CN113512029A - Preparation and application of substituted pyrazole compound containing pyrimidinamine - Google Patents

Preparation and application of substituted pyrazole compound containing pyrimidinamine Download PDF

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CN113512029A
CN113512029A CN202010277446.4A CN202010277446A CN113512029A CN 113512029 A CN113512029 A CN 113512029A CN 202010277446 A CN202010277446 A CN 202010277446A CN 113512029 A CN113512029 A CN 113512029A
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halo
alkyl
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alkoxy
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CN113512029B (en
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王立增
关爱莹
孙旭峰
王军峰
常秀辉
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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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
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    • 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
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    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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Abstract

The invention discloses a substituted pyrazole compound containing pyrimidinamine, which has a structure shown as a general formula I:

Description

Preparation and application of substituted pyrazole compound containing pyrimidinamine
Technical Field
The invention belongs to the field of agricultural sterilization, insecticide and acaricide, and particularly relates to preparation and application of a novel pyrimidine amine-containing substituted pyrazole compound.
Background
Patent WO9507278 discloses substituted pyrazoles containing pyrimidinamines represented by the following general formula 1 and specific compounds CK1 and CK2, and application of the substituted pyrazoles as agricultural bactericides, insecticides, acaricides and the like.
Figure BDA0002445325790000011
The following compounds CK3, CK4 and CK5 were retrieved online by Scfinider, but no specific reference is made.
Figure BDA0002445325790000012
Patent CN106167484 and EP3299366 report the application of pyrimidine-containing substituted pyrazole compounds shown in the following general formula 2 and specific compound CK6 as agricultural bactericidal, insecticidal and miticidal agents.
Figure BDA0002445325790000013
However, the pyrimidine amine-containing substituted pyrazole compound with the structure shown in the general formula I and the activity thereof are not reported.
Disclosure of Invention
The invention aims to provide a substituted pyrazole compound containing pyrimidinamine for controlling various germs and pest mites, which can be used for preparing medicines for preventing and controlling germs and/or pest mites in agriculture or other fields.
The technical scheme of the invention is as follows:
the invention provides a substituted pyrazole compound containing pyrimidinamine, which is shown as a general formula I:
Figure BDA0002445325790000021
in the formula:
I
R1selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C12Alkyl, halo C1-C12Alkyl radical, C3-C12Cycloalkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C1-C12Alkylthio, halo C1-C12Alkylthio radical, C1-C12Alkyl sulfinylBase, C1-C12Alkylsulfonyl radical, C2-C12Alkenyl, halo C2-C12Alkenyl radical, C2-C12Alkynyl, halo C2-C12Alkynyl, C3-C12Alkenyloxy, halogeno C3-C12Alkenyloxy radical, C3-C12Alkynyloxy, halo C3-C12Alkynyloxy, C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, C1-C12Alkylaminocarbonyl, halogeno C1-C12Alkylaminocarbonyl radical, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl or C1-C2Alkylthio group C1-C12An alkyl group;
R2selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy or halo C1-C12An alkoxy group;
wherein R is1And R2Can also form a five-membered, six-membered, seven-membered or eight-membered ring containing C, N, O or S together with the connected pyrimidine ring;
R3selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylthio radical, C2-C12Alkenylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, halo C2-C12Alkenyl, halo C2-C12Alkynyl, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, di (halo C)1-C12Alkyl) amino, C1-C12Alkyl hydrazino, C1-C12Alkoxyamino group, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkylsulfinyl, halogeno C1-C12Alkylsulfinyl radical, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylaminosulfonyl, di (C)1-C12Alkyl) aminosulfonyl, C1-C12Alkylsulfonylaminocarbonyl group, C1-C12Alkylcarbonylaminosulfonyl radical, C3-C12Cycloalkyloxycarbonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkyl carbonyl radical C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C1-C12Alkylaminocarbonyl, di (C)1-C12Alkyl) aminocarbonyl, C2-C12Alkenyloxycarbonyl radical, C2-C12Alkynyloxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkoxycarbonyl group, C1-C12Alkylaminosulfenyl, di (C)1-C12Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 51-C6Alkyl, heteroaryl C1-C6Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C1-C6Alkyloxy, heteroaryl C1-C6Alkyloxy, aryl C1-C6Alkylamino, heteroaryl C1-C6Alkylamino, the group beingHalogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
y is selected from NR3O or S;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy or halo C1-C12An alkoxy group;
wherein R is4And R5And optionally C connected thereto to form C3-C8A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy or halo C1-C12An alkoxy group;
wherein R is6And R7And optionally C connected thereto to form C3-C8A ring of (a);
m is an integer from 0 to 5;
R8selected from hydrogen, cyano, halogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R9selected from hydrogen, cyano, halogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonylA phenyl or heteroaryloxycarbonyl group;
R10selected from halogen, hydroxy, amino, cyano, nitro, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, halo-di (C)1-C12Alkyl) amino, C (═ O) NR11R12、C1-C12Alkylthio, halo C1-C12Alkylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, C2-C12Alkenyloxy, halogeno C2-C12Alkenyloxy radical, C2-C12Alkynyloxy, halo C2-C12Alkynyloxy, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl, halo C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C1-C12Alkylthio carbonyl group C1-C12Alkyl, halo C1-C12Alkylthio carbonyl group C1-C12Alkyl radical, C1-C12Alkylcarbonyloxy, halo C1-C12Alkylcarbonyloxy, C1-C12Alkoxycarbonyloxy, halo C1-C12Alkoxycarbonyloxy, C1-C12Alkylsulfonyloxy, halo C1-C12Alkylsulfonyloxy, C1-C12Alkoxy radical C1-C12Alkoxy or halo C1-C12Alkoxy radical C1-C12An alkoxy group;
n is an integer of 0 to 5, and when n is 0, no substituent is arranged on a benzene ring; when n is greater than 1, R10May be the same or different;
R11、R12can be the same or different and are respectively selected from hydrogen and C1-C12Alkyl or halo C1-C12An alkyl group;
w is selected from hydrogen, halogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C3-C8Cycloalkyl radical, C1-C12Alkoxy radical, C1-C12Alkylthio or C1-C12An alkylsulfonyl group.
Preferred compounds of the invention are: in the general formula I
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C6Alkyl, halo C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio radical, C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl, halo C1-C6Alkylthio radical, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C2-C6Alkynyl, halo C2-C6Alkynyl, C3-C6Alkenyloxy, halogeno C3-C6Alkenyloxy radical, C3-C6Alkynyloxy, halo C3-C6Alkynyloxy, C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, C1-C6Alkylaminocarbonyl, halogeno C1-C6Alkylaminocarbonyl radical, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl or C1-C6Alkylthio group C1-C6An alkyl group;
R2selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is1And R2Can also form a five-membered ring or a six-membered ring containing C, N, O or S together with the connected pyrimidine ring;
R3selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylthio radical, C2-C6Alkenylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, halo C2-C6Alkenyl, halo C2-C6Alkynyl, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, di (halo C)1-C6Alkyl) amino, C1-C6Alkyl hydrazino, C1-C6Alkoxyamino group, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkylsulfinyl, halogeno C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylaminosulfonyl, di (C)1-C6Alkyl) aminosulfonyl, C1-C6Alkylsulfonylaminocarbonyl group, C1-C6Alkylcarbonylaminosulfonyl radical, C3-C6Cycloalkyloxycarbonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkyl carbonyl radical C1-C6Alkyl radical, C1-C6Alkoxycarbonyl radical C1-C6Alkyl radical, C1-C6Alkylaminocarbonyl, di (C)1-C6Alkyl) aminocarbonyl, C2-C6Alkenyloxycarbonyl radical, C2-C6Alkynyloxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkoxycarbonyl group, C1-C6Alkylaminosulfenyl, di (C)1-C6Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 51-C6Alkyl, heteroaryl C1-C6Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C1-C6Alkyloxy, heteroaryl C1-C6Alkyloxy, aryl C1-C6Alkylamino, heteroaryl C1-C6Alkylamino, the following groups being halogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
y is selected from NR3O or S;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is4、R5And optionally C connected thereto to form C3-C6A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is6、R7And optionally C connected thereto to form C3-C6A ring of (a);
m is an integer from 0 to 4;
R8selected from hydrogen, cyano, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R9selected from hydrogen, cyano, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R10selected from halogen, hydroxy, amino, cyano, nitro, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, halo-di (C)1-C6Alkyl) amino, C (═ O) NR11R12、C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, halo C2-C6Alkynyloxy, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkoxycarbonyl radical C1-C6Alkyl, halo C1-C6Alkoxycarbonyl radical C1-C6Alkyl radical, C1-C6Alkylthio carbonyl group C1-C6Alkyl, halo C1-C6Alkylthio carbonyl group C1-C6Alkyl radical, C1-C6Alkylcarbonyloxy, halo C1-C6Alkylcarbonyloxy, C1-C6Alkoxycarbonyloxy, halo C1-C6Alkoxycarbonyloxy, C1-C6Alkylsulfonyloxy, halo C1-C6Alkylsulfonyloxy, C1-C6Alkoxy radical C1-C6Alkoxy or halo C1-C6Alkoxy radical C1-C6An alkoxy group;
n is an integer of 0 to 5, and when n is 0, no substituent is arranged on a benzene ring; when n is greater than 1, R10May be the same or different;
R11、R12can be the same or different and are respectively selected from hydrogen and C1-C6Alkyl or halo C1-C6An alkyl group;
w is selected from hydrogen, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio or C1-C6An alkylsulfonyl group;
the position of attachment of Y to the pyrazole ring is selected from the 3, 4 or 5 positions; when Y is attached to the pyrazole ring at position 3, then R8In the 4 position, R9At position 5; when Y is attached to the pyrazole ring at the 4-position, then R8In the 3 position, R9At position 5; when Y is attached to the pyrazole ring at the 5-position, then R8In the 3 position, R9At 4 bits.
Further preferred compounds of the invention are: in the general formula I
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylthio radical, C2-C4Alkenyl, halo C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkynyl, C3-C4Alkenyloxy, halogeno C3-C4Alkenyloxy radical, C3-C4Alkynyloxy, halo C3-C4Alkynyloxy, C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, C1-C4Alkylaminocarbonyl, halogeno C1-C4Alkylaminocarbonyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl or C1-C4Alkylthio group C1-C4An alkyl group;
R2selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4Alkoxy radicalA group;
wherein R is1And R2Can also form a five-membered ring or a six-membered ring containing C, N, O or S together with the connected pyrimidine ring;
R3selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, di (halo C)1-C4Alkyl) amino, C1-C4Alkyl hydrazino, C1-C4Alkoxyamino group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylaminosulfonyl, di (C)1-C4Alkyl) aminosulfonyl, C1-C4Alkylsulfonylaminocarbonyl group, C1-C4Alkylcarbonylaminosulfonyl radical, C3-C4Cycloalkyloxycarbonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkyl carbonyl radical C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radicalC1-C4Alkyl radical, C1-C4Alkylaminocarbonyl, di (C)1-C4Alkyl) aminocarbonyl, C2-C4Alkenyloxycarbonyl radical, C2-C4Alkynyloxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkoxycarbonyl group, C1-C4Alkylaminosulfenyl, di (C)1-C4Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 51-C4Alkyl, heteroaryl C1-C4Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C1-C4Alkyloxy, heteroaryl C1-C4Alkyloxy, aryl C1-C4Alkylamino, heteroaryl C1-C4Alkylamino, the following groups being halogen, nitro, cyano, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
y is selected from O;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is4、R5And optionally C connected thereto to form C3-C4A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is6、R7And optionally C connected thereto to form C3-C4A ring of (a);
m is an integer from 0 to 3;
R8selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R9selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R10selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR11R12、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C2-C4Alkenyloxy, halogeno C2-C4Alkenyloxy radical, C2-C4Alkynyloxy, halo C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
n is an integer of 0 to 5, and when n is 0, no substituent is arranged on a benzene ring; when n is greater than 1, R10May be the same or different;
R11、R12can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
w is selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio or C1-C4An alkylsulfonyl group;
y is O, the position of the connection of the O and the pyrazole ring is selected from 3, 4 or 5; when O is attached to the 3-position of the pyrazole ring, then R8In the 4 position, R9At position 5, the structural formula is shown as I-1; when O is attached to the 4-position of the pyrazole ring, then R8In the 3 position, R9At position 5, the structural formula is shown as I-2; when O is attached to the 5-position of the pyrazole ring, then R8In position 3，R9At the 4-position, the structural formula is shown as I-3;
Figure BDA0002445325790000061
further preferred compounds of the invention are:
the compound shown in the structure of general formula I-1, I-2 or I-3 as I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-2A, I-2B, I-2C, I-3A, I-3B, I-3C, I-4A, I-4B or I-4C,
Figure BDA0002445325790000062
Figure BDA0002445325790000071
in the formula:
R1selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C2-C4Alkenyl, halo C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkynyl, C3-C4Alkenyloxy, halogeno C3-C4Alkenyloxy radical, C3-C4Alkynyloxy, halo C3-C4Alkynyloxy, C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, C1-C4Alkylaminocarbonyl, halogeno C1-C4Alkylaminocarbonyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxy radicalCarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl or C1-C4Alkylthio group C1-C4An alkyl group;
R2selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R3selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, di (halo C)1-C4Alkyl) amino, C1-C4Alkyl hydrazino, C1-C4Alkoxyamino group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylaminosulfonyl, di (C)1-C4Alkyl) aminosulfonyl, C1-C4Alkylsulfonylaminocarbonyl group, C1-C4Alkylcarbonylaminosulfonyl radical, C3-C4Cycloalkyloxycarbonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkyl carbonyl radical C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylaminocarbonyl, di (C)1-C4Alkyl) aminocarbonyl, C2-C4Alkenyloxycarbonyl radical, C2-C4Alkynyloxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkoxycarbonyl group, C1-C4Alkylaminosulfenyl, di (C)1-C4Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 51-C4Alkyl, heteroaryl C1-C4Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C1-C4Alkyloxy, heteroaryl C1-C4Alkyloxy, aryl C1-C4Alkylamino, heteroaryl C1-C4Alkylamino group: halogen, nitro, cyano, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is4、R5And optionally C connected thereto to form C3-C4A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is6、R7And optionally C connected thereto to form C3-C4A ring of (a);
R8selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R9selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R10selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR11R12、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C2-C4Alkenyloxy, halogeno C2-C4Alkenyloxy radical, C2-C4Alkynyloxy, halo C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
n is an integer of 0 to 5, and when n is 0, no substituent is arranged on a benzene ring; when n is greater than 1, R10May be the same or different;
R11、R12can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
R13、R14、R15or R16Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy or C3-C4A cycloalkyl group;
R17、R18can be the same or different and are respectively selected from hydrogen, halogen,C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C3-C4Cycloalkyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R19is selected from C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R20selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R21is selected from C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R22selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R23、R24each independently selected from C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R25、R26each independently selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
w is selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio or C1-C4An alkylsulfonyl group.
Still further preferred compounds of the invention are:
a compound shown as a general formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-2A, I-2B, I-2C, I-3A, I-3B, I-3C, I-4A, I-4B or I-4C, wherein the compound is shown in the formula
R1Selected from hydrogen, fluoro, chloro, bromo, iodo, cyano, nitro, amino, carboxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxymethyl, ethoxymethyl or trifluoroethoxymethyl;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, cyano, nitro, amino, carboxy, formyl, methyl, ethyl, methoxy, ethoxy or trifluoroethoxy;
R3selected from the group consisting of hydrogen, chloro, hydroxy, amino, hydroxyamino, hydrazino, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, cyclopropyloxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, trifluoromethylamino, trifluoroethylamino, cyclopropylamino, dimethylamino, diethylamino, methylhydrazino, ethylhydrazino, tert-butylhydrazino, methoxyamino, ethoxyamino, methylthio, ethylthio, allyl, propargyl, methylsulfonyl, ethylsulfonyl, trifluoroethylsulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl, ethylsulfonyl, ethylaminosulfonyl, and combinations thereof, Diethylaminosulfonyl, methylsulfonylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, vinyloxycarbonyl, acetylenyloxycarbonyl, methylaminothio, ethylaminothio, dimethylaminosulfanyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2, 4-triazolyl, 1,2, 3-triazolyl, tetrazolyl, indolyl, morpholinyl, piperazinyl, benzopyrazolyl, benzimidazolyl, benzylamino, 4-chlorobenzylamine, 4-fluorobenzylamine, 4-bromobenzylamine, 4-methylbenzylamine, 4-methoxybenzylamine, 4-trifluoromethoxybenzylamineAmino group, phenethylamino group, 4-chlorophenylethylamino group, 4-fluorophenylethylamino group, 4-bromophenylethylamino group, 4-methylphenylethylamino group, 4-methoxyphenylethylamino group, 4-trifluoromethoxy phenylethynylethylamino group, 3-chlorophenylethylamino group, 3-fluorophenylethylamino group, 3-bromophenylethylamino group, 3-methylphenylethylamino group, 3-trifluoromethylphenethylamino group, 2-chlorophenylethylamino group, 2-fluorophenylethylamino group, 2-bromophenylethylamino group, 2-methylphenylethylamino group or 2-trifluoromethylphenethylamino group;
R4、R5which may be the same or different, are each selected from hydrogen, fluoro, chloro, bromo, iodo, 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;
R6、R7which may be the same or different, are each selected from hydrogen, fluoro, chloro, bromo, iodo, 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;
R8selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl or trifluoromethyl;
R9selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl or trifluoromethyl;
R10selected from fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl or dimethylaminocarbonyl;
n is an integer of 0 to 5, and when n is 0, no substituent is arranged on a benzene ring; when n is greater than 1, R10May be the same or different;
R13、R14、R15or R16Which may be the same or different, are each selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy or trifluoroethoxy;
R17、R18which may be identical or different, are each chosen from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R19selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, cyclopropyl, methylsulfonyl, ethylsulfonyl, methylcarbonyl, ethylcarbonyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R20selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonylA phenyl or heteroaryloxycarbonyl group;
R21selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, cyclopropyl, methylsulfonyl, ethylsulfonyl, methylcarbonyl, ethylcarbonyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R22selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R23、R24each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, trifluoroethoxycarbonyl, unsubstituted or substituted with 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R25、R26each independently selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, unsubstituted or substituted with 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl；
W is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl.
Still further preferred compounds of the invention are:
compounds of the general formula I-1A, I-1B, I-1C, I-2A, I-2B, I-2C, I-4A, I-4B or I-4C, wherein
R1Selected from hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl or difluoromethyl;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, nitro, amino, formyl, methyl, ethyl, methoxy or ethoxy;
R3selected from the group consisting of chloro, amino, hydroxyamino, hydrazino, methyl, ethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, cyclopropylamino, dimethylamino, diethylamino, methylhydrazino, tert-butylhydrazino, methoxyamino, ethoxyamino, methylthio, ethylthio, methylaminothio, dimethylaminosulthio, pyrazolyl, 1,2, 4-triazolyl, benzylamino, 4-chlorobenzylamino, 4-methoxybenzylamino, 4-trifluoromethoxybenzylamino, phenethylamino, 4-chlorobenzylethylamino, 4-fluorobenzylethylamino, 4-bromobenzylethylamino, 4-methylphenylethylamino, 3-bromobenzylethylamino or 2-fluorobenzylethylamino;
R4、R5can be the same or different and is respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R6、R7are all selected from hydrogen;
R8selected from hydrogen;
R9selected from hydrogen;
R10selected from fluoro, chloro, bromo, iodo, cyano, nitro, methyl, trifluoromethyl, methoxy or trifluoromethoxy;
n is an integer of 0 to 5, and when n is 0, no substituent is arranged on a benzene ring; when n is greater than 1, R10May be the same or different;
R13、R14、R15or R16Can be the same or different and is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl;
R17、R18can be the same or different and is respectively selected from hydrogen, fluorine, chlorine, bromine or iodine;
w is selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl.
