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A kind of triazolopyrimidine sulfonamide herbicide and its preparation method and application

An azolopyrimidine sulfonamide and herbicide technology, which is applied in the field of triazolopyrimidine sulfonamide herbicides, can solve the problems of long residual effect period, slow degradation, influence on quality and yield of subsequent crops, and achieves short residual effect period, Highly active effect

Inactive Publication Date: 2011-11-30
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that it degrades slowly in the soil and has a long residual period, which affects the quality and yield of subsequent crops.

Method used

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  • A kind of triazolopyrimidine sulfonamide herbicide and its preparation method and application
  • A kind of triazolopyrimidine sulfonamide herbicide and its preparation method and application
  • A kind of triazolopyrimidine sulfonamide herbicide and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Compound I——N-2,6-difluorophenyl-5-methoxy-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide preparation

[0019] Intermediate 2 - Synthesis of 3-amino-5-benzylthio-1,2,4-triazole:

[0020] Dissolve 8.0 grams (0.2 moles) of sodium hydroxide in 100 milliliters of water, add 23.2 grams (0.2 moles) of 3-amino-5-mercapto-1,2,4-triazole under stirring, continue stirring for 0.5 hours, then add dropwise Dissolve 25.2 grams (0.2 moles) of benzyl bromide in 20 milliliters of ethanol, drop it, stir at room temperature, track the reaction by thin-layer chromatography until the raw material point disappears, the reaction takes about 6 hours, filter with suction, and concentrate the filtrate under reduced pressure to obtain a light yellow solid 39.2 g, yield 95%.

[0021] Intermediate 3 - Synthesis of 2-benzylthio-5,7-dihydroxy-1,2,4 triazolo[1,5-a]pyrimidine:

[0022] Add 60 milliliters of absolute methanol in a 250 milliliter three-necked flask, add 6.9 grams of sodium metal in bat...

Embodiment 2

[0035] Herbicidal activity test (greenhouse pot method)

[0036] A test material cultivation

[0037] The soil used in the test is pastoral soil, mountain soil collected from areas where pesticides are not used, and purchased decomposed organic soil, prepared at a volume ratio of 1:1:1, mixed and stirred evenly, and used as test soil. Take flower pots with a diameter of 9.5 cm and a depth of 8 cm, and fill 3 / 4 of the pot with soil. Add water until the soil is completely wet, sow the seeds of nine kinds of broad-leaved grasses and three kinds of grass weeds into the pots respectively, and ensure 10-15 seeds for each weed. After sowing, cover with 1-3 cm thick mixed sand After the soil in the flower pot is saturated with water, let off the water at the bottom of the flower pot, and then put it in the greenhouse for cultivation and growth. Replenish water every day to keep the soil humidity around 80% (relative humidity), the growth temperature is 15-30°C, and the air humidity is...

Embodiment 3

[0044] Crop Safety Evaluation Test

[0045] A test material cultivation

[0046] The soil used in the test is pastoral soil, mountain soil collected from untreated plots, and purchased decomposed organic soil, prepared at a volume ratio of 1:1:1, mixed and stirred evenly, and used as the soil for the test. Take a flower pot with a diameter of 12 cm and fill the soil with 3 / 4 of the pot. Add water until the soil is completely moist, sow the seeds of each crop into the pots, 5 to 8 seeds of each kind, cover with 1 to 3 cm thick mixed sand and fine soil after sowing, and release the seeds after the soil in the flower pot is saturated with water. Water is accumulated at the bottom of the flower pot, and then placed in the greenhouse for cultivation and growth. Replenish water every day to keep the soil humidity around 80% RH, the growth temperature is 15-35°C, and the air humidity is above 50%.

[0047] B test method

[0048] Six crops of rice, cotton, soybean, corn, rapeseed ...

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Abstract

The present invention relates to a triazolopyrimidine sulfonamide herbicide and its preparation method and application. The chemical name of the herbicide is N-2,6-difluorophenyl-5-methoxy-1,2,4 -Triazolo[1,5-a]pyrimidine-2-sulfonamide, chemical structural formula such as I. The compound has significant herbicidal activity on the broad-leaved weeds Chenopodium chinensis, Cassia, mustard greens, retroflexus, sausage, roll ear, purslane, velvetleaf and shepherd's purse. Compared with the commercial medicine Kuocaoqing, it has the advantages of high efficacy, short residual period and safer for crops.

Description

technical field [0001] The invention relates to a triazolopyrimidine sulfonamide herbicide, a preparation method and application thereof. Background technique [0002] The discovery of acetohydroxyacid synthase (AHAS) inhibitors represented by sulfonylurea super-efficient herbicides in the 1980s was an important milestone in the history of pesticide chemistry, and it marked that herbicide chemistry has begun to step forward. A new development path of ultra-high efficiency, low toxicity, and low residue. Among them, triazolopyrimidine sulfonamide herbicides are important representatives of acetohydroxyacid synthase (AHAS) inhibitors. Flumetsulam, N-2,6-difluorophenyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide is an American Dow Proprietary The first commercial triazolopyrimidine sulfonamide herbicide developed by the agricultural company in the early 1990s. Its high efficiency and broad spectrum can control most annual and perennial broad-leaved weeds, and can ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A01P13/00
Inventor 陈超南刘祖明杨光富
Owner HUAZHONG NORMAL UNIV
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