Cyclohexadiene oxime ether compound and application thereof

A technology of cyclohexadiene oxime ether and compound, applied in the field of pharmaceutical synthesis, can solve the problems of limited application scope, unusable herbicides and the like

Pending Publication Date: 2022-03-01
ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of herbicide is an efficient, safe, and highly selective ACCase inhibitor. It is only effective for most annual and perennial grass weeds and is safe for dicotyledonous crops. Therefore, this type of herbicide is mainly used to control soybean, Grass weeds in broad-leaved crop fields such as cotton, peanut and rapeseed, because grass crops are very sensitive to ACCase inhibitors, this type of herbicide cannot be used on grass crops such as rice, wheat, corn, etc., so its use is limited. Application range

Method used

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  • Cyclohexadiene oxime ether compound and application thereof
  • Cyclohexadiene oxime ether compound and application thereof
  • Cyclohexadiene oxime ether compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] This embodiment provides a kind of compound 1, and the structural formula of this compound 1 is as follows:

[0042]

[0043] The synthetic method of above-mentioned compound 1 comprises: in reactor, add 14.8g O-[2-(4-chloro-phenoxy group)-propyl group]-hydroxylamine and 19g propionyl triketone, 100ml sherwood oil, 5ml acetic acid, in The reaction was carried out at 25° C. for 24 hours. After the reaction, the solvent was removed, washed with water and concentrated to obtain 31 g of a reddish-brown viscous liquid, namely compound 1, with a yield of 97%.

[0044] Wherein, the proton nuclear magnetic spectrum of the compound 1: 1HNMR (400MHz CDCl3): δ7.2 (2H, m), δ6.8 (2H, m), δ4.6 (1H, m), δ4.1 (2H, m),δ2.8(2H,m),δ2.5(2H,m),δ2.2(2H,m),δ2.1(1H,m),δ1.5(2H,m),δ1. 2(11H,m), δ0.9~1.1(4H,m).

Embodiment 2

[0046] This embodiment provides a kind of compound 2, and the structural formula of this compound 2 is as follows:

[0047]

[0048] The synthetic method of above-mentioned compound 2 comprises: in reactor, add 15.3g 4-(1-aminooxymethyl-butyl-2-enoxy)-benzonitrile and 17.8g 5-ethoxymethyl-2 -Verylcyclohexane-1,3-dione, 150ml petroleum ether, 3ml acetic acid, reacted at 30°C for 12h, removed the solvent after the reaction, washed with water and concentrated to obtain 30g of reddish-brown viscous liquid, namely compound 2, and The yield was 94%.

[0049] Wherein, the proton nuclear magnetic spectrum of the compound 2: 1HNMR (400MHz CDCl3): δ7.3 (2H, d), δ6.9 (2H, d), δ5.5 (2H, m), δ4.1 (1H, m), δ3.8(2H,d), δ3.3(5H,m), δ2.3(5H,m), δ1.8(3H,d), δ1~1.3(12H,m).

Embodiment 3

[0051] This embodiment provides a kind of compound 3, and the structural formula of this compound 3 is as follows:

[0052]

[0053] The synthetic method of above-mentioned compound 3 comprises: in reactor, add 14g O-[2-(4-chloro-phenoxy)-propyl]-hydroxylamine and 20.9g 1-(4-ethylthiomethyl-2, 6-dimethoxy-cyclohexyl-1,5-dienyl)-pentan-1-one, 120ml petroleum ether, 15ml acetic acid, react at 15°C for 28h, remove the solvent after the reaction, wash with water and concentrate to get 31 g of reddish-brown viscous liquid, namely compound 3, and the yield was 92%.

[0054] Wherein, the proton nuclear magnetic spectrum of the compound 3: 1HNMR (400MHz CDCl ): δ7.2 (2H, d), δ6.6 (2H, d), δ4.6 (1H, d), δ3.8 (3H, m), δ3.4 (6H, s), δ2.2 (7H, m), δ1.5 (3H, d), δ1.2~1.4 (9H, m), δ0.9 (3H, t).

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PUM

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Abstract

The invention provides a cyclohexadiene oxime ether compound which has a structural formula shown in the specification, in which a group R1 and a group R3 are respectively selected from H, an aliphatic substituent group containing 1-6 carbon atoms, a halogenated aliphatic substituent group, a cyano-substituted aliphatic substituent group, an amino group or amide, a phenyl group, a halogenated aromatic substituent group or a cyano-substituted aromatic substituent group; the group R1 is selected from H, aliphatic substituent containing 1-6 carbon atoms, halogenated aliphatic substituent, cyano-substituted aliphatic substituent, amido or amide, phenyl, halogenated aromatic substituent, cyano-substituted aromatic substituent or heterocyclic aromatic substituent, the heterocyclic aromatic substituent is selected from H, halogen,-CN,-NO2,-CF3 and-C (CF3) 3, and n is the number of substituents and is selected from 1, 2 and 3. The invention also provides an application of the cyclohexadiene oxime ether compound in preparation of herbicides.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a cyclohexadiene oxime ether compound and its application. Background technique [0002] Due to the succession and change of weed populations and the emergence and rapid development of resistance to chemical pesticides, people's awareness of ecological environment protection has been continuously strengthened. The emphasis on the issue of whereabouts continues to increase. With the gradual reduction of the world's arable land, the continuous growth of the population and the increase in the demand for food, people are forced to rapidly develop agricultural production technology, improve and improve the farming system, and need to continuously invent new and improved herbicidal compounds and compositions. [0003] Cyclohexenone herbicides were developed in the 1960s. This type of herbicide is a very important class of herbicides. It destroys the biosynthesis of fatty acids by inhibit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/47C07C255/54C07D213/64C07C251/54C07D207/36A01N35/10A01N37/40A01N43/40A01N37/02A01N43/36A01P13/00
CPCC07C323/47C07C255/54C07D213/64C07C251/54C07D207/36A01N35/10A01N37/40A01N43/40A01N37/02A01N43/36C07C2601/16C07C2601/02C07C2601/14
Inventor 邓照西胡合伟郭少雄岑金谭宾杜兵兵杨莉娜李君沛孙金凤
Owner ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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