WO2014036952A1 - Composé pyridazinone et utilisation associée - Google Patents

Composé pyridazinone et utilisation associée Download PDF

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WO2014036952A1
WO2014036952A1 PCT/CN2013/082984 CN2013082984W WO2014036952A1 WO 2014036952 A1 WO2014036952 A1 WO 2014036952A1 CN 2013082984 W CN2013082984 W CN 2013082984W WO 2014036952 A1 WO2014036952 A1 WO 2014036952A1
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compound
group
alkyl
cucumber
alkyloxy
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PCT/CN2013/082984
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English (en)
Chinese (zh)
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徐玉芳
赵振江
李宝聚
钱旭红
朱维平
石延霞
韩景龙
李洪林
曹贤文
常康
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华东理工大学
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines

Definitions

  • the present invention relates to a pyridazinone compound and use thereof. Background technique
  • Pesticides are mainly used to prevent various diseases (pests, mites, nematodes, pathogens, weeds and rodents) and to regulate plant growth in the production of agriculture, forestry and animal husbandry.
  • pesticides were mainly used for "killing" of harmful substances, but since the 1980s, the concept of pesticides has changed a lot.
  • Today, we don't pay attention to "killing", but we are more focused on regulation. Therefore, the purpose of modern pesticides is to effectively control pests, non-target organisms and environmental safety. China is a big agricultural country. Since the liberation, China's pesticide industry has flourished, and the variety and output of pesticides have doubled.
  • China's pesticide production has been able to meet the needs of agriculture, and there are a certain number of exports, but the varieties are still insufficient.
  • China uses 65 to 700,000 tons of pesticides per year, and the amount of active ingredients is 22 to 250,000 tons. There are very few harmful organisms that can be prevented. About 90% of the pesticides are lost in the farmland, especially the highly toxic pesticides pollute the environment.
  • Pesticides have a long history of development in the world for about 150 years.
  • the scientific research, development and production of chemical pesticides were unprecedentedly active, and new types of pesticides with high efficiency, low toxicity and novel mechanism of action, such as pyrethroids, pyridinium Azole, pyridine, nicotine, pyrrole, benzoylurea insecticide; carbamate, ⁇ -methoxy acrylate, benzimidazole, triazole fungicide; imidazolinone Classes, sulfonylurea herbicides, etc. emerge in an endless stream, prompting chemical pesticides to enter the fast-growing fast lane.
  • TMV disease resistance gene encoding protein
  • SA systemic acguired resistance
  • a plant disease activator refers to a substance that has no direct bactericidal activity to the compound itself and its metabolites, but which stimulates the immune system of the plant and the plant produces a system that acquires disease resistance.
  • This resistance has four characteristics, namely: systemic, SAR is expressed in the non-inducing factor treatment site of the plant; persistence, which can last for weeks or even months after SAR production; broad-spectrum, SAR simultaneously for several fungi, bacteria Inhibition of diseases caused by pathogens; Safety, these inducers do not produce a toxic effect on the pathogens, but induce the plant to produce resistance, so there is no side effect on the environment. Therefore, the research and development of such fungicides has broad application prospects.
  • Pyridazines are a class of heterocyclic compounds with high activity such as herbicidal, insecticidal and acaricidal, and plant growth regulation. Many varieties also have low toxicity and low residue.
  • pyridazine derivatives have become an important class of aromatic heterocyclic compounds, and pyridazinone compounds are an important class of pyridazine derivatives.
  • 4-hydroxypyridazinone has a strong inhibitory effect on plant cell division and is used as a plant growth regulator in agricultural production.
  • Pyridazinone pesticides have high activity and environmental friendliness. They play an important role in the integrated pest control and reduce the environmental pollution of pesticides.
  • the research on the resistance of plant systems has started late in China.
