WO1999052882A1 - 1,2,3-thiadiazole derivative or salt thereof and pest control agent, and method of use thereof - Google Patents

Abstract

1,2,3-thiadiazole derivative represented by general formula (I): wherein either R1 or R2 is -W-CH2-CH2-C(X)=CF2 wherein W is -O-, -S(O)n- where n is 0 to 2, -C(=Z)-Y- wherein Z is O or S, Y is O, S, NR3 where R3 is H or an alkyl, or NR4 where R4 is H or an alkyl, X is H or F, and the other of R?1 and R2¿ is H, a halogen, a cyano, a substituted or unsubstituted alkyl, an alkenyl, an alkynyl, a cycloalkyl, an aryl, an arylalkyl, a heteroaryl, a heteroarylalkyl or the like, or a salt thereof and a pest control agent comprising the above-mentioned compound as an active component and a method of the use thereof.

Description

 1, 2, 3 '"-Derivatives or salts thereof, pesticides and methods of use

 The present invention relates to a novel 1,2,3-thiadiazole light derivative or a salt thereof useful as a pesticide, particularly a pesticide, an acaricide or a nematicide, a use thereof, and a method of using the same. .

Background art

 Examples of the haloolefin compound having insecticidal activity include JP-A-63-500037, JP-A-2-280, JP-A-2-85267, JP-A-2-134372, and EP 371 925. Publication, JP-A-2-286678, JP-A-3-128369, EP-364395, WO-94241111, JP-T095-110197, GB-2287465 And Japanese Patent Application Laid-Open No. 10-287659 disclose insecticides, acaricides, and nematicides, but 1,2,3-thiadiazos represented by the general formula (I) of the present invention. No description is made on the derivative or its salts.

Disclosure of the invention

 As the number of existing pesticides increases over the years after development, those that lose their effectiveness due to the increased resistance of the target pests are increasing. The use of existing agents at high concentrations and the repeated use of the same agents are increasing the burden on the human body and the environment, which is becoming a problem. An object of the present invention is to provide a novel pesticide having excellent activity at a low dose.

The present inventors have conducted intensive studies to create a novel pest control agent. As a result, the 1,2,3-thiadiazol derivative represented by the general formula (I) of the present invention or a salt thereof is described in the literature. A pest control agent which is an undescribed new compound and further comprises the 1,2,3-thiadiazol derivative or a salt thereof as an active ingredient has excellent effect on various pests at a low dose. The inventors have found that the present invention has been completed. The present invention provides a compound represented by the general formula (I):

[Wherein one of Ri and R ₂ is

-W-CH ₂ -CH ₂ -C = CF ₂

 X

(Where W is O, — S (O) n — (where n is an integer of 0 to 2), one C (= Z) — Y— (where Y is an oxygen atom, sulfur An atom or NR ₃ (wherein R ₃ represents a hydrogen atom or a (C ^) alkyl group), Z represents an oxygen atom or a sulfur atom.) Or NR ₄ (where R ₄ is hydrogen Represents an atom or a) alkyl group. X represents a hydrogen atom or a fluorine atom. And the other is a hydrogen atom, a halogen atom, a cyano group, which may be the same or different and may have one or more substituents. (Ci) An alkyl group, the same or (C ₂ _ ₈ ) alkenyl groups which may be different and have one or more substituents, may be the same or different and may have one or more substituents (c _{2 a} ) alkynyl group , same or different is also rather good, 1 or more substituents which may have on the ring (C _{3 8)} cycloalkyl group, the same or may be different, have one or more substituents good Ariru group, which may be the same or different dates, one or more substituents which may have on the ring Ariru (d_ ₆₎ alkyl group, which may be identical or different, on one or more substituents the ring Aryloxy that you may have

) Alkyl group, which may be identical or different, one or more substituents which may have on the ring Ariru _(d-:) alkoxy (C, - ₆₎ alkyl group, which may be the same or different dates, 1 Heteroaryl groups which may have the above substituents, which may be the same or different, and heteroaryl groups which may have one or more substituents on the ring) alkyl groups, which may be the same or different, 1 A heteroaryloxy which may have the above substituent (s) on the ring) an alkyl group, which may be the same or different, and A heteroaryl (d- ₆ ) alkoxy (d- ₆ ) alkyl group, which may have a ring, one COR ₅ (wherein R ₅ is a hydrogen atom, a halogen atom, a hydroxyl group,

(C, - ₆₎ alkyl groups, halo (C, - ₆₎ alkyl, (C ₂ - ₈₎ alkenyl, halo (C ₂ _ ₈₎ alkenyl, (C ₂ - ₆₎ alkynyl, halo (C ₂ - ₆₎ alkynyl group, an Ariru group which may have a substituent, which may have a substituent Ariru

(C, _ ₆ ) represents a heteroaryl group which may have an alkyl group or a substituent. ), 1) alkyl COR _s , wherein R ₅ is as defined above.

-CONR ₅ R _e (wherein, R ₅ is also the, R ₆ is the same as R _s.), -

(C, - ₆₎ alkyl CONR ₅ R _6, (wherein, R ₅ and R ₆ are as defined above.) - (. Wherein, R ₅ is as defined above) COOR _5, one _(d-6) alkyl COOR ₅

(Wherein, R ₅ is the same as above.), Mono (d- ₆ ) alkyl O—C〇R ₅ (wherein, Re is the same as above.), Mono (C — ₆ ) alkyl S (O) n R ₅ (where n is an integer of 0 to 2 and R ₅ is the same as above), one CSNR ₅ R ₆ (where R ₅ and Re are the same as above), and one Si R _s R ₆ R ₇ (wherein, R ₅ and R ₆ to the same Ku said, R ₇ is a hydrogen atom, a halogen atom, arsenic Dorokishiru group, (CI- ₆₎ alkyl group, halo (c had _s) alkyl group , (c ₂ - ₈₎ alkenyl group, Nono b (c ₂ - _s) alkenyl Le group, (c ₂ - ₆₎ alkynyl, halo (c ₂ - ₆₎ alkynyl group, Ariru group or § Li Ichiru (C shows _ ₆₎ alkyl group.), one CONR ₅ S0 ₂ R ₆ (wherein, R ₅ and R ₆ are as defined above.) one _(d-6) alkyl CONR ₅ S_〇 ₂ R ₆ (wherein Wherein, R ₅ and R ₆ are the same as described above.), A (d- ₆ ) alkyl NR ₅ R ₆ (wherein , R ₅ and R ₆ are the same as above.), One CR ₅ = NR ₆ (where R _s and R ₆ are the same as above.), And one CR _S -NNR ₆ R ₈ (R ₅ and R ₆ are the same as above.) the same to, Rs is (〇 Bok ₆₎ alkyl group, or which may be identical or different,. indicating one or more may be have a substituent Ariru group), in one CR ₅ = NOR ₆ (wherein, R ₅ and R ₆ are the same as described above.) Or CR ₅ = NOCONR ₆ R ₇ (R ₆ , R ₆ and R ₇ are the same as described above.). However, a substituted phenyl group in which the 4-position of the 1,2,3-thiadiazole ring is substituted by a hydrogen atom, a nitrogen atom, ₆ ) an alkyl group, a halo (C) alkyl group, a phenyl group or a chlorine atom When W represents -S (O) n- (wherein, n is the same as above), X excludes a fluorine atom. ] It is intended to provide a 1,2,3-thiadiazole derivative represented by the formula (1) or a salt thereof, a pesticidal agent containing them as an effective component, and a method for using the same.

BEST MODE FOR CARRYING OUT THE INVENTION

Examples of each substituent in the present invention are shown below. In the abbreviated notation of the chemical formula in the present invention, "n_" represents normal, "i-" represents iso, "sec-" represents secondary, "t-" represents tertiary, and the substituent number of carbon atoms, for example "(Ji _{6)", "(d-12)",} and the like having 1 to 6 carbon atoms refers to the 1-12. In the 1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention, “halogen atom” in the definition of each substituent indicates a chlorine atom, a bromine atom, an iodine atom or a fluorine atom, “(^ _ ₁₂ ) alkyl group” refers to a linear, branched or cyclic alkyl group, such as methyl, ethyl, n-propyl, i-propyl, n-butynole, i —Butynole group, sec—butynole group, t-butyl / le group, neopentynole group, 1,2-dimethylpropyl group, _n— hexyl group, cyclohexyl group, _n— heptyl group, n-octyl group, n —Decyl group, n-dodecyl group and the like.

“(C,-^) alkyl group which may be the same or different and may have one or more substituents” means that one or more of the hydrogen atoms is replaced by another substituent. Represents a (c- ₁₂ ) alkyl group, and examples of the substituent include a halogen atom, a cyano group, a nitro group, a formyl group, a hydroxyl group, a (d) alkoxy group (eg, a methoxy group, an ethoxy group, - butoxy), halo (C, - ₆₎ alkoxy group (e.g. Jifuruorome butoxy group, chloro difluoromethyl O Lome butoxy group, 2, 2, 2-preparative Riffle O b ethoxy, 2, 2, 2-trichloro port Echiru Group, 1,2-dibromoethoxy group, etc.), (d- ₆ ) alkylthio group (eg, methylthio group, ethylthio group, etc.), ₆ ) alkylsulfenyl group (eg, methylsulfenyl group, i-propylsulfenyl) To n— Shirusurufueniru group), (C, - ₆₎ alkyl Rusuruhoniru group (e.g. methylsulfonyl group, Echirusuruhoniru group, 2, 3-di-methyl-propylsulfonyl group, etc.), (c ₃ _ _s) a cycloalkyl group (such as cyclopropyl Propyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, etc., amino group, mono- or di (C, ^) alkylamino group (for example, methylamino group, ethylamino group, dimethylamino group, ethylamino group, methyl) Ethylamino, di One n- Buchiruamino group),) alkylcarbonyl group (e.g. Asechiru group, a propionyl group, a cyclohexyl group, etc.) to n-, (C -! ₆₎ alkoxy force carbonyl group (e.g., main-butoxycarbonyl group, an ethoxycarbonyl group, t- butoxy aryloxycarbonyl group), § amino carbonyl group, mono- or di (d _ ₆₎ alkylamino Bruno carbonyl group (e.g., methyl § amino group, such as methyl E chill § amino carbonitrile group), or (flicking ₆₎ alkyl Carbonyloxy group (for example, methylcarbonyldioxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, i-propylcarboeroxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, sec —Butylcarbonyloxy group, t-butylcarbonyloxy group, n-pentino Indicating the carbonyl O alkoxy group, 0 or 1 or more identical or different and may substituents selected from cyclohexyl carbonyl O alkoxy group) to n-.

“(C _{2 s} ) alkenyl group” refers to a linear or branched alkenyl group having one or more double bonds, such as a vinyl group, an aryl group, an i-propyl group, an Methyl-2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-hexenyl group, etc., and “alkynyl group” means one or more triple Represents a linear or branched alkynyl group having a bond, for example, an ethynyl group, a 2-propynyl group, a 1-methyl-2-propyl group, a 1-butyl group, a 2-butynyl group, a 3-butynyl group, etc. Show.

(C ₂ - ₈₎ alkenyl or - As (C _{2 6)} substituents on an alkynyl group, which may be the same or different For example, one or more halogen atoms, arsenate Dorokishiru group, a nitro group, Shiano group, (C , ^) Represents a substituent selected from an alkoxycarbonyl group or a carboxyl group or a salt thereof.

The “(C ₃ _ ₈ ) cycloalkyl group” refers to a cyclic alkyl group, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, or the like. Examples of the substituent on the ring include a halogen atom or a (C ^ ₆ ) alkyl group (eg, a methyl group, an ethyl group, a butyl group, an n-butyl group, an i-butyl group, a sec-butyl group). And at least one substituent which may be the same or different and is selected from a group, a t-butyl group, an n-pentyl group, and an _n- hexyl group. "Halo (C, _ ₆₎ alkyl""halo _(d- έ) alkenyl group" or "halo (C, - ₆₎ alkyl" and, from one or more of the same or different and may a halogen atom It represents an alkyl group, alkenyl group or alkynyl group having a selected substituent.

