JP2003034685A - Thiadiazole derivatives, agricutural and horticultural chemicals and their use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide thiadiazole derivatives having excellent insecticidal, tickcidal, germicidal and herbicidal effects. SOLUTION: The thiadiazole derivatives represented by general formula (I) [wherein, R is H, CN, NO2 , a 1-6C alkyl, a 3-6C cycloalkyl, a substituted 1-6C alkyl or 1-6C alkoxycarbonyl or the like; Y is a halogen, (halo) 1-6C alkyl, (halo) 3-6C cycloalkyl, (substituted) phenyl, (substituted) heterocyclic or the like; A is a group represented by formula (II) (wherein, X<1> to X<4> are each hydrogen, a halogen, CN, NO2 , a (halo)1-6C alkyl, (halo)3-6 cycloalkyl, (substituted) phenyl, (substituted) heterocyclic or the like; W is C or N; Q is a group represented by formula T-U (III) (wherein, T is -O-, -S-, -SO-, SO2 -, CH2 -, -N (C=O)V- (wherein, V is a (halo)1-6C alkyl, (halo)1-6C alkoxy, (substituted) phenyl, (substituted) heterocyclic or the like); U is H, a (halo)1-6C alkyl, (halo)2-6C alkenyl, (halo)2-6C alkinyl, (halo)1-6C alkylthio or the like); and Z is O or S]; an agricultural and horticultural agent containing the derivatives as an active ingredient; and a method for using the same.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a thiadiazole derivative, an agricultural and horticultural drug containing the compound as an active ingredient, and a method for using the same.

[0002]

2. Description of the Related Art JP-A-48-23935, JP-A-5-35
6-158703, JP-A-57-81467, WO99 / 47597, WO98 / 1107.
No. 3, Bioorg. Med. Chem. Lett. , Vol. 7 (4)
, P385 (1997), JP-A-8-208632, W
O94 / 04516, WO2000 / 02781
No. 9, JP-A-5-186611, J. Inst. C
hem. , 61 (3), 89 (1989), Pharmazie, 45 (1), 3
4 (1990), JP-A-60-233067, US-4.
141984, J. Econ. Entomol. , 76 (3), 3
99 (1983), DE-270488, Ukraine. Farm. Z
h. , 1995 (3), 75, Hecheng Huaxue, 2 (4), 330
(1994) and Huaxue Shiji, 16 (4), 211 (1994),
Compounds similar to the thiadiazole derivatives of the present invention are disclosed.

[0003]

DISCLOSURE OF THE INVENTION The inventors of the present invention have conducted extensive studies to develop new agricultural and horticultural chemicals, and as a result, the thiadiazole derivative represented by the general formula (I) of the present invention has not been described in the literature. The present invention has been completed by discovering that it is a novel compound and useful as an agricultural and horticultural agent, specifically, an insecticide, acaricide, fungicide, and herbicide.

[0004]

The present invention has the general formula (I)

[Chemical 3] {In the formula, R may be a hydrogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group or the same or different, C ₁ -C ₆ alkoxy group, mono C ₁ -C ₆ alkylamino group, substituted C ₁ -C having one or more substituents selected from the same or different di C ₁ -C ₆ alkylamino groups
₆ alkyl group or C ₁ -C ₆ alkoxycarbonyl group is shown.
Y is a halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkylthio group or a phenoxy group-substituted halo C ₁ -C ₆ alkyl group, C ₃ -C ₆ Cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ alkoxy group, halo C
₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆
Alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C
_1- C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkyl which may be the same or different Amino group, monohalo C ₁ -C ₆ alkylamino group, dihalo C ₁ -C ₆ alkylamino group which may be the same or different, phenyl group,

Halogen atoms, which may be the same or different,
C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₃-C₆Cyclo
Alkyl group, halo C₃-C₆Cycloalkyl group, C₁-C₆Arco
Xyl group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio
Group, halo c₁-C₆Alkylthio group, C ₁-C₆Alkyl sulfi
Nyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group, halo C₁-C₆An alkylsulfonyl group,
Mono C₁-C₆Alkylamino group, which may be the same or different
The C₁-C₆Alkylamino group, monohalo C₁-C₆Alkylami
Group or dihalo C which may be the same or different₁-C₆Al
A device having one or more substituents selected from a kylamino group.
A substituted phenyl group, a heterocyclic group or the same or different
H, halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Archi
Lu group, C₃-C₆Cycloalkyl group, halo C₃-C₆Cycloalk
Lu group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁
-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-C₆
Alkylsulfinyl group, halo C₁-C₆Alkyl sulfi
Nyl group, C₁-C₆Alkylsulfonyl group, halo C₁-C₆Archi
Lesulfonyl group, Mono C₁-C₆Alkylamino group, same or
Can be different C₁-C₆Alkylamino group, monohalo C
₁-C₆Alkylamino group or may be the same or different
Dihalo C₁-C₆One or more selected from alkylamino groups
A substituted heterocyclic group having a substituent is shown.

A is the formula (II)

[Chemical 4] (In the formula, X¹, X², X³, X^FourMay be the same or different
Hydrogen atom, halogen atom, cyano group, nitro group, C₁-C₆ 
Alkyl group, halo C₁-C₆ Alkyl group, C₃-C₆Cycloal
Kill group, halo C₃-C₆Cycloalkyl group, C₁-C₆Alkoxy
Group, halo c₁-C₆Alkoxy group, C₁-C₆Alkylthio group, ha
B C₁-C₆Alkylthio group, C₁-C₆Alkylsulfinyl
Group, halo c₁-C₆Alkylsulfinyl group, C₁-C₆Alkyl
Sulfonyl group, halo C₁-C₆Alkylsulfonyl group, mono
C₁-C₆Alkylamino group, di-C which may be the same or different₁-
C₆Alkylamino group, monohalo C₁-C₆Alkylamino
Groups, dihalo C which may be the same or different₁-C₆Alkylami
Group, phenyl group, same or different, halogen
Atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C ₆
Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Alkyl
Thio group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsul
Finyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆
Alkylsulfonyl group, halo C₁-C₆Alkylsulfonyl
Group, Mono C₁-C₆Alkylamino group, the same or different
Good di C₁-C₆Alkylamino group, monohalo C ₁-C₆Alkyl
Amino group or dihalo C which may be the same or different₁-C₆
Having one or more substituents selected from alkylamino groups
A substituted phenyl group,

Heterocyclic groups, which may be the same or different, and are halo.
Gen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁
-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Al
Kirthio group, halo C₁-C₆Alkylthio group, C₁-C₆Alkyl
Sulfinyl group, halo C₁-C₆Alkylsulfinyl group, C
₁-C₆Alkylsulfonyl group, halo C₁-C₆Alkyl sulfo
Nyl group, Mono C₁-C₆Alkylamino group, same or different
May be good C₁-C₆Alkylamino group, monohalo C₁-C₆Al
Killamino group or dihalo C which may be the same or different₁
-C₆One or more substituents selected from alkylamino groups
Having a substituted heterocyclic group, a phenoxy group or the same or different
Can be a halogen atom, C₁-C₆Alkyl group, halo C
₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Arco
Xy group, C ₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Base, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Alkyl
Sulfinyl group, C₁-C₆Alkylsulfonyl group, halo C₁-
C₆Alkylsulfonyl group, Mono C₁-C₆ Alkylamino
Groups, which may be the same or different, di C₁-C₆ Alkylamino
Group, monohalo C₁-C₆Alkylamino group or the same or
Dihalo C that may be different₁-C₆Select from alkylamino group
A substituted phenoxy group having one or more substituents
However, W represents a carbon atom or a nitrogen atom.

Q is the formula (III) TU (III) (In the formula, T is -O-, -S-, -SO-, -SO₂-,
-CH₂-Or-N ((C = O) V)-(wherein V is C₁-C
₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo c₁-C₆Alkoxy group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C₁-C₆Alkylamino
Group, monohalo C₁-C₆Alkylamino group, same or different
May be dihalo C₁-C₆Alkylamino group, C₁-C₆Arcoki
C₁-C₆Alkyl group, halo C₁-C₆Alkoxy C₁-C₆Archi
Lu group, C₁-C₆Alkylthio C₁-C₆Alkyl group, halo C₁-C₆
Alkylthio C₁-C₆Alkyl group, C₁-C₆Alkyl sulfi
Nil C ₁-C₆Alkyl group, halo C₁-C₆Alkylsulfini
Le C₁-C₆Alkyl group, C₁-C₆Alkylsulfonyl C₁-C₆A
Rukiru group, halo C₁-C₆Alkylsulfonyl C₁-C₆Archi
Group, phenyl group,

Halogen atoms, which may be the same or different,
C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Arco
Xyl group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio
Group, halo c₁-C₆Alkylthio group, C₁-C₆Alkyl sulfi
Nyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group, halo C₁-C₆An alkylsulfonyl group,
Mono C₁-C₆Alkylamino group, which may be the same or different
The C₁-C₆Alkylamino group, monohalo C₁-C₆Alkylami
Group or dihalo C which may be the same or different₁-C₆Al
A device having one or more substituents selected from a kylamino group.
A substituted phenyl group, a heterocyclic group, which may be the same or different,
Rogen atom, C₁-C₆Alkyl group, halo C₁-C₆An alkyl group,
C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆A
Rukiruthio group, halo C₁-C₆Alkylthio group, C₁-C₆Archi
Rusulfinyl group, halo C₁-C₆Alkylsulfinyl
Base, C₁-C₆Alkylsulfonyl group, halo C₁-C₆Alkyls
Ruphonyl group, Mono C₁-C₆ Alkylamino group, same or different
You can become C₁-C₆Alkylamino group, monohalo C₁-C₆
Alkylamino group or same or different diha
B C ₁-C₆ One or more units selected from alkylamino groups
A substituted heterocyclic group having a substituent,

