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CN115232083B - Substituted isoxazole ethylamine compounds and preparation method and use thereof - Google Patents

Substituted isoxazole ethylamine compounds and preparation method and use thereof Download PDF

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Publication number
CN115232083B
CN115232083B CN202110435945.6A CN202110435945A CN115232083B CN 115232083 B CN115232083 B CN 115232083B CN 202110435945 A CN202110435945 A CN 202110435945A CN 115232083 B CN115232083 B CN 115232083B
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alkyl
halogenated
alkoxy
butyl
hydrogen
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CN115232083A (en
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李淼
杨吉春
赵杰
吴峤
李志念
刘长令
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses a substituted isoxazole ethylamine compound, the structure of which is shown as a general formula I, wherein the definition of each substituent group in the formula is shown in the specification. The compound has broad-spectrum bactericidal activity and excellent control effects on cucumber downy mildew, powdery mildew, corn rust disease, anthracnose, rice blast and the like.

Description

Substituted isoxazole ethylamine compound and preparation method and application thereof
Technical Field
The invention belongs to the field of chemistry, and in particular relates to a substituted isoxazole ethylamine compound, a preparation method thereof and application thereof as a bactericide.
Background
The literature Bioorganic & MEDICINAL CHEMISTRY (2015), 23 (6), 1260-1275 and patent WO 9219604 disclose substituted isoxazoleethylamines which are used in the medical field as receptor antagonists and lipoxygenase and cyclooxygenase inhibitors, respectively.
In the prior art, although the disclosed compounds have certain similarities with the compounds of the invention, the compounds shown in the general formula of the invention are obviously different from the prior art, and have good bactericidal activity.
Disclosure of Invention
The invention aims to provide a substituted isoxazole ethylamine compound capable of controlling various germs, a preparation method thereof and application thereof in preparing medicines for controlling germs in agriculture or other fields.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
A substituted isoxazole ethylamine compound is characterized in that the substituted isoxazole ethylamine compound is a compound shown in a general formula I;
Wherein:
R 1 is selected from hydrogen, C 1-C12 alkyl, halogenated C 1-C12 alkyl, C 3-C12 cycloalkyl, C 1-C12 alkoxy, halogenated C 1-C12 alkoxy, C 2-C12 alkenyl, halogenated C 2-C12 alkenyl, C 2-C12 alkynyl, halogenated C 2-C12 alkynyl, C 3-C12 alkenyloxy, halogenated C 3-C12 alkenyloxy, C 3-C12 alkynyloxy, halogenated C 3-C12 alkynyloxy, C 1-C12 alkoxy C 1-C12 alkyl or C 1-C12 alkylthio C 1-C12 alkyl;
R 2 is selected from halogen, hydroxy, amino, cyano, nitro, C 1-C12 alkyl, halogenated C 1-C12 alkyl, C 1-C12 alkoxy, halogenated C 1-C12 alkoxy, C 3-C12 cycloalkyl, C 1-C12 alkylamino, halogenated C 1-C12 alkylamino, Di (C 1-C12 alkyl) amino, di (halogenated C 1-C12 alkyl) amino, C 1-C12 alkylthio, halogenated C 1-C12 alkylthio, C 2-C12 alkenyl, C 2-C12 alkynyl, C 2-C12 alkenyloxy, halogenated C 2-C12 alkenyloxy, C 2-C12 alkynyloxy, Halogenated C 2-C12 alkynyloxy, C 1-C12 alkylsulfonyl, halogenated C 1-C12 alkylsulfonyl, C 1-C12 alkylcarbonyl, Halogenated C 1-C12 alkylcarbonyl, C 1-C12 alkoxycarbonyl, halogenated C 1-C12 alkoxycarbonyl, C 1-C12 alkoxyC 1-C12 alkyl, Halogenated C 1-C12 AlkoxyC 1-C12 alkyl, C 1-C12 alkylthio C 1-C12 alkyl, halogenated C 1-C12 alkylthio C 1-C12 alkyl, C 1-C12 Alkoxycarbonyl C 1-C12 alkyl, haloC 1-C12 alkoxycarbonyl C 1-C12 alkyl, C 1-C12 alkylthio carbonyl C 1-C12 alkyl, Halogenated C 1-C12 AlkylthiocarbonylC 1-C12 alkyl, C 1-C12 Alkylcarbonyloxy, halogenated C 1-C12 Alkylcarbonyloxy, C 1-C12 Alkoxycarbonyloxy halogenated C 1-C12 alkoxy carbonyl oxygen radical C 1-C12 Alkylsulfonic acid an acyloxy group acyl oxygen a base group, C 1-C12 Alkoxy C 1-C12 Alkoxy or halo C 1-C12 Alkoxy C 1-C12 Alkoxy, R 2 is not selected from cyano or hydroxy when in the 4-position of the phenyl ring;
n is an integer from 0 to 5, and when n is 0, there is no substituent, and when n is greater than 1, R 2 are the same or different;
R 3 is selected from hydrogen, hydroxy, formyl, C 1-C12 alkyl, halogenated C 1-C12 alkyl, C 1-C12 alkoxy, Halogenated C 1-C12 alkoxy, C 3-C12 cycloalkyl, C 2-C12 alkenyl, C 2-C12 alkynyl, halogenated C 2-C12 alkenyl, Halogenated C 2-C12 alkynyl, C 1-C12 alkoxyC 1-C12 alkyl, halogenated C 1-C12 alkoxyC 1-C12 alkyl, C 1-C12 alkylthio C 1-C12 alkyl, haloC 1-C12 alkylthio C 1-C12 alkyl, C 1-C12 alkylsulfinyl, halogenated C 1-C12 alkylsulfinyl, C 1-C12 alkylsulfonyl, halogenated C 1-C12 alkylsulfonyl, C 1-C12 alkylaminosulfonyl, Di (C 1-C12 alkyl) aminosulfonyl, C 1-C12 alkylsulfonylaminocarbonyl, C 1-C12 alkylcarbonylaminosulfonyl, C 3-C12 cycloalkyloxycarbonyl, C 1-C12 Alkylcarbonyl, haloC 1-C12 Alkylcarbonyl, C 1-C12 alkoxycarbonyl, haloC 1-C12 alkoxycarbonyl, C 1-C12 Alkylcarbonyl C 1-C12 alkyl, C 1-C12 Alkoxycarbonyl C 1-C12 alkyl, C 1-C12 Alkylaminocarbonyl, Di (C 1-C12 alkyl) aminocarbonyl, C 2-C12 alkenyloxycarbonyl, C 2-C12 alkynyloxycarbonyl, C 1-C12 alkoxy C 1-C12 alkoxycarbonyl, Arylcarbonyl C 1-C6 alkyl, arylcarbonyl, aryloxycarbonyl, arylC 1-C6 alkyloxycarbonyl, arylC 1-C6 alkyl, heteroarylcarbonyl C 1-C6 alkyl, unsubstituted or substituted with 1 to 5, Heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylC 1-C6 -alkyloxycarbonyl, heteroarylC 1-C6 -alkyl, a halogen, nitro, cyano, C 1-C6 -alkyl, halo C 1-C6 -alkyl, C 1-C6 alkoxy or halo C 1-C6 alkoxy;
R 4、R5 is the same or different and is selected from hydrogen, halogen, C 1-C12 alkyl, halogenated C 1-C12 alkyl, C 1-C12 alkoxy or halogenated C 1-C12 alkoxy respectively;
Wherein, the C to which R 4、R5 is attached may also form a ring of C 3-C8;
R 6、R7 is the same or different and is selected from hydrogen, halogen, C 1-C12 alkyl, halogenated C 1-C12 alkyl, C 1-C12 alkoxy or halogenated C 1-C12 alkoxy respectively;
wherein, the C to which R 6、R7 is attached may also form a ring of C 3-C8;
q is selected from aryl, heteroaryl which is unsubstituted or substituted by 1-5R 8.
R 8 is selected from halogen, hydroxy, amino, cyano, nitro, C 1-C12 alkyl, halogenated C 1-C12 alkyl, C 1-C12 alkoxy, halogenated C 1-C12 alkoxy, C 3-C12 cycloalkyl, C 1-C12 alkylamino, halogenated C 1-C12 alkylamino, Di (C 1-C12 alkyl) amino, halo di (C 1-C12 alkyl) amino, C 1-C12 alkylthio, halo C 1-C12 alkylthio, C 2-C12 alkenyl, C 2-C12 alkynyl, C 2-C12 alkenyloxy, halogenated C 2-C12 alkenyloxy, C 2-C12 alkynyloxy, Halogenated C 2-C12 alkynyloxy, C 1-C12 alkylsulfonyl, halogenated C 1-C12 alkylsulfonyl, C 1-C12 alkylcarbonyl, Halogenated C 1-C12 alkylcarbonyl, C 1-C12 alkoxycarbonyl, halogenated C 1-C12 alkoxycarbonyl, C 1-C12 alkoxyC 1-C12 alkyl, Halogenated C 1-C12 AlkoxyC 1-C12 alkyl, C 1-C12 alkylthio C 1-C12 alkyl, halogenated C 1-C12 alkylthio C 1-C12 alkyl, C 1-C12 Alkoxycarbonyl C 1-C12 alkyl, haloC 1-C12 alkoxycarbonyl C 1-C12 alkyl, C 1-C12 alkylthio carbonyl C 1-C12 alkyl, Halogenated C 1-C12 AlkylthiocarbonylC 1-C12 alkyl, C 1-C12 Alkylcarbonyloxy, halogenated C 1-C12 Alkylcarbonyloxy, C 1-C12 Alkoxycarbonyloxy halogenated C 1-C12 alkoxy carbonyl oxygen radical C 1-C12 Alkylsulfonic acid an acyloxy group acyl oxygen a base group, C 1-C12 alkoxy C 1-C12 alkoxy or halogenated C 1-C12 alkoxy C 1-C12 alkoxy.
