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CN-122010788-A - Hydrazinoformate compound, and preparation method and application thereof

CN122010788ACN 122010788 ACN122010788 ACN 122010788ACN-122010788-A

Abstract

The application relates to a hydrazino formate compound, a preparation method and application thereof, wherein the hydrazino formate compound is a compound shown in a formula (I), or an isotopically-labeled compound, or an optical isomer, a geometric isomer, a tautomer or an isomer mixture, or a pharmaceutically acceptable salt thereof. The hydrazinoformate compound provided by the application has broad-spectrum antibacterial activity on plant pathogenic bacteria such as pathogenic fungi, and particularly has excellent antibacterial activity on tobacco red star pathogenic bacteria, cabbage black spot pathogenic bacteria, tomato early blight pathogenic bacteria, apple anthracnose pathogenic bacteria, corn curvularia pathogenic bacteria, wheat red fungus pathogenic bacteria, watermelon wilt pathogenic bacteria, potato dry rot pathogenic bacteria, rice blast pathogenic bacteria, pumpkin wilt pathogenic bacteria, cotton wilt pathogenic bacteria, apple ring rot pathogenic bacteria, apple rot pathogenic bacteria, grape downy mildew pathogenic bacteria, melon powdery mildew pathogenic bacteria and the like. (I)

Inventors

  • ZHOU BOHANG
  • ZHOU LE
  • WANG YIWEI

Assignees

  • 陕西省生物农业研究所

Dates

Publication Date
20260512
Application Date
20260324

Claims (10)

  1. 1. A hydrazinoformate compound which is a compound of formula (I), or an isotopically-labeled compound thereof, or an optical isomer, a geometric isomer, a tautomer or a mixture of isomers, or a pharmaceutically acceptable salt thereof, (I) Wherein, the Each R 1 is independently selected from halogen; Each R 2 is independently selected from halogen, methyl, trifluoromethyl or trifluoromethoxy; X is selected from bond 、—CH 2 —、—CH 2 CH 2 —、—CH 2 CH 2 CH 2 —、—CH 2 OCH 2 CH 2 —、—CH 2 CH 2 CH 2 CH 2 — or-OCH 2 CH 2 OCH 2 CH 2 -, and N and m are each independently selected from any integer from 0 to 5, Further, wherein R 2 is not 3-trifluoromethyl and R 1 and R 2 are not all Cl and when X is selected from the group consisting of a bond, -CH 2 -, or-CH 2 CH 2 -, n and m are not all 0.
  2. 2. The hydrazinoformate compound according to claim 1, wherein the halogen is selected from fluorine, chlorine, bromine or iodine.
  3. 3. The hydrazinoformate compound according to claim 1, wherein n is 1, r 1 is selected from 4-fluoro, 4-chloro, 4-bromo or 4-iodo.
  4. 4. The hydrazinoformate compound of claim 1 wherein m is 1, R 2 is selected from 2-fluoro, 3-fluoro, 4-fluoro, 3-chloro, 4-chloro, 3-bromo, 4-iodo, 3-methyl, 4-trifluoromethyl or 4-trifluoromethoxy, or m is 2, R 2 is selected from 2, 4-difluoro, 3, 5-difluoro, 2-fluoro-3-chloro, 2-fluoro-4-chloro or 4-fluoro-3-chloro.
  5. 5. The hydrazinoformate compound according to claim 1, wherein X is selected from —CH 2 CH 2 CH 2 —、—CH 2 OCH 2 CH 2 —、—CH 2 CH 2 CH 2 CH 2 — or-OCH 2 CH 2 OCH 2 CH 2 -.
  6. 6. The process for preparing a hydrazinoformate compound according to any one of claims 1 to 5, comprising the steps of condensing a compound of formula (II) with a compound of formula (III), or a corresponding hydrochloride, sulfate or acetate thereof, to obtain a compound of formula (I); (II) (III)。
  7. 7. a fungicidal composition comprising at least one of the hydrazinoformate compounds according to any one of claims 1 to 5 as an active ingredient, and optionally a pesticidally acceptable carrier and/or adjuvant.
  8. 8. Use of the hydrazinoformate compound according to any one of claims 1 to 5 or the fungicidal composition according to claim 7 for controlling plant diseases caused by phytopathogens.
  9. 9. Use according to claim 8, wherein the phytopathogen is a phytopathogen fungus, preferably selected from the group consisting of phylum plasmodiophoromycota, oomycota, phylum chytrium, zygomycota, ascomycota, basidiomycota or deuteromycota.
  10. 10. The use according to claim 9, wherein the plant pathogen is selected from the group consisting of alternaria alternata, alternaria solani, alternaria alternate, alternaria wheat, watermelon fusarium, potato, rice blast, pumpkin fusarium, cotton fusarium, apple ring rot, apple rot, downy mildew or melon powdery mildew.