“Aryl group” refers to a phenyl or naphthyl group, and “aryl) alkyl group” refers to a linear, branched or cyclic alkyl group having a phenyl or naphthyl ring, such as benzyl, phenethyl, It represents phenylpropyl, phenylbutyl, α-methylbenzyl, ct, α-dimethylbenzyl and the like, and “aryloxy (C _{t 6} ) alkyl group” means a linear or branched group having a phenyl or naphthyl ring. Represents an oxyalkyl group in the form of “aryl (^ _ ₆ ) alkoxy

(C, - ₆₎ the alkyl group "represents a linear or branched alkoxyalkyl group having phenyl or naphthyl ring. "Aryl group", "Aryl (d- ₆ ) alkyl group", "Aryloxy (d- ₆ ) alkyl group" or "Aryl group"

Substituents on the ring of the (C, _ ₆ ) alkoxy (C ^) alkyl group ”may be the same or different and include a halogen atom, a nitro group, a cyano group, a (d ₁₂ ) alkyl group, a halo (d — ₆ ) alkyl group, (d- ₆ ) alkoxy group, halo (d) alkoxy group, —S (O) n (d ₆ ) alkyl group (where n is an integer of 0 to 2), halo (C -! _[delta]) alkylthio, (- ₆₎ alkylcarbonyl groups, (C, - ₆₎ alkoxycarbonyl group, a carboxyl group, (C) alkoxy force Ruponiru (! C ₆₎ alkoxy groups, di _(d-6 ) alkylamino group, (C ₂ - _s) alkenyl, (C ₂ - ₆₎ alkynyl, § amino carbonyl) alkyl, mono- or di (〇 I ₆₎ alkylaminocarbonyl (C, - ₆₎ alkyl group, § Minokarubo group, which may be identical or different, (C ^ ₆₎ alkyl group, Enyl, which may be identical or different, a halogen atom, a nitro group, Shiano group, (C, - ₆₎ alkyl groups, halo (C, - ₅₎ alkyl, (C,) alkoxy groups, halo (C) alkoxy Group, one S (O) n (C, _ _fc ) alkyl group (where n is as defined above), one S (O) n halo (C, _έ ) alkyl group (where η is as defined above) same.), (C, ₆₎ alkyl group,) alkoxycarbonyl, di (C _{1 -6)} alkylamino group, (C _2.) alkenyl, (C _{2 6)} Arukini Or a phenyl (c _1-6 ) alkyl group having one or more substituents selected from a phenyl group, an aminocarbonyl group, a mono- or di- (C, _-ό ) alkylaminocarbonyl group, may be different, a halogen atom, a nitro group, Shiano group, (Cn) alkyl, halo (d_ ₆₎ alkyl group, (C, - ₆₎ alkoxy groups, halo (C ^ ₆₎ alkoxy group, one S (O ) n (C ^ e) alkyl group (where n is as defined above), —S (O) n halo — 6) alkyl group (where n is as defined above), (C ^ e) alkylcarbonyl group, (d_ ₆₎ alkoxycarbonyl - group, di _(d-6) alkylamino group, (C ₂ _ ₆₎ alkenyl, (C ₂ - ₆₎ § Rukiniru group, § amino group or a mono- or Having at least one substituent selected from di (d- ₆ ) alkylaminocarbonyl groups To phenyl (c _t _ ₆₎ § amino carbonyl group having 1-2 substituents selected from alkyl group, Aminokaru Boniru - ₆₎ alkyl, mono- or di _(d-6) alkylaminocarbonyl

A (C _1-6 ) alkyl group, —NRC OR ₆ (R ₆ is as defined above),

NR ₆ CO Re (R ₆ and R ₆ are the same as described above), one NR ₅ CO NR ₆ R ₇ (R ₆ , R ₆ and R ₇ are the same as described above), a phenyl group, which may be the same or different. Good, halogen atom, (C _t — ₈ ) alkyl group, (C n) alkoxy group, halo (d- ₆ ) alkyl group, (C, _ _s ) haloalkoxy group, one S (O) n (d— ₆ ) alkyl groups (n is as defined above), one S (〇) n halo (C -.! ₆₎ alkyl group (n is as defined above), (C -.! ₆₎ alkylcarbonyl group, (C, _ ₆₎ alkoxy force Lupo group, di (C -! ₆₎ alkylamino group, (C ₂ - ₆₎ alkenyl, (C ₂ - ₆₎ alkynyl, § amino carbonyl group, mono- or di (C _! ₆ ) a alkyl group having 1 to 5 substituents selected from an alkylaminocarbonyl group, a nitro group, or a cyano group, a phenyloxy group, which may be the same or different, and Androgenic atom, a nitro group, Shiano group, (^ _-5) alkyl group, (C n) alkoxy groups, Nono port (C, - ₆₎ alkyl groups, (CH) haloalkoxy group,

One S (O) n (C, - 6) alkyl group, one S (O) n halo (C, - ₆₎ (n is as defined above.) (. N is as defined above) alkyl, (C, - ₆₎ alkylcarbonyl groups, (C, -,) alkoxycarbonyl group, di) alkylamino group, (C ₂ - ₆₎ alkenyl, (C ₂ - ₆₎ alkynyl, § amino carbonyl group or Mo Fuunyloxy, phenyl (d- ₆ ) alkyloxy having 1 to 5 substituents selected from di or di (C, _-ό ) alkylaminocarbonyl, or the same or different, halogen, nitro Group, cyano group, (d- ₆ ) alkyl group, (d- ₆ ) alkoxy group, halo) alkyl group, halo (C.-a) alkoxy group, _S (O) n (d- ₆ ) alkyl group (N is the same as above.), One S (O) n halo (d- ₆ ) alkyl group (n is the same as above), (d- ₆ ) alkylcarbonyl group, (d- ₆ ) alkoxycarbo- group, di (C _{1 →)} alkylamino group, (C ₂ - ₆₎ alkenyl, - selected from (C _{2 6)} alkynyl group, § amino group or a mono- or di (CH) alkylamino carbonylation le radical phenyl having 1-5 substituents on the ring _(d-6) alkyl Or shows from 1 to 5 substituents selected from Okishi group, or substituted in the adjacency carbon to on the benzene ring is bonded to an annular (C ₃ - ₄₎ alkylene group or (C, - ₂ ) Represents an alkylenedioxy group (for example, a methylenedioxy group, an ethylenedioxy group, etc.).

"Heteroariru group", "Heteroariru _(d-6) alkyl group", "heteroaryl Ariruokishi) alkyl group" or "Heteroariru ₆₎ alkoxy (C, - ₆₎ alkyl" and Teroariru to the aromatic heterocyclic group (The heterocyclic group includes a compound in which one double bond is reduced and a compound in which a heteroatom atom in an aromatic heterocyclic ring is oxidized. For example, thiazoline to thiazole, pyridine to N-pyridine And the heterocyclic ring includes, for example, furan, thiophene, pyrroic acid, pyrroline, cyxazonole, oxazoline, isoxazole, thiazole, thiazoline, isothiazol, imidazole, pyrazol, Virazoline, 1,2,4_oxaziazol, 1,3,4-oxaziazol, 1,2,4-thiadiazol, 1,3,4-thiadiazol, 1,2,3-thiadiazole, 1,2,5-thiadiazole, 1,2,3-triazol, 1,2,4-triazole, tetrazole, pyridine, pyrimidine , Pyridazine, pyrazine, oxazine, thiazine, triazine, pyrrofuran, pyrrolofurazan, pyrromid imidazol, pyrropyridine, pyridine, floisoxazol, flopyridine, flopyrimidine, thienofuran, chenoxazol, chenobiridazine, chenobirazine Oxazoloisoxazole, Oxazolopyridine, Isothiazoloxazole, Imidazoloxazol, Imidazolopyridine, Isoxazolofurazan, Thiazopyridazine, Isotizazolopyridine, Imidazo Examples thereof include pyrazole, pyrazolofurazan, pyranopyridine, pyridopyrazine, indoline, quinolidine, purine, naphthyridine, and pyrazoxoxazole, and the aromatic heterocyclic group may be a benzo derivative. “Benzo derivatives” include, for example, benzofuran, isobenzofuran, 1-benzothiophene, 2-benzothiophene, indole, isoindole, 1,2-benzothiazole, 1,3-benzothiazole, and 2,1-benzothiazole. Azoles, indazoles, benzimidazoles, quinolines, isoquinolines, quinazolines, quinoxalines, cinnolines, phthalazines, 1,2,3-benzothiasiazo / res, benzotriazo / res, benzoxazines, benzothiazines, benzopyridazines, 1-oxophthalenes 1 thia 4-azanaphthalene, etc.

Examples of the substituent of the heterocyclic group may be the same or different, a halogen atom, shea Anomoto, human Dorokishi group, _(d-8) alkyl groups, halo (C! ₆₎ alkyl group, (C ₂ _ ₈₎ alkenyl, halo (C _{2 6)} alkenyl group, (C _{2 6)} alkynyl, halo (C _{2 6)} alkynyl, (C _{3 8)} cycloalkyl group, (d ₆₎ § alkoxy group, halo ( C, - ₆₎ alkoxy groups, (C _{2 6)} Arukeniruokishi group, Nono port (C ₂ - ₆₎ Arukeniruokishi group, _(d-6) alkoxy (C, - ₆₎ alkyl, (C doctor ₆ ) alkylthio groups, halo (d _s) alkylthio group, an amino group, 1 or 2 identical or different and good (C, - ₆₎ amino group substituted by an alkyl group, (d _s) Ashiruamino group, a carboxyl group or (C! ₆₎ alkyl ester group, a force Rubamoiru group, 1 or 2 identical or It is even better (d ₆₎ can show a 5-membered or 6-membered ring formed by the divalent polymethylene group together with the nitrogen atom of the substituted force Rubamoiru group or force Rubamoiru group alkyl Le group.

Examples of the salts of the 1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumaric acid and the like. Organic acid salts such as salt, maleate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, sodium ion, potassium ion Salts with metal ions such as on and calcium ions can be exemplified.

As 1, 2, 3 over thiadiazole derivatives or salts thereof represented by the general formula (I) of the present invention, preferred substituents, or R ₂ any group

One W—CH ₂ —CH ₂ —CX may be CF ₂ , W is a sulfur atom or a carbonyloxy group, X is a hydrogen atom, and the other substituent is a part of the substituent. A substituent having an aryl or a heteroaryl, for example, an aryl group optionally having a substituent, an arylalkyl group optionally having a substituent, an aryloxyalkyl group optionally having a substituent, A heteroaryl group which may have a substituent, preferably CO—R ₅ (R ₅ is an aryl group which may have a substituent or a heteroaryl group which may have a substituent), is preferably an aryl ring. or to halo gen atoms as a substituent on heteroaryl ring, (CI- ₆₎ alkyl group, (C -! ₆₎ alkoxy groups, halo (C -! ₆₎ § alkyl group, Nono b _(Ci- έ) alkoxy And a substituent such as an alkoxycarbonyl group. More preferably, X is a hydrogen atom, W is a sulfur atom or a carbonyloxy group, and the other or R ₂ is an aryl group such as a phenyl group, a phenoxymethyl group, a naphthyl group or a pyridyl group; A substituted or unsubstituted halogen atom, a (d- ₆ ) alkyl group, a halo (d- ₆ ) alkyl group, a (〇 ぃ₆ ) substituents such as alkoxy or halo (〇 Bok _O) alkoxy groups are preferred.

 Hereinafter, typical methods for producing the 1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention will be described, but the present invention is not limited thereto.

In each of the production methods, and R ₂ have the same meaning as the other of R and R ₂ in the general formula (I), except that one is not W—CH ₂ —CH ₂ —CX = CF ₂ . In the following Reaction Formulas 1 to 4, as a typical example of the reaction, the substituent at the 4-position of 1,2,3-thiazazole is R, and the substituent at the 5-position is

While indicating _{-W-CH 2 -CH 2 -CX =} CF 2 or a substituent of the precursor, 5-position, 4-position one W- CH ₂ - For CX = CF _2, compound - CH ₂ Can also be produced according to the illustrated references. That is, a starting compound (Illb) in which the substituents at the 4- and 5-positions are replaced with (Ilia) can be produced, and are shown below. The final target compound (I), (la), (lb), (Ic), (Id), (Ie), etc., corresponding to the final target compound is replaced according to the above method. Can be manufactured.

 (Production method 1)

(Wherein and X is also the, W, one 0-one S- or one NR ₄ -. (Wherein, R ₄ represents the same) to said, M is sodium or hydrogen, potassium And L represents an alkali metal atom such as lithium, L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, an alkylsulfonate group, or an arylsulfonate group, and n represents an integer of 1 or 2.)

General formula (Ilia) as a starting compound of the present invention can be produced according to a known method. That is, the compound (Ilia) in which W, is an oxygen atom can be produced according to the method described in Hemushi's Berichte (Chem. Ber., 99, 1618-1631, 1966). The compound (Ilia) that is a sulfur atom is disclosed in In accordance with Japanese Patent No. 2771, Japanese Patent Application Laid-Open No. 59-39884, European Patent Publication EP-104403 and the like, the starting compound (Il lb) can be produced according to the method described in European Patent Publication No. EP-25252474. Compounds in which W _t is a nitrogen atom are described in Journal of 'The Chemical. Society. Perkin' Transaction (J. Chem. Soc. Perkin Trans. I, 1994, 2895-2897), Journal of · Heterocyclic 'chemistry (J. Heterocyclic Chem., 13, 1141-1145, (1976)) or (Illb) type is described in DE 28 52 067, etc. It can be manufactured according to the method described above.

 The compound represented by the general formula (Ilia) produced according to the above method is reacted with the compound (IV) in the presence or absence of an inert solvent, and in the presence or absence of a base as necessary. Thus, a compound represented by the general formula (V) is obtained. Further, the compound represented by the general formula (Ie) can be produced by isolating or not isolating the compound (V) and conducting a bromine elimination reaction in the presence of an inert solvent and a catalyst.

 Similarly, the compound represented by the general formula (VI) can be reacted with (Ilia) in place of the compound (IV) to obtain the compound (Ie).