Phenoxy C₁-C₆Alkyl group or same
May be different, halogen atom, C ₁-C₆Alkyl
Group, halo c₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁
-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆A
Rukiruthio group, C₁-C₆Alkylsulfinyl group, halo C₁-
C₆Alkylsulfinyl group, C₁-C₆Alkylsulfonyl
Group, halo c₁-C₆Alkylsulfonyl group, Mono C₁-C₆ Al
Killamino group, di-C which may be the same or different₁-C₆ Archi
Luamino group, monohalo C₁-C₆Alkylamino group or same
Or it may be different Dihalo C₁-C₆Alkylamino group
A substituted phenyl having on the ring one or more substituents selected from
Noxy C₁-C₆Indicates an alkyl group. ),

U is a hydrogen atom, C ₁ -C ₈ alkyl group, halo C ₁
-C ₈ alkyl group, C ₂ -C ₈ alkenyl group, halo C ₂ -C ₈ alkenyl group, C ₃ -C ₅ alkynyl group, halo C ₃ -C ₅ alkynyl group,
C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁
-C ₆ alkyl group, C ₁ -C ₆ alkylcarbonyl group, monoalkyl C ₁ -C ₆ carbamoyl group, phenyl group, which may be the same or different, halogen atom, C ₁ -C ₆ alkyl group, halo C _1-
C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -
C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, may be the same or different, di C ₁ -C ₆ alkylamino group, monohalo C ₁ -C ₆ alkylamino group, or may be the same or different, dihalo C A substituted phenyl group having one or more substituents selected from one or more selected from ₁ -C ₆ alkylamino groups, a heterocyclic group, which may be the same or different,
Halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C
₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group , Mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, monohalo C _1-
C ₆ alkylamino group or a substituted heterocyclic group having the same or different and may dihalo C ₁ -C ₆ 1 or more substituents selected from alkyl group,

Phenoxy C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, C ₁ -C ₆ alkyl group, halo C
₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, Halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C _1-
C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, may be the same or different, di C ₁ -C ₆ alkylamino group, monohalo C ₁ -C ₆ alkylamino group, or may be the same or different, dihalo C Substituted phenoxy C ₁ having on the ring one or more substituents selected from ₁ -C ₆ alkylamino groups
-C ₆ alkyl group, phenyl C ₁ -C ₆ alkyl group or the same or different, a halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, Halo c ₁
-C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C _1-
C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, diC ₁ -C ₆ alkylamino group which may be the same or different , A monohalo C ₁ -C ₆ alkylamino group or a substituted phenyl C ₁ -C ₆ alkyl group having on the ring one or more substituents selected from dihalo C ₁ -C ₆ alkylamino groups which may be the same or different. Show. ) Is shown. However, the general formula (II
When T represents -O- in I), U excludes a hydrogen atom. )
Indicates. Z represents an oxygen atom or a sulfur atom. } The thiadiazole derivative represented by these, the agricultural and horticultural chemical | medical agent which uses this compound as an active ingredient, and its usage.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION The thiadiazole derivative of the present invention
In the definition of general formula (I), “halogen atom” means chlorine.
Atom, bromine atom, iodine atom or fluorine atom,
"-" Means normal, "s-" means secondary,
"T-" indicates tertiary, and "C-" ₁-C₆Alkyl "
Is, for example, methyl, ethyl, n-propyl, i-pro
Pill, n-butyl, i-butyl, s-butyl, t-butyl
Directly, for example, n-pentyl, neopentyl, n-hexyl, etc.
Indicates a chain or branched alkyl group having 1 to 6 carbon atoms.
Then, "Hello C₁-C₆“Alkyl” may be the same or different.
Good straight or straight chain substituted by one or more halogen atoms
Indicates a branched chain alkyl group having 1 to 6 carbon atoms, for example
For example, trifluoromethyl group, difluoromethyl group, perf
Luoroethyl group, perfluoroisopropyl group, chloro
Methyl group, bromomethyl group, 1-bromoethyl group, 2,
Examples thereof include a 3-dibromopropyl group, and "C
₂-C₈"Alkenyl" means vinyl, allyl, 2-butenyl,
3-butenyl, prenyl, 4,6-octadienyl, etc.
Linear or branched carbon atom having one or more double bonds
The alkenyl group of 2 to 8 is represented by "C₃-C_FiveAlkini
"Lu" means 2-propynyl, 2-butynyl, 3-pentyl.
A straight or branched chain having one or more triple bonds such as nyl
An alkynyl group having 3 to 5 carbon atoms is shown. "Heterocycle
The `` group '' is selected from oxygen atom, sulfur atom or nitrogen atom.
5- or 6-membered heterocycle having one or more heteroatoms selected
Group, for example, pyridyl group, pyridine-N-oxide
Group, pyrimidinyl group, furyl group, tetrahydrofuryl
Group, thienyl group, tetrahydrothienyl group, tetrahydr
Lopyranyl group, tetrahydrothiopyranyl group, oxazo
Ryl group, isoxazolyl group, oxadiazolyl group, thia
Zolyl group, isothiazolyl group, thiadiazolyl group, imimi
Examples include dazolyl group, triazolyl group, pyrazolyl group, etc.
You can

The thiadiazole derivative represented by the general formula (I) of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula, and may have two or more optical isomers. Body and diastereomer may exist,
The present invention includes all optical isomers and mixtures containing them in arbitrary ratios. Further, the thiadiazole derivative represented by the general formula (I) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in the structural formula, but the present invention is not limited to these. The present invention also includes all geometric isomers of ## STR4 ## and mixtures thereof in any proportion.

Thiasia represented by the general formula (I) of the present invention
In the sol derivative, Z is an insecticide and acaricide.
An oxygen atom is preferred, R is a hydrogen atom, C₁-C₆Alkyl
Preferably Y is (halo) C₁-C₆Alkyl, is preferred,
W is preferably a carbon atom, and X is ¹Is a halogen atom, X²Is water
Elementary atom is preferred, X³Is preferably a halogen atom, and X is^Four
Is preferably a hydrogen atom, and T is preferably -O- or -S-.
U, C is₁-C₈ Alkyl group, halo C₁-C₈ Alkyl group, C₁
-C₈ Alkenyl group, halo C₁-C₈ Alkenyl groups are preferred
Yes. As a germicide, Z is preferably an oxygen atom and R is water.
Elementary atom, C₁-C₆Alkyl is preferred Y is (halo) C₁-C₆
Alkyl is preferred, W is preferably a carbon atom, X ¹~
X^FourIs hydrogen atom, halogen atom, C₁-C₆ Alkyl group is preferred
It is preferable that T is -S- or -N ((C = O) V)-.
U is hydrogen atom, C₁-C₈ Alkyl groups are preferred and V is
C₁-C₆Alkoxy C₁-C₆Alkyl group, C₁-C₆Alkoxy group
Is preferred. As a herbicide, Z is preferably an oxygen atom.
R is hydrogen atom, C₁-C₆Alkyl is preferred and Y is
B) C₁-C₆Alkyl is preferred, W is preferably a carbon atom
X ¹Is preferably a halogen atom, and X is²Is a hydrogen atom
Much better, X³Is preferably a hydrogen atom or a halogen atom, and X is^Four
Is preferably a hydrogen atom, T is —S—, —SO—, —SO
₂-Is preferred, U is C₁-C₈ Alkyl group, halo C₁-C₈ A
Rukiru group, C₁-C₈ Alkenyl group, C₃-C_Five Alkynyl group
preferable.

The thiadiazole derivative represented by the general formula (I) of the present invention can be produced, for example, by the production method illustrated below. Manufacturing method 1.

[Chemical 5] (In the formula, R, X ¹ , X ² , X ³ , X ⁴ , W, and Y are the same as above, Q is TU, and T is -O-, -S-, -SO.
_{-, ─SO 2 -, - CH} 2 - indicates, U is as defined above. ) Aromatic carboxylic acid derivative represented by the general formula (IV) and 2-aminothiadiazoles represented by the general formula (V) are reacted in the presence of an inert solvent and a base using a condensing agent or the like. Thus, the thiadiazole derivative represented by the general formula (I-1) can be produced.

Examples of the condensing agent used in this reaction include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), chlorocarbonic acid esters, and iodide 2
-Chloro-1-methylpyridinium etc. can be illustrated. Examples of the base used in this reaction include inorganic bases and organic bases.Examples of the inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, sodium hydride and potassium hydride. Alkali metal hydrides, sodium ethoxide, potassium t
Examples of alkali metal salts of alcohols such as butoxide, carbonates such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate and the like, and organic bases include, for example, triethylamine, pyridine, DBU, etc. It may be used by selecting from the range of equimolar to excess molar to the aromatic carboxylic acid derivative represented by IV).

The inert solvent used in this reaction may be any one which does not markedly hinder the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform and carbon tetrachloride. Halogenated hydrocarbons such as, chlorobenzene, dichlorobenzene and other halogenated aromatic hydrocarbons, diethyl ether,
Chain or cyclic ethers such as dioxane and tetrahydrofuran, esters such as ethyl acetate, amides such as dimethylformamide and dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and acetone, methyl ethyl ketone and the like. Examples thereof include active solvents, and these inert solvents may be used alone or
A mixture of two or more species can be used. Since this reaction is an equimolar reaction, each reaction agent may be used in an equimolar amount.
Any one of the reactants may be used in excess, the reaction temperature may be room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but is from several minutes to 48 minutes. It should be done within the range of time. After completion of the reaction, it may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by refining it by recrystallization, column chromatography or the like, if necessary.

Manufacturing method 2.

