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Preparation and Application of Herbicidal Compounds with Different Substituents of Phenol Esters

A compound and a secondary substitution technology, applied in the field of pesticides, can solve problems such as insufficient duration, high cost, and poor weeding efficacy, and achieve the effects of reducing dosage and cost, reducing residues, and mitigating potential threats

Active Publication Date: 2020-12-22
HUNAN AGRI BIOTECH RES CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the herbicidal efficacy of organic acid herbicides in the prior art is still poor, especially for some specific weeds, the duration is not enough, and the cost is high

Method used

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  • Preparation and Application of Herbicidal Compounds with Different Substituents of Phenol Esters
  • Preparation and Application of Herbicidal Compounds with Different Substituents of Phenol Esters
  • Preparation and Application of Herbicidal Compounds with Different Substituents of Phenol Esters

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] This example provides a 2,4-disubstituted phenol organic acid ester: nonanoic acid-2-nitro-4-methylphenyl ester, the preparation method is as follows:

[0032] 3.0g (19.6mmol) of 2-nitro-4-methylphenol was dissolved in 30mL of N,N-dimethylformamide, 3.8g (21.6mmol) of nonanoyl chloride was added, 2.18g of triethylamine (21.6mmol ), refluxed for 3-4h, cooled and poured into the ice water of ammonium carbonate, stirred for 1h, left standstill, precipitated solid, filtered to obtain nonanoic acid-2-nitro-4-methylphenyl ester, dried and weighed 5.38g, produced Rate: 85%.

[0033] The relevant data are as follows: 1HNMR (400MHz, DMSO-d6) δ: 7.80 (d, 1H), 7.53 (d, 1H), 7.40 (d, 1H), 2.81 (t, 2H), 2.23 (s, 3H), 1.70 (m, 2H), 1.42 (m, 2H), 1.38 (m, 2H), 1.30 (m, 6H), 0.9 (s, 3H). MS: (M+Na)+: 316.18

Embodiment 2

[0035] This example provides a 2,4-disubstituted phenol organic acid ester: 2-bromo-4-sulfonic acid phenyl dodecanoate, the preparation method is as follows:

[0036] 3.0g (13.7mmol) of 2-bromo-4-sulfonic acid phenol, dissolved in 30mL of dimethyl sulfoxide, added 3.3g (15mmol) of dodecanoyl chloride, 1.65g of triethylamine (16.5mmol), and refluxed for 3-4h , cooled and poured into ice water of ammonium carbonate, stirred for 1 h, allowed to stand still, the solid precipitated, filtered to obtain 2-bromo-4-sulfonic acid phenyl dodecanoate, weighed 3.35g after drying, yield: 61%.

[0037] The relevant data are as follows: 1HNMR (400MHz, DMSO-d6) δ: 9.10 (br, 1H), 8.81 (d, 1H) 8.33 (dd, 1H), 7.90 (dd, 1H), 2.78 (t, 2H), 2.13 ( m, 2H), 1.70 (m, 2H), 1.38 (m, 2H), 1.32 (m, 2H), 1.28 (m, 10H), 0.9 (s, 3H). MS: (M+Na)+: 424.66

Embodiment 3

[0039]This example provides a 2,4-disubstituted phenol organic acid ester: 2,4-hexadienoic acid 2-bromo-4-nitrophenyl ester, the preparation method is as follows:

[0040] 5.0g (23mmol) of 2-nitro-4-methylphenol was dissolved in 30mL of dimethyl sulfoxide, and 3.0g (23mmol) of 2,4-hexadienoyl chloride, 2.55g of triethylamine (25.3mmol) were added , refluxed for 3-4h, cooled and poured into ice water with ammonium carbonate, stirred for 1h, stood still, precipitated solid, filtered to obtain 2-bromo-4-nitrophenyl 2,4-dihexenoic acid, weighed 5.56 g, Yield: 78%.

[0041] The relevant data are as follows: 1HNMR (400MHz, DMSO-d6) δ: 8.68 (d, 1H), 7.83 (dd, 1H), 7.41 (d, 1H), 7.52 (d, 1H), 6.33 (m, 1H), 6.10 (d, 1H), 5.44 (m, 1H), 1.7 (d, 3H), 1.30 (m, 6H), 0.9 (s, 3H). MS: (M+Na)+: 334.06

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PUM

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Abstract

The invention provides preparation of a phenolic ester herbicidal compound with different substituents, and applications. The structure contained by the herbicidal compound is shown as a general formula (I); and in the general formula (I), R1 represents -NO2, -Br, -Cl, -F, -SO3H or -CN, R2 represents -CH3, -NO2, -Br, -Cl, -F, -SO3H, -CN or -SO3NH2, and R3 represents C6-C12 alkyl or C6-C8 alkenyl.The herbicidal compound can effectively reduce the using amount and costs of herbicides, so that residuals can be reduced, and potential threats of pesticide to environments can be mitigated.

Description

technical field [0001] The invention relates to the field of pesticides, more specifically, to the preparation and application of herbicidal compounds with different substituents of phenolic esters. Background technique [0002] Weeds in rice cultivation will affect the yield and quality of rice. Different weeds such as rice planthopper, rice stink bug, rice armyworm, armyworm, etc. are the hosts of pests, which not only make rice suffer from weed damage, but also It also increases the possibility of pests and diseases. For a long time, chemical control has been an effective means of controlling weeds in paddy fields, which saves time and labor. However, the cost of using chemical herbicides in the prior art is relatively high, the control cost is relatively high, and the environment is damaged. With the implementation of measures to ban highly toxic and highly toxic pesticides, organic acid herbicides have become a research hotspot. [0003] Organic acids are a large cla...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/22C07C69/587C07C67/14
CPCA01N37/02A01N37/06A01N41/04
Inventor 李祖任柏连阳罗丁峰
Owner HUNAN AGRI BIOTECH RES CENT
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