JP2000239262A - Triazole compound and its use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having an ethoxycarbonyl or methoxycarboyl group, and having excellent insecticidal, miticidal and nematocidal efficacies and high safety to mammals, therefore useful as an active ingredient of insecticides, miticides and nematocides. SOLUTION: This new compound is a compound of formula I (R1 is ethoxycarbonyl or methoxycarbonyl; R2 is methoxymethyl when R1 is ethoxycarbonyl, being ethoxymethyl or methoxymethyl when R1 is methoxycarbonyl), e.g. 3-dichlorofluoromethylsulfenyl-1-(2,6-dichloro-4- trifluoromethylphenyl)-5-[N-ethoxycarbonyl-N-(ethoxymethyl)amino]-1,2, 4-triazole. The compound of formula I is obtained by reaction between a compound of formula II and a compound of the formula X-R21 (R21 is methoxymethyl or the like; X is an eliminable group) pref. in a solvent in the presence of a base, at -5 to 150 deg.C for 1-24 h.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a triazole compound and its use.

[0002]

BACKGROUND OF THE INVENTION JP-A-10-158250 describes that certain triazole compounds have excellent insecticidal, acaricidal and nematicidal efficacy. When such compounds are used in limited spaces such as indoors and greenhouses, or when used in fields, etc., depending on the form of use, a high degree of safety is required for their residents and sprayers. There is a need for insecticides, acaricides, and nematicides that are superior in animal safety.

[0003]

Means for Solving the Problems The present inventors have made intensive studies in view of the above situation, and as a result, have found that a triazole compound represented by the following general formula 2 has excellent insecticidal, acaricidal and nematicidal efficacy. And found that it has more excellent safety for mammals, and thus has accomplished the present invention. That is, the present invention provides a compound represented by the general formula:

Embedded image [Wherein, R ¹ represents an ethoxycarbonyl group or a methoxycarbonyl group, R ¹ represents an ethoxycarbonyl group, R ² represents an ethoxymethyl group, and R ¹ represents a methoxycarbonyl group, and R ² represents an ethoxymethyl group. Or a methoxymethyl group. [Hereinafter referred to as the compound of the present invention] and an insecticide, acaricide, and nematicide containing the same as an active ingredient.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention is a compound represented by the general formula (2), wherein R ¹ is an ethoxycarbonyl group and R ² is an ethoxymethyl group. -1- (2,6-dichloro-
4-trifluoromethylphenyl) -5- [N-ethoxycarbonyl-N- (ethoxymethyl) amino] -1,
2,4-triazole, in the above general formula 2, R
3-dichlorofluoromethylsulfenyl- wherein ¹ is a methoxycarbonyl group and R ² is a methoxymethyl group
1- (2,6-dichloro-4-trifluoromethylphenyl) -5- [N-methoxycarbonyl-N- (methoxymethyl) amino] -1,2,4-triazole; Wherein R ¹ is a methoxycarbonyl group and R ² is an ethoxymethyl group, 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- [N
-Methoxycarbonyl-N- (ethoxymethyl) amino] -1,2,4-triazole.

Next, a method for producing the compound of the present invention will be described. The compound of the present invention can be produced, for example, according to the following (production method). (Production method) The compound of the present invention has the general formula

Embedded image [Wherein, R ¹ represents the same meaning as described above. And a compound represented by the general formula

Embedded image [Wherein, R ²¹ represents a methoxymethyl group or an ethoxymethyl group, and X represents a leaving group (for example, a chlorine atom, a bromine atom,
Iodine atom, trifluoromethylsulfonyloxy group,
Methanesulfonyloxy group). And the compound represented by the formula (I) is usually reacted in a solvent in the presence of a base and, if necessary, in the presence of a catalyst. The reaction temperature of the reaction is usually about -5 ° C to 150 ° C, and the reaction time is usually 1 hour to 24 hours. The amount of the reagent used for the reaction is determined by the amount of the compound 1 represented by the general formula (3).
The compound represented by the general formula 1 is usually 1 to
The ratio is 10 moles, and the amount of the base is usually from 1 mole to a large excess mole. As the base, for example, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate;
Sodium methoxide, alkali metal alkoxides such as sodium ethoxide, triethylamine, pyridine,
Organic bases such as 4-dimethylaminopyridine, N, N-dimethylaniline and the like can be mentioned. Reaction solvents that can be used include, for example, hexane, heptane, ligroin, aliphatic hydrocarbon solvents such as petroleum ether, aromatic hydrocarbons such as benzene, dichloroethane, chlorobenzene, halogenated hydrocarbon solvents such as dichlorobenzene, diethyl ether, Ether solvents such as diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, ketone solvents such as cyclohexanone, ethyl acetate, ester solvents such as butyl acetate,
Acetonitrile, nitrile solvents such as isobutyronitrile, nitrates such as nitroethane and nitrobenzene, formamide, N, N-dimethylformamide, N, N-
Examples thereof include acid amides such as dimethylacetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, water and the like, and mixtures thereof. Examples of the catalyst used as needed include crown ether and the like. After completion of the reaction, the reaction mixture is subjected to post-treatment operations such as pouring the mixture into water, extracting the mixture with an organic solvent, and concentrating the organic layer to obtain the target compound of the present invention. The compound can be subjected to operations such as chromatography and recrystallization.

The compound represented by the general formula (3) is 5-amino-3-dichlorofluoromethylsulfenyl-1-
(2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazole and a compound of the general formula 3

Embedded image [Wherein, R ¹ and X represent the same meaning as described above. And the compound represented by the formula (I) is usually reacted in a solvent in the presence of a base and, if necessary, in the presence of a catalyst. The reaction temperature of the reaction is usually about -5 ° C to 150 ° C.
° C, and the reaction time is usually 1 hour to 24 hours.
The amount of the reagent used for the reaction is based on 1 mol of 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazole. The compound represented by the general formula 5 is usually in a proportion of 1 to 10 mol, and the amount of the base is usually in a proportion of 1 mol to a large excess mol. As the base, for example,
Inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc., alkali metal alkoxides such as sodium methoxide, sodium ethoxide, triethylamine, pyridine, 4-dimethylaminopyridine, N , N-
Organic bases such as dimethylaniline and the like can be mentioned. As a reaction solvent that can be used, for example, hexane, heptane, ligroin, aliphatic hydrocarbon solvents such as petroleum ether, aromatic hydrocarbons such as benzene, dichloroethane, chlorobenzene, halogenated hydrocarbon solvents such as dichlorobenzene,
Ether solvents such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl ether; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; ester solvents such as ethyl acetate and butyl acetate; acetonitrile and isobutyronitrile Nitrile solvents such as nitroethane, nitrobenzene, etc., acid amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, sulfur compounds such as dimethyl sulfoxide, sulfolane, water and the like, and mixtures thereof. can give. Examples of the catalyst used as needed include crown ether and the like. After the completion of the reaction, the reaction solution is poured into water, extracted with an organic solvent, and subjected to a post-treatment operation such as concentration of the organic layer to obtain a target compound. The compound can be subjected to operations such as chromatography and recrystallization.