Further preferred compounds of the invention are:
compounds of the general formula I-1A, I-1B, I-1C, I-2A, I-2B, I-2C, I-4A, I-4B or I-4C, wherein
R1Selected from fluoro, chloro, bromo, iodo, methyl, ethyl or difluoromethyl;
R2selected from fluorine, chlorine, bromine, iodine, nitro, amino, formyl, methyl or methoxy;
R3selected from the group consisting of chloro, amino, methoxy, ethoxy, n-propoxy, n-butoxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, dimethylamino, diethylamino, methoxyamino, pyrazolyl, 1,2, 4-triazolyl, benzylamino, 4-methoxybenzylamino, 4-chlorobenzylethylamino, 4-fluorobenzylethylamino, 4-bromobenzylethylamino, 4-methylphenylethylamino, 3-bromobenzylethylamino or 2-fluorobenzylethylamino;
R4、R5may be the same or different and is independently selected from hydrogen or methyl;
R6、R7are all selected from hydrogen;
R8selected from hydrogen;
R9selected from hydrogen;
R10selected from fluoro, chloro, bromo, iodo, cyano, nitro, methyl, trifluoromethyl, methoxy or trifluoromethoxy;
n is an integer of 1 to 5, and when n is greater than 1, R10May be the same or different;
R13、R14、R15、R16are all selected from hydrogen;
R17selected from hydrogen;
R18selected from chlorine;
w is selected from hydrogen, fluorine, chlorine, bromine or iodine.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl groups: straight-chain or branched alkyl groups, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl groups: substituted or unsubstituted cyclic alkyl groups, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, and the like. Halogenated alkyl 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. Alkyl hydrazine group: the linear or branched alkyl group is attached to the structure via a hydrazino (-NHNH-) group, such as a methylhydrazino group. Alkylsulfinyl group: straight or branched chain alkyl groups are attached to the structure via a sulfinyl (-SO-) group, such as methylsulfinyl. Haloalkylsulfinyl group: straight-chain or branched alkylsulfinyl groups in which the hydrogen atoms of the alkyl group may be partially or fully substituted by halogen atoms. Haloalkylsulfonyl group: straight-chain or branched alkylsulfonyl wherein the hydrogen atoms of the alkyl group may be partially or wholly substituted by halogen atoms. Alkylaminosulfenyl: such as CH3NHS-、C2H5NHS-. Dialkylaminosulfenyl: such as (CH)3)2NS-、(C2H5)2NS-. Alkylaminosulfonyl: alkyl-NH-SO2-. Dialkylaminosulfonyl: (alkyl group)2-N-SO2-. Alkylsulfonylaminocarbonyl group: alkyl-SO2-NH-CO-. Alkylcarbonylaminosulfonyl: alkyl-CO-NH-SO2-. Alkylcarbonylalkyl group: alkyl-CO-alkyl-. Alkylsulfonyloxy group: alkyl-S (O)2-O-. Haloalkylsulfonyloxy: the hydrogen atoms of the alkyl group of the alkylsulfonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF3-SO2-O. CycloalkanesAn oxycarbonyl group: such as cyclopropyloxycarbonyl, cyclohexyloxycarbonyl, and the like. Alkoxy groups: straight or branched chain alkyl groups attached to the structure via oxygen atom linkages. Haloalkoxy groups: straight-chain or branched alkoxy groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy and the like. Halogenated alkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyl group may be partially or wholly replaced by halogen atoms, e.g. ClCH2CH2OCO-、CF3CH2OCO-, etc. Alkoxyalkyl groups: alkyl-O-alkyl-, e.g. CH3OCH2-. Haloalkoxyalkyl groups: the hydrogen atoms of the alkyl groups of alkoxyalkyl groups may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2OCH2-、CF3CH2OCH2-and the like. Alkoxycarbonylalkyl groups: alkoxycarbonyl-alkyl-, e.g. CH3OCOCH2-. Haloalkoxycarbonylalkyl: the hydrogen atoms of the alkyl group of the alkoxycarbonylalkyl group may be partially or fully substituted by halogen atoms, e.g. CF3CH2OCOCH2-. Alkylcarbonyloxy group: such as CH3COO-, etc. Haloalkylcarbonyloxy: the hydrogen atoms of the alkylcarbonyloxy group may be partially or fully substituted by halogen atoms, e.g. CF3COO-, etc. Alkoxycarbonyloxy: alkoxycarbonyl-oxy-, e.g. CH3OCOO-. Haloalkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF3OCOO-. Alkylthio-carbonylalkyl: alkylthiocarbonyl-alkyl-, e.g. CH3SCOCH2-. Haloalkylthiocarbonylalkyl: the hydrogen atoms of the alkyl group of the alkylthiocarbonylalkyl group may be partially or wholly substituted by halogen atoms, e.g. CF3CH2SCOCH2-. Alkoxyalkoxy group: such as CH3OCH2O-, etc. Haloalkoxyalkyl: the hydrogen atoms of the alkoxy groups being partially or wholly replaced by halogen atoms, e.g. CF3OCH2O-is formed. Alkoxy alkoxycarbonyl group: such as CH3OCH2CH2OCO-, etc. Alkylthio group: straight or branched chain alkyl groups attached to the structure via a sulfur atom. Haloalkylthio: straight-chain or branched alkylthio groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like. Alkylthioalkyl: alkyl-S-alkyl-, e.g. CH3SCH2-. Haloalkylthioalkyl: the hydrogen atoms of the alkyl group of an alkylthioalkyl group may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2SCH2-、CF3CH2SCH2-and the like. Alkylamino group: straight or branched chain alkyl, linked to the structure via a nitrogen atom. Haloalkylamino group: straight-chain or branched alkylamino groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms. Dialkylamino group: such as (CH)3)2N-，(CH3CH2)2N-is provided. Halogenated dialkylamino group: the hydrogen atoms of the alkyl groups being partially or wholly replaced by halogen atoms, e.g. (CF)3)2N-，(CF3CH2)2N-is provided. Alkenyl: straight-chain or branched alkenes, for example ethenyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1, 2-allenyl and 2, 4-hexadienyl. Halogenated alkenyl groups: straight-chain or branched alkenes in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenyloxy: linear or branched alkenes linked to the structure via oxygen atoms. Haloalkenyloxy: straight-chain or branched alkenyloxy groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenylthio group: linear or branched alkenes linked to the structure via a sulfur atom bond. Such as CH2＝CHCH2S-. Alkenyloxycarbonyl radical: such as CH2＝CHCH2OCO-, etc. Alkynyl: straight-chain or branched alkynes, for example 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. Halogenated alkynyl group: straight-chain or branched alkynes, on these alkynesThe hydrogen atoms may be partially or completely substituted by halogen atoms. Alkynyloxy: straight or branched alkynes, linked to the structure via oxygen atom bonds. Haloalkynyloxy: straight-chain or branched alkynyloxy, in which the hydrogen atoms may be partially or completely substituted by halogen atoms. Alkynyloxycarbonyl group: such as CH ≡ CCH2OCO-, etc. An alkylsulfonyl group: straight or branched chain alkyl via sulfonyl (-SO)2-) is attached to a structure, such as a methylsulfonyl group. Haloalkylsulfonyl group: straight-chain or branched alkylsulfonyl wherein the hydrogen atoms of the alkyl group may be partially or wholly substituted by halogen atoms. An alkylcarbonyl group: the alkyl radical being bound to the structure via a carbonyl group, e.g. CH3CO-，CH3CH2CO-. Halogenated alkylcarbonyl group: the hydrogen atoms of the alkyl group of the alkylcarbonyl group may be partially or fully substituted by halogen atoms, e.g. CF3CO-. Alkoxycarbonyl group: the alkoxy group is attached to the structure via a carbonyl group. Such as CH3OCO-，CH3CH2OCO-. Aminocarbonyl group: such as NH2CO-. Alkyl amino carbonyl: alkyl-NH-CO-, e.g. CH3NHCO-，CH3CH2NHCO-. Dialkylaminocarbonyl group: such as (CH)3)2NCO-，(CH3CH2)2NCO-. The aryl moiety in aryl, heteroaryl, fused ring aryl, hetero-fused ring aryl, arylalkyl, heteroarylalkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, arylalkyloxy, heteroarylalkyloxy, arylalkylamino, heteroarylalkylamino, heteroarylmethylcarbonyl, arylcarbonylalkyl, heteroarylcarbonylalkyl, aryloxycarbonyl, heteroaryloxycarbonyl, arylalkyloxycarbonyl, heteroarylalkyloxycarbonyl includes phenyl or naphthyl and the like. Heteroaryl is a five or six membered ring containing 1 or more heteroatoms N, O, S. Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and the like. A fused heterocyclic aromatic group is a five or six membered fused ring containing 1 or more heteroatoms of N, O, S. Such as: indolyl, benzopyrazolyl, and the like. Aryl: such as phenyl, and the like. Heteroaryl group: such as pyridyl, etc. Arylalkyl: such as benzyl, phenethyl, p-chlorobenzyl. Heteroaromatic compoundsAlkyl radical: such as 2-chloropyridin-5-yl, 2-chloro-thiazol-5-yl, and the like. Arylamino group: such as anilino groups, and the like. Heteroarylamino group: such as pyridylamine groups, and the like. Aryloxy group: such as phenoxy, and the like. Heteroaryloxy group: such as pyridyloxy and the like. Arylalkyloxy group: such as benzyl alcohol group, phenethyl alcohol group, and the like. Heteroarylalkyloxy group: such as pyridine ethanol group, etc. Arylalkyl amino: such as benzylamino, phenethylamino, and the like. Heteroarylalkylamino group: such as pyridine benzylamine, pyridine ethylamino, etc. Aryl carbonyl group: such as benzoyl, 4-chlorobenzoyl and the like. Heteroaryl carbonyl group: such as picolinoyl, 3-chloropicolinoyl, and the like. Arylmethylcarbonyl, heteroarylmethylcarbonyl: such as PhCH2CO-, etc. Arylcarbonylalkyl, heteroarylcarbonylalkyl: such as PhCOCH2-and the like. Aryloxycarbonyl, heteroaryloxycarbonyl: such as phenoxycarbonyl, 4-chlorophenoxycarbonyl, 4-nitrophenoxycarbonyl, naphthyloxycarbonyl, etc. Arylalkyloxycarbonyl group: such as benzyloxycarbonyl, 4-chlorobenzyloxycarbonyl, 4-trifluoromethylbenzyloxycarbonyl and the like. Arylalkyloxycarbonyl, heteroarylalkyloxycarbonyl: such as PhCH2OCO-、4-Cl-PhCH2OCO-, etc.
Tables 1,2,3, 4,5, 6, 7, 8 and 9 respectively show the R in the general formula I1、R2、R3、R4And R5、R6And R7、R8、R9、R10And W are not limited to these substituents.
Figure BDA0002445325790000131
TABLE 1R1Substituent group
Figure BDA0002445325790000141
TABLE 2R2Substituent group
R2 R2 R2 R2
H F Cl Br
I CN NO2 NH2
CHO CH3 C2H5 n-C3H7
i-C3H7 n-C4H9 s-C4H9 i-C4H9
t-C4H9 OCH3 OC2H5 OC3H7-n
OC3H7-i OC4H9-n OC4H9-i OC4H9-t
OCH2F OCHF2 OCF3 OCH2CF3
TABLE 3R3Substituent group
Figure BDA0002445325790000142
Figure BDA0002445325790000151
Figure BDA0002445325790000161
Figure BDA0002445325790000171
TABLE 4R4(R5) Substituent group
Figure BDA0002445325790000172
Figure BDA0002445325790000181
TABLE 5R6(R7) Substituent group
Figure BDA0002445325790000182
TABLE 6R8Substituent group
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 7R9Substituent group
R9 R9 R9 R9
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 8R10Substituent group
Figure BDA0002445325790000191
Figure BDA0002445325790000201
TABLE 9W substituents
Figure BDA0002445325790000202
Some of the compounds of the present invention can be illustrated by specific compounds listed in tables 10 to 63, but are not intended to limit the present invention. The general formula compounds I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-2A,In I-2B, I-2C, I-3A, I-3B, I-3C, I-4A, I-4B or I-4C, W ═ R6＝R7＝R8＝R9＝R13＝R14＝R15＝R16＝R17＝H。
In the general formula I-1A,
Figure BDA0002445325790000203
when R is1＝Cl、R2＝Cl、R3＝NHCH3、R4＝R5When (R) is H10)nThe substituents are shown in Table 10, and represent the compound numbers of 10-1-10-279 in sequence.
Watch 10
Figure BDA0002445325790000211
Figure BDA0002445325790000221
Figure BDA0002445325790000231
TABLE 10-1: in the general formula I-1A, when R is1＝Cl、R2＝CH3、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are in turn 10-1-10-1-279.
Table 10-2: in the general formula I-1A, when R is1＝Cl、R2＝OCH3、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are in turn 10-2-1-10-2-279.
Tables 10 to 3: in the general formula I-1A,when R is1＝Cl、R2＝CHO、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are in turn 10-3-1 to 10-3-279.
Tables 10 to 4: in the general formula I-1A, when R is1＝Cl、R2＝Br、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are in turn 10-4-1-10-4-279.
Table 11: in the general formula I-1A, when R is1＝CH3、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are in turn 11-1-11-279.
Table 12: in the general formula I-1A, when R is1＝C2H5、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are in turn 12-1-12-279.
Table 12-1: in the general formula I-1A, when R is1＝CH3、R2＝R3＝Cl、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are in turn 12-1-12-1-279.
Table 12-2: in the general formula I-1A, when R is1＝C2H5、R2＝R3＝Cl、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are in turn 12-2-1-12-2-279.
Tables 12 to 3: in the general formula I-1A, when R is1＝CHF2、R2＝R3＝Cl、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are in turn 12-3-1-12-3-279.
Tables 12 to 4: in the general formula I-1A, when R is1＝CF3、R2＝R3＝Cl、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are in turn 12-4-1-12-4-279.
Table 13: in the general formula I-1A, when R is1＝CHF2、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 13-1-13-279 in turn.
Table 14: in the general formula I-1A, when R is1＝CF3、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 14-1-14-279 in turn.
Table 15: in the general formula I-1A, when R is1＝Cl、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 15-1-15-279 in turn.
Table 16: in the general formula I-1A, when R is1＝CH3、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are in turn 16-1-16-279.
Table 17: in the general formula I-1A, when R is1＝C2H5、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are in turn 17-1-17-279.
Table 18: in the general formula I-1A, when R is1＝CHF2、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 18-1-18-279 in turn.
Table 19: in the general formula I-1A, when R is1＝CF3、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are in turn 19-1-19-279.
Table 20: in the general formula I-1B, when R is3＝Cl、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 20-1-20-279 in turn.
TABLE 20-1: in the general formula I-1B, when R is3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 20-1-20-1-279 in turn.
Table 20-2: in the general formula I-1B, when R is3＝N(CH3)2、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 20-2-1-20-2-279 in turn.
Tables 20 to 3: in the general formula I-1B, when R is3＝HNOCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are 20-3-1 to 20-3-279 in turn.
Tables 20 to 4: in the general formula I-1B, when R is3＝OCH3、R4＝R5When H, getSubstituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 20-4-1-20-4-279 in turn.
Tables 20 to 5: in the general formula I-1B, when R is3＝OC2H5、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are 20-5-1 to 20-5-279 in turn.
Table 21-1: in the general formula I-1B, when R is3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 21-1-1-21-1-279 in turn.
Table 21-2: in the general formula I-1B, when R is3＝N(CH3)2、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 21-2-1-21-2-279 in turn.
Tables 21 to 3: in the general formula I-1B, when R is3＝HNOCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 21-3-1-21-3-279 in turn.
Tables 21 to 4: in the general formula I-1B, when R is3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 21-4-1-21-4-279 in turn.
Tables 21 to 5: in the general formula I-1B, when R is3＝OC2H5、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 21-5-1-21-5-279 in turn.
TABLE 22-1: in the general formula I-1C, when R is3＝NHCH3、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 22-1-22-1-279 in turn.
Table 22-2: in the general formula I-1C, when R is3＝NHCH3、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 22-2-1-22-2-279 in turn.
Tables 22 to 3: in the general formula I-1C, when R is3＝NHCH3、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 22-3-1-22-3-279 in turn.
Table 23-1: in the general formula I-1C, when R is3＝N(CH3)2、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 23-1-23-1-279 in turn.
Table 23-2: in the general formula I-1C, when R is3＝N(CH3)2、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 23-2-1-23-2-279 in turn.
Tables 23 to 3: in the general formula I-1C, when R is3＝N(CH3)2、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 23-3-1-23-3-279 in turn.
Table 24-1: in the general formula I-1C, when R is3＝OCH3、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 24-1-24-1-279 in turn.
Table 24-2: in the general formula I-1C, when R is3＝OCH3、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 24-2-1-24-2-279 in turn.
Tables 24 to 3: in the general formula I-1C, when R is3＝OCH3、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 24-3-1-24-3-279 in turn.
TABLE 25-1: in the general formula I-1C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 25-1-25-1-279 in turn.
Table 25-2: in the general formula I-1C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 25-2-1-25-2-279 in turn.
Tables 25 to 3: in the general formula I-1C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 25-3-1-25-3-279 in turn.
TABLE 26-1: in the general formula I-1C, when R is3＝OCH3、R4＝H、R5＝CH3，R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 26-1-26-1-279 in turn.
TABLE 26-2: in the general formula I-1C, when R is3＝OCH3、R4＝H、R5＝CH3，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 26-2-1-26-2-279 in turn.
Table 26-3: in the general formula I-1C, when R is3＝OCH3、R4＝H、R5＝CH3，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 26-3-1-26-3-279 in turn.
TABLE 27-1: in the general formula I-2A, when R is1＝Cl、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 27-1-27-1-279 in turn.
Table 27-2: in the general formula I-2A, when R is1＝CH3、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 27-2-1-27-2-279 in turn.
Tables 27 to 3: in the general formula I-2A, when R is1＝C2H5、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 27-3-1-27-3-279 in turn.
Tables 27 to 4: in the general formula I-2A, when R is1＝CHF2、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 27-4-1-27-4-279 in turn.
Tables 27 to 5: in the general formula I-2A, when R is1＝CF3、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nWatch and watch10 are consistent and sequentially correspond to 10-1-10-279 of the table 10, and represent that the compound numbers are sequentially 27-5-1-27-5-279.
TABLE 28-1: in the general formula I-2A, when R is1＝Cl、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 28-1-28-1-279 in turn.
TABLE 28-2: in the general formula I-2A, when R is1＝CH3、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 28-2-1-28-2-279 in turn.
Table 28-3: in the general formula I-2A, when R is1＝C2H5、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 28-3-1-28-3-279 in turn.
Tables 28 to 4: in the general formula I-2A, when R is1＝CHF2、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 28-4-1-28-4-279 in turn.
Tables 28 to 5: in the general formula I-2A, when R is1＝CF3、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 28-5-1-28-5-279 in turn.
TABLE 29-1: in the general formula I-2A, when R is1＝Cl、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 of Table 10The compound numbers in the table are 29-1-29-1-279 in sequence.
