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CN-122010780-A - 2-Cyano-3-amino-3-substituted phenyl acrylate compound and application thereof in preventing and controlling crop fungal diseases

CN122010780ACN 122010780 ACN122010780 ACN 122010780ACN-122010780-A

Abstract

The invention discloses a 2-cyano-3-amino-3-substituted phenyl acrylate compound and application thereof in preventing and controlling crop fungal diseases, and belongs to the field of pesticides. The structural formula of the 2-cyano-3-amino-3-substituted phenyl acrylate compound is shown as a formula (I), and the compound has good broad-spectrum bactericidal activity, especially against plant fungal diseases caused by pyriform, rhizoctonia, fusarium, acaschersonia, anthrax, cercospora, verticillium, black rot, alternaria, helminthosporium, rhizoctonia, helminthosporium, botrytis, puccinia, coralloides and Cladosporium fungi. Therefore, the compound can be used for preparing bactericides in the fields of agriculture, gardening, industry and the like, and has the advantages of broad spectrum, high efficiency, low toxicity, environmental friendliness and the like.

Inventors

  • ZHANG FENG
  • GENG YIMING
  • XU SHU
  • CHEN YU
  • FENG XIU
  • LIU FEI
  • LIU SONGTAO
  • YU WEI
  • LI LINWEI
  • CHU XINYAN
  • JIA FANGYING
  • SONG GUOHONG
  • LI WANGYANG

Assignees

  • 南京农业大学三亚研究院
  • 江苏省中国科学院植物研究所

Dates

Publication Date
20260512
Application Date
20260130

Claims (10)

  1. 1. The 2-cyano-3-amino-3-substituted phenyl acrylate compound is characterized in that the structural formula of the 2-cyano-3-amino-3-substituted phenyl acrylate compound is shown as formula I: Wherein R 1 、R 2 is independently selected from H, a substituted or unsubstituted sulfonate or carboxylate group; Wherein R 1 、R 2 is not H at the same time; Wherein the substituents are independently selected from C 1 – C 10 alkyl, C 3 – C 8 cycloalkyl, C 1 – C 8 haloalkyl, C 1 – C 8 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl.
  2. 2. The 2-cyano-3-amino-3-substituted phenylacrylate compound according to claim 1, wherein said substituents are independently selected from C 1 – C 8 alkyl, C 3 – C 8 cycloalkyl, C 1 – C 8 haloalkyl, C 1 – C 4 alkylamino, 5 to 14 membered heteroaryl, halogenated 5 to 14 membered heteroaryl, 6 to 10 membered aryl or halogenated 6 to 10 membered aryl.
  3. 3. The 2-cyano-3-amino-3-substituted phenyl acrylate compound of claim 1, wherein said group R 1 、R 2 comprises two of: in the case ①, R 2 is H; r 1 is a sulfonate group or a carboxylate group; Wherein the sulfonate and carboxylate groups are optionally substituted with one or more substituents independently selected from C 1 – C 8 alkyl, C 3 – C 8 cycloalkyl, C 1 – C 8 haloalkyl, C 1 – C 4 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl; In the case ②, R 1 is H; r 2 is a sulfonate group or a carboxylate group; Wherein the sulfonate and carboxylate groups are optionally substituted with one or more substituents independently selected from C 1 – C 8 alkyl, C 3 – C 8 cycloalkyl, C 1 – C 8 haloalkyl, C 1 – C 4 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl.
  4. 4. The 2-cyano-3-amino-3-substituted phenyl acrylate compound of claim 1, wherein said group R 1 、R 2 comprises two of: in the case ①, R 2 is H; r 1 is a sulfonate group or a carboxylate group; Wherein the sulfonate and carboxylate groups are optionally substituted with one or more substituents independently selected from C 1 – C 8 alkyl, C 3 – C 8 cycloalkyl, C 1 – C 8 haloalkyl, C 1 – C 4 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl, preferably the substituents are independently selected from C 1 – C 8 alkyl, C 3 – C 4 cycloalkyl, C 1 – C 8 haloalkyl, C 1 – C 2 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl, further preferably the substituents are independently selected from C 1 – C 8 alkyl, C 3 – C 4 cycloalkyl, C 1 – C 3 haloalkyl, C 1 – C 2 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl; In the case ②, R 1 is H; r 2 is a sulfonate group or a carboxylate group; Wherein the sulfonate and carboxylate groups are optionally substituted with one or more substituents independently selected from C 1 – C 8 alkyl, C 3 – C 8 cycloalkyl, C 1 – C 8 haloalkyl, C 1 – C 4 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl, preferably the substituents are independently selected from C 1 – C 8 alkyl, C 3 – C 4 cycloalkyl, C 1 – C 8 haloalkyl, C 1 – C 2 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl, further preferably the substituents are independently selected from C 1 – C 8 alkyl, C 3 – C 4 cycloalkyl, C 1 – C 3 haloalkyl, C 1 – C 2 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl.
  5. 5. The 2-cyano-3-amino-3-substituted phenyl acrylate compound according to claim 1, wherein the 2-cyano-3-amino-3-substituted phenyl acrylate compound is selected from at least one of the following structural formula: 。
  6. 6. A pesticidal formulation comprising 0.001% to 99.99% by weight of the 2-cyano-3-amino-3-substituted phenyl acrylate compound of claim 1.
  7. 7. A pesticide formulation according to claim 6, wherein the formulation of the pesticide formulation is any one of a suspension, a dispersible oil suspension, a dispersible liquid, a suspended seed coating, a tablet, a microemulsion, a water aqua, an emulsion, an emulsifiable concentrate, an aqueous suspension, a powder, a wettable powder, a soluble liquid, a granule, a soluble granule, a water dispersible granule, a capsule, a microcapsule suspension or a nano-formulation.
  8. 8. The use of a 2-cyano-3-amino-3-substituted phenyl acrylate compound according to any one of claims 1 to 5 or a pesticide preparation according to claim 6 for controlling fungal diseases of crops.
  9. 9. The use according to claim 8, wherein the crop fungal disease is a disease caused by any one or more of the genus pyriform, the genus chloromyces, the genus fusarium, the genus apotheca, the genus anthrax, the genus cercospora, the genus verticillium, the genus black rot, the genus alternaria, the genus megabase, the genus rhizoctonia, the genus moeba, the genus botrytis, the genus puccinia, the genus corallosporium and the genus clavuliform, preferably a disease caused by any one or more of the genus pyriform, the genus green core, the genus fusarium, the genus apotheca, the genus anthrax, the genus cercospora, the genus verticillium, the genus black rot, the genus alternaria, the genus megabase, the genus rhizoctonia, the genus momyces, the genus botrytis, the genus clavuliform or the genus panus, most preferably a disease caused by any one or more of the genus pyriform, the genus puccinia, the genus momyces, the genus momyceliophthora, the genus momyces and the genus clavuliform; And/or the number of the groups of groups, The disease is any one or more diseases of rice blast, false smut, wheat scab, rice bakanae disease, banana vascular wilt, wheat stem rot, wheat take-all, strawberry anthracnose, apple anthracnose, grape anthracnose, osmanthus fragrans anthracnose, citrus anthracnose, rubber tree anthracnose, corn anthracnose, soybean anthracnose, onion anthracnose, chilli anthracnose, medlar anthracnose, mango anthracnose, camellia anthracnose, yam anthracnose, peanut brown spot, cotton verticillium, apple tree rot, tomato early blight, summer spot blight, wheat sheath blight, corn leaf spot, gray mold or cucumber target spot, preferably any one or more diseases of rice blast, tomato early blight, wheat sheath blight, corn leaf spot, gray mold, soybean rust, corn leaf rust, wheat stripe rust or cucumber target spot.
  10. 10. The use according to claim 8, wherein the application amount of the 2-cyano-3-amino-3-substituted phenyl acrylate compound is 1-1000 g per hectare.

Description

2-Cyano-3-amino-3-substituted phenyl acrylate compound and application thereof in preventing and controlling crop fungal diseases Technical Field The invention belongs to the field of pesticides, and particularly relates to a 2-cyano-3-amino-3-substituted phenyl acrylate compound and application thereof in preventing and controlling crop fungal diseases. Background The acrylic ester compound has better bioactivity and ecological safety, and is applied to the fields of medicines and pesticides to a certain extent. For example, the 2-cyanoacrylate bactericide of the variety cyanogen alkene fungus esters can effectively prevent and treat diseases such as wheat scab, bakanae disease of rice and the like. However, the fenhexamid is the only variety of the current cyanoacrylate bactericide on the market, has very narrow bactericidal spectrum, has no control effect on important fungal diseases such as anthracnose, rice blast, false smut, gray mold and the like which are seriously harmful to agriculture, seriously influences the large-scale application of the bactericide on the control of agricultural diseases, and seriously influences the economic value of the bactericide. The development of acrylic acid ester bactericides is slow in recent years, and the main development is still limited to improving the control effect of the cyanogen mycoester for controlling target wheat scab, and no report of expanding the control spectrum is seen. How to expand the prevention spectrum of the acrylic bactericide and improve the application value of the acrylic bactericide is a hot spot for the current development of the pesticide. Patent document CN1160318C discloses a 2-cyano-3-substituted phenyl acrylic ester compound shown in the following general formula (A), and the compound has an effect of preventing various diseases caused by Fusarium such as wheat scab. Patent document CN101381326a discloses a class of 2-cyano 3- (substituted) amino-3-phenyl acrylate compounds shown in the following general formula (B), and the compounds have control effect on fusarium. Patent document CN109879834A discloses a 3-amino-2-cyano-3-amino-3-substituted phenyl acrylic ester compound shown in the following general formula (C), and the Mannich base bactericide has good prevention and control effects on Fusarium. Patent document CN109879841B discloses a class of (Z) -3-imino-1-propenol compounds represented by the following general formula (D), which have a control effect on wheat scab causing plant diseases and can reduce the production of wheat gibberellin (DON). Patent document CN109867623A discloses a 3-pyridyl 3-amino-2-cyanoacrylate compound shown in the following general formula (E), which has control effect on wheat scab. Patent document CN 114790152A discloses a class of 2-cyanoacrylate compounds represented by the following general formula (F), which have a control effect on fusarium fungi. Patent document CN 119431188A discloses a 2-cyano-3-disubstituted phenyl acrylate compound shown in the following general formula (G), which has control effect on various diseases caused by Rhizoctonia, fusarium, acremonium, anthrax, cercospora and Verticillium and black rot. 。 Disclosure of Invention The invention aims to provide a 2-cyano-3-amino-3-substituted phenyl acrylate compound to solve the problems of narrow control spectrum and poor sterilization effect of the existing acrylate bactericides. The second technical problem to be solved by the invention is to provide a preparation method of the 2-cyano-3-amino-3-substituted phenyl acrylate compound. The third technical problem to be solved by the invention is to provide the application of the 2-cyano-3-amino-3-substituted phenyl acrylate compound in preventing and controlling crop fungal diseases. In order to solve the technical problems, the invention adopts the following technical proposal: The invention discloses a 2-cyano-3-amino-3-substituted phenyl acrylic ester compound, wherein the structural formula of the 2-cyano-3-amino-3-substituted phenyl acrylic ester compound is shown as formula I: ; Wherein R 1、R2 is independently selected from H, a substituted or unsubstituted sulfonate or carboxylate group; Wherein R 1、R2 is not H at the same time; Wherein the substituents are independently selected from C 1– C10 alkyl, C 3 – C8 cycloalkyl, C 1– C8 haloalkyl, C 1– C8 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl. As a preferred embodiment, the 2-cyano-3-amino-3-substituted phenyl acrylate compound is preferably at least one of the following structural formulas (II) - (V): ; Wherein R 3、R4、R5、R6 is independently selected from C 1– C10 alkyl, C 3 – C8 cycloalkyl, C 1– C8 haloalkyl, C 1– C8 alkylamino, 5-to 14-membered heteroaryl, halo 5-to 14-membered heteroaryl, 6-to 10-membered aryl, or halo 6-to 10-membered aryl. In some embodiments, the substituents are independently selected from C 1– C8 alkyl, C 3 – C8 cy