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CN-121974906-A - Sulfonamide compound and preparation method and application thereof

CN121974906ACN 121974906 ACN121974906 ACN 121974906ACN-121974906-A

Abstract

The application provides a sulfonamide compound, a preparation method and application thereof, wherein the structure of the sulfonamide compound is shown as a formula I: -I. The sulfonamide compound has excellent pest killing activity. The application also provides a preparation method of the sulfonamide compound, which is simple and easy to produce. The application also provides application of the sulfonamide compound in preparation of insecticide or acaricide, and has good commercial development value.

Inventors

  • SUN JIALONG
  • LIU KE
  • ZHAI XIAOLU
  • ZHANG WEIJIE
  • REN HONGHUA

Assignees

  • 济南乐丰作物科学有限公司

Dates

Publication Date
20260505
Application Date
20260402

Claims (10)

  1. 1. The sulfonamide compound or the pharmaceutically acceptable salt thereof is characterized in that the structure of the sulfonamide compound is shown as a formula I: I; wherein R is selected from 、 - (CH 2 ） n3 -C3-C8 cycloalkyl, - (CH 2 ） n4 -C3-C8 heterocycle or- (CH 2 ） n5 -substituted C3-C8 heterocycle), R 1 、R 2 、R 3 、R 4 is independently selected from cyano, C1-C6 alkyl, halogen substituted C1-C6 alkyl, n1, n2, n3, n4, n5 are independently selected from integers from 0 to 5, het is selected from 、 、 、 、 、 、 Ar is selected from R 5 is selected from cyano, C1-C6 alkyl, halogen substituted C1-C6 alkyl, n6 is selected from integers from 0 to 5; R 6 is selected from hydrogen, C1-C6 alkyl, R 7 is selected from C1-C6 alkyl, halogen substituted C1-C6 alkyl.
  2. 2. The sulfonamide compound according to claim 1, wherein R 1 、R 4 is independently selected from cyano, C1-C3 alkyl, halogen substituted C1-C3 alkyl, R 2 、R 3 is independently selected from C1-C3 alkyl, R 6 is selected from hydrogen, C1-C3 alkyl, R 7 is selected from fluoro substituted C1-C3 alkyl, C3-C8 cycloalkyl is selected from 、 、 The substituted C3-C8 heterocycle is selected from the group consisting of a C1-C3 alkyl substituted C3-C8 heterocycle, an amino substituted C3-C8 heterocycle, and-N (CH 3 ） 2 substituted C3-C8 heterocycle).
  3. 3. The sulfonamide compound or an agropharmaceutically acceptable salt thereof according to claim 1, wherein the sulfonamide compound has a structure as shown in formula I-1: ; wherein Het is selected from 、 、 Ar is selected from 、 R 51 、R 52 、R 53 、R 54 、R 55 is independently selected from halogen, halogen substituted C1-C3 alkyl.
  4. 4. A sulfonamide compound according to claim 3, wherein Ar is selected from the group consisting of 、 、 。
  5. 5. The sulfonamide compound of claim 1, or an agropharmaceutically acceptable salt thereof, wherein the sulfonamide compound is selected from the group consisting of the following structures: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。
  6. 6. a process for the preparation of a sulfonamide compound according to any one of claims 1 to 5, or a pharmaceutically acceptable salt thereof, wherein the sulfonamide compound is prepared according to the following reaction scheme: ; Wherein X is halogen; The preparation of the sulfonamide compound comprises the steps of reacting a compound A with a compound B under the action of an acid binding agent to obtain a reaction solution containing the sulfonamide compound, and purifying to obtain the sulfonamide compound.
  7. 7. An agricultural insecticidal and acaricidal composition comprising a sulfonamide compound according to any one of claims 1 to 5 or an agropharmaceutically acceptable salt thereof.
  8. 8. The agricultural insecticidal and acaricidal composition according to claim 7, wherein the mass percentage of the sulfonamide compound or the agriculturally acceptable salt thereof in the agricultural insecticidal and acaricidal composition is 0.1% to 99.9%.
  9. 9. The agricultural insecticidal and acaricidal composition according to claim 7, further comprising an auxiliary agent, wherein the mass percentage of the auxiliary agent in the agricultural insecticidal and acaricidal composition is 0.1-99.9%.
  10. 10. Use of a sulfonamide compound according to any one of claims 1 to 5 or an agropharmaceutically acceptable salt thereof or an insecticidal and acaricidal composition according to any one of claims 7 to 9 for the preparation of an insecticide and/or for the preparation of an acaricide.

