WO2022001047A1 - Dérivé de quinoléine phénol ou sel à activité pesticide acceptable de celui-ci, composition et utilisation associée - Google Patents

Dérivé de quinoléine phénol ou sel à activité pesticide acceptable de celui-ci, composition et utilisation associée Download PDF

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WO2022001047A1
WO2022001047A1 PCT/CN2020/140687 CN2020140687W WO2022001047A1 WO 2022001047 A1 WO2022001047 A1 WO 2022001047A1 CN 2020140687 W CN2020140687 W CN 2020140687W WO 2022001047 A1 WO2022001047 A1 WO 2022001047A1
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alkyl
halogenated
alkoxy
alkenyl
formula
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PCT/CN2020/140687
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English (en)
Chinese (zh)
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葛家成
杨春河
邢阳阳
刘明东
孙鹏
胡亚卓
胡堂路
李丽
马娥
白光耀
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海利尔药业集团股份有限公司
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Publication of WO2022001047A1 publication Critical patent/WO2022001047A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the invention belongs to the technical field of pesticides, in particular to a quinoline phenol derivative or its acceptable salts and compositions as pesticides, and to the use of these compounds or their acceptable salts and compositions as pesticides as fungicides.
  • the present invention provides a quinoline phenol derivative or its salt acceptable as a pesticide, a composition and its use.
  • quinoline phenol derivatives especially 2,3-dimethyl-6-tert-butyl-8-fluoro-4-hydroxyquinoline derivatives or salts acceptable as pesticides are not only effective against rice Blast has excellent biological activity, has satisfactory control activity against other control objects except rice blast, and has excellent safety to crops.
  • R 1 represents H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 1 -C 6 alkoxy or halogenated C 1 -C 6 alkoxy;
  • R 2 represents H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 1 -C 6 alkoxy or halogenated C 1 -C 6 alkoxy;
  • R 1 and R 2 together form a group -(CH 2 ) t -, where t represents an integer from 2 to 8;
  • R 3 , R 4 , R 5 are independently selected from H, halogen, CN, nitro, aldehyde, carboxyl, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, halo C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, phenyl or phenyl-substituted C 1- C 6 alkyl;
  • X represents halogen, CN, nitro, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy or C 3 -C 6 ring Alkyl, m represents an integer of 0-3.
  • R 1 represents H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogenated C 1 -C 6 alkoxy base;
  • R 2 represents H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogenated C 1 -C 6 alkoxy;
  • R 1 and R 2 together form a group -(CH 2 ) t -, where t represents an integer from 2 to 7;
  • R 3 and R 4 are independently selected from H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, halogenated C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, halogenated C 1 -C 6 alkoxy or C 3 -C 6 cycloalkyl;
  • R 5 is selected from H, halogen, CN, nitro, aldehyde, carboxyl, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, halogenated C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, phenyl or benzyl;
  • X represents halogen, CN, nitro, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy or C 3 -C 6 ring Alkyl, m represents an integer of 1-3;
  • R 3 and R 4 are both Me or Et, X is 6-t-Bu, and m is 1.
  • R 1 and R 2 together form a group -(CH 2 ) t -, and t represents an integer of 2-5.
  • R 3 and R 4 are the same and selected from H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, halogenated C 2 -C 6 alkenyl, C 1 -C 6 alkoxy or C 3 -C 6 cycloalkyl; preferably, R 3 and R 4 are the same, selected from H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH 2 Cl, CHCl 2, CCl 3, CH 2 F, CHF 2, CF 3, CH 2 Br, CHBr 2, CBr 3, OMe, OEt, vinyl, cyclopropane.
