SPECIFICATION
COMPOSITION FOR PREVENTING HARMFUL ORGANISMS
TECHNICAL FIELD
[0001]
The present invention relates to a composition for preventing
harmful organisms containing one or two or more compounds selected
from compounds represented by the general formula (1), and one or
two or more kinds selected from other insecticides, miticides or
bactericides as active ingredients,
[0002]
[0003]
wherein, in the formula, AI, A2, A3 and A4 independently represent
a carbon atom, a nitrogen atom or an oxidized nitrogen atom; GI and
G2 independently represent an oxygen atom or a sulfur atom; RI and
R2 independently represent a hydrogen atom or a Cl to C4 alkyl group;
Xs may be the same or different and represent a hydrogen atom, a
halogen atom or a trifluoromethyl group;
Qi represents a phenyl group,
a substituted phenyl group having one or more substituents which
may be the same or different and are selected from a halogen atom,
a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group,
a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4
haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6
halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy
group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a
C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a
C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a
C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group,
a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an
acetylamino group and a phenyl group,
a heterocyclic group (The heterocyclic group herein represents
a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group,
a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group,
an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a
thiazolyl group, an isothiazolyl group, an imidazolyl group, a
triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl
group.), or
a substituted heterocyclic group having one or more substituents
which may be the same or different and are selected from a halogen
atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl
group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4
haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6
halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy
group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a
C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a
C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a
C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group,
a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an
acetylamino group and a phenyl group (The heterocyclic group
represents the same as those described above.); and
Q2 is represented by the general formula (2) or (3),
[0004]
(2)
[0005]
wherein, in the formula, YI and YS may be the same or different
and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl
group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3
alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3
alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano
group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6
perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or
a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 represent a
hydrogen atom, a halogen atom or a C1-C4 alkyl group, or
[0006]
[0007]
wherein, in the formula, Y6 and Yg may be the same or different
and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl
group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3
alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3
alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano
group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6
perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6
perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl
group; and Yj represents a hydrogen atom, a halogen atom or a C1-C4
alkyl group.
BACKGROUND ART
[0008]
In WO 2000 / 55120 and US Patent No. 6548514, a compound similar
to the compound represented by the general formula (1) for medical
use was described. But activity against insects was never
described therein. Furthermore, it is obvious that such compounds
are not included in the claims of the present invention.
[0009]
In WO 2000 / 7980, a compound similar to the compound represented
by the general formula (1) for medical use was described. But
activity against insects was never described therein. Furthermore,
it is obvious that such a compound is not included in the claims
of the present invention.
[0010]
In US Patent Laid-Open No. 2002-032238, a compound similar to
the compound represented by the general formula (1) for medical
use was described. But activity against insects was never
described therein. Furthermore, it is obvious that such a compound
is not included in the claims of the present invention.
[0011]
Furthermore, insecticides, miticides and bactericides that are
second active ingredients in the present invention are compounds
known in the documents respectively disclosed in Pesticide Manual
(The Pesticide Manual Thirteenth Edition) and the like.
[0012]
However, there is a harmful organism that cannot be controlled
or is difficult to be controlled with the use of a single agent
of these active compounds.
Patent Document 1: WO 2000 / 55120
Patent Document 2: US Patent No. 6548514
Patent Document 3: WO 2000 / 7980
Patent Document 4: US Patent Laid-Open No. 2002-032238
Non-Patent Document 1: Pesticide Manual (The Pesticide Manual
Thirteenth Edition, 2003)
DISCLOSURE OF THE INVENTION
[0013]
There is a harmful organism that cannot be controlled or is
difficult to be controlled with the use of a single agent of the
compound represented by the general formula (1) according to the
present invention, an insecticide, a miticide, or a bactericide.
Accordingly, an object of the present invention is to provide a
composition for preventing harmful organisms for effectively
controlling such a harmful organism.
[0014]
In order to solve the aforementioned object, the present
inventors have repeatedly conducted an extensive study and as a
result, have found that one or two more compounds selected from
compounds represented by the general formula (1), and one or two
or more compounds selected from insecticides, miticides or
bactericides are used in combination thereof, whereby it is
possible to effectively control a plurality of harmful organisms.
Thus, the present invention has been completed.
[0015]
That is, the present invention relates to the following.
[0016]
[1] a composition for preventing harmful organisms containing
one or two or more compounds selected from compounds represented
by the general formula (1), and one or two or more kinds selected
from other insecticides, miticides or bactericides as active
ingredients,
[0017]
Q,
[0018]
wherein, in the formula, AI, A?,, Aj and A4 independently represent
a carbon atom, a nitrogen atom or an oxidized nitrogen atom; GI and
G2 independently represent an oxygen atom or a sulfur atom; RI and
R2 independently represent a hydrogen atom or a C1-C4 alkyl group;
Xs may be the same or different and represent a hydrogen atom, a
halogen atom or a trifluoromethyl group; Qi represents a phenyl
group,
a substituted phenyl group having one or more substituents which
may be the same or different and are selected from a halogen atom,
a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group,
a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4
haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6
halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy
group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a
C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a
C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a
C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group,
a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an
acetylamino group and a phenyl group,
a heterocyclic group (The heterocyclic group herein represents
a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group,
a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group,
an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a
thiazolyl group, an isothiazolyl group, an imidazolyl group, a
triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl
group.) or
a substituted heterocyclic group having one or more substituents
which may be the same or different and are selected from a halogen
atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl
group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4
haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6
halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy
group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a
C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a
C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a
C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group,
a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an
acetylamino group and a phenyl group (The heterocyclic group
represents the same as those described above.); and
Q2 is represented by the general formula (2) or (3),
[0019]
(2)
[0020]
wherein, in the formula, YI and YS may be the same or different
and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl
group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3
alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3
alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano
group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6
perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or
a C1-C6 perfluoroalkylsulfonyl group; and ¥2 and ¥4 represent a
hydrogen atom, a halogen atom or a C1-C4 alkyl group; or
[0021]
(3)
V N Y8
[0022]
wherein, in the formula, Ye and Y9 may be the same or different
and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl
group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3
alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3
alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano
group; YS represents a C1-C4 haloalkoxy group, a C2-C6
perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6
perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl
group; and ¥7 represents a hydrogen atom, a halogen atom or a C1-C4
alkyl group;
[2] the composition for preventing harmful organisms as set
forth [1] containing one or two or more compounds selected from
compounds represented by the general formula (la) in which all of
AI, A?, A3 and A4 in the general formula (1) are carbon atoms, and
one or two or more kinds selected from other insecticides,
miticides or bactericides as active ingredients,
[0023]
10
[0024]
wherein, in the formula, RI, R2, GI, G2 and Ch represent the same
as those described in [1] ; Q2 is represented by the general formula
(2) or (3),
(2)
[0025]
wherein, in the formula, YI and Y5 may be the same or different
and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl
group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3
alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3
alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano
group; Y3 represents a C1-C6 perfluoroalkylthio group, a C1-C6
perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl
group; and Y2 and Y4 represent a hydrogen atom, a halogen atom or
a C1-C4 alkyl group, or
[0026]
11
[0027]
wherein, in the formula, Y6 and Y9 may be the same or different
and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl
group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3
alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3
alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano
group; Y8 represents a C1-C4 haloalkoxy group, a C1-C6
perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group,
a C1-C6 perfluoroalkylsulfonyl group; and ¥7 represents a hydrogen
atom, a halogen atom or a C1-C4 alkyl group;
Xi and X2 are independently a hydrogen atom or a fluorine atom;
and X3 and X4 are hydrogen atoms;
[3] the composition for preventing harmful organisms as set
forth in [2] containing one or two or more compounds selected from
compounds represented by the general formula (la) in which all of
AI, A2, A3 and A4 in the general formula (1) are carbon atoms, and
one or two or more kinds selected from other insecticides,
miticides or bactericides as active ingredients,
[0028]
12
[0029]
wherein, in the formula, GI, G2 and Ch represent the same as those
described in [1]; Ch is represented by the general formula (2) or
(3),
[0030]
[0031]
wherein, in the formula, YI and ¥5 may be the same or different
and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl
group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3
alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3
alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano
group; Y3 represents a C2-C6 perfluoroalkyl group; and Y2 and Y4
represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group,
or
[0032]
13
[0033]
wherein, in the formula, Y6 and Y9 may be the same or different
and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl
group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3
alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3
alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano
group; Y8 represents a C2-C6 perfluoroalkyl group; and Y7 represents
a hydrogen atom, a halogen atom or a C1-C4 alkyl group;
Xi and X2 independently represent a hydrogen atom or a fluorine
atom; Xs and X4 are hydrogen atoms; and when any one of RI and R2
is a hydrogen atom, the other one is a C1-C4 alkyl group, or both
of R! and R2 are C1-C4 alkyl groups;
[4] the composition for preventing harmful organisms as set
forth in any one of [1] to [3], wherein insecticides, miticides
and bactericides are one or two or more compounds selected from
azinphos-methyl, acephate, isoxathion, isofenphos, ethion,
etrimfos, oxydemeton-methyl, oxydeprofos, quinalphos,
chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, cyanophos,
dioxabenzofos, dichlorvos, disulfoton, dimethylvinphos,
dimethoate, sulprofos, diazinon, thiometon, tetrachlorvinphos,
temephos, tebupirimfos, terbufos, naled, vamidothion, pyraclofos,
pyridafenthion, pirimiphos-methyl, fenitrothion, fenthion,
phenthoate, flupyrazophos, prothiofos, propaphos, profenofos,
14
oxime, phosalone, phosmet, formothion, phorate, malathion, carbarn,
mesulfenfos, methamidophos, methidathion, parathion, methyl
parathion, monocrotophos, trichlorphon, EPN, isazophos,
isamidofos, cadusafos, diamidaphos, dichlofenthion, thionazin,
fenamiphos, fosthiazate, fosthietan, phosphocarb, DSP,
ethoprophos, alanycarb, aldicarb, isoprocarb, ethiofencarb,
carbaryl, carbosulfan, xylylcarb, thiodicarb, pirimicarb,
fenobucarb, furathiocarb, propoxur, bendiocarb, benfuracarb,
methomyl, metolcarb, XMC, carbofuran, aldoxycarb, oxamyl,
acrinathrin, allethrin, esfenvalerate, empenthrin, cycloprothrin,
cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cyfluthrin,
beta-cyfluthrin, cypermethrin, alpha-cypermethrin,
zeta-cypermethrin, silafluofen, tetramethrin, tefluthrin,
deltamethrin, tralomethrin, bifenthrin, phenothrin, fenvalerate,
fenpropathrin, furamethrin, prallethrin, flucythrinate,
fluvalinate, flubrocythrinate, permethrin, resmethrin,
ethofenprox, cartap, thiocyclam, bensultap, acetamiprid,
imidacloprid, clothianidin, dinotefuran, thiacloprid,
thiamethoxam, nitenpyram, chlorfluazuron, diflubenzuron,
teflubenzuron, triflumuron, novaluron, noviflumuron,
bistrifluron, fluazuron, flucycloxuron, flufenoxuron,
hexaflumuron, lufenuron, chromafenozide, tebufenozide,
halofenozide, methoxyfenozide, diofenolan, cyromazine,
pyriproxyfen, buprofezin, methoprene, hydroprene, kinoprene,
triazamate, endosulfan, chlorfenson, chlorobenzilate, dicofol,
bromopropylate, acetoprole, fipronil, ethiprole, pyrethrin,
rotenone, nicotine sulphate, BT agent, spinosad, abamectin,
15
acequinocyl, amidoflumet, amitraz, etoxazole, chinomethionat,
clofentezine, fenbutatin oxide, dienochlor, cyhexatin,
spirodiclofen, spiromesifen, tetradifon, tebufenpyrad,
binapacryl, bifenazate, pyridaben, pyrimidifen, fenazaquin,
fenothiocarb, fenpyroximate, fluacrypyrim, fluazinam, flufenzin,
hexythiazox, propargite, benzomate, polynactins, milbemectin,
lufenuron, mecarbam, methiocarb, mevinphos, halfenprox,
azadirachtin, diafenthiuron, indoxacarb, emamectin benzoate,
potassium oleate, sodium oleate, chlorfenapyr, tolfenpyrad,
pymetrozine, fenoxycarb, hydramethylnon, hydroxy propyl starch,
pyridalyl, flufenerim, flubendiamide, flonicamid, metaflumizole,
lepimectin, TPIC, albendazole, oxibendazole, oxfendazole,
trichlamide, fensulfothion, fenbendazole, levamisole
hydrochloride, morantel tartrate, dazomet, metam-sodium, a
compound represented by the general formula (A),
[0034]
(A)
[0035]
wherein, in the formula, Rll represents a methyl group or a
chloro group; R12 represents a methyl group, a chloro group, a bromo
group or a cyano group; R13 represents a chloro group, a bromo group,
a trifluoromethyl group or a cyanomethoxy group; and R14 represents
a methyl group or an isopropyl group (This compound is disclosed
in WO 2003315519, while insecticidal activity and a production
16
method thereof are described),
a compound represented by the general formula (B),
[0036]
(B)
[0037]
wherein, in the formula, R21 represents a
1,1,1,2,3,3,3-heptafluoro-2-propyl group or a
1,1,2,2,3,3,3-heptafluoro-1-propyl group (This compound is
disclosed in Japanese Patent Laid-open No. 2001-342186, while
insecticidal activity and a production method thereof are
described),
triadimefon, hexaconazole, propiconazole, ipconazole,
prochloraz, triflumizole, tebuconazole, epoxiconazole,
difenoconazole, flusilazole, triadimenol, cyproconazole,
metconazole, fluguinconazole, bitertanol, tetraconazole,
triticonazole, flutriafol, penconazole, diniconazole,
fenbuconazole, bromuconazole, imibenconazole, simeconazole,
myclobutanil, hymexazole, imazalil, furametpyr, thifluzamide,
etridiazole, oxpoconazole, oxpoconazole fumarate, pefurazoate,
prothioconazole, pyrifenox, fenarimol, nuarimol, bupirimate,
mepanipyrim, cyprodinil, pyrimethanil, metalaxyl, oxadixyl,
benalaxyl, thiophanate, thiophanate-methyl, benomyl, carbendazim,
fuberidazole, thiabendazole, manzeb, propineb, zineb, metiram,
maneb, ziram, thiuram, chlorothalonil, ethaboxam, oxycarboxin,
17
carboxin, flutolanil, silthiofam, mepronil, dimethomorph,
fenpropidin, fenpropimorph, spiroxamine, tridemorph, dodemorph,
flumorph, azoxystrobin, kresoxim-methyl, metominostrobin,
orysastrobin, fluoxastrobin, trifloxystrobin, dimoxystrobin,
pyraclostrobin, picoxystrobin, iprodione, procymidone,
vinclozolin, chlozolinate, flusulfamide, dazomet, methyl
isothiocyanate, chloropicrin, methasulfocarb, hydroxyisoxazole,
potassium hydroxyisoxazole, echlomezol, D-D, carbarn, basic copper
chloride, basic copper sulfate, copper nonylphenolsulfonate,
oxine copper, DBEDC, anhydrous copper sulfate, copper sulfate
pentahydrate, cupric hydroxide, inorganic sulfur, wettable sulfur,
lime sulfur, zinc sulfate, fentin, sodium hydrogen carbonate,
potassium hydrogen carbonate, sodium hypochlorite, silver,
edifenphos, tolclofos-methyl, fosetyl, iprobenfos, dinocap,
pyrazophos, carpropamid, fthalide, tricyclazole, pyroquilon,
diclocymet, fenoxanil, kasugamycin, validamycin, polyoxins,
blasticiden S, oxytetracycline, mildiomycin, streptomycin, rape
seed oil, machine oil, benthiavalicarbisopropyl, iprovalicarb,
propamocarb, diethofencarb, fluoroimide, fludioxanil,
fenpiclonil, quinoxyfen, oxolinic acid, chlorothalonil, captan,
folpet, probenazole, acibenzolar-S-methyl, tiadinil,
cyflufenamid, fenhexamid, diflumetorim, metrafenone,
picobenzamide, proquinazid, famoxadone, cyazofamid, fenamidone,
zoxamide, boscalid, cymoxanil, dithianon, fluazinam,
dichlofluanide, triforine, isoprothiolane, ferimzone,
diclomezine, tecloftalam, pencycuron, chinomethionat,
iminoctadine acetate, iminoctadine albesilate, ambam,
18
polycarbamate, thiadiazine, chloroneb, organonickel, guazatine,
dodine, quintozene, tolylfluanid, anilazine, nitrothalisopropyl,
fenitropan, dimethirimol, benthiazole, harpin protein, flumetover,
mandipropamide and penthiopyrad; ^ ,. - r<1 •»
* * • -^as Stt TOhth inL^Jy
[5] the composition for preventing harmful organisms^wherein
insecticides, miticides and bactericides are one or two or more
compounds selected from fenitrothion, fenthion, isoxathion,
acephate, buprofezin, pyriproxyfen, silafluofen, dinotefuran,
imidacloprid, ethofenprox, thiamethoxam, clothianidin,
acetamiprid, nitenpyram, thiacloprid, benfuracarb, methomyl,
fenobucarb, spinosad, pymetrozine, flonicamid, fipronil,
ethiprole, abamectin, a compound represented by the general
formula (B),
[.•0038]
H fV
/^x^vHx-N\^x^iX
R21-J- I I (B)
O^CH,
[0039]
wherein, in the formula, R21 represents a
1,1,1,2,3,3,3-heptafluoro-2-propyl group or a
1,1,2,2,3,3,3-heptafluoro-l-propyl group (This compound is
disclosed in Japanese Patent Laid-open No. ,2001-342186, while
insecticidal activity and 'a production method thereof are
described),
fenpyroximate, pyridaben, hexythiazox, fenbutatin oxide,
tebufenpyrad, pyrimidifen, etoxazole, polynactins, milbemectin,
19
acequinocyl, bifenazate, spirodiclofen, dienochlor, spiromesifen,
tetradifon, chlorfenapyr, clofentezine, tolfenpyrad,
fluacrypyrim, propargite, diafenthiuron, flufenoxuron,
penthiopyrad, flusulfamide, iminoctadine acetate, iminoctadine
albesilate, acibenzolar-S-methyl, ferimzone, pyroquilon,
orysastrobin, azoxystrobin, carpropamid, diclocymet, probenazole,
tiadinil, isoprothiolane, tricyclazole, fthalide, kasugamycin,
fenoxanil, mepronil, diclomezine, pencycuron, validamycin,
edifenphos, furametpyr, thifluzamide, flutolanil,
metominostrobin, iprobenfos and oxolinic acid; and
[6] the composition for preventing harmful organisms as set
forth in any one of [1] to [5], wherein one or more compounds of
other insecticides, miticides or bactericides are respectively
contained in an amount of 0.001 to 95 weight %.
[0040]
The mixed composition of the present invention is capable of
exerting a remarkable control effect even on a harmful organism
which failed to bring about a sufficient control effect with the
use of a single agent and a plurality of harmful organisms showing
chemical resistance and the like so that it can have a remarkable
control effect on a harmful organism that cannot be controlled with
the use of a single agent and a plurality of harmful organisms
showing chemical resistance and the like. Accordingly, the
composition for preventing harmful organisms of the present
invention can greatly contribute to labor saving in agriculture.
BEST MODE FOR CARRYING OUT THE INVENTION
20
[0041]
Wordings used in general formulae such as the general formula
(1) and the like of the present invention have the respective
meanings as described hereinafter in terms of definitions.
[0042]
The term "halogen atom" represents a fluorine atom, a chlorine
atom, a bromine atom or an iodine atom.
[0043]
In expression of "Ca-Cb (a and b represent an integer of not less
than 1)," for example, "C1-C3" refers to 1 to 3 carbon atoms,
"C2-C6" refers to 2 to 6 carbon atoms, and "C1-C4" refers to 1 to
4 carbon atoms.