 Further, the compound (Ie) in which is a sulfur atom among the compounds obtained by the above reaction was oxidized by a conventional method, for example, in an inert solvent in the presence of a suitable oxidizing agent, whereby the sulfur atom was oxidized. Compound (la) ′ can be produced.

 In this reaction, the steps from general formula (Ilia) to (Ie) via (V) to (Ie), the steps from (Ilia) to (Ie) and the step of oxidizing (Ie) can be carried out according to a conventional method or a special method. Table 9

It can be manufactured according to the manufacturing method disclosed in Japanese Patent Application Laid-Open No. 501-0175, or is as follows.

 1-1. Process from compound (Ilia) to compound (V)

The reaction is usually carried out in an inert solvent in the presence of a base, and the reaction temperature range varies depending on the reagents used and the reaction solvent, but usually ranges from 180 ° C to 200 ° C. Yes, it is preferably in the range of 120 ° C to 100 ° C. Reaction times are typically from instantaneous to 24 hours. The amount of the reactants used in the reaction is different from the compound (Ilia), but the compound (VI) varies depending on the reactivity, economics and other conditions of the compound. And preferably 0.7 to 1.5 equivalents. If a base is used, the base is usually in a proportion ranging from 1 to 5 equivalents, preferably in a proportion ranging from 1 to 2 equivalents. In particular, in the case of a compound (Ilia) in which M is an alkali metal, the reaction can be performed without using a base.

 Examples of the base used in the reaction include alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, sodium carbonate, and carbonate. Inorganic bases such as alkali metal carbonates such as potassium and sodium bicarbonate; alkali metal hydrides such as sodium hydride and calcium hydride; triethylamine, pyridine; 1,8-diazabicyclo [5.4.0] 7 (hereinafter referred to as DBU), and organic bases such as n-butyllithium and lithium diisopropylamide.

 Examples of the inert solvent used in the reaction include alcohol solvents such as acetonitrile, methanol, ethanol, etc., glycol solvents such as ethylene glycol, halogenated hydrocarbon solvents such as dichloromethane, toluene, xylene, and chloroform. Aromatic solvents such as benzene, ether solvents such as tetrahydrofuran (hereinafter referred to as THF), diethyl ether and the like, polyether solvents such as methyl cello sonolev and ethyl solvent, dimethylformamide ( Hereinafter, amides such as DMF), dimethylacetamide (hereinafter, referred to as DMA), dimethyl sulfoxide (hereinafter, referred to as DMSO), water, and the like. These solvents may be used alone or in combination of two or more, and may be solvent-free. If necessary, a phase transfer catalyst such as a quaternary ammonium salt such as tetra-n-butylammonium bromide and triethylbenzylammonium chloride, and a crown ether can also be used.

 1-2. Process from compound (V) to compound (Ie)

The production of compound (Ie) by elimination of hydrogen bromide is carried out by a known method, for example, the method described in The Chemistry of Functional Groups, supplement D part. 2, pp. 1173-1227, 1983, published by Wiley) or can be produced according to the method described in the following, or It is.

 This reaction is usually carried out in an inert solvent in the presence or absence of a base, and the reaction temperature range varies depending on the reagents and the reaction solvent used, but is usually from 180 ° C to 250 ° C. C, preferably in the range of 120 ° C to 150 ° C. Reaction times typically range from instantaneous to 24 hours.

 Examples of the base used in the reaction include alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide; sodium carbonate and potassium carbonate. , Triethylamine, pyridine, DBU, 1,5-diazabicyclo [3.4.0] nonene-5 (hereinafter referred to as DBN), and the like. The amount of the base used depends on the compound (V). On the other hand, the base is usually in a ratio of 1 to 5 equivalents, preferably in a ratio of 1 to 2 equivalents.

 Examples of the inert solvent used in the reaction include alcohol solvents such as acetonitrile, methanol, and ethanol; glycol solvents such as ethylene glycol; halogenated hydrocarbon solvents such as dichloromethane; toluene, xylene; Aromatic solvents such as benzene, ether solvents such as THF and diethyl ether, polyether solvents such as methyl-solve and ethyl-solve, amides such as DMF and DMA, DMS〇 and water, etc. Is mentioned. These solvents may be used alone or in combination of two or more, and may be solvent-free.

 If necessary, phase transfer catalysts such as quaternary ammonium salts such as tetra-n-butylammonium bromide and triethylbenzylammonium chloride, and crown ethers can also be used.

1-3. Process from compound (Ie) to compound (la)

 Oxidizing agents that can be used in the reaction include, for example, hydrogen peroxide, peracids such as metabenzo-perbenzoic acid and benzoyl peroxide, potassium permanganate, sodium periodate, sodium perborate, and acylated nitrous acid. The use amount is 1 equivalent to a small excess with respect to the starting material (Ie) when n == l, preferably about 1 to 1.1 equivalent, and 2 when n = 2. Equivalent to 4 equivalents.

Inert solvents that can be used include, for example, water, alcohols, glycol solvents, Halogenated hydrocarbon solvents, aromatic solvents and the like can be used. These inert solvents may be used alone or as a mixture of two or more.

 As shown in the above Reaction Scheme 1, the desired compound (Ie) can be prepared by reacting the starting compound (XIV) with the compound (XV) in an inert solvent in the presence or absence of a base. ) Can be manufactured. The starting compound (XIV) is available from Heterocycles, Vol. 36, No. 33-36 (1993), Japanese Unexamined Patent Publication No. 59-39884, or the journal “Ob 'Chemical” Society ( 1965) 5166-5176) and the like. The compound (XV) to be reacted can be produced according to the production method disclosed in Japanese Patent Application Laid-Open No. Hei 9-501175. 1-4. Process from compound (XIV) to compound (Ie)

 The reaction temperature range of this reaction varies depending on the reagents and reaction solvents used, etc., but is usually in the range of 78 ° C. to 250 ° C., preferably in the range of 0 ° C. to 150 ° C. It is. Reaction times typically range from instantaneous to 48 hours.

 Since this reaction is an equimolar reaction, the compound represented by the general formula (XV) is in a range of 0.5 to 2 equivalents per 1 equivalent of the compound represented by the general formula (XIV), and is preferably The range is from 0.8 to 1.2 equivalents.

 This reaction can be carried out in the same manner as in the step from compound (Ilia) to compound (V) to produce the desired product.

(Production method 2)

(Wherein, R,, R ₂ , L, M, Y and X are as defined above, R ₃ is a hydrogen atom,

(C _1-6 ) represents an alkyl group or a phenyl group which may have a substituent. The compound represented by the above general formula (VII) or (νπ ′), which is the starting compound for this reaction, can be obtained by a known method, that is, JP-A-8-325110 (a compound having 5-position COOH). 'Berichte (Chem. Ber., 99, 1618-1631, 1966) (compounds in which the 4-position is a carboxylic acid derivative and compounds in which the 5-position represents a hydroxyl group, a mercapto group or an amino group), etc. The compound (lb) can be derived by proceeding the reaction according to the conditions disclosed in the above-mentioned patent publications and the like. Each reaction may be performed according to the above-mentioned known methods. That is, the compound of the general formula (VII) is represented by the general formula (VIII) by using a suitable halogenating agent such as thionyl chloride and phosphorus oxychloride. When the acid halide is reacted with a compound of the general formula (IX) or (X) in an inert solvent in the presence of a base, usually in the presence of a base, the compound ( lb). When the acid halide is reacted with ammonia, a primary amine or an aniline represented by the general formula (XVI), an amide represented by the general formula (Π) is produced, and the amide (Ι Ι ′) is produced. The compound (lb) can be obtained by reacting the compound (IV) or (VI) with the compound (IV) according to the step of producing (le) from the compound (Ilia) in the above Reaction Scheme 1. Next, a thioamide (If) can be produced by reacting the compound (lb) with a sulfurizing reagent such as a Lawesson reagent.

 (Production method 3) Reaction formula 3

(Wherein, L, X are the same as above, R ₄ represents a (C, — ₆ ) alkyl group, and M, represents a hydrogen atom or a sodium atom.)

The compound represented by the above general formula (XI), which is a starting compound of this reaction, is disclosed in JP-A-59-39884, JP-A-Ichiguppa Patent Publication No. EP 104444, etc. Can be produced according to the method described in (1). By treating compound (XI) with a base, a mercaptothiadiazole or a salt thereof represented by the general formula (XII) can be produced. The compound (XII) can be isolated or not isolated and reacted with the compound (VI) to produce the compound represented by the general formula (Ic). The process from compound (XI) to compound (Ic) It is carried out in accordance with the conditions disclosed in Japanese Patent Application Laid-Open No. Hei 9-151197, or as follows.

 3-1. Step from compound (XI) to compound (XII) to (Ic)

 This reaction is usually carried out in an inert solvent in the presence of a base, and the reaction temperature is usually in the range of 80 ° C to 200 ° C, preferably -20 ° C to 100 ° C, and more preferably 0 ° C to 100 ° C. ° C to room temperature. Reaction times usually range from instantaneous to 24 hours. The amount of the base used in the reaction is usually 1 to 5 mol, preferably 1 to 2 mol, per 1 mol of compound (XI). Examples of the base used in the reaction include inorganic bases such as alkali metal hydroxides such as powdered potassium hydroxide, alkali metal alkoxides such as sodium methoxide, sodium methoxide and potassium t-butoxide; DBU, DBN, etc. Organic bases and the like.

 Examples of the inert solvent used in the reaction include alcohol solvents such as acetonitrile, methanol and ethanol, glycol solvents such as ethylene glycol, halogenated hydrocarbon solvents such as dichloromethane, toluene, xylene, and chlorobenzene. Aromatic solvents, ether solvents such as THF and getyl ether, and polyether solvents such as methyl sorb and ethyl sorb.

 The amount of the compound (VI) to be subsequently reacted is 0.5 to 2 equivalents, preferably 0.8 to 1.2 equivalents, per 1 equivalent of the compound (XI).

(Production method 4) Reaction formula 4 i) CIF ₂ COONa

(Wherein, R is the same as described above.)

Compound (XIII), which is a starting material for this reaction, is generally produced according to the method described in JP-A-59-39884, JP-A-Tsubaki Patent Publication No. EP 104403 or the like. can do.

 Deriving the compound represented by the general formula (XIII) using, for example, a Wittig reaction or a similar method such as the Horner-Emmons or Pezworth-Emmons reaction,

The compound represented by (Id) can be produced. In this reaction, chlorodifluoroacetic acid and a phosphorus compound such as a triarylphosphine such as triphenylphosphine or a trialkylphosphine or a trialkylphosphite form a ylide compound and then react with the aldehyde. And a method in which the same reaction is carried out using dibromodifluoromethane. This reaction can be carried out according to the method described in Tetrahedron Lett. (Tetrahedron Lett., 23, 1461-1463, 1964), Japanese Patent Publication No. 8-503932, and the like.

 Hereinafter, typical compounds of the 1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention are shown in Table 1, Table 2, Table 3, Table 4, and Table 5. . In the table

“Me” represents methyl, “E t” represents ethyl, “P r” represents propyl, “Bu” represents butyl, “He x” represents hexyl, “Oct” represents octyl, and “Ph”. "" Indicates phenyl, "Bn" indicates benzyl, "n-" indicates normal, "i-1" indicates iso, "t-1" indicates tertiary, and "Me 0" indicates methoxy.

Table 1 Compound properties

 R n (refractive index nDZ melting point mp)

I- 1 Me 0 1.5312 (23.2 ° C) I- 21- Pr 0 1.5189 (22.8.C) I-32-Me-Ph 0 1.5864 (21.6 ° C ) I-42-Me-Ph 1.5522 (22.3.C) I-52-Me-Ph 21.5786 (22.2 ° C) I-63-Me-Ph 0 1.5942 (21.6.C) I- 73-Me-Ph 1 1.5820 (22.3.C) I-83-Me-Ph 2 1.5562 (22.2 ° C) I-94- Me-Ph 0 1. 5922 (20.8.C) I- 10 4-Me-Ph 77. G 80. 4 ° C I- 11 4-Me-Ph 2 Paste

I- 12 2-Cl-Ph 0 1.5978 (21.2 ° C) Table 1 (continued) Compound properties

 Number n (refractive index nDZ melting point mp)

I- 13 2-Cl-Ph 1 paste

 I- 14 2-Cl-Ph 2 paste

 I- 15 4-Cl-Ph 0 1.6092 (21.0 ° C)

I-164-CI-Ph1 89. G 90.4. C

I- 17 4- CI- Ph 2 90.2- 91.2 ° C

I- 18 4-F-Ph 0 1.5615 (23.4 ° C)

I- 19 4-t-Bu-Ph 0 1.5802 (19.8.C)

I- 20 2, 4-CI ₂ -Ph 0 1.5800 (22.