[Chemical 6] (In the formula, R, X ¹ , X ² , X ³ , X ⁴ , W, Y and Q are the same as above, and Hal represents a halogen atom.) Aromatic carboxylic acid represented by the general formula (IV) The derivative is converted into an acyl halide derivative (VI) by using a halogenating agent or the like in the presence or absence of an inert solvent, and the acyl halide derivative (VI) is isolated or not isolated to give a general compound. A thiadiazole derivative represented by the general formula (I-1) can be produced by reacting an aminothiadiazole derivative represented by the formula (V) with a base or the like in the presence of an inert solvent. it can.

1. General formula (IV) → general formula (VI). Examples of the halogenating agent used in this reaction include thionyl chloride,
Examples thereof include halogenating agents such as phosphorus oxychloride, phosphorus trichloride, phosphorus tribromide, phosphorus oxybromide, and dichloromethyl methyl ether. The amount of the aromatic hydrocarbon represented by the general formula (IV) is It may be used by appropriately selecting from the range of 1 to 100 equivalents with respect to the acid derivative. The inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction, for example, benzene, toluene,
Inert solvents such as aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, and esters such as ethyl acetate. And these inert solvents may be used alone or
A mixture of two or more species can be used. The reaction temperature can be room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be several minutes to 48 hours. After completion of the reaction, it can be isolated from the reaction system containing the desired product by a conventional method or can be used for the next reaction without isolation.

2. General formula (VI) → general formula (I-1). As the base or the inert solvent used in this reaction, the base or the inert solvent exemplified in Production Method 1 can be used. Since this reaction is an equimolar reaction, each reaction agent may be used in an equimolar amount, but either reaction agent can be used in excess, and the reaction temperature ranges from room temperature to the boiling point range of the inert solvent used. It can be carried out, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out within the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by refining it by recrystallization, column chromatography or the like, if necessary. Among the thiadiazole derivatives represented by the general formula (I) of the present invention, the compound in which Q is —SO—U or —SO ₂ —U is a compound in which Q is —S—U, according to a conventional method. For example, it can be produced by oxidizing with an oxidizing agent such as m-chloroperbenzoic acid and hydrogen peroxide.

Manufacturing method 3.

[Chemical 7] (In the formula, R, X ¹ , X ² , X ³ , X ⁴ , W, Y, and V are the same as above.) In the aromatic carboxylic acid derivative represented by the general formula (I), Q is NH (( In the case of the compound (I-2) represented by C═O) V), the nitroaromatic carboxylic acid derivative represented by the general formula (IV-1) is led to the amide body (VII), and the amide derivative (VII) The nitro group of VII) is reduced to an amine derivative (VIII) in the presence or absence of an inert solvent, and then, with an acylating agent or the like in the presence or absence of an inert solvent and in the presence of a base. It can be produced by modifying an amino group.

General formula (IV-1) → general formula (VII). This reaction can be carried out according to Production Method 1 or 2. General formula (VII) → general formula (VIII). As the reduction method that can be used in this reaction, a conventional method for reducing a nitro group, for example, a method using a metal such as iron, zinc, tin and formic acid, acetic acid, an acid such as hydrochloric acid as a reducing agent, Raney nickel under a hydrogen atmosphere, The method of using palladium, platinum, etc. can be mentioned. The inert solvent used in this reaction may be any one which does not significantly inhibit the progress of this reaction, and examples thereof include alcohols such as methanol, ethanol and 2-propanol, tetrahydrofuran, dioxane and 1,2-dimethoxyethane. Examples thereof include ethers, acids such as formic acid, acetic acid, propionic acid, hydrochloric acid, and inert solvents such as water. These inert solvents can be used alone or in admixture of two or more. The reaction temperature can be room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be several minutes to 48 hours. After completion of the reaction, it can be isolated from the reaction system containing the desired product by a conventional method or can be used for the next reaction without isolation.

General formula (VIII) → general formula (I-2). Examples of the acylating agent used in this reaction include acetyl chloride,
Examples thereof include acid halides such as benzoyl chloride, halogenated carbonic acid esters such as methyl chlorocarbonate, ethyl chlorocarbonate and phenyl chlorocarbonate. The amino group can also be modified with halogenated carbamic acids such as dimethylcarbamoyl chloride and diphenylcarbamoyl chloride, and isocyanates such as methyl isocyanate, ethyl isocyanate and phenyl isocyanate. Examples of the base used in this reaction include inorganic bases and organic bases.Examples of the inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, sodium hydride and potassium hydride. Alkali metal salts of alcohols such as alkali metal hydrides, sodium ethoxide and potassium t-butoxide,
Examples of carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and the like, and organic bases include, for example, triethylamine, pyridine, DBU and the like. The inert solvent used in this reaction may be any one that does not significantly hinder the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride,
Halogenated hydrocarbons such as chloroform and carbon tetrachloride,
Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, tetrahydrofuran, dioxane, 1,
Examples thereof include inert solvents such as ethers such as 2-dimethoxyethane and esters such as ethyl acetate. These inert solvents can be used alone or in combination of two or more kinds.

Since this reaction is an equimolar reaction, it is sufficient to use each of the reactants in an equimolar amount. However, any one of the reactants can be used in excess, and the reaction temperature is from room temperature to the inert solvent used. It can be carried out in the boiling range, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out within the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by refining it by recrystallization, column chromatography or the like, if necessary. The aromatic carboxylic acid derivative represented by the general formula (IV) can be produced according to a conventional method or a known method, for example, the method shown below.

Manufacturing method 4.

[Chemical 8] (In the formula, X ¹ , X ² , X ³ , X ⁴ , W, and U are the same as above.) Of the aromatic carboxylic acid derivatives represented by the general formula (IV), a compound in which Q is OU ( IV-3) is a conventional method, for example,
The hydroxycarboxylic acid derivative (IV-2) is esterified by heating in an alcohol solvent such as ethanol in the presence of an acid catalyst such as sulfuric acid and borane trifluoride diethyl etherate, and the ester form (IX) is converted into, for example, a base. Produced by treating with an alkyl halide in the presence or by an Mitsunobu reaction to give an ether form (IX-1) and hydrolyzing the ether form (IX-1) using a conventional method, for example, sodium hydroxide. can do.

Manufacturing Method 5.

[Chemical 9] (In the formula, X ¹ , X ² , X ³ , X ⁴ , W and U are the same as the above.) Among the aromatic carboxylic acid derivatives represented by the general formula (IV), a compound in which Q is SU ( IV-5) is, for example, a disulfide derivative (X ), Reduction to a thiol by a conventional method, alkylation by various alkylation methods, and hydrolysis followed by production.

Manufacturing method 6.

[Chemical 10] (In the formula, X ¹ , X ² , X ³ , X ⁴ , W and U are the same as the above.) Further, among the aromatic carboxylic acid derivatives represented by the general formula (IV), Q is a compound represented by SU. As an alternative to (IV-5), for example, a known method (J.Org.Chem., 31 , 3980 (196) of a hydroxycarboxylic acid derivative represented by the general formula (IX) is used.
6)) lead to thionocarbamate form (XI),
It can be produced by hydrolyzing via rearrangement to a thiol carbamate body (XII), further alkylating by various alkylating methods, and then hydrolyzing. The aminothiadiazole derivative represented by the general formula (V) can be synthesized according to a known method (J. Het. Chem., 3 , 336 (1966)).

Representative compounds of the present invention are shown in Tables 1 to 5 below, but the present invention is not limited thereto. In the table, “c-Pr” is a cyclopropyl group, “c-Pen” is a cyclopentyl group, and “c-He”.
“X” is a cyclohexyl group, “Ph” is a phenyl group,
"Pyd" represents a pyridyl group, "Pyz" represents a pyrazolyl group, and "Thi" represents a thienyl group.

General formula (I-3)

[Table 1]

[0031]

[Table 2]

[0032]

[Table 3]

[0033]

[Table 4]

[0034]

[Table 5]

General formula (I-4)

[Table 6]

General formula (I-5)

[Table 7]

[0037]

[Table 8]

[0038]

[Table 9]

General formula (I-6)

[Chemical 11]

[0040]

[Table 10]

[0041]

[Table 11]

General formula (I-7)

[Chemical 12]

[0043]

[Table 12]

[0044]

EXAMPLES Representative examples of the present invention will be illustrated below, but the present invention is not limited thereto. Example 1 3,5-dichloro-2-methoxy-N- (5
-Trifluoromethyl-1,3,4-thiadiazole-
Preparation of 2-yl) benzamide (Compound No. 1-22) 10.0 g of 3,5-dichlorosalicylic acid and 7.5 g of borane trifluoride diethyl etherate were dissolved in 100 ml of methanol and stirred at reflux temperature for 5 hours. After returning to room temperature, methanol was distilled off under reduced pressure, the residue was dissolved in ethyl acetate, and washed with an aqueous sodium hydrogen carbonate solution. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 4.5 g of ethyl 3,5-dichlorosalicylate. 1.0 g of ethyl 3,5-dichlorosalicylate was dissolved in 15 ml of tetrahydrofuran,
After adding 0.3 g of weight percent potassium hydroxide powder and 6.1 g of methyl iodide, the mixture was sealed with a rubber balloon and stirred at reflux temperature for 4 hours. The reaction solution was returned to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in diethyl ether and washed with water. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 3,5-dichloro-
1.0 g of ethyl 2-methoxybenzoate was obtained. 3,5-
3.4 g of ethyl dichloro-2-methoxybenzoate was dissolved in 30 ml of methanol and 10 ml of water, 1.3 g of 85 weight percent potassium hydroxide was added, and the mixture was stirred for 1 hour. Methanol was distilled off under reduced pressure, the residue was dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by adding a few drops of concentrated sulfuric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 3,5
-3.7 g of dichloro-2-methoxybenzoic acid were obtained. ¹ H-NMR (CDCl ₃ / TMS, δ value): 4.06 ppm (s, 3
H), 7.63 ppm (d, 1H), 8.00 ppm (d,
1H)