[0007] 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazole is prepared by the following (method 1) or (method 2). ). (Method 1) 3,3'-di [5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4
[Triazolyl] disulfide and trichlorofluoromethane or bromodichlorofluoromethane, in the absence of a solvent or in a solvent, in the presence of a reducing agent. The reaction temperature of the reaction is generally about −20 ° C. to 150 ° C., and the reaction time is generally 1 hour to
24 hours. The amount of reagent used for the reaction is 3,3 '
-Di [5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazolyl]
Trichlorofluoromethane or bromodichlorofluoromethane is usually in a proportion of 2 mol to a large excess mol per mol of disulfide, and the amount of the reducing agent is usually 2 to 6 mol. Examples of the reducing agent include hydroxymethanesulfinate (a salt formed from hydroxymethanesulfinate anion and various cations; for example, alkali metal salts of hydroxymethanesulfinate such as sodium hydroxymethanesulfinate), dithionite Acid alkali metal salts (eg, sodium dithionite and the like) and the like. Examples of usable reaction solvents include aliphatic hydrocarbon solvents such as hexane, heptane, ligroin, petroleum ether, aromatic hydrocarbons such as benzene, halogenated hydrocarbon solvents such as dichloroethane, chlorobenzene and dichlorobenzene, and diethyl ether. Ether solvents such as ter, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone, and ester solvents such as ethyl acetate and butyl acetate. , Acetonitrile, nitrile solvents such as isobutyronitrile, nitrates such as nitroethane and nitrobenzene, formamide, N, N-
Examples thereof include acid amides such as dimethylformamide and N, N-dimethylacetamide; sulfur compounds such as dimethylsulfoxide and sulfolane; water; and mixtures thereof. After the completion of the reaction, the reaction solution is poured into water, extracted with an organic solvent, and subjected to a post-treatment operation such as concentration of the organic layer to obtain a target compound. The compound can be subjected to operations such as chromatography and recrystallization.

(Method 2) 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-mercapto-1,2,4-triazole, trichlorofluoromethane or bromodichlorofluoromethane Can be produced in the absence of a solvent or in a solvent in the presence of a reducing agent. The reaction temperature of the reaction is generally about −20 ° C. to 150 ° C., and the reaction time is generally 1 hour to
24 hours. The amount of the reagent used in the reaction was as follows: 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-mercapto-1,2,4-triazole and 1 mol of trichlorofluoromethane. Alternatively, bromodichlorofluoromethane is usually in a proportion of 1 mol to a large excess mol, and the amount of the reducing agent is usually 1 to 6 mol.
Examples of the reducing agent include hydroxymethanesulfinate (a salt formed from hydroxymethanesulfinate anion and various cations; for example, alkali metal salts of hydroxymethanesulfinate such as sodium hydroxymethanesulfinate), dithionite Acid alkali metal salts (eg, sodium dithionite and the like) and the like. Examples of usable reaction solvents include aliphatic hydrocarbon solvents such as hexane, heptane, ligroin, petroleum ether, aromatic hydrocarbons such as benzene, halogenated hydrocarbon solvents such as dichloroethane, chlorobenzene and dichlorobenzene, and diethyl ether. -Ter, diisopropyl ether,
Ether solvents such as dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone,
Ketone solvents such as cyclohexanone, ester solvents such as ethyl acetate and butyl acetate, nitrile solvents such as acetonitrile and isobutyronitrile, nitrates such as nitroethane and nitrobenzene, formamide, N, N-dimethylformamide, N, N-dimethylacetamide Acid amides, sulfur compounds such as dimethyl sulfoxide and sulfolane, water and the like, and mixtures thereof. After completion of the reaction, the reaction solution was poured into water, extracted with an organic solvent, and subjected to post-treatment operations such as concentration of the organic layer.
The desired compound can be obtained. The compound can be subjected to operations such as chromatography and recrystallization.

3,3,3 which is a raw material for producing 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazole '-Di [5-amino-1-
(2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazolyl] disulfide and 5
-Amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-mercapto-1,2,4-triazole can be obtained, for example, according to the method described in JP-A-10-158250. Can be manufactured.
As the trichlorofluoromethane, for example, a commercially available reagent (for example, Sigma-Aldrich Japan Co., Ltd.) can be used. Bromodichlorofluoromethane is described, for example, in J. Am. Fluorine Chem. , Volume 20, 89
-97 (1982).

The harmful insects, harmful mites and harmful nematodes to which the compound of the present invention exerts control effects include, for example,
The following are listed. Oniscus asell
us, Armadillidium vulgare,
(Polypod beetle), Porcellio scabe
Isopoda pests such as r;
diplopoda pests such as s guttulatus (a kind of millipede); Geophilus
carpophagus, Scutigera sp
p. , Scolopendra subspinipe
s (Tobisumkade), Thereunema spp.
(Chiropoda) pests such as (comrades of gezi); Symphyla pests such as Scutigellaella immaculata; Ctenole
Pisma villasa (Yamatoshimi), Lepi
Thysanura pests, such as sma saccharina (a kind of red croak spot); Tro
Psocoptera pests such as gium pulsatorium; Onych
Colembola pests such as urus armathus (a kind of white-spotted beetle); Ranidae (Mastertermitidae), Zoot
genus thermopsis, Archotermopsis
Genus, Termite (Hodotermopsis ja)
genus Hodothermopsis, P. ponica)
Termites of the genus orotetmes (Termo)
psidae), genus Kalotermes, Neotermes koshuensi
s), Neotermes, and termites (C)
genus Cryptotermes such as ryptotermes domesticus, and In such as Incitermes minor.
genus cistermes, termite (Glypt
Glyptotermes such as Otermes satsumaensis, G. nakajimai, and G. fuscus.
Genus, etc. (Kalotermitida)
e), genus Hodotetermes, Microhotot
ermes, Anacanthotermes, etc.
e), termites (Retitulitermes)
Speratus), termites (R.s.)
p), Reti such as the termite (R. flavoriceps) and the amami termite (R. miyatakei)
genus cultermes, Heterotermes
Genus, termite (Coptotermes form)
osanus) and the genus Copttermes, Sch
Rhotermitidae, Serotermitidae, Amit
ermes, Drepanotermes, Hop
genus italitermes, Trinerviterm
es genus, Macrotermes genus, Chinese termite (Odontotermes formosanus)
Odontotermes genus, Microterm
es genus, Takasago termites (Nasutermes)
Takasugoensis)
genus mes, Nitobe termite (Pericapriter
mes nitobei) etc.
Isopteridae (Isopt) such as termites (Termitidae) of the genus Rmes and Anoplottermes
era) pests;