I-212, 4-CI ₂ -Ph 1 1.5665 (22.2 ° C)

I- 22, 2, 4- CI ₂ -Ph 2 1.5474 (22.4 ° C)

I-233-Piricil "0 1.582 (23.6 ° C)

I-24 cyclohexane. 0 1.5197 (22.5 ° C)

I- 25 C (= 0) CH ₃ 0 Paste

I- 26 4-C0 ₂ Me-Ph 0 Paste

I-27 4- C0 ₂ Et-Ph 0 Paste

I- 28 2, 4-F ₂ -Ph 0 1.5275 (13.8.C)

I- 29 4-MeS-Ph 0 1. 6494 (14.3 ° C)

I- 30 4- Ph- 0-Ph 0 1. 6236 (21.5 ° C)

I-313,4-Methylenesi ', Oxyfu :: R 0 37.3-38.3. C

I-32 2-Frill 0 1.5928 (20.8 ° C)

I- 33 2 -h / h 0 1.6105 (20.5 ° C) Table 1 (continued) Compound properties

 R, n (refractive index nDZ melting point mp) τ-one 4-C00H-Ph 0 168.5 174.8 ° C

T— J Ph 0 1.5234 (22.5C)

 Ph 2 1.5661 (22.7 ° C) τ_ 4-1 -Ph 0 1.5064 (21, 8 ° C)

Τ 一 οοο 3-MeO-Ph 0 1.5157

_{Q 4- MeS0 2 - Ph 1 144.1} 147.6C τ one _{4- MeS0 2 - Ph 2 104.1 109.8} ° C τ one Me 1 1.5370 (21.5C)

 Me 2 1.5128 (21.6C) 1't 2-Br-Ph 0 1.6056 (20.6 ° C)

Τ-44 2-Br-Ph 1 1.5795 (22.2C)

I-2-Br-Ph 2 1.5550 (22.2 ° C)

I- 46 3-Br-Ph 0 1.6132 (20.8 ° C)

I-47 3-Br-Ph 1 1.5756 (21.9 ° C)

I- 48 3-Br-Ph 2 1.5738

 I- 49 4-Br-Ph 0 1.6146 (21.1 ° C)

50 4-Br-Ph 1 88.0 90.2 ° C

I-51 4-Br-Ph 2 1.5780 (21.6C)

I- 52 4-n-Bu-Ph 0 1.5738 (18.2C)

53 4-n-Bu-Ph 1 1.5602 (21.3C)

I- 54 4-n-Bu-Ph 2 1.o3oo (21.0 ° C) Table 1 (continued) Compound properties

 R> n (refractive index nD / melting point mp)

I- 55 4-n-0ct-Ph 0 1.5575 (19.5 ° C)

I- 56 2-F-Ph 0 1. 5841 (20.4 ° C)

I- 57 3, 4- CI 2 -Ph 0 1.6012 (18.4 ° C)

I-58 3, 4-CI ₂ Ph 1 1.5705 (22.5 ° C)

I-59 3, 4-CI ₂ -Ph 2 1.5415 (22.5 ° C)

I- 60 2, 5-CI ₂ -Ph 1 paste

I-61 2, 5-CI ₂ -Ph 2 paste

 I-62 2, 3, 4-CI 3-Ph 0 Paste

I- 63 4-N0 ₂ -Ph 0 56.2 to 57.0 ° C

I-64 4-t-Bu-S-Ph 0 Paste

 I-65 4-MeO-Ph 0 1.6029 (13.0.C)

I-66 3- F_4-Me-Ph 0 Paste

 I- 67 4-t-Bu-Ph 1 1.5670 (21.7 ° C)

I-68 4-t-Bu-Ph 2 1.555 (21.7 ° C)

I- 69 4- Ph- 0- Ph 1 1.6197 (19.9 ° C)

I- 70 4-Ph-O-Ph 2 1.6080 (19.9 ° C)

I-71 3-F-Ph 0 1.5831 (18.3 ° C)

I-72 4-t-BuOCO-Ph 0 1.5562 (22.4 ° C)

_{I- 73 4 - H 2 NC0- Ph} 0 111. 5 ~ 113. 8. C

I- 74 -C (= N0H) CH ₃₀ paste

I- 75 -C (= N0C0 marauder e ₂ ) CH ₃₀ paste Table 1 (continued) Compound properties

 Number R n (refractive index nD / melting point mp)

I-76-C (= N0CH ₂ 0 Paste type

(4-C0 ₂ tens Bu- Ph)) CH ₃

 I-772-thenyl 153.0-54.5. C

I-78 2-Thenyl 2 75.6 to 80.0 ° C

I- 79 1,2,3,4-tetrahydronaphthalene

 1 6-yl 0 1.6008 (19.5.C)

I-80 2-H. Resil "0 1.5992 (21.7 ° C)

I-81 4-Piricil "0 57.8 to 59.4. C

I-82 5-Me -Fran-2-yl 0 1.5908 (23.6 ° C)

I-83 5—Me—Fran—2—Ill 1 62.0-64.0. C

I-84 5_Me—Fran-2-yl 2 54.0 to 56 · 0. C

I-85 5-Br-Chi-Shen Fen-2-yl 0 1.6512 (24.6 ° C)

I-865—Br—Chisheng Fen-2-yl 1 86.0-87.0. C

I-87 5—Br-chi-fen-2-yl 2 76.0 to 78.0 ° C

I-88 -C (= NOCH ₃ ) CH ₃ 0 1.5478 (23.2 ° C)

I-89 -C (= N0CH ₂ -CH = CH ₂ ) CH ₃ 0 1.5356 (23.2 ° C)

I - 90 -C (= NH- Ph) CH 3 0 91.4~ 96.2. C

I-91 4-F-3-Me-Ph 1 Paste

 I-92 2-Naphthyl 0 paste

 I-93 4-C1- 2-F-5-Me-Ph 0 paste

I-94 3-BnO-Ph 0 Paste Table 1 (continued) Compound properties

Number n (refractive index _n D // melting point mp)

95 3, 4-F ₉ -Ph 0 1.5755 (21.5 ° C)

I-96 4-CN-Ph 0 paste

 I-97 3-chille 0 1.5589 (16.1 ° C)

I—98 to “nso” [b] Franc-one 2-yl 0 60.6 to 61 · 0. C

 I-99 2, 5-Meu-Ph 0 Paste

I-100 2, 5-Me ₂ -Ph 1 paste

I-101 2, 5-Me ₂ -Ph 2 paste

1-102 3-CF ₃ -Ph 0 1.555 (22.4 ° C)

1-103 p-biphenyl 0 1. 6390 (22.1.C)

1-104 4-CF ₃ -Ph 0 1.5498 (21.9 ° C)

1-105 2, 6-F ₂ -Ph 0 1.5628 (21.9 ° C)

1-106 3-N0 ₂ -Ph 0 Paste

 1-107 2-Cl- 4- F- 5- Me-Ph 0 Paste

1-108 (4-Cl-Ph) S-CH 2 0 1. 6150 (22. 7 ° C)

1-109 (4-Me-Ph) S-CH ₂ 0 1.5939 (22.7 ° C)

1-110 (4- N0 ₂ -Ph) S-CH ₂ 0 1. 6376 (22.8.C) I—111 2 -Pilicil, 'Luthio; I tyl 0 1.6013 (22.8 ° C)

1-112 n-Hex 0 1.513 (20.7 ° C) 1-113 1-Naphthyl 0

1-114 2, 4-Me ₂ -Ph 0 paste

1-115 2-i-Pr-Ph 0 Paste Table 1 (continued) Compound properties

 Number n (refractive index nD / melting point immediately)

I- -116 2-i-Pr-Ph 2 paste

I- -117 2 -Piricil "hydrochloride 0 72.5 to 78.5 C

I- -118 4 -Pirisi hydrochloride 0

I- -119 3, 4- (MeO) ₂ -Ph 0 ヽ

I- -120 3, 4, 5- (MeO) ₃ -Ph 0 I. o / 4 Δ \). 4)

I- -121 3, 4-Me ₂ -Ph 0 ^

 Bird

 I- -122 4-BnO-Ph 0

 ΊΛ

 I- -123 4-Et-Ph 0 丄. ^ Ί / o¾ f Z ヮ 丄. 9

 I- -124 0 i

I- -125 1 55.5-57 · 0. C

I- -126 4-n-Pr-Ph 0 1.5748 (20.8 ° C)

I- -127 4-n-Pr-Ph 1 49.0〜50.0 ° C

I- -128 3-Ph0-Ph 0 1.6062 (20.8 ° C)

I- -129 3-Ph0-Ph 1 Paste

I- -130 2-Bn0-Ph 0 1.6072 (19.7 ° C)

I- -131 4-Et-Ph 1 42〜43.5 ° C

I- -132 3, 4-Me ₂ -Ph 1 73 ~ 75 ° C

 I- -133 4-BnO-Ph 19 93. C

 I- -134 4-C1-2-F-5 0 Paste

-(MeOCO-CH ₂ 0) -Ph

I- -135 3— Me—Pili—2—yl 0 Paste Table 1 (continued) Compound properties

 Number n (refractive index nD / melting point mp)

1-136 5-C, 'Nso, [b] Fran-2-yl 0 83.0-84.3. C

1-137 3-F-4-MeO-Ph 0 1.5902 (20.7 ° C)

1-138 2—Me-thiazole ”4-yl 0 1.5940 (1.2 ° C) 1-139 Imita” [1,2—a] pyridin-2-yl 0 110.5 to 112.0 ° C

1-140 4- (3-C1- 4-Me-PhHCO) -Ph 0141 -142.5. C

1-141 4-Cl-PhCO 0 50.5-53.2 ° C

1-142 4-MeNHCO-Ph 0 106.5 〜108 ° C

1-143 4-Me ₂ NC0-Ph 0 Paste

1-144 4- (Ph-C (Me ₂ )-NHCO)-Ph 0 paste

_{1-145 EtOCO- C (Me) 2 -} 0 1.5038 (20.5 ° C)

1-146 t ° Rishi, N-Oxide_2-ylthiomethyl 0 Paste

1—147 4, 6-Me ₂ —pyrimine—2-ylthiomethyl 0 1.5696 (22.9 ° C)

_{1-148 HOCO-C (Me) 2} - 0 pasty

1-149 (4-Cl-PhNHCO)-C (Me) ₂₀ 90 ~ 92 ° C

Ι-ΙδΟ 4,6-Me ₂ -Pi j j

 2-I 'Les / Lephonylmethy;

 1-151 Me-CH (OH) 0 1.5418 (26.0.C)

1-152 Me ₃ CCO-0-CH (Me) 0 1.4890 (26.0 ° C)

1-153 4-F-Ph-C (Me) ₂ 1 1.5298 (24.2 ° C)

I-154 4-F-Ph-C (Me) ₂ 2 1.5471 (21.2 ° C)

1-155 4-F-Ph-C (Me) ₂ 0 Paste Table 1 (continued) Compound properties

 No.Rin (refractive index nD / melting point mp)

1-156 t-Bu-NHCO-C (Me) ₂ 0 1.5187 (21.8 ° C)

1-157 Me ₂ NC0-C (Me) ₂ 0 Paste

1-158 4-Me-Ph-C (Me) ₂ 0 1.5503 (22.7 ° C)

1-159 Chioff: ^ -n-2-yl-C (Me) ₂ 0 1.5737 (22.8.C)

1-160 PhO-CH (Me) 0 Paste

 1-161 (4-MeO-Ph) O-CH (Me) 0 1.5358 (25.8 ° C)

1-162 (4-F-Ph) O-CH (Me) 0 1.5375 (25.8 ° C)

1-163 Ph-C (Me) ₂ 0 1.5591 (27.2 ° C)

1-164 1—Ph to cyclo. 0 1.5699 (27.2 ° C)

1-165 (3- CI- Ph)-C (Me) ₂ 0 1.5642 (26.7 ° C)

1-166 (4- CI- Ph)-C (Me) ₂ 0 1.5444 (26.2 ° C)

1-167 2, 3-si, dani ni P-inen-5-yl 0 1.6059 (18.3 ° C)

1-168 2, 4-F ₂ -Ph 2 1.5444 (18.8 ° C)

1-169 2-furyl 1 60.2 ~ 62.5. C

1-170 2-ruffle 2 69.5-71.0 ° C

Table 2 (X = H) Compound property number Yz (refractive index nDZ melting point mp)

II- 1 Me 0 0 1.4818 (20.5 ° C)

II- 2 Ph 0 0 1.5320 (25.5 ° C)

II- 3 4-Cl-Ph 0 0 Paste

II- 4 4-Me- Ph 0 0 Paste

II- □ PhO-CH ₂ 0 1.5372 (26.1 ° C)

II- 6 4-F-PhO- CH ₂ 0 1.5 320 (25.5 ° C)

II- 7 4-MeO-Ph 0 0 1.5770 (21.0 ° C)

II-82-naphthyl 0 0 1.6138 (21.8 ° C)

II-92-Piricil "0 0 1.5285 (21.7 ° C)

II-10 4-Pirishi, / 0 0 1.5550 (21.8 ° C)

II- 11 2, 4-Me ₂ -Ph 0 0 1.5332 (23.4 ° C)

II- 12 4-MeS-Ph 0 0 1.6030 (20.6 ° C)

II- 13 4-MeSO-Ph 0 0 1.5696 (20.5 ° C)