  • the research on the mechanism of plant-induced disease resistance mainly focuses on the transmission mechanism of disease resistance signals, physiological and biochemical mechanisms and the cloning and application of related disease resistance genes, while new plants
  • the development of disease resistance activators is relatively slow. Only a few plant disease activators have been successfully developed so far, among which NCI, BTH, TDL and other commercially successful plant disease resistance activators can induce plants to produce broad-spectrum resistance to bacteria, fungi and viruses ( Michiko Yasuda., J. Pestic. Sci. 2004, 29: 46-49).
  • the present inventors have designed and synthesized a series of pyridazinone compounds, namely compounds of formula I, using computer drug design, medicinal chemistry and molecular biology methods and techniques, and these compounds inhibit agricultural and horticultural and forest pathogenic fungi.
  • each is independently selected from the group consisting of: hydrogen, C1-C6 fluorenyl, C1-C6 decyloxy, halogen, halogenated C1-C6 fluorenyl, halogenated C1-C6 decyloxy, nitro, amino, CN , NCO, NCS, carboxy, C1-C3 decyloxycarbonyl, C1-C3 amide;
  • X is selected from the group consisting of oxygen, sulfur and nitrogen; 16 is 11, optionally substituted C1-C3 fluorenyl and optionally substituted Phenyl substituted, 5-10 membered heteroaryl;
  • R 7 is optionally H, substituted C1-C3 fluorenyl and optionally substituted phenyl.
  • and 15 are each independently H, halo, halo C1-C6 fluorenyl, and halo C1-C6 decyloxy.
  • R 3 and R 4 are each independently H, halo, halo C1-C6 fluorenyl, and halo C1-C6 decyloxy.
  • it is selected from the group consisting of H, halogen, C1-C6 decyloxy, halo C1-C6 fluorenyl, nitro, halogenated C1-C6 decyloxy, and C1-C6 fluorenyl.
  • 16 is 11.
  • R 7 is H or a C1-C6 fluorenyl group.
  • X is zero.
  • R 2 , R 4 , R 5 and R 6 are H, and R 3 is selected from the group consisting of H, halogen, C1-C6 decyloxy, halo C1-C6 fluorenyl, nitro, halo Generation C1-C6 decyloxy and C1-C6 fluorenyl, X is 0.
  • R 3 , R 5 and R 6 are H, and R 2 and R 4 are selected from the group consisting of H, halogen and C1-C6-decyloxy, and X is 0.
  • RrR 5 is independently selected from the group consisting of hydrogen, C 1-C6 decyloxy, halogen, nitro and halogenated C1-C6 decyloxy.
  • RrR 5 is independently selected from the group consisting of hydrogen, C 1-C6 decyloxy, halogen, nitro and halogenated C1-C6 decyloxy.
  • the invention further relates to the use of a compound of formula I as a plant disease resistance activator.
  • the present invention relates to a compound of formula I and an agriculturally acceptable carrier or adjuvant for the preparation of a plant disease resistance activator, an anti-plant virus agent, an insecticide, a fungicide, a plant growth regulator and a weed control Use in the agent.
  • the compounds of formula I of the invention inhibit pathogenic fungi and induce plant disease resistance.
  • Plants which can be controlled by the compounds of formula I of the present invention include various agricultural plants, horticultural plants, and forestry plants including, but not limited to, cucumber, tomato, rice, and the like.
  • the plant diseases which can be controlled by the compound of the general formula I of the present invention include, but are not limited to, cucumber blight, cucumber brown spot, cucumber bacterial leaf spot, tomato late blight, rice stalk Disease, cucumber gray mold and cucumber wilt disease.
  • the plant diseases which can be controlled by the compound of the general formula I of the present invention are tomato late blight, cucumber brown spot, cucumber blight, and rice sheath blight.
  • the compound of the formula I of the present invention can be used to control the bacterium , Corynespora cassiicola, Pseudomonas syringae Cucumber horn 3 ⁇ 4E disease to the pathogenic type I Pseudomonas syringae pv.
  • the present invention also relates to the preparation of compounds of formula I.