  • R 1 and R 2 together form a group -(CH 2 ) t -, and t represents an integer of 2-5;
  • R 3 and R 4 are independently selected from H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt, vinyl, cyclopropane ;
  • R 5 is selected from H, F, Cl, Br, CN, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH 2 Cl, CHCl 2, CCl 3, CH 2 F, CHF 2 , CF 3, CH 2 Br, CHBr 2, CBr 3, CH 2 CF 3, CH 2 CH 2 Cl, vinyl, OMe, OEt, n-PrO , i-PrO, n- BuO, i-BuO, s-BuO, t-BuO, cyclopropanyl, cyclopropanyloxy, nitro, aldehyde, carboxyl, hydroxyl;
  • X represents H, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt, vinyl, cyclopropane, m is 1 or 2.
  • R 1 and R 2 together form a group -(CH 2 ) t -, and t represents an integer of 3-4;
  • R 3 and R 4 are both Me or Et
  • R 5 is selected from H, F, Cl, Br, CN, Me, Et, n-Pr, i-Pr, CH 2 Cl, CHCl 2 , CCl 3 , CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CH 2 CH 2 Cl, vinyl, OMe, OEt, nitro;
  • X represents a tert-butyl group, and m is 1.
  • the pesticide-acceptable salt can be the salt obtained by reacting the quinoline phenol derivatives of the present invention with a chemically acceptable acid, wherein the chemically acceptable acid can be an inorganic acid (such as hydrochloric acid, sulfuric acid, Phosphoric acid or hydrobromic acid, etc.) or organic acid (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzoic acid, etc.); the acceptable salt of the pesticide can also be the quinoline of the present invention
  • the salt obtained by reacting phenolic derivatives with a chemically acceptable base wherein the chemically acceptable base can be an inorganic base (such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate) or organic bases (such as trimethylamine, triethylamine, etc.).
  • the pesticide acceptable salt can be potassium salt, sodium salt, ammonium salt, calcium salt, pyridinium salt or choline salt.
  • the present invention also discloses a bactericidal composition, comprising a bactericidal effective amount of at least one of the above-mentioned quinoline phenol derivatives or salts acceptable as pesticides; further, a formulation carrier or formulation aid agent.
  • the present invention also discloses a method for controlling plant diseases, comprising adding a biologically effective amount of the above-mentioned quinoline phenol derivatives or at least one of the salts acceptable as pesticides or the above-mentioned bactericidal composition applied to plants.
  • the present invention also discloses the use of the above-mentioned quinoline phenol derivatives or at least one of the pesticide-acceptable salts thereof or the above-mentioned fungicidal composition in controlling plant diseases; preferably, the plant The disease is bacterial disease or fungal disease.
  • Halogen or halogen refers to fluorine, chlorine, bromine, iodine.
  • C 1 -C 6 alkyl a straight or branched chain alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl or tert-butyl.
  • Halogenated C 1 -C 6 alkyl groups straight or branched chain alkyl groups with 1 to 6 carbon atoms, the hydrogen atoms on these alkyl groups may be partially or completely substituted by halogens, for example, chloromethyl, dichloromethane Chloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.
  • C 2 -C 6 alkenyl straight-chain or branched alkenyl having 2 to 6 carbon atoms, such as vinyl, propenyl, and the like.
  • Halogenated C 2 -C 6 alkenyl straight-chain or branched alkenyl with 2 to 6 carbon atoms, and the hydrogen atoms on these alkenyl groups may be partially or completely substituted by halogen, for example, vinyl chloride and the like.
  • C 1 -C 6 alkoxy a straight or branched chain alkyl group with 1 to 6 carbon atoms connected to the structure through an oxygen atom bond.
  • Halogenated C1-C6 alkoxy straight-chain or branched alkoxy with 1-6 carbon atoms, the hydrogen atoms on these alkoxy groups may be partially or completely substituted by halogen, for example, chloromethoxy , dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.
  • the synthesis method of the compound of formula I specifically, the compound of formula III and the compound of formula II (in the following chemical formulae, unless otherwise defined, the substituents and symbols are the same as those defined in formula I. Meaning)
  • the target product compound of formula I is obtained after the reaction is carried out in the presence or absence of a basic reagent and in the presence or absence of a solvent.