Description

Hydrazinoformate compound, and preparation method and application thereof Technical Field The application relates to the technical field of plant antibacterial agents, in particular to a hydrazinoformate compound, a preparation method and application thereof. Background Plant pathogenic fungi are one of the main biological disasters affecting the stable and high yield of food in the world. In the growing and storage stages of the field, the superposition of fungal diseases can lead to 25 percent of yield reduction of main grain crops35, And produces mycotoxin pollution, further reducing commodity value and market competitiveness of agricultural products. Although measures such as agricultural control, disease-resistant breeding and biological agents are continuously popularized, the chemical bactericide has irreplaceable status in comprehensive disease treatment due to the characteristics of quick response, low cost, convenient use and the like. It is counted that the reasonable use of the bactericide can restore about 15% of the grain yield worldwide each year, and has important effects on guaranteeing the grain supply and stabilizing the income of peasants. Since the 60 s of the 20 th century, nearly 200 active components of bactericides are commercially applied, a multi-class and multi-variety product system is formed, and important support is provided for modern agricultural production. However, long-term high-frequency use causes the decline of the prevention effect of part of traditional germicides, the rise of the risk of re-infection in the field, and the demand of agricultural production for efficient, safe and long-lasting substitute medicines is increasingly urgent. Therefore, the novel bactericide which has good environmental compatibility and low risk to non-target organisms is developed, and has important significance for guaranteeing sustainable development of agriculture and grain safety. Disclosure of Invention For the sake of brevity, the "compound of formula (N) (e.g., compound of formula (I)" described hereinafter may also encompass any optical isomer, geometric isomer, tautomer or mixture of isomers, or agriculturally acceptable salt of the compound of formula (N). The term "optical isomer" means that when a compound has one or more chiral centers, each chiral center may exist in either the R or S configuration, and thus the various isomers constituted are optical isomers. Optical isomers include all diastereoisomers, enantiomers, meso, racemates or mixtures thereof. For example, the optical isomers may be separated by chiral chromatography columns or by chiral synthesis. The term "geometric isomer" means that when a double bond is present in a compound, the compound may exist as cis, trans, E and Z isomers. Geometric isomers include cis, trans, E, Z, or mixtures thereof. The term "tautomer" refers to an isomer that results from the rapid movement of an atom in a molecule at two positions. Those skilled in the art will appreciate that tautomers may be transformed into each other and may exist in an equilibrium state in a certain state. Unless otherwise indicated, references herein to "a compound of formula (N) (e.g., a compound of formula (I)" also encompass isotopically-labeled compounds in which any one of the atoms of the compound is replaced by an isotopic atom thereof. That is, the present invention includes all agriculturally acceptable isotopically-labeled compounds of formula (N) wherein one or more atoms are replaced by an atom having the same atomic number but a different atomic mass or mass number as found in nature. Examples of isotopes suitable for inclusion in compounds of the invention include isotopes of hydrogen, such as 2 H (D) and 3 H (T), isotopes of carbon, such as 11C、13 C and 14 C, isotopes of chlorine, such as 37 Cl, isotopes of fluorine, such as 18 F, isotopes of iodine, such as 123 I and 125 I, isotopes of oxygen, such as 15O、17 O and 18 O. Isotopically-labeled compounds of formula (N) can generally be prepared by conventional techniques known to those skilled in the art or by using an appropriate isotopically-labeled reagent in place of the non-labeled reagent previously used, in a manner analogous to those described in the examples and preparations attached herein. The compounds of formula (N) may be present in the form of agriculturally acceptable salts, for example, acid addition salts and/or base addition salts of the compounds of formula (N). As used herein, unless otherwise indicated, "agriculturally acceptable salts" include acid addition salts or base addition salts that may occur within the compounds of formula (N). Agriculturally acceptable salts of the compound of formula (N) include acid addition salts and base addition salts thereof. Suitable acid addition salts are formed from acids that form non-toxic salts. Examples include, but are not limited to, acetates, adipates, aspartate, benzoate, benzenesulfonate, bicarbonate/carbonate, bisulfate/sulfa