  • the preparation method of the present invention comprises: using a substituted aniline (a compound of the formula A) as a starting material, adding hydrochloric acid and sodium nitrite to form a diazonium salt, and then adding the formed diazonium salt to 1,3 - An aqueous solution of dimethyl ketone dicarboxylate and sodium acetate in an aqueous solution of ethanol at room temperature (for example, 20 min) to obtain an intermediate benzoquinone (compound represented by formula B).
  • a substituted aniline a compound of the formula A
  • Intermediate B is heated under reflux in o-dichlorobenzene (for example, about 2 h) to obtain compound II; intermediate B is dissolved in aqueous sodium hydroxide solution (for example, 2 M aqueous sodium hydroxide solution), and concentrated hydrochloric acid is added dropwise to precipitate a solid.
  • aqueous sodium hydroxide solution for example, 2 M aqueous sodium hydroxide solution
  • mercapto includes both branched and straight chain fluorenyl groups, usually having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms.
  • Examples of mercapto groups include, but are not limited to, methyl, ethyl, propyl, butyl, t-butyl, isobutyl and the like.
  • Alkoxy means a "mercapto-O-" group, wherein the fluorenyl group may be a C1-C6 straight or branched fluorenyl group, preferably a C1-C4 straight or branched fluorenyl group.
  • the fluorenyl group in the fluorenyl group or the fluorenyloxy group may be optionally substituted with a halogen, a hydroxyl group or the like.
  • halodecyl or halodecyloxy include, but are not limited to, one or several? , (: 1 and / or Br-substituted C1 -C6 or C1-C6 alkyl with embankment group, specific examples such as trifluoromethyl, -O-CF 3 and the like.
  • Aryl means a monocyclic, bicyclic or tricyclic aromatic radical containing from 6 to 14 carbon atoms and includes phenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, fluorenyl, tetrahydronaphthyl, Hydrogenated fluorenyl and the like.
  • the aryl group may be optionally substituted with from 1 to 5 (for example, 1, 2, 3, 4 or 5) substituents selected from the group consisting of halogen, -4- aldehyde group, -6 straight chain or branched fluorenyl group, a cyano group, a nitro group, an amino group, a hydroxyl group, a hydroxymethyl group, a halogen-substituted fluorenyl group (for example, a trifluoromethyl group), a halogen-substituted decyloxy group (for example, a trifluoromethoxy group), a carboxyl group, a C 4 decyloxy group, Ethoxycarbonyl, N(CH 3 ) and C 4 acyl groups.
  • 1 to 5 for example, 1, 2, 3, 4 or 5
  • substituents selected from the group consisting of halogen, -4- aldehyde group, -6 straight chain or branched fluorenyl group, a
  • an aryl group may be substituted with from 1 to 5 groups selected from the group consisting of: halogen, -OH, d_4 methoxy, C 4 fluorenyl, -NO 2 , -NH 2 , -N(CH 3 ) 2 , Carboxyl group, and ethoxylated group.
  • heteroaryl means that the ring contains 5-10 atoms and 6, 10 or 14 electrons are shared on the ring system. Further, the ring atom contained is a carbon atom and optionally 1 - 3 hetero atoms from oxygen, nitrogen and sulfur.
  • Useful heteroaryl groups include thienyl, furyl, pyranyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, including but not limited to 2-pyridyl, 3-pyridyl and 4-pyridyl, pyridyl Azinyl, pyrimidinyl and the like.
  • the heteroaryl group may be optionally substituted by one to five (e.g., 1, 2, 3, 4 or 5) substituents selected from the group consisting of: halogen, d- 4 aldehyde group, d- 6 straight or branched fluorenyl group , cyano, nitro, amino, hydroxy, hydroxymethyl, halogen-substituted fluorenyl (eg trifluoromethyl), halogen-substituted oxirane (eg trifluoromethoxy), carboxyl, CM methoxy, Ethoxycarbonyl, N(CH 3 ) and CM acyl groups.
