WO1994008982A1 - Oxazole and thiazole derivatives - Google Patents

Abstract

Compounds represented by general formula (I), a process for producing the same, and a pest control agent containing the same and having an excellent control effect particularly on cockroach and mite, wherein X1 represents halogen, alkyl, alkoxy, alkylthio, etc.; X2 represents hydrogen, halogen, alkyl, alkoxy, alkylthio, etc.; X represents halogen, alkyl, alkoxy, alkylthio, etc.; m represents 0 to 3; A represents (a) or (b) (wherein Z represents oxygen or sulfur, and R represents hydrogen, halogen, alkyl, etc.); B represents (c), (d), (e) or (f) (wherein R?1, R2, R3 and R4¿ represent each hydrogen, halogen, alkyl, cycloalkyl, alkoxycarbonyl, alkylcarbamoyl, alkylthiocarbamoyl, phenylcarbamoyl, phenylthiocarbamoyl, -Q-r1 or -SO¿i-r?3, and D represents Cr4r5, oxygen or NOr6); and Y represents hydrogen, halogen, C¿1?-C14 alkyl, etc.

Description

 Description Oxazole and thiazole derivatives Technical field:

 The present invention relates to novel oxazole and thiazole derivatives, a method for producing the same, and a pesticidal agent. Background technology:

 Many insecticides and acaricides have been used in the past, but their efficacy was insufficient, their use was limited due to drug resistance problems, and phytotoxicity and contamination of plants occurred. However, because of their high toxicity to humans and fishes, many of them are not necessarily satisfactory control agents. Therefore, there is a demand for the development of a drug that can be used safely with few such disadvantages.

 The following are disclosures of compounds similar to the compounds of the present invention. USP4, 153, 703 describes insecticidal and acaricidal activity of 2,4-diphenylthiazole derivatives and a method for producing the same. However, its biological activity is insufficient for practical use. E P 4 0 2, 7 6 2 has 2-benzyloxazole, dizol derivative

gg ¹ : H, CH ₃

g C アルキル のリポキシゲナーゼ阻害作用について述べ医薬としての有用性が記載してあるがg ² : H, nourogen

It describes the lipoxygenase inhibitory effect of g C alkyl and describes its usefulness as a drug.

However, there is no description on the control of pests that infest agricultural and horticultural crops. In J. Indian Chem. Soc., Vol. LI, pp. 564 (1974), the following compounds are described, but no biological activity is described. _{g H, CH 3, C l} , OCH s

g H、 C I g CHOCOC e H s .C recitation, C = 0

g H, CI

 g H, C I

 An object of the present invention is to provide a pesticidal agent which is surely effective and can be used safely.

Disclosure of the invention:

 The present invention has the general formula (I):

(In the formula, X ¹ is a halogen atom, an optionally substituted lower alkyl group, an optionally substituted lower alkoxy group, an optionally substituted lower alkylthio group, an optionally substituted lower alkoxy group. It represents Ruponiru group or an optionally substituted § mi Roh group, X ² is a hydrogen atom, a halogen atom, an optionally substituted lower alk kill group, optionally substituted lower alkoxy group, substituted Represents an optionally substituted lower alkylthio group, an optionally substituted lower alkoxycarbonyl group or an optionally substituted amino group, and X represents a halogen atom, an optionally substituted lower alkyl group, or an optionally substituted lower alkylcarbonyl group. An optionally substituted lower alkoxy group, an optionally substituted lower alkylthio group, an optionally substituted lower alkoxycarbonyl group or There stands also good A Mi Roh group, m represents an integer of 0 to 3, A is

[In the formula, Z represents an oxygen atom or a sulfur atom, and R represents a hydrogen atom, an amino group, an alkoxy group, a halogen atom, a lower alkyl group or a phenyl group. ], B Is