TABLE 29-2: in the general formula I-2A, when R is1＝CH3、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 29-2-1-29-2-279 in turn.
Table 29-3: in the general formula I-2A, when R is1＝C2H5、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 29-3-1-29-3-279 in turn.
Tables 29 to 4: in the general formula I-2A, when R is1＝CHF2、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 29-4-1-29-4-279 in turn.
Tables 29 to 5: in the general formula I-2A, when R is1＝CF3、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 29-5-1-29-5-279 in turn.
TABLE 30-1: in the general formula I-2A, when R is1＝Cl、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 30-1-30-1-279 in turn.
Table 30-2: in the general formula I-2A, when R is1＝CH3、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nWatch and watch10 are consistent and sequentially correspond to 10-1-10-279 of the table 10, and represent that the compound numbers are sequentially 30-2-1-30-2-279.
Tables 30 to 3: in the general formula I-2A, when R is1＝C2H5、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are 30-3-1 to 30-3-279 in turn.
Tables 30 to 4: in the general formula I-2A, when R is1＝CHF2、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 30-4-1-30-4-279 in turn.
Tables 30 to 5: in the general formula I-2A, when R is1＝CF3、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 30-5-1-30-5-279 in turn.
TABLE 31-1: in the general formula I-2B, when R is3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 31-1-1-31-1-279 in turn.
Table 31-2: in the general formula I-2B, when R is3＝N(CH3)2、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 31-2-1-31-2-279 in turn.
Tables 31 to 3: in the general formula I-2B, when R is3＝HNOCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 31-3-1-31-3-279 in turn.
TABLE 31-4: in the general formula I-2B, when R is3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 31-4-1-31-4-279 in turn.
Tables 31 to 5: in the general formula I-2B, when R is3＝OC2H5、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 31-5-1-31-5-279 in turn.
TABLE 32-1: in the general formula I-2B, when R is3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 32-1-32-1-279 in turn.
Table 32-2: in the general formula I-2B, when R is3＝N(CH3)2、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 32-2-1-32-2-279 in turn.
Table 32-3: in the general formula I-2B, when R is3＝HNOCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 32-3-1-32-3-279 in turn.
Tables 32 to 4: in the general formula I-2B, when R is3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 32-4-1-32-4-279 in turn.
Tables 32 to 5: in the general formula I-2B, when R is3＝OC2H5、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 32-5-1-32-5-279 in turn.
TABLE 33-1: in the general formula I-2C, when R is3＝NHCH3、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 33-1-33-1-279 in turn.
Table 33-2: in the general formula I-2C, when R is3＝NHCH3、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 33-2-1-33-2-279 in turn.
Table 33-3: in the general formula I-2C, when R is3＝NHCH3、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 33-3-1-33-3-279 in turn.
TABLE 34-1: in the general formula I-2C, when R is3＝N(CH3)2、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 34-1-34-1-279 in turn.
TABLE 34-2: in the general formula I-2C, when R is3＝N(CH3)2、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 34-2-1-34-2-279 in turn.
Table 34-3: in the general formula I-2C, when R is3＝N(CH3)2、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 34-3-1-34-3-279 in turn.
TABLE 35-1: in the general formula I-2C, when R is3＝OCH3、R4＝R5＝R18When H, the substituent (R)10)nTo watch 10AThus, the numbers of the representative compounds correspond to 10-1-10-279 in sequence to Table 10, and are 35-1-35-1-279 in sequence.
Table 35-2: in the general formula I-2C, when R is3＝OCH3、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 35-2-1-35-2-279 in turn.
Table 35-3: in the general formula I-2C, when R is3＝OCH3、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 35-3-1-35-3-279 in turn.
TABLE 36-1: in the general formula I-2C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 36-1-36-1-279 in turn.
TABLE 36-2: in the general formula I-2C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 36-2-1-36-2-279 in turn.
Table 36-3: in the general formula I-2C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 36-3-1-36-3-279 in turn.
TABLE 37-1: in the general formula I-2C, when R is3＝OCH3、R4＝H、R5＝CH3，R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 37-1-37-1-279 in turn.
TABLE 37-2: in the general formula I-2C, whenR3＝OCH3、R4＝H、R5＝CH3，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 37-2-1-37-2-279 in turn.
Table 37-3: in the general formula I-2C, when R is3＝OCH3、R4＝H、R5＝CH3，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 37-3-1-37-3-279 in turn.
TABLE 38-1: in the general formula I-3A, when R is1＝Cl、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 38-1-38-1-279 in turn.
TABLE 38-2: in the general formula I-3A, when R is1＝CH3、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 38-2-1-38-2-279 in turn.
Table 38-3: in the general formula I-3A, when R is1＝C2H5、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 38-3-1-38-3-279 in turn.
Table 38-4: in the general formula I-3A, when R is1＝CHF2、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 38-4-1-38-4-279 in turn.
Table 38-5: in the general formula I-3A, when R is1＝CF3、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 38-5-1-38-5-279 in turn.
TABLE 39-1: in the general formula I-3A, when R is1＝Cl、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 39-1-39-1-279 in turn.
TABLE 39-2: in the general formula I-3A, when R is1＝CH3、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 39-2-1-39-2-279 in turn.
Tables 39 to 3: in the general formula I-3A, when R is1＝C2H5、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 39-3-1-39-3-279 in turn.
Tables 39 to 4: in the general formula I-3A, when R is1＝CHF2、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 39-4-1-39-4-279 in turn.
Tables 39 to 5: in the general formula I-3A, when R is1＝CF3、R2＝Cl、R3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 39-5-1-39-5-279 in turn.
TABLE 40-1: in the general formula I-3A, when R is1＝Cl、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 40-1-40-1-279 in turn.
TABLE 40-2: in the general formula I-3A, when R is1＝CH3、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 40-2-1-40-2-279 in turn.
Tables 40 to 3: in the general formula I-3A, when R is1＝C2H5、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 40-3-1-40-3-279 in turn.
Tables 40 to 4: in the general formula I-3A, when R is1＝CHF2、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 40-4-1-40-4-279 in turn.
Tables 40 to 5: in the general formula I-3A, when R is1＝CF3、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 40-5-1-40-5-279 in turn.
Table 41-1: in the general formula I-3A, when R is1＝Cl、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 41-1-1-41-1-279 in turn.
Table 41-2: in the general formula I-3A, when R is1＝CH3、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are 41-2-1 to 41-2-279 in turn.
Tables 41 to 3: in the general formula I-3A, when R is1＝C2H5、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are 41-3-1 to 41-3-279 in turn.
Tables 41 to 4: in the general formula I-3A, when R is1＝CHF2、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are 41-4-1 to 41-4-279 in turn.
Tables 41 to 5: in the general formula I-3A, when R is1＝CF3、R2＝Cl、R3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are 41-5-1 to 41-5-279 in turn.
TABLE 42-1: in the general formula I-3B, when R is3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 42-1-42-1-279 in turn.
Table 42-2: in the general formula I-3B, when R is3＝N(CH3)2、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 42-2-1-42-2-279 in turn.
Table 42-3: in the general formula I-3B, when R is3＝HNOCH3、R4＝R5When H, the substituent (R)10)nIn accordance with Table 10, the data of Table 10 are sequentially mapped10-1-10-279, which represents a compound with the number of 42-3-1-42-3-279 in sequence.
Tables 42 to 4: in the general formula I-3B, when R is3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 42-4-1-42-4-279 in turn.
Tables 42 to 5: in the general formula I-3B, when R is3＝OC2H5、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 42-5-1-42-5-279 in turn.
TABLE 43-1: in the general formula I-3B, when R is3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 43-1-43-1-279 in turn.
Table 43-2: in the general formula I-3B, when R is3＝N(CH3)2、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 43-2-1-43-2-279 in turn.
Table 43-3: in the general formula I-3B, when R is3＝HNOCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 43-3-1-43-3-279 in turn.
Tables 43-4: in the general formula I-3B, when R is3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 43-4-1-43-4-279 in turn.
Tables 43 to 5: in the general formula I-3B, when R is3＝OC2H5、R4＝H、R5＝CH3When (R) is substituted10)nIn accordance with Table 10Which sequentially correspond to 10-1-10-279 of Table 10 and represent that the compound numbers are sequentially 43-5-1-43-5-279.
TABLE 44-1: in the general formula I-3C, when R is3＝NHCH3、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 44-1-44-1-279 in turn.
Table 44-2: in the general formula I-3C, when R is3＝NHCH3、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 44-2-1-44-2-279 in turn.
Table 44-3: in the general formula I-3C, when R is3＝NHCH3、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 44-3-1-44-3-279 in turn.
TABLE 45-1: in the general formula I-3C, when R is3＝N(CH3)2、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 45-1-45-1-279 in turn.
TABLE 45-2: in the general formula I-3C, when R is3＝N(CH3)2、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 45-2-1-45-2-279 in turn.
Tables 45 to 3: in the general formula I-3C, when R is3＝N(CH3)2、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 45-3-1-45-3-279 in turn.
TABLE 46-1: in the general formula I-3C, when R is3＝OCH3、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 46-1-46-1-279 in turn.
TABLE 46-2: in the general formula I-3C, when R is3＝OCH3、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 46-2-1-46-2-279 in turn.
Table 46-3: in the general formula I-3C, when R is3＝OCH3、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 46-3-1-46-3-279 in turn.
TABLE 47-1: in the general formula I-3C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 47-1-47-1-279 in turn.
Table 47-2: in the general formula I-3C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 47-2-1-47-2-279 in turn.
Table 47-3: in the general formula I-3C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 47-3-1-47-3-279 in turn.
TABLE 48-1: in the general formula I-3C, when R is3＝OCH3、R4＝H、R5＝CH3，R18When H, the substituent (R)10)nCorresponding in sequence to 10-1-10-279 of Table 10 in accordance with Table 10, represents the compoundThe material numbers are 48-1-48-1-279 in sequence.
TABLE 48-2: in the general formula I-3C, when R is3＝OCH3、R4＝H、R5＝CH3，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 48-2-1-48-2-279 in turn.
TABLE 48-3: in the general formula I-3C, when R is3＝OCH3、R4＝H、R5＝CH3，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 48-3-1-48-3-279 in turn.
TABLE 49-1: in the general formula I-4A, when R is1＝R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 49-1-49-1-279 in turn.
TABLE 49-2: in the general formula I-4A, when R is1＝Cl、R2＝OCH3、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 49-2-1-49-2-279 in turn.
Table 49-3: in the general formula I-4A, when R is1＝Cl、R2＝CHO、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 49-3-1-49-3-279 in turn.
Tables 49 to 4: in the general formula I-4A, when R is1＝CH3、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 49-4-279 in turn.
Tables 49 to 5: in the general formula I-4A,when R is1＝C2H5、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 49-5-1-49-5-279 in turn.
Tables 49 to 6: in the general formula I-4A, when R is1＝CHF2、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 49-6-1-49-6-279 in turn.
Tables 49 to 7: in the general formula I-4A, when R is1＝CF3、R2＝Cl、R3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 49-7-1-49-7-279 in turn.
TABLE 50-1: in the general formula I-4A, when R is1＝Cl、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 50-1-50-1-279 in turn.
TABLE 50-2: in the general formula I-4A, when R is1＝Cl、R2＝CHO、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 50-2-1-50-2-279 in turn.
Table 50-3: in the general formula I-4A, when R is1＝CH3、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1 to 10-279 in Table 10 indicates that the compound numbers are 50-3-1 to 50-3-279 in turn.
Tables 50-4: in the general formula I-4A, when R is1＝C2H5、R2＝Cl、R3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 50-4-1-50-4-279 in turn.
TABLE 51-1: in the general formula I-4B, when R is3＝NHCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound number is 51-1-1-51-1-279 in turn.
TABLE 51-2: in the general formula I-4B, when R is3＝N(CH3)2、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound number is 51-2-1-51-2-279 in turn.
Tables 51-3: in the general formula I-4B, when R is3＝HNOCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 51-3-1-51-3-279 in turn.
Tables 51-4: in the general formula I-4B, when R is3＝OCH3、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 51-4-1-51-4-279 in turn.
Tables 51-5: in the general formula I-4B, when R is3＝OC2H5、R4＝R5When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 51-5-1-51-5-279 in turn.
Table 52-1: in the general formula I-4B, when R is3＝NHCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 52-1-52-1-279 in turn.
TABLE 52-2: in the general formula I-4B, when R is3＝N(CH3)2、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 52-2-1-52-2-279 in turn.
Table 52-3: in the general formula I-4B, when R is3＝NOCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 52-3-1-52-3-279 in turn.
Table 52-4: in the general formula I-4B, when R is3＝OCH3、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 52-4-1-52-4-279 in turn.
Tables 52 to 5: in the general formula I-4B, when R is3＝OC2H5、R4＝H、R5＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 52-5-1-52-5-279 in turn.
TABLE 53-1: in the general formula I-4C, when R is3＝NHCH3、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 53-1-53-1-279 in turn.
TABLE 53-2: in the general formula I-4C, when R is3＝NHCH3、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 53-2-1-53-2-279 in turn.
Table 53-3: in the general formula I-4C, when R is3＝NHCH3、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 of Table 10, the numbers of the representative compounds are in accordance with Table 10The number of the secondary channels is 53-3-1-53-3-279.
TABLE 54-1: in the general formula I-4C, when R is3＝OCH3、R4＝R5＝R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 54-1-54-1-279 in turn.
TABLE 54-2: in the general formula I-4C, when R is3＝OCH3、R4＝R5＝H，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound number is 54-2-1-54-2-279 in turn.
Table 54-3: in the general formula I-4C, when R is3＝OCH3、R4＝R5＝H，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 54-3-1-54-3-279 in turn.
TABLE 55-1: in the general formula I-4C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18When H, the substituent (R)10)nCorresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 55-1-55-1-279 in turn.
TABLE 55-2: in the general formula I-4C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 55-2-1-55-2-279 in turn.
TABLE 55-3: in the general formula I-4C, when R is3＝NHCH3、R4＝H、R5＝CH3，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 55-3-1-55-3-279 in turn.
TABLE 56-1: in the general formula I-4C, when R is3＝OCH3、R4＝H、R5＝CH3，R18When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 56-1-56-1-279 in turn.
TABLE 56-2: in the general formula I-4C, when R is3＝OCH3、R4＝H、R5＝CH3，R18When Cl is not satisfied, a substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 56-2-1-56-2-279 in turn.
TABLE 56-3: in the general formula I-4C, when R is3＝OCH3、R4＝H、R5＝CH3，R18＝CH3When (R) is substituted10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 56-3-1-56-3-279 in turn.
Table 57: in the general formula I-1D, when R is3＝NHCH3、R4＝R5＝H、R19＝CH3、R20When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 57-1-57-279 in turn.
Table 58: in the general formula I-1E, when R is3＝NHCH3、R4＝R5＝H、R21＝CH3、R22When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 58-1-58-279 in turn.
Table 59: in the general formula I-1F, when R is3＝NHCH3、R4＝R5＝H、R23When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 59-1-59-279 in turn.
Table 60: in the general formula I-1G, when R is3＝NHCH3、R4＝R5＝H、R24When H, the substituent (R)10)nCorresponding to Table 10 in turn from 10-1 to 10-279 in Table 10, the numbers of the representative compounds are 60-1 to 60 in turn-279。
Table 61: in the general formula I-1H, when R is3＝NHCH3、R4＝R5＝H、R25When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 61-1-61-279 in turn.
Table 62: in the general formula I-1I, when R is3＝NHCH3、R4＝R5＝H、R26When H, the substituent (R)10)nCorresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 62-1-62-279 in turn.
In the general formula I-1B, when R is4＝R5＝H、(R10)nWhen 4-Cl, the substituent R3(R3Not Cl, NHCH3、N(CH3)2、HNOCH3、OCH3、OC2H5In time) are different substituents as shown in Table 63, representing the compound numbers 63-1-63-180 in sequence.
Table 63
Figure BDA0002445325790000311
Figure BDA0002445325790000321
Figure BDA0002445325790000331
Figure BDA0002445325790000341
The compounds of the general formula I according to the invention are prepared according to the following process, the reaction scheme is as follows, wherein the radicals are as defined above unless otherwise stated.
The preparation of the compounds of the general formula I differs depending on the definition of Y in the following two cases, which are prepared in different ways to give the corresponding compounds of the general formula I:
(1) when Y ═ O, compounds of formula I are prepared according to the difference in the position of attachment of O to the pyrazole ring, i.e. formulae I-1, I-2 and I-3, respectively, as follows:
the compound I-1 of the general formula is prepared by the following method:
Figure BDA0002445325790000342
intermediates T-1 and R3And reacting the H in a proper solvent under the alkaline condition to obtain the compound shown in the general formula I-1.
Suitable bases may be selected from, for example, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide, sodium tert-butoxide, etc.
The reaction is carried out in a suitable solvent, which may be selected from, for example, 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, and is generally from 20 to 100 ℃.
The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
The intermediate T-1 is a key intermediate for preparing the compound with the general formula I-1, and is prepared by the following method:
Figure BDA0002445325790000351
intermediates II are commercially available in part and can also be prepared by known methods, for example, by methods described in references JP2000007662, US4977264, US6090815, US20040092402, JP09124613, US5468751, US4985426, US4845097, Journal of the American Chemical Society (1957),79,1455, Journal of Chemical Society (1955), p.3478-3481.
Intermediate X-1 is reacted with substituted or unsubstituted ethyl acrylate in a suitable solvent at a suitable temperature for 30 minutes to 20 hours, typically 1 to 10 hours, to produce intermediate M-1, according to the procedures described in CN103588708, WO9703969 and Organic & Biomolecular Chemistry (2011),9(5), 1443-1453; m-1 is oxidized to give M-2, according to the procedures described in DE19652516, WO9703969 and Bulletin of the Korean Chemical Society (2010),31(11), 3341-3347; m-2 was reacted with the corresponding halide to give III, which was carried out in accordance with U.S. Pat. No. 5,2012, to U.S. Pat. No. 4,20100158860, WO2011133444 and Bioorganic & Medicinal Chemistry,20(20), 6109-. The intermediates II and III are reacted under basic conditions to give F-1, in accordance with CN106167484, EP3299366, by reacting F-1 with the acylating agent phosgene or phosgene in solid form to give T-1, in accordance with WO 2015057963.
The intermediates were derived from: intermediates X-1, R3H is commercially available or can be prepared according to conventional methods.
The appropriate temperature of the reaction is preferably 0-50 ℃; the reaction time is 30 minutes to 20 hours, preferably 0.5 to 10 hours.
Suitable solvents are selected from ethyl acetate, methyl formate, benzene, toluene, xylene, chloroform, dichloromethane, water, tetrahydrofuran, acetonitrile, dioxane, N-dimethylformamide, N-methylpyrrolidone or dimethylsulfoxide, and the like.
Suitable acids are selected from hydrochloric acid, trifluoroacetic acid, sulfuric acid, acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, fumaric acid, maleic acid, benzoic acid or phthalic acid, and the like.
Suitable bases may be selected from, for example, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide, sodium tert-butoxide, etc.
The compound I-2 of the general formula is prepared by the following method:
Figure BDA0002445325790000361
intermediates T-2 and R3And reacting the H in a proper solvent under the alkaline condition to obtain the compound shown in the general formula I-2.
Suitable bases may be selected from, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, sodium tert-butoxide or potassium tert-butoxide, etc.
The reaction is carried out in a suitable solvent, which may be selected from, for example, 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, and is generally from 20 to 100 ℃.
The time should be from 30 minutes to 20 hours, usually from 1 to 10 hours.