  • substituents selected from the group consisting of: halogen, d- 4 aldehyde group, d- 6 straight or branched fluorenyl group , cyano, nitro, amino, hydroxy, hydroxymethyl, halogen-substituted fluorenyl (eg trifluoromethyl), halogen-substi
  • the aryl group may further contain other substituents as described above, such as Cl, Br, -OH, d_ 4 decyloxy, d_ 4 fluorenyl Chain, -NO 2 , -NH 2 , -N(CH 3 ) 2 , carboxyl group, and ethoxylated group.
  • the invention also includes a pesticidal composition comprising a compound of the invention.
  • the pesticidal composition of the present invention further comprises a pesticidally acceptable carrier. And a carrier acceptable for pesticides.
  • composition may contain 0.01% to 95% by weight of the compound of the formula I or hydrazine of the present invention as an active ingredient.
  • the agrochemically acceptable carrier includes a variety of solid carriers, liquid carriers, gas carriers, and the like, which are known in the art.
  • the solid carrier can be, for example, fine powder or granules of clay materials such as kaolin, diatomaceous earth, synthetic hydrated silica, bentonite, Fubasami clay and acid clay; various types of talc, ceramics and other inorganic materials such as sericite, quartz, sulfur Fine powder or granules of activated carbon, calcium carbonate and hydrated silica; and fine powder or granules of chemical fertilizers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride.
  • clay materials such as kaolin, diatomaceous earth, synthetic hydrated silica, bentonite, Fubasami clay and acid clay
  • various types of talc, ceramics and other inorganic materials such as sericite, quartz, sulfur Fine powder or granules of activated
  • the liquid carrier may include, for example, water; alcohols such as methanol and ethanol; ketones such as acetone and methyl ethyl ketone; hydrocarbons such as hexamethylene, cyclohexanthene, kerosene and light oil; esters such as ethyl acetate and butyl acetate Esters; nitriles such as acetonitrile and isobutyronitrile; ethers such as diisopropyl ether and dioxins; amides such as N, N-dimethylformamide and N, N-dimethylacetamide; halogenated hydrocarbons Such as methylene chloride, trichloroacetic acid and carbon tetrachloride; dimethyl sulfoxide; and vegetable oils such as soybean oil and cottonseed oil.
  • alcohols such as methanol and ethanol
  • ketones such as acetone and methyl ethyl ketone
  • hydrocarbons such as he
  • the gas carrier or propellant may include, for example, Freon gas, Tween gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide.
  • the pesticide composition of the present invention may further contain a surfactant such as a mercaptosulfate, a mercaptosulfonate, a mercaptoarylsulfonate, a mercaptoaryl ether, and a polyepoxyquinone derivative thereof, Polyglycol ethers, polyol esters and sugar alcohol derivatives.
  • a surfactant such as a mercaptosulfate, a mercaptosulfonate, a mercaptoarylsulfonate, a mercaptoaryl ether, and a polyepoxyquinone derivative thereof, Polyglycol ethers, polyol esters and sugar alcohol derivatives.
  • the pesticidal composition of the present invention may further contain an adjuvant such as a fixing agent or a dispersing agent, for example, casein, gelatin, polysaccharides (such as starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, bentonite, and sugar.
  • an adjuvant such as a fixing agent or a dispersing agent, for example, casein, gelatin, polysaccharides (such as starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, bentonite, and sugar.
  • synthetic water-soluble polymers such as polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acid.
  • the pesticidal composition of the present invention may also include stabilizers such as PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids and esters thereof.
  • stabilizers such as PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol
  • PAP isopropyl acid phosphate
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • BHA 2-tert- a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol
  • vegetable oils mineral oils
  • the agricultural pharmaceutical composition of the present invention can be prepared by mixing various components in the agricultural chemical composition of the present invention with each other.
  • the agricultural chemical composition of the present invention thus formulated can be used as it is or after being diluted with water.
  • This can be mixed with other insecticides, nematicides, acaricides, fungicides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners and/or animal feeds. Or don't mix it but use it at the same time.
  • the present invention also encompasses a method of controlling crop diseases, including, for example, spraying a crop, applying a root of a crop in the soil, and the like.
  • an appropriate application amount and concentration can be set according to the conditions including the type, the number of times, the place and the application method, the type of pest, and the degree of damage.
  • Example 1 The invention is further illustrated by the following examples, which are intended to illustrate and not to limit the scope of the invention.
  • Example 1 is
  • reaction liquid A Take 870 mg of dimethyl 1,3-acetone dicarboxylate and 3 g of sodium acetate in a 100 mL eggplant-shaped flask, add 10 mL of water and 3 mL of ethanol, and stir magnetically at room temperature to obtain a reaction solution 8.
  • the reaction solution A was slowly added dropwise to the reaction liquid B, and a yellow precipitate was precipitated. After 10 min, the reaction was completed, suction filtration, water washing, and drying.
  • the crude product was purified by silica gel column chromatography (EtOAc /EtOAcEtOAc
  • Example 6 The conditions and procedures were the same as in Example 1 except that aniline was used instead of p-fluoroaniline in Example 1.
  • Compound D5 was obtained in a yield of 73% and a melting point of 246.0 to 246.5 °C. 1H NM (400 MHz, DMSO- 6 ): ⁇ 7.42-7.51 (m, 5 ⁇ ), 6.20 (s, 1 ⁇ ).
  • HRMS (ESI) Calculated C n H 8 N 2 O 4 [M+H]+ 233.0557, The experimental value is 233.0577.
  • Example 6 Example 6
  • Example 1 The conditions and procedures were the same as in Example 1 except that 3,5-dichloroaniline was used instead of p-fluoroaniline in Example 1, to give Compound D7, yield 74%, melting point 263.4 to 263.6 °C.
  • 1H NMR 400 MHz, DMSO- 6 ): ⁇ 7.71 (s, 1H), 7.7 (s, 2H), 6.14 (s, 1H).
  • Example 9 The conditions and procedures were the same as in Example 2 except that 3,5-dichloroaniline was used instead of p-fluoroaniline in Example 2 to obtain Compound D8 in a yield of 71%.
  • Example 9
  • Example 2 The conditions and procedures were the same as in Example 2 except that p-nitroaniline was used instead of p-fluoroaniline in Example 2.
  • the compound D13 was obtained in a yield of 72%, and the melting point was from 200 to 212 °C.
  • HRMS (ESI) calcd for C 12 H 9 N 3 O 6 [M+H]+ 292.0564,
  • Example 15 The conditions and procedures were the same as in Example 2 except that 4-trifluoromethylaniline was substituted for p-fluoroaniline in Example 2 to give Compound D14 in a yield of 69%.
  • Example 15 Example 15
  • Example 16 Other conditions and steps are the same as in Example 1 except that 4-bromoaniline is substituted for p-fluoroaniline in Example 1. In the same manner, Compound D15 was obtained in a yield of 83%.
  • Example 17 The conditions and procedures were the same as in Example 2 except that 4-bromoaniline was used instead of p-fluoroaniline in Example 2 to give Compound D16 in a yield of 69%.
  • Example 17 Example 17
  • Example 18 The conditions and procedures were the same as in Example 1 except that 3-trifluoromethylaniline was used instead of p-fluoroaniline in Example 1, to obtain Compound D17 in a yield of 81%.
  • Example 18
  • Example 20 The conditions and procedures were the same as in Example 1 except that 4-trifluoromethoxyaniline was used instead of p-fluoroaniline in Example 1, to give Compound D19 in a yield of 83%.
  • Example 21 The conditions and procedures were the same as in Example 1 except that 2-trifluoromethylaniline was used instead of p-fluoroaniline in Example 1, to obtain Compound D20 in a yield of 85%.
  • Example 21 Example 21
  • Example 23 Example 23
  • Example 24 The conditions and procedures were the same as in Example 2 except that 2-methoxyaniline was used instead of p-fluoroaniline in Example 2 to give Compound D23 in a yield of 66%.
  • Example 24 Example 24
  • Example 25 The conditions and procedures were the same as in Example 1 except that 3,5-dimethoxyaniline was substituted for p-fluoroaniline in Example 1, to obtain Compound D24 in a yield of 77%.
  • Example 25
  • Example 26 The conditions and procedures were the same as in Example 2 except that 3,5-dimethoxyaniline was replaced by p-fluoroaniline in Example 2 to give Compound D25 in a yield of 67%.
  • Example 26
  • Example 27 The conditions and procedures were the same as in Example 1 except that 3,4-difluoroaniline was used instead of p-fluoroaniline in Example 1, to obtain Compound D26 in a yield of 78%.
  • Example 27
  • Example 28
  • Example 29 The conditions and procedures were the same as in Example 1 except that 3-fluoroaniline was used instead of p-fluoroaniline in Example 1, to obtain Compound D28 in a yield of 79%.
  • Example 29 Example 29
  • Example 30 The conditions and procedures were the same as in Example 2 except that 4-trifluoromethylaniline was substituted for the p-fluoroaniline of Example 2.
  • the compound D29 was obtained in a yield of 66%.
  • Example 30 Example 30
  • Example 31 The conditions and procedures were the same as in Example 2 except that 2-fluoroaniline was used instead of p-fluoroaniline in Example 2 to obtain Compound D30 in a yield of 59%.
  • Example 32 The conditions and procedures were the same as in Example 1 except that 4-fluoro-3-trifluoromethylaniline was used instead of p-fluoroaniline in Example 1, to obtain Compound D31, yield 78%.
  • Example 32
  • Example 33 The conditions and procedures were the same as in Example 1 except that 4-chloro-3-trifluoromethylaniline was used instead of p-fluoroaniline in Example 1, to obtain Compound D32 in a yield of 78%.
  • 1H NM (400 MHz, DMSO- 6 ): ⁇ 8.09 (d, J 2.0 ⁇ , ⁇ ), 7.87-7.93 (m, 2H), 6.17 (s, 1H).
  • Example 34 Activity test
  • Test concentration This test uses 100 mg/L test concentration.
  • Test method Seed various crops in advance, and weigh the sample quantitatively, dissolve it with DMF and add appropriate amount of surfactant, and dilute to the set concentration with water.
  • the drug treatment was carried out in four steps, 7 days, 5 days, 3 days, and 1 day before the inoculation, and then the pathogens were simultaneously inoculated at one time. The experiment was carried out by potting and repeated 3 times.
  • the present invention uses 11 methods for the induction of disease resistance of five diseases by the method described above for the 11 4-hydroxy-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid derivatives.
  • the activity was tested and the pre-compound test activity data is shown in Table 1 below: Table 1

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Abstract

La présente invention concerne un composé pyridazinone de formule (I) et son utilisation comme activateur de résistance induite par une plante. Dans la formule, R1-R5 sont indépendamment choisis parmi : l'hydrogène, un alkyle en C1-C6, un alcoxy en C1-C6, un halogène, un haloalkyle en C1-C6, un haloalcoxy en C1-C6, un nitro, un amino, CN, NCO, NCS, un carboxyle, un alcoxy formacyle en C1-C3 et un amido en C1-C3 ; X est choisi parmi l'oxygène, le soufre et l'azote ; R6 est H, un alkyle en C1-C3 éventuellement substitué, un phényle éventuellement substitué et un hétéroaryle à 5 à 10 chaînons ; et R7 est H, un alkyle en C1-C3 éventuellement substitué et un phényle éventuellement substitué.
PCT/CN2013/082984 2012-09-06 2013-09-05 Composé pyridazinone et utilisation associée WO2014036952A1 (fr)

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CA3019009A1 (fr) * 2016-04-15 2017-10-19 Syngenta Participations Ag Composes herbicides de type de pyridazinone
CN107372496B (zh) * 2017-06-05 2021-01-15 华中师范大学 苯肼基酮类化合物在作为农用杀菌剂的用途
CN114190399A (zh) * 2021-12-31 2022-03-18 山东耘歌生物科技有限公司 含有草铵膦与丙炔氟草胺的除草剂组合物及其制备方法和应用

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