[0011] Blatta orientalis (Periplaneta americana), Periplaneta amer
icana (Water cockroach), p. fuligino
sa (black cockroach), Leucophaea mad
erae (Madela cockroach), Blattella g
ermanica (German cockroaches), such as Dictoptera pests;
pa spp. (A kind of vignetting), Acheta dom
esticus, Teleogryl
rus emma (Emaku cricket), Locusta
migratoria, Mela
noplus differentialialis (a kind of grasshopper), Schistocerca gregari
Orthop (Orthop)
tera) pests; Labidurariparia (Toothbill beetle), Forficula auricul
Dermaptera pests, such as aria (a kind of earwigs); Phthirus p
ubis, pediculus huma
nus (head lice), Haematopinus
suls (porcine lice), Haematopinus
eurysternus (bovine lice), Damali
nia obis (sheep lice), Linognat
hus spp. (A kind of white lice), Soleno
potes spp. (Anoplura) pests such as (a kind of white lice); Trichodict
es spp. (A kind of louse louse), Trome
nopon spp. (A kind of white lice), Bovicola spp. (A kind of psyllid lice), Felicola spp. (Mallophaga) pests such as (a kind of lice)
Frankliniella intonsa (Thysanoptera: Thrips), Trips tabaci (Thysanoptera: Thrips); Thysanoptera pests such as palmi (Thysanoptera: Thrips);
Nezara spp. (A kind of green stink bug),
Eurygaster spp. (A kind of stink bug), Dysdercus intermedius
(A kind of stink bug), Cimex lectula
rius (bed bugs), Triatoma spp.
(A kind of turtle), Rhodnius prolix
us (a kind of horse turtle), Nezara ante
nnata (Coleoptera), Cletus pu
Heteroptera pests, such as netiger (Heteroptera); Aleurocan
thus spiniferus (whiteflies), Bemisiatabaci (whiteflies), Trialeurodes vapororio
rum (Aphid whiteflies), Aphis goss
ypii (cotton aphid), Brevocoryne
brassicae (radish aphid), Cry
ptomyzus ribis (a kind of aphid),
Aphis Fabae, Macrosiphume
uphorbiae (tulip beetle aphid), Myzus persicae (peach peach aphid), Phorodon humuli (hope wart aphid), Empoasca spp. (A kind of leafhopper), Nephotettix cincti
ceps (Leafhopper), Lecanium c
orni (Maduki beetle), Saiset
ia oleae (olive beetle), La
odelphax striatellas (Pyrocarpaceae), Nilaparvata lugens (Pyrocarpaceae), Aonidiella lauranti
i (Red-tailed scale), Aspidiotus
hederae, Pseudo
ococcus spp. (A kind of stag beetle), Psylla spp. (A kind of lice), P
Homoptera pests, such as hyloxera vasatrix (grape aphids);

Pectinophora gossip
iella (Limegrass beetle), Lithocolle
tis blankcardella (a kind of hosoga),
Plutella xylostella (conaga),
Malacosoma neustria (Obikareja), Euprotis subflava (Dokuga), Lymantria dispar (Gypsy moth), Bucculatrixpyrivorella
(Nasitibiga), Phyllocnistis cit
rella, Citrus agrotis, Agrotis s
pp. (A kind of Kaburayaga), Euxoa spp.
(A kind of noctuids), Earias insulana (a kind of waterlinga), Heliothis spp. (A kind of beetle), Spodoptera exigu
a. litura (Spodoptera litura), Spodoptera spp. (A kind of armyworm), Mamestra brassicae (armyworm), Trichoplusia ni (a kind of armyworm), Carpocapsa pomonella
(Codlinga), Pieris spp. (A kind of cabbage butterfly), Chilo spp. (A kind of potato), Pyrausta nubilalis (a kind of potato), Ephessia kuehniella
(Sujiko nomadameiga), Galleria mel
lonella (Honey moth), Tineolabis
selliella (koiga), Tenea tran
slucens (Iga), Homona magnan
ima (chahamaki), Tortrixviridan
a (Lepidoptera)
ra) Pests: Anobium punctatum (a kind of beetle), Rhizopertha domi
Nicca, Acanthosce
rides obectus (Pink beetle), Agelastica alni (a kind of leaf beetle), Leptinotarsa decemli
neata (Colorado potato beetle), Phaedon co
chleariae (a kind of beetle), Diabrot
ica spp. (A kind of corn rootworm), Ps
ylliodes angusticollis (Eggplant flea beetle), Phyllotretastriola
ta (Eurasian flea beetle), Epilachna sp
p. (A kind of ladybird)
iaspp. (A kind of beetle), Oryzaeph
ilus surinamensis, Anthonomus spp. (A kind of weevil), Sitophilus spp. (A kind of weevil), Otiohynchus sulc
atus, Cosmopo
lites sordidus, ceuthorhyncidius albos
uturalis (hyper weevil), Hypera
postica (alfalfa weevil), D
ermestes spp. A kind of cutlet bug),
Trogoderma spp. (A kind of beetle beetle), Attagenus unicolor
(Himekatsuobushimushi), Lyctus dentat
um (Alageniferus bark beetle), L. planico
llis (American Flycatcher beetle), L. sine
nsis (Keyaki Hirataki Beetle), L. n. linea
ris (Narahira bark beetle), L. brunneu
s (Hirata bark beetle); africanus (African fly bark beetle) and other leaf beetle families (L
yctridae), Meligethes aene
us (a kind of poppy), Ptinusspp. (A kind of leopard beetle), Gibbium psyllo
ides (Triple leopard beetle), Triboliu
m spp. (A kind of succulent), Teneb
rio molitor (Acalycium beetle), Agriotes spp. (A kind of Munaboshi beetle), Melolontha mololoth
a (a kind of stag beetle), genus Xyleborus, S
bark beetles of the genus coloplatypus (S
(corytidae), genus Monochamus, Hy
genus lotrupes, Hesperophanus,
Chlorophorus, Palaeocalli
genus, Semanotus, Purpuric
Enumus, Stromium and the like, Cerambycidae, Crossotar
Platypoidae, such as genus sus and Platypus, Dinoderus
Genus, Botrychus, Sinoderus, etc.
Genus Ernobius, genus Anobium, Xyleti
genus nus, genus Xestobium, Ptilinus
Genus, Nicobium, Ptilineurus, etc., Coleoptera (Anobiidae), Coleoptera (Bupresidae), etc., Coleoptera (Coleo)
ptera) pest; Diprion spp. (A kind of black-spotted wasp), Hoplocampa spp.
(A kind of bee), Lasius spp. (A kind of black ant), Formica japonica (Black ant), Vespa spp. Hymenoptera (Hymenop) such as the wasp family (Siricidae) of the genus Urocerus, Sirex, etc.
tera) pests; Aedes spp. (A kind of sea lion), Anopheles spp. (A kind of anopheles), Culex spp. (A kind of Culex), Dro
sophila melanogaster (a kind of Drosophila melanogaster), Musca domestici
ca (housefly), Fannia spp. (A kind of Musca domestica), Calliphora spp. (A kind of blowfly), Lucilia spp. (A kind of fly), Chrysomya spp. (A kind of lobster), Cuterebra spp. , Gastr
ophilusspp. (A kind of horsefly), Storm
oxys spp. (A kind of flies), Oestru
s spp. (A kind of sheep fly), Hypoderm
a spp. (A kind of bullflies), Tabanus s
pp. (A kind of flies), Biohortullan
us (a kind of flies), Pegomyia hyosc
yami (a kind of fly), Ceratitis c
apitata (Diptera), Dacus
dorsalis (Fruit fruit fly), Tipula
paludosa (a kind of gagbo), Simuliu
m spp. (A kind of blackflies), Eusimulium
spp. , Phlebotomus spp. (A kind of sandfly), Culicoides spp.
(A kind of Nukaka), Chrysops spp. (A kind of black fly), Haematopota spp.
(A kind of flies), Braula spp. (A kind of honeybee fly), Morellia spp.
(A kind of fly), Glossina spp. (A kind of tsetse fly), Wohlfahrtia sp
p. , Sarcophaga spp. (A kind of flies), Lipoptena spp. (A kind of lice) and Melophagus spp. (A kind of lice), Muscina spp. (Diptera) pests such as (a house fly); Xenop
sylla cheopis,
Ctenocephalides felis (cat flea), Ctenocephalides canis
(Dog flea), Ceratophyllus spp.
(A kind of spiny flea), Pulex spp. (One of the human fleas), such as Siphonaptera pests; Scorpio maurus, Latrodec
tus mactans, Chiracantium
spp. (Ara)
chnida) pests;

Otodictes spp. (A kind of mites), Acarus siro (Acari: Acarina) Argas spp. (A kind of ticks), O
rnithodoros spp. (A kind of mites), Ornithonyssus spp. (A kind of house dust mite), Dermanyssus spp. (A kind of mites), Eriophys spp. (A kind of mites), Haemaphyxalis longic
ornis (Tickle tick), Boophilus
microplus, Rhipic
ephalus spp. (A kind of red tick), C
helicaropsis moorei (Small mites), Dermatophagoides spp.
(A kind of Dermatophagoides mite), Hyalomma spp.
(A kind of Ixodid tick), Ixodesovatus (Yamato-mite), Ixodes persulcatus
(Schulze tick), Psoroptes equi
(Kyusen mite), Chorioptes s
pp. (A kind of red mite), Sarcopt
es spp. (Scarlet mite), Tarsone
mus spp. (A kind of dust mite), Bryobi
a Praetiosa (Clover spider mite), Pano
nychus spp. (A kind of Citrus spider mite), Te
tranychus spp. (A kind of spider mite),
Dermacentor spp. (A kind of Oxodid tick), Haemaphysalis spp. (A kind of tick), Railietia spp. , Pne
umonyssus spp. (A kind of Salmonid mite), Sternostoma spp. , Acar
apisspp. (A kind of bee mite), Cheyl
etiella spp. (A kind of claw mite), Myo
bia spp. (A kind of mite mite), Psorer
gatespp. (A kind of sheep mite), Dem
odex spp. (A kind of acne mites), Tromb
icula spp. (A kind of chiggers), List
rophorus spp. (A kind of woodpecker), T
yrophagus spp. (A kind of Acarina mites), Sarcoptes spp. (A kind of red mite), Notoedres spp. (A kind of cat mite), Cytodid
es spp. (A kind of dust mite), Laminoshi
optes spp. Acarina
Pests; Pratylenchus spp. (Negusa nematode species), Grobodera spp. , H
eterodera spp. (Cyst nematodes), Meloidogyne spp. (A kind of root-knot nematode), Aphelenchoides sp
p. (Singare nematodes), Notylench
us spp. (Messiah species), Bursap
Pests of plant parasitic nematodes, such as elenchus lignicolus (pine wood nematode). Furthermore, the compounds of the present invention are also effective against pests that have developed resistance to existing insecticides, mites and nematicides.

When the compound of the present invention is used as an active ingredient of an insecticide, acaricide, or nematicide, the compound of the present invention or a salt of the compound of the present invention—an inorganic acid (such as hydrochloric acid or sulfuric acid) or an organic acid (p-toluene sulfone) An acid or the like) and a pharmaceutically acceptable salt thereof may be used as it is without adding any other components, but usually, a solid carrier, a liquid carrier, a gaseous carrier,
Mix with feed, etc., or impregnate into a substrate such as a porous ceramics plate or a non-woven fabric, and add a surfactant or other formulation auxiliary agent, if necessary, to make oils, emulsions, wettable powders, flowables, It is used in the form of granules, powders, aerosols, aerosols (eg, fogging), heat transpiration agents, smokers, poison baits, mites, resin formulations, etc. In these preparations, the compound of the present invention is usually contained in an amount of 0.01% to 9% by weight as an active ingredient.
Contains 5%.

[0015] Examples of the solid carrier used in the formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (cellulose). Fine powder or granular materials such as cite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc., and chemical fertilizers (ammonium sulfate, phosphorous ammonium, nitrate, urea, salt ammonium, etc.). For example, water, alcohols (such as methanol and ethanol), ketones (such as acetone and methyl ethyl ketone), aromatic hydrocarbons (such as benzene, toluene, xylene, ethylbenzene and methylnaphthalene), and aliphatic hydrocarbons (such as hexane and ethanol) Cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile , Isobutyronitrile), ethers (diisopropyl e - ether, dioxane),
Acid amides (N, N-dimethylformamide, N, N-
Dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), vegetable oils such as dimethylsulfoxide, soybean oil, cottonseed oil and the like. , LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide and the like.

