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WO2020169046A1 - Utilisation d'un composé de 1,1-dicyanohydrazone comme bactéricide agricole - Google Patents

Utilisation d'un composé de 1,1-dicyanohydrazone comme bactéricide agricole Download PDF

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Publication number
WO2020169046A1
WO2020169046A1 PCT/CN2020/075806 CN2020075806W WO2020169046A1 WO 2020169046 A1 WO2020169046 A1 WO 2020169046A1 CN 2020075806 W CN2020075806 W CN 2020075806W WO 2020169046 A1 WO2020169046 A1 WO 2020169046A1
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Prior art keywords
acid
compound
general formula
alkyl
halogenated
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PCT/CN2020/075806
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English (en)
Chinese (zh)
Inventor
张立新
张静
张力群
康卓
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沈阳化工大学
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Publication of WO2020169046A1 publication Critical patent/WO2020169046A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines

Definitions

  • the present invention belongs to the field of agricultural bactericides, and specifically relates to the application of a 1,1-dicyanohydrazone compound as an agricultural bactericide.
  • Bacterial diseases have become the second most common disease in my country’s agricultural production after fungal diseases. According to incomplete statistics, the area of bacterial diseases currently occurring in my country is 120 million mu, and the market capacity of bacterial disease prevention and control exceeds 20. 100 million yuan.
  • agents for the prevention and control of bacterial diseases mainly include relatively large amounts of copper preparations (including organic or inorganic copper preparations) and antibiotic products; among them, copper preparations have low control effect and a large amount of heavy metals are sprayed into the environment. Pollution of soil, water and food has caused environmental and food safety concerns.
  • the large-scale use of antibiotics may cause human pathogens to become resistant to medical antibiotics.
  • the purpose of the present invention is to provide a 1,1-dicyanohydrazone compound represented by general formula I for controlling plant bacterial diseases in agriculture or forestry.
  • W is selected from one of the groups represented by W 1 -W 3 :
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 and X 19 are each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1- C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1 -C 6 Dialkylamino, C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkoxycarbonyl;
  • G is selected from hydrogen, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, cyano C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkyl Carbonyl or C 1 -C 6 alkoxycarbonyl;
  • W is selected from one of the groups represented by W 1 -W 3 ;
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 and X 19 are each independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxy, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 1- C 4 alkoxy, halogenated C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogenated C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, C 1 -C 4 Dialkylamino, C 1 -C 4 alkylcarbonyl or C 1 -C 4 alkoxycarbonyl;
  • G is selected from hydrogen, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, cyano C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl, C 3 -C 6 cycloalkyl Carbonyl or C 1 -C 4 alkoxycarbonyl;
  • compound of general formula I and hydrochloric acid hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, apple Salts of acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid or citric acid.
  • W is selected from one of the groups represented by W 1 -W 3 ;
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 and X 19 are each independently selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, hydroxyl, mercapto, amino, carboxy, methyl, ethyl, n-propyl, isopropyl, n-butyl , Isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoro Methyl, trifluoromethyl, 2,2,2-trifluoroethyl, heptaflu
  • G is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, Monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, cyanomethyl , Acetyl, n-propionyl, cyclopropylformyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl or n-butoxycarbonyl;
  • compound of general formula I and hydrochloric acid hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, apple Salts of acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid or citric acid.
  • W is selected from one of the groups represented by W 1 -W 3 ;
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 and X 19 are each independently selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, carboxy, methyl, ethyl, tert-butyl, trifluoromethyl, methoxy, trifluoromethoxy Group, methoxycarbonyl or ethoxycarbonyl;
  • G is selected from hydrogen, methyl, ethyl, acetyl, cyclopropylformyl, methoxycarbonyl or ethoxycarbonyl;
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • Alkyl straight or branched chain alkyl, such as methyl, ethyl, n-propyl, isopropyl or different butyl, pentyl or hexyl isomers.
  • Halogenated alkyl groups straight or branched chain alkyl groups.
  • the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogens, such as monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, and dichloromethyl.
  • Cyanoalkyl straight-chain or branched-chain alkyl.
  • the hydrogen atoms on these alkyl groups can be partially or completely replaced by cyano groups, such as cyanomethyl (CNCH 2 -), cyanoethyl (CNCH 2 CH 2 -) ), CNCH 2 CH 2 CH 2 -, CNCH 2 CH 2 CH 2 CH 2 -etc.
  • Alkoxy straight or branched chain alkyl, connected to the structure via oxygen atom bond, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, etc. .
  • Halogenated alkoxy groups straight or branched chain alkoxy groups, the hydrogen atoms on these alkoxy groups can be partially or completely replaced by halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluorine Methoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, 2,2,2-trifluoroethoxy, etc.
  • halogen such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluorine Methoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, 2,2,2-trifluoroethoxy, etc.
  • Alkylthio straight or branched chain alkyl, connected to the structure via a sulfur atom bond, such as methylthio, ethylthio and the like.
  • Halogenated alkylthio linear or branched alkylthio, the hydrogen atoms on these alkylthio groups can be partially or completely replaced by halogen, such as difluoromethylthio, trifluoromethylthio, 2,2,2- Trifluoroethylthio and so on.
