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Herbicidal activity of tetrazoleone derivative containing 7-fluoro-2-methyl benzoxazine-3-one structure

A technology of methylbenzoxazine and herbicidal activity, which is applied in the field of herbicidal activity of tetrazolone derivatives, and can solve the problems of no specific records, no specific records of compound herbicidal activity, etc.

Inactive Publication Date: 2013-09-25
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Although the above-mentioned documents report the herbicidal activity of various 2,5-disubstituted tetrazolone compounds, there is no specific description of the 7-fluoro-2-methylbenzoxazine-3-containing compounds mentioned in this patent. Tetrazolone compounds with a ketone structure, and there is no specific description of the herbicidal activity of these compounds

Method used

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  • Herbicidal activity of tetrazoleone derivative containing 7-fluoro-2-methyl benzoxazine-3-one structure
  • Herbicidal activity of tetrazoleone derivative containing 7-fluoro-2-methyl benzoxazine-3-one structure
  • Herbicidal activity of tetrazoleone derivative containing 7-fluoro-2-methyl benzoxazine-3-one structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: 1-ethyl-4-(7-fluoro-2-methyl-4-allylbenzoxazin-3-one-6-yl)tetrazolone (I-1)

[0019] Take 4mmol of 4-(7-fluoro-2-methyl-4-allylbenzoxazin-3-one-6-yl)tetrazolone and 6mmol of bromoethane into a 50mL two-necked bottle, add 30mL of THF, and stir to dissolve Then add 20mmol triethylamine, reflux for 8h. The reaction solution was poured into an aqueous solution, and the organic phase was separated and dried. The pure product was obtained by column chromatography.

Embodiment 2

[0020] Embodiment 2: 1-(3-chloropropyl-1)-4-(7-fluoro-2-methyl-4-allyl benzoxazin-3-one-6-yl)tetrazolone ( I-2)

[0021] Take 3.5mmol of 4-(7-fluoro-2-methyl-4-allylbenzoxazin-3-one-6-yl)tetrazolone and 5.2mmol of 1-bromo-3-chloropropane into a 50mL two-necked bottle, Add 30mLTHF, stir to dissolve, then add 22mmol triethylamine, and reflux for 7.4h. The reaction solution was poured into an aqueous solution, and the organic phase was separated and dried. The pure product was obtained by column chromatography.

Embodiment 3

[0022] Example 3: 1-ethyl-4-(7-fluoro-2,4-dimethylbenzoxazin-3-one-6-yl)tetrazolone (I-3)

[0023] Take 2.4mmol of 4-(7-fluoro-2,4-dimethylbenzoxazin-3-one-6-yl)tetrazolone and 4.3mmol of bromoethane into a 50mL two-necked bottle, add 33mL of THF, and stir to dissolve Then add 20mmol triethylamine, reflux for 5.9h. The reaction solution was poured into an aqueous solution, and the organic phase was separated and dried. The pure product was obtained by column chromatography.

[0024] Compound (I) was synthesized according to a similar method, and the physical parameter results of the compound are shown in Table 1.

[0025] The physical property characterization of compound (I) of table 1

[0026]

[0027]

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Abstract

The invention relates to the herbicidal activity of tetrazoleone derivative containing a 7-fluoro-2-methyl benzoxazine-3-one structure. R<1>=CH3, CH2CH=CH2 and FORMULA; R<2>=C2H5, CH2CH=CH2, CH2(CH2)2Cl, CH2COOC2H5 and CHCH3COOC2H5. If 3g of the medicine is applied to each mu, a herbicidal effect on amaranth is shown before and after seedling.

Description

(1) Technical field [0001] The present invention relates to the herbicidal activity of tetrazolone derivatives containing 7-fluoro-2-methylbenzoxazin-3-one structure. (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 o...

Claims

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Application Information

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IPC IPC(8): C07D413/04A01P13/00
Inventor 朱有全王丹阳程杰王晓芳张海利
Owner NANKAI UNIV
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