Examples of the bait bait include bait ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid. Examples thereof include an ingestion inhibitor such as pepper powder, an attractive flavor such as a cheese flavor and an onion flavor. Examples of the surfactant include an alkyl sulfate, an alkyl sulfonate, and an alkyl allylate.
Sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives and the like. Examples of auxiliary agents for preparations such as fixing agents and dispersants include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers ( Polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), and examples of the stabilizer include PAP (acidic isopropyl phosphate) and BHT.
(2,6-di-tert-butyl-4-methylpheno-
), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, surfactant, fatty acid or ester thereof and the like. can give.

When the compound of the present invention is used as an insecticide, acaricide or nematicide for agriculture, the application rate is usually 0.1 to 100 g per 10 ares, and emulsions, wettable powders, flowables and the like are used. When diluted with water, the application concentration is usually 1 to 10000 ppm, and granules, powders, and the like are applied as they are without dilution. When used as an insecticide, miticide or nematicide for epidemic prevention, the emulsion, wettable powder, flowable and the like are usually 0.1 ppm to 5 ppm in water.
It is applied after being diluted to 00 ppm, and oils, aerosols, aerosols, poison baits, anti-mite sheets and the like are applied as they are. These application rates and application concentrations differ depending on the type of preparation, application time, application place, application method, type of pest, degree of damage, and the like, and can be increased or decreased without being affected by the above range.

The compounds of the present invention are particularly suitable for controlling animal ectoparasites because of their high safety for mammals. When the compound of the present invention is used as an insecticide or acaricide for the purpose of controlling ectoparasites of animals such as livestock such as cattle and pigs, pets such as dogs and cats, the compound of the present invention or a salt of the compound of the present invention is used. Used in a veterinary manner. For example, systemic control (systemic controller)
ol), a method such as tablet, capsule, immersion liquid, boli, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is used for non-systemic suppression ( For the purpose of non-systemic control, methods such as spraying, pouring (pour-on), and dropping (spot-on) an oily or aqueous solution, and forming a resin formulation into a suitable shape such as a collar or ear tag It is used by using a molded article. The compound of the present invention
Usually, 0.01 to 100 mg of the compound of the present invention is applied to 1 kg of a host animal.

The compound of the present invention can be used with other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. They can be mixed or used in combination. Examples of the active ingredient of such insecticides, nematicides, and miticides include, for example, fenitrothion [O,
O-dimethyl O- (3-methyl-4-nitrophenyl) phosphorothioate], phenthione [O, O-dimethyl O- (3-methyl-4- (methylthio) phenyl) phosphorothioate], diazinon [O, O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate], chloropyrifos [O, O-diethyl-O-3,5,6-trichloro-2
-Pyridyl phosphorothioate], acephate [O,
S-dimethylacetyl phosphoramidothioate], methidathion [S-2,3-dihydro-5-methoxy-2-
Oxo-1,3,4-thiadiazol-3-ylmethyl O, O-dimeterphosphorodithioate], disulfoton [O, O-diethyl S-2-ethylthioethylphosphorodithioate] , DDVP [2,2-dichlorovinyl dimethyl phosphate], sulphophos [O-ethyl O-4- (methylthio) phenyl S-propyl phosphorodithioate], cyanophos [O-4-cyanophenyl O, O-dimethyl phosphorothioate], dioxabenzophos [2-methoxy-4H-1, 3,2-benzodioxaphosphorin-2-sulfide], dimethoate [O, O-dimethyl-S- (N-methylcarbamoylmethyl) dithiophosphate], fentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate], malachi Emissions [diethyl (dimethoxy phosphino Chi oil thio) Sakushine - DOO], trichlorfon [dimethyl 2,2,2-trichloro-1-hydroxyethyl phosphate bone - DOO], azinphos-methyl [S-
3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O, O-dimethylphosphorodithioate], monocrotophos [dimethyl (E) -1
-Methyl-2- (methylcarbamoyl) vinyl phosphate], ethion [O, O, O ', O'-tetraethyl S, S'-methylenebis (phosphorodithioate)]
BPMC (2-sec-butylphenyl methylcarbamate), benfracarb [ethyl N- [2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl (methyl) aminothio] ] -N-isopropyl-β-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-
2,2-dimethyl-7-benzo [b] furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl-N-methylcarbamate], mesomil [S-methyl] -N-[(methylcarbamoyl) oxy] thioacetimidate], ethiophenecarb [2
-(Ethylthiomethyl) phenylmethylcarbamoy
G], aldicarb [2-methyl-2- (methylthio)
Propionaldehyde O-methylcarbamoyloxime], oxamyl [N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide], phenothiocarb [S- (4-phenoxybutyl) -N, N-dimethylthiocarbame -G) -based carbamate compounds;

Etofenprox [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS) -α-
Cyano-3-phenoxybenzyl (RS) -2- (4
-Chlorophenyl) -3-methylbutyrate], esfenvalerate [(S) -α-cyano-3-phenoxybenzyl (S) -2- (4-chlorophenyl) -3-
Methyl butyrate], fenpropatrin [(RS)-
α-cyano-3-phenoxybenzyl 2,2,3,3
-Tetramethylcyclopropanecarboxylate], cypermethrin [(RS) -α-cyano-3-phenoxybenzyl (1RS) -cis, trans-3- (2,2
-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1RS) -cis, trans-3- (2,2-
Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], cyhalothrin [(RS) -α-cyano-3-phenoxybenzyl (Z)-(1RS) -ci
s-3- (2-Chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S) -α-cyano-3-phenoxy] Benzyl (1R) -cis-3-
(2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate], cycloprothrin [(R
S) -α-Cyano-3-phenoxybenzyl (RS)
-2,2-dichloro-1- (4-ethoxyphenyl) cyclopropanecarboxylate], fluvalinate (α
-Cyano-3-phenoxybenzyl N- (2-chloro-α, α, α-trifluoro-p-tolyl) -D-barynate), bifenthrin (2-methylbiphenyl-3)
-Ylmethyl) (Z)-(1RS) -cis-3- (2
-Chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxyle-
G, 2-methyl-2- (4-bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) ether, tralomethrin [(S) -α-cyano-3-phenoxybenzyl (1R) -cis-3- ( 1, 2, 2, 2-
Tetrabromoethyl) -2,2-dimethylcyclopropanecarboxylate], silafluofen [4-ethoxyphenyl {3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane], d-phenothrin [3-phenoxy Benzyl (1R-cis, trans)
-Chrysanthemate], cyphenothrin [(RS) -α
-Cyano-3-phenoxybenzyl (1R-cis, trans) -chrysanthemate), d-resmethrin [5
-Benzyl-3-furylmethyl (1R-cis, trans) -chrysanthemate], acrinasulin [(S)-
α-cyano-3-phenoxybenzyl (1R-cis (Z))-(2,2-dimethyl-3- (3-oxo-3)
-(1,1,1,3,3,3-hexafluoropropyloxy) propenyl) cyclopropanecarboxyle-
G), cyfluthrin [(RS) -α-cyano-4-fluoro-3-phenoxybenzyl 3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], tefluthrin [2,3 5,6-tetrafluoro-4-methylbenzyl (1RS-cis (Z))
-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], transfluthrin [2,3,5,6
-Tetrafluorobenzyl (1R-trans) -3-
(2,2-dichlorovinyl) -2,2-dimethylcyclopropane ruboxylate], tetramethrin [3,
4,5,6-tetrahydrophthalimidomethyl (1R
S) -cis, trans-chrysanthemate], aletrin [(RS) -3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS) -cis, trans-chrysanthemate], praletrin [ (S) -2-methyl-4-oxo-3- (2-propynyl) cyclopent-2-enyl (1R) -cis, trans-chrysanthemate], empentrin [(RS) -1-ethynyl-2-methyl -2-pentenyl (1R) -cis, trans-chrysanthemate], imiprosulin [2,5-
Dioxo-3- (prop-2-ynyl) imidazolidin-1-ylmethyl (1R) -cis, trans-2,2
-Dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate], d-framethrin [5
-(2-propynyl) furfuryl (1R) -cis, trans-chrysanthemate], 5- (2-propynyl)
Pyrethroid compounds such as furfuryl 2,2,3,3-tetramethylcyclopropanecarboxylate;