_{II- 14 4- eS0 2 -Ph 0 0} 1.5550 (20.6 ° C)

II- 15 4- CI- Ph NH 0 107.5 to 108.5. C Table 2 (continued) Compound properties

 Number Ri Y Z (refractive index nD / melting point mp)

II- 16 4-Me-Ph NH 0 128.0 129.5 ° C

II- 17 PhS-CH ₂ NH 0 paste

II- 18 4-Cl-PhS-CH ₂ NH 0 paste

_{II- 19 4-N0 2 -PhS-} CH 2 NH 0 pasty

 II-20 Ph NH 0 86.2 88 ° C

II- 21 Ph O e 0 Paste

CF ₃ NH 0 44.5 48.0 ° C

4-MeO-Ph NH 0 120.5 122.5 ° C

2-Piricil NH 0 66.5 69.0. C

_{II- 25 4-N0 2 -Ph NH} 0 121.0 127.0. C

II- 26 Ph NH s 85.0 87.0 C

Table 3 Compound properties

 Number XYZ (refractive index nD / melting point mp)

III- 1 Ph H 0 0 1.555 (20.7 ° C)

III- 2 Me H 0 0 1.4968 (20.7 ° C)

III- 3 4- CI-Ph H 0 0 1. 5714 (20.8 ° C)

III- 4 4-Me-Ph H 0 0 1.5545 (20.8 ° C)

III-δ 4-MeO-Ph H 0 0 1.5690 (20.8.C)

III-6 2-Naphthyl H 0 0 53. 0 to 56 ° C

III- 7 2, 4-Me ₂ -Ph H 0 0 1. 5430 (21.4 ° C)

III- 8, 2, 4-Me ₂ -Ph H 0 0 1.5662 (20.4 ° C)

III-9 Me H NH 0 1.5146 (22.8 ° C)

 III-19 4-Cl-Ph H NH s Paste

111-20 4-Me-Ph H NH s Paste

Table 4

Compound No. R, Physical properties (refractive index nD / melting point mp)

IV- 1 4-Me-Ph 1.5530 (23.4 ° C)

Table 5

 Compound properties

R ₁ n (refractive index nDZ melting point mp)

V-1 cyclopropyl ° 1.5304 (26.1 ° C) V-2 cyclopropyl. Lohi. 11.5168 (24.1 ° C) V-3 cyclof. Lohi. 21.5148 (24.1 ° C) V-4 4-F-Ph 0 1.5574 (24.9 ° C) V-5 4-F-Ph 1 100.6 to 103.8 ° C V -6 4-F-Ph 2 72.6 to 74.2 ° C V- 7 4- e-Ph 0 1.5588 (25.9 ° C) V- 8 4-t-Bu-Ph 0 1.5578 (22. 6 ° C) V- 9 4-CN-Ph 0 1. 5968 (22. 7 ° C) V- 10 3- N0 2 -Ph 0 1. 5523 (25. 8 ° C) V- 11 4 _{-. N0 2 -Ph 0 65. 2~65} 9. CV-124-Br-Ph 0 1.6136 (25.0 ° C) V-132 -Pilicil 0 1.5950 (24.8 ° C) V-14 3 -Piricil 0 1.5912 (24.8 ° C) V- 15 2-furyl 0 1.5766 (25.0 ° C) V-16 2-thenyl 0 1.5840 (25.0 ° C) ¹ shows ¹ H—NMR data of a compound in the form of a strike. Table 6 Compound No. NMR data [δ value _{(CDC1 3 / TMS, (ppm} )) ]

I-1 11 2.2-2.4 (m, 2H), 2.47 (s, 3Η), 3.08 (t, 2Η),

 3.9-4.2 (m, IH), 7.38 (d, 2H), 7.91 (d, 2H).

 I-13 2.3-2.4 (m, IH), 2.92 (t, 2H), 4.0—4.2 (m, IH)

 7.4-7.6 (m, 4H).

 I 14 2.3-2.4 (m, 2H), 3.07 (t, 2H), 4.0—4.2 (m, IH),

 7.4-7.6 (m, 4H).

 I-25 2.4-2.6 (m, 2H), 2.82 (s, 3H), 3.05 (t, 2H),

 4.2-4.4 (m, IH)

 I-26 2.4-2.5 (m, 2H), 3. ll (t, 2H), 3.95 (s, 3H),

 4.1-4.3 (m, IH), 8.0-8.1 (m, 2H), 8.1-8.2 (m, 2H).

I-1 27 1.42 (t, 3H), 2.4-2.5 (ra, 2H), 3. ll (t, 2H),

 4.1—4.3 (m, IH), 4.41 (q, 2H), 8.0—8.1 (m, 2H),

8.1-8.2 (m, 2H).

 I-1 60 2.28-2.63 (m, 2H), 2.98 (t, 2H), 4.07-4.23 (m, IH)

 7.46-7.57 (m, 3H).

 I-61 2.41 (q, 2H), 3.04 (t, 2H), 4.10— 4.32 (m, IH),

 7.33 (d, IH).

 I-62 2.41 (q, 2H), 3.04 (t, 2H), 4.10—4.32 (m, IH),

 7.33 (d, IH), 7.53 (d, IH).

 I-66 2.37 (d, 3H), 2.35-2.48 (m, 2H), 3.08 (t, 2H),

7.72 (m, IH), 7.80 (m, IH). Table 6 (Continued) Compound number. H-band _R data [ _δ value (cod / TMS, (ppm))]

I-74 2.35-2.55 (m, 2H), 2.59 (s, 3H), 3.06 (t, 2H),

 4.20-4.40 (m, IH), 7.50-8.50 (m, IH).

 I-75 2.40-2.60 (ra, 2H), 2.66 (s, 3H), 2.90-3.10 (m, 8H),

 4.20-4.40 (m, IH).

 I-76 1.58 (s, 9H), 2.35-2.50 (m, 2H), 2.57 (s, 3H),

 2.99 (t, 2H), 4.10-4.40 (m, IH), 5.30 (s, 2H),

7.4-7.55 (ra, 2H), 7.9-8.05 (m, 2H)

I-91 2.30-2.43 (m, 2H), 2.38 (s, 3H), 3.01 (t, 2H),

4.08-4.25 (m, IH), 7.18 (dd, IH), 7.54-7.61 (m, IH) _:

7.71 (dd, IH).

 I-92 2.40-2.51 (m, 2H), 3.11 (t, 2H), 4.09—4.33 (m, IH)

 7.52-7.59 (m, 2H), 7.88-7.98 (m, 2H), 7.99 (d, IH), 8.12 (dd, IH), 8.41 (s, IH).

 I-94 2.3-2.5 (ra, 2H), 3.08 (s, 2H), 4.1-4.3 (m, IH),

 7.26 (s, 2H), 7.0-7.1 (m, IH), 7.3- 7.5 (m, 6H) 7.5-7.6 (m, 2H)

 I-96 2.4-2.6 (m, 2H), 3.15 (t, 2H), 4.1-4.3 (m, IH),

 7.81 (d, 2H), 8.12 (d, 2H).

 I-99 2.20 (s, 3H), 2.3-2.δ (m, 5H), 2.99 (t, 2H),

4.1-4.3 (m, IH), 7.1-7.3 (m, 3H). Table 6 (continued) Compound number-NMR data [δ value (CDC1 TMS, (ppm))]

I-one 100 2.1-2.3 (m, 4H), 2.37 (s, 3H), 2, 4—2.6 (m, IH),

 2.83 (t, 2H), 4.0-4.2 (m, IH), 7.12 (s, IH) 7.4-7.6 (m, IH), 7.9—8.1 (m, IH).

 I -101 2.17 (s, 3H), 2.2-2.4 (m, 2H), 2.39 (s, 3H),

 2.95 (t, 2H), 2.95 (t, 2H), 4.0-4.2 (m, IH) 7.2-7.3 (m, 3H).

 I-I 106 2.4-2.6 (m, 2H), 3.16 (t, 2H), 4.1-4.3 (m, IH),

 7.6-7.7 (m, IH), 8.2-8.4 (ra, 2H), 8.8-8.9 (m, IH).

I-107 2.31 (s, 3H), 2.3-2.5 (m, 2H), 3.02 (t, 2H),

 4.1-4.3 (m, IH), 7.2-7.4 (m, 2H).

 I -113 2.2-2.4 (m, 2H), 2.97 (t, 2H), 4.0-4.2 (m, IH),

 7.4—7.7 (ra, 5H), 7.9—8.1 (m, 2H).

I -114 2.23 (s, 3H), 2.3-2.5 (m, 5H), 2.98 (t, 2H) ₍

 4.1-4.3 (m, IH), 7.1—7.3 (m, 3H).

 I -115 1.31 (d, 6H), 2.4-2.6 (m, 2H), 2.9-3.1 (m, 5H),

 4.1-4.3 (m, IH), 7.38 (d, 2H), 7.88 (d, 2H).

 I -116 1.31 (d, 6H), 2.2—2.4 (m, 2H), 2.9—3.1 (m, 5H),

 3.9-4.2 (m, IH), 7.43 (d, 2H), 7.94 (d, 2H).

I -121 2.3-2.5 (m, 2H), 3.07 (t, 2H), 4.1-4.3 (m, IH),

7.28 (d, IH), 7.66 (d, IH), 7.74 (s, IH). to to

 o

,,,) (() () 4 IH 6sH.24.4 5.62.29 I 7sH. 1

 ,,,,) (() () 252 ョ 2H 2.61sH..733.76t 2H—

 o ^

 ,) (I 4143 H ..--,,,,) () (() l 2∞3s6H.42.6 2H 3022..3 mH1- ,,),) () (I 8mH.2 IH 7.77 .88.3 .——

 ,, ,,,, () () () 452H 7.m IH.5s.07.23m I 77.H—- si

 ,,,,,, () () () 2426426 2H0t 2H. · 3.8424.4 ョ IH——

,,, (()) 7922H 84d 2H.d.0.

 ,, ,,,) (() (,) 4 4.4.3 6.9b IH 72s.7.5 5H —- ,,,) (), () 1.866H 22. 2H 3l 1.46. Lt 2H—

 , ,, ,, () () () 2dH Ί 57dH 7.5728002H ... d

 ,,,,) (), (() 2H 2H 2.4.63.03.m 8H 4 I 3 T4.3mH-1

 3 ^

 \ ',), (() 27.7. IH 7 I I 3.67.7H-1

 ,,,, ()) (2.63s 3H 307tH.2

 ,,,) ,, ((()) 4.73s 2H7.122H.3dd 722H

 ,,,, () (). 0tH 3H 352.79s 3

 ,) (7.07 ョ 9H 5.-,,, ()) (4. ョ IH 22H 2.26.99t- ,,,,, () () () 2.15H1d 2H 5 s 5s 7.3.37.71

 ,, (,,) ()) (25 ョ 2H.0H 4 I 2.3.36t 2. Τ4.3 · H—

(/ MSCDCT * Table 6 (continued) Compound No. negation R data [δ value _{(CDC1 3 / TMS, (ppm} )) ]

I -155 2.0-2.2 (m, 2H), 2.17 (s, 6H), 3.10 (t, 2H),

 3.8-4.0 (ra, IH), 7.0-7.1 (m, 2H), 7.3-7.4 (m, 2H).

 I-157 1.80 (3, 6H), 2.3-2.5 (m, 2H), 2.47 (bs, 3H),

 2.96 (bs, 3H), 3.04 (t, 2H), 4.1-4.3 (m, IH).

 I-160 1.84 (d, 3H), 2.3-2.5 (m, 2H), 2.99 (t, 2H),

 4.1-4.3 (m, IH), 5.95 (q, IH), 6.9-7.0 (m, 3H),

 7.1-7.3 (ra, 2H).

 II- 3 2.3-2.5 (m, 2H), 4.0— 4.2 (m, IH), 4.33 (t, 2H),

 7.49 (d, 2H), 7.87 (d, 2H).

 II- 4 2.3-2.5 (ra, 2H), 2.41 (s, 3H), 4.0-4.2 (m, IH),

 4.28 (t, 2H), 7.28 (d, 2H), 7.76 (d, 2H).

 II- 17 2.2-2.4 (m, 2H), 3.4-3.5 (m, 2H), 4.1-4.3 (m, IH),

 4.70 (s, 2H), 6.84 (bs, IH), 7.2-7.4 (m, 5H)

 II- 18 2.2-2.4 (m, 2H), 3.4-3.5 (m, 2H), 4.1- 4.3 (m, IH),

 4.70 (s, 2H), 6.62 (bs, lH), 7.2-7.3 (m, 4H).

 II- 19 2.2-2.4 (ra, 2H), 3.5-3.6 (m, 2H), 4.1-4.3 (m, IH),

 4.90 (s, 2H), 6.33 (bs, IH), 7.55 (d, 2H), 8.13 (d, 2H).

II- 21 2.2-2.4 (m, 2H), 2.60 (s, 3H), 2.60 (s, 3H), 3.56 (t, 2H) _:

 4.0-4.2 (m, IH), 7.4-7.5 (m, 3H), 7.8-7.9 (m, 2H).

