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Synthesis of 4-substituted methoxy acrylate-1,2,4-triazolinones derivatives and herbicidal activity

A methoxyacrylate and triazolinone technology is applied in the field of synthesis and herbicidal activity of a class of 4-substituted methoxyacrylate-1,2,4-triazolinone derivatives, and can solve the problem of No problems such as reports have been reported, and the effect of significant herbicidal activity has been achieved

Inactive Publication Date: 2009-12-30
HUBEI RUNZENG GREEN PLANT PROTECTION CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its structural feature is that it contains the structural unit of β-methoxyacrylate. People have derived it based on this and developed a large number of new varieties of fungicides. Several compounds with insecticidal activity have also been found. Compounds with herbicidal activity have not been reported

Method used

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  • Synthesis of 4-substituted methoxy acrylate-1,2,4-triazolinones derivatives and herbicidal activity
  • Synthesis of 4-substituted methoxy acrylate-1,2,4-triazolinones derivatives and herbicidal activity
  • Synthesis of 4-substituted methoxy acrylate-1,2,4-triazolinones derivatives and herbicidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] preparation of

[0027] Step A: Preparation of intermediate pyruvate-2-fluoro-4-chlorophenylhydrazone

[0028] Add 20 grams (0.137 moles) of 2-fluoro-4-chloro-aniline and 160 milliliters of concentrated hydrochloric acid to a 500 milliliter three-necked flask under nitrogen protection, cool to -9°C in an ice-salt bath, and slowly add 50 milliliters of 9.5 g (0.137 moles) of sodium nitrite in aqueous solution (about 30 minutes), after addition, stirred at -9°C-0°C for 1 hour. Then at this temperature, 68 milliliters of concentrated hydrochloric acid solution (about 40 minutes) containing 68.1 grams (0.3 moles) of tin chloride was added dropwise. 110 ml of water were added and 125 ml of an aqueous solution containing 12.2 g (0.137 mol) of pyruvic acid was added within 5 minutes. Continue to stir for 30 minutes, filter with suction, wash with water, and dry to obtain 27.7 g of the product, m.p.162-163°C. This process was repeated 3 more times.

[0029] Step B: Prepar...

Embodiment 2

[0032] preparation of

[0033] Step A: Preparation of intermediate 2-(2-fluoro-4chloro-5-nitrophenyl)-5-methyl-1,2,4-triazolin-3-one

[0034] Dissolve 0.05 mole of 2-(2-fluoro-4-chlorophenyl)-5-methyl-1,2,4-triazol-3-one in 100 ml of concentrated sulfuric acid, slowly add 68% nitric acid 4.5 gram, control the reaction temperature below 25°C, after the addition is complete, stir at 25°C for 1 hour, pour into ice water, filter, wash, and dry to obtain 9.5 grams of the product. This process was repeated 3 more times.

[0035] Step B: Preparation of intermediate 2-(2-fluoro-4chloro-5-aminophenyl)-5-methyl-1,2,4-triazolin-3-one

[0036] 0.01 mole of 2-(2-fluoro-4-chloro-5-nitrophenyl)-5-methyl-1,2,4-triazolin-3-one, 0.55 g of ammonium chloride and 2.24 g (0.04 mol) reduced iron powder was added to 25 milliliters of ethanol and 3 milliliters of water, heated and refluxed for 4-6 hours, cooled, then filtered with diatomaceous earth and washed with ethanol. The filtrate was conc...

Embodiment 3

[0051] preparation of

[0052] In a 250 ml single-necked flask, add 80 ml of N,N-dimethylformamide solution, 0.01 mole of 2-(2-fluoro-4 chlorophenyl)-5-methyl-1,2,4-tri Azolin-3-one, 2.1 g (0.015 mol l) of anhydrous potassium carbonate and 0.011 mol of (E)-methyl 2-(2-bromomethylphenyl)-3-methoxyacrylate. After stirring at room temperature for 24 hours, the reaction mixture was poured into ice water, and a large amount of white solid was precipitated, left to stand, filtered with suction, dried, and column chromatography (acetone:petroleum ether=1:6v / v) gave the product, white solid, yield 43%; m.p. 113-115°C.

[0053] Elemental Analysis: Calculated C% 58.41 H% 4.43 N% 9.73

[0054] Measured value C% 58.09 H% 4.28 N% 9.74

[0055] 1 H NMR (400MHz, CDCl 3 , δ / ppm): δ1.93 (s, 3H, CH 3 ), 3.64 (s, 3H, CO 2 CH 3 ), 3.87 (s, 3H, OCH 3 ), 4.66, 4.86 (ss, 2H, CH 2 ), 7.19-7.57 (m, 8H, ArH, CH=);

[0056] MS (EI 70eV) m / z (%): 432 ([M] + , 56), 399 (67.28), 205 (...

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Abstract

The invention relates to the composition and the herbicidal activity of 4-substituted methoxyl acrylic ester-1, 2, 4-triazolinone derivative with the general formula I. In the formula, X and Y represent H, F, Cl, and Br, or methyl Z represents H and Cl; W represents H, methylsulfonyl amino, ethyl sulfonamide, phenylsulfonamido, and methoxyl; Q represents C or N. The chemical compound of the invention can generate remarkable herbicidal activity to cockspur grass, crab grass, green bristlegrass, leaf mustard, redroot amaranth and chenopodium serotinum Linn when the dosage is 300 grams of effective component per hectare, thereby being used as a herbicide. The chemical compound is safe when being used for paddy rice, thereby being used as a paddy field herbicide.

Description

Technical field: [0001] The invention relates to the synthesis and herbicidal activity of a class of 4-substituted methoxyacrylate-1,2,4-triazolinone derivatives. Background technique: [0002] Strobilurin fungicides are a new type of high-efficiency and broad-spectrum fungicides developed by the British Zeneca Company in the late 1980s. Its structural feature is that it contains the structural unit of β-methoxyacrylate. People have derived it based on this and developed a large number of new varieties of fungicides. Several compounds with insecticidal activity have also been found. However, compounds with herbicidal activity have not been reported. [0003] 1,2,4-Triazolinone derivatives have a wide range of herbicidal activities, which belong to protoporphyrinogen oxidase inhibitors, and have been favored by major pesticide companies and scientific research institutions in recent years. Many relevant patents have been applied for such derivatives, and several commercial ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12A01N43/653A01P13/00
Inventor 杨光富骆焱平刘祖明王国栋
Owner HUBEI RUNZENG GREEN PLANT PROTECTION CO LTD
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