CN113512029B - 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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CN113512029B
CN113512029B CN202010277446.4A CN202010277446A CN113512029B CN 113512029 B CN113512029 B CN 113512029B CN 202010277446 A CN202010277446 A CN 202010277446A CN 113512029 B CN113512029 B CN 113512029B
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CN113512029A (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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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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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
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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 a pyrimidine amine-containing substituted pyrazole compound shown as the following general formula 1 and specific compounds CK1 and CK2, and application of the compound as agricultural bactericide, insecticide, acaricide and the like.
Figure BDA0002445325790000011
The following compounds CK3, CK4, CK5 were retrieved on-line by Scifinder, but no specific reference is made.
Figure BDA0002445325790000012
Patents CN106167484 and EP3299366 report the use of pyrimidine-containing substituted pyrazoles of the general formula 2 and CK6 as agricultural fungicides, insecticides, acaricides, etc.
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
R 1 selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 3 -C 12 Cycloalkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 1 -C 12 Alkylthio, halogeno C 1 -C 12 Alkylthio radical, C 1 -C 12 Alkylsulfinyl radical, C 1 -C 12 Alkylsulfonyl radical, C 2 -C 12 Alkenyl, halo C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, halo C 2 -C 12 Alkynyl, C 3 -C 12 Alkenyloxy, halogeno C 3 -C 12 Alkenyloxy radical, C 3 -C 12 Alkynyloxy, halo C 3 -C 12 Alkynyloxy, C 1 -C 12 Alkylamino radical, di (C) 1 -C 12 Alkyl) amino, C 1 -C 12 Alkylaminocarbonyl, halogeno C 1 -C 12 Alkylaminocarbonyl radical, C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl or C 1 -C 2 Alkylthio group C 1 -C 12 An alkyl group;
R 2 selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy or halo C 1 -C 12 An alkoxy group;
wherein R is 1 And R 2 Can also form a five-membered ring, a six-membered ring, a seven-membered ring or an eight-membered ring containing C, N, O or S together with a connected pyrimidine ring;
R 3 selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 3 -C 12 Cycloalkyl, C 1 -C 12 Alkylthio radical, C 2 -C 12 Alkenylthio radical, C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, halo C 2 -C 12 Alkenyl, halo C 2 -C 12 Alkynyl, C 1 -C 12 Alkylamino, halogeno C 1 -C 12 Alkylamino radical, di (C) 1 -C 12 Alkyl) amino, di (halo C) 1 -C 12 Alkyl) amino, C 1 -C 12 Alkyl hydrazino, C 1 -C 12 Alkoxyamino group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylsulfinyl, halogeno C 1 -C 12 Alkylsulfinyl radical, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl radical, C 1 -C 12 Alkylaminosulfonyl, di (C) 1 -C 12 Alkyl) aminosulfonyl, C 1 -C 12 Alkylsulfonylaminocarbonyl group, C 1 -C 12 Alkylcarbonylaminosulfonyl radical, C 3 -C 12 Cycloalkyloxycarbonyl radical, C 1 -C 12 Alkylcarbonyl, halo C 1 -C 12 An alkylcarbonyl group,C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkyl carbonyl group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylaminocarbonyl, di (C) 1 -C 12 Alkyl) aminocarbonyl, C 2 -C 12 Alkenyloxycarbonyl radical, C 2 -C 12 Alkynyloxycarbonyl group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkylaminosulfenyl, di (C) 1 -C 12 Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 5 1 -C 6 Alkyl, heteroaryl C 1 -C 6 Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C 1 -C 6 Alkyloxy, heteroaryl C 1 -C 6 Alkyloxy, aryl C 1 -C 6 Alkylamino, heteroaryl C 1 -C 6 Alkylamino, the following groups being halogen, nitro, cyano, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
y is selected from NR 3 O or S;
R 4 、R 5 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy or halo C 1 -C 12 An alkoxy group;
wherein R is 4 And R 5 And optionally C connected thereto to form C 3 -C 8 A ring of (a);
R 6 、R 7 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy or halo C 1 -C 12 An alkoxy group;
wherein R is 6 And R 7 And optionally C connected thereto to form C 3 -C 8 A ring of (a);
m is an integer from 0 to 5;
