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CN-119841817-B - Aromatic ester compound containing benzo five-membered ring, and preparation method and application thereof

CN119841817BCN 119841817 BCN119841817 BCN 119841817BCN-119841817-B

Abstract

The invention provides an aromatic ester compound containing benzo five-membered ring, a preparation method and application thereof, in particular to a compound shown in a formula (I) or pharmaceutically acceptable salt thereof and application thereof in preparing bactericides in the agronomic field or the gardening field, The compound represented by the formula (I) exhibits excellent biological activity against various pathogens in the agronomic or horticultural fields and can achieve excellent effects at a low dose.

Inventors

  • TANG JIANFENG
  • CHI HUIWEI
  • CHEN XUECHENG
  • ZHANG DONGDONG
  • HAN JUN
  • TENG WENWEN
  • GAO YUEHENG
  • CHEN YUSHI

Assignees

  • 山东省联合农药工业有限公司

Dates

Publication Date
20260512
Application Date
20241217

Claims (8)

  1. 1. Aromatic ester compounds containing benzo five-membered ring or pharmaceutically acceptable salts thereof shown in the following formula (I), formula (II) or formula (III), (I) (II) (III) 。
  2. 2. A process for producing a aromatic ester compound having a benzo five-membered ring represented by the formula (I) in claim 1 or a pharmaceutically acceptable salt thereof, wherein the process comprises: Method (1) Reacting a compound shown in a formula (V) with a compound shown in a formula (IV) to obtain a compound shown in a formula (I); Wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 , A, W, X, Y have the definition as defined in claim 1.
  3. 3. The use of the aromatic ester compound containing a benzo five-membered ring or a pharmaceutically acceptable salt thereof according to claim 1 in the preparation of a bactericide.
  4. 4. Use according to claim 3, wherein the fungicide is used in the agronomic or horticultural field.
  5. 5. A composition comprising at least one of the aromatic ester compound containing a benzo five-membered ring or the pharmaceutically acceptable salt thereof according to claim 1 as an active ingredient.
  6. 6. Use of the composition of claim 5 as a fungicide in the agronomic or horticultural field.
  7. 7. A method for controlling pathogens or diseases in the agronomic or horticultural fields, wherein the method comprises applying an effective amount of at least one of the aromatic ester compound containing a benzo five-membered ring according to claim 1 or a pharmaceutically acceptable salt thereof or the composition according to claim 5 to a growth medium for pathogens or diseases.
  8. 8. The method according to claim 7, wherein the aromatic ester compound containing a benzo five-membered ring or a pharmaceutically acceptable salt thereof according to claim 1 or the composition according to claim 5 is used for controlling Pyricularia oryzae, rhizoctonia solani, botrytis cinerea, rhizoctonia solani, alternaria tricornata, fusarium xanthophyllum, citrus resina, fusarium solani, sclerotinia sclerotiorum, fusarium pseudograminearum, verticillium zeae, solanum tuberosum, rhizoctonia cerealis or a corresponding disease.

Description

Aromatic ester compound containing benzo five-membered ring, and preparation method and application thereof Technical Field The invention belongs to the technical field of agricultural or horticultural bactericides, and particularly relates to an aromatic ester compound containing a benzo five-membered ring, a preparation method and application thereof. Background In the agricultural field, along with the popularization of straw returning and no-tillage technologies, plant residues are insufficiently treated in production, and a large number of plant pathogenic bacteria remain in soil due to the fact that a large number of pathogens pass through the plant body for overwintering and over-summer. In addition, as the problem of disease resistance becomes more serious, farmers need to increase the dosage, but this causes an increase in drug residues, which causes pollution and burden to the environment. Therefore, there is a need to develop new agricultural chemicals with high effectiveness. Patent document WO2016039459 discloses aromatic ester compounds CK 1 (compound number 82) and CK 2 (compound number 291) as follows: Patent document JP2016056100 discloses an aromatic ester compound CK 3 (compound number 105) as follows: Patent document JP2016056117 discloses an aromatic ester compound CK 4 (compound number 49) as follows: However, the biological activity of the above compounds is still to be further improved. The inventors have conducted intensive studies in order to find a bactericide which is more excellent in performance. Disclosure of Invention In order to solve the technical problems, the invention provides aromatic ester compounds containing benzo five-membered rings shown in the following formula (I) or pharmaceutically acceptable salts thereof, Wherein R 1 is selected from hydrogen, C 1-C6 alkyl, C 3-C6 cycloalkyl, C 3-C6 cycloalkyl C 1-C6 alkyl or NR ARB; R A or R B are identical or different and are selected independently of one another from hydrogen, C 1-C6 alkyl, C 3-C6 cycloalkyl, C 3-C6 cycloalkyl C 1-C6 alkyl or COOC 1-C6 alkyl; R 2 is selected from hydrogen or C 1-C6 alkyl; Or R 1 and R 2 are joined together to form R 3 is selected from hydrogen or C 1-C6 alkyl; R 4、R5, which are identical or different, are independently of one another selected from hydrogen, cyano, hydroxy, C 1-C6 alkyl, C 1-C6 alkoxy, C 1-C6 haloalkyl, C 1-C6 haloalkoxy or NHR 8; r 8 is selected from hydrogen or C 1-C6 alkyl; A is selected from phenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, naphthyl, triazinyl, pyrrolyl, thienyl, thiazolyl, isothiazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl or benzoC 3-C6 cycloalkyl; W is selected from O, S (O) n、CH2, C (=o) or NR 9; n is selected from 0, 1 or 2; R 9 is selected from hydrogen or C 1-C6 alkyl; X, Y are identical or different and are independently selected from CH 2, O, S or Se, wherein X, Y are not simultaneously CH 2 and when one of X or Y is selected from CH 2, the other is selected from Se; R 6、R7, which are identical or different, are independently of one another selected from hydrogen, halogen, hydroxy, cyano, amino, C 1-C6 alkyl, C 1-C6 alkoxy, C 1-C6 haloalkyl, C 1-C6 haloalkoxy, or R 6、R7 together with the carbon atoms to which they are attached form C=O or C=S; with the proviso that the compound of formula I is not According to an embodiment of the invention, R 1 is selected from hydrogen, C 1-C4 alkyl,Or NR ARB; R A or R B are identical or different and are selected independently of one another from hydrogen, C 1-C4 alkyl, Or COOC 1-C4 alkyl; R 2 is selected from hydrogen or C 1-C4 alkyl; Or R 1 and R 2 are joined together to form R 3 is selected from hydrogen or C 1-C4 alkyl; R 4、R5, which are identical or different, are independently of one another selected from hydrogen, cyano, hydroxy, C 1-C4 alkyl, C 1-C4 alkoxy, C 1-C4 haloalkyl, C 1-C4 haloalkoxy or NHR 8; r 8 is selected from hydrogen or C 1-C4 alkyl; A is selected from phenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, naphthyl, triazinyl, pyrrolyl, thienyl, thiazolyl, isothiazolyl, triazolyl, tetrazolyl or isoxazolyl; W is selected from O, S, CH 2 or NR 9; R 9 is selected from hydrogen or C 1-C4 alkyl; X, Y, identical or different, are independently selected from O or S; R 6、R7, which are identical or different, are independently of one another selected from hydrogen, fluorine, chlorine, bromine, hydroxyl, cyano, amino, C 1-C4 alkyl, C 1-C4 alkoxy, C 1-C4 haloalkyl, C 1-C4 haloalkoxy, or R 6、R7 together with the carbon atoms to which they are attached form a C=O or C=S group. According to an embodiment of the invention, R 1 is selected from hydrogen, methyl, ethyl,Amino or NHCOOC (CH 3)3; According to an embodiment of the invention, R 2、R3, identical or different, are selected independently of one another from hydrogen, methyl or ethyl; Or R 1 and R 2 are joined together to form According to an embodiment of the invention, R 4、R5, identical or different, are independently of each other