Description

Sulfonamide compound and preparation method and application thereof Technical Field The application relates to the technical field of pesticides, in particular to a sulfonamide compound, a preparation method and application thereof. Background The existing agricultural pest control means still mainly depend on the use of pesticides, the wide use of traditional pesticides is accompanied with the problems of development of pest resistance, environmental pollution risk and the like, and the long-term use of some classical pesticides causes serious drug resistance to many pests, so that the insecticidal effect of the pesticides is poor. In addition, with the increase of environmental requirements, the development of green pesticides will be a new trend in the development of future plant protection. Therefore, it would be desirable to provide a more efficient insecticide. Disclosure of Invention In order to find and discover pesticide lead and candidate compounds which are more efficient, broad-spectrum, low-toxicity and free of cross resistance, the application innovatively designs and synthesizes a sulfonamide compound (shown as a formula I). According to the national pesticide bioassay specifications, the inventor carries out insecticidal activity test on the series of compounds, and related bioassay data show that the compound designed and synthesized by the inventor shows good insecticidal activity at a lower concentration, has low toxicity to non-target organisms, is safe to mammals, has no negative effect on the environment, meets the development requirement of environment-friendly green pesticides, and has higher value. The application has strong academic value, social value and economic significance for developing sulfonamide compound pesticides with novel structure and good environmental compatibility. In order to solve at least one of the above technical problems, in a first aspect, the present application provides a sulfonamide compound or an agropharmaceutically acceptable salt thereof, wherein the structure of the sulfonamide compound is shown in formula I: I; wherein R is selected from 、- (CH 2）n3 -C3-C8 cycloalkyl, - (CH 2）n4 -C3-C8 heterocycle or- (CH 2）n5 -substituted C3-C8 heterocycle), R 1、R2、R3、R4 is independently selected from cyano, C1-C6 alkyl, halogen substituted C1-C6 alkyl, n1, n2, n3, n4, n5 are independently selected from integers from 0 to 5, het is selected from、、、、、、Ar is selected fromR 5 is selected from cyano, C1-C6 alkyl, halogen substituted C1-C6 alkyl, n6 is selected from integers from 0 to 5; R 6 is selected from hydrogen, C1-C6 alkyl, R 7 is selected from C1-C6 alkyl, halogen substituted C1-C6 alkyl. Preferably, R 1、R4 is independently selected from cyano, C1-C3 alkyl, halo-substituted C1-C3 alkyl, R 2、R3 is independently selected from C1-C3 alkyl, R 6 is selected from hydrogen, C1-C3 alkyl, R 7 is selected from fluoro-substituted C1-C3 alkyl, C3-C8 cycloalkyl is selected from、、The substituted C3-C8 heterocycle is selected from the group consisting of a C1-C3 alkyl substituted C3-C8 heterocycle, an amino substituted C3-C8 heterocycle, and-N (CH 3）2 substituted C3-C8 heterocycle). Preferably, the structure of the sulfonamide compound is shown as a formula I-1: ; preferably Het is selected from 、、。 Preferably Ar is selected from、R 51、R52、R53、R54、R55 is independently selected from halogen, halogen substituted C1-C3 alkyl. Preferably Ar is selected from、、。 Preferably, n1, n2 are each independently selected from integers from 0 to 3. Preferably, R is selected from、R 1、R4 is independently selected from cyano, -CHF 2、-CF3. Preferably, R 2、R3 are both methyl. Preferably, the sulfonamide compound is selected from the following structures: 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、、 、、。 Preferably, the sulfonamide compound is selected from the following structures: 、、、 、、、 、、、 、、、 、、、 。 preferably, the pharmaceutically acceptable salt of the sulfonamide compound is prepared by reacting the sulfonamide compound with a pharmaceutically acceptable acid, wherein the pharmaceutically acceptable acid is an inorganic acid or an organic acid, the inorganic acid is at least one of hydrochloric acid, sulfuric acid, phosphoric acid and hydrobromic acid, and the organic acid is at least one of oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid and benzoic acid. In a second aspect, the present application provides a method for preparing the sulfonamide compound or the pharmaceutically acceptable salt thereof according to the first aspect of the present application, wherein the reaction formula for preparing the sulfonamide compound is as follows: ; Wherein X is halogen. Preferably, the reaction formula for preparing the sulfonamide compound is as follows: ; Wherein X is Cl. Preferably, the preparation of the sulfonamide compound comprises the steps of rea