  • the compounds represented by formula II and III can be obtained commercially, or can be obtained by referring to the method described in EP407192A:
  • the solvent is selected from acetonitrile, N,N-dimethylformamide, NN-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, dichloromethane, benzene, toluene, xylene, dichloroethane, acetic acid a mixture of one or more solvents in ethyl esters;
  • reaction can be carried out under normal pressure or high pressure, preferably under atmospheric pressure, and post-treatment can be carried out according to conventional methods.
  • the compounds of formula I of the present invention or their acceptable salts and compositions as pesticides are respectively suitable as fungicides, especially suitable as fungicides or bactericides with significant efficacy, some of which are systemically effective and can be used as foliar Fungicides, fungicides for seed dressing and soil fungicides are used in crop protection. Furthermore, they are suitable for controlling harmful fungi which occur in particular on wood or plant roots, in particular by treating the fungi or bacteria with an effective amount of at least one compound of formula I as defined in the invention or a salt, composition which is acceptable as a pesticide, or Materials, plants, soil or seeds to be protected from fungal or bacterial attack.
  • the compound I of the present invention or its salts and compositions acceptable as pesticides are suitable for use on various cultivated plants such as cereals, such as wheat, rye, barley, triticale, oats or rice; sugar beets, such as sugar beets or fodder beets ; Fruits, such as pomes, stone fruits or berries, such as apples, pears, plums, peaches, almonds, cherries, strawberries or blueberries; Legumes, such as lentils, peas, alfalfa or soybeans; Oil plants, such as canola, mustard, olives , sunflower, coconut, cocoa beans, castor oil plants, oil palm, peanuts or soybeans; cucurbits such as pumpkin, cucumber or melon; fibrous plants such as cotton, flax or jute; citrus fruits such as oranges, lemons, Grapefruit or oranges; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, gourds or bell peppers; laurels such as avocado
  • compound I or its salts and compositions acceptable as pesticides are used in field crops, such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybean, rape, bean Control of fungal or bacterial diseases on plants, sunflowers, coffee or sugar cane; fruits; ornamental plants or vegetables such as cucumbers, tomatoes, beans or squash.
  • field crops such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybean, rape, bean Control of fungal or bacterial diseases on plants, sunflowers, coffee or sugar cane; fruits; ornamental plants or vegetables such as cucumbers, tomatoes, beans or squash.
  • the present invention also provides fungicidal compositions comprising compounds of formula I.
  • the compounds of formula I can be formulated in a variety of ways depending on the usual biological and/or chemical and/or physical parameters. Examples of suitable formulation choices are: wettable powder (WP), wettable liquid (SL), soluble powder (SP), dispersible liquid (DC), aqueous (AS), microemulsion (ME), emulsifiable concentrate ( EC), Emulsion in Water (EW), Sprayable Solution, Suspension (SC), Dispersible Oil Suspension (OD), Powder (DP), Microcapsule Suspension (CS), Water Dispersible Granules (WG), Water Soluble Granules (SG), Large Granules (GG), Granules (GR) for broadcasting and soil application, Aerosol (AE), Ultra Low Volume (ULV) and Waxes. Necessary formulation auxiliaries, such as inert substances, surfactants, solvents and other additives.
  • WP wettable powder
  • suitable additives are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners , humectants, repellents, attractants, food stimulants, compatibilizers, antifreeze agents, defoamers, colorants, tackifiers and adhesives.
  • Suitable solvents and liquid carriers are water and/or organic solvents, such as medium to high boiling mineral oil fractions, such as kerosene, diesel; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, such as toluene, Paraffins, tetralin, alkylated naphthalenes; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; dimethyl sulfoxide (DMSO); ketones, such as cyclohexanone; Esters, such as lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof .
  • medium to high boiling mineral oil fractions such as kerosene, diesel
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • Suitable solid carriers or fillers are mineral earths such as silicates, silica gel, talc, kaolin, limestone, lime, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides , such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of vegetable origin, such as grain flour, bark flour, wood flour, and nutshell flour, and mixtures thereof.
  • mineral earths such as silicates, silica gel, talc, kaolin, limestone, lime, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides such as cellulose, starch
  • fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea
  • Suitable surfactants are surface-active substances such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof; such surfactants can be used as emulsifiers, dispersants, Solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants.
  • Suitable adjuvants are compounds which have negligible or even no pesticidal activity themselves and improve the biological properties of compound I on the target; examples are surfactants, mineral or vegetable oils and other adjuvants.
  • Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates and the like.
  • Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol, among others.
  • Suitable antifoaming agents are polysiloxanes, long chain alcohols and fatty acid salts and the like.
  • Suitable colorants are low water-soluble pigments and water-soluble dyes, which may be inorganic colorants (such as iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (such as Alizarin colorants, azo colorants and phthalocyanine colorants).
  • inorganic colorants such as iron oxide, titanium oxide, iron hexacyanoferrate
  • organic colorants such as Alizarin colorants, azo colorants and phthalocyanine colorants.
  • suitable active substances that can be mixed with the active substances of the present invention are, for example, known substances in "World New Pesticide Variety Technology Encyclopedia” (China Agricultural Science and Technology Press, 2010.9).
  • the fungicidal active substances mentioned below can be mixed with the mixture of formula I, (note: the name of the compound, or the common name according to the International Organization for Standardization (ISO), or the chemical name, with a designation where appropriate): nitrile pyrimidine Azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxystrobin (flufenoxystrobin), fluoxastrobin, kresoxim-methyl, metminostrobin, orysastrobin, picoxystrobin, pyraclostrobin ( pyraclostrobin), pyrametostrobin, pyraoxystrobin, trifloxystrobin
  • the pyrazole structure is introduced, and the obtained quinoline phenol derivatives or their use as pesticides
  • the acceptable salt not only has excellent biological activity against rice blast, but also has satisfactory control activity against other control objects except rice blast, and has excellent safety to crops.
  • Powder Weigh 20% of the compound of formula (I), mix 80% of kaolin clay uniformly, and pulverize to obtain the product.
  • Wettable powder Weigh 20% of the compound of formula (I), 8% of calcium lignosulfonate, 2% of sodium dodecyl sulfate, 3% of white carbon black, and kaolin and added to 100%. Mix evenly, and get the product after jet pulverization.
  • Water-dispersible granules weigh 60% of the compound of formula (I), 6% of sodium lignosulfonate, 4% of NNO (alkylnaphthalene sulfonate formaldehyde condensate), 2% of pull-open powder BX (dibutyl) sodium naphthalene sulfonate), 3% K-12 (sodium dodecyl sulfate), 5% carboxymethyl (ethyl) cellulose, 5% diatomaceous earth, 5% glucose, kaolin were added to 100%. Mix evenly, after jet pulverization, weigh the powder, add water to mix, granulate in a granulator, then dry and sieve to obtain a granular product.
  • Suspending agent weigh 15% of the compound of formula (I), 4% FS3000 (phosphate ester type anionic surfactant), 2% NS-500LQ (non-ionic hydroxypolyethylene oxide block copolymer), 0.2% xanthan gum, 1% magnesium aluminum silicate, 5% ethylene glycol, 0.1% BIT (1,2-benzisothiazolin-3-one), 0.3% organo-modified siloxane defoamer, Deionized water was added to 100% to make a slurry, and the product was obtained after sanding.
  • the host crop is rice (Ludao No. 1), and the specific operations are as follows:
  • a certain mass of compound samples were weighed, dissolved in acetone, and prepared into a mother solution for later use.
  • compound samples and control agents were prepared into a series of concentration gradient liquids with 0.1% Tween 80 water for in vivo screening.
  • Select potted rice seedlings with three leaves and one heart and consistent growth, and arrange them in order after marking for experimental use.
  • the type of sprayer is spray tower, spray 30ml liquid medicine for each treatment, and let it dry naturally. After 24h, the pathogenic bacteria were inoculated, and a blank control was set.
  • test materials were moved into a humidification box (room) or an artificial climate chamber.
  • the relative humidity was > 95%, and the temperature was 26-28°C, and cultivated under dark conditions. After 24 hours, they were moved in. 12h light-dark alternation, light intensity greater than 20000lx incubator (room) or greenhouse high-humidity culture, 5 to 7 days later, depending on the incidence of the blank control to conduct a graded investigation.
  • control effect is less than 50%
  • the host crop is rice (Shannong 13).
  • the specific operations are as follows:
  • a certain mass of compound samples were weighed, dissolved in acetone, and prepared into a mother solution for later use.
  • compound samples and control agents were prepared into a series of concentration gradient liquids with 0.1% Tween 80 water for in vivo screening.
  • Select potted rice seedlings with three leaves and one heart and consistent growth, and arrange them in order after marking for experimental use.
  • the type of sprayer is spray tower, spray 30ml liquid medicine for each treatment, and let it dry naturally. After 24h, the pathogenic bacteria were inoculated, and blank control and other drug control were set.
  • control effect is less than 50%
  • the host crop is cucumber (Jinyou No. 1), and the potted seedling method is adopted.
  • the specific operations are as follows:
  • a certain mass of compound samples were weighed, dissolved in acetone, and prepared into a mother solution for later use.
  • compound samples and control agents were prepared into a series of concentration gradient liquids with 0.1% Tween 80 water for in vivo screening.
  • the 2-4 leaf stage potted cucumber seedlings with uniform growth were selected as the experimental host plants for cucumber powdery mildew.
  • the type of sprayer is spray tower, spray 30ml liquid medicine for each treatment, and let it dry naturally. After 24h, the pathogenic bacteria were inoculated, and blank control and other drug control were set.
  • the fresh spores of powdery mildew produced on the leaves of diseased cucumbers within 24 hours were made into a suspension (concentration of 1 ⁇ 10 5 spores/mL), sprayed on the inoculated leaves, and cultivated under suitable conditions. After 7 to 10 days, the clear water control completely developed the disease, and the test results were investigated.
  • control effect is between 50-79%
  • control effect is less than 50%
  • Table 5 shows the protective test results of melon powdery mildew.
  • the compounds of the present invention can be used as fungicides for controlling plant diseases, especially for rice, wheat and/or melons.

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Abstract

La présente invention relève du domaine des pesticides, et concerne en particulier un dérivé de quinoléine phénol ou un sel à activité pesticide acceptable de celui-ci, une composition et une utilisation associée, le composé ayant la structure de formule (I). La définition de chaque groupe dans la formule (I) est telle que définie dans la description. Le composé ayant une structure de quinoléine phénol selon la présente invention a une activité biologique plus élevée que les composés connus, peut détruire de manière efficace les bactéries et présente une sécurité suffisante pour les cultures, et ne génère pas facilement de résistance.
PCT/CN2020/140687 2020-07-01 2020-12-29 Dérivé de quinoléine phénol ou sel à activité pesticide acceptable de celui-ci, composition et utilisation associée WO2022001047A1 (fr)

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CN202010621034.8 2020-07-01
CN202010621034.8A CN113880840A (zh) 2020-07-01 2020-07-01 一种喹啉酚类衍生物或其作为农药可接受的盐、组合物及其用途

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CN115872999A (zh) * 2022-06-20 2023-03-31 江苏吉贝尔药业股份有限公司 一种噻唑烷酸类衍生物或其药学上可接受的盐、组合物及其用途

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