Buprofezin (2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-
Thiadiazine derivatives such as thiadiazin-4-one), nitroimidazolidine derivatives, cartap (S, S'-)
(2-dimethylaminotrimethylene) bis (thiocarbamate)], thiocyclam [N, N-dimethyl-1,
Neraistoxin derivatives such as 2,3-trithian-5-ylamine] and bensultap [S, S'-2-dimethylaminotrimethylene di (benzenethiosulfonate)], N-cyano-N'-methyl N-cyanoamidine derivatives such as -N '-(6-chloro-3-pyridylmethyl) acetamidine; endosulfan [6,7,8.
9,10,10-hexachloro-1,5,5a, 6,
9,9a-Hexahydro-6,9-methano-2,4,3
-Benzodioxathiepine oxide], gamma-
BHC (1, 2, 3, 4, 5, 6-hexachlorocyclohexane), 1,1-bis (chlorophenyl) -2,
Chlorinated hydrocarbon compounds such as 2,2-trichloroethanol and chlorofluazurone [1- (3,5-dichloro-4)
-(3-chloro-5-trifluoromethylpyridine-2
-Yloxy) phenyl) -3- (2,6-difluorobenzoyl) urea], teflubenzuron [1- (3,
5-dichloro-2,4-difluorophenyl) -3-
(2,6-difluorobenzoyl) urea], flufenoxuron [[1- (4- (2-chloro-4-trifluoromethylphenoxy) -2-fluorophenyl] -3-
(2,6-difluorobenzoyl) urea] and other benzoylphenylurea-based compounds, amitraz [N, N ′
[(Methylimino) dimethylidin] di-2,4-xylysine], chlorodimform [N ′-(4-chloro-2-
Meterphenyl) -N, N-dimethylmethanimidamide]
Formamidine derivatives, diafenthiuron [N-
(2,6-diisopropyl-4-phenoxyphenyl)
Thiourea derivatives such as -N'-tert-butylcarbodiimide], phenylpyrazole compounds, methoxadiazone [5-methoxy-3- (2-methoxyphenyl)-
1,3,4-oxadiazol-2- (3H) -one], bromopropylate [isopropyl 4,4′-
Dibromobenzylate], tetradiphone [4-chlorophenyl 2,4,5-trichlorophenyl sulfone],
Quinometeone [S, S-6-methylquinoxaline-
2,3-diyldithiocarbonate], propargite [2- (4-tert-butylphenoxy) cyclohexylprop-2-yl sulfite], fenbutatin oxide [bis [tris (2-methyl-2-phenylpropionate)] Ru) tin] oxide], hexthiazox [(4RS, 5RS) -5- (4-chlorophenyl)
-N-chlorohexyl-4-meter-2-oxo-1,
3-thiazolidine-3-carboxamide], clofentezine [3,6-bis (2-chlorophenyl) -1,
2,4,5-tetrazine], pyridaben [2-tert]
-Butyl-5- (4-tert-butylbenzylthio)
-4-chloropyridazin-3 (2H) -one], fenpyroximate [tert-butyl (E) -4-
[(1,3-dimeter-5-phenoxypyrazol-4)
-Yl) methyleneaminooxymethyl] benzoe-
G], debufenpyrado [N-4-tert-butylbenzyl) -4-chloro-3-ethyl-1-methyl-5-
Pyrazole carboxamide], polynactin complex [tetranactin, dinactin, trinactin],
Pyrimidiphene [5-chloro-N- [2- {4- (2-
Ethoxyethyl) -2,3-dimethylphenoxy) ethylco-6-ethylpyrimidin-4-amine, milbemectene, abamectin, iva-mectin, azadirachtin [AZAD] and the like.

[0022]

EXAMPLES The present invention will be described in more detail with reference to Production Examples, Formulation Examples, Test Examples, etc., but the present invention is not limited to these Examples. First, Production Examples of the compound of the present invention and Reference Production Examples of production intermediates are shown. Production Example 1 3-dichlorofluoromethylsulfenyl-1- (2,
6-dichloro-4-trifluoromethylphenyl) -5
To a mixture of 1.30 g (2.60 mmol) of-(N-ethoxycarbonylamino) -1,2,4-triazole and 13 ml of tetrahydrofuran was added 0.140 g (3.40 mmol) of sodium hydride (oily, containing about 60%). ) Was added under ice cooling, and the mixture was stirred for 15 minutes. Next, 0.320 g (3.40 mmol) of chloromethyl ethyl ether
And several drops of 15-crown-5, and the mixture was stirred at room temperature for 15 hours. After evaporating the solvent under reduced pressure, water was poured into the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 3-dichlorofluoromethylsulfenyl-1-
(2,6-dichloro-4-trifluoromethylphenyl) -5- [N-ethoxycarbonyl-N- (ethoxymethyl) amino] -1,2,4-triazole [hereinafter,
[Compound 1 of the present invention] was obtained. ¹ H-NMR (250 MHz, CDCl ₃ / TMS): δ
(Ppm) = 7.75 (s, 2H), 5.09 (s, 2
H), 4.13 (q, J = 7.1 Hz, 2H), 3.60
(Q, J = 7.0 Hz, 2H), 1.16 (t, J = 7.
1 Hz, 3H), 1.08 (t, J = 7.0 Hz, 3H)

