co~npositiono f the present
invention. The lower limit of the content is preferably 0.1% by Inass or above. The
upper limit of the content is preferably 30% by Inass or below.
15 [0032] Conlpound A in the composition of the present invention described in [2]
to [9] is prcsent as a solid dispersed in water. A content of Compound A is usually
0.05% by mass to 50% by mass based on a total mass of the con~positiono f the prescnt
invention. The lower litnit of the content is preferably 0.1% by mass or above, 1% by
mass or above, 3% by mass or above, 4% by Inass or above, or 5% by mass or above.
20 The upper limit of the content is preferably 30% by Inass or below, 20% by Inass or
below, or 15% by mass or below.
Meanwhile, Compound A in the co~npositiono f the prcsent invention described in
[lo] to [23] is present as bcing dissolved in a solvent, and these are emulsified in water.
A content of Cotnpountl A is usually 0.05% by tnass to 30% by liiass based on a total
25 mass oftlie composition of the present invention. The lower liniit of the content is
preferably 0.1% by inass or above, and more preferably 1% by Inass or above. Tl~e
upper liniit of tlie content is prcferably 20% by niass or below, and more preferably 10%
by mass or below.
Note that Compound A above can be obtained, for exanlple, by the tilethod
8
described in Patent Document 1 (Synthesis Exa~nple2 3).
[0033] The composition of the preseut invention can further contain pesticide
active ingredients other than Co~npoundA , particularly microbicides, bactericides,
nematicides, niiticides, or insecticitles. Specific exa~npleso f the microbicides,
5 bactericides, ne~naticidesm, iticides, and insecticides, which can further be contained,
will be listed below as common names.
[0034] Microbicides: atnisulbrom, acibenzolar, aampropyfos, anilazine,
azaconazole, azoxystrobin, benalaxyl, benodanil, beno~nylb, enzamacril, binapacryl,
biphenyl, bite~tanolb, ethoxazine, bordeaux mixture, blastieidin-S, brotnoconazole,
10 bupirimate, buthiobate, calcium polysulfide, captafol, captan, coliper oxychloride,
carpropamid, carbendazim, carboxin, cliinometl~ionatc, lilobentl~iazonec, lilorfenazol,
cl~lorotleb,c lilorotl~alonilc, hlozolinate, cufianeb, cytnoxanil, cyproconazol, cyprodinil,
cyprofuram, debacarb, dichlorophen, diclobutrazol, dichlofluanid, diclomezine, tlicloran,
diethofencarb, diclocymet, difenoconazole, diflumetorim, dimetliirin~ol,d imethomorpb,
15 diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos,
dithianon, dodemorph, dodine, diazoxolon, edifenphos, epoxiconazole, etaconazole,
etliirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenfuram, fenpiclonil,
fet~propidinf,e tlpropimorph, fentin, ferbam, feri~nzonef, luazinao~f,l udioxonil,
fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet,
20 fosetyl-aluminium, fuberidazole, fiiralaxyl, fetianlidone, fcnhcxamid, guazatine,
l~exachlorobenze~h~eex,a conazole, hymexazol, imazalil, imibenconazole, iminoctadine,
ipconazole, iprobenfos, iprodione, isopmtliiolane, iprovalicarb, isopyrazam, kasugamycin,
kresoxim-methyl, mancoppel; mancozeb, maneb, mepanipyrim, mepronil, ~uetalaxyl,
metconazole, tnetira~nm, netominostrobin, myclobutanil, nabam, nickel
25 bis(dimethylditl~iocarbamate), nitrothal-isopropyl, nuarimol, octhilinone, ofurace,
oxadixyl, oxycarboxin, oxpoconazolc fumarate, pefi~rzoate:p enconazole, peacyeuron,
phthalide, pipcralin, polyoxins, pmbenazole, prochloraz, procymidone, propamocarb
hydrochloride, propieonazole, propineb, pyrazophos, pyrifenos, pyri~nethanil,p yroquilon,
quiooxyfen, quintozene, sulfur, spi~uxaminet,e buconazole, tecnazene, tetm~onazole~
9
thiabcndazole, tliiflu~amitlet,l iiopllanate-iiietl~yl,t lliranl, tolclofos-metliyl, tolylfluanid,
triadi~nefon,t oriadimenol, triazoxidc, tricyclazole, tridemorph, triflumizolc, triforine,
triticonazole, validamycin, vinclozoli~z~i,n eb, ziraoi, and oxine-copper.
[0035] Bactericides: streptomycin, oxytetracycline, and oxolinic acid.
5 [0036] Nematicides: aldoxycarb, fosthiazate, fostllietan, oxamyl, and
fenamiphos.
[0037] Miticides: amitraz, brornopropylate, chinotnet1~ionatc, hlorobezilate,
clofcntezine, cye~lopyrafenc, pliexatine, dicofol, dienochlor, etoxazole, fenazaquin,
fenbutatin oxide, fenpropathrin, fenproximate, halfcnprox, hexythiazox, milbemectiil,
10 propargitc, pyridaben, pyrimidifen, and tebufenpyrad.
Insecticides: abarnectin, acephate, acetamipirid, azinphos-methyl, bet~diocasb,
benfiiracarb, bensultap, bifentltrin, buprofezin, butocarboxim, carbaryl, carbofuratl,
casbosulfan, cartap, chlorat~trai~iliprolceh, lorfenapyr, chlorpyrifos, cl~lorfet~vinphos,
cldorfluazuron, clothianidin, chrotnafenozide, chlorpyrifos-methyl, cyatltraniliprole,
15 cyfluthrin, beta-cyfluthrin, cypernlethrin, cyromazine, cyhalothrin, lambda-cyhalothrin,
deltatnethrin, diafenthiuron, diazinon, diacloden, diflubenzuron, dimethylvinphos,
diofet~olaod, isulfoton, dimethoate, EPN, esfenvalerate, ethiofencarb, ethiprole,
etofenprox, etrirnfos, fenitrothion, feuobucarb, fenoxycarb, fenpropathrin, fenvalerate,
fipronil, Flubendiatnide, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate,
20 fonophos, formetanate, fonnothion, furathiocarb, l~alofenozidel, ~exaflumuron,
hydra~nethylnon,i n~iclacloprid,i sofenplios, indoxacarb, isoprocarb, isoxathion, lufenuron,
tnalatl~ioni,n etaldehyde, metha~nidopl~oms,e tl~idathionm, ethacrifos, metalcarb,
tnethomyl, inethoprene, nietl~oxychlor~, nethoxyfenozide,t ~~onocrotophonsi,u scalure,
nitenpyrain, omcthoate, oxydemeton-metliyl, oxaniyl, parathion, parathion-methyl,
25 pennethrin, phenthoate, phoxim, phorate, phosalone, phosinet, pl~ospharnido~pii,r imicarb,
pirimiplios-methyl, profenofos, pymetrozine, pyraclofos, pyriproxpfen, rotenone,
sull)rofos, silafluofen, spinosad, sulfotcp, sulfoxaflor, tebfenozide, teflubenzuroil,
tefluthorin, terbufos, tetrachlorvinphos, tliiodicarb, tl~ia~netlioxamth, iofa~loxt,h iometon,
tolfenpyrad, tralomethrin, triclilorfon, triazuron, triflumuro~l,a nd vamidothion.
10
[003S] Pesticide active ingredients other than Compound A can be used singly,
or can be used as a mixture of two or more of them.
A total content of pcsticide active itigredients other than Compound A is usually
0.05% by riiass to 50% by tliass based on a total mass of the composition of the present
5 invention. The lower litiiit of the total content is preferably 0.1 % by mass or above, and
more preferably 1% by mass or above. The upper limit of tlie total content is preferably
40% by mass or below, 30% by tliass or below, and ulore preferably 20% by ~liasso r
below. Peslicide active ingredients other than Cornpoutid A may be dissolved in a
solvent, or niay be dispersed in water without being dissolved in a solvent.
10 [0039] [(b) Surfactant and Protective Colloid]
Examples of the surfactant used in the composition of tlie present invention include
(A) Nouiouic surfactants, (B) Anionic surfactants, (C) Cationic surfactants, (D)
Amplioteric Surfactants, and (E) Other surfactants.
[0040] (A) Nonionic surfactants:
15 (A-1) Polyethylene glycol surfactants: Examples thereof include polyoxyethyleue
alkyl (for exa~ilpleC 8.18) ether, cthyletle oxide adduct of alkyl naphthol, polyoxyethylene
(mo~loo r di) alkyl (for exanlple C8.12) phenyl ether, fonnalin condensate of a
polyoxyetliyle~ie(m ot10 or di) alkyl (for exaniple C8.12) plietiyl ether, polyoxyethylene
(mono, di, or tri) phenyl phetiyl ether, polyoxyethyle~le( mono, di, or tri) bcnzyl phenyl
20 ether, polyoxypropylene (mono, di, or tri) betlzyl phenyl ether, polyoxyethylene (mono,
di, or tri) styrylphenyl ether, polyoxypropylene (mono, di, or tri) styrylphenyl etlier,
polymer of polyoxyetliylene (mono, di, or tri) styrylphenyl ether,
polyoxyetliylene-polyoxypropylene (mono, di, or tri) styrylplieiiyl ether,
polyoxyetliylene-polyoxypropyle~ibel ock poly~ne~al;k yl (for example Cs~ls)
25 polyoxyethyle~ie-polyoxypropyleneb lock polymer ether, alkyl (for example CS.,~p)h enyl
[~olpoxyethylene-polyoxypropylenbelo ck polymer ether, polyoxyetliylene bisphenyl
cthel; polyox)~etI~ylenre sin acid ester, polyoxyethylene fatty acid (for example Cs.ls)
monoester, pol)~oxyetl~ylenfaet ty acid (for cxa~npleC 12.18) diestel; polyoxyetl~ylene
sol-bitan (mono, di, or tri) fatty acid (for example C8.18) estel; glycerol fatty acid ester
11
ethylene oxide adduct, polyoxyethylene castor oil ether, hydrogenated caslor oil ethylene
oxide adduct, alkyl (for cxa~iipleC 8.1s) atililie ethyler~eo xide adtluct, ant1 fatty acid (for
example Cs-ls) amide ethylene oxide adtluct.
(A-2) Polyhydric alcollol surfacta~itsE: xamples thereof include glycerol fatty acid
5 ester, polyglpcerol fatty acid ester, pentaerythritol fatty acid ester, sorbitol fatty acid (for
cxaniple C8.18) ester, sorbitall (mono, di, or tri) fatty acid (for exa~nplec 8.1~e)s tel;
sucrose fatty acid ester, polyliydric alcohol alkyl ether, aalid fatty acid alkanol amide.
(A-3) Acetylene surfactants: Examples thereof inclutie acetylene glycol, acetylene
alcohol, ethylene oxide adduct of acetylene glycol, atid ethylene oxide adduct of
10 acetylene alcoliol.
(A-4) Other surfactants: Examples thereof include alkyl glycosides.
[0041] (B) Anionic surfactants:
(l-1) Carhoxylic acid surfactants: Examples thereof include carboxylic acids, such
as poly acrylic acid, poly methacrylic acid, poly maleic acid, copolymer of maleic acid
15 and an olefin (for exaniple, isohutylenc, and diisohutylene), copoly~~loefr acrylic acid
and itaconic acid, copolymer of methacrylic acid and itaconic acid, copolymer of maleic
acid and styrene, copolymer of acrylic acid and methacrylic acid, copolymer of acrylic
acid and a methyl acrylate ester, copolymer of acrylic acid and vinyl acetate, copolymer
of acrylic acid and tnaleic acid, polyoxyethylene alkyl (for example C8-18) ether acetic
20 acid, N-methyl-fatty acid (C12.18) sarcosinate, resin acid, and fatty acid (for example
C8.18); aud salts of thesc carboxylic acids.
(B-2) Sulfuric acid ester su~factantsE: xamples thereof include sulfuric acid esters,
such as an alkyl (for example C12.18) sulfilric acid ester, polyoxyethylene alkpl (for
example Ce18)e ther sulfuric estei; polpoxyetl~yle~(m~eo no or di) alkyl (for example
25 C8.12)p lle~lyle ther sulf~~raiccid ester, sulhric acid ester of a polymer of a
polyoxyethylene (mono or di) alkyl (for exaniple C8.12) plienpl cthel; polyoxyethylene
(mono, di, or td) phenyl phenyl ether sulfuric acid ester, polyoxyethylene (mono, di, or
tri) be~izylp lienyl ether sulfuric acid cstcl; polyoxpetliylene (mono, di, or tri)
styrylphenyl ether sulfuric acid ester, sulfi~rica cid ester of a polymer of a
12
polyoxycthylenc (mono, di, or tri) styrylphenyl cthcl; sulfitric acid ester of a
polyoxyethylene-polyoxypropylene block polymer, sulfated oil, sulfated fatty acid ester,
sulfated fatty acid, and sulfated olefin; and salts of these sulfuric acid esters.
(R-3) Sulfonic acid surfactants: Examples thcreof include sulfotiic acids, such as
5 paraffin (for example Cs.22) sulfonic acid, alkyl (for example C8-12) benzene sulfonic acitl,
formalin condensate of an alkyl (Cs.12) benzene sulfonic acid, fornialin condensate of a
cresol sulfonic acid, a-olefin (for example CS.16s) ulfonic acid, dialkyl (for example Cs.]2)
sulfo succinic acid, lignin sulfotiic acid, polyoxycthylenc (nio~ioo r di) alkyl (for example
Cs.j2) phenyl ether sulfonic acid, polyoxyetliylene alkyl (for example C8.18) etlier sulfo
10 succinic acid half cstel; naphthalene sulfotiic acid, (mono or di) alkpl (for example CI.~)
naphthalene sulfonic acid, formalin condensate of a naphthalene sulfonic acid, fornialin
condensate of a (mono or di) alkyl (for example C1.6) naphthalene sulfonic acid, formalin
condensate of a creosote oil sulfonic acid, alkyl (for example C8.12) diplienyl ether
disulfotiic acid, Igepon T (product name), polystyrene sulfonic acid, and copolymer of a
15 styrene sulfonic acid and ~nethacrylica cid; and salts of these sulfonic acids.
(B-4) Phosphoric acid ester surfactants: Exatiiples thereof include pliosphoric acid
esters, such as an alkyl (for exa~npleC 8.12) pliosphoric acid ester, polyoxyethylene alkyl
(for example Cs.18) ether phosphoric acid ester, polyoxyethylene (tnotio or di) alkyl
(Cs-12)p lieuyl ether phosphoric acid ester, pliosphoric acid ester of a polymer of a
20 polyoxyethylene (tnono, di, or tri) alkyl (for example C8.12) plienyl ether,
polyoxyethylene (niono, di, or tri) phenyl phenyl etlier pliosphoric acid ester,
polyoxyetliylene (mono, di, or tri) benzyl phenyl etlier phosplioric acid estel;
polyoxyetliylene (mono, di, or tri) slyl-ylphenyl etlier pliosphoric acid estel; pliosphoric
acid ester of a polplncr of a polyoxyethylene (mono, di, or tri) styrylphenyl etlier,
25 phosphoric acitl ester of a polyoxyctliylene-polyoxyplupyle~ieb lock polynier,
pliosphatidylcholine, pl~ospliatidylctlia~ioliminea,n d condensed phosphoric acid (for
example, tripoly phosplioric acid); and salts of these phosphoric acid esters.
Examples of counter ions for salts in (B-I) to (B-4) above include alkali metals
(lithium, sodium, potassium, and the like), alkaline earth ~iictals(c alcium, magnesium,
13
and the like), amtnonium, and various amines (for example, alkylami~~cey,c loalkylaoiine,
and alkaliol arnine).
[0042] (C) Cationic surfactants:
Examples thcrcof include alkylamiiie salt, alkyl quater~iarya rn~~~onisualmt,
5 ethylene oxide adduct of an alkylamine, atid ethylene oxide adduct of an alkyl quaternary
atiitiionium salt.
[0043] (D) Ampl~oterics urfactants:
(D-1) Betaine surfactants: Examples thereof include alkyl (for example Cs.ls)
dimethylamino acetic acid betaine, acyl (for exaniple Cs.ls) a~ninopropyldimethylami~io
10 acetic acid betaine, alkyl (Tor example Cs.18) hydroxysulfo betaine, and 2-alkyl (for
example Cs.ls)-N-carboxymetliyl-N-hydroxyethylim idazolinium betaitie.
(D-2) Amino acid surfactatits: Exa~iiplesth ereof include alkyl (for example Cs.18)
anii~~proo pionic acid, alkyl (for example c8.1~)a mino dipropionic acid, a~idN -acyl (for
example Cs.18)-N'-carboxyetl~yl-N'-hydroxyethyl ethylenedia~nine.
15 (D-3) Amine oxide surfactants: Examples thereof include alkyl (for exaniple CS.~~)
dimetliylaniine oxide, and acyl (for example C8.1S) aminopropyl tlitnethylaniine oxide.
[0044] (E) Other surfactants:
(E-1) Silicon surfactants: Examples thel.eof include polyoxyethylene-methyl
polysiloxan copolymer, polyoxypropyletic-~netliylp olysiloxati copolymel; and
20 poly(oxyetliyle~ie-oxypropylene)-metl polysiloxa~ci opolymer.
(E-2) Fluorinated surfactants: Exan~plesth ereof include perfluoro alkeriyl
benzenesulfonate, perfluoro alkyl sulfonate, pel-kluoro alkyl carboxylate, perfluoro
alkenyl polyoxyethyle~iee tlier, perflooro alkyl polyoxyethylene etliel; atid perfluoro alkyl
trimethyl ammonium salt.
25 [0045] Among the surfactants above, polyoxyetliylene (~iionod, i, or tri)
styrylphe~~eytlli el; polyoxyethyle~ie-polyoxypropyle~biel ock polymer, acetyle~ied iol,
polyoxyetliylaie nono no, di, or tri) styrylphenyl etlier sulfuric acid ester or a salt thereof,
polyoxyetliylc~ie( IIIOIIOd,i , or tri) styrylphenyl etlier phosphoric acid ester or a salt
thereof, and dialkyl (CS.12) s~lfosi~cci~a~rea ptree ferable; a~idp olyoxpethylenc
14
tristyrylphenyl ether, ~~olyoxyctliylene-j>o1~~oxj~propbylloec1ki ep olymel; acetylene diol,
polyoxyetliylene tristyrylphenyl ether sulfuric acid ester salt, polyoxyetliylene
tristyrylphenyl ether phosphoric acid ester, and dioctyl sulfosnccinate are inore
preferable.
5 200461 Ill the composition of the present invention described in [2] to 191,
atnotlg tlie surfactants above, polyoxyetliylene (niono, di, or tri) styrglplienyl ether,
polyoxyethylene-polyoxypropylene block polymer, acetylene diol, polyoxyetliylene
(mono, di, or tri) styrylphenyl ether sulfuric acid ester or a salt thereof, and
polyoxyethylene (1110110, di, or tri) styrylphe~~eytlh er phosphoric acid ester or a salt
10 thereof are preferable; and polyoxyethylene tristyrylplienyl ether,
polyoxyethyletie-polyoxypropyleiie block polyme~; acetylene diol, polyoxyethylene
tristyrylphenyl ether sulfuric acid ester salt, and polyoxycthyiene tristyrylphenyl ether
phosphoric acid ester are Inore preferable.
[0047] Meanwhile in the coniposition of the present invention described in [lo]
15 to [23], among the surfacta~itsa bove, polyoxyethyle~ie( mono, di, or tri) styrylphenyl
ether, polyoxyethylene-polyoxypmpyle~ieb lock polynlet; and dialkyl (Cs.j2)
sulfosuccinate are preferable; and polyoxyetliylene tristyrylphenyl ether,
polyoxyethylene-polyoxyp~.opylenbelo ck polynier, aud dioctyl sulfosnccinate are niore
preferable.
20 [0048] The surfactant can be used singly, or can be used as a mixture of two or
niore of thetn. A total content of the surfactant is usually 0% by mass to 20% by tnass
based on a total Inass of the coniposition of tlie present invention. Note that as (b), a
content of tlie surfactant and a content of tlie later-mentioned protective colloid will not
concurrently be 0% by mass.
25 In the co~npositiono f the present invention described in [2] to [9], a total content of
the surfactant is usually 0.1% by mass to 20% by mass based on a total mass of tlie
con~positiono f the present inventio~~.T lie lower limit of the total content is preferably
0.1 % by tnass or above or 0.5% by tilass or above, and more preferably 1% by nlass or
above. Tlie upper li~iliot rthe total content is preferably 20% by mass or below or 10%
15
by mass or bclow, ant1 more preferably 5% by mass or below.
