KR890002192A - 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivatives and agricultural and horticultural fungicide compositions containing the same - Google Patents

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5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative and an agricultural / horticultural germicide composition containing the same.

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Claims (21)

5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative represented by the following general formula (I). Wherein X is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenyl group, a phenoxy group, a cyano group or a nitro group, Y is an alkynyl group which may be substituted with a hydrogen atom, a halogen atom, a haloalkyl group, an alkoxy group, a phenyl group or It is a cyano group. A compound according to claim 1, wherein in formula (I), X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a phenyl group, and Y is a hydrogen atom, a halogen group, a chloroalkyl group or a phenyl group, C which may be substituted with a cyano group 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative, characterized in that it is a _2-3 alkynyl group. The compound of claim 2, wherein in the general formula (I), X is a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group or a phenyl group, and Y is a hydrogen atom, a halogen atom or a cyano group. 1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative. 5H-1,3,4-thiadiazolo [3,2-a] according to claim 3, wherein in formula (I), X is a hydrogen atom and Y is a hydrogen atom, a halogen atom or a cyano group. Pyrimidin-5-one derivatives. The 5H-1,3,4-thiadiazole according to claim 3, wherein in the general formula (I), X is a halogen atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group or a phenyl group, and Y is a hydrogen atom. [3,2-a] pyrimidin-5-one derivatives. The method of claim 1, wherein the derivative is 2-benzylsulfonyl-7-fluoro-5H-1,3,4-thiadizolo [3,2-a] pyrimidin-5-one, 2-benzylsulfonyl -6-methyl-5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one, 2-benzylsulfonyl-6-methoxy-5H-1,3,4-thia Diazolo [3,2-a] pyrimidin-5-one, 2-benzylsulfonyl-6-fluoro-5H-1,3,4-thiadiazolo [3,2-a] pyrimidine-5- On, 2-benzylsulfonyl-6-chloro-5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one, 2-benzylsulfonyl-5H-1,3,4 -Thiadiazolo [3,2-a] pyrimidin-5-one or 2-benzylsulfonyl-7-cyano-5H-1,3,4-thiadiazolo [3,2-a] pyrimidine- 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative, characterized in that it is 5-one. And 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative represented by the following general formula (I) Wherein X is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenyl group, a phenoxy group, a cyano group or a nitro group, and Y is an alkynyl group which may be substituted with a hydrogen atom, a halogen atom, a haloalkyl group, an alkoxy group, or a phenyl group A cyano group) Agrohorticultural sterilization composition comprising a carrier that can be accommodated for agrohorticulture. The 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one represented by the general formula (I) wherein X is a hydrogen atom or a halogen atom , A lower alkyl group, a lower alkoxy group or a phenyl group, Y is a compound for farming and horticultural use, characterized in that the compound is a C _2-3 alkynyl group which may be substituted with a hydrogen atom, a halogen group, a chloroalkyl group or a phenyl group, a cyano group. The 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one of claim 8, wherein X is a hydrogen atom, a halogen atom, a methyl group, an ethyl group, A horticultural germicidal composition, wherein the compound is a methoxy group, an ethoxy group or a phenyl group and Y is a hydrogen atom, a halogen atom or a cyano group. 10. The compound of claim 8, wherein 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one represented by formula (I) is X is a hydrogen atom, Y is a hydrogen atom, a halogen Agrohorticultural germicidal composition, characterized in that the compound is an atom or a cyano group. The 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one represented by the general formula (I) is a halogen atom, a methyl group, an ethyl group, a methoxy group, A horticultural germicidal composition comprising an ethoxy group or a phenyl group and Y is a hydrogen atom. The 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one represented by formula (I) is 2-benzylsulfonyl-7-fluoro-5H. -1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one, 2-benzylsulfonyl-6-methyl-5H-1,3,4-thiadiazolo [3,2- a] pyrimidin-5-one, 2-benzylsulfonyl-6-methoxy-5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one, 2-benzylsulfonyl -6-fluoro-5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one, 2-benzylsulfonyl-6-chloro-5H-1,3,4-thia Diazolo [3,2-a] pyrimidin-5-one, 2-benzylsulfonyl-5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one or 2-benzyl A horticultural germicidal composition, characterized in that sulfonyl-7-cyano-5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one. By oxidizing the compound of formula (II) by a known method. Where X is as defined below A process for preparing 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one represented by the general formula (I). Wherein X is a hydrogen atom, a halogen atom, an alkynyl, alkoxy group, a phenyl group, a phenoxy group, a cyano group or a nitro group, and Y is a hydrogen atom, a halogen atom, a haloalkyl group, an alkoxy group, an alkyl which may be substituted with a phenyl group Diary or cyanogi). 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative represented by formula (II). Wherein X is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenyl group, a phenoxy group, a cyano group or a nitro group, and Y is an alkynyl group which may be substituted with a hydrogen atom, a halogen atom, a haloalkyl group, an alkoxy group, a phenyl group or It is a cyano group. 15. A compound according to claim 14, wherein X in formula (II) is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a phenyl group, and Y is C ₂ which may be substituted with a hydrogen atom, a halogen group, a chloroalkyl group or a phenyl group. 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative, which is a _-3 alkynyl group or a cyano group. 16. The compound of claim 15, wherein X in formula (II) is a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, or a phenyl group, and Y is a hydrogen atom, a halogen atom or a cyano group 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative. 16. The 5H-1,3,4-thiadiazolo [3,2-a] compound according to claim 15, wherein X in formula (II) is a hydrogen atom and Y is a hydrogen atom, a halogen atom or a cyano group. ] Pyrimidin-5-one derivatives. 16. The 5H-1,3,4-thia of claim 15, wherein X in General Formula (II) is a halogen atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, or a phenyl group, and Y is a hydrogen atom. Diazolo [3,2-a] pyrimidin-5-one derivatives. The compound represented by the following general formula (III) β-ketoester derivative (IV) and Wherein X ¹ is a hydrogen atom or a halogen atom, Y ¹ is a haloalkyl group, R ¹ is an alkyl group, and when X ¹ is a hydrogen atom, it can be converted to a halogen atom. A method for producing 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one represented by. Wherein X ¹ is a hydrogen atom or a halogen atom and Y ¹ is haloalkyl. Compound represented by the general formula (III) And β-formyl ester or 2-propenoate represented by the following general formula (VI) (X ² is a hydrogen atom, a halogen source, an alkyl group, an alkoxy group, a phenyl group or a phenoxy group, R ³ is an alkyl group and R ³ is a hydroxyl group or an alkoxy group. When X ² is a hydrogen atom it can be converted to a halogen atom and R ^{When 2} is a halogen atom, it may be converted to a cyano group). 5H-1,3,4-thiadiazolo [3,2-a] pyrimidine-5 represented by the general formula (IV). Method for preparing a -one derivative. Wherein X ² is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenyl group or a phenoxy group). The compound represented by the following general formula (III) Malonate derivatives represented by the general formula X ⁴ CH (CO ₂ R ⁴ ) 2 (Wherein X ⁴ is a hydrogen atom or an alkyl group and R ⁴ is a phenyl group or a substituted phenyl group). Wherein X ⁴ is as described above. The hydroxyl group at the 7-position of the resultant compound is converted into a halogen atom by a known method as desired, and if necessary, a halogen atom is converted into a cyano group or an alkynal group. A process for preparing a 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivative characterized by the following general formula (iii). (Wherein X ⁴ is a hydrogen atom or an alkyl group and Y ² is a halogen atom, an alkynyl group or a cyano group.) ※ Note: The disclosure is based on the initial application.