Production Example 2 0.208 g of sodium hydride (oil-based, containing about 60%)
(5.20 mmol) was suspended in 20 ml of tetrahydrofuran and cooled under ice-cooling to give 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- (N-methoxy 1.95 g (4.00 of carbonylamino) -1,2,4-triazole
(Mmol) was added little by little, and the mixture was stirred at 0 to 5 ° C for 30 minutes. Next, one drop of 15-crown-5 and 0.419 g (5.20 mmol) of chloromethyl methyl ether were added under ice-cooling, and the mixture was further stirred at room temperature for 5 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- [N
-Methoxycarbonyl-N- (methoxymethyl) amino] -1,2,4-triazole [hereinafter referred to as the present compound 2] 1.50 g was obtained. ¹ H-NMR (250 MHz, CDCl ₃ / TMS): δ
(Ppm) = 7.76 (s, 2H), 5.08 (s, 2
H), 3.65 (s, 3H), 3.41 (s, 3H)

Production Example 3 0.208 g of sodium hydride (oil-based, containing about 60%)
(5.20 mmol) was suspended in 20 ml of tetrahydrofuran and cooled under ice-cooling to give 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- (N-methoxy 1.95 g (4.00 of carbonylamino) -1,2,4-triazole
(Mmol) was added little by little, and the mixture was stirred at 0 ° C to 5 ° C for 30 minutes. Next, one drop of 15-crown-5 and 0.492 g (5.20 mmol) of chloromethyl ethyl ether were added under ice-cooling, and the mixture was further stirred at room temperature for 5 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure was subjected to silica gel column chromatography to give 3-dichlorofluoromethylsulfenyl-1-
(2,6-dichloro-4-trifluoromethylphenyl) -5- [N-methoxycarbonyl-N- (ethoxymethyl) amino] -1,2,4-triazole [hereinafter,
1.50 g of the present compound 3) was obtained. ¹ H-NMR (250 MHz, CDCl ₃ / TMS): δ
(Ppm) = 7.76 (s, 2H), 5.12 (s, 2
H), 3.66 (s, 3H), 3.65 (q, J = 7.0)
Hz, 2H), 1.12 (t, J = 7.0 Hz, 3H)

Reference Production Example 1 2.2 g of sodium hydride (oil-based, containing about 60%)
5 mmol) and ice-cooled in suspension in 250 ml of tetrahydrofuran, 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4. 10.8 g (25 mmol) of triazole were added and stirred for 15 minutes.
Next, 2.7 g (25 mmol) of ethyl chloroformate was added, and the mixture was stirred at room temperature for 1 hour. After evaporating the solvent under reduced pressure, water was poured into the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- (N-ethoxycarbonylamino) 10.0 g of -1,2,4-triazole was obtained. ¹ H-NMR (250 MHz, CDCl ₃ / TMS): δ
(Ppm) = 8.32 (br.s, 1H), 7.76 (s,
2H), 4.10 (q, J = 7.1 Hz, 2H), 1.21
(T, J = 7.1 Hz, 3H)

Reference Production Example 2 3,3'-di [5-amino-1- (2,6-dichloro-4
-Trifluoromethylphenyl) -1,2,4-triazolyl] disulfide 44.6 g (68 mmol), N, N
-To a mixture of 408 ml of dimethylformamide and 20 ml of water were added 31.4 g (204 mmol) of sodium hydroxymethanesulfinate dihydrate and 28.2 g (204 mmol) of trichlorofluoromethane at 10 ° C or lower. After the addition, the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-
36.0 g of (trifluoromethylphenyl) -1,2,4-triazole were obtained. 205.7 ° C. ¹ H-NMR (300 MHz, CDCl ₃ / TMS): δ
(Ppm) = 7.80 (s, 2H), 4.78 (br.s, 2
H)

Next, preparation examples are shown. Parts represent parts by weight, and the compound of the present invention is represented by the aforementioned compound number. Formulation Example 1 Emulsion Ten parts of each of the present compounds 1 to 3 are dissolved in 35 parts of xylene and 35 parts of dimethylformamide, and 14 parts of polyoxyethylenestyrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added thereto. Mix well with stirring to obtain each 10% emulsion. Formulation Example 2 Wettable powder 20 parts of each of the present compounds 1 to 3 are added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of silicon earth. , And stirred with a Juice mixer to mix 2 parts of each.
0% wettable powder is obtained.

Formulation Example 3 Granules 5 parts of each of Compounds 1 to 3 of the present invention, 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate
Parts, 30 parts of bentonite and 55 parts of clay are added and thoroughly mixed. Then, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain 5% granules of each. Formulation Example 4 Dust One part of each of Compounds 1 to 3 of the present invention is dissolved in an appropriate amount of acetone.
0.3 parts and Cle-93.7 parts were added, and the mixture was stirred and mixed with a Juice mixer, and acetone was evaporated to remove 1% of each.
Obtain a powder.

Formulation Example 5 Flowable agent 20 parts of each of compounds 1 to 3 of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture is mixed with a sand grinder. After pulverizing (particle size: 3 μm or less), 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate are added thereto, and 10 parts of propylene glycol are further added. To obtain each 20% flowable. Formulation Example 6 Oil agent 0.1 part of each of the present compounds 1 to 3 is dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this is deodorized kerosene 8
Mix 9.9 parts to obtain 0.1% oil for each

Formulation Example 7 Oily Azole 1 part, 0.2 part of tetramethrin, 0.1 part of d-phenothrin, 10 parts of trichloroethane and 59.6 parts of deodorized kerosene are mixed and dissolved, and the mixture is filled in an aerosol container, and the valve is attached. Then, 30 parts of a propellant (liquefied petroleum gas) is filled under pressure to obtain each oily aerosol. Formulation Example 8 aqueous azole 0.2 parts of each of the present compounds 1 to 3, 0.2 parts of d-alethrin, 0.2 parts of d-phenothrin, 5 parts of xylene,
A mixture of 3.4 parts of deodorized kerosene and 1 part of an emulsifier (Atmos 300 (registered trademark of Atlas Chemical)) and 50 parts of pure water were charged into an aerosol container, and a valve was attached. 40 parts of propellant (liquefied petroleum gas) are pressure-filled through the parts to obtain each aqueous aerosol.

Formulation Example 9 Mosquito Incense Incense 0.3 g of each of the present compounds 1 to 3 is added with 0.3 g of d-allethrin, dissolved in 20 ml of acetone, and a carrier for a mosquito incense stick (tab powder: meal powder: wood powder 4: 3). : 3)) 99.4g and uniformly stirred and mixed, then 120ml of water
, And the resulting mixture is molded and dried to obtain each mosquito coil. Formulation example 10 Electric mosquito collecting mat Acetone is added to each of 0.4 g of each of the present compounds 1 to 3, 0.4 g of d-allethrin, and 0.4 g of pipenyl butoxide to make 10 ml in total. 0.5 ml of this solution is 2.5 cm × 1.5 cm, thickness 0.3 c
m of an electric mat (a fibril of a mixture of cotton linter and pulp solidified into a plate) is uniformly impregnated to obtain each electric mosquito repellent.

Formulation Example 11 Heat Smoke Agent 100 mg of each of the present compounds 1 to 3 is dissolved in an appropriate amount of acetone, and impregnated into a porous ceramic plate having a size of 4.0 cm × 4.0 cm and a thickness of 1.2 cm. Obtain a heat smoker. Formulation Example 12 Poison bait 10 mg of each of Compounds 1 to 3 of the present invention was added to acetone 0.5 m
The resulting solution is treated with 5 g of solid feed powder for animals (solid feed powder for breeding and breeding, CE-2, trade name of Nippon Clea Co., Ltd.) and uniformly mixed. The acetone is then air dried to obtain each 0.2% poison bait.

Formulation Example 13 Anti-mite sheet Each of Compounds 1 to 3 of the present invention is diluted with acetone, impregnated into a non-woven fabric in an amount of 1 g per 1 m ² , and the acetone is air-dried to give each anti-mite sheet. obtain. Formulation Example 14 Anti Danishi - each of the bets present compounds 1-3 was diluted with acetone, filter paper was added dropwise impregnated so that 1 m ² per 1g, acetone air dried, each proof Danishi - get the door. Formulation Example 15 Spot-on agent 5 parts of each of the present compounds 1 to 3 and 95 parts of diethylene glycol monoethyl ether were added and mixed, and 5 parts of each compound was added.
% Spot-on agent is obtained.

Next, Test Examples show that the compound of the present invention is useful as an active ingredient of an insecticide and has excellent safety for mammals. The compounds of the present invention are indicated by the above compound numbers. As a comparative control compound, 1- (2,6-dichloro-4-trifluoromethylphenyl) -5- [N, described in JP-A-10-158250.
N-di (ethoxycarbonyl) amino] -3-trifluoromethylsulfenyl-1,2,4-triazole [hereinafter referred to as comparative compound A. ] Was used.

Test Example 1 (Acute oral toxicity test in rats) Acute oral toxicity was examined using 7 weeks old CRj: CD (SD) IGS rats. After adjusting each of the test compounds to 10 mg / ml with corn oil, about 20 mg
10m to rats (weight 210-229g) fasted for an hour
After being forcibly administered to the stomach at a rate of 1 / kg body weight, food and water were given from the end of observation 4 hours after administration, and the animals were bred for 7 days. Table 1 shows the results of observing the state of death during the breeding period.

[Table 1]

Test Example 2 (Test for topical application of German cockroaches) Compounds 1 to 3 of the present invention and 0.2 μm each of comparative compound A
g / μl of an acetone solution (1 μl) was mixed with German cockroaches (B
The adult female (Lattella germanica) was treated on the thoracic ventral surface and fed with food (solid feed for raising rats; Oriental Yeast Co., Ltd.) and water. Seven days after the treatment, the mortality was determined (10 animals per group, 3 repetitions). Inventive Compounds 1 to 3 and Comparative Compound A all showed a mortality of 100%. Test Example 3 (Housefly filter paper contact test) A filter paper of the same size was spread on the bottom of a polyethylene cup having a diameter of 5.5 cm, and the compounds of the present invention 1 to 3 obtained according to Formulation Example 1.
Each of the emulsions of Comparative Compound A and Comparative Compound A was used when the active ingredient concentration was 5
Diluted with water to give a concentration of 0.7 ppm
was dropped on a filter paper, and 30 mg of sucrose was uniformly added as a bait. Among them, housefly (Musca domes)
tica) Ten adult females were released, and after 24 hours with the lid covered, their survival was examined to determine the mortality. Compound 1 of the present invention
3 all showed 100% mortality, and Comparative Compound A showed 90% mortality. Test Example 4 (Cat flea parasite test using spray-treated mice) 2 ml of a 0.005 wt% ethanol solution of each of Compounds 1 to 3 of the present invention was administered to mice (Std: ddY strain, female, 1
A 0 week-old body weight of about 30 g of living weight) was uniformly sprayed with an atomizer. After air-drying for several minutes, the mouse was placed and fixed in a bag-shaped wire mesh and placed in a glass bottle. Next, the cat flea (Ctenocep) was placed in the glass bottle.
20 adults were infested with the mice and two days later, the mortality was determined (two replicates).
All of the present compounds 1 to 3 showed a mortality of 90% or more. Test Example 5 (Cat flea parasitic test using orally administered mouse) Each of the present compounds 1 to 3 was 2 mg / m2 in corn oil.
After adjusting to be 1 l, a mouse (Std: ddY strain, female, 10 weeks old, live weight of about 30 g) was added to a mouse at 10 ml / kg.
It was forcibly administered intragastrically at the rate of body weight (20 mg / kg). After administration, the mouse was placed in a bag-shaped wire net and fixed, and this was placed in a glass bottle. Subsequently, 20 cat flea (Ctenocephalides felis) adults were placed in a glass bottle, and the mice were parasitized. One day later, the mortality of the cat flea was determined (3 replicates). All of the present compounds 1 to 3 showed a mortality of 90% or more. Test Example 6 (Termite application topical test) 0.2 μl of an acetone solution containing 0.1% by weight of a test compound was added to a house termite (Copttermes formosa).
nus) The ant's chest back plate was treated and transferred to a 9 cm diameter resin petri dish with a filter paper moistened with water at the bottom. Seven days after the treatment, the mortality was determined (10 animals per group, 3 repetitions). All of the present compounds 1 to 3 exhibited a mortality of 100%.

Industrial Applicability The compound of the present invention is effective for killing insects, killing mites,
It has nematicidal activity and excellent safety for mammals.

Claims (2)

[Claims] 1. A compound represented by the general formula: [Wherein, R ¹ represents an ethoxycarbonyl group or a methoxycarbonyl group, R ¹ represents an ethoxycarbonyl group, R ² represents an ethoxymethyl group, and R ¹ represents a methoxycarbonyl group, and R ² represents an ethoxymethyl group. Or a methoxymethyl group. ] The triazole compound shown by these. 2. An insecticide, acaricide, and nematicide comprising the compound according to claim 1 as an active ingredient.