Pyrimidinoxy salicylic acid derivative

A technology for pyrimidyloxysalicylic acid and derivatives, which is applied in the field of pyrimidyloxysalicylic acid derivatives, can solve problems such as selectivity and limited application range of crops, and achieve good herbicidal effect, high herbicidal activity, and effective herbicidal activity. Effect

Inactive Publication Date: 2004-03-17
中国中化股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above various pyrimidine salicylic acid compounds have high activity, but they also show inhibitory activity on rapeseed and other crops, that is, their selectivity and application range of crops are limited

Method used

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  • Pyrimidinoxy salicylic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0038] Synthesis Intermediate (IV)-1 R 1 =H, R 2 = 2-pyridyl

[0039] The 250ml round bottom flask is connected with a water separator, a condenser and a calcium chloride drying tube. 62.0g of salicylaldehyde, 47.0g of 2-aminopyridine, 100ml of toluene and a catalytic amount of p-toluenesulfonic acid are added to the bottle, electromagnetic stirring The temperature was raised and refluxed for 6 hours, the toluene was evaporated and then cooled, an orange solid was precipitated, which was recrystallized by 100 ml of petroleum ether-ethyl acetate with a molar ratio of 1:4 to obtain 80 g of orange crystals.

[0040] H 1 NMR: δ 13.47 (S, 1H); δ 9.45 (S, 1H); δ 6.94-8.92 (M, 8H).

[0041] MS: 198(M - ).

Synthetic example 2

[0043] Synthetic compound (I)-1 R 1 =H, R 2 = 2-pyridyl

[0044] After drying the reaction system to remove water, add 5.58 g of sodium hydride solid (55% paraffin wax suspension agent) and 100 ml of anhydrous tetrahydrofuran to a 1000 ml round bottom flask under the protection of nitrogen flow, and add dropwise under electromagnetic stirring at room temperature. Example 1 prepared 19.8 g (IV)-1 in 150 ml of anhydrous tetrahydrofuran solution. During this process, hydrogen gas was released, resulting in an orange-yellow suspension. Then, a solution of 21.8 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine (V) in 500 ml of anhydrous tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature overnight. After filtration, the mother liquor was concentrated, and recrystallized with tetrahydrofuran-petroleum ether at a molar ratio of 2:1 to obtain 20.5 g of yellow crystals.

[0045] H 1 NMR: δ 9.29 (S, 1H); δ 5.78 (S, 1H); δ 3.80 (S, 1H);

[0046] δ 6.48-8.45 (M, 8H...

Synthetic example 3

[0049] Synthesis Intermediate (IV)-12 R 1 =H, R 2 = 2-(6-methyl)benzothiazolyl

[0050] Add 1.22 g of salicylaldehyde, 40 ml of methanol, and 1.84 g of 2-amino-(6-chloro)benzothiazole to a 100 ml round-bottom flask. The temperature is raised and refluxed for 10 minutes under electromagnetic stirring, and then slowly cooled, orange crystals are precipitated, and filtered. 1.4 g of the product was obtained.

[0051] MS: 288(M + ).

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Abstract

A category of pyramidinyloxy salicylic acid derivatives as shown by the structural formula [I], where R' represents low class alkyl radical with H or 1-6 c atoms; R2 represents the group with the following structure: [a] group is pyridyl radical or R3 substituted pyridyl radical, the group represented by R3 includes alkyl radical with 1-6 C atoms, halogen or OH; in [b] group, A is O,S or NH, B is CH or N, R4 is H, halogen, OH, NO2, CF3, alkyl radical with 1-6 C atoms or alkoxy radical; in [c] group, A is O,S or NH, and R5 is H or alkyl radical with 1-6 C atoms. This category of derivatives has high weedicidal activity and selectivity, low toxicity, and is effective ingredients for compounding weedicide for rope, cotton and rice.

Description

Technical field [0001] The present invention relates to a new class of pyrimidinoxysalicylic acid derivatives with herbicidal activity, their preparation methods, and pesticide formulations containing these new compounds. technical background [0002] Pyrimidine salicylic acid herbicides were first developed by the Japan Combination-Anhara Chemical Company in 1987 (EP223406, 27.5.1987). It is another class of super efficient herbicides after sulfonylurea and thick sulfonylurea herbicides. Herbicides, their mechanism of action also exerts herbicidal effects by inhibiting the activity of acetolactate synthase (ALS), and these compounds have good activity against broad-leaved weeds. [0003] After 12 years of development, there are now 4 varieties: KIH-2031 at 70~105g.ai / ha (gram active compound / ha), can completely control most of the weeds in cotton fields, and is safe for cotton; KIH-6127 (EP435170) 30~90g.ai / ha can completely control most of the weeds in p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/54C07D239/46
Inventor 彭伟立陈杰吴军李明智夏旭建
Owner 中国中化股份有限公司
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