 III-1 18 2.4-2.6 (m, 2H), 3.8—3.9 (m, 2H), 4.1—4.3 (m, IH),

7.3-7.5 (ra, 5H), 9.08 (bs, IH). Table 6 (continued) Compound No. NMR data [δ value _{(CDC1 3 / TMS, (ppm} )) ] ΙΠ- 19 2. 4-2. 6 (m , 2H), 3. 8-3. 9 (m, 2H), 4 1—4.3 (m, 1H),

 7.3-7.5 (m, 4H), 9.15 (bs, 1H).

 111-20 2.42 (s, 3H), 2.4-2.6 (m, 2H), 3.8-3.9 (m, 2H),

 7.25 (d, 2H), 7.37 (d, 2H), 8.95 (bs, 1H). The 1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention or a salt thereof Pest control agent which is an active ingredient is suitable for various pests such as agriculture, forestry, horticulture, storage pests and sanitary pests, mites and nematodes that infest rice, vegetables, fruit trees, other crops and flowers, etc. For example, apple oysters (Adoxophyes orana fasciata), cynopods (Adoxophyes sp.), Apple crocodile (Graphol ita inopinata), pear ita molesta (Graphol ita molesta), and glyceminola ), Teyanozuma: \-(Homona magnaniraa), Chianohosoga (Calopti lia thevivora), Ringohosoga

 (Calopti lia zachrysa), Kimmonhosogah (Phyl lonorycter ringoniel la), Nashihosogah (Spulerrina astaurota), Monsirothe (Piers rapae crucivora), Ootano koga (Hel iothi s es po) (Plutel la xylostel la), apple turtle, Argyresthia conjugel la, peach mosquito (Carposina niponensis, two turtles ^! 77 (Chi lo suppressal is), kobume meiga (Cnaphalocrocis)

medinalis), Jamadame (Ephestia elutel la), Kunomeiga

(Glyphodes pyloal is), Sancimega Scirpophaga incertulas, Λ モ シ Par (Sesamia inferens), モ ン モ ン era opt era ), Lepidopteran pests, Cyanomi dorichme 3 Connos (Empoasca brassicae), Tsumak, 3 Noki (Nephotettix cinticeps), brown porpoises (Nilaparvata lugens), brown planthoppers (Sogatella furcifera), citrus white lice (Diaphorina citri), citrus whiteflies (Dialeurodes citri), red winged white lice (Bemicia tabaci), and white-tailed abalone (Bemicia tabacides) brassicae), Aphid gophids (Aphis gossipii),

(Rhopalosiphum padi) _s Momoka aphid (Myzus persicae), Cranop beetle (Ceroplastes cerciferus), Citrus stag beetle (Pulvinaria aurantii), Citrus mosquito (Pseudaonidia duplex) "Hemiptera pests such as" Yasparis yanonensis "(Anomala rufocuprea), beetles (Popillia japonica), Lasioderma serricorne, and yctus brunゥ (Epilachna

vigintiotopunctata, 7 s = Callosobruchus chinensis, Insect beetle (Listroderes costirostris, Scarab beetle (Sitophilus zeamais), Anthonomus gradis gradis, Din; femoral is), Oroema oryzae, Damin (Zeugodacus;

cucurbitae), citrus fruit (Dacus (Bactrocera) dorsalisj, rice ヽ moku, linoki (Agromyza oryzae J), evening magnolia (Delia antique), tanenoku (Delia platura), evening, (Asphondylia sp.), Jeno n

(usca domes tica), diptera insects such as Acaie force (Culex pipiens pipiens), flea beetle (Phyllotreta striolata), and pine beetle

(Toraicus piniperda), Korofudo: ^ Leptinotarsa

 decemlineata), Mexican beetle (Epilachna varivestis), cone root worms (Diabrotica sp.)

(Panonychus citri), Lin-ino-Yu, '; n (Panonychus ulmi), Namino-Yu,' Ni (Tetranychus urticae Koch), Fuzonsa-no-utani Tetranychus kanzawai Kishida), Ni! ^^^^^^^^ (Tetranychus cinnabarinus) phoenici s), grape spiders (Brevipalpus lewisi), and other spiders such as Cleoptera (Calacarus carinatus), Citrus avidani (Aculops pelekassi), Epitrimerus pyri (Epitrimerus pyri) Polyphagotarsonemus), mites such as Tyrophagus putrescentiae (Tyrophagus putrescentiae),

(Pratylenchus cof f eae), potato cyst cenyu (Globodera

Rostochiensis), Meloidogyne sp., Tylenchulus semipenetrans, Aphelenchus avenae, Aphelenchoides ritzemabosi, etc. It is. Scientific names are based on agricultural and forestry harmful animals. Insect Directory, 1987 edition (edited by the Japan Society of Applied Animal Entomology).

 The pesticidal agent of the present invention containing a 123-thiadiazol derivative represented by the general formula (I) or a salt thereof as an active ingredient damages paddy rice, vegetables, fruit trees, other crops, flowers and the like. It has a remarkable insecticidal activity against the above-mentioned pests or sanitary pests. Therefore, before the pests are generated or at the time when the pests are confirmed to occur, the rice and fruit The pest control agent of the present invention can be applied to vegetables, other crops, flowers, etc. by treating paddy water, foliage or soil, etc., and sanitary pests in houses and trenches around houses that damage humans and animals. However, the present invention is not limited to only these embodiments.

When a 123-thiadiazol derivative or a salt thereof represented by the general formula (I) of the present invention is used as a pesticide, it is formulated into a convenient form in accordance with a conventional method for pesticide formulation. It is common to use it. That is, the 1,23-thiadiazole derivative compound represented by the general formula (I) of the present invention or a salt thereof can be prepared by adding these to a suitable inert carrier and, if necessary, together with an auxiliary. And dissolving, separating, suspending, mixing, impregnating, and adsorbing it in an appropriate ratio to prepare an appropriate dosage form such as a suspension, emulsion, liquid, wettable powder, granule, powder, tablet, etc. Just use it. The inert carrier that can be used in the present invention may be either solid or liquid. Examples of the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, sawdust, tapako stalk flour. , Walnut powder, bran, cellulose powder, residue after extracting plant extract, crushed synthetic tree Synthetic polymers such as fats, clays (eg, kaolin, bentonite, acid clay), talcs (eg, talc, pyrophyllide, etc.), silicas (eg, diatomaceous earth, silica sand, mica, white carbon, etc.) Synthetic polymer silicic acid, also known as hydrous silicic acid, contains calcium silicate as a main component depending on the product.]), Activated carbon, zeolite powder, pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, calcium carbonate Examples include inorganic mineral powders, chemical fertilizers such as ammonium sulfate, phosphorous ammonium, ammonium nitrate, and salt salt, and compost, which are used alone or in the form of a mixture of two or more. Materials that can be liquid carriers are selected from those that have a solvent function per se, and those that can disperse the active ingredient with the aid of adjuvants even without the solvent function. Examples thereof include the following carriers, which may be used alone or in the form of a mixture of two or more types. Examples thereof include water, alcohols (eg, methanol, ethanol, isoprono, phenol, and butanol). ^^, ethylene glycolone, etc.), ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, di Propyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (E.g., benzene, tosoleene, xylene, sonoleventnaphtha, alequinolenaphthalene, etc.); Ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, etc., amides (eg, dimethylformamide, getylformamide, dimethylacetamide, etc.), nitriles (eg, acetonitrile, etc.), Dimethyl sulfoxides and the like can be mentioned. Examples of the other adjuvants include the following representative adjuvants. These adjuvants are used according to the purpose, and may be used alone or in combination of two or more kinds. In some cases, it is possible to use no auxiliaries at all.

Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compounds, such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene higher fatty acid ester, Xyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, Examples thereof include surfactants such as polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonic acid condensate, lignin sulfonate, and higher alcohol sulfate ester.

 For the purpose of stabilizing the dispersion of the active ingredient compound, sticking and Z or bonding, the following auxiliaries can be used. For example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic Auxiliary agents such as polyvial alcohol, pine oil, bran oil, bentonite, and ligninsulfonate can also be used.

 The following auxiliaries can be used to improve the flowability of solid products. For example, auxiliaries such as wax, stearate, alkyl phosphate and the like can be used. As a peptizer for the suspension product, an auxiliary agent such as a naphthalenesulfonic acid condensate and a condensed phosphate may be used.

 As an antifoaming agent, for example, an auxiliary agent such as silicone oil can be used. The compounding ratio of the active ingredient compound can be adjusted according to need. For example, 0.01 to 50% by weight in the case of powder or granules, and 0 in the case of emulsion or wettable powder. 0.1 to 50% by weight is suitable.

 The pesticidal agent of the present invention is used for controlling various pests, as it is, or in an appropriately diluted or suspended form with water or the like, in an amount effective for pest control in crops in which the occurrence of the pest is predicted. Alternatively, it may be applied to a place where generation is not preferable. The amount of the pest control agent of the present invention depends on various factors, for example, the purpose, the target pest, the growth status of the crop, the tendency of the pest, the weather environment condition, the dosage form, the method of application, the place of application, the time of application, etc. Although it fluctuates, the active ingredient compound may be appropriately selected from the range of 0.01 g to 5 kg per 10 ares according to the purpose.

 The pesticidal agent of the present invention can be further used in combination with other agricultural or horticultural insecticides or fungicides for the purpose of extending pests to be controlled, suitable period of control, or reducing the amount of drugs. .

Example

Hereinafter, typical examples, formulation examples, and test examples of the present invention are shown, but the present invention is not limited to these. Example 1 Preparation of 4- (4-chlorophenyl) -15- (4,4-difluorobut-3-enylthio) —1,2,3-thiadiazole (Compound No. 1-15) Preparation of sodium methoxide. 5 N methanol solution 10 ml at room temperature, {{4- (4-chlorophenyl) -1,2,3-thiadiazole 5-yl} thio} methyl propionate 1.57 g (5 mmol) Was added dropwise. After stirring for 1 hour, the reaction mixture was concentrated under reduced pressure, the residue was dissolved in 10 ml of THF, and 1.34 g (5 mmol) of 4-bromo-1,4,4-difluorobutyl-1-methanesulfonate was added at room temperature. Was added dropwise. After reacting at room temperature for 10 hours, ethyl acetate was added, and the insoluble matter was filtered off. The solvent was distilled off from the filtrate, the residue was dissolved in 10 ml of THF, 1.07 g (7 mmol) of DBU was added, and the mixture was reacted under reflux for 5 hours. The reaction mixture was poured into water, extracted twice with ethyl acetate, washed once with a saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting brown liquid was purified by silica gel chromatography to obtain 1.11 g (78% yield) of the desired product as a colorless oil.

Physical properties: nD 1.6092 (21.0 ° C)

Example 2.4 of 4- (4-chloropheninole) -5- (4,4-difluorobut-3-enylsulfinyl) -1,2,3-thiadiazole (Compound No. 1-16)

4— (4—Chloro-Feninole)-5-(4,4-Diphnoleolobutol 3-Jenie / Retio) 1-1,2,3-Thiadiazole 0.64 g (2 mimol) ) Was dissolved in 1 Oml of black mouth form, and 0.49 g (2 mmol) of m-black mouth perbenzoic acid was added in several portions under ice-cooling. After stirring at room temperature for 3 hours, the reaction mixture was poured into water, extracted twice with ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained colorless liquid was purified by silica gel column chromatography to obtain 0.61 g (yield 92%) of the desired product as a colorless oil. Physical properties: Melting point 89.1-90.4 ° C

Example 3.4 Preparation of 4-((4-chlorophenyl) -1-5- (4,4-difluorobutho-3-enylsulfonyl) —1,2,3-thiadiazol (Compound No. I-17) Using 2 equivalents of m-chloroperbenzoic acid, 0.67 g (95% yield) of the target compound was obtained as a colorless oil in the same manner as above.

Physical properties: Melting point 90.2 ~ 91.2 ° C

Example 4. Preparation of 4-methyl-1,1,2,3-thiadiazolecarboxylic acid 4,4-difluorobutou-3-enyl ester (Compound No. II-11)

 4-Bromo_4,4-difluoro-4-butanol 0.57 g (3 mmol), triethylamine 0.4 g (4 mmol) in THF solution 5 m 1 in 4-methyl-1,2,3-thiadiazolecarboxylic acid A solution of 0.49 g (3 mmol) of chloride in THF (2 ml) was added dropwise under ice cooling. After reacting at room temperature for 3 hours, the formed triethylamine hydrochloride was filtered and washed twice with THF. To the obtained filtrate, 0.61 g (4 mmol) of DBU was added and reacted under reflux for 5 hours. The reaction mixture was poured into water, extracted twice with ethyl acetate, washed once with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off. The obtained yellow liquid was purified by silica gel column chromatography to obtain 0.49 g (yield 70%) of the desired product as a colorless oil. Physical properties: nD 1.481 8 (20.5 ° C)

Example 5 Production of Ν- (4,4-diphthreo-but-3-butenyl) -1-5-phenyl-1,2,3-thiadiazole-4-carbothioamide (Compound No. III-18)

Ν- (4,4-diphnolerobutou 3-enisile) 1-5-phenyl 1,2,3 —thiadiazolu-l 4-carboxylic acid amide 0.29 g (1 mmol) of dioxane 10 m Then, 0.20 g (0.5 mmol) of Lawesson's reagent was added and reacted at 70-80 ° C for 5 hours. The solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 4: 1) to obtain 0.32 g (yield: 100%) of the target compound.

