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CN-122010867-A - L-carvone hydrazone derivative and application thereof

CN122010867ACN 122010867 ACN122010867 ACN 122010867ACN-122010867-A

Abstract

The invention discloses an L-carvone hydrazone derivative and application thereof. The L-carvone hydrazone derivative has the advantages of low raw material cost, simple synthetic route and the like, and the obtained L-carvone hydrazone product has excellent antibacterial effect on rhizoctonia solani, botrytis cinerea, sclerotinia sclerotiorum, gibberella wheat, apple rot germ and phytophthora capsici, and can be used for preventing and controlling various plant fungal diseases.

Inventors

  • ZHU YINGGUANG
  • CHEN KANG
  • CHEN HONGYI
  • ZHANG HONGLIN
  • Mai Ziyun
  • MIAO JINFENG

Assignees

  • 南京农业大学

Dates

Publication Date
20260512
Application Date
20241112

Claims (10)

  1. 1. An L-carvone hydrazone derivative shown in a formula (I) or a tautomer, a meso form, a racemate, an enantiomer, a diastereomer or a mixture thereof or a pharmaceutically acceptable salt thereof; Wherein A is selected from R 1、 R 2、 R 3 is independently selected from hydrogen, halogen, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 1 -C 6 alkoxy, hydroxy, said C 1 -C 6 alkyl, C 1 -C 6 alkoxy optionally substituted with one, two or three substituents selected from halogen, hydroxy or methoxy.
  2. 2. The L-carvone hydrazone derivatives of formula (I) according to claim 1 or a tautomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3 are independently selected from hydrogen, halogen, substituted or unsubstituted C1-C3 alkyl, substituted or unsubstituted C1-C3 alkoxy, hydroxy, said C1-C3 alkyl, C1-C3 alkoxy being optionally substituted by one, two or three halogens.
  3. 3. The L-carvone hydrazone derivatives of the formula (I) or a tautomer, mesomer, racemate, enantiomer, diastereomer or mixture thereof or a pharmaceutically acceptable salt thereof according to claim 2, R 1 is selected from hydrogen atom, halogen, trifluoromethyl, methyl, methoxy and hydroxyl, R 2 is selected from hydrogen atom, halogen, trifluoromethyl, methyl and methoxy, and R 3 is selected from hydrogen atom, halogen, trifluoromethyl, methyl, methoxy and tert-butyl.
  4. 4. The L-carvone hydrazone derivatives of the formula (I) or a tautomer, mesomer, racemate, enantiomer, diastereomer or mixture thereof or a pharmaceutically acceptable salt thereof according to claim 3, R 1 is selected from the group consisting of a hydrogen atom, 4-methyl, 2-fluoro, 4-trifluoromethyl, 4-fluoro, 4-chloro, 4-methoxy, 2-methoxy, 4-hydroxy; R 2 is selected from the group consisting of a hydrogen atom, 4-methyl, 2-methyl, 4-trifluoromethyl, 4-fluoro, 4-chloro, 4-methoxy, 2-methoxy, 4-bromo, 2-chloro, 3-methoxy, 3-methyl; R 3 is selected from the group consisting of a hydrogen atom, 4-methyl, 4-trifluoromethyl, 4-fluoro, 4-chloro, 4-methoxy, 4-bromo, 4-t-butyl, 2-methyl, 2-chloro, 2-fluoro, 3, 5-dimethyl, 3-chloro-4-fluoro, 3-chloro, 2, 4-dichloro, 3-methyl, 2-trifluoromethyl.
  5. 5. An L-carvone hydrazone derivative or a tautomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or a pharmaceutically acceptable salt thereof, as shown below:
  6. 6. a bactericide comprising the L-carvone hydrazone derivative according to any one of claims 1 to 5 or a tautomer, meso, racemate, enantiomer, diastereomer, or mixture thereof or a pharmaceutically acceptable salt thereof.
  7. 7. Use of the L-carvone hydrazone derivatives according to any one of claims 1 to 5 or a tautomer, mesomer, racemate, enantiomer, diastereomer or mixture thereof or a pharmaceutically acceptable salt thereof, or the bactericide according to claim 6 for controlling plant fungal diseases.
  8. 8. The use according to claim 7, wherein the fungal disease is sheath blight of rice, botrytis cinerea, gibberella wheat, sclerotinia sclerotiorum, phytophthora capsici or apple rot.
  9. 9. Use of the L-carvone hydrazone derivatives according to any one of claims 1 to 5 or a tautomer, mesomer, racemate, enantiomer, diastereomer or mixture thereof or a pharmaceutically acceptable salt thereof, or the fungicide according to claim 6 for the preparation of a medicament for controlling plant fungal diseases.
  10. 10. The use according to claim 9, wherein the fungal disease is sheath blight of rice, botrytis cinerea, gibberella wheat, sclerotinia sclerotiorum, phytophthora capsici or apple rot.

Description

L-carvone hydrazone derivative and application thereof Technical Field The invention relates to the field of pesticides, in particular to an L-carvone hydrazone derivative, and also relates to application of the derivative in preventing and controlling plant fungal diseases, and has application of a pesticide bactericide. Background The prevention and control inhibition of plant pathogens is an important field of pesticide science research, chemical prevention and control is still a main method for preventing epidemic outbreaks of plant pathogenic fungi in agriculture, and the wide use of bactericides enables a plurality of plant pathogens to be effectively controlled. However, as the use scale of bactericides continues to expand, plant pathogens have developed resistance to traditional bactericides. Meanwhile, the problems of high toxicity to non-target organisms and serious environmental pollution in the existing medicaments also cause great limitation in production application. Therefore, the development of the novel bactericide which has high efficiency, good target biospecificity and environmental friendliness has important effect and significance for guaranteeing the yield and stable yield of agriculture and grain safety. L-carvone is a natural product which is mainly existed in spearmint, also called spearmint oil, has a sweet and slightly cool smell similar to peppermint, and is often applied to the fields of food, daily chemical addition, medicine and the like. By chemically modifying the active functional group of L-carvone, the bioactive compound with novel structure can be derived, and valuable exploration is provided for the creation of novel medicines. On the other hand, the L-carvone derivative has good medical activity, and has broad-spectrum sterilization effect, so that the L-carvone derivative is expected to be developed in the field of pesticide creation. In conclusion, the L-carvone compound has various biological activities and is expected to become an important novel pesticide lead compound. The carbonyl of L-carvone is chemically modified to prepare a series of novel compounds with high-efficiency broad-spectrum plant pathogenic fungi inhibition activity. Disclosure of Invention The invention aims to provide an L-carvone hydrazone derivative. The 2 nd object of the present invention is to provide the use of the above derivatives. In a first aspect, the present invention provides an L-carvone hydrazone derivative having a structure represented by general formula (I) or a tautomer, meso, racemate, enantiomer, diastereomer, or mixture thereof, or a pharmaceutically acceptable salt thereof; Wherein A is selected from R 1、R2、R3 is independently selected from hydrogen, halogen, substituted or unsubstituted C 1-C6 alkyl, substituted or unsubstituted C 1-C6 alkoxy, hydroxy, said C 1-C6 alkyl, C 1-C6 alkoxy optionally substituted with one, two or three substituents selected from halogen, hydroxy or methoxy. In a specific embodiment, the R1, R2, R3 are independently selected from hydrogen, halogen, substituted or unsubstituted C1-C3 alkyl, substituted or unsubstituted C1-C3 alkoxy, hydroxy, the C1-C3 alkyl, C1-C3 alkoxy optionally substituted with one, two or three halogens. In specific embodiments, R 1 is selected from the group consisting of hydrogen, halogen, trifluoromethyl, methyl, methoxy, hydroxy, R 2 is selected from the group consisting of hydrogen, halogen, trifluoromethyl, methyl, methoxy, R 3 is selected from the group consisting of hydrogen, halogen, trifluoromethyl, methyl, methoxy, t-butyl. In a more specific embodiment, R 1 is selected from the group consisting of a hydrogen atom, 4-methyl, 2-fluoro, 4-trifluoromethyl, 4-fluoro, 4-chloro, 4-methoxy, 2-methoxy, 4-hydroxy, R 2 is selected from the group consisting of a hydrogen atom, 4-methyl, 2-methyl, 4-trifluoromethyl, 4-fluoro, 4-chloro, 4-methoxy, 2-methoxy, 4-bromo, 2-chloro, 3-methoxy, 3-methyl, R 3 is selected from the group consisting of a hydrogen atom, 4-methyl, 4-trifluoromethyl, 4-fluoro, 4-chloro, 4-methoxy, 4-bromo, 4-t-butyl, 2-methyl, 2-chloro, 2-fluoro, 3, 5-dimethyl, 3-chloro-4-fluoro, 3-chloro, 2, 4-dichloro, 3-methyl, 2-trifluoromethyl. The invention also protects the L-carvone hydrazone derivatives shown below or tautomers, meso forms, racemates, enantiomers, diastereomers, or mixtures thereof or pharmaceutically acceptable salts thereof: In a second aspect, the invention provides a fungicide comprising an L-carvone hydrazone derivative as defined in any preceding claim or a tautomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or a pharmaceutically acceptable salt thereof. In a third aspect, the invention also provides a preparation method of the L-carvone hydrazone derivative (I), particularly when A in the L-carvone hydrazone derivative (I) isThe preparation method comprises the following steps of reacting carboxylic acid (II) with substituted phenylhydrazine in the presence of trieth