0.9 g of 3,5-dichloro-2-methoxybenzoic acid was dissolved in 15 ml of toluene, and 1.3 g of thionyl chloride was added. After that, the mixture was stirred at reflux temperature for 2 hours and returned to room temperature, and then the reaction mixture was concentrated under reduced pressure to obtain 0.9 g of 3,5-dichloro-2-methoxybenzoyl chloride. Two
0.3 g of -amino-5-trifluoromethyl-1,3,4-thiadiazole was dissolved in 5 ml of tetrahydrofuran, 0.2 g of triethylamine was further added, and 3,5-dichloro-2-methoxybenzoic acid chloride was added under ice-cooling. 0.
3 g was added dropwise. After dropping, the mixture was stirred for 3 hours, the reaction mixture was added to water, and the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 0.3 g of the desired product. Physical properties: melting point 116 ° C

Example 2 3-Chloro-2- (1-methylethoxy) -N- (5-trifluoromethyl-1,3,3)
Preparation of 4-thiadiazol-2-yl) benzamide (Compound No. 1-60). 0.3 g of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole was dissolved in 5 ml of tetrahydrofuran, 0.2 g of triethylamine was further added, and 3-chloro-2-isopropoxybenzoic acid chloride was added under ice-water cooling. 0.3g was dripped. After dropping, the mixture was stirred for 3 hours, the reaction mixture was added to water, and the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 0.3 g of the desired product. Physical properties: melting point 102 ° C

Example 3 Preparation of 3,5-dichloro-2-ethylthio-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) benzamide (Compound
No.3-46). 2.6 g of 3,5-dichlorosalicylic acid ethyl ester was dissolved in 30 ml of tetrahydrofuran, and the mixture was cooled with ice water to 60 g.
% Sodium hydride 0.5 g was added. The mixture was stirred at room temperature for 1 hour, then 1.4 g of N, N-dimethylthiocarbamoyl chloride was added at room temperature, and the mixture was stirred for 3 hours. After returning the reaction solution to room temperature, it was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 3,5-dichloro-2-N, N-.
Ethyl dimethylthiocarbamoyloxybenzoate 3.7
g was obtained. ¹ H-NMR (CDCl ₃ / TMS, δ value): 1.35 ppm (t, 3
H), 3.42 ppm (s, 3H), 3.49 ppm (s,
3H), 4.36ppm (q, 2H), 7.62ppm
(D, 1H), 7.89 ppm (d, 1H) 3.7 g of ethyl 3,5-dichloro-2-N, N-dimethylthiocarbamoyloxybenzoate was heated and stirred on an oil bath at 180 ° C. for 5 hours, 3.7 g of 3,5-dichloro-2-N, N-dimethylcarbamoylthiobenzoic acid ethyl ester was obtained. ¹ H-NMR (CDCl ₃ / TMS, δ value): 1.35 ppm (t, 3
H), 3.02 ppm (brs, 3H), 3.15 ppm (b
rs, 3H), 4.34ppm (q, 2H), 7.62pp
m (d, 1H), 7.92ppm (d, 1H)

2.0 g of ethyl 3,5-dichloro-2-N, N-dimethylcarbamoylthiobenzoate was added to ethanol 3
It was dissolved in 0 ml, 0.6 g of lithium hydroxide monohydrate was added, and the mixture was stirred at reflux temperature for 3 hours. Thereafter, the temperature was returned to room temperature, 1.1 g of ethyl iodide was added, and the mixture was stirred for 1 hour. Ethanol was distilled off under reduced pressure, the residue was dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by adding concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 3,5-dichloro-2-
1.9 g of ethylthiobenzoic acid was obtained. 0.9 g of 3,5-dichloro-2-ethylthiobenzoic acid and 15 ml of toluene
And thionyl chloride (1.3 g) was added. After that, the mixture was stirred at reflux temperature for 2 hours, then returned to room temperature,
The reaction mixture was concentrated under reduced pressure to obtain 0.9 g of 3,5-dichloro-2-ethylthiobenzoic acid chloride. 2-amino-5
-Trifluoromethyl-1,3,4-thiadiazole 0.6 g was dissolved in tetrahydrofuran 5 ml, triethylamine 0.4 g was added, and 3,5-dichloro-2-ethylthiobenzoic acid chloride 0.9 g was added under ice-water cooling. Dropped. After dropping, the mixture was stirred for 3 hours, the reaction mixture was added to water, and the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 0.2 g of the desired product. Physical properties: melting point 101 ° C

Example 4 3-Bromo-2-methylsulfinyl-N- (5-trifluoromethyl-1,3,4-
Production of thiadiazol-2-yl) benzamide (Compound No. 3-28) 0.6 g of 3-bromo-2-methylthio-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) benzamide Was dissolved in 5 ml of chloroform, and 0.1 g of metachloroperbenzoic acid was added under cooling with ice water. After that, the mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was added to ice water, and sodium bicarbonate water was further added to make the mixture alkaline, and then extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 0.2 g of the desired product. Physical properties: melting point 169 ° C

Example 5 Preparation of 3-bromo-2-methylsulfonyl-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) benzamide (compound
No.3-29) 0.6 g of 3-bromo-2-methylsulfinyl-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) benzamide was dissolved in 5 ml of chloroform and cooled with ice water. Was added with 0.1 g of metachloroperbenzoic acid. After that, the mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was added to ice water, and sodium bicarbonate water was further added to make the mixture alkaline, and then extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 0.2 g of the desired product. Physical properties: melting point 198 ° C

Example 6 Preparation of 2-ethoxycarbonylamino-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) benzamide (Compound No.
4-18) 2-Amino-5-trifluoromethyl-1,3,4-thiadiazole (0.9 g) was dissolved in tetrahydrofuran (15 ml), pyridine (0.4 g) was added, and the mixture was cooled with ice water to give 2-.
1.0 g of nitrobenzoic acid chloride was added dropwise. After dropping 3
After stirring for an hour, the reaction mixture was added to water, and the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue, which was purified by silica gel column chromatography to give 2-nitro-N- (5-trifluoromethyl-1,3,4). 1.7 g of thiadiazol-2-yl) benzamide were obtained.
2-nitro-N- (5-trifluoromethyl-1,3,3
4-thiadiazol-2-yl) benzamide 1.7 g
20 ml of acetic acid was added to 1.5 g of iron powder, and then 6
The mixture was heated to 0 ° C. and stirred for 1 hour. Then, the temperature was returned to room temperature, 30 ml of ethyl acetate was added to the reaction mixture, and the mixture was stirred. The insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure, and the obtained crystals were washed with ethanol and treated with 2-amino-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl). 1.0 g of benzamide was obtained. Physical properties: melting point 249 ° C. ¹ H-NMR (DMSO-d6 / TMS, δ value): 6.59 ppm (t,
1H), 6.82ppm (dd, 1H), 7.32ppm
(T, 3H), 7.92ppm (dd, 3H), 8.90p
0.3 g of pm (brs, 2H) 2-amino-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) benzamide was dissolved in 10 ml of tetrahydrofuran, and 0.1 g of triethylamine was added, 0.1 g of ethyl chloroformate was added dropwise while cooling with ice water. At room temperature after dropping 3
After stirring for an hour, the reaction mixture was added to water and the desired product was extracted with ethyl acetate.The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue, which was purified by silica gel column chromatography. 0.1 g of the desired product was obtained. Physical properties: melting point 227 ° C

Example 7 2- (3-Methylbutyl) -N
Preparation of-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl) benzamide (Compound No. 5-
4). 0.5 g of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole was dissolved in 5 ml of tetrahydrofuran, 0.3 g of triethylamine was added, and 2- (3-methylbutyl) benzoic acid chloride was added under ice-cooling. .6g
Was dripped. After dropping, the mixture was stirred for 3 hours, the reaction mixture was added to water, and the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 0.3 g of the desired product. Physical properties: melting point 121 ° C. The thiadiazole derivative represented by the general formula (I) of the present invention exhibits pest control activity, for example, insecticidal activity, acaricidal activity, bactericidal activity, herbicidal activity, and can be used as an agricultural / horticultural agent. it can.