Mcanwl~ilcin the composition of the present invct~tiond escribed in [lo] to [23], a
total content of the surfactant is usually 0% by mass to 20% by mass based on a total
mass of the composition of the prcseot inve~itioil. In the case where the composition of
5 the present invention contains a surfactant, the lower limit of the total content is
preferably 0.1% by Illass or above, and more preferably 0.3% by Illass or abovc. The
upper linlit of the total content is preferably 20% by tnass or below, and marc preferably
10% by tnass or bclow.
[0049] The surfactant above can be used also as an adjuvant, for the purpose of
10 enhancing insecticidal and t~liticidala ctivities of the co~~ipositiootfi the present invention.
Exatiiples of other adjuvants include vegetable oils and niineral oils. 'These adjuvants
may be used by being contained in advance in the composition of the present inve~ition,
or ]nay be used by being mixed in a diluted solution of the composition of the present
invention.
15 [0050] A protective colloid used in the composition of the present invention is
not particularly limited, atid examples thereof iticl~~wdea ter soluble celluloses, such as
methylcellulose, hydroxyetliylcellulose, hydroxypropylcellulosc,
hydroxypropyltnethylcellulose, and carboxytnethylcellulose; polyalkylene glycols, such
as polyethylene glycol and polypropylene glycol; polyvinylalcohols;
20 polyvinylpyrrolidone; guar gem; gum arabic; gelatin; polyacrylates; arid alginates.
Among the protective colloids above, polyvinylalcohols are preferable.
[0051] The protective colloid can be used singly, or can be used as a mixture of
two or tilore ofthem. A total content of the protective colloid is usually 0% by mass to
10% by mass based on a total mass of thk composition of the present invention. As
25 previously mentioned, a content of tlie surfactant and a conte~iot f tlie protective colloid
will not concun-ently be 0% by mass as (b).
In the case where the coniposition of the present invention contains a protective
colloid, the lower limit ofthc total content is preferably 0.1% by niass or above, and
more preferably 0.3% by mass or above. The upper limit of the total content is
16
prcfcrably 10% by mass or bclow, and more preferably 5% by mass 01- belo\\?.
[0052] Ihe surfactant aud the protective colloid can be usetl singly, or can be
uscd in combination.
[0053] [(c) Solve~lt]
5 The solve~lut sed it1 the colnpositiorl of the present invention is not particularly
limited, and examples Illel-eof include fatty acid dimethylamide, N-alkyl-2-pyrrolido~~e,
aromatic hydrocarbon, and ester solvetlt. Examples of the ester solvc~i~~tl cluded ibasic
acid ester, fatty acid ester, and aromatic carboxylic acid ester,
100541 111 the composition of the present i~lventiond escribed in [2] to [9], a
10 nonpolar solvent is preferably used as a solvent, and the nonpolar solvent is i~sually
dispersed in water that is (d) ingredient. The nonpolar solvent is uot particularly limited,
aud the one usually has aqueous solubility at 20°C of less than 2 gIL, preferably of less
than 1.5 g k , attd more preferably of less than 1 g/L. Exa~liplesth ereof include aromatic
carboxylic acid ester, dibasic acid ester, fatty acid ester, and aromatic hydrocarbon. One
15 of, or a mixture of two or inore of these not~polars olvents nlay be used. A total content
of the nonpolar solvetlt is usually 1% by mass to 60% by mass based on a total mass of
the cornposition of the present invention. The lower lirnit of the total content is
preferably 20% by mass or above, and more preferably 30% by mass or above. The
upper limit of the total conteut is preferably 60% by mass or belo\\; and more preferably
20 50% by mass or below.
[0055] Examples of the aromatic carboxylic acid ester include aromatic
carboxylic acid esters that are esters of aro~ilaticc arboxylic acids, such as benzoic acid,
pllthalic acid, isophthalic acid, terephthalic acid, tri~llellitica cid, and pyromellitic acid
and C1.[3 alcoliols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol,
25 hexanol, octanol, 2-ethyl hexanol, isono~lyla lcohol, decyl alcohol, isodecyl alcohol,
tridecyl alcohol, and benzyl alcohol. Among the aromatic carboxylic acid esters above,
phthalic acid alkpl esters having C84) alkyl groups, such as ditridecyl plithalate,
bis(2-et1~yllicxyl)~11~tl~aantde ,d iaikyl (C10.12p) llthalate; and trimellitic acid alkyl esters
having Cs.lo elkyl groups, such as a trialkyl (Cs or Clo) trimellitate, tris(2-ethylhexyl)
17
11-imellitate,a nd triisodecyl trimellitate are prcfelable.
[0056] Exanlples of the dibasic acid ester iilclutle dibasic acid esters that are
cstcrs of C2.jo dicarboxylic acids, such as oxalic acid, malonic acid, succiaic acid, glutaric
acid, 2-~netliylglutarica cid, adipic acid, pimelic acid, suberic acid, azelaic acid, and
5 sebacic acid and Cl.lo alcol~olss, uch as metl~anole, thanol, pi-opanol, isopropanol, butanol,
isobutanol, hexanol, octanol, 2-ethyl hexanol, isononyl alcohol, decyl alcohol, and
isodecyl alcohol. Anlong the dibasic acid esters above, dibasic acid esters that are esters
of C6.{0 dicarboxylic acids, such as diisobutyl adipate and bis(2-ethylhexyl) sebacate aud
C4.S alcol~oisa re preferable.
10 [0057] Examples of tlle fatty acid ester include fatty acid esters that are esters of
Cl-18fa tty acids, such as fornlic acid, acetic acid, lactic acid, propionic acid, butyric acid,
valeric acid, caproic acid, caprylic acid, 2-ethylhexaaoic acid, capric acid, lauric acid,
myristic acid, pal~nitica cid, stearic acid, and oleic acid atld Cl.ts alcohols, such as
methanol, ethat~olp, ropanol, isopropaool, butanol, isobutanol, hexanol, octanol,
15 2-ethylhexanol, decyl alcohol, isodecyl alcohol, lauryl alcohol, tridecpl alcohol,
isotridecyl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, and oleyl alcohol or
polyhydric alcohols, such as ethylene glycol, propylene glycol, glycerin, sorbitan, and
pentaerpthitol; and fatty acid esters derived from vegetable oils, such as soybean oil,
flaxseed oil, castor oil, cocot~uot il, rapeseed oil, aud cottonseed oil. Among the fatty
20 acid esters above, fatty acid esters that are esters of Cs.18 fatty acids, such as
2-ethylhexanoic acid cetyl ester, methyl oleate, and isobutyl oleate aud C1.16 alcohols;
fatty acid triglycerides, suc11 as 2-etl~ylhexanoica cid triglyceride; and fatty acid esters
del.ived from vegetable oils, such as soybean oil fatty acid are preferable.
[0058] Exa~npleso fthe aro~llatich ydrocarbo~li nclude aromatic hydrocarbons,
25 such as xylene, alkyl (C9.13 and the like) benzene, phenylxylpl ethane,
dimethylnaphthalene, alkyl (Cl, C3, CIZ.~a.~n,d the like) naphthalcnc, alkyl biphenyl, and
alkyl diphenyl alkane; and aromatic hydrocarbons Iiavitlg boiling poiuts of 150°C to
35OoC. Among tlle aromatic hptlrocarbons above, plienylxylyl ethane is preferable.
[0059] Further, solvents other than the nonpolar solvents above can be uscd in
18
tlie composition of the present invention. Examples of other solvents include aliphatic
hydrocarbons, such as machine oil, normal paraffin, isoparaffin, and naplitliene; a mixture
of an aroiiiatic hydrocarbon ant1 aliphatic Iiydrocarbori, such as kerosene; alcohols, such
as ethanol, isopropanol, cyclohexanol, phcnoxyetha~iola, nd benzyl alcohol; polyhydric
5 alcohols, such as ethylene glycol, propyleric glycol, tliethylcne glycol, hexyletie glycol,
polyethylene glycol, and polypropylene glycol; ethers, such as propyl cellosolve, butyl
cellosolve, pheiiyl cellosolve, propylene glycol monomethyl ether, propylene glycol
monoetl~yel ther, propylene glycol ~iio~iopropcytll iel; propylene glycol tnonobutyl ether,
and propylene glycol nionophenyl etlier; ketones, such as acetophenone and
10 cyclohexa~ione;la ctones, such as y-butyrolactone; fatty acid dimcthylan~idesc omposed
of CI.12f atty acids, such as N,N-dimetliylforma~nideN, ,N-dimefhylacetatnide,
N,N-dimethyl octane amide, N,N- dimetliyl decane aniide, and N,N-dinietlyl dodecane
atnide; N-C1.12 alkyl-2-pyrrolid01les, such as N-methyI-2-pyrrolido11e,
N-ethyl-2-pymlidone, N-octyl-2-pyrrolidone, atld N-dodecyl-2-pyrrolidone; 5- to 6-
15 membered cyclic ureas, such as 1,3-dimethyl-2-imidazolidinonea nd N,N'-dimethyl
propylene urea; 4-acyln101-pllolines,s uch as 4-fomyfmorpl~oline,4 -acetylmorpholi~~e,
4-propionyliiiorpholinc, 4-butanoylniorpholitie, 4-pentaaoyln1orplloline,
4-hexa~~oylmorpholin4e-,h eptatloyln~orpholine,4 -octanoylmorplioli~ie,
4-nonanoyl1norphaline, 4-decanoylmorplioline, 4-undecanoylniorplioline, and
20 4-dodecanoyl~norpl~olinfea;t s and oils, such as soybean oil, flaxseed oil, canola oil,
cocoiiut oil, cottonseed oil, and castor oil; and dimetliyl sulfoxidc.
[0060] 't'he solvent used in the composition of the present invention described in
[lo] to [23] is not particularly limited, and tlie solvent is usually a solvent that has
aqueous solubility at 20°C of less tliat~ 100 g/L, preferably of less than 75 g/L, and more
25 preferably of less than 50 g/L. The solvent is not particularly limited, and examples
thereof include fatty acid di~nethylamide,N -elkyl-2-pyrrolidone, aromatic hydrocarbon,
and ester solvent. 111 order to fitrtlicr improve tlie preservation stability at low
temperatures of tlie composition of the present invention, a mixture of at least one
selected f i w t~he group (e) below and at Icast one selected fiom the group (0b elow is
19
preferably used as a solvent.
(e) A fatty acid dimethylamide and an N-alkyl-2-pyrrolidone.
