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Triazolopyrimidine sulfonamides herbicide as well as preparation method and application thereof

An azolopyrimidine sulfonamide and herbicide technology, applied in the field of triazolopyrimidine sulfonamide herbicides, can solve the problems of long residual effect period, slow degradation, affecting the quality and yield of subsequent crops, and achieve short residual effect period, highly active effect

Inactive Publication Date: 2009-07-22
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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  • Triazolopyrimidine sulfonamides herbicide as well as preparation method and application thereof
  • Triazolopyrimidine sulfonamides herbicide as well as preparation method and application thereof
  • Triazolopyrimidine sulfonamides herbicide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Compound I—Preparation of N-2,6-Difluorophenyl-5-methoxy-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

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

[0020] Dissolve 8.0 g (0.2 mol) of sodium hydroxide in 100 ml of water, add 23.2 g (0.2 mol) of 3-amino-5-mercapto-1,2,4-triazole with stirring, continue stirring for 0.5 hours, add dropwise 25.2 g (0.2 mol) of benzyl bromide dissolved in 20 ml of ethanol, after dropping, stirring at room temperature, thin layer chromatography to track the reaction until the raw material disappears, the reaction takes about 6 hours, suction filtration, and the filtrate is concentrated under reduced pressure to obtain a pale yellow solid 39.2 grams, with a yield of 95%.

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

[0022] Add 60 ml of anhydrous methanol to a 250 ml three-necked flask, add 6.9 g of sodium metal in batches, then add 45 ml of anhydrous ethanol and ...

Embodiment 2

[0036] Weeding activity test (greenhouse pot method)

[0037] A test material training

[0038] The soil for the test is the pastoral soil, mountain soil and the purchased decomposed organic soil collected in the area where pesticides are not used, prepared in a volume ratio of 1:1:1, mixed and stirred evenly and used as the special soil for the test. Take 9.5 cm diameter and 8 cm deep flower pots respectively, and fill 3 / 4 of the pot with soil. After adding water and waiting for the soil to be completely moistened, sow the seeds of nine broad-leaved grasses and three gramineous weeds into the pots. Each weed guarantees 10-15 seeds. After sowing, cover with 1 to 3 cm thick mixed sand. After the soil in the flowerpot is saturated with water, let go of the accumulated water at the bottom of the flowerpot, and then place it in the greenhouse for cultivation. Replenish water every day to keep the soil moisture at about 80% (relative humidity), the growth temperature is 15-30°C, and th...

Embodiment 3

[0045] Crop safety evaluation test

[0046] A test material training

[0047] The test soil is the pastoral soil, mountain soil and purchased decomposed organic soil collected from the unused plots, prepared in a volume ratio of 1:1:1, mixed and stirred evenly and used as the special soil for the test. Take a flowerpot with a diameter of 12 cm and fill 3 / 4 of the flowerpot with soil. After adding water and waiting for the soil to be completely moistened, sow the seeds of each crop into the pots, each with 5-8 seeds, after sowing, cover 1~3 cm thick mixed sand and fine soil, and let the soil in the flowerpot become saturated with water. Water accumulates at the bottom of the flowerpot, and then it is placed in a greenhouse for cultivation and growth. Replenish water every day to keep the soil humidity around 80% RH, the growth temperature 15-35°C, and the air humidity above 50%.

[0048] B test method

[0049] The greenhouse potting method is used to spray post-emergence of 6 crops...

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Abstract

The invention relates to a triazolo-pyrimidine sulfonamide herbicide, a method for preparing the same and application thereof. The chemical name of the herbicide is N-2,6-difluorophenyl-5-methoxy-1,2,4-triazolo-[1,5-a] pyrimidine-2-sulfonamide as shown in a chemical structural formula I. The compound has remarkable weeding activity to broad leaved weeds such as chenopodium serotinum, cassia tora, mustard, amaranthus retroflexus, eclipta prostrate, cerastium arvense, purslane, pieprint and bitter cress. Compared with a merchandized medicine flumetsulam, the triazolo-pyrimidine sulfonamide herbicide has the advantages of high drug effect, short residual period, more safety to crops, and the like.

Description

Technical field [0001] The invention relates to a triazolopyrimidine sulfonamide herbicide and its preparation method and application. Background technique [0002] The discovery of acetohydroxy acid synthase (AHAS) inhibitors represented by sulfonylurea super-efficient herbicides in the 1980s was an important milestone in the history of pesticide chemistry. It marked the beginning of herbicide chemistry. On the new development path of super high efficiency, low toxicity and low residue. Among them, triazolopyrimidine sulfonamide herbicides are important representatives of acetohydroxy acid synthase (AHAS) inhibitors. Flumetsulam, N-2,6-difluorophenyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide The first commercial triazolopyrimidine sulfonamide herbicide developed by the Agricultural Corporation in the early 1990s. It is highly effective and broad-spectrum, can control most annual and perennial broad-leaved weeds, and can be used for soybean, corn, wheat and barley, p...

Claims

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Application Information

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IPC IPC(8): A01N43/90C07D487/04A01P13/00
Inventor 陈超南刘祖明杨光富
Owner HUAZHONG NORMAL UNIV
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