Agro-horticultural agent containing the thiadiazole derivative represented by the general formula (I) of the present invention as an active ingredient,
Especially agricultural and horticultural insecticides or acaricides are paddy rice, fruit trees, vegetables,
It is suitable for pest control such as agricultural, forestry, horticulture, storage pests, sanitary pests, nematodes, etc. that damage other crops and flowers. For example, apple cockroach beetle (Adoxophyes orana)
fasciata), Spodoptera litura (Adoxophyes s)
p.), apple coconut oyster (Grapholita inopinata), nasihime shinobi (Grapholita molesta), bean candy squid (Leguminivora glycinivorella), kuwahamaki (Ole)
threutes mori), Chanohosuga (Caloptilia thevivor)
a), apple hosogah (Caloptilia zachrysa), quinmon hosogah (Phyllonorycter ringoniella), and nashihosuga (S
pulerrina astaurota), Pieris rapae (Piers rapae)
crucivora), Helicoverpa armigera (Heliothis sp.), codling moth (Laspey resia pomonella), diamondback moth (Plutella)
xylostella), apple clover (Argyresthia conj)
ugella), peach squid (Carposina niponensis), long-spotted squid (Chilo suppressalis), cobno squid (Cnaph)
alocrocis medinalis), Chamadara meiga (Ephestia e)
lutella), Kwanomaiga (Glyphodes pyloalis), Sankamaiga (Scirpophaga incertulas),

Parrotara guttata,
Armyworm (Pseudaletia separata), rice armyworm (Ses
amia inferens), Spodoptera litura (Spodoptera litura)
, Lepidopteran pests such as Spodoptera egigua, Spodoptera egigua, and Macrosteles fascifron
s), leafhopper (Nephotettix cincticeps), brown planthopper (Nilaparvata lugens), sedge planthopper (S
ogatella furcifera), orange lice (Diaphorina c)
itri), grape whitefly (Aleurolobus taonabae), tobacco whitefly (Bemisia tabaci), whitefly whitefly (Trialeurodes vaporariorum), black radish aphid (Lipaphis erysimi), green peach aphid (Myz)
us persicae), weevil (Ceroplastes ceriferus)
, Orange worm (Pulvinaria aurantii),
Hemoptera insect pests such as the mandarin orange scale bug (Pseudaonidiaduplex), the pear insect scale bug (Comstockaspis perniciosa), and the field insect scale bug (Unaspis yanonensis).
onica), tobacco beetle (Lasioderma serricorne)
,

Japanese platypus (Lyctus brunneus),
Red-tailed Ladybird (Epilachna vigintiotopuncta
ta), adzuki bean weevil (Callosobruchus chinensis), green weevil (Listroderes costirostris), weevil (Sitophilus zeamais), weevil (Anthono)
mus gradis gradis), rice weevil (Lissorhoptru)
soryzophilus), corn rootworm (Aulacophora femoralis)
, Oedema oryzae, Phyllotreta striolata, Pine beetle (T
omicus piniperda), Colorado potato beetle (Leptin
otarsa decemlineata), Mexican bean beetle (E
pilachna varivestis), Corn rootworms (Diabro
tica sp.) and other beetle pests such as Dacus (Zeugod
acus) cucurbitae), the fruit fly (Dacus (Bactroce
ra) dorsalis), rice leaf fly (Agromyza oryzae)
, Onion fly (Delia antiqua), sandfly (Dalia
platura), soybean fly (Asphondylis sp.),
Housefly (Musca domestica), Culex pip
Diptera pests such as iens pipiens), Minacarpus nebulae (Pratylenchus coffeae), potato cyst nematode (Glabodera rostchiensis),

Root-knot nematode (Meloidogyne sp.),
Citrus unshiu (Tylenchulus semipenetrans),
Panicchus citr (Paneonychus citr)
i), apple spider mite (Panonychus ulmi), spider mites (Tetranychus cinnabarinus), kanzawa spider mites (Tet
ranychus kanzawai Kishida)
s urticae Koch), Acaphylla the
ae), citrus red mite (Aculops pelekassi), green rust mite (Calacarus carinatus), pear mite (E
It has a strong insecticidal effect against pests such as pitrimerus pyri).

Agro-horticultural agent containing the thiadiazole derivative represented by the general formula (I) of the present invention as an active ingredient,
In particular, agricultural and horticultural fungicides are roughly classified into filamentous fungal diseases, for example, defective fungi (for example, Botrytis (Botritis)).
ytis) genus disease, Helminthospori
um), Fusarium, Septoria, Cercospora, Pyricularia, Alternaria, Basidiomycetes (eg Hemileia) Genus disease, Rhizoctonia
Genus diseases, Puccinia diseases, etc., ascomycetes (eg Venturia diseases, Podosphaera diseases, Erysiphe)
Genus disease, Monilinia genus disease, Unsinula genus disease, etc., and other fungi (for example, Ascochyta genus disease, Phoma genus disease, Pythium genus disease, Corticium (Cor)
ticium), Pyrenophora (Pyrenophora, etc.) and the like can be used for controlling diseases and the like.

Examples of individual diseases include rice blast (Pyricularia oryzae) and rice blight (Rhizoctonia s).
olani), rice sesame leaf blight (Cochiobolus miyabeanus),
Rhizopus chinensis, Pythium gram
inicola, Fusarium graminicola, Fusarium roseum, Mu
cor sp., Phoma sp., Tricoderma sp.), rice scabanae disease (Gibberella fujikuroi), barley and wheat powdery mildew (Erysiphe graminis), and cucumber powdery mildew (Sphaerotheca fuliginea) and other host plants. Powdery mildew of Pseudoce
rcosporella herpotrichoides), wheat, etc.
rocystis tritici), barley and wheat (Fusarium univale, Pythium iwayamai, Typhla ishik)
ariensis, Sclerotinia borealis), oat crown rust (Puccinia coronata) and other plant rust, cucumber, strawberry and other gray mold (Botrytis cinerea), tomato, cabbage and other sclerotinia sclerotioru
m), potato, tomato, etc. (Phytophthora infes
tans) and other plant epidemics, cucumber downy mildew (Pseudoper
onospora cubensis), downy mildew (Plasmopara vitic)
Downy mildew of various plants such as ola), and apple scab (Venturi)
a inaequalis), Apple leaf spot disease (Alternariamali)
, Pear black spot (Alternaria kikuchiana), citrus black spot (Diaporthe citri), citrus scab (E)
lsinoe fawcetti), sugar beet leaf spot (Cercosporabetico)
la), peanut leaf spot (Cercospora arachidicola)
, Peanut black spot (Cercospora personata), Wheat leaf blight (Septoria tritici), Wheat wilt (Septoria
nodorum), barley cloud disease (Rhynchosporium secali
s), wheat linseed scab (Tilletia caries), leaf rot (Rhizoctonia solani) of turf, and dollar spot disease (Sclerotinia homoeocarpa) of turf.

Agro-horticultural agent containing the thiadiazole derivative represented by the general formula (I) of the present invention as an active ingredient,
Especially herbicide for agriculture and gardening is, for example, barnyard grass (1st year Gramineae,
Paddy field weeds), Tamaya periwinkle (Cyperaceae 1st year grass, paddy field weeds), Pine scabbard (Cyperaceae perennial grass, swamps, canals, paddy fields, paddy field perennial weeds), Cucurbitaceae (Odaka family, paddy field, wetland) , Perennial herb that occurs in ditches), Firefly (perennial perennial grass, occurring in paddy fields, wetlands, and ditches), Scutellaria baicalensis (weeds in grasses, paddy fields, occurring in low swamps), oats (perennial grass, flatland,
Occurring in wastelands and fields, mugwort (Asteraceae perennial grass, mountains,
Occurrence in the field), Betula communis (1st grass of grass family, field, severely damaging grass in orchard), Rumex japonicum (perennial of Polygonaceae family, field, occurring at roadside), Kogomegayasuri (1st year grass of Cyperaceae, Amaranthaceae 1) Annual grasses, vacant lots, roadsides, fields, spruce (Asteraceae 1st year grass, upland field weeds), Abutilon (Mallow family 1st year grass, field land weeds), Pleurotus dwarf (Convolvulaceae 1st year grass) , Paddy field, field, orchard, wetland, etc., etc., Prunus vulgaris (1st to 2nd year grass, phytograss in field), Yaemgra (Rubiaceae 1st year grass, field, horticultural plant) It is useful for weeding annual and perennial weeds.

The agricultural and horticultural agents containing the thiadiazole derivative represented by the general formula (I) of the present invention as an active ingredient, especially agricultural and horticultural insecticides, acaricides, fungicides and herbicides are paddy field crops,
Upland crops, fruit trees, vegetables, since it has a remarkable control effect against the above-mentioned pests, diseases, weeds that damage other crops and flowers, etc., in accordance with the time when the occurrence of pests, diseases, weeds is predicted, Pests, diseases, weeds before or at the time of occurrence is confirmed paddy fields, fields, fruit trees, vegetables, other crops, seeds such as flowers, paddy water, foliage or soil for treating agricultural and horticultural use of the present invention. The desired effects of insecticides, acaricides, fungicides, and herbicides are exhibited.

The agricultural and horticultural chemicals of the present invention are generally used by formulating them into a convenient shape according to a conventional method for agricultural chemicals. That is, the thiadiazole derivative represented by the general formula (I) is dissolved, separated, suspended, mixed or impregnated by mixing these in an appropriate inert carrier or, if necessary, an auxiliary agent in an appropriate ratio. It may be adsorbed or adhered to be used in a suitable dosage form such as suspensions, emulsions, solutions, wettable powders, wettable granules, granules, powders, tablets and packs.

The inert carrier which can be used in the present invention may be either solid or liquid, and examples of the material which can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, sawdust powder, Tobacco stem powder, walnut shell powder, bran, fibrous powder, residue after extraction of plant extracts, synthetic polymers such as ground synthetic resins, clays (eg kaolin, bentonite, acid clay), talcs (eg talc, pyrophyllite) Etc.), silica {for example, diatomaceous earth, silica sand, mica, white carbon (Synthetic highly dispersed silicic acid also called hydrous fine powder silicon, hydrous silicic acid, and some products contain calcium silicate as a main component)}, activated carbon, sulfur powder , Pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, calcium carbonate, inorganic mineral powder such as calcium phosphate, polyethylene, polypropylene Plastic carriers such as polyvinylidene chloride, ammonium sulfate, ammonium phosphate, ammonium nitrate, can be mentioned urea, fertilizer salts depreciation etc., compost and the like, which are used alone or in the form of a mixture of two or more.

The material which can be used as a liquid carrier is selected from those having solvent ability per se and those having no solvent ability but capable of dispersing the active ingredient compound with the aid of an auxiliary agent. Typical examples of the carrier include the following, which are used alone or in the form of a mixture of two or more kinds, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones. (For example, acetone, methyl ethyl ketone, methyl isobutyl ketone,
Diisobutyl ketone, cyclohexanone, etc.), ethers (eg ethyl ether, dioxane, cellosolve,
Dipropyl ether, tetrahydrofuran etc.), aliphatic hydrocarbons (eg kerosene, mineral oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, alkylnaphthalene etc.), halogenated hydrocarbons (eg dichloroethane) , Chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate etc.), amides (eg dimethylformamide, diethylformamide, dimethylacetamide etc.) , Nitriles (for example, acetonitrile), dimethyl sulfoxides, and the like.