[0044]
"n-" refers to normal, "i-" refers to iso, "s-" refers to
secondary and "t-" refers to tertiary.
[0045]
The term "alkyl group which may be substituted" refers to a
linear, branched or cyclic alkyl group which may be the same or
different and is substituted with a hydrogen atom, a halogen atom,
a hydroxy group, a cyano group, a nitro group, a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6
haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6
haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy group, a C1-C6
haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino
21
group, di C1-C6 alkylamino groups, a phenyl group which may be
substituted, a phenylcarbonyl group which may be substituted, a
phenylamino group which may be substituted or a heterocyclic group
which may be substituted.
[0046]
The term "C1-C4 alkylcarbonyl group which may be substituted"
refers to a linear, branched or cyclic alkylcarbonyl group having
1 to 4 carbon atoms which may be the same or different and is
substituted with a hydrogen atom, a halogen atom, a hydroxy group,
a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl
group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl
group, a C1-C6 alkylcarbonyloxy group, a C1-C6
haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino
group, di C1-C6 alkylamino groups, a phenyl group which may be
substituted, a phenylcarbonyl group which may be substituted, a
phenylamino group which may be substituted or a heterocyclic group
which may be substituted.
[0047]
The term "phenyl group which may be substituted" refers to a
phenyl group which may be the same or different and is substituted
with a hydrogen atom, a halogen atom, a hydroxy group, a cyano group,
a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6
22
alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6
alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6
alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6
alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, an
amino group, a C1-C6 alkylamino group, di C1-C6 alkylamino groups,
an acetylamino group, a phenyl group which may be substituted, a
phenylcarbonyl group which may be substituted, a phenylamino group
which may be substituted or a heterocyclic group which may be
substituted.
[0048]
The term "naphthyl group which may be substituted" refers to a
naphthyl group which may be the same or different and is substituted
with a hydrogen atom, a halogen atom, a hydroxy group, a cyano group,
a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6
alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6
alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6
alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6
alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, an
amino group, a C1-C6 alkylamino group, di C1-C6 alkylamino groups,
an acetylamino group, a phenyl group which may be substituted, a
phenylcarbonyl group which may be substituted, a phenylamino group
which may be substituted or a heterocyclic group which may be
substituted.
[0049]
23
The term "heterocyclic group which may be substituted" refers
to a heterocyclic group which may be the same or different and is
substituted with a hydrogen atom, a halogen atom, a hydroxy group,
a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl
group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl
group, a C1-C6 alkylcarbonyloxy group, a C1-C6
haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino
group, di C1-C6 alkylamino groups, an acetylamino group, a phenyl
group which may be substituted, a phenylcarbonyl group which may
be substituted, a phenylamino group which may be substituted or
a heterocyclic group which may be substituted.
[0050]
The term "C1-C3 alkyl group" refers to a linear or branched alkyl
group having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl,
i-propyl, cyclopropyl or the like, UC1-C4 alkyl group" refers to
a linear or branched alkyl group having 1 to 4 carbon atoms such
as n-butyl, s-butyl, i-butyl, t-butyl or the like in addition to
"C1-C3 alkyl group," and "C1-C6 alkyl group" refers to a linear
or branched alkyl group having 1 to 6 carbon atoms such as n-pentyl,
2-pentyl, 3-pentyl, neopentyl, n-hexyl, 2-hexyl,
4-methyl-2-pentyl, 3-methyl-n-pentyl or the like in addition to
"C1-C4 alkyl group."
[0051]
24
The term "C1-C3 haloalkyl group" refers to a linear or branched
alkyl group having 1 to 3 carbon atoms which is substituted with
one or more halogen atoms and may be the same or different, such
as monofluoromethyl, difluoromethyl, trifluoromethyl,
monochloromethyl, dichloromethyl, trichloromethyl,
monobromomethyl, dibromomethyl, tribromomethyl, 1-fluoroethyl,
2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,
1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl,
2,2,2-trichloroethyl, 1-bromoethyl, 2-bromoethyl,
2,2-dibromoethyl, 2,2,2-tribromoethyl, 2-iodoethyl,
pentafluoroethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl,
3-bromo-n-propyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl,
1,1,l-trifluoro-2-propyl, l-chloro-3-fluoro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl,
2,2,3,3,3-pentafluoro-n-propyl, heptafluoro-i-propyl,
heptafluoro-n-propyl or the like, and "C1-C4 haloalkyl group"
refers to a linear or branched alkyl group having 1 to 4 carbon
atoms which is substituted with one or more halogen atoms and may
be the same or different, such as 4-fluoro-n-butyl,
nonafluoro-n-butyl, nonafluoro-2-butyl or the like in addition to
"C1-C3 haloalkyl group."
[0052]
The term "C2-C4 alkenyl group" refers to an alkenyl group of 2
to 4 carbon atoms having a double bond in the carbon chain such
as vinyl, allyl, 2-butenyl, 3-butenyl or the like, and "C2-C4
haloalkenyl group" refers to a linear or branched alkenyl group
25
of 2 to 4 carbon atoms having a double bond in the carbon chain
which is substituted with one or more halogen atoms and may be the
same or different, such as 3,3-difluoro-2-propenyl,
3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl,
2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl,
3,4,4-tribromo-3-butenyl or the like.
[0053]
The term "C2-C4 alkynyl group" refers to a linear or branched
alkynyl group of 2 to 4 carbon atoms having a triple bond in the
carbon chain such as propargyl, l-butyn-3-yl,
l-butyne-3-methyl-3-yl or the like, and "C2-C4 haloalkynyl group"
refers to a linear or branched alkenyl group of 2 to 4 carbon atoms
having a triple bond in the carbon chain which is substituted with
one or more halogen atoms and may be the same or different.
[0054]
The term "C3-C6 cycloalkyl group" refers to a cycloalkyl group
of 3 to 6 carbon atoms having a ring structure, such as cyclopropyl,
cyclobutyl, cyclopentyl, 2-methylcyclopentyl,
3-methylcyclopentyl, cyclohexyl or the like, and "C3-C6
halocycloalkyl group" refers to a cycloalkyl group of 3 to 6 carbon
atoms having a ring structure which is substituted with one or more
halogen atoms and may be the same or different, such as
2,2,3, 3-tetraf luorocyclobutyl', 2-chlorocyclohexyl,
4-chlorocyclohexyl or the like.
[0055]
The term "C1-C3 alkoxy group" refers to a linear or branched
alkoxy group having 1 to 3 carbon atoms such as methoxy, ethoxy,
26
n-propyloxy, isopropyloxy or the like, "C1-C3 haloalkoxy group"
refers to a linear or branched haloalkoxy group having 1 to 3 carbon
atoms which is substituted with one or more halogen atoms and may
be the same or different, such as monofluoromethoxy,
difluoroethoxy, trifluoromethoxy,
1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy,
2-chloroethoxy, 3-fluoro-n-propyloxy or the like, and "C1-C4
haloalkoxy group" refers to a linear or branched haloalkoxy group
having 1 to 4 carbon atoms which is substituted with one or more
halogen atoms and may be the same or different, such as
1,1,1,3,3,4,4,4-octafluoro-2-butyloxy or the like, in addition to
"C1-C3 haloalkoxy group."
[0056]
The term "C1-C3 alkylthio group" refers to a linear or branched
alkylthio group having 1 to 3 carbon atoms such as methylthio,
ethylthio, n-propylthio, i-propylthio, cyclopropylthio or the
like, "C1-C4 alkylthio group" refers to a linear or branched
alkylthio group having 1 to 4 carbon atoms such as n-butylthio,
i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio or
the like, in addition to "C1-C3 alkylthio group," "C1-C3
haloalkylthio group" refers to a linear or branched alkylthio group
having 1 to 3 carbon atoms which is substituted with one or more
halogen atoms and may be the same or different, such as
trifluoromethylthio, pentafluoroethylthio,
2,2,2-trifluoroethylthio, heptafluoro-n-propylthio,
heptafluoro-i-propylthio or the like, and "C1-C4 haloalkylthio
group" refers to a linear or branched alkylthio group having 1 to
27
4 carbon atoms which is substituted with one or more halogen atoms
and may be the same or different, such as nonafluoro-n-butylthio,
nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio or the like,
in addition to "C1-C3 haloalkylthio group."
[0057]
The term "C1-C3 alkylsulfinyl group" refers to a linear or
branched alkylsulfinyl group having 1 to 3 carbon atoms, such as
methylsulfinyl, ethylsulfinyl, n-propylsulfinyl,
i-propylsulfinyl, cyclopropylsulfinyl or the like, and "C1-C3
haloalkylsulfinyl group" refers to a linear or branched
alkylsulfinyl group having 1 to 3 carbon atoms which is substituted
with one or more halogen atoms and may be the same or different,
such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl,
2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl,
heptafluoro-i-propylsulfinyl or the like.
[0058]
The term "C1-C3 alkylsulfonyl group" refers to a linear or
branched alkylsulfonyl group having 1 to 3 carbon atoms, such as
methylsulfonyl, ethylsulfonyl, n-propylsulfonyl,
i-propylsulfonyl, cyclopropylsulfonyl or the like, and "C1-C3
haloalkylsulfonyl group" refers to a linear or branched
alkylsulfonyl group having 1 to 3 carbon atoms which is substituted
with one or more halogen atoms and may be the same or different,
such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl,
2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl,
heptafluoro-i-propylsulfonyl or the like.
[0059]
28
The term "arylsulfonyl group" refers to an arylsulfonyl group
of 6 to 14 carbon atoms having an aromatic ring, such as
phenylsulfonyl, p-toluenesulfonyl, 1-naphthylsulfonyl,
2-naphthylsulfonyl, anthrylsulfonyl, phenanthrylsulfonyl,
acenaphthylenylsulfonyl or the like.