Preferably, in the compounds of formula I:
R 1 is selected from hydrogen, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 3-C6 cycloalkyl, C 1-C6 alkoxy, halogenated C 1-C6 alkoxy, C 2-C6 alkenyl, halogenated C 2-C6 alkenyl, C 2-C6 alkynyl, halogenated C 2-C6 alkynyl, C 3-C6 alkenyloxy, halogenated C 3-C6 alkenyloxy, C 3-C6 alkynyloxy, halogenated C 3-C6 alkynyloxy, C 1-C6 alkoxy C 1-C6 alkyl or C 1-C6 alkylthio C 1-C6 alkyl;
R 2 is selected from halogen, hydroxy, amino, cyano, nitro, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 1-C6 alkoxy, halogenated C 1-C6 alkoxy, C 3-C6 cycloalkyl, C 1-C6 alkylamino, halogenated C 1-C6 alkylamino, Di (C 1-C6 alkyl) amino, di (halogenated C 1-C6 alkyl) amino, C 1-C6 alkylthio, halogenated C 1-C6 alkylthio, C 2-C6 alkenyl, C 2-C6 alkynyl, C 2-C6 alkenyloxy, halogenated C 2-C6 alkenyloxy, C 2-C6 alkynyloxy, Halogenated C 2-C6 alkynyloxy, C 1-C6 alkylsulfonyl, halogenated C 1-C6 alkylsulfonyl, C 1-C6 alkylcarbonyl, Halogenated C 1-C6 alkylcarbonyl, C 1-C6 alkoxycarbonyl, halogenated C 1-C6 alkoxycarbonyl, C 1-C6 alkoxyC 1-C6 alkyl, Halogenated C 1-C6 AlkoxyC 1-C6 alkyl, C 1-C6 alkylthio C 1-C6 alkyl, halogenated C 1-C6 alkylthio C 1-C6 alkyl, C 1-C6 Alkoxycarbonyl C 1-C6 alkyl, haloC 1-C6 alkoxycarbonyl C 1-C6 alkyl, C 1-C6 alkylthio carbonyl C 1-C6 alkyl, Halogenated C 1-C6 AlkylthiocarbonylC 1-C6 alkyl, C 1-C6 Alkylcarbonyloxy, halogenated C 1-C6 Alkylcarbonyloxy, C 1-C6 Alkoxycarbonyloxy halogenated C 1-C6 alkoxy carbonyl oxygen radical C 1-C6 Alkylsulfonic acid an acyloxy group acyl oxygen a base group, C 1-C6 Alkoxy C 1-C6 Alkoxy or halo C 1-C6 Alkoxy C 1-C6 Alkoxy, R 2 is not selected from cyano or hydroxy when in the 4-position of the phenyl ring;
n is an integer from 0 to 5, and when n is 0, there is no substituent, and when n is greater than 1, R 2 are the same or different;
r 3 is selected from hydrogen, hydroxy, formyl, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 1-C6 alkoxy, Halogenated C 1-C6 alkoxy, C 3-C6 cycloalkyl, C 2-C6 alkenyl, C 2-C6 alkynyl, halogenated C 2-C6 alkenyl, Halogenated C 2-C6 alkynyl, C 1-C6 alkoxyC 1-C6 alkyl, halogenated C 1-C6 alkoxyC 1-C6 alkyl, C 1-C6 alkylthio C 1-C6 alkyl, haloC 1-C6 alkylthio C 1-C6 alkyl, C 1-C6 alkylsulfinyl, Halogenated C 1-C6 alkylsulfinyl, C 1-C6 alkylsulfonyl, halogenated C 1-C6 alkylsulfonyl, C 1-C6 alkylaminosulfonyl, di (C 1-C6 alkyl) aminosulfonyl, C 1-C6 alkylsulfonylaminocarbonyl, C 1-C6 alkylcarbonylaminosulfonyl, C 3-C6 cycloalkyloxycarbonyl, C 1-C6 Alkylcarbonyl, haloC 1-C6 Alkylcarbonyl, C 1-C6 alkoxycarbonyl, haloC 1-C6 alkoxycarbonyl, C 1-C6 Alkylcarbonyl C 1-C6 alkyl, C 1-C6 Alkoxycarbonyl C 1-C6 alkyl, C 1-C6 Alkylaminocarbonyl, Di (C 1-C6 alkyl) aminocarbonyl, C 2-C6 alkenyloxycarbonyl, C 2-C6 alkynyloxycarbonyl, C 1-C6 alkoxy C 1-C6 alkoxycarbonyl, Arylcarbonyl C 1-C6 alkyl, arylcarbonyl, aryloxycarbonyl, arylC 1-C6 alkyloxycarbonyl, arylC 1-C6 alkyl, heteroarylcarbonyl C 1-C6 alkyl, unsubstituted or substituted with 1 to 5, Heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylC 1-C6 -alkyloxycarbonyl, heteroarylC 1-C6 -alkyl, a halogen, nitro, cyano, C 1-C6 -alkyl, halo C 1-C6 -alkyl, C 1-C6 alkoxy or halo C 1-C6 alkoxy;
R 4、R5 is the same or different and is selected from hydrogen, halogen, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 1-C6 alkoxy or halogenated C 1-C6 alkoxy respectively;
wherein, the C to which R 4、R5 is attached may also form a ring of C 3-C6;
R 6、R7 is the same or different and is selected from hydrogen, halogen, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 1-C6 alkoxy or halogenated C 1-C6 alkoxy respectively;
Wherein, the C to which R 6、R7 is attached may also form a ring of C 3-C6;
q is selected from aryl, heteroaryl which is unsubstituted or substituted by 1-5R 8.
R 8 is selected from halogen, hydroxy, amino, cyano, nitro, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 1-C6 alkoxy, halogenated C 1-C6 alkoxy, C 3-C6 cycloalkyl, C 1-C6 alkylamino, halogenated C 1-C6 alkylamino, Di (C 1-C6 alkyl) amino, halo di (C 1-C6 alkyl) amino, C 1-C6 alkylthio, halo C 1-C6 alkylthio, C 2-C6 alkenyl, C 2-C6 alkynyl, C 2-C6 alkenyloxy, halogenated C 2-C6 alkenyloxy, C 2-C6 alkynyloxy, Halogenated C 2-C6 alkynyloxy, C 1-C6 alkylsulfonyl, halogenated C 1-C6 alkylsulfonyl, C 1-C6 alkylcarbonyl, Halogenated C 1-C6 alkylcarbonyl, C 1-C6 alkoxycarbonyl, halogenated C 1-C6 alkoxycarbonyl, C 1-C6 alkoxyC 1-C6 alkyl, Halogenated C 1-C6 AlkoxyC 1-C6 alkyl, C 1-C6 alkylthio C 1-C6 alkyl, halogenated C 1-C6 alkylthio C 1-C6 alkyl, C 1-C6 Alkoxycarbonyl C 1-C6 alkyl, haloC 1-C6 alkoxycarbonyl C 1-C6 alkyl, C 1-C6 alkylthio carbonyl C 1-C6 alkyl, Halogenated C 1-C6 AlkylthiocarbonylC 1-C6 alkyl, C 1-C6 Alkylcarbonyloxy, halogenated C 1-C6 Alkylcarbonyloxy, C 1-C6 Alkoxycarbonyloxy halogenated C 1-C6 alkoxy carbonyl oxygen radical C 1-C6 Alkylsulfonic acid an acyloxy group acyl oxygen a base group, C 1-C6 alkoxy C 1-C6 alkoxy or halogenated C 1-C6 alkoxy C 1-C6 alkoxy.
Further preferred, in the compounds of formula I:
R 1 is selected from the group consisting of hydrogen, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 3-C6 cycloalkyl, C 1-C6 alkoxy, halogenated C 1-C6 alkoxy, C 2-C6 alkenyl, halogenated C 2-C6 alkenyl, C 2-C6 alkynyl, halogenated C 2-C6 alkynyl;
R 2 is selected from halogen, hydroxy, amino, cyano, nitro, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy, Halogenated C 1-C4 alkoxy, C 3-C4 cycloalkyl, C 1-C4 alkylamino, halogenated C 1-C4 alkylamino, Di (C 1-C4 alkyl) amino, di (halogenated C 1-C4 alkyl) amino, C 1-C4 alkylthio, halogenated C 1-C4 alkylthio, C 2-C4 alkenyl, C 2-C4 alkynyl, C 2-C4 alkenyloxy, halogenated C 2-C4 alkenyloxy, C 2-C4 alkynyloxy, Halogenated C 2-C4 alkynyloxy, C 1-C4 alkylsulfonyl, halogenated C 1-C4 alkylsulfonyl, C 1-C4 alkylcarbonyl, Halogenated C 1-C4 alkylcarbonyl, C 1-C4 alkoxycarbonyl, halogenated C 1-C4 alkoxycarbonyl, C 1-C4 alkoxyC 1-C4 alkyl, Halogenated C 1-C4 AlkoxyC 1-C4 alkyl, C 1-C4 alkylthio C 1-C4 alkyl, halogenated C 1-C4 alkylthio C 1-C4 alkyl, C 1-C4 Alkoxycarbonyl C 1-C4 alkyl, haloC 1-C4 alkoxycarbonyl C 1-C4 alkyl, C 1-C4 alkylthio carbonyl C 1-C4 alkyl, Halogenated C 1-C4 AlkylthiocarbonylC 1-C4 alkyl, C 1-C4 Alkylcarbonyloxy, halogenated C 1-C4 Alkylcarbonyloxy, C 1-C4 Alkoxycarbonyloxy halogenated C 1-C4 alkoxy carbonyl oxygen radical C 1-C4 Alkylsulfonic acid an acyloxy group acyl oxygen a base group, C 1-C4 Alkoxy C 1-C4 Alkoxy or halo C 1-C4 Alkoxy C 1-C4 Alkoxy, R 2 is not selected from cyano or hydroxy when in the 4-position of the phenyl ring;
n is an integer from 0 to 5, and when n is 0, there is no substituent, and when n is greater than 1, R 2 are the same or different;
R 3 is selected from hydrogen, hydroxy, formyl, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy, Halogenated C 1-C4 alkoxy, C 3-C4 cycloalkyl, C 2-C4 alkenyl, C 2-C4 alkynyl, halogenated C 2-C4 alkenyl, Halogenated C 2-C4 alkynyl, C 1-C4 alkoxyC 1-C4 alkyl, halogenated C 1-C4 alkoxyC 1-C4 alkyl, c 1-C4 alkylthio C 1-C4 alkyl, haloC 1-C4 alkylthio C 1-C4 alkyl, C 1-C4 alkylsulfinyl, halogenated C 1-C4 alkylsulfinyl, C 1-C4 alkylsulfonyl, halogenated C 1-C4 alkylsulfonyl, C 1-C4 alkylaminosulfonyl, Di (C 1-C4 alkyl) aminosulfonyl, C 1-C4 alkylsulfonylaminocarbonyl, C 1-C4 alkylcarbonylaminosulfonyl, C 3-C4 cycloalkyloxycarbonyl, c 1-C4 alkylcarbonyl, halogenated C 1-C4 alkylcarbonyl, C 1-C4 alkoxycarbonyl, halogenated C 1-C4 alkoxycarbonyl;
R 4、R5 is the same or different and is selected from hydrogen, halogen, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy or halogenated C 1-C4 alkoxy respectively;
Wherein, the C to which R 4、R5 is attached may also form a ring of C 3-C4;
R 6、R7 is the same or different and is selected from hydrogen, halogen, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy or halogenated C 1-C4 alkoxy respectively;
Wherein, the C to which R 6、R7 is attached may also form a ring of C 3-C4;
Q is selected from phenyl, pyridinyl, thiophenyl, furanyl, pyrazolyl, thiazolyl, isothiazolyl, pyrazines, pyridazines, unsubstituted or substituted with 1-5R 8;
R 8 is selected from halogen, hydroxy, amino, cyano, nitro, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy, Halogenated C 1-C4 alkoxy, C 3-C4 cycloalkyl, C 1-C4 alkylamino, halogenated C 1-C4 alkylamino, Di (C 1-C4 alkyl) amino, halo di (C 1-C4 alkyl) amino, C 1-C4 alkylthio, halo C 1-C4 alkylthio, C 2-C4 alkenyl, C 2-C4 alkynyl, C 2-C4 alkenyloxy, halogenated C 2-C4 alkenyloxy, C 2-C4 alkynyloxy, Halogenated C 2-C4 alkynyloxy, C 1-C4 alkylsulfonyl, halogenated C 1-C4 alkylsulfonyl, C 1-C4 alkylcarbonyl, Halogenated C 1-C4 alkylcarbonyl, C 1-C4 alkoxycarbonyl, halogenated C 1-C4 alkoxycarbonyl, C 1-C4 alkoxyC 1-C4 alkyl, Halogenated C 1-C4 AlkoxyC 1-C4 alkyl, C 1-C4 alkylthio C 1-C4 alkyl, halogenated C 1-C4 alkylthio C 1-C4 alkyl, C 1-C4 Alkoxycarbonyl C 1-C4 alkyl, haloC 1-C4 alkoxycarbonyl C 1-C4 alkyl, C 1-C4 alkylthio carbonyl C 1-C4 alkyl, Halogenated C 1-C4 AlkylthiocarbonylC 1-C4 alkyl, C 1-C4 Alkylcarbonyloxy, halogenated C 1-C4 Alkylcarbonyloxy, C 1-C4 Alkoxycarbonyloxy halogenated C 1-C4 alkoxy carbonyl oxygen radical C 1-C4 Alkylsulfonic acid an acyloxy group acyl oxygen a base group, C 1-C4 alkoxy C 1-C4 alkoxy or halogenated C 1-C4 alkoxy C 1-C4 alkoxy.
Still further preferred, in the compounds of formula I:
R 1 is selected from the group consisting of hydrogen, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 3-C6 cycloalkyl, C 1-C6 alkoxy, halogenated C 1-C6 alkoxy, C 2-C6 alkenyl, halogenated C 2-C6 alkenyl, C 2-C6 alkynyl, halogenated C 2-C6 alkynyl;
R 2 is selected from halogen, hydroxy, amino, cyano, nitro, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy, Halogenated C 1-C4 alkoxy, C 3-C4 cycloalkyl, C 1-C4 alkylamino, halogenated C 1-C4 alkylamino, Di (C 1-C4 alkyl) amino, di (halogenated C 1-C4 alkyl) amino, C 1-C4 alkylthio, halogenated C 1-C4 alkylthio, C 2-C4 alkenyl, C 2-C4 alkynyl, C 2-C4 alkenyloxy, halogenated C 2-C4 alkenyloxy, C 2-C4 alkynyloxy, Halogenated C 2-C4 alkynyloxy, C 1-C4 alkylsulfonyl, halogenated C 1-C4 alkylsulfonyl, C 1-C4 alkylcarbonyl, Halogenated C 1-C4 alkylcarbonyl, C 1-C4 alkoxycarbonyl, halogenated C 1-C4 alkoxycarbonyl, C 1-C4 alkoxyC 1-C4 alkyl, Halogenated C 1-C4 AlkoxyC 1-C4 alkyl, C 1-C4 alkylthio C 1-C4 alkyl, halogenated C 1-C4 alkylthio C 1-C4 alkyl, C 1-C4 Alkoxycarbonyl C 1-C4 alkyl, haloC 1-C4 alkoxycarbonyl C 1-C4 alkyl, C 1-C4 alkylthio carbonyl C 1-C4 alkyl, Halogenated C 1-C4 AlkylthiocarbonylC 1-C4 alkyl, C 1-C4 Alkylcarbonyloxy, halogenated C 1-C4 Alkylcarbonyloxy, C 1-C4 Alkoxycarbonyloxy halogenated C 1-C4 alkoxy carbonyl oxygen radical C 1-C4 Alkylsulfonic acid an acyloxy group acyl oxygen a base group, C 1-C4 Alkoxy C 1-C4 Alkoxy or halo C 1-C4 Alkoxy C 1-C4 Alkoxy, R 2 is not selected from cyano or hydroxy when in the 4-position of the phenyl ring;
n is an integer from 0 to 5, and when n is 0, there is no substituent, and when n is greater than 1, R 2 are the same or different;
R 3 is selected from hydrogen, hydroxy, formyl, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy, Halogenated C 1-C4 alkoxy, C 3-C4 cycloalkyl, C 2-C4 alkenyl, C 2-C4 alkynyl, halogenated C 2-C4 alkenyl, Halogenated C 2-C4 alkynyl, C 1-C4 alkoxyC 1-C4 alkyl, halogenated C 1-C4 alkoxyC 1-C4 alkyl, c 1-C4 alkylthio C 1-C4 alkyl, haloC 1-C4 alkylthio C 1-C4 alkyl, C 1-C4 alkylsulfinyl, halogenated C 1-C4 alkylsulfinyl, C 1-C4 alkylsulfonyl, halogenated C 1-C4 alkylsulfonyl, C 1-C4 alkylaminosulfonyl, Di (C 1-C4 alkyl) aminosulfonyl, C 1-C4 alkylsulfonylaminocarbonyl, C 1-C4 alkylcarbonylaminosulfonyl, C 3-C4 cycloalkyloxycarbonyl, c 1-C4 alkylcarbonyl, halogenated C 1-C4 alkylcarbonyl, C 1-C4 alkoxycarbonyl, halogenated C 1-C4 alkoxycarbonyl;
R 4、R5 is the same or different and is selected from hydrogen, halogen, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy or halogenated C 1-C4 alkoxy respectively;
Wherein, the C to which R 4、R5 is attached may also form a ring of C 3-C4;
R 6、R7 is the same or different and is selected from hydrogen, halogen, C 1-C4 alkyl, halogenated C 1-C4 alkyl, C 1-C4 alkoxy or halogenated C 1-C4 alkoxy respectively;
Wherein, the C to which R 6、R7 is attached may also form a ring of C 3-C4;
Q is selected from the following substituents:
R 8 is selected from halogen, amino, cyano, nitro, C 1-C4 alkyl, halo C 1-C4 alkyl, C 1-C4 alkoxy, halo C 1-C4 alkoxy, C 3-C4 cycloalkyl, C 1-C4 alkylamino, halo C 1-C4 alkylamino, di (C 1-C4 alkyl) amino, halo di (C 1-C4 alkyl) amino, aminocarbonyl, di C 1-C4 alkylaminocarbonyl, dihalo C 1-C4 alkylaminocarbonyl, C 1-C4 alkylthio, halo C 1-C4 alkylthio, C 1-C4 alkylsulfonyl, halo C 1-C4 alkylsulfonyl.
M is selected from integers from 0 to 5, when m is 0, there is no substituent, and when m is greater than 1, R 8 are the same or different.
Still more preferably, the compound of formula I:
R 1 is selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl, or trifluoromethyl;
R 2 is selected from fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, R 2 is not selected from cyano or hydroxyl when in the 4-position of the benzene ring;
n is an integer from 0 to 5, and when n is 0, there is no substituent, and when n is greater than 1, R 2 are the same or different;
R 3 is selected from the group consisting of hydrogen, hydroxy, formyl, acetyl, propionyl, butyryl, trifluoroacetyl, benzoyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoroethoxy, cyclopropyloxy, allyl, propargyl, methylsulfonyl, ethylsulfonyl, trifluoroethylsulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methanesulfonylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethyleneoxycarbonyl, acetyleneoxycarbonyl;
R 4、R5 is the same or different and is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;
r 6、R7 is the same or different and is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;
Q is selected from the following substituents:
R 8 is selected from fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methylsulfonyl, ethylsulfonyl;
m is selected from integers from 0 to 5, when m is 0, there is no substituent, and when m is greater than 1, R 8 are the same or different.
Still more preferably, the compound of formula I:
r 1 is selected from hydrogen or methyl;
R 3 is selected from hydrogen;
R 2 is selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, methylthio or trifluoromethoxy, and R 2 is not selected from cyano when in the 4-position of the benzene ring.
R 4、R5 are the same or different and are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
r 6、R7 are each selected from hydrogen;
n is an integer from 0 to 5, and when n is 0, there is no substituent on the ring, and when n is greater than 1, R 2 are the same or different;
Q is selected from the following substituents:
R 8 is selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy;
m is selected from integers from 0 to 4, when m is 0, there is no substituent, and when m is greater than 1, R 8 are identical or different.
In the definition of compounds of the general formula I given above, the terms used in the collection are generally defined as follows:
Halogen means fluorine, chlorine, bromine or iodine. Alkyl, straight-chain or branched alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl, substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, and the like. Haloalkyl groups-straight-chain or branched alkyl groups in which the hydrogen atoms may be partially or completely substituted with halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl and the like. Alkylsulfinyl-straight or branched chain alkyl groups are attached to the structure via a sulfinyl (-SO-) group, such as methylsulfinyl. Haloalkyl sulfinyl, straight-chain or branched alkyl sulfinyl, wherein the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms. Haloalkylsulfonyl, a linear or branched alkylsulfonyl group in which hydrogen atoms on the alkyl group may be partially or completely substituted with halogen atoms. Alkylaminothio groups such as CH 3NHS-、C2H5 NHS-. Dialkylaminothio such as (CH 3)2NS-、(C2H5)2 NS-. Alkylaminosulfonyl: alkyl-NH-SO 2 -. dialkylaminosulfonyl (alkyl) 2-N-SO2 -. Alkyl sulfonyl aminocarbonyl, alkyl-SO 2 -NH-CO-. Alkyl carbonyl sulfamoyl, alkyl-CO-NH-SO 2 -. Alkyl carbonyl alkyl-CO-alkyl-. Alkylsulfonyloxy alkyl-S (O) 2 -O-. Haloalkylsulfonyloxy the hydrogen atoms on the alkyl group of the alkylsulfonyloxy group may be partially or completely substituted by halogen atoms, for example, CF 3-SO2 -O. Cycloalkyloxycarbonyl such as cyclopropoxycarbonyl, cyclohexyloxycarbonyl, and the like. Alkoxy groups, straight or branched chain alkyl groups, linked to the structure via an oxygen atom linkage. Haloalkoxy groups are straight-chain or branched alkoxy groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy and the like. Haloalkoxycarbonyl, the hydrogen atoms on the alkyl group of the alkoxycarbonyl group may be partially or wholly substituted with halogen atoms, such as ClCH 2CH2OCO-、CF3CH2 OCO-, etc. alkoxyalkyl-alkyl-O-alkyl-, such as CH 3OCH2 -. haloalkoxyalkyl the hydrogen atoms on the alkyl groups of the alkoxyalkyl groups may be partially or fully substituted with halogen atoms, such as ClCH 2CH2OCH2-、CF3CH2OCH2 -, and the like. Alkoxycarbonylalkyl-alkoxycarbonyl-alkyl-, such as CH 3OCOCH2 -. Haloalkoxycarbonylalkyl the hydrogen atoms on the alkyl groups of the alkoxycarbonylalkyl groups may be partially or fully substituted with halogen atoms, such as CF 3CH2OCOCH2 -. Alkylcarbonyloxy such as CH 3 COO-, etc. Haloalkylcarbonyloxy the hydrogen atoms of the alkylcarbonyloxy groups may be partially or fully substituted with halogen atoms, such as CF 3 COO-, etc. Alkoxycarbonyloxy-alkoxycarbonyl-oxy-such as CH 3 OCOO-. Haloalkoxycarbonyl oxy the hydrogen atoms on the alkyl groups of the alkoxycarbonyloxy groups may be partially or fully substituted by halogen atoms, for example CF 3 OCOO-. Alkylthiocarbonylalkyl-alkylthio carbonyl-alkyl-such as CH 3SCOCH2 -. Haloalkylthiocarbonylalkyl the hydrogen atoms on the alkyl groups of the alkylthio carbonylalkyl groups may be partially or fully substituted with halogen atoms, such as CF 3CH2SCOCH2 -. Alkoxyalkoxy groups such as CH 3OCH2 O-and the like. Haloalkoxyalkoxy-the hydrogen atoms on the alkoxy group may be partially or fully substituted with halogen atoms, such as CF 3OCH2 O-. Alkoxycarbonyl groups such as CH 3OCH2CH2 OCO-, etc. alkylthio, a straight or branched chain alkyl group, is attached to the structure via a sulfur atom linkage. Haloalkylthio-straight-chain or branched alkylthio groups in which the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogen atoms. For example, the number of the cells to be processed, chloromethylthio, dichloromethylthio trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, and the like. Alkylthioalkyl-alkyl-S-alkyl-, such as CH 3SCH2 -. Haloalkylthioalkyl the hydrogen atoms on the alkyl groups of the alkylthio alkyl groups may be partially or fully substituted with halogen atoms, such as ClCH 2CH2SCH2-、CF3CH2SCH2 -, and the like. alkylamino, straight or branched chain alkyl, is attached to the structure via a nitrogen atom linkage. Haloalkylamino: straight or branched alkylamino, the hydrogen atoms on these alkyl groups may be partially or fully substituted with halogen atoms. Dialkylamino groups such as (CH 3)2N-,(CH3CH2)2 N-halodialkylamino groups: the hydrogen atoms on the alkyl groups can be partially or completely substituted by halogen atoms, such as (CF 3)2N-,(CF3CH2)2 N-). Alkenyl groups are straight-chain or branched alkenyl groups such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl groups also include polyenes such as 1, 2-allenyl and 2, 4-hexadienyl. Haloalkenyl groups are linear or branched alkenyl groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenyloxy, a straight or branched chain alkene, linked to the structure via an oxygen atom linkage. Halogen alkenyloxy-straight-chain or branched alkenyloxy, the hydrogen atoms on these alkenyloxy groups may be partially or completely replaced by halogen atoms. Alkenylthio, a straight or branched chain alkene, linked to the structure via a sulfur atom linkage. Such as CH 2＝CHCH2 S-. Alkenyloxycarbonyl such as CH 2＝CHCH2 OCO-, and the like. Alkynyl groups are straight-chain or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. Alkynyl also includes groups consisting of multiple triple bonds, such as 2, 5-hexadiynyl. Haloalkynyl-straight-chain or branched alkynes in which the hydrogen atoms may be partially or fully replaced by halogen atoms. alkynyloxy, a straight or branched chain alkyne, linked to the structure via an oxygen atom bond. Haloalkynyloxy-linear or branched alkynyloxy, the hydrogen atoms on these alkynyloxy groups may be partially or fully substituted with halogen atoms. Alkynyloxycarbonyl groups such as CH.ident.CCH 2 OCO-, and the like. Alkylsulfonyl, a straight or branched chain alkyl group is attached to a structure, such as methylsulfonyl, through a sulfonyl group (-SO 2 -). Haloalkylsulfonyl, a linear or branched alkylsulfonyl group in which hydrogen atoms on the alkyl group may be partially or completely substituted with halogen atoms. Alkylcarbonyl alkyl is attached to the structure via a carbonyl group, such as CH 3CO-,CH3CH2 CO-. Haloalkylcarbonyl the hydrogen atoms on the alkyl groups of the alkylcarbonyl group may be partially or fully substituted by halogen atoms, such as CF 3 CO-. Alkoxycarbonyl groups, alkoxy groups are attached to the structure via a carbonyl group. Such as CH 3OCO-,CH3CH2 OCO-. Aminocarbonyl groups such as NH 2 CO-. Alkylaminocarbonyl alkyl-NH-CO-, such as CH 3NHCO-,CH3CH2 NHCO-. Dialkylaminocarbonyl groups such as (CH 3)2NCO-,(CH3CH2)2 NCO-. the aryl moiety in the (hetero) aryl, (hetero) arylalkyl, (hetero) arylcarbonyl, (hetero) arylmethylcarbonyl, (hetero) arylcarbonylalkyl, (hetero) aryloxycarbonyl, (hetero) arylalkyloxycarbonyl includes phenyl or naphthyl, and the like. Heteroaryl is a five-membered or six-membered ring containing 1 or more N, O, S heteroatoms. Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and the like. (hetero) aryl groups such as phenyl and the like. (hetero) arylalkyl groups such as benzyl, phenethyl, p-chlorobenzyl, 2-chloropyridin-5-yl, 2-chloro-thiazol-5-yl and the like. (hetero) arylcarbonyl groups such as benzoyl, 4-chlorobenzoyl and the like. (hetero) arylmethylcarbonyl groups such as PhCH 2 CO-. (hetero) arylcarbonylalkyl groups such as PhCOCH 2 -. (hetero) aryloxycarbonyl such as phenoxycarbonyl, 4-chlorophenoxycarbonyl, 4-nitrophenoxycarbonyl, naphthyloxycarbonyl and the like. Arylalkyloxycarbonyl such as benzyloxycarbonyl, 4-chlorobenzyloxycarbonyl, 4-trifluoromethyl benzyloxycarbonyl and the like. (hetero) arylalkyl-oxycarbonyl groups such as PhCH 2OCO-、4-Cl-PhCH2 OCO-, and the like.
Table 1, table 2, table 3, table 4, table 5 show some of the specific substituents of R 1、R3、R4 and R 5、R6 and R 7 and Q in the general formula I, respectively, but they are not limited to these substituents.
TABLE 1R 1 substituents
R8 R8 R8 R8
H CN CH3 C2H5
n-C3H7 i-C3H7 n-C4H9 s-C4H9
i-C4H9 t-C4H9 CF3 CCl3
CHF2 CH2F CH2Cl CH2CF3
CF2CF3 COOCH3 Ph Ph-4-Cl
TABLE 2R 3 substituents
Table 3R 4(R5) substituents
Table 4R 6(R7) substituents
TABLE 5Q substituents
Some of the compounds of the present invention may be described using the specific compounds listed in tables 6-34, but are not limiting to the invention. In the general formula compound I referred to in the table, R 1＝R3＝R4＝R5＝R6＝R7 =h.
In the general formula I, when the five-membered ring is a double bond, the general formula structure is as follows:
in the general formula I-1, when Q=Q1, (R 2)n substituent is shown in table 6, and the serial numbers of the representative compounds are 6-1 to 6-288 in sequence.
TABLE 6
In the general formula I-1, when Q=Q2, the substituents (R 2)n is identical to the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 7-1-7-288 in the order shown in Table 6).
In the general formula I-1, when Q=Q3, the substituents (R 2)n is identical to the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 8-1-8-288 in the order shown in Table 6).
In the general formula I-1, when Q=Q4, the substituents (R 2)n is identical to the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 9-1-9-288 in the order shown in Table 6).
In the general formula I-1, when Q=Q5, the substituents (R 2)n is identical to the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 10-1-10-288 in the order shown in Table 6).
In the general formula I-1, when Q=Q6, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 11-1-11-288 in the order shown in Table 6).
In the general formula I-1, when Q=Q7, the substituents (R 2)n is identical to the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 12-1-12-288 in the order shown in Table 6).
In the general formula I-1, when Q=Q8, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 13-1-13-288 in the order shown in Table 6).
Table 14 in the general formula I-1, when Q=Q9, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 14-1-14-288 in the order shown in Table 6).
In the general formula I, when the five-membered ring is a single bond, the general formula structure is as follows:
In the general formula I-2, when Q=Q1, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 15-1-15-288 in the order shown in Table 6).
In the general formula I-2, when Q=Q2, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 16-1-16-288 in the order shown in Table 6).
In the general formula I-2, when Q=Q3, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 17-1-17-288 in the order shown in Table 6).
In the general formula I-2, when Q=Q4, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 18-1-18-288 in the order shown in Table 6).
In the general formula I-2, when Q=Q5, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 19-1-19-288 in the order shown in Table 6).
In the general formula I-2, when Q=Q6, the substituents (R 2)n is identical to the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 20-1-20-288 in the order shown in Table 6).
In the general formula I-2, when Q=Q7, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 21-1-21-288 in the order shown in Table 6).
In the general formula I-2, when Q=Q8, the substituents (R 2)n is identical to the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 22-1-22-288 in the order shown in Table 6).
In the general formula I-2, when Q=Q9, the substituents (R 2)n is the same as the substituents shown in Table 6, the substituents correspond to 6-1-6-288 in the order shown in Table 6, and the numbers of the representative compounds are 23-1-23-288 in the order shown in Table 6).
In the general formula I-1, when q=q1, the substituent R 3 (when not hydrogen) is a different substituent as shown in table 24, and the numbers of representative compounds are 24-1 to 24-140 in sequence.
Table 24
The compounds of the invention are prepared according to the following method, wherein the reaction formula is as follows, and each group is defined as before unless otherwise indicated:
The preparation of the compound of the general formula I adopts the following method:
The intermediates II and III are reacted under basic conditions in a suitable solvent to give the compounds of the general formula I.
Suitable bases may be selected from, for example, triethylamine, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide, or sodium tert-butoxide, and the like.
The reaction is carried out in a suitable solvent which may be selected from, for example, methylene chloride, tetrahydrofuran, 1, 4-dioxane, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetone or butanone.
The reaction temperature may be between room temperature and the boiling temperature of the solvent, typically 20-100 ℃.
The reaction time is 30 minutes to 20 hours, usually 1 to 10 hours.
Intermediate III is commercially available and can be prepared by known methods, such as CN108947892, journal of MEDICINAL CHEMISTRY,46 (23), 4895-4903;2003 and the like.
Intermediate II is a key intermediate for preparing the compounds of the general formula I according to the invention, and is prepared as follows:
4-Bromobutylkyne is reacted with a potassium phthalimide salt in a suitable solvent at a suitable temperature for 30 minutes to 20 hours, typically 1 to 10 hours, to give intermediate M1, which is described in WO2002028395 and Organic Letters,7 (4), 733-736;2005; 4-chlorobenzaldehyde oxime is chlorinated and reacted with M1 in a suitable solvent under alkaline conditions to give M2, which is described in WO2006065280 and Chemical Communications (Cambridge, united Kingdom), 47 (11), 3198-3200;2011; M2 is deaminated in a suitable solvent under alkaline conditions to give II, which is described in European Journal of Organic Chemistry,2013 (23), 5143-5148;2013 and WO2016011209 etc.
Although the compounds of formula I of the present invention also belong to the class of substituted isoxazoleethylamines with certain compounds disclosed in the prior art, there is still a significant difference in structural features. And the compounds of the present invention have better bactericidal activity due to these structural differences.
The compounds of the general formula I show excellent activity against various germs in agriculture or other fields, and therefore, the technical scheme of the invention also comprises the application of the compounds of the general formula I in preparing bactericides in agriculture or other fields.
The following examples of diseases are only illustrative of the present invention, but are in no way limiting.
The compounds of the general formula I can be used for controlling oomycetes diseases, such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, luffa downy mildew, white gourd downy mildew, melon downy mildew, cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, cabbage white rust), damping-off (rape damping-off, tobacco damping-off, eggplant damping-off, chilli damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cotton rot (chilli cotton rot, luffa cotton rot, white gourd cotton rot), epidemic (broad bean epidemic), Bacterial diseases such as wilt (sweet potato wilt, cotton wilt, sesame wilt, castor wilt, tomato wilt, bean wilt, cucumber wilt, luffa, pumpkin wilt, winter melon wilt, watermelon wilt, melon wilt, capsicum wilt, broad bean wilt, rape wilt, soybean wilt), root rot (capsicum root rot, eggplant root rot, bean root rot, cucumber root rot), etc, Bitter gourd root rot, cotton black root rot, broad bean root rot), damping off (cotton seedling damping off, sesame damping off, pepper damping off, cucumber damping off, cabbage damping off), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, sang Tanju, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, bitter gourd anthracnose, pumpkin anthracnose, white gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, sunflower verticillium wilt, tomato verticillium wilt, capsicum verticillium wilt, eggplant verticillium), black star (pumpkin black star), White gourd scab, melon scab), gray mold (cotton boll gray mold, kenaf gray mold, tomato gray mold, pepper gray mold, bean gray mold, celery gray mold, spinach gray mold, kiwi gray mold), brown spot (cotton brown spot, jute brown spot, beet brown spot, peanut brown spot, pepper brown spot, white gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot, broad bean brown spot), black spot disease (flax black spot disease, rape black spot disease, sesame black spot disease, sunflower black spot disease, castor black spot disease, tomato black spot disease, pepper black spot disease, eggplant black spot disease, bean black spot disease, cucumber black spot disease, celery black spot disease), Carrot black rot, carrot black spot, apple black spot, peanut black spot), spot blight (tomato spot, pepper spot, celery spot), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean ring spot, sesame ring spot, bean ring spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), stem rot (bean stem rot, kidney bean stem rot), and others (maize round spot, kenaf waist folding, rice blast, chestnut black sheath, sugarcane eye spot, cotton boll leaf mold, peanut crown rot), Soybean stem blight, soybean black spot, melon and leaf spot, peanut web spot, tea red leaf spot, pepper white spot, white gourd leaf spot, celery black rot, spinach heart rot, kenaf leaf mold, kenaf leaf spot, jute stem spot, soybean purple spot, sesame leaf spot, castor bean gray spot, tea brown leaf spot, eggplant brown round spot, bean red spot, balsam pear white spot, watermelon spot, jute seed cake, rhizome rot, bean carbon rot, soybean target spot, eggplant rod leaf spot, cucumber target spot, leaf spot, eggplant leaf mold, broad bean red spot, etc.), basidiomycetes diseases such as rust (wheat stripe rust, wheat straw rust, basidiomycetes, etc. Wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust, and the like, smut (maize head smut, maize smut, sorghum head smut, sorghum loose smut, sorghum smut, gao Liangzhu smut, chestnut grain smut, sugarcane smut, bean rust, and the like); ascomycete diseases such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, luffa powdery mildew, pumpkin powdery mildew, white gourd powdery mildew, Melon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia (flax sclerotinia, rape sclerotinia, soybean sclerotinia, peanut sclerotinia, tobacco sclerotinia, capsicum sclerotinia, eggplant sclerotinia, bean sclerotinia, pea sclerotinia, cucumber sclerotinia, balsam pear sclerotinia, wax gourd sclerotinia, watermelon sclerotinia, celery sclerotinia), cladosporium (apple cladosporium, pear cladosporium) and the like.
Due to their positive properties, the above-mentioned compounds can be advantageously used for protecting crops, domestic animals and breeding stock of agricultural and horticultural importance, as well as the environment normally seen by humans, from pathogens, harmful insects and mites.
The amount of the compound used to achieve the desired effect will vary depending upon a variety of factors, such as the compound used, the crop to be protected, the type of pest, the degree of infection, the climatic conditions, the method of application, the dosage form employed.
A dosage of 10 g-5 kg of compound per hectare provides adequate control.
The technical scheme of the invention also comprises a method for preventing and controlling pathogenic bacteria and pest mites, wherein the bactericidal, insecticidal and acaricidal compound is applied to the pathogenic bacteria or growth media thereof. A more suitable effective amount is typically selected from 10 to 1000 grams per hectare, with an effective amount of 20 to 500 grams per hectare being preferred.
For certain applications, such as agriculture, one or more other bactericides, acaricides, herbicides, plant growth regulators or fertilizers and the like may be added to the bactericidal, insecticidal and acaricidal compositions of the invention, thereby producing additional advantages and effects.
Detailed Description
The following examples are provided to further illustrate the invention, but the invention is by no means limited to these examples (all materials are commercially available unless otherwise noted).
Synthetic examples
Example 1 preparation of intermediate 2- (3- (4-p-chlorophenyl) isoxazol-5-yl) -1-ethylamine
1) Preparation of N- (3-butyne) phthalimide
13.30G (0.10 mol) of 4-bromobutyne and 18.5g (0.1 mol) of phthalimide potassium salt are put into 100ml of N, N-dimethylformamide solvent under stirring at room temperature, 50-100ml of water is added into the reaction liquid after stirring and reacting for 5-7 hours at 60 ℃, and the white solid is obtained by suction filtration and water washing, and the yield is 92%.
2) Preparation of 2- (3- (4-p-chlorophenyl) isoxazol-5-yl) -1-ethylamine
15.5G (0.1 mol) of 4-chlorobenzaldehyde oxime was dissolved in 50ml of N, N-dimethylformamide, 14.7g (0.11 mol) of NCS was added to the reaction flask in portions with stirring, the reaction was carried out at 50℃for 3 to 4 hours, after TLC monitoring the complete reaction of 4-chlorobenzaldehyde oxime, 19.9g (0.1 mol) of N- (3-butyne) phthalimide and 8.4g (0.1 mol) of sodium hydrogencarbonate were added, the reaction was continued for 4 hours, after TLC monitoring the reaction was completed, the reaction solution was poured into water with stirring for 30 minutes, and filtered and washed with water to obtain 13.2g of a white solid, the yield of which was 37.4%.
The white solid obtained above was dissolved in 300ml THF and 60ml DCM, 9.4g hydrazine hydrate was added and reacted for 3-4 hours at 50 ℃, after TLC monitoring that N- (2- (3- (4-chlorophenyl) isoxazol-5-yl) ethyl) phthalimide was completely reacted, cooled, filtered, the filtrate was concentrated under reduced pressure, DCM was added to dissolve, the organic phase was washed with sodium hydroxide solution, dried over anhydrous magnesium sulfate to obtain 7.3g of 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine as a pale yellow solid, and the yield was 87.6%.
EXAMPLE 2 preparation of intermediates
1) Preparation of N- (3-butene) phthalimide
13.50G (0.10 mol) of 4-bromobutyne and 18.5g (0.1 mol) of phthalimide potassium salt are put into 100ml of N, N-dimethylformamide solvent under stirring at room temperature, 50-100ml of water is added into the reaction liquid after stirring and reacting for 5-7 hours at 60 ℃, and 17.6g of white solid is obtained after suction filtration and water washing, and the yield is 87.6%.
2) Preparation of 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine
15.5G (0.1 mol) of 4-chlorobenzaldehyde oxime was dissolved in 50ml of N, N-dimethylformamide, 14.7g (0.11 mol) of NCS was added to the reaction flask in portions with stirring, the reaction was carried out at 50℃for 3 to 4 hours, after TLC monitoring the complete reaction of 4-chlorobenzaldehyde oxime, 20.1g (0.1 mol) of N- (3-butyne) phthalimide and 8.4g (0.1 mol) of sodium hydrogencarbonate were added, the reaction was continued for 4 hours, after TLC monitoring the reaction was completed, the reaction solution was poured into water with stirring for 30 minutes, and filtered and washed with water to obtain 14.3g of a white solid with a yield of 40.3%.
The white solid obtained above was dissolved in 300ml THF and 60ml DCM, 10g hydrazine hydrate was added and reacted at 50 ℃ for 3-4 hours, after TLC monitoring that N- (2- (3- (4-chlorophenyl) isoxazol-5-yl) ethyl) phthalimide was completely reacted, cooled, filtered, the filtrate was concentrated under reduced pressure, DCM was added to dissolve, the organic phase was washed with sodium hydroxide solution, dried over anhydrous magnesium sulfate to give 6.9g of 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine as a pale yellow solid, yield 76.2%.
EXAMPLE 3 preparation of Compounds 6-19
0.22G (10 mmol) of 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine was dissolved in 20ml of acetonitrile, 0.23g (11 mol) of o-trifluoromethylbenzoyl chloride dissolved in 5ml of acetonitrile was dropwise added to the reaction flask with stirring, the reaction was carried out at room temperature for 3 to 4 hours, after the completion of the TLC monitoring, the solvent was distilled off under reduced pressure, ethyl acetate was added (3X 50 ml) to extract, the organic phase was washed with 50ml of saturated brine, and the residue after desolventizing was column-chromatographed to give 0.24g of yellow oil in 60.8% yield.
1 H-NMR (600 MHz, internal standard TMS, solvent CDCl3)δ(ppm):7.69(m,3H),7.54(m,2H),7.50(m,1H),7.42(m,2H),6.41(s,1H),6.15(s,1H),3.85(m,2H),3.17(m,2H).)
EXAMPLE 4 preparation of Compounds 16-19
0.22G (10 mmol) of 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine was dissolved in 20ml of acetonitrile, 0.24g (11 mol) of o-trifluoromethylbenzoyl chloride dissolved in 5ml of acetonitrile was dropwise added to the reaction flask with stirring, the reaction was carried out at room temperature for 3 to 4 hours, after the completion of the TLC monitoring, the solvent was distilled off under reduced pressure, ethyl acetate was added (3X 50 ml) to extract, the organic phase was washed with 50ml of saturated brine, and the residue after desolventizing was column-chromatographed to give 0.20g of a white solid in a yield of 49.4%.
1 H-NMR (600 MHz, internal standard TMS, solvent CDCl3)δ(ppm):δ(CDCl3):7.61(m,2H),7.50(s,1H),7.40(m,2H),4.92(m,1H),3.82(m,1H),3.62(m,1H),3.55(m,1H),3.05(m,1H),2.05(m,2H).)
Other compounds of the invention can be prepared with reference to the above examples.
Physical property data and nuclear magnetic data (1 HNMR,600MHz, internal standard TMS, ppm) of a part of the compounds are as follows:
compounds of formula (I) 6-1:oil.δ(CDCl3):7.74(m,2H),7.68(m,1H),7.54(m,3H),7.43(m,3H),6.42(s,1H),6.24(s,1H),3.85(m,2H),3.17(m,2H).
Compounds of formula (I) 6-4:oil.δ(CDCl3):7.79(m,2H),7.68(m,1H),7.57(m,2H),7.52(m,1H),7.28(m,2H),6.42(s,1H),6.16(s,1H),3.85(m,2H),3.18(m,2H).
Compound 6-17 melting point 96.0℃.δ(CDCl3):7.70(m,2H),7.58(m,1H),7.53(m,2H),7.48(m,1H),7.39(m,1H),7.34(m,1H),6.59(s,1H),6.09(s,1H),3.87(m,2H),3.21(m,2H).
Compounds of formula (I) 6-21:oil.δ(CDCl3):7.70(m,1H),7.66(m,1H),7.59(m,2H),7.54(m,2H),7.34(m,1H),6.59(s,1H),6.08(s,1H),3.87(m,2H),3.21(m,2H).
Compounds of formula (I) 6-49:oil.δ(CDCl3):7.90(m,2H),7.75(m,2H),7.70(m,1H),7.55(m,2H),7.25(m,1H),6.50(s,1H),6.07(s,1H),3.88(m,2H),3.21(m,2H).
Compounds of formula (I) 6-57:oil.δ(CDCl3):7.67(m,1H),7.62(m,2H),7.47(m,2H),7.45(m,1H),7.22(m,2H),6.38(s,1H),6.28(s,1H),3.83(m,2H),3.13(m,2H),2.38(s,3H).
Compound 6-55 melting point 90.8℃.δ(CDCl3):7.69(m,1H),7.57(m,1H),7.52(m,2H),7.45(m,1H),7.33(m,1H),7.26(m,2H),6.30(s,1H),6.16(s,1H),3.86(m,2H),3.18(m,2H),2.45(s,3H).
Compounds of formula (I) 6-60:oil.δ(CDCl3):7.70(m,1H),7.58(m,1H),7.53(m,2H),7.29(s,1H),7.16(m,2H),6.29(s,1H),6.15(s,1H),3.86(m,2H),3.18(m,2H),2.40(s,3H),2.34(s,3H).
Compounds 6 to 69, melting point 153.9℃.δ(CDCl3):7.90(m,2H),7.70(m,3H),7.59(m,1H),7.52(m,2H),6.49(s,1H),6.08(s,1H),3.88(m,2H),3.21(m,2H).
Compounds of formula (I) 6-78:oil.δ(CDCl3):7.72(m,2H),7.68(m,1H),7.54(m,2H),7.48(m,1H),7.12(m,2H),6.39(s,1H),6.22(s,1H),3.84(m,2H),3.16(m,2H).
Compound 6-151 melting point 117.0℃.δ(CDCl3):7.70(m,2H),7.58(m,1H),7.53(m,2H),7.24(m,1H),7.08(m,1H),6.57(s,1H),6.07(s,1H),3.87(m,2H),3.20(m,2H).
Compound 7-4, melting point 161.8 ℃. Delta (CDCl 3): 7.77 (m, 2H), 7.15 (m, 2H), 7.12 (s, 1H), 6.40 (s, 1H), 3.90 (m, 2H), 3.20 (m, 2H).
Compounds 7-19 delta (CDCl 3) 7.72 (m, 2H), 7.44 (m, 2H), 7.12 (s, 1H), 6.41 (s, 1H), 3.90 (m, 2H), 3.21 (m, 2H).
Compounds of formula (I) 9-19:oil.δ(CDCl3):8.61(m,1H),8.22(m,1H),7.71(m,3H),7.43(m,2H),6.48(s,1H),6.20(s,1H),3.90(m,2H),3.24(m,2H),3.11(s,3H).
Compounds of formula (I) 10-19:δ(CDCl3):7.91(s,1H),7.71(m,2H),7.43(m,2H),6.81(t,1H),6.59(s,1H),6.39(s,1H),3.91(s,3H),3.80(m,2H),3.14(m,2H).
Compounds of formula (I) 10-21:oil.δ(CDCl3):7.90(s,1H),7.58(m,1H),7.47(m,1H),7.31(m,1H),6.80(t,1H),6.58(s,1H),6.41(s,1H),3.90(s,3H),3.81(m,2H),3.15(m,2H).
Compound 11-4 melting point 103.9.δ(CDCl3):7.74(m,2H),7.29(m,2H),7.24(m,1H),7.13(m,2H),6.43(s,1H),6.15(s,1H),3.90(m,2H),3.21(m,2H).
Compounds of formula (I) 11-19:δ(CDCl3):7.70(m,2H),7.43(m,2H),7.25(m,3H),6.45(s,1H),6.10(s,1H),3.90(m,2H),3.22(m,2H).
Compound 12-4, melting Point 126℃.δ(CDCl3):8.45(m,1H),8.08(m,1H),7.76(m,2H),7.34(m,1H),7.15(m,2H),6.76(s,1H),6.41(s,1H),3.90(m,2H),3.21(m,2H).
Compounds of formula (I) 12-19:δ(CDCl3):8.451(d,1H),7.72(m,2H),7.65(s,1H),7.51(m,1H),7.43(m,1H),6.55(s,1H),6.40(s,1H),3.87(m,2H),3.19(m,2H).
Compounds of formula (I) 13-19:oil.δ(CDCl3):7.71(m,2H),7.34(m,2H),6.28(s,1H),6.29(s,1H),6.24(s,1H),4.10(s,3H),3.78(m,2H),3.15(m,2H),2.23(s,3H).
Compounds of formula (I) 14-19:δ(CDCl3):7.70(m,2H),7.42(m,2H),6.40(s,1H),6.39(s,1H),3.83(m,2H),3.16(m,2H),2.72(s,3H).
Compounds of formula (I) 15-4:oil.δ(CDCl3):7.68(m,1H),7.63(m,2H),7.58(m,1H),7.53(m,2H),7.45(s,1H),7.09(m,1H),6.37(s,1H),4.87(m,1H),3.70(m,1H),3.61(m,1H),3.48(m,1H),3.06(m,1H),2.09(m,1H),1.98(m,1H).
Compounds of formula (I) 15-17:oil.δ(CDCl3):7.69(m,1H),7.59(m,2H),7.53(m,2H),7.43(m,1H),7.35(m,1H),7.30(m,1H),6.33(s,1H),4.90(m,1H),3.73(m,1H),3.63(m,2H),3.25(m,1H),2.10(m,1H),2.04(m,1H).
Compounds of formula (I) 15-19:δ(CDCl3):7.70(m,1H),7.63(m,2H),7.58(m,3H),7.38(m,2H),6.31(s,1H),4.88(m,1H),3.70(m,2H),3.50(m,1H),3.05(m,1H),2.05(m,2H),.
Compounds 15 to 21 melting Point 102.2℃.δ(CDCl3):7.69(m,1H),7.55(m,4H),7.45(s,1H),7.28(m,1H),6.30(s,1H),4.90(m,1H),3.71(m,1H),3.62(m,2H),3.22(m,1H),2.05(m,2H).
Compounds of formula (I) 15-60:oil.δ(CDCl3):7.70(m,1H),7.58(m,1H),7.52(m,2H),7.15(m,2H),7.11(m,1H),6.33(s,1H),4.81(m,1H),3.74(m,1H),3.60(m,1H),3.55(m,1H),3.13(m,1H),2.48(s,3H),2.34(s,3H),2.09(m,1H),1.99(m,1H).
Compounds 15 to 69, melting point 139℃.δ(CDCl3):7.77(m,2H),7.70(m,1H),7.66(m,2H),7.60(m,1H),7.54(m,2H),6.26(s,1H),4.94(m,1H),3.71(m,1H),3.64(m,1H),3.53(m,1H),3.10(m,1H),2.13(m,1H),2.02(m,1H).
Compounds of formula (I) 15-78:oil.δ(CDCl3):7.68(m,3H),7.58(m,1H),7.53(m,2H),7.25(m,2H),6.37(s,1H),4.89(m,1H),3.68(m,1H),3.61(m,1H),3.50(m,1H),3.06(m,1H),2.09(m,1H),1.99(m,1H).
Compounds 15 to 151 melting Point 60.5℃.δ(CDCl3):7.69(m,1H),7.60(m,2H),7.53(m,2H),7.18(m,1H),7.03(m,1H),6.31(s,1H),4.90(m,1H),3.73(m,1H),3.61(m,2H),3.22(m,1H),2.10(m,1H),2.01(m,1H).
Compounds of formula (I) 15-288:oil.δ(CDCl3):7.69(m,1H),7.58(m,3H),7.52(m,2H),7.42(m,2H),6.35(s,1H),4.85(m,1H),3.73(m,1H),3.61(m,1H),3.50(m,1H),3.06(m,1H),2.09(m,1H),1.97(m,1H),1.33(s,3H).
Compounds of formula (I) 16-4:oil.δ(CDCl3):7.65(m,2H),7.51(s,1H),7.11(m,2H),4.90(m,1H),3.83(m,1H),3.62(m,1H),3.52(m,1H),3.06(m,1H),2.12(m,1H),2.02(m,1H).
Compounds of formula (I) 16-17:oil.δ(CDCl3):7.60(m,1H),7.52(s,1H),7.43(m,1H),7.37(m,1H),7.31(m,1H),4.93(m,1H),3.85(m,1H),3.65(m,2H),3.26(m,1H),2.07(m,2H).
Compounds 16 to 21, melting Point 112.8℃.δ(CDCl3):7.59(m,1H),7.48(s,1H),7.45(m,1H),7.30(m,1H),4.93(m,1H),3.84(m,1H),3.63(m,2H),3.24(m,1H),2.07(m,2H).
Compounds of formula (I) 16-60:oil.δ(CDCl3):7.58(s,1H),7.16(m,1H),7.12(m,2H),4.85(m,1H),3.85(m,1H),3.63(m,1H),3.57(m,1H),3.12(m,1H),2.49(s,3H),2.34(s,3H),2.09(m,1H),2.01(m,1H).
Compounds 16 to 69, melting point 104.8℃.δ(CDCl3):7.78(m,3H),7.67(m,2H),7.47(s,1H),4.96(m,1H),3.83(m,1H),3.62(m,1H),3.54(m,1H),3.09(m,1H),2.14(m,1H),2.04(m,1H).
Compounds of formula (I) 16-78:oil.δ(CDCl3):7.70(m,2H),7.50(s,1H),7.25(m,2H),4.93(m,1H),3.83(m,1H),3.63(m,1H),3.52(m,1H),3.07(m,1H),2.13(m,1H),2.02(m,1H).
Compounds 16 to 151 melting point 106.1℃.δ(CDCl3):7.63(m,1H),7.50(s,1H),7.19(m,1H),7.05(m,1H),4.92(m,1H),3.85(m,1H),3.63(m,2H),3.24(m,1H),2.07(m,2H).
Compounds 16 to 288, melting point 142℃.δ(CDCl3):7.60(m,2H),7.54(s,1H),7.43(m,2H),4.89(m,1H),3.84(m,1H),3.63(m,1H),3.52(m,1H),3.07(m,1H),2.11(m,1H),2.00(m,1H),1.33(s,3H).
Compounds 17 to 19, melting Point 184.1℃.δ(CDCl3):8.00(d,1H),7.88(m,1H),7.80(m,1H),7.59(m,2H),7.40(m,2H),6.69(s,1H),4.92(m,1H),3.80(m,1H),3.64(m,1H),3.51(m,1H),3.08(m,4H),2.13(m,1H),2.03(m,1H).
Compounds 18 to 19, melting Point 189.1℃.δ(CDCl3):8.60(d,1H),8.22(m,1H),7.78(m,1H),7.57(m,2H),7.39(m,2H),6.65(s,1H),4.92(m,1H),3.79(m,1H),3.63(m,1H),3.52(m,1H),3.12(s,3H),3.08(m,1H),2.14(m,1H),2.02(m,1H).
Compounds of formula (I) 19-19:δ(CDCl3):7.88(s,1H),7.59(m,2H),7.37(m,2H),6.90(t,1H),6.64(s,1H),4.87(m,1H),3.93(s,3H),3.61(m,2H),3.46(m,1H),3.03(m,1H),2.03(m,2H).
Compounds of formula (I) 20-19:δ(CDCl3):7.57(m,2H),7.37(m,2H),7.25(m,3H),6.27(s,1H),4.93(m,1H),3.68(m,2H),3.48(m,1H),2.07(m,2H).
Compounds of formula (I) 21-19:δ(CDCl3):8.52(d,1H),7.71(m,1H),7.60(m,2H),7.54(m,1H),7.39(m,2H),6.97(s,1H),4.92(m,1H),3.82(m,1H),3.56(m,2H),3.07(m,1H),2.05(m,2H).
Compounds of formula (I) 22-19:oil.δ(CDCl3):7.70(m,2H),7.35(m,2H),6.29(s,1H),6.27(s,1H),6.24(s,1H),4.11(s,3H),3.79(m,2H),3.16(m,2H),2.23(s,3H).
Compounds of formula (I) 23-19:δ(CDCl3):7.58(m,2H),7.38(m,2H),6.64(s,1H),4.86(m,1H),3.62(m,2H),3.48(m,1H),3.05(m,1H),2.74(s,3H),2.01(m,2H).
Meanwhile, other compounds represented by the general formula I of the present invention can be obtained by substituting the corresponding raw materials according to the descriptions in the above synthesis examples.
Biological Activity assay example
The compound of the invention has good activity on various germs in the agricultural field.
Example 5 determination of Bactericidal Activity
The compound sample is used for carrying out in-vitro antibacterial activity or in-vivo protection effect test on various fungal diseases of plants. The results of the bactericidal activity measurement are shown in the following examples.
(1) In vitro bactericidal activity assay
The assay method comprises dissolving a sample of a compound to be tested in a suitable solvent (such as acetone, methanol, DMF, etc., and selected according to its ability to dissolve the sample) to obtain a desired concentration of the solution to be tested. Under the ultra-clean working environment, the liquid to be detected is added into the micropores of the 96-hole culture plate, then the pathogenic bacteria propagule suspension is added into the micropores, and the treated culture plate is placed in a constant temperature incubator for culture. Investigation was performed 24 hours later, and the germination or growth of the pathogenic bacteria propagules was visually examined at the time of investigation, and the bacteriostatic activity of the compound was evaluated according to the germination or growth of the control treatment.
The results of the in vitro bacteriostatic activity (expressed as inhibition) test for some compounds are as follows:
Inhibition rate of rice blast germ:
At the dosage of 25ppm, the compound provided by the invention has good inhibition rate to rice blast, for example, the inhibition rate to rice blast is more than 80% for compounds 12-19 and the like.
