JPH10152482A - 1,2,3-thiadiazole derivatives or salts thereof, agricultural and horticultural disease controlling agents and methods of using the same - Google Patents

Abstract

(57) [Summary] [Solution] General formula (I) [Wherein R ¹ is H, (halo) C ₁ -C ₄ alkyl, substituted or unsubstituted phenyl, 5 to 5 having 1 to 3 O, N or S]
A, such as a 6-membered heterocycle, is (Wherein R ² and R ³ are H, halogen, cyano, formyl,
Alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenyl, phenylcarbonyl, or R ² and R ³ together represent -O-, -S
(O) n- (n is 0 to 2), - CO- or -NR ⁸ - may also form a 3- to 7-membered ring by a good C ₂ -C ₆ alkylene group which may be interrupted by. ), B represents cyano, or an optionally substituted 5- to 6-membered heterocycle having 1 to 3 heteroatoms selected from O, N or S, and m represents 0 to 4). A 1,2,3-thiadiazole derivative or a salt thereof,
And an agricultural and horticultural disease controlling agent comprising the derivative or a salt thereof as an active ingredient, and a method for using the same. [Effect] It shows excellent control activity against blast and the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a 1,2,3-thiadiazole derivative or a salt thereof, an agricultural and horticultural disease control agent containing the compound as an active ingredient, and a method for using the same.

[0002]

BACKGROUND OF THE INVENTION With respect to 1,2,3-thiadiazoles,
Derivatives, process for preparing the same, compounds containing the compounds and having herbicidal and growth regulating effects.
JP, JP-A-3-181463, JP-A-4-234
No. 881 and Canadian Patent No. 947297 as herbicides or plant growth regulators.
JP-A-340 and JP-A-7-252242 disclose a bactericide.

[0003]

The inventors of the present invention have conducted intensive studies in order to create a novel agricultural and horticultural disease control agent. The present inventors have found that a 3-thiadiazole derivative or a salt thereof is a novel compound not described in the literature and is useful as an agricultural and horticultural disease controlling agent, and has completed the present invention.

[0004]

The present invention provides a compound represented by the general formula (I):

Embedded image Wherein R ¹ is a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C
₄ alkyl group, phenyl group, may be the same or different,
Halogen atom, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo C ₁ -C ₄ alkoxy or C ₁ -C ₄ A substituted phenyl group having 1 to 5 substituents selected from an alkoxycarbonyl group, a 5 to 6-membered heterocyclic ring having 1 to 3 oxygen atoms, nitrogen atoms or sulfur atoms, which may be the same or different, or The same or different, a halogen atom,
Cyano group, a hydroxyl group, a mercapto group, C ₁ -C ₄ alkyl group,
C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, carbonyl group, carboxyl group, carboxy C ₁ -C ₄ alkyl group,
C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group, amino group, which may be the same or different, from 1 to 2 C ₁ -C ₄ alkyl groups or phenyl groups A substituted amino group having a substituent selected, a carbamoyl group, which may be the same or different, and a substituted carbamoyl group having a substituent selected from _{1 to} 2 C ₁ -C ₄ alkyl groups or phenyl groups, carbamoyl C _1- C ₄ alkyl group or a substituted or unsubstituted carbamoyl C ₁ -C ₄ alkyl group having a substituent selected from _{1 to} 2 C ₁ -C ₄ alkyl groups or phenyl groups, which may be the same or different. It has 1 to 4 substituents, which may be the same or different, and has 5 to 6 substituents having 1 to 3 oxygen atoms, nitrogen atoms, or sulfur atoms.
A membered heterocyclic ring, wherein A is

[0005]

Embedded image (Wherein R ² and R ³ may be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a formyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ Alkylthio group,
C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, phenyl group, which may be the same or different, halogen atom, hydroxyl group , Cyano group, nitro group, C ₁ -C
₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo C ₁ -C ₄ alkoxy groups, 1 to 5 substituents selected from C ₁ -C ₄ alkoxycarbonyl group Having a substituted phenyl group, a phenylcarbonyl group, or the same or different, a halogen atom, a hydroxyl group, a cyano group, C ₁
-C ₄ alkyl group, or a C ₁ -C ₄ alkoxy from 1 to 5 substituents selected from group a substituted phenylcarbonyl group having on the ring, R ² and R ³ together -O -
, -S (O) n- (wherein, n represents an integer of 0 to 2), -CO
-Or

[0006] -NR ⁸ - (wherein, R ⁸ is a hydrogen atom, a formyl group, C ₁ -C ₈ alkyl group, halo C ₁ -C ₄ alkyl group, C ₂ -C ₄ alkenyl group, a halo
C ₂ -C ₄ alkenyl group, C ₂ -C ₄ alkynyl group, halo C ₂ -C ₄
Alkynyl group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄
Alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, carbamoyl group, which may be the same or different, C ₁ -C ₄
A substituted carbamoyl group having 1 to 2 substituents selected from an alkyl group or a phenyl group, a phenyl group, which may be the same or different, a halogen atom, a cyano group, a hydroxyl group,
A substituted phenyl group having 1 to 5 substituents selected from a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, or a C ₁ -C ₄ alkoxycarbonyl group, a phenyl C ₁ -C ₄ alkyl group ,
May be the same or different, a halogen atom, a cyano group, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, or a C ₁
A substituted phenyl C ₁ -C ₄ alkyl group having 1 to 5 substituents on the ring selected from —C ₄ alkoxycarbonyl groups,
A phenylcarbonyl group, or 1 which may be the same or different and is selected from a halogen atom, a cyano group, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, or a C ₁ -C ₄ alkoxycarbonyl group; It represents a substituted phenylcarbonyl group having up to 5 substituents on the ring. ) May form a 3- to 7-membered ring with a C ₂ -C ₆ alkylene group which may be interrupted by a group represented by the formula: wherein the 3- to 7-membered ring is one or more halogen atoms or It can also have a substituent selected from C ₁ -C ₄ alkyl groups. m shows the integer of 0-4. ),

[0007]

Embedded image Wherein R ² and R ³ are the same as above.

Embedded image (Wherein, R ² and R ³ are the same as described above), or

[0008]

Embedded image (Wherein, R ² and R ³ are the same as described above), and B is a cyano group, which may be the same or different when m is 0 in the definition of A, and is an oxygen atom, a nitrogen atom, or a sulfur atom. A 5- to 6-membered heterocyclic ring having 1 to 3 heteroatoms selected from the same or different, and may be a halogen atom, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, carbonyl group, carboxyl group, carboxy C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group , An amino group, which may be the same or different,
Amino groups substituted with _one or more C ₁ -C ₄ alkyl groups or phenyl groups, carbamoyl groups, which may be the same or different,
1-2 C ₁ -C ₄ alkyl group or a carbamoyl group substituted by a phenyl group, a carbamoyl C ₁ -C ₄ alkyl group or the same or different and may, 1-2 C ₁ -C ₄ alkyl group Or carbamoyl substituted by a phenyl group
It has ₁ to 4 substituents selected from C ₁ -C ₄ alkyl groups, which may be the same or different, and has 1 to 3 hetero atoms selected from an oxygen atom, a nitrogen atom, or a sulfur atom Substituted 5- to 6-membered heterocycle, or

-C (= X) R ⁴ (wherein R ⁴ is a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C
₄ alkyl group, C ₂ -C ₄ alkenyl group, halo C ₂ -C ₄ alkenyl group, C ₂ -C ₄ alkynyl group, halo C ₂ -C ₄ alkynyl group, phenyl group, which may be the same or different, halogen atom , A cyano group, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, or a substituted phenyl group having 1 to 5 substituents selected from a C ₁ -C ₄ alkoxycarbonyl group, phenyl C ₁ -C ₄ alkyl group, which may be the same or different, halogen atom, cyano group, hydroxyl group, C ₁ -C ₄ alkyl group, C ₁ -C
Substituted phenyl C ₁ having 1 to 5 substituents selected from ₄ alkoxy groups or C ₁ -C ₄ alkoxycarbonyl groups
-C ₄ alkyl group, which may be the same or different, an oxygen atom,
A 5- to 6-membered heterocyclic ring having 1 to 3 heteroatoms selected from a nitrogen atom or a sulfur atom, or the same or different, a halogen atom, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl Group, C ₁ -C ₄ alkoxy group, C ₁ -C
₄ alkylthio group, carbonyl group, carboxyl group, carboxy C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group,
Amino groups, the same or different and a substituted amino group having 1 to 2 substituents selected from C ₁ -C ₄ alkyl group or a phenyl group, a carbamoyl group, the same or different and, C ₁ - A substituted carbamoyl group having 1 to 2 substituents selected from a C ₄ alkyl group or a phenyl group, a carbamoyl C ₁ -C ₄ alkyl group, or a C ₁ -C ₄ alkyl group or a phenyl group which may be the same or different; A substituted or substituted carbamoyl C ₁ -C ₄ alkyl group having 1 to 2 substituents selected from a group having ₁ to 4 substituents, which may be the same or different, an oxygen atom, a nitrogen atom Or substituted 5-6 having 1-3 heteroatoms selected from sulfur atoms
Represents a membered heterocycle.

X is O, S, NR ⁶ (where R ⁶ is shown below), NO-R ⁶ (where R ⁶ is shown later), N (→ O) -R ⁶ ( In the formula, R ⁶ is described below.), NN (R ⁶ ) R ⁷ (where R ⁶ and R ⁷ are described later), or NN = C (R ⁶ ) R ⁷ (wherein R ⁶ And R ⁷ may be the same or different and include a hydrogen atom, a halogen atom, a formyl group, a C ₁ -C ₄ alkyl group,
C ₂ -C ₄ alkenyl group, C ₂ -C ₄ alkynyl group, C ₁ -C ₄ alkylsulfonyl group, halo C ₁ -C ₄ alkylsulfonyl group,
C ₁ -C ₂₀ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, phenyl group, which may be the same or different, halogen atom, hydroxyl group, cyano group, nitro group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo
A substituted phenyl group having 1 to 5 substituents selected from a C ₁ -C ₄ alkoxy group, an amino group or a C ₁ -C ₄ alkoxycarbonyl group, a phenyl C ₁ -C ₄ alkyl group, which may be the same or different well, a halogen atom, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl groups, C ₁ -C
₁ to 5 selected from ₄ alkoxy groups, halo C ₁ -C ₄ alkoxy groups, amino groups and C ₁ -C ₄ alkoxycarbonyl groups
Substituted phenyl C ₁ -C ₄ alkyl group having two substituents on the ring, phenylcarbonyl group, which may be the same or different,
Halogen atom, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo C ₁ -C ₄ alkoxy or C ₁ -C ₄ A substituted phenylcarbonyl group having 1 to 5 substituents selected from an alkoxycarbonyl group,

Carbamoyl groups which may be the same or different
A C ₁ -C ₄ alkyl group, a phenyl group or the same or different, a halogen atom, a C ₁ -C ₄ alkyl group, a halo C ₁ -C
₁ to 2 substituents selected from substituted phenyl groups having 1 to 5 substituents on the ring selected from ₄ alkyl groups, C ₁ -C ₄ alkoxy groups or halo C ₁ -C ₄ alkoxy groups Having a substituted carbamoyl group, a phenylsulfonyl group, which may be the same or different, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, or a C ₁ -C ₄ A substituted phenylsulfonyl group having 1 to 5 substituents selected from an alkoxycarbonyl group,
Thiocarbamoyl groups, the same or different C ₁ may be -C ₄ alkyl group or a thiocarbamoyl group substituted by a phenyl group, C ₁ -C ₄ alkoxy carbon imidoyl group, the same or different and good C ₁ -C ₄ A C ₁ -C ₄ alkoxycarbonimidoyl group having a substituent selected from an alkyl group or a phenyl group on a nitrogen atom, a C ₁ -C ₄ alkylthiocarbonimidoyl group, which may be the same or different, C ₁ -C ₄ A C ₁ -C ₄ alkylthiocarbonimidoyl group having a substituent selected from an alkyl group or a phenyl group on a nitrogen atom, C ₁
-C ₄ alkylsulfinyl carbon imidoyl group, the same or different C ₁ -C ₄ has a substituent on the nitrogen atom which is also selected from a good C ₁ -C ₄ alkyl group or a phenyl group alkylsulfinyl carbon imidoyl group, C ₁ -C ₄ alkylsulfonyl carbon imidoyl group, the same or different C ₁ -C ₄ alkylsulfonyl carbon imide having a substituent on the nitrogen atom which is also selected from a good C ₁ -C ₄ alkyl group or a phenyl group-yl Group, an amidino group, which may be the same or different, an amidino group substituted by a C ₁ -C ₆ alkyl group or a phenyl group, which may be the same or different, and 1 to be selected from an oxygen atom, a nitrogen atom or a sulfur atom 5-6 membered heterocyclic ring having three heteroatoms, or the same or different and may a halogen atom, a cyano group, a hydroxyl group, a mercapto group, C ₁ -C ₄ alkyl group C ₁ -C ₄ alkoxy groups, C ₁ -C ₄
Alkylthio group, carbonyl group, carboxyl group, carboxy C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group, amino group, same or different well, 1-2 C ₁ -C ₄ alkyl group or an amino group substituted by a phenyl group, a carbamoyl group, the same or different and, 1-2 C ₁
A carbamoyl group substituted by a -C ₄ alkyl group or a phenyl group, a carbamoyl C ₁ -C ₄ alkyl group, or the same or different, and substituted by _{1 to} 2 C ₁ -C ₄ alkyl groups or a phenyl group; Having 1 to 4 substituents selected from carbamoyl C ₁ -C ₄ alkyl groups, which may be the same or different, and 1 to 3 hetero atoms selected from an oxygen atom, a nitrogen atom or a sulfur atom A substitution 5-6 having
R ⁶ and R ⁷ together represent —O—,
-S (O) n- (wherein n is as defined above), -CO- or -N (R ⁸ )-(wherein R ⁸ is as defined above). And a 3- to 7-membered ring may be formed by a C ₂ -C ₆ alkylene group which may be one or more halogen atoms or C ₁ -C ₄ alkyl groups which may be the same or different. It can also have selected substituents. ). ).