(f) An aromatic hydrocarbon and an cstcr solvent.
[0061] A content of at least one solvent selected from the group (e) is t~sually
5 5% by 111ass to 50% by mass based on a total 111ass of the conipositioii of the pxscnt
invention. The lower limit of tlie content is preferably 10% by mass or above, and more
preferably 20% by mass or above. The upper limit of tlie content is preferably 50% by
mass or below, and more preferably 35% by mass or below.
A content of at least one solvent selected from the group (f) is usually 1% by mass
10 to 20% by mass based on a total mass of the co~npositiono f the present invention. The
lower limit of the content is preferably 1% by mass or above, and more preferably 2.5%
by mass or above. The upper limit of the colitent is prefelably 20% by mass or below,
and tilore preferably 17.5% by mass or below.
Also, a total content of solvent(s) is usually 10% by mass to 60% by mass based on
15 a total mass of the conipositiotl of the present invention. The lower limit of the total
content is preferably 10% by mass or above, and more preferably 20% by mass or above.
The upper limit of the total content is preferably 55% by mass or belowv, and moiE
preferably 50% by mass or below.
[0062] Examples of the fatty acid dimethylamide include fatty acid
20 dimethylamides composcd of C1.12 fatty acids, such as N,N-dimetliylformaniide,
N,N-dimethylacetamide, N,N-dimethyl lactic acid amide, N,N-dimethyl octane amide,
N,N-dimethyl decane amide, and N,N-dimethyl dodecane amide. Among the fatty acid
dimethylamides above, fatty acid dimethylamides colnposed of Cs.10 fatty acids, such as
N,N-dimethyl octane amidc, N,N-dimethyl decane a~nidea, nd mixtures thereof are
25 preferable.
[0063] Exaniples of the N-alkyl-2-pyrrolidone include N-alkyl-2-pyrrolidones
having a CI.12 alkyl group, such as N-1nethyl-2-pyrrolidonc, N-ethyl-2-pyrrolidone,
N-octyl-2-py1.rolidone,a nd N-laurpl-2-ppn.olido~ie. Among the N-alkyl-2-pyn.olidol,es
above, N-oclyl-2-pyrrolidone is preferable.
20
[0064] Exainples of the aromatic hydrocarbon include abniatic hydrocarbons,
such as xylene, alkyl (Ce.l, and the like) benzenc, plicnylsylyl ethane,
diniethylnaphtliale~le, alkyl (CI, C3, CI2.l4, and the like) naphtl~alenca, lkyl biphenyl, and
alkyl diphenyl alkane; a~ida rortiatic ilydrocarbons haviiig boilii~gp oints of 150°C to
5 350%
100651 The cster solvent used in the composition of the preseut inventio~is not
particularly limited, and the ester solve~iits usually a solvent that has aqueous solubility
at 20°C of less that1 100 g/L, preferably of less than 75 g/L, aud Inore prcfcrably of less
than 50 dL. Specific examples thereof iliclude aro~naticc arboxylic acid esters, such as
10 dibasic acid ester, fatty acid ester and benzoic acid estel; phthalic acid alkyl cster,
isophthalic acid ester, terephthalic acid ester, tritnellitic acid alkyl ester, and pyrotnellitic
acid ester. Alnol~gth e ester solvents above, dibasic acid cster aud fatty acid ester are
preferable.
[0066] Examples of the dibasic acid ester include dibasic acid esters that are
15 esters of C2.10 dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, glutaric
acid, 2-tnethylglutaric acid, adipic acid, pi~nelica cid, suberic acid, azelaic acid, and
sebacic acid and Cl.lo alcohols, such as methanol, ethanol, propanol, isopropanol, butanol,
isobutanol, hexanol, octanol, 2-ethyl hexanol, isono~~ayllc ohol, decyl alcoliol, and
isodecyl alcohol. Alllong the dibasic acid esters above, dibasic acid esters that are esters
20 of C4-6 dicarboxylic acids, soch as diisobutyl succinate, diisobutyl glutarate,
2-~nethylgiutarica cid dimethyl ester, and diisobutyl adipate aud C1.4 alcohols are
preferable.
100671 Examples of the fatty acid ester include fatty acid esters that are esters of
CI.18 fatty acids, sucl~a s forinic acid, acetic acid, lactic acid, pmpionic acid, butyric acid,
25 valeric acid, caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid,
~nyristica cid, palinitic acid, stearic acid, and oleic acid and c1.1a8lc ohols, such as
methanol, ethanol, propanol, isopropanol, butanol, isobuta~~oll~,e xal~oolc,t al~ol,
2-ethylhexanol, decyl alcohol, isodecyl alcohol, lauryl alcohol, tridecyl alcol~ol,
isotridecyl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, and oleyl alcohol or
21
polpllydric alcohols, such as ctllylene glycol, propylene glycol, glycerin, sorbitan, and
pentaerythritol; and fatty acid estel-s derived fro111 vegetable oils, such as soybean oil,
flaxseed oil, castor oil, coconut oil, rapeseed oil, and cottonseed oil. Among thc fatty
acid esters above, fatty acid esters that are esters of C3.8 fatty acids, soch as butyl lactate,
5 lactic acid 2-ethylhexyl cster, and ~nctliycl aprylate autl alcoliols are preferable.
[0068] Further, solvents other than the solvents above call be used in tlie
co~npositiono f the present invention. Examples of other solvents include aliphatic
hydrocarbons, such as tnacl~ineo il, normal paraffin, isoparaffin, and naphthene; a mixture
of aromatic hydrocarbon and aliphatic hydrocarbon, such as kerosene; alcohols, such as
10 ethanol, isopropanol, cyclohexanol, phenoxyethanol, and benzyl alcohol; polyhydric
alcohols, such as ethylene glycol, propylene glycol, dietliylene'glycol, hexylene glycol,
polyethylene glycol, and polypropylene glycol; ethers, such as propyl ccllosolve, buty1
cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol
molloetllyl ether, propyle~~gley col monopropyl ether, propylene glycol tnonobutyl ethel;
15 and propylene glycol monopbe~iyel ther; ketones, such as acetophenone and
cyclohexanone; lactones, such as y-butyrolactone; 5- to 6- me~nbefed cyclic ureas, such
as 1,3-dimethyl-2-i1nidazolidinonaen d N,N'-dimethyl propylene urea; 4-acylmotpi~olines,
such as 4-fornlyl11iorpholi11e4, -acetylmorp11oline, 4-propionylniorl~holine,
4-butanoylmorpliolitie, 4-pe1itanoylt1iorpl~oline4,- hexanoylmorpholine,
20 4-l~eptatloplmorplloli1~4e-,o ctanoyltnor~~holin4e-,n onanoylmorpliolitie,
4-decanoyl~norplioline4, -undecanoylmorpholine, and 4-dodecanoyl~norrplioline;f ats and
oils, such as soybean oil, flaxseed oil, canola oil, coconut oil, cottonseed oil, and castor
oil; and dimethyl sulfoxide.
[0069] [(d) Water]
25 A liquid cotnposition of the present invention contains water, and a content thereof
is usually 25% by mass to 75% by mass based on a total mass of the composition of tlie
prezent invention.
[0070] [Auxiliary ingredient]
Examples of auxiliary ingredients that call be furtlier used iri the composition of the
22
present in\rcntion include tliickcncrs, antifreezing agents, pH regulators, tiecomposition
inhibitors, antifaanling agents, and preservatives.
[0071] The thickener is not particularly limited, and olganic or inorganic
substances, whiclt are natural, synthetic, or scmisy~~tl~ecatinc b e used. Specific
5 exanlples thereof include Iieteropolysaccharidcs, such as xanthan gum, welan gum, and
rliatnsan gum; water-soluble polymer compounds, such as polyvinpl alcoliol, polyvinyl
pyrrolidone, polyacrylic acid, sodiuni polyacrylate, and polyacrylamide; cellulose
derivatives, sucli as methyl cellulose, carboxymctllyl cellulose, carboxyethyl cellulose,
hydroxyethyl cellulose, and hydroxypropyl cellulose; and slnectite clay minerals, such as
10 monttnorillonite, saponite, liectorite, bentonite, Laponite, and synthetic smectite. These
thickeners can be used singly, or two or tnore of thetn can be used as a mixture, and any
mixing ratio can be selected. These thickeners can be added directly, or can be added
after being dispersed in water.
[0072] As the antifreezing agent, for exanlple, ethylene glycol, dietliylcne glycol,
15 propylene glycol, and glycerin can be used. Among them, propylene glycol and
glycerin are preferable. As a content of tlie antifteezing agent in the coniposition of the
present invention, any amount can be selected.
[0073] Examples of the pH regulator include sodium carbonate, sodium
bicarbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, calciutn
20 hydroxide, sodium borate, l~yd~ocl~loarciidc, nitric acid, phosphoric acid, citric acid,
acetic acid, oxalic acid, plltl~alica cid, benzoic acid, succinic acid,
ethylenediatninetetraacetic acid, sodiuni citrate, disodiuln Iiydrogen ~~hosphatseo,d iuni
dihydrogen phospllate, dipotassiurn hydrogen phosphate, and potassium dihydrogen
phosphate.
25 [0074] Examples of the antifoan~ingag etit include silico~iee mulsion.
[0075] The method for producing the composition of the present inventiou is not
particularly limited, and the tnethod includes adding tl~eaf orementioned ing~.edientsi n
watcl; and mixing them with a ~nixerto obtain the composition. In addition to the
conventiot~alm ixer, for example, emulsifying dispcrscrs, such as planetary mixers,
23
Microfluidizers, Ilomomixers, homorlispers, homogenizers, antl colloid tnills can be used.
If necessary, each of pesticide active ingredients, st~rfactantsa, ud othel. auxiliary agents
]nay be pulverized in a tlry or wet pulverizer individually, or as a mixture thereof.
Dry pulverization can be conducted by using an impact pulverizer, a bba mill, a jet
5 mill, or the like. \Vet pnulerization can be conducted by using a wet pulverizer, such as
an attritol; a sand grinder, a dyno-mill, a pearl tnill, an apex mill, a visco mill, and an
ultra visco mill.
[a0761 By using the composition of the present invention in common methods
used by those skilled in the art, such as a foliage treatment, a soil treat~nenta, tray
10 treatment, and a seed disinfection, pest control for l~annfuol rganisms can be conducted.