R RCII 1 2 1 1

(Wherein, R ¹ , R ² , R ³ , and R ⁴ are the same or different and are each a hydrogen atom, a halogen atom, a lower alkyl group, an RR-CII cycloalkyl group, a lower alkoxycarbonyl group, a lower alkyl group, a lower alkyl group, Lower alkylthio group, optionally substituted phenylcarbamoyl group, optionally substituted phenylthio group, -Q-r ¹ (wherein Q is an oxygen atom, a sulfur atom or Nr ² (r ² represents a hydrogen atom or a lower alkyl group.), and r ¹ represents a hydrogen atom, a cyano group, an optionally substituted lower alkyl group, an optionally substituted phenyl group, a cycloalkyl group, Lower alkoxycarbonyl group, lower alkyl group rubamoyl group, lower alkyl group rubamoyl group, optionally substituted phenylcarbamoyl group, optionally substituted Phenylthiocarbamyl group or an optionally substituted lower alkylcarbonyl group. Or —S 0 i —r ³ [wherein j represents 1 or 2, and r ³ represents an optionally substituted lower alkyl group or an optionally substituted phenyl group. D represents Cr ⁴ r ⁵ (r ⁴ and r ⁵ each independently represent hydrogen, a halogen atom, an optionally substituted lower alkyl group.), Oxygen atom or NO r ⁶ ( and r ⁶ represents a hydrogen atom, a lower alkyl group, a lower alkylcarbonyl group or a lower alkyl group. Y represents a hydrogen atom, a halogen atom, an optionally substituted C alkyl group, an optionally substituted C 2 -H alkenyl group, an optionally substituted C ₂ -H alkynyl group, An optionally substituted phenyl group, an optionally substituted C ₃ _ ₈ cycloalkyl group, SO jr ⁷ (wherein, r ⁷ is an optionally substituted C alkyl group, an optionally substituted C ₂ - _{1 4} alkenyl group, optionally substituted C ₂ - _{1 4} alkynyl group, an optionally substituted Fuweniru group, optionally substituted C ₃ - ₈ cycloalkyl group and Table, j is 0 ,. which represents 1 or 2.), in N r ⁸ r ⁹ (wherein, r ⁸ and r ⁹ are their respective independently hydrogen, optionally substituted C I _{1 4} alkyl group, substituted hand Which may C ₁₄ alkenyl group, optionally substituted C ₂ - to Table ₈ cycloalkyl group - ₁₄ alkynyl group, an optionally substituted Fuweniru group, optionally C ₃ substituted. ), 0 r ^{1 Q} (wherein, r ^{1 (1} is hydrogen, an optionally substituted C ₁₄ alkyl group, an optionally substituted C _{2 14} alkenyl group, an optionally substituted C ₂ , ₄ alkynyl group, optionally substituted Fuweniru group, optionally substituted C ₃ -. ₈ cycloalkyl group, which represents a heterocyclic ring which may be substituted), CO r ¹¹ (wherein, r ¹¹ is hydrogen, optionally substituted C alkyl group, optionally substituted C ₂ - ₁₄ alkenyl group, optionally substituted C _{2 14} alkynyl group, it may also be substituted I Fuweniru groups, substituted which may be C ₃ -. representing the ₈ cycloalkyl group), S, 0 Moshiku the optionally substituted sulfamoyl group or an optionally substituted phenoxy group, or two Y contains N May form a ring which may be substituted, and n is 0 to 5 The compound represented by}, its production method, and a pesticidal agent.

In the present invention, examples of the alkyl-substituting group include a halogen atom, a C ₃ -cycloalkyl group, a hydroxy group, an optionally substituted phenyl group, an optionally substituted phenyl group, a lower alkoxy group. And a carbonyl group. Examples of the group that substitutes phenyl include a halogen atom and a lower alkyl group. Examples of the group for substituting the hetero ring include a halogen atom, a lower alkyl group optionally substituted with a halogen atom, and the like. Examples of the group that substitutes sulfamoyl include a lower alkyl group. Examples of the group that substitutes the ring formed by two Y include a lower alkyl group. Examples of the group for substituting amino include a lower alkyl group. Usually, the lower alkyl group has 1 to 6 carbon atoms, and the cycloalkyl group has 3 to 8 carbon atoms.

The production method of the compound of the present invention is as follows. (1-1)

 C I 'one 1

 (1-2)

(Wherein X ¹ , X ² , X, m, R, B, Y, n, and Hal have the same meanings as described above.) The reaction of (1 — 1) and (1 — 2) , Alcohol, DMF, acetonitrile, DMS0 or solvents such as chloroform, halogenated hydrocarbons such as methylene chloride, ethers such as dioxane, etc. Room temperature in the presence of an organic base such as pyridine, N, N-dimethylaniline, DBU or an inorganic base such as sodium hydride, sodium carbonate, sodium carbonate, sodium hydroxide, etc. ~ 200 ° C, preferably at 60-180 ° C. For similar synthetic methods, see R. H. • Wyley et al., “Organic Reactions, Vol. 6, p. 367 (John Wiley & Sons, Inc., New York 1951).