When m is 1 or more, B is a hydrogen atom, a halogen atom, a cyano group, and 5 to 5 carbon atoms having 1 to 3 hetero atoms which may be the same or different and are selected from an oxygen atom, a nitrogen atom and a sulfur atom. A 6-membered heterocyclic ring, which may be the same or different, a halogen atom, a hydroxyl group, a cyano group, a mercapto group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a carbonyl group Carboxyl group, carboxy C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group, amino group, carbamoyl group, which may be the same or different 1 ~
A substituted carbamoyl group having a substituent selected from two C ₁ -C ₄ alkyl groups or phenyl groups, carbamoyl C ₁ -C
₄ alkyl groups or 1 to 2 which may be the same or different
Substituted C ₁ -C ₄ alkyl groups or substituted carbamoyl having a substituent selected from phenyl groups having ₁ to 3 substituents selected from C ₁ -C ₄ alkyl groups, which may be the same or different A substituted 5- to 6-membered heterocycle having 1 to 3 heteroatoms selected from an oxygen atom, a nitrogen atom or a sulfur atom,

-C (= X) R ⁵ (wherein X is as defined above, R ⁵ is a hydrogen atom, C ₁ -C ₈
Alkyl group, halo C ₁ -C ₄ alkyl group, C ₂ -C ₄ alkenyl group, halo C ₂ -C ₄ alkenyl group, C ₂ -C ₄ alkynyl group, halo C ₂ -C ₄ alkynyl group, a phenyl group, the same Or may be different, ₁ to 5 substituents selected from a halogen atom, a cyano group, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group or a C ₁ -C ₄ alkoxycarbonyl group Having a substituted phenyl group, a phenyl C ₁ -C ₄ alkyl group, which may be the same or different, a halogen atom, a cyano group, a hydroxyl group, a C ₁ -C ₄
An alkyl group, a substituted phenyl C ₁ -C ₄ alkyl group having 1 to 5 substituents on a ring selected from a C ₁ -C ₄ alkoxy group or a C ₁ -C ₄ alkoxycarbonyl group, which may be the same or different A 5- to 6-membered heterocyclic ring having 1 to 3 heteroatoms selected from an oxygen atom, a nitrogen atom or a sulfur atom,
Which may be identical or different, a halogen atom, a cyano group, a hydroxyl group, a mercapto group, C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ alkylthio group, carbonyl group, carboxyl group, carboxy C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄
Alkyl group, amino group, which may be the same or different, C ₁ -C
A substituted amino group having 1 to 2 substituents selected from a ₄ alkyl group or a phenyl group, a carbamoyl group, which may be the same or different, and ₁ to 2 selected from a C ₁ -C ₄ alkyl group or a phenyl group. Substituted carbamoyl groups having 1 to 2 substituents, carbamoyl C ₁ -C ₄ alkyl groups, or may be the same or different and have ₁ to 2 substituents selected from C ₁ -C ₄ alkyl groups or phenyl groups Having 1 to 4 substituents selected from a substituted carbamoyl C ₁ -C ₄ alkyl group, which may be the same or different, and 1 to 3 hetero atoms selected from an oxygen atom, a nitrogen atom or a sulfur atom A substituted 5-6 membered heterocycle having

OR ⁶ (where R ⁶ is as defined above), S (O) nR ⁶ (where n and R ⁶ are as defined above) or N (R ⁶ ) R ⁷ (wherein R ⁶ and R ⁷ are the same as described above). ),

Embedded image (Wherein, R ⁵ is as defined above, and R ⁹ and R ¹⁰ may be the same or different, and include a formyl group, a C ₁ -C ₄ alkylcarbonyl group, a C ₁ -C ₄ alkoxycarbonyl group, and a phenylcarbonyl group. Or may be the same or different, and ₁ to 5 selected from a halogen atom, a cyano group, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, or a C ₁ -C ₄ alkoxycarbonyl group A substituted phenylcarbonyl group having a substituent on the ring, wherein R ⁹ and R ¹⁰ together represent —O—
, -S (O) n- (wherein n is as defined above), -CO- or

Forming a 3- to 7-membered ring by a C ₂ -C ₆ alkylene group which may be interrupted by a group represented by -N (R ⁸ )-(wherein R ⁸ is the same as defined above). also, the 3-7 membered ring may have one or more identical or different substituents is also selected from halogen atom or a C ₁ -C ₄ alkyl group. ), OR ⁶ (wherein R ⁶ is as defined above), S (O) nR ⁶ (where R ⁶ and n are as defined above), N (R ⁶ ) R ⁷ (where R is ⁶ and R ⁷ are the same as above), N = C (R ⁶ ) R ⁷ (wherein R ⁶ and R ⁷ are the same as above) or ON = C (R ⁶ ) R ⁷ (wherein R ⁶ and R ⁷ are the same as described above). ). And a salt thereof, an agricultural and horticultural disease controlling agent containing the compound as an active ingredient, and a method for using the same.

[0016]

BEST MODE FOR CARRYING OUT THE INVENTION In the definition of each substituent in the 1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention, "halogen atom" means chlorine atom, bromine atom, iodine atom or Represents a fluorine atom, "C ₁ -C ₈ alkyl group"
Represents a linear or branched alkyl group having 1 to 8 carbon atoms, for example, methyl, ethyl, n-propyl, i
-Propyl, n-butyl, i-butyl, s-butyl, t
-Alkyl, such as -butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl, and "halo C ₁ -C ₄
May be the same or different from the alkyl group "refers to one or more linear or branched alkyl group having 1 to 4 carbon atoms substituted with a halogen atom," C ₂ -C ₄ alkenyl group " Represents a linear or branched alkenyl group having 2 to 4 carbon atoms having a double bond, and is a “halo C ₂ -C ₄ alkenyl group”
And may be the same or different and represent a linear or branched alkenyl group having 2 to 4 carbon atoms substituted with one or more halogen atoms.

The term "C ₂ -C ₄ alkynyl group" refers to a linear or branched alkynyl group having 2 to 4 carbon atoms having a triple bond, and is referred to as "halo C ₂ -C ₄ alkynyl group". May be the same or different and represents a linear or branched alkynyl group having 2 to 4 carbon atoms substituted with one or more halogen atoms, and may be the same or different, and may be an oxygen atom, a nitrogen atom, Or a 5- to 6-membered heterocycle having at least one heteroatom selected from a sulfur atom ”is, for example, furan, thiophene,
Pyrrole, oxazole, thiazole, isothiazole, pyrazole, imidazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,2
4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, pyrrolidine, piperidine, morpholine,
Thiomorpholine, dithiolane, dithiane, piperazine,
A 5- to 6-membered heterocyclic ring such as dioxolane or imidazolidine is shown.

The salts of the 1,2,3-thiadiazole derivative represented by the general formula (I) include, for example, alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium and magnesium, and ammonium salts. Or may be different, one or more C ₁ -C ₁₂ alkyl groups, phenyl groups,
Examples include a substituted phenyl group, a benzyl group, or an ammonium salt or a guadinium salt substituted with a substituted benzyl group.

1, 2, 3 represented by the general formula (I) of the present invention.
The thiadiazole derivative or a salt thereof can be produced, for example, by a production method exemplified below. Manufacturing method 1.

Embedded image (Wherein, R ¹ is the same as described above, and R ¹¹ represents a C ₁ -C ₈ alkyl group.) A compound represented by the general formula (II) is subjected to a reduction reaction in the presence of a reducing agent to obtain a compound represented by the general formula A 1,2,3-thiadiazole derivative represented by the formula (I-1), wherein the derivative (I-1) is isolated or not isolated and subjected to an oxidation reaction in the presence of an oxidizing agent, The 1,2,3-thiadiazole derivative represented by (I-1) can be produced. This reaction is described in "New Experimental Chemistry Course", Volume 15 (II), page 191 (Maruzen Co., Ltd.), "Experimental Chemistry Course (4th Edition)", Volume 23 (V), page 43 (Maruzen Corporation). And the like.

Manufacturing method 2.

Embedded image (Wherein, R ¹ and R ¹¹ are the same as above, and R ^{4 ′} is a phenyl group, which may be the same or different, a halogen atom, a cyano group, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ An alkoxy group,
Or a C ₁ -C ₄ alkoxycarbonyl group selected from 1 to
A substituted phenyl group having 5 substituents, a 5- or 6-membered heterocyclic ring having 1 to 3 heteroatoms which may be the same or different and selected from an oxygen atom, a nitrogen atom or a sulfur atom,
Or the same or different, a halogen atom, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl group, a C ₁ -C
₄ alkoxy groups, C ₁ -C ₄ alkylthio groups, carbonyl groups, carboxyl groups, carboxy C ₁ -C ₄ alkyl groups, C ₁
-C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group, amino group, which may be the same or different, and ₁ to 2 selected from C ₁ -C ₄ alkyl group or phenyl group A substituted carbamoyl group having ₁ to 2 substituents selected from a C ₁ -C ₄ alkyl group or a phenyl group, which may be the same or different, or a carbamoyl C _1- A C ₄ alkyl group or a carbamoyl C ₁ -C ₄ alkyl group which may be the same or different and has ₁ to 2 substituents selected from a C ₁ -C ₄ alkyl group or a phenyl group; The same or different having from 4 to 4 substituents, an oxygen atom,
It represents a substituted 5- to 6-membered heterocycle having 1 to 3 heteroatoms selected from a nitrogen atom or a sulfur atom. )

The compound represented by the general formula (II) is hydrolyzed and then reacted with thionyl chloride to obtain the compound represented by the general formula (III), and the compound (III) is isolated or isolated. The 1,2,3-thiadiazole derivative represented by the general formula (I-3) can be produced by reacting with the compound represented by the general formula (IV) in the presence of a catalyst without separation. . This reaction is based on the new experimental chemistry course, Vol. 14 (I
I), can be produced according to the method described on page 794.

Manufacturing method 3.

Embedded image (Wherein R ^1, R ⁴ and R ⁶ are the same as described above.) A 1,2,3-thiadiazole derivative represented by the general formula (I-4) is reacted with a compound represented by the general formula (V) By doing so, a 1,2,3-thiadiazole derivative represented by the general formula (I-5) can be produced. This reaction can be produced according to the method described in “Experimental Chemistry Course (4th edition)”, Vol. 20, (V), p. 353.

Manufacturing method 4.

Embedded image (In the formula, R ¹ and R ⁴ , R ⁶ and R ⁷ are the same as described above.)
By reacting the 1,2,3-thiadiazole derivative represented by the general formula (I-4) with the compound represented by the general formula (VI), the 1,2 represented by the general formula (I-6) is obtained. , 3-thiadiazole derivatives can be produced. This reaction is described in Org.
Synth. , Coll. Vol.1, p12 (1988)
Can be produced according to the method described in (1).

Manufacturing method 5.

Embedded image (In the formula, R ¹ and R ⁶ are as defined above, and Hal represents a halogen atom.)

A halogenation reaction is carried out with a 1,2,3-thiadiazole derivative represented by the general formula (I-1) using a halogenating agent such as thionyl chloride or phosphorus tribromide, and then represented by the general formula (III '). The compound (III ') is isolated or not isolated and reacted with sodium formimide, and then reacted with an acid such as hydrochloric acid, whereby the compound represented by the general formula (1-7) is obtained. A salt of a 1,2,3-thiadiazole derivative;
By reacting (1-7) with the general formula (VII),
The 1,2,3-thiadiazole derivative represented by (I-8) or the general formula (I-9) can be produced. In addition, the general formula (I
-7) by reacting a salt of the 1,2,3-thiadiazole derivative represented by the general formula (VIII) with an isocyanate represented by the general formula (VIII). 2,3-
A thiadiazole derivative can be produced. This reaction is described in "Experimental Chemistry Course (4th edition)", 19 (I), 438
Synthesis, 615 (1990), “Experimental Chemistry Course (4th edition)”, Volume 22 (II), p.
It can be produced according to the method described in "New Experimental Chemistry Course", Vol. 14, (III), p.

Manufacturing method 6.

Embedded image (Wherein R ¹ , R ⁶ and Hal are the same as above). By reacting in the presence of 1, represented by the general formula (I-10)
A 2,3-thiadiazole derivative can be produced. This reaction can be produced according to the method described in “Experimental Chemistry Course (4th edition)”, vol. 22, (V), p.

Manufacturing method 7.

Embedded image (Wherein R ¹ , R ⁶ and Hal are the same as above, and n ′ is 1 to
Indicates an integer of 2. By reacting the 1,2,3-thiadiazole derivative represented by the general formula (I-1) with the compound represented by the general formula (IX) in the presence of a base, the compound represented by the general formula (I-11) 1, represented by
A 2,3-thiadiazole derivative is isolated, and the derivative (I-11) is isolated or isolated and subjected to an oxidation reaction in the presence of an oxidizing agent to give a compound represented by the general formula (I-12). , 2,3-
A thiadiazole derivative can be produced. This reaction is described in "New Laboratory Chemistry", Vol. 14, (III), 1716
Page, “Experimental Chemistry Course (4th edition)”, Volume 24 (VI), 3
It can be produced according to the method described on page 65 and the like.

Manufacturing method 8.

Embedded image (Wherein, R ¹ and Hal are the same as described above, and R ¹² and R ¹³ may be the same or different, and include a C ₁ -C ₄ alkyl group, a carboxyl group, a carboxy C ₁ -C ₄ alkyl group, a C _1- C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group, a carbamoyl group, the same or different and,
1-2 selected from C ₁ -C ₄ alkyl groups or phenyl groups
Carbamoyl groups having 3 substituents, carbamoyl C ₁ -C
₄ alkyl groups, or may be the same or different, C ₁ -C
A carbamoyl C ₁ -C ₄ alkyl group having 1 to 2 substituents selected from a ₄ alkyl group and a phenyl group. )

By reacting the compound represented by the general formula (X) with phosphorus pentasulfide and then reacting with the compound represented by the general formula (XI), the compound represented by the general formula (I-13) is obtained. , 2,3
-It is possible to produce thiadiazole derivatives. This reaction is described in "New Laboratory Chemistry", Vol. 14, (IV), 2198.
Page, Org. Synth. , Coll. Vol. II
I. It can be produced according to the method described in p332 (1955) and the like.

Manufacturing method 9.

Embedded image (Wherein, R ¹ is the same as above, and R ¹⁴ is a hydrogen atom or C ₁ -C
₄ represents an alkyl group, W is may be substituted by C ₁ -C ₄ alkyl group, -O-, -NR ⁶ -, (wherein, R ⁶ is as defined above.)

[0031] (wherein, n same. The) -S (O) n-shown, or may be interrupted by -CO- C ₃ -C ₆ alkylene group. The compound represented by the general formula (X) is subjected to a dehydration reaction to obtain a compound represented by the general formula (I
-14), a derivative of the general formula (I-14) isolated or not isolated
The 1,2,3-thiadiazole derivative represented by the general formula (I-15) can be produced by reacting with the compound represented by the formula (XII). This reaction can be produced according to the method described in “New Experimental Chemistry Course”, vol. 14, (II), p.

Manufacturing method 10.

Embedded image (In the formula, R ¹ , R ² , R ³ and B are the same as described above.)

