WO2019031384A1 - 1,3,5,6-tetrasubstituted thieno[2,3-d]pyrimidine-2,4-(1h,3h)dione compound and agricultural or horticultural bactericide - Google Patents

Abstract

The present invention relates to a compound represented by formula (I) or a salt thereof. (In formula (I), R ¹ represents (unsubstituted) C _1-6 alkyl, R ² represents a hydrogen atom, etc., R ³ represents a C _1-6 alkoxycarbonyl group (no) substituted, etc. R ⁴ and R ^{4 '} each represent a hydrogen atom, etc., Z represents an oxygen atom, R ⁵ represents an (unsubstituted) C _1-6 alkyl group, etc., X is a halo radical, etc., and n is an integer from 0 to 5.)

Description

1,3,5,6-Tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds and fungicides for agriculture and horticulture

The present invention relates to 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds and fungicides for agriculture and horticulture. More specifically, the present invention provides 1,3,5,6-tetra-substituted thieno [2,3-d] pyrimidine-2,4 (which has excellent bactericidal activity, safety, and industrially advantageous synthesis). The present invention relates to a 1H, 3H) dione compound and an agricultural and horticultural fungicide containing the same as an active ingredient.
Priority is claimed on Japanese Patent Application No. 2017-152327, filed on Aug. 7, 2017, and Japanese Patent Application No. 2018-058857, filed on March 26, 2018, the contents of which are incorporated herein by reference. Is incorporated herein by reference.

In the cultivation of agricultural and horticultural crops, numerous control agents have been proposed for crop diseases. Most of the proposed control agents are inadequate in their control efficacy, their use is restricted by the emergence of drug-resistant pathogens, they cause phytotoxicity and pollution in plants, or they are toxic to pelvic fish And the impact on the environment is large, so it is not satisfactory. Therefore, there is a strong demand for the emergence of a safe controlling drug that can be used with few such drawbacks.

By the way, the compound etc. which are represented by Formula (A) are disclosed by patent document 1. FIG.

Patent Document 2 discloses a compound represented by Formula (B) and the like.

Patent Document 3 discloses a compound represented by Formula (C) and the like.

Patent Document 4 discloses a compound represented by Formula (D) and the like.

Patent Document 5 discloses a compound represented by Formula (E) and the like.

Patent Document 6 discloses a compound represented by Formula (F) and the like. Patent Document 7 discloses agricultural and horticultural fungicide applications such as compounds represented by formula (F).

WO 2013/071169 A WO 2015/007451 A WO 2017/075056 A WO 2017/91600 A WO 2017/091602 A WO 2017/901617 A WO 2017/091627 A

The object of the present invention is to provide 1,3,5,6-tetra-substituted thieno [2,3-d] pyrimidine-2,4 (1H, 1 (H), which is excellent in bactericidal activity, safety and industrially advantageous synthesis. 3H) A dione compound, and an agricultural and horticultural fungicide containing the same as an active ingredient.

As a result of earnest studies to solve the above problems, the present invention including the following embodiments has been completed.

[1] A compound represented by the formula (I) or a salt thereof.

式(I)中、
　Ｒ¹は、置換若しくは無置換のＣ１～６アルキル基である。
　Ｒ²は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ１～６アルコキシカルボニル基、置換若しくは無置換のアミノカルボニル基、置換若しくは無置換のアミノ基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換の５～６員ヘテロアリール基、またはシアノ基である。
　Ｒ³は、置換若しくは無置換のＣ１～６アルコキシカルボニル基、または置換若しくは無置換のアミノカルボニル基である。
　Ｒ⁴およびＲ^4’は、それぞれ独立して、水素原子、または置換若しくは無置換のＣ１～６アルキル基である。
　Ｚは、酸素原子である。
　Ｒ⁵は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ３～８シクロアルキル基、または５～６員環飽和ヘテロシクリル基である。
　Ｘは、ハロゲノ基、または置換若しくは無置換のＣ１～６アルコキシ基である。
　ｎは、化学的に許容されるＸの個数を示し、かつ０～５のいずれかの整数である。
　ｎが２以上のときＸは互いに同じでも異なってもよい。

In formula (I),
R ¹ is a substituted or unsubstituted C1-6 alkyl group.
R ² represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C1 to 6 group 6 alkoxycarbonyl group, substituted or unsubstituted aminocarbonyl group, substituted or unsubstituted amino group, substituted or unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted 5 to 6 membered heteroaryl group, or cyano group It is.
R ³ is a substituted or unsubstituted C1-6 alkoxycarbonyl group or a substituted or unsubstituted aminocarbonyl group.
R ⁴ and R ^{4 ′} are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Z is an oxygen atom.
R ⁵ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, or a 5- to 6-membered ring saturated heterocyclyl group.
X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
n represents the number of chemically acceptable Xs, and is an integer of 0 to 5.
When n is 2 or more, X may be the same or different.

[2] the substituents on substituted C1 ~ 6 alkyl group in R ⁵ is a halogeno group, hydroxyl group, C1 ~ 6 alkoxy group, C1 ~ 6 alkylthio group, C1 ~ 6 alkylsulfinyl group, C1 ~ 6 alkylsulfonyl group, C3 The compound represented by the formula (I) according to claim 1, which is a -8 cycloalkyl group, a cyano group or an aminothiocarbonyl group, or a salt thereof.

[3] An agricultural and horticultural germicidal agent comprising at least one compound selected from the group consisting of the compounds according to the above [1] or [2] and salts thereof as an active ingredient.

The 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds of the present invention are excellent in bactericidal activity, have certain effects, and are excellent in safety. And, it can be advantageously synthesized industrially.
The fungicide for agricultural and horticultural use of the present invention has an excellent control effect, does not cause phytotoxicity on plants, and has less adverse effects on human beings and fishes and environment.

[Compound represented by Formula (I)]
The 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound of the present invention is a compound represented by the formula (I) (hereinafter referred to as a compound (I) Or a salt of compound (I).

In the present invention, the term "unsubstituted" means that it is only a mother core group. When there is no description of "substituted" and only the name of the mother core group is described, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of a group to be a mother nucleus is substituted with a group (substituent) having the same or a different structure as that of the mother nucleus. Thus, the “substituent” is another group bonded to the mother core. The number of substituents may be one or two or more. The two or more substituents may be the same or different.
Terms such as "C1-6" indicate that the number of carbon atoms of the group to be a mother nucleus is 1 to 6, and the like. The number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified into a C2 alkoxy C4 alkyl group.

The “substituent” is chemically acceptable and is not particularly limited as long as the effects of the present invention are obtained. The groups that can be "substituents" are exemplified below.
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. An alkyl group;
Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc. A C2-6 alkenyl group of
A C2-6 alkynyl group such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;

A C 3-8 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cuvanyl group;
A C 6-10 aryl group such as phenyl group and naphthyl group;
C6-10 aryl C1-6 alkyl groups such as benzyl group, phenethyl group and the like;
3 to 6 membered heterocyclyl group;
3 to 6 membered heterocyclyl C 1-6 alkyl group;

Hydroxyl group;
C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like;
A C 2-6 alkenyloxy group such as a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group;
A C2-6 alkynyloxy group such as ethynyloxy group, propargyloxy group;
A C 6-10 aryloxy group such as phenoxy group and naphthoxy group;
C 6-10 aryl C 1-6 alkoxy groups such as benzyloxy group, phenethyloxy group and the like;
5- to 6-membered heteroaryloxy group such as thiazolyloxy group, pyridyloxy group and the like;
5- to 6-membered heteroaryl C1-6 alkyloxy group such as thiazolylmethyloxy group, pyridylmethyloxy group;

Formyl group;
A C1-6 alkylcarbonyl group such as an acetyl group and a propionyl group;
Formyloxy group;
A C1-6 alkylcarbonyloxy group such as an acetyloxy group, a propionyloxy group and the like;
A C 6-10 arylcarbonyl group such as benzoyl group;
C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like;
C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group and the like;
Carboxyl group;

Halogeno groups such as fluoro, chloro, bromo and iodo;
A C 1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group and the like;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group;
C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
C1-6 haloalkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy, 2,3-dichlorobutoxy and the like;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C 1-6 haloalkyl carbonyl group such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group;

Amino group;
C1-6 alkyl substituted amino group such as methylamino group, dimethylamino group, diethylamino group;
A C 6-10 arylamino group such as anilino group, naphthylamino group;
C 6-10 aryl C 1-6 alkylamino groups such as benzylamino group, phenethylamino group and the like;
Formylamino group;
A C 1-6 alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group, an i-propylcarbonylamino group;
A C 1-6 alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group and the like;
An aminocarbonyl group having a non-substituted or substituted group such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, an N-phenyl-N-methylaminocarbonyl group;
Imino C1-6 alkyl groups such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group;
N-hydroxy-iminomethyl group, (1- (N-hydroxy) -imino) ethyl group, (1- (N-hydroxy) -imino) propyl group, N-methoxy-iminomethyl group, (1- (N-methoxy) group A substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as -imino) ethyl group;
Aminocarbonyloxy group;
A C 1-6 alkyl substituted aminocarbonyloxy group such as ethylaminocarbonyloxy group, dimethylaminocarbonyloxy group and the like;

Mercapto group;
A C1-6 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group and the like;
A C 1-6 haloalkylthio group such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group;
A C 6-10 arylthio group such as phenylthio group and naphthylthio group;
5- to 6-membered heteroarylthio groups such as thiazolylthio group, pyridylthio group and the like;

C1-6 alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl and t-butylsulfinyl;
A C 1-6 haloalkylsulfinyl group such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group;
A C 6-10 arylsulfinyl group such as a phenylsulfinyl group;
5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl group, pyridylsulfinyl group and the like;

A C 1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group and the like;
A C 1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group;
A C 6-10 arylsulfonyl group such as a phenylsulfonyl group;
A 5- to 6-membered heteroarylsulfonyl group such as thiazolylsulfonyl group, pyridylsulfonyl group and the like;
C1-6 alkylsulfonyloxy group such as methylsulfonyloxy group, ethylsulfonyloxy group, t-butylsulfonyloxy group and the like;
A C 1-6 haloalkylsulfonyloxy group such as a trifluoromethylsulfonyloxy group, a 2,2,2-trifluoroethylsulfonyloxy group;

Tri C 1-6 alkyl substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
Tri C 6-10 aryl substituted silyl groups such as triphenyl silyl group;
Cyano group; nitro group; aminothiocarbonyl group;

Moreover, as for these "substituents", any hydrogen atom in the said substituent may be substituted by the group of a different structure. As the “substituent” in that case, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group and the like can be mentioned.

Further, the above-mentioned “3 to 6-membered heterocyclyl group” is a group containing 1 to 4 hetero atoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as a constituent atom of the ring. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is a hetero ring, the remaining rings may be any of saturated alicyclic, unsaturated alicyclic or aromatic rings. Examples of the “3 to 6-membered heterocyclyl group” include a 3 to 6-membered saturated heterocyclyl group, a 5 to 6-membered heteroaryl group, a 5 to 6-membered partially unsaturated heterocyclyl group and the like.

Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like.

Examples of 5-membered heteroaryl groups include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group and the like. Can.
Examples of the 6-membered heteroaryl group include pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group.

{R ¹ }
In formula (I), R ¹ is a substituted or unsubstituted C1-6 alkyl group.

The “C1-6 alkyl group” in R ¹ may be linear or branched. As the alkyl group, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group And i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

Specific examples of the “C1-6 alkyl group having a substituent” in R ¹ include
Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoro Ethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1 C1-6 haloalkyl groups such as trifluoromethylethyl group, perfluoropropan-2-yl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group;

Hydroxy C 1-6 alkyl groups such as hydroxymethyl group, hydroxyethyl group;
C1 to C4 such as methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group and the like 6 alkoxy C1-6 alkyl groups;
C6-10 aryl C1-6 alkyl groups such as benzyl group, phenethyl group and the like;
And C3-8 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group and the like.

The substituent on the "C1-6 alkyl group" for R ¹ is preferably a halogeno group such as a fluoro group, a chloro group, a bromo group or an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group And C1-6 alkoxy groups such as n-butoxy, s-butoxy, i-butoxy and t-butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy and the like And C1-6 haloalkoxy groups; cyano groups;

R ¹ is preferably a methyl group.

{R ² }
In formula (I), R ² represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted Or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted aminocarbonyl group, substituted or unsubstituted amino group, substituted or unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted 5-6 membered hetero It is an aryl group or a cyano group.

Examples of the “halogeno group” in R ² include fluoro, chloro, bromo and iodo groups.

Examples of the “C1-6 alkyl group” for R ² include the same as those exemplified for R ¹ above.

As the “C2-6 alkenyl group” for R ² , a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-Methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl And 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.

Examples of the “C2-6 alkynyl group” for R ² include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl And 1,1-dimethyl-2-butynyl group.

Examples of the "C1-6 alkoxycarbonyl group" in R ² include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like. it can.
Among these, a methoxycarbonyl group and an ethoxycarbonyl group are preferable.

Preferable substituents on the “C1-6 alkyl group” and the “C1-6 alkoxycarbonyl group” for R ² include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group.

The “substituted or unsubstituted aminocarbonyl group” in R ² is a group represented by Formula (a).

In formula (a), * is a bonding position, and R ^a and R ^b are each independently a hydrogen atom or a C1-6 alkyl group.

Examples of the “C1-6 alkyl group” for R ^a and R ^b include the same as those exemplified for R ¹ above.

The “substituted or unsubstituted aminocarbonyl group” in R ² is preferably a methylaminocarbonyl group or a dimethylaminocarbonyl group.

The “substituted or unsubstituted amino group” in R ² is a group represented by “—NR ^c R ^d ”. In the formulae, R ^c and R ^d each independently represent a hydrogen atom or a C1-6 alkylcarbonyl group.

Examples of the "C1-6 alkylcarbonyl group" in R ^c and R ^d include an acetyl group, a propionyl group and the like.

The “substituted or unsubstituted amino group” in R ² is preferably an acetylamino group.

Examples of the “C3-8 cycloalkyl group” in R ² include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cuvanyl group.

The “5 to 6-membered heteroaryl group” for R ² is a pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group And 5-membered heteroaryl groups such as tetrazolyl group; and 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group.
Among these, a 5-membered heteroaryl group is preferable, and a triazolyl group or a pyrazolyl group is particularly preferable.

Preferred substituents on the "C3-8 cycloalkyl group" and the "5- to 6-membered heteroaryl group" for R ² include a methyl group, an ethyl group, an n-propyl group, an n-butyl group and an n-pentyl group , N-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group Mention may be made of C1-6 alkyl groups such as groups.

R ² is preferably a halogeno group, a C2-6 alkenyl group, a C1-6 alkoxycarbonyl group, a substituted or unsubstituted amino group, a 5-membered heteroaryl group or a cyano group, and a halogeno group or a C1-6 alkoxy Particularly preferred is a carbonyl group or a 5-membered heteroaryl group.

{R ³ }
In formula (I), R ³ is a substituted or unsubstituted C1-6 alkoxycarbonyl group or a substituted or unsubstituted aminocarbonyl group.

"C1 ~ 6 alkoxycarbonyl group" in R ^3, and "substituted or unsubstituted aminocarbonyl group" is the same thing can be mentioned those exemplified in the R ^2.

Preferred examples of the substituent on the “C1-6 alkoxycarbonyl group” for R ³ include halogeno groups such as fluoro, chloro, bromo and iodo.

R ³ is preferably a substituted or unsubstituted aminocarbonyl group, more preferably an isopropylaminocarbonyl group.

{R ⁴ , R ^{4 '} }
In formula (I), R ⁴ and R ^{4 ′} are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.

Examples of the “substituted or unsubstituted C1-6 alkyl group” for R ⁴ and R ^{4 ′} can be the same as those specifically exemplified for R ¹ .

R ⁴ and R ^{4 ′} are preferably methyl groups.

{Z}
In formula (I), Z is an oxygen atom.

{R ⁵ }
In formula (I), R ⁵ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, or a 5- to 6-membered ring saturated heterocyclyl group.

Examples of the “C1-6 alkyl group” for R ⁵ include the same as those exemplified for R ¹ above.

Preferred substituents on "C1 ~ 6 alkyl group" in R ^5, a halogeno group, hydroxyl group, C1 ~ 6 alkoxy group, C1 ~ 6 alkylthio group, C1 ~ 6 alkylsulfinyl group, C1 ~ 6 alkylsulfonyl group, C3 And -8 cycloalkyl groups, cyano groups, or aminothiocarbonyl groups.

Specifically, halogeno groups such as fluoro, chloro, bromo and iodo; hydroxy; methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i C1-6 alkoxy groups such as -butoxy group and t-butoxy group; methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group C1-6 alkylthio group such as a group; C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group; C1-6 alkyl such as a methylsulfonyl group, an ethylsulfonyl group and a t-butylsulfonyl group Sulfonyl group; cyclopropyl group, cyclobutyl group, cyclopentyl group, And amino thiocarbonyl group; a cyano group; Kurohekishiru group, C3 ~ 8 cycloalkyl group such as Kyubaniru group.

Examples of the “substituted or unsubstituted C3-8 cycloalkyl group” for R ⁵ include the same as those exemplified for R ² above.

Examples of the “5- to 6-membered ring saturated heterocyclyl group” in R ⁵ include pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, tetrahydropyranyl group, morpholinyl group, dioxolanyl group, dioxanyl group, etc. it can.
Among these, a tetrahydropyranyl group is preferable.

R ⁵ is preferably a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.

{X}
In formula (I), X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.

Examples of the "halogeno group" for X include the same as those exemplified for R ² above.

As the "C1-6 alkoxy group" for X, methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, Examples thereof include s-butoxy group, t-butoxy group, and i-hexyloxy group.

Preferred examples of the substituent on the "C1-6 alkoxy group" for X include halogeno groups such as fluoro, chloro, bromo and iodo.

{N}
n represents the number of chemically acceptable Xs, and is an integer of 0 to 5. When n is 2 or more, X may be the same or different.

A wavy line indicating a bond (NO undefined stero bond) between N (nitrogen atom) and Z (oxygen atom) in the formula (I) is an E form or a Z form or a mixture thereof by nitrogen carbon double bond Indicates that there is.

The salt of compound (I) is not particularly limited as long as it is an agronomically acceptable salt. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron, copper and the like And salts of transition metals such as ammonia, triethylamine, tributylamine, pyridine, and salts of organic bases such as hydrazine.

The salt of compound (I) or compound (I) is not particularly limited depending on the method for producing it. In addition, the salt of compound (I) can be obtained from compound (I) by a known method. For example, Compound (I) or a salt of Compound (I) of the present invention can be obtained by a known production method described in the Examples and the like.

[Compound represented by Formula (II)]
The 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound of the present invention is preferably a compound of the formula (II).

　式(II)中、Ｒ²およびＲ⁵は、式(I)中のそれらと同じ意味である。

In formula (II), R ² and R ⁵ have the same meaning as those in formula (I).

A wavy line indicating a bond (NO undefined stero bond) between N (nitrogen atom) and O (oxygen atom) in formula (II) is an E form or a Z form or a mixture thereof by nitrogen carbon double bond Indicates that there is.

[Fungicide for agriculture and horticulture]
The fungicide for agricultural and horticultural use of the present invention contains at least one selected from compound (I) or a salt thereof as an active ingredient. The amount of compound (I) or a salt thereof contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it exhibits a bactericidal effect.

The agricultural and horticultural fungicides of the present invention may be conjugated to a wide variety of filamentous fungi such as, for example, Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, It can be used to control plant diseases derived from fungi belonging to the fungus (Zygomycetes).

Examples of plant diseases (pathogenic bacteria) to be controlled are shown below.
Sugar beet: Brown spot disease (Cercospora beticola), black root disease (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc. ), Rust (Puccinia arachidis), damping-off (Pythium debaryanum), rust (Alternaria alternata), white scab (Sclerotium rolfsii), black affliction (Mycosphaerella berkeleyi), etc. cucumber: powdery mildew (Sphaerotheca fuliginea), Downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine blight (Fusarium oxysporum), sclerotis disease (Sclerotinia sclerotiorum), Botrytis cinerea, Anthracnose (Colletotrichum orbiculare), (Cladosporium cucumerinum), brown spot (Corynespora cassiicola), seedling blight (Pythium debaryanum, Rhizoctonia solani Kuhn), homoposis root rot (Phomopsis sp.) Spotted blight (Pseudomonas syrin) Gae pv. Lechrymans, etc. Tomato: Botrytis cinerea, Cladosporium fulvum, Phytophthora infestans, Verticillium albo-atrum, Verticillium dahliae, powdery mildew Eggplant: Botrytis cinerea (Alternaria solani), sour mildew (Pseudocercospora fuligena), etc. Eggplant: Botrytis cinerea, Corynespora melongenae, powdery mildew (Erysiphe cichoracearum), mycosis (Mycovellosi atlassiii) , Sclerotinia sclerotiorum, Verticillium dahliae, Phomopsis vexans etc. Strawberry: Botrytis cinerea, powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae, plague (Phytophthora cactorum), soft rot (Rhizopus stolonifer), yellow rot (Fusarium oxysporum), wilt (Verticillium dahliae) etc. Onion: Color rot (Botrytis allii), Botrytis cinerea, Botrytis scamosa, Peronospora destructor, Phytophthora porri etc. Cabbage: Plasmodiophora brassicae, Soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. Campestris), black spot blight (Pseudomonas syringae pv. Maculicola, P. s. Pv. Alisalensis), downy mildew (Peronospora parasitica), scab disease Sclerotinia sclerotiorum, black rot (Alternaria brassicicola), gray mold (Botrytis cinerea), etc. Bean: sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), phaeiogliosis griseola) etc

Apple: powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), Monilia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), scab (Valsa mali), spotted leaf diseases (Alternaria mali), red star disease (Gymnosporangium) yamadae), Botryosphaerus (Botryosphaeria berengeriana), Anthracnose (Glomerella cingulata, Colletotrichum acutatum), Brown Spot Disease (Diplocarpon mali), Soot Spot Disease (Zygophiala jamaicensis), Soot Spot Disease (Gloeodes pomigena), Purple Coat Leaf Disease (Helicobasidium mompa), gray mold (Botrytis cinerea), etc. Ume: scab (Cladosporium carpophilum), gray mold (Botrytis cinerea), scab (Monilinia mumecola), etc. oyster (Phyllactinia kakicola), anthrax Disease (Gloeosporium kaki), scaly leaf disease (Cercospora kaki), etc. peach: Aspergoniasis (Monilinia fructicola), scab (Cladosporium carpophilum), homoposis rot (Phomopsis sp.), Perforation fine Diseases (Xanthomonas campestris pv. Pruni) etc. Almonds: Hypton disease (Monilinia laxa), spot disease (Stigmina carpophila), scab (Cladosporium carpophilum), leaf blight disease (Polystigma rubrum), spot leaf disease (Alternaria alternata), Anthracnose (Colletotrichum gloeospoides) etc. Sweet cherry: Monascus disease (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Juvenile blight (Monilinia kusanoi) etc. Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis) etc. Pear: scab (Venturia nashicola), scab (Gymnosporangium asiaticum), black scab (Alternaria kikuchiana) Ring blight (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown leaf blight (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: Peblet disease (Pestalotiopsis longiseta, P . theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum) etc. Citrus: scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), melanose disease (Diaporthe citri), scab (Xanthomonas campestris pv. Citri), powdery mildew (Oidium sp.), Etc.

Wheat: powdery mildew (Blumeria graminis f. Sp. Tritici), mildew (Gibberella zeae), red rust (Puccinia recondita), brown snow blight (Pythium iwayamai), red snow blight (Monographella nivalis), eyelid Disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow blight (Typhula incarnata), snow blight (Myriosclerotinia borealis), blight (Gaeumannomyces graminis graminis) ), Ergot disease (Claviceps purpurea), lumber scab (Tilletia caries), naked scion (Ustilago nuda), etc. Barley: plague (Pyrenophora graminea), web blight (Pyrenophora teres), cloud disease (Rhynchosporium secalis), Bare scab (Ustilago tritici, U. nuda), etc. Rice: Pyricularia (Pyricularia oryzae), sheath blight (Rhizoctonia solani), fool seedling (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicola , Blight leaf blight (Xanthomonas oryzae), seedling blight (Burkholderia plantarii), brown leaf blight (Acidovorax avenae), leaf blight (Burkholderia glumae), leaf blight (Cercospora oryzae), rice blight (Ustiliginoidea) virens), brown rice (Alternaria alternata, Curvularia intermedia), belly black rice (Alternaria padwickii), reddish rice (Epicoccum purpurascens), etc. Tobacco: sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), Epithelium phiteophyhio ), Etc. Tulip: Gray mold (Botrytis cinerea), etc. Sunflower: Downy mildew (Plasmopara halstedii), sclerotis disease (Sclerotinia sclerotiorum), etc. Bentograss: snowfever scleroderma (Sclerotinia borealis), large patch (Rhizoctonia solani) , Brown patch (Rhizoctonia solani), duller spot (Sclerotinia homoeocarpa), rice blast (Pyricularia sp.), Red burn (Pythium aphanidermatum) ), Anthracnose (Colletotrichum graminicola), etc. Orchard grass: powdery mildew (Erysiphe graminis), etc. Soybean: Purple spot (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyriz) , Sclerotinia sclerotiorum, Anthracnose (Colletotrichum truncatum), Botrytis cinerea, Elsinoe glycines, Diaporthe phaseolorum var. Sojae etc. Potato: Phytophthora infestans , Phytophthora blight (Alternaria solani), black bruise (Thanatephorus cucumeris), half-body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens) etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola) etc. Rape: sclerotinia sclerotiorum, root scab (Phoma lingam), black spot (Alternaria brassicae) etc. Coffee: rust (Hemileia vas) tatrix), anthracnose (Colletotrichum coffeanum), brown eye disease (Cercospora coffeicola), etc. Sugar cane: brown rust (Puccinia melanocephala) etc. Maize: scab (Gloeocercospora sorghi), rust (Puccinia sorghi), southern part (Puccinia sorghi) ), Panicle Blight (Ustilago maydis), Sesame Leaf Blight (Cochliobolus heterostrophus), Ssu (Setosphaeria turcica), etc. Cotton: Seedling blight (Pythium sp.), Rust (Phakopsora gossypii), Mildew (Mycosphaerella) areola), anthrax (Glomerella gossypii), etc.

The fungicides for agricultural and horticultural use of the present invention are used on cereals, vegetables, root vegetables, potatoes, fruit trees, trees such as fruits, tea, coffee, cacao, grasses, grasses, grasses, cotton etc. Is preferred.

The fungicides for agricultural and horticultural use of the present invention can be applied to each part of plants, for example, leaves, stems, handles, flowers, buds, fruits, seeds, sprouts, roots, tubers, tubers, shoots, cuttings, etc. . In addition, improved varieties and varieties, cultivars, mutants, hybrids and genetically modified organisms (GMOs) of these plants can also be targeted.

The fungicide for agricultural and horticultural use of the present invention is used for seed treatment, foliage application, soil application, water surface application, etc. which are carried out to control various diseases occurring in agricultural and horticultural crops including florets, turf and grass. Can.

The fungicide for agricultural and horticultural purposes of the present invention contains components other than the 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds of the present invention. It is also good. Other components include known carriers used for formulation and the like. Moreover, as other ingredients, conventionally known fungicides, insecticides / acaricides, nematocides, soil insecticides, plant regulators, synergists, fertilizers, soil conditioners, animal feed and the like can be mentioned. be able to. By including such other components, a synergistic effect may be exhibited.

Specific examples of the bactericide which can be used in combination or in combination with the agricultural and horticultural bactericide of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitors:
(a) RNA polymerase I inhibitors: benalaxyl (benalaxyl), benalaxyl-M (benalaxyl-M), fulalaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), oxadixyl (oxadixyl), clozilacon ), Off-race (ofurace);
(b) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethyrimol (ethirimol);
(c) DNA / RNA synthesis inhibitors: hymexazol, octilinone;
(d) DNA topoisomerase II inhibitor: oxolinic acid.

(2) Mitotic proliferation inhibitors and cytostatics:
(a) β-tubulin polymerization inhibitor: benomyl (benomyl), carbendazim (carbendazim), chlorphenazole (chlorfenazole), fuberidazole (fuberidazole), thiabendazole (thiabendazole), thiophanate (thiophanate), thiophanate methyl (thiophanate-methyl) , Dietophencarb (diethofencarb), zoxamide (zoxamide), etaboxam (ethaboxam);
(b) cell division inhibitors: penccuron;
(c) Delocalized inhibitors of spectrin-like protein: fluopicolide.

(3) Respiratory inhibitor:
(a) Complex I NADH oxidoreductase inhibitors: diflumetrim, tolfenpyrad;
(b) Complex II succinate dehydrogenase inhibitors: benodanyl (benodanil), flutolanil (flutolanil), mepronil (mepronil), isofetamide (isofemid), fluopyram (fluopyram), fenfuram (fenfuram), flumecyclox (furmecyclox) Carboxin, Oxycarboxin, Thifluzamide, Benzovindiflupyr, Bixafen, Fluxapiroxad, Flamethopyr, Isopyrazam, Penflufen, penthiopyrad, sedaxane, boscalid, pyradiflumid;
(c) Complex III ubiquinol oxidase Qo inhibitors: azoxystrobin (azoxystrobin), coxoxystrobin (coumoxystrobin), comethoxystrobin (coumethoxystrobin), enoxastrobin (enoxastrobin), fluphenoxystrobin (flufenoxystrobin) , Picoxystrobin (pyroxystrobin), pyraclostrobin, pyraclostrobin, pyrametostrobin, triclopyricarb (triclopyricarb), kresoxim-methyl (kresoxim-methyl), trifloxyst Robin (trifloxystrobin), Dimoxystrobin (dimoxystrobin), Phenaminstrobin (fenaminstrobin), Metominostrobin (metominostrobin), Orysastrobin (orysastrobin), Famoxadone (famoxadone), Fluoxastrobin (fluoxastrobin), Fenamide (Fenamidone), pyribencarb (pyribencarb), Man Oldest Robin (mandestrobin);
(d) Complex III ubiquinol reductase Qi inhibitors: Cyazofamid (cyazofamid), amisulbrom (amisulfrom);
(e) Uncoupling agent for oxidative phosphorylation: binapacryl (binapacryl), meptyldinocap (meptyldinocap), dinocup (dinocap), fluazinam (fluazinam), ferimzone (ferimzone);
(f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthetase): Fentin acetate, Fentin chloride, Fentin hydroxide;
(g) ATP production inhibitors: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): amethocrazine (ametoctradin).

(4) Amino acid and protein synthesis inhibitors (a) Methionine biosynthesis inhibitors: Andoprim (andoprim), cyprodinil (cyprodinil), mepanipyrim (mepanipyrim), pyrimethanyl (pyrimethanil);
(b) Protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.

(5) Signal transduction inhibitors:
(a) Signal transduction inhibitors: quinoxyfen (quinoxyfen), proquinazid (proquinazid);
(b) MAP and histidine kinase inhibitors in osmotic signaling: fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone, vinclozolin.

(6) Lipid and cell membrane synthesis inhibitors:
(a) Phospholipid biosynthesis, methyl transferase inhibitor: Edifenphos (edifenphos), iprobenphos (iprobenfos), pyrazophos (pyrazophos), isoprothiolane (isoprothiolane);
(b) Lipid peroxides: biphenyl (biphenyl), chloroneb (chloroneb), dichloran (dichloran), quintozene (quintozene), tecnazen (tecnazene), tolclofos methyl (tolclofos-methyl), etridiazole (etridiazole);
(c) Agents that act on cell membranes: iodocarb (iodocarb), propamocarb (propamocarb), propamocarb hydrochloride (propamocarb-hydrochloride), propamocarb busetylate (propamocarb-foseylate), prothiocarb (prothiocarb);
(d) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis (bacillus subtilis), Bacillus subtilis QST 713 (bacillus subtilis strain QST 713), Bacillus subtilis FZB 24 (bacillus subtilis strain FZB24), , Bacillus subtilis strain D747 (bacillus subtilis strain D747), Bacillus amyloliquefaciens (bacillus amyloliquefaciens);
(e) Agents that disrupt cell membranes: extracts of Goseika Jupte (tea tree) (melaleuca alternifolia (tea tree) extract).

(7) Sterol biosynthesis inhibitor of cell membrane:
(a) Demethylation inhibitors at position C14 in sterol biosynthesis: Triforine, pyrifenox, pyrisoxazole, phenarimol, fenarimol, flurprimidol, fluarimidol, nuarimol, Imazalil (imazalil), Imazalil sulfate (imazalil-sulphate), Oxpoconazole fumarate (oxpoconazole fumarate), peflazoate (pefurazoate), prochloraz (prochloraz), triflumizole (triflumizole), viniconazole (viniconazole), azaconazole azaconazole), bitertanol, bromuconazole (bromuconazole), cyproconazole (cyproconazole), diclobutrazol (diclobutrazol), difenoconazole (difenoconazole), diniconazole (diniconazole), diniconazole-M (diniconazole-M), Ciconazole (epoxiconazole), etaconazole (etaconazole), fenbuconazole (fenbuconazole), fluquinconazole (fluquinconazole), flusilazole (flusilazole), flutriahol (flutriafol), fluconazole (furconazole), fluconazole-cis (furconazole-cis), Hexaconazole (hexaconazole), imibenconazole (imibenconazole), ipconazole (ipconazole), metconazole (metconazole), microbutanil (myclobutanil), penconazole (penconazole), propiconazole (propiconazole), fluquinconazole (fluquinconazole), simeconazole simeconazole), tebuconazole (tebuconazole), tetraconazole (tetraconazole), triadimefon (triadimefon), triadimenol (triadimenol), triticonazole (triticonazole), prothioconazo Le (prothioconazole), voriconazole (voriconazole), main phen triflupromazine Kona tetrazole (mefentrifluconazole);
(b) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperaline, piperalin, spiroxamine;
(c) 3-Keto reductase inhibitors at C4 demethylation of sterol biosynthesis system: fenhexamid, fenpyrazamine;
(d) Squalene epoxidase inhibitors of sterol biosynthetic system: pyributicarb, naphthifine (naftifine), terbinafine (terbinafine).

(8) Cell wall synthesis inhibition (a) Trehalase inhibitor: validamycin
(b) Chitin synthetase inhibitors: polyoxins (polyoxins), polyoxorim (polyoxorim);
(c) Cellulose synthetase inhibitors: dimethomorph, flumorph, pyrimorph, benthiavalicarab-isopropyl, iprovaricarb, tolprocarb, valifenalate (valilifelate) ), Mandipropamide.

(9) Melanin Biosynthesis Inhibitor (a) Reductase Inhibitor of Melanin Biosynthesis: Phthalide, phthaloquilon, tricyclazole;
(b) Dehydratase inhibitor of melanin biosynthesis: Carpropamide (carpropamid), diclocymet (diclocymet), phenoxanyl (fenoxanil).

(10) Host plant resistance inducer:
(a) Agents acting on the salicylic acid synthesis pathway: Acibenzolar-S-methyl (acibenzolar-S-methyl);
(b) Others: probenazole (probenazole), thiazinyl (tiadinil), isotianil (isotianil), laminarin (laminarin), extract of reedoutria sachalinensis.

(11) Agents with unknown activity: shimoxanil (cymoxanil), fosetyl-aluminium, phosphoric acid (phosphate) (phosphoric acid (phosphate)), teclophthalam (teclofalam), triazoxide (triazole), flusulfamide flusulfamide), diclomezine, methasulfocarb, cyflufenamide, metrafenone, pyriofenone, dodine, dodine free base, flutianil.

(12) Agents having multiple action points: copper (copper salt) (copper (copper salt)), Bordeaux solution (bordeaux mixture), copper hydroxide (copper hydroxide), copper naphthalate (copper naphthalate), copper oxide (copper oxide) , Copper oxychloride (copper oxychloride), copper sulfate (copper sulfate), sulfur (sulfur), sulfur product (sulfur product), calcium polysulfide (calcium polysulfide), ferbam (ferbam), mancozeb (mancozeb), maneb (maneb) , Mankapper (mancopper), methylam (metiram), polycarbamate (polycarbamate), propineb (propineb), thiram (thiram), zineb (zineb), ziram (ziram), captan (captan), captafol, phorpet (Folpet), chlorothalonil, dichlofluanid, tolylfluanid, guazatine Iminoctadine acetate (iminoctadine triacetate), iminoctadine carbonochloridate tagine Alves Sil salt (iminoctadine trialbesilate), Anirajin (anilazine), dithianon (dithianon), Kinomechioneto (quinomethionate), Furuoruimido (fluoroimide).

(13) Other agents: DBEDC, fluorophorpet (fluorofolpet), guazatine acetate, bis (8-quinolinolato) copper (II) (bis (8-quinolinolato) copper (II)), propamidine ( propamidine), chloropicrin (chloropicrin), cyprofuram, agrobacterium (agrobacterium), bethoxazine, bethoxazin, diphenylamine, methyl isothiocyanate (MITC), methyl isothiocyanate, mildiomycin, Capsaicin (capsaicin), cuflaneb (cufraneb), cyprosulfamide (cyprosulfamide), dazomet (dazomet), debacarb (debacarb), dichlorophen (dichlorophen), flumethover (flumetover), fosetyl calcium (fosetyl-calcium), fosetyl sodium ( fosetyl-sodium), irumamycin (irumamycin), Tamycin (natamycin), nitrothal isopropyl (oxamocarb), pyrrolitrin (pyrolnitrin), tebufuroquin (tebufloquin), tolnifanide (tolnifanide), zarilamide (zarilamide), argophase (algophase), amicalthiazole (amicarthiazol) ), Oxathiapiprolin (oxathiapiprolin), methylam zinc (metiram zinc), benzazole (benthiazole), trichlamide (trichlamide), uniconazole (uniconazole), oxyfenthiin (oxyfenthiin), picalbutrazox (picarbutrazox) Picoxamide (fenpicoxamide), dicloventiazox (dichlobentiazox), quinofumelin (quinofumelin) thiuram (thiuram), ambam (ambam), Agrobacterium radiobacter (agrobacterium radiobacter), coniothium minitans (co Niothyrium minitans, Pseudomonas fluorescens (pseudomonas fluorescens), Pseudomonas rhodesia (pseudomonas rhodesiae), Talaromyces flavaus (talaromyces flavus), Trichoderma atroviride (trichoderma), non-pathogenic simplex), Variovorax paradoxus, Lactobacillus plantarum.

Specific examples of the bactericide which can be used in combination or in combination with the agricultural and horticultural bactericide of the present invention are shown below.

(1) Acetylcholinesterase inhibitors:
(a) Carbamate system: alanical (alanycarb), aldicarb (aldicarb), bendiocarb (bendiocarb), benfuracarb (benfuracarb), butocarboxim (butocarboxim), butoxycarboxim (butoxycarboxim), carbaryl (carbaryl), carbofuran (carbofuran), Carbosulfan (carbosulfan), ethiophenecarb (ethiofencarb), fenobucarb (fenobucarb), formetanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb), methiocarb (methiocarb), methomil (methomyl), oxamyl (oximyl) ), Propoxur, thiodicarb, thiophanox, triazamate, triazamate, trimethacarb, XMC, xylylcarb, phenothioca) Rub (fenothiocarb), MIPC, MPMC, MTMC, aldoxycarb, aldoxycarb, allyxycarb, aminocarb, aminocarb, bufencarb, cloetocarb, metam-sodium, promecarb );

(b) Organophosphorus: Acephate, azamethiphos (azamethiphos), azinphos-ethyl (azinphos-ethyl), azinphos-methyl, azinphos-methyl, cadusafos, chloroethoxyphos, chlorphenbinfos Phos (chlorfenvinphos), chlormephos (chlormephos), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl (chlorpyrifos-methyl), coumaphos (coumaphos), cyanophos (cyanophos), demeton-S-methyl (demeton-S-methyl), diazinon (diazinon) ), Dichlorvos / DDVP, dicrotophos, dimethoate, dimethoate, dimethylvinphos, disulfoton (disulfoton), EPN, ethion, ethionophos (ethoprophos), famhur (famphur), fenamiphos fenamiphos), fenitrothion (fenitr) othion, fenthion, fosthiazate, heptenophos (heptenophos), imicyafos (imicyafos), isofenphos (isofenphos), isocarbophos (isocarbophos), isoxathion, malathion, malcarbion (methhamidophos), methidathion, mevinphos (mevinphos), monocrotophos (monocrotophos), naled, omethoate, oxydimeton-methyl, parathion, parathion, parathion-parathion methyl), phenthoate, phorate, phosalone, phosmet, phosmet, phosphamidon, phoxim, pholymiphos-methyl, pirimiphos-methyl, profenofos, profenofos Tamphos (propetamphos), prothiophos (prothiofos), pyracophofos, pyridaphenthion (pyridaphenthion), quinalphos (quinalphos), sulfotep (sulfotep), tebupilinfos (tebupirimfos), temephos (temephos), terbuphos (terbufos) tetrachlorvin phos), thiomethon, thioazophos, trichlorphos (trichlorfon), vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanophenphos, cyanophos, CYAP, Demeton-S-methylsulfone (demeton-S-methyl sulfone), dialiphos (dialifos), diclofenthion (dichlofenthion), dioxabenzophos (dioxabenzofos), etrimphos (etrimfos), fensulfothion (phensulfothion), Lupyrazophos (flupyrazofos), phonophos (fonofos), formothione (formothion), phosmethilan (fosmethilan), isazofos (isazofos), iodophenphos (jodfenphos), methaphis (methacrifos), pyrimiphos-ethyl (pirimiphos-ethyl), phosphocarb , Propaphos, prothoate, sulprofos.

(2) GABA-agonizing chloride channel antagonist: acetoprole, acetoprole, chlordane, endosulfan (endosulfan), ethyprole (ethiprole), fipronil (fipronil), pyrafluprole (pyrafluprole), pyriprole (pyriprole), Camphechlor, heptachlor, dienochlor.
(3) Sodium channel modulators: acritanthrin (acrinathrin), d-cis-trans arethrin (d-cis-trans allethrin), d-trans allethrin (d-trans allethrin), bifenthrin (bifenthrin), bioallethrin (bioallethrin), biot Allethrin s-cyclopentyl isomer (bioallethrin s-cyclopentyl isomer), bioresmethrin (bioresmethrin), cycloprothrin (cycloprothrin), cyfluthrin (cyfluthrin), beta-cyfluthrin (β-cyfluthrin), cyhalothrin (cyhalothrin), lambda-cyhalothrin (λ -cyhalothrin), gamma-cyhalothrin (γ-cyhalothrin), cypermethrin (cypermethrin), alpha-cypermethrin (α-cypermethrin), beta-cypermethrin (β-cypermethrin), theta-cypermethrin (θ-cypermethrin), zeta -Cypermethrin (ζ-cypermethrin), cifeno Trin [(1R) -trans isomer] (cyphenothrin [(1R) -trans isomer)], deltamethrin (deltamethrin), enpentrin [(EZ)-(1R) -isomer] (Empenthrin [(EZ)-(1R) ], Esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate (τ) -fluvalinate), halfenprox (halfenprox), imiprothrin (imiprothrin), cadestrin (kadethrin), permethrin (permethrin), phenothrin [(1R)-trans isomer] (phenothrin [(1R)-trans isomer)], prarethrin ( prallethrin), pyrethrum (pyrethrum), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin), tetramethrin [(1R) -isomer] tetramethrin [(1R) -isomer], tralomethrin (tralomethrin), transfluthrin (transfluthrin), allethrin (allethrin), pyrethrin (pyrethrins), pyrethrin I (pyrethrin I), pyrethrin II (pyrethrin II), profluthrin (profluthrin) , Dimefluthrin, bioethanomethrin, biopermethrin, biopermethrin, transpermethrin, transflumethrin, fenfluthrin, fenpyritrin, flubrocythrinate, flufen Prox (flufenprox), metofluthrin (metofluthrin), protrifenbute (protrifenbute), pyrethmethrin (pyresmethrin), terarethrin (terallethrin).

(4) Nicotinic acetylcholine receptor agonists: acetamiprid (acetamiprid), clothianidin (clothianidin), dinotefuran (dinotefuran), imidacloprid (imidacloprid), nitenpyram (nitenpyram), nithiazine (nithiazine), tiacloprid, thiamethoxam tha Sulfoxaflor (sulfoxaflor), nicotine (nicotine), flupyradifurone (flupyradifurone), flupyrimine (flupyrimine).
(5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad.
(6) Chloride channel activators: Abamectin (abamectin), emamectin benzoate (emamectin-benzoate), lepimectin (lepimectin), milbemectin, milvermectin, ivermectin, selamectin, doramectin, emrinometin (Eprinomectin), moxidectin (moxidectin), milbemycin (milbemycin), milbemycin oxime (milbemycin oxime), nemadectin (nemadectin).
(7) Juvenile hormone-like substances: hydroprene (hydroprene), kinoprene (methoprene), methoprene (phenopycarb), pyriproxyfen (pyriproxyfen), diophenolan (diofenolan), epofenonane (epofenonane), triprene (triprene) ).
(8) Other nonspecific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar emetic.
(9) Homoptera order selective antifeedants: flonicamid (flonicamid), pimetrozin (pymetrozine), pyrifluquinazon (pyrifluquinazon).

(10) Acaride growth inhibitor: clofenthezin (clofentezine), diflovidazine (diflovidazin), hexythiazox (hexythiazox), etoxazole (etoxazole).
(11) Microorganism-derived insect midgut inner membrane disrupting agent: Bacillus thuringiensis subsp. Islaelensis (bacillus thuringiensis subsp. Israelensis), Bacillus sphaericus (bacillus sphaericus), Bacillus thuringiensis subsp. Squirrel (bacillus thuringiensis subsp. Aizawai) , Bacillus thuringiensis subsp. Kurstaki (bacillus thuringiensis subsp. Kurstaki), Bacillus thuringiensis subsp. Bacillus thuringiensis subsp. Tenebrionis, Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A. 105, Cry2 Ab3 , Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
(12) Mitochondrial ATP biosynthesis enzyme inhibitor: diafenthiuron (diafenthiuron), azocyclotin (azocyclotin), cyhexatin (cyhexatin), fenbutatin oxide oxidized, propargite (propargite), tetradiphone (tetradifon).
(13) Oxidative phosphorylation and uncoupling agent: chlorfenapyr (chlorfenapyr), sulfluramide (sulfluramid), DNOC, binapacryl (binacapacryl), dinobuton (dinobuton), dinocap (dinocap).
(14) Nicotinic acetylcholine receptor channel blocker: bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium salt, thiocyclam.
(15) Chitin synthesis inhibitors: bistrifluron (bistrifluron), chlorfluazuron (chlorfluazuron), diflubenzuron (diflubenzuron), flucycloxuron (flucycloxuron), flufenoxuron (flufenoxuron), hexaflumuron (hexaflumuron), Rufenuron (lufenuron), novaluron (novaluron), noviflumuron (noviflumuron), teflubenzuron (teflubenzuron), triflumuron (triflumuron), buprofezin (buprofezin), fluazuron (fluazuron).
(16) Diptera molt-disrupting agents: cyromazine.
(17) Molting hormone receptor agonist: Chromafenozide (halofenozide), halofenozide (halofenozide), methoxyfenozide (methoxyfenozide), tebufenozide (tebufenozide).
(18) Octopamine receptor agonists: amitraz (amitraz), demiditraz (demiditraz), chlordimeform (chlordimeform).
(19) Mitochondrial electron transport complex III inhibitor: acequinocyl, fluacrypyrim, hydramethylnon.
(20) Mitochondrial electron transport complex I inhibitor: phenazaquin (fenazaquin), fenpyroximate, fenimidoxime, pyridadifen, pyridaben (pyridaben), tebufenpyrad (tebufenpyrad), tolfenpyrad (tolfenpyrad), rotenone (rotenone).

(21) Voltage-gated sodium channel blockers: indoxacarb, metaflumizone (metaflumizone).
(22) Acetyl CoA carboxylase inhibitor: spirodiclofen (spirodiclofen), spiromesifen (spiromesifen), spirotetramat.
(23) Mitochondrial electron transport complex IV inhibitor: aluminum phosphide, calcium phosphide, phosphine, phosphine, zinc phosphide, cyanide.
(24) Mitochondrial electron transport complex II inhibitor: sienopyraphen (cyenopyrafen), ciflumethophene (cyflumetofen), pyflubumide (pyflubumide).
(25) Ryanodine receptor modulators: chlorantraniliprole (chlororantriliprole), cyanantraniliprole (cyantraniliprole), flubendiamide (flubendiamide), cyclaniliprol (cycliliprole), tetraniliprol (tetraniliprole).
(26) Mixed Function Oxidase Inhibitor Compound: Piperonyl butoxide.
(27) Latrophin receptor agonist: depsipeptide (depsipeptide), cyclic depsipeptide (cyclodepsipeptide), 24-membered cyclic depsipeptide (24 membered cyclodepsipeptide), emodepside (emodepside).
(28) Other agents (the mechanism of action is unknown): azadirachtin (azadirachtin), benzoxiate (benzoximate), biphenazate (bifenazate), bromopropyrate (bromopropylate), quinomethionate (quinomethionate), cryolite (crolite), dicophor (dichophorate) dicofol), pyridalyl, benclothiaz, sulfur, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate benzomate), meta aldehyde (metaldehyde), chlorobenzilate, clothiazoben, dicyclanil, dicyclanil, fenoxacrim, fentrifanil, fentrifanil, flubenzimine, fluphenazine , Gossip Rua (gossyplure), japonilure (japonilure), methoxadiazon (metoxadiazone), petroleum (oil), potassium oleate (potassium oleate), tetrasul (tetrasul), triaracene (triarathene), afido piropen (afidopyropen), flomethoquin (flometoquin), flufiprole), fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide, flula la caride, (Fluxatamide), 5- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -2- (1H-1,2,4-triazole-1) - Yl) benzonitrile (CAS: 943137-49-3) (5- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazole-3-yl] -2- (1H-1,2 (4-triazole-1-yl) benzonitrile (CAS: 943137-49-3)), brofranilide (broflanilide), other metadiamides, stynerneema carpocapsae (steinernema carpocapsae), stynernema grascerei (steinernema glaseri), pastoria penetrans (pasteuria penetrans) ), Pequilomices tenuipes (paecilomyces tenuipes), Pequilomyces fumosoroseus (paecilomyces fumosoroseus), Bovelia Basiana (beavelia bassiana), Bovelia bronniartii (beauveria brongniartii), Metalidium anifolie.

(29) Antiparasitic agent:
(a) Benzimidazole: fenbendazole (fenbendazole), albendazole (albendazole), triclabendazole (triclabendazole), oxybendazole (oxibendazole), mebendazole (mebendazole), oxfendazole (oxfendazole), perbendazole ( parbendazole), flubendazole (flubendazole), febantel (febantel), netobimin (netobimin), thiophanate (thiophanate), thiabendazole (thiabendazole), cambendazole (cambendazole);
(b) Salicylanilides: closantel, oxyclozanide, rafoxanide (rafoxanide), niclosamide (niclosamide);
(c) Substituted phenolics: nitroxinil, nitroscanate;
(d) Pyrimidines: pyrantel, morantel;
(e) Imidazothiazole system: levamisole (levamisole), tetramisole (tetramisole);
(f) Tetrahydropyrimidines: praziquantel, epsiprantel;
(g) Other anthelmintics: cyclodiene (cyclodiene), lyania (ryania), clorsulon (melornazol), metronidazole (metronidazole), demiditraz (demiditraz), piperazine (piperazine), diethyl carbamazine (diethylcarbamazine), dichlorophen (dichlorophene) , Monetantel (monepantel), tribenzimidin (tribendimidin), amidantel (amidantel), thiacetarsamide (thiacetarsamide), melarsomine (melarsomine), arsenamide (arsenamide).

Specific examples of the plant regulator which can be used in combination or in combination with the pest control agent of the present invention are shown below.
Abscisic acid (abscisic acid), kinetin (kinetin), benzylaminopurine (Benzylaminopurine), 1,3-diphenylurea (1,3-diphenylurea), forchlorfenuron (forchlorfenuron), thidiazuron (thidiazuron), chlorphenuron ( chlorfenuron), dihydrozeatin (gibberellin A4), gibberellin A4 (gibberellin A4), gibberellin A7 (gibberellin A7), gibberellin A3 (gibberellin A3), 1-methylcyclopropane (1-methylcyclopropane) -Acetylaminoethoxyvinylglycine (alias: abiglycine) (N-acetyl aminoethoxyvinyl glycine (aviglycine)), aminooxyacetic acid (aminooxyacetate), silver nitrate (silver nitrate), cobalt chloride (cobalt chloride), IAA, 4-CPA, cloprop (Cloprop), 2,4-D, MCPB, indole-3- Acid (indol-3-butyrate), dichlorprop (dichlorprop), phenothiol (phenothiol), 1-naphthyl acetamide (1- naphthhyl acetamide), ethychlozate, cloxifonac (cloxyfonac), maleic acid hydrazide (maleic (maleic) acid hydrazide, 2,3,5-triiodobenzoic acid, 2,3-5 triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid ((-)-jasmonic acid ), Methyl jasmonate (methyl jasmonate), (+)-strigol ((+)-strigol), (+)-deoxystrigol ((+)-deoxystrigol), (+)-orovancol ((+)-) orobanchol), (+)-Sorgolactone ((+)-sorbolactone), 4-oxo-4- (2-phenylethyl) aminobutyric acid (4-oxo-4- (2-phenylethyl) aminobutyric acid), ethephon (ethephon) , Chlormequat, mepicor Tocolide (mepiquat chloride), benzyl adenine (benzyladenine), 5-amino levulinic acid (5-amino levulinic acid), daminozide (daminozide).

[Formulation prescription]
The fungicides for agricultural and horticultural use of the present invention are not particularly limited by the dosage form. For example, dosage forms such as wettable powders, emulsions, powders, granules, aqueous solvents, suspensions, water dispersible granules, tablets and the like can be mentioned. The preparation method for the preparation is not particularly limited, and known preparation methods can be adopted depending on the dosage form.
Some of the formulation examples are shown below. The preparation formulations shown below are merely illustrative and can be modified without departing from the scope of the present invention, and the present invention is not limited at all by the following formulation examples. "Parts" means "parts by weight" unless otherwise noted.

Formulation Example 1: Wettable powder
40 parts of the 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and alkylnaphthalene Three parts of the sulfonate are uniformly mixed and finely ground to obtain a wettable powder of 40% active ingredient.

Formulation Example 2 Emulsion
Thirty parts of a 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and polyoxyethylene alkyl Seven parts of allyl ether are mixed and dissolved to obtain an emulsion of 30% active ingredient.

Formulation Example 3 Granule
5 parts of 1,3,5,6-tetra-substituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and alkyl 7 parts of sodium sulfate is uniformly mixed, finely ground, and then granulated to a particle diameter of 0.5 to 1.0 mm to obtain granules of 5% of active ingredient.

Formulation Example 4 Granules
5 parts of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds of the present invention, 73 parts of clay, 20 parts of bentonite, dioctyl sulfosuccinate sodium salt 1 part and 1 part of potassium phosphate were mixed uniformly and ground. Water is added thereto and thoroughly mixed, and then granulated and dried to obtain granules of 5% active ingredient.

(Preparation Example 5: Suspension)
10 parts of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, polycarboxylic acid sodium salt Two parts, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water are mixed and wet-milled to a particle size of 3 microns or less to obtain a 10% active agent suspension.

(Formulation example 6: Granulating water dispersible powder)
40 parts of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds of the present invention, 36 parts of clay, 10 parts of potassium chloride, alkyl benzene sulfonic acid sodium salt One part, 8 parts of lignin sulfonic acid sodium salt, and 5 parts of formaldehyde condensate of alkylbenzene sulfonic acid sodium salt are uniformly mixed and finely ground, and then an appropriate amount of water is added and then kneaded to form clay. The clay is granulated and then dried to obtain a water-dispersible powder with 40% active ingredient.

Next, the present invention will be described more specifically by showing synthetic examples. However, the present invention is not limited at all by the following synthesis examples.

Example 1
(2- (1- (2- (5-fluoro-2-methoxyphenyl) -2- (methoxyimino) ethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-) Synthesis of triazol-2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide (Compound No. 1)

(Step 1) 2- (1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazole) Synthesis of -2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide

　Ｎ－イソプロピル－２－メチル－２－（５－メチル－２，４－ジオキソ－６－（２Ｈ－１，２，３－トリアゾール－２－イル）－１，４－ジヒドロチエノ［２，３－ｄ］ピリミジン－３（２Ｈ）－イル）プロパンアミド（０．５６ｇ）をＮ，Ｎ－ジメチルホルムアミド（１０ｍｌ）に溶解させた。これに、氷冷下、炭酸カリウム（０．６２ｇ）および２－ブロモ－５’－フルオロ－２’－メトキシアセトフェノン（０．４４ｇ）を加え、室温にて一晩撹拌した。得られた液を氷水に注加し、酢酸エチルで抽出し、抽出相を水で洗浄し、次いで飽和食塩水で洗浄した。その後、無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：ｎ－ヘキサン／酢酸エチル）で精製し、目的化合物０．６２ｇ（収率７７％）を得た。
　得られた目的物の¹Ｈ－ＮＭＲを以下に示す。
　¹H-NMR (CDCl₃,δppm): 1.14(d,6H), 1.82(s,6H), 2.65(s,3H), 3.99(s,3H), 5.22(s,2H), 6.98-7.02(m,1H), 7.24-7.31(m,1H), 7.58-7.63(m,1H), 7.76(s,2H)

N-isopropyl-2-methyl-2- (5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol-2-yl) -1,4-dihydrothieno [2,3-d Pyrimidin-3 (2H) -yl) propanamide (0.56 g) was dissolved in N, N-dimethylformamide (10 ml). To this, under ice-cooling, potassium carbonate (0.62 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (0.44 g) were added and stirred overnight at room temperature. The resulting solution was poured into ice water, extracted with ethyl acetate, and the extracted phase was washed with water and then with brine. After that, it was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.62 g (yield 77%) of a target compound.
The ¹ H-NMR of the desired product obtained is shown below.
¹ H-NMR (CDCl ₃ , δ ppm): 1.14 (d, 6 H), 1.82 (s, 6 H), 2. 65 (s, 3 H), 3.99 (s, 3 H), 5.22 (s, 2 H), 6.98-7.02 ( m, 1 H), 7.24-7. 31 (m, 1 H), 7.58-7. 63 (m, 1 H), 7. 76 (s, 2 H)

(Step 2) 2- (1- (2- (5-fluoro-2-methoxyphenyl) -2- (methoxyimino) ethyl) -5-methyl-2,4-dioxo-6- (2H-1,2 Synthesis of 3, 3-Triazol-2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide

　２－（１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－６－（２Ｈ－１，２，３－トリアゾール－２－イル）－１，４－ジヒドロチエノ［２，３－ｄ］ピリミジン－３（２Ｈ）－イル）－Ｎ－イソプロピル－２－メチルプロパンアミド（０．２ｇ）をエタノール（５ｍｌ）に懸濁させた。これに、メトキシアミン塩酸塩（０．０５９ｇ）およびピリジン（０．０６２ｇ）を加え、一晩加熱還流した。得られた液を減圧濃縮し、濃縮液を氷水に注加し、酢酸エチルで抽出し、抽出相を水で洗浄し、次いで飽和食塩水で洗浄した。その後、無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：ｎ－ヘキサン／酢酸エチル）で精製し、目的化合物０．１４ｇ（収率６６％）を得た。
　得られた目的物の¹Ｈ－ＮＭＲを以下に示す。
　¹H-NMR (CDCl₃,δppm): 1.11(d,6H), 1.69(s,6H), 2.59(s,3H), 3.77(s,3H), 3.81(s,3H), 4.02-4.11(m,1H), 4.89(s,2H), 6.83-7.06(m,3H), 7.82(s,2H)

2- (1- (2- (5-Fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol-2-yl) ) -1, 4-Dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide (0.2 g) was suspended in ethanol (5 ml). To this was added methoxyamine hydrochloride (0.059 g) and pyridine (0.062 g) and heated to reflux overnight. The resulting solution was concentrated under reduced pressure, the concentrate was poured into ice water, extracted with ethyl acetate, the extracted phase was washed with water and then with saturated brine. After that, it was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.14 g (yield 66%) of a target compound.
The ¹ H-NMR of the desired product obtained is shown below.
¹ H-NMR (CDCl ₃ , δ ppm): 1.11 (d, 6 H), 1. 69 (s, 6 H), 2.59 (s, 3 H), 3. 77 (s, 3 H), 3.81 (s, 3 H), 4.02-4. 11 ( m, 1H), 4.89 (s, 2H), 6.83-7.06 (m, 3H), 7.82 (s, 2H)

Table 1 shows some of the compounds of the present invention prepared in the same manner as in the above examples. In the table, properties, melting point (mp) or refractive index (n _D ) are shown together as physical properties of each compound. The configuration E or Z in the table indicates a geometric isomer of oxime. "E" indicates that it is in E configuration, "Z" indicates that it is in Z configuration, "E / Z" indicates that the compound is a mixture of compounds in both configurations, and "E or Z" is that , Compounds in the E configuration and compounds in both the Z configuration.

Among the compounds shown in Table ^{1, 1} H-NMR (CDCl ₃ ) was measured for compounds having physical properties of viscous oil or amorphous. Table 2 shows the measured values.

[Biological test]
It is shown below that the 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds of the present invention are useful as active ingredients for agricultural and horticultural fungicides. In the test example of

(Preparation of emulsion for test)
5 parts by weight of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds, 93.5 parts by weight of dimethylformamide, and polyoxyethylene sorbitan monolaurate (Twin 20) 1.5 parts by weight was mixed and dissolved to obtain an emulsion (I) with a 5% active ingredient.

The control value was calculated by the following equation.
Control value (%) =
100-
100 × {spot area rate in treated area / spot area rate in untreated area}

Test Example 1 Apple Scab Control Test The concentration of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound in emulsion (I) is 125 ppm. As above, water was added and dissolved to obtain a drug solution. Subsequently, the above drug solution was applied to apple seedlings (variety "Obayashi", 3-4 leaf stage) grown in a pot for raising seedlings. After air-drying, conidia of apple scab (Venturia inaequalis) were inoculated (treatment section). As a control, apple seedlings which were not sprayed with the drug solution were similarly inoculated (untreated zone). They were placed in a 20 ° C. wet room with 12 hours of light and dark repeated.
Two weeks after inoculation, the leaves of the apple seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

An apple scab control test was conducted on the compounds of the compound numbers shown in Table 3. All compounds showed a control value of 75% or more.

(Test Example 2) Cucumber gray mold control test The concentration of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound in emulsion (I) was 125 ppm. Then, water was added to dissolve to obtain a drug solution. Subsequently, the above drug solution was applied to cucumber seedlings (cultivar "ground", cotyledon stage) grown in a pot for raising seedlings. After air drying, a conidia suspension of cucumber gray mold fungus (Botrytis cinerea) was dropped and inoculated (treatment section). As a control, cucumber seedlings which had not been sprayed with the drug solution were drop-inoculated in the same manner as described above (untreated zone). They were placed in a 20 ° C. wet room.
Four days after the inoculation, the leaves of the cucumber seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

A cucumber gray mold control test was conducted on the compounds No. 1, 2, 6 and 11. All compounds showed a control value of 75% or more.

Test Example 3 Wheat powdery mildew control test The emulsion (I) had a concentration of 125 ppm of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds. Then, water was added to dissolve to obtain a drug solution. Subsequently, the above drug solution was applied to wheat seedlings (cultivar "Chihoku", 1-2 leaf stage) grown in a pot for raising seedlings. After air-drying, conidia of wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) were sprinkled and inoculated (treatment group). As a control, wheat seedlings which were not sprayed with the drug solution were inoculated in the same manner as described above (untreated zone). They were placed in a 20 ° C. greenhouse.
The leaves of the wheat seedlings were visually observed on the day 6 days after the inoculation to determine the lesion area ratio, and the control value was calculated.

The wheat powdery mildew control test was conducted on the compounds of the compound numbers shown in Table 4. All compounds showed a control value of 75% or more.

(Experimental Example 4) Wheat leaf rust control test The concentration of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound in emulsion (I) is 125 ppm. As above, water was added and dissolved to obtain a drug solution. Subsequently, the above drug solution was applied to wheat seedlings (variety "Agriculture No. 61", 1-2 leaf stage) grown in a pot for raising seedlings. After air drying, wheat seedlings sprayed with the drug solution were inoculated with summer spore of wheat rust fungus (Puccinia recondita) and inoculated (treatment section). As a control, wheat seedlings which had not been sprayed with the drug solution were inoculated as described above (untreated zone). They were placed in a 20 ° C. greenhouse.
The leaves of the wheat seedlings were visually observed on the day after 12 days from the inoculation to determine the lesion area rate, and the control value was calculated.

A wheat leaf rust control test was conducted on the compounds of the compound numbers shown in Table 5. All compounds showed a control value of 75% or more.

Test Example 5 Acute Toxicity Test of Daphnia magna 1,3,5,6-Tetrasubstituted Thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione Compound as N, N-Dimethyl Compound It was dissolved in formamide. This was added to water and mixed to obtain a harmful composition for controlling harmful organisms on water of a final concentration of 0.001 μg / L, 0.01 μg / L, 0.1 μg / L, and 1 μg / L.
Ten Daphnia magna were exposed to the above-mentioned aquatic aquatic harmful biocidal control composition at about 20 ° C. for 48 hours. Next, the swimming inhibition rate of 10 Daphnia magna was measured. The half-effect concentration (EC 50 value) was calculated from the measured values by the drawing method.

With respect to the compound No. 1, an acute toxicity test of Daphnia magna was conducted. The half-effect concentration (EC 50 value) of the compound was> 100 μg / L.

Test Example 6 Acute Toxicity Test of Zebrafish (Danio rario) 1,3,5,6-Tetrasubstituted Thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione Compound N, N- It was dissolved in dimethylformamide. This was added to water and mixed to obtain a harmful composition for controlling harmful organisms on water of a final concentration of 0.001 μg / L, 0.01 μg / L, 0.1 μg / L, and 1 μg / L.
Twelve zebrafish fertilized eggs were exposed to the test solution at about 25 ° C. for 96 hours, and the mortality was measured. The half lethal concentration (LD50) was calculated by the drawing method from the measured values.

The acute toxicity test of zebrafish was carried out for the compound No. 1 compound. The half lethal concentration (LD50) of the compound was> 100 μg / L.

(Experimental example 7) Acute toxicity test of yellow medaka (Oryzias latipes) 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compound as N, N-dimethyl It was dissolved in formamide. This was added to water and mixed to obtain a harmful composition for controlling harmful organisms on water of a final concentration of 0.001 μg / L, 0.01 μg / L, 0.1 μg / L, and 1 μg / L.
Five adult adults were exposed to the test solution at about 23 ° C. for 96 hours, and the mortality was measured. The half lethal concentration (LD50) was calculated by the drawing method from the measured values.

The compound No. 1 compound was subjected to the acute toxicity test of Hemada. The half lethal concentration (LD50) of the compound was> 100 μg / L.

Since compounds selected at random among the compounds of the present invention exert the effects as described above, the compounds of the present invention, including compounds which could not be exemplified, have a bactericidal effect and cause phytotoxicity on plants. It can be understood that the compound is less toxic to humans and animals and has less environmental impact.

Claims (3)

The compound or its salt represented by a formula (I).

(In the formula (I),
R ¹ is a substituted or unsubstituted C1-6 alkyl group,
R ² represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C1 to 6 group 6 alkoxycarbonyl group, substituted or unsubstituted aminocarbonyl group, substituted or unsubstituted amino group, substituted or unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted 5 to 6 membered heteroaryl group, or cyano group And
R ³ is a substituted or unsubstituted C1-6 alkoxycarbonyl group, or a substituted or unsubstituted aminocarbonyl group,
R ⁴ and R ^{4 ′} are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
Z is an oxygen atom,
R ⁵ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, or a 5- to 6-membered saturated heterocyclyl group,
X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group,
n represents the number of chemically acceptable X, and is an integer from 0 to 5, and
When n is 2 or more, X may be the same or different. ) Substituents on substituted C1 ~ 6 alkyl group in R ⁵ is a halogeno group, hydroxyl group, C1 ~ 6 alkoxy group, C1 ~ 6 alkylthio group, C1 ~ 6 alkylsulfinyl group, C1 ~ 6 alkylsulfonyl group, C3 ~ 8 cycloalkyl The compound represented by the formula (I) according to claim 1, which is an alkyl group, a cyano group or an aminothiocarbonyl group, or a salt thereof. An agricultural and horticultural fungicide containing at least one compound selected from the group consisting of the compounds according to claim 1 and a salt thereof as an active ingredient.