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Triazolopyrimidine antibacterial agent and pesticide composition thereof

A pesticide composition, azolopyrimidine technology, applied in the directions of fungicides, biocides, biocides, etc., can solve problems such as failure to achieve the broad-spectrum antibacterial activity of triazolopyrimidine, and achieve excellent antibacterial performance, good antibacterial activity and the like. performance effect

Inactive Publication Date: 2019-05-21
赵言元
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In fact, it has also failed to achieve the broad-spectrum antibacterial activity of triazolopyrimidine

Method used

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  • Triazolopyrimidine antibacterial agent and pesticide composition thereof
  • Triazolopyrimidine antibacterial agent and pesticide composition thereof
  • Triazolopyrimidine antibacterial agent and pesticide composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of compound (I-1)

[0039](1) Synthesis of 2-mercapto-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine (II-1)

[0040] Add 23.4g 5-amino-3-mercapto-1,2,4 triazole and 28.6g ethyl acetoacetate, 10g solid NaOH, 50g glacial acetic acid as reaction solvent in a 250mL three-necked flask, heat to reflux, react for 8h, and then A yellow solid formed. After the reaction, cool to room temperature, distill off the solvent under reduced pressure, filter and wash with water, dry to obtain needle-like crystals, recrystallize with acetic acid to obtain pure products, and dry to obtain the product 2-mercapto-5,7-dimethyl-[1,2 ,4] Triazolo[1,5-a]pyrimidine (II-1), the yield is 96%.

[0041] 1 HNMR:2.33(s,3H,5-CH 3 ), 2.53(s,3H,7-CH 3 ), 7.16 (s, 1H, 6-H), 12.61 (s, 1H, SH). Anal. Calcd. for C 7 h 8 N 4 S: C.46.51, H.4.42, N.31.04, S.18.03. m / z:180.05,Found:180.23.

[0042] (2) Synthesis of 2-mercapto-5,7-dimethyl-6-(1-piperidinyl)-[1,2,4]triazolo[1...

Embodiment 2

[0050] Embodiment 2: compound (I-2) 2-(2-(4H-1,2,4triazol-3-yl)-ethylthio)-5,7-dimethyl-6-(4-methylpiperidin-1-yl)-[ 1,2,4]triazolo[1,5-a]pyrimidine.

[0051] 1 HNMR:0.96(d,3H,4-piperdin-CH 3 ), 1.59~1.67 (m, 5H, piperdin-CH 2 -, -CH-), 3.06~3.10 (m, 4H, -CH 2 -), 2.35(s,6H,Ar-CH 3 ), 3.22(t,2H,S-CH 2 -), 2.89(t,2H,-CH 2 -), 8.13 (s, 1H, triazolyl-H). Anal.Calcd.for C 17 h 24 N 8 S: C.54.82, H.6.49, N.30.08, S.8.61. m / z: 372.18, Found: 372.49.

Embodiment 3

[0052] Embodiment 3: compound (I-3) 2-(2-(4H-1,2,4triazol-3-yl)-ethylthio)-5,7-dimethyl-[1,2,4]triazolo[1,5-a ] pyrimidine.

[0053] 1 HNMR:7.06(s,1H,Ar-H),2.33(s,3H,5-CH 3 ), 2.50(s,3H,7-CH 3 ), 3.26(t,2H,S-CH 2 -), 2.92(t,2H,-CH 2 -), 8.13 (s, 1H, triazolyl-H). Anal.Calcd.for C 11 h 13 N 7 S: C.47.98, H.4.76, N.35.61, S.11.65. m / z: 275.12, Found: 275.31.

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PUM

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Abstract

The invention relates to a triazolopyrimidine antibacterial agent. The structure of the triazolopyrimidine antibacterial agent is shown in a formula (I), wherein R1 and R2 are independently H, halogenatoms, C1-C6 alkyl, C1-C6 alkoxy, and C1-C6 halogenated alkyl; R3 is H, 1-piperidyl and 4-methyl-1-piperidyl; A is -O-, -S- and -NH-. The compound is high in broad-spectrum antibacterial activity under low concentration. The riazolopyrimidine antibacterial agent and paclobutrazol can be used as pesticide compositions and are composited to use, so that the coordinative synergistic effect is realized; the antibacterial performance is further improved; plant diseases caused by harmful fungus to crops such as wheat, cotton and fruit can be greatly prevented and treated, so that the crop output isincreased.

Description

technical field [0001] The present invention relates to an antibacterial agent for pesticides, in particular to a pyrimidotriazole antibacterial active compound and a synthesis method thereof, and also to a pesticide composition, which uses the pyrimidotriazole compound and paclobutrazol as active ingredients . Background technique [0002] Triazolopyrimidine compounds are broad-spectrum antibacterial agents, and are a type of agricultural fungicides with the largest sales volume and many varieties in the market. Pyrimidine triazole fungicides have been used in my country for more than ten years, and many bacteria have developed resistance to them, resulting in an increasing dosage of pesticides, no significant improvement in control efficiency, increased pesticide application costs, and may even cause phytotoxicity to crops . Therefore, there is an urgent need to modify the existing triazolopyrimidine compounds or find alternative compounds with better effects. [0003] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P3/00
Inventor 赵言元李志娟
Owner 赵言元