By reacting a 1,2,3-thiadiazole derivative represented by the general formula (I-16) with a compound represented by the general formula (XIII) or a compound represented by the general formula (XIV), A 1,2,3-thiadiazole derivative represented by the general formula (I-17) can be produced. This reaction is described in "New Experimental Chemistry Course", vol. 14, (I), p. 224, JP-A-7-165.
It can be manufactured according to the method described in JP-A-757.

In the present invention, 1,2,3 represented by the general formula (I)
-The compound represented by the general formula (II), which is a raw material compound for producing a thiadiazine derivative, can be produced, for example, by the following production method.

Embedded image (Wherein, R ¹ is as defined above, R ¹¹ represents a C ₁ -C ₈ alkyl group, and R ¹² has a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, or a substituent. The compound represented by the general formula (XVI) is reacted with the compound represented by the general formula (XVI) to obtain a compound represented by the general formula (XVII), and the compound (XVII ) Can be isolated or subjected to a ring closure reaction with thionyl chloride without isolation to produce a compound represented by the general formula (II). This reaction is described in J. A
m. Chem. Soc. , 77 , 5359 (1955)
And the like.

The following are typical examples of the 1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention, but the present invention is not limited thereto. The abbreviations in Table 1 indicate the following groups. Ph: phenyl group cyclo: alicyclic hydrocarbon

Embedded image

[0036]

Embedded image

[0037]

Embedded image General formula (I)

Embedded image

[0038]

[Table 1] Table 1 ────────────────────────────────── No R ¹ AB physical properties ─── ─────────────────────────────── 1 H − COPh mp60-61 ℃ 2 H CH ₂ Cl 3 H CH ₂ OH 4 _{H CH 2 OCH 3 5 H CH} 2 OCH 2 Ph 6 H CH 2 OCH 2 -Q 1 7 CH 3 - CHO nD 1.5555 (26 ℃) 8 CH 3 - COCH 3 9 CH 3 - COPh nD 1.6145 (22 ℃) ─ ─────────────────────────────────

[0039]

[Table 2] Table 1 (continued) ────────────────────────────────── No R ¹ AB Physical Properties ────────────────────────────────── 10 CH ₃ − CO (2-Cl-Ph) 11 CH ₃ − CO (4-Cl-Ph) 12 CH ₃ -CO (2-CH ₃ -Ph) 13 CH ₃ -CO (4-CH ₃ -Ph) 14 CH ₃ -CO (4-iC ₃ H ₇ -Ph) 15 CH ₃ -CO (4-CH ₃ O-Ph) 16 CH ₃ -CO (4-tC ₄ H ₉ -Ph) 17 CH ₃ -CO- (1-CH ₃ -Q ₂ ) mp85-90 ℃ 18 CH ₃ − CN mp50.4 ℃ 19 CH ₃ − CH = NOH mp270 ℃ (dec.) 20 CH ₃ − CH = NOCH ₃ mp97 ℃ 21 CH ₃ − CH = NOCH ₂ Ph nD 1.5998 (25 ℃) 22 CH ₃ − CH = NOCH ₂ (2-Cl-Ph) 23 CH ₃ -CH = NOCH ₂ (3-Cl-Ph) 24 CH ₃ -CH = NOCH ₂ (4-Cl-Ph) mp70-80 ℃ 25 CH ₃ -CH = NOCH ₂ (2-CH ₃ -Ph) 26 CH ₃ -CH = NOCH ₂ (3-CH ₃ -Ph) 27 CH ₃ -CH = NOCH ₂ (4-CF ₃ -Ph) 28 CH ₃ -CH = NOCH ₂ ( 4-OH-Ph) 29 CH ₃ − CH = NOCH ₂ (4-CH ₃ O-Ph) 30 CH ₃ − CH = NOCH ₂ (4-CF ₃ O-Ph) 31 CH ₃ − CH = NOCH ₂ (4 -NH ₂ -Ph) ─────── ──────────────────────────

[0040]

[Table 3] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 32 CH ₃ − CH = NOCH ₂ (4-NO ₂ -Ph) 33 CH ₃ − CH = NOCH ₂ (4-CN-Ph) 34 CH ₃ − CH = NOCH ₂ (4-COOCH ₃ -Ph) 35 CH ₃ − CH = NNH ₂ mp81 ℃ 36 CH ₃ − CH = NNHCH ₃ 37 CH ₃ − CH = NNHPh mp 218 ℃ 38 CH ₃ − CH = NNH (2-Cl-Ph) 39 CH ₃ − CH = NNH (2-F-4-Cl-Ph) 40 CH ₃ − CH = NNH (3, 5-Cl ₂ -Ph) 41 CH ₃ -CH = NNH (3-Cl-Ph) 42 CH ₃ -CH = NNH (3-iC ₃ H ₇ O-Ph) 43 CH ₃ -CH = NNH (4-CF ₃ -Ph) 44 CH ₃ − CH = NNH (4-Cl-Ph) 45 CH ₃ − CH = NNHCOOCH ₃ 46 CH ₃ − CH = NNHCOOC ₄ H ₉ -t 47 CH ₃ − CH = NNHCONHCH ₃ 48 CH ₃ − _{CH = NNHCONHC 2 H 5 49 CH} 3 - CH = NNHCON (CH 3) Ph 50 CH 3 - CH = NNHCONH (4-Cl-Ph) 51 CH 3 - CH = NNHCONH (4-tC 4 H 9 -Ph) 52 CH ₃ − CH = NNHCONH (4-CF ₃ -Ph) 53 CH ₃ − CH = NNHCONH (4-iC ₃ H ₇ O-Ph) ─────────────── ───────────────────

[0041]

[Table 4] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 54 CH ₃ − CH = NNHCONH (4-CF ₃ O-Ph) 55 CH ₃ − CH = NNHCSNHCH ₃ 56 CH ₃ − CH = NNHC (N (CH ₃ ) ₂ ) = NCH ₃ 57 CH ₃ − CH = NNHC (OCH ₃ ) = NCH ₃ 58 CH ₃ − CH = NNHC (SCH ₃ ) = NCH ₃ 59 CH ₃ − CH = NNHC (SOCH ₃ ) = NCH ₃ 60 CH ₃ − CH = NNH- (4,6- (CH ₃ ) ₂ -Q ₃ ) mp182-183 ° C 61 CH ₃ −C ( Ph) = NOH mp172 ° C 62 CH ₃ -C (Ph) = NOCH ₃ nD 1.5905 (22.8 ° C) 63 CH ₃ -C (Ph) = NOC ₈ H ₁₇ 64 CH ₃ -C (Ph) = NOCH ₂ CH = CH ₂ 65 CH ₃ − C (Ph) = NOCH ₂ CCl = CH ₂ 66 CH ₃ − C (Ph) = NOCH ₂ C≡CH nD 1.5945 (22.8 ° C) 67 CH ₃ − C (Ph) = NOCH ₂ C≡CBr 68 CH ₃ − C (Ph) = NOCH ₂ C≡CCl 69 CH ₃ − C (Ph) = NOCH ₂ Ph nD 1.6183 (23.9 ° C) 70 CH ₃ − C (Ph) = NOCH ₂ (4-Cl-Ph) 71 CH ₃ − C (Ph) = NOCH ₂ (3,4-Cl ₂ -Ph) 72 CH ₃ − C (Ph) = NOCH ₂ (2,4,6-Cl ₃ -Ph) 73 CH ₃ − C ( Ph) = NOCH ₂ (2- CH ₃ -Ph) 74 CH ₃ -C (Ph) = NOCH ₂ (3-CH ₃ -Ph) 75 CH ₃ -C (Ph) = NOCH ₂ (4-CH ₃ -Ph) ─────── ───────────────────────────

[0042]

[Table 5]

[0043]

[Table 6] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 96 CH ₃ − 4-CH ₂ COOH-Q ₇ mp 196 ℃ 97 CH _{3 - 4-CH 2 CONH 2} -Q 7 mp182 ℃ 98 CH 3 - 4-CH 2 COOC 2 H 5 -Q 7 mp98 ℃ 99 CH 3 - 4-CH 2 CONHCH 3 -Q 7 mp155 ℃ 100 CH 3 - 4 -CH ₂ CON (C ₂ H ₅ ) ₂ -Q ₇ mp132 ℃ 101 CH ₃ − 5-Ph-Q ₈ mp 154 ℃ 102 CH ₃ − 5-SH-Q ₈ mp 182 ℃ 103 CH ₃ − 5-SCH ₃ -Q _{8 mp65 ℃ 104 CH 3 CH 2} Cl nD 1.5590 (26 ℃) 105 CH 3 CH 2 OH nD 1.553 (21 ℃) 106 CH 3 CH 2 OCH 3 nD 1.5180 (26 ℃) 107 CH 3 CH 2 OC 4 H 9 - n 108 CH ₃ CH ₂ OC ₈ H ₁₇ -n 109 CH ₃ CH ₂ OCH ₂ Ph nD 1.5730 (25 ° C) 110 CH ₃ CH ₂ OCH ₂ (2-Cl-Ph) 111 CH ₃ CH ₂ OCH ₂ (3- Cl-Ph) 112 CH ₃ CH ₂ OCH ₂ (4-Cl-Ph) 113 CH ₃ CH ₂ OCH ₂ (2-CH ₃ -Ph) 114 CH ₃ CH ₂ OCH ₂ (3-CH ₃ -Ph) 115 CH ₃ CH ₂ OCH ₂ (4-tC ₄ H ₉ -Ph) 116 CH ₃ CH ₂ OCH ₂ (4-CF ₃ -Ph) 117 CH ₃ CH ₂ OCH ₂ (2,4- (CH ₃ ) ₂ -Ph) ─────────────────────────────── ───

[0044]

[Table 7] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 118 CH ₃ CH ₂ OCH ₂ (3,4- (CH ₃ ) ₂ -Ph) 119 CH ₃ CH ₂ OCH ₂ (4-OH-Ph) 120 CH ₃ CH ₂ OCH ₂ (4-CH ₃ O-Ph) 121 CH ₃ CH ₂ OCH ₂ (4-CF ₃ O-Ph) 122 CH ₃ CH ₂ OCH ₂ (2,4- (CH ₃ O) ₂ -Ph) 123 CH ₃ CH ₂ OCH ₂ (3,4- (CH ₃ O) ₂ -Ph) 124 CH ₃ CH ₂ OCH ₂ ( 4-NH ₂ -Ph) 125 CH ₃ CH ₂ OCH ₂ (4-NO ₂ -Ph) 126 CH ₃ CH ₂ OCH ₂ (4-COOCH ₃ -Ph) 127 CH ₃ CH ₂ OCH ₂ (4-COOC ₄ H ₉ -t-Ph) 128 CH ₃ CH ₂ OCH ₂ (4-CN-Ph) 129 CH ₃ CH ₂ OCH ₂ (4-CH ₃ -Q ₁ ) nD 1.547 (26.3 ° C) 130 CH ₃ CH ₂ OPh 131 CH ₃ CH ₂ O (2-Cl-Ph) 132 CH ₃ CH ₂ O (3-Cl-Ph) 133 CH ₃ CH ₂ O (4-Cl-Ph) 134 CH ₃ CH ₂ O (2-CH ₃ -Ph ) 135 CH ₃ CH ₂ O (3-CH ₃ -Ph) 136 CH ₃ CH ₂ O (4-tC ₄ H ₉ -Ph) 137 CH ₃ CH ₂ O (4-CF ₃ -Ph) 138 CH ₃ CH ₂ O (2,4- (CH ₃ ) ₂ -Ph) 139 CH ₃ CH ₂ O (3,4- (CH ₃ ) ₂ -Ph) ───── ─────────────────────────────

[0045]

[Table 8] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 140 CH ₃ CH ₂ O (4-OH-Ph) 141 CH ₃ CH ₂ O (4-CH ₃ O-Ph) 142 CH ₃ CH ₂ O (4-CF ₃ O-Ph) 143 CH ₃ CH ₂ O (2,4- (CH ₃ O) ₂ -Ph) 144 CH ₃ CH ₂ O (3,4- (CH ₃ O) ₂ -Ph) 145 CH ₃ CH ₂ O (4-NH ₂ -Ph) 146 CH ₃ CH ₂ O (4-NO ₂ -Ph) 147 CH ₃ CH ₂ O (4-COOCH ₃ -Ph) 148 CH ₃ CH ₂ O (4-COOC ₄ H ₉ -t-Ph) 149 CH ₃ CH ₂ O (4-CN-Ph) 150 CH ₃ CH ₂ O-COCH ₃ nD 1.3580 (25 ° C) 151 CH ₃ CH ₂ O-COC ₂ H ₅ 152 CH ₃ CH ₂ O-COC ₃ H ₇ -n 153 CH ₃ CH ₂ O-COC ₃ H ₇ -i 154 CH ₃ CH ₂ O-COC ₄ H ₉ -t 155 CH ₃ CH ₂ O-COC ₄ H ₉ -s 156 CH ₃ CH ₂ O-COC ₁₇ H ₃₅ -n 157 CH ₃ CH ₂ O-COC ₆ H ₁₁ -cyclo 158 CH ₃ CH ₂ O -COCH = CH ₂ 159 CH ₃ CH ₂ O-COCH = CHPh 160 CH ₃ CH ₂ O-COCH ₂ Cl 161 CH ₃ CH ₂ O-COCF ₃ ──────────────── ────────────── ────

[0046]

[Table 9] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 162 CH ₃ CH ₂ O-COPh mp50-53 ℃ 163 CH ₃ CH ₂ O-CO (2-Cl-Ph) 164 CH ₃ CH ₂ O-CO (3-Cl-Ph) 165 CH ₃ CH ₂ O-CO (4-Cl-Ph) 166 CH ₃ CH ₂ O-CO ( 2-CH ₃ -Ph) 167 CH ₃ CH ₂ O-CO (3-CH ₃ -Ph) 168 CH ₃ CH ₂ O-CO (4-tC ₄ H ₉ -Ph) 169 CH ₃ CH ₂ O-CO ( 4-CF ₃ -Ph) 170 CH ₃ CH ₂ O-CO (2,4- (CH ₃ ) ₂ -Ph) 171 CH ₃ CH ₂ O-CO (3,4- (CH ₃ ) ₂ -Ph) 172 CH ₃ CH ₂ O-CO (4-CH ₃ O-Ph) 173 CH ₃ CH ₂ O-CO (4-CF ₃ O-Ph) 174 CH ₃ CH ₂ O-CO (2,4- (CH ₃ O ) ₂ -Ph) 175 CH ₃ CH ₂ O-CO (3,4- (CH ₃ O) ₂ -Ph) 176 CH ₃ CH ₂ O-CO (4-NO ₂ -Ph) 177 CH ₃ CH ₂ O- CO (4-COOCH ₃ -Ph) 178 CH ₃ CH ₂ O-CO (4-COOC ₄ H ₉ -t-Ph) 179 CH ₃ CH ₂ O-CO (4-CN-Ph) 180 CH ₃ CH ₂ O -COOC ₂ H ₅ nD 1.5041 (26 ° C) 181 CH ₃ CH ₂ O-COOC ₄ H ₉ -i 182 CH ₃ CH ₂ ON = C (CH ₃ ) ₂ 183 CH ₃ CH ₂ ON = C (CH ₃ ) C ₂ H ₅ ─── ──────────────────────────────