As the other auxiliary agents, there may be mentioned the representative auxiliary agents exemplified below. These auxiliary agents are used depending on the purpose, and may be used alone or in some cases in combination of two or more kinds of auxiliary agents. However, in some cases it is also possible to use no adjuvant at all. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compound, for example polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene. Resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonic acid condensate,
Examples thereof include surfactants such as lignin sulfonate and higher alcohol sulfate. In addition, for the purpose of stabilizing the dispersion of active ingredient compounds, adhering and / or binding, auxiliary agents exemplified below can be used, for example, casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl. Auxiliary agents such as alcohol, pine oil, bran oil, bentonite, lignin sulfonate and the like can also be used.

The following auxiliary agents may be used for improving the fluidity of the solid product, for example, waxes, stearates, alkyl phosphates and the like. As a deflocculant for a suspending product, an auxiliary agent such as a naphthalenesulfonic acid condensate or a condensed phosphate can be used. As the defoaming agent, for example, an auxiliary agent such as silicone oil can be used. As preservatives, 1, 2
-Benzisothiazolin-3-one, parachlorometaxylenol, butyl paraoxybenzoate and the like can also be added. Further, if necessary, a functional spreader, an activity enhancer such as a metabolic degradation inhibitor such as piperonyl butoxide, an antifreezing agent such as propylene glycol, an antioxidant such as BHT, an ultraviolet absorber and the like are added. Agents can also be added. The compounding ratio of the active ingredient compound can be adjusted according to need, and is 0.
It may be appropriately selected from the range of 01 to 90 parts by weight and used, for example, 0.01 to 50% by weight in the case of powder or granules, and 0.01 to 5% in the case of emulsion or wettable powder.
0 wt% is suitable. The agricultural and horticultural insecticides, acaricides, fungicides, and herbicides of the present invention are used for controlling various pests, diseases, weeds as they are, or appropriately diluted with water or the like, or for controlling pests in a suspended form. The effective amount may be applied to the crops where the pests, diseases and weeds are predicted to occur or the places where the occurrence is not preferable and used.

The amount of the agricultural or horticultural agent of the present invention to be used depends on various factors such as purpose, target pest, growth condition of crop, pest, disease, tendency of weeds, weather, environmental conditions, dosage form, application method and application. 0.001 g to 10 k per 10 are as an active ingredient compound, although it varies depending on the location, application period, etc.
g, preferably 0.01 g to 1 kg may be appropriately selected according to the purpose. The agricultural and horticultural agent of the present invention is a pesticide to be controlled, disease, weeds, other agricultural and horticultural insecticides, acaricides and nematicides for the purpose of expanding the control period or for the purpose of reducing the dosage. It is also possible to use it as a mixture with a fungicide, a herbicide, a biopesticide or the like, or it can be used as a mixture with a plant growth regulator, fertilizer or the like depending on the use scene. Other agricultural and horticultural insecticides used for such purposes, acaricides, nematicides include, for example, ethione, trichlorfon, methamidophos, acephate, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, formothion, mecarbam, bamidthione,
Thiomethone, disulfoton, oxydeprophos, nared, methyl parathion, fenitrothion, cyanophos, propaphos,

Phenthion, prothiophos, profenophos, isofenphos, temephos, fentoate, dimethylvinphos, chlorfevinphos, tetrachlorbinphos, hoxime, isoxathion, pyraclophos, metidathione, chloropyrifos, chlorpyrifos-methyl, pyridafenthion, diazinon, pyrimiphos-methyl, fosalon. , Phosmet, dioxabenzophos, quinalphos, terbufos, etoprophos, kazusaphos, mesulfenphos, DPS (NK-0795), phosphocarb, fenamiphos, isamidophos, fostiazate, isazophos, enaprophos, fenthion, fostiethane, diclofenthion, thionazine, sulprofos, fensulfone. , Diamidaphos, pyrethrin, allethrin, prala Phosphorus, resmethrin, permethrin, tefluthrin, bifenthrin, fenpropathrin, cypermethrin, alpha-cypermethrin, cyhalothrin, lambda-cyhalothrin, deltamethrin,
Acrinathrin,

Fenvalerate, esfenvalerate, flucitrinate, fluvalinate, cycloprotoline, etofenprox, halfenprox,
Silafluofen, flucitrinate, fluvalinate, mesomil, oxamyl, thiodicarb, aldicarb, alanicalub, cartap, metolcarb, xilicarb, propoxur, phenoxycarb, fenobucarb, etiophencarb, phenothiocarb, bifenazeto, BPMC, carbaryl, carmifurfan, carbofuran, carbofuran. Fratiocarb, benfuracarb, aldoxicarb, diafenthiuron, diflubenzuron, teflubenzuron, hexaflumuron, novalron, rufenuron, flufenoxuron,
Chlorfluazuron, fenbutatin oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, methoprene, hydroprene, vinapacryl, amitraz, dicofol, quelsen, chlorbenzilate, phenisobromolate, tetradiphone, bensultap, benzomate, Tebufenozide, methoxyphenozide,

Chromafenozide, propargit, acequinocyl, endosulfan, diophenolane, chlorfenapyr, fenpyroximate, tolfenpyrad, fipronil, tebufenpyrad, triazamate, etoxazole, hexithiazox, nicotine sulfate, nitenpyram, acetamiprid, thiacloprid,
Imidacloprid, thiamethoxam, clothianidin,
Nizinotefuran, fluazinam, pyriproxyfen,
Hydramethylnon, pyrimidifen, pyridaben, cyromazine, TPIC (tripropyl isocyanurate),
Pymetrozine, clofentezine, buprofezin, thiocyclam, fenazaquin, quinomethionate, indoxacarb, polynactin complex, milbemectin, abamectin, emamectin benzoate, spinosad, BT (Bacillus thuringiensis), azadirachtin, rotenone, hydroxypropyl starch, Agricultural and horticultural insecticides such as levamisole hydrochloride, metam sodium, morantel tartrate, dazomet, trichlamide, bastria, monacrosporium fimatopagum, acaricides and nematicides can be exemplified, and agriculture used for the same purpose. As a gardening fungicide,

For example, sulfur, lime-sulfur mixture, basic copper sulfate, iprobenphos, edifenphos, tolclofos-methyl, thiram, polycarbamate, zineb, manzeb, mancozeb, propineb, thiophanate, thiophanatemethyl, benomyl, iminoctadine acetate, iminoctadine Albesylate, mepronil, flutolanil, penciclone, flametopyr, tifluzamide, metalaxyl, oxadixyl, carpropamide, diclofluanid, fursulfamide, chlorothalonil, kresoxim methyl, phenoxanil (NNF-942).
5), hymexazole, ecromezole, fluorimide, procymidone, vinclozolin, iprodione, triadimefon, triflumizole, bitertanol, triflumizole, ipconazole, fluconazole, propiconazole, difenoconazole, microbutanil, tetraconazole, hexaconazole, tebuconazole, tebuconazole.

Imibenconazole, prochloraz, pefurazoate, cyproconazole, isoprothiolane, phenalimol, pyrimethanil, mepanipyrim, pyrifenox, fluazinam, triforin, diclomedine, azoxystrobin, thiadiazine, captan, probenazole, acibenzofural-S-methyl ( CGA-2
45704), fusalide, tricyclazole, pyroquilon, quinomethionate, oxolinic acid, dithianon, kasugamycin, validamycin, polyoxine,
Blasticidin, it is possible to exemplify agricultural and horticultural fungicides such as streptomycin. Similarly, as herbicides, for example, glyphosate, sulfosate, glufosinate, bialaphos, butamifos, esprocarb, prosulfocarb, bench iocarb, pyributicarb, ashram,
Linuron, Daimlon, Bensulfuron-methyl, Cyclosulfamuron, Cinosulfuron, Pyrazosulfuron-ethyl, Azimsulfuron, Imazosulfuron, Tenilchlor, Araclor, Pretilachlor, Chromeprop, Etobenzanide, Mefenacet,

Pendimethalin, bifenox, acifluofen, lactofen, cyhalofop-butyl,
Aioxynil, bromobutide, alloxydim, cetoximium, napropamide, indanophan, pyrazolate, benzophenap, pyraflufen-ethyl, imazapyr, sulfentrazone, cafenstrol, bentoxazone, oxazoazone, paraquat, diquat, pyriminobac, simazine, atrazine, dimetamethrin. , Triazifram, benfresate, furthiaset methyl, quizalofop ethyl, bentazone, calcium peroxide and the like herbicides.

Examples of biological pesticides include Nuclear polyhedrosis virus (NPV), Granulosis virus (GV), Cytoplasmic polyhedrosis virus (CPV), Insect pox virus (Entomopox) virus, EPV) and other virus preparations, Monosporium fimatopagum (Mona
crosporium phymatophagum), Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, and other microbial pesticides and trichoderma used as nematicides.
Lignolan (Trichoderma lignorum), Agrobacterium radiobactor
), Non-pathogenic Erwinia carotobora (Erwinia car
otovora), Bacillus subtilis
The same effect can be expected by mixing with a microbial pesticide used as a bactericide such as) and a biopesticide used as a herbicide such as Xanthomonas campestris.