 ( twenty one )

 C I '3]

 ( twenty two )

(I'-1) In the formula, X ¹ , X ² , X, m, R, B, Y, n, and Hal have the same meanings as described above. In the reaction of (2-1) and (2-2), first, [VII] and [VIII], or [IX] and [X] are converted to alcohol, DMF, acetonitrile, DMSO, or black form. In solvents such as halogenated hydrocarbons such as methylene chloride and ethers such as dioxane, and in some cases, organic bases such as triethylamine, pyridine, N, N-dimethylaniline and DBU, or hydrogenated sodium Reaction at room temperature to 200 ° C, preferably 60 to 180 ° C, in the presence of an inorganic base such as sodium carbonate, sodium carbonate, sodium carbonate, sodium hydroxide, etc. An ester derivative [VI] or [XI] is obtained. Next, the keto ester derivative is reacted with an ammonium salt such as ammonium acetate in an organic solvent at room temperature to 150 ° C., preferably 80 to 120 ° C. A similar synthetic method is described in R. Lakhan R. A dvncesin Heterocyclic Chemistry, Vol. 7, pp. 99 (1974) (Academic Press Res. Inc. New York). ing.

 Further, the compound of the present invention can also be produced by appropriately selecting a reaction similar to the following reaction formula or a known reaction depending on the type of substitution.

R * ¹

 I

a. A r— A— CH ₂ — P h> A r -A- CH- P h

 0 G

A r-A-(G ≠ H) O

 II

A r-A-CP h

A r— A (G ¹ ≠ H)

0 C 0 R " ¹

 I

 d. A r -A- CH- P h

OH 0 G ²

 ~> A r -A- CH- P h ~ N c = A r -A- C-P h

 o

 G p

 h

いずれの方法で反応を行った場合も反応終了後は通常の後処理を行うことによ り目的物を得ることができる。

When the reaction is carried out by any of the methods, the target product can be obtained by performing ordinary post-treatment after the reaction.

 The structure of the compound of the present invention was determined from IR, NMR, MS and the like. BEST MODE FOR CARRYING OUT THE INVENTION

Next, the present invention will be described in more detail by way of examples. Example 1 Synthesis of 2_ (4_cyclopentyl) (2,6-difluorophenyl) thiazol (Compound No. 41)

 F

1.3 g of α-promo 2,6-difluoroacetophenone and 1.0 g of 4-chlorobenzoylthioamide were dissolved in 30 ml of ethanol and refluxed for 2 hours. The reaction product was poured into iced water, extracted with black hole form, dried over magnesium sulfate and concentrated. Sheet purified by Karamukuroma Togurafi over the re dim, 2- (4-black port base Nji Le) - 4 - (2, 6-difluorophenyl) to give the thiazole Ichiru ^{_{0. 9 g (n D 24 1.}} 6 Example 3 Synthesis of 4- (2,6-difluorophenyl) -2- (4-isopropoxybenzyl) oxazole (Compound No. 59)-

F 2-isopropoxyphenylacetic acid (2 g) was dissolved in 3 O ml of DMF, 60 g of NaOH (4 g) was added, and the mixture was stirred and reacted at room temperature for 30 minutes. 2.4 g of α-bromo_2,6-difluoroacetophenone was added dropwise so as not to exceed 50 ° C. Thereafter, the reaction was allowed to proceed for 1 hour at room temperature, and the reaction product was poured into ice water and extracted with ethyl acetate. After drying over magnesium sulfate, the mixture was concentrated and purified by silica gel column chromatography to obtain an ester. '1.3 g of this ester was dissolved in 30 ml of acetic acid, 1.3 g of ammonium acetate was added, and the mixture was reacted at 100 ° C for 1 hour. The reaction product was poured into ice water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated. Purification by silica gel column chromatography-I yielded 0.38 g (mp. 40 — 41 ° C) of 41- (2,6-difluorophenyl) 1-2- (4-isopropoxybenzyl) oxazole. Was. Example 3 Synthesis of 4— (2—clomouth—6_fluorophenyl) 1-2— (4—isopropoxybenzyl) thiazole (Compound No. 80)

Dissolve 3.0 g of 4-α-bromo-1-pheno-acetone and 2.0 g of 4-hydroxyphenylthioacetamide in 30 ml of ethanol and reflux for 2 hours. I let it. The reaction product was poured into iced water, extracted with a black hole form, dried over magnesium sulfate, and concentrated. The obtained crystals are washed with black-mouthed form, and 4 — (2 — 3.4 g of lor-6-fluorophenyl) 1-2 (4-hydroxybenzyl) thiazole was obtained. 0.7 g of this thiazole was dissolved in 30 ml of DMF, and 0.1 g of sodium hydride was added. After reacting at room temperature for 1 hour, 0.5 g of isopropyl iodide was dropped, and the mixture was reacted at room temperature for 2 hours. After the reaction is completed, the reaction mixture is poured into ice water, extracted with ethyl acetate, dried and concentrated, and then purified by column chromatography. Then, 4- (2-chloro-1-6-fluorophenyl) -12- (4-isopropoxybenzyl) thiazole 0. was obtained ^{_{2 g (n D 25. °}} 1. 5 9 3 5). Example 4 Synthesis of 4- (2,6-difluorophenyl) 1-2- [α, α-methylidene-1 (4-isopropoxy) benzyl] thiazole (Compound No. 64)

 4 Dissolve 2 g of (2,6-difluorophenyl) 1-2- (4-isopropoxybenzyl) thiazol in 20 ml of N, N-dimethylformamide, and cool the mixture under ice cooling. 0.25 g of tritium (60% oil) was added, and the mixture was returned to room temperature and stirred for 30 minutes. Under ice-cooling again, 0.335 g of paraformaldehyde was added, and the mixture was returned to room temperature and stirred for 3 hours and further at 50 ° C for 1 hour.