[0047]

[Table 10] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 184 CH ₃ CH ₂ ON = C ₆ H ₁₀ -cyclo 185 CH ₃ CH ₂ ON = CHPh 186 CH ₃ CH ₂ ON = CH (2-Cl-Ph) 187 CH ₃ CH ₂ ON = CH (3-Cl-Ph) 188 CH ₃ CH ₂ ON = CH (4-Cl-Ph) 189 CH ₃ CH ₂ ON = CH (2-CH ₃ -Ph) 190 CH ₃ CH ₂ ON = CH (3-CH ₃ -Ph) 191 CH ₃ CH ₂ ON = CH (4-C ₄ H ₉ -t- Ph) 192 CH ₃ CH ₂ ON = CH (4-CF ₃ -Ph) 193 CH ₃ CH ₂ ON = CH (2,4- (CH ₃ ) ₂ -Ph) 194 CH ₃ CH ₂ ON = CH (3, Ph) 4- (CH ₃ ) ₂ -Ph) 195 CH ₃ CH ₂ ON = CH (4-OH-Ph) 196 CH ₃ CH ₂ ON = CH (4-CH ₃ O-Ph) 197 CH ₃ CH ₂ ON = CH (4-CF ₃ O-Ph) 198 CH ₃ CH ₂ ON = CH (2,4- (CH ₃ O) ₂ -Ph) 199 CH ₃ CH ₂ ON = CH (3,4- (CH ₃ O) ₂ -Ph) 200 CH ₃ CH ₂ ON = CH (4-NH ₂ -Ph) 201 CH ₃ CH ₂ ON = CH (4-NO ₂ -Ph) 202 CH ₃ CH ₂ ON = CH (4-COOCH ₃ -Ph ) 203 CH ₃ CH ₂ ON = C (CH ₃ ) Ph 204 CH ₃ CH ₂ OSO ₂ CH ₃ 205 CH ₃ CH ₂ OSO ₂ CF ₃ ─────────── ───────────────────────

[0048]

[Table 11] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 206 CH ₃ CH ₂ OSO ₂ Ph 207 CH ₃ CH ₂ OSO ₂ ( 4-Br-Ph) 208 CH ₃ CH ₂ OSO ₂ (4-CH ₃ -Ph) Paste 209 CH ₃ CH ₂ SPh nD 1.636 (24.6 ° C) 210 CH ₃ CH ₂ SOPh 211 CH ₃ CH ₂ SO ₂ Ph mp 118 ° C. 212 CH ₃ CH ₂ SO ₂ (4-CH ₃ -Ph) 213 CH ₃ CH ₂ SO ₂ (4-NO ₂ -Ph) 214 CH ₃ CH ₂ SCH ₂ Ph nD 1.612 (24.6 ° C) 215 CH ₃ CH ₂ SO _{2 CH 2 Ph mp116 ℃ 216 CH} 3 CH 2 SCON (CH 2 CH = CH 2) 2 217 CH 3 CH 2 SCO-Q 9 218 CH 3 CH 2 SCOOC 2 H 5 219 CH 3 CH 2 SCSN (C 2 H 5 ) ₂ 220 CH ₃ CH ₂ NH ₂・ HCl mp> 250 ° C 221 CH ₃ CH ₂ N (C ₂ H ₅ ) ₂ paste 222 CH ₃ CH ₂ N (CH ₂ CH = CH ₂ ) ₂ paste 223 CH ₃ CH _{2 NHPh 224 CH 3 CH 2 NH (} 4-CH 3 -Ph) 225 CH 3 CH 2 NHCOCH 3 226 CH 3 CH 2 NHCOC 2 H 5 227 CH 3 CH 2 NHCOC 3 H 7 -n ──────── ─────── ──────────────────

[0049]

[Table 12] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 228 CH ₃ CH ₂ NHCOC ₃ H ₇ -i 229 CH ₃ CH ₂ NHCOC ₄ H ₉ -t mp 93-94 ℃ 230 CH ₃ CH ₂ NHCOC ₄ H ₉ -s 231 CH ₃ CH ₂ NHCOC ₁₇ H ₃₅ -n 232 CH ₃ CH ₂ NHCOC ₃ H ₅ -cyclo mp 75-78 ℃ 233 CH ₃ CH ₂ NHCO (2,2-Cl ₂ -C ₃ H ₅ -cyclo) 234 CH ₃ CH ₂ NHCOC ₆ H ₁₁ -cyclo 235 CH ₃ CH ₂ NHCOCH = CH ₂ 236 CH ₃ CH ₂ NHCOCH = CHPh 237 CH ₃ CH ₂ NHCOCH ₂ Cl 238 CH ₃ CH ₂ NHCOCF ₃ 239 CH ₃ CH ₂ NHCOPh mp96 ° C 240 CH ₃ CH ₂ NHCO (2-Cl-Ph) 241 CH ₃ CH ₂ NHCO (3-Cl-Ph) 242 CH ₃ CH ₂ NHCO (4-Cl-Ph) 243 CH 3 CH 2 NHCO (2-CH 3 -Ph) 244 CH 3 CH 2 NHCO (3-CH 3 -Ph) 245 CH 3 CH 2 NHCO (4-tC 4 H 9 - Ph) 246 CH ₃ CH ₂ NHCO (3-CF ₃ -Ph) 247 CH ₃ CH ₂ NHCO (4-CF ₃ -Ph) 248 CH ₃ CH ₂ NHCO (2,4- (CH ₃ ) ₂ -Ph) 249 _{CH 3 CH 2 NHCO (3,4- (} CH 3) 2 -Ph) ─────────── ──────────────────────

[0050]

[Table 13] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 250 CH ₃ CH ₂ NHCO (4-OH-Ph) 251 CH ₃ CH ₂ NHCO (4-CH ₃ O-Ph) 252 CH ₃ CH ₂ NHCO (4-CF ₃ O-Ph) 253 CH ₃ CH ₂ NHCO (2,4- (CH ₃ O) ₂ -Ph) 254 CH ₃ CH ₂ NHCO (3,4- (CH ₃ O) ₂ -Ph) 255 CH ₃ CH ₂ NHCO (4-NH ₂ -Ph) 256 CH ₃ CH ₂ NHCO (4-NO ₂ -Ph) 257 CH ₃ CH ₂ NHCO (4-COOCH ₃ -Ph) 258 CH ₃ CH ₂ NHCO (2,4-Cl ₂ -Ph) 259 CH ₃ CH ₂ NHCO (3,4-Cl ₂ -Ph) 260 CH ₃ CH ₂ N (CHO) ₂ mp 70-75 ° C 261 CH ₃ CH ₂ Q ₁₀ 262 CH ₃ CH ₂ 3,3,4,4,5,5-F ₆ -Q ₁₁ 263 CH ₃ CH ₂ Q ₁₂ mp 124-125 ° C. 264 CH ₃ CH _{2 NHCOOCH 3 265 CH 3 CH 2 NHCOOC} 2 H 5 paste _{266 CH 3 CH 2 NHCOOC 4 H} 9 -i 267 CH 3 CH 2 NHCOOC 4 H 9 -t 268 CH 3 CH 2 NHCOO (4-NO 2 -Ph) 269 CH _{3 CH 2 NHCOOPh 270 CH 3 CH} 2 NHCONHCH 3 271 CH 3 CH 2 NHCONHC 2 H 5 ───────────────── ────────────────

[0051]

[Table 14] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 272 CH ₃ CH ₂ NHCONHC ₃ H ₇ -i 273 CH ₃ CH ₂ NHCONHPh mp145 ° C 274 CH ₃ CH ₂ NHCONH (2-Cl-Ph) 275 CH ₃ CH ₂ NHCONH (3-Cl-Ph) 276 CH ₃ CH ₂ NHCONH (4-Cl-Ph) 277 CH ₃ CH ₂ NHCONH (2 -CH ₃ -Ph) 278 CH ₃ CH ₂ NHCONH (3-CH ₃ -Ph) 279 CH ₃ CH ₂ NHCONH (4-tC ₄ H ₉ -Ph) 280 CH ₃ CH ₂ NHCONH (3-CF ₃ -Ph) 281 CH ₃ CH ₂ NHCONH (4-CF ₃ -Ph) 282 CH ₃ CH ₂ NHCONH (2,4- (CH ₃ ) ₂ -Ph) 283 CH ₃ CH ₂ NHCONH (3,4- (CH ₃ ) _2- Ph) 284 CH ₃ CH ₂ NHCONH (4-OH-Ph) 285 CH ₃ CH ₂ NHCONH (3-CH ₃ O-Ph) 286 CH ₃ CH ₂ NHCONH (4-iC ₃ H ₇ O-Ph) 287 CH ₃ CH ₂ NHCONH (4-CF ₃ O-Ph) 288 CH ₃ CH ₂ NHCONH (2,4- (CH ₃ O) ₂ -Ph) 289 CH ₃ CH ₂ NHCONH (3,4- (CH ₃ O) _2- Ph) 290 CH ₃ CH ₂ NHCONH (4-NH ₂ -Ph) 291 CH ₃ CH ₂ NHCONH (4-NO ₂ -Ph) 292 CH ₃ CH ₂ NHCONH (4-COOCH ₃ -Ph) 293 CH ₃ CH ₂ N HCONH (2,4-Cl ₂ -Ph) ──────────────────────────────────

[0052]

[Table 15] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 294 CH ₃ CH ₂ NHCSNHCH ₃ 295 CH ₃ CH ₂ NHCSNHPh mp171-172 ° C 296 CH ₃ CH ₂ NHC (= NCH ₃ ) OC ₂ H ₅ 297 CH ₃ CH ₂ NHC (= NPh) N (C ₂ H ₅ ) ₂ 298 CH ₃ CH ₂ NHC (= NPh) SCH ₃ 299 CH ₃ CH ₂ NHSO ₂ (4-CH ₃ -Ph) paste 300 CH ₃ CH ₂ NHNH ₂ 301 CH ₃ CH ₂ NHN = C (CH ₃ ) ₂ 302 CH ₃ CH ₂ NHN = CHPh 303 CH ₃ CH ₂ NHN = C (CH ₃ ) Ph 304 CH ₃ CH ₂ Q ₁₃ 305 CH ₃ CH ₂ Q ₁₄ 306 CH ₃ CH ₂ Q ₁₅ 307 CH ₃ CH ₂ CHO 308 CH ₃ CH ₂ CN 309 CH ₃ CH ₂ COOCH ₃ 310 CH ₃ CH ₂ COOC ₂ H ₅ 311 CH ₃ CH ₂ COOC ₃ H ₇ -i 312 CH ₃ CH ₂ COOC ₈ H ₁₇ -n 313 CH ₃ CH ₂ COOCH ₂ CH = CH ₂ 314 CH ₃ CH ₂ CONH ₂ 315 CH ₃ CH ₂ CONHCH ₃ ─ ─────────────────────────────────

[0053]

[Table 16] Table 1 (continued) ────────────────────────────────── No R ¹ AB Physical Properties ────────────────────────────────── 316 CH ₃ CH ₂ CONHC ₃ H ₇ -i 317 CH ₃ CH ₂ CON (CH ₃ ) ₂ 318 CH ₃ CH ₂ CO-Q ₁₆ 319 CH ₃ CH ₂ CO-Q ₁₇ 320 CH ₃ CH ₂ CO-Q ₁₈ 321 CH ₃ CH ₂ CO-Q ₁₉ 322 CH ₃ CH ₂ CH (COCH ₃ ) ₂ 323 CH ₃ CH ₂ CH (COOC ₂ H ₅ ) ₂ 324 CH ₃ CH ₂ C (NHCOCH ₃ ) (COOC ₂ H ₅ ) ₂ mp93-97 ℃ 325 CH ₃ CH ₂ CH (SCH ₃ ) (SOCH ₃ ) 326 CH ₃ CH ₂ Q ₂₀ 327 CH ₃ CHCl COOCH ₃ nD 1.5456 (23 ° C) 328 CH ₃ CHCH ₃ CN 329 CH ₃ CHCH ₃ COOCH ₃ 330 CH ₃ C (CH ₃ ) ₂ CN 331 CH ₃ C (CH ₃ ) ₂ COOCH ₃ 332 CH ₃ CHPh Cl nD 1.5979 (21.8 ℃) 333 CH ₃ CHPh OH mp93.2 ℃ 334 CH ₃ CHPh OCH ₃ 335 CH ₃ CHPh CN 336 CH ₃ CHPh COOH 337 CH ₃ CH ₂ CH ₂ COOCH ₃ ─ ─────────────────────────────────

[0054]

[Table 17] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 338 CH ₃ CH = CH (E) COOCH ₃ mp70 ℃ 339 CH ₃ CH = CH (E) CON (CH ₃ ) ₂ 340 CH ₃ CH = CH (E) CONHPh 341 CH ₃ CH = CH (Z) COOCH ₃ mp80-85 ℃ 342 CH ₃ CH = CH (E, Z mixed) CHO mp77-78 ℃ 343 CH ₃ C = C (SCH ₃ ) ₂ CN 344 CH ₃ Q ₂₁ CN 345 CH ₃ C = C (COOCH ₃ ) ₂ H 346 CH ₃ C = C (COOCH ₃ ) CN H paste 347 CH _{3 Q 22 CN 348 C 2 H 5} CH 2 Cl 349 C 2 H 5 CH 2 OH 350 C 2 H 5 CH 2 OCH 3 351 C 2 H 5 CH 2 OCH 2 Ph 352 C 2 H 5 CH 2 OCH 2 (4- C ₂ H ₅ -Q ₁ ) 353 C ₃ H ₇ -i CH ₂ F 354 C ₃ H ₇ -i CH ₂ Cl 355 C ₃ H ₇ -i CH ₂ Br 356 C ₃ H ₇ -i CH ₂ I 357 C ₃ H ₇ -i CH ₂ OH 358 C ₃ H ₇ -i CH ₂ OCH ₃ 359 C ₃ H ₇ -i CH ₂ OCH ₂ Ph ─────────────────── ───────────────

[0055]

[Table 18] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 360 C ₃ H ₇ -i CH ₂ OCH ₂ (4-iC ₃ H ₇ -Q ₁ ) 361 C ₃ H ₇ -i CH ₂ NH ₂・ HCl 362 C ₃ H ₇ -i CH ₂ N (CH ₃ ) ₂ 363 C ₃ H ₇ -i CH ₂ N (CH ₂ CH = CH ₂ ) ₂ 364 C ₃ H ₇ -i CH ₂ NHCOCH ₃ 365 CH ₂ Cl CH ₂ OH Paste 366 CF ₃ CH ₂ OH 367 Ph-Q ₄ mp 150 ℃ 368 Ph-Q ₅ mp 158 ℃ 369 Ph-5- (CH _{3 ) 2 -Q 5 mp147 ℃ 370 Ph} - 4-CH 3 -Q 7 mp161 ℃ 371 Ph - 4-tC 4 H 9 -Q 7 mp110 ℃ 372 Ph - 4-COOCH 3 -Q 7 mp124 ℃ 373 Ph - 4- CONHCH ₃ -Q ₇ mp 187 ℃ 374 Ph − 4-CH ₂ COOH-Q ₇ mp 137 ℃ 375 Ph − 4-CH ₂ CONH ₂ -Q ₇ mp 137 ℃ 376 Ph − 4-CH ₂ CONHCH ₃ -Q ₇ mp 154 ℃ 377 Ph − 5-CH ₃ -Q ₂₃ mp85 ℃ 378 Ph CH ₂ Cl 379 Ph CH ₂ OH 380 Ph CH ₂ OCH ₃ 381 Ph CH ₂ OCH ₂ Ph ───────────────── ─── ─────────────

[0056]

[Table 19] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 382 Ph CH ₂ OCH ₂ (4-Ph-Q ₁ ) 383 Ph CH ₂ COOCH ₃ 384 Ph CH ₂ CON (CH ₃ ) Ph 385 Ph CH ₂ CONH (4-CH ₃ O-Ph) mp 129 ℃ 386 2-Cl-Ph CH ₂ OH 387 3-Cl-Ph CH ₂ OH 388 4 -Cl-Ph CH ₂ OH 389 4-CH ₃ -Ph CH ₂ OH 390 3-CH ₃ -Ph CH ₂ OH 391 4-CH ₃ -Ph CH ₂ OH 392 4-tC ₄ H ₉ -Ph CH ₂ OH 393 2-CF ₃ -Ph CH ₂ OH 394 4-CF ₃ -Ph CH ₂ OH 395 2,4- (CH ₃ ) ₂ -Ph CH ₂ OH 396 3,4- (CH ₃ ) ₂ -Ph CH ₂ OH 397 4-OH-Ph CH ₂ OH 398 4-CH ₃ O-Ph CH ₂ OH 399 4-CF ₃ O-Ph CH ₂ OH 400 4-PhO-Ph CH ₂ OH 401 2,4- (CH ₃ O) ₂ -Ph CH ₂ OH 402 3,4- (CH ₃ O) ₂ -Ph CH ₂ OH 403 4-COOCH ₃ -Ph CH ₂ OH ───────────────

[0057]

[Table 20] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 404 2,4-Cl ₂ -Ph CH ₂ OH 405 3,4 -Cl ₂ -Ph CH ₂ OH 406 Q ₂₄ CH ₂ OH 407 Q ₂₅ CH ₂ OH 408 Q ₂₆ CH ₂ OH 409 Q ₂₇ CH ₂ OH mp 158 ℃ 410 Q ₂₈ CH ₂ OH 411 6-Cl-Q ₂₇ CH ₂ OH 412 Q ₂₇ -CN mp 129 ℃ 413 4-F-Ph CH ₂ O-CO- (4-Cl-Ph) mp 79 ℃ 414 4-F-Ph CH ₂ O- (4-CH ₃ O-Ph) mp 86 ℃ 415 4-F-Ph CH ₂ O-CO-CH _2- (4-CH ₃ -Ph) mp113 ℃ 416 4-F-Ph CH ₂ O-CO-NH-Ph mp 99 ℃ 417 4-F-Ph CH ₂ ON = C (CH ₃ ) (4-Cl-Ph) mp 91 ℃ 418 4-F-Ph CH ₂ OH mp100 ℃ 419 4-F-Ph CH ₂ Br mp 88 ℃ 420 4-F-Ph CH ₂ O-CO-CH ₃ mp 59 ° C 421 Q ₂₆ − CN mp 190 ° C 422 Ph CH ₂ CONH- (4-CH ₃ O-Ph) mp 129 ° C 423 Ph C = NOH (NH ₂ ) mp130 ° C 424 Ph − CN 425 CH ₃ - Q ₈ paste ─────────────────────────────── ──

[0058]

[Table 21] Table 1 (continued) ────────────────────────────────── No R ¹ AB physical properties ────────────────────────────────── 426 CH ₃ − 5-CH ₃ -Q ₈ nD 1.5661 (26.4 ° C ) 427 CH ₃ − SCH ₂ CH = CH ₂ paste 428 CH ₃ − SCH ₂ C≡CH paste 429 CH ₃ − SCH ₂ -Ph mp89 ° C 430 CH ₃ − SCH _2- (4-tC ₄ H ₉ -Ph) mp79 ℃ 431 CH ₃ − SC ₃ H ₇ -i Paste 432 CH ₃ − S-CH ₂ -Q ₂₇ mp 78 ℃ 433 CH ₃ − S-CH ₂ -Q ₂₈ mp 97 ℃ ──────────── ──────────────────────

In Table 1, H-NM of the compound having the physical properties of the paste is shown.
Table 2 shows the R data.

Table 2 Table 2 No H-NMR [CDCl ₃ / TMS , Δ value (ppm)] ────────────────────────────────── 208 2.46 (s.3H), 2.63 (s.3H), 5.35 (s.2H), 7.35 (d.2H), 7.77 (d.2H) .221 1.05 (t.6H), 2.54 (q.4H), 2.63 (s.3H), 3.78 (s.2H) .222 2.61 (s.3H), 3.10-3.12 (m.4H), 3.80 (s.2H), 5.16-5.24 (m.4H), 5.78-5.89 (m.2H). ────────────────────────────────

[0060]

[Table 23] Table 2 (continued) ────────────────────────────────── No H-NMR [CDCl ₃ / TMS, δ value (ppm)] 265 265 1.25 (t.3H ), 2.63 (s.3H), 4.15 (q.2H), 4.59 (d.2H), 5.2-5.35 (br.1H) .299 2.44 (s.3H), 2.58 (s.3H), 4.42 (d .2H), 5.37 (br.t.1H), 7.31 (d.2H), 7.70 (d.2H) .346 1.41 (t.3H), 2.90 (s.3H), 4.20 (q.2H), 8.34 (s.1H) .365 2.58 (t.1H), 5.03 (s.2H), 5.16 (d.2H) .426 3.08 (s, 3H), 3.96 (d, 2H), 5.27 (d, 1H), 5.43 (d, 1H), 6.00 (m, 1H) .427 3.08 (s, 3H), 5.23 (d, 2H), 6.28 (s, 1H) .430 1.55 (d, 6H), 3.08 (s, 3H) , 4.02 (m, 1H).

In the following, the compound represented by the general formula (I) of the present invention,
Representative examples, formulation examples and test examples of the 2,3-thiadiazole derivative or salts thereof will be shown, but the present invention is not limited thereto. Embodiment 1 FIG. Production of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde (Compound No. 7).

Embedded image 9.9 g (46 mmol) of pyridinium chlorochromate and 10 g of silica gel are suspended in 25 ml of methylene chloride and 3.0 g (23 mmol) of 4-methyl-1,
2,3-Thiadiazol-5-ylmethanol was added,
The mixture was stirred at room temperature for 4 hours to carry out a reaction. After completion of the reaction, the reaction solution was diluted with ether, and florisil was filtered. The obtained filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 3: 1).
Purification yielded 2.0 g of the desired product. Physical properties:
nD 1.5555 (26 ° C) Yield: 62%

Embodiment 2 FIG. Production of 5-benzoyl-4-methyl-1,2,3-thiadiazole (Compound No. 9).

Embedded image 0.50 g (3.5 mmol) of 4-methyl-1,2,2
2.0 g of 3-thiadiazole-5-carboxylic acid (15
Of thionyl chloride and stirred for 2 hours while heating, and then the polythionyl chloride was distilled off under reduced pressure. The resulting residue was added to a solution of 1.8 g (15 mmol) of aluminum chloride and 20 ml of benzene for 3 hours. The reaction was performed under heating. After completion of the reaction, the reaction solution was poured into ice water, the desired product was extracted with ethyl acetate, the organic layer was washed with saturated saline, then dried, and the solvent was distilled off under reduced pressure. Purification by chromatography (n-hexane: ethyl acetate = 4: 1) gave 0.69 g of the desired product
Obtained. Physical properties: nD 1.6145 (22 ° C) Yield: 97%

Embodiment 3 FIG. O-benzyl-4-methyl-
Production of 1,2,3-thiadiazole-5-carbaldehyde oxime (Compound No. 21).

Embedded image 0.40 g (3.1 mmol) of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde obtained in Example 1, 0.60 g (3.8 mmol) of benzyloxyamine hydrochloride and 0% .50 g (3.8 mmol) of sodium acetate was added to 10 ml of ethanol, and the mixture was reacted under heating and reflux for 4 hours. After completion of the reaction, ethyl acetate was added to the reaction solution, followed by filtration to remove a precipitate. The residue obtained by concentration under reduced pressure was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 4: 1). Purification yielded 0.66 g of the desired product. Physical properties: nD 1.5998 (25 ° C) Yield: 91%

Embodiment 4 FIG. 5- (5-mercapto-1,
3,4-oxadiazol-2-yl) -4-methyl-
Production of 1,2,3-thiadiazole (Compound No. 10
2).

Embedded image 1.1 g (7.2 mmol) of 4-methyl-1,2,3
-Dissolve thiadiazole-5-carbohydrazide in 15 ml of ethanol and add 0.3 g of potassium hydroxide in 1 m
Then, 0.6 ml of carbon disulfide was added, and the mixture was reacted under heating and refluxing for 6.5 hours. After the reaction,
The solvent was distilled off under reduced pressure, water was added, the mixture was acidified with acetic acid, and the precipitated crystals were collected by filtration to obtain 0.82 g of the desired product. Physical properties: m. p. 182 ° C Yield: 59%

Embodiment 5 FIG. 4-methyl-5- (5-methylthio-1,3,4-oxadiazol-2-yl)-
Production of 1,2,3-thiadiazole (Compound No. 103)
).

Embedded image 0.40 g (2.0 mmol) of 5- (5-mercapto-1,3,4-thiadiazol-2-yl) -4-methyl-1,2,3-thiadiazole, 0.43 g (3.0
Mmol) of methyl iodide and 0.83 g (6.0 mmol) of potassium carbonate in 10 ml of acetone.
The reaction was carried out under heating and refluxing for hours. After completion of the reaction, the precipitate was removed by filtration, and the residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to obtain the target compound (0.1%). 41
g was obtained. Physical properties: m. p. 65 ° C yield: 96%

Embodiment 6 FIG. Production of 5-chloromethyl-4-methyl-1,2,3-thiadiazole (Compound No. 10
4).

Embedded image Under ice cooling, 0.50 g (3.8 mmol) of 4-methyl-
1,2,3-thiadiazol-5-ylmethanol
The reaction was conducted by adding 2 ml of thionyl chloride and stirring at room temperature for 2 hours. Next, water was added to the reaction solution to stop the reaction, the desired product was extracted with ethyl acetate, washed with water and dried, and the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography (n-hexane). : Ethyl acetate = 3:
Purification in 1) gave 0.46 g of the desired product. Physical properties: nD 1.5590 (26 ° C) Yield: 81%

Embodiment 7 FIG. Production of 4-methyl-1,2,3-thiadiazol-5-ylmethanol (Compound No. 1
05).

Embedded image 0.10 g (2.5 mmol) of sodium hydroxide
Dissolved in 0 ml of ethanol, 1.0 g (5.8 mmol) of 4-methyl-1,2,3-thiadiazole-5-
Ethyl carboxylate was added, and then 0.33 g (8.7 mmol) of sodium borohydride was added to carry out the reaction at room temperature. After completion of the reaction, water was added to the reaction solution to decompose excess sodium borohydride, and then the target product was extracted with ethyl acetate.After washing with water and drying, the solvent was distilled off under reduced pressure.
The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to obtain 0.36 g of the desired product. Physical properties: nD 1.553 (21 ° C.) Yield: 48%

Embodiment 8 FIG. Production of 4-methyl-5-benzyloxymethyl-1,2,3-thiadiazole (Compound No. 109).

Embedded image 0.40 g (3.1 mmol) of 4-methyl-1,2,2
3-Thiadiazol-5-ylmethanol was dissolved in 10 ml of acetone, 1.6 g (12 mmol) of potassium carbonate and 0.80 g (4.5 mmol) of benzyl bromide were added, and the reaction was heated under reflux for 10 hours. went. After completion of the reaction, the precipitate was filtered off, the solvent was distilled off under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (n
-Hexane: ethyl acetate = 3: 1) to obtain 0.65 g of the desired product. Physical properties: nD 1.5730 (25 ° C) Yield: 96%

Embodiment 9 FIG. 4,4′-dimethyl-5,
Production of 5′-oxybis (methyl-1,2,3-thiadiazole) (Compound No. 129).

Embedded image 2.0 g (15 mmol) of 4-methyl-1,2,3-
Thiadiazol-5-ylmethanol and 3.9 g (3
9 mmol) of triethylamine was dissolved in 20 ml of tetrahydrofuran, and 3.5 g (18 mmol) of tosyl chloride was added thereto under ice-cooling, followed by a reaction at room temperature for one day. Next, a saturated saline solution was added to the reaction solution to stop the reaction,
The desired product is extracted with ethyl acetate, and the extract is washed with diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline in this order, the solvent is concentrated under reduced pressure, and the obtained residue is subjected to silica gel column chromatography (n-hexane). : Ethyl acetate = 4:
Purification in 1) gave 1.1 g of the desired product. Physical properties: nD 1.547 (26 ° C) Yield: 57%

Embodiment 10 FIG. 4-methyl-1,2,3-
Preparation of thiadiazol-5-ylmethyl acetate) (Compound No. 150).

Embedded image 0.50 g (3.8 mmol) of 4-methyl-1,2,2
3-thiadiazol-5-ylmethanol, 0.50 g
(5.7 mmol) of acetyl chloride and 0.80 g
(7.6 mmol) of triethylamine was dissolved in 10 ml of tetrahydrofuran and reacted at room temperature for 18 hours. Then, the reaction was quenched by adding saturated saline to the reaction solution, the target substance was extracted with ethyl acetate, washed with water and dried, the solvent was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (n-hexane). : Ethyl acetate = 3:
By refining in 1), 0.70 g of the desired product was obtained. Physical properties: nD 1.3580 (25 ° C) Yield: 100%

Embodiment 11 FIG. Ethyl 4-methyl-1,
Production of 2,3-thiadiazol-5-ylmethyl carbonate (Compound No. 180).

Embedded image 0.50 g (3.8 mmol) of 4-methyl-1,2,2
3-Thiadiazol-5-ylmethanol was dissolved in 5 ml of tetrahydrofuran, 0.80 g (7.6 mmol) of triethylamine and 0.60 g (5.7 mmol) of ethyl chlorocarbonate were added, and the mixture was reacted at room temperature for 22 hours. Was done. Next, water was added to the reaction solution to stop the reaction, the target substance was extracted with ethyl acetate, washed with water and dried, and then the solvent was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (n-hexane: acetic acid). Purification with ethyl (5: 1) yielded 0.50 g of the desired product. Physical properties: nD 1.5041 (26 ° C) Yield: 68%

Embodiment 12 FIG. Production of 4-methyl-5-phenylthiomethyl-1,2,3-thiadiazole (Compound No. 209).

Embedded image 0.50 g (3.8 mmol) of 4-methyl-1,2,2
3-Thiadiazol-5-ylmethanol under ice-cooling, 3
The reaction was carried out for 4 hours with the addition of thionyl chloride, and then concentrated under reduced pressure. To the concentrate, 1.30 g (11.5 mmol) of potassium carbonate and 0.38 g (3.4 mmol) of potassium carbonate were added.
Of thiophenol and 10 ml of acetone were added, and the reaction was carried out under heating and refluxing for 7 hours. After completion of the reaction, the reaction solution was cooled to room temperature, the precipitate was filtered off, the solvent was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 5: 1). Purification yielded 0.64 g of the desired product. Physical properties: nD 1.636 (25 ° C) Yield: 85%

Embodiment 13 FIG. Production of 4-methyl-5-phenylsulfonylmethyl-1,2,3-thiadiazole (Compound No. 211).

Embedded image 0.20 g (0.99 mmol) of 4-methyl-5-phenylthiomethyl-1,2,3-thiadiazole.
Dissolve in 0 ml of methylene chloride and add 0.40 g to the solution.
(2.3 mmol) of metachloroperbenzoic acid and 2
The reaction was performed for 0 hours at room temperature. Next, an aqueous solution of sodium hydrogen sulfite was added to the reaction solution to stop the reaction, the target product was extracted with ethyl acetate, the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, and the solvent was concentrated under reduced pressure. Silica gel column chromatography (n-hexane:
Purification by ethyl acetate (2: 1) yielded 0.23 g of the desired product. Physical properties: m. p. 118 ° C yield: 100%

Embodiment 14 FIG. Production of 5-aminomethyl-4-methyl-1,2,3-thiadiazole hydrochloride (Compound No. 220).

Embedded image 7.0 g (47 mmol) of 5-chloromethyl-4-methyl-1,2,3-thiadiazole and 9.0 g (94
(Mmol) of sodium formimide was added to 50 ml of acetonitrile, and the reaction was carried out under reflux for 16 hours. After completion of the reaction, the reaction solution was cooled to room temperature, saturated saline was added thereto, and the desired product was extracted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. Next, 40 ml of water was added to the obtained crystals, and 30 ml of concentrated hydrochloric acid was added with stirring. After 10 minutes, water and hydrochloric acid were distilled off under reduced pressure, and the residue was washed with ethyl acetate to obtain 6.6 g of the desired product. Physical properties: m. p. > 250 ° C Yield: 77%

Embodiment 15 FIG. Production of 5- (N, N-diallylamino) methyl-4-methyl-1,2,3-thiadiazole (Compound No. 222).

Embedded image 0.50 g (3.0 mmol) of 5-aminomethyl-4
-Methyl-1,2,3-thiadiazole hydrochloride, 1.1
0 g (9.0 mmol) of allyl bromide and 2.1 g (1
(5 mmol) of potassium carbonate was added to 15 ml of acetone, and the reaction was carried out under reflux with heating for 20 hours. After the reaction,
The reaction solution was filtered to remove the precipitate, the solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1) to obtain the target substance in an amount of 0.1%. 42 g were obtained. Physical property: Paste Yield: 67% H-NMR [CDCl ₃ / TMS, δ value (ppm)] 2.61 (s.3H), 3.10-3.12 (m.4H), 3.80 (s.2H), 5.16- 5.24
(m.4H), 5.78-5.89 (m.2H).

Embodiment 16 FIG. Methyl (E) -3- (4-methyl-1,2,3-thiadiazol-5-yl) -2-propenoate (Compound No. 338) and (Z) -3- (4
-Methyl-1,2,3-thiadiazol-5-yl)-
Production of methyl 2-propenoate (Compound No. 341).

Embedded image 0.40 g (3.1 mmol) of 4-methyl-1,2,2
3-Thiadiazole-5-carbaldehyde was dissolved in tetrahydrofuran, and 1.1 g (3.4 mmol) of methyl triphenylphosphoranylideneacetate was added to the solution, and the mixture was reacted at room temperature for 16 hours. After completion of the reaction, the reaction solution was cooled to room temperature, saturated saline was added thereto, and the desired product was extracted with ethyl acetate. After washing with water and drying, the solvent was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography ( By purifying with n-hexane: ethyl acetate = 5: 1), 0.49 g of the target E-isomer and 0.05 g of the Z-isomer were obtained. Physical properties: E-form m. p. 70 ° C Yield: 90% Z-form m. p. 80-85 ° C Yield: 10%

Embodiment 17 FIG. 2-cyano-3- (4-methyl-1,2,3-thiadiazol-5-yl) -2-
Production of ethyl propenoate (Compound No. 346).

Embedded image 1.5 g (12 mmol) of 4-methyl-1,2,3-
Thiadiazole-5-carbaldehyde, 1.5 g (13
Mmol) of ethyl cyanoacetate, 0.40 g (6.0 mmol) of pyrrolidine and 0.20 g (1.2 mmol) of tosylic acid were added to 50 ml of toluene, and Dean was added.
The reaction was carried out under heating and reflux for 2 hours in a reaction vessel equipped with a -Stark dehydrator. After completion of the reaction, a saturated saline solution was added to the reaction solution, and the desired product was extracted with ethyl acetate.The organic layer was washed with diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline in this order, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1) to give the desired product in 0.73.
g was obtained. Physical properties: Paste Yield: 30% H-NMR [CDCl ₃ / TMS, δ value (ppm)] 1.41 (t.3H), 2.90 (s.3H), 4.20 (q.2H), 8.34 (s. 1H).

Embodiment 18 FIG. 4-phenyl-3,4
5,6-tetrahydropyrimidin-2-yl-1,2,2
Production of 3-thiadiazole (Compound No. 368).

Embedded image 0.95 g (5.0 mmol) of 4-phenyl-1,
2,3-thiadiazole-5-carbonitrile and 3.
8 g (50 mmol) of 1,3-propanediamine was dissolved in 10 ml of ethanol, 0.05 g of sodium ethoxide was added, and the mixture was reacted under heating and refluxing for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the desired product was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the obtained oil was recrystallized from a small amount of ethyl acetate to obtain 0.68 g of the desired product. Physical properties: m. p. 158 ° C Yield: 55%

Embodiment 19 FIG. 2- (4-phenyl-1,
2,3-thiadiazol-5-yl) thiazole-4-
Preparation of methyl carboxylate (Compound No. 372).

Embedded image 1.1 g (5.0 mmol) of 4-phenyl-1,2,2
3-thiadiazole-5-carbothioamide and 0.9
2 g (5.0 mmol) of methyl bromopyruvate
It was dissolved in 0 ml of chlorobenzene and reacted under heating and reflux for 3 hours. After completion of the reaction, the reaction solution is cooled to room temperature,
A saturated aqueous sodium hydrogen carbonate solution was added, and the desired product was extracted with ethyl acetate. The solvent of the extract is concentrated under reduced pressure, and the obtained residue is subjected to silica gel column chromatography (n-
The product was purified by hexane: ethyl acetate = 3: 1) to obtain 0.74 g of the desired product. Physical properties: n. p. 124 ° C Yield: 41%

The 1,2,3 represented by the general formula (I) of the present invention
Thiadiazole derivatives or salts thereof are useful as agricultural and horticultural disease control agents, for example, rice blast (Pyriculari
a oryzae), rice blight (Rhizoctonia solani), rice sesame leaf blight (Cochiobolus miyabeanus), powdery mildew on barley and wheat, etc. (Erysiphe graminis) Powdery mildew on various host plants, oat crown Rust (Puccin
ia coronata) and other plant rust, tomato plague (Phytophthara infestans) and other plant plague, cucumber downy mildew (Pseudoperonospora cubensis) and grape downy mildew (Plasmopara viticola). Disease, apple scab (Venturia inaequalis), apple spot leaf rot (Alternaria mali), pear black spot (Alternar)
ia kikuchiana), citrus black spot (Diaporthe cit)
r), Pseudomonas species such as cucumber spot bacterial disease (P
seudomonas syringae pv. lachrymans), tomato bacterial wilt (Pseudomonas solanacearum), xanthomonas species, such as cabbage black rot (Xanthomonascampestris), rice white blight (Xanthomonas oryzae), citrus canker (Xan
thomonas citri), Erwinia species, for example, bacterial diseases such as cabbage soft rot (Erwinia carotovora), and virus diseases such as tobacco mosaic virus (Tobacco mosaic virus).

According to the present invention, 1,2,3-
Agricultural and horticultural disease control agents containing a thiadiazole derivative or a salt thereof as an active ingredient include paddy crops, field crops, fruit trees, vegetables,
Since it has a remarkable control effect on the disease that damages other crops and flowers, etc., according to the time when the disease is expected to occur, before or at the time when the disease is confirmed to occur The desired effect of the agricultural and horticultural disease controlling agent of the present invention can be obtained by treating paddy water, foliage, or soil of paddy fields, fields, fruit trees, vegetables, other crops, flowers, and the like. The agricultural and horticultural disease controlling agent of the present invention is generally used after being formulated into a convenient form according to a conventional method for agricultural chemical formulation. That is, the 1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention or a salt thereof is mixed with a suitable inert carrier or, if necessary, together with an auxiliary in a suitable ratio. Dissolved, separated, suspended,
It may be mixed, impregnated, adsorbed or adhered, and formulated into an appropriate dosage form, for example, a suspension, emulsion, liquid, wettable powder, granule, powder, tablet or the like.

The inert carrier which can be used in the present invention may be either solid or liquid. Examples of the material which can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and the like. Tobacco stem flour, walnut shell flour, bran, fibrous powder, residue after extracting plant extract, synthetic polymers such as pulverized synthetic resin, clays (eg, kaolin, bentonite, acid clay), talcs (eg, talc, pyrophyllide) Etc.), silicas (for example, diatomaceous earth, silica sand, mica, white carbon [synthetic high-dispersion silicic acid also called hydrous finely divided silicon or hydrous silicic acid, some of which contain calcium silicate as a main component depending on the product]), activated carbon, sulfur powder , Pumice, calcined diatomaceous earth, brick crushed material, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, ammonium sulfate,
Examples include chemical fertilizers such as phosphorous, nitrate, urea, and salt, and composts, and these are used alone or in the form of a mixture of two or more.

The material that can be a liquid carrier is selected from those having a solvent function per se, and those capable of dispersing the active ingredient compound with the aid of an adjuvant even without the solvent function. The following carriers can be exemplified as typical examples, and they are used alone or in the form of a mixture of two or more kinds. Examples thereof include water, alcohols (eg, 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 and the like), dimethyl sulfoxides and the like. 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 ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene higher fatty acid esters, Polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate,
Surfactants such as lignin sulfonate and higher alcohol sulfate can be exemplified. For the purpose of stabilizing the dispersion of the active ingredient compound, adhering and / or binding, the following exemplified auxiliaries can be used. For example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose, acacia, polyvinyl Auxiliaries such as alcohol, pine oil, bran oil, bentonite, ligninsulfonate and the like can also be used. The following auxiliaries can be used to improve the flowability of the solid product. For example, auxiliaries such as wax, stearate, alkyl phosphate and the like can be used. As peptizers for suspension products, auxiliary agents such as, for example, naphthalenesulfonic acid condensates, condensed phosphates and the like can also 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.
In the case where it is used as an emulsion or a wettable powder, it is suitably from 0.01 to 50% by weight.

The agricultural and horticultural disease controlling agent of the present invention can be used in an amount effective for controlling the disease as it is or as appropriately diluted or suspended with water or the like to control various diseases. It may be used by applying it to a place where predicted crops or outbreaks are not preferable. It can be used in a seed disinfection method or the like. In addition to spraying on stems, leaves and the like for diseases such as wheat, it can be used by treating soil or the like and absorbing it from the roots.
The amount of the agricultural and horticultural disease control agent used in the present invention depends on various factors, such as the purpose, the target disease, the growth status of the crop, the tendency of the disease to occur, the weather, the environmental conditions, the dosage form, the application method, the application place, and the application time. The active ingredient compound may be appropriately selected from the range of 0.1 g to 10 kg per 10 ares according to the purpose. The agricultural and horticultural disease controlling agent of the present invention can be further used in combination with other agricultural and horticultural disease controlling agents for the purpose of controlling the disease to be controlled, extending the suitable period of control, or reducing the amount of the drug. .

Hereinafter, typical examples and test examples of the present invention will be described, but the present invention is not limited to these.
In addition, in the formulation examples, "parts" indicates parts by weight. Formulation Example 1. Compound shown in Table 1 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts More than one was uniformly mixed and dissolved to form an emulsion. Formulation example 2. Compounds listed in Table 1 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to give a powder.

Formulation Example 3 Compounds listed in Table 1 5 parts Bentonite and clay mixed powder 90 parts lignin sulfonate 5 parts Mix uniformly, add appropriate amount of water, knead, granulate,
Dry to granules. Formulation Example 4. Compounds listed in Table 1 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to obtain a wettable powder.

Test Example 1 Rice blast control test by water application. Paddy rice cultivated in 1 / 10,000 are pots (5-6
At the leaf stage), a drug containing the compound shown in Table 1 as an active ingredient was applied to the surface of the water at a rate of 200 g / 10a as an active ingredient, left in a greenhouse for 1 week, and then treated with rice blast (Pyriculari).
a oryzae) by spray inoculation. After inoculation, leave it in a wet room for 1 day, transfer it to a greenhouse, leave it for 6 days after inoculation to cause sufficient disease, investigate the number of lesions on each leaf, and calculate the control value in comparison with the untreated plot. The determination was made according to the following criteria. A: Control value 100-95% B: Control value 94-85% C: Control value 84-60% D: Control value 59-0%

As a result of the above test, the compounds shown in Table 1 showed excellent blast control activity, and
1, 24, 35, 36, 60, 62, 66 to 69, 7
7, 83, 84, 87 to 89, 91, 93 to 100, 1
02, 104 to 106, 109, 129, 150, 16
2,180,209,220-222,229,23
9, 260, 263, 273, 295, 299, 32
7, 338, 341, 342, 346, 365, 36
7, 369, 371, and 376 are judgments of C or higher, and particularly compounds 7, 37, 88, 89, 91, 104, and 10
5, 109, 129, 150, 220, 221, 22
2,239,260,263,273,299,32
7, 342, 367, and 371 show the control effect of A.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Kazuhiro Takagi 4-12-10-1124 Kitahorie, Nishi-ku, Osaka-shi, Osaka Person Takayoshi Tajima 2-10-9-301 Nagai, Sumiyoshi-ku, Osaka-shi, Osaka

Claims (6)