[0060]
The term "C1-C4 alkylamino group" refers to a linear, branched
or cyclic alkylamino group having 1 to 4 carbon atoms, such as
methylamino, ethylamino, n-propylamino, i-propylamino,
n-butylamino, cyclopropylamino or the like, and "di C1-C4
alkylamino group" refers to a linear or branched amino group which
is substituted with two alkyl groups having 1 to 4 carbon atoms
and may be the same or different, such as dimethylamino,
diethylamino, N-ethyl-N-methylamino or the like.
[0061]
The term "C1-C4 alkylcarbonyl group" refers to a linear,
branched or cyclic alkylcarbonyl group having 1 to 4 carbon atoms,
such as formyl, acetyl, propionyl, isopropylcarbonyl,
cyclopropylcarbonyl or the like.
[0062]
The "C1-C4 haloalkylcarbonyl group" refers to a linear or
branched alkylcarbonyl group having 1 to 4 carbon atoms which is
substituted with one or more halogen atoms and may be the same or
different, such as fluoroacetyl, difluoroacetyl, trifluoroacetyl,
chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl,
iodoacetyl, 3,3,3-trifluoropropionyl,
2,2,3,3,3-pentafluoropropionyl or the like.
29
[0063]
The term "C1-C4 alkylcarbonyloxy group" refers to a linear or
branched alkylcarbonyloxy group having 1 to 4 carbon atoms, such
as acetoxy, propionyloxy or the like.
[0064]
The term "C1-C4 alkoxycarbonyl group" refers to a linear or
branched alkoxycarbonyl group having 1 to 4 carbon atoms, such as
methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl or the
like.
[0065]
The term "C1-C4 perfluoroalkyl group" refers to a linear or
branched alkyl group having 1 to 4 carbon atoms which is all
substituted with fluorine atoms, such as trifluoromethyl,
pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl,
nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl or
the like, and "C2-C6 perfluoroalkyl group" refers to a linear or
branched alkyl group having 2 to 6 carbon atoms which is all
substituted with fluorine atoms, such as pentafluoroethyl,
heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl,
nonafluoro-2-butyl, nonafluoro-i-butyl, perfluoro-n-pentyl,
perfluoro-n-hexyl or the like.
[0066]
The term "C1-C6 perfluoroalkylthio group" refers to a linear or
branched alkylthio group having 1 to 6 carbon atoms which is all
substituted with fluorine atoms, such as trifluoromethylthio,
pentafluoroethylthio, heptafluoro-n-propyIthio,
heptafluoro-i-propylthio, nonafluoro-n-butylthio,
30
nonafluoro-2-butylthio, nonafluoro-i-butylthio,
perfluoro-n-pentylthio, perfluoro-n-hexylthio or the like.
[0067]
The term "C1-C6 perfluoroalkylsulf inyl group" refers to a linear
or branched alkylsulfinyl group having 1 to 6 carbon atoms which
is all substituted with fluorine atoms, such as
trifluoromethylsulfinyl, pentafluoroethylsulfinyl,
heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl,
nonafluoro-n-butylsuIfinyl, nonafluoro-2-butylsulfinyl,
nonafluoro-i-butylsulfinyl, perfluoro-n-pentylsulfinyl,
perfluoro-n-hexylsulfinyl or the like.
[0068]
The term "C1-C6 perf luoroalkylsulf onyl group" refers to a linear
or branched alkylsulfonyl group having 1 to 6 carbon atoms which
is all substituted with fluorine atoms, such as
trifluoromethylsulfonyl, pentafluoroethylsulfonyl,
heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl,
nonafluoro-n-butylsulfonyl, nonafluoro-2-butylsulfonyl,
nonafluoro-i-butylsulfonyl, perfluoro-n-pentylsulfonyl,
perfluoro-n-hexylsulfonyl or the like.
[0069]
The compound represented by the general formula (1) of the
present invention contains one or more asymmetric carbon atoms or
asymmetric centers in its structural formula in some cases and has
two or more optical isomers in some cases. The present invention
also includes all of the respective optical isomers and mixtures
comprising of these isomers in any ratio. Furthermore, the
31
compound represented by the general formula (1) of the present
invention has two or more geometrical isomers derived from a
carbon-carbon double bond in its structural formula in some cases.
The present invention also includes all of the respective
geometrical isomers and mixtures comprising of these isomers in
any ratio.
[0070]
Preferable examples of the substituents or atoms in the
compounds represented by the general formula (1) and the like of
the present invention are listed below.
[0071]
In AI, A2, Aa and. A4, it is preferable that AI is a carbon atom,
a nitrogen atom or an oxidized nitrogen atom and all of Aa, A3 and
A4 are carbon atoms at the same time. it is more preferable that
11 of AI, A2, AS and A4 are carbon atoms.
[0072]
RI is preferably a hydrogen atom or a C1-C4 alkyl group, and
further preferably a hydrogen atom, a methyl group or an ethyl
group.
[0073]
R2 is preferably a hydrogen atom or a C1-C4 alkyl group, and
further preferably a hydrogen atom, a methyl group or an ethyl
group.
[0074]
GI and G2 are independently preferably an oxygen atom or a sulfur
atom, and further preferably both of GI and 62 are oxygen atoms.
[0075]
32
X is preferably a hydrogen atom or a halogen atom, and further
preferably a hydrogen atom or a fluorine atom.
[0076]
n is preferably 0, 1 or 2, and further preferably 0 or 1.
[0077]
Xi is preferably a hydrogen atom or a halogen atom, and further
preferably a hydrogen atom or a fluorine atom.
[0078]
X2 is preferably a hydrogen atom or a fluorine atom, and further
preferably a hydrogen atom.
[0079]
Xa and X$ are preferably hydrogen atoms.
[0080]
Qi is preferably a phenyl group,
a substituted phenyl group having one or more substituents which
may be the same or different and are selected from a halogen atom,
a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group,
a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4
haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6
halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy
group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a
C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a
C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a
C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group,
a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an
acetylamino group,
33
a pyridyl group, or
a pyridyl group having one or more substituents which may be the
same or different and are selected from a halogen atom, a C1-C4
alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4
haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group,
a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3
alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group,
a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3
haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3
haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4
alkylamino group, a cyano group, a nitro group, a hydroxy group,
a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a
C1-C4 alkoxycarbonyl group and an acetylamino group, and
further preferably a phenyl group,
a substituted phenyl group having one to three substituents
which may be the same or different and are selected from a fluorine
atom, a chlorine atom, a bromine atom, an iodine atom, a methyl
group, a trifluoromethyl group, a methoxy group, a
trif luoromethoxy group, a methylthio group, a methylsulfinyl group,
a methylsulfonyl group, a trifluoromethylthio group, a
trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group,
a methylamino group, a dimethylamino group, a cyano group and a
nitro group,
a pyridyl group, or
a pyridyl group having one to two substituents which may be the
same or different and are selected from a fluorine atom, a chlorine
atom, a bromine atom, an iodine atom, a methyl group, a
34
trifluoromethyl group, a methoxy group, a trifluoromethoxy group,
a methylthio group, a methylsulfinyl group, a methylsulfonyl group,
a trifluoromethylthio group, a trifluoromethylsulfinyl group, a
trifluoromethylsulfonyl group, a methylamino group, a
dimethylamino group, a cyano group and a nitro group.
[0081]
Q2 is preferably a substituted phenyl group or a substituted
pyridyl group represented by the general formula (2) or (3),
wherein YI and Y5 are independently preferably a chlorine atom, a
bromine atom, an iodine atom, a methyl group, an ethyl group, an
n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl
group, a trifluoromethyl group, a methylthio group, a
methylsulfinyl group, a methylsulfonyl group, a
trifluoromethylthio group, a trifluoromethylsulfinyl group, a
trifluoromethylsulfonyl group, a cyano group, a methoxy group, an
ethoxy group, an n-propyloxy group, a trifluoromethoxy group, a
difluoromethoxy group or a pentafluoroethoxy group; and
YS and Y9 are independently preferably a chlorine atom, a bromine
atom, an iodine atom, a methyl group, an ethyl group, an n-propyl
group, an i-propyl group, an n-butyl group, a 2-butyl group, a
trifluoromethyl group, a methylthio group, a methylsulfinyl group,
a methylsulfonyl group, a trifluoromethylthio group, a
trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group,
a cyano group, a trifluoromethylsulfinyl group, a
trifluoromethylsulfonyl group, a cyano group, a methoxy group, an
ethoxy group, an n-propyloxy group, a trifluoromethoxy group, a
difluoromethoxy group or a pentafluoroethoxy group; Y2, Y4 and Y7
35
are preferably a hydrogen atom, a halogen atom or a methyl group,
and further preferably a hydrogen atom; Y3 is preferably a
pentafluoroethyl group, a heptafluoro-n-propyl group, a
heptafluoro-i-propyl group, a nonafluoro-n-butyl group, a
nonafluoro-2-butyl group, a nonafluoro-i-butyl group, a
trifluoromethylthio group, a pentafluoroethylthio group, a
heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group,
a nonafluoro-n-butylthio group, a nonafluoro-2-butylthio group,
a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group,
a heptafluoro-n-propylsulfinyl group, a
heptafluoro-i-propylsulfinyl group, a nonafluoro-n-butylsulfinyl
group, a nonafluoro-2-butylsulfinyl group, a
trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group,
a heptafluoro-n-propylsulfonyl group, a
heptafluoro-i-propylsulfonyl group, a nonafluoro-n-butylsulfonyl
group or a nonafluoro-2-butylsulfonyl group; and Yg is preferably
a pentafluoroethyl group, a heptafluoro-n-propyl group, a
heptafluoro-i-propyl group, a nonafluoro-n-butyl group, a
nonafluoro-2-butyl group, a nonafluoro-i-butyl group, a
trifluoromethylthio group, a pentafluoroethylthio group, a
heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group,
a nonafluoro-n-butylthio group, a nonafluoro-2-butylthio group,
a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group,
a heptafluoro-n-propylsulfinyl group, a
heptafluoro-i-propylsulfinyl group, a nonafluoro-n-butylsulfinyl
group, a nonafluoro-2-butylsulfinyl group, a
trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group,
36
a heptafluoro-n-propylsulfonyl group, a
heptafluoro-i-propylsulfonyl group, a nonafluoro-n-butylsulfonyl
group, a nonafluoro-2-butylsulfonyl group, a pentafluoroethoxy
group or a i,1,1,3,3,3-hexafluoro-i-propyloxy group.
[0082]
L is preferably a chlorine atom, a bromine atom or a hydroxy
group.
[0083]
Ria is preferably a hydrogen atom or a Cl to C4 alkyl group, and
further preferably a hydrogen atom, a methyl group or an ethyl
group.
[0084]
R2a is preferably a hydrogen atom or a Cl to C4 alkyl group, and
further preferably a hydrogen atom, a methyl group or an ethyl
group.
[0085]
Gia and G2a are independently preferably an oxygen atom or a
sulfur atom, and further preferably, both Gia and G2a are oxygen
atoms.
[0086]
Xia is preferably a hydrogen atom or a halogen atom, and further
preferably a hydrogen atom or a fluorine atom.
[0087]
X2a is preferably a hydrogen atom or a fluorine atom, and further
preferably a hydrogen atom.
[0088]
and X4a are preferably hydrogen atoms.
[0089]
Yia and Y5a are independently preferably a chlorine atom, a
bromine atom, an iodine atom, a methyl group, an ethyl group, an
n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl
group, a trifluorornethyl group, a methylthio group, a
methylsulfinyl group, a methylsulfonyl group, a
trifluoromethylthio group, a trifluoromethylsulfinyl group, a
trifluoromethylsulfonyl group or a cyano group.
[0090]
¥23 and ¥43 are each preferably a hydrogen atom, a halogen atom
or a methyl group, and further preferably a hydrogen atom.
[0091]
Qia is preferably a phenyl group,
a substituted phenyl group having one or more substituents which
may be the same or different and are selected from a halogen atom,
a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group,
a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4
haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6
halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy
group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a
C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a
C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a
C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group,
a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an
acetylamino group,
a pyridyl group, or
38
a pyridyl group having one or more substituents which may be the
same or different and are selected from a halogen atom, a C1-C4
alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4
haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group,
a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3
alkoxy group, a C1--C3 haloalkoxy group, a C1-C3 alkylthio group,
a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3
haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3
haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4
alkylamino group, a cyano group, a nitro group, a hydroxy group,
a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a
C1-C4 alkoxycarbonyl group and an acetylamino group, and
further preferably a phenyl group,
a substituted phenyl group having one to three substituents
which may be the same or different and are selected from a fluorine
atom, a chlorine atom, a bromine atom, an iodine atom, a methyl
group, a trifluoromethyl group, a methoxy group, a
trif luoromethoxy group, a methylthio group, a methylsulf inyl group,
a methylsulfonyl group, a trifluoromethylthio group, a
trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group,
a methylamino group, a dimethylamino group, a cyano group and a
nitro group,
a pyridyl group, or
a pyridyl group having one to two substituents which may be the
same or different and are selected from a fluorine atom, a chlorine
atom, a bromine atom, an iodine atom, a methyl group, a
trifluoromethyl group, a methoxy group, a trifluoromethoxy group,
39
a methylthio group, a methylsulfinyl group, a methylsulfonyl group,
a trifluoromethylthio group, a trifluoromethylsulfinyl group, a
trifluoromethylsulfonyl group, a methylamino group, a
dimethylamino group, a cyano group and a nitro group.
[0092]
Ra and Rb are independently preferably a fluorine atom, a
trifluoromethyl group, a pentafluoroethyl group or a
heptafluoro-n-propyl group, and further preferably a fluorine atom,
a trifluoromethyl group or a pentafluoroethyl group.
[0093]
Rc is preferably a hydroxy group, a chlorine atom, a bromine atom,
an iodine atom, a methoxy group, an ethoxy group, a
methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a
phenylsulfonyloxy group, a p-toluenesulfonyloxy group, an acetoxy
group or a trifluoroacetoxy group, more preferably a hydroxy group,
a chlorine atom, a bromine atom, a methoxy group, a
methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a
phenylsulfonyloxy group or a p-toluenesulfonyloxy group, and
further preferably a hydroxy group, a chlorine atom or a bromine
atom.
[0094]
Rc' is preferably a hydroxy group.
[0095]
Rc'' is preferably a chlorine atom or a bromine atom.
[0096]
J, J' and J'' are independently preferably a hydroxy group, a
chlorine atom or a bromine atom, and further preferably a chlorine
40
atom.
[0097]
Typical preparation methods of the compound represented by the
general formula (1) according to the present invention are
illustrated below. The compound represented by the general formula
(1) of the present invention can be prepared according to the
methods, but the preparation method paths are not restricted to
the following preparation methods.
[0098]
In the general formulae shown in the following preparation
methods, Xlf X2, X3, X4, YI, Y2, Y4, Y5, d, G2, RI, R2 and Qi may
correspond to Xia, X2a, X3a, X4a, Yia, Y2a, Y4a, Y5a, da, G2a, Rxa,
R2a and Gha respectively, or vice versa. Furthermore, Q2 represents
the same as those described in [1] or the general formula (2), (3)
or (18),
(2)
[0100]
wherein, in the formula, YI, Y2, Y3, Y4 and Y5 represent the same
as those described above,
[0101]
41
Yc
Y,
N Yc
(3)
[0102]
wherein, in the formula, Y6, Y7, Y8 and Y9 represent the same as
those described above, or
[0103]
(18)
[0104]
wherein, in the formula, Yia, Y2a, Y4a, Y5a, Ra, Rb and Rc represent
the same as those described above.
Preparation Method 1
[0105]
NO,
4
(X)n
/VA-;
(19)
NH,
A2 A,
(X)n
(22)
(20)
G,
^Ai Ql
(23)
NO,
R, Reduction Reaction
(X)n
(21)
R, 1 -L Q/>
-R,
(X)n
(24) (26)
42
[0106]
wherein, in the formula, AI, A2, A3, A4, GI, G2, RI, R2/ X, n, Ch
and Q2 represent the same as those described above; and L represents
a functional group having a leaving ability such as a halogen atom,
a hydroxyl group or the like.
l-(i) General formula (19) + General formula (20) -+ General
formula (21)
By reacting an m-nitroaromatic carboxylic acid derivative
having a leaving group represented by the general formula (19) with
an aromatic amine derivative represented by the general formula
(20) in an appropriate solvent or without a solvent, an aromatic
carboxylic acid amide derivative having a nitro group represented
by the general formula (21) can be prepared. In this process, an
appropriate base can also be used.
[0107]
Solvents may not remarkably hinder the progress of the reaction
and examples thereof include water; aromatic hydrocarbons such as
benzene, toluene, xylene and the like; halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride and the
like; chained ethers or cyclic ethers such as diethyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like;
esters such as ethyl acetate, butyl acetate and the like; alcohols
such as methanol, ethanol and the like; ketones such as acetone,
methylisobutyl ketone, cyclohexanone and the like; amides such as
dimethylformamide, dimethylacetamide and the like; nitriles such
as acetonitrile and the like; and inert solvents such as
1,3-dimethyl-2-imidazolidinone and the like. These solvents can
43
be used singly or in combination of two or more kinds.
[0108]
Furthermore, examples of the base include organic bases such as
triethylamine, tri-n-butylamine, pyridine,
4-dimethylaminopyr.idine and the like; alkali metal hydroxides such
as sodium hydroxide, potassium hydroxide and the like; carbonates
such as sodium hydrogen carbonate, potassium carbonate and the
like; phosphates such as di-potassium mono-hydrogen phosphate,
tri-sodium phosphate and the like; alkali metal hydrides such as
sodium hydride and the like; and alkali metal alcoholates such as
sodium methoxide, sodium ethoxide and the like. These bases may
be suitably selected in the range of 0.01 to 5 mole equivalents,
based on the compound represented by the general formula (19) and
used accordingly.
[0109]
The reaction temperature may be suitably selected in the range
of -20 degree centigrade to the reflux temperature of a solvent
in use, while the reaction time may be properly selected in the
range of several minutes to 96 hours.
[0110]
Of the compounds represented by the general formula (19), an
aromatic carboxylic acid halide derivative can be easily prepared
from an aromatic carboxylic acid according to a usual method using
a halogenating agent. Examples of the halogenating agent include
thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl
chloride, phosphorus trichloride and the like.
On the other hand, the compound represented by the general
44
formula (21) can be prepared from the m-nitroaromatic carboxylic
acid derivative and the compound represented by the general formula
(20) without using a halogenating agent. As a method thereof, a
method suitably using an additive such as 1-hydroxybenzotriazole
or the like and employing a condensation agent using
N,N'-dicyclohexylcarbodiimide according to a method as described,
for example, in Chern. Ber. p. 788 (1970) can be exemplified. Other
condensation agents to be used in this case include, for example,
l-ethyl-3-(3-dimethylaminopropyl)carbodiimide,
1,1'-carbonylbis-lH-imidazole and the like.
[0111]
Furthermore, as other method for preparing the compound
represented by the general formula (21), a mixed anhydride
procedure using chloroformate esters can be cited. Also, the
compound represented by the general formula (21) can be prepared
according to a method as described in J. Am. Chem. Soc. p. 5012
(1967) . Examples of chloroformate esters to be used in this case
include isobutyl chloroformate, isopropyl chloroformate and the
like. In addition to chloroformate esters, diethylacetyl chloride,
trimethylacetyl chloride and the like can be cited.
Both the method using a condensation agent and mixed anhydride
procedure are not restricted to the solvent, reaction temperature
and reaction time as described in the above document, and an inert
solvent which does not remarkably hinder the suitable progress of
the reaction may be used. The reaction temperature and reaction
time may be suitably selected as the reaction proceeds.
l-(ii): General formula (21) -» General formula (22)
45
An aromatic carboxylic acid amide derivative having a nitro
group represented by the general formula (21) can be made into an
aromatic carboxylic acid amide derivative having an amino group
represented by the general formula (22) by the reduction reaction.
As the reduction reaction, a method employing the hydrogenation
reaction and a method employing a metallic compound (for example,
stannous chloride (anhydride), iron powder, zinc powder and the
like) can be cited.
[0112]
The former method can be carried out in a proper solvent in the
presence of a catalyst, in an ordinary pressure or a reduced
pressure, in a hydrogen atmosphere. Such a catalyst includes, for
example, palladium catalysts such as palladium carbon and the like,
nickel catalysts such as Raney nickel and the like, cobalt
catalysts, ruthenium catalysts, rhodium catalysts, platinum
catalysts and the like. The solvent includes, for example, water;
alcohols such as methanol, ethanol and the like; aromatic
hydrocarbons such as benzene, toluene and the like; chained ethers
or cyclic ethers such as ether, dioxane, tetrahydrofuran and the
like; and esters such as ethyl acetate and the like. The pressure
may be suitably selected in the range of 0.1 to 10 MPa, the reaction
temperature may be suitably selected in the range of -20 degree
centigrade to the reflux temperature of a solvent in use, and the
reaction time may be properly selected in the range of several
minutes to 96 hours. The compound of the general formula (22) can
be more effectively prepared.
[0113]
46
As the latter method, a method employing stannous chloride
(anhydride) as a metallic compound according to the conditions as
described in "Organic Syntheses" Coll. Vol. Ill P. 453 can be cited.
l-(iii) : General formula (22) + General formula (23) -> General
formula (24)
By reacting an aromatic carboxylic acid amide derivative having
an amino group represented by the general formula (22) with a
compound represented by the general formula (23) in an appropriate
solvent, a compound represented by the general formula (24) of the
present invention can be prepared. In this process, an appropriate
base can also be used.
[0114]
Solvents may not remarkably hinder the progress of the reaction
and examples thereof include water; aromatic hydrocarbons such as
benzene, toluene, xylene and the like; halogenated hydrocarbons
such as dichloromethane, chloroform, carbon tetrachloride and the
like; chained ethers or cyclic ethers such as diethyl ether,
dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like;
esters such as ethyl acetate, butyl acetate and the like; alcohols
such as methanol, ethanol and the like; ketones such as acetone,
methylisobutyl ketone, cyclohexanone and the like; amides such as
dimethylformamide, dimethylacetamide and the like; nitriles such
as acetonitrile and the like; and inert solvents such as
1,3-dimethyl-2-imidazolidinone and the like. These solvents can
be used singly or.in combination of two or more kinds.
Furthermore, examples of the base include organic bases such as
triethylamine, tri-n-butylamine, pyridine,
4-dimethylaminopyridine and the like; alkali metal hydroxides such
as sodium hydroxide, potassium hydroxide and the like; carbonates
such as sodium hydrogen carbonate, potassium carbonate and the
like; phosphates such as di-potassium mono-hydrogen phosphate,
tri-sodium phosphate and the like; alkali metal hydrides such as
sodium hydride and the like; and alkali metal alcoholates such as
sodium methoxide, sodium ethoxide and the like. These bases may
be suitably selected in the range of 0.01 to 5 mole equivalents
based on the compound represented by the general formula (22) and
used accordingly. The reaction temperature may be suitably
selected in the range of -20 degree centigrade to the reflux
temperature of a solvent in use, while the reaction time may be
properly selected in the range of several minutes to 96 hours.
Furthermore, a method employing a condensation agent and a mixed
anhydride procedure as described in l-(i) can also be used.
l-(iv) : General formula (24) + General formula (25) -> General
formula (26)
By reacting a compound represented by the general formula (24)
with an alkyl compound having a leaving group represented by the
general formula (25) in a solvent or without a solvent, a compound
represented by the general formula (26) of the present invention
can be prepared. Examples of the compound represented by the
general formula (25) include alkyl halides such as methyl iodide,
ethyl iodide, n-propyl bromide and the like. Furthermore, in this
process, a suitable base or solvent can be used. As the base or
solvent, the bases or solvents cited in l-(i) can be used. The
reaction temperature and reaction time cited in l-(i) can also be
48
used.
[0115]
Furthermore, the compound represented by the general formula
(26) can also be prepared by an another method comprising reacting
an alkylating agent such as dimethyl sulfate, diethyl sulfate or
the like with the compound represented by the general formula (24)
instead of the compound represented by the general formula (25).
Preparation Method 2
[0116]
r- A ,X-- *Y *A" *V , .A. (23) ' I . A. A*. (20 — R^
[0117]
wherein, in the formula, AI, A2, A3, A4, G\, 62/ RI, R2, X, n, Qlf
Q2, L and Hal represent the same as those described above.
2-(i): General formula (27) + General formula (23) -> General
formula (28)
By reacting carboxylic acids having an amino group represented
by the general formula (27) as a starting material with a compound
represented by the general formula (23) in accordance with the
conditions described in l-(i), carboxylic acids having an
acylamino group represented by the general formula (28) can be
prepared.
2-(ii): General formula (28) -» General formula (29)
A compound represented by the general formula (29) can be
49
prepared by a known usual method comprising reacting a compound
represented by the general formula (28) with thionyl chloride,
oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus
pentachloride, phosphorus trichloride, thionyl bromide,
phosphorus tribromide, diethylaminosulfur trifluoride or the
like.
2-(iii): General formula (29) + General formula (20) -» General
formula (30)
By reacting a compound represented by the general formula (29)
with a compound represented by the general formula (20) according
to the conditions described in l-(i), a compound represented by
the general formula (30) can be prepared.
2-(iv) : General formula (28) + General formula (20) -» General
formula (30)
By reacting a compound represented by the general formula (28)
with a compound represented by the general formula (20) according
to the conditions using a condensation agent or a mixed anhydride
procedure described in 1- (i) , a compound represented by the general
formula (30) can be prepared.
Preparation Method 3
[0118]
S. ft
HNT ' HN" ' " " ' "" '
Lawson Reagent I wi '
R2 A-"^A "» t23)
-*»
(X)n o Wn
(31) (32) (33)
[0119]
50
wherein, in the formula, AI, A2, AS, A4, GI, RI, RZ, X, n, Qi, Q2
and L represent the same as those described above.
3-(i): General formula (31) -» General formula (32)
By reacting a compound represented by the general formula (31)
with a Lawson reagent according to the known conditions described
in Synthesis p. 463 (1993), Synthesis p. 829 (1984) and the like,
a compound represented by the general formula (32) can be prepared.
The conditions such as a solvent, reaction temperature and the like
are not restricted to those described in the documents.
3-(ii) : General formula (32) + General formula (23) -> General
formula (33)
By reacting a compound represented by the general formula (32)
with a compound represented by the general formula (23) according
to the conditions described in l-(i), a compound represented by
the general formula (33) can be prepared.
Preparation Method 4
[0120]
o
Lawson Reagent JL
or
(X)n
(X)n
(34) (35) (36)
[0121]
wherein, in the formula, AI, A2, A3, A4, RI, R2, X, n, Qi and Q2
51
represent the same as those described above.
Compounds represented by the general formulae (35) and (36) can
be prepared from a compound represented by the general formula (34)
according to the conditions described in 3-(i). The conditions
such as a solvent, reaction temperature and the like are not
restricted to those described in the documents. These two
compounds can be easily separated and purified by a known method
of separation and purification technique such as silica gel column
chromatography and the like.
Preparation Method 5
[0122]
Hal UM^RI
A^*' ^ A/X R; (23)
i ! j_ r>2
(X)n' G2 (X)n' 2 l ' ^2 W G
<37> (38) (39) '
[0123]
wherein, in the formula, AI, A2/ A3, A4, d, G2, RI, R2, X, n, Ch,
Q2 and L represent the same as those described above.
5-(i): General formula (37) -» General formula (38)
A compound represented by the general formula (38) can be
prepared by carrying out an amination reaction using ammonia
according to the conditions described, for example, in J. Org. Chem.
p. 280 (1958) . The conditions such as a reaction solvent and the
like are not restricted to those described in the documents, and
an inert solvent which does not remarkably hinder the proper
52
progress of the reaction may be used. The reaction temperature
and reaction time may be suitably selected as the reaction proceeds.
Furthermore, examples of the amination agent include methylamine,
ethylamine or the like, in addition to ammonia.
5-(ii) : General formula (38) -t- General formula (23) -» General
formula (39)
By reacting a compound represented by the general formula (38)
with a compound represented by the general formula (23) according
to the conditions described in l-(i), a compound represented by
the general formula (39) can be prepared.
Preparation Method 6
[0124]
HN
SH
Y,
(40)
I—Rj
(41)
R,
t
(42)
Halogenation UN Oxidation
(43)
Methylation
Oxidation
y, (0)m
(44)
(43-2)
Y< (0)m
(44-2)
[0125]
wherein, in the formula, R2 represents the same as those
described above; YI and Y5 independently represent a methyl group,
a chlorine atom, a bromine atom or an iodine atom; ¥2 and Y4 represent
the same as those described above; Rf represents a C1-C6
53
perfluoroalkyl group; and m represents 1 or 2.
6-(i): General formula (40) + General formula (41) -> General
formula (42)
By reacting aminothiophenols represented by the general formula
(40) with haloalkyl iodide represented by the general formula (41)
in accordance with a method described in J. Fluorine Chem. p. 207
(1994), a compound represented by the general formula (42) can be
prepared.
[0126]
Examples of the haloalkyl iodide represented by the general
formula (41) include trifluoromethyl iodide, pentafluoroethyl
iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide,
nonafluoro-n-butyl iodide, nonafluoroisopropyl iodide and the
like. These may be suitably used in the range of 1 to 10 mole
equivalents, based on the compound represented by the general
formula (40).
[0127]
The solvent to be used in this process is not restricted to
solvents described in the above documents and may not remarkably
hinder the progress of the reaction. Examples thereof include
water; aromatic hydrocarbons such as benzene, toluene, xylene and
the like; halogenated hydrocarbons such as dichloromethane,
chloroform, carbon tetrachloride and the like; chained ethers or
cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran,
1,2-dimethoxyethane and the like; esters such as ethyl acetate,
butyl acetate and the like; alcohols such as methanol, ethanol and
the like; ketones such as acetone, methylisobutyl ketone,
54
cyclohexanone and the like; amides such as dimethylformamide,
dimethylacetamide and the like; nitriles such as acetonitrile and
the like; and inert solvents such as
1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide
and the like. These solvents can be used singly or in combination
of two or more kinds. Particularly preferable is a polar solvent.
The reaction temperature may be suitably selected in the range of
-20 degree centigrade to the reflux temperature of a solvent in
use, while the reaction time may be properly selected in the range
of several minutes to 96 hours.
6-(ii): General formula (42) -> General formula (43)
A compound represented by the general formula (43) can be
prepared by using a suitable halogenating agent. For example, a
method as described in Synth. Commun. p. 1261 (1989) can be cited.
[0128]
Examples of the halogenating agent include chlorine, bromine,
iodine, N-chlorosuccinic acid imide, N-bromosuccinic acid imide,
N-iodosuccinic acid imide and the like. These may be suitably used
in the range of 1 to 10 mole equivalents, based on a compound
represented by the general formula (42).
[0129]
In this process, an appropriate solvent can also be used, but
a solvent in use is not restricted to solvents described in the
above documents and may not remarkably hinder the progress of the
reaction. Examples thereof include water; aromatic hydrocarbons
such as benzene, toluene, xylene and the like; halogenated
hydrocarbons such as dichloromethane, chloroform, carbon
55
tetrachloride and the like; chained ethers or cyclic ethers such
as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane
and the like; esters such as ethyl acetate, butyl acetate and the
like; alcohols such as methanol, ethanol and the like; ketones such
as acetone, methylisobutyl ketone, cyclohexanone and the like;
amides such as dimethylformamide, dimethylacetamide and the like;
nitriles such as acetonitrile and the like; and inert solvents such
as 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide
and the like. These solvents can be used singly or in combination
of two or more kinds. Particularly preferable is a polar solvent.
The reaction temperature may be suitably selected in the range of
-20 degree centigrade to the reflux temperature of a solvent in
use, while the reaction time may be properly selected in the range
of several minutes to 96 hours.
6-(iii): General formula (43) -» General formula (44)
A compound represented by the general formula (44) can be
prepared by using a suitable oxidant. For example, a method
described in Tetrahedron Lett. p. 4955 (1994) can be cited.
[0130]
Examples of the oxidant include organic peroxides such as
m-chloroperbenzoic acid and the like, sodium metaperiodate,
hydrogen peroxide, ozone, selenium dioxide, chromic acid,
dinitrogen tetraoxide, acyl nitrate, iodine, bromine,
N-bromosuccinic acid imide, iodosylbenzyl, t-butyl hypochlorite
and the like.
[0131]
The solvent to be used in this process is not restricted to
56
solvents described in the above documents and may not remarkably
hinder the progress of the reaction. These solvents can be used
singly or in combination of two or more kinds. Particularly
preferable is a polar solvent. The reaction temperature may be
suitably selected in the range of -20 degree centigrade to the
reflux temperature of a solvent in use, while the reaction time
may be properly selected in the range of several minutes to 96
hours.
6-(iv): General formula (43) -> General formula (43-2)
A compound represented by the general formula (43-2) (wherein,
in the formula, any one of Y! and ¥5 must represent a methyl group)
can be prepared from a compound represented by the general formula
(43) by using a suitable methylating agent. In this process, for
example, a method described in Tetrahedron Lett. p. 6237 (2000)
can be cited.
[0132]
6-(v): General formula (43-2) - General formula (44-2)
A compound represented by the general formula (44-2) (wherein,
in the formula, any one of YI and Y5 must represent a methyl group)
can be prepared according to the method described in preparation
method 6-(iii).
[0133]
Furthermore, the compound of the present invention can be
prepared by suitably selecting a preparation method illustrated
in the present invention using an aniline derivative represented
by the general formula (43), (44), (43-2) or (44-2).
57
Preparation Method 7
[0134]
I-
(41) Oxidation
»*•
(47)
[0135]
• wherein, in the formula, R2, YI, Y2, Y4, Y5, Rf and m represent
the same as those described in the preparation method 6.
An aniline derivative represented by the general formula (47)
can be prepared using a compound represented by the general formula
(45) as a starting raw material according to the preparation method
6. Furthermore, by suitably selecting a preparation method
illustrated in the present invention, the compound of the present
invention can be prepared.
Preparation Method
[0136]
NO,,
(X)n
[0137]
wherein, in the formula, AI, A2, A3, A4, X, n, G2, R2 and Q2
represent the same as those described above.
58
By reacting a compound represented by the general formula (48)
with a suitable reactant using a suitable base in a proper solvent,
a compound represented by the general formula (49) can be prepared.
[0138]
Solvents may not remarkably hinder the progress of the reaction
and examples thereof include aliphatic hydrocarbons such as hexane,
cyclohexane, methylcyclohexane and the like; aromatic
hydrocarbons such as benzene, xylene, toluene and the like;
halogenated hydrocarbons such as dichloromethane, chloroform,
carbon tetrachloride, 1,2-dichloroethane and the like; ethers such
as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane
and the like; amides such as dimethylformamide, dimethylacetamide
and the like; nitriles such as acetonitrile, propionitrile and the
like; ketones such as acetone, methylisobutyl ketone,
cyclohexanone, methylethyl ketone and the like; esters such as
ethyl acetate, butyl acetate and the like; alcohols such as
methanol, ethanol and the like; and solvents such as
1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide;
water and the like. These solvents can be used singly or in
combination of two or more kinds.
[0139]
Examples of the base include organic bases such as triethylamine,
tributylamine, pyridine, 4-dimethylaminopyridine and the like;
alkali metal hydroxides such as sodium hydroxide, potassium
hydroxide and the like; carbonates such as sodium hydrogen
carbonate, potassium carbonate and the like; phosphates such as
potassium mono-hydrogen phosphate, tri-sodium phosphate and the
59
like; alkali metal hydrides such as sodium hydride and the like;
alkali metal alkoxides such as sodium methoxide, sodium ethoxide
and the like; organolithiums such as n-butyl lithium and the like;
and Grignard reagents such as ethyl magnesium bromide and the like.
[0140]
These bases may be suitably selected in the range of 0.01 to 5
mole equivalents based on the compound represented by the general
formula (48) or may be used as a solvent.
[0141]
Examples of the reactant include halogenated alkyls such as
methyl iodide, ethyl bromide, trifluoromethyl iodide,
2 , 2 , 2-trifluoroethyl iodide and the like; halogenated allyls such
as allyl iodide and the like; halogenated propargyls such as
propargyl bromide and the like; halogenated acyls such as acetyl
chloride and the like; acid anhydrides such as trifluoroacetic
anhydride and the like; and alkyl sulfuric acids such as dimethyl
sulfate, diethyl sulfate and the like.
[0142]
These reactants may be suitably selected in the range of 1 to
5 mole equivalents, based on the compound represented by the
general formula (48) or may be used as a solvent.
[0143]
The reaction temperature may be suitably selected in the range
of -80 degree centigrade to the reflux temperature of a solvent
in use, while the reaction time may be properly selected in the
range of several minutes to 96 hours.
60
Preparation Method 9
[0144]
NH2
A R2
**ii 1* \i
A%fY% (X)n &2
(22)
[0145]
wherein, in the formula, AI, A2, A3, A4, X, n, G2, RI, R2 and Q2
represent the same as those described above.
9-(i): General formula (22) -» General formula (50)
By reacting a compound represented by the general formula (22)
with aldehydes or ketones in an appropriate solvent, adding a
suitable catalyst and reacting the resultant in a hydrogen
atmosphere, a compound represented by the general formula (50) can
be prepared.

WE CLAIM
1. A composition for preventing harmful organisms containing one or two or more
compounds selected from compounds represented by the general formula (1), and one or two or
more kinds selected from other insecticides, miticides or fungicides as active ingredients,
wherein, in the formula, Ai, A2, A3 and A4 independently represent a carbon atom, a
nitrogen atom or an oxidized nitrogen atom; Gi and G2 independently represent an oxygen atom
or a sulfur atom; Ri and R2 independently represent a hydrogen atom or a C1-C4 alkyl group;
Xs may be the same or different and represent a hydrogen atom, a halogen atom or a
trifluoromethyl group; Qi represents a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or
different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group,
a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4
haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy
group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a
C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a
C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a
cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl
group,
a heterocyclic group (The heterocyclic group herein represents a pyridyl group, a pyridine
N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl
group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an
isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or
^ 293
a tetrazolyl group.) or
a substituted heterocyclic group having one or more substituents which may be the same or
different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group,
a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4
haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy
group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a
C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulflnyl group, a C1-C3 alkylsulfonyl group, a
C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a
cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl
group (The heterocyclic group represents the same as those described above.); and
Q2 is represented by the general formula (2) or (3),
y?A (2)
Y4
wherein, in the formula, Yi and Y5 may be the same or different and represent a halogen
atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3
haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulflnyl group, a C1-C3 alkylsulfonyl group, a C1-C3
haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a
C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6
perfluoroalkylsulfonyl group; and Y2 and Y4 represent a hydrogen atom, a halogen atom or a
C1-C4 alkyl group; or
Y ^ N ^ Y 8
^ 294
wherein, in the formula, Y6 and Y9 may be the same or different and represent a halogen
atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3
haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3
haloalkylsulfonyl group or a cyano group; Y8 represents a C2-C6 perfluoroalkyl group, a
C1-C6 perfiuoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6
perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4
alkyl group,
wherein insecticides, miticides and fungicides are one or two or more compounds selected from
azinphos-methyl, acephate, isoxathion, isofenphos, ethion, etrimfos, oxydemeton-methyl,
oxydeprofos, quinalphos, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, cyanophos,
dioxabenzofos, dichlorvos, disulfoton, dimethylvinphos, dimethoate, sulprofos, diazinon,
thiometon, tetrachlorvinphos, temephos, tebupirimfos, terbufos, naled, vamidothion,
pyraclofos, pyridafenthion, pirimiphos-methyl, fenitrothion, fenthion, phenthoate,
flupyrazophos, prothiofos, propaphos, profenofos, phoxime, phosalone, phosmet, formothion,
phorate, malathion, mecarbam, mesulfenfos, methamidophos, methidathion, parathion, methyl
parathion, monocrotophos, trichlorphon, EPN, isazophos, isamidofos, cadusafos, diamidaphos,
dichlofenthion, thionazin, fenamiphos, fosthiazate, fosthietan, phosphocarb, DSP, ethoprophos,
alanycarb, aldicarb, isoprocarb, ethiofencarb, carbaryl, carbosulfan, xylylcarb, thiodicarb,
pirimicarb, fenobucarb, furathiocarb, propoxur, bendiocarb, benfuracarb, methomyl, metolcarb,
XMC, carbofuran, aldoxycarb, oxamyl, acrinathrin, allethrin, esfenvalerate, empenthrin,
cycloprothrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cyfluthrin, beta-cyfluthrin,
cypermethrin, alpha-cypermethrin, zeta-cypermethrin, silafluofen, tetramethrin, tefluthrin,
deltamethrin, tralomethrin, bifenthrin, phenothrin, fenvalerate, fenpropathrin, furamethrin,
prallethrin, flucythrinate, fluvalinate, flubrocythrinate, permethrin, resmethrin, ethofenprox,
cartap, thiocyclam, bensultap, acetamiprid, imidacloprid, clothianidin, dinotefuran, thiacloprid,
thiamethoxam, nitenpyram, chlorfluazuron, diflubenzuron, teflubenzuron, triflumuron,
novaluron, noviflumuron, bistrifluron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron,
W 295
lufenuron, chromafenozide, tebufenozide, halofenozide, methoxyfenozide, diofenolan,
cyromazine, pyriproxyfen, buprofezin, methoprene, hydroprene, kinoprene, triazamate,
endosulfan, chlorfenson, chlorobenzilate, dicofol, bromopropylate, acetoprole, fipronil,
ethiprole, pyrethrin, rotenone, nicotine sulphate, BT(Bacillus Thuringiensis) agent, spinosad,
abamectin, acequinocyl, amidoflumet, amitraz, etoxazole, chinomethionat, clofentezine,
fenbutatin oxide, dienochlor, cyhexatin, spirodiclofen, spiromesifen, tetradifon, tebufenpyrad,
binapacryl, bifenazate, pyridaben, pyrimidifen, fenazaquin, fenothiocarb, fenpyroximate,
fluacrypyrim, fluazinam, flufenzin, hexythiazox, propargite, benzomate, polynactin complex,
milbemectin, lufenuron, mecarbam, methiocarb, mevinphos, halfenprox, azadirachtin,
diafenthiuron, indoxacarb, emamectin benzoate, potassium oleate, sodium oleate, chlorfenapyr,
tolfenpyrad, pymetrozine, fenoxycarb, hydramethylnon, hydroxy propyl starch, pyridalyl,
flufenerim, flubendiamide, flonicamid, metaflumizole, lepimectin, TPIC, albendazole,
oxibendazole, oxfendazole, trichlamide, fensulfothion, fenbendazole, levamisole
hydrochloride, morantel tartrate, dazomet, metam-sodium, a compound represented by the
general formula (A),
R13
0 R14
wherein, in the formula, Rl 1 represents a methyl group or a chloro group; R12 represents a
methyl group, a chloro group, a bromo group or a cyano group; R13 represents a chloro group,
a bromo group, a trifluoromethyl group or a cyanomethoxy group; and R14 represents a methyl
group or an isopropyl group,
a compound represented by the general formula (B),
9 296
-ox s>
(AcH,
wherein, in the formula, R21 represents a l,l,l,2,3,3,3-heptafluoro-2-propyl group or a
1,1,2,2,3,3,3-heptafluoro-l-propyl group,
triadimefon, hexaconazole, propiconazole, ipconazole, prochloraz, triflumizole,
tebuconazole, epoxiconazole, difenoconazole, flusilazole, triadimenol, cyproconazole,
metconazole, fluquinconazole, bitertanol, tetraconazole, triticonazole, flutriafol, penconazole,
diniconazole, fenbuconazole, bromuconazole, imibenconazole, simeconazole, myclobutanil,
hymexazole, imazalil, furametpyr, thifluzamide, etridiazole, oxpoconazole, oxpoconazole
fumarate, pefurazoate, prothioconazole, pyrifenox, fenarimol, nuarimol, bupirimate,
mepanipyrim, cyprodinil, pyrimethanil, metalaxyl, oxadixyl, benalaxyl, thiophanate,
thiophanate-methyl, benomyl, carbendazim, fuberidazole, thiabendazole, manzeb, propineb,
zineb, metiram, maneb, ziram, thiuram, chlorothalonil, ethaboxam, oxycarboxin, carboxin,
flutolanil, silthiofam, mepronil, dimethomorph, fenpropidin, fenpropimorph, spiroxamine,
tridemorph, dodemorph, flumorph, azoxystrobin, kresoxim-methyl, metominostrobin,
orysastrobin, fluoxastrobin, trifloxystrobin, dimoxystrobin, pyraclostrobin, picoxystrobin,
iprodione, procymidone, vinclozolin, chlozolinate, flusulfamide, dazomet, methyl
isothiocyanate, chloropicrin, methasulfocarb, hydroxyisoxazole, potassium hydroxyisoxazole,
echlomezol, D-D, carbarn, basic copper chloride, basic copper sulfate, copper
nonylphenolsulfonate, oxine copper, DBEDC, anhydrous copper sulfate, copper sulfate
pentahydrate, cupric hydroxide, inorganic sulfur, wettable sulfur, lime sulfur, zinc sulfate,
fentin, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hypochlorite, silver,
edifenphos, tolclofos-methyl, fosetyl, iprobenfos, dinocap, pyrazophos, carpropamid, fthalide,
tricyclazole, pyroquilon, diclocymet, fenoxanil, kasugamycin, validamycin, polyoxins,
blasticiden S, oxytetracycline, mildiomycin, streptomycin, rape seed oil, machine oil,
benthiavalicarbisopropyl, iprovalicarb, propamocarb, diethofencarb, fluoroimide, fludioxanil,
^ 297
fenpiclonil, quinoxyfen, oxolinic acid, chlorothalonil, captan, folpet, probenazole,
acibenzolar-S-methyl, tiadinil, cyflufenamid, fenhexamid, diflumetorim, metrafenone,
picobenzamide, proquinazid, famoxadone, cyazofamid, fenamidone, zoxamide, boscalid,
cymoxanil, dithianon, fluazinam, dichlofluanide, triforine, isoprothiolane, ferimzone,
diclomezine, tecloftalam, pencycuron, chinomethionat, iminoctadine acetate, iminoctadine
albesilate, ambam, polycarbamate, thiadiazine, chloroneb, nickel dimethyldithiocarbamate,
guazatine, dodecylguanidine-acetate, quintozene, tolylfluanid, anilazine, nitrothalisopropyl,
fenitropan, dimethirimol, benthiazole, harpin protein, flumetover, mandipropamide and
penthiopyrad.
2. The composition for preventing harmful organisms as set forth in claim 1 containing one or
two or more compounds selected from compounds represented by the general formula (la) in
which all of Ai, A2, A3 and A4 in the general formula (1) are carbon atoms, and one or two or
more kinds selected from other insecticides, miticides or fungicides as active ingredients,
^ Y Y />2 da)
wherein, in the formula, Gi, G2 and Qi represent the same as those described in claim 1; Q2
is represented by the general formula (2) or (3),
vrVS (2)
Y4
wherein, in the formula, Yj and Y5 may be the same or different and represent a halogen
atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3
haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
* 298
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3
haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group; and Y2
and Y4 represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or
wherein, in the formula, Y6 and Y9 may be the same or different and represent a halogen
atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3
haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3
alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3
haloalkylsulfonyl group or a cyano group; Yg represents a C2-C6 perfluoroalkyl group; and Y7
represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group;
Xi and X2 independently represent a hydrogen atom or a fluorine atom; X3 and X4 are
hydrogen atoms; and when any one of Ri and R2 is a hydrogen atom, the other one is a C1-C4
alkyl group, or both of Ri and R2 are C1-C4 alkyl groups.
3. The composition for preventing harmful organisms as set forth in claim 1, wherein
insecticides, miticides and fungicides are one or two or more compounds selected from
fenitrothion, fenthion, isoxathion, acephate, buprofezin, pyriproxyfen, silafluofen, dinotefuran,
imidacloprid, ethofenprox, thiamethoxam, clothianidin, acetamiprid, nitenpyram, thiacloprid,
benfuracarb, methomyl, fenobucarb, spinosad, pymetrozine, fionicamid, fipronil, ethiprole,
abamectin, a compound represented by the general formula (B),
» A
mxXHA0
wherein, in the formula, R21 represents a 1,1,1,2,3,3,3-heptafluoro-2-propyl group or a
299
I fenpyroximate, pyridaben, hexythiazox, fenbutatin oxide, tebufenpyrad, pyrimidifen,
etoxazole, polynactins, milbemectin, acequinocyl, bifenazate, spirodiclofen, dienochlor,
spiromesifen, tetradifon, chlorfenapyr, clofentezine, tolfenpyrad, fluacrypyrim, propargite,
diafenthinron, flufenoxuron, penthiopyrad, flusulfamide, iminoctadine acetate, iminoctadine
albesilate, acibenzolar-S-methyl, ferimzone, pyroquilon, orysastrobin, azoxystrobin,
carpropamid, diclocymet, probenazole, tiadinil, isoprothiolane, tricyclazole, fthalide,
kasugamycin, fenoxanil, mepronil, diclomezine, pencycuron, validamycin, edifenphos,
furametpyr, thifluzatnide, flutolanil, metominostrobin, iprobenfos and oxolinic acid.
4. The composition for preverfang harmful organisms as set forth in claim 1, wherein one or
more compounds of other insecticides, miticides or fungicides are respectively contained in an
amount of 0.001 to 95 weight %.