Weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone

A technology based on aminocarbonyltetrazolone and benzoxazinone, which is applied in the field of herbicidal activity, and can solve the problems of no specific record and no specific record of compound herbicidal activity, etc.

Inactive Publication Date: 2013-01-16
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although the above-mentioned documents report the herbicidal activity of a variety of 2,5-disubstituted tetrazolone compounds, there is no specific description of the 2-benzoxazinone-5-cyclohexylaminocarbonyl tetrazolene mentioned in this patent. Azolone compounds, let alone any specific description of the herbicidal activity of these compounds

Method used

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  • Weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone
  • Weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone
  • Weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: 2-(7-chloro-4-methyl-oxobenzoxazinone-6-yl)-5-cyclohexyl (methyl)aminocarbonyl tetrazolone (I-1)

[0018] Take 3mmol 2-(7-chloro-4-methyl-oxobenzoxazinon-6-yl)tetrazolone and 3.3mmol cyclohexyl (methyl)carbamoyl chloride into a 50mL two-necked bottle, add 15mLTHF, Stir to dissolve, then add 10mmol triethylamine, and reflux for 5h. The reaction solution was poured into saturated ammonium chloride solution, 50 ml of ethyl acetate was added, the organic phase was separated, and dried over anhydrous Na2SO4. The pure product was obtained by column chromatography.

Embodiment 2

[0019] Example 2: 2-(7-chloro-4-ethyl-oxobenzoxazinone-6-yl)-5-cyclohexyl(methyl)aminocarbonyltetrazolone (I-2)

[0020] Take 3mmol of 2-(7-chloro-4-methyl-oxobenzoxazinone-6-yl)tetrazolone and 3.3mmol of cyclohexyl (methyl)carbamoyl chloride into a 50mL two-necked bottle, add 15mLTHF, and stir After dissolving, add 10mmol triethylamine and reflux for 5h. The reaction solution was poured into saturated ammonium chloride solution, 50 ml of ethyl acetate was added, the organic phase was separated, and anhydrous Na 2 SO 4 dry. The pure product was obtained by column chromatography.

[0021] Example 2: 2-(7-Chloro-4-propenyl-oxobenzoxazinone-6-yl)-5-cyclohexyl(methyl)aminocarbonyltetrazolone (I-3)

[0022] Take 3mmol of 2-(7-chloro-4-methyl-oxobenzoxazinon-6-yl)tetrazolone and 3.3mmol of cyclohexyl (methyl)carbamoyl chloride into a 50mL two-necked bottle, add 15mL of THF, Stir to dissolve, then add 10mmol triethylamine, and reflux for 5h. The reaction solution was poured int...

Embodiment 4

[0023] Example 4: 2-(7-fluoro-4-methyl-oxobenzoxazinon-6-yl)-5-cyclohexyl(methyl)aminocarbonyltetrazolone (I-9)

[0024] Take 3mmol 2-(7-fluoro-4-methyl-oxobenzoxazinon-6-yl)tetrazolone and 3.3mmol cyclohexyl (methyl)carbamoyl chloride into a 50mL two-necked bottle, add 15mLTHF, Stir to dissolve, then add 10mmol triethylamine, and reflux for 5h. The reaction solution was poured into saturated ammonium chloride solution, 50 ml of ethyl acetate was added, the organic phase was separated, and anhydrous Na 2 SO 4 dry. The pure product was obtained by column chromatography.

[0025] Compound (I) was synthesized according to a similar method, and the physical parameter results of the compound are shown in Table 1.

[0026] Table 1 Characterization of physical properties of compound (I)

[0027]

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Abstract

The invention relates to weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone,Wherein R1 is CH3 and C2H5; R2 is CH3, C2H5, CH2CH=CH2 and propargyl group; and R3 is F and Cl.When 1500g of weedicide per hectare is applied, the weedicide has broad spectrum for cockspur grass, crab grass, amaranth and rape before and after seedling.

Description

(1) Technical field [0001] The present invention relates to the herbicidal activity of 2-benzoxazinonyl-5-cyclohexylaminocarbonyltetrazolones. (2) Background technology [0002] Herbicides are the most widely used pesticide species in the current society. Among them, heterocyclic herbicides have attracted more and more attention because of their characteristics of good selectivity, high activity, low dosage and low toxicity. The development of herbicides with tetrazolone as the mother nucleus is another important field of herbicide development. This type of herbicide has the advantages of high efficiency, low toxicity, and safety to subsequent crops. By changing its substituent, it can greatly change its weed spectrum and crop selectivity. It is a class of pesticides with great development prospects. [0003] In 1990, Theodoridis et al. (Pestic Sci, 1990, 30: 259-274.) reported that 2-aryl-5-substituted alkyl tetrazolone derivatives are a new class of efficient herbicides t...

Claims

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Application Information

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IPC IPC(8): C07D413/04A01N47/38A01P13/00
Inventor 朱有全王丹阳袁燕伟程杰王晓芳
Owner NANKAI UNIV
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