Physical properties: Paste-like

'H- NMR de one data _{[δ (CDC1 3 / TMS, (} ppm) ]

 2.4-2.6 (ra, 2H), 3.8-3.9 (m, 2H), 4.G 4.3 (m, 1), 7.3-7.5 (m, 5H),

 9.08 (bs, 1H).

Example 6. Production of 4- (4-methylphenyl) -1-5- (4,4-difluorobut-2-ene-loxy) -1,2,3-thiadiazol (Compound No. IV-1) 0.40 g (3.6 mmol) of potassium t-butoxide was suspended in 20 ml of t-butanol, 0.39 g (4 benzyl) of difluorobutul alcohol was added, and the mixture was heated to 40 ° C. . 40. After reaction with C for 30 minutes, 0.77 g (3 mmol) of 4- (4-methylphenyl) -1-bromo-1,2,3-thiadiazol was added, and the mixture was reacted at the same temperature for 5 hours. After cooling to room temperature, the solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain 0.29 g of the desired product (yield 34%).

Physical properties: nD 1.5530 (23.4 ° C)

Example 7. Preparation of 4- (2-pyridyl) -1-5- (4,4-difluorobuto-3-enylthio) 1-1,2,3-thiadiazole (Compound No. 1-80)

 Methyl {{4- (2-pyridyl) -1,2,3-thiadiazol-1-5-yl} thio} propionate in 15 ml of 0.5 M sodium methoxide in methanol at room temperature 1.50 g (5.3 mmol) of the ester were added dropwise. After stirring for 1 hour, the reaction mixture was concentrated under reduced pressure, the residue was dissolved in 15 ml of THF, and 1.42 g (5.3 mm) of 4-bromo-4,4-difluorobutyl-1-methanesulfonate was added at room temperature. ) Was added dropwise, and the mixture was reacted at room temperature for 10 hours. Then, ethyl acetate was added, and the insoluble matter was filtered. The solvent was distilled off from the filtrate, the residue was dissolved in 15 ml of THF, 1.22 g (8 mmol) of DBU was added, and the mixture was reacted under reflux for 10 hours. The reaction mixture was poured into water, extracted twice with ethyl acetate, washed once with a saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting brown liquid was purified by silica gel column chromatography to obtain 0.67 g of the target product as a colorless oil.

(44% yield).

Physical properties: nD 1.5992 (21.7 ° C)

Example 8.4 Preparation of 4- (2-furyl) -15- (4,4-difluorobut-3-enylsulfier) —1,2,3-thiadiazol (Compound No. 1-169)

Dissolve 0.89 g (3.2 mmol) of 4- (2-furyl) -5- (4,4-difluorobuto-3-enylthio) 1-1,2,3-thiadiazole in 15 ml of Cloform-form Then, under ice-cooling, add 0.80 g (3.2 mmol) of m-chloroperbenzoic acid in several portions, stir at room temperature for 5 hours, pour the reaction mixture into water, and add ethyl acetate. Extract twice, wash sequentially with saturated aqueous sodium bicarbonate and saturated saline, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and purify the resulting colorless liquid by silica gel gel chromatography to obtain the desired product. The product was obtained as a colorless oil (0.43 g, yield 43%). Thereafter, the oil crystallized.

Physical properties: Melting point 60.2-62.5 ° C

Example 9. Preparation of 4- (2-furyl) -1-5- (4,4-difluorobut-3-enylsulfonyl) -1,2,3-thiadiazole (Compound No. 1-170)

 Using 2 equivalents of m-chloroperbenzoic acid, 0.40 g (yield: 41%) of the target compound was obtained as a colorless oil in the same manner as in Example 8. Thereafter, the oil crystallized.

Physical properties: Melting point 69.5-71.0 ° C

Example 10. Production of 4- (2-pyridyl) -1-5- (3,4,4-trifluoropto-3-enylthio) -1,1,3-thiadiazol (Compound No. V-13)

 {(4- (2-Pyridyl) —1,2,3-thiadiazol-1-5-yl) thio} propionic acid methyl ester in 4 ml of 0.5 M methanol solution of sodium methoxide at room temperature 0 56 g (2 mmol) were added dropwise. After stirring for 1 hour, the reaction mixture was concentrated under reduced pressure, the residue was dissolved in 10 ml of THF, and 0.38 g (2 mmol) of 4-bromo-1,1,2-trifluoro-1-butene was added dropwise at room temperature. Time After reacting at room temperature, water was added, extracted twice with ethyl acetate, washed once with a saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting brown liquid was purified by silica gel column chromatography to obtain 0.43 g (yield: 71%) of the desired product as a colorless oil.

Physical properties: nD 1.5950 (24.8 ° C)

Reference Production Example. Production of 5-phenyl-1,2,3-thiadiazole-4 monoethyl rubonate

Dissolve 5.77 g (30 mmol) of ethyl benzoyl acetate in 30 ml of acetonitrile, cool to 0 ° C, add triethylamine 3.03 g (30 mmol), and add tosyl azide 5. 92 ml (30 mmol) of acetonitrile solution (10 ml) was slowly added dropwise. Keep the reaction temperature below 5 ° C and continue stirring for 2 hours. After that, the solvent was distilled off at a low temperature using a liquid evaporator, water was added to the residue, extracted with t-butyl methyl ether, and washed sequentially with a 7% aqueous potassium hydroxide solution, water, and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off to obtain crude α-diazobenzyl acetate ethyl ester, which was used for the next reaction as it was. The obtained crude diazobenzoyl acetic acid ethyl ester was dissolved in THF 4 Om 1, 6.07 g (15 millimol) of Lawesson's reagent was added, and the mixture was reacted under reflux for 6 hours. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate was added, extracted with ethyl acetate, and washed sequentially with water and saturated saline. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 4: 1) to give the desired product (6.30 g, yield 90). %).

Physical properties: n D 1.5 7 10 (23.4 ° C)

 The resulting 5-phenyl-1,1,2,3-thiadiazo-1-olethiol 4-carboxylate is hydrolyzed with alkali in the usual manner to give 5-phenyl-1,2,3-thiadiazo-1,4-hydroxyl. Rubonic acid was obtained and used for the preparation of derivatives.

 The following is a typical prescription example. In the formulation examples, “parts” means “parts by weight”.

Prescription example 1.

 50 parts of compounds described in Tables 1 to 5

 40 copies

 Polyoxyethylene nonylphenyl ether

 0 parts mixture with calcium alkylbenzenesulfonate

 The above are uniformly mixed and dissolved to form an emulsion.

Prescription example 2.

 3 parts of compounds described in Tables 1 to 5

 Cray powder 8 2 parts

 Diatomaceous earth powder 1 5 parts

 The above is uniformly mixed and pulverized to obtain a powder.

Prescription example 3.

 Compounds listed in Tables 1 to 5 5 parts

90 parts mixed powder of bentonite and clay 5 parts calcium lignin sulfonate

The above components are mixed uniformly, kneaded by adding an appropriate amount of water, granulated and dried to obtain granules ₍ Formulation Example 4.

 Compounds listed in Tables 1 to 5 20 parts

 Kaolin and synthetic high dispersion silicic acid 75 parts

 Polyoxyethylene nonylphenyl ether

 5 parts mixture with calcium benzylbenzenesulfonate

 The above is uniformly mixed and pulverized to obtain a wettable powder.

Test example 1. Insecticidal effect test against Japanese moth (Plutel la xylostel la)

The Chinese cabbage seedlings produced by the Japanese Conger eggs are immersed in a chemical solution diluted to 50 ppm with the drugs containing the compounds listed in Tables 1 to 5 as active ingredients for 30 seconds, air-dried, and then placed in a plastic container. It was stoppered and stored in a constant temperature room at 25 ° C. Processing investigate death number insects after 6 days, to calculate the mortality from the following equation, _c 1 ° 2 0 mice that were determined according to criteria below. Two consecutive.

 Number of eggs inoculated-number of surviving insects

Mortality (%) = X 100

 Inoculated egg count Criteria:

 A: Mortality rate 100%

 B: Death rate 90-99%

 C: Mortality rate 80-89%

 D: Mortality rate 50-79%

 Table 7 shows the results.

Test example 2. Insecticidal effect test on brown squid (Ni laparvata lugens)

A preparation containing the compounds described in Tables 1 to 5 of the present invention as active ingredients is dispersed in water and diluted to a drug solution of 500 ppm, and rice seedlings (variety: Nipponbare) are immersed in the drug solution for 30 seconds. After air-drying, they were placed in a glass test tube, inoculated with 10th instar larvae of the three-instar larvae, and then cotton-plugged and stored in a constant temperature room at 25 ° C. Eight days after the inoculation, the number of live and dead insects was examined, and the mortality was calculated by the following formula. Untreated plot survival rate-treated plot survival rate

 Corrected mortality (%) = X100

 Untreated plot survival rate Survival rate-number of surviving insects / inoculated insects.

 Table 7 shows the results.

Test Example 3. Insecticidal effect test on Namihadani (Tetranychus urticae)

Filled with water in a plastic power-up diameter 8 _c m, a lid with holes having a diameter of 1 cm, place the filter paper cuts part on the lid, while suspended from the lid in water The filter paper was kept moist due to capillary action. A leaf of 2 cm in diameter was prepared from the primary leaves of the kidney beans (variety: top crop), and 10 female adults were inoculated. Place the leaf disk on the filter paper, and uniformly spray a chemical solution 5 Om 〖diluted with the chemicals containing the compounds listed in Tables 1 to 5 to 50 ppm on a turntable and then spray 25 ° C. The sample was placed in the constant temperature room of C. Two days after drug treatment, the numbers of abnormal insects and dead insects were investigated, and the ratios of abnormal and dead insects were calculated according to the following formula, and judged according to the same criteria as in Test Example 1. Two consecutive. Abnormal and dead insect count

 Mortality (%) = X 100

 Table 7 shows the results.

Test example 4. Insecticidal effect test on Satsuma Moneko-Senyu (Meloidogyne incognita)

 A chemical solution prepared by diluting a compound containing the compounds shown in Tables 1 to 5 to 50 ppm with water is irrigated into the seedlings of the seedlings of corn soybeans grown in pots in a greenhouse. Inoculated with a water suspension of sweet potato nematode (Nematoda ca. 500 / m1) in the treated and untreated plots (soil irrigation), and placed the pot in a greenhouse at 25 ° C. Was.

 Eight days after the inoculation, the number of root nodules was examined, and compared with the number of root nodules in the untreated group, and judged according to the following criteria.

Judgment criteria

 A: No root nodule.

B: There are root nodules, but the number is clearly smaller than the untreated area. Blank: Number of nodules equal to or greater than that of the untreated area

Table 7 shows the results.

 Table 7 Compound No.Test example 1.Test example 2.Test example 3.Test example 4

1 AACA 2 AADA 3 AAAA 4 AABA 5 AA 6 AAAA 7 AACA 8 AA 9 AAAA 10 AAAA 11 AA 12 AAA 13 AAAA

Table 7 (Continued: Compound No. Test Example 1. Test Example 2. Test Example 3. Test Example 4

14 AA 15 AAAA 16 AABA 17 AA 18 AAAA 19 AAA 20 AAAA 21 AAA 22 AAA 23 AAAA 24 AADA 25 AAA 26 AAAA 27 AAAA 28 AAA 29 AAA 30 ABA 31 AAAA 32 AAAA 33 AAAA 34 ACA 35 AAAA Table 7 (Continued) Compound No. Test Example Test Example 2. Test Example 3. Test Example 4

36 AA 37 AAAA 38 AAA 39 AA 40 AA 41 AABA 42 ABA 43 AAAA 44 AAAA 45 AA 46 AAAA 47 AAA 48 ABA 49 AAAA 50 AAA 51 ADA 52 AAAA 53 ACA 54 ADA 55 A 56 AAAA 57 AAAA Table 7 (Continued) Compound No. Test Example 1. Test Example 2. Test Example 3. Test Example 4

58 AAA 59 AA 60 ACA 61 AA 62 AAA 63 AAA 64 AAA 65 AAAA 66 AAAA 67 AAA 68 AD 69 AA 70 ABA 71 AAAA 72 AAAA 73 AA 74 AA 75 AA 76 DA 77 AAA 78 ADA 79 AAAA Table 7 (Continued) Compound No. Test Example Test Example 2. Test Example 3. Test Example 4

80 AAAA 81 AAA ■ 82 AAAA 83 ABA. 84 ABA. 85 AAAA. 86 AAAA. 87 AA-88 AAAA-89 AAAA-90 AAA-91 ABA-92 AAA-93 AAAA-94 BAA-95 AAA-96 AAA-97 AAA-98 AAAA-99 AAA -100 AA -101 AA Table 7 (Continued) Compound No. Test Example 1. Test Example 2. Test Example 3. Test Example 4

-102 A A A -103 A A A A -104 A A A -105 A A A -106 A A A -107 A A A -108 A A A A -109 A A A -110 A A

 -111 A A A -112 A A -113 A

 -114 A

 -115 A

 -116 A A-117 A A -118 A

-119 AA -120 AA -121 AA -122 AA -123 AA Table 7 (continued) Compound number Test example 1. Test example 2. Test example 3. Test example 4.