[Claims] 1. A compound of the general formula (I)[Wherein, R¹ Is a hydrogen atom, C₁-C₈Alkyl group, halo C₁-C
_FourAn alkyl group, a phenyl group, which may be the same or different,
Halogen atom, hydroxyl group, cyano group, nitro group, C₁-C_FourA
Lucyl group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoxy
Group, halo C₁-C_FourAlkoxy group or C₁-C_FourAlkoxycal
Substitution having 1 to 5 substituents selected from a bonyl group
A phenyl group, which may be the same or different, 1 to 3 oxygens
5-6 membered hetero with an atom, nitrogen or sulfur atom
A ring, or the same or different, a halogen atom,
Cyano group, hydroxyl group, mercapto group, C₁-C_Four Alkyl group,
C₁-C_FourAlkoxy group, C₁-C_FourAlkylthio group, carbonyl
Group, carboxyl group, carboxy C₁-C_FourAlkyl group,
C₁-C_Four Alkoxycarbonyl group, C₁-C_FourAlkoxycal
Bonil C₁-C_Four Alkyl group, amino group, same or different
Also good, 1-2 C₁-C_Four Alkyl group or phenyl group
Substituted amino group having a selected substituent, carbamoy
Groups, which may be the same or different,₁-C_Four Al
Having a substituent selected from a kill group or a phenyl group;
Substituted carbamoyl group, carbamoyl C₁-C_Four An alkyl group or
May be the same or different, and 1 to 2 C₁-C_Four Archi
Having a substituent selected from a phenyl group or a phenyl group
Carbamoyl C₁-C_Four 1-4 selected from alkyl groups
And may be the same or different, and have 1 to 3
Substitution 5-6 having an oxygen atom, a nitrogen atom or a sulfur atom
A membered heterocyclic ring, wherein A is(Where R^TwoAnd R^ThreeMay be the same or different, and
Atom, halogen atom, cyano group, formyl group, C₁-C_FourAl
Kill group, C₁-C_FourAlkoxy group, C₁-C_FourAlkylthio group,
C₁-C_FourAlkylsulfinyl group, C₁-C_FourAlkylsulfo
Nyl group, C₁-C_FourAlkylcarbonyl group, C₁-C_FourAlkoki
Cycarbonyl group, phenyl group, same or different
Halo, hydroxyl, cyano, nitro, C₁-C
_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoki
Si group, halo C₁-C_FourAlkoxy group, C₁-C_FourAlkoxycal
Substitution having 1 to 5 substituents selected from a bonyl group
A phenyl group, a phenylcarbonyl group, or the same or
May be different, halogen atom, hydroxyl group, cyano group, C₁
-C_FourAlkyl group, or C₁-C_FourAn alkoxycarbonyl group
Substituted 1 to 5 substituents selected from
A carbonyl group; R^TwoAnd R^ThreeTogether -O-
 , -S (O) n- (wherein, n represents an integer of 0 to 2), -CO
-Or-NR⁸-(Where R⁸Is hydrogen atom, formyl group, C₁-C₈Alkyl
Group, halo C₁-C_FourAlkyl group, C_Two-C_FourAlkenyl group, halo
C_Two-C_FourAlkenyl group, C_Two-C_FourAlkynyl group, halo C_Two-C_Four
Alkynyl group, C₁-C_FourAlkylthio group, C₁-C_FourAlkyl
Sulfinyl group, C₁-C_FourAlkylsulfonyl group, C₁-C_Four
Alkylcarbonyl group, C₁-C_FourAlkoxycarbonyl
Group, carbamoyl group, which may be the same or different, C₁-C_Four
1 to 2 positions selected from an alkyl group or a phenyl group
Substituted carbamoyl group, phenyl group,
May be different, a halogen atom, a cyano group, a hydroxyl group,
C₁-C_FourAlkyl group, C₁-C_FourAlkoxy group, or C₁-C_Four A
1 to 5 substituents selected from alkoxycarbonyl groups
A substituted phenyl group having phenyl C₁-C_FourAlkyl group,
May be the same or different, halogen atom, cyano group, water
Acid group, C₁-C_FourAlkyl group, C₁-C_FourAlkoxy group, or C₁
-C_Four 1 to 5 groups selected from an alkoxycarbonyl group
Substituted phenyl C having a substituent on the ring₁-C_FourAlkyl group,
Phenylcarbonyl group or same or different
, Halogen atom, cyano group, hydroxyl group, C₁-C_FourAlkyl
Group, C₁-C_FourAlkoxy group, or C₁-C_Four Alkoxycarbo
Having 1 to 5 substituents on the ring selected from nyl groups
Shows a substituted phenylcarbonyl group. ) With a medium
C may be rejected_Two-C₆A 3- to 7-membered ring with an alkylene group
The 3- to 7-membered ring may be one or more of the same or
Halogen atom or C which may be different₁-C_FourFrom an alkyl group
It can also have selected substituents. m is 0-4
Indicates an integer. ), Embedded image(Where R^TwoAnd R^ThreeIs the same as above. ), Embedded image(Where R^TwoAnd R^ThreeIs the same as above. ) Or(Where R^TwoAnd R^ThreeIs the same as above. ) And B is the constant of A
In the definition, when m is 0, a cyano group may be the same or different
Selected from oxygen, nitrogen, or sulfur
5-6 membered heterocycle having 1-3 heteroatoms, identical
Or may be different, halogen atom, cyano group, hydroxyl
Group, mercapto group, C₁-C_Four Alkyl group, C₁-C_FourAlkoki
Si group, C₁-C_FourAlkylthio, carbonyl, carboxyl
Sil group, carboxy C₁-C_FourAlkyl group, C₁-C_Four Alkoki
Cicarbonyl group, C₁-C_FourAlkoxycarbonyl C₁-C_Four A
Alkyl group, amino group, which may be the same or different,
C₁-C_Four Substituted by an alkyl or phenyl group
Amino group, carbamoyl group, which may be the same or different,
1-2 C₁-C_Four Substituted by alkyl group or phenyl group
Carbamoyl group, carbamoyl C₁-C_Four Alkyl group
Or may be the same or different, and 1 to 2 C₁-C_Four A
Carbamoyl substituted by alkyl or phenyl groups
C₁-C_Four Having 1 to 4 substituents selected from alkyl groups
And may be the same or different, and include an oxygen atom, a nitrogen atom,
Has 1 to 3 heteroatoms selected from sulfur atoms
Substituted 5- to 6-membered heterocycle, or -C (= X) R^Four (Where R^FourIs a hydrogen atom, C₁-C₈Alkyl group, halo C₁-C
_FourAlkyl group, C_Two-C_FourAlkenyl group, halo C_Two-C_FourArche
Nyl group, C_Two-C_FourAlkynyl group, halo C_Two-C_FourAlkynyl
Group, phenyl group, which may be the same or different,
Child, cyano group, hydroxyl group, C₁-C_FourAlkyl group, C₁-C_FourAl
Coxy group, or C₁-C_FourSelect from alkoxycarbonyl groups
A substituted phenyl group having 1 to 5 substituents,
Nil C₁-C_FourAlkyl group, which may be the same or different, halo
Gen atom, cyano group, hydroxyl group, C₁-C _FourAlkyl group, C₁-C
_FourAlkoxy group, or C₁-C_FourAn alkoxycarbonyl group
Substituted phenyl C having 1 to 5 substituents selected from₁
-C_FourAn alkyl group, which may be the same or different, an oxygen atom,
1 to 3 hetero atoms selected from a nitrogen atom or a sulfur atom
5- or 6-membered heterocyclic ring having atoms, or same or different
Halogen, cyano, hydroxyl, merka
Put group, C₁-C_FourAlkyl group, C₁-C_FourAlkoxy group, C₁-C
_FourAlkylthio, carbonyl, carboxyl,
Ruboxy C₁-C_FourAlkyl group, C₁-C_FourAlkoxycarboni
Group, C₁-C_FourAlkoxycarbonyl C₁-C_FourAlkyl group,
Amino group, which may be the same or different, C₁-C_FourAlkyl group
Or having 1 to 2 substituents selected from a phenyl group
Substituted amino group, carbamoyl group, same or different
Well, C₁-C_FourSelected from alkyl groups or phenyl groups
A substituted carbamoyl group having 1 to 2 substituents,
Moyle C₁-C_FourAlkyl group, or the same or different
Well, C₁-C_FourSelected from alkyl groups or phenyl groups
Substituted carbamoyl C having 1 to 2 substituents₁-C_FourAl
Having 1 to 4 substituents selected from the group consisting of
May be different from oxygen, nitrogen or sulfur
Substituted 5 to 6 having 1 to 3 heteroatoms selected from
Represents a membered heterocycle. X is O, S, N-R⁶ (Where R⁶Is shown below. ), NO-R⁶ (Where R⁶Is shown below. ), N (→ O) -R⁶ (Where R⁶Is shown below. ), NN (R⁶) R⁷ (Where R⁶And R⁷Is shown below. ) Or NN = C (R⁶) R⁷ (Where R⁶And R⁷May be the same or different, and hydrogen
Atom, halogen atom, formyl group, C₁-C_FourAlkyl group,
C_Two-C_FourAlkenyl group, C_Two-C_FourAlkynyl group, C₁-C_FourAl
Killsulfonyl group, halo C₁-C_FourAlkylsulfonyl group,
C₁-C₂₀Alkylcarbonyl group, C₁-C_FourAlkoxycarbo
Nyl group, phenyl group, which may be the same or different, halogen
Atom, hydroxyl group, cyano group, nitro group, C₁-C_FourAlkyl
Group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoxy group, halo
C₁-C_FourAlkoxy group, amino group or C₁-C_FourAlkoxyka
A group having 1 to 5 substituents selected from a rubonyl group;
Substituted phenyl group, phenyl C₁-C_FourAlkyl group, same or different
May be halogen, hydroxyl, cyano, nitro
B group, C₁-C_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C
_FourAlkoxy group, halo C₁-C_FourAlkoxy group, amino group or
Is C₁-C_Four1 to 5 selected from an alkoxycarbonyl group
Phenyl C having three substituents on the ring₁-C_FourAlkyl
Group, a phenylcarbonyl group, which may be the same or different,
Halogen atom, hydroxyl group, cyano group, nitro group, C₁-C_FourA
Lucyl group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoxy
Group, halo C₁-C_FourAlkoxy group or C₁-C_FourAlkoxycal
Substitution having 1 to 5 substituents selected from a bonyl group
Phenylcarbonyl group, carbamoyl group, same or different
Good C₁-C_FourAlkyl group, phenyl group or the same
Or a halogen atom, C₁-C_FourAlkyl
Group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoxy group or ha
B c₁-C_Four1 to 5 substituents selected from an alkoxy group
One or two selected from substituted phenyl groups having on the ring
Substituted carbamoyl group having a substituent of
Nil group, which may be the same or different, halogen atom, hydroxyl
Group, cyano group, nitro group, C₁-C_FourAlkyl group, C₁-C_FourA
Lucoxy group, or C₁-C_FourSelect from alkoxycarbonyl groups
Substituted phenylsulfo having 1 to 5 substituents selected
Nil group, thiocarbamoyl group, may be the same or different
C₁-C_FourThio substituted by an alkyl or phenyl group
Carbamoyl group, C₁-C_FourAlkoxy carbon imidoyl
Group, C which may be the same or different₁-C_FourAlkyl group or
C having on the nitrogen atom a substituent selected from a nyl group₁-C
_FourAlkoxy carbon imidoyl group, C₁-C_FourAlkyl
Ocarbonimidoyl group, which may be the same or different₁-C
_FourA substituent selected from an alkyl group or a phenyl group
C on elementary atom₁-C_FourAlkylthiocarbonimide
Group, C₁-C_FourAlkylsulfinyl carbon imidoyl
Group, C which may be the same or different₁-C_FourAlkyl group or
C having on the nitrogen atom a substituent selected from a nyl group₁-C
_FourAlkylsulfinylcarbonimidoyl group, C₁-C_Four
Alkylsulfonylcarbonimidoyl groups, the same or different
May be C₁-C_FourSelect from alkyl group or phenyl group
Having a substituent on the nitrogen atom₁-C_FourAlkylsul
Honyl carbon imidoyl group, amidino group, same or different
May be, C₁-C₆By an alkyl or phenyl group
A substituted amidino group, which may be the same or different, and
1 to 3 atoms selected from an atom, a nitrogen atom or a sulfur atom
A 5- to 6-membered heterocycle having a heteroatom, or
May be different, a halogen atom, a cyano group, a hydroxyl group,
Mercapto group, C₁-C_Four Alkyl group, C₁-C_FourAlkoxy
Group, C₁-C_FourAlkylthio group, carbonyl group, carboxy
Carboxy C₁-C_FourAlkyl group, C₁-C_Four Alkoxy
Carbonyl group, C₁-C_FourAlkoxycarbonyl C₁-C_Four Al
A kill group, an amino group, which may be the same or different, 1-2
C₁-C_Four A substituted by an alkyl or phenyl group
A mino group, a carbamoyl group, which may be the same or different,
~ 2 C₁-C_Four Substituted by an alkyl or phenyl group
Carbamoyl group, carbamoyl C₁-C_Four Alkyl group,
Or may be the same or different, and 1 to 2 C₁-C_Four A
Carbamoyl substituted by alkyl or phenyl groups
C₁-C_Four Having 1 to 4 substituents selected from alkyl groups
And may be the same or different, and include an oxygen atom, a nitrogen atom or
Having 1 to 3 heteroatoms selected from sulfur atoms
Represents a substituted 5- to 6-membered heterocyclic ring;⁶And R⁷Are together
-O-, -S (O) n- (where n is the same as above), -CO-
Or -N (R⁸)-(Where R⁸Is the same as above. Is interrupted by the group indicated by)
May be C_Two-C₆Forming a 3- to 7-membered ring with an alkylene group
And the 3- to 7-membered ring may be one or more same or different.
Halogen atom or C₁-C_FourSelected from alkyl groups
It can also have a substituent that is ). )
You. When m is 1 or more, B is a hydrogen atom, a halogen atom,
Cyano group, which may be the same or different, oxygen atom, nitrogen atom
1 to 3 heteroatoms selected from
Having a 5- to 6-membered heterocyclic ring, which may be the same or different,
Rogen atom, hydroxyl group, cyano group, mercapto group, C₁-C_Four
Alkyl group, C₁-C_FourAlkoxy group, C₁-C_FourAlkylthio
Group, carbonyl group, carboxyl group, carboxy C₁-C_Four
Alkyl group, C₁-C_FourAlkoxycarbonyl group, C₁-C_FourA
Lucoxycarbonyl C₁-C_FourAlkyl group, amino group, cal
Bamoyl group, one or two C, which may be the same or different₁-C_Four
Having a substituent selected from an alkyl group or a phenyl group
Substituted carbamoyl group, carbamoyl C₁-C_FourAlkyl
Group, or one or two C which may be the same or different₁-C_Four
Having a substituent selected from an alkyl group or a phenyl group
Substituted carbamoyl C₁-C_Four1 selected from an alkyl group
Having up to 3 substituents, which may be the same or different,
1 to 3 atoms selected from an atom, a nitrogen atom or a sulfur atom
Substituted 5- to 6-membered heterocycle having a hetero atom, -C (= X) R^Five (Wherein X is as defined above, R^FiveIs a hydrogen atom, C₁-C₈
Alkyl group, halo C₁-C_FourAlkyl group, C_Two-C_FourAlkenyl
Group, halo C_Two-C_FourAlkenyl group, C_Two-C_FourAlkynyl group, ha
B c_Two-C_FourAlkynyl group, phenyl group, same or different
Good, halogen atom, cyano group, hydroxyl group, C₁-C_FourAl
Kill group, C₁-C_FourAlkoxy group or C₁-C_FourAlkoxycal
Substitution having 1 to 5 substituents selected from a bonyl group
Phenyl group, phenyl C₁-C_FourAlkyl groups, identical or different
May be halogen atom, cyano group, hydroxyl group, C₁-C_Four
Alkyl group, C₁-C_FourAlkoxy group or C₁-C_FourAlkoxy
1 to 5 substituents selected from a carbonyl group
Having substituted phenyl C₁-C_FourAlkyl group, same or different
May be selected from oxygen, nitrogen and sulfur atoms.
A 5-6 membered heterocycle having 1-3 heteroatoms,
May be the same or different, halogen atom, cyano group, water
Acid group, mercapto group, C₁-C_FourAlkyl group, C₁-C_FourArco
Xyl group, C₁-C_FourAlkylthio group, carbonyl group, carbo
Xyl group, carboxy C₁-C_FourAlkyl group, C₁-C_FourArco
Xycarbonyl group, C₁-C_FourAlkoxycarbonyl C₁-C_Four
Alkyl group, amino group, which may be the same or different, C₁-C
_Four1 to 2 alkyl groups or phenyl groups
A substituted amino group having a substituent, a carbamoyl group,
May be different, C₁-C_FourAlkyl group or phenyl group
Substituted carbamoy having one or two substituents selected from
Carbamoyl C₁-C_FourAn alkyl group or the same
May be different, C₁-C_FourAlkyl group or phenyl group
Substituted carbamoy having one or two substituents selected from
Le C₁-C_Four1 to 4 substituents selected from alkyl groups
May be the same or different, and may be an oxygen atom, a nitrogen atom or
Has 1 to 3 heteroatoms selected from sulfur atoms
Substituted 5- to 6-membered heterocycle, O-R⁶ (Where R⁶Is the same as above. ), S (O) n-R⁶ (Wherein n and R⁶Is the same as above. ) Or N (R⁶) R⁷ (Where R⁶And R⁷Is the same as above. ). ),(Where R^FiveIs the same as above, and R⁹And R^TenIs the same or
May be different from a formyl group, C₁-C_FourAlkyl carb
Nyl group, C₁-C_FourAlkoxycarbonyl group, phenylcar
A carbonyl group, or the same or different, halogen
Atom, cyano group, hydroxyl group, C₁-C_FourAlkyl group, C₁-C_FourA
Lucoxy group, or C₁-C_FourSelect from alkoxycarbonyl groups
Substituted phenyl having 1 to 5 substituents selected on the ring
A carbonyl group;⁹And R^TenTogether -O-
 , -S (O) n- (wherein n is as defined above), -CO- or -N (R⁸)-(Where R⁸Is the same as above. Is interrupted by the group indicated by)
May be C_Two-C₆Forming a 3- to 7-membered ring with an alkylene group
And the 3- to 7-membered ring may be one or more same or different.
Halogen atom or C₁-C_FourSelected from alkyl groups
It can also have a substituent that is ), O-R⁶ (Where R⁶Is the same as above. ), S (O) n-R⁶ (Where R⁶And n are the same as above. ), N (R⁶) R⁷ (Where R⁶And R⁷Is the same as above. ), N = C (R⁶) R⁷ (Where R⁶And R⁷Is the same as above. ) Or ON = C (R⁶) R⁷ (Where R⁶And R⁷Is the same as above. ). ]
1,2,3-thiadiazole derivative or salt thereof
Kind. 2. R ¹ represents a hydrogen atom, a C ₁ -C ₈ alkyl group or a halo C ₁ -C ₄ alkyl group, and A represents (Wherein R ² and R ³ may be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a formyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ Alkylthio group,
C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, phenyl group, which may be the same or different, halogen atom, hydroxyl group , Cyano group, nitro group, C ₁ -C
₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo C ₁ -C ₄ alkoxy groups, 1 to 5 substituents selected from C ₁ -C ₄ alkoxycarbonyl group Having a substituted phenyl group, a phenylcarbonyl group, or the same or different, a halogen atom, a hydroxyl group, a cyano group, C ₁
A substituted phenylcarbonyl group having 1 to 5 substituents selected from a -C ₄ alkyl group or a C ₁ -C ₄ alkoxycarbonyl group on a ring, and m represents an integer of 0 to 4. )
Is shown. In the definition of A, when m is 0, B is a cyano group, which may be the same or different, and has 5 to 3 heteroatoms selected from an oxygen atom, a nitrogen atom, or a sulfur atom.
A 6-membered hetero ring, which may be the same or different, a halogen atom, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a carbonyl group, Carboxyl group, carboxy C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group, amino group, which may be the same or different, 1-2 An amino group substituted by a C ₁ -C ₄ alkyl group or a phenyl group, a carbamoyl group, which may be the same or different, and a carbamoyl group substituted by _{1 to} 2 C ₁ -C ₄ alkyl groups or a phenyl group, A carbamoyl C ₁ -C ₄ alkyl group, which may be the same or different,
1-4 selected from carbamoyl C ₁ -C ₄ alkyl groups substituted by two C ₁ -C ₄ alkyl groups or phenyl groups
Substituted or 5- or 6-membered heterocycle having 1 to 3 heteroatoms selected from an oxygen atom, a nitrogen atom, or a sulfur atom, or -C (= X) R ⁴ (wherein R ⁴ is a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C
₄ alkyl group, phenyl group, may be the same or different,
Halogen atom, cyano group, hydroxyl group, C ₁ -C ₄ alkyl group,
A substituted phenyl group having 1 to 5 substituents selected from a C ₁ -C ₄ alkoxy group, or a C ₁ -C ₄ alkoxycarbonyl group, or the same or different, and an oxygen atom, a nitrogen atom or a sulfur atom shows the 5-6 membered heterocyclic ring having 1-3 heteroatoms selected from, X is ^{O, S, NO-R 6} ( wherein, R ⁶ is shown later.), NN (R ⁶⁾ R ⁷ (wherein, R ⁶ and R ⁷ may be the same or different and each represent a hydrogen atom, a halogen atom, a formyl group, a C ₁ -C ₄ alkyl group,
C ₂ -C ₄ alkenyl group, C ₂ -C ₄ alkynyl group, C ₁ -C ₄ alkylsulfonyl group, halo C ₁ -C ₄ alkylsulfonyl group,
C ₁ -C ₂₀ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, phenyl group, which may be the same or different, halogen atom, hydroxyl group, cyano group, nitro group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo
A substituted phenyl group having 1 to 5 substituents selected from a C ₁ -C ₄ alkoxy group, an amino group or a C ₁ -C ₄ alkoxycarbonyl group, a phenyl C ₁ -C ₄ alkyl group, which may be the same or different well, a halogen atom, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl groups, C ₁ -C
₁ to 5 selected from ₄ alkoxy groups, halo C ₁ -C ₄ alkoxy groups, amino groups and C ₁ -C ₄ alkoxycarbonyl groups
Substituted phenyl C ₁ -C ₄ alkyl group having two substituents on the ring, phenylcarbonyl group, which may be the same or different,
Halogen atom, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo C ₁ -C ₄ alkoxy or C ₁ -C ₄ A substituted phenylcarbonyl group having 1 to 5 substituents selected from an alkoxycarbonyl group, a carbamoyl group, a C ₁ -C ₄ alkyl group which may be the same or different, a phenyl group or a halogen atom which may be the same or different A substituted phenyl group having 1 to 5 substituents selected from a C ₁ -C ₄ alkyl group, a halo C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group or a halo C ₁ -C ₄ alkoxy group A substituted carbamoyl group having 1 to 2 substituents selected from a phenylsulfonyl group, which may be the same or different, a halogen atom, a hydroxyl group,
Cyano group, C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group or
Substituted with a substituted phenylsulfonyl group having 1 to 5 substituents selected from a C ₁ -C ₄ alkoxycarbonyl group, a thiocarbamoyl group, a C ₁ -C ₄ alkyl group which may be the same or different, or a phenyl group Thiocarbamoyl group,
C ₁ -C ₄ alkoxy carbon imidoyl group, the same or different C ₁ -C ₄ has a substituent on the nitrogen atom which is also selected from a good C ₁ -C ₄ alkyl group or a phenyl group alkoxy carbon imidoyl group, Having a substituent on the nitrogen atom selected from a C ₁ -C ₄ alkylthiocarbonimidoyl group, a C ₁ -C ₄ alkyl group which may be the same or different, or a phenyl group
C ₁ -C ₄ alkylthio carbon imidoyl group, C ₁ -C ₄ alkylsulfinyl carbon imidoyl group, the same or different substituent which is selected from a good C ₁ -C ₄ alkyl group or a phenyl group on the nitrogen atom C ₁ -C ₄ alkylsulfinyl carbon imidoyl group, C ₁ -C ₄ alkylsulfonyl carbon imidoyl group, the same or different and good C ₁ -C also having
₄ alkyl or C ₁ -C ₄ alkylsulfonyl carbon imide-yl group having a substituent selected from a phenyl group on the nitrogen atom, an amidino group, the same or different and good C ₁ -C be
_{4 represents} an amidino group substituted by an alkyl group or a phenyl group, or a 5- to 6-membered heterocyclic ring which may be the same or different and has 1 to 3 hetero atoms selected from an oxygen atom, a nitrogen atom or a sulfur atom . ). ). When m is 1 or more, B is a hydrogen atom, a halogen atom,
A cyano group, which may be the same or different, a 5- to 6-membered heterocyclic ring having 1 to 3 heteroatoms selected from an oxygen atom, a nitrogen atom or a sulfur atom, which may be the same or different, a halogen atom, a hydroxyl group, Cyano group, mercapto group, C ₁ -C ₄
Alkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, carbonyl group, carboxyl group, carboxy C ₁ -C ₄
Alkyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxycarbonyl C ₁ -C ₄ alkyl group, amino group, carbamoyl group, one or two C ₁ -C ₄ which may be the same or different
A substituted carbamoyl group having a substituent selected from an alkyl group or a phenyl group, a carbamoyl C ₁ -C ₄ alkyl group, or one or two C ₁ -C ₄ which may be the same or different;
₁ selected from a substituted carbamoyl C ₁ -C ₄ alkyl group having a substituent selected from an alkyl group or a phenyl group
A substituted 5- to 6-membered heterocyclic ring having 1 to 3 heteroatoms selected from an oxygen atom, a nitrogen atom or a sulfur atom, ) R ^{5 1} (wherein, X is the same comb in the, R ⁵ is a hydrogen atom, C ₁ -C
₈ alkyl groups, halo C ₁ -C ₄ alkyl groups, phenyl groups, which may be the same or different, a halogen atom, a cyano group, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, or C ₁ -C
A substituted phenyl group having 1 to 5 substituents selected from ₄ alkoxycarbonyl groups, which may be the same or different, and 1 selected from an oxygen atom, a nitrogen atom or a sulfur atom
A 5- to 6-membered heterocycle having up to 3 heteroatoms, OR ⁶ (wherein R ⁶ is as defined above), S (O) nR ⁶ (where n and R ⁶ are as defined above) Or N (R ⁶ ) R ⁷ (wherein R ⁶ and R ⁷ are as defined above). ) OR ⁶ (wherein, R ⁶ is as defined above.), S (O) nR 6 ( wherein, n and R ⁶ are as defined ^{above.) N (R 6) R} 7 ( wherein, R ⁶ and R ⁷ is as defined ^{above.) N = C (R 6} ) R 7 ( wherein, R ⁶ and R ⁷ are the same as defined above.) or ^{oN = C (R 6) R} 7 ( wherein, R ⁶ and R The 1,2,3-thiadiazole derivative or a salt thereof according to claim 1, wherein ⁷ is the same as described above. 3. A disease control agent for agricultural and horticultural use, comprising the 1,2,3-thiadiazole derivative or a salt thereof according to claim 1 as an active ingredient. 4. An agricultural and horticultural disease control agent comprising the 1,2,3-thiadiazole derivative or a salt thereof according to claim 2 as an active ingredient. 5. An agricultural and horticultural disease controlling agent characterized by treating an agricultural and horticultural disease controlling agent according to claim 3 with an effective amount of a plant in which the occurrence of a plant disease is not preferable. A method for controlling plant diseases, characterized in that: 6. An agricultural and horticultural disease controlling agent characterized by treating an agricultural and horticultural disease controlling agent according to claim 4 with respect to a plant in which occurrence of a plant disease is not preferable. A method for controlling plant diseases, characterized in that: