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WO2013064079A1 - Utilisation d'un composé d'amides de pyrazole en tant que fongicide agricole - Google Patents

Utilisation d'un composé d'amides de pyrazole en tant que fongicide agricole Download PDF

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Publication number
WO2013064079A1
WO2013064079A1 PCT/CN2012/083868 CN2012083868W WO2013064079A1 WO 2013064079 A1 WO2013064079 A1 WO 2013064079A1 CN 2012083868 W CN2012083868 W CN 2012083868W WO 2013064079 A1 WO2013064079 A1 WO 2013064079A1
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group
alkyl
alkoxy
hydrogen
halogenated
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PCT/CN2012/083868
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English (en)
Chinese (zh)
Inventor
刘长令
王立增
兰杰
孙旭峰
孙芹
张金波
Original Assignee
中国中化股份有限公司
沈阳化工研究院有限公司
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Priority to CN201280043368.5A priority Critical patent/CN103781357B/zh
Publication of WO2013064079A1 publication Critical patent/WO2013064079A1/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
    • 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

Definitions

  • the invention belongs to the field of agricultural fungicides, and in particular relates to the use of a pyrazole amide compound as an agricultural fungicide. Background technique
  • Patent US 4,950,668 A discloses that N-benzylpyrazole amide derivatives such as tebufenpyrad have insecticidal and acaricidal activity.
  • Patent US 5,091,693 A discloses that a phenoxy-substituted N-benzylpyrazole amide derivative such as tolfenpyrad has insecticidal and acaricidal activity.
  • Patent CN1927860A discloses that a pyrazole amide derivative of a phenylbiaryl group has insecticidal and acaricidal activity. No bactericidal activity was reported.
  • Patent WO02083647A1 discloses pyridylamide derivatives containing biphenyl having bactericidal, insecticidal and acaricidal activity.
  • Patent US 5,091,693 discloses a compound of the formula having insecticidal and acaricidal activity, but the patent does not disclose its bactericidal activity.
  • Patent EP0394043A1, US5264448A discloses a compound of the formula having insecticidal and acaricidal activity
  • Patent EP 0 365 925 A1 discloses a compound of the formula having insecticidal and acaricidal activity. Although the compound of the patent is partially identical to the compound of the formula (I), the patent does not report any bactericidal activity.
  • Patent WO2009024342A2 discloses a compound of the following formula and a specific compound CK1 (patent number 1.581), and some compounds have a minimum of 50% for wheat powdery mildew, barley net blotch, wheat brown rust, wheat black carp at 0.02% active ingredient content. %.
  • Patent WO02089583A1 discloses a compound of the general formula and a specific compound azole amide (patent number No. 4), CK2 (patent number No. 5), CK3 (patent number No. 2), CK4 (patent No. l), With sterilization
  • Patent WO02083647A1 discloses a compound of the following formula and a specific compound CK5 (patent number No. 18) having bactericidal, insecticidal and acaricidal activity.
  • the present invention has intensively studied the bactericidal activity of pyrazole amide compounds represented by the following formula, and found that the compounds have a broad spectrum of sterilization.
  • Activity - can be used to control diseases caused by various pathogens such as Oomycetes, Basidiomycetes, Ascomycetes and Deuteromycetes on various crops, and because of the high biological activity of these compounds, at very low doses You can get good results.
  • R 2 is selected from the group consisting of hydrogen, halogen, cyano, C r C 8 alkyl, halogenated C r C 8 alkyl, 8 -alkoxy, halo- -3 ⁇ 4 alkoxy, cyano dC 8 alkyl, cyano dC 8 alkoxy, unsubstituted or substituted by 1 to 5 phenyl groups independently selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, decyl, dC 8 alkyl, halo dC 8 An alkyl group, a dC 8 alkoxy group or a halogenated CrC 8 alkoxy group;
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, dC 8 alkyl, halo dC 8 alkyl, dC 8 alkoxy, halogenated dC 8 alkoxy, 8 -alkylthio or dC 8 alkyl sulfonate Acyl group
  • A is selected from -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH(CH 3 )-, -C(CH 3 ) 2 -, -C(CN)(CH 3 ) - or -CH(CN)-;
  • R 5 may be the same or different and are respectively selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, amino, dC 8 alkyl, halogenated Ci-C 8 3 ⁇ 43 ⁇ 4 ⁇ 4 Ci-Cg ⁇ ⁇ Ci-Cg C 3 -C 8 ring; ⁇ group, C 2 -C 8 ⁇ 3 ⁇ 4 C 2 -C 8 block group, C 2 -C 8 alkenyloxy group, ⁇ 3 ⁇ 4-3 ⁇ 4 alkenyloxy group, 3 ⁇ 4-3 ⁇ 4 Blockoxy, ⁇ 3 ⁇ 4 8 oxy, 8 alkylthio, ⁇ -3 ⁇ 4 alkane, Ci-C8 3 ⁇ 43 ⁇ 43, 3
  • Q is selected from hydrogen, halo, cyano, nitro, hydroxy, amino, dC 8 alkyl, haloalkyl dC 8 alkyl, dC 8 alkoxy, substituting ⁇ dC 8 alkoxy, C 3 -C 8 cycloalkyl a group, a C 2 -C 8 alkenyl group, a C 2 -C 8 block group, a C 2 -C 8 alkenyloxy group, a C 2 -C 8 alkenyloxy group, an 8-oxyl group, a halogenated 8- oxyl group, dC 8 thiol, halogenated dC 8 alkylthio, dC 8 alkoxy dC 8 alkyl, 13 ⁇ 4 generation Ci-Cs, alkoxy-Ci-Cs, Ci-Cs, thio-Ci-Cs, 13 ⁇ 4 generation Ci-Cs Institute thio-Ci-Cs, dC 8 alkyls
  • the pyrazole amide compound as an agricultural bactericide is a compound selected from the group consisting of pyridyloxy groups in the formula I, and has a structure such as
  • Ci-C 6 alkyl Selected from hydrogen, Ci-C 6 alkyl, ⁇ dC 6 alkyl, Ci-C 6 alkoxy C r C 3 alkyl, cyano dC 6 alkyl or C 3 -C 6 cycloalkyl;
  • R 2 is selected from the group consisting of hydrogen, halogen, cyano, dC 6 alkyl, halo dC 6 alkyl, dC 6 alkoxy, halo C r C 6 alkoxy, cyano dC 6 alkyl, cyano dC 6 Alkoxy, unsubstituted or substituted by 1 to 5 phenyl groups independently selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, decyl, dC 6 alkyl, halogenated C r C 6 alkyl, C r C 6 alkoxy or halo CC 6 alkoxy;
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, dC 6 alkyl, halo dC 6 alkyl, dC 6 alkoxy, halogenated dC 6 Alkoxy, 6 alkylthio or c r c 6 alkylsulfonyl;
  • R 5 may be the same or different and are respectively selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, amino, C r C 6 alkyl, halogenated C r C 6 alkyl, C r C 6 alkoxy, ⁇ Generation C r C 6 alkoxy, C 2 -C 6 alkenyloxy, ⁇ C 2 -C 6 alkenyloxy, C 2 -C 6 -oxyl, halo C 2 -C 6 -oxyl, C r C 6 alkylsulfinyl, halogenated C r C 6 alkylsulfinyl, C r C 6 alkylsulfonyl, halogenated C r C 6 alkylsulfonyl, C r C 6 alkylamino, halogen Generation C r C 6 alkylamino or C 2 -C 6 dialkylamino; is selected from hydrogen, halo, cyano, nitro, hydroxy
  • A is selected from -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH(CH 3 )- or -CH(CN)-.
  • a further preferred embodiment of the present invention is a pyrazole amide compound represented by the formula (I-A) as an agricultural bactericide:
  • R 2 is selected from the group consisting of hydrogen, halogen, cyano, C r C 6 alkyl, halogenated C r C 6 alkyl, C r C 6 alkoxy, halogenated C r C 6 alkoxy, cyano 6 alkyl , cyano 6 alkoxy, unsubstituted or substituted by 1 to 5 phenyl groups independently selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, decyl, C r C 6 alkyl, Halogenated C r C 6 alkyl, C r C 6 alkoxy or halo 6 alkoxy;
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C r C 6 alkyl, halogenated C r C 6 alkyl, C r C 6 alkoxy, halogenated C r C 6 alkoxy, 6 alkane Thio or c r c 6 alkylsulfonyl;
  • R 5 is selected from hydrogen
  • n is selected from an integer from 0 to 4; when n is greater than 1, it may be the same or different;
  • A is selected from -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH(CH 3 )- or -CH(CN)-.
  • a still further preferred embodiment of the present invention is a pyrazole amide compound represented by the formula (I-A) as an agricultural bactericide:
  • R 2 is selected from hydrogen, halo, cyano, C r C 4 alkyl, C r C 4 halogenated alkyl, alkoxy, halo ⁇ 4 alkoxy, cyano dC 3 alkyl, cyano - 3 ⁇ 4 alkoxy, unsubstituted or substituted by 1 to 3 phenyl groups independently selected from the group consisting of halogen, cyano, nitro, C r C 4 alkyl, halogenated C r C 4 alkyl, C r C 4 alkoxy or halo 4 alkoxy;
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C r C 4 alkyl, halogenated C r C 4 alkyl, C r C 4 alkane Oxy or halogenated C r C 4 alkoxy;
  • R 5 is selected from hydrogen
  • n selected from An integer from 0 to 4; when n is greater than 1, it may be the same or different;
  • A is selected from -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH(CH 3 )- or -CH(CN)-.
  • a still further preferred embodiment is the pyrazole amide compound represented by the general formula (IA) as an agricultural bactericide: Selected from hydrogen, methyl, ethyl, cyclopropyl or cyclohexyl;
  • R 2 is selected from the group consisting of hydrogen, chlorine, bromine, methyl, ethyl, chloromethyl, difluoromethyl, trifluoromethyl, methoxymethyl, methoxy, ethoxy, monofluoromethoxy, Trifluoromethoxy, trifluoroethoxy, cyanomethyl, cyanomethoxy, phenyl, p-chlorophenyl, p-fluorophenyl, p-methylphenyl, p-trifluoromethylphenyl, P-methoxyphenyl, p-trifluoromethoxyphenyl, 2,4-dichlorophenyl or 2,4-dimethylphenyl;
  • R 3 is selected from the group consisting of hydrogen, chlorine, bromine or methyl
  • R 5 is selected from hydrogen
  • n is selected from an integer of 0 to 4; when n is greater than 1, it may be the same or different;
  • A is selected from -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH(CH 3 )- or -CH(CN)-.
  • R 2 is selected from the group consisting of methyl, ethyl, phenyl, p-chlorophenyl, p-fluorophenyl, p-methylphenyl, p-trifluoromethylphenyl, p-methoxyphenyl, p-trifluoromethoxy Phenyl, 2,4-dichlorophenyl or 2,4-dimethylphenyl;
  • R 3 is selected from the group consisting of hydrogen, chlorine or methyl
  • R 5 is selected from hydrogen
  • n is selected from an integer from 0 to 4; When n is greater than 1, it may be the same or different;
  • A is selected from -CH 2 -, -CH 2 CH 2 - or -CH 2 CH 2 CH 2 -.
  • R 2 is selected from the group consisting of methyl, ethyl, phenyl, p-chlorophenyl or p-fluorophenyl;
  • R 3 is selected from the group consisting of hydrogen, chlorine or methyl
  • R 5 is selected from hydrogen
  • n is selected from the integers from 1 to 3;
  • A is selected from -CH 2 -, -CH 2 CH 2 - or -CH 2 CH 2 CH 2 -.
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • Alkyl a linear or branched alkyl group such as methyl, ethyl, propyl, isopropyl, n-butyl or t-butyl.
  • Cycloalkyl a substituted or unsubstituted cyclic alkyl group such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like.
  • Haloalkyl a straight or branched alkyl group in which a hydrogen atom may be partially or completely substituted by a halogen atom, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, Fluoromethyl, trifluoromethyl, and the like.
  • Alkoxy A linear or branched alkyl group bonded to a structure via an oxygen atom.
  • Alkoxyalkyl Alkoxy is attached to the structure via an alkyl group. For example, CH 3 OCH 2 -, CH 3 CH 2 OCH 2 -.
  • Haloalkoxyalkyl group The hydrogen atom on the alkyl group of the alkoxyalkyl group may be partially or completely substituted by a halogen atom. Such as ClCH 2 CH 2 OCH 2 -.
  • Haloalkoxy a linear or branched alkoxy group, and a hydrogen atom on these alkoxy groups may be partially or completely substituted by a halogen atom.
  • Alkylthio a linear or branched alkyl group bonded to a structure via a sulfur atom bond.
  • Alkylthioalkyl An alkylthio group is attached to the structure via an alkyl group. Such as CH 3 SCH 2 -.
  • Haloalkylthio a linear or branched alkylthio group in which a hydrogen atom may be partially or completely substituted by a halogen atom. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like.
  • Haloalkylthioalkyl A haloalkylthio group is attached to the structure via an alkyl group, such as ClCH 2 SCH 2 -.
  • Alkylamino a linear or branched alkyl group bonded to the structure via a nitrogen atom.
  • Haloalkylamino group a linear or branched alkylamino group in which a hydrogen atom may be partially or completely substituted by a halogen atom.
  • Alkenyl a linear or branched olefin such as a vinyl group, a 1-propenyl group, a 2-propenyl group and a different butenyl, pentenyl group and hexenyl isomer.
  • Alkenyl groups also include polyenes such as 1,2-propadienyl and 2,4-hexyl Dienyl.
  • Haloalkenyl group a linear or branched olefin in which a hydrogen atom on these alkenyl groups may be partially or completely substituted by a halogen atom.
  • Block base A linear or branched block type, such as an ethyl group, a 1-propyl block, a 2-propyl block, and different butyr, pentyl and hexyl isomers.
  • the block group also includes a group consisting of a plurality of triple bonds, such as a 2,5-hexane block.
  • Halogenated block A linear or branched block, in which a hydrogen atom may be partially or completely replaced by a halogen atom.
  • Alkenyloxy A linear or branched olefin that is bonded to the structure via an oxygen atom.
  • Haloalkenyloxy a linear or branched alkenyloxy group, and a hydrogen atom on these alkenyloxy groups may be partially or completely substituted by a halogen atom.
  • Block Oxygen A linear or branched block that is attached to a structure via an oxygen atom.
  • Halo blockoxy a linear or branched blockoxy group, and a hydrogen atom on these blockoxy groups may be partially or completely substituted by a halogen atom.
  • Alkylsulfinyl A straight or branched alkyl group is attached to the structure via a sulfinyl group (-SO-), such as a methylsulfinyl group.
  • Haloalkylsulfinyl a linear or branched alkylsulfinyl group in which a hydrogen atom on the alkyl group may be partially or completely substituted by a halogen atom.
  • Alkylsulfonyl A straight or branched alkyl group is attached to the structure via a sulfonyl group (-so 2 -), such as a methylsulfonyl group.
  • Haloalkylsulfonyl a linear or branched alkylsulfonyl group in which a hydrogen atom on the alkyl group may be partially or completely substituted by a halogen atom.
  • Alkylcarbonyl An alkyl group is attached to the structure via a carbonyl group, such as CH 3 CO-, CH 3 CH 2 CO-.
  • Haloalkylcarbonyl The hydrogen atom on the alkyl group of the alkylcarbonyl group may be partially or completely substituted by a halogen atom such as CF 3 CO-.
  • Alkylaminocarbonyl such as CH 3 NHCO-, CH 3 CH 2 NHCO-.
  • Alkoxycarbonyl alkoxy is attached to the structure via a carbonyl group.
  • CH 3 OCO-, CH 3 CH 2 OCO alkylcarbonyloxy such as CH 3 COO-, CH 3 CH 2 NHCOO-.
  • Alkylcarbonylamino such as CH 3 CONH-, CH 3 CH 2 NHCONH -.
  • Heteroaryl The heteroaryl group referred to in the present invention is a five-membered or six-membered ring aryl group containing one or more N, O, s hetero atoms.
  • Heteroaryloxy A heteroaryl ring is attached to the structure via an oxygen group, such as a pyridyloxy group, a pyrimidinyloxy group or the like.
  • L is a leaving group and is a halogen, a methanesulfonate or a p-toluenesulfonate.
  • the other groups are defined as before.
  • the compound of the formula (VI-1) and (V) are reacted in a suitable solvent in the presence of a suitable base to give (IV-1).
  • the specific preparation can be carried out by referring to the method described in Fine Chemicals, 2005, 22(12): 944-960.
  • the reaction is usually carried out at a temperature ranging from room temperature to the boiling point of the solvent, and a suitable reaction temperature is 20 to 100 °C.
  • the reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
  • Suitable solvents may be selected from, for example, acetone, butanone, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide, dimethyl sulfoxide, methanol or ethanol, and the like.
  • Suitable bases may be selected from, for example, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, triethylamine, pyridine or sodium hydride, and the like.
  • (IV-1) is hydroreduced in the presence of a suitable catalyst and aqueous ammonia in a suitable solvent to give (11-1).
  • a suitable catalyst and aqueous ammonia in a suitable solvent to give (11-1).
  • Specific preparation Reference may be made to the literature J. Am. Chem. Soc, 70, 3788 (1948); 82, 681 (1960); 82, 2386 (1960); Can. J. Chem, 49, 2990 (1971); J. Org. Chem, 37, 335 (1972); Organic Syntheses, Coll. Vol. 3, p. 229, p. 720 (1955), Vol. 23, p. 71 (1943) or Vol. 27, p. 18 (1947).
  • the reaction is usually carried out at a temperature ranging from room temperature to the boiling point of the solvent, and a suitable reaction temperature is 20 to 100 °C.
  • the reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
  • Suitable solvents may be selected from the group consisting of methanol, ethanol, isopropanol, benzene, toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, chloroform, dichloromethane, methyl acetate, ethyl acetate, tetrahydrofuran, dioxane. , N,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
  • Suitable catalysts may be selected from the group consisting of Raney nickel, palladium carbon or platinum oxide.
  • the compound represented by the formula (IA-1) may be an amine represented by the formula (II-1) and a pyrazolecarbonyl chloride represented by the formula (III) in a suitable solvent in the presence of a suitable base (also Can be obtained without condensation.
  • a suitable solvent may be selected from the group consisting of benzene, toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methylpyrrolidone, dimethylene.
  • Suitable bases may be selected from, for example, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, triethylamine, pyridine or sodium hydride, and the like.
  • the reaction temperature may be between room temperature and the boiling point of the solvent, and is usually from 20 to 100 °C.
  • the reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
  • A is a corresponding structure having one carbon atom less than A.
  • the other groups are defined as before.
  • reaction conditions obtained by the reaction of (VI-2) and (V), the intermediate (IV-2) and (II-2) (IA-2) and the choice of solvent, base and metal catalyst are the same as the first In the case of (VI-1) and (V), the corresponding steps of (IA-1) are obtained via intermediates (IV-1) and (II-1).
  • Boc 2 0 refers to di-tert-butyl dicarbonate.
  • the other groups are defined as before.
  • the di-tert-butyl dicarbonate is reacted with the corresponding aminophenol at 0 to 100 ° C in a suitable solvent in the presence of a suitable base to first obtain a Boc-protected aminophenol (VII).
  • the reaction temperature is preferably 0 to 50 ° C; the reaction time is 30 minutes to 20 hours, preferably 0.5 to 10 hours.
  • Suitable solvents are selected from the group consisting of benzene, toluene, xylene, chloroform, dichloromethane, tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide;
  • the base is selected from alkali metal carbonates such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate or potassium hydrogencarbonate.
  • (VII) and (V) are condensed in a suitable solvent in the presence of a suitable base at 0 to 100 ° C to obtain a (VII1) o reaction time of 30 minutes to 20 hours, preferably 0.5 to 10 hours.
  • suitable solvents are selected from the group consisting of benzene, toluene, xylene, chloroform, dichloromethane, acetone, butanone, tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methylpyrrolidone or dimethylene.
  • a suitable base is selected from metal hydrides such as sodium hydride, alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, alkali metal carbonates such as sodium carbonate or potassium carbonate, and organic amines such as pyridine or triethylamine.
  • Suitable solvents are selected from the group consisting of ethyl acetate, methyl acetate, methyl formate, benzene, toluene, xylene, chloroform, dichloromethane, water, tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide; etc.; suitable acids are selected from the group consisting of hydrochloric acid, trifluoroacetic acid, sulfuric acid, acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, and stearic acid.
  • the base is selected from the group consisting of metal hydrides such as sodium hydride, alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali metal carbonate
  • metal hydrides such as sodium hydride, alkali metal hydroxides such as sodium hydroxide or potassium hydroxide
  • alkali metal carbonate For a specific preparation method of a salt such as sodium carbonate or potassium carbonate, uuuuu is described in WO2004093800A.
  • the compound represented by the formula (IA-3) may be an amine represented by the formula ( ⁇ -3) and a pyrazolecarbonyl chloride represented by the formula (III) in a suitable solvent in the presence of a suitable base (also Can be obtained without condensation.
  • a suitable solvent also Can be obtained without condensation.
  • the reaction conditions and the choice of solvent and base are the same as those obtained by the reaction of ( ⁇ -1) and (III) in the first case (I-A-l) o
  • the raw materials involved in the preparation method of the above compound of the general formula (I) are as follows:
  • the compounds represented by the general formulae (VI-1), (VI-2) and (V) are commercially available, (VI-3)
  • the compounds shown are either commercially available or prepared according to known methods such as those reported in JP61024550, US4843160, US4746754, US2396580, JP02017164, Afmidad, 42(397), 270-2; 1985, and the like.
  • the compound of the formula (III) is commercially available or can be reported according to known literature such as Annalen der Chemie Justus Liebig's, 536, 97 (1938) Bull. Soc. Chim. France, 293 (1966) US 4950668 JP 2292263 JP 2053776 JP4069361 or JP 4069379. Method preparation.
  • the present invention can be illustrated by the compounds listed in Tables 1 to 3 below, but does not limit the present invention.
  • the present invention Since the present invention has found for the first time that a pyrazole amide compound represented by the general formula (I) has excellent bactericidal activity, the compound can be applied to various crops in agricultural fields such as agriculture, horticulture and flower cultivation.
  • the disease is especially suitable for controlling the following plant diseases: cucumber downy mildew, corn rust, etc.
  • the plant pathogen which can be controlled by the compound of the present invention is not limited to the above. Accordingly, the technical solution of the present invention includes the use of a pyrazole amide compound represented by the formula (I), particularly a pyrazole amide compound represented by the formula (I-A), as an agricultural bactericide.
  • the use of the pyrazole amide compound (preferably the compound of the formula (IA)) represented by the formula (I) proposed by the present invention as an agricultural bactericide further comprises providing a bactericidal composition containing bactericidal activity in the composition
  • the compound of the formula (I) (preferably the compound of the formula (IA)) as an active ingredient, the active ingredient in the composition is present in an amount of from 0.1 to 99% by weight.
  • the composition also contains an agriculturally acceptable carrier and surfactant.
  • the above compositions can be prepared into a desired dosage form according to known methods, such as wettable powders, powders, granules and solutions, emulsifiable concentrates, emulsions, suspension concentrates, aerosols and aerosols.
  • carrier and surfactant in the formulation is well known to those skilled in the art.
  • bactericides By incorporating other one or more bactericides into the composition, it has a broader spectrum of activity than the compound of formula (I) alone. Further, other bactericides have a synergistic effect on the bactericidal activity of the compound of the formula (I).
  • the compound of the formula (I) can also be used in combination with other insecticides or at the same time with another fungicide and other insecticides. detailed description
  • the organic layer was poured into 20 mL of water, and the organic layer was washed successively with 5% diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and then evaporated and evaporated. Pure product 0.38 g was obtained, the yield was 88.0%, and the melting point was 97-98 °C.
  • Compound 170 melting point 145-146 ° C o 5 ppm 1.23 (3H, t), 2.60-2.63 (2H, m), 2.96 (2H, t), 3.74-3.76 (2H, (m), 4.12 (3H, s) ).
  • Compound 176 mp 157-158°C o 5ppm 1.22 (3H, t), 2.57-2.64 (2H, m), 2.96 (2H, t), 3.74-3.79 (2H, m), 4.13 (3H, s), 7.12(2H, d), 7.30(2H, d), 7.85(1H, s).
  • Compound 972 Melting point 100-lOr. Sppm 1.23(3H, t), 1.42(3H, t), 2.59-2.67(2H, m), 4.00-4.07(2H, m), 4.15(3H, s), 4.56(2H, d), 6.88(2H , d), 7.27 (2H, d).
  • Example 8 60% wettable powder
  • Kaolin is made up to 100%
  • the components (both solids) are mixed and comminuted in a pulverizer until the granules reach the standard.
  • Example 9 30% aqueous suspension
  • Compound 53 was pulverized together with 80% of the water to be added and sodium dodecylnaphthalene sulfonate in a ball mill (1 mm beads). The other components were dissolved in the remaining water, and then the other components were stirred.
  • the compound 54 and the other components are thoroughly mixed, and the thus obtained suspension concentrate is diluted with water to obtain a diluent of any desired concentration.
  • test method is as follows:
  • the test was carried out using a potted seedling assay.
  • the two-leaf stage potted cucumber seedlings with uniform growth were selected as test materials for cucumber downy mildew; the two-leaf potted corn seedlings with uniform growth were selected as test materials for corn rust; the two-leaf potted wheat seedlings with uniform growth were selected as wheat white powder.
  • Disease test material The compound of the present invention was subjected to foliar spray treatment at a designed concentration, and a blank control of sprayed water was additionally provided, three times of repetition, and the disease was inoculated the next day after the treatment. After inoculation, the plants are placed in an artificial climate chamber (temperature: ⁇ 25 °C, night 20 °C, relative humidity: 95 ⁇ 99%).
  • the control effect of the compounds 53, 54, 115, 169, 170, 972, 973, 1024, 1025, 1027, 1028, etc. is 100%; the control effect of the compound 189, 591, etc. is 98%; The control effect of 519 is 95%; the control effect of compound 157 is 85%;
  • the control effects of the compounds 53, 54, 115, 169, 170, 972, 973, 1024, 1027, etc. are 100%; the control effect of the compound 1025 is 80%;
  • the control effects of the compounds 53, 54, 169, 1024, etc. are 100%; the control effects of the compounds 115, 972 are 98% and 95%, respectively;
  • the concentration of the chemical solution is 12.5 ppm, the control effect of the compound 53, 54 and the like is 100%; the control effect of the compound 1024 is 85%; and when the concentration of the chemical liquid is 3.125 ppm, the control effect of the compound 53 is 95%.
  • the control effects of the compounds 115, 169, 519, 972, 973, 1024, 1025, 1026, 1027, 1028, etc. are 100%, and the control effect of the compound 189 or the like is 95%;
  • the control effect of the compounds 972, 973, 1024, 1026, 1027, etc. is 100%; the control effect of the compound 1025 is 95%;
  • the concentration of the chemical solution is 25 ppm
  • the control effect of the compounds 973, 1024, 1027, etc. is 100%
  • the control effect of the compound 1026 is 90%
  • the compound 973 and 1024 have a control effect of 90% or more.
  • the determination method is as follows:
  • the high-throughput screening method is adopted, that is, the sample of the test compound is dissolved in a suitable solvent (such as acetone, methanol, DMF, etc., and selected according to the solvency of the sample) to prepare a desired concentration.
  • a suitable solvent such as acetone, methanol, DMF, etc., and selected according to the solvency of the sample
  • the liquid to be tested In the ultra-clean working environment, the test solution is added to the micropores of the 96-well culture plate, and the pathogen propagule suspension is added thereto, and the treated plate is placed in a constant temperature incubator for cultivation, and then investigated after 24 hours. .
  • the germination or growth of the pathogen of the pathogen was visually observed at the time of the investigation, and the bacteriostatic activity of the compound was evaluated based on the germination or growth of the control treatment.
  • the control effects of the compounds 115, 181, 499, 519, 973, 1024, 1028, etc. are 100%; the control effects of the compounds 155, 972, 1025, 1027 are all 80%;
  • the concentration of the chemical solution is 0.9 ppm
  • the control effect of the compound 115 and 519 is 100%
  • the control effect of the compound 973 is 80%
  • the control effect of the compound 115, 519, etc. is 100%; the control effect of the compound 499 is 80%; when the concentration of the chemical solution is 8.3 ppm, the control effect of the compound 519 is 100%; 80%;
  • the compound 519 had an effect of 80%.
  • the test was carried out in July 2011 in Yitian District, Yuhong District, Shenyang City, Liaoning Republic. The test was carried out in accordance with the relevant standards of the National Standard for Pesticide Field Efficacy Test of the People's Republic of China.
  • the concentration of the compound of the present invention 54 (10% concentrated suspension of Example 10, the same hereinafter) was 400, 100 ppm, and the concentration of the control agent 50% dimethomorph wettable powder (commercially available) was 200 ppm.
  • the area of the plot is 20m 2 , randomly arranged, and repeated twice. The amount of liquid spray is about 600 L/hm 2 , and fresh water is used as a blank control.
  • Table 5 The results of the test of compound 54 against cucumber downy mildew field plot are shown in Table 5.

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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)
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  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention a trait à l'utilisation d'un composé d'amides de pyrazole comme indiqué dans la formule générale (I) en tant que fongicide agricole. Les définitions de chaque substituant dans la formule (I) sont données dans la description. Le composé selon la présente invention est doté d'un large spectre d'activité fongistatique et d'une excellente activité contre les maladies telles que le mildiou du concombre, la piriculariose du riz, la rouille du maïs, l'oïdium du blé, la moisissure grise du concombre, etc. En particulier, le composé est doté d'une plus grande activité contre les maladies telles que le mildiou du concombre, la piriculariose du riz, etc., et peut fournir un excellent effet à une très faible concentration.
PCT/CN2012/083868 2011-11-02 2012-10-31 Utilisation d'un composé d'amides de pyrazole en tant que fongicide agricole WO2013064079A1 (fr)

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