WO2020255946A1 - 2,4-dioxo-1,4-dihydrothienopyrimidine compound, agricultural and horticultural bactericide - Google Patents

Abstract

The present invention provides: a 2,4-dioxo-1,4-dihydrothienopyrimidine compound which has excellent bactericidal activity and safety, and can be industrially advantageously synthesized; and an agricultural and horticultural bactericide containing the same as an active ingredient.　The 2,4-dioxo-1,4-dihydrothienopyrimidine compound is a compound represented by formula (I) or a salt thereof.　In formula (I), R¹ is a substituted or unsubstituted C1-C6 alkyl group, and R² is a substituted or an unsubstituted C1-C6 alkoxycarbonyl group, or the like. R³, R⁴, R⁵, and R⁶ are each independently a hydrogen atom, or a substituted or an unsubstituted C1-C6 alkyl group, or the like. R⁷ is a hydrogen atom, or a hydroxyl group, or the like, and R⁸ is a hydrogen atom. X is a halogeno group, or the like. Q is a group represented by formula (Q-1), or formula (Q-2), or the like.

Description

2,4-Dioxo-1,4-dihydrothienopyrimidine compounds and fungicides for agriculture and horticulture

The present invention relates to 2,4-dioxo-1,4-dihydrothienopyrimidine compounds and fungicides for agriculture and horticulture. More specifically, the present invention contains a 2,4-dioxo-1,4-dihydrothienopyrimidine compound having excellent bactericidal activity, excellent safety, and industrially advantageous synthesis, and an active ingredient thereof. Regarding agricultural and horticultural fungicides.
The present application claims priority to Japanese Patent Application No. 2019-11199 filed on June 17, 2019, the contents of which are incorporated herein by reference.

In cultivating agricultural and horticultural crops, various compounds having control activity against diseases of crops have been proposed. In order to put such a compound into practical use as a fungicide for agriculture and horticulture, it is not only highly effective, it is unlikely to cause drug resistance, it does not cause phytotoxicity or soil contamination to plants, and it is resistant to livestock and fish. It is required to have low toxicity.

By the way, Patent Document 1 discloses a compound represented by the formula (A) and the like.

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

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

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

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

Patent Document 6 discloses a compound represented by the formula (F) and the like. Further, Patent Document 7 discloses the use of a fungicide for agriculture and horticulture such as a compound represented by the formula (F).

Patent Document 8 discloses a compound represented by the formula (G) and the like.

Patent Document 9 discloses a compound represented by the formula (H) and the like.

WO 2013/071169 A WO 2015/007451 A WO 2017/075056 A WO 2017/091600 A WO 2017/091602 A WO 2017/091617 A WO 2017/091627 A WO 2018/171698 A WO 2018/171699 A

An object of the present invention is that a 2,4-dioxo-1,4-dihydrothienopyrimidine compound (hereinafter, simply referred to as "thienopyrimidine compound") has excellent bactericidal activity, is excellent in safety, and can be synthesized industrially advantageously. There is), as well as an agricultural and horticultural fungicide containing this as an active ingredient.

As a result of diligent studies to solve the above problems, the present inventors have completed the present invention including the following forms.
[1] A compound represented by the formula (I) or a salt thereof.

(In formula (I),
R ¹ is a substituted or unsubstituted C1-6 alkyl group.
R ² is a substituted or unsubstituted C1 to 6 alkoxycarbonyl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a cyano group or a group represented by the formula "-CR ^a = N-OR ^b ". ..
R ^a is a hydrogen atom and R ^b is a substituted or unsubstituted C1-6 alkyl group.
R ³ , R ⁴ , R ⁵ and R ⁶ are independently hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups.
R ³ and R ⁴ may be combined together to form a C2-6 alkylene group.
R ³ and R ⁵ may be combined together to form a C1-5 alkylene group.
R ⁵ and R ⁶ may be combined together to form a C2-6 alkylene group.
R ⁷ is a hydrogen atom, a hydroxyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a substituted or unsubstituted C1 to 6 alkylcarbonyloxy group, or a substituted or unsubstituted C2 to 6 alkenyloxy group.
R ⁸ is a hydrogen atom.
R ⁷ and R ⁸ may be combined together to form a substituted or unsubstituted C1-6 alkoxyimino group.
X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
n is an integer of 0 to 5, and when n is 2 or more, X may be the same or different from each other.
Q is a group represented by the formula (Q-1), the formula (Q-2) or the formula (Q-3).

In formulas (Q-1), formulas (Q-2) and formulas (Q-3), arrows indicate binding sites.
In formula (Q-1), R ^c and R ^d are independently hydrogen atoms, substituted or unsubstituted C1 to 6 alkyl groups, substituted or unsubstituted C1 to 6 alkoxy groups, substituted or unsubstituted. It is a C3-8 cycloalkyl group, a substituted or unsubstituted 5-membered heterocyclyl group, or a group represented by the formula "-CR ^g = N-OR ^h ".
R ^g is a hydrogen atom and R ^h is a substituted or unsubstituted C1-6 alkyl group.
In formula (Q-2), R ^e and R ^f are independently hydrogen atoms or substituted or unsubstituted C1 to 6 alkyl groups.
In formula (Q-3), R ⁱ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group. )
[2] A fungicide for agriculture and horticulture containing at least one selected from the group consisting of the compound according to [1] or a salt thereof as an active ingredient.

The thienopyrimidine compound of the present invention has excellent bactericidal activity, reliable effect, excellent safety, and can be synthesized industrially advantageously.
The fungicide for agriculture and horticulture of the present invention has an excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to humans, livestock and fish and has little influence on the environment.

[Thienopyrimidine compound]
The thienopyrimidine compound of the present invention is a compound represented by the formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I).

In the present invention, the term "unsubstituted" means that there are only parental groups. When only the name of the parent group is described, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of the parent group is substituted with a group having the same or different structure as the mother nucleus. Therefore, a "substituent" is another group attached to a parent group. The number of substituents may be one or two or more. The two or more substituents may be the same or different.

The "substituent" is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
Specific examples of groups that can be "substituents" include the following groups.
Halogeno groups such as fluoro group, chloro group, bromo group, iod group;
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. Alkyl group;
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 group, 2-hexenyl group, 3-hexenyl group, 4 -C2-6 alkenyl groups such as hexenyl group, 5-hexenyl group;

Ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-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 group, 1,1-dimethyl-2-butynyl group, etc. C2-6 alkynyl groups;
C3-8 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cubicyl group;
C3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group;
C6-10 aryl groups such as phenyl group and naphthyl group;
5-membered heteroaryl groups such as pyrrolyl group, frill group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isooxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group;
A 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, and a triazinyl group;
Heteroaryl groups of fused rings such as indrill groups, benzofuryl groups, benzothienyl groups, benzoimidazolyl groups, benzoxazolyl groups, benzothiazolyl groups, quinolyl groups, isoquinolyl groups, quinoxalinyl groups;
Cyclic ether groups such as oxylanyl group, tetrahydrofuryl group, dioxolanyl group, dioxanyl group;
Cyclic amino groups such as aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group;

Hydroxy group;
Oxy 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;
C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
5- to 6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups;

Carboxylic group;
Formylation group;
C1-6 alkylcarbonyl groups such as acetyl group, propionyl group;
Formyloxy group;
C1-6 alkylcarbonyloxy groups such as acetyloxy group, propionyloxy group;
C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;

C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
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;
C3-6 halocycloalkyl groups such as 3,3-difluorocyclobutyl group;
C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group;

Cyano group;
Nitro group;
Amino group;
C1-6 alkylamino groups such as methylamino group, dimethylamino group, diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
Formylamino group;
C1-6 alkylcarbonylamino groups such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group;
C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group;
C1-6 alkyl sulfoxide imino groups such as S, S-dimethyl sulfoxide imino groups;

Aminocarbonyl group;
C1-6 alkylaminocarbonyl groups such as methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group, etc.;
Imino C1-6 alkyl groups such as iminomethyl group, 1-iminoethyl group, 1-imino-n-propyl group;
Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, 1- (hydroxyimino) ethyl group, 1- (hydroxyimino) -n-propyl group;
C1-6 alkoxyimino C1-6 alkyl groups such as methoxyiminomethyl group, 1- (methoxyimino) ethyl group;

Mercapto group;
C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group;
C2-6 alkenylthio groups such as vinylthio groups and allylthio groups;
C2-6 alkynylthio groups such as ethynylthio group and propargylthio group;
C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl groups, 2,2,2-trifluoroethylsulfinyl groups;
C2-6 alkenylsulfinyl groups such as allylsulfinyl groups;
C2-6 alkynylsulfinyl groups such as propargylsulfinyl groups;
C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, t-butylsulfonyl groups;
C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups, 2,2,2-trifluoroethylsulfonyl groups;
C2-6 alkenylsulfonyl groups such as allylsulfonyl groups;
C2-6 alkynylsulfonyl groups such as propargylsulfonyl groups;
Aminothiocarbonyl group;

Tri-C1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
Tri-C6-10 arylsilyl groups such as triphenylsilyl groups

In these "substituents", any hydrogen atom in the substituent may be substituted with a group having a different structure.

Terms such as "C1 to 6" indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the parent group is a butyl group and the substituent is an ethoxy group.

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

The "C1 to 6 alkyl group" in R ¹ may be a straight chain or a branched chain. As the alkyl group, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, and a t-butyl group. , I-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

As the substituent on the "C1-6 alkyl group" in R ¹ , preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, C1-6 alkoxy groups such as n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group and the like. Examples thereof include C1 to 6 alkoxy-substituted phenyl groups such as C1 to 6 haloalkoxy groups; cyano groups; methoxyphenyl groups and ethoxyphenyl groups.

[R ² ]
In formula (I), R ² is a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a cyano group, or the formula "-CR ^a = N-OR ^b ". It is a group represented by.

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

As the substituent on the "C1 to 6 alkoxycarbonyl group" in R ² , preferably, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group can be mentioned.

The "5- to 6-membered heteroaryl group" in R ² includes a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group and a thiadiazolyl group. , A 5-membered heteroaryl group such as a tetrazolyl group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group and a triazinyl group can be mentioned.

As the substituent on the "5- to 6-membered heteroaryl group" in R ² , preferably, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be mentioned.

In R ^2: - R ^a in "formula" CR ^a = N-OR ^b "group represented by" is hydrogen atom, R ^b is a substituted or unsubstituted C1 ~ 6 alkyl group.
Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R ^b include the same ones specifically exemplified in R ¹ .

Examples of the "group represented by the formula:" -CR ^a = N-OR ^b "" in R ² include a methoxyiminomethyl group, an ethoxyiminomethyl group, an n-propoxyiminomethyl group, an isopropoxyiminomethyl group and the like. be able to.

[R ³ , R ⁴ , R ⁵ , R ⁶ ]
In formula (I), R ³ , R ⁴ , R ⁵ and R ⁶ are independently hydrogen atoms or substituted or unsubstituted C1 to 6 alkyl groups.
Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R ³ , R ⁴ , R ⁵ and R ⁶ include the same ones specifically exemplified in R ¹ .

R ³ and R ⁴ may be combined to form a C2-6 alkylene group.
Examples of the "C2 to 6 alkylene group" formed by R ³ and R ⁴ together include an ethylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.

R ³ and R ⁵ may be combined together to form a C1-5 alkylene group.
Examples of the "C1 to C5 alkylene group" formed by R ³ and R ⁵ together include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.

R ⁵ and R ⁶ may be combined to form a C2-6 alkylene group.
Examples of the "C2 to 6 alkylene group" formed by R ⁵ and R ⁶ together include those similar to those described above.

[R ⁷ ]
In formula (I), R ⁷ is a hydrogen atom, a hydroxyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a substituted or unsubstituted C1 to 6 alkylcarbonyloxy group, or a substituted or unsubstituted C2 to 6 alkenyloxy group. Is.
Examples of the "C1 to 6 alkoxy group" in R ⁷ include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group. Can be mentioned.

Examples of the "C1 to 6 alkylcarbonyloxy group" in R ⁷ include an acetyloxy group and a propionyloxy group.
Examples of the "C2 to 6 alkenyloxy group" in R ⁷ include C2 to 6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group and butenyloxy group.
As the substituent on the "C1-6 alkoxy group", "C1-6 alkylcarbonyloxy group" and "C2-6alkenyloxy group" in R ⁷ , preferably a fluoro group, a chloro group, a bromo group, an iodo group and the like are used. Halogeno group; cyano group, C1-6 alkoxy group can be mentioned.

[R ⁸ ]
In formula (I), R ⁸ is a hydrogen atom.
R ⁷ and R ⁸ may be combined together to form a substituted or unsubstituted C1-6 alkoxyimino group.
Examples of the "C1 to 6 alkoxyimino group" formed by R ⁷ and R ⁸ together include a methoxyimino group and an ethoxyimino group.
As the substituent on the "C1-6 alkoxyimino group" formed by R ⁷ and R ⁸ together, preferably, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group can be mentioned.

[X]
In formula (I), X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
Examples of the "halogeno group" in X include a fluoro group, a chloro group, a bromo group, an iod group and the like.
Examples of the "substituted or unsubstituted C1 to 6 alkoxy groups" in X include the same groups specifically exemplified in R ⁷ .

[N]
In formula (I), n is an integer of 0 to 5, and when n is 2 or more, X may be the same or different from each other.

[Q]
In formula (I), Q is a group represented by formula (Q-1), formula (Q-2) or (Q-3).

In formulas (Q-1), formulas (Q-2) and (Q-3), arrows indicate binding sites.
In formula (Q-1), R ^c and R ^d are independently hydrogen atoms, substituted or unsubstituted C1 to 6 alkyl groups, substituted or unsubstituted C1 to 6 alkoxy groups, substituted or unsubstituted. A C3 to 8 cycloalkyl group, a substituted or unsubstituted 5-membered heterocyclyl group, or a group represented by the formula "-CR ^g = N-OR ^h ".
R ^g in the "group represented by the formula" -CR ^g = N-OR ^h "" in the formula (Q-1) is a hydrogen atom, and R ^h is a substituted or unsubstituted C1 to 6 alkyl group. Is.
In formula (Q-2), R ^e and R ^f are independently hydrogen atoms or substituted or unsubstituted C1 to 6 alkyl groups.
In formula (Q-3), R ⁱ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group.

Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R ^c and R ^d include the same ones specifically exemplified in R ¹ , and "substituted or unsubstituted C1 to 6 alkoxy groups". , The same as those specifically exemplified in R ⁷ can be mentioned.

Examples of the "C3-8 cycloalkyl group" in R ^c and R ^d include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cubicyl group and the like.
Preferred examples of the substituent on the "C3-8 cycloalkyl group" in R ^c and R ^d include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; and a cyano group.

The "5-membered heterocyclyl group" in R ^c and R ^d includes 1 to 4 hetero atoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent atoms.
Examples of the "5-membered heterocyclyl group" include a 5-membered saturated heterocyclyl group, a 5-membered heteroaryl group, and a 5-membered partially unsaturated heterocyclyl group.

Examples of the 5-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, an imidazolidinyl group, a pyrazolidinyl group, an oxazolidinyl group, an isooxazolidinyl group, a thiazolidinyl group and an isothiazolidinyl group. ..
Examples of the 5-membered heteroaryl group include a pyrrolyl group, a frill group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be done.
Examples of the 5-membered partially unsaturated heterocyclyl group include a pyrrolinyl group, a dihydrofuranyl group, a dihydrothiophenyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isooxazolinyl group, a thiazolinyl group and an isothiazolinyl group. ..

As the substituent on the "5-membered heterocyclyl group" in R ^c and R ^d, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a methyl group, an ethyl group, an n-propyl group and an i- C1-6 alkyl groups such as propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group , S-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group C1 to 6 haloalkyl groups such as; cyano group; oxo group and the like can be mentioned.

Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R ^h include the same ones specifically exemplified in R ¹ .
Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R ^e and R ^f include the same ones specifically exemplified in R ¹ .

〔salt〕
The salt of compound (I) is not particularly limited as long as it is an horticulturally 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. Transition metal salts; salts of organic bases such as triethylamine, tributylamine, pyridine, hydrazine; ammonia and the like.

〔Production method〕
The method for producing the compound (I) or the salt of the compound (I) is not limited. For example, the compound (I) of the present invention or the salt of the compound (I) can be obtained by a known method as described in Examples and the like. Further, the salt of compound (I) can be obtained from compound (I) by a known method.

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

The agricultural and horticultural fungi of the present invention include a wide variety of filamentous fungi, such as algae fungi (Oomycetes), ascomycetes (Ascomycetes), imperfect fungi (Deuteromycetes), basidiomycetes, and zygomycetes. It can be used to control plant diseases derived from fungi belonging to fungi (Zygomycetes).

Examples of plant diseases (pathogens) to be controlled are shown below.
Cercospora beticola, black root disease (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), Spots Diseases (Ramularia beticola), seedling blight (Aphanomyces cochlioides, Pythium ultimum), etc .;
Peanuts: brown spot (Mycosphaerella arachidis), plaque (Ascochyta sp.), Rust (Puccinia arachidis), blight (Pythium debaryanum), rust (Alternaria alternata), white silk (Sclerotium rolfsii) black Astringency (Mycosphaerella berkeleyi), etc .;
Cucumber: Udonko disease (Sphaerotheca fuliginea), sticky disease (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine blight (Fusarium oxysporum), mycorrhizal disease (Sclerotinia sclerotiorum), Botrytis cinerea Colletotrichum orbiculare, Cladosporium cucumerinum, Corynespora cassiicola, Pythium debaryanum, Rhizoctonia solani Kuhn, Phomopsis sp. syringae pv. Lechrymans) etc .;
Tomatoes: Botrytis cinerea, Cladosporium fulvum, Phytophthora infestans, Verticillium albo-atrum, Verticillium dahliae, powdery mildew (Oidium neolycopersici), powdery mildew (Alternaria) solani), powdery mildew (Pseudocercospora fuligena), etc .;
Eggplant: Botrytis cinerea, Corynespora melongenae, powdery mildew (Erysiphe cichoracearum), soot mold (Mycovellosiella nattrassii), sclerotinia sclerotiorum, Verticillium dah Brown spot disease (Phomopsis vexans), etc .;
Strawberries: Botrytis cinerea, powdery mildew (Sphaerotheca humuli), colletotrichum acutatum, Colletotrichum fragariae, plague (Phytophthora cactorum), soft rot (Rhizopus stolonifer), chlorosis (Fusarium oxyspor) Disease (Verticillium dahliae) etc .;
Onions: Botrytis allii, Botrytis cinerea, Botrytis squamosa, Peronospora destructor, Phytophthora porri, Ciborinia allii Such;
Welsh onion: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black rotium cepivorum (Sclerotium cepivorum), rust (Puccinia allii), white spot blight (Botrytis squamosa) Such;
Cabbage: root-knot disease (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. Campestris), black rot (Pseudomonas syringae pv. Maculicola, P. s. Pv. Alisalensis), downy mildew Diseases (Peronospora parasitica), sclerotinia sclerotiorum, black rot (Alternaria brassicicola), Botrytis cinerea, etc.;
Green beans: Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc.;

Apples: Udonko disease (Podosphaera leucotricha), scab (Venturia inaequalis), Monilinia mali, black spot disease (Mycosphaerella pomi), rot disease (Valsa mali), spot deciduous disease (Alternaria mali), gymnosporangium yamadae), ring pattern disease (Botryosphaeria berengeriana), charcoal disease (Glomerella cingulata, Colletotrichum acutatum), brown spot disease (Diplocarpon mali), soot spot disease (Zygophiala jamaicensis), soot spot disease (Gloeodes pomigena), purple spot feather disease (Helicobasidium mompa), Botrytis cinerea, Erwinia amylovora, etc .;
Plum: Cladosporium carpophilum, Botrytis cinerea, Monilinia mumecola, Peltaster sp., Etc.;
Persimmon: Powdery mildew (Phyllactinia kakicola), charcoal disease (Gloeosporium kaki), keratosespora kaki, deciduous circle (Mycosphaerella nawae), etc.;
Peach: Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp., Xanthomonas campestris pv. Pruni, Taphrina deformans, Colletotrichum gloeosporioides) etc .;
Almonds: Monilinia laxa, Stigmina carpophila, Cladosporium carpophilum, Polystigma rubrum, Alternaria alternata, Colletotrichum gloeospoides, etc .;
Outou: Monilinia fructicola, Colletotrichum acutatum, Alternaria sp., Monilinia kusanoi, Mycosphaerella cerasella, etc.;
Grapes: 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), downy mildew (Phakopsora ampelopsidis), Botrytis cinerea (pathogen unidentified), etc.;
Pear: Black spot disease (Venturia nashicola), Gymnosporangium asiaticum, Black spot disease (Alternaria kikuchiana), Ring stain disease (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali), Body blight (Phomopsis fukushii), Brown spots Diseases (Stemphylium vesicarium), powdery mildew (Glomerella cingulata), etc .;
Cha: Ring spot disease (Pestalotiopsis longiseta, P. theae), charcoal disease (Colletotrichum theae-sinensis), net blast disease (Exobasidium reticulatum), etc.;
Cankits: powdery mildew (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), powdery mildew (Xanthomonas campestris pv.Citri), Powdery mildew (Oidium sp.), Epidemic (Phytophthora citrophthora), Charcoal disease (Colletotrichum fioriniae), etc .;

Wheat: Udonko disease (Blumeria graminis f.sp. Tritici), Fusarium head blight (Gibberella zeae), Fusarium head blight (Puccinia recondita), Yellow rust (Puccinia striiformis), Brown snow rot (Pythium iwayamai), Monographella nivalis Disease (Monographella nivalis), Eye print disease (Pseudocercosporella herpotrichoides), Leaf blight (Septoria tritici), Fusarium head blight (Leptosphaeria nodorum), Typhula incarnata, Myriosclerotinia borealis ), Gaeumannomyces graminis, Claviceps purpurea, Tilletia caries, Ustilago nuda, Pyricularia grisea, etc.;
Barley: Pyrenophora graminea, Pyrenophora teres, Rhynchosporium secalis, Ustilago tritici, U.nuda, etc.;
Rice: blast (Pyricularia oryzae), blight (Rhizoctonia solani), bakanae (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythiumgraminicola), white leaf blight (Xanthomonas oryzae), Seedling blight (Burkholderia plantarii), brown streak (Acidovorax avenae), fir blight (Burkholderia glumae), streak leaf blight (Cercospora oryzae), rice plant disease (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), belly black rice (Alternaria padwickii), red rice (Epicoccum purpurascens), etc.;
Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), plague (Phytophthora nicotianae), etc.;
Tulips: Botrytis cinerea, etc .;
Sunflower: Downy mildew (Plasmopara halstedii), sclerotinia sclerotiorum, Botrytis cinerea, etc .;
Bentgrass: Sclerotinia borealis, Large patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Blast (Pyricularia sp.), Red burn (Pythium aphanidermatum), Charcoal disease (Colletotrichum graminicola), etc .;
Orchardgrass: Powdery mildew (Erysiphe graminis), etc .;
Soybeans: purple spot disease (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem epidemic (Phytophthora sojae), rust disease (Phakopsora pachyrhizi), sclerotinia sclerotiorum, Botrytis cinerea (Colletotrichum truncatum) (Botrytis cinerea), black downy mildew (Elsinoe glycines), black spot disease (Diaporthe phaseolorum var. Sojae), etc.;
Potatoes: plague (Phytophthora infestans), summer plague (Alternaria solani), black blight (Thanatephorus cucumeris), half-body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), black rot (Pectobacterium atrosepticum) Diseases (Pectobacterium carotovorum), etc .;
Bananas: Panama disease (Fusarium oxysporum), black sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc .;
Mango: Colletotrichum aenigma, etc .;
Rapeseed: Sclerotinia sclerotiorum, Phoma lingam, Alternaria brassicae, etc .;
Coffee: rust (Hemileia vastatrix), anthrax (Colletotrichum coffeanum), brown eye disease (Cercospora coffeicola), etc .;
Sugar cane: brown rust (Puccinia melanocephala), etc .;
Corn: Gloeocercospora sorghi, Puccinia sorghi, Puccinia polysora, Ustilago maydis, Cochliobolus heterostrophus, Setosphaeria turcica, etc.;
Cotton: Seedling blight (Pythium sp.), Rust (Phakopsora gossypii), Mildew (Mycosphaerella areola), Anthrax (Glomerella gossypii), etc.

The fungicide for agriculture and horticulture of the present invention is used for cereals; vegetables; root vegetables; potatoes; fruit trees, tea, coffee, cacao and other trees; pastures; turf; cotton and other plants. Is preferable.

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

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

The agricultural and horticultural fungicide of the present invention may contain components other than the thienopyrimidine compound of the present invention. Examples of other components include known carriers used for formulation. In addition, as other components, conventionally known fungicides, insecticides / acaricides, nematode insecticides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds and the like can be mentioned. be able to. By containing such other components, a synergistic effect may be produced.

Specific examples of the fungicide that can be mixed or used in combination with the agricultural and horticultural fungicide of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitor:
(A) RNA polymerase I inhibitor: Benalaxil, Benalaxil-M, Flaluxil, Metalaxil, Metalaxil-M; Oxadixil; Closilacon, Offrace;
(B) Adenosine deaminase inhibitors: bupirimate, dimethilimol, etilimol;
(C) DNA / RNA synthesis inhibitors: himexazole, octinenone;
(D) DNA topoisomerase II inhibitor: oxolinic acid.

(2) Mitotic and fission inhibitors:
(A) β-tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; etaboxam;
(B) Cell division inhibitor: pencyclon;
(C) Inhibitor of spectrin-like protein delocalization: fluoricolide.

(3) Respiratory inhibitor:
(A) Complex I-NADH Oxidoreductase Inhibitor: Diflumetrim; Torfenpyrad;
(B) Complex II-succinate dehydrogenase inhibitors: benodanyl, flutranyl, mepronil; isofetamide; fluopirum; fenfurum, flumecyclox; carboxin, oxycarboxyne; tifluzamide; benzobindiflupill, bixaphen, fluxapiroki Sad, flametopil, isopyrazam, penflufen, penthiopyrado, sedaxan; boscalide, pidiflumethofen, isoflusifram, pyraziflumid, impylfurxam;
(C) Complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, spumoxystrobin, kumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin; pyracrostrobin , Pyrametostrobin, triclopyricalve; cresoxime-methyl, trifloxystrobin; dymoxystrobin, phenaminestrobin, metminostrobin, orythastrobin; famoxadon; fluoroxastrobin; phenamiden; pyribenecarb; methyltetraprol; man Destrobin;
(D) Complex III-Ubiquinol Reductase Qi Inhibitor: Siazofamide; Amisulbrom; Fempicoxamide (e) Decoupling agent for oxidative phosphorylation: Binapacryl, Meptyldinocup, Dinocup; Fluazinum; Felimzone;
(F) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(G) ATP production inhibitor: silthiofam;
(H) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): amethoctrazine.

(4) Amino acid and protein synthesis inhibitors:
(A) Methionine biosynthesis inhibitors: andprim, cyprodinyl, mepanipyrim, pyrimethanyl;
(B) Protein synthesis inhibitor: Blasticidin-S, casugamycin, casugamycin hydrochloride, streptomycin, oxytetracycline.

(5) Signal transduction inhibitor:
(A) Signal transduction inhibitors: quinoxyphen, proquinazide;
(B) MAP / histidine kinase inhibitors in osmotic signaling: fenpicronyl, fludioxonyl; clozolinate, iprodion, procymidone, vinclozoline.

(6) Lipid and cell membrane synthesis inhibitor:
(A) Phospholipid biosynthesis, methyltransferase inhibitor: edifenephos, iprobenphos, pyrazophos; isoprothiolane;
(B) Lipid oxidizers: biphenyl, chloroneb, dichloran, kinden, technazen, turquophosmethyl; etridiazole;
(C) Agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb hosetylate, prothiocarb;
(D) Pathogens Microorganisms that disrupt cell membranes: Bacillus subtilis, Bacillus subtilis QST713, Bacillus subtilis FZB24, Bacillus subtilis MBI600, Bacillus subtilis D747;
(E) Agent that disturbs cell membranes: Extract of Gosei Kayupte (tea tree).

(7) Cell membrane sterol biosynthesis inhibitor:
(A) Demethylation inhibitor at position C14 in sterol biosynthesis: trifoline; pyriphenox, pyrisoxazole; phenalimol, fluconazole, nuarimol; imazalyl, imazalyl sulfate, oxypoconazole, pefrazoate, prochloraz, fluconazole , Biniconazole; azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, diphenoconazole, diniconazole, diniconazole-M, epoxyconazole, etaconazole, fenbuconazole, fluconazole, fluconazole, fluconazole Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, fluconazole, simeconazole, tebuconazole, tetraconazole, triazimephone, triazimenol, triticonazole; prothioconazole, Voriconazole, mefentrifluconazole;
(B) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperarin; spiroxamine;
(C) 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis system: fenhexamide; fenpyrazamine;
(D) Squalene epoxidease inhibitor of sterol biosynthesis system: pyribuchicarb; naftifine, terbinafine.

(8) Inhibition of cell wall synthesis:
(A) Trehalase inhibitor: validamycin;
(B) Chitin synthase inhibitors: polyoxine, polyoxolim;
(C) Cellulose Synthetic Enzyme Inhibitors: Dimethmorph, Fulmorph, Pyrimorph; Bench Avaricarb, Iprovaricarb, Variphenalate; Mandipropamide.

(9) Melanin biosynthesis inhibitor (a) Melanin biosynthesis reductase inhibitor: fusalide; pyrokyron; tricyclazole;
(B) Dehydrating enzyme inhibitor for melanin biosynthesis: calpropamide; diclosimet; phenoxanyl;
(C) Inhibitor of melanin biosynthesis polyketide synthesis: toluprocarb.

(10) Host plant resistance inducer:
(A) Agent acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(B) Others: probenazole, thiazinyl, isothianil, diclobenazox, laminarin, Reynoutria sachalinensis extract.

(11) Agents of unknown activity: simoxanyl, Josetylaluminum, phosphate (phosphate), tecrophthalam, triazoxide, flusulfamide, dichromedin, metasulfocarb, ciflufenamide, metrafenone, pyriophenone, dodine, dodine free base, fluthianyl.

(12) Agents having multiple points of action: copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ferbum, mancozeb, maneb, Mancopper, methylam, polycarbamate, propineb, tiram, dineb, dilam; captan, captahole, folpet; chlorotalonyl; diclofluanide, trillfluanide; guazatin, iminoctadine acetate, iminoctadine albesilate (iminoctadine) trialbesilate); anilazine; dithianone; quinomethionate; fluorimide.

(13) Other agents: DBEDC, fluorofolpet, guazatin acetate, bis (8-quinolinolato) copper (II), propamidin, chloropyrrolnitrin, cyprofram, agrobacterium, betoxazine, diphenylamine, methylisothianate (MITC) ), Mildeomycin, Capsaicin, Cufraneb, Ciprosulfamide, Dazomet, Devacarb, Dichlorophene, Diphenzoquat, Difenzoquat Methylsulfonate, Flumetbel, Josetil Calcium, Josetyl Sodium, Irmamycin, Natamicin, Nitrotal Isopropyl , Oxamocarb, pyrrolnitrin, tevflokin, tornifanide, zariramid, algophase, Amicarthiazol, oxathiapiprolin, methylamzinc, benchazole, tricramide, uniconazole, myldeomycin, oxyphene Oxyfenthiin, Picarbutrazox, Quinofumelin, Florylpicoxamid, Pyrapropoyne, Fluindapyr, Aminopyrifen, pyridalomethyl , Ipflufenoquin.

Specific examples of insecticides / acaricides, nematodes, soil pesticides, anthelmintics, etc. that can be mixed or used in combination with the agricultural and horticultural fungicides of the present invention are shown below.

(1) Acetylcholinesterase inhibitor:
(A) Carbamates: Aranicalb, Aldicarb, Bengiocarb, Benfracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiophenacarb, Phenoccarb, Formanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Oxamil, Pyrimicarb, Propoxyl, Thiodicarb, thiofanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIMOC, MPMC, MTMC, aldicarb, alixicalve, aminocarb, butocarboxim, chlorocarb, metam sodium, promecarb;

(B) Organophosphorus: acephate, azamethifos, azinephos-ethyl, azinephos-methyl, kazusaphos, chlorethoxyphos, chlorpyrifos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, bearphos, cyanophos, demeton-S-methyl, diazinone, Dichlorvos / DDVP, Dichlorpyrifos, Dimethoate, Dimethylbinphos, Disulfoton, EPN, Ethion, Etoprophos, Famfur, Fenamiphos, Fenitrothione, Fention, Hostiazeto, Heptenophos, Imiciaphos, Isophenphos, Isocarbofos, Isoxathione, Malathion, Mecarbammid Monochrometophos, Nared, Omethoate, Oxydimethoate-Methyl, Palathion, Palatin-Methyl, Fentate, Holate, Hosalon, Hosmet, Phosphamide, Hoxim, Pyrimiphos-Methyl, Prophenofus, Propetamphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep Temephos, terbuphos, tetrachlorvos, thiometon, triazophos, trichlorfon, bamidthione; bromophos ethyl, BRP, carbophenothione, cyanophenphos, CYAP, demeton-S-methylsulfos, dichlorpyrifos, dichlorphenthione, dioxabenzophos, ethis , Fensulfothione, flupyrifos, honophos, formotione, phosmethilan, isazophos, iodophenphos, methacryphos, pyrimiphos-ethyl, phosphocarbs, propaphos, protoate, sulprophos.

(2) GABA-operated chlorine ion channel antagonists: acetoprol, chlordane, endosulfan, ethiprol, fipronil, pilafprowl, pyriprol, campechlor, heptachlor, dienochlor.
(3) Sodium channel modulators: acrinathrin, d-cis-trans-allethrin, d-trans-allethrin, bifentrin, bioallethrin, bioarethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cifluthrin, beta-cifluthrin, sihalothrin, lambda- Cihalothrin, Gamma-Pyrethrin, Cipermethrin, Alpha-Permethrin, Beta-Cipermethrin, Theta-Permethrin, Zeta-Cipermethrin, Ciphenothrin [(1R) -trans isomer], Deltamethrin, Empentrin [(EZ)-( 1R) -isomer], esphenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halphenprox, imiprothrin, cadesrin, permethrin, phenotrin [(1R) -trans Heterogeneous], Praletrin, Pyrethrum, Resmethrin, Silafluofen, Tefluthrin, Tetramethrin [(1R) -isomer], Tralomethrin, Transfluthrin, Allethrin, Pyrethrin, Pyrethrin I, Pyrethrin II, Profluthrin, Dimefluthrin, Bioethanomethrin Permethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metoflutrin, protrifenbut, pyrethrin, terraretrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradiflon.
(5) Nicotinic acetylcholine receptor allosteric modulator: spinetram, spinosad.
(6) Chloride channel activator: abamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, dramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadetin.
(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diophenolan, epophenonan, triprene.
(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, liquor stone.
(9) Diptera selective feeding inhibitors: fronicamid, pimetrodin, pyrifluquinazone.

(10) Tick growth inhibitors: clofentezine, difluorovidazine, hexitiazox, etoxazole.
(11) Microbial-derived insect mid-intestinal membrane-destroying agent: Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringensis subspecies Isawai, Bacillus thuringiensis subspecies Kurstaki, Bacillus thuringiensis subspecies Teneblionis, Bt Crop proteins (Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1).
(12) Mitochondrial ATP biosynthetic enzyme inhibitor: diafentiurone, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradiphon.
(13) Oxidative phosphorylation decoupling agent: chlorfenapyr, sulfamide, DNOC, binapacryl, dinobutone, dinocup.
(14) Nicotinic Acetylcholine Receptor Channel Blocker: Bensultap, Cartap Hydrochloride; Nelystoxin; Thiosultap Monosodium Salt, Thiocyclum.
(15) Chitin synthesis inhibitors: bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflubenzuron, buprofezin, fluazuron.
(16) Diptera molting disturber: Cyromazine.
(17) Moulting hormone receptor agonists: chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
(18) Octopamine receptor agonists: Amitraz, Demiditraz, Chlordimeform.
(19) Mitochondrial electron transport chain complex III inhibitor: acequinosyl, fluacripirim, hydramethylnon.
(20) Mitochondrial electron transport chain complex I inhibitor: phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, rotenone.

(21) Voltage-gated sodium channel blockers: indoxacarb, metaflumisone.
(22) Acetyl-CoA carboxylase inhibitor: spirodiclophen, spiromesiphen, spirotetramato.
(23) Mitochondrial electron transport chain complex IV inhibitor: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
(24) Mitochondrial electron transport chain complex II inhibitor: sienopyraphen, siflumethofen, pifrubmid.
(25) Ryanodine receptor modulators: chloranthraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole.
(26) Mixed Function Oxidase Inhibitor Compound: Piperonyl butoxide.
(27) Latrophilin receptor agonists: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (mechanism of action unknown): azadilactin, benzoximate, biphenazate, bromopropirate, quinomethionate, cryolite, dicoform, pyridalyl, bencrothias, sulfur, amide flumet, 1,3-dichloropropene, DCIP, Phenisobromolate, benzomate, metaldehyde, chlorbenzylate, clothiazoben, disicranyl, phenoxacrim, fentrifanyl, flubenzimine, flufenazine, gossiplua, japonilua, methoxadiazone, petroleum, potassium oleate, tetrasul, triazolesen, afidopyropen ), Fromotkin, flufiprole, fluensulphon, meperfluthrin, tetramethylfluthrin, traropyryl, dimefluthrin, methylneodecanamide, flularanel, afoxolanel, fluxametamide, 5- [5- (3,5-dichlorophenyl) -5-trifluoro Methyl-4,5-dihydroisoxazole-3-yl] -2- (1H-1,2,4-triazole-1-yl) benzonitrile (CAS: 943137-49-3), asinonapill, brofuranilide and other metaldehydes Kind.

(29) Anthelmintic:
(A) Benzimidazole system: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; fevantel, netobimin, thiophanate; thiabendazole, cambendazole;
(B) Salicylanilide system: closantel, oxyclozanide, lafoxanide, niclosamide;
(C) Substituted phenolic system: nitroxynyl, nitroscanate;
(D) Pyrimidines: Pyrantel, Morantel;
(E) Imidazothiazole type: levamisole, tetramisole;
(F) Tetrahydropyrimidines: Praziquantel, Epsiprantel;
(G) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetalsamide, merolsamine, arsenamide.

Specific examples of plant growth regulators that can be mixed or used in combination with the agricultural and horticultural fungicides of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorphenurone, tidiazulone, chlorphenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abscisic acid), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indol-3-butyric acid, gibberellin, phenothiol, 1 -Naphtylacetamide, ethicrozeto, cloxyhonac, hydrazide maleate, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonate, methyl jasmonate, (+)-strigol, (+) -Deoxystrigor, (+)-Orovancol, (+)-Solgolactone, 4-oxo-4- (2-phenylethyl) aminobutyric acid; etephon, chlormecoat, mepicote chloride, benzyladenin, 5-aminoleverellin.

[Prescription]
The agricultural and horticultural fungicide of the present invention is not particularly limited depending on the dosage form. For example, dosage forms such as wettable powders, emulsions, powders, granules, aqueous solvents, suspensions, granule wettable powders, and tablets can be mentioned. The preparation method for the preparation is not particularly limited, and a known preparation method can be adopted depending on the dosage form.

Some examples of formulations are shown below. It should be noted that the formulation formulation shown below is merely an example and can be modified without contrary to the gist of the present invention, and the present invention is not limited by the following formulation examples. "Part" means "part by mass" unless otherwise specified.

(Formulation Example 1: Wettable powder)
40 parts of the thienopyrimidine compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate ester and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder having 40% of the active ingredient.

(Formulation Example 2: Emulsion)
30 parts of the thienopyrimidine compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide and 7 parts of polyoxyethylene alkylallyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

(Formulation Example 3: Granules)
5 parts of the thienopyrimidine compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite and 7 parts of sodium alkyl sulfate are uniformly mixed, finely pulverized, and then formed into a particle diameter of 0.5 to 1.0 mm. Granules to obtain 5% active ingredient granules.

(Formulation Example 4: Granules)
5 parts of the thienopyrimidine compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctyl sulfosuccinate and 1 part of potassium phosphate were uniformly mixed and pulverized. Water is added to this and kneaded well, and then granulated and dried to obtain a granule having 5% of the active ingredient.

(Formulation Example 5: Suspension)
10 parts of the thienopyrimidine compound of the present invention, 4 parts of polyoxyethylene alkylallyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum and 73.8 parts of water are mixed, and the particle size is 3 microns or less. Wet grind to obtain a suspension of 10% active ingredient.

(Formulation Example 6: Granule wettable powder)
40 parts of thienopyrimidine compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzene sulfonic acid salt, 8 parts of sodium lignin sulfonic acid salt and 5 parts of formaldehyde condensate of sodium alkylbenzene sulfonic acid salt are uniformly mixed. After finely crushing, add an appropriate amount of water and knead to make it clay-like. The clay-like material is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.

Next, a synthetic example will be shown, and the present invention will be described more specifically. However, the present invention is not limited by the following synthetic examples.

[Example 1]
3- (1- (2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -6-((methoxyimino) methyl) -5-methyl-2,4-dioxo-1,4-dihydrothieno [2, 3-d] Synthesis of pyrimidin-3 (2H) -yl) -N-isopropyl-2,2-dimethylpropanamide

(Step 1)
Ethy1 3-(3- (tert-butoxy) -2,2-dimethyl-3-oxopropyl) -5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine -6-carboxylate synthesis

Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate (15 g) is dissolved in methylene chloride (250 ml), triphosgene (5.85 g) and triethylamine (25 ml) are added under ice cooling, and the mixture is stirred at room temperature for 2 hours. After that, tert-butyl 3-amino-2,2-dimethylpropanoate (13 g) was added, and the mixture was further stirred at room temperature for 3 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, the mixture was extracted with chloroform, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the obtained residue was dissolved in t-butyl alcohol (180 ml), cesium carbonate (39 g) was added, and the mixture was stirred at 80 ° C. for 5 hours. The reaction mixture was concentrated, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 11.5 g of the target compound. Yield 48%
The ¹ H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 4.35 (2H, q), 4.19 (2H, s), 2.83 (3H, s), 1.45 (9H, s), 1.37 (3H, t), 1.20 (6H, s) ).

(Step 2)
Ethyl 1-(2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -3- (3- (isopropylamino) -2,2-dimethyl-3-oxopropyl) -5-methyl-2,4-dioxo Synthesis of -1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate

Ethyl 3-(3- (tert-butoxy) -2,2-dimethyl-3-oxopropyl) -5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine -6-carboxylate (16.5 g) was dissolved in N, N-dimethylformamide (220 ml), and under ice-cooling, potassium carbonate (7.60 g), 2-bromo-5'-fluoro-2'-methoxyacetophenone (. 13.5 g) was added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the resulting solid was filtered. The obtained solid was dissolved in methylene chloride (250 ml), trifluoroacetic acid (25 ml) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, methylene chloride (230 ml), isopropylamine (12 g), triethylamine (11 g), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinan. 40 ml of -2,4,6-trioxide (50% ethyl acetate solution, about 1.7 mol / L) was added, and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, extracted with chloroform, and the organic layer was washed with water, 1N HCl aqueous solution, saturated sodium hydrogen carbonate aqueous solution, and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was washed with diethyl ether to obtain 20 g of the target compound. Yield 89% ^{1 1} H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 7.64-7.61 (1H, m), 7.33-7.31 (1H, m), 7.04-7.01 (1H, m), 5.95 (1H, d), 5.30 (2H, s) , 4.32 (2H, q), 4.23 (2H, s), 4.09-3.98 (1H, m), 4.03 (3H, s), 2.88 (3H, s), 1.34 (3H, t,), 1.23-1.10 ( 12H, m).

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

Ethyl 1-(2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -3- (3- (isopropylamino) -2,2-dimethyl-3-oxopropyl) -5-methyl-2,4-dioxo -1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate (18 g) is dissolved in tetrahydrofuran (150 ml) and methanol (150 ml), 1N aqueous sodium hydroxide solution (75 ml) is added, and room temperature Was stirred for 4 hours. The reaction mixture was concentrated, a 2N HCl aqueous solution (50 ml) was added, the mixture was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the obtained residue was dissolved in tetrahydrofuran (250 ml), carbonyldiimidazole (6 g) was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was added to water (250 ml) in which sodium borohydride (2.2 g) was dissolved, and the mixture was stirred overnight at room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction solution, the mixture was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 10.3 g of the target compound. Yield 62%
The ¹ H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 7.34-7.27 (1H, m), 6.96-6.79 (2H, m), 5.91 (1H, d), 5.47-5.41 (1H, m), 4.77 (2H, s) , 4.35-4.01 (5H, m), 3.89 (3H, s), 2.46 (3H, s), 1.28-1.16 (12H, m).

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

3- (1- (2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -6- (hydroxymethyl) -5-methyl-2,4-dioxo-1,4-dihydrothieno [2,3-d] ] Pyrimidin-3 (2H) -yl) -N-isopropyl-2,2-dimethylpropanamide (2.6 g) was dissolved in chloroform (40 ml), manganese dioxide (5 g) was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered, the mother liquor was concentrated, the obtained residue was dissolved in ethanol (35 ml), pyridine (0.6 g) and methoxyamine hydrochloride (0.6 g) were added at 70 ° C., and the mixture was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 2.3 g of the target compound (molecular configuration of oxime bond E: Z = 1: 1). Mixture) was obtained.
The ¹ H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 8.28, 7.70 (1H, s), 7.34-7.22 (1H, m), 6.99-6.94 (1H, m), 6.84-6.81 (1H, m), 5.87-5.41 ( 2H, m), 4.34-3.94 (11H, m), 2.66, 2.53 (3H, s), 1.25-1.16 (12H, m).

[Example 2]
3- (1- (2- (2-cyanoethoxy) -2- (5-fluoro-2-methoxyphenyl) ethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol) -2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -Synthesis of N-isopropyl-2,2-dimethylpropanamide

(Step 1)
Ethyl 2-(3- (3- (tert-butoxy) -2,2-dimethyl-3-oxopropyl) ureado) -4-methyl-5- (2H-1,2,3-triazol-2-yl) thiophene -3-carboxylate synthesis

Ethyl 2-amino-4-methyl-5- (2H-1,2,3-triazol-2-yl) thiophene-3-carboxylate (4.64 g) was dissolved in dichloromethane (90 ml), and at room temperature, triphosgene (triphosgene) 1.86 g) was added. Triethylamine (5.59 g) was added dropwise to this solution under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was ice-cooled again, tert-butyl 3-amino-2,2-dimethylpropanoate (3.20 g) was added, and the mixture was stirred overnight at room temperature. The reaction solution was poured into a saturated aqueous solution of ammonium chloride, extracted with dichloromethane, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 8.32 g of the target compound. Yield 100% ^{1 1} H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 1.05-1.58 (m, 18H), 2.26 (s, 3H), 3.39-3.43 (m, 2H), 4.35 (q, 2H), 6.24 (brs, 1H), 7.82 (s, 2H), 10.89 (brs, 1H).

(Step 2)
tert-butyl 2,2-dimethyl-3- (5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol-2-yl) -1,4-dihydrothieno [2,3- d] Synthesis of pyrimidin-3 (2H) -yl) propanoate

Ethyl 2-(3- (3- (tert-butoxy) -2,2-dimethyl-3-oxopropyl) ureido) -4-methyl-5- (2H-1,2,3-triazol-2-yl) thiophene -3-carboxylate (8.32 g) was suspended in t-butyl alcohol (120 ml), cesium carbonate (18 g) was added, and the mixture was heated under reflux overnight. The reaction solution was poured into a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 8.32 g of the target compound. Yield 96%
The ¹ H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 1.24-1.43 (m, 15H), 2.63 (s, 3H), 4.21 (s, 2H), 7.81 (s, 2H).

(Step 3)
tert-butyl 3-(1-(2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol-2) Synthesis of -yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -2,2-dimethylpropanoate

tert-butyl 2,2-dimethyl-3- (5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol-2-yl) -1,4-dihydrothieno [2,3- d] Pyrimidin-3 (2H) -yl) propanoate (7.14 g) was dissolved in N, N-dimethylformamide (50 ml), and under ice cooling, potassium carbonate (7.3 g), 2-bromo-5'- Fluoro-2'-methoxyacetophenone (4.8 g) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 5.88 g of the target compound. Yield 58%
The ¹ H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 1.12-1.26 (m, 6H), 1.43 (s, 9H), 2.69 (s, 3H), 3.99 (s, 3H), 4.25 (s, 2H), 5.26 (s) , 2H), 6.95-7.04 (m, 1H), 7.24-7.29 (m, 1H), 7.58-7.63 (m, 1H), 7.77 (s, 2H).

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

tert-butyl 3-(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) -2,2-dimethylpropanoate (5.88 g) was dissolved in dichloromethane (30 ml), and the mixture was cooled with ice. Fluoroacetic acid (6.5 ml) was added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was suspended in dichloromethane (30 ml), isopropylamine (1.22 g), N, N-diisopropylethylamine (2.66 g), O- (7-azabenzotriazole-). 1-Il) -N, N, N', N'-tetramethyluronium hexafluorophosphate (3.92 g) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, poured into ice water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 3.48 g of the target compound. Yield 61%
The ¹ H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 1.09-1.12 (m, 12H), 2.69 (s, 3H), 4.00 (s, 3H), 4.25 (s, 2H), 5.27 (s, 2H), 5.99-6.03 (m, 1H), 6.99-7.02 (m, 1H), 7.24-7.30 (m, 1H), 7.58-7.76 (m, 1H), 7.77 (s, 2H).

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

3- (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-2,2-dimethylpropanamide (3.48 g) mixed with methanol (10 ml) and tetrahydrofuran (30 ml) To, sodium tetrahydroborate (0.48 g) was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, poured into ice water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 3.10 g of the target compound. Yield 89%
The ¹ H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 1.15-1.26 (m, 12H), 2.69 (s, 3H), 3.90 (s, 3H), 4.00-4.31 (m, 4H), 5.40-5.48 (m, 1H) , 5.82-5.86 (m, 1H), 6.80-6.83 (m, 1H), 6.93-6.98 (m, 1H), 7.30-7.35 (m, 1H), 7.82 (s, 2H).

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

3- (1- (2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -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-2,2-dimethylpropanamide (0.24 g) was dissolved in dichloromethane (5 ml) and cooled with ice. Acrylonitrile (0.23 g) and Triton B (0.18 g) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.24 g of the target compound. Yield 91%
The ¹ H-NMR of the obtained target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ: 1.13-1.26 (m, 12H), 2.54 (t, 2H), 2.65 (s, 3H), 3.45-4.22 (m, 9H), 5.26-5.30 (m, 1H) , 6.11-6.14 (m, 1H), 6.80-6.83 (m, 1H), 6.95-7.02 (m, 1H), 7.18-7.22 (m, 1H), 7.82 (s, 2H).

Tables 1 and 2 show some of the compounds of the present invention produced by the same method as in the above Examples. In the table, the physical properties, melting point (mp) or refractive index (n _D ) of each compound are also shown. The configuration E or Z in Table 1 indicates the geometric isomer of the oxime group in R ² . "E" indicates an E configuration, "Z" indicates a Z configuration, and "E / Z" indicates that the compound is a mixture of compounds in both configurations. In Table 1, Me indicates a methyl group, Et indicates an ethyl group, and an arrow indicates a binding site. The configuration E or Z in Table 2 indicates the geometric isomer of the oxime group. "E" indicates an E configuration, "Z" indicates a Z configuration, and "E / Z" indicates that the compound is a mixture of compounds in both configurations.

Among the compounds shown in Tables 1 and 2, ¹ H-NMR data is shown below for viscous oil or amorphous physical property compounds.
Compound No. a-2: ^{1 1} H-NMR (CDCl ₃ , δppm): 0.91-1.49 (m, 15H), 2.43-2.2.88 (m, 6H), 3.42-4.39 (m, 10H), 5.22-5.55 ( m, 2H), 6.75-7.22 (m, 3H).
Compound No. a-3: ^{1 1} H-NMR (CDCl ₃ , δppm): 0.91-1.49 (m, 15H), 2.83 (s, 3H), 3.01-3.23 (m, 1H), 3.56-4.39 (m, 9H) , 5.29-5.48 (m, 2H), 6.75-7.28 (m, 3H).
Compound No. a-9: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.17-1.43 (m, 15H), 2.87 (s, 3H), 3.93-4.39 (m, 10H), .5.41-5.49 (m, 1H) ), 5.77-5.82 (m, 1H), 6.82-6.85 (m, 1H), 6.95-7.00 (m, 1H), 7.33-7.36 (m, 1H).
Compound No. a-10: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.26-1.39 (m, 9H), 2.49-2.54 (m, 2H), 2.66 (s, 3H), 3.45-4.25 (m, 11H) , 5.18-5.21 (m, 1H), 6.83-7.15 (m, 3H), 7.56 (d, 1H), 8.67 (d, 1H).
Compound No. a-14: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.03-1.54 (m, 9H), 2.50-2.74 (m, 5H), 3.00-4.15 (m, 10H), 5.13-5.60 (m, 2H), 6.79-7.33 (m, 3H), 8.25 (s, 1H).
Compound No. a-15: ^{1 1} H-NMR (CDCl ₃ , δppm): 0.95-1.54 (m, 9H), 2.50-2.74 (m, 7H), 3.00-4.15 (m, 12H), 5.13-5.60 (m, 2H), 6.75-7.26 (m, 3H), 8.25 (s, 1H).
Compound No. a-16: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.23-1.31 (m, 6H), 2.49-2.52 (m, 2H), 2.66 (s, 3H), 3.41-4.28 (m, 12H) , 5.16-5.21 (m, 1H), 6.84-7.56 (m, 4H).
Compound No. a-17: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.26 (s, 6H), 2.50-2.52 (m, 2H), 2.66 (s, 3H), 3.41-4.24 (m, 12H), 5.22 -5.26 (m, 1H), 6.82-7.18 (m, 3H), 8.99 (s, 1H).
Compound No. a-18: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.09-1.33 (m, 12H), 2.53-2.55 (m, 2H), 2.64 (s, 3H), 2.72-3.20 (m, 3H) , 3.43-4.30 (m, 7H), 4.61 (brs, 1H), 5.17-5.20 (m, 1H), 6.80-7.18 (m, 3H).
Compound No. a-27: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.11 (d, 6H), 1.39 (t, 3H), 2.48-2.58 (m, 4H), 2.79 (s, 3H), 3.39-3.71 (m, 2H), 3.84 (s, 3H), 4.00-4.36 (m, 5H), 5.30-5.32 (m, 1H), 5.97-6.01 (m, 1H), 6.84-7.26 (m, 3H).
Compound No. a-28: ¹ H-NMR (CDCl ₃ , δppm): 0.99-1.40 (m, 9H), 2.52-2.58 (m, 2H), 2.85 (s, 3H), 3.60-4.40 (m, 14H) , 5.26-5.30 (m, 1H), 6.79-7.25 (m, 3H).
Compound No. a-29: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.13 (d, 6H), 2.52-2.63 (m, 2H), 2.69 (s, 3H), 3.81-4.45 (m, 10H), 5.34 -5.42 (m, 1H), 5.76-5.82 (m, 1H), 6.77-7.01 (m, 2H), 7.24-7.30 (m, 1H), 7.82 (s, 2H).
Compound No. a-30: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.15-1.26 (m, 12H), 2.18 (s, 3H), 2.44 (s, 3H), 3.86 (s, 3H), 4.00-4.31 (m, 4H), 6.48 (s, 1H), 6.58-6.12 (m, 4H), 7.68-7.72 (m, 2H).
Compound No. a-31: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.15-1.26 (m, 12H), 2.41 (s, 3H), 3.82 (s, 3H), 4.00-4.31 (m, 4H), 5.26 -5.30 (m, 1H), 6.13-6.17 (m, 1H), 6.46 (s, 1H), 6.79-6.18 (m, 3H), 7.68-7.72 (m, 2H).
Compound No. a-33: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.19 (s, 6H), 2.41 (s, 3H), 2.49-2.55 (m, 2H), 2.82-2.90 (m, 2H), 3.39 -4.21 (m, 12H), 5.22-5.29 (m, 1H), 6.28-6.35 (m, 1H), 6.46 (s, 1H), 6.78-7.02 (m, 4H), 7.13-7.21 (m, 3H) , 7.67 (s, 1H), 7.72 (s, 1H).
Compound No. a-34: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.23 (s, 6H), 2.43 (s, 3H), 2.85-2.92 (m, 2H), 3.41-3.48 (m, 2H), 3.82 (s, 3H), 3.84 (s, 3H), 3.97-4.49 (m, 4H), 5.40-5.45 (m, 1H), 6.28-6.32 (m, 1H), 6.47 (s, 1H), 6.77-7.36 (m, 7H), 7.67 (s, 1H), 7.72 (s, 1H).
Compound No. a-36: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.12-1.28 (m, 12H), 2.43 (s, 3H), 2.52-2.59 (m, 2H), 3.24 (s, 3H), 3.51 -3.60 (m, 2H), 3.84 (s, 3H), 4.00-4.21 (m, 5H), 6.10-6.17 (m, 1H), 6.47 (s, 1H), 6.57-7.16 (m, 4H), 7.67 (s, 1H), 7.73 (s, 1H).
Compound No. a-37: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.12-1.28 (m, 12H), 2.43 (s, 3H), 3.33 (s, 3H), 3.51-3.60 (m, 2H), 3.86 (s, 3H), 3.95-4.35 (m, 7H), 6.02-6.12 (m, 1H), 6.47 (s, 1H), 6.57-7.16 (m, 4H), 7.67 (s, 1H), 7.73 (s) , 1H).
Compound No. a-41: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.05-1.09 (m, 6H), 1.39 (t, 3H), 1.72-2.22 (m, 6H), 2.85 (s, 3H), 3.31 -3.46 (m, 1H), 3.72-4.42 (m, 7H), 5.32-5.72 (m, 3H), 6.82-7.25 (m, 3H).
Compound No. a-42: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.05-1.09 (m, 6H), 1.39 (t, 3H), 1.72-2.25 (m, 6H), 2.61-2.66 (m, 2H) , 2.85 (s, 3H), 3.23-3.46 (m, 1H), 3.72-4.41 (m, 9H), 5.27-5.65 (m, 2H), 5.98-6.10 (m, 1H), 6.78-7.25 (m, 3H).
Compound No. b-1: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.06-1.32 (m, 15H), 2.42 (s, 3H), 3.80 (s, 3H), 3.99-4.29 (m, 7H), 4.97 (s, 2H), 6.47 (s, 1H), 6.68-7.05 (m, 3H), 7.64-7.73 (m, 2H).
Compound No. b-3: ^{1 1} H-NMR (CDCl ₃ , δppm): 1.15 (d, 6H), 1.24 (s, 6H), 2.41 (s, 3H), 3.05-3.09 (m, 2H), 3.83 (s) , 3H), 3.99-4.13 (m, 3H), 4.22 (s, 2H), 6.13-6.18 (m, 1H), 6.46 (s, 1H), 6.81-6.89 (m, 1H), 7.12-7.25 (m) , 2H), 7.64 (s, 1H), 7.72 (s, 1H).

[Biological test]
The following test examples show that the thienopyrimidine compound of the present invention is useful as an active ingredient of a fungicide for agriculture and horticulture.

(Preparation of test emulsion)
5 parts by weight of the thienopyrimidine compound, 93.5 parts by weight of N, N-dimethylformamide, and 1.5 parts by weight of polyoxyethylene sorbitan monolaurate (TWEEN® 20) are mixed and dissolved to dissolve the active ingredient. A 5% emulsion (I) was obtained.

The control price was calculated by the following formula.

[Number 1]
Control value (%) = 100- {Ratio of lesion area in treated plot / Ratio of lesion area in untreated plot} × 100

(Test Example 1) Apple scab control test Water was added to the emulsion (I) so that the concentration of the thienopyrimidine compound was 125 ppm, and the mixture was dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on apple seedlings (cultivar "Orin", 3-4 leaf stage) cultivated in a seedling raising pot. After air drying, conidia of apple scab (Venturia inaequalis) were inoculated (treatment plot). As a control, apple seedlings that were not sprayed with the drug solution were similarly inoculated (untreated plot). They were allowed to stand in a wet room at 20 ° C. in which light and darkness was repeated every 12 hours.
On the day 2 weeks after inoculation, the leaves of apple seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

Compound Nos. a-1, a-2, a-3, a-4, a-5, a-6, a-7, a-8, a-9, a-10, a-11, a-12, a-13, a-14, a-15, a-16, a-18, a-19, a-20, a-21, a-22, a-23, a-24, a-25, a- 26, a-27, a-28, a-29, a-30, a-31, a-32, a-33, a-34, a-35, a-36, a-37, a-38, The apple scab control test was carried out on the thienopyrimidine compounds of a-39, a-40, a-41, a-42, b-1, b-2 and b-3. Both compounds showed a control value of 75% or more.

(Test Example 2) Cucumber Botrytis cinerea control test Water was added to the emulsion (I) so that the concentration of the thienopyrimidine compound was 125 ppm, and the mixture was dissolved to obtain a drug solution. Subsequently, the drug solution was sprayed on the cucumber seedlings (cultivar "Crawling" type, cotyledon stage) cultivated in the seedling raising pot. After air-drying, a conidia suspension of Botrytis cinerea was inoculated dropwise (treatment group). As a control, cucumber seedlings to which the drug solution was not sprayed were inoculated by dropping in the same manner as above (untreated plot). They were allowed to stand in a wet room at 20 ° C.
On the day 4 days after inoculation, the leaves of the cucumber seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

Compound Nos. a-1, a-4, a-5, a-7, a-12, a-14, a-18, a-21, a-22, a-23, a-25, a-26, Cucumbers for thienopyrimidine compounds of a-28, a-29, a-30, a-31, a-32, a-33, a-34, a-36, a-37, a-38 and b-3. A gray mold control test was conducted. Both compounds showed a control value of 75% or more.

(Test Example 3) Wheat powdery mildew control test Water was added to the emulsion (I) so that the concentration of the thienopyrimidine compound was 125 ppm, and the mixture was dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on wheat seedlings (cultivar "Chihoku", 1-2 leaf stage) cultivated in a seedling raising pot. After air-drying, conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were sprinkled and inoculated (treatment plot). As a control, wheat seedlings that were not sprayed with the drug solution were inoculated in the same manner as above (untreated plot). They were allowed to stand in a greenhouse at 20 ° C.
On the day 6 days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

Compound Nos. a-1, a-2, a-3, a-4, a-7, a-8, a-9, a-11, a-12, a-13, a-14, a-18, a-19, a-20, a-21, a-22, a-23, a-24, a-25, a-26, a-29, a-30, a-31, a-32, a- 33, a-34, a-35, a-36, a-37, a-38, a-39, a-40, a-41, a-42, b-1, b-2 and b-3 A wheat udonko disease control test was conducted on the thienopyrimidine compound. Both compounds showed a control value of 75% or more.

(Test Example 4) Wheat Red Rust Control Test Water was added to the emulsion (I) so that the concentration of the thienopyrimidine compound was 125 ppm, and the mixture was dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on wheat seedlings (cultivar "Norin 61", 1-2 leaf stage) cultivated in a seedling raising pot. After air-drying, the wheat seedlings sprayed with the chemical solution were inoculated by sprinkling summer spores of wheat leaf rust (Puccinia recondita) (treatment plot). As a control, wheat seedlings to which the drug solution was not sprayed were inoculated in the same manner as above (untreated plot). They were allowed to stand in a greenhouse at 20 ° C.
On the day 12 days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

Compound Nos. a-1, a-4, a-12, a-14, a-15, a-19, a-21, a-22, a-23, a-25, a-26, a-29, Wheat for the thienopyrimidine compounds of a-30, a-31, a-32, a-33, a-34, a-36, a-37, a-38, a-40, a-41 and b-3. A red rust control test was conducted. Both compounds showed a control value of 75% or more.

Since randomly selected thienopyrimidine compounds of the present invention exert the above-mentioned effects, the thienopyrimidine compounds of the present invention have a bactericidal effect, including compounds that could not be exemplified. It is a compound that does not cause phytotoxicity to plants and has little toxicity to humans, livestock and fish and has little impact on the environment, and is useful as a pesticide.

Claims (2)

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

   

   (In formula (I),
   R ¹ is a substituted or unsubstituted C1-6 alkyl group.
   R ² is a substituted or unsubstituted C1 to 6 alkoxycarbonyl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a cyano group or a group represented by the formula "-CR ^a = N-OR ^b ". ..
   R ^a is a hydrogen atom and R ^b is a substituted or unsubstituted C1-6 alkyl group.
   R ³ , R ⁴ , R ⁵ and R ⁶ are independently hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups.
   R ³ and R ⁴ may be combined together to form a C2-6 alkylene group.
   R ³ and R ⁵ may be combined together to form a C1-5 alkylene group.
   R ⁵ and R ⁶ may be combined together to form a C2-6 alkylene group.
   R ⁷ is a hydrogen atom, a hydroxyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a substituted or unsubstituted C1 to 6 alkylcarbonyloxy group, or a substituted or unsubstituted C2 to 6 alkenyloxy group.
   R ⁸ is a hydrogen atom.
   R ⁷ and R ⁸ may be combined together to form a substituted or unsubstituted C1-6 alkoxyimino group.
   X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
   n is an integer of 0 to 5, and when n is 2 or more, X may be the same or different from each other.
   Q is a group represented by the formula (Q-1), the formula (Q-2) or the formula (Q-3).
   

   

   Formula (Q-1) In formulas (Q-2) and (Q-3), arrows indicate binding sites.
   In formula (Q-1), R ^c and R ^d are independently hydrogen atoms, substituted or unsubstituted C1 to 6 alkyl groups, substituted or unsubstituted C1 to 6 alkoxy groups, substituted or unsubstituted. It is a C3-8 cycloalkyl group, a substituted or unsubstituted 5-membered heterocyclyl group, or a group represented by the formula "-CR ^g = N-OR ^h ".
   R ^g is a hydrogen atom and R ^h is a substituted or unsubstituted C1-6 alkyl group.
   In formula (Q-2), R ^e and R ^f are independently hydrogen atoms or substituted or unsubstituted C1 to 6 alkyl groups.
   In formula (Q-3), ^Ri is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. )
2. A fungicide for agriculture and horticulture containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.