 The reaction solution was poured into ice water, extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. '

The obtained crude product was separated and purified by silica gel column chroma Togurafi one to obtain the desired compound ^{0. 5 g (n D 2 2} · 8 1. 5 8 4 9). Example 5 2- (α, α-dichloromethylidene- (4-isopropoxy) benzyl) _4- (2,6-difluorophenyl)] thiazole (Compound No. 286- Synthesis of

 Dissolve 1-g of 4- (2,6-difluorophenyl) -2- (4-isopropoxybenzoyl) thiazol and 1.46 g of triphenylphosphine in 20 ml of carbon tetrachloride The mixture was refluxed for 20 hours.

After returning the reaction solution to room temperature, concentrated under reduced pressure, the obtained crude product was separated and purified by silica Kagerukaramu chroma Togurafi over target product ^{_{0. 8 6 g (n D 2}} ° -. 7 l 6 2 0 1 ). Example 6 Synthesis of 4- (2,6-difluorophenyl) -12-Ca, α-ethylidene-1 (4-isopropoxybenzyl)] thiazole (Compound No. 285)

F 0 C ₃ H 7 i

 S

N

C H C H

 F α —Promo 2,6 —Difluoroacetophenone 12 g and 2,2 —ethylidene mono (4-isopropoxyphenyl) acetamide 12 g dissolved in dioxane 20 m 1 Heated to reflux for a minute.

After returning the reaction solution to room temperature, it was diluted with ethyl acetate, washed with water, and the organic layer was dried. Dried over magnesium sulfate.

. This was concentrated under reduced pressure, and silica force resulting crude product gel column chroma Bok photography was separated and purified by an object thereof ^{_{0. 5 g (n D 25 -}} . 5 l 5 9 6 3) was obtained. Example 7 Synthesis of 2- (a, α-difluoro-1-4-isopropoxybenzyl) -14 (2,6-difluorophenyl) thiazole (Compound No. 28 1)

0 C ₃ H ₇ i 0 C ₃ H

4 — (2,6-Difluorophenyl) — 2 — (4_Isopropoxybenzoyl) thiazol 1g and getylaminosulfur trifluoride (DAST) 2.2m1 at 60 ° C Stirred for 9 hours.

Ice chips and water were sequentially added to the reaction solution under ice cooling, extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried over anhydrous magnesium sulfate. The crude product obtained this was concentrated under reduced pressure was separated and purified by silica force gel column chroma Bok photography chromatography to obtain the desired compound ^{_{0. 1 5 g (n D 22}} '2 l. 5 5 3 2) . Example 8 Synthesis of 5-amino-4 (2,6-difluorophenyl) 1-2 (4-isopropoxybenzyl) thiazole (Compound No. 290)

F C N

N- (α-cyano-1,2,6-difluorobenzyl) -14-isopropoxyphenylacetamide lg and 1.22 g of Lawesson's reagent were dissolved in 20 ml of benzene, and 9 The mixture was refluxed for 0 minutes.

After returning to room temperature, the crude product obtained by concentration under reduced pressure was separated and purified by silica gel column chromatography to obtain 0.33 g of the desired product. (Mp109-111) Representative examples of the compounds of the present invention including the above Examples are shown in Table 1.

Table 1

A *: In the table,

Pth

 S

xth represents 9 ΐ

 c ^) Halla τ m

6SM0 / e6cif / JDd Z8680 / W OAV

01 Table 1 (continued)

0 z

0 z

6SM0 / £ 6df / IOd Z8680 / fr6 OAV

肃 zz

 (ΐ

6SM0 / e6df / I3d ^ 8680 / ^ 6 OM Table 1 (continued)

CH ₃

 C H

CH ₃

* * 1 4 1 C F

本発明化合物は農業上の有害生物、 衛生害虫、 貯殻害虫、 衣類害虫、 家屋害虫 等の防除に使用でき、 その代表例と して、 下記のものが挙げられる。

The compound of the present invention can be used for controlling agricultural pests, sanitary pests, husk pests, clothing pests, house pests, and the like.