R 8 selected from hydrogen, cyano, halogen, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R 11 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 9 selected from hydrogen, cyano, halogen, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl, unsubstituted or substituted by 1-5R 11 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 10 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 3 -C 12 Cycloalkyl radical, C 1 -C 12 Alkylamino, halogeno C 1 -C 12 Alkylamino radical, di (C) 1 -C 12 Alkyl) amino, halo-di (C) 1 -C 12 Alkyl) amino, C (= O) NR 11 R 12 、C 1 -C 12 Alkylthio, halogeno C 1 -C 12 Alkylthio radical, C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, C 2 -C 12 Alkenyloxy, halogeno C 2 -C 12 Alkenyloxy radical, C 2 -C 12 Alkynyloxy, halo C 2 -C 12 Alkynyloxy, C 1 -C 12 Alkyl sulfonyl radicalHalogen substituted C 1 -C 12 Alkylsulfonyl radical, C 1 -C 12 Alkylcarbonyl, halo C 1 -C 12 Alkylcarbonyl group, C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylcarbonyloxy, halo C 1 -C 12 Alkylcarbonyloxy, C 1 -C 12 Alkoxycarbonyloxy, halo C 1 -C 12 Alkoxycarbonyloxy, C 1 -C 12 Alkylsulfonyloxy, halo C 1 -C 12 Alkylsulfonyloxy, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxy or halo C 1 -C 12 Alkoxy radical C 1 -C 12 An 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, R 10 May be the same or different;
R 11 、R 12 can be the same or different and are respectively selected from hydrogen and C 1 -C 12 Alkyl or halo C 1 -C 12 An alkyl group;
w is selected from hydrogen, halogen, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 3 -C 8 Cycloalkyl, C 1 -C 12 Alkoxy radical, C 1 -C 12 Alkylthio or C 1 -C 12 An alkylsulfonyl group.
Preferred compounds of the invention are: in the general formula I
R 1 Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 1 -C 6 Alkylthio radical, C 1 -C 6 Alkylsulfinyl radical, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylthio radical, C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkynyl, C 3 -C 6 Alkenyloxy, halogeno C 3 -C 6 Alkenyloxy radical, C 3 -C 6 Alkynyloxy, halo C 3 -C 6 Alkynyloxy, C 1 -C 6 Alkylamino radical, di (C) 1 -C 6 Alkyl) amino, C 1 -C 6 Alkylaminocarbonyl, halogeno C 1 -C 6 Alkylaminocarbonyl radical, C 1 -C 6 Alkoxycarbonyl, halo C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl or C 1 -C 6 Alkylthio group C 1 -C 6 An alkyl group;
R 2 selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
wherein R is 1 And R 2 Can also form a five-membered ring or a six-membered ring containing C, N, O or S together with the connected pyrimidine ring;
R 3 selected from hydrogen, halogen, hydroxy, amino, hydroxylamino, hydrazino, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkylthio radical, C 2 -C 6 Alkenylthio radical, C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkynyl, C 1 -C 6 Alkylamino, halogeno C 1 -C 6 Alkylamino radical, di (C) 1 -C 6 Alkyl) amino, di (halo C) 1 -C 6 Alkyl) amino, C 1 -C 6 Alkyl hydrazino, C 1 -C 6 Alkoxyamino group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylsulfinyl, halogeno C 1 -C 6 Alkylsulfinyl radical, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylaminosulfonyl, di (C) 1 -C 6 Alkyl) aminosulfonyl, C 1 -C 6 Alkylsulfonylaminocarbonyl group, C 1 -C 6 Alkylcarbonylaminosulfonyl radical, C 3 -C 6 Cycloalkyloxycarbonyl radical, C 1 -C 6 Alkylcarbonyl, halo C 1 -C 6 Alkylcarbonyl group, C 1 -C 6 Alkoxycarbonyl, halo C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkyl carbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylaminocarbonyl, di (C) 1 -C 6 Alkyl) aminocarbonyl, C 2 -C 6 Alkenyloxycarbonyl radical, C 2 -C 6 Alkynyloxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkylaminosulfenyl, di (C) 1 -C 6 Alkyl) aminosulfanyl, aryl which is unsubstituted or further substituted by 1 to 5Cyclic aryl, hetero-condensed cyclic aryl, aryl C 1 -C 6 Alkyl, heteroaryl C 1 -C 6 Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C 1 -C 6 Alkyloxy, heteroaryl C 1 -C 6 Alkyloxy, aryl C 1 -C 6 Alkylamino, heteroaryl C 1 -C 6 Alkylamino, the following groups being halogen, nitro, cyano, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
y is selected from NR 3 O or S;
R 4 、R 5 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
wherein R is 4 、R 5 And optionally C connected thereto to form C 3 -C 6 A ring of (a);
R 6 、R 7 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
wherein R is 6 、R 7 And optionally C connected thereto to form C 3 -C 6 A ring of (a);
m is an integer from 0 to 4;
R 8 selected from hydrogen, cyano, halogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl, halo C 1 -C 6 Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R 11 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 9 selected from hydrogenCyano, halogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl, halogeno C 1 -C 6 Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R 11 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 10 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkylamino, halogeno C 1 -C 6 Alkylamino radical, di (C) 1 -C 6 Alkyl) amino, halo-di (C) 1 -C 6 Alkyl) amino, C (= O) NR 11 R 12 、C 1 -C 6 Alkylthio, halogeno C 1 -C 6 Alkylthio radical, C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, C 2 -C 6 Alkenyloxy, halogeno C 2 -C 6 Alkenyloxy radical, C 2 -C 6 Alkynyloxy, halo C 2 -C 6 Alkynyloxy, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylcarbonyl, halo C 1 -C 6 Alkylcarbonyl group, C 1 -C 6 Alkoxycarbonyl, halo C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylcarbonyloxy, halo C 1 -C 6 Alkylcarbonyloxy, C 1 -C 6 Alkoxycarbonyloxy, halo C 1 -C 6 Alkoxycarbonyloxy, C 1 -C 6 Alkylsulfonyloxy, halo C 1 -C 6 Alkylsulfonyloxy, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxy or halo C 1 -C 6 Alkoxy radical C 1 -C 6 An 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, R 10 May be the same or different;