(2) Living body protective Activity assay
The measurement method comprises dissolving a sample of a compound to be measured in a small amount of solvent (such as acetone, methanol, DMF, etc., and selected according to its solubility to the sample) with a volume ratio of solvent amount to spray amount equal to or less than 0.05, and diluting with water containing 0.1% Tween 80 to obtain a desired concentration of the solution to be measured. The liquid to be tested is sprayed on the disease host plants (the host plants are standard pot seedlings cultivated in a greenhouse) on a crop sprayer, and disease inoculation is carried out after 24 hours. According to the disease characteristics, the disease plants needing to be subjected to temperature control and moisture preservation culture are inoculated and then placed in a climatic chamber for culture, after the infection of the disease is completed, the disease plants are transferred into a greenhouse for culture, and the disease plants not needing to be subjected to moisture preservation culture are directly inoculated and cultured in the greenhouse. The disease control effect of the compound is assessed after the control is sufficiently ill (typically a week).
The results of the in vivo protective activity test for some compounds are as follows:
(1) Downy mildew of cucumber
The compound provided by the invention has good inhibition rate on cucumber downy mildew at 400ppm dosage, for example, the compound 6-1、6-4、6-19、6-57、6-78、6-288、7-4、10-21、11-4、12-4、12-19、13-19、14-19、15-19、15-21、15-151、15-69、16-4、16-17、16-19、16-21、16-60、16-69、16-78、16-151、16-288、19-19、20-19、21-19、23-19 and the like have the control effect on cucumber downy mildew of more than 80 percent;
at the dosage of 100ppm, the compounds 6-19, 6-288, 12-19, 13-19, 16-69 and 16-151 have good inhibition rate on cucumber downy mildew, and the control effect on the cucumber downy mildew is more than 85%;
At the dosage of 25ppm, the compounds 6-19 and 12-19 have better inhibition rate on cucumber downy mildew, for example, the control efficiency on cucumber downy mildew is more than 90%;
(2) Powdery mildew of wheat
At the dosage of 400ppm, the compound provided by the invention has good inhibition rate on wheat powdery mildew, for example, the compound 6-57, 6-288, 11-4, 12-19, 16-4, 16-60, 23-19 and the like, and the control efficiency on the wheat powdery mildew is more than 80%;
at the dosage of 100ppm, the compounds 6-57, 6-288 and 16-60 have good inhibition rate on wheat powdery mildew, and the control efficiency on the wheat powdery mildew is more than 85%;
At the dosage of 25ppm, the compounds 6-57 and 6-288 have better inhibition rate to the wheat powdery mildew, and the prevention effect to the wheat powdery mildew is more than 90%;
(3) Rust disease of corn
At the dosage of 400ppm, the compound provided by the invention has good inhibition rate on corn rust, for example, the compounds 6-1, 7-4, 10-21, 11-4, 12-19 and the like have the prevention effect on corn rust of more than 80%;
At the dosage of 100ppm, the compounds 7-4, 10-21, 11-4 and 12-4 have good inhibition rate on corn rust disease and the prevention effect on corn rust disease is more than 85%;
(4) Anthracnose of cucumber
The compound provided by the invention has good inhibition rate to melon anthracnose at 400ppm dosage, for example, the control efficiency to melon anthracnose is more than 80% for compounds 6-151, 16-17, 16-19, 16-21, 16-60, 16-151, 18-19 and the like.
At the dosage of 100ppm, the compounds 16-17, 16-19, 16-21, 16-69 and 16-151 have good inhibition rate on melon anthracnose and control effect on corn rust disease is more than 85%;
At the dosage of 25ppm, the compounds 16-19, 16-21 and 16-151 have good inhibition rate on melon anthracnose and control effect on wheat powdery mildew is more than 90%;
From the data, the compound shown in the general formula I with novel structure shows good activity on various germs in the agricultural field, and the compound shows outstanding activity effect at some low doses, and has excellent activity effect compared with a control compound.
The other compounds of the invention of the general formula I are tested in accordance with the above-described biological activity assay, which may also have corresponding activity.

Claims (5)

1.一种取代异噁唑乙胺类化合物，其特征在于：取代异噁唑乙胺类化合物为通式I所示化合物；1. A substituted isoxazole ethylamine compound, characterized in that: the substituted isoxazole ethylamine compound is a compound represented by general formula I; 式中：Where: R1选自氢、C1-C6烷基、卤代C1-C6烷基；R 1 is selected from hydrogen, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl; R2选自卤素、羟基、氨基、氰基、硝基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基、卤代C1-C4烷硫基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基，R2处于苯环4位时，不选自氰基或者羟基； R2 is selected from halogen, hydroxyl, amino, cyano, nitro, C1 - C4 alkyl, halogenated C1- C4 alkyl, C1 - C4 alkoxy, halogenated C1- C4 alkoxy, C1 - C4 alkylthio, halogenated C1-C4 alkylthio , C1 - C4 alkoxycarbonyl, halogenated C1 - C4 alkoxycarbonyl, and when R2 is at the 4th position of the benzene ring, it is not selected from cyano or hydroxyl; n选自0至5的整数，当n为0时，无取代基；当n大于1时，R2相同或不同；n is an integer selected from 0 to 5, when n is 0, there is no substituent; when n is greater than 1, R2 are the same or different; R3选自氢、羟基、C1-C4烷基、卤代C1-C4烷基；R 3 is selected from hydrogen, hydroxy, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl; R4、R5相同或不同的分别选自氢、卤素、C1-C4烷基、卤代C1-C4烷基；R 4 and R 5 are the same or different and are selected from hydrogen, halogen, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl; R6、R7相同或不同的分别选自氢、卤素、C1-C4烷基、卤代C1-C4烷基；R 6 and R 7 are the same or different and are selected from hydrogen, halogen, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl; Q选自如下取代基：Q is selected from the following substituents: R8选自卤素、氨基、氰基、硝基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C3-C4环烷基、C1-C4烷硫基、卤代C1-C4烷硫基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基；R 8 is selected from halogen, amino, cyano, nitro, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogenated C 1 -C 4 alkoxy, C 3 -C 4 cycloalkyl, C 1 -C 4 alkylthio, halogenated C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, halogenated C 1 -C 4 alkylsulfonyl; m选自0至5的整数，当m为0时，无取代基；当m大于1时，R8相同或不同。m is an integer selected from 0 to 5. When m is 0, there is no substituent; when m is greater than 1, R 8 are the same or different. 2.根据权利要求1所述的取代异噁唑乙胺类化合物，其特征在于：通式I所示化合物中：2. The substituted isoxazole ethylamine compound according to claim 1, characterized in that: in the compound represented by general formula I: R1选自氢、甲基、乙基或三氟甲基； R1 is selected from hydrogen, methyl, ethyl or trifluoromethyl; R2选自氟、氯、溴、碘、羟基、氰基、氨基、硝基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、二氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、甲硫基、乙硫基、三氟甲氧基、三氟乙氧基、甲氧基羰基、乙氧基羰基，R2处于苯环4位时，不选自氰基或者羟基； R2 is selected from fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromonochloromethyl, dichloromonofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, and when R2 is at the 4-position of the benzene ring, it is not selected from cyano or hydroxyl; n选自0至5的整数，当n为0时，无取代基；当n大于1时，R2相同或不同；n is an integer selected from 0 to 5, when n is 0, there is no substituent; when n is greater than 1, R2 are the same or different; R3选自氢、羟基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氟乙基； R3 is selected from hydrogen, hydroxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl; R4、R5相同或不同的分别选自氢、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基；R 4 and R 5 are the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl; R6、R7相同或不同的分别选自氢、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基；R 6 and R 7 are the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl; Q选自如下取代基：Q is selected from the following substituents: R8选自氟、氯、溴、碘、氰基、氨基、硝基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、二氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、甲硫基、乙硫基、三氟甲氧基、三氟乙氧基、甲基磺酰基、乙基磺酰基；R 8 is selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromonochloromethyl, dichloromonofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methylsulfonyl, ethylsulfonyl; m选自0至5的整数，当m为0时，无取代基；当m大于1时，R8相同或不同。m is an integer selected from 0 to 5. When m is 0, there is no substituent; when m is greater than 1, R 8 are the same or different. 3.根据权利要求2所述的取代异噁唑乙胺类化合物，其特征在于：通式I所示化合物中：3. The substituted isoxazole ethylamine compound according to claim 2, characterized in that: in the compound represented by general formula I: R1选自氢或甲基； R1 is selected from hydrogen or methyl; R3选自氢； R3 is selected from hydrogen; R2选自氟、氯、溴、碘、氰基、硝基、甲基、乙基、三氟甲基、二氟甲基、甲氧基、甲硫基或三氟甲氧基，R2处于苯环4位时，不选自氰基；R 2 is selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, methylthio or trifluoromethoxy, and when R 2 is at the 4-position of the benzene ring, it is not selected from cyano; R4、R5相同或不同的分别选自氢、氟、氯、溴或甲基；R 4 and R 5 are the same or different and are selected from hydrogen, fluorine, chlorine, bromine or methyl; R6、R7均选自氢；R 6 and R 7 are both selected from hydrogen; n选自0至5的整数，当n为0时，环上无取代基；当n大于1时，R2相同或不同；n is an integer selected from 0 to 5. When n is 0, there is no substituent on the ring; when n is greater than 1, R2 are the same or different; Q选自如下取代基：Q is selected from the following substituents: R8选自氟、氯、溴、碘、氰基、氨基、硝基、甲基、乙基、三氟甲基、二氟甲基、甲氧基、乙氧基、甲硫基、乙硫基、三氟甲氧基、三氟乙氧基；R 8 is selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy; m选自0至4的整数，当m为0时，无取代基；当m大于1时，R8相同或不同。m is an integer selected from 0 to 4. When m is 0, there is no substituent; when m is greater than 1, R 8 are the same or different. 4.一种按权利要求1所述的取代异噁唑乙胺类化合物的制备方法，其特征在于：通式I所示化合物的制备方法为：4. A method for preparing a substituted isoxazole ethylamine compound according to claim 1, characterized in that: the method for preparing the compound represented by general formula I is: 5.一种按照权利要求1所述的取代异噁唑乙胺类化合物在用作制备杀菌药物制剂的用途。5. Use of the substituted isoxazole ethylamine compound according to claim 1 in preparing a bactericidal pharmaceutical preparation.
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