Lepidopteran pests, for example, Hasmonyoto, Ganoderma, Tamanayaga, Aomushi, Yumanaginaba, Konaga, Chino Kokamakumaki, Chiyamahamaki, Momomosinigaga, Nashihime Shingui, Mikanhamogiga, Chinohogashoga, Chiyanogomagaガ, ブ, 口 口, ビ ビ ア ン, メ リ 、, 、 ジ へ, ス へ, へ コ, グ ロ, 、, ド リ 力 、 ミHemiptera insects such as bugs, for example, peach aphid, peter aphid, scorpion aphid, oak biloba aphid, hosohelikamushi, okasukamemushi, yanonekai-mushi, kukonakaigaramushi, onshi-kami-boshi, tobacco Whiteflies, pear psyllids, pear beetles, brown beetle, brown beetle, cephalomorpha, black beetle, and others Scarlet beetle, Scarlet beetle, Diablotica, Tobacco beetle, Platypus quercivorus, Matsunomadara power beetle, Sesame beetle beetle, Agriotis spp. Pests, e.g., fly, oak mouth flies, senchiniku flies, peri-mipa'e, mikanko mipa'e, tanebae, rice hamogliba-e, kirosho-ejo-no-noe, sashibae, kogatakaie power, anetaishima power, Shinano, Mada Pests such as power, Pterodactyl pests, for example, southern yellow thistle, juvenile yellow thistle, etc., Hymenoptera, pests, e.g., Himeari, Kisuzume wasps, power brachioides, etc., Orthoptera pests, e.g., Japanese cockroaches,ヮ Isopteran pests, such as cockroaches, black cockroaches, horned locusts, etc., such as house termites and yamato termites; For example, Namihada two, Nisenamihada two, Kansahada two, Mikan red mite, Lingo red mite, Mikansabida ni, Lingo savida ni, Chiya nokoko mite, Brevipalpas genus, Goth tranicas genus, Robinne mite, Kona nigari, Kona nigari nikonii Plant parasitisers Nematodes, for example, Sammai Monet Cobb centimeters Yu, Negu Saleh centimeters Yu, Daizushisu Tosenchiyuu, Ineshin Gareshentiyu, Matsunozacentiyu, etc.

 In addition, in recent years, many insect pests such as moth moth, pinworm, leafhopper and aphid have developed resistance to organic phosphorus agents and carbamates, which has led to a problem of insufficient efficacy of these agents. Also effective drugs are desired. The compound of the present invention is an agent having an excellent insecticidal effect not only on susceptible strains, but also against pests of organic phosphorus agents, carbamates, pyrethroids, and resistant systems.

 The pesticidal composition of the present invention contains a compound represented by the general formula [I] as an active ingredient, and can be used as a pure active ingredient compound. It is used in the form to be obtained, that is, wettable powder, water solvent, powder, emulsion, granule, flowable and the like. When a solid agent is used as the additive and carrier, mineral powders such as soybean flour, flour and other vegetable powders, diatomaceous earth, apatite, gypsum, talc, bentonite, clay, etc. Organic and inorganic compounds such as powder, sodium benzoate, urea, and sodium sulfate are used.

 For liquid dosage forms, vegetable oils, mineral oils, petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, Use dichloromethane, methylisobutyl ketone, water, etc. as the solvent. In these preparations, a surfactant can be added if necessary to obtain a uniform and stable form. The wettable powder, emulsion, aqueous solution, and flowable thus obtained are diluted to a predetermined concentration with water to form a suspension or emulsion, and powders and granules are sprayed on plants as they are. Used in.

 It goes without saying that the compound of the present invention alone is sufficiently effective, but it can also be used in combination with various insecticides, acaricides, nematicides, fungicides and synergists.

 Representative examples of insecticides and acaricides that can be used by mixing with the compound of the present invention are shown below.

Organophosphorus and carbamate pesticides:

Phenthione, phenytrothion, diazinon, chlorpyrifos, ESP, palmidothion, phenate, dimate, formotion, marathon, tris Chlorfon, thiomethon, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxidimethonmethyl, ethione, salicion, cyano hos, isoxathion, pyridaphthion, hosalon, methatithion , Sulprofos, chlorfuninbinphos, tetrachlorbinphos, dimethylphosphin, propaphos, isofenphos, ethylthiomethone, propofinophos, pyraclofos, monochlorotophos, azidinfosmethyl, aldicarb, mesomil, thiodicarb. , Carbofuran, carbosulfan, benfracarb, flachiocalp, proboxil, BPMC, MTMC, MIPC, kylevalyl, pirimicarb, etiofenkalp, phenoxycarp, cartap, thiop Crumb, Bensuruta Tsu-flops, etc.

