Isoxazoline-containing tetrahydrophthalimide compound and use thereof

A kind of technology of tetrahydrophthalimide and isoxazoline, applied in the field of tetrahydrophthalimide compounds

Active Publication Date: 2016-07-20
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to develop new herbicides to solve the increasingly serious problem of herbicide res...

Method used

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  • Isoxazoline-containing tetrahydrophthalimide compound and use thereof
  • Isoxazoline-containing tetrahydrophthalimide compound and use thereof
  • Isoxazoline-containing tetrahydrophthalimide compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] The preparation of embodiment 1 compound 6

[0125]

[0126] 1) Preparation of 2-chloro-4-fluoro-5-nitrobenzaldehyde oxime

[0127] Dissolve 42g (0.206mol) of 2-chloro-4-fluoro-5-nitrobenzaldehyde in 200ml of ethanol, drop to 0°C, add dropwise 17.4g (0.25mol) of an aqueous solution of hydroxylamine hydrochloride under stirring, and then raise to room temperature Stir the reaction. After 2 hours, TLC monitored the reaction to be complete. Poured into water, filtered to obtain 38.3g of white solid. The melting point is 103°C.

[0128] 2) Preparation of ethyl 3-(2-chloro-4-fluoro-5-nitrophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate

[0129] Dissolve 43.7g (0.2mol) of 2-chloro-4-fluoro-5-nitrobenzaldehyde oxime in 150ml of N,N-dimethylformamide, raise the temperature to 30°C, and add 32g (0.24 mol) NCS to form a light yellow solution, which was kept at 35° C. for 1 hour. Cool down to room temperature, add 300ml of dichloromethane, then wash twice with 1N hydr...

Embodiment 2

[0136] The preparation of embodiment 2 compound 5

[0137] Referring to the preparation of compound 6 in Example 1, the ethyl methacrylate added in the (2nd) step was replaced with methyl methacrylate. Oil. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm): 1.72(s,3H), 1.83(m,4H), 2.43(m,4H), 3.40(d,1H), 3.96(s,3H), 4.01(d,1H), 7.38( d,1H), 7.70(d,1H).

Embodiment 3

[0138] The preparation of embodiment 3 compound 4

[0139] 8g (0.019mol) of compound 6 was added to 20ml of ethanol, 1.52g (0.038mol) of sodium hydroxide aqueous solution was added, and the reaction was stirred at room temperature for 4 hours. The completion of the reaction was monitored by TLC, poured into water, adjusted to pH 3 with 1N hydrochloric acid, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain 7.2 g of light yellow oil.

[0140] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):1.69(s,3H),1.85(m,4H),2.44(m,4H),3.41(d,1H),3.88(d,1H),7.35(d,1H),7.69( d, 1H).

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Abstract

The invention belongs to the field of agricultural herbicides, and concretely relates to an isoxazoline-containing tetrahydrophthalimide compound and a use thereof. The isoxazoline-containing tetrahydrophthalimide compound is represented by general formula (I), has very good weeding activity, can effectively control Zinnia elegans, piemarker, setaria viridis, barnyard grass and other weeds, realizes a very good weeding effect under a low dosage, is highly safe to crops, such as corn, wheat and rice, and can be used as a herbicide in the agricultural field.

Description

technical field [0001] The invention belongs to the field of agricultural herbicides, and in particular relates to a tetrahydrophthalimide compound containing isoxazoline and its application. Background technique [0002] Tetrahydrophthalimide herbicides were developed earlier and were mostly used as upland herbicides. Although there are fewer studies in recent years, there are patent reports from time to time. As Nissan Chemical Industries discloses the following general formula in patents JP2229157 and JP1139581 structure. However, the control effect of these known compounds on weeds is not always completely satisfactory. [0003] [0004] Wherein: Q1 is a five-membered heterocycle such as oxadiazole, oxazole or benzoxazole. Q2 is F or H. [0005] In the prior art, although the disclosed compounds have certain similarities with the compounds of the present invention, the compounds represented by the general formula of the present invention are significantly different...

Claims

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Application Information

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IPC IPC(8): C07D413/10C07D413/14A01N43/82A01N47/12A01P13/00
Inventor 杨吉春吴峤崔东亮关爱莹卢政茂王秀丽刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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