Sulfonyl urea compounds and herbicidal activity thereof

A compound, sulfonylurea technology, applied in organic chemistry, animal repellents, plant growth regulators, etc., can solve problems such as large differences in crop sensitivity

Inactive Publication Date: 2005-11-30
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Among the reported sulfonylurea compounds, most of them have strong selectivity, and their sensitivities to different crops vary greatly. Since these compounds may cause serious harm to the next crops, some sulfonylurea compounds are used as Active ingredient herbicides (such as chlorsulfuron) have been restricted in some areas

Method used

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  • Sulfonyl urea compounds and herbicidal activity thereof
  • Sulfonyl urea compounds and herbicidal activity thereof
  • Sulfonyl urea compounds and herbicidal activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1: the synthesis of 2-methoxy ester group 5-nitrobenzenesulfonamide

[0063] In the 100ml three-necked round-bottomed flask that is connected with tail gas absorption device, spherical condenser and thermometer, drop into 9.00 grams of 6-nitrosaccharin (Syntheses of saccharin and Cyclanate Derivatives Bearing Polymerizable Vinyl Group, Hiroyoshi K, et al.Bull.Chem. Soc.Jpn., 1982,55:3824-3827), add about 55ml of dry methanol, make it saturated with HCl gas, heat in an oil bath with stirring and slowly heat up to solvent reflux, continue to keep the temperature for 7 hours with HCl. The solvent methanol was distilled off under reduced pressure, and then saturated NaHCO 3 The pH value of the residual solid was adjusted to about 7.0, filtered, the filter residue was fully washed with water, and dried to obtain 6.45 g of white powder with a yield of 62.9% and a melting point of 196-198°C.

Embodiment 2

[0064] Embodiment 2: the synthesis of 2-methoxy ester group 5-nitrophenyl isocyanate

[0065] Add 3.9 grams (0.015mol) of 2-methoxy ester group 5-nitrobenzenesulfonamide, 30ml anhydrous toluene, 0.075mol in the 100ml three-neck round-bottomed flask equipped with drying tube, tail gas absorption reflux condenser and thermometer Oxalyl chloride, and add 0.25gDABCO (triethylenediamine) as a catalyst under stirring. Slowly raise the temperature to 60°C under stirring, keep at 60-65°C for 6 hours, then slowly raise the temperature to 90°C, react at 90-100°C for 18 hours, remove the solid by filtration, remove toluene and excess oxalyl chloride under reduced pressure The brown oily crude isocyanate was obtained, which was directly used in the next reaction without purification.

Embodiment 3

[0066] Embodiment 3: the synthesis of 6-aminosaccharin

[0067] Add 125ml of absolute ethanol, 5.0 grams (0.02mol) of 6-nitrosaccharin and 0.25 grams of 10% Pd / C in a 250ml three-necked flask, and introduce H for 4 hours under stirring. 2 , the insolubles were removed by filtration, and the filtrate was precipitated to obtain 3.93 g of a light yellow solid with a yield of 90.5% and a melting point of 286-289°C.

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Abstract

The invention relates to a sulfonylurea compound synthesizing method and grass-clearing active. The general formula of the compound is (I), in which R1 is 1-6 alkyl, 1-6 alkoxy, 1-6 carbonyl, halogen or nitro group; R2 is 1-6 alkyl, 1-6 alkoxy, 1-4 alkyl sulfide, 1-4 alkylamino radical, halogen or nitro group; R3 is 1-6 alkyl, 1-6 alkoxy, 1-6 alkyl substitution, 1-6 acylaminosulfonamides, 1-6 alkylamine, aryl, aryl substituent, halogen or nitro group. The invention possesses elite grass-clearing active and selective to crop, and it especially can be used as weed killer to eliminate broadleaf weed in corn field.

Description

technical field [0001] This invention relates to sulfonylurea compounds and their herbicidal activity. Background technique [0002] Among the reported sulfonylurea compounds, most of them have strong selectivity, and their sensitivities to different crops vary greatly. Since these compounds may cause serious harm to the next crops, some sulfonylurea compounds are used as Active ingredient herbicides (such as chlorsulfuron) have been restricted in some areas. [0003] European patent EP502740 discloses the compound of following formula: [0004] [0005] The sulfonylurea compound substituted at the 5-position of the aromatic ring not only has high activity, but also has a fast degradation rate, and has little or no influence on subsequent crops. [0006] Because the cultivation system of crops in our country is different from that in foreign countries, the main crops in developed countries are only planted once a year, while in our country we have to plant multiple crop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/57
Inventor 李正名穆小丽范志金李永红刘斌赵卫光王建国王素华王宝雷
Owner NANKAI UNIV
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