Sulfonylurea compound

A technology for sulfonylureas and compounds, applied in the field of organic compounds, can solve the problems of reduced herbicidal activity and selectivity, and achieve the effects of low residue, low residue and good selectivity

Inactive Publication Date: 2013-05-01
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] These compounds all have similar structural features, and the substituents on the aromatic ring have the form of single substitution or double substitution, but none of the substit

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of (2-methoxycarbonyl-4-nitro)phenyl tert-butyl sulfide

[0034] Take a 250mL round bottom flask, put it into an oil bath, set the temperature of the oil bath to 25°C, and 2 Under atmosphere, add 10mL DMSO, 2.4g KOH, stir, after 20min, add 6mL tert-butylmercaptan to the round bottom flask, and continue stirring for 30min. Add 7.84g of methyl 2-chloro-5-nitrobenzoate to the round bottom flask, set the temperature of the oil bath to 110°C after the addition is complete, a yellow solid is formed during the heating process, and react for 90 minutes after the temperature reaches 110°C . The heating was stopped, and the flask was cooled to room temperature, and there was a yellow-black solid at the bottom of the bottle. Add 150mL of water to the round bottom flask, a yellow solid precipitates, stir, filter with suction, wash with water to obtain a yellow solid, extract the filtrate with 2×200mL ethyl acetate, combine the ethyl acetate filtrate, and wash with 2×100...

Embodiment 2

[0043] Adopt existing method to prepare following sulfonylurea compounds:

[0044]

[0045] NMR hydrogen spectrum (TMS is internal standard, CDCl 3 is the solvent) shows that the compound contains 10 hydrogens, and the peak is assigned to 12.225 (s 1H SO 2 NH)8.330~8.353(m2HArH)8.384~8.407(m2HArH)7.310(s1HCONH)6.513(s1HArH)4.012(s3HOCH 3 ).

Embodiment 1 and 2

[0047] The herbicidal activity experiment of sulfonylurea compound A and B in embodiment 1 and 2:

[0048] Plant barnyardgrass seeds in the seed germination box, spray with 1ppm of A and B herbicides after 5 days of germination, the results show that the sulfonylurea compound with general formula (I) has high herbicidal activity, and the product meets the requirements of environmental friendliness .

[0049] Table 2 Herbicidal activity of target compounds 1 and 3

[0050]

[0051]

[0052] ++++ means that all the branches and leaves are scorched, and there are no new sprouts;

[0053] +++ indicates that the branches and leaves are withered and yellow, and there are no new sprouts;

[0054] ++ indicates that the branches and leaves are withered and yellow, and there are a small amount of newly sprouted leaves;

[0055] + means only a few branches and leaves are withered and yellow, and there are more new green branches and leaves

[0056] 0 There are more new green br...

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Abstract

The invention relates to the technical field of organic compounds, and provides a sulfonylurea compound with the following general formula I (refer to the Specification). In the formula, R1 is at least one of hydroxyl, halogen atom, hydroxyl, amino, nitro, amide group and carboxyl, amino, dialkyl amino alkyl and alkane hydroxyl; R2 is any one of hydrogen, alkyl carbonyl oxygen and halogen atom; R3 and R4 are same or different alkoxy or halogen atoms; and X1, X2 and X3 are same or different N or CH. The sulfonylurea compound has the characteristics of higher weeding activity, good selectivity and low residue.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, in particular to sulfonylurea compounds. Background technique [0002] At present, sulfonylurea compounds have been widely used in agriculture as herbicides, but long-term use has caused weeds to develop a certain degree of resistance. Therefore, it is of practical significance to design and synthesize new sulfonylurea compound herbicides with high efficiency, safety, low residue and high selectivity. [0003] There are many reports about sulfonylurea compound herbicides, such as U.S. Patent US5160365, US6228808, Chinese patents CN1080116A, CN1106393A, CN1702064A, CN1391440A, CN1569844A, CN1080116A, etc. all relate to sulfonylurea compounds, and their similar structures are as follows: [0004] [0005] These compounds all have similar structural features, and the substituents on the aromatic ring have the form of single substitution or double substitution, but none of the substitue...

Claims

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Application Information

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IPC IPC(8): C07D239/47A01P13/00
CPCA01N47/36C07D239/47
Inventor 王明良杨海朋林小雄陈苗刘剑洪
Owner SHENZHEN UNIV
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