The intermediate T-2 is a key intermediate for preparing the compound with the general formula I-2, and the preparation method is as follows:
Figure BDA0002445325790000362
the intermediate N-4 can be prepared by taking N-1 as a raw material and referring to the following documents: DE3012193, JP60100547, WO2010076553, Organic Preparations and products International (2002),34(1),98-102 and Science of Synthesis (2002),12, 15-225; journal of Medicinal Chemistry (2016),59(4), 1370-; the preparation method of N-4 to IV is the same as that of M-2 to III in I-1. The intermediates II and IV react under alkaline conditions to obtain F-2, the operation method of the step is the same as that of the F-1 in the step I-1, and the preparation method of F-2 to T-2 is the same as that of the F-1 to T-1 in the step I-1.
Suitable solvents may be selected from methanol, ethanol, tetrahydrofuran, 1, 4-dioxane, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetone, butanone, or the like.
Suitable acids may be selected from hydrochloric acid, sulfuric acid or nitric acid, and the like.
Suitable bases may be selected from, for example, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide, sodium tert-butoxide, etc.
The compound I-3 of the general formula is prepared by the following method:
Figure BDA0002445325790000371
intermediates T-3 and R3And reacting the H in a proper solvent under the alkaline condition to obtain the compound shown in the general formula I-3.
Suitable bases may be selected from, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, sodium tert-butoxide or potassium tert-butoxide, etc.
The reaction is carried out in a suitable solvent, which may be selected from, for example, 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, and is generally from 20 to 100 ℃.
The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
Intermediate T-3 is a key intermediate for preparing the compound of the general formula I-3 of the invention, and the preparation method is as follows:
Figure BDA0002445325790000372
the intermediate Q-1 can be prepared by taking X-1 as a raw material and referring to the following documents: WO2009069044, WO2000031042 and WO2008059370, Bioorganic & Medicinal Chemistry (2006),14(14), 5061-; q-1 to V are prepared by the same method as M-2 to III in I-1. The intermediate II and V react under alkaline conditions to produce F-3, which is operated in the same manner as F-1 in I-1, and F-3 to T-3 are operated in the same manner as F-1 to T-1 in I-1.
(2) When Y is NR3Or S, the compounds of formula I can be prepared as follows.
Figure BDA0002445325790000381
The specific preparation method of the compound I can refer to the preparation method of I-1, the specific preparation method of the intermediate VI can refer to WO2003049739, WO2000031072 and the like, and the specific preparation methods of F and T can refer to F-1 and T-1.
Figure BDA0002445325790000382
Although the compounds of the general formula I of the invention also belong to the substituted pyrazoles containing pyrimidinamines, compared with certain compounds disclosed in the prior art, the structural characteristics still have significant difference. And due to these structural differences, the compounds of the present invention have better bactericidal and/or insecticidal and acaricidal activity.
The compound of the general formula I shows excellent activity on various germs in agriculture or other fields, and also shows better activity on pests and mites. Therefore, the technical scheme of the invention also comprises the application of the compound shown in the general formula I in preparing bactericides, insecticides and acaricides in agriculture or other fields.
The examples of diseases mentioned below are intended only to illustrate the invention, but in no way limit it.
The compounds of the general formula I can be used for controlling the following diseases: oomycete 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, loofah downy mildew, wax gourd downy mildew, melon downy mildew, Chinese cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, Chinese cabbage white rust), damping-off (rape damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cotton rot (hot pepper rot, loofah sponge rot, wax gourd blight), epidemic diseases (broad bean blight, cucumber blight, pumpkin blight, melon blight, hot pepper, leek blight, garlic blight, cotton blight, tomato blight, etc.; fungi imperfecti diseases such as wilt (sweet potato wilt, cotton wilt, sesame wilt, castor wilt, tomato wilt, bean wilt, cucumber wilt, pumpkin wilt, winter melon wilt, watermelon wilt, sweet melon wilt, hot pepper wilt, broad bean wilt, rape wilt, soybean wilt), root rot (hot pepper root rot, eggplant root rot, bean rot, cucumber root rot, bitter gourd root rot, cotton black root rot, broad bean root rot), damping off (seedling blight of cotton, sesame seedling blight, hot pepper seedling blight, cucumber damping off, cabbage stalk rot), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry leaf, hot pepper, bean disease, cucumber anthracnose, red sesame anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, eggplant disease, hot pepper anthracnose, vegetable bean disease, and cucumber blight, Balsam pear anthracnose, pumpkin anthracnose, wax gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, sunflower verticillium wilt, tomato verticillium wilt, hot pepper verticillium wilt, eggplant verticillium wilt), scab (pumpkin scab, wax gourd scab, melon scab), gray mold (boll gray mold, red ramie gray mold, tomato gray mold, hot 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, wax gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot, broad bean brown spot), black spot (flax brown spot, rape black spot, sesame black spot, sunflower black spot, castor black spot, tomato black spot, tomato black spot, tomato black spot, tomato black spot, tomato black spot, tomato, Pepper black spot, eggplant black spot, bean black spot, cucumber black spot, celery black spot, carrot black rot, carrot black spot, apple black spot, peanut black spot), spot blight (tomato spot blight, pepper spot blight, celery spot blight), 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 base rot (tomato stem base rot, bean stem base rot), and others (corn round spot, kenaf waist fold, rice blast, black sheath blight, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem blight, soybean black spot, melon big spot, peanut net spot, tea leaf spot, red leaf spot, black leaf spot, peanut net spot, tea leaf spot, tomato black spot, potato leaf spot, potato black spot, tomato leaf spot, etc, Pepper white spot disease, white gourd leaf spot disease, celery black rot disease, spinach heart rot disease, kenaf leaf mold disease, kenaf spot disease, jute stem spot disease, soybean purple spot disease, sesame leaf spot disease, castor gray spot disease, tea brown leaf spot disease, eggplant brown orbicular spot disease, kidney bean red spot disease, bitter gourd leukoderma, watermelon spot disease, jute bottom rot disease, sunflower root stem rot disease, kidney bean carbon rot disease, soybean target spot disease, eggplant rod spore leaf spot disease, cucumber target spot disease, tomato leaf mold, eggplant leaf mold, broad bean red spot disease and the like); basidiomycete diseases such as rust (wheat stripe rust, wheat stalk rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut (maize head smut, maize smut, sorghum head smut, sorghum loose smut, sorghum stalk smut, chestnut kernel smut, sugarcane head smut, kidney bean rust) and others (such as wheat sharp eyespot, rice sheath blight, etc.); ascomycetous 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, towel gourd powdery mildew, pumpkin powdery mildew, wax gourd powdery mildew, melon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia rot (flax sclerotinia rot, rape sclerotinia rot, soybean sclerotinia rot, peanut sclerotinia rot, tobacco sclerotinia rot, pepper sclerotinia rot, eggplant sclerotinia rot, kidney bean sclerotinia rot, pea sclerotinia rot, cucumber sclerotinia rot, bitter gourd sclerotinia rot, wax gourd sclerotinia rot, watermelon sclerotinia rot, celery sclerotinia rot), scab (apple scab, pear scab) and the like.
The compounds of the general formula I can be used for controlling the following pests:
coleoptera (Coleoptera) (beetle): bean species (Acanthoscelides spp.) (elephant), phaseolus vulgaris (Acanthoscelides obtectus) (common pisiform), Ceratoptera alba (Agrilus planipes) and Ceratopteris versicolor (Quadrifolia narrow Germin), Flammulina species (Agriotes spp.) (wireworm), Anoplophora glabripennis (Aphis longipes), Gomphytus species (Anthonoma spp.) (Arthrobacter flavidus), Gomphytus grandis (Anthronus grandis) (Arthrobacter asiaticus), Gomphytus species (Aphidius spp.) (Aprionus spp.) (Arthrospora), Cochlothiaoma sp. (Anacardia), Cochlothiajaponica (Aponia spp.) (grub), Cochlothuroides (Atacys specularis) (Black piss specula (Atanthus spec), Pieris versicolor (Pieris indica) (Pieris indica), Pieris indica (Pieris indica) (Pieris) and Pieris (Pieris indica) (Pieris chinensis (Pieris) of (Pieris) variety (Pieris illustrates (Pieris) and Pieris (Pieris) such as Pieris (Pieris sinensis (Pieris variety (Pieris) and Pieris (Pieris) such as (Pieris) A variety (Pieris) such as Pieris variety (Pieris) and Pieris variety (Pieris) including Pieris variety (Pieris) such, Pieris variety (Pieris) such as Pieris (Pieris variety (Pieris) such, Pieris (Pieris variety (Pieris) including Pieris) such as Pieris (Pieris variety, Pieris) and Pieris variety (Pieris) such), Pieris (Pieris) including Pieris variety (Pieris) and Pieris (Pieris) such), Pieris) such (Pieris) such), Pieris) such as (Pieris variety (Pieris) and Pieris variety (Pieris) such), Pieris variety (Pieris) variety (Pieris variety, Pieris (Pieris) and Pieris) including Pieris (Pieris) variety (Pieris) such) including Pieris variety (Pieris) such (Pieris variety (Pieris) including Pieris (Pieris variety, Pieris (Pieris variety (Pieris) including Pieris variety (Pieris) including Pieris, Cacoesia species (Cacoesia spp.), Callosobruchus maculatus (Callosobruchus maculatus) (southern cowpea weevil), yellow spot dew beetle (Carpophilus hemiptera) (stemona), testudina caragana (Cassida vittata), longicorn species (ccroscrna spp.), cerrotoma species (Ccrotoma spp.), trichomonas sp (chrysomella), leuconychus (ceromorpha trifoliatus) (setaria viridis), chlorophyta species (ceromorpha spp.), elephantopus (ceromorpha spp.), Chinese cabbage turtle species (ceromorphus assius) (cabbage caterpillar), turnip elephant species (ceromorphus purpureus), western cabbage beetle (ceromorphus), western red beetle (collybia), western red beetle (ceromorphus flavus), red beetle (collybia), red beetle (collygus purpurea), red beetle (collygus purpurea), red beetle (collygus), red beetle (red beetle), red beetle (collygus), red beetle (red beetle) and red beetle (red beetle), red beetle (red beetle), red beetle (red beetle), red beetle (red beetle, red beetle (red beetle) and red beetle (red beetle) are (red beetle, red beetle (red beetle), red beetle), red beetle (red beetle, red beetle (red beetle, red, Examples of such plants include, but are not limited to, Cryptolepis pusillus (Cryptolepis pulillus) (Aphelenchus fasciatus), Rhynchophyllus (Cryptolepis grain beetle), Ctenodera species (Ctenodera spp.) (nematodes), elephant species (Curculio spp.) (weevil), Rhinocephalus species (Cycleephora spp.) (Holotrichia dioides), Rhinocephalus degraphus (Hyponella fasciata) (Trichophyllus fasciatus), Rhinocephalus (Deporus marginatus) (Margarita fasciatus), Rhizophora paragua (Mesorus paraphyllus), Rhizophora paragua (Mesorus) (Pharmanopsis paraphyllus), Rhizophora striatus (Hypoglaucus) and Rhizophora leucotrichia (Meadora), Rhizophora leucotrichia (Piropis leucotrichia), Rhizophora leucotrichia (Piropis fasciata (Meadowrue), Rhizophora leucotrichia fasciata (Pilus) and Rhizophora) species (Meadowraenophora), Rhizophora fascicularia), Rhizophora (Piropis sp. (Pirophus fascicularis) and Rhizophyllus (Piropis) or Piropis sp. (Meadonis (Pirophus fascicularia) or Piropis (Piropis) or Pirophus fasciatus (Piropis) or A) or Piropis) or Pirophus fasciatus (Piropis) or Piropis (Pirophus fasciatus), Piropis fasciatus (Piropis) or Piropis fasciatus (Piropis L. hamus) or Piropis (Piropis L. hamus) and Piropis (Piropis) of Piropis (Pirops) of Piropis (Piropis of Pirops) of Pirops, Pirophus fasciatus (Piropis (Pirophus fasciatus), Pirophus fasciatus (Pirophus fasciatus), Piropis of Pirophus fasciatus (Pirophus fasciatus), Pirophus fasciatus (Pirophus fasciatus), Piropis (Pirophus fasciatus), Piropis of Piropis) of Pirophus fasciatus (Piropis ) of Piropis, Pirophus fasciatus (Pirophus fasciatus), Piropis) of Pirophus fasciatus (Piropis of Piropis, Piropis of Pirop, Lucerne medicago sativa (hyperbaric) (medicago sativa), medicago species (hyperboes spp.) (argentina stem weevil (Hyperodes weevil)), coffee chervil (polyphnemus hamperei) (coffee chervil), scotland species (Ips spp.) (echinacea purpurea), tobacco beetle (Lasioderma serricorne) (tobacco beetle), potato beetle (leptotarsa decemlata) (colorado potato beetle), lipoglorys fuscus, lipogynys suturalis, rice water weevil (lisurena oryzophilus) (rice water weevil), silphigus species (lycospera spellensis), meldonia sp.) (meclizia purpurea/tenera), meldonia terrestris (meldonia), meldonia spp (meldonia spp.) (Mewlela spp.) (Mewlera), Mesorrel louse beetle (Mewlela spp.) (Messoides), Mesorrel louse beetle sporulata (Mewlela spp. (Messochloes sporea), Mewless beetle spp. (Messel beetle spruce) Rhinoceros rhynchophylla (oriycetes rhinoceros) (date palm beetle), ceremony saw beetle (oryzaephiulus mercator) (market saw beetle), cercaria terrestris (elephant), cercaria terrestris (odontobrama), cercaria species (oxytrophus spp), cercaria nigripes (auricle melas mellea) (orange leaf beetle), cercaria terrestris (auricle oryzae), cerbrotica rosea (purpureus), cercaria species (panomyopis p), panopis palustris (ostrinia nubilalis), cercaria terrestris (purpurea), cercaria macrotrichia (peruvignonensis), cercaria terrestris (purpurea), cercaria macrotrichia (pernya), cercaria stris (purpurea), cercaria macrotrichia terrestris (purpurea), cercaria terrestris (bullosa) (common beetle species), cercaria stringta (bullosa) (common beetle species (pink) (common beetle species), cerifera), cerbrotica striga (mangle), cerifera), cerbrotica striga (mangle), cercospinus mangle), cerifera (mangle) and cerifera) including rhizopus mangle (mangle) and cerifera (mangle, cerifera) including rhizopus mangle, cerifera, mangle, cerifera, cerbrotica, kayas, cerbrotica, and eugles, cerbrotica, and eugles (mange, kayas, and eugles (mangle, chaeta, kayas (mange, picea (mangle, picea (mangle, picea mangle, picea mange, picea mangle, picea (mangle, picea mange, picea mange, picea mangle, picea mange, picea mange, picea mangle, picea mange, picea, pic, Root gill species (rhizomorphous spp.) (european scarab (european chafer)), cryptorhynchophorus species (ryophorus spp.) (elephant), silly species (Scolytus spp.) (wooddull moth), shonophorus species (shonophorus spp.) (cereal elephant), pisum sativum leaf (Sitona linkuntze) (pea leaf weevil (pca leaf weevil)), rice weevil species (Sitophilus spp.) (cereal weevil), rice elephant (Sitophilus grandis) (paddy insect (granavirus), rice elephant (Sitophilus oryzae) (rice weevil), rice paneum (stewartum), triphyllum sativum (triborum), and red beetle (Tribolium), red beetle (Tribolium sativum), red beetle (Tribolium), red beetle (red beetle), red beetle (red beetle, red beetle.
Dermaptera (Dcrmaptcra) (earwigs).
Vein winged order (Dictyoptera) (cockroach): german cockroach (Blattella germanica) (German cockroach), blattaria orientalis (Blatta orientalis), Blatta palustris (Blatta cockroach), Blatta australiana (parcoblata penylvanica), Periplaneta americana (perilanta americana) (austria americana), Blatta australiana (australia cockroach)), Periplaneta fusca (pcripa rubra) (australia cockroach), Periplaneta fuliginosa (brown cockroach), Periplaneta smokosa (perilanta fuliginosa) (Periplaneta fuliginosa (cockroach)), and Periplaneta fuliginosa (brown cockroach) (Periplaneta subcapium (brown cockroach)), and Periplaneta fuligina (brown cockroach) (Periplaneta rubra americana (brown cockroach)).
Diptera (Diptera) (flies): mosquito species (Aedes spp.) (mosquito), lucerne fly larvae (Agromyza frontella) (alfa blotch), agromyzis species ((Agromyza spp.) (leaf miner), trypetid species (anastrep spp.) (fruit fly), garleria persica (anastrepa subsp.) (fruit fly), garleria persica (garleria persica) (garleria persica (tail fly)), mosquito species (anophes spp.) (mosquito), fruit fly species (batrachta spp.) (fruit fly), melon fly (Bactrocera bitrae) (melon), citrus fruit fly (Bactrocera persica), mosquito species (ceitis spp.) (mosquito), mosquito fly larvae (sea fly larvae) (sea fly), sea fly larvae (sea fly larvae) (deer spp.) (moth), sea fly larvae (sea fly larvae) (moth larvae) (bilus persica spp.) (fruit fly) (moth larvae) (mosquito larvae) (deer spp.) (fruit fly) (garrisb) (mosquito larvae) (sea fly) (moth) Leaf of rape mosquito (Dasineura brassicae) (cabbage mosquito), Dimochi species (Delia spp.), Grapholitha platura (root maggot (seed corn bug)), Drosophila species (Drosophila spp.) (vinegar fly), Musca species (Fannia spp.) (housefly), yellow belly fly (Fannia canthus) (summer fly (litter house fly)), Grey belly fly (grey belly fly) (Grey belly fly), Gasterophilus intestinalis (Gasterophilus intestinalis) (horse bot), Gracillia persea, Haematobia irritani (Haematobia irrita) (fly), Black fly species (Hymenea spp.) (root maggot) (root fly), Musca (cabbage fly), Musca fly (seedling fly), Musca fly (leaf fly), Musca fly (cabbage fly) (fly), Musca fly (leaf fly), Musca fly (cabbage fly (leaf fly) (fly), Musca fly (leaf fly) (fly, cabbage fly (leaf fly) (fly), Musca fly (leaf fly) (fly), Musca fly (leaf fly) (fly) and Musca fly (leaf fly) (fly) of Musca fly), Musca fly (leaf, Musca fly) (fly) of Musca fly), Musca fly (fly) (fly, Musca fly) (fly, Musca fly) (fly) of Musca fly, Musca fly) (fly ), Musca) of Musca fly (fly, Musca) of Musca fly (leaf, Musca fly (fly, fly) (fly, Musca) of Musca, Musca) and Musca, Musca) of Musca, Musca variety, Musca variety (fly) (fly ) (fly, The plant includes, but is not limited to, the species fall houseflies (Musca australis) (face fly), houseflies (Vusca domestica) (house fly), sheep houseflies (oesteurs ovis) (sheep nose fly (sheet boot fly)), european stem flies (ostrinia sativa) (stem fly), beet spring flies (pegomya beta) (spinach leaf miner), Musca sp (Phorbia spp.), carrot stem flies (psilla rosella (carrot leaf fly)), cherry fruit flies (rhagophylla cerasi) (cherry fruit fly)), apple fruit flies (rhapontella pomonella) (apple maggot)), red mud fly (Sitodiplosis), orange fruit fly (horsefly), and cattle fly (stable fly) (horse fly).
Hemiptera (Hemiptera) (stinkbug): apolygus lucorum (Acrosteronum hieron) (green stink bug), Oryza sativa (Blissus leucopterus) (long stink bug), Oryza sativa (Caloris norvegicus) (potato stink bug), Tropical stink bug (Cimex hemipterus) (tropical stink), stinkbug (Cimex leucopterus) (bed bug), Daghertus fasciatus, Dichelops furcatus, Oryza sativa (Eucotton stainer), Edestabunda (Oryza sativa), Oryza sativa (Lepidorum), Oryza sativa (Oryza sativa) and Oryza sativa (Oryza sativa) by (Oryza sativa) and/or Oryza sativa (Oryza sativa) for treating plant (Oryza sativa) and/Oryza sativa (Oryza sativa) for treating plant, Lygus hesperus (Lygus hesperus) (western tarnished plant bug), hibiscus syriacus linnaeus (macrocytoericcus hirsutus), neuroolpus longirostris, rice green bugs (Nezara viridula) (southern green stink bug), Lygus planterum (phytolocoris spp.) (Lygus), california planterus (phytoorius californicus), phytoorius relatus, piezocoritus guilidingdinggi, tetrad bugs (podocarpus utilis linus) (folulated plant bug), psycaninum vaccicola, pseudostellaria persica, scorpio corina and trypanosoma (trypanosoma) seed (nose cone).
Homoptera (Homoptera) (aphid, scale, whitefly, leafhopper): piper pisum (Acrythosiphopkinsum) (pea aphid)), Coccinum species (Adelges spp.) (adelgids), Beeuglena brassicae (Aleurodes proteella) (Beeuglena cabbage whitefly), Aleurodicus disperses (Aleurodicus disperses), Aleurothrix striatus (Aleurothrix luteus) (gloomy whitley), Begoniothyria albonensis species (Aluaspis spp.) (Aluraceae biguella), Pectinatus species (Aphrophola sp.) (Aphrophophora spp.) (leafhopper), Rhodococcus rhododendron (Aoniella natura), Begoniothrix gloeosporioides (Begonioth), Begoniothrix gloeosporus (Begoniothrix), Begoniothrix aphid (Begoniothrix), Begoniothrix) aphid (Begoniothrix), Begoniothrix sp (Begoniothrix) and Begoniothrix aphid (Begoniothrix) Aphis (Begonioth), Begonioth (Aphis) Aphis sp), Begonioth (Begonia), Begonioth (Aphis sp), Begonioth (Begonioth) Aphis sp), Begonia), Begonioth (Begonia), Begoniothrix) and Begoniothrix) species (Begoniothrix) of Aphis, Begoniothrix, Aphis, asparagus tubular aphid (Brachyryyncria asparagi) (Asparagus aphid), Brevennia rehi, cabbage aphid (Brevicornus brassicae) (cabbage aphid), Lecanicillium species (Ceroplastes spp.) (scale), Ceriporiococcus rubens (Ceroplastes rubens) (red wax scale), Cestrum species (Chionastis spp.) (Iceltica), Lecanicillium species (Chrysomophagus spp.) (scale), Ceriporiococcus species (Coccus spp.) (scale), apple pink aphid (Dysapphigenia plantaginea) (sysplex aphid), Phyllopsis viridis (apple aphid) and Lecanicola (apple aphid) plant (apple aphid), Phyllospora major (apple aphid), Phyllospora (apple aphid) and Lecanicola (apple aphid), Phyllospora grandis (apple aphid), Phyllophora gossypium (apple aphid), Leonicola (apple aphid (apple), and Leonicola (apple aphid), Phyllophora variety (apple aphid) and Leonicola (apple aphid) of Leonicola (apple aphid (apple), Leonicola (apple aphid), and leaf, apple aphid (apple), and leaf, leaf strain (apple stem) (maize) plant, leaf strain (apple stem, leaf, Leaf of the species Mylopharyngodium (Macrosiphum grandium) (English grandis)), Long pipe aphid (Macrosiphum rosae) (Rose aphid (rose aphid)), four-leaf hopper (Macrosteles quadratus) (purple leaf hopper (ash leaf hopper)), Mahanarva frimbiola, Meopodium diricum (wheat germ) aphid (rose aphid), Midis Longicornis, peach aphid (Myzus persicae) (peach aphid (green apple aphid)), Nephophylum spruce (Nephotettix spreng) (leaf hopper), Nephotettix cinctix (green leaf hopper), Phosphaera (brown apple aphid) (Phosphaera), Phosphaera (brown apple aphid) (leaf hopper), Phosphaera (leaf hopper), Phosphaericoides) (leaf hopper) (leaf hopper), leaf hopper (leaf hopper) (leaf hopper (leaf), leaf hopper (leaf hopper (leaf hopper) and leaf hopper (leaf hopper) (leaf hopper (leaf hopper) leaf, leaf hopper (leaf hopper) Pygeum sp (mealybugs), pygeus sp (mealybugs), begecky sp (Pseudococcus spp), mealybugs (Pseudococcus brcvps) (pink apple), pernicia pelyridis (quadrspididatus) (saint josephse), pygecky sp (Rhapalosiphum sp.) (aphid), corn leaf aphid (rhaalophilus maida) (corn aphid), corn leaf aphid (bitter orange apple tree), red apple wax apple tree (white apple tree) (black apple tree) (black apple tree), white apple tree (white apple tree) (black apple tree), apple tree) (black apple tree) (black apple, Whitefly species (Trialeurodes spp.) (whitefly), greenhouse whitefly (Trialeurodes vaporariorum) (greenhouses whitefly), brown wing whitefly (Trialeurodes abutiloneus) (bandtwing whitefly), cupula species (Unaspis spp.) (scale), arrowhead (Unaspis yanonensis) (arrowhead scale), and Zulia entreriana.
Hymenoptera (Hymenoptera) (ants, wasps and bees): incised leaf ant species (Acrommerx spp.), Sinkiang leaf bees (Athalia rosae), leaf ant species (Atta spp.), Ieafcutting ants, Black ant species (Camponus spp.), wooden ants (carpenter ant), pine leaf bee species (Diprion spp.), leaf bees (sawfly), Formica spp. (Formica spp.), Argentina argentea (Iridogyrmex pollicis) (Argentintinentant), Coccinum subspecies (Monoririum spp.), little termites (little termite) and Solomon bee species (Melothrix spp.), Taenia Solenopsis (Solomon), Queensis (Meloth spp.)), New Penny leaf bee species (Neurospori spp.) (Meloth) and domestic bee species (Solomon spp.) (Meloth bee species), and Queensis bee species (Solomon spp.) (Meloth bee species), Melothrix spp. (Melothrix spp.) (Melothrix) and bee species (Solomon bee), Melothrix spp. (Melothrix spp.) (Meloth bee), and Melothrix spp. (Melothrix spp.) (Meloth. solveus spp.) (Ant) and Queen bee species (Solomon bee), Meloth bee species (Solomon bee) and Meloth bee species (Meloth. solemx spp. (Meloth) and Melothianus spp. (Melothiastrum bee), and Melothiastrum bee species (Melothiao bee) and Meloth bee (Meloth (Melothiao bee), and Melothrix spp. (Melothiastrum spp. (Melothrix spp. (Melothiao, Wasp species (vespela spp.) (yellow jack) and trichogramma species (Xylocopa spp.) (carpenter bee).
Isoptera (Isoptera) (termites): coptotermes spp, Coptotermes curcus, Coptotermes flavus, Coptotermes formosanus, Coptotermes spp, Coptotermes formosanus, Coptotermes spp, Coptotermes formosanus, Coptotermes formotermes spp, Heterotermes spp, Coptotermes formotermes formosanus, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes termes spp, Coptotermes formosanus spp, Coptotermes termes spp, Coptotermes formosanus termes, Coptotermes termes, Coptotermes spp, Coptotermes termes formosanus spp, Coptotermes termes, Coptotermes termes, Coptotermes termes, Coptotermes termes, Cotermes termes, Coter, Reticulitermes banyulensis, Spodoptera grassland (Reticulitermes grassei), Reticulitermes flavipes (Reticulitermes flavipes) (eastern soil-dwelling termites), Reticulitermes flavipes (Reticulitermes hagenii), West Scleropectium (Reticulitermes heperus) (West soil-dwelling termites), Moraxeticles sanguineus (Reticulitermes santonensis), Norterex benthamoides (Reticulitermes speratus), Reticulitermes nigripes (Reticulitermes tibialis), Reticulitermes virginicus (Reticulitermes virginicus), Reticulitermes formosanus species (Schedorthes spp.) and Zootes spp (Zooter termite spp.).
Lepidoptera (Lepidoptera) (moths and butterflies): achoea janata, Trichosporon species (Adoxophyceae spp.), Trichosta gossypii (Adoxophyceae orana), Gekko sp (Agrotis spp.), cutworm ((Agrotis ipsilon) (Black cutter), Trichosta gossypii (Alabama argillacea) (Cotton leaf worm), Amorbia cuneata (Amomum cubensis), Amorbia cuneata, Amylosis trastuella (Na orange) Teng, Anacoptida, Spodoptera fortunei (Na orange), Anacoptids degelata, Spodoptera cuneata (Anarctia lineata) (peach twigs borrer), Athiophylla (Anomyia sanguinea), Trichosta (Boomula japonica) (Boyloptera), Trichosta niponica (Boyloptera), Spodoptera (Ostrinia), Spodoptera (Boyloptera), Spodoptera fructicola (Boyloides kura), Spodoptera (Boyloptera) variety (Boyloptera), Spodopterocarpus (Boyloptera), Spodoptera (Boyloptera) and Boylophyta (Boylopterocarpus (Boylophysa) variety (Boylophysa) including Boylophysa, Spodopterocarpus (Boylophysa) and Boylophysa (Boylophysa) can, The species of the genus Spodoptera (Caloptilia spp.) (Spodoptera exigua), Capua reticulana, peach fruit moth (Carposina niponensis) (peach fruit moth)), Bombycis (Chilo spp.), mango lateral-thread Philippine moth (Chuumetia transversa) (mango shoot front borner), rose leaf roller (Choristeura rosaria) (oblitera rosea) (oblitera), noctuid barrel (noctuid roller), Spodoptera species (Chrysodexis p.), Ostrinia punctata (Cnaphaloceras medialis) (Spodoptera grasses (Spodoptera)), Spodoptera litura (Spodoptera), Coprinus litura (apple leaf moth) (apple moth (Cypress), Spirochaeta (Spirochaeta), Plutella xylostella (Spirocha), Spirochalia xylostella), Spirochalia striata (Conemonorhala), Spirochalia xylostella (Spodoptera), Spirochalia xylostella (Sporina), Spirochada (Sporina), Spirocha (Sporina), Sporina (Sporidina (Sporina), Sporina) and Sporina) species (Sporina) of the family, Sporina (Sporina) and Sporina (Sporina) in the family, Sporina (Sporina) of the family, Sporina (Sporina) and Sporina (Sporina) of the family, Sporigana (Sporigana) of the genus Sporigana, Sporigana (Sporigana, Sporigana (Sporigana) of the family, Sporigana (Sporigana, Sporigana (Sporigana) of the family, Sporigana, Spiritis (Sporigana, Sporigana (Sporigana, Sp, the species Darna diducta, Diaphania sp (Diaphania spp.) (stem borer)), borer sp (Diaphania spp.) (stem borer (staged borer)), borer (Diaphania saccharalis) (sungar borer), southwestern corn stalk (Diaphania grandiflora) (southwestern corn borer), diamond-back seed (eared diamond-back) eared (eared diamond-back), cotton bollworm (eared bollworm), and diamond-back (earia insulata) (egyptiana boreworm), diamond-back (eared diamond-back) (roughh northern pink bollworm), dynastigma (apple stem borer), ostrinia (ostrinia), ostrinia nubila (ostrinia nubila), ostrinia nubilalis (ostrinia nubilalis), ostrinia nubilalis) (ostrinia nubilalis), ostrinia nubilalis (ostrinia nubilalis) (ostrinia nubila nubilalis), ostrinia nubilalis (ostrinia nubilalis), ostrinia nubilalis) (ostrinia nubilalis (ostrinia nubila nubilalis) (ostrinia nubilalis), ostrinia nubilalis (ostrinia nubila nubilalis), ostrinia nubila nubilalis (ostrinia nubilalis), ostrinia nubila nubilalis (ostrinia nubila, ostrinia nubila nubilalis), ostrinia nubila, ostrinia nubila (ostrinia nubila, ostrinia nubila (ostrinia nubila, ostrinia (ostrinia nubila, ostrinia nubila, ostrinia nubila, ostrinia nubila, ostrinia nubila (ostrinia, ostrinia nubila, ostrinia nubila, ostrinia nubila, Noctuid (epiotia aporema), scolyptera bananas (eriodictyon x) (banana skipper), euglenopsis lucida (Eupoecilia ambiguella) (grape berry moth (grape berry moth)), Euxoa auricularia (Euxoa auricularis) (army cutworm), cutworm (ferula sp.) (cutworm), hornworm (gorworm sp.) (moth), oriental moth (grapholitta molesta) (peach (apricot) seed heart worm (original fruit moth)), borer (moth) (soybean leaf moth (cabbage leaf moth)), budworm sp.) (Helicoverpa sp.) (Helicoverpa sp.)), cotton bollworm (corn earworm) (Helicoverpa punctifera), Helicoverpa punctifera (Helicoverpa punctifera) (Helicosa (Helicoverpa sp.)), Helicoverpa sp.) (Helicosa (Helicoverpa sp.)) and Helicoverpa sp.) (Helicoverpa sp.))), Tomato moth (Keifera lycopersicella) (tomato pinum), white-fin webworm (Leucinodes orbornata) of Solanum, egg plant fruit moth (egg plant fruit borrelia), leaf miner (Leucoptera malinella), the species Plutella xylostella (Lithocollectis spp.), grape leaf moth (Lobesia borrelia) (grape fruit mot), the species Loxagrus (Loxagrus spp.), the species Laurella punctata (Laurella punctata), the species Laurella cerifera (Loxagrus alburena), the species Laurella punctata (Bean white-leaf diculus (Bean) of Leguminosae), the species Lymantria (Lymantria disparis) (grape fruit bud), the species Lymantria dispar) (gypsylla), the species (Lyonetia punctifera), the species Lyonella (apple leaf moth (apple leaf miner), the oil bag (cabbage), the species (cabbage moth) (cabbage leaf borer), the species (leaf moth (Lymantria), the species (Lyonetia punctifera), the species (Lyoneura) of Plutella (Plutella), the species (Plutella) of Plutella (Plutella), the species (Plutella) of Spinacea brueckea fructia (Spinacea), the species of Spinacea (Spodophylla) of Plutella (Spinacea), the species of Spinacea (Spinea), the genus (Spinacea) of Spinacea (Spinaceus) of Spinaceus (Spinaceus) of Spinaceus (Spinaceus) of Spinaceus, Spinaceus (Spinaceus) of Spinaceus (Spinaceus) of Spinaceus), Spinaceus (Spinaceus) of Spinaceus (Spinaceus) of Spinaceus (Spinacia), Spinaceus (Spinaceus) of Spinaceus (Spinaceus) of Spinaceus (Spinacia), Spinaceus (Spinaceus) of Spinaceus (Spinacia), Spinaceus (Spinac, Winter loopers (Operphthora briata) (winter moth)), European corn borer (Ostrinia nubilalis) (European corn borer (European corn borner)), Oxydia vesula, Ostrinia fructicola (Pandemia cerosa) (common grape leaf moth (common currant torax)), apple leaf moth (Pandemia hepiali) (brown apple pitridix), African damascena (Papilio demodula), Red wheat moth (Pectinophora gossypiella) (red bell (pink bollworm)), Arctia species (Peridroma spp.) (Rhizopus), European red tiger (Peridroma sacchrina) (cabbage caterpillar (cabbage)), European red cabbage looper (Peripleria punctatus), European red cabbage moth (cabbage caterpillar), European red cabbage caterpillar (Peripleria spodoptera), European red cabbage caterpillar (cabbage caterpillar), European red cabbage caterpillar (cabbage caterpillar), European cabbage caterpillar (cabbage caterpillar), cabbage caterpillar (cabbage caterpillar) (cabbage caterpillar variety of the species (cabbage caterpillar), cabbage caterpillar (cabbage caterpillar) of the species (cabbage caterpillar, cabbage caterpillar (cabbage caterpillar), cabbage caterpillar (cabbage caterpillar ) of the species of the genus of, Cabbage moth (Plutella xylostella) (diamondback moth), grape berry moth (polychrosia virosa) (grapple berry mountain moth), orange fruit moth (Prays endocarps), olive moth (prasys oleae) (olive moth), armyworm species (pseudotales spp.) (noctuid), pseudolitea unipicta (marcescens), soybean looper (pseudolitea includens) (soybe looper), looper (raphanus nu), tryporyza incertulas (scirphaga incertulas), stem borer (Sesamia fischeri), stem moth (Sesamia infusoriana) and Spirospongia armyworm (Spodoptera), cabbage looper (Spirochaetes), cabbage looper (Spirocha spongiosa), cabbage looper (Spodoptera spongiosa), cabbage looper (Spodopterocarpus niponensis) (Spodoptera spongiosa), cabbage looper (Spodopterocarpus niponaria), cabbage looper (Spodopterocarpus nipona), cabbage looper) (Spodoptera), Spodopterocarpus (Spodoptera), Spodoptera) moth (Spodopterocarpus (Spodoptera), Spodoptera) and Spodopterocarpus (Spodopterocarpa) are) species (Spodopterocarpus (Spodopterocarpa) including Spodoptera) and Spodoptera) including Spodopterocarpus (Spodoptera) and Spodoptera) including rice stem moth (Spodopterocarpus (Spodoptera) and Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) including rice stem moth (Spodoptera variety, Spodoptera variety (Spodoptera) and Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) and Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) and Spodoptera) including rice stem moth (Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) and rice stem moth (Spodoptera) such as well, Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) and rice stem moth (Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera variety, Spodoptera) and rice stem moth (Spodoptera) including rice stem moth (Spodoptera) and rice stem moth (Spodoptera variety (Spodoptera) and rice stem moth (Spodoptera) including rice stem moth (Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera variety (Spodoptera) including rice moth (Spodoptera variety, Southern Spodoptera oridania (southern armyworm), athetosis species (synanthondon spp.) (root borer), Therla basilides, Thermia gemmatalis, Chlamydomonas (tienola bisselella) (webbings moth.), Trichoplusia ni (Trichoplusia ni) (camera bbeller), Tolyta domestica (Tuts absoluta), Nematoda species (Yponomeuta spp.), Coffeta (Zeuzeracow corn), and Zeuzera pyrina (Pleurotus parviensis).
Mallophaga ((Mallophaga) feather louse (chewing lice)): sheep feather louse (Bovicola ovis) (sheet biting louse), turkey short horn feather louse (chicken body louse), and chicken feather louse (Menopon gallina) (common henhouse).
Orthoptera (Orthoptera) (grasshopper, locust and cricket): arana nigra (anacrus simplex) (Mormon horns (Mormon cricket)), mole cricket (Gryllotalpidae) (mole cricket)), eastern asia migratory locust (Locusta migratoria), grasshopper species (Melanoplus spp.) (grasshopper), acephalus wing slender thorns (Microcentrum rethreshold) (angular wing broad katydid)), pterophyces species (pterophyces spp.) (pterophyces sp.) (grasshopper), steleophaga egr, pterygrasus furcifera (scudderis) (harlequin bushy bush (fork tailed bustydidid)), and tuberous ridge (vani.
Phthiraptera (Phthiraptera) (sucking lice): the blood sucking lice species (haemattopinus spp.) (cattle and pig lice), sheep jaw lice (sheep lice), head lice (pedigree capitis) (body lice), human body lice (pedigree humanus (body lice) and crab lice (crab lice)).
Siphonaptera (daphnaptera) (fleas): ctenocephalides canis (dog flea), Ctenocephalides felis (cat flea) and human flea (Pulex irutans) (human flea).
Thysanoptera (thrips): frankliniella fusca (Frankliniella fusca) (tobaco third), Frankliniella occidentalis (western flower) Frankliniella hultrias (western flower), Frankliniella shultzii (Frankliniella williamsii) (corn Thrips), Frankliniella glasshouse Thrips (IIelothrips hamoralidis) (greenhous third), Riphisprothrips cruentus, Scirpus sp (Sciroththrips spp), Platycodon grandiflorum (Scirthricirris) (citrus trough), Frankliniella tabacum (Scirthrips spp), Talothriparia (yellow Thrips spp), and Throughthrips (Thripus spp).
Thysanoptera (Thysanura) (bristletail): chlamydomonas species (Lepisma spp.) (silverfish) and locusta species (Thermobia spp.) (locusta spp.).
From the order of Acarina (Acarina) (mites (mite) and cicadas (tick)): woodbee scutellariae (acarapis woodi) (parasitic mites in the trachea of bees), dermatophagoides farinae (Acarus spp.), dermatophagoides farinae (food mites), Acarus macrorhizus (Acarus sriro) (corn mite (grain mite)), mangifera gemini (Aceria mangifera) (mango bud mite), acanthophyrus stictus (Acarus spp.), acanthophycus solani (acanthophyrus sp.), acanthophysalis lycopersici (acanthophyrus sp.), tomaticus setosum (tomatophysus) tomatin (tomatophyceae), acanthophycus purpureus (acanthophyceae), acanthophyrus stictus (acanthophyceae) (apple pythium sp.), procumbens (acanthophyrus sp.), procumbens (mangiferus sp.), rhipifera (mangiferus sp.), rhynchopus sp.), euonymus (bracteus sp.), rhynchopus sp.), euonymus (mangiferus sp.), and mangiferus sp (mangiferus sp.), euonymus sp (mangiferus sp.), euonymus sp (mangiferus sp.), euonymus sp (mangiferus sp.), euonymus sp (mangiferus sp.), euonymus (mangiferus sp.), euonymus (mangiferus sp.), euonymus (mangiferus sp.) A (mangiferus sp.), euonymus (mangiferus sp.), gra (mangiferus sp.), euonymus (mangiferus sp.), gra (mangiferus sp.), euonymus (mangiferus sp.), gra. sp.), euonymus (mangiferus sp.), gra (mangifer (mangiferus sp.), gra, House dust mite (Dermatophagoides pteronyssinus) (house dust mite), Tetranychus sp (Eototryanus spp.), Carpinus horneri sp (Eototryanus carpini (yellow spider mite), Tetranychus sp.), Acarinus sp (Eriophenous spp.), Stephania sp (hard tick sp.; es sp.), ticks (tick), Tetranychus sp. (Tetranychus sp.), Acarinus sp. (Notoedressi spec), Acarinus sp. (Notoerdorhycus sp.), Acarinus gracilis (Notoedressi. sp.), Acarinus parvus (Oligonychus spyricus sp.), Acarinus gracilis (Ocigonurus), Acarinus wintergreen (Oligonychus (Oligonus) (sorred mite), Acarinus fuliginosus (Tetranychus), Acarinus pallidus (Tetranychus), Acarinus fuliginosus (Tetranychus), Acarinus tetranychus (Tetranychus urticae), Acarinus (Tetranychus urticae), Acarinus) (Tetranychus urticae (Tetranychus), Acarinus) (Tetranychus) or Tetranychus urticae), Acarinus (Tetranychus) (Phoenii (Tetranychus) and Tetranychus (Tetranychus) or Tetranychus (Tetranychus) or (Tetranychus) or Tetranychus (Tetranychus) or Tetranychus (Tetrasticus) or (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus), Rhizomorpha species (rhizomorph spp.) (root mite (bulb mite)), Sarcoptes scabies (Sarcoptes scabies) (itch mite), coronaria avocado (tetragonophys perseafarae), Tetranychus species (Tetranychus spp.), Tetranychus urticae (Tetranychus urticae) (twospoked spider mite)) and Varroa destructor (Varroa destructor) (honey bee mite).
Nematoda (nematodes): the species Aphelenchoides (Aphelenchoides spp.) (bud and leaf and pine wood nematodes (bud and leaf & pine wood nematodes)), the species nematodiasis (Belonolaevis spp.) (sting nematodes), the species Cyclotella minor (Criconella spp.) (ring nematodes), the species Dirofilaria immitis (dog heartword), the species Ditylenchus spp. (stem and bulb nematodes), the species Trichophythora (Heterodera spp.) (Cytospora spp.), the species Heterocladia (Heterocladia zeae) (maize nematodides), the species Melilodinia spp. (Hichlamyella spp.) (Melilotus spp.)), the species Heterocladospora spp.) (Melilotus spp.)), the species Melilotus spp.) (Melilotus spp.)), the species (Melilotus spp.)), the species), Melilotus spp.) (Melilotus) and Melilotus spp.) (Melilotus, Melilotus spp.) (Melilotus) and Melilotus spp.) (Melilotus, Melilotus spp.) (Melilotus) and Melilotus, Melilotus spp.) (Melilotus, Melilotus spp.) (Melilotus, Melilotus spp.) (Melilotus ) and Melilotus, Melilotus spp.) (Melilotus, Melilo, The species of the genus Rapholus (Rapholus spp.) (Burrowing nematode) and the species of the Leptochloa (Rotylenchus reniformis) (kidney-shaped nematode).
General class (general classes of insects): white pine worm (Scutigerella immaculata).
Owing to their positive properties, the abovementioned compounds can be used advantageously for protecting crops, domestic animals and breeding animals of agricultural and horticultural importance, as well as the environment in which humans are often exposed, against harmful germs, pests and mites.
The amount of the compound used to achieve the desired effect will vary depending on factors such as the compound used, the crop to be protected, the type of pest, the extent of infection, the climatic conditions, the method of application, and the dosage form employed.
A dose of 10 g to 5 kg of compound per hectare provides adequate control.
The invention also discloses a sterilization, disinsection and acaricidal composition which takes the compound shown in the general formula I as an active component. The weight percentage of the active components in the composition for killing bacteria, insects and mites is between 0.5 and 99 percent. The composition also comprises a carrier acceptable in agriculture, forestry and sanitation.
The compositions of the present invention may be administered in the form of a formulation. The compounds of formula I as active ingredients are dissolved or dispersed in carriers or formulated to be more easily dispersible for bactericidal, insecticidal use. For example: the chemical preparations can be prepared into wettable powder, oil suspension, water suspension, aqueous emulsion, aqueous solution or missible oil and the like. In these compositions, at least one liquid or solid carrier is added, and when necessary, a suitable surfactant may be added.
The technical scheme of the invention also comprises a method for preventing and controlling germs, pests and mites, which comprises the following steps: the sterilizing, insecticidal and acaricidal composition is applied to the pathogenic bacteria or the growth medium thereof. Preferably, an effective amount of 10 to 1000 grams per hectare is generally selected, with an effective amount of 20 to 500 grams per hectare being preferred.
For certain applications, for example in agriculture, one or more other fungicides, insecticides, acaricides, herbicides, plant growth regulators or fertilizers and the like can be added to the fungicidal, insecticidal and acaricidal compositions of the present invention, whereby additional advantages and effects can be produced.
It should be understood that various changes and modifications may be made within the scope of the present invention as defined by the claims.
Detailed Description
The following specific examples are intended to further illustrate the invention, but the invention is in no way limited to these examples (all materials are commercially available unless otherwise indicated).
Synthetic examples
Example 1: preparation of intermediate 4, 5-dichloro-6-methylpyrimidine
1) Preparation of 4-hydroxy-5-chloro-6-methylpyrimidine
Figure BDA0002445325790000461
To a solution of 11.30g (0.11mol) formamidine acetate in 50mL of methanol was slowly added dropwise, while stirring at room temperature, a solution of 8.80g (0.16mol) of sodium methoxide in methanol, and stirring was continued for 2 hours at room temperature after completion of the addition. Then, 11.17g (0.068mol) of intermediate ethyl 2-chloroacetoacetate was added dropwise to the above solution, and the reaction was continued with stirring at room temperature for 5 to 7 hours. After TLC monitoring reaction, decompressing and distilling off solvent, adjusting pH to 5-6 with hydrochloric acid, filtering to obtain orange yellow solid, extracting water phase with (3X 50ml) ethyl acetate, drying with anhydrous magnesium sulfate, filtering and desolventizing. The residue was dissolved in 50mL ethyl acetate, left overnight and filtered to give 6.48g of an orange-yellow solid. The yield is 66 percent, and the melting point is 181-184 ℃.
2) Preparation of 4, 5-dichloro-6-methylpyrimidine
Figure BDA0002445325790000462
14.5g (0.1mol) of 4-hydroxy-5-chloro-6-methylpyrimidine is dissolved in 50mL of toluene solution, 50mL of phosphorus oxychloride is dripped into a reaction bottle under stirring, and the temperature is increased after dripping for reflux reaction for 5 to 7 hours. After completion of the TLC monitoring reaction, toluene and excess phosphorus oxychloride were distilled off under reduced pressure, the reaction was poured into ice water with stirring, the aqueous phase was extracted with ethyl acetate (3X 50mL), the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and desolventized. The residue was subjected to column chromatography (eluent ethyl acetate and petroleum ether at a volume ratio of 1:5) to give 14.43g of a yellow liquid with a yield of 88.5%.
Example 2: preparation of 4, 5-dichlorothieno [2,3-d ] pyrimidine
Figure BDA0002445325790000463
Taking 2-amino-3-cyano-4-oxo-5, 5-dihydrothiophene and 250mL of phosphorus oxychloride (POCl)3) In the reaction flask, 38ml of N, N-dimethylformamide was slowly dropped at room temperature over about 30 minutes. The reaction was carried out at room temperature for 1 hour and then at 75 ℃ for 3 hours. After cooling to room temperature, the reaction solution was poured into crushed ice and filtered to obtain 89.1g of dark gray solid with a yield of 86.9% and a melting point of 160-.
Example 3: preparation of intermediate 4-chloroquinazoline
1) Preparation of quinazolin-4 (3H) -ones
Figure BDA0002445325790000471
13.7g (0.1mol) of anthranilic acid and 20ml of formamide are taken in a 250ml three-necked flask and heated to 140 ℃ for reaction for 5-8 hours. After the completion of the TLC monitoring reaction, the reaction solution was cooled to 100 ℃ and 80mL of water was added dropwise with stirring, followed by cooling to room temperature, filtration and washing of the filter cake with anhydrous ether to obtain 10.96g of reddish brown with a yield of 75.1%.
2) Preparation of 4-chloroquinazoline
Figure BDA0002445325790000472
14.6g (0.1mol) of quinazolin-4 (3H) -one is taken in a 250mL single-neck bottle, 50mL of thionyl chloride is taken as a solvent, and the temperature is increased to reflux reaction for 4 to 6 hours. After the completion of the TLC monitoring reaction, the reaction solution was cooled and poured into water and stirred for 30min, filtered and washed with anhydrous ether to obtain a reddish brown solid 10.96g, yield 92.7%.
Example 4: synthesis of intermediate 2- (1- (4-chlorophenyl) -1H-pyrazole-3-oxy) ethylamine hydrochloride
1) Preparation of N-Boc-2-bromoethylamine
Figure BDA0002445325790000473
20.5g (0.1mol) of bromoethylamine bromate was placed in 80mL of tetrahydrofuran, 10.08g (0.12mol) of sodium bicarbonate and 50mL of water were sequentially added, 21.80g (0.1mol) of di-tert-butyl dicarbonate was added dropwise under stirring at room temperature, and the reaction was continued for 4 to 10 hours after completion of the dropwise addition. After the reaction, the solvent was distilled off under reduced pressure, ethyl acetate (3X 50mL) was added for extraction, and the organic phase was washed with 50mL of saturated brine to obtain 21.84g of a colorless oily liquid with a yield of 97.5%.
2) Preparation of N-Boc-2- (1- (4-chlorophenyl) -1H-pyrazol-3-yloxy) ethylamine
Figure BDA0002445325790000474
2.24g (0.01mol) of N-Boc-2-bromoethylamine and 1.94g (0.01mol) of 1- (4-chlorophenyl) -1H-3-hydroxypyrazole (preparation method is referred to Organic precursors and products International,34(1), 98-102; 2002) were added to 50mL of butanone, 2.76g (0.02mol) of potassium carbonate was added, the mixture was heated to reflux with stirring, the reaction was carried out for 4 to 10 hours, after the completion of the TLC monitoring, the solvent was distilled off under reduced pressure, 3X 50mL of ethyl acetate was added for extraction, the Organic phase was washed with 50mL of saturated saline solution by column chromatography, and 2.73g of a yellow solid was obtained after the precipitation (the eluent was ethyl acetate and petroleum ether in a volume ratio of 1:6), with a yield of 81.1%.
3) Preparation of 2- (1- (4-chlorophenyl) -1H-pyrazol-3-oxy) ethylamine hydrochloride
Figure BDA0002445325790000475
3.37g (0.01mol) of N-Boc-2- (1- (4-chlorophenyl) -1H-pyrazol-3-oxyl) ethylamine was added into 50mL of ethyl acetate, 6mL of concentrated hydrochloric acid was added dropwise with stirring at room temperature to dissolve the solid, stirring was continued for 4 to 5 hours, after the reaction was monitored by TLC, the solvent was distilled off under reduced pressure, 10mL of dichloromethane was added and stirred for half an hour, filtration was carried out, and the filter cake was washed with dichloromethane to obtain 2.16g of a white solid.
Example 5: preparation of compound F-C-1(N- (2- (1- (4-chlorophenyl) -1H-pyrazol-3-yloxy) ethyl) quinazolin-4-amine)
Figure BDA0002445325790000481
1.64g (0.01mol) of 4-chloroquinazoline and 2.74g (0.01mol) of 2- (1- (4-chlorophenyl) -1H-pyrazol-3-yloxy) ethylamine hydrochloride were added to 50ml of toluene. 4.45g (0.022mol) of triethylamine is added, the mixture is heated to reflux and reacted for 4 to 10 hours, after the TLC monitoring reaction is finished, the solvent is evaporated under reduced pressure, ethyl acetate (3X 50mL) is added for extraction, an organic phase is washed by 50mL of saturated saline, and after desolventization, column chromatography is carried out on a residue (eluent is ethyl acetate and petroleum ether (boiling range is 60 to 90 ℃) with the volume ratio of 1:4) to obtain 2.56g of white solid with the yield of 70.1 percent. Melting point 176.4 ℃.1H NMR(600MHz,CDCl3)δ8.67(s,1H),7.81(d,J＝8.0Hz,1H),7.72(d,J＝2.6Hz,1H),7.68(t,J＝7.7Hz,1H),7.61(d,J＝7.8Hz,1H),7.54(d,J＝8.9Hz,2H),7.40(d,J＝8.9Hz,2H),7.22(t,J＝7.6Hz,1H),6.78(s,1H),5.96(d,J＝2.6Hz,1H),4.71–4.56(m,2H),4.09(dd,J＝9.8,5.0Hz,2H).
Example 6: preparation of compound 20-19(2- (1- (4-chlorophenyl) -1H-pyrazol-3-oxy) ethyl (quinazolin-4-yl) carbamoyl chloride)
Figure BDA0002445325790000482
Compound F-C-1(0.002mol) and triethylamine (0.004mol) were added to 30mL of dichloromethane. Triphosgene (0.0024mol) was added thereto in portions with stirring at room temperature, the reaction mixture was continuously heated under reflux for 5 hours, after completion of the TLC monitoring reaction, the solvent was distilled off under reduced pressure, ethyl acetate (3X 30mL) was added for extraction, the organic phase was washed with 50mL of saturated brine, dried over anhydrous magnesium sulfate, and subjected to column chromatography (elution) on the residue after desolventizationThe solvent is ethyl acetate and petroleum ether (60-90 ℃), the volume ratio is 1:4) to obtain 0.69g of light yellow liquid, and the yield is 81.0%. Melting point 114.6 ℃.1H NMR(600MHz,CDCl3)δ9.27(s,1H),8.13(d,J＝8.5Hz,1H),8.05(d,J＝8.3Hz,1H),7.94(ddd,J＝8.4,7.0,1.3Hz,1H),7.67–7.62(m,1H),7.54(d,J＝2.6Hz,1H),7.41(d,J＝8.9Hz,2H),7.33(d,J＝8.9Hz,2H),5.40(d,J＝2.6Hz,1H),4.57(s,2H),4.53(s,2H).
Example 7: preparation of Compounds 20-1-19
Figure BDA0002445325790000483
Methylamine hydrochloride (0.001mol) and triethylamine (0.002mol) were added to 30mL of dichloromethane. 20mL of a dichloromethane solution of 20-19(0.001mol) was added dropwise thereto while stirring at room temperature, the reaction mixture was allowed to continue to react at room temperature for 3 hours, after completion of the TLC monitoring reaction, the solvent was distilled off under reduced pressure, ethyl acetate (3X 30mL) was added for extraction, the organic phase was washed with 50mL of saturated brine, dried over anhydrous magnesium sulfate, and column chromatography was performed on the residue after the precipitation (eluent, ethyl acetate and petroleum ether (60-90 ℃ C.) in a volume ratio of 1:4) to obtain 0.34g of a pale yellow liquid in a yield of 79.5%. Melting Point 147.0 ℃.1H NMR(600MHz,CDCl3)δ9.06(s,1H),7.98(d,J＝8.5Hz,1H),7.89(d,J＝8.4Hz,1H),7.81(t,J＝7.0Hz,1H),7.57(d,J＝2.5Hz,1H),7.55–7.49(m,1H),7.39(d,J＝8.8Hz,2H),7.33(d,J＝8.9Hz,2H),6.03(d,J＝3.2Hz,1H),5.64(t,J＝2.4Hz,1H),4.57(t,J＝5.2Hz,2H),4.51(t,J＝5.3Hz,2H),2.86(d,J＝4.6Hz,3H).
Other compounds of the invention may be prepared by reference to the above examples.
Physical property data and nuclear magnetic data of some of the compounds (1HNMR, 300MHz, internal standard TMS, ppm) as follows:
compounds 12-2-19:1H NMR(600MHz,CDCl3)δ8.94(s,1H),7.63(d,J＝2.6Hz,1H),7.47(d,J＝8.9Hz,2H),7.36(d,J＝8.9Hz,2H),5.65(d,J＝2.6Hz,1H),4.51(d,J＝15.3Hz,2H),4.32(s,2H),3.01(q,J＝7.5Hz,2H),1.34(t,J＝7.5Hz,3H).
compounds 20-2-19:1H NMR(600MHz,CDCl3)δ8.95(s,1H),7.97(d,J＝8.4Hz,1H),7.87(d,J＝8.5Hz,1H),7.80(ddd,J＝8.3,7.0,1.2Hz,1H),7.63(d,J＝2.6Hz,1H),7.50–7.46(m,3H),7.35(d,J＝8.9Hz,2H),5.74(d,J＝2.6Hz,1H),4.72(t,J＝5.4Hz,2H),4.45(t,J＝5.4Hz,2H),2.68(s,6H).
compounds 20-4-19:1H NMR(600MHz,CDCl3)δ9.17(s,1H),8.05(d,J＝8.4Hz,1H),7.87(d,J＝8.1Hz,1H),7.85(d,J＝8.2Hz,1H),7.54(d,J＝7.9Hz,1H),7.52(d,J＝2.6Hz,1H),7.42(d,J＝8.8Hz,2H),7.33(d,J＝8.8Hz,2H),5.40(d,J＝2.5Hz,1H),4.54(t,J＝5.2Hz,2H),4.48(t,J＝5.3Hz,2H),3.69(s,3H).
compounds 20-5-19:1H NMR(600MHz,CDCl3)δ9.16(s,1H),8.04(d,J＝8.4Hz,1H),7.88(d,J＝8.4Hz,1H),7.85(t,J＝7.6Hz,1H),7.53(d,J＝8.1Hz,1H),7.52(d,J＝2.6Hz,1H),7.42(d,J＝8.7Hz,2H),7.33(d,J＝8.8Hz,2H),5.40(d,J＝2.4Hz,1H),4.55(t,J＝5.2Hz,2H),4.49(t,J＝5.3Hz,2H),4.17(q,J＝7.0Hz,2H),1.10(t,J＝7.0Hz,3H).
compounds 63-15:1H NMR(600MHz,CDCl3)δ9.04(s,1H),7.96(d,J＝8.4Hz,1H),7.85(d,J＝8.4Hz,1H),7.78(t,J＝7.4Hz,1H),7.62(d,J＝2.5Hz,1H),7.48(t,J＝7.6Hz,1H),7.40(d,J＝8.8Hz,2H),7.32(d,J＝8.8Hz,2H),6.01(s,1H),5.71(d,J＝2.5Hz,1H),4.60(t,J＝4.9Hz,2H),4.49(t,J＝4.9Hz,2H),1.36(s,9H).
compounds 63-19:1H NMR(600MHz,CDCl3)δ9.17(s,1H),8.04(d,J＝8.4Hz,1H),7.90(d,J＝8.4Hz,1H),7.84(ddd,J＝8.3,7.0,1.3Hz,1H),7.53(d,J＝9.6Hz,1H),7.51(d,J＝3.0Hz,1H),7.42(d,J＝8.9Hz,2H),7.33(d,J＝8.9Hz,2H),5.41(d,J＝2.6Hz,1H),4.55(t,J＝5.2Hz,2H),4.50(t,J＝5.3Hz,2H),4.06(t,J＝6.6Hz,2H),1.46(dd,J＝13.8,6.9Hz,2H),0.67(t,J＝7.0Hz,3H).
compounds 63-21:1H NMR(600MHz,CDCl3)δ9.16(s,1H),8.04(d,J＝8.4Hz,1H),7.89(d,J＝8.2Hz,1H),7.85(t,J＝7.7Hz,1H),7.53(d,J＝8.9Hz,1H),7.51(d,J＝3.6Hz,1H),7.42(d,J＝8.8Hz,2H),7.33(d,J＝8.8Hz,2H),5.41(d,J＝2.5Hz,1H),4.55(t,J＝5.2Hz,2H),4.49(t,J＝5.3Hz,2H),4.11(t,J＝6.6Hz,2H),1.46–1.35(m,2H),1.07(d,J＝6.8Hz,2H),0.75(t,J＝7.3Hz,3H).
compounds 63-99:1H NMR(600MHz,CDCl3)δ9.00(s,1H),7.93(d,J＝8.3Hz,1H),7.85(d,J＝8.4Hz,1H),7.77(t,J＝7.6Hz,1H),7.54(d,J＝2.4Hz,1H),7.45(t,J＝7.6Hz,1H),7.36(d,J＝8.8Hz,2H),7.32–7.28(m,4H),7.26(d,J＝6.7Hz,3H),6.49(s,1H),5.54(d,J＝2.3Hz,1H),4.61(t,J＝5.1Hz,2H),4.50(t,J＝5.1Hz,2H),4.47(d,J＝5.5Hz,2H).
compounds 63-114, mp 113.1 ℃.1H NMR(600MHz,DMSO)δ9.05(s,1H),8.25(s,1H),7.95(d,J＝7.9Hz,1H),7.91–7.86(m,1H),7.74(d,J＝8.0Hz,1H),7.65(d,J＝8.0Hz,2H),7.47(d,J＝7.6Hz,2H),7.38(d,J＝6.4Hz,1H),7.18(d,J＝7.4Hz,2H),6.95(d,J＝7.6Hz,1H),6.85(d,J＝7.5Hz,2H),5.70(s,1H),4.50(t,J＝5.7Hz,2H),4.39(t,J＝5.8Hz,2H),4.19(d,J＝4.2Hz,2H),3.72(s,3H).
Compounds 63-118, melting point 152.0 ℃.1H NMR(600MHz,DMSO)δ9.04(s,1H),8.27(s,1H),7.94(d,J＝8.0Hz,1H),7.91–7.85(m,1H),7.66(d,J＝8.5Hz,2H),7.53–7.49(m,1H),7.47(d,J＝8.3Hz,2H),7.40(d,J＝7.8Hz,1H),7.35(s,1H),7.30(d,J＝6.9Hz,2H),7.21(d,J＝7.6Hz,2H),5.73(s,1H),4.46(t,J＝5.0Hz,2H),4.35(t,J＝4.6Hz,2H),3.31(d,J＝5.6Hz,2H),2.74(t,J＝6.5Hz,2H).
Compounds 63-121, mp 144.1 ℃.1H NMR(600MHz,DMSO)δ9.04(s,1H),8.27(d,J＝2.4Hz,1H),7.94(d,J＝8.3Hz,1H),7.89(t,J＝7.5Hz,1H),7.69(d,J＝8.3Hz,1H),7.66(d,J＝8.8Hz,2H),7.52(t,J＝7.5Hz,1H),7.48(d,J＝8.8Hz,2H),7.36(t,J＝5.2Hz,1H),7.06(s,4H),5.73(d,J＝2.4Hz,1H),4.47(t,J＝5.7Hz,2H),4.36(t,J＝5.6Hz,2H),3.29(dd,J＝13.1,6.7Hz,2H),2.68(t,J＝7.3Hz,2H),2.24(s,3H).
Compounds 63-122, mp 138.8 ℃.1H NMR(600MHz,DMSO)δ9.04(s,1H),8.27(s,1H),7.94(d,J＝8.2Hz,1H),7.90–7.86(m,1H),7.66(d,J＝8.2Hz,3H),7.54–7.50(m,1H),7.47(d,J＝8.5Hz,2H),7.34–7.28(m,1H),7.24–7.19(m,2H),7.16(t,J＝8.5Hz,1H),7.07(t,J＝8.5Hz,2H),5.73(s,1H),4.47(t,J＝5.1Hz,2H),4.37(t,J＝4.7Hz,2H),3.31(d,J＝5.8Hz,2H),2.73(t,J＝6.7Hz,2H).
Compounds 63-123, melting Point 124.5℃。1H NMR(600MHz,DMSO)δ9.05(s,1H),8.26(s,1H),7.95(d,J＝7.3Hz,1H),7.91–7.86(m,1H),7.69(d,J＝7.4Hz,1H),7.66(d,J＝7.4Hz,2H),7.56–7.51(m,1H),7.47(d,J＝7.5Hz,2H),7.39(d,J＝4.0Hz,1H),7.27(d,J＝4.9Hz,2H),7.19(d,J＝7.1Hz,1H),7.15–7.08(m,2H),5.72(d,J＝1.6Hz,1H),4.47(t,J＝5.4Hz,2H),4.36(t,J＝5.5Hz,2H),3.32(t,J＝5.3Hz,2H),2.78(t,J＝5.5Hz,2H).
The melting point of the compound is between 63 and 125 and is 162.2 ℃.1H NMR(600MHz,DMSO)δ9.04(s,1H),8.27(s,1H),7.94(d,J＝8.3Hz,1H),7.88(s,1H),7.66(d,J＝8.8Hz,2H),7.52(d,J＝8.3Hz,1H),7.48(d,J＝8.6Hz,2H),7.43(d,J＝8.0Hz,2H),7.34(s,1H),7.25(d,J＝7.9Hz,1H),7.15(d,J＝7.9Hz,2H),5.73(s,1H),4.46(t,J＝5.2Hz,2H),4.36(t,J＝5.1Hz,2H),3.31(d,J＝6.1Hz,2H),2.71(t,J＝6.7Hz,2H).
Compounds 63-127, melting point 131.2 ℃.1H NMR(600MHz,DMSO)δ9.04(s,1H),8.26(s,1H),7.94(d,J＝7.6Hz,1H),7.91–7.86(m,1H),7.66(s,3H),7.51(d,J＝8.0Hz,1H),7.47(d,J＝7.6Hz,2H),7.40(d,J＝8.5Hz,2H),7.35(s,1H),7.22(d,J＝12.5Hz,2H),5.73(s,1H),4.46(t,J＝5.5Hz,2H),4.35(t,J＝5.4Hz,2H),3.34(dd,J＝12.9,6.5Hz,2H),2.75(t,J＝6.8Hz,2H).
Compounds 63-173:1H NMR(600MHz,CDCl3)δ9.12(s,1H),8.19(d,J＝2.7Hz,1H),8.01(d,J＝8.4Hz,1H),7.81(d,J＝8.4Hz,1H),7.79–7.74(m,1H),7.49(d,J＝2.6Hz,1H),7.42(t,J＝7.7Hz,1H),7.39(d,J＝8.9Hz,2H),7.32(d,J＝8.9Hz,2H),7.04(s,1H),6.16(dd,J＝2.6,1.5Hz,1H),5.34(d,J＝2.6Hz,1H),4.73(t,J＝5.2Hz,2H),4.67(t,J＝4.9Hz,2H).
compounds 63-175:1H NMR(600MHz,CDCl3)δ9.12(s,1H),8.87(s,1H),8.07(d,J＝8.5Hz,1H),7.89(d,J＝8.4Hz,1H),7.85(t,J＝7.7Hz,1H),7.52(d,J＝9.5Hz,1H),7.51(d,J＝2.6Hz,1H),7.42(s,1H),7.39(d,J＝8.8Hz,2H),7.33(d,J＝8.8Hz,2H),5.38(d,J＝2.5Hz,1H),4.72(t,J＝5.2Hz,2H),4.65(t,J＝5.0Hz,2H).
other compounds of formula I can be prepared by following the procedures described in the above examples and the preparation procedures described in the summary of the invention.
Examples of measurement of biological Activity
The compound of the invention shows good activity to various germs, pests and mites in the agricultural field.
Example 8: measurement of fungicidal Activity
The compound sample of the invention is used for carrying out in vitro bacteriostatic activity or in vivo protection effect tests 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 measurement method is as follows: the high-throughput screening method is adopted, i.e. a compound sample to be detected is dissolved by using a proper solvent (the type of the solvent is acetone, methanol, DMF, and the like, and is selected according to the dissolving capacity of the solvent on the sample), and a liquid to be detected with the required concentration is prepared. Under an ultraclean working environment, adding a solution to be detected into micropores of a 96-hole culture plate, adding a pathogen propagule suspension into the micropore, and placing the treated culture plate in a constant-temperature incubator for culture. And (4) after 24 hours, carrying out investigation, visually observing the germination or growth condition of the pathogen propagules during the investigation, and evaluating the bacteriostatic activity of the compound according to the germination or growth condition of the control treatment.
The results of the in vitro bacteriostatic activity (expressed as inhibition) test of some compounds are as follows:
inhibition rate against rice blast germs:
at a dose of 25ppm, the compounds with the inhibition rate of more than 80 percent on rice blast comprise: 20-19, 20-1-19, 20-2-19, etc. The inhibition ratios of the control drugs CK1, CK2, CK3, CK4, CK5 and CK6 on rice blast were 0.
Inhibition rate of cucumber botrytis cinerea:
at a dose of 25ppm, the compounds with the inhibition rate of more than 80% comprise: 20-2-19, and the like. The inhibition ratio of the control drugs CK1, CK2, CK3, CK4 and CK5 on Botrytis cinerea is 0.
(2) Living body protecting Activity assay
The measurement method is as follows: the living potted plant determination method is adopted, i.e. a sample of the compound to be tested is dissolved by a small amount of solvent (the type of the solvent is acetone, methanol, DMF, etc., and is selected according to the dissolving capacity of the solvent to the sample, and the volume ratio of the solvent amount to the liquid spraying amount is equal to or less than 0.05), and diluted by water containing 0.1 percent of Tween 80 to prepare the liquid to be tested with the required concentration. The solution to be tested is sprayed on diseased host plants (the host plants are standard potted seedlings cultured in a greenhouse) on a crop sprayer, and disease inoculation is carried out after 24 hours. According to the characteristics of diseases, inoculating the disease plants needing temperature and moisture control culture, then culturing in an artificial climate chamber, transferring into a greenhouse for culture after the diseases are infected, and directly inoculating and culturing the disease plants without moisture control culture in the greenhouse. The compound disease control effect evaluation is carried out after the control is sufficiently ill (usually, one week).
The results of the in vivo protective activity test of some compounds are as follows:
in vivo protective activity against cucumber downy mildew:
at a dose of 400ppm, the compounds with more than 80 percent of control effect on cucumber downy mildew comprise: 12-2-19, 20-1-19, 20-2-19, 20-4-19, 20-5-19, 63-15, 63-19, 63-173, 63-175, etc.;
at a dose of 100ppm, the compounds with more than 80 percent of control effect on cucumber downy mildew comprise: 12-2-19, 20-1-19, 20-5-19, 63-15, 63-173, etc.;
at a dose of 25ppm, the compounds with more than 80 percent of control effect on cucumber downy mildew comprise: 20-1-19, 20-5-19, 63-15, 63-173, etc.;
at a dose of 12.5ppm, the compounds with more than 80 percent of control effect on cucumber downy mildew comprise: 20-1-19, 20-5-19, 63-15, 63-173, etc.;
at the dose of 6.25ppm, the compounds with the control effect on cucumber downy mildew of more than 80 percent comprise: 20-1-19, 20-5-19, 63-173, etc.
In vivo protective activity against wheat powdery mildew:
at a dose of 400ppm, the compounds with the control effect on wheat powdery mildew of more than 80 percent comprise: 12-2-19, 20-2-19, 20-4-19, 63-21, 63-99, etc.;
at a dose of 100ppm, the compounds with the control effect on wheat powdery mildew of more than 80 percent comprise: 12-2-19;
at a dose of 25ppm, the compounds with the control effect on wheat powdery mildew of more than 80 percent comprise: 12-2-19.
In vivo protective activity against corn rust:
at a dose of 400ppm, the compounds with the corn rust prevention effect of more than 80 percent comprise: 12-2-19 and 20-19.
In vivo protective activity against cucumber anthracnose:
at a dose of 400ppm, more than 80% of compounds with cucumber anthracnose control effect comprise: 12-2-19, 20-4-19, 20-5-19, 63-175;
at a dose of 100ppm, more than 80 percent of compounds have the control effect on cucumber anthracnose: 20-5-19;
at a dose of 25ppm, more than 80% of compounds with cucumber anthracnose control effect comprise: 20-5-19, and the like.
(3) Test results for partial Compounds and control Agents
Activity comparisons of some compounds with control agents were performed and the results are shown in tables 64-67 (where "///" indicates no test).
TABLE 64 in vivo protective Activity against cucumber downy mildew
Figure BDA0002445325790000521
TABLE 65 in vivo protective Activity against wheat powdery mildew
Figure BDA0002445325790000522
TABLE 66 in vivo protective Activity against corn rust
Figure BDA0002445325790000523
Figure BDA0002445325790000531
TABLE 67 Activity for cucumber anthracnose in vivo protection
Figure BDA0002445325790000532
Example 9: determination of insecticidal and acaricidal Activity
Several insects were tested for insecticidal activity using the compounds of the present invention. The measurement method is as follows:
after dissolving a test compound in a mixed solvent of acetone/methanol (1: 1), the test compound was diluted with water containing 0.1% (wt) Tween 80 to a desired concentration.
The insecticidal activity is determined by taking diamondback moth and tetranychus cinnabarinus as targets and adopting an airrbrush spraying method.
(1) Activity assay for killing diamondback moth
The determination method comprises the following steps: the cabbage leaves were punched out into a 2 cm-diameter disk by a punch, and the pressure of airbrush spray treatment was 10psi (approximately 0.7 kg/cm)2) Spraying on the front and back sides of each leaf disc, wherein the liquid spraying amount is 0.5 ml. After drying in the shade, 10 test insects of 2 years old are inoculated in each treatment, and the treatment is repeated for 3 times. And (4) after treatment, placing the treated mixture into an observation room with the temperature of 25 ℃ and the relative humidity of 60-70% for culture, investigating the number of the survival insects after 72 hours, and calculating the mortality.
Partial test results for plutella xylostella are as follows:
at a dose of 600ppm, the compounds with the fatality rate to diamondback moth of more than 80 percent have the following components: 20-1-19, 63-15, and the like.
(2) Activity measurement for killing tetranychus cinnabarinus
The determination method comprises the following steps: collecting two bean seedlings of true leaf vegetable, inoculating Tetranychus cinnabarinus, examining the base number, and treating with airrbrush sprayer under 10psi (about 0.7 kg/cm)2) The amount of the sprayed liquid was 0.5 ml. Each treatment was repeated 3 times, and after treatment, the treated mites were placed in a standard observation room, and after 72 hours, the number of live mites was investigated, and the mortality was calculated.
Partial test results on tetranychus cinnabarinus are as follows:
at a dose of 600ppm, the compounds with a lethality rate of more than 80% to tetranychus cinnabarinus comprise 12-2-19, 20-4-19, 63-15, 63-19, 63-173, 63-175 and the like;
at the dose of 100ppm, the compounds with the lethality rate of more than 80 percent to tetranychus cinnabarinus are 12-2-19, 63-173 and the like.
(3) Test results for partial Compounds and control Agents
Activity comparisons of some compounds with control agents were performed and the results are shown in tables 68-69 (where "///" indicates no test).
TABLE 68 control of plutella xylostella
Figure BDA0002445325790000533
Figure BDA0002445325790000541
TABLE 69 control Effect on Tetranychus cinnabarinus
Figure BDA0002445325790000542

Claims (11)

1. A substituted pyrazole compound containing pyrimidinamine is characterized in that: the compound is shown as a general formula I:
Figure FDA0002445325780000011
R1selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C12Alkyl, halo C1-C12Alkyl radical, C3-C12Cycloalkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C1-C12Alkylthio, halo C1-C12Alkylthio radical, C1-C12Alkylsulfinyl radical, C1-C12Alkylsulfonyl radical, C2-C12Alkenyl, halo C2-C12Alkenyl radical, C2-C12Alkynyl, halo C2-C12Alkynyl, C3-C12Alkenyloxy, halogeno C3-C12Alkenyloxy radical, C3-C12Alkynyloxy, halo C3-C12Alkynyloxy, C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, C1-C12Alkylaminocarbonyl, halogeno C1-C12Alkylaminocarbonyl radical, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl or C1-C2Alkylthio group C1-C12An alkyl group;
R2selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy or halo C1-C12An alkoxy group;
wherein R is1And R2Can also form a five-membered, six-membered, seven-membered or eight-membered ring containing C, N, O or S together with the connected pyrimidine ring;
R3selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylthio radical, C2-C12Alkenylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, halo C2-C12Alkenyl, halo C2-C12Alkynyl, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, di (halo C)1-C12Alkyl) amino, C1-C12Alkyl hydrazino, C1-C12Alkoxyamino group, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkylsulfinyl, halogeno C1-C12Alkylsulfinyl radical, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylaminosulfonyl, di (C)1-C12Alkyl) aminosulfonyl, C1-C12Alkylsulfonylaminocarbonyl group, C1-C12Alkylcarbonylaminosulfonyl radical, C3-C12Cycloalkyloxycarbonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkyl carbonyl radical C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C1-C12Alkylaminocarbonyl, di (C)1-C12Alkyl) aminocarbonyl, C2-C12Alkenyloxycarbonyl radical, C2-C12Alkynyloxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkoxycarbonyl group, C1-C12Alkylaminosulfenyl, di (C)1-C12Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 51-C6Alkyl, heteroaryl C1-C6Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C1-C6Alkyloxy, heteroaryl C1-C6Alkyloxy, aryl C1-C6Alkylamino, heteroaryl C1-C6Alkylamino, the following groups being halogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
y is selected from NR3O or S;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy or halo C1-C12An alkoxy group;
wherein R is4And R5And optionally C connected thereto to form C3-C8A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy or halo C1-C12An alkoxy group;
wherein R is6And R7And optionally C connected thereto to form C3-C8A ring of (a);
m is an integer from 0 to 5;
R8selected from hydrogen, cyano, halogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R9selected from hydrogen, cyano, halogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R10selected from halogen, hydroxy, amino, cyano, nitro, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, halo-di (C)1-C12Alkyl) amino, C (═ O) NR11R12、C1-C12Alkylthio, halo C1-C12Alkylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, C2-C12Alkenyloxy, halogeno C2-C12Alkenyloxy radical, C2-C12Alkynyloxy, halo C2-C12Alkynyloxy, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl, halo C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C1-C12Alkylthio carbonyl group C1-C12Alkyl, halo C1-C12Alkylthio carbonyl group C1-C12Alkyl radical, C1-C12Alkylcarbonyloxy, halo C1-C12Alkylcarbonyloxy, C1-C12Alkoxycarbonyloxy, halo C1-C12Alkoxycarbonyloxy, C1-C12Alkylsulfonyloxy, halo C1-C12Alkylsulfonyloxy, C1-C12Alkoxy radical C1-C12Alkoxy orHalogen substituted C1-C12Alkoxy radical C1-C12An alkoxy group;
n is an integer from 0 to 5;
R11、R12can be the same or different and are respectively selected from hydrogen and C1-C12Alkyl or halo C1-C12An alkyl group;
w is selected from hydrogen, halogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C3-C8Cycloalkyl radical, C1-C12Alkoxy radical, C1-C12Alkylthio or C1-C12An alkylsulfonyl group.
2. The pyrimidine-containing substituted pyrazole compound according to claim 1, wherein: in the general formula I
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C6Alkyl, halo C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio radical, C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl, halo C1-C6Alkylthio radical, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C2-C6Alkynyl, halo C2-C6Alkynyl, C3-C6Alkenyloxy, halogeno C3-C6Alkenyloxy radical, C3-C6Alkynyloxy, halo C3-C6Alkynyloxy, C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, C1-C6Alkylaminocarbonyl, halogeno C1-C6Alkylaminocarbonyl radical, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl or C1-C6Alkylthio group C1-C6An alkyl group;
R2selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is1And R2Can also form a five-membered ring or a six-membered ring containing C, N, O or S together with the connected pyrimidine ring;
R3selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylthio radical, C2-C6Alkenylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, halo C2-C6Alkenyl, halo C2-C6Alkynyl, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, di (halo C)1-C6Alkyl) amino, C1-C6Alkyl hydrazino, C1-C6Alkoxyamino group, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkylsulfinyl, halogeno C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylaminosulfonyl, di (C)1-C6Alkyl) aminosulfonyl, C1-C6Alkylsulfonylaminocarbonyl group, C1-C6Alkylcarbonylaminosulfonyl radical, C3-C6Cycloalkyloxycarbonyl radical, C1-C6Alkyl carbo groupRadical, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkyl carbonyl radical C1-C6Alkyl radical, C1-C6Alkoxycarbonyl radical C1-C6Alkyl radical, C1-C6Alkylaminocarbonyl, di (C)1-C6Alkyl) aminocarbonyl, C2-C6Alkenyloxycarbonyl radical, C2-C6Alkynyloxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkoxycarbonyl group, C1-C6Alkylaminosulfenyl, di (C)1-C6Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 51-C6Alkyl, heteroaryl C1-C6Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C1-C6Alkyloxy, heteroaryl C1-C6Alkyloxy, aryl C1-C6Alkylamino, heteroaryl C1-C6Alkylamino, the following groups being halogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
y is selected from NR3O or S;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is4、R5And optionally C connected thereto to form C3-C6A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is6、R7And optionally C connected thereto to form C3-C6A ring of (a);
m is an integer from 0 to 4;
R8selected from hydrogen, cyano, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R9selected from hydrogen, cyano, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R10selected from halogen, hydroxy, amino, cyano, nitro, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, halo-di (C)1-C6Alkyl) amino, C (═ O) NR11R12、C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, halo C2-C6Alkynyloxy, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkoxycarbonyl radical C1-C6Alkyl, halo C1-C6Alkoxycarbonyl radical C1-C6Alkyl radical, C1-C6Alkylthio carbonyl group C1-C6Alkyl, halo C1-C6Alkylthio carbonyl group C1-C6Alkyl radical, C1-C6Alkylcarbonyloxy, halo C1-C6Alkylcarbonyloxy, C1-C6Alkoxycarbonyloxy, halo C1-C6Alkoxycarbonyloxy, C1-C6Alkylsulfonyloxy, halo C1-C6Alkylsulfonyloxy, C1-C6Alkoxy radical C1-C6Alkoxy or halo C1-C6Alkoxy radical C1-C6An alkoxy group;
n is an integer from 0 to 5;
R11、R12can be the same or different and are respectively selected from hydrogen and C1-C6Alkyl or halo C1-C6An alkyl group;
w is selected from hydrogen, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio or C1-C6An alkylsulfonyl group;
the position of attachment of Y to the pyrazole ring is selected from the 3, 4 or 5 positions; when Y is attached to the pyrazole ring at position 3, then R8In the 4 position, R9At position 5; when Y is attached to the pyrazole ring at the 4-positionWhen they are connected, then R8In the 3 position, R9At position 5; when Y is attached to the pyrazole ring at the 5-position, then R8In the 3 position, R9At 4 bits.
3. The pyrimidine-containing substituted pyrazole compound according to claim 2, wherein: in the general formula I
R1Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylthio radical, C2-C4Alkenyl, halo C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkynyl, C3-C4Alkenyloxy, halogeno C3-C4Alkenyloxy radical, C3-C4Alkynyloxy, halo C3-C4Alkynyloxy, C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, C1-C4Alkylaminocarbonyl, halogeno C1-C4Alkylaminocarbonyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl or C1-C4Alkylthio group C1-C4An alkyl group;
R2selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is1And R2Can also form a five-membered ring or a six-membered ring containing C, N, O or S together with the connected pyrimidine ring;
R3selected from hydrogen, halogen,Hydroxy, amino, hydroxyamino, hydrazino, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, di (halo C)1-C4Alkyl) amino, C1-C4Alkyl hydrazino, C1-C4Alkoxyamino group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylaminosulfonyl, di (C)1-C4Alkyl) aminosulfonyl, C1-C4Alkylsulfonylaminocarbonyl group, C1-C4Alkylcarbonylaminosulfonyl radical, C3-C4Cycloalkyloxycarbonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkyl carbonyl radical C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylaminocarbonyl, di (C)1-C4Alkyl) aminocarbonyl, C2-C4Alkenyloxycarbonyl radical, C2-C4AlkynyloxycarbonylBase, C1-C4Alkoxy radical C1-C4Alkoxycarbonyl group, C1-C4Alkylaminosulfenyl, di (C)1-C4Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 51-C4Alkyl, heteroaryl C1-C4Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C1-C4Alkyloxy, heteroaryl C1-C4Alkyloxy, aryl C1-C4Alkylamino, heteroaryl C1-C4Alkylamino, the following groups being halogen, nitro, cyano, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
y is selected from O;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is4、R5And optionally C connected thereto to form C3-C4A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is6、R7And optionally C connected thereto to form C3-C4A ring of (a);
m is an integer from 0 to 3;
R8selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R9selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R10selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR11R12、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C2-C4Alkenyloxy, halogeno C2-C4Alkenyloxy radical, C2-C4Alkynyloxy, halo C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
n is an integer from 0 to 5;
R11、R12can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
w is selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio or C1-C4An alkylsulfonyl group;
y is O, the position of the connection of the O and the pyrazole ring is selected from 3, 4 or 5; when O is attached to the 3-position of the pyrazole ring, then R8In the 4 position, R9At position 5, the structural formula is shown as I-1; when O is attached to the 4-position of the pyrazole ring, then R8In the 3 position, R9At position 5, the structural formula is shown as I-2; when O is attached to the 5-position of the pyrazole ring, then R8In the 3 position, R9At the 4-position, the structural formula is shown as I-3;
Figure FDA0002445325780000051
4. the pyrimidine-containing substituted pyrazole compound according to claim 3, wherein: the compound shown in the general formula I-1, I-2 or I-3 is shown in the general formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-2A, I-2B, I-2C, I-3A, I-3B, I-3C, I-4A, I-4B or I-4C,
Figure FDA0002445325780000052
Figure FDA0002445325780000061
in the formula:
R1selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C2-C4Alkenyl, halo C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkynyl, C3-C4Alkenyloxy, halogeno C3-C4Alkenyloxy radical, C3-C4Alkynyloxy, halo C3-C4Alkynyloxy, C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, C1-C4Alkylaminocarbonyl, halogeno C1-C4Alkylaminocarbonyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl or C1-C4Alkylthio group C1-C4An alkyl group;
R2selected from hydrogen, halogen, cyanogenRadical, nitro, amino, carboxyl, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R3selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, di (halo C)1-C4Alkyl) amino, C1-C4Alkyl hydrazino, C1-C4Alkoxyamino group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylaminosulfonyl, di (C)1-C4Alkyl) aminosulfonyl, C1-C4Alkylsulfonylaminocarbonyl group, C1-C4Alkylcarbonylaminosulfonyl radical, C3-C4Cycloalkyloxycarbonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkyl carbonyl radical C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylaminocarbonyl, di (C)1-C4Alkyl) aminocarbonyl, C2-C4Alkenyloxycarbonyl radical, C2-C4Alkynyloxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkoxycarbonyl group, C1-C4Alkylaminosulfenyl, di (C)1-C4Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 51-C4Alkyl, heteroaryl C1-C4Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C1-C4Alkyloxy, heteroaryl C1-C4Alkyloxy, aryl C1-C4Alkylamino, heteroaryl C1-C4Alkylamino group: halogen, nitro, cyano, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is4、R5And optionally C connected thereto to form C3-C4A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is6、R7And optionally C connected thereto to form C3-C4A ring of (a);
R8selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R9selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R10selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR11R12、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C2-C4Alkenyloxy, halogeno C2-C4Alkenyloxy radical, C2-C4Alkynyloxy, halo C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
n is an integer from 0 to 5;
R11、R12can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
R13、R14、R15or R16Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy or C3-C4A cycloalkyl group;
R17、R18can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C3-C4Cycloalkyl, unsubstituted or substituted by 1-5R10Substituted aryl radicals,Heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R19is selected from C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R20selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R21is selected from C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R22selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R23、R24each independently selected from C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R25、R26each independently selected from hydrogen, cyano, halogen, C1-C4Alkyl, halo C1-C4Alkyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
w is selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio or C1-C4An alkylsulfonyl group.
5. The compound of claim 4, wherein: the compound shown in the general formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-2A, I-2B, I-2C, I-3A, I-3B, I-3C, I-4A, I-4B or I-4C, wherein in the formula
R1Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methyl, ethyl, propyl, isopropyl, tert-butyl, methyl, propyl, isopropyl, tert-butyl, isopropyl, tert-butyl, isopropyl, tert-butyl, isopropyl, tert-butyl, isopropyl, tert-butyl, isopropyl, tert-butyl, and isopropyl, and isopropyl, and isopropyl, and tert-butyl, and,A fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxymethyl, ethoxymethyl or trifluoroethoxymethyl group;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, cyano, nitro, amino, carboxy, formyl, methyl, ethyl, methoxy, ethoxy or trifluoroethoxy;
R3selected from the group consisting of hydrogen, chloro, hydroxy, amino, hydroxyamino, hydrazino, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, cyclopropyloxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, trifluoromethylamino, trifluoroethylamino, cyclopropylamino, dimethylamino, diethylamino, methylhydrazino, ethylhydrazino, tert-butylhydrazino, methoxyamino, ethoxyamino, methylthio, ethylthio, allyl, propargyl, methylsulfonyl, ethylsulfonyl, trifluoroethylsulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl, ethylsulfonyl, ethylaminosulfonyl, and combinations thereof, Diethylaminosulfonyl, methylsulfonylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, vinyloxycarbonyl, acetylenyloxycarbonyl, methylaminothio, ethylaminothio, dimethylaminosulfanyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2, 4-triazolyl, 1,2, 3-triazolyl, tetrazolyl, indolyl, morpholinyl, piperazinyl, benzopyrazolyl, benzimidazolyl, benzylamino, 4-chlorobenzylamino, 4-fluorobenzylamino, 4-bromobenzylamino, 4-methylbenzylamino, 4-methoxybenzylamino, 4-trifluoromethoxybenzylamino, phenethylamino, 4-chlorophenylethylamino, 4-fluorobenzylethylamino, 4-bromobenzlethylamino, isopropoxycarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, ethyleneoxycarbonyl, acetylenecarbonyl, acetamido, ethylaminocarbonyl, ethynyl, benzothiazolyl, 4-chlorobenzylamino, 4-yl, 4-bromobenzylamino, N-yl, N-amino, N-D-amino, N-methyl-amino, N-, 4-methylphenylethylamino, 4-methoxyphenylethylamino, 4-trifluoromethoxy phenylethylamino, 3-chlorophenylethylamino, 3-fluorophenylethylamino, 3-bromophenylethylamino, 3-methylphenylethylamino, 3-trifluoromethylphenethylamino, 2-chlorophenylethylamino, 2-fluorophenylethylamino, 2-bromophenylethylaminoEthylamino, 2-methylphenylethylamino or 2-trifluoromethylphenethylamino;
R4、R5which may be the same or different, are each selected from hydrogen, fluoro, chloro, bromo, iodo, 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;
R6、R7which may be the same or different, are each selected from hydrogen, fluoro, chloro, bromo, iodo, 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;
R8selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl or trifluoromethyl;
R9selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl or trifluoromethyl;
R10selected from fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl or dimethylaminocarbonyl;
n is an integer from 0 to 5;
R13、R14、R15or R16Which may be the same or different, are each selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy and trifluorobutoxyA fluoroethoxy group;
R17、R18which may be identical or different, are each chosen from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, unsubstituted or substituted by 1 to 5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R19selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, cyclopropyl, methylsulfonyl, ethylsulfonyl, methylcarbonyl, ethylcarbonyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R20selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R21selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, cyclopropyl, methylsulfonyl, ethylsulfonyl, methylcarbonyl, ethylcarbonyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylA carbonyl group, an arylmethylcarbonyl group, a heteroarylmethylcarbonyl group, an aryloxycarbonyl group or a heteroaryloxycarbonyl group;
R22selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, unsubstituted or substituted by 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R23、R24each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, trifluoroethoxycarbonyl, unsubstituted or substituted with 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R25、R26each independently selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, unsubstituted or substituted with 1-5R10Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
w is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl.
6. The compound of claim 5, wherein: compounds of the general formula I-1A, I-1B, I-1C, I-2A, I-2B, I-2C, I-4A, I-4B or I-4C, wherein
R1Selected from hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl or difluoromethyl;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, nitro, amino, formyl, methyl, ethyl, methoxy or ethoxy;
R3selected from the group consisting of chloro, amino, hydroxyamino, hydrazino, methyl, ethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, cyclopropylamino, dimethylamino, diethylamino, methylhydrazino, tert-butylhydrazino, methoxyamino, ethoxyamino, methylthio, ethylthio, methylaminothio, dimethylaminosulthio, pyrazolyl, 1,2, 4-triazolyl, benzylamino, 4-chlorobenzylamino, 4-methoxybenzylamino, 4-trifluoromethoxybenzylamino, phenethylamino, 4-chlorobenzylethylamino, 4-fluorobenzylethylamino, 4-bromobenzylethylamino, 4-methylphenylethylamino, 3-bromobenzylethylamino or 2-fluorobenzylethylamino;
R4、R5can be the same or different and is respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R6、R7are all selected from hydrogen;
R8selected from hydrogen;
R9selected from hydrogen;
R10selected from fluoro, chloro, bromo, iodo, cyano, nitro, methyl, trifluoromethyl, methoxy or trifluoromethoxy;
n is an integer from 0 to 5;
R13、R14、R15or R16Can be the same or different and is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl;
R17、R18can be the same or different and is respectively selected from hydrogen, fluorine, chlorine, bromine or iodine;
w is selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl.
7. The compound of claim 6, wherein: compounds of the general formula I-1A, I-1B, I-1C, I-2A, I-2B, I-2C, I-4A, I-4B or I-4C, wherein
R1Selected from fluoro, chloro, bromo, iodo, methyl, ethyl or difluoromethyl;
R2selected from fluorine, chlorine, bromine, iodine, nitro, amino, formyl, methyl or methoxy;
R3selected from the group consisting of chloro, amino, methoxy, ethoxy, n-propoxy, n-butoxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, dimethylamino, diethylamino, methoxyamino, pyrazolyl, 1,2, 4-triazolyl, benzylamino, 4-methoxybenzylamino, 4-chlorobenzylethylamino, 4-fluorobenzylethylamino, 4-bromobenzylethylamino, 4-methylphenylethylamino, 3-bromobenzylethylamino or 2-fluorobenzylethylamino;
R4、R5may be the same or different and is independently selected from hydrogen or methyl;
R6、R7are all selected from hydrogen;
R8selected from hydrogen;
R9selected from hydrogen;
R10selected from fluoro, chloro, bromo, iodo, cyano, nitro, methyl, trifluoromethyl, methoxy or trifluoromethoxy;
n is an integer from 1 to 5;
R13、R14、R15、R16are all selected from hydrogen;
R17selected from hydrogen;
R18selected from chlorine;
w is selected from hydrogen, fluorine, chlorine, bromine or iodine.
8. A process for the preparation of compounds of the general formulae I-1, I-2 and I-3 according to claim 3, of the formulae:
(1) the compound I-1 of the general formula is prepared by the following method:
Figure FDA0002445325780000111
(2) the compound I-2 of the general formula is prepared by the following method:
Figure FDA0002445325780000112
(3) the compound I-3 of the general formula is prepared by the following method:
Figure FDA0002445325780000121
the substituents in the formula are as described in claim 3.
9. Use of the pyrimidine amine-containing substituted pyrazole compounds according to any one of claims 1 to 7 in agriculture or other fields for preparing fungicides, insecticides and acaricides.
10. The bactericidal, insecticidal and acaricidal composition is characterized by comprising the following components in parts by weight: containing as active ingredient a compound of general formula I according to any one of claims 1 to 7, the composition containing 0.1 to 99% by weight of active ingredient.
11. Use of a composition according to claim 10 for controlling germs, pests and mites in agriculture or other fields.
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