Further, as biological pesticides, for example, honeybee wasp (Encarsia formosa), coleman bee (Ap)
hidius colemani), gypsy fly (Aphidoletes)
aphidimyza), Yellow-bellied wasp (Diglyphus isaea)
), Mosquito beetle (Dacnusa sibirica), dust mite (Phytoseiulus persimilis), Amblyseius cucumeris, and other natural creatures such as Orius sauteri, Boberia
Microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate,
(E, Z) -4,10-tetradecadienyl acetate, (Z) -8-dodecenyl acetate, (Z) -1
1-tetradecenyl = acetate, (Z) -13-icosen-10-one, (Z) -8-dodecenyl = acetate, (Z) -11-tetradecenyl = acetate,
(Z) -13-icosen-10-one, 14-methyl-
It is also possible to use it together with a pheromone agent such as 1-octadecene.

Typical formulation examples and test examples of the present invention are shown below, but the present invention is not limited thereto.
In the formulation examples, “part” means “part by weight”. Formulation Example 1. Compounds described in Tables 1 to 5 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 10 parts The above components are uniformly mixed and dissolved to obtain an emulsion. Formulation example 2. Compounds described in Tables 1 to 5 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain a powder.

[0076] Formulation example 3.   5 parts of compounds shown in Tables 1 to 5   90 parts of mixed powder of bentonite and clay   Calcium lignin sulfonate 5 parts     Mix the above uniformly, add an appropriate amount of water and knead, granulate and dry to make granules . Formulation example 4.   20 parts of compounds shown in Tables 1 to 5   Kaolin and synthetic highly dispersed silicic acid 75 parts   With polyoxyethylene nonyl phenyl ether   Mixture with calcium alkylbenzene sulfonate 5 parts     The above is uniformly mixed and pulverized to obtain a wettable powder.

Test Example 1. Diamondback moth (Plutella xylostella)
Insecticidal test against Chinese cabbage seedlings, adult adults of diamondback moth are released and laid, and 2 days after releasing, Chinese cabbage seedlings with laying eggs are shown in Tables 1 to 5
500ppm of drugs containing the compounds listed in the table as active ingredients
It was dipped in the chemical solution diluted to about 30 seconds, air-dried and then allowed to stand in a thermostatic chamber at 25 ° C. The number of hatching worms was examined 6 days after the immersion in the chemical solution. As a result, 1-41, 1-56, 3-13, 3-4
The compounds of 5, 4-7, 4-33, 5-4 showed good insecticidal activity.

Test Example 2. Namihadani (Tetranychus urti)
Mite-killing test against cae) A leaf disk having a diameter of 2 cm was prepared from green leaf, placed on a wet filter paper, and inoculated with a female adult, and then diluted to 500 ppm on a turntable.
50 ml of a drug solution containing the compound shown in the table as an active ingredient was uniformly sprayed, and after spraying, it was allowed to stand in a thermostatic chamber at 25 ° C. The number of living and dead insects was investigated 2 days after the drug treatment. As a result 1-1
3, 1-17, 1-222, 1-23, 1-24, 1-
26, 1-28, 1-29, 1-30, 1-32, 1-
34, 1-39, 1-45, 1-47, 1-49, 1-
52, 1-53, 1-55, 1-56, 1-60, 1-
65, 1-68, 1-69, 1-71, 1-73, 1-
74, 1-75, 1-76, 1-79, 1-80, 1-
83, 1-87, 1-90, 1-93, 3-6, 3-1
The compounds of 0, 3-15, 3-39, 3-46 and 3-50 showed good insecticidal activity.

Test Example 3. Herbicidal effect test on paddy field weeds before emergence. A 75 cm ² plastic pot was filled with soil (a clay loam), and 1 c of seeds of paddy weeds such as barnyard grass and firefly were planted.
At the depth of m, seeds of Azena are sown on the surface, and the water depth is 5 cm.
Was flooded. On the next day, a predetermined effective dose (3000 g / ha) of the drug containing the compounds of the present invention shown in Tables 1 to 5 prepared according to the formulation examples was diluted with water and added dropwise to the water surface. . Then, the plants were grown in a greenhouse, and 21 days after the treatment, the herbicidal effect was investigated. As a result, 3-10,
3-11, 3-12, 3-15, 3-16, 3-18,
3-27, 3-28, 3-38, 3-39, 3-46,
The compounds 3-48 and 4-12 showed good herbicidal activity.

Test Example 4 Control Test for Tomato Epidemic Disease The agents containing the compounds of the present invention shown in Tables 1 to 5 as active ingredients, which were prepared according to the formulation examples, were diluted with water to a predetermined concentration and cultivated in pots. The foliage was sprayed on tomatoes (cultivar: Ponteroza) at the 3-leaf stage. One day after spraying, Phytophthora infestans (Ph
Ytophthora infestans) was spray-inoculated with a zoosporangium suspension. Five days after the inoculation, the degree of disease on each leaf was investigated. As a result, 3-14, 3-15, 3-19, 3-20, 4-
7, 4-9, 4-10, 4-18, 4-19, 4-2
The compounds of 2, 4-23, 4-26, 4-29, 4-31 showed good bactericidal activity.

Test Example 5 Control test against apple scab disease The agents containing the compounds of the present invention shown in Tables 1 to 5 and prepared according to the formulation examples are diluted with water to a predetermined concentration and cultivated in pots. The foliage was applied to the apple seedlings (variety: Wanglin) that had been harvested. One day after spraying, apple scab (Venturia i)
Naequalis) was spray inoculated with a conidia suspension. Inoculation 2
After a week, the degree of disease on each leaf was investigated. As a result, 1-1
8, 1-22, 1-29, 1-45, 1-47, 1-4
9, 1-55, 1-60, 1-67, 1-74, 1-7
9, 1-80, 3-5, 3-6, 3-7, 3-38, 3
-46, 3-49, 3-50, 4-1, 4-18, 4-
Compounds 29 and 4-32 showed good bactericidal activity.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Masayuki Morimoto             1-28-305 Nishinoyamacho, Kawachinagano City, Osaka Prefecture (72) Inventor Shinsuke Fujioka             474-1-103 Ueharamachi, Kawachinagano City, Osaka Prefecture (72) Inventor Tsuyoshi Takemoto             1-28-402 Nishinoyama-cho, Kawachinagano City, Osaka Prefecture (72) Inventor Hiroki Mezuka             374-205 Kitamachi, Kawachinagano City, Osaka Prefecture F-term (reference) 4C036 AD08 AD22 AD27                 4H011 AA01 AB01 AC01 AC04 BA01                       BB10 BC01 BC03 BC07 BC09                       BC18 DA02 DA15 DA16 DC05                       DD03 DD04

Claims (5)

