# US 2014/0194625 A1 · Preparation of 2-methyl-4-amino-5(substituted-1h-1,2,3-triazolyl)methylpyrimidine derivatives and microbicidal activity thereof

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- Number: US 2014/0194625 A1
- Document ID: US20140194625A1
- Status: Published application
- Kind: A1
- Application number: 14/204,225
- Filed: 2014-03-11
- Published: 2014-07-10
- Earliest claimed: 2011-09-13
- Assignees: Central China Normal University
- Applicants: Central China Normal University
- Inventors: Hongwu He; Junbo He; Fang Wang; Xiaoguo Wang; Xiaosong Tan; Hao Peng
- Web page: https://patentgrep.com/patent/US20140194625A1

## CPC

- C07D 403/06: linked by a carbon chain containing only aliphatic carbon atoms
- A01N 43/647: Triazoles; Hydrogenated triazoles
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

Disclosed is a derivative of 2-methyl-4-amino-5-(substituted-1H-1,2,3-triazol)methylpyrimidine of general formula I and microbicidal activity thereof. In the formula, R1 represents hydrogen, I; X represents O or NH; Y represents phenyl of substituted phenyl, benzoyl or substituted benzoyl, phenyloxyacetyl or substituted phenyloxyacetyl; the substituents on the phenyl rings which Y involves are: H, halogen, nitro, cyano, CF3, C1˜4 alkyl, methoxyl, C1˜2 carboxyl or carboxylic ester groups; any position of phenyl rings can be mono- or multi-substituted by identical or different substituents. The compound has a significant inhibition effect on cucumber bacterial angular leaf spot, tomato bacterial leaf spot, cucumber brown blot, cucumber downy mildew, rice sheath blight, Gibberella saubinetii, Alternaria solani, Botrytis cinerea, Alternaria alternate and Colletotrichum orbiculare and it can be used as an effective ingredient of microbicides.

## Claims

### Claim 1

A 2-methyl-4-amino-5-(substituted-1H-1,2,3-triazolyl)methylpyrimidine derivative, having a structure of formula I:
wherein R1 represents hydrogen or iodine, X represents O or NH, Y represents phenyl or substituted phenyl, benzoyl or substituted benzoyl, phenoxyacetyl or substituted phenoxyacetyl; and
wherein each substituent on the benzene ring of Y is H, halogen, nitro, cyano, CF3, C1-4 alkyl, methoxy, C1-2 carboxy or carboxylate, the substituents are mono- or multi-substituted at any position of the benzene ring, and the substituents are the same or different.

### Claim 2 (depends on 1)

A method for preparing the 2-methyl-4-amino-5-(substituted-1H-1,2,3-triazolyl)methylpyrimidine derivative of claim 1,
wherein the 2-methyl-4-amino-5-(substituted-1H-1,2,3-triazolyl)methylpyrimidine derivative has a structure of formula I-1;
wherein the structure of formula I-1 is prepared by reacting a compound of formula II with a compound of formula III:
and
wherein in formula I-1 and formula III, R1 is defined as in formula I, R2 is H, halogen, nitro or C1-4 alkyl, and R3 is H, halogen, nitro, cyano, CF3, C1-4 alkyl, methoxy, C1-2 carboxy or carboxylate.

### Claim 3 (depends on 1)

A method for preparing the 2-methyl-4-amino-5-(substituted-1H-1,2,3-triazolyl)methylpyrimidine derivative of claim 1,
wherein the 2-methyl-4-amino-5-(substituted-1H-1,2,3-triazolyl)methylpyrimidine derivative has a structure of formula I-2;
wherein the structure of formula I-2 is prepared by reacting a compound of formula II with a compound of formula IV:
and
wherein in formula I-2 and formula IV, X is defined as in formula I, R1 represents hydrogen or iodine, R2 is H, halogen or nitro, and R3 is H, halogen, nitro or C1-4 alkyl.

### Claim 4 (depends on 1)

A method for preparing the 2-methyl-4-amino-5-(substituted-1H-1,2,3-triazolyl)methylpyrimidine derivative of claim 1,
wherein the 2-methyl-4-amino-5-(substituted-1H-1,2,3-triazolyl)methylpyrimidine derivative has a structure of formula I-3;
wherein the structure of formula I-3 is prepared by reacting a compound of formula II with a compound of formula V:
and
wherein in formula I-3 and formula V, X is defined as in formula I, R1 represents hydrogen, R2 is H, halogen, nitro, CF3 or C1-4 alkyl, and R3 is H, halogen, nitro, C1-4 alkyl or methoxy.

### Claim 5 (depends on 1)

Use of a compound represented by formula I of claim 1 as microbicidal active component.

### Claim 6 (depends on 1)

Use of a compound represented by formula I of claim 1 as microbicidal active component against bacterial spot of cucumber, tomato bacterial leaf spot, corynespora leaf spot of cucumber downy mildew of cucumber, rice sheath blight disease, wheat scab, early blight of tomato, gray mold of cucumber, tobacco brown spot, and anthracnose of cucumber.