In cases of a foliage treatment or a soil treatment, the co~npositiono f tlle present
invention can be applied to crops, trees, or soil wllere they gmw, by spraying the
cornposition as diluted approxirnately 10 times to 5,000 tirnes usually with water, by
using a sprayer or the like; or by spraying the co~npositiona s straight or as diluted
15 approximately 2 tin~etso 100 titnes with water, fro111 the air by using a flying helicopter
or the like. Note that when the co~npositiono f the present invention is actually applied
(at the time of spraying), a concentration of Cotnpound A is usually 5 ppm to 200 ppm.
Exatnples
20 [0077] Hereinafter, the present invention will be explained in furtiler detail
according to Examples, Comparative Examples, and Test Examples below; however, the
present itlventio~ils not li~nitedto these examples. Note that the "part(s)" described
below refers to part(s) by mass.
[0078] [Example I]
25 I. Preparation of Pulverized Slurry
In 11.3 1 parts ofwater, 2 parts of polyoxyethylene tristyrylphenyl ether phosphate
ester [product name: SOPROPEIOR 3D33, n~anufactoredb y Rhodia Nicca, Ltd.], 0.5
parts of polyoxyethylenc polyoxypropylene glycol [product name: EI'AN 750,
n~anofacturedb y Dai-ichi Kogyo Seiyaku Co. Ltd.], 0.05 parts of
24
2,4,7,9-tetrarnethyl-5-decyne-4,7-diol[p roduct oalne: Surfynol 104PG50, nianufactured
by Air Proclucts and Chetnicals, Inc.], 0.2 parts of a silicone antifoaming agelit [product
name: KM-73, inanufactured by Shin-Etsu Chemical Co., Ltd.], 0.9 parts of citric acid,
aud 5 parts ofpropylene glycol were dispersed. In the obtained dispersion liquid, 10.04
5 parts of Compound A as a technical product (purity: 99.6%) was further dispersed, and
then the dispersion liquid was wet milled with glass beads having sizes of 0.8 nim+ to 1.2
mm$ by using a sand grinder [manufactured by AIMEX Co., Ltd.] to obtain 30 parts of
pulverized slurry.
2. Preparation of Dispersion Medium
10 111 37.8 parts of water, 0.1 parts of xanthan gum lproduct name: KELZAN ASX,
manufactured by SANSHO Co., Ltd.] and 0.1 parts of 1,2-benzisothiazolin-3-one
[product name: PKOXEL GXL, Manufactured by Nitto Denko Avecia Inc.] were
dispersed to obtain 38 parts of a dispersion medium.
3. Preparation ofAqueous Suspension Pesticide Composition
15 30 parts of the pulverized slurry and 38 parts of the dispersion medium were mixed,
and then 32 parts of ditridecpl phthalate [product name: VINYCIZER 20, nianufactured
by Kao Corporation] was added thereto, to be dispersed unifortnly, so that 100 parts of an
aqueous suspension pesticide colnposition of the present invention was obtained.
[0079] [Example 21
20 I'roduction was conducted by the same mcthod as in the case of Example 1, except
that 37.8 parts of water for a dispersion ~nediu~inu E xample 1 was changed to 21.8 parts,
and 32 parts of ditridecyl phthalate in Example 1 was changed to 18 parts to obtain 100
parts of an aqueous suspension pesticide con~position.
[0080] [Example 31
25 Production was conducted by the same method as in the case of Example 1, except
that 37.8 palls of water for a dispersion medium in Example 1 was changed to 22 parts,
0.1 parts of xanthan gum in Example 1 was changed to 0 parts, 0.1 parts of
1,2-be1izisotl1iazolin-3-onien Example 1 was changed to 0 parts, and 32 parts of
ditridecyl plitlialate in Exan~ple1 was changed to 48 parts of bis(2-etliylliexyl)phtha~alate
25
[product namc: VINYCIZER 80, manufactured by Kao Corporatioi~]to obtain 100 pasts
of an aqueous suspension pesticide composition.
[008 11 [Example 41
Production was conducted by the same method as in the case of Example 3, except
5 that 48 parts of bis(2-etI~yll~exyl)p1~tii~n aEtxea mple 3 was changed to 48 parts of
dialkyl (CI~.12p)h thalate [product name: VINYCIZER 124, manufactured by Kao
Corporation] to obtain 100 parts of an aqueous suspe~lsiorpl esticide composition.
[0082] [Example 51
Productio~lw as conducted by the same uiethod as in the case of Example 2, except
10 that 48 parts of ditridecyl phthalate in Example 2 was changed to 48 parts of trialkyl (Cs
or Clo)t rimellitate [product name: TRIMEX N-08, n~ailufacturedb y Kao Corporatiou] to
obtaiu 100 parts of an aqueous suspension pesticide cotnposition.
[0083] [Example 61
Production was conducted by the same tnethod as in the case of Exaiuple 5, except
15 that 11.3 1 paits of water for pulverized sluriy in Example 5 was changed to 12.2 1 parts, 2
parts of polyoxyetllylene tristyrylphenyl ether pl~osphorica cid ester in Example 5 was
cllailged to 2 parts of a mixture of polyoxyethylene tristyrylphenyl ether and a
polyoxyalkylene glycol [product name: SORPOL 3353, matmfactured by TOW0
CHEMICAL MDUSTRY Co., Ltd.], and 0.9 parts of citric acid in Exainple 5 was
20 changed to 0 parts to obtain 100 parts of an aqueous suspension pesticide composition.
[0084] [Example 71
Productiotl was conducted by the same mcthod as in the case of Example 6, except
that 2 parts of a inixtoi-e of polyoxyethylcne tristyrylphenyl ether and a polyoxyalkylene
glycol in Example 6 was changed to 2 pasts of a polyoxyethylene tristyrylphenyl ether
25 sulfnric acid ester ammoniuin salt Cproduct ]lame: SORPOL'r-ISSPG, manufactored by
TOHO CHEMICAL INDUSTRY Co., Ltd.] to obtaitl 100 parts of an aqueous sospension
pesticide coinposition.
[0085] [Example 81
I'soduction was conducted by the same method as in the case of Example 2, except
26
that 48 parts of ditridecyl plithalate in Esamplc 2 was changed to 48 parts of
tris(2-ethylhexyl) trimellitate [product name: 'I'RIMEX T-08, manufactured by Kao
Corporation] to obtain 100 parts of an aqueous suspension pesticide composition.
[0086] [Example 91
5 Production was conducted by the same niethod as in the case of Example 2, except
that 48 parts of ditridecyl phthalate in Exa~nple2 was changed to 48 parts of triisodccyl
triinellitate [product name: TRIMEX T-10, manufactured by Kao Corporatioii] to obtain
100 parts of an aqueous suspension pesticide composition.
[0087] [Example 101
10 Production was conducted by the satlie method as in the case of Example 3, cxcept
that 48 parts of bis(2-etliylliexyl)phtl~alatein Exaniple 3 was changed to 48 parts of
diisodecyl adipate [product name: VINYCIZER 50, niaiiufactured by Kao Corporation]
to obtain 100 pats of an aqucous suspensiozi pesticide cotnposition.
[0088] [Example 1 1 ]
15 Production was conducted by the same method as in the case of Example 2, except
that 11.3 1 patts of water for pulverized slurry in Exatnple 2 was changed to 11.07 parts,
10.04 parts of ConipoundA as a technical product (purity: 99.6%) in Example 2 was
changed to 10.28 palls of Compound A as a technical product (purity: 97.3%), and 48
parts of ditridecyl phthalate it1 Example 2 was changed to 48 parts of bis(2-etliylhexyl)
20 sebacate to obtain 100 parts of an aqueous suspc~isionp esticide composition.
[0089] [Example 121
Prod~ictiouw ss conducted by the same method as in tlie case of Example 1, except
that 32 parts of ditridecyl plithalate in Exatnple 1 was changed to 32 pats of tiietliyl
oleate [product name: EXCEPARL M-OL, inanufactured by Kao Corporatioil] to obtain
25 100 parts of an aqueous suspension pesticide composition.
[0090] [Example 131
Production was conducted by the same method as in the case of Esaniplc 2, except
that 48 parts of ditridecyl plithalate in Example 2 was changed to 48 parts of isobutyl
olcate [product name: VINYCIZEII 30, maniifactu~-edb y Kao Corporation] to obtain 100
27
parts of an aqueous suspension pesticide composition.
[0091] [Example 141
Productioo was conducted by the same method as it1 the case of Examplc 2, exccpt
that 48 parts of ditridecyl phtltalate in Example 2 was changed to 48 parts of
S 2-ethylhexanoic acid cetyl ester [product name: EXCEPARL HO, matlofactured by Kao
Corporation] to obtain 100 parts of an aqueous suspension pesticide composition.
[0092] [Example 151
Production was conducted by the sarne method as in the case of Example 2, except
that 48 palls of ditridecyl phthalate in Example 2 was chailged to 48 parts of a vegetable
10 oil fatty acid ester [procluct natne: VEGE-SOL MM, ma~lufacturedb y KANEDA Co.,
Ltd.] to obtain 100 parts of an aqueous suspension pesticide composition.
[0093] [Example 161
Production was coiiducted by the same method as in the case of Example 11, except
that 48 paits of bis(2-ethylhexyl) sebacate ia Example 11 was changed to 48 parts of a
15 soybean oil fatty acid ester [product name: VEGE-SOL CM, manufactured by KANEDA
Co., Ltd.] to obtain 100 palts of an aqueous suspe~~siopens ticide composition.
[0094] [Example 171
Production was conducted by the same method as in the case of ~xampl2e, exccpt
that 48 parts of ditridecyl phthalate in Example 2 was changed to 48 parts of
20 2-cthyll~exanoica cid triglyceride [product natne: EXCEPARLTGO, manufactured by
Kao Co~-poration]to obtain 100 parts of an aqueous suspension pesticide composition.
[009S] [Example 181
Production was conducted by the same method as in the case of Example 11, except
that 48 parts of bis(2-ethplhexyl) sebacate in Example 11 was changed to 48 parts of
25 phenylxylyl ethane [product natne: Nisseki Hisol SAS-296, manufactured by Nippon
Petrochemicals Co., Ltd.] to obtaiu 100 parts of an aqueous suspension pesticide
composition.
[0096] [Example 191
In 48.67 parts of water, 0.06 parts of xanthan gun1 [product name: KELZAN S,
28
manufactu~.ed by SANS110 Co., Lttl.] was dispersed, and then 0.03 parts of
1,2-be1izisothiazolin-3-one[p roduct name: Proxel GXL(S), nlanufactured by Nitto Dcnko
Avecia Inc.], 0.1 parts of a silicone antifoaming agent [product name: KM-73,
manufactured by Shin-Etsu Cheniical Co., Ltd.], 5 parts ofpropylene glycol, atld 6 parts
5 of polyoxyethylene styrylphetiyl ether [product name: Noigc~Ei A-207D, ma~iufach~rcd
by DKS Co. Ltd.] were dispersed to obtain a dispersion ~nediu~nN. ext, 5.14 parts of
CompoundA as a technical product (purity: 97.3%), 30 parts of a mixture of
N,N-dimethyl octane amide and N,N-dimethyl decalie alnidc [product name: Agniquc
AMD 810, manufactured by BASF Corporation], and 5 parts of an aroinatic hydrocarbon
10 [product name: Cactus Fine SF-02, manufacturcd by JX Nippoll Oil & Energy
Corporation] were nlixed to obtain a Con~poundA solution. The Compound A solution
was added to tlie dispersion medium, and was dispersed uniformly to obtain 100 parts of
an oil-in-water emulsion pesticide composition.
[a0971 [~xampl2i0 1
15 Production was conducted by the same method as in the case of Exa~~ip1l9e, except
that 48.67 parts of water in Exarnple 19 was changed to 43.67 parts, and 5 parts of an
aromatic hydrocarbon in Example 19 was changed to 10 parts to obtain 100 parts of an
oil-in-water emulsion pesticide composition.
[0098] [Example 211
20 Production was conducted by the same method as in the case of Example 19, except
that 48.67 paits of water in Example 19 was cllanged to 38.67 parts, and 5 parts of an
aromatic hydrocarbon in Exan~ple1 9 was changed to 15 parts to obtain 100 parts of an
oil-in-water emulsion pesticide composition.
[0099] [Example 221
25 Production was conducted by the sanie method as in the case of Example 19, except
that 48.67 parts ofwater in Example 19 was changed to 53.67 parts, and 5 parts of an
aromatic hydrocarbon in Example 19 was changed to 0 parts to obtain 100 parts of an
oil-in-water elnulsiotl pesticide composition.
[0100] [Example 231
29
111 50.61 parts of water, 0.1 parts of xantlian gum [product name: KE1,ZAN S,
~nanufactured by SANSIIO Co., Ltd.] was dispersed, and then 0.05 parts or
1,2-benzisot11iazolin-3-on[pe roduct name: Proxel GXL(S), manufactured by Nitto Denko
Axrecia Inc.], 0.1 parts of a silicone antifoatning agent [product name: Kh4-73,
5 manufactured by Shin-Etsu Chemical Co., Ltd.], 5 parts of glycerin, alid 4 parts of
polpoxyethylene styrplpllenyl ether [product name: Noigell EA-207D, manufactured by
DKS Co. Ltd.] were dispersed to obtain a dispersion medium. Next, 5.14 parts of
Compound A as a tech~iicapl roduct (purity: 97.3%), 25 parts of N-octyl-2-pyrrolidone,
and 10 parts of an aromatic hydrocarbot~ [product name: Cactus Fine SF-02,
10 manufactured by JX Nippon Oil & Energy Corporation] were mixed to obtain a
Conlpound A solutiot~. The Con~poundA solution was added to the dispersion medium,
and was dispersed unifonnly to obtain 100 parts of an oil-in-water emulsion pesticide
co~nposition.
[0101] [Example 241
15 Production was conducted by the same method as in the case of Exa~llple2 3, except
that 50.61 palis of water in Exatnple 23 was changed to 60.61 parts, and 10 parts of an
aromatic hydrocarbon in Exaniple 23 was changed to 0 parts to obtain 100 parts of an
oil-in-water emulsion pesticide composition.
[O 1021 [Example 251
20 In 46.61 parts of watcr, 0.1 parts of xanthan gum [product name: KELZAN S,
manufactured by SANSHO Co., Ltd.] was dispersed, and then 0.05 palis of
1,2-benzisotl1iazoli11-3-on[pe roduct name: Proxel GXL(S), manufactured by Nitto Det~ko
Avecia Inc.], 0.1 parts of a silicone antifoaming agent [product name: KM-73,
manufactured by Shin-Etsu Chemical Co., Ltd.], 5 parts of glycerin, and 3 parts of a
25 polyoxyetl~ylene-poI)~ox)~~~ropylbeloncek copolymer [product name: EPAN U-108,
manufactured by DKS Co. Ltd.] were dispersed to obtain a dispersion medium. Next,
5.14 parts of Compound A as a technical pl-odoct (pufity: 97.3%), 30 parts of a mixture of
N,N-dimethyl octane amide and N,N-dirnethyl decane amide [product name: Agoique
AMI) 810, nranufactul-ed by BASI: Corporation], and I0 parts of an aromatic
30
hydrocarbon [product name: Cactus Fine SF-02, manufactured by JX Nippon Oil &
E11crgy Corporation] werc mixed to obtaiu a Compound A solution. The Compound A
solutio~wi as added to the dispersion medium, and was dispersed ~tnifonnlpto obtain 100
parts of an oil-in-water cm~rlsionp esticide composition.
5 [0103] [Example 261
Production was conducted by the same method as in the case of Example 25, except
that 46.61 parts of water in Example 25 was changed to 56.61 parts, and 10 parts of an
aromatic hydrocarbon in Example 25 was changed to 0 parts to obtain 100 parts of an
oil-in-water e~iiulsionp esticide cotnpositio~~.
10 [Ol 041 [Example 271
In 42.1 1 parts of water, 0.1 parts of xanthatl gum [product name: KELZAN S,
~nanufacturedb y SANSHO Co., Ltd.] was dispersed, and then 0.05 parts of
1,2-benzisotl1iazoli11-3-on[pe roduct name: Proxel GXL(S), manufactured by Nitto Denko
Avecia Inc.], 0.1 parts of a silicone antifoaming agent [product name: KM-73,
15 manufactured by Shin-Etsu Chemical Co., Ltd.], 5 parts of propylenc glycol, 0.5 parts of
dioctyl sulfosuccinate sodium salt [product name: AlRKOLL CT- lL, manufactured by
TOHO CHEMICAL INDUSTRY Co., Lid.], and 7 pxts of a 20% polyvinyl alcohol
aqueous solutiotl [product name: Polyace A-520G, manufactured by TAISEl KAYAKU
CO., Ltd.] were dispersed to obtain a dispcrsio~m~e dium. Next, 5.14 parts of
20 Compound A as a technical product (purity: 97.3%), 30 parts of a mixtore of
N,N-dimethyl octane amide and N,N-dimethyl decane amide [product name: Agnique
AMD 810, manufactut.ed by BASF Corporation], and 10 parts of an aromatic
hydrocarbon [product name: Cactus Fi~icS F-02, manufactured by JX Nippon Oil &
Energy Corporation] were n~ixedto obtain a C O ~ ~ ~ JAO soUluItiIo~n. The Con~l~ounAd
25 solution was added to the dispersion medium, and was disj~ersed uniformly to obtain 100
parts of an oil-in-water enlr~lsionp esticide compositioil.
[OI 051 [Example 281
Production was conductetl by the same method as in the case of Example 27, except
that 42.1 1 parts of \+later in Example 27 was changed to 52.1 1 parts, and I0 parts of an
31
aromatic llydrocarbon in Example 27 was changed to 0 parts to obtain 100 pats oran
oil-in-water emulsion pesticide co~nposition.
[O 1061 [Exatmiple 291
In 40.61 parts of water, 0.1 parts of xantliati gum [product nanme: KELZAN S,
5 matiufactu~-edb y SANSHO Co., Ltd.] was dispersed, a ~th~end 0 .05 parts of
1,2-betizisothiazoli1i-3-one [product name: Proxel GXL(S), manufactured by Nitto Denko
Avecia Inc.], 0.1 parts of a silicone antifoaming agent [product riame: KM-73,
manufactured by Shin-Etsu Chemical Co., Ltd.], 5 parts of glycerin, and 9 parts of a 20%
polyvi~iylalcoliol aqueous solution [product name: Polyace A-520G, manufactured by
10 TAISEI KAYAKU CO., Ltd.] were dispersed to obtain a dispersion medium. Next, 5.14
parts of Cotnpound A as a teclnmical product (purity: 97.3%), 30 parts of a ~nixtureo f
N,N-ditnethyl octane ainide and N,N-dimethyl decane amide [product name: Agiiique
AMD 810, nianufactured by BASF Corporation], arid 10 parts of an aromatic
hydrocarbon [product name: Cactus Fine SF-02, manufactured by JX Nippon Oil &
15 Energy Corporation] were nmixed to obtain a Compound A solution. The Co~npoundA
solution was added to the dispersion medium, and was dispersed uniformly to obtain 100
parts of an oil-in-water e~nulsionp esticide composition.
[0107] [Example 301
Production was conducted by the same nietliod as in the case of Exanmple 29, except
20 that 10 parts of an aromatic hydrocarbon in Example 29 was changed to 10 parts of
diisobutyl adipate [product name: VINYCIZER 40, ~uanufactured by Kao Corporation] to
obtain 100 parts of an oil-in-water einulsion pesticide composition.
[0108] [Example 3 I]
Production was conducted by the same method as in the case of Example 29, except
25 that 10 parts of an aromatic hydrocarbon in Example 29 was changed to 10 parts of a
2-~i~ethylglutaraici d diniethyl ester [product name: Khodiasolv IRIS, manufactured by
Rhodia Nicca, Ltd.] to obtain 100 parts of an oil-in-water emulsion pesticide
compositioii.
[Ol09] [Example 321
32
Production was conducted by the same methoti as in the case oTExarnl11e 29, except
that 10 parts of an aromatic l~ydrocarbonin Example 29 was changed to 10 parts of a
mixture of diisobutyl glutarate, diisobntyl succinate, and diisobutyl adipatc [product
name: Rhodiasolv DIB, manufactnrcd by Rhodia Nicca, Ltd.] to obtain 100 parts of an
5 oil-in-water emulsion pesticide co~nposition.
101 101 [Example 331
Production was conducted by the same method as in the case of Example 29, except
that 10 parts of an aromatic hydrocarbon in Example 29 was changed to 10 parts of a
lactic acid 2-etl~yll~exeyslt er [product name: Purasolv EHL, manufactured by Corbion
10 I'urac Co., Ltd.] to obtain 100 parts of an oil-in-water e~nulsionp esticide con~position.
[Ol 1 11 [Example 341
Production was conducted by the same method as in the case of Example 29, exccpt
that 10 parts of an aromatic hydrocai-ban in Example 29 was changed to 10 parts ofbutyl
lactate lproduct name: Purasolv BL, manufactured by Corbion Purac Co., Ltd.] to obtain
15 100 parts of an oil-in-water emulsion pesticide composition.
[0112] [Example 351
Production was conducted by the same method as in the case of Example 29, except
that 10 parts of an aromatic liydrocarbotl in Example 29 was changed to 10 parts of
lnetllyl caprylate [product name: PASTELL M-8, manufactured by Lion Corporation] to
20 obtain 100 parts of an oil-in-water emulsion pesticide cotnposition.
101 131 [Example 361
Production was conducted by the same method as in the case of Example 29, except
that 40.61 parts of water in Exan~ple2 9 was changed to 50.61 parts, and 10 parts of an
aromatic hydrocarbon in Example 29 was changed to 0 parts to obtain 100 parts of an
25 oil-in-water enlulsion pesticide con~posilion.
[0114] [Co~nparativeE xa~nple1 1 Preparation of Pesticide Emulsifier
Composition
10.04 parts of Compound A as a technical product (purity: 99.6%), 5 parts of
polpoxyethylene tristyrylphenyl ether [product name: SORPOLT-20, tnanufactured by
33
'1'01-10 CHEMICAL INDUSTRY Co., Ltd.], 5 parts of calciu~nd odccylbenzenesulfonate
[product iialilc: SORPOL EX-1 5, manufactured by 'SOH0 CllEMICAL INDUS'1'KY Co.,
I,td.], 55 parts of cyclohexatione, and 24.96 parts of an aromatic hydrocarbon [product
name: Cactus Fine SF-02, manufactured by JX Nippon Oil & Energy Corporation] were
5 ~nixettlo obtain 100 parts of a pesticide eniulsifier composition.
[0115] [Test Exa~nple1 1 Eff~cacyT est for Melon Thrips (T/?ripspc~lt~Fteil)u ale
Adult Insect
A styrol cup (having tlie diameter of the lid of 7.5 cm, and the height of 4 c~nw) as
filled with tap water, atid a lid having a hole in its center was placed on the styrol cup,
10 and a filter paper was placed on tlie lid to absorb tap water. An absorbent cottoll (5 cm
x 5 cni) wetted with tap water was placed on the filter paper, and a leaf disk (having the
diameter of 3 cm) made of a cucuniber leaf was placed on the absorbent cotton. On the
leaf disk, 10 of melon thrips female adult insects were released. Each of tlie test
eotitainers was treated with a spray solution beitig unifomiy sprayed by using a rotary
15 spraying tower (2.5 rnglcn~~). The spray solutions were prepared by diluting pesticide
co~npositionso btained in Examples 1 to 18 and Comparative Example with water. The
concentrations of Compounds A of the spray solutions were adjusted to 25 ppin or 12.5
ppm, and some of tlie spray solutiotis were used imlnediately after the adjustments, atid
others were used after storing at 2S°C for 4 days after the adjustments. Examinations
20 were conducted 2 days after spraying, and the ~nortalityw as calculated according to the
calculating equation below. Note that cach of the tests was conducted in two plots.
The mortality (%) = {the number of dead insects I (the number of dead insects t tlie
number of survived insects)} x 100
Results are shown in Table 1 below.
25
n.t.: the test was not conducted.
[0117] [Test Example 21 Efficacy Test for Two-Spotted Spider Mite
5 (TCIWZJJC~urUfSic ae) Fentale Adult Insect
A styrol cup (Itaving the diameter of the lid of 7.5 cnt, aud the height of 4 cm) was
filled with tap water, and a lid having a 11ole in its center was placed on the sty101 cup,
and a filter paper was placed on the lid to absorb tap water. A leaf disk (2 c n x~ 2 cm)
tilade of a colmnon bean leaf was placed on the filter paper. On the leaf disk, 10 of
10 two-spotted spider mite female adult insects were released. Each of the test containers
was treated with a spray solution being uniformly sprayed by using a rotary sj~raying
tower (2.5 mg/cn12). Tl~scp ray solutions were prepak-ed by diluting pesticide
co~npositionso btained in Exantples 1 to 18 and Comparative Exattlple with water. l h e
concentratiot~so f Con~poundAs of the spray solutions were adjusted to 12.5 ppm, and
15 sollle of the spray solutions were used i~itmediatelya fter the adjustments, and othe~ws ere
used after storing at 25°C for 6 days after the adjustments. Examinations were
conducted 2 days after sl~rayinga, nd the ~l~ortaliwtya s calculated according to the
calculating equation described it1 Test Exantple 1. Note that each of the tests was
contlucted in two plots. Results are show~itn Table 2 below.
20
The mo~tality( %) of melon-[llrips female adult insects
Example 5 Co~nparative~ xaulple1
Imntediately
after
preparation of
diluted
solutio~ls
100
60
In~~nediately
after
preparation of
diluted
solutiotts
n.t.
100
days after
preparation of
dilutcd
solutions
100
95
4 days after
prel~aration of
diluted
solutions
- -
-. 25
20
Each of the aqueous suspensioll pesticide compositio~o~bst ained ia Exanlple 1 to 18
[O 1 1 81 [Table 21 -- .-
The m-o~r- tality (%) of two-spottcd spider tnitc fc~nalca dult insccts
was placed in a 30 mL glass vial container, and was stored in a thennostatic clian~ber
5 adjusted to 54OC for 14 days. A particle size and viscosity i~nmcdiatclya fter productiotl
Example 5
and after storage, and supernatant separation after storage were measured. Each of
Cotnparntive Example I
Concentration Immaefdteiar tely
(1)~lll) ])reparation of
tneasurelnents was conducted under the conditions show11 below.
Ll.-: I~nnlediately
after 6 days after
prcparatior~ of
[0120] [Measurement of Particle Size]
6 days after
preparation of
Name of nlodel: Particle size analyzer LS-13320, manufactured by Beckman
diluted
solutions
95
Measurement method: Laser diffraction scattering method
101 191 rrest Exanlple 31 Preservation Stability
preparation of
diluted
solutions
100
diluted
solutio~~s
100
Pa~ticlesi ze: Volu~nell ledia~di iameter
diluted
solutio~is
45
The percentage of particle growill (%) was calculated according to Equation I
below, wllerc a particle size inltnediately after production is XI (pm), and a particle size
15 after storage is Y I (pn).
Equation 1: The percentage of particle growth (%) = [(YI - XI) / XI] x 100
[0121] [Viscometrp]
Name of model: B-type visconleter [VISCOMETER DV-I1 + Pro], manufactured by
BROOKFIELD
20 Measurement condition: Using a rotor of No. 2, or using a rotor of No. 3 if the
viscosity is 1,000 mPa.s or. above. The viscosity 2 ~ninutesa ftcr the beginning of the
measurement was ineasu~eda t a rotating speed of 30 rptn.
The percentage of viscosity change (%) was calculated according to Equation 2
below, where viscosity i~nmediatelya ftcr production is Xz (mPa.s), aud viscosity aftet
36
storage is Y2 (nlPas).
Equation 2: l'lic percentage of viscosity change (%) = [(Y2 - X2) / X2] x 100
[O 1221 [Measuremeut of Supernatant Scparatiot~]
The separation of supernatatit was calculated according to Equation 3 below, w1ic1-e
5 a height fiom tlie bottom part of a vial co~itai~iteor the top of a sample is X3 (ctn), a~ida
height of supclnatatit (a clear phase formed upside) after storage is Y3 (cm).
Equation 3: The separation (%) = [Y3 I X3] X 100
[0123] As a rcsult of measuring particle sizes, among the tested aqueous
suspension pesticide conipositions, aqueous suspension pesticide compositions having
10 percentages of pasticle growths (%) of 15% or less are sshowli below.
Examples 1,2,4,5,6,7,8,9, 10, 13, 14, 16, and 17.
Also, as a result of measuring viscosity, among the tested aqueous suspension
pesticide cotnpositions, aqueous suspension pesticide co~npositionsli aving perceutages of
viscosity chai~gcs(% ) of -15 to 15% are shown below.
15 Examples 2,5,6,7,8,9, 14, and 17.
Further, as a result of nleasuri~lgs upernatant separations, atnong tlie tested aqueous
suspension pesticide compositions, aqueous suspension pesticide compositions having
separations (%) of 5% or less are shown below.
Examplcs2,5,6,7, 8, 9,14, 16, and 17.
20 [0124] [Test Exanlplc 41 Efficacy Test for Melon'l'hrips (Thripspaltiii) Female
Adult Insect
A styrol cup (liaving tlie diameter of tlie lid of 7.5 cm, and the height of 4 cm) was
filled with tap watel; and a lid having a hole in its center was placed on tlie styrol cup,
ant1 a filter paper was placed on the lid to absorb tap watel: An absorbent cotton (5 cm
25 x 5 cm) wetted with tap water was placed on the filter paper, and a leaf disk (having the
diameter of 3 cm) made of a cucumber leaf was placed on the absorbent cotton. 011 tlie
leaf disk, I0 of inelo~l.thripsf cmale adult insects were released. Each of the test
containers was treated with a spray solution being uniformly sprayed by using a rotary
spraying tower (2.5 mglcm2). The spray solutions were prepared by diluting pesticide
37
compositions obtained in Examples 19 to 36 and Comparative Exaliiple. The
coacentratiotls of Compou~~Ads o f tlie spray solutions were acl~josledto 12.5 ppni, and
some of the spray solutions were used i~innediatelya ftcr the adjustments, and others were
used after storing at 2S°C for 4 days after thc adjnstnients. Esamiiations were
5 conducted 2 days after spraying, atid the mortality was calculated according to the
calculating equation below. Note that each of the tests was conducted in two plots.
'fl~em prtality (%) = {the number of dead insects I (tlie number of dead insects + tlie
number of survived insects)) x 100
Results are shown in Table 3 below,
(Teri~att)~cIiuusr ticae) Female Adult Insect
10 [0125] [Table 31
A styrol cup (having tlie diameter of the lid of 7.5 cm, and the height of 4 ctn) was
Concentration
( P P ~ )
12.5
filled with tap water, and a lid having a hole in its ce~itewr as placed on the styrol cup,
15 and a filter paper was placed on the lid to absorb tap water. A lcaf disk (2 cm x 2 em)
[0126] [~est'~xamp5l1e E fficacy Test for Two-Spotted Spider Mite
The mortality (%) of melon tlirips female adult insects
made of a coninion beat1 leaf was placed on the filter paper. On the leaf disk, 10 of
two-spotted spider mite female adult insects were released. Each of the test containers
ExanlAe
Im~nediately
after
preparation of
diluted
solutions
100
was treated with a spray solution being uniformly sprayed by using a rotary spraying
29
4 days after
preparation of
diluted
solutions
100
Comparative Example 1
tower (2.5 mg/cm2). Tile spray solutions were prepared by diluting pesticide
20 compositions obtained in Examples 19 to 36 and Comparative Example. lhe
Imn~ediately
after
preparation of
diluted
solutions
100
concentrations of Compounds A of the spray solutions wel-e adjusted to 12.5 ppm, and
4 days after
preparation of
diluted
solutions
20
some of the spray solutions werc used immediately after the adjustments, and others were
used after storing at 25°C for 6 days after the adjustments. Examinations \\rere
conducted 2 days after spraying, and the mortality was calculated according to tlie
3 5
calculating equation described in 'Test Example 4. Note that each of the tests was
conducted in two plots. Results are shown in Table 4 below.
5 Each of oil-in-water emulsion pesticide co~~lpositionosb tained in Exat~~ple1s9 to 36
[O 1271 rSable 41
was placed in a 15 mL glass vial containel; and was stored in a thermostatic chamber
Concentration
OP~I)
12.5
adjusted to -S°C for 7 days. The appearances after storage were visually observed.
Results are shown in Table 5. Note that the signs in the table refer to the meaning as
[0128] [Test Example 61 Low 'Semperature Stability
'I'he nlortality (%) of two-spotted spider mite feniale adult insects
follows.
10 o: The oil phase and the aqueous phase are not separated,
Example 29
x: The oil phase and the aqueous phase are separated.
101291 [Table 51
The appearances after storage
at-5°C for 7 days
I~nmcdiately
after
preparation of
diluted
solutions
100
Comparative Example 1
Example 19
Example 20
Example 21
Example 22 x
6 days after
preparation of
diluted
solutions
100
Immediately
after
preparation of
diluted
solutions
100
6 days after
preparation of
diluted
solutions
45
Example 26
Example 27
Example 30
Example 23
Example 24 .
Examole 25
o
x
o
Example 3 1
Exan~ple3 2
Example 33
Example 34
Example 35
Example 36
o
- o
o
o
o
x
[0130] The composition of the prcscnt invention can be used Tor pest 'co~itrool f
5 hiirtiiful organisms, particulal.ly of harmful insects and inites.

CLAIMS
1. A liquid pesticide cotnposition containing:
(a)
5 (Z)-4-[5-(3,5-dichloropl1enyl)-5-trifluoroniethyl-4,5-di1~y~Iroisoxazole-3-yl]-N-(tiietlioxyi
tninotnet11yl)-2-nretliyl benzoic acid a~nideas a pesticide active ingredient;
(b) at least one selected from the group consisting of surfactant and protective
colloid;
(c) a solve~ita; nd
10 (d) water.
2. The liquid pesticide conlposition according to claim I, characterized in that (b) at
least one selected from the group consisting of surfactant and protective colloid is a
surfactant, that (c) tlie solvent is a nonpolar solvent, and that (a) tlte pesticide active
15 ingredient is pt~senat s a solid dispersed in (d) water.
3. The liquid pesticide cotnposition according to claim 2, wherein (c) the nonpolar
solvent is at least one selected from the group consisting of aromatic carboxylic acid estel;
dibasic acid ester, fatty acid ester, and aromatic hydrocarbon.
20
4. The liquid pesticide con~positiona ccol-dingt o claim 2, wherein (c) the nonpolar
solvent is at least one selected fiom tlie group consisting of plithalic acid alkyl ester
llavitig a Cs.13 alkyl group; tritliellitic acid alkyl ester haviiig a Cs.10 alkyl group; dibasic
acid ester that is an ester of a Cs.10 dicarboxylic acid and a C4.s alcohol; fatty acid ester
25 derived from a vegetable oil; falty acid ester that is an ester of a C8.18 fatty acid and a
Cl.16 alcohol; fatty acid triglyceride; and an ammatic hydrocarbon.
5. Tlic liquid pesticide composition according to claim 2, wherein (c) the nonpola~
solvent is at least one selected fsoni tlie group consisting of ditridecyl plltlialate,
41
bis(2-cthylhexyl) phthalate, dialkyl (CI0.12p) litlialatc, trialkyl (Cs or CIOt)r imcllitatc,
tris(2-etl~ylliexyl)tr imellitate, triisodecyl trimellitatc, diisobutyl adipate,
bis(2-cthylliexyl) scbacate, soybean oil fatty acid ester, methyl oleate, isobutyl oleate,
cetyl2-etliylhexanoate, 2-ctl~plliexanoica cid triglyceride, and phenylxylyl ethane.
5
6. The liquid pcsticide composition according to any one of claims 2 to 5, wherein a
content of (c) the nonpolar solvent is 30% by mass to 50% by ~ilassb ased on a total niass
of the liquid pesticide composition.
10 7. The liq~~pieds ticide colnpositio~a~c coding to any one of claims 2 to 6, wherein
(b) the surfactant is at least one selected fiom the group consisting of polyoxyethylene
styrylphenyl ether, polyoxyetl~yiene-polyoxypropyletibel ock polymer, acetylene diol,
polyoxyethylene styrylphenyl ether sulfuric acid ester or a salt thereof, and
polyoxyethylene styrylphe~~eytlh er pl~osphorica cid ester or a salt thereof.
15
8. The liquid pesticide colnposition according to clai1117, wlierein (b) the surfactal~t
is at least one selected from the group consisting of polyoxyethylene tnonostyrylphenyl
ether, polyoxyethylene distyl.ylplieny1 ether, polyoxyethylene tristyrylphenyl ether,
polyoxycthylene-polyoxypl-opylene block polymer, acetylene diol, polyoxyethylene
20 styrylplienyl ether sulft~rica cid ester salt, and polyoxyethylene styrylplienyl ether
phosphoric acid ester.
9. The liquid pesticide colnpositio~al ccording to any one of claims 2 to 8, wherein a
total content of (b) the surfactant is 0.1% by mass to 10% by mass based on a total mass
25 of the liquid pesticide composition.
10.1'1>e liquid pesticide composition according to claim 1, characterized in that (a)
the pesticide active ingrcdicnt is dissolved in (c) the solvcnt, and the solvent is prcscnt as
being emulsified iil (d) water
11. TIIC liquid pesticide composition accortling to claim 10, wlterein (c) the solvent
is at least one selected from the group cotlsisting of fatty acid dimethylamide,
N-alkyl-2-pynrolidonc, arotnatie hydrocarbon, and ester solvetit.
5
12. The liquid pesticide composition according to clai~ii1 0, wherein (c) the solvent
is at least one selected from the group consisting of fatty acid dimethylarnide,
N-alkyl-2-pyrrolidone, aromatic hydrocarboti, dibasic acid ester, and fatty acid ester.
10 13. The liquid pesticide compositiot~a ccording to claim 10, characterized in that (c)
the solve~ltis a mixture of at least one selected fro111t he group co~isistingo f fatty acid
dimethylanlide and N-alkyl-2-pyrrolido~ie; and at least one selected fiom the group
consisting of aronlatic Ilydrocarbon and ester solvent.
15 14. The liquid pesticide composition according to claim 10, characterized in that (c)
the solvent is a ~uixtureo f at least one selcctcd fiom the group co~isistit~ogf fatty acid
dimethylamide and N-alkyl-2-pyrrolidone; and at least one selected fro111 the group
consisting of aromatic hydrocal-bon, dibasic acid ester, and fatty acid ester.
20 15. The liquid pesticide cornpositio~al ccording to claim 10, characterized in that (c)
the solvent is a mixture of at least one selected kom the group consisting of fatty acid
dimethylamide co~llposedo f a Cs.10 fatty acid and N-alkyl-2-pyrrolidone; and at least one
selected frotn the group consisting of aromatic hydrocarbon, dibasic acid ester that is an
estcr of a C44 dicarboxylic acid and a (21.4 alcohol, and fatty acid estcr that is an ester of a
25 C3.S fatty acid and a Cl.g alcohol.
16. The liquid pesticide co~npositiona ccording to claim 10, characterized in that (c)
the solvent is a mixture of at least one selected fro111 the group consisting of dimethyl
octane amide, dimethyl decane ainide, and N-octyl-2-py~.rolidone;a nd at least one
43
selected from the group consisting of aro~natich ydrocarbon, tliisobutyl succinate,
diisobutyl glutarate, dimethyl 2-methylglutaratc, diisobutyl adipate, butyl lactate, lactic
acid 2-ethylhexyl ester, and methyl caprylate.
5 17. The liquid pesticide co~npositioral ccording to clai~ll1 3, wherein a content of at
least one selected from the group consisting of aromatic hydrocarbon and ester solvent is
2.5% by tnass to 17.5% by mass based on a total mass of thc liquid pesticide
composition.
10 IS. The liquid pesticide compositiotl according to any one of claims 10 to 17,
wherein (b) the surfactant is a tlonionic surfactant or a sulfouic acid surfactant.
19. The liquid pesticide con~positiona ccording to claim 18, whereitl (b) the
surfactant is selected from the group consisting of polyoxyethyletle styrylphenyl ether,
15 polyoxyethylene-polyoxypropylene block polymer, and dialkyl (C8.12) sulfosucci~late.
20. The liquid pesticide composition accordiug to claim 18, wherein (b) the
surfactant is selected from the group consisting of polyoxyethylene styrylphenyl ether,
polyoxpethylene-polyoxypropplet~eb lock polymer, and dioctyl sulfosuccinate.
20
21. The liquid pesticide co~npositioial ccording to any one ofclai~ns1 0 to 20,
wherein a total content of (b) the surfactant is 0.1% by mass to 10% by mass based on a
total Illass of the liquid pesticide cotnposition.
25 22. The liquid pesticide composition according to any oue of claims 10 to 21,
wherein (b) the protective colloid is a polyvinyl alcohol.
23. The liquid pesticide co~npositiona ccording to claim 22, wherein a coutent of the
protecti\ie colloid is 0.1% by mass to lO%by mass based on a total mass of the liquid
pesticide composition.