[Claims] 1. The general formula (I) [Chemical 1] {In the formula, R is a hydrogen atom, a cyano group, a nitro group, C₁-C₆A
Rukiru group, C₃-C₆Cycloalkyl group, the same or different
Also good, C₁-C₆Alkoxy group, Mono C₁-C₆Alkylamino
Groups or di-C which may be the same or different₁-C₆Alkyla
Substituted C having one or more substituents selected from mino groups₁-C
₆Alkyl group or C₁-C₆Indicates an alkoxycarbonyl group.
Y is a halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Archi
Lu group, C₁-C₆Substituted with an alkylthio group or phenoxy group
Halo C₁-C₆Alkyl group, C₃-C₆Cycloalkyl group, ha
B C₃-C₆Cycloalkyl group, C₁-C₆Alkoxy group, halo C
₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆
Alkylthio group, C₁-C₆Alkylsulfinyl group, halo C
₁-C₆Alkylsulfinyl group, C₁-C₆Alkyl sulfoni
Lu group, halo C₁-C₆Alkylsulfonyl group, Mono C₁-C₆Al
Killamino group, di-C which may be the same or different₁-C₆Archi
Luamino group, monohalo C₁-C₆Alkylamino group, same or
May be different Dihalo C₁-C₆Alkylamino group,
Nyl group, which may be the same or different, a halogen atom, C₁-C
₆Alkyl group, halo C₁-C₆Alkyl group, C₃-C₆Cycloal
Kill group, halo C₃-C₆Cycloalkyl group, C₁-C₆Alkoxy
Group, halo c₁-C₆Alkoxy group, C₁-C₆Alkylthio group, ha
B C₁-C₆Alkylthio group, C₁-C₆Alkylsulfinyl
Group, halo c₁-C₆Alkylsulfinyl group, C₁-C₆Alkyl
Sulfonyl group, halo C₁-C₆Alkylsulfonyl group, Mono C
₁-C₆Alkylamino group, di-C which may be the same or different₁-C
₆Alkylamino group, monohalo C₁-C₆Alkylamino group
May be the same or different dihalo C₁-C₆Alkyla
Substituted Fe having one or more substituents selected from mino groups
Nyl group, heterocyclic group or the same or different.
Rogen atom, C₁-C₆Alkyl group, halo C₁-C₆An alkyl group,
C₃-C₆Cycloalkyl group, halo C₃-C₆Cycloalkyl group,
C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆A
Rukiruthio group, halo C₁-C₆Alkylthio group, C₁-C₆Archi
Rusulfinyl group, halo C₁-C₆Alkylsulfinyl
Base, C₁-C₆Alkylsulfonyl group, halo C₁-C₆Alkyls
Ruphonyl group, Mono C₁-C₆Alkylamino group, same or different
You can become C ₁-C₆Alkylamino group, monohalo C₁-C₆
Alkylamino group or same or different diha
B C₁-C₆One or more substitutions selected from alkylamino groups
A substituted heterocyclic group having a group is shown. A is the formula (II) [Chemical 2] (In the formula, X¹, X², X³, X^FourMay be the same or different
Hydrogen atom, halogen atom, cyano group, nitro group, C₁-C₆ 
Alkyl group, halo C₁-C₆ Alkyl group, C₃-C₆Cycloal
Kill group, halo C₃-C₆Cycloalkyl group, C₁-C₆Alkoxy
Group, halo c₁-C₆Alkoxy group, C₁-C₆Alkylthio group, ha
B C₁-C₆Alkylthio group, C₁-C₆Alkylsulfinyl
Group, halo c₁-C₆Alkylsulfinyl group, C₁-C₆Alkyl
Sulfonyl group, halo C₁-C₆Alkylsulfonyl group, mono
C₁-C₆Alkylamino group, di-C which may be the same or different₁-
C₆Alkylamino group, monohalo C₁-C₆Alkylamino
Groups, dihalo C which may be the same or different₁-C₆Alkylami
Group, phenyl group, same or different, halogen
Atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C ₆
Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Alkyl
Thio group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsul
Finyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆
Alkylsulfonyl group, halo C₁-C₆Alkylsulfonyl
Group, Mono C₁-C₆Alkylamino group, the same or different
Good di C₁-C₆Alkylamino group, monohalo C ₁-C₆Alkyl
Amino group or dihalo C which may be the same or different₁-C₆
Having one or more substituents selected from alkylamino groups
Substituted phenyl group, heterocyclic group, same or different
H, halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Archi
Lu group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁
-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-C₆
Alkylsulfinyl group, halo C₁-C₆Alkyl sulfi
Nyl group, C₁-C₆Alkylsulfonyl group, halo C₁-C₆Archi
Lesulfonyl group, Mono C₁-C ₆Alkylamino group, same or
Can be different C₁-C₆Alkylamino group, monohalo C
₁-C₆Alkylamino group or may be the same or different
Dihalo C₁-C₆One or more selected from alkylamino groups
A substituted heterocyclic group having a substituent, a phenoxy group or the same
May be different, halogen atom, C₁-C₆Alkyl
Group, halo c₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁
-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆A
Rukiruthio group, C₁-C₆Alkylsulfinyl group, halo C₁-
C₆Alkylsulfinyl group, C₁-C₆Alkylsulfonyl
Group, halo c₁-C₆Alkylsulfonyl group, Mono C₁-C₆ Al
Killamino group, di-C which may be the same or different₁-C₆ Archi
Luamino group, monohalo C₁-C₆Alkylamino group or same
Or it may be different Dihalo C₁-C₆Alkylamino group
Substituted phenoxy having one or more substituents selected from
Represents a group, and W represents a carbon atom or a nitrogen atom. Q is the formula (III) TU (III) (In the formula, T is -O-, -S-, -SO-, -SO₂-,
-CH₂-Or-N ((C = O) V)-(wherein V is C₁-C
₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo c₁-C₆Alkoxy group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C₁-C₆Alkylamino
Group, monohalo C₁-C₆Alkylamino group, same or different
May be dihalo C₁-C₆Alkylamino group, C₁-C₆Arcoki
C₁-C₆Alkyl group, halo C₁-C₆Alkoxy C₁-C₆Archi
Lu group, C₁-C₆Alkylthio C₁-C₆Alkyl group, halo C₁-C₆
Alkylthio C₁-C₆Alkyl group, C₁-C₆Alkyl sulfi
Nil C ₁-C₆Alkyl group, halo C₁-C₆Alkylsulfini
Le C₁-C₆Alkyl group, C₁-C₆Alkylsulfonyl C₁-C₆A
Rukiru group, halo C₁-C₆Alkylsulfonyl C₁-C₆Archi
Group, phenyl group, same or different, halogen
Atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Alkyl
Thio group, halo C₁-C₆Alkylthio group, C₁-C₆Alkyls
Rufinyl group, halo C ₁-C₆Alkylsulfinyl group, C₁-
C₆Alkylsulfonyl group, halo C₁-C₆Alkyl sulfoni
Ru group, Mono C₁-C₆Alkylamino group, the same or different
Also good C₁-C₆Alkylamino group, monohalo C₁-C₆Archi
Luamino group or dihalo C which may be the same or different₁-C
₆Having one or more substituents selected from alkylamino groups
Substituted phenyl group, heterocyclic group, which may be the same or different
H, halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Archi
Lu group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁
-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-C₆
Alkylsulfinyl group, halo C₁-C₆Alkyl sulfi
Nyl group, C₁-C₆Alkylsulfonyl group, halo C₁-C₆Archi
Lesulfonyl group, Mono C₁-C₆ Alkylamino group, same or
Can be different C₁-C₆Alkylamino group, monohalo C
₁-C₆Alkylamino group or may be the same or different
Dihalo C₁-C₆ 1 or more selected from alkylamino groups
Phenoxy C, a substituted heterocyclic group having a substituent of₁-C₆Al
Kill group or may be the same or different and may be a halogen source.
Child, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆A
Lucoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylchi
O group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulf
Inyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆A
Rukylsulphonyl group, halo C₁-C₆Alkylsulfonyl
Group, Mono C₁-C₆ Alkylamino group, the same or different
Good di C₁-C₆ Alkylamino group, monohalo C₁-C₆Archi
Luamino group or dihalo C which may be the same or different₁-C
₆One or more substituents selected from alkylamino groups
Substituted phenoxy C having on₁-C₆Indicates an alkyl group. )
, U is a hydrogen atom, C₁-C₈Alkyl group, halo C₁-C₈
Alkyl group, C ₂-C₈Alkenyl group, halo C₂-C₈Alkenyl
Base, C₃-C_FiveAlkynyl group, halo C₃-C_FiveAlkynyl group, C₁-C
₆Alkoxy C₁-C₆Alkyl group, halo C₁-C₆Alkoxy C₁-
C₆Alkyl group, C₁-C₆Alkylthio C₁-C₆Alkyl group, ha
B C₁-C₆Alkylthio C₁-C₆Alkyl group, C₁-C₆Alkyl
Sulfinyl C₁-C₆Alkyl group, halo C₁-C₆Alkylsul
Finil C₁-C₆Alkyl group, C₁-C₆Alkylsulfonyl C₁
-C₆Alkyl group, halo C₁-C₆Alkylsulfonyl C₁-C₆A
Rukiru group, C₁-C₆Alkylcarbonyl group, monoalkyl C
₁-C₆Carbamoyl group, phenyl group, the same or different
Well, halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Al
Kill group, C₁-C₆Alkoxy group, halo C₁-C₆An alkoxy group,
C₁-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-C
₆Alkylsulfinyl group, halo C₁-C₆Alkyl sulfi
Nyl group, C₁-C₆Alkylsulfonyl group, halo C₁-C₆Archi
Lesulfonyl group, Mono C₁-C₆Alkylamino group, same or
Can be different C₁-C₆Alkylamino group, monohalo C
₁-C₆Alkylamino group or same or different
I Jihalo C₁-C₆One or more selected from alkylamino groups
Substituted phenyl having one or more substituents selected from
Groups, heterocyclic groups, which may be the same or different, and
Child, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆A
Lucoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylchi
O group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulf
Inyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆A
Rukylsulphonyl group, halo C₁-C₆Alkylsulfonyl
Group, Mono C₁-C₆Alkylamino group, the same or different
Good di C₁-C₆Alkylamino group, monohalo C₁-C₆Archi
Luamino group or dihalo C which may be the same or different₁-C
₆Having one or more substituents selected from alkylamino groups
Substituted heterocyclic group, phenoxy C₁-C₆Alkyl group, same
Or may be different, halogen atom, C₁-C₆Alkyl
Group, halo c₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁
-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆A
Rukiruthio group, C₁-C₆Alkylsulfinyl group, halo C₁-
C ₆Alkylsulfinyl group, C₁-C₆Alkylsulfonyl
Group, halo c₁-C₆Alkylsulfonyl group, Mono C₁-C₆ Al
Killamino group, di-C which may be the same or different₁-C₆Archi
Luamino group, monohalo C₁-C₆Alkylamino group or same
Or it may be different Dihalo C₁-C₆Alkylamino group
A substituted phenyl having on the ring one or more substituents selected from
Noxy C₁-C₆ Alkyl group, phenyl C₁-C₆ Alkyl group
May be the same or different, halogen atom, C₁-C₆
Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo c₁-C₆Alkoxy group, C₁-C₆Alkylthio group, ha
B C₁-C₆Alkylthio group, C₁-C₆Alkylsulfinyl
Group, halo c₁-C₆Alkylsulfinyl group, C₁-C₆Alkyl
Sulfonyl group, halo C₁-C₆Alkylsulfonyl group, Mono C
₁-C₆Alkylamino group, di-C which may be the same or different₁-C
₆Alkylamino group, monohalo C₁-C₆Alkylamino group
May be the same or different dihalo C₁-C₆Alkyla
A moiety having one or more substituents selected from the mino group on the ring.
Converted phenyl C₁-C₆ Indicates an alkyl group. ) Is shown. However
When T represents —O— in the general formula (III), U represents a hydrogen atom.
except. ) Is shown. Z represents an oxygen atom or a sulfur atom. }
The thiadiazole derivative represented by. 2. In the general formula (I), A, Z, R, X
¹ , X ² , X ³ , Q, U and V are the same as in claim 1, and Y
Represents a halo C ₁ -C ₆ alkyl group, W represents a carbon atom,
T is -O -, - S -, - SO -, - SO 2 -, - N
The thiadiazole derivative according to claim 1, which represents ((C = O) V)-, and X ⁴ represents a hydrogen atom. 3. An agricultural and horticultural chemical comprising the thiadiazole derivative according to claim 1 or 2 as an active ingredient. 4. The agricultural / horticultural chemical according to claim 3, wherein the agricultural / horticultural chemical is an agricultural / horticultural insecticide, an acaricide, a fungicide, or a herbicide. 5. An agricultural plant characterized by treating a target plant or soil with an effective amount of the agricultural or horticultural chemical according to claim 3 or 4 for controlling harmful insects, diseases or weeds from useful plants. How to use gardening chemicals.