R 11 、R 12 can be the same or different and are respectively selected from hydrogen and C 1 -C 6 Alkyl or halo C 1 -C 6 An alkyl group;
w is selected from hydrogen, halogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkoxy radical, C 1 -C 6 Alkylthio or C 1 -C 6 An 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 3-position of the pyrazole ring, then R 8 In the 4 position, R 9 At position 5; when Y is attached to the pyrazole ring at the 4-position, then R 8 In the 3-position, R 9 At position 5; when Y is attached to the pyrazole ring at the 5-position, then R 8 In the 3 position, R 9 At 4 bits.
Further preferred compounds of the invention are: in the general formula I
R 1 Selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 1 -C 4 Alkylthio radical, C 1 -C 4 Alkylsulfinyl radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl, halo C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkynyl, C 3 -C 4 Alkenyloxy, halogeno C 3 -C 4 Alkenyloxy radical, C 3 -C 4 Alkynyloxy, halo C 3 -C 4 Alkynyloxy, C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkylaminocarbonyl, halogeno C 1 -C 4 Alkylaminocarbonyl radical, C 1 -C 4 Alkoxycarbonyl, halogeno C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl or C 1 -C 4 Alkylthio group C 1 -C 4 An alkyl group;
R 2 selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 1 And R 2 Can also form a five-membered ring or a six-membered ring containing C, N, O or S together with the connected pyrimidine ring;
R 3 selected from hydrogen, halogen, hydroxy, amino, hydroxyamino, hydrazino, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkenyl, halo C 2 -C 4 Alkynyl, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, di (halo C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkyl hydrazino, C 1 -C 4 Alkoxyamino group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylsulfinyl, halogeno C 1 -C 4 Alkylsulfinyl radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylaminosulfonyl, di (C) 1 -C 4 Alkyl) aminosulfonyl, C 1 -C 4 Alkylsulfonylaminocarbonyl group, C 1 -C 4 Alkylcarbonylaminosulfonyl radical, C 3 -C 4 Cycloalkyloxycarbonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkyl carbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylaminocarbonyl, di (C) 1 -C 4 Alkyl) aminocarbonyl, C 2 -C 4 Alkenyloxycarbonyl radical, C 2 -C 4 Alkynyloxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkylaminosulfenyl, di (C) 1 -C 4 Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 5 1 -C 4 Alkyl, heteroaryl C 1 -C 4 Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy, aryl C 1 -C 4 Alkyloxy, heteroaryl C 1 -C 4 Alkyloxy, aryl C 1 -C 4 Alkylamino, heteroaryl C 1 -C 4 Alkylamino, the following groups being halogen, nitro, cyano, C 1 -C 4 Alkyl, haloGeneration C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
y is selected from O;
R 4 、R 5 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 4 、R 5 And optionally C connected thereto to form C 3 -C 4 A ring of (a);
R 6 、R 7 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 6 、R 7 And optionally C connected thereto to form C 3 -C 4 A ring of (a);
m is an integer from 0 to 3;
R 8 selected from hydrogen, cyano, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R 11 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl, or heteroaryloxycarbonyl;
R 9 selected from hydrogen, cyano, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R 11 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 10 selected from halogen, hydroxyl,Amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, halo-di (C) 1 -C 4 Alkyl) amino, C (= O) NR 11 R 12 、C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogeno C 2 -C 4 Alkenyloxy radical, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylcarbonyloxy, halo C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo C 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo C 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy or halo C 1 -C 4 Alkoxy radical C 1 -C 4 An 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, R 10 May be the same or different;
R 11 、R 12 can be the same or different and are respectively selected from hydrogen and C 1 -C 4 Alkyl or halo C 1 -C 4 An alkyl group;
w is selected from hydrogen, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkoxy radical, C 1 -C 4 Alkylthio or C 1 -C 4 An 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 R 8 In the 4 position, R 9 At the 5-position, the structural formula is shown as I-1; when O is attached to the 4-position of the pyrazole ring, then R 8 In the 3 position, R 9 At position 5, the structural formula is shown as I-2; when O is attached to the 5-position of the pyrazole ring, then R 8 In the 3 position, R 9 At 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:
R 1 selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 1 -C 4 Alkylsulfinyl radical, C 1 -C 4 Alkylsulfonyl radical, C 2 -C 4 Alkenyl, halo C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkynyl, C 3 -C 4 Alkenyloxy, halogeno C 3 -C 4 Alkenyloxy radical, C 3 -C 4 Alkynyloxy, halo C 3 -C 4 Alkynyloxy, C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkylaminocarbonyl, halogeno C 1 -C 4 Alkylaminocarbonyl radical, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl or C 1 -C 4 Alkylthio group C 1 -C 4 An alkyl group;
R 2 selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
R 3 selected from hydrogen, halogen, hydroxy, amino, hydroxyamino, hydrazino, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkenyl, haloC 2 -C 4 Alkynyl, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, di (halo C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkyl hydrazino, C 1 -C 4 Alkoxyamino group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylsulfinyl, halogeno C 1 -C 4 Alkylsulfinyl radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylaminosulfonyl, di (C) 1 -C 4 Alkyl) aminosulfonyl, C 1 -C 4 Alkylsulfonylaminocarbonyl group, C 1 -C 4 Alkylcarbonylaminosulfonyl radical, C 3 -C 4 Cycloalkyloxycarbonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkyl carbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylaminocarbonyl, di (C) 1 -C 4 Alkyl) aminocarbonyl, C 2 -C 4 Alkenyloxycarbonyl radical, C 2 -C 4 Alkynyloxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkylamino thio, di (C) 1 -C 4 Alkyl) aminosulfanyl, aryl, heteroaryl, fused-ring aryl, fused-ring heteroaryl, aryl C, unsubstituted or further substituted by 1 to 5 1 -C 4 Alkyl, heteroaryl C 1 -C 4 Alkyl, arylamino, heteroarylamino, aryloxy, heteroaryloxy,Aryl radical C 1 -C 4 Alkyloxy, heteroaryl C 1 -C 4 Alkyloxy, aryl C 1 -C 4 Alkylamino, heteroaryl C 1 -C 4 An alkylamino group: halogen, nitro, cyano, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
R 4 、R 5 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 4 、R 5 And optionally C connected thereto to form C 3 -C 4 A ring of (a);
R 6 、R 7 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 6 、R 7 And optionally C connected thereto to form C 3 -C 4 A ring of (a);
R 8 selected from hydrogen, cyano, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl, halogeno C 1 -C 4 Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R 11 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 9 selected from hydrogen, cyano, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R 11 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl,Arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 10 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, halo-di (C) 1 -C 4 Alkyl) amino, C (= O) NR 11 R 12 、C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogeno C 2 -C 4 Alkenyloxy radical, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylcarbonyloxy, halo C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo C 1 -C 4 An alkoxycarbonyloxy group,C 1 -C 4 Alkylsulfonyloxy, halo C 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy or halo C 1 -C 4 Alkoxy radical C 1 -C 4 An 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, R 10 May be the same or different;
R 11 、R 12 can be the same or different and are respectively selected from hydrogen and C 1 -C 4 Alkyl or halo C 1 -C 4 An alkyl group;
R 13 、R 14 、R 15 or R 16 Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy or C 3 -C 4 A cycloalkyl group;
R 17 、R 18 can be the same or different and are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 3 -C 4 Cycloalkyl, unsubstituted or substituted by 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 19 is selected from C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl, aminoSubstituted or by 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 20 selected from hydrogen, cyano, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl, unsubstituted or substituted by 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 21 is selected from C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl, unsubstituted or substituted by 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 22 selected from hydrogen, cyano, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl, unsubstituted or substituted by 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 23 、R 24 each independently selected from C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halogeno C 1 -C 4 Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl, or heteroaryloxycarbonyl;
R 25 、R 26 each independently selected from hydrogen, cyano, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl, unsubstituted or substituted by 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
w is selected from hydrogen, halogen, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkoxy radical, C 1 -C 4 Alkylthio or C 1 -C 4 An alkylsulfonyl group.
Still further preferred compounds of the invention are:
compounds of the general formulae 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, in which
R 1 Selected 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;
R 2 selected from hydrogen, fluoro, chloro, bromo, iodo, cyano, nitro, amino, carboxy, formyl, methyl, ethyl, methoxy, ethoxy or trifluoroethoxy;
R 3 selected 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-propoxy<xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 3238 zxft 3238- , 3262 zxft 3262- , , , , , , , ,4- ,4- ,4- ,4- ,4- ,4- , ,4- ,4- ,4- ,4- ,4- ,4- ,3- ,3- ,3- ,3- ,3- , </xnotran> 2-chlorophenylethylamino, 2-fluorophenylethylamino, 2-bromophenylethylamino, 2-methylphenylethylamino or 2-trifluoromethylphenethylamino;
R 4 、R 5 which 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;
R 6 、R 7 can be the same or different and are respectively selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxyEthoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;
R 8 selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl or trifluoromethyl;
R 9 selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl or trifluoromethyl;
R 10 selected 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, R 10 May be the same or different;
R 13 、R 14 、R 15 or R 16 Which may be the same or different, are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, 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;
R 17 、R 18 which 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 5R 10 Substituted byAryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 19 selected 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 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 20 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 by 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 21 selected 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 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl, or heteroaryloxycarbonyl;
R 22 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 by 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl,An aryloxycarbonyl or heteroaryloxycarbonyl group;
R 23 、R 24 each 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 1-5R 10 Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R 25 、R 26 each 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 1-5R 10 Substituted 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, in which
R 1 Selected from hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl or difluoromethyl;
R 2 selected from hydrogen, fluoro, chloro, bromo, iodo, nitro, amino, formyl, methyl, ethyl, methoxy or ethoxy;
R 3 selected from the group consisting of chloro, amino, hydroxyamino, hydrazino, methyl, ethyl, methoxy, ethoxy, n-propoxy, isopropylOxy, 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, dimethylaminothio, pyrazolyl, 1,2,4-triazolyl, benzylamino, 4-chlorobenzylamine, 4-methoxybenzylamine, 4-trifluoromethoxybenzylamine, phenethylamino, 4-chlorobenzylethylamino, 4-fluorobenzylethylamino, 4-bromobenzylethylamino, 4-methylphenylethylamino, 3-bromobenzylethylamino or 2-fluorobenzylethylamino;
R 4 、R 5 can be the same or different and are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R 6 、R 7 are all selected from hydrogen;
R 8 selected from hydrogen;
R 9 selected from hydrogen;
R 10 selected 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, R 10 May be the same or different;
R 13 、R 14 、R 15 or R 16 Can be the same or different and is respectively selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl;
R 17 、R 18 can 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, in which
R 1 Selected from fluoro, chloro, bromo, iodo, methyl, ethyl or difluoromethyl;
R 2 selected from fluorine, chlorine, bromine, iodine, nitro, amino, formyl and methylOr methoxy;
R 3 selected 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-methoxybenzylamine, 4-chlorophenylethylamino, 4-fluorophenylethylamino, 4-bromophenylethylamino, 4-methylphenylethylamino, 3-bromophenylethylamino and 2-fluorophenylethylamino;
R 4 、R 5 may be the same or different and is independently selected from hydrogen or methyl;
R 6 、R 7 are all selected from hydrogen;
R 8 selected from hydrogen;
R 9 selected from hydrogen;
R 10 selected 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, R 10 May be the same or different;
R 13 、R 14 、R 15 、R 16 are all selected from hydrogen;
R 17 selected from hydrogen;
R 18 selected 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: a substituted or unsubstituted cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, and the like. A haloalkyl group: straight-chain or branched alkyl groups in which hydrogen atoms may be partially or wholly replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl and the like. Alkyl hydrazine group: straight-chain or branched alkyl hydrazines(-NHNH-) groups are attached to the structure, such as methylhydrazino groups. 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 CH 3 NHS-、C 2 H 5 NHS-. Dialkylaminosulfenyl: such as (CH) 3 ) 2 NS-、(C 2 H 5 ) 2 NS-. Alkylamino sulfonyl group: alkyl-NH-SO 2 -. Dialkylaminosulfonyl: (alkyl group) 2 -N-SO 2 -. Alkylsulfonylaminocarbonyl group: alkyl-SO 2 -NH-CO-. Alkylcarbonylaminosulfonyl: alkyl-CO-NH-SO 2 -. 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. CF 3 -SO 2 -O. Cycloalkyloxycarbonyl 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. ClCH 2 CH 2 OCO-、CF 3 CH 2 OCO-, etc. Alkoxyalkyl groups: alkyl-O-alkyl-, e.g. CH 3 OCH 2 -. Haloalkoxyalkyl groups: the hydrogen atoms of the alkyl groups of alkoxyalkyl groups may be partially or fully substituted by halogen atoms, e.g. ClCH 2 CH 2 OCH 2 -、CF 3 CH 2 OCH 2 -and the like. Alkoxycarbonylalkyl groups: alkoxycarbonyl-alkyl-, e.g. CH 3 OCOCH 2 -. Haloalkoxycarbonylalkyl: the hydrogen atoms of the alkyl group of the alkoxycarbonylalkyl group may be partially or fully substituted by halogen atoms, e.g. CF 3 CH 2 OCOCH 2 -. Alkylcarbonyloxy group: such as CH 3 COO-, etc. Haloalkylcarbonyloxy: the hydrogen atoms of the alkylcarbonyloxy group may be partially or fully substituted by halogen atoms, e.g. CF 3 COO-, etc. Alkoxycarbonyloxy: alkoxycarbonyl-oxy-, e.g. CH 3 OCOO-. Haloalkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyloxy group may be partially or fully substituted by halogen atoms, e.g. CF 3 OCOO-. Alkylthio-carbonylalkyl: alkylthiocarbonyl-alkyl-, e.g. CH 3 SCOCH 2 -. Haloalkylthiocarbonylalkyl: the hydrogen atoms of the alkyl group of the alkylthiocarbonylalkyl group may be partially or wholly substituted by halogen atoms, e.g. CF 3 CH 2 SCOCH 2 -. Alkoxy groups: such as CH 3 OCH 2 O-, etc. Haloalkoxyalkyl: the hydrogen atoms of the alkoxy groups being partially or wholly replaced by halogen atoms, e.g. CF 3 OCH 2 O-is formed. An alkoxyalkoxycarbonyl group: such as CH 3 OCH 2 CH 2 OCO-, 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. CH 3 SCH 2 -. Haloalkylthioalkyl: the hydrogen atoms of the alkyl group of an alkylthioalkyl group may be partially or fully substituted by halogen atoms, e.g. ClCH 2 CH 2 SCH 2 -、CF 3 CH 2 SCH 2 -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 ) 2 N-，(CH 3 CH 2 ) 2 N-is provided. Halogenated dialkylamino group: alkane (I) and its preparation methodThe hydrogen atoms of the radicals being partially or wholly substituted by halogen atoms, e.g. (CF) 3 ) 2 N-，(CF 3 CH 2 ) 2 N-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 CH 2 ＝CHCH 2 S-. Alkenyloxycarbonyl radical: such as CH 2 ＝CHCH 2 OCO-, 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, in which the hydrogen atoms may be partially or completely replaced 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 ≡ CCH 2 OCO-, 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. CH 3 CO-，CH 3 CH 2 CO-. 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. CF 3 CO-. Alkoxycarbonyl group: the alkoxy group is attached to the structure via a carbonyl group. Such as CH 3 OCO-，CH 3 CH 2 OCO-. An aminocarbonyl group: such as NH 2 CO-. Alkyl amino carbonyl: alkyl-NH-CO-, e.g. CH 3 NHCO-，CH 3 CH 2 NHCO-. Dialkylaminocarbonyl group: such as (CH) 3 ) 2 NCO-，(CH 3 CH 2 ) 2 NCO-. 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 N, O, S heteroatoms. Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and the like. The heteroaryl fused ring aryl group is a five or six membered fused ring containing 1 or more heteroatoms N, O, S. Such as: indolyl, benzopyrazolyl, and the like. Aryl: such as phenyl, and the like. Heteroaryl group: such as pyridyl, and the like. Arylalkyl: such as benzyl, phenethyl, p-chlorobenzyl. Heteroarylalkyl group: such as 2-chloropyridin-5-yl, 2-chloro-thiazol-5-yl, and the like. An 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 PhCH 2 CO-, etc. Arylcarbonylalkyl, heteroarylcarbonylalkyl: such as PhCOCH 2 -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, heteroarylAn alkyloxycarbonyl group: such as PhCH 2 OCO-、4-Cl-PhCH 2 OCO-, etc.
Tables 1,2,3, 4,5, 6, 7, 8 and 9 respectively show the R in the general formula I 1 、R 2 、R 3 、R 4 And R 5 、R 6 And R 7 、R 8 、R 9 、R 10 And W are not limited to these substituents.
Figure BDA0002445325790000131
TABLE 1R 1 Substituent group
Figure BDA0002445325790000141
TABLE 2R 2 Substituent group
R 2 R 2 R 2 R 2
H F Cl Br
I CN NO 2 NH 2
CHO CH 3 C 2 H 5 n-C 3 H 7
i-C 3 H 7 n-C 4 H 9 s-C 4 H 9 i-C 4 H 9
t-C 4 H 9 OCH 3 OC 2 H 5 OC 3 H 7 -n
OC 3 H 7 -i OC 4 H 9 -n OC 4 H 9 -i OC 4 H 9 -t
OCH 2 F OCHF 2 OCF 3 OCH 2 CF 3
TABLE 3R 3 Substituent group
Figure BDA0002445325790000142
Figure BDA0002445325790000151
Figure BDA0002445325790000161
Figure BDA0002445325790000171
TABLE 4R 4 (R 5 ) Substituent group
Figure BDA0002445325790000172
Figure BDA0002445325790000181
TABLE 5R 6 (R 7 ) Substituent group
Figure BDA0002445325790000182
TABLE 6R 8 Substituent group
R 8 R 8 R 8 R 8
H CN CH 3 C 2 H 5
n-C 3 H 7 i-C 3 H 7 n-C 4 H 9 s-C 4 H 9
i-C 4 H 9 t-C 4 H 9 CF 3 CCl 3
CHF 2 CH 2 F CH 2 Cl CH 2 CF 3
CF 2 CF 3 COOCH 3 Ph Ph-4-Cl
TABLE 7R 9 Substituent group
R 9 R 9 R 9 R 9
H CN CH 3 C 2 H 5
n-C 3 H 7 i-C 3 H 7 n-C 4 H 9 s-C 4 H 9
i-C 4 H 9 t-C 4 H 9 CF 3 CCl 3
CHF 2 CH 2 F CH 2 Cl CH 2 CF 3
CF 2 CF 3 COOCH 3 Ph Ph-4-Cl
TABLE 8R 10 Substituent 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. In the general formula compounds 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 mentioned in the table, W = R 6 ＝R 7 ＝R 8 ＝R 9 ＝R 13 ＝R 14 ＝R 15 ＝R 16 ＝R 17 ＝H。
In the general formula I-1A,
Figure BDA0002445325790000203
when R is 1 ＝Cl、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When (= H), (R) 10 ) n The 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 is 1 ＝Cl、R 2 ＝CH 3 、R 3 ＝NHCH 3 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 10-1-10-1-279.
Table 10-2: in the general formula I-1A, when R is 1 ＝Cl、R 2 ＝OCH 3 、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to 10-1-10-279 of Table 10 in sequence in accordance with Table 10, and representing that the compound numbers are 10-2-1-10-2-279 in sequence.
Tables 10 to 3: in the general formula I-1A, when R is 1 ＝Cl、R 2 ＝CHO、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝Cl、R 2 ＝Br、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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: general formula I-1In A, when R is 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝R 3 ＝Cl、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 1 ＝C 2 H 5 、R 2 ＝R 3 ＝Cl、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝R 3 ＝Cl、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CF 3 、R 2 ＝R 3 ＝Cl、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 1 ＝Cl、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝Cl、R 4 ＝R 5 When = H, substituent (R) 10 ) n Watch and watch10 are consistent and sequentially correspond to 10-1 to 10-279 of the table 10, and represent that the compound numbers are sequentially 20-1 to 20-279.
TABLE 20-1: in the general formula I-1B, when R 3 ＝NHCH 3 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝HNOCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OC 2 H 5 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to 10-1-10-279 of Table 10 in sequence in accordance with Table 10, and representing that the compound numbers are 20-5-1-20-5-279 in sequence.
Table 21-1: in the general formula I-1B, when R is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n In accordance with Table 10, table 10 is sequentially mapped10-1-10-279 of (1), represents a compound number of 21-2-1-21-2-279 in sequence.
Tables 21 to 3: in the general formula I-1B, when R is 3 ＝HNOCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 21-3-1-21-3-279.
Tables 21 to 4: in the general formula I-1B, when R is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 21-4-1-21-4-279.
Tables 21 to 5: in the general formula I-1B, when R is 3 ＝OC 2 H 5 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝R 18 When = H, takeSubstituent (R) 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 23-3-1-23-3-279.
Table 24-1: in the general formula I-1C, when R is 3 ＝OCH 3 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 (= H), substituent (R) 10 ) n Corresponding 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: tong (Chinese character of 'tong')In the formula I-1C, when R is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 1 ＝Cl、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 27-4-1-27-4-279.
Tables 27 to 5: in the general formula I-2A, when R is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 27-5-1-27-5-279 in turn.
TABLE 28-1: in the general formula I-2A, when R is 1 ＝Cl、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the compound numbers 28-2-1-28-2-279 in turn.
Table 28-3: in the general formula I-2A, when R 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the compound numbers 28-5-1-28-5-279 in turn.
TABLE 29-1: in the general formula I-2A, when R 1 ＝Cl、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 29-1-29-1-279 in turn.
TABLE 29-2: in the general formula I-2A, when R is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 29-2-1-29-2-279.
Table 29-3: in the general formula I-2A, when R is 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝Cl、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing compound numbers 30-1-30-1-279 in turn.
Table 30-2: in the general formula I-2A, when R is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn, 10-1-10-279 in Table 10 indicates that the compound numbers are 30-2-1-30-2-279 in turn.
Tables 30 to 3: in the general formula I-2A, when R is 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing compound numbers 30-4-1-30-4-279 in turn.
Tables 30 to 5: in the general formula I-2A, when R is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 31-2-1-31-2-279.
Tables 31 to 3: in the general formula I-2B, when R is 3 ＝HNOCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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.
Tables 31 to 4: in the general formula I-2B, when R is 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OC 2 H 5 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 3 ＝N(CH 3 ) 2 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝HNOCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝OC 2 H 5 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 3 ＝NHCH 3 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding 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 3 ＝NHCH 3 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing a compound number of 34-1-34-1-279 in turn.
TABLE 34-2: in the general formula I-2C, when R is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing a compound number of 34-2-1-34-2-279 in turn.
Table 34-3: in the general formula I-2C, when R is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 35-1-35-1-279 in turn.
Table 35-2: in the general formula I-2C, when R 3 ＝OCH 3 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 35-3-1-35-3-279.
TABLE 36-1: in the general formula I-2C, when R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = H, substituent (R) 10 ) n In agreement with Table 10, the correspondence is made to 10-1 of Table 100 to 279, which represents the compound number of 36-1-36-1-279 in sequence.
TABLE 36-2: in the general formula I-2C, when R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = H, substituent (R) 10 ) n Corresponding 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, when R is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝Cl、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding 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-3AWhen R is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding 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 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝Cl、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 39-5-1-39-5-279.
TABLE 40-1: in the general formula I-3A, when R is 1 ＝Cl、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing a compound number of 40-2-1-40-2-279 in turn.
Tables 40 to 3: in the general formula I-3A, when R 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing a compound number of 40-3-1-40-3-279 in turn.
Tables 40 to 4: in the general formula I-3A, when R is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝Cl、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 41-4-1-41-4-279.
Tables 41 to 5: tong (Chinese character of 'tong')In the formula I-3A, when R is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding 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 is 3 ＝HNOCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 42-3-1-42-3-279 in turn.
Tables 42 to 4: in the general formula I-3B, when R is 3 ＝OCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OC 2 H 5 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 43-2-1-43-2-279.
Table 43-3: in the general formula I-3B, when R is 3 ＝HNOCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 43-3-1-43-3-279.
Tables 43-4: in the general formula I-3B, when R is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝OC 2 H 5 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 43-5-1-43-5-279 in turn.
TABLE 44-1: in the general formula I-3C, when R 3 ＝NHCH 3 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1 to 10-279 of Table 10, representative of the compoundsThe serial numbers are 44-3-1-44-3-279 in sequence.
TABLE 45-1: in the general formula I-3C, when R is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝H，R 18 (= Cl), substituent (R) 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 45-3-1-45-3-279.
TABLE 46-1: in the general formula I-3C, when R is 3 ＝OCH 3 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding 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 3 ＝OCH 3 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 3 ＝OCH 3 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 47-3-1-47-3-279.
TABLE 48-1: in the general formula I-3C, when R is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 in Table 10, the numbers of the representative compounds are 48-1-48-1-279 in turn.
TABLE 48-2: in the general formula I-3C, when R 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding in sequence to 10-1-10-279 of Table 10 in accordance with Table 10, represents the compoundThe materials are numbered 49-1-49-1-279 in sequence.
TABLE 49-2: in the general formula I-4A, when R is 1 ＝Cl、R 2 ＝OCH 3 、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝Cl、R 2 ＝CHO、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 49-3-1-49-3-279.
Tables 49 to 4: in the general formula I-4A, when R is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 49-5: in the general formula I-4A, when R is 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CHF 2 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 1 ＝CF 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding 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 1 ＝Cl、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 1 ＝Cl、R 2 ＝CHO、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝CH 3 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 1 ＝C 2 H 5 、R 2 ＝Cