JPH10152483A - Bis-thiadiazole derivative or its salt, agrochemical for controlling damage to agricultural or horticultural crop by disease, and usage of the agrochemical - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound useful as agrochemicals for controlling damages to agricultural or horticultural crops by diseases. SOLUTION: This compound is shown by formula I (R<1> and R<2> are each H, a 1-8C alkyl or the like; X<1> and X<2> are each O or S; Y<1> and Y<2> are each O, S or the like; and R is a 0-30C alkylene), e.g. bis(4-methyl-1,2,3-thiadiazole-5- carboxylic acid)ethylene. The objective compound is obtained by hydrolyzing and then halogenating a product from the reaction between compounds shown by formulas II and III (R' is a 1-8C alkyl; and R'' is a 1-4C alkyl or the like), after cyclizing the product with thionyl chloride, to produce a compound shown by formula IV (Hal is a halogen), and then by reacting it with a compound shown by formula V in the presence of a base in an inert solvent. The objective compound shows a very high controlling effect against crop diseases, including bacterial diseases, e.g. rice blast, wheat powdery mildew, grape downy mildew and cabbage slimy soft rot, and viral diseases, e.g. tobacco mosaic.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a bis-thiadiazole derivative or a salt thereof, and an agricultural and horticultural disease control agent containing the compound as an active ingredient.

[0002]

2. Description of the Related Art With respect to 1,2,3-thiadiazole derivatives, JP-A-2-149579 discloses a therapeutic agent for central nervous system diseases.
Nos. 181463, 4-234881 and Canadian Patent No. 947297 disclose it as a herbicidal and growth regulator.
No. 252242 discloses a bactericide.

[0003]

SUMMARY OF THE INVENTION The present inventors have conducted intensive studies in order to create a novel agricultural and horticultural disease controlling agent. The present invention has been found to be useful as an 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 and R ² may be the same or different, a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₄ alkyl group, a phenyl group, which may be the same or different, a halogen atom, nitro group, cyano group, hydroxyl group, mercapto 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, C ₁ -C ₄ Alkylthio group, halo C _1
1 to 5 substituents selected from a substituted amino group having 1 to 2 substituents selected from a -C ₄ alkylthio group, an amino group, or a C ₁ -C ₄ alkyl group or a phenyl group which may be the same or different Substituted or substituted phenyl group, which may be the same or different, a 5- to 6-membered heterocyclic ring having 1 to 3 hetero atoms selected from an oxygen atom, a sulfur atom or a nitrogen atom, or the same or different Good, halogen atom, nitro group, cyano group, hydroxyl group, mercapto group, C ₁ -C
₄ alkyl groups, halo C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy groups, halo C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ alkylthio groups, halo C ₁ -C ₄ alkylthio groups, amino groups, Or ₁ to 5 substituents selected from a substituted amino 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, and And represents a substituted 5- to 6-membered heterocycle having 1 to 3 heteroatoms selected from an oxygen atom, a sulfur atom or a nitrogen atom.

[0005] X ¹ and X ² may be the same or different,
Represents an oxygen atom or a sulfur atom, Y ¹ and Y ² may be the same or different, and an oxygen atom, a sulfur atom or

Embedded image wherein —N (R ³ ) — (wherein R ³ is described below). R is a C ₀ -C ₃₀ alkylene group,

Embedded image (Wherein R ³ and R ⁴ may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a 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, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylsulfinyl groups, C ₁ -C ₄ alkylsulfonyl group, hydroxy C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, an amino group, the same or different and, C ₁ -C ₄ alkyl group, phenyl group, or may be the same or different,
Halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl groups, C ₁ -C
₄ alkoxy group, halo C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, amino group, or C ₁ -C ₄ alkyl group which may be the same or different or phenyl group A substituted amino group having 1 to 2 substituents selected from substituted phenyl groups having 1 to 5 substituents selected from substituted amino groups having 1 to 2 substituents selected from:

An amino C ₁ -C ₄ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl group, a halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, amino group, or C ₁ -C ₄ which may be the same or different
Having 1-2 substituents selected from substituted phenyl groups having 1-5 substituents selected from substituted amino groups having 1-2 substituents selected from alkyl groups or phenyl groups Amino C ₁ -C ₄ alkyl group, phenyl group,
May be the same or different, halogen atom, nitro group, cyano group, hydroxyl group, mercapto 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
An alkoxy group, a C ₁ -C ₄ alkylthio group, a halo C ₁ -C ₄ alkylthio group, an amino group, or a C ₁ -C ₄ alkyl group or a phenyl group which may be the same or different.
1 to 1 selected from a substituted amino group having two substituents
Substituted phenyl group having 5 substituents, phenyl C ₁ -C ₄
An alkyl group, which may be the same or different, a halogen atom,

Nitro group, cyano group, hydroxyl group, mercapto group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄
From an alkoxy group, a halo C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a halo C ₁ -C ₄ alkylthio group, an amino group, or a C ₁ -C ₄ alkyl group or a phenyl group which may be the same or different. A substituted phenyl C ₁ -C ₄ alkyl group having 1 to 5 substituents selected from a substituted amino group having 1 to 2 substituents selected on the ring, a phenoxy group, which may be the same or different , halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto 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, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, an amino group, or the same or different Also good
1-2 selected from C ₁ -C ₄ alkyl groups or phenyl groups
1 to 5 selected from substituted amino groups having three substituents
Phenoxy group having two substituents on the ring, phenoxy C ₁ -C ₄ alkyl group, which may be the same or different, halogen atom, nitro group, cyano group, hydroxyl group, mercapto group, C ₁ -C ₄ alkyl group , Halo C ₁ -C ₄ alkyl group, C ₁ -C ₄
From an alkoxy group, a halo C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a halo C ₁ -C ₄ alkylthio group, an amino group, or a C ₁ -C ₄ alkyl group or a phenyl group which may be the same or different. A substituted phenoxy C ₁ -C ₄ alkyl group having 1 to 5 substituents selected from a substituted amino group having 1 to 2 substituents on the ring, which may be the same or different, and 5 to 6-membered heterocyclic ring having 1 to 3 heteroatoms selected from an atom, a sulfur atom or a nitrogen atom, which may be the same or different, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto 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 group, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, amino group, or may be the same or different C ₁
Having from 1 to 4 substituents selected from substituted amino groups having from 1 to 2 substituents selected from -C ₄ alkyl groups or phenyl groups, which may be the same or different, an oxygen atom,
Substituted 5- to 6-membered heterocyclic ring having 1 to 3 hetero atoms selected from a sulfur atom or a nitrogen atom, which may be the same or different, and 1 to 3 selected from an oxygen atom, a sulfur atom or a nitrogen atom 5- to 6-membered heterocycle C ₁ -C having the following heteroatoms:
₄ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, hydroxyl group, mercapto group, C ₁ -C
₄ alkyl groups, halo C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy groups, halo C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ alkylthio groups, halo C ₁ -C ₄ alkylthio groups, amino groups, Or _{1 to 4} substituents selected from a substituted amino 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, and And may be a substituted 5- to 6-membered heterocyclic C ₁ -C ₄ alkyl group having 1 to 3 heteroatoms selected from an oxygen atom, a sulfur atom or a nitrogen atom, or

[0008]

Embedded image (Wherein, R ⁶ is a C ₁ -C ₆ alkylene group, one or more halogen atoms which may be the same or different or a C ₁ -C ₆ alkylene group substituted by a C ₁ -C ₄ alkyl group, or

Embedded image —O—,

-S (O) n- (wherein, n is an integer of 0 to 2) or

[0009]

Embedded image -N (R ⁸⁾ - (wherein, R ⁸ is a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, A phenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto 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, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio groups An amino group, or ₁ to 5 substituents which may be the same or different and which are substituted amino groups having 1 to 2 substituents selected from a C ₁ -C ₄ alkyl group or a phenyl 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 nitro group, a cyano group, a hydroxyl group,
Mercapto 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, C ₁
-C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, amino group, or the same or different and having 1 to 2 substituents selected from C ₁ -C ₄ alkyl group or phenyl group A substituted phenyl C ₁ -C ₄ alkyl group having 1 to 5 substituents selected from an amino group, or

[0010]

Embedded image (Wherein, R ¹¹ may C ₁ -C ₆ alkylene group, or the same or different, C ₁ -C ₆ alkylene having one or more substituents selected from halogen atom or a C ₁ -C ₄ alkyl group R ¹² represents a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁
-C ₄ alkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, hydroxyl group, mercapto 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 group, C ₁ -C ₄
An alkylthio group, a halo C ₁ -C ₄ alkylthio group, an amino group, or a substituted amino 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 A substituted phenyl group having 1 to 5 substituents selected, a 5 to 6-membered heterocyclic ring having 1 to 3 hetero atoms which may be the same or different and selected from an oxygen atom, a sulfur atom or a nitrogen atom Or the same or different, a halogen atom, a nitro group, a cyano group,
A hydroxyl group, a mercapto 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, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, an amino group, or be the same or different and, C ₁ -C
₄ has 1 to 4 substituents selected from a substituted amino group having 1 to 2 substituents selected from an alkyl group or a phenyl group, may be the same or different, an oxygen atom, a sulfur atom or A substituted 5- to 6-membered heterocycle having 1 to 3 heteroatoms selected from a nitrogen atom, wherein Y ⁴ is

[0011]

Embedded image —O—,

Embedded image or —S— or

Embedded image -N (R ¹³⁾ - (. Wherein, R ¹³ is showing a hydrogen atom or a C ₁ -C ₄ alkyl group) indicates, X ⁴ represents an oxygen atom or a sulfur atom, q
Represents an integer of 0 to 1, and r represents an integer of 0 to 1. ). ) Represents a C ₁ -C ₆ alkylene group which may be interrupted, R ⁷ is a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group, a phenyl group, which may be the same or different, halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄
From an alkoxy group, a halo C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a halo C ₁ -C ₄ alkylthio group, an amino group, or a C ₁ -C ₄ alkyl group or a phenyl group which may be the same or different. A substituted phenyl group having 1 to 5 substituents selected from a substituted amino group having 1 to 2 substituents selected, a phenyl C ₁ -C ₄ alkyl group, which may be the same or different, and a halogen atom , nitro group, cyano group, hydroxyl group, mercapto 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, C ₁ -C ₄ alkylthio groups, halo C ₁ -C ₄ alkylthio groups, amino groups, or C ₁ -C ₄ which may be the same or different
A substituted phenyl C ₁ -C ₄ alkyl group having 1 to 5 substituents on a ring selected from a substituted amino group having 1 to 2 substituents selected from an alkyl group or a phenyl group, the same or different Which may have 1 to 3 heteroatoms selected from an oxygen atom, a sulfur atom, or a nitrogen atom;
A 6-membered hetero ring, or the same or different, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl group, a halo C ₁ -C ₄ alkyl group, a C ₁ -C ₄
From an alkoxy group, a halo C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a halo C ₁ -C ₄ alkylthio group, an amino group, or a C ₁ -C ₄ alkyl group or a phenyl group which may be the same or different. Having 1 to 5 substituents selected from a substituted amino group having 1 to 2 substituents on the ring,
Which may be identical or different, an oxygen atom, a sulfur atom, or a substituted 5-6 membered heterocyclic ring having 1-3 heteroatoms selected from nitrogen atom, Y ³ is

[0012]

Embedded image —O—,

Embedded image or —S— or

Embedded image -N (R ⁸⁾ - (. Wherein, R ⁸ is as defined above) indicates, X ³ represents an oxygen atom or a sulfur atom, m represents an integer of 0 to 5, p is 0
Or an integer of 1. A) represents an integer of 0 to 30. R ³ and R ⁴ may together form a ^3- to 8-membered ring by a C ₀ -C ₇ alkylene group, wherein the 3- to 8-membered ring is

[0013]

Embedded image —O—,

-S (O) n- (wherein, n represents an integer of 0 to 2),

-N (R ⁸ )-(wherein R ⁸ is as defined above) or

Embedded image -C (R ⁹ ) (R ¹⁰ ) — (wherein R ⁹ and R ¹⁰ may be the same or different, and include a halogen atom, a C ₁ -C ₄ alkyl group, or

[0014]

Embedded image Wherein R ¹¹ , R ¹² , X ⁴ , Y ⁴ , q and r are as defined above, and R ⁹ and R ¹⁰ are taken together to form a 3- to 7-membered C ₂ -C ₆ alkylene group. Rings can also be formed. )
Can also be interrupted. Or a C ₀ -C ₃₀ alkylene group which may be interrupted by one or more groups shown below, which may be the same or different.

Embedded image —O—,

-S (O) n- (wherein n is as defined above),

Embedded image —N (R ³ ) — (wherein R ³ is as defined above);

[0015]

-C (R ³ ) = C (R ⁴ )-(wherein R ³ and R ⁴ are the same as above),

Embedded image -C≡C-,

Embedded image (In the formula, Z is a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl group, a halo C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a halo C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ alkylthio groups, halo C ₁ -C ₄ alkylthio groups, amino groups, or C ₁ -C ₄ which may be the same or different
A substituted amino group having 1 to 2 substituents selected from an alkyl group or a phenyl group, or

[0016]

Embedded image (Wherein, R ⁶ , R ⁷ , Y ³ , X ³ , m and p are the same as above). ) Or

Embedded image (Wherein, Z is as defined above). The present invention relates to a bis-thiadiazole derivative represented by the formula (I) or a salt thereof, a plant disease controlling agent for agricultural and horticultural use containing the compound as an active ingredient, and a method for using the same.

In the bis-thiadiazole derivative represented by the general formula (I) of the present invention, in the definition of each substituent, "halogen atom" represents a chlorine atom, bromine atom, iodine atom or fluorine atom, and "C ₁ -C ₈ alkyl group "means having 1 to 1 carbon atoms.
8 represents a linear or branched alkyl group, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n - hexyl, n- heptyl, n- octyl an alkyl group such as, may be the same or different from the "halo C ₁ -C ₄ alkyl group", one or more carbon atoms 1 substituted with a halogen atom 4 represents a linear or branched alkyl group, which may be the same or different, and is a 5- to 6-membered heterocyclic ring having 1 to 3 hetero atoms selected from an oxygen atom, a nitrogen atom or 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,
A 5- to 6-membered heterocycle such as 2,4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, pyrrolidine, piperidine, morpholine, thiomorpholine, dithiolane, dithiane, piperazine, dioxolane, and imidazolidine is shown.

The salts of the bis-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, even if they are the same or different. Examples thereof include ammonium salts, guanidinium salts, and the like, which are well substituted with one or more C ₁ -C ₁₂ alkyl groups, phenyl groups, substituted phenyl groups, benzyl groups, or substituted benzyl groups. As preferred substituents in the general formula (I) of the present invention, R ¹ and R ² may be the same or different and include a methyl group, an ethyl group, an i-propyl group, a cyclopropyl group and the like.
X ¹ and X ² represent an oxygen atom, Y ¹ and Y ² represent an oxygen atom or —NH—, R represents a phenylene group,
An alkylene group having 2 to 6 carbon atoms,

Embedded image-(CH ₂ CH ₂ O) _1-3 -or

Embedded image And the like.

The bis-thiadiazole derivative represented by the general formula (I) of the present invention or a salt thereof can be produced, for example, by the following production methods. Manufacturing method 1.

Embedded image (In the formula, R, R ¹ , R ² , Y ¹ and Y ² are the same as above, and Hal represents a halogen atom.) The compound represented by the general formula (II) is prepared in the presence or absence of a base. Under the presence and absence or presence of an inert solvent, a compound of the general formula (I
V) by reacting with a compound represented by the general formula (I)
The bis-thiadiazole derivative represented by the following formula can be produced. This reaction is described in “New Experimental Chemistry Course”, Volume 15 (I
I), page 1012 (Maruzen Co., Ltd.) and the method described on page 1142, etc.

Manufacturing method 2. (When Y ¹ and Y ² are oxygen atoms)

Embedded image (In the formula, R, R ¹ , R ² and Hal are the same as described above.) The compound represented by the general formula (III) and the compound represented by the general formula (V) are present in the presence or absence of a base. The bis-thiadiazole derivative represented by the general formula (II) can be produced by reacting the mixture under the presence or absence of an inert solvent or in the absence thereof. This reaction can be produced according to the method described in Shin-Jikken Kagaku Koza, vol. 15, (II), p. 1008.

Manufacturing method 3.

Embedded image (Wherein R, R ¹ , R ² , Y ¹ , Y ² and Hal are the same as described above). In the presence or absence of the compound represented by the general formula (I
V) by reacting with a compound represented by the general formula (VI)
By reacting the compound (VI) with a compound represented by the general formula (II ′) without isolation or by isolating the compound represented by the general formula (I ′) -It is possible to produce thiadiazole derivatives. This reaction can be produced according to the known method described in Production Method 1.

The compounds represented by the general formula (II) and the general formula (III), which are the starting compounds of the production methods shown in the production methods 1, 2 and 3, can be produced by, for example, the following known production methods. Can be.

Embedded image (Wherein R ¹ and Hal are as defined above, and R ′ is C ₁ -C
_{8 represents} an alkyl group, and R ″ represents a C ₁ -C ₄ alkyl group, C ₁ -C ₄
It represents an alkoxy group or an amino group which may have a substituent. )

The compound represented by the general formula (X) and the compound represented by the general formula (IX)
By reacting a compound represented by the general formula (VIII), and isolating or not isolating the compound (VIII) to carry out a ring closure reaction with thionyl chloride to obtain a compound represented by the general formula (V
II), the compound (VII) is isolated,
Alternatively, the compound represented by the general formula (III) is hydrolyzed without isolation to give a compound represented by the general formula (III). The compound represented by (II) can be produced. This reaction is described in J. Am. Chem. Soc. , 77 , 5359
(1955) and the like. The compound represented by the general formula (II ') can be produced by the same method.

The following are typical examples of the bis-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. Me: methyl group, Et: ethyl group, Pr: propyl group,
Bu: butyl group, Ph: phenyl group or phenylene group,

Embedded image

[0025]

Embedded image

[0026]

Embedded image General formula (I)

Embedded image

[0027]

[Table 1] Table 1 ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 1 Me OO CH ₂ Me OO 2 Me OO (CH ₂ ) ₂ Me OO 3 Me OO (CH ₂ ) ₃ Me OO 4 Me OO (CH ₂ ) ₄ Me OO 5 Me OO (CH ₂ ) ₅ Me OO 6 Me OO (CH ₂ ) ₆ Me OO 7 Me OO (CH ₂ ) ₇ Me OO 8 Me OO (CH ₂ ) ₈ Me OO 9 Me OO (CH ₂ ) ₉ Me OO 10 Me OO (CH ₂ ) ₁₀ Me OO 11 Me OO (CH ₂ ) ₁₁ Me OO 12 Me OO (CH ₂ ) ₁₂ Me OO 13 Me OO (CH ₂ ) ₁₃ Me OO 14 Me OO (CH ₂ ) ₁₄ Me OO 15 Me OO (CH ₂ ) ₁₅ Me OO 16 Me OO (CH ₂ ) ₁₆ Me OO 17 Me OO (CH ₂ ) ₁₇ Me OO 18 Me OO (CH ₂ ) ₁₈ Me OO 19 Me OO (CH ₂ ) ₁₉ Me OO 20 Me OO (CH ₂ ) ₂₀ Me OO 21 Me OO CH ₂ CH (Me) Me OO 22 Me OO CH ₂ CH (CH ₂ F) Me OO ──────────────────────────────────

[0028]

[Table 2] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 23 Me OO CH ₂ CH (CH ₂ Cl) Me OO 24 Me OO CH ₂ CH (CH ₂ Br) Me OO 25 Me OO CH ₂ CH (Et) Me OO 26 Me OO CH ₂ CH (n-Pr) Me OO 27 Me OO CH ₂ CH (i- Pr) Me OO 28 Me OO CH ₂ CH (n-Bu) Me OO 29 Me OO CH ₂ CH (i-Bu) Me OO 30 Me OO CH ₂ CH (t-Bu) Me OO 31 Me OO CH ₂ CH ( nC ₆ H ₁₃ ) Me OO 32 Me OO CH ₂ CH (nC ₈ H ₁₇ ) Me OO 33 Me OO CH ₂ CH (nC ₁₀ H ₂₁ ) Me OO 34 Me OO CH ₂ CH (nC ₁₂ H ₂₅ ) Me OO 35 Me OO CH ₂ CH (Ph) Me OO 36 Me OO CH ₂ CH (2-Cl-Ph) Me OO 37 Me OO CH ₂ CH (3-Cl-Ph) Me OO 38 Me OO CH ₂ CH (4-Cl -Ph) Me OO 39 Me OO CH ₂ CH (2-Me-Ph) Me OO 40 Me OO CH ₂ CH (3-Me-Ph) Me OO 41 Me OO CH ₂ CH (4-Me-Ph) Me OO 42 Me OO CH ₂ CH (4-i-Pr-Ph) Me OO 43 Me OO CH ₂ CH (3-i-PrO-Ph) Me OO 44 Me OO CH ₂ CH (4-Br-Ph) Me OO ─ ────────── ───────────────────────

[0029]

[Table 3] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 45 Me OO CH ₂ CH (4- CF ₃ -Ph) Me OO 46 Me OO CH (Me) CH (Me) Me OO 47 Me OO CH ₂ C (Me) ₂ Me OO 48 Me OO CH (Me) C (Me) ₂ Me OO 49 Me OOC ( Me) ₂ C (Me) ₂ Me OO 50 Me OO CH ₂ CH (CH ₂ OMe) Me OO 51 Me OO CH ₂ CH (CH ₂ OPh) Me OO 52 Me OO CH ₂ CH (CH ₂ O (3-Cl -Ph)) Me OO 53 Me OO CH ₂ CH (CH ₂ O (4-MeO-Ph)) Me OO 54 Me OO CH ₂ CH (CH ₂ O-CH ₂ Ph) Me OO 55 Me OO CH ₂ CH ( CH ₂ O-COMe) Me OO 56 Me OO CH ₂ CH (CH ₂ O-COBu-t) Me OO 57 Me OO CH ₂ CH (CH ₂ O-COPh) Me OO 58 Me OO CH ₂ CH (CH ₂ O -CO (2-Cl-Ph)) Me OO 59 Me OO CH ₂ CH (CH ₂ O-CO (3-Cl-Ph)) Me OO 60 Me OO CH ₂ CH (CH ₂ O-CO (4-Cl -Ph)) Me OO 61 Me OO CH ₂ CH (CH ₂ O-CO (4-CF ₃ -Ph)) Me OO 62 Me OO CH ₂ CH (CH ₂ SMe) Me OO 63 Me OO CH ₂ CH (CH ₂ SOMe) Me OO 64 Me OO CH ₂ CH (CH ₂ SO ₂ Me) Me OO 65 Me OO CH ₂ CH (CH ₂ N (Me) ₂ ) Me OO 66 Me OO CH ₂ CH (CH ₂ N (Et) ₂ ) Me OO ────────────────── ────────────────

[0030]

[Table 4] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 67 Me OO CH ₂ CH (CH ₂ -Q ₁ ) Me OO 68 Me OO CH ₂ CH (CH ₂ -Q ₂ ) Me OO 69 Me OO CH ₂ CH (CH ₂ NHCOMe) Me OO 70 Me OO CH ₂ CH (CH ₂ NHCOEt) Me OO 71 Me OO CH ₂ CH (CH ₂ NHCOPr-i) Me OO 72 Me OO CH ₂ CH (CH ₂ NHCOBu-n) Me OO 73 Me OO CH ₂ CH (CH ₂ NHCOPh) Me OO 74 Me OO CH ₂ CH (CH ₂ NHCO (2-Cl-Ph) Me OO 75 Me OO CH ₂ CH (CH ₂ NHCO (3-Cl-Ph) Me OO 76 Me OO CH ₂ CH (CH ₂ NHCO (4-Cl-Ph) Me OO 77 Me OO CH ₂ CH (CN) Me OO 78 Me OO CH (Ph) CH (Ph) (meso) Me OO 79 Me OO CH (Ph) CH (Ph) (+/-) Me OO 80 Me OO CH ₂ CH ₂ CH (Me) Me OO 81 Me OO CH ₂ CH (Me) CH ₂ Me OO 82 Me OO CH ₂ C (Me) ₂ CH ₂ Me OO 83 Me OO CH ₂ C (CH ₂ Br) ₂ CH ₂ Me OO 84 Me OO CH (Me) CH ₂ CH (Me) Me OO 85 Me OO CH (Me) CH ₂ C (Me) ₂ Me OO 86 Me OOC (Me) ₂ CH ₂ C (Me) ₂ Me OO 87 Me OO CH ₂ CM e) (Et) CH ₂ Me OO 88 Me OO CH ₂ C (Et) ₂ CH ₂ Me OO ─────────────────────────── ───────

[0031]

[Table 5] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 89 Me OO CH ₂ C (Me) (n-Pr) CH ₂ Me OO 90 Me OO CH (i-Pr) C (Me) ₂ CH ₂ Me OO 91 Me OO CH (n-Pr) C (Et) ₂ CH ₂ Me OO 92 Me OO CH ₂ C (Et) (n-Bu) CH ₂ Me OO 93 Me OO CH ₂ C (Me) (CH ₂ O-COQ ₃ ) CH ₂ Me OO 94 Me OO CH ₂ C (NO ₂ ) (CH ₂ O-COQ ₃ ) CH ₂ Me OO 95 Me OO CH ₂ C (Et) (CH ₂ O-COQ ₃ ) CH ₂ Me OO 96 Me OO CH ₂ C (Et) (CH ₂ O-COQ ₃ ) CH ₂ Me OO 97 Me OO CH ₂ CH (Cl) CH ₂ Me OO 98 Me OO CH ₂ CH (Br) CH ₂ Me OO 99 Me OO CH ₂ C (Br) (NO ₂ ) CH ₂ Me OO 100 Me OO CH ₂ CH (OH) CH ₂ Me OO 101 Me OO CH ₂ CH (OMe) CH ₂ Me OO 102 Me OO CH ₂ CH (OCH ₂ Ph) CH ₂ Me OO 103 Me OO CH ₂ CH (O-COMe) CH ₂ Me OO 104 Me OO CH ₂ CH (O-COPh) CH ₂ Me OO 105 Me OO CH ₂ CH (O-CO (4-Cl-Ph)) CH ₂ Me OO 106 Me OO CH ₂ CH (O-COQ ₃ ) CH ₂ Me OO 107 Me OO CH ₂ CH (O-COOMe) CH ₂ Me OO 108 Me OO CH ₂ CH (NH ₂ ) CH ₂ Me OO 109 Me OO CH ₂ C (Me) (NHCOQ ₃ ) CH ₂ Me OO 110 Me OO CH ₂ C (Et) (NHCOQ ₃ ) CH ₂ Me OO ────── ────────────────────────────

[0032]

[Table 6] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 111 Me OO CH ₂ C (CH ₂ COQ ₃ ) (NHCOQ ₃ ) CH ₂ Me OO 112 Me OO CH ₂ CH (NHCOMe) CH ₂ Me OO 113 Me OO CH ₂ CH (NHCOPh) CH ₂ Me OO 114 Me OO CH ₂ CH (NHCOQ ₃ ) CH ₂ Me OO 115 Me OO CH ₂ CH (SMe) CH ₂ Me OO 116 Me OO CH ₂ C (COOMe) ₂ CH ₂ Me OO 117 Me OO CH ₂ C (COOEt) ₂ CH ₂ Me OO 118 Me OO CH ₂ C (COOPr -i) ₂ CH ₂ Me OO 119 Me OO CH ₂ C (CN) ₂ CH ₂ Me OO 120 Me OO CH ₂ CH ₂ C (Me) ₂ Me OO 121 Me OO CH (Me) CH ₂ C (Me) ₂ Me OO 122 Me OO CH (Me) CH ₂ CH ₂ C (Me) ₂ Me OO 123 Me OO CH ₂ CH (Cl) CH (Cl) CH ₂ Me OO 124 Me OO CH ₂ CH (Br) CH (Br) CH ₂ Me OO 125 Me OO CH ₂ CH ₂ CH (OH) CH ₂ Me OO 126 Me OO CH ₂ CH ₂ CH (O-COQ ₃ ) CH ₂ Me OO 127 Me OO CH ₂ CH (O-COQ ₃ ) CH (O-COQ ₃ ) CH ₂ Me OO 128 Me OO CH ₂ CH (COOMe) CH (COOMe) CH ₂ Me OO 129 Me OO CH ₂ CH (COOEt) CH (COOEt ) CH ₂ Me OO 130 Me OO CH ₂ CH ₂ CH ₂ CH (Me) Me OO 131 Me OO CH ₂ CH ₂ CH ₂ CH ₂ CH (Me) Me OO 132 Me OO (CH ₂ ) ₃ C (NO ₂ ) ((CH ₂ ) ₃ O-COQ ₃ ) (CH ₂ ) ₃ Me OO ──────────────────────────────── ──

[0033]

[Table 7] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 133 Me OO CH ₂ CH = CHCH ₂ (E) Me OO 134 Me OO CH ₂ CH = CHCH ₂ (Z) Me OO 135 Me OO CH ₂ C (Me) = C (Me) CH ₂ (E) Me OO 136 Me OO CH ₂ CH = C (Me ) CH ₂ (E) Me OO 137 Me OO CH ₂ CH = C (Me) CH ₂ (Z) Me OO 138 Me OO CH ₂ CH = C (Cl) CH ₂ (E) Me OO 139 Me OO CH ₂ CH _{= C (Cl) CH 2 (} Z) Me OO 140 Me OO CH 2 C≡CCH 2 Me OO 141 Me OO 1-cyclo-C 5 H 8 -2 Me OO 142 Me OO 1-cyclo-C 5 H 8 - 3 Me OO 143 Me OO 1-cyclo-C ₆ H ₁₀ -2 Me OO 144 Me OO 1-cyclo-C ₆ H ₁₀ -3 Me OO 145 Me OO 1-cyclo-C ₆ H ₁₀ -4 Me OO 146 Me OOQ ₂₀ Me OO 147 Me OO 1- (5-O-COQ ₃ -cyclo-C ₆ H ₁₀ ) -3 Me OO 148 Me OO CH ₂ -1-cyclo-C ₆ H ₁₀ -1 Me OO 149 Me OO CH _{2 -1-cyclo-C 6 H} 10 -2-CH 2 Me OO 150 Me OOQ 21 Me OO 151 Me OOQ 22 Me OO 152 Me OO 1-cyclo-C 8 H 14 -2 Me OO 153 Me OOQ 23 Me OO 154 M e OO 1-Ph-2 Me OO ──────────────────────────────────

[0034]

[Table 8]

[0035]

[Table 9]

[0036]

[Table 10]

[0037]

[Table 11] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 202 Me OO CH ₂ CH ₂ SOCH ₂ CH ₂ Me OO 203 Me OO CH ₂ CH ₂ SO ₂ CH ₂ CH ₂ Me OO 204 Me OO CH ₂ CH ₂ CH ₂ SCH ₂ CH ₂ CH ₂ Me OO 205 Me OO CH ₂ CH ₂ (SCH ₂ CH ₂ ) ₂ Me OO 206 Me OO CH ₂ CH ₂ NHCH ₂ CH ₂ Me OO 207 Me OO CH ₂ CH ₂ N (Me) CH ₂ CH ₂ Me OO 208 Me OO CH ₂ CH ₂ N (Et) CH ₂ CH ₂ Me OO 209 Me OO CH ₂ CH ₂ N (Ph) CH ₂ CH ₂ Me OO 210 Me OO CH ₂ CH ₂ N (3-Cl-Ph) CH ₂ CH ₂ Me OO 211 Me OO CH ₂ CH ₂ N (COMe) CH ₂ CH ₂ Me OO 212 Me OO CH ₂ CH ₂ N (COEt) CH ₂ CH ₂ Me OO 213 Me OO CH ₂ CH ₂ N (COBu-t) CH ₂ CH ₂ Me OO 214 Me OO CH ₂ CH ₂ N (COPh ) CH ₂ CH ₂ Me OO 215 Me OO CH ₂ CH ₂ N (CO (4-Cl-Ph)) CH ₂ CH ₂ Me OO 216 Me OO CH ₂ CH ₂ N (COQ ₃ ) CH ₂ CH ₂ Me OO 217 Me OO CH ₂ CH ₂ N (COOMe) CH ₂ CH ₂ Me OO 218 Me OO CH (Me) CH ₂ N (COQ ₃ ) CH ₂ CH (Me ) Me OO 219 Me OO CH ₂ CH ₂ N (CH ₂ CH ₂ O-COQ ₃ ) CH ₂ CH ₂ Me OO 220 Me OO CH (Me) CH ₂ N (CH ₂ CH ₂ O-COQ ₃ ) CH ₂ CH ₂ Me OO 221 Me OO CH ₂ CH ₂ -Q ₄ -CH ₂ CH ₂ Me OO 222 Me OO CH ₂ CH ₂ (N (COMe) CH ₂ CH ₂ ) ₂ Me OO 223 Me OO CH ₂ CH ₂ (N ( COEt) CH ₂ CH ₂ ) ₂ Me OO ──────────────────────────────────

[0038]

[Table 12] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 224 Me OO CH ₂ CH ₂ (N (COPh) CH ₂ CH ₂ ) ₂ Me OO 225 Me OO CH ₂ CH ₂ (N (COQ ₃ ) CH ₂ CH ₂ ) ₂ Me OO 226 Me OO CH ₂ -CO-CH ₂ Me OO 227 Me OO CH _2- CO-CH (OH) CH ₂ Me OO 228 Me OO CH ₂ -CO-CH (O-COQ ₃ ) CH ₂ Me OO 229 Me OO CH ₂ -CO-CO-CH ₂ Me OO 230 Me OOQ ₅ Me OO 231 Me OOQ ₆ Me OO 232 Me OOQ ₇ Me OO 233 Me OOQ ₈ Me OO 234 Me OO (CH ₂ ) ₂ Me OS 235 Me OO (CH ₂ ) ₃ Me OS 236 Me OO (CH ₂ ) ₄ Me OS 237 Me OO (CH ₂ ) ₅ Me OS 238 Me OO (CH ₂ ) ₆ Me OS 239 Me OO (CH ₂ ) ₇ Me OS 240 Me OO (CH ₂ ) ₈ Me OS 241 Me OO CH (Me) CH ₂ Me OS 242 Me OO CH (Me) C (Me) Me OS 243 Me OO CH ₂ CH (O-COQ ₃ ) CH ₂ Me OS 244 Me OO CH ₂ CH (S-COQ ₃ ) CH ₂ Me OS 245 Me OO CH ₂ (S _{-COQ 3) CH (S-COQ} 3) CH 2 Me OS ───────────────── ─────────────────

[0039]

[Table 13] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 246 Me OO (CH ₂ ) ₂ Me O N-Me 247 Me OO (CH ₂ ) ₂ Me O N-Et 248 Me OO (CH ₂ ) ₂ Me O N-Pr-n 249 Me OO (CH ₂ ) ₂ Me O N-Pr-i 250 Me OO (CH ₂ ) ₂ Me O N-Bu-t 251 Me OO (CH ₂ ) ₂ Me O N-Ph 252 Me OO (CH ₂ ) ₂ Me O NCH ₂ Ph 253 Me OO (CH ₂ ) ₃ Me O NH 254 Me OO (CH ₂ ) ₄ Me O NH 255 Me OO (CH ₂ ) ₅ Me O NH 256 Me OO (CH ₂ ) ₆ Me O NH 257 Me OO (CH ₂ ) ₇ Me O NH 258 Me OO (CH ₂ ) ₈ Me O NH 259 Me OO CH ₂ CH (Me) Me O NH 260 Me OO CH ₂ CH (Et) Me O NH 261 Me OO CH ₂ CH (Ph) Me O NH 262 Me OO CH ₂ CH (CH ₂ Ph ) Me O NH 263 Me OO CH ₂ C (Me) ₂ Me O NH 264 Me OO CH (Ph) CH ₂ Me O NH 265 Me OO CH (3-Q ₃ COOPh) CH ₂ Me O NH 266 Me OO CH ( 4-Q ₃ COOPh) CH ₂ Me O NH 267 Me OO CH (Ph) CH ₂ Me O N-Me ──────────────── ──────────────────

[0040]

[Table 14] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 268 Me OO CH (CH ₂ Ph) CH ₂ Me O NH 269 Me OO CH (Ph) CH (Me) Me O NH 270 Me OO CH (Ph) CH (Me) Me O N-Me 271 Me OO CH (4-Q ₃ COOPh) CH (Me) Me O N-Me 272 Me OOQ ₉ Me O − 273 Me OOQ ₁₀ Me O − 274 Me OO 2,2,6,6-Me ₄ -Q ₁₀ Me O − 275 Me OO CH ₂ -Q ₁₁ Me O − 276 Me OO CH ₂ -Q ₉ Me O − 277 Me OO CH ₂ -Q ₁₀ Me O − 278 Me OO CH ₂ CH ₂ -Q ₁₁ Me O − 279 Me OO CH ₂ CH ₂ -Q ₉ Me O − 280 Me OO CH ₂ CH ₂ -Q ₁₀ Me O − 281 Me OO 1-Ph-2 Me O NH 282 Me OO 1-Ph-3 Me O NH 283 Me OO 1-Ph-3 Me O NH 284 Me OO 1- (5 -Cl-Ph) -2 Me O NH 285 Me OO 1- (4-Me-Ph) -2 Me O NH 286 Me OO 1- (4-t-Bu-Ph) -2 Me O NH 287 Me OO 1 -(2-Me-Ph) -3 Me O NH 288 Me OO 1- (2,6-Cl ₂ -Ph) -4 Me O NH 289 Me OO 1- (4-Me-Ph) -3 Me O NH ──────────── ─────────────────────

[0041]

[Table 15]

[0042]

[Table 16] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 310 Me O NH (CH ₂ ) ₂ Me O N-Pr-i 311 Me O NH (CH ₂ ) ₃ Me O NH 312 Me O NH (CH ₂ ) ₃ Me O N-Me 313 Me O NH (CH ₂ ) ₄ Me O N-Pr-n 314 Me O NH (CH ₂ ) ₅ Me O NH 315 Me O NH (CH ₂ ) ₆ Me O NH 316 Me O NH (CH ₂ ) ₇ Me O NH 317 Me O NH (CH ₂ ) ₈ Me O NH 318 Me O NH (CH ₂ ) ₉ Me O NH 319 Me O NH (CH ₂ ) ₁₀ Me O NH 320 Me O NH (CH ₂ ) ₁₁ Me O NH 321 Me O NH (CH ₂ ) ₁₂ Me O NH 322 Me O NH CH ₂ CH (Me) Me O NH 323 Me O NH CH ₂ C (Me) ₂ CH ₂ Me O NH 324 Me O NH CH ₂ CH (COOEt) Me O NH 325 Me O NH CH ₂ CH ₂ CH (COOEt) Me O NH 326 Me O NH CH ₂ CH ₂ CH ₂ CH (COOEt) Me O NH 327 Me O NH CH ₂ CH ₂ CH ₂ CH ₂ CH (COOEt) Me O NH 328 Me O NH CH ₂ CH ₂ OCH ₂ CH ₂ Me O NH 329 Me O NH CH ₂ CH ₂ (OCH ₂ CH ₂ ) ₂ Me O NH 330 Me O NH CH ₂ CH ₂ (OCH ₂ CH ₂ ) ₃ Me O NH 331 Me O NH CH ₂ CH ₂ (OCH ₂ CH ₂ ) ₄ Me O NH ───────────────────────── ─────────

[0043]

[Table 17] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ────────────────────────────────── 332 Me O NH CH ₂ CH ₂ N (Me) CH ₂ CH ₂ Me O NH 333 Me O NH CH ₂ CH ₂ N (COQ ₃ ) CH ₂ CH ₂ Me O NH 334 Me O NH CH ₂ CH ₂ (N (COQ ₃ ) CH ₂ CH ₂ ) ₂ Me O NH 335 Me O NH CH ₂ CH ₂ (N (COQ ₃ ) CH ₂ CH ₂ ) ₃ Me O NH 336 Me O NH CH ₂ CH ₂ (N (COQ ₃ ) CH ₂ CH ₂ ) ₄ Me O NH 337 Me O NH CH ₂ CH ₂ (N (COQ ₃ ) CH ₂ CH ₂ ) ₅ Me O NH 338 Me O NH CH ₂ CH ₂ (N (COQ ₃ ) CH ₂ CH ₂ ) ₆ Me O NH 339 Me O NH CH ₂ CH ₂ N (COQ ₃ )-(CH ₂ ) ₃ Me O NH 340 Me O NH CH ₂ CH ₂ N (Me)-(CH ₂ ) ₃ Me O NH 341 Me O NH (CH ₂ ) ₃ N (COQ ₃ )-(CH ₂ ) ₃ Me O NH 342 Me O NH (CH ₂ ) ₄ N (COQ ₃ )-(CH ₂ ) ₄ Me O NH 343 Me O NH (CH ₂ ) ₄ (N (COQ ₃ )- (CH ₂ ) ₄ ) ₂ Me O NH 344 Me O NH (CH ₂ ) ₄ (N (COQ ₃ )-(CH ₂ ) ₄ ) ₃ Me O NH 345 Me O NH (CH ₂ ) ₆ N (COQ ₃ ) -(CH ₂ ) ₆ Me O NH 346 Me O NH 1-cyclo-C ₆ H ₁₀ -2 Me O NH 347 Me O NH 1-cyclo-C ₆ H ₁₀ -5 Me O NH 348 Me O NH Q ₁₀ Me O − 349 Me O NH CH ₂ CH ₂ Q ₁₀ Me O − 350 Me O NH 1-Ph-2 Me O NH 351 Me O NH 1-Ph-3 Me O NH 352 Me O NH 1-Ph-4 Me O NH 353 Me O NH 1- (4-Cl- Ph) -2 Me O NH ──────────────────────────────────