-124 A D -125 A -126 A A -128 A

 -129 A A -130 D

 -131 B A -134 A

 -135 A

 -136 A

 -137 A

 -138 A A -139 D A-141 A A A -142 A A -143 A A -144 A A -145 A D

 -146 A A A -147 A A A A A -149 A

-150 A Table 7 (Continued) Compound No. Test Example Test Example 2. Test Example 3. Test Example 4

-151 A-152 A A-153 A A A

 -154 A

 -155 A

 -156 A A A -157 A -158 A A

 -159 A A A -160 A A A A -161 A A A -162 A A A -163 A A

 -164 A A A -165 A A A-166 A A

-167 AAAA -168 A-169 AAA -166 ACAI-1 AAAAI 1 2 AAA Table 7 (Continued) Compound No. Test Example 1. Test Example 2. Test Example 3. Test Example 4

II- 3 A A A II- 4 A A A II- 5 A A A II- 6 A A A II- 7 A A A A A II- 8 A A A II- 9 A A A II- 10 A A A I I- 11 A A A II- 15 A A II- 16 A

II- 17 A II- 18 C

II-19 A

II-20 A

II-22 A

II- 24 A A

 II- 26 A D

III- 1 AAA III- 2 AAA III- 3 AAA Table 7 (Continued) Compound No. Test Example Test Example 2. Test Example 3. Test Example 4

III-4 A A A III-5 A A

III-6 A A A III-7 A A A 111-12 C A III-14 A

III- 18 A A III- 19 C C

 III-20 A A

IV- 1 A A A A V- 8 D V- 9 A V- 12 A V- 15 A V- 16 A A

Claims

The scope of the claims

-General formula (I)

[Wherein, one of R, and R ₂ is -W-CH ₂ -CH ₂ -C = CF ₂

 X

(Where W is one O—, — S (O) n- (where n is an integer of 0 to 2), one C (= Z) — Y— (where Y is an oxygen atom (wherein, R ₃ is a hydrogen atom or a (C,. which - ₆₎ alkyl group) sulfur atom or NR _3. indicates, Z is an oxygen atom or a sulfur atom) or NR ₄ (wherein, R ₄ represents a hydrogen atom or a (d_ ₆ ) alkyl group.) X represents a hydrogen atom or a fluorine atom.), And the other represents a hydrogen atom, a halogen atom, A cyano group, which may be the same or different, and may have one or more substituents, and a (C ^ ₁₂ ) alkyl group, which may be the same or different, and which may have one or more substituents (C ₂ - ₈₎ alkenyl groups, the same or different and may have one or more substituents (c ₂ - ₈₎ alkynyl groups, the same or different and rather good, on one or more substituents the ring To have Even better (C ₃ - _s) cycloalkyl group, the same or may be different, one or more substituents better Ariru group which may have, may be the same or different dates, on one or more substituents the ring (D- ₆ ) alkyl group, which may be the same or different, and may have one or more substituents on the ring

) An alkyl group, which may be the same or different, and may have one or more substituents on the ring, an aryl (Ci- ₆ ) alkoxy (C ^ ₆ ) alkyl group, which may be the same or different, and A heteroaryl group which may have the same or different substituents, and which may have one or more substituents on the ring (d- ₆ ) alkyl A heteroaryloxy (d- ₆ ) alkyl group, which may be the same or different and may have one or more substituents on the ring, may be the same or different and has one or more substituents on the ring have good Heteroariru _(d-6) alkoxy (C -! ₆₎ alkyl group, in one COR _s (wherein, R ₅ is a hydrogen atom, a halogen atom, arsenic Dorokishiru group, (C. -e) alkyl group, halo (C - ₆₎ alkyl, (C ₂ - ₈₎ alkenyl, halo (C ₂ - ₈₎ alkenyl, (C ₂ - ₆₎ alkynyl, halo (C ₂ - ₆₎ alkynyl group, a substituted group Aryl groups which may have a substituent, aryl groups which may have a substituent

(C. -e) represents a heteroaryl group which may have an alkyl group or a substituent. ),

— (D- ₆ ) alkyl COR ₅ (wherein R ₅ is as defined above),

-CONR ₆ R ₆ (wherein, R ₅ is the same as above, and R ₆ is the same as R ₅ ),-(C, _ ₆ ) alkyl CONR _s R ₆ (wherein, R ₅ and R ₆ are the same as above) ), -COOR ₅ (wherein, R ₅ is the same as above.), — (Ds) alkyl COOR ₅

(. Wherein, R ₅ is as defined above), I) the alkyl O-COR ₅ (wherein, R ₅ is as defined above), one (C, -. ₆₎ alkyl S (O) n R ₅ (formula Wherein n and R _s are the same as above.

— CSNR ₅ R ₆ (wherein, R ₅ and R ₆ are the same as above;), — Si R ₅ R ₆ R ₇ (where R _s and R ₆ are the same as above, and R ₇ is hydrogen atom, a halogen atom, human de port hexyl group, ₆₎ alkyl groups, halo _(d-6) alkyl, (C ₂ - _s) § alkenyl group, halo (C ₂ - ₈₎ alkenyl, (C ₂ - ₆ ) alkynyl, halo (C ₂ - ₆₎ alkynyl group, shows the Ariru group or Ariru _(d-6) alkyl group. ), One CONR ₅ S 0 ₂ R ₆ (wherein R ₅ and R ₆ are the same as above.),-(C, _ ₆ ) alkyl CONR ₅ S 0 ₂ R ₆ (wherein, R ₅ and R ₆ wherein the same is.) one _(d-6) in the alkyl NR _S R ₆ (wherein, R ₅ and R ₆ are the same as above.) one CR ₅ = NR ₆ (wherein, R ₅ and R ₆ is the same as above.), One CR ₅ = NNR ₆ R ₈ (R ₅ and R ₆ are the same as above, and R ₈ is a (d- ₆ ) alkyl group or may be the same or different, and It indicates which may have a substituent § Li Ichiru group be), -.. CR ₅ two NO R _s (wherein, R ₅ and R ₆ are as defined above) or one CR ₅ = NOCONR ₆ R ₇ (R ₆ , R ₆ and R, are the same as above.). However, the 4-position of the 1,2,3-thiadiazole ring is a hydrogen atom, a halogen atom, (C _1-e ) an alkyl group, a halo (d_ ₄ ) alkyl group, a phenyl group or a substituted phenyl group substituted by a chlorine atom, W is -S (O) n- (where n is Same as above.) When X is shown, X excludes a fluorine atom. ]

12. A 3-thiadiazole derivative or a salt thereof represented by the formula:

2. One of R, and R ₂

-W-CH, -CH ₂ -C = CF,

 "I"

 X

(Where W is —O—, one S (O) n- (where n is an integer of 0 to 2) or one C (= Z) Y— (where Y is an oxygen atom (wherein, R ₃ is a hydrogen atom or a (C,. which - ₆₎ alkyl group) sulfur atom or NR _3.. indicates, Z is shown an oxygen atom or a sulfur atom) shows the X represents a hydrogen atom or Represents a fluorine atom), and the other is a hydrogen atom, a halogen atom, a cyano group, which may be the same or different and may have one or more substituents (Ci-) An alkyl group, which may be the same or different, may have one or more substituents, and a (C _{2 s} ) alkenyl group, which may be the same or different, may have one or more substituents ( C ₂ - ₆₎ alkynyl group, even if the same or different may, may have one or more substituents on the ring (c ₃ _ ₈₎ cycloalkyl group, which may be the same or different, 1 or more Aryl groups which may have the same or different substituents, and aryl groups which may have one or more substituents on the ring (d alkyl groups, which may be the same or different and have one or more substituents) group which may have on the ring § Riruokishi (C - ₆₎ alkyl group, which may be identical or different, may have one or more substituents on the ring Ariru _(d-6) alkoxy (d — ₆ ) an alkyl group, a heteroaryl group which may be the same or different and may have one or more substituents on the ring, may be the same or different and has one or more substituents on the ring which may Heteroariru (C, - ₆₎ alkyl group, which may be identical or different, one or more substituents which may have on the ring hetero § reel O carboxymethyl (C -! ₆₎ alkyl group, the same or different May be

A heteroaryl (C ₅ ) alkoxy (C _t _,) alkyl group which may have one or more substituents on the ring, one COR ₅ (where R ₅ is a hydrogen atom, a halogen atom, a hydroxyl group, ( C, — _ό ) alkyl group, halo (C _t — ₆ ) alkyl group, (C ₂ — ₈ ) Alkenyl, halo (c ₂ - ₈₎ alkenyl, (C ₂ - ₆₎ alkynyl group, a halo

Shown (C ₂ _ _e) alkynyl group, a substituent having even better Ariru group, good Heteroariru group which may have a good Ariru) alkyl group or a substituent which may have a substituent. ), A monoalkyl CO R ₅ (wherein R ₅ is as defined above),

— CONR ₅ R ₆ (wherein, R ₅ is the same as above, and R ₆ is the same as R ₅ ),-(C) alkyl CONR _s R ₆ (wherein, R ₅ and R _s are the same as above). .), -COOR, (wherein, R ₅ is as defined above), one (C, - ₆₎ alkyl COOR ₅

(Wherein, R ₅ is the same as above.), Mono (d- ₆ ) alkyl O—COR ₅ (wherein, R ₆ is the same as above.), Mono (d- ₆ ) alkyl S (O) n R ₆ (wherein, n and R ₆ have the same meanings as defined above.), _C S NR ₅ R ₆ (wherein, R ₅ and R ₆ are the same as above.), one _{S i R s R 6 R 7} ( wherein among, R ₅ and R _s is also the, R ₇ is water atom, a halogen atom, arsenic Dorokishiru group, (d-) alkyl group, halo (C _t _ ₆₎ alkyl, (C ₂ - ₈₎ shows the - ₍₆ C ₂₎ alkynyl group, Ariru group or § Li one Le (C _{1 -6)} alkyl group alkenyl group, halo (C ₂ _ ₈₎ alkenyl, (C ₂ _ ₆₎ alkynyl group, a halo. _{), -. CONR 5 S0 2} R 6 ( wherein, R ₅ and R ₆ are as defined above), one _(d-6) in the alkyl CON R ₅ S0 ₂ R ₆ (wherein, Rs and R _e in the same.) one _(Ct-6) alkyl _{NR 5 R 6 (Rs, R} 6 and R, are as defined above.) (Wherein, R ₅ and R _f same as above.) In one _{CR 5 = NR 6, - CR} 5 = NO R 6 (. Wherein, R ₅ and R ₆ are as defined above) or -CR ₆ = The 1,2,3-thiadiazol derivative or a salt thereof according to claim 1, which is represented by NOCONR ₆ R ₇ (wherein R ₅ , R ₆ and R ₇ are the same as described above).

3. One of R, and R ₂ is

-W-CH ₂ -CH ₂ -C = CF ₂

 X

(Wherein, W is 110, 1 S (O) n — (wherein n represents an integer of 0 to 2) or —COY— (Y represents an oxygen atom or a sulfur atom). X represents a hydrogen atom.) And the other is a hydrogen atom, a halogen atom, which may be the same or different, and may have one or more substituents (d-iJ Alkyl group, same or May be different, and may have one or more substituents. (C ₃ _ ₈ ) cycloalkyl groups, which may be the same or different, aryl groups which may have one or more substituents, the same or An aryloxy (d ₆ ) alkyl group which may be different and have one or more substituents; a heteroaryl group which may be the same or different and which has one or more substituents; , - ₆₎ alkyl S (O) n R ₅ (wherein, n same comb in the, R ₅ is a hydrogen atom, a halogen atom, arsenic Dorokishiru group, _(d-6) alkyl groups, halo (C, - ₆ ) alkyl group, (C _{2 8)} alkenyl group, Nono b (C _{2 8)} Aruke - le group, (C _{2 6)} alkynyl, halo (C _{2 6)} alkynyl group, Ariru group or Ari Le (d_ ₆₎ an alkyl group.) one CR ₅ = NR ₆ (R ₅ is the same comb in the, R ₆ are as R _5.) or single CR ₅ = NOR ₆ (R _s and R ₆ are Come to show the same.). 3. The 1,2,3-thiadiazole derivative or a salt thereof according to claim 2, which is represented by the following formula:

 4. A pesticidal composition comprising the 1,2,3-thiadiazol derivative or a salt thereof according to any one of claims 1 to 3 as an active ingredient.

 5. A method for using a pesticide, which comprises applying an effective amount of the pesticide according to claim 4 to a target useful plant or soil in order to control pests that damage useful plants.