Pyrethroid insecticides:

 Permethrin, cypermethrin, deltamethrin, humperate rate, fenproprin, pyrethrin, areleslin, tetranurin, resmetrine , Dimethrin, propasulin, phenotrin, protoline, full-palinate, siflutrin, cyhalothrin, full-citrinet, ethoproxin, siclin Loprotoline, trolamethrin, sirafluorfen, profenprox, acrisrin, etc.

Benzoyl Rare Other Insecticides:

 Difluvenzuron, chlorfluazuron, hexaflumuron, triflumuron, tefluvenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyphen, methoprene, benzepin, jafenthiuron, ィMidacloprid, fipronil, dicotin sulfate, rotenonone, metal aldehyde, mechanical oil, microbial pesticides such as BT and insect pathogenic viruses.

Nematicide:

 Phenamiphos, phosthiazetate, etc.

Acaricide:

Chlorbenzilate, phenisobromolate, dicophor, amitraz, BPPS, benzomate, hexithiax, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetrazion, avermectin, Milbemectin , Clofenthedin, cyhexatin, pyridaven, fenpyroximate, tebufenvirad, pyrimidiphene, phenothocalp, dienochlor and the like.

Fungicide :

 Thiophane methyl, benomyl, carbendazole, thiabendazole, forpet, thiuram, ziram, zineb, maneb, polycarbamate, IBP, EDDP, fusaride, probenazole, Isoprothiolane, TPN, captan, polioxin, blastostidine S, kasugamycin, strebtomycin, noridamycin, tricyclazole, pyrokirolone, phenazine oxide, mepronil, flutranil , Penciclone, iprodione, himexazole, metalaxyl, triflumizole, trifolin, triazimefon, vitel-nor, fenarymol, propiconazol, simoxanil, prochloraz,ぺ Frazoet, Hexaconazole, Microbuta Le, dichloroethylene Lome Jin, Tech port Futaramu, pro Binebu, Jichiano down, fosetyl, Bink Rozori down, Puroshi Mi Dong, Okisajikishi Le, Guazachin, Puropamokarupu hydrochloride, fluazinam, Okiso Li Knitting click acid, arsenate Dorokishii Sokisazoru.

 Next, examples of the preparation are shown, but the carrier, surfactant and the like to be added are not limited to these examples.

Example 9 Emulsion

 Compound of the present invention 10 parts

 Alkyl phenyl polyoxyethylene 5 parts

 Jim Chilformam Mid 50

 Xylene 3 5 parts

 Mix and dissolve the above, dilute with water before use and spray as an emulsion.

Example 10 wettable powder

 Compound of the present invention 10 parts

 Higher alcohol sulfate 5 parts

 Diatomaceous earth 80 parts

 Silicon 5 parts

Mix the above, pulverize into fine powder, dilute with water before use and spray as a suspension Example 1 1 Dust

 5 parts of the compound of the present invention

 Talc 9 4.7 parts

 0.3 parts of silica

 Mix and grind the above, and spray as it is when using.

Example 1 2 granules

 Compound of the present invention '' 5 parts

 Cray 7 3 copies

 Bentonite 20

 Dioctyl sulfosac sine tonadium salt 1 part

 1 part of sodium phosphate

 Granulate the above and apply as it is when used. Industrial applicability:

Test Example 1 Efficacy against tabular beetle

10 days after germination, seeds of seedlings sown in 3-inch pots were inoculated with adult Aphid aphids. One day later, the adults were removed, and the nymphs, which were born by the nymphs, were diluted with water to a compound concentration of 125 ppm according to the emulsion formulation shown in Example 9 of the drug. Sprayed drug solution was sprayed. The plants were placed in a constant temperature room at a temperature of 25 and a humidity of 65%, and the insecticidal rate was examined 6 days later. The results are shown in Table 2.

Insect kill rate after compound number 6 (%)

1 9 0

 2 7 0 0

 4 1 0 0

 4 3 0 0

 4 4 0 0

 4 8 0 0

 5 9 0 0

 1 1 0 0

 1 7 9 2

 2 6 0 0

 2 8 0 0

 2 2 0 0 0

 2 5 3 0 0

 2 5 8 0 0

 2 8 4 0 0

 2 9 9 0 0

 3 2 0 0 0

 3 3 2 0 0

 3 3 6 9 6

Control compound A

Control compound B 100

Control compound A

対照化合物 B (CH ₃ ) ₂ N (Pirimi curve)

Control compound B

 S

(CH 0) ₂ P-SCH ₂ CH ₂ SC ₂ H ₅

(Tiomethone) Test Example 2 Efficacy against Namihadaji

 Seventeen to ten days after the germination of the seeds sown in two-size pots, 17 female adults of Nami-nada (Namidada two) resistant to organic phosphate were inoculated on one true leaf. According to the formula of wettable powder shown in the above, a chemical solution diluted with water was sprayed so that the compound concentration became 125 ppm. Place in a constant temperature room with a temperature of 25 V and a humidity of 65% .After 3 days from spraying, remove the adults and investigate on the 11th day whether the eggs laid during these 3 days have grown to adults. Then, the effectiveness of killing mites was determined. The results are shown in Table 3. The acaricidal effectiveness was determined by the following equation. Number of adults without treatment _ Number of adults with treatment

 Acaricidal effectiveness (%) = X 1 0 0

Number of untreated adults

Table 3

Compound number Acaricidal effectiveness (%) Compound number Acaricidal effectiveness (%)

3 9 7 2 3 1 9 2

 4 1 0 0 2 3 6 1 0 0

 6 9 5 2 4 8 9 9

 7 9 9 2 5 4 1 0 0

 1 1 1 0 0 2 6 1 1 0 0

 1 2 1 0 0 2 6 5 9 6

 1 4 1. 0 0 2 6 6 8 3

 1 5 1 0 0 2 7 1 1 0 0

 1 6 1 0 0 2 7 5 1 0 0

 1 7 8 4 2 7 6 1 0 0

 1 8 9 4 2 7 7 1 0 0

 3 4 1 0 0 2 7 8 1 0 0

 4 3 9 1 2 8 1 1 0 0

 4 4 9 8 2 8 2 1 0 0

 4 8 8 4 2 8 3 1 0 0

 5 2 9 0 2 8 4 8 8

 5 5 1 0 0 2 8 5 1 0 0

 5 6 1 0 0 2 8 6 9 5

 8 0 1 0 0 2 8 8 1 0 0

 8 6 1 0 0 2 9 1 8 3

 8 8 1 0 0 2 9 4 1 0 0

 9 1 9 9 2 9 5 1 0 0

 9 4 1 0 0 2 9 6 9 6

 1 1 1 1 0 0 2 9 8 1 0 0

 1 2 8 1 0 0 2 9 9 1 0 0

 2 1 5 9 1 3 0 0 9 7

 2 1 6 1 0 0 3 0 1 1 0 0

 1 7 1 0 0 3 0 2 1 0 0

 2 1 8 1 0 0 3 0 5 1 0 0

 2 1 9 1 0 0 3 0 6 1 0 0

 2 2 0 1 0 0 3 2 0 1 0 0

 1 1 0 0? 1 Q o Q o

 2 2 2 8 4 3 2 9 9 9

 2 2 3 1 0 0 3 3 2 1 0 0

 2 2 4 1 0 0 3 3 3 1 0 0

 2 2 5 1 0 0 3 3 4 9 9

 2 2 6 1 0 0 3 3 5 1 0 0

 2 2 7 1 0 0 3 3 6 9 8

 2 2 8 1 0 0 3 3 7 1 0 0

 2 2 9 1 0 0 3 3 8 1 0 0

 2 3 0 1 0 0 3 4 2 9 7

 Control compound C 5 5 Control compound C

CH ₃

C 1 — <〇> _ N = CH— N (CH ₃ ) ₂ HC 1

Claims

1. General formula [I] RRCII

one (In the formula, X ¹ is a halogen atom, a lower alkyl group which may be substituted, a lower alkoxy group which may be substituted, a lower alkylthio group which may be substituted, a lower alkyl group which may be substituted. X ² represents a hydrogen atom, a halogen atom, an optionally substituted lower alkyl group, an optionally substituted lower alkyl group, X ² represents a oxycarbonyl group or an optionally substituted amino group; Represents a lower alkylthio group which may be substituted, a lower alkoxycarbonyl group which may be substituted or an amino group which may be substituted, and X represents a halogen atom or a lower alkyl group which may be substituted. An optionally substituted lower alkoxy group, an optionally substituted lower alkylthio group, an optionally substituted lower alkoxy group, Represents an amino group which may be substituted, m represents an integer of 0 to 3, and A represents Is

 [In the formula, 表 し represents an oxygen atom or a sulfur atom, and R represents a hydrogen atom, an amino group, an alkoxy group, a halogen atom, a lower alkyl group or a phenyl group. And 、 is R ¹ R ³  C-C-C R C R R ² R ⁴ Wherein R ¹ , R ² , R ³ , and R ⁴ are the same or different and are each a hydrogen atom, a halogen atom, a lower alkyl group, a cycloalkyl group, a lower alkoxycarbonyl group, a lower alkyl group, a rubamoyl group, or a lower alkylthio group. Rubamoyl group, which may be substituted Hue carbamoylmethyl group, an optionally substituted off We two thio force Rubamoiru group, - Q - r ¹ wherein, Q is an oxygen atom, a sulfur atom or N r ² (r ² represents a hydrogen atom or a lower alkyl group And r ¹ is a hydrogen atom, a cyano group, an optionally substituted lower alkyl group, an optionally substituted phenyl group, a cycloalkyl group, a lower alkoxycarbonyl group, a lower alkyl group, a lower alkyl group, Lower alkylthio represents a rubamoyl group which may be substituted, a phenylcarbamoyl group which may be substituted, a phenylcarbamoyl group which may be substituted or a lower alkylcarbyl group which may be substituted. Or —S 0 i — r ³ [wherein, i represents 1 or 2, and r ³ represents an optionally substituted lower alkyl group or an optionally substituted phenyl group. And D represents Cr ⁴ r ⁵ (r ⁴ and! " ⁵ each independently represent a hydrogen atom, a halogen atom, an optionally substituted lower alkyl group.), An oxygen atom or NO r ⁶ (where r ⁶ represents a hydrogen atom, a lower alkyl group, a lower alkylcarbonyl group or a lower alkyl group), and Y represents a hydrogen atom, a halogen atom, or an optionally substituted C ぃ₁₄ alkyl group, optionally substituted C ₂ - ₁₄ alkenyl group, optionally substituted C ₂ - ₁₄ alkynyl group, an optionally substituted phenyl group, an optionally substituted C _{3 8} cycloalkyl group during SO ir ⁷ (wherein, r ⁷ is an optionally substituted C I ₁₄ alkyl group, optionally substituted C _{2 14} alkenyl group, optionally substituted C ₂ - ₁₄ alkynyl group, is substituted Optionally substituted phenyl group, substituted Good C ₃ can have -. And Table ₈ cycloalkyl group, j is represents 0, 1 or ^{2), N r 8 r 9} ( wherein, r ⁸ and r ⁹ are their respective independently hydrogen , optionally substituted C I ₁₄ alkyl group, optionally substituted C 2 - H alkenyl group, an optionally substituted C _{2 14} alkynyl group, an optionally substituted Fuweniru groups, substituted Table to also be C _{3 8} cycloalkyl group optionally.), O r ^1Q (wherein, r ^{1 ()} is hydrogen, optionally substituted C alkyl group, optionally C _{2 4} alkenyl optionally substituted It represents ₈ cycloalkyl group, a heterocyclic ring optionally substituted - group, optionally substituted C ₂ - ₁₄ alkynyl group, an optionally substituted Fuweniru group, an optionally substituted C ₃ ), CO r ¹¹ (wherein, r ¹¹ is hydrogen, an optionally substituted C alkyl group, or an optionally substituted C ₂ - ₁₄ alkenyl group, optionally substituted C 2 - H alkynyl group, optionally substituted I Fuweniru group, an optionally substituted C ₃ _ ₈ cycloalkyl group. ) Represents an optionally substituted sulfamoyl group or an optionally substituted phenoxy group, or two Y's may contain S, 0 or N and may form a substituted or unsubstituted ring. Often, n represents an integer from 0 to 5. } A compound represented by the formula: 2. —General formula [II] [In the formula, X ¹ represents a halogen atom. ]

[Wherein, B, Y, and η represent the same meaning as described above. Wherein the compound represented by the general formula [I′-1 1] (I'-1)

[In the formula, X ′, X ² , X, m, R, Β, Υ, and η represent the same meaning as described above. ] The manufacturing method of the compound represented by these. 3. —General formula [IV] (IV)

[Wherein, X ¹ , X ² , X and m represent the same meaning as described above. And a compound represented by the general formula (V).  (Y) n ocy (v)

[Wherein, B, Y, n, R, and H a1 represent the same meaning as described above. Wherein the compound represented by the general formula [I′-1 2] [I '— 2]

[Wherein, X ¹ , X ² , X, m, R, B, Y, and n represent the same meaning as described above. ] The manufacturing method of the compound represented by these. 4. General formula [VI] [VI]

[Wherein, X ¹ , X ² , X, m, R, B, Y, and n represent the same meaning as described above. Wherein the compound represented by the general formula [I'1-3] [I '3]

[Wherein, X ¹ , X ² , X, m, R, B, Y, and n represent the same meaning as described above. ] The manufacturing method of the compound represented by these. 5. General formula [VII] [XI]

[Wherein, X ¹ , X ² , X, m, R, Β, Υ, and η represent the same meaning as described above. Wherein the compound represented by the general formula [1 ' - Four〕 CI '— 4]

[Wherein, X ¹ , X ² , X, m, R, B, Y, and n represent the same meaning as described above. ] The manufacturing method of the compound represented by these. 6. General formula [I] C I]

[Wherein, X ¹ , X ² , X, m, A, B, Y and n represent the same meaning as described above. ] A pesticidal composition characterized by containing one or more of the compounds represented by the formula (1) as an active ingredient.