[0044]

[Table 18] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ───────────────────────────────── 354 Me O NH 1- (4,5 -Me ₂ -Ph) -2 Me O NH 355 Me O NH 1- (4-OMe-Ph) -2 Me O NH 356 Me O NH 1- (2-Me-Ph) -3 Me O NH 357 Me O NH 1- (4-Me-Ph) -3 Me O NH 358 Me O NH 1- (4-OMe-Ph) -3 Me O NH 359 Me O NH 1- (2-Cl-Ph) -4 Me O NH 360 Me O NH 1- (2,5-Cl ₂ -Ph) -4 Me O NH 361 Me O NH 1- (2,6-Cl ₂ -Ph) -4 Me O NH 362 Me O NH 1- ( 2-OMe-Ph) -4 Me O NH 363 Me O NH 1- (1,3,5,6-Me ₄ -Ph) -4 Me O NH 364 Me ON-Me (CH ₂ ) ₂ Me ON -Me 365 Me O N-Et (CH ₂ ) ₂ Me O N-Et 366 Me ON-Pr-n (CH ₂ ) ₂ Me ON-Pr 367 Me ON-Pr-i (CH ₂ ) ₂ Me O N-Pr 368 Me O − Q ₄ Me O − 369 Me O − Q ₁₂ Me O − 370 Me O − Q ₁₃ Me O − 371 Me O − Q ₁₄ Me O − 372 Et OO (CH ₂ ) ₂ Et OO 373 Pr-i OO (CH ₂ ) ₂ Pr-i OO 374 CH ₂ Cl OO (CH ₂ ) ₂ CH ₂ Cl OO 375 CF ₃ OO (CH ₂ ) ₂ CF ₃ OO ──────────────────────────────────

[0045]

[Table 19] Table 1 (continued) ────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² ─────────────────────────────────── 376 Ph OO (CH ₂ ) ₂ Ph OO 377 2-Cl-Ph OO (CH ₂ ) ₂ 2-Cl-Ph OO 378 3-Cl-Ph OO (CH ₂ ) ₂ 3-Cl-Ph OO 379 4-Cl-Ph OO (CH ₂ ) ₂ 4-Cl-Ph OO 380 2-Me-Ph OO (CH ₂ ) ₂ 2-Me-Ph OO 381 3-Me-Ph OO (CH ₂ ) ₂ 3-Me-Ph OO 382 4-Me-Ph OO ( CH ₂ ) ₂ 4-Me-Ph OO 383 4-t-Bu-Ph OO (CH ₂ ) ₂ 4-t-Bu-Ph OO 384 2-CF ₃ -Ph OO (CH ₂ ) ₂ 2-CF _3- Ph OO 385 4-CF ₃ -Ph OO (CH ₂ ) ₂ 4-CF ₃ -Ph OO 386 2,4-Me ₂ -Ph OO (CH ₂ ) ₂ 2,4-Me ₂ -Ph OO 387 3,4 -Me ₂ -Ph OO (CH ₂ ) ₂ 3,4-Me ₂ -Ph OO 388 4-OH-Ph OO (CH ₂ ) ₂ 4-OH-Ph OO 389 4-MeO-Ph OO (CH ₂ ) ₂ 4-MeO-Ph OO 390 4-CF ₃ O-Ph OO (CH ₂ ) ₂ 4-CF ₃ O-Ph OO 391 4-PhO-Ph OO (CH ₂ ) ₂ 4-PhO-Ph OO 392 2,4 -(MeO) ₂ -Ph OO (CH ₂ ) ₂ 2,4- (MeO) ₂ -Ph OO 393 3,4- (MeO) ₂ -Ph OO (CH ₂ ) ₂ 3,4- (MeO) _2- Ph OO 394 4-C OOMe-Ph OO (CH ₂ ) ₂ 4-COOMe-Ph OO 395 2,4-Cl ₂ -Ph OO (CH ₂ ) ₂ 2,4-Cl ₂ -Ph OO 396 3,4-Cl ₂ -Ph OO ( (CH ₂ ) ₂ 3,4-Cl ₂ -Ph OO 397 Q ₁₅ OO (CH ₂ ) ₂ Q ₁₅ OO ───────────────────────── ─────────

[0046]

[Table 20] Table 1 (continued) ─────────────────────────────────── No R ¹ X ¹ Y ¹ RR ² X ² Y ² 398 398 Q ₁₆ OO (CH ₂ ) ₂ Q ₁₆ OO 399 Q ₁₇ OO (CH ₂ ) ₂ Q ₁₇ OO 400 Q ₁₈ OO (CH ₂ ) ₂ Q ₁₈ OO 401 Q ₁₉ OO (CH ₂ ) ₂ Q ₁₉ OO 402 6-Cl-Q ₁₉ OO ( _{CH 2) 2 6-Cl-} Q 19 OO 403 Me S NH (CH 2) 2 Me S NH 404 Me S NH (CH 2) 3 Me S NH 405 Me S NH (CH 2) 4 Me S NH 406 Me S NH 1-Ph-2 Me S NH 407 Me S NH 1-Ph-3 Me S NH 408 Me S NH 1-Ph-4 Me S NH ─────────────────表 In Table 1, for example, R of compound No. 141 is “1-cyclo-C ₅ H ₈
“-2” indicates that Y ¹ and Y ² are bonded to the ^1- and 2-positions of the cyclopentyl ring, respectively, and the compound No.
The R in 154 is "1-Ph-2" because the 1,2-position in which Y ¹ and Y ² are bonded to the ^1- and 2-positions of the phenyl ring, respectively.
It represents a phenylene group.

Table 2 shows the physical properties of representative compounds shown in Table 1.

Table 2 ────────────────────────────────── Physical properties of Compound No. 表───────────────────────────── 2 m. p. 54 ° C 4 m. p. 91 ° C. 21 paste [NMR (CDCl ₃ / TMS, δ value (ppm))] 1.47 (d, 6.6 Hz, 3H), 2.94 (s, 6H), 4.40 (dd, 6.7 Hz, 12.1 Hz, 1H) 4.60 ( dd, 3.2 Hz, 12.1 Hz, 1 H), 5.4-5.6 (m, 1 H) 35 nD 1.5722 (22 ° C.) 82 nD 1.5403 (22 ° C.) 95 m. p. 95 ° C 96 m. p. 190 ° C. 106 paste [NMR (CDCl ₃ / TMS, δ value (ppm))] 2.97 (s.9H), 4.60 (dd.2H), 4.75 (dd.2H), 5.65-5.80 (m.1H). m. p. 79 ° C 156 m. p. 205 ° C 166 m. p. 184 ° C 176 m. p. 149 ° C 184 m. p. 122 ° C 187 nD 1.5416 (26 ° C) 188 nD 1.5325 (26 ° C) 196 nD 1.5222 (26 ° C) ───────────────────── ─────────────

[0048]

Table 22 (Continued) 化合物 Compound No. Physical Properties ── ──────────────────────────────── 197 paste [NMR (CDCl ₃ / TMS, δ value (ppm))] 2.95 (s.6H), 3.50-3.70 (m. ≒ 24H), 3.76-3.82 (m.4H), 4.45-4.52 (m.4H) .198 paste [NMR (CDCl ₃ / TMS, δ value (ppm)) ] 2.97 (s.6H), 3.57-3.75 (m. ≒ 38H), 3.76-3.83 (m.4H), 4.45-4.53 (m.4H). 214 nD 1.5627 (21 ° C.) 219 paste [NMR ( CDCl ₃ / TMS, δ value (ppm))] 2.92 (s.69H), 2.96-3.06 (m.6H), 4.34-4.45 (m.6H). 281 m. p. 112 ° C 282 m. p. 152 ° C 283 m. p. 167 ° C 288 m. p. 164 ° C. 306 m. p. 149 ° C 350 m. p. 189 ° C 351 m. p. 210 ° C. 352 m. p. 260 ℃ ──────────────────────────────────

The following are typical examples, prescription examples and test examples of the present invention, but the present invention is not limited to these. Embodiment 1 FIG. Production of bis (4-methyl-1,2,3-thiadiazole-5-carboxylic acid) ethylene (Compound No. 2).

Embedded image 0.80 g (4.9 mmol) of 4-methyl-1,2,2
30 m of 3-thiadiazole-5-carbonyl chloride
l of tetrahydrofuran and 0.12 g (2.0
Mmol) of ethylene glycol, and 0.50 ml of triethylamine was added dropwise with stirring at room temperature.
The reaction was performed at room temperature for 4 hours. After completion of the reaction, ethyl acetate was added to the reaction solution, and the organic layer was washed with aqueous hydrochloric acid and aqueous sodium bicarbonate in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to obtain 0.34 g of the desired product. Physical properties m. p. 54 ° C, 56% yield

Embodiment 2 FIG. (Bis (4-methyl-1,
Production of 2,3-thiadiazole-5-carboxylic acid) 2-butynylene (Compound No. 140).

Embedded image 0.70 g (4.3 mmol) of 4-methyl-1,2,2
30 m of 3-thiadiazole-5-carbonyl chloride
l of tetrahydrofuran, and 0.15 g (1.7
Mmol) of 2-butyne-1,4-diol
While stirring at room temperature, 0.50 ml of triethylamine was added dropwise, and the reaction was carried out at room temperature for 4 hours. After the reaction,
Ethyl acetate was added to the reaction solution, and the organic layer was washed with aqueous hydrochloric acid and aqueous sodium bicarbonate in that order, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 2: Purification in 1) gave 0.34 g of the desired product. Physical properties m. p. 79 ° C, 61% yield

Embodiment 3 FIG. (Bis (4-methyl-1,
Production of 2,3-thiadiazole-5-carboxylic acid) p-phenylene (Compound No. 156).

Embedded image 1.0 g (6.2 mmol) of 4-methyl-1,2,3
30 ml of thiadiazole-5-carbonyl chloride
Was dissolved in tetrahydrofuran, 0.27 g (2.5 mmol) of p-hydroquinone was added, and 0.50 ml of triethylamine was added dropwise with stirring at room temperature, and the reaction was carried out at room temperature for 4 hours. After completion of the reaction, ethyl acetate was added to the reaction solution, and the organic layer was washed with aqueous hydrochloric acid and aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane:
Purification with ethyl acetate (2: 1) yielded 0.30 g of the desired product. Physical properties m. p. 205 ° C, 34% yield

Embodiment 4 FIG. (Bis (4-methyl-1,
2,3-thiadiazole-5-carboxylic acid) p-α, α
-Production of xylylene (compound No 184).

Embedded image 0.50 g (3.5 mmol) of 4-methyl-1,2,2
3-Thiadiazole-5-carboxylic acid is dissolved in 30 ml of acetonitrile, and 0.37 g (1.4 mmol) of p-α, α-xylylene dibromide and 0.50 g
(3.6 mmol) of anhydrous potassium carbonate was added, and the mixture was refluxed for 4 hours under heating. After completion of the reaction, ethyl acetate was added to the reaction solution, and the organic layer was dried over anhydrous magnesium sulfate.
The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to obtain 0.15 g of the desired product. Physical properties m. p. 122 ° C, 27% yield

Embodiment 5 FIG. (Bis (4-methyl-1,
Production of 2,3-thiadiazole-5-carboxylic acid) poly (oxyethylene) average n = 4 (Compound No. 196).

Embedded image 1.60 g (10 mmol) of 4-methyl-1,2,3
30 ml of thiadiazole-5-carbonyl chloride
Was dissolved in tetrahydrofuran, 0.50 g (2.5 mmol) of PEG200 (polyethylene glycol) was added, and 0.50 ml of triethylamine was added dropwise with stirring at room temperature, and the mixture was reacted at room temperature for 4 hours. After completion of the reaction, ethyl acetate was added to the reaction solution, and the organic layer was washed with aqueous hydrochloric acid.
After washing with aqueous sodium bicarbonate solution and drying over anhydrous magnesium sulfate,
The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 0.59 g of the desired product. Physical Properties nD 1.5222 (26 ° C) Yield 52%

Embodiment 6 FIG. (4-methyl-1,2,3-
Thiadiazole-5-carboxylic acid 2,6-dichloro-
4- (4-methyl-1,2,3-thiadiazole-5-
Preparation of ylcarbonylamino) phenyl (Compound No 288).

Embedded image 1.0 g (4.1 mmol) of 4-methyl-1,2,3
30 ml of thiadiazole-5-carbonyl chloride
Of tetrahydrofuran, 0.20 g (2.0 mmol) of 2,6-dichloro-p-aminophenol was added, and 1.0 ml of triethylamine was added dropwise with stirring at room temperature. A time reaction was performed. After completion of the reaction, ethyl acetate was added to the reaction solution, and the organic layer was washed with aqueous hydrochloric acid and aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.62 g of the desired product. Physical properties m. p. 260 ° C, 33% yield

Embodiment 7 FIG. (N, N'-p-phenylenebis (4-methyl-1,2,3-thiadiazole-5-
Production of carboxamide (Compound No. 352).

Embedded image 0.80 g (4.9 mmol) of 4-methyl-1,2,2
30 m of 3-thiadiazole-5-carbonyl chloride
l of tetrahydrofuran, 0.20 g (1.9
(Mmol) of p-phenylenediamine, 1.0 ml of triethylamine was added dropwise with stirring at room temperature, and the mixture was reacted at room temperature for 4 hours. After completion of the reaction, ethyl acetate was added to the reaction solution, and the organic layer was washed with aqueous hydrochloric acid and aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.62 g of the desired product. Physical properties m. p. 164 ° C, 73% yield

The bis-thiadiazole derivative represented by the general formula (I) or a salt thereof according to the present invention is useful as an agricultural and horticultural disease controlling agent, for example, rice blast (Pyricularia oryz).
ae), rice blight (Rhizoctonia solani), rice sesame leaf blight (Cochiobolus miyabeanus), powdery mildew (Erysiphe graminis) such as barley and wheat, and crown rust of oats on various host plants. Disease (Puccinia cor
onata) and other plant rust, tomato blight (Phytop)
hthora infestans) and plague of other plants, downy mildew of cucumber (Pseudoperonospora cubensis), downy mildew of grape (Plasmopara viticola), etc., downy mildew of apple (Venturia inaequalis), apple spot leaf spot (Alternaria mali), pear black spot (Alternaria kikuc)
hiana), citrus black spot (Diaporthe citri), Pseudomonas species such as cucumber spot bacterial disease (Pseudomona)
s syringae pv. lachrymans), tomato bacterial wilt (Pseudom)
onas solanacearum), Xanthomonas species, such as cabbage black rot (Xanthomonas campestris), rice leaf blight (Xan
thomonas oryzae), citrus canker (Xanthomonas c
itri), Erwinia species, such as cabbage soft rot (Erwin
ia carotovora), bacterial diseases such as tobacco mosaic disease (Tobacc
o Mosaic virus), and has an extremely high control effect against diseases such as viral diseases.

The agricultural and horticultural disease control agent comprising the bis-thiadiazole derivative represented by the general formula (I) or a salt thereof as an active ingredient of the present invention includes paddy field crops, field crops, fruit trees, vegetables, other crops and flowers and the like. Since it has a significant control effect on the disease that damages, paddy fields, fields, fruit trees, before or at the time the occurrence of the disease is confirmed, in accordance with the time when the occurrence of the disease is predicted 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 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 bis-thiadiazole derivative represented by the general formula (I) of the present invention or a salt thereof is dissolved in a suitable inert carrier or, if necessary, mixed with a suitable ratio together with an auxiliary, and dissolved. It may be separated, suspended, 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 that can be used in the present invention may be either solid or liquid. Examples of the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, 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 [a synthetic high-dispersion silicic acid also referred to as hydrous finely divided silicon or hydrous silicic acid, some of which contain calcium silicate as a main component depending on the product)], activated carbon, Inorganic mineral powders such as sulfur powder, pumice stone, calcined diatomaceous earth, crushed bricks, fly ash, sand, calcium carbonate, calcium phosphate, 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 which 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 auxiliary agent without the solvent function. The following carriers can be exemplified as typical examples. These can be used alone or in the form of a mixture of two or more types. 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 for controlling various diseases as it is, or appropriately diluted or suspended with water or the like. It can be used by applying it to places 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 thereto.
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 showed 2,82,96,1
06, 140, 156, 166, 176, 187, 18
8, 196, 219, 281, 282, 283, 28
8, 351 and 352 are judgments of C or higher, and in particular, compounds 2, 106, 156, 166, 188, 196, 21
9, 282, 283, 288, 351 and 352 show the control effect of A.

Continued on the front page (72) Inventor Takayoshi Tajima 2-10-9-301 Nagai, Sumiyoshi-ku, Osaka-shi, Osaka

Claims (5)

[Claims] 1. A compound of the general formula (I)[Wherein, R¹ And R^TwoMay be the same or different, and hydrogen
Atom, C₁-C₈Alkyl group, halo C₁-C_FourAlkyl group, Fe
Nyl group, which may be the same or different, a halogen atom, a nitro group
B, cyano, hydroxyl, mercapto, C₁-C_FourArchi
Le group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoxy group, ha
B c₁-C_FourAlkoxy group, C₁-C_FourAlkylthio group, halo C₁
-C_FourAn alkylthio group, an amino group, or the same or different
Good C₁-C_FourSelected from alkyl or phenyl
Selected from substituted amino groups having one or two substituents
A substituted phenyl group having 1 to 5 substituents,
May be different from oxygen, sulfur or nitrogen
5 to 6 members having 1 to 3 heteroatoms selected from
A terrorist ring or a halogen atom which may be the same or different
Child, nitro group, cyano group, hydroxyl group, mercapto group, C₁-C
_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoki
Si group, halo C₁-C_FourAlkoxy group, C₁-C_FourAlkylthio
Group, halo C₁-C_FourAn alkylthio group, an amino group, or the same
Or may be different C₁-C_FourAlkyl group or phenyl group
Substituted amino group having 1 to 2 substituents selected from
Having 1 to 5 substituents selected from the same or different
May be selected from oxygen, sulfur or nitrogen
Substituted 5- to 6-membered hetero atoms having 1 to 3 hetero atoms
B shows a ring. X¹And X^TwoMay be the same or different,
Represents an oxygen atom or a sulfur atom;¹And Y^TwoAre the same or
May be different from each other, and may be an oxygen atom, a sulfur atom, or -N (R^Three)-(Wherein, R^ThreeIs shown below. ). R is C₀-C₃₀Al
Kilen group, embedded image(Where R^ThreeAnd R^FourMay be the same or different, and hydrogen
Atom, halogen atom, hydroxyl group, nitro group, cyano group, C₁
-C_Four Alkyl group, halo C₁-C_FourAlkyl group, C₁-C_FourArco
Xyl group, halo C₁-C_FourAlkoxy group, C₁-C_Four Alkylthio
Group, C₁-C_FourAlkylsulfinyl group, C₁-C_Four Alkyls
Ruphonyl group, hydroxy C₁-C_FourAlkyl group, C₁-C_Four Al
Koxy C₁-C_FourAlkyl group, C₁-C_Four Alkoxycarbonyl
Group, amino group, which may be the same or different, C₁-C_FourArchi
A phenyl group, a phenyl group, or the same or different,
Halogen atom, nitro group, cyano group, hydroxyl group, mercap
Group, C₁-C_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C
_FourAlkoxy group, halo C₁-C_FourAlkoxy group, C₁-C_FourAl
Kirthio group, halo C₁-C_FourAlkylthio group, amino group, or
Is the same or different C₁-C_FourAlkyl group or
Having one or two substituents selected from phenyl groups
Substitution having 1 to 5 substituents selected from amino groups
A unit having one or two substituents selected from a phenyl group
Substituted amino group, amino C₁-C_FourAlkyl group, same or different
May be halogen atom, nitro group, cyano group, hydroxyl
Group, mercapto group, C₁-C_FourAlkyl group, halo C₁-C_FourAl
Kill group, C₁-C_FourAlkoxy group, halo C₁-C_FourAlkoxy
Group, C₁-C_FourAlkylthio group, halo C₁-C_FourAlkylthio
Group, amino group, or C which may be the same or different₁-C_Four
1 to 2 positions selected from an alkyl group or a phenyl group
1 to 5 positions selected from substituted amino groups having a substituent
1 to 2 groups selected from substituted phenyl groups having a substituent
Amino C having a substituent₁-C_FourAlkyl group, phenyl group,
May be the same or different, and may include a halogen atom, a nitro group,
Ano group, hydroxyl group, mercapto group, C₁-C_FourAlkyl group, ha
B c₁-C_FourAlkyl group, C₁-C_FourAlkoxy group, halo C₁-C_Four
Alkoxy group, C₁-C_FourAlkylthio group, halo C₁-C_FourAl
Kirthio group, amino group, or same or different
C₁-C_Four1 selected from an alkyl group or a phenyl group
1 to 1 selected from a substituted amino group having two substituents
Substituted phenyl group having 5 substituents, phenyl C₁-C_Four
Alkyl group, which may be the same or different,
Child, nitro group, cyano group, hydroxyl group, mercapto group, C₁-C
_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoki
Si group, halo C₁-C_FourAlkoxy group, C₁-C_FourAlkylthio
Group, halo C₁-C_FourAn alkylthio group, an amino group, or the same
Or may be different C₁-C_FourAlkyl group or phenyl group
Substituted amino group having 1 to 2 substituents selected from
Substituted 1 to 5 substituents on the ring selected from
Henil C₁-C_FourAlkyl group, phenoxy group, same or
May be different, a halogen atom, a nitro group, a cyano group,
Hydroxyl group, mercapto group, C₁-C_FourAlkyl group, halo C₁-C_Four
Alkyl group, C₁-C_FourAlkoxy group, halo C₁-C_FourAlkoki
Si group, C₁-C_FourAlkylthio group, halo C₁-C_FourAlkylthio
Group, amino group, or C which may be the same or different₁-C_Four
1 to 2 positions selected from an alkyl group or a phenyl group
1 to 5 positions selected from substituted amino groups having a substituent
Substituted phenoxy group having a substituent on the ring, phenoxy C₁-C
_FourAlkyl group, which may be the same or different, halogen
Atom, nitro group, cyano group, hydroxyl group, mercapto group, C₁
-C_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C_FourArco
Xyl group, halo C₁-C_FourAlkoxy group, C₁-C_FourAlkylthio
Group, halo C₁-C_FourAn alkylthio group, an amino group, or the same
Or may be different C₁-C_FourAlkyl group or phenyl group
Substituted amino group having 1 to 2 substituents selected from
Substituted 1 to 5 substituents on the ring selected from
Enoxy C₁-C_FourAn alkyl group, which may be the same or different,
1-3 selected from an oxygen atom, a sulfur atom or a nitrogen atom
5- or 6-membered heterocycle having two heteroatoms, identical or different
Halogen atom, nitro group, cyano group, water
Acid group, mercapto group, C₁-C_FourAlkyl group, halo C₁-C _FourA
Lucyl group, C₁-C_FourAlkoxy group, halo C₁-C_FourAlkoxy
Group, C₁-C_FourAlkylthio group, halo C₁-C_FourAlkylthio
Group, amino group, or C which may be the same or different₁-C_Four
1 to 2 positions selected from an alkyl group or a phenyl group
1 to 4 positions selected from substituted amino groups having a substituent
Having the same or different substituents, such as oxygen atom, sulfur
1 to 3 heteroatoms selected from atoms or nitrogen atoms
Substituted or 6-membered heterocycle having the same or different
Selected from oxygen, sulfur or nitrogen
5- to 6-membered heterocycle C having up to 3 heteroatoms₁-C_FourA
Alkyl group, which may be the same or different, a halogen atom,
Toro, cyano, hydroxyl, mercapto, C₁-C_FourAl
Kill group, halo C₁-C_FourAlkyl group, C₁-C_FourAn alkoxy group,
Halo C₁-C_FourAlkoxy group, C₁-C_FourAlkylthio group, halo
C₁-C_FourAlkylthio group, amino group, or the same or different
May be C₁-C_FourSelect from alkyl group or phenyl group
Selected from substituted amino groups having one or two substituents
Having 1 to 4 substituents, which may be the same or different
Selected from oxygen, sulfur or nitrogen
Substituted 5- to 6-membered heterocycle C having up to 3 heteroatoms₁-C
_FourAn alkyl group, or(Where R⁶Is C₁-C₆Alkylene group, one or more identical or
Halogen atom or C which may be different₁-C_FourBy alkyl group
Replaced C₁-C₆An alkylene group, or -O-, -S (O) n- (where n is an integer of 0 to 2) or -N (R⁸)-(Wherein, R⁸Is a hydrogen atom, a halogen atom, C₁-C_FourArchi
Le group, halo C₁-C_FourAlkyl group, C₁-C_FourAlkoxycarbo
Nyl group, phenyl group, which may be the same or different, halogen
Atom, nitro group, cyano group, hydroxyl group, mercapto group,
C₁-C_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C_FourAl
Coxy group, halo C₁-C_FourAlkoxy group, C₁-C_FourAlkyl
O group, halo C₁-C_FourAlkylthio group, amino group, or the same
Or may be different, C₁-C_FourAlkyl group or phenyl
Substituted amino group having 1 to 2 substituents selected from
A substituted group having 1 to 5 substituents selected from
Nyl group, phenyl C₁-C_FourAlkyl groups, identical or different
Good, halogen atom, nitro group, cyano group, hydroxyl group,
Mercapto group, C₁-C_FourAlkyl group, halo C₁-C_FourAlkyl
Group, C₁-C_FourAlkoxy group, halo C₁-C_FourAlkoxy group, C₁
-C_FourAlkylthio group, halo C₁-C_FourAlkylthio group, ami
Or a group which may be the same or different, C₁-C_FourArchi
One or two substituents selected from a phenyl group or a phenyl group
Having 1 to 5 substituents selected from substituted amino groups having
Having substituted phenyl C₁-C_FourAn alkyl group, or(Where R¹¹Is C₁-C₆An alkylene group, or the same or
May be different, a halogen atom or C₁-C_FourAlkyl group
C having one or more substituents selected from₁-C₆Alkylene
A group represented by R¹²Is a hydrogen atom, C₁-C₈Alkyl group, halo C₁
-C_FourAlkyl group, phenyl group, same or different
, Halogen atom, nitro group, cyano group, hydroxyl group, mel
Capto group, C₁-C_FourAlkyl group, halo C₁-C_FourAlkyl group,
C₁-C_FourAlkoxy group, halo C₁-C_FourAlkoxy group, C₁-C_Four
Alkylthio group, halo C₁-C_FourAlkylthio group, amino
Group, or may be the same or different, C₁-C_FourAlkyl
Group having one or two substituents selected from
Having 1 to 5 substituents selected from substituted amino groups
Substituted phenyl groups, which may be the same or different,
1 to 3 atoms selected from
A 5- to 6-membered heterocyclic ring having a telo atom, or the same or
May be different, a halogen atom, a nitro group, a cyano group,
Hydroxyl group, mercapto group, C₁-C_FourAlkyl group, halo C₁-C_Four
Alkyl group, C₁-C_FourAlkoxy group, halo C₁-C_FourAlkoki
Si group, C₁-C_FourAlkylthio group, halo C₁-C_FourAlkylthio
Group, amino group, or the same or different, C₁-C
_Four1 to 2 alkyl groups or phenyl groups
1-4 of a substituted amino group having a substituent
Having a substituent, which may be the same or different, and
1 to 3 hetero atoms selected from a yellow atom or a nitrogen atom
A substituted 5- to 6-membered heterocyclic ring having^FourIs -O-, -S- or -N- (R¹³)-(Wherein, R¹³Is a hydrogen atom or C₁-C_FourRepresents an alkyl group
You. ) And X^FourRepresents an oxygen atom or a sulfur atom, and q
Represents an integer of 0 to 1, and r represents an integer of 0 to 1. )
Show. C) may be interrupted by₁-C₆Indicates an alkylene group
Then R⁷Is a hydrogen atom, C₁-C₈Alkyl group, halo C₁-C₈A
Alkyl group, phenyl group, same or different, halo
Gen atom, nitro group, cyano group, hydroxyl group, mercapto
Group, C₁-C_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C_Four
Alkoxy group, halo C₁-C_FourAlkoxy group, C₁-C_FourArchi
Luthio group, halo C₁-C_FourAn alkylthio group, an amino group, or
C may be the same or different₁-C_FourAlkyl group or
Substituted with one or two substituents selected from
A substituted group having 1 to 5 substituents selected from amino groups;
Phenyl group, phenyl C₁-C_FourAlkyl group, same or different
May be halogen atom, nitro group, cyano group, hydroxyl
Group, mercapto group, C₁-C_FourAlkyl group, halo C₁-C_FourAl
Kill group, C₁-C_FourAlkoxy group, halo C₁-C_FourAlkoxy
Group, C₁-C_FourAlkylthio group, halo C₁-C_FourAlkylthio
Group, amino group, or C which may be the same or different₁-C_Four
1 to 2 positions selected from an alkyl group or a phenyl group
1 to 5 positions selected from substituted amino groups having a substituent
Substituted phenyl C having a substituent on the ring₁-C_FourAlkyl group,
One or different, oxygen, sulfur, or nitrogen
5 having 1 to 3 heteroatoms selected from atoms
A 6-membered heterocyclic ring, or
Gen atom, nitro group, cyano group, hydroxyl group, mercapto
Group, C₁-C_FourAlkyl group, halo C₁-C_FourAlkyl group, C₁-C_Four
Alkoxy group, halo C₁-C_FourAlkoxy group, C₁-C_FourArchi
Luthio group, halo C₁-C_FourAn alkylthio group, an amino group, or
C may be the same or different₁-C_FourAlkyl group or
Substituted with one or two substituents selected from
Having 1 to 5 substituents on the ring selected from a mino group,
Same or different, oxygen atom, sulfur atom or nitrogen atom
Having 1 to 3 heteroatoms selected from elementary atoms
A 5- to 6-membered heterocyclic ring;^ThreeIs -O-, -S- or -N- (R⁸)-(Wherein, R⁸Is the same as above. ) And X^ThreeIs an oxygen atom
Or m represents an integer of 0 to 5;
Or an integer of 1. A) represents an integer of 0 to 30
Show. R^ThreeAnd R^FourAre together, C₀-C₇Alkylene
A 3- to 8-membered ring may be formed by the group;
The ring is represented by the following formulas: -O-, -S (O) n- (wherein n is an integer of 0 to 2), and -N-R (R⁸)-(Wherein, R⁸Is the same as above. ) Or -C (R⁹) (R^Ten)-(Wherein, R⁹And R^TenMay be the same or different, and halo
Gen atom, C₁-C_FourAn alkyl group, or(Where R¹¹, R¹², X^Four, Y^Four, Q and r are as defined above.
Same. ) And R⁹And R^TenIs together C_Two-C₆Al
A 3- to 7-membered ring can be formed by a kylene group. )
Can also be interrupted. Alkyre represented by)
Groups which may be the same or different,
C that may be interrupted by the above groups₀-C₃₀Indicates an alkylene group
You. -O-, -S (O) n- (wherein n is as defined above), -N- (R^Three)-(Wherein, R^ThreeIs the same as above. ), And -C (R^Three) = C (R^Four)-(Wherein, R^ThreeAnd R^FourIs the same as above. ), [Chemical Formula 24] -C≡C-, [Chemical Formula 25](Where Z is a halogen atom, a nitro group, a cyano group, a hydroxyl group,
Group, mercapto group, C₁-C_FourAlkyl group, halo C₁-C_FourAl
Kill group, C₁-C_FourAlkoxy group, halo C₁-C_FourAlkoxy
Group, C₁-C_FourAlkylthio group, halo C₁-C_FourAlkylthio
Group, amino group, C which may be the same or different₁-C_FourAl
1 or 2 substituents selected from a kill group or a phenyl group
Or a substituted amino group having(Where R⁶, R⁷, Y^Three, X^Three, M and p are as defined above.
Same. ). ) Or(Wherein, Z is as defined above). Screws represented by
-A thiadiazole derivative or a salt thereof. 2. R ¹ and R ² may be the same or different and represent a hydrogen atom, a C ₁ -C ₈ alkyl group or a halo C ₁ -C ₄ alkyl group, and X ¹ and X ² are the same or different. And Y ¹ and Y ² may be the same or different, and represent an oxygen atom, a sulfur atom, or —N (R ³ ) — (wherein R ³ is Wherein R is a C ₀ -C ₃₀ alkylene group, (Wherein R ³ and R ⁴ may be the same or different and each represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a halo C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkoxycarbonyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, hydroxyl group, mercapto 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 group, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, amino group, or a substituted phenyl having from 1 to 5 substituents selected from substituted amino groups having one or two substituents selected from a good C ₁ -C ₄ alkyl group or a phenyl group which may be identical or different Group, or (In the formula, R ⁶ is a C ₁ -C ₆ alkylene group, a C ₁ -C ₆ alkylene group substituted by a C ₁ -C ₄ alkyl group, or —O— or —S (O) n- (where n is an integer of 0 to 2) C ₁ -C which may be interrupted
₆ represents an alkylene group, R ⁷ is a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group, a phenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a hydroxyl group, mercapto 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, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, amino group, or C ₁ -C ₄ which may be the same or different
A substituted phenyl group having 1 to 5 substituents selected from a substituted amino group having 1 to 2 substituents selected from an alkyl group or a phenyl group, which may be the same or different, an oxygen atom, a sulfur atom Or a 5- to 6-membered heterocyclic ring having 1 to 3 heteroatoms selected from a nitrogen atom, or the same or different, and may be a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl groups, halo C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy groups, halo
C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, halo C ₁ -C
₁ to 5 substituents selected from substituted alkyl groups having 1 to 2 substituents selected from ₄ alkylthio groups, amino groups, or C ₁ -C ₄ alkyl groups or phenyl groups which may be the same or different having a group on the ring, which may be the same or different, an oxygen atom, a sulfur atom, or a 5-6 membered substituted heterocycle having 1-3 heteroatoms selected from nitrogen atom, Y ³ is embedded image -O-, embedded image -S- or embedded image -N (R ⁸⁾ - (wherein, R ⁸ is a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl group, halo C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxycarbonyl group, a phenyl group, which may be identical or different, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto 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, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio groups An amino group, or ₁ to 5 substituents which may be the same or different and which are substituted amino groups having 1 to 2 substituents selected from a C ₁ -C ₄ alkyl group or a phenyl 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 nitro group, a cyano group, a hydroxyl group,
Mercapto 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, C ₁
-C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, amino group, or substituted having one or two substituents which may be the same or different and are selected from C ₁ -C ₄ alkyl group or phenyl group A substituted phenyl C ₁ -C ₄ alkyl group having 1 to 5 substituents selected from an amino group, or (Wherein, R ¹¹ may C ₁ -C ₆ alkylene group, or the same or different, C ₁ -C ₆ alkylene having one or more substituents selected from halogen atom or a C ₁ -C ₄ alkyl group R ¹² represents a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁
-C ₄ alkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, hydroxyl group, mercapto 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 group, C ₁ -C ₄
An alkylthio group, a halo C ₁ -C ₄ alkylthio group, an amino group, or a substituted amino 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 A substituted phenyl group having 1 to 5 substituents selected, a 5 to 6-membered heterocyclic ring having 1 to 3 hetero atoms which may be the same or different and selected from an oxygen atom, a sulfur atom or a nitrogen atom Or the same or different, a halogen atom, a nitro group, a cyano group,
A hydroxyl group, a mercapto 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, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio group, an amino group, or be the same or different and, C ₁ -C
₄ has 1 to 4 substituents selected from a substituted amino group having 1 to 2 substituents selected from an alkyl group or a phenyl group, may be the same or different, oxygen atom, sulfur atom or A substituted 5- to 6-membered heterocyclic ring having 1 to 3 heteroatoms selected from a nitrogen atom, wherein Y ⁴ is -O-, -S- or -N (R ¹³ ) — (wherein, R ¹³ represents a hydrogen atom or a C ₁ -C ₄ alkyl group), X ⁴ represents an oxygen atom or a sulfur atom, and q
Represents an integer of 0 to 2, and r represents an integer of 0 to 1. ). ) Indicates, X ³ represents an oxygen atom or a sulfur atom,
m may be the same or different and represents an integer of 0 to 10;
Represents an integer of 0 or 1. ), And a represents an integer of 0 to 30. R ³ and R ⁴ may be taken together to form a ^3- to 8-membered ring by a C ₀ -C ₇ alkylene group,
The 8-membered ring is represented by the following formula: -O-, -S (O) n- (wherein n is an integer of 0 to 2), or -N (R ⁸ ) (Wherein R ⁸ is as defined above). Or a C ₀ -C ₃₀ alkylene group which may be interrupted by one or more groups shown below, which may be the same or different. Embedded image -O-, embedded image (wherein, n as defined above.) -S (O) n-, embedded image -N (R ³⁾ - (wherein, R ³ is the -C (R ³ ) = C (R ⁴ )-(wherein R ³ and R ⁴ are the same as above), -C≡C-, or 48 (In the formula, Z is a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a C ₁ -C ₄ alkyl group, a halo C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a halo C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ alkylthio groups, halo C ₁ -C ₄ alkylthio groups, amino groups, or C ₁ -C ₄ which may be the same or different
A substituted amino group having 1 to 2 substituents selected from an alkyl group or a phenyl group, or (Wherein, R ⁶ , R ⁷ , Y ³ , X ³ , m and p are the same as above). ) Represents a C ₀ -C ₃₀ alkylene group which may be interrupted. 2. The bis-thiadiazole derivative according to claim 1 or a salt thereof. 3. R ¹ and R ² may be the same or different and each represent a hydrogen atom, a C ₁ -C ₈ alkyl group or a halo C ₁ -C ₄ alkyl group, and X ¹ and X ² are the same or different. And may represent an oxygen atom or a sulfur atom, and Y ¹ and Y ² may be the same or different, and represent an oxygen atom, a sulfur atom, or —N (R ³ ) — wherein R ³ is Wherein R is a C ₀ -C ₃₀ alkylene group; (Wherein, R ³ and R ⁴ may be the same or different, and include a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a halo C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkoxycarbonyl group, phenyl group, or (Wherein, R ⁶ is a C ₁ -C ₆ alkylene group or a C ₁ -C ₆ alkylene group substituted by a C ₁ -C ₄ alkyl group, or —O— or S (O) n- (wherein, n an integer. 0-2) shows the interrupted with good C ₁ -C ₆ alkylene group by, R ⁷ is a hydrogen atom, C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group,
A phenyl group, which may be the same or different, a halogen atom,
Nitro group, cyano group, hydroxyl group, mercapto 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, C ₁ -C ₄ Alkylthio group,
_{1 selected from a} halo C ₁ -C ₄ alkylthio group, an amino group, or a substituted amino group having 1-2 substituents selected from the same or different C ₁ -C ₄ alkyl group or phenyl group A phenyl group having from 5 to 5 substituents, which may be the same or different, and from 5 to 6 having from 1 to 3 heteroatoms selected from an oxygen atom, a sulfur atom, or a nitrogen atom;
Membered heterocyclic ring, or may be the same or different, halogen atom, nitro group, cyano group, hydroxyl group, mercapto 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, C ₁ -C ₄ alkylthio group, halo C ₁ -C ₄ alkylthio groups ₁ to 5 substituents selected from a substituted amino group having 1 to 2 substituents selected from an amino group, or a C ₁ -C ₄ alkyl group which may be the same or different, or a phenyl group; 5 to 6 having 1 to 3 hetero atoms selected from an oxygen atom, a sulfur atom, or a nitrogen atom, which may be the same or different.
Y ³ represents —O— or —S—, X ³ represents an oxygen atom or a sulfur atom, and m may be the same or different, and 10 represents an integer, and p represents an integer of 0 or 1. ), And a represents an integer of 0 to 30. Alkylene) or a group represented by or the same or different and may be interrupted in one or more groups shown in good below C ₀
-C _{30 represents an} alkylene group. Embedded image -O-, embedded image (wherein, n as defined above.) -S (O) n-, embedded image -N (R ³⁾ - (wherein, R ³ is the -C (R ³ ) = C (R ⁴ )-(wherein R ³ and R ⁴ are the same as above), -C≡C- or Embedded image (Where Z is a halogen atom, a nitro group, a cyano group, a C ₁ -C
₄ alkyl groups, halo C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy groups, halo C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ alkylthio groups, halo C ₁ -C ₄ alkylthio groups, or 63] ^3. The bis-thiadiazole derivative according to claim 2, wherein R ⁶ , R ⁷ , Y ³ , X ³ , m and p are as defined above. 4. The screw according to claim 1, wherein:
An agricultural and horticultural disease controlling agent comprising a thiadiazole derivative or a salt thereof as an active ingredient. 5. An agricultural and horticultural disease controlling agent, which comprises treating an agricultural and horticultural disease controlling agent according to claim 4 with respect to a plant in which the occurrence of a plant disease is not desired. A method for controlling plant diseases, characterized in that: