JP2021028298A - 1,3,5,6-tetrasubstituted thieno[2,3-d]pyrimidine-2,4(1h,3h)dione compound, and agricultural and horticultural fungicide - Google Patents

Abstract

To provide a novel agricultural and horticultural fungicide.SOLUTION: The present invention relates to a 1,3,5,6-tetrasubstituted thieno [2,3-d]pyrimidine-2,4(1H,3H) dione compound, represented by formula (1), or a salt thereof (R6 is *-O...N=C(Ra) (Rb) or the like).SELECTED DRAWING: None

Description

The present invention relates to 1,3,5,6-tetra-substituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds and fungicides for agriculture and horticulture. More specifically, the present invention has excellent bactericidal activity, excellent safety, and industrially advantageous synthesis of 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidin-2,4 ( 1H, 3H) Regarding dione compounds and agricultural and horticultural fungicides containing them as active ingredients.

Various compounds having a control activity against diseases of crops have been proposed for cultivation of agricultural and horticultural crops. 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).

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

The subject of the present invention is 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 1H,) which is excellent in bactericidal activity, excellent in safety, and can be synthesized industrially advantageously. 3H) To provide a dione compound (hereinafter, may be simply referred to as a "thienopyrimidine compound") and an agricultural and horticultural bactericidal agent containing the same as an active ingredient.

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

〔式(I)中、
Ｒ¹は、置換若しくは無置換のＣ１〜６アルキル基であり、
Ｒ²は、Ｃ１〜６アルコキシカルボニル基、または５員ヘテロアリール基であり、
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Ｃ１〜６アルキルアミノカルボニル基であり、
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アルキル基であり、
Ｒ^6'は、水素原子であり、
Ｘは、ハロゲノ基、または置換若しくは無置換のＣ１〜６アルコキシ基であり、
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り、ｎが２以上のときＸは互いに同じでも異なってもよく、且つ
Ｒ⁶は、式（Q-1）で表される基、または（１，３−ジオキソイソインドリン−２−イル）オキシ基である。

（式（Q-1）中、＊は結合位置であり、
Ｒ^aは、置換若しくは無置換のＣ１〜６アルキル基、またはＣ３〜６シクロアルキル基であり、
Ｒ^bは、水素原子、またはＣ１〜６アルキル基であり、Ｒ^aとＲ^bとが結合して、それらが結合する炭素原子と伴に置換若しくは無置換の５〜６員環を形成してもよい。）〕 [1] A compound represented by the formula (I) or a salt thereof.

[In equation (I),
R ¹ is a substituted or unsubstituted C1-6 alkyl group.
R ² is a C1-6 alkoxycarbonyl group, or a 5-membered heteroaryl group.
R ³ is a substituted or unsubstituted C1-6 alkoxycarbonyl group or a substituted or unsubstituted C1-6 alkylaminocarbonyl group.
R ⁴ and R ^{4 'are} each independently a hydrogen atom or a substituted or unsubstituted C1~6 alkyl,
R ^6'is a hydrogen atom
X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
n indicates the number of chemically acceptable Xs and is an integer of 0 to 5. When n is 2 or more, Xs may be the same or different from each other, and R ⁶ is the formula ( It is a group represented by Q-1) or an oxy group (1,3-dioxoisoindoline-2-yl).

(In equation (Q-1), * is the connection position,
^Ra is a substituted or unsubstituted C1-6 alkyl group or C3-6 cycloalkyl group.
R ^b is a hydrogen atom or a C1 to 6 alkyl group, and R ^a and R ^b are bonded to form a substituted or unsubstituted 5 to 6-membered ring together with the carbon atom to which they are bonded. May be good. )]]

[2] A fungicide for agriculture and horticulture containing at least one selected from the group consisting of the compound according to the above [1] and salts 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, has little toxicity to humans, livestock and fish, and has little effect 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 the 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 groups, chloro groups, bromo groups and iod groups;
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 group;
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 to 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 indolyl 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 groups and propargyloxy groups;
C6-10 aryloxy groups such as phenoxy group, naphthoxy group;
5-6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups;

Carboxyl group;
Holmil 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;

Cyanide group;
Nitro group;
Amino group;
C1-6 alkylamino groups such as methylamino group, dimethylamino group, diethylamino group;
C6-10 arylamino groups such as anilino groups and naphthylamino groups;
Formylamino group; C1-6 alkylcarbonylamino group 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-imino) ethyl group, (1-imino) -n-propyl group;
Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) 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;

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 "C1-6 alkyl group" in R ¹ may be a straight chain or a branched chain. The alkyl group includes 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 a specific example of the "C1-6 alkyl group having a substituent" in ^{R 1,}
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 -Trifluoromethylethyl group, 1,1,1,3,3,3-hexafluoropropan-2-yl group, perfluoropropan-2-yl group, perfluorohexyl group, perchlorohexyl group, 2,4 , C1-6 haloalkyl groups such as 6-trichlorohexyl group;

Hydroxy C1-6 alkyl groups such as hydroxymethyl group and hydroxyethyl group;
C1 to methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group, etc. 6 alkoxy C1-6 alkyl groups;
C6 to 10 aryl C1 to 6 alkyl groups such as benzyl group and phenethyl group;
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 can be mentioned.

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. C1-6 haloalkoxy groups; cyano groups; can be mentioned.

[R ² ]
In formula (I), R ² is a C1-6 alkoxycarbonyl group or a 5-membered heteroaryl group.

Examples of the "C1-6 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.

Examples ^{of the "5-membered heteroaryl group" in R 2} include pyrrolyl group, frill group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isooxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group and thiadiazolyl group. Examples thereof include a tetrazolyl group.

[R ³ ]
In formula (I), R ³ is a substituted or unsubstituted C1-6 alkoxycarbonyl group or a substituted or unsubstituted C1-6 alkylaminocarbonyl group.

The "C1-6 alkoxycarbonyl groups" in R ³ can be the same as those specifically exemplified in ^{R 2.}

Examples of the "C1 to 6 alkylaminocarbonyl group" in R ³ include a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group, and an i-propylaminocarbonyl group.

Examples of the substituent on the "C1-6 alkoxycarbonyl group" and "C1-6 alkylaminocarbonyl group" in R ³ include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group. ..

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

"Substituted or unsubstituted C1~6 alkyl group" for R ⁴ and R ^{4 'may} be the same as those as specifically illustrated in R ^1.

[R ⁶ ]
In formula (I), R ⁶ is a group represented by formula (Q-1) or a (1,3-dioxoisoindoline-2-yl) oxy group.

In formula (Q-1), * is the bond position, ^Ra is a substituted or unsubstituted C1-6 alkyl group or C3-6 cycloalkyl group, and R ^b is a hydrogen atom or C1 to C1. It is a 6-alkyl group. R ^a and R ^b may be bonded to form a substituted or unsubstituted 5- to 6-membered ring with the carbon atom to which they are bonded.

The wavy line showing the bond (NO undefined stero bond) between N (nitrogen atom) and O (oxygen atom) in the formula (Q-1) is the E-form or Z-form by the nitrogen-carbon double bond or theirs. Indicates a mixture.

"Substituted or unsubstituted C1~6 alkyl group" in R ^a may be cited the same as those as specifically illustrated in R ^1.

As "C3~6 cycloalkyl group" in R ^a may be mentioned cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, etc. Kyubaniru group.

As a substituent on "C3~6 cycloalkyl group" in R ^a, preferred examples include fluoro, chloro, bromo group, a halogeno group such as iodo groups.

The “substituted or unsubstituted C1-6 alkyl groups” in R ^b can be the same as those specifically exemplified in ^{R 1.}

The ^{5- to 6-membered ring (hereinafter, may be referred to as Y) formed by bonding R a} and R ^b together with the carbon atom to which they are bonded includes a cyclopentane ring, a cyclohexane ring, and a dioxolane ring. , Dioxane ring and the like.
The 5- to 6-membered ring may have a substituent. Examples of the substituent on Y include a hydroxyl group and an alkoxy group. In addition, any two substituents on Y are formed by combining them with a methylenedioxy group (-OCH ₂ O-), an ethylenedioxy group (-OCH ₂ CH ₂ O-), and a tri. It may be a C1-6 alkylenedioxy group such as a methylenedioxy group.

[R ^6' ]
In formula (I), R ^6'is a hydrogen atom.

[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 "C1-6 alkoxy group" in X include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, and an i-butoxy group. Examples thereof include an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.

As the substituent on the "C1-6 alkoxy group" in X, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be preferably mentioned.

[N]
In formula (I), n represents the chemically acceptable number of Xs and is an integer of 0-5. When n is 2 or more, X may be the same or different from each other.

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 ammonia, triethylamine, tributylamine, pyridine, hydrazine and the like can be mentioned.

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

[Fungicide for agriculture and horticulture]
The agricultural and horticultural fungicide of the present invention contains at least one selected from compound (I) and 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 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.
Tensai: brown spot disease (Cercospora beticola), black root disease (Aphanomyces cochlioides), root rot (Rhizoctonia solani), leaf rot (Thanatephorus cucumeris), etc. Lakkasei: brown spot disease (Mycosphaerella arachidis), stain disease (Ascochyta sp. ), Puccinia arachidis, Pythium debaryanum, Alternaria alternata, Sclerotium rolfsii, Cercosporidium personatum, etc. Cucumber: Sphaerotheca fuliginea, Root rot (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine oxysporum (Fusarium oxysporum), mycorrhizal disease (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), charcoal disease (Colletotrichum orbiculare), scab (Cladosporium cucumerinum), brown spot disease (Corynespora cassiicola), seedling blight (Pythium debaryanum, Rhizoctonia solani Kuhn), homopsis root rot (Phomopsis sp.) Spotted bacterial disease (Pseudomonas syringae pv. Lechrymans), etc. Disease (Botrytis cinerea), Leaf mold (Cladosporium fulvum), Epidemic (Phytophthora infestans), Half-body wilt (Verticillium albo-atrum, Verticillium dahliae), Udonko disease (Oidium neolycopersici), Ring scab (Alternaria solani) Mold disease (Pseudocercospora fuligena), etc. Nath: Gray mold disease (Botrytis cinerea), Black blight (Corynespora melongenae), Udonko disease (Erysiphe cichoracearum), Susuka disease (Mycove) llosiella nattrassii), Botrytis cinerea, Sphaerotheca humuli, Botrytis cinerea, Sphaerotheca humuli, etc. Strawberry: Botrytis cinerea, Sphaerotheca humuli, Verticillium dahliae, Phomotis cinerea, etc. Colletotrichum acutatum, Colletrichum fragariae, plague (Phytophthora cactorum), soft rot (Rhizopus stolonifer), cinerea (Fusarium oxysporum), wilt (Verticillium dahliae), etc. Botrytis cinerea (Botrytis allii), gray cinerea ), Botrytis cinerea, Peronospora destructor, Phytophthora porri, etc. Cabbets: cinerea (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv) .campestris), Botrytis cinerea (Pseudomonas syringae pv. Maculicola, P. s. Pv. Alisalensis), Botrytis cinerea (Peronospora parasitica), Botrytis cinerea (Sclerotinia sclerotiorum), Botrytis cinerea (Alternaria brassicicola), Botrytis cinerea Diseases (Botrytis cinerea), etc. Ingen: Botrytis cinerea, Botrytis cinerea, Colletotrichum lindemuthianum, Phaeoiisariopsis griseola, etc.

Apples: Udonko disease (Podosphaera leucotricha), scab (Venturia inaequalis), Monilinia mali, black spot disease (Mycosphaerella pomi), rot disease (Valsa ceratosperma), spot foliar disease (Alternaria mali), red portic disease (Gymno) yamadae), 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), Gray mold (Botrytis cinerea), etc. Ume: Black spot disease (Cladosporium carpophilum), Gray mold disease (Botrytis cinerea), Monilinia mumecola, etc. Kaki: Udonko disease (Phyllactinia kakicola), charcoal Diseases (Gloeosporium kaki), keratotic foliar disease (Cercospora kaki), etc. Peach: Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp., Perforated bacterial disease (Xanthomonas campestris pv. ) Etc. Almonds: Monilinia laxa, Stigmina carpophila, Cladosporium carpophilum, Polystigma rubrum, Alternaria alternata, Colletotrichum gloeospoides, etc. Monilinia fructicola, Colletotrichum acutatum, Alternaria sp., Monilinia kusanoi, etc. Grape: Botrytis cinerea, Udonko disease (Uncinul a 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: Black rot (Venturia nashicola), Gymnosporangium asiaticum, Black rot (Alternaria kikuchiana), Ring rot (Botryosphaeria berengeriana), Powdery mildew (Phyllinia) ), Body blight (Phomopsis fukushii), Brown spot disease (Stemphylium vesicarium), Carbony mildew (Glomerella cingulata), etc. Cha: Ring spot disease (Pestalotiopsis longiseta, P. theae), Powdery mildew (Colletotrichum theae-sinensis), Exobasidium reticulatum, etc. Cankits: scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black rot (Diaporthe citri), powdery mildew (Xanthomonas campestris pv.Citri), powdery mildew (Oidium sp.), Etc.

Wheat: Udonko disease (Blumeria graminis f.sp. Tritici), red mold disease (Gibberella zeae), red rust disease (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eye print Diseases (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Phaeosphaeria nodorum), snow rot small-grain sclerotia (Typhula incarnata), snow-rot large-grain fungus (Myriosclerotinia borealis), wilt (Gaeumannomyces graminis) ), Claviceps purpurea, Tilletia caries, Ustilago nuda, etc. Omugi: Pyrenophora graminea, Pyrenophora teres, Rhynchosporium secalis, Naked scab (Ustilago tritici, U.nuda), etc. Rice: blast (Pyricularia oryzae), blight (Rhizoctonia solani), stupid seedling disease (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicolum), white leaf blight (Xanthomonas oryzae), seedling blight (Burkholderia plantarii), brown streak (Acidovorax avenae), fir blight (Burkholderia glumae), streak blight (Cercospora oryzae), rice Ustilaginoidea virens, brown rice (Alternaria alternata, Curvularia intermedia), hungry black rice (Alternaria padwickii), reddish rice (Epicoccum purpurascens), etc. Tobacco: sclerotinia sclerotiorum, erysiphe cichoracearum, Epidemic (Phytophthora nicotiana e), etc. Tulip: Botrytis cinerea, etc. Sunflower: Sticky disease (Plasmopara halstedii), Sclerotinia sclerotiorum, etc. Bentgrass: Sclerotinia borealis, Large patch (Rhizoctonia solani) ), Brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Blast (Pyricularia sp.), Red burning disease (Pythium aphanidermatum), Charcoal disease (Colletotrichum graminicola) Orchardgrass: Udonko disease (Erysiphe graminis) Soybeans: Purpura kikuchii, Peronospora manshurica, Phytophthora sojae, Phakopsora pachyrhizi, Sclerotinia sclerotiorum, Colletotrichum truncatum, gray Diseases (Botrytis cinerea), black scab (Elsinoe glycines), black spot disease (Diaporthe phaseolorum var. Sojae), etc. Potatoes: plague (Phytophthora infestans), summer plague (Alternaria solani), black bruise (Thanatephorus cucumeris), half-body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens) Banana: Panama disease (Fusarium oxysporum), Black Shigatoka disease (Mycosphaerella fijiensis), Yellow Shigatoka disease (Mycosphaerella musicola), etc. Rhizoctonia: Sclerotinia sclerotium ), Phoma lingam, Alternaria brassicae, etc. Coffee: rust (Hemileia vastatrix), Colletotrichum coffeanum, brown eye disease (Cercospo) ra coffeicola), etc. Sugar cane: brown rust (Puccinia melanocephala), etc. Corn: leopard disease (Gloeocercospora sorghi), rust (Puccinia sorghi), southern rust (Puccinia polysora), black ear disease (Ustilago maydis), sesame leaf blight (Bipolaris maydis), soot scab (Setosphaeria turcica), etc. Wata: seedling blight (Pythium sp.), Rust (Phakopsora gossypii), white mold (Mycosphaerella areola), charcoal disease (Glomerella gossypii), etc.

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

The agricultural and horticultural bactericide of the present invention can be applied to various parts of plants, for example, leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tubers, 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 shall be 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; Crodiracon, Offrace;
(b) Adenosine deaminase inhibitors: bupirimate, dimethilimol, etilimol;
(c) DNA / RNA synthesis inhibitors: himexazole, octylineone;
(d) DNA topoisomerase II inhibitor: oxolinic acid.

(2) Mitotic and fission inhibitors:
(a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; etaboxam;
(b) Cell division inhibitor: pencyclon;
(c) Spectrin-like protein delocalization inhibitor: fluoricolide.

(3) Respiratory inhibitor:
(a) Complex I NADH Oxidoreductase Inhibitor: Diflumetrim; Torphenpyrad;
(b) Complex II succinate dehydrogenase inhibitors: benodanyl, flutranyl, mepronil; isofetamide; fluopirum; fenfuram, flumecyclox; carboxyne, oxycarboxyne; tifluzamide; benzobindiflupill, bixaphen, fluxapyroxado , Flametopil, isopyrazam, penflufen, penthiopyrado, sedaxan; boscalid;
(c) Complex III Ubiquinol Oxidase Qo Inhibitors: Azoxystrobin, Spiderxtrobin, Kumethoxystrobin, Enokistrobin, Fluphenoxystrobin, Picoxystrobin, Pyraoxystrobin; Pyrametostrobin, triclopyricalve; cresoxime-methyl, trifloxystrobin; dymoxystrobin, phenaminestrobin, metminostrobin, orythastrobin; famoxadon; fluoroxastrobin; fenamiden;
(d) Complex III Ubiquinol Reductase Qi Inhibitor: Ciazofamide; Amisulbrom;
(e) Oxidative phosphorylation decoupling agents: binapacryl, meptylzinocup, dinocup; fluazinum; ferlimzone;
(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 inhibitors: 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 inhibitors: edifenphos, iprobenphos, pyrazophos; isoprothiolane;
(b) Lipid Peroxidizers: Biphenyl, Chloroneb, Dichloran, Kindzen, Technazen, Torquelophosmethyl; Etridiazol;
(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 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(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; pyrifenox, pyrisoxazole; phenalimol, fluluprimidol, nuarimol; imazalyl, imazalyl sulfate, oxypoconazole, pefrazoate, prochloraz, triflumizole , Biniconazole; azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, diphenoconazole, diniconazole, diniconazole-M, epoxyconazole, etaconazole, fenbuconazole, fluconazole, fluconazole, fluconazole, fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, fluconazole, simeconazole, tebuconazole, tetraconazole, triazimephone, triazimenol, triticonazole; prothioconazole, triticonazole, Voriconazole;
(b) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperarin; spiroxamine;
(c) 3-ketoreductase 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: polyoxin, polyoxolim;
(c) Cellulose Synthetic Enzyme Inhibitors: Dimethmorph, Fulmorph, Pyrimorph; Bench Avaricarb, Iprovaricarb, Torprocarb, Variphenalate; Mandipropamide.

(9) Melanin biosynthesis inhibitor
(a) Reductase inhibitor of melanin biosynthesis: fusalide; pyrokyron; tricyclazole;
(b) Dehydrating enzyme inhibitors of melanin biosynthesis: calpropamide; diclosimet; phenoxanyl.

(10) Host plant resistance inducer:
(a) Agents that act on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: probenazole; thiazinyl; isothianil; 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 with multiple points of action: copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; Man copper, methylam, polycarbamate, propineb, tiram, dineb, dilam; captan, captahole, folpet; chlorotalonyl; diclofluanide, trilfluanide; guazatin, iminoctadine triacetate, iminoctadine albesilate 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, Diphenzoquat Methylsulfonate, Flumetbel, Josetylcalcium, Josetilsodium, Irmamycin, Natamycin, Nitrotalisopropyl , Oxamocarb, pyrrolnitrin, tebufloxin, tornifanide, zariramid, algophase, amicarthiazol, oxathiapiprolin, methylamzinc, benchazole, tricramide, uniconazole, mildeomycin, oxyphene Oxyfenthiin, picarbutrazox.

Specific examples of insecticides / acaricides, nematode pesticides, soil pesticides, anthelmintic agents, 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) Carbamate: Aranicarb, Aldicarb, Bengiocarb, Benfracarb, Butocarboxim, Butoxycarboxym, Carbaryl, Carbofuran, Carbosulfan, Ethiophenacarb, Phenoccarb, Formetanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Oxamil, Pyrimicarb, Propoxil Thiodicarb, thiofanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldicarb, alixcarb, aminocarb, butocarboxim, chlorocarb, metam sodium, promecarb;

(b) Organophosphorus: acephate, azamethifos, azinephos-ethyl, azinephos-methyl, kazusaphos, chlorethoxyphos, chlorphenbinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, bearphos, cyanophos, demeton-S-methyl, diazinone, Dichlorvos / DDVP, Dichlorvos, Dimethoate, Dimethylbinphos, Disulfoton, EPN, Ethion, Etoprophos, Famfur, Fenamiphos, Fenitrothione, Fention, Hostizate, Heptenophos, Imiciaphos, Isophenphos, Isocarbhos, Isoxathion, Malathion, Mecarbamme, Metaphos Monochrometophos, Naredo, Ometoate, Oxydimethoate-Methyl, Palathion, Palatin-Methyl, Fentate, Phorate, Hosalon, Hosmet, Phosphamide, Hoxim, Pyrimiphos-Methyl, Prophenofus, Propetamphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep, Tebupyrinphos Temephos, terbuphos, tetrachlorvos, thiometon, triazophos, trichlorfon, bamidthione; bromophos ethyl, BRP, carbophenothione, cyanophenphos, CYAP, demeton-S-methylsulfos, dichlorvos, 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, pilafrol; camfechlor, heptachlor, dienochlor.
(3) Sodium channel modulators: acrinathrin, d-cis-trans-allethrin, d-trans-allethrin, bifentrin, bio-allethrin, bio-allethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cifluthrin, beta-cifluthrin, sihalothrin, lambda- Cihalothrin, Gamma-Pyrethrin, Cipermethrin, Alpha-Cipermethrin, Beta-Cipermethrin, Theta-Cipermethrin, Zeta-Cipermethrin, Ciphenotrin [(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, Bioetanomethrin Permethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metoflutrin, protrifenbut, pyrethrin, terraretrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazin, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradiflon.
(5) Nicotinic acetylcholine receptor allosteric modulators: 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: Fluoricamide, Pymetrodin, Pyrifluquinazone.

(10) Mite 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 thuringiensis subspecies Isawai, Bacillus thuringiensis subspecies Kurstaki, Bacillus thuringiensis subspecies Teneblionis, Bt Crop protein: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
(12) Mitochondrial ATP biosynthetic enzyme inhibitor: diaffentiurone, 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: spirodiclofen, 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), brofuranilide, and other metaldehydes ..

(29) Anthelmintic:
(a) benzimidazoles: 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) Imidazothiazoles: 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, chlorphenurone, 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, indole-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 the preparation 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 weight" 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 alkyl allyl 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 and finely pulverized, and then the particle diameter is adjusted to 0.5 to 1.0 mm. Granules are obtained to obtain granules having 5% of the active ingredient.

(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 thienopyrimidine compound of the present invention, 4 parts of polyoxyethylene alkylallyl ether, 2 parts of sodium polycarboxylic acid 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. Wet grind to the following to give 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 synthesis 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]
(2- (1-(2-((Etyrimidineamino) oxy) -2- (5-fluoro-2-methoxyphenyl) ethyl) -5-methyl-2,4-dioxo-6- (2H-1,2) , 3-Triazole-2-yl) -1,4-dihydrothieno [2,3-d] Pyrimidine-3 (2H) -yl) -Synthesis of 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０．４４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た。有機相を、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、次いで溶媒を減圧留去した。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を得た。収率７７％
¹H-NMR (CDCl₃,δppm) 1.14(d,6H),1.82(s,6H),2.65(s,3H),3.99(s,3H),4.01-4.05(m,1H),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) . (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-Isopropyl-2-methyl-2- (5-methyl-2,4-dioxo-6- (2H-1,2,3-triazole-2-yl) -1,4-dihydrothieno [2,3-d] ] Pyrimidine-3 (2H) -yl) propanamide 0.56 g was dissolved in 10 ml of N, N-dimethylformamide. To this, 0.62 g of potassium carbonate and 0.44 of 2-bromo-5'-fluoro-2'-methoxyacetophenone were added under ice-cooling, and the mixture was stirred overnight at room temperature. The obtained liquid was poured into ice water and extracted with ethyl acetate. The organic phase was washed with water and then with saturated brine. Then, it was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.62 g of the target compound. Yield 77%
^{1 1} H-NMR (CDCl ₃ , δppm) 1.14 (d, 6H), 1.82 (s, 6H), 2.65 (s, 3H), 3.99 (s, 3H), 4.01-4.05 (m, 1H), 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).

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１．２７ｇをテトラヒドロフラン１５ｍｌおよびメタノール５ｍｌの混合溶媒に溶解させた。これに、氷冷下、テトラヒドロホウ酸ナトリウム０．１１ｇを加え、室温で２時間撹拌した。得られた液を減圧下で濃縮した。濃縮液を氷水に注加し、酢酸エチルで抽出した。有機相を、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、次いで溶媒を減圧留去した。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１．０ｇを得た。収率７９％
¹H-NMR (CDCl₃,δppm) 1.19(d,6H),1.83(s,6H),2.63(s,3H),3.92-4.25(m,6H),5.29-5.35(m,1H),6.78-7.30(m,3H),7.81(s,2H). (Step 2) 2- (1- (2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-) Synthesis of triazole-2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide

2- (1- (2- (5-Fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazole-2-yl) ) -1,4-Dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide 1.27 g was dissolved in a mixed solvent of 15 ml of tetrahydrofuran and 5 ml of methanol. To this, 0.11 g of sodium tetrahydroborate was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The obtained liquid was concentrated under reduced pressure. The concentrate was poured into ice water and extracted with ethyl acetate. The organic phase was washed with water and then with saturated brine. Then, it was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 1.0 g of the target compound. Yield 79%
^{1 1} H-NMR (CDCl ₃ , δppm) 1.19 (d, 6H), 1.83 (s, 6H), 2.63 (s, 3H), 3.92-4.25 (m, 6H), 5.29-5.35 (m, 1H), 6.78 -7.30 (m, 3H), 7.81 (s, 2H).

２−（１−（２−（５−フルオロ−２−メトキシフェニル）−２−ヒドロキシエチル）−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１．０ｇをテトラヒドロフラン２０ｍｌに溶解させた。これに、Ｎ−ヒドロキシフタルイミド０．６ｇ、およびトリフェニルホスフィン０．９７ｇを加えた。この液に氷冷下、アゾジカルボン酸ジイソプロピル０．７４ｇを加え、室温にて一晩撹拌した。得られた液から溶媒を減圧下で留去した。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０．７ｇを得た。収率５５％
¹H-NMR (CDCl₃,δppm) 1.18-1.24(m,6H),1.83-1.90(m,6H),2.62(s,3H),3.82(s,3H),4.13-4.45(m,3H),5.68-5.75(m,1H),6.17-6.24(m,1H),6.79-7.70(m,7H),7.80(s,2H). (Step 3) 2- (1- (2-((1,3-Dioxoisoindoline-2-yl) oxy) -2- (5-fluoro-2-methoxyphenyl) ethyl) -5-methyl-2 , 4-Dioxo-6- (2H-1,2,3-triazole-2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2 -Synthesis of methylpropanamide

2- (1- (2- (5-Fluoro-2-methoxyphenyl) -2-hydroxyethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazole-2-) Ill) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide 1.0 g was dissolved in 20 ml of tetrahydrofuran. To this was added 0.6 g of N-hydroxyphthalimide and 0.97 g of triphenylphosphine. 0.74 g of diisopropyl azodicarboxylate was added to this solution under ice-cooling, and the mixture was stirred overnight at room temperature. The solvent was distilled off from the obtained liquid under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.7 g of the target compound. Yield 55%
^{1 1} H-NMR (CDCl ₃ , δppm) 1.18-1.24 (m, 6H), 1.83-1.90 (m, 6H), 2.62 (s, 3H), 3.82 (s, 3H), 4.13-4.45 (m, 3H) , 5.68-5.75 (m, 1H), 6.17-6.24 (m, 1H), 6.79-7.70 (m, 7H), 7.80 (s, 2H).

２−（１−（２−（（１，３−ジオキソイソインドリン−２−イル）オキシ）−２−（５−フルオロ−２−メトキシフェニル）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０．２３ｇをジクロロメタン５ｍｌに溶解させた。これに、メチルヒドラジン３０ｍｇを加え、室温にて３時間撹拌した。得られた液を濾過し、濾液を減圧濃縮した。濃縮液をジクロロメタン５ｍｌに溶解させた。得られた液にアセトアルデヒド４４ｍｇを加え、室温にて一晩撹拌し、次いで溶媒を減圧下に留去した。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０．１９ｇを得た。収率９８％
¹H-NMR (CDCl₃,δppm) 1.14-1.24(m,6H),1.59-1.85(m,9H),2.67-2.69(m,3H),3.84-3.86(m,3H),4.10-4.25(m,2H),5.45-5.54(m,1H),5.98-5.99(m,1H),6.66-7.48(m,4H),7.83(s,2H). (Step 4) 2- (1- (2-((Etyrimidineamino) oxy) -2- (5-fluoro-2-methoxyphenyl) ethyl) -5-methyl-2,4-dioxo-6- (2H-) Synthesis of 1,2,3-triazole-2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide

2- (1-(2-((1,3-Dioxoisoindoline-2-yl) oxy) -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) -N-isopropyl-2-methylpropanamide 0.23 g was dissolved in 5 ml of dichloromethane. To this, 30 mg of methylhydrazine was added, and the mixture was stirred at room temperature for 3 hours. The obtained liquid was filtered, and the filtrate was concentrated under reduced pressure. The concentrate was dissolved in 5 ml of dichloromethane. 44 mg of acetaldehyde was added to the obtained solution, and the mixture was stirred at room temperature overnight, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.19 g of the target compound. Yield 98%
^{1 1} H-NMR (CDCl ₃ , δppm) 1.14-1.24 (m, 6H), 1.59-1.85 (m, 9H), 2.67-2.69 (m, 3H), 3.84-3.86 (m, 3H), 4.10-4.25 ( m, 2H), 5.45-5.54 (m, 1H), 5.98-5.99 (m, 1H), 6.66-7.48 (m, 4H), 7.83 (s, 2H).

Table 1 shows a part of the compound of the present invention produced by the same method as in the above-mentioned Examples. In the table, the physical characteristics, melting point (mp) or refractive index (n _D ) of each compound are also shown. The configuration E or Z in the table indicates the geometric isomer of the (alkylideneamino) oxy 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 Table 1, ¹ H-NMR (CDCl ₃ ) was measured for compounds having viscous oil or amorphous physical characteristics. Table 2 shows the measured values.

[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 dimethylformamide, and 1.5 parts by weight of polyoxyethylene sorbitan monolaurate (twin 20) are mixed and dissolved to obtain an emulsion (I) containing 5% of the active ingredient. Obtained.

The control value was calculated by the following formula.

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 above-mentioned chemical solution was sprayed on apple seedlings (cultivar "Orin", 3-4 leaf stage) cultivated in a seedling raising pot, and then air-dried. This was inoculated with conidia of apple scab (Venturia inaequalis) (treatment plot). As a control, apple 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 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.

Apple scab control tests were performed on the thienopyrimidine compounds of Compound Nos. 1, 2, 3 and 4. Both compounds showed a control value of 75% or more.

(Test Example 2) Cucumber Botrytis cinerea emulsion 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 the cucumber seedlings (cultivar "Crawling" type, cotyledon stage) cultivated in the seedling raising pot, and then air-dried. This was inoculated with a suspension of conidia of Botrytis cinerea cucumber (treatment group). As a control, cucumber 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 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.

Cucumber Botrytis cinerea control tests were carried out on the thienopyrimidine compounds of Compound Nos. 2, 4, 7 and 8. 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, and then air-dried. This was inoculated by sprinkling conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) (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.

A wheat powdery mildew control test was conducted on the thienopyrimidine compounds of Compound Nos. 1, 2, 3 and 4. 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, and then air-dried. This was inoculated by sprinkling summer spores of wheat leaf rust (Puccinia recondita) (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 12 days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

A wheat red rust control test was carried out on the thienopyrimidine compounds of Compound Nos. 1, 2, 3 and 4. 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 can be understood that 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.

Claims (2)

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

[In equation (I),
R ¹ is a substituted or unsubstituted C1-6 alkyl group.
R ² is a C1-6 alkoxycarbonyl group, or a 5-membered heteroaryl group.
R ³ is a substituted or unsubstituted C1-6 alkoxycarbonyl group or a substituted or unsubstituted C1-6 alkylaminocarbonyl group.
R ⁴ and R ^{4 'are} each independently a hydrogen atom or a substituted or unsubstituted C1~6 alkyl,
R ^6'is a hydrogen atom
X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
n indicates the number of chemically acceptable Xs and is an integer of 0 to 5. When n is 2 or more, Xs may be the same or different from each other, and R ⁶ is the formula ( It is a group represented by Q-1) or an oxy group (1,3-dioxoisoindoline-2-yl).

(In equation (Q-1), * is the connection position,
^Ra is a substituted or unsubstituted C1-6 alkyl group or C3-6 cycloalkyl group.
R ^b is a hydrogen atom or a C1-6 alkyl group.
R ^a and R ^b may be bonded to form a substituted or unsubstituted 5- to 6-membered ring with the carbon atom to which they are bonded. )]] A fungicide for agriculture and horticulture containing at least one selected from the group consisting of the compound according to claim 1 and salts thereof as an active ingredient.