  • Alkylamino straight or branched chain alkyl, connected to the structure via a nitrogen atom bond, such as methylamino, ethylamino, n-propylamino, isopropylamino or isomeric butylamine.
  • Dialkylamino Two identical or different linear or branched alkyl groups are connected to the structure via a nitrogen atom bond, such as N,N-dimethylamino, N-methyl-N-ethylamino, etc.
  • Alkylcarbonyl The alkyl group is connected to the structure via the carbonyl group, such as acetyl (CH 3 CO-), n-propionyl (CH 3 CH 2 CO-) and so on.
  • Cycloalkylcarbonyl A cycloalkyl is attached to the structure via a carbonyl group, such as cyclopropylformyl.
  • Alkoxycarbonyl alkyl-O-CO-, such as methoxycarbonyl (CH 3 OCO-), ethoxycarbonyl (CH 3 CH 2 OCO-), n-propoxycarbonyl (CH 3 CH 2 CH 2 OCO-), n-butoxycarbonyl (CH 3 CH 2 CH 2 CH 2 OCO-), etc.
  • the compound of general formula I when G is a hydrogen atom, the compound of general formula I has the following tautomers, and the compound of general formula I also includes, in this case, all tautomers.
  • G Numbering G Numbering G Numbering G Numbering G Numbering G Numbering G 8.1 H 8.2 CH 3 8.3 CH 2 CH 3 8.4 CH 2 CH 2 CH 3 8.5 CH 2 CH 2 CH 2 CH 3 8.6 2,2,2-Trifluoroethyl 8.7 Acetyl 8.8 Cyclopropylformyl 8.9 Methoxycarbonyl 8.10 Ethoxycarbonyl 8.11 N-propoxycarbonyl 8.12 N-Butoxycarbonyl
  • the compound of general formula I of the present invention can be prepared according to the following method (each group in the formula is defined as before unless otherwise specified):
  • the compound of the general formula II can be prepared by the conventional diazotization reaction to produce the corresponding diazonium salt product, that is, the compound of the general formula III.
  • the compound of general formula III can be reacted with malononitrile in the presence of a suitable base in a suitable solvent at a temperature from -10°C to the boiling point of the solvent for 0.5-48 hours to prepare a compound of general formula I-1.
  • Suitable base can be sodium acetate, potassium acetate, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or tertiary Sodium butoxide and so on.
  • Suitable solvent can be water, dichloromethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, methanol, ethanol, ethyl acetate, acetonitrile, dioxane, THF, DMF, DMSO or a mixture of the above solvents Solvent.
  • the compound of the general formula I-1 and the compound of the general formula G-LG can be reacted in a suitable solvent in an alkali-free or alkali-free environment at a temperature from -10°C to the boiling point of the solvent for 0.5-48 hours to obtain the general formula I -2 compounds.
  • Suitable base can be sodium acetate, potassium acetate, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or tertiary Sodium butoxide and so on.
  • Suitable solvent can be water, dichloromethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, methanol, ethanol, ethyl acetate, acetonitrile, dioxane, THF, DMF, DMSO or a mixture of the above solvents Solvent.
  • LG represents a leaving group
  • a suitable leaving group can be halogen or other conventional nucleating groups, such as C 1 -C 4 alkoxy or C 1 -C 4 alkyl sulfide Group, specifically, methoxy, ethoxy, methylthio or ethylthio.
  • the compound of general formula II, the compound of general formula G-LG and other raw materials and reagents are usually commercially available, and they can also be made by conventional methods.
  • the compounds of the present invention can also be prepared according to the methods disclosed in US3755598A, US3660462A, US3202698, US3157569, US3062635, JP07206800A, WO9735863A1, US4115104A, JP48087020A, JP48087019A, US3213124, US3135736 or European Journal of Biochemistry, 33(2), 247-52; 1973, etc. , Or refer to other known methods.
  • the compound represented by the general formula I of the present invention is used to control plant bacterial diseases, and can be used to prevent and control a variety of plant bacterial diseases, such as fruit spot (such as melon fruit spot, etc.), leaf spot (such as tomato bacteria) Leaf spot disease, etc.), bacterial wilt (such as tomato bacterial wilt, potato bacterial wilt, etc.), bacterial blight, canker disease (such as citrus canker, kiwi fruit canker, etc.), soft rot (such as soft Chinese cabbage) Rot, etc.), bacterial angular leaf spot (such as cucumber bacterial angular leaf spot, etc.), bacterial leaf streak (such as rice bacterial leaf spot, etc.), leaf blight, bacterial leaf blight (such as rice white leaf Blight, etc.), wildfire and bacterial scab.
  • plant bacterial diseases such as fruit spot (such as melon fruit spot, etc.), leaf spot (such as tomato bacteria) Leaf spot disease, etc.), bacterial wilt (such
  • the compounds represented by the general formula I of the present invention can be prepared separately, which are further specifically described as follows:
  • Example 10 Determination of the control effect on plant bacterial diseases
  • the compound of the present invention has been used to determine the prevention effect of various plant bacterial diseases.
  • the test procedure is as follows:
  • melon fruit spot disease For melon fruit spot disease, dissolve the test compound with a small amount of N,N dimethylformamide and dilute with water to the required concentration.
  • the pathogenic bacteria cultivated to the stable growth stage are mixed with the quantitative compound solution uniformly, the melon seeds that have been germinated are soaked in the mixture of the bacterial solution and the compound for half an hour, and then the seeds are sown in the earthworm soil culture cup and placed in the greenhouse Medium moisturizing culture, usually cultured for two weeks, after the control has fully developed the disease, the control effect will be investigated.
  • the compound is sprayed on the surface of the plant test material, and after the surface drug solution is air-dried in a cool place, the pathogenic bacteria liquid cultured to a stable growth stage is sprayed on the surface of the plant test material, and then the plant test material is placed in a greenhouse for moisturizing culture. Usually cultured for about ten days, after the control is fully onset, the control effect investigation is carried out.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne l'utilisation d'un composé de 1,1-dicyanohydrazone tel que représenté dans la formule générale (I) en tant que bactéricide agricole. La définition de chaque substituant dans la formule est décrite dans la description. Le composé de formule générale (I) présente une excellente activité bactéricide et peut être utilisé pour lutter contre diverses maladies bactériennes des plantes.
PCT/CN2020/075806 2019-02-22 2020-02-19 Utilisation d'un composé de 1,1-dicyanohydrazone comme bactéricide agricole WO2020169046A1 (fr)

Applications Claiming Priority (4)

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CN201910134161.2 2019-02-22
CN201910134161 2019-02-22
CN201910133130.5 2019-02-22
CN201910133130 2019-02-22

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3062635A (en) * 1958-07-18 1962-11-06 Du Pont Method for inhibiting plant and fungal growth
US3157569A (en) * 1962-11-08 1964-11-17 American Cyanamid Co Method of controlling insects with cyanide hydrazones
US3660462A (en) * 1968-12-12 1972-05-02 Bayer Ag N-acyl-dicyanocarbonyl-phenyl-hydrazones
JPS4887020A (fr) * 1972-02-26 1973-11-16
US4115104A (en) * 1977-02-14 1978-09-19 Monsanto Company Dicyanovinylhydrazonomalononitriles and the herbicidal use thereof
WO1997035863A1 (fr) * 1996-03-22 1997-10-02 Hoechst Schering Agrevo Gmbh Methylidene-hydrazino-phenylsulfonyl-urees disubstituees, leur procede de production et leur utilisation comme herbicides et comme regulateurs de la croissance des plantes
WO1999039575A2 (fr) * 1998-02-09 1999-08-12 Yissum Research Development Company Of The Hebrew University Of Jerusalem Activite biocide synergique de complexes de biocides charges negativement (constituant a), d'ions de metal de transition (constituant b) et de chelateurs neutres (constituant c)
CN101302217A (zh) * 2008-07-02 2008-11-12 南开大学 三唑类化合物及其制备与应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755600A (en) * 1969-12-09 1973-08-28 Bayer Ag N acyl dicyanocarbonyl phenyl hydrazones as arthropodicides and fungicides
US3755598A (en) * 1970-02-24 1973-08-28 Monsanto Co Mosquito control agents

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3062635A (en) * 1958-07-18 1962-11-06 Du Pont Method for inhibiting plant and fungal growth
US3157569A (en) * 1962-11-08 1964-11-17 American Cyanamid Co Method of controlling insects with cyanide hydrazones
US3660462A (en) * 1968-12-12 1972-05-02 Bayer Ag N-acyl-dicyanocarbonyl-phenyl-hydrazones
JPS4887020A (fr) * 1972-02-26 1973-11-16
US4115104A (en) * 1977-02-14 1978-09-19 Monsanto Company Dicyanovinylhydrazonomalononitriles and the herbicidal use thereof
WO1997035863A1 (fr) * 1996-03-22 1997-10-02 Hoechst Schering Agrevo Gmbh Methylidene-hydrazino-phenylsulfonyl-urees disubstituees, leur procede de production et leur utilisation comme herbicides et comme regulateurs de la croissance des plantes
WO1999039575A2 (fr) * 1998-02-09 1999-08-12 Yissum Research Development Company Of The Hebrew University Of Jerusalem Activite biocide synergique de complexes de biocides charges negativement (constituant a), d'ions de metal de transition (constituant b) et de chelateurs neutres (constituant c)
CN101302217A (zh) * 2008-07-02 2008-11-12 南开大学 三唑类化合物及其制备与应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DEVAPRIYA SINHA, STUTI PANDEY, RAJA SINGH, VINOD TIWARI, KIRTI SAD, VIBHA TANDON: "Synergistic efficacy of Bisbenzimidazole and Carbonyl Cyanide 3-Chlorophenylhydrazone combination against MDR bacterial strains", SCIENTIFIC REPORTS, vol. 7, 44419, 17 March 2017 (2017-03-17), pages 1 - 14, XP055729519, ISSN: 2045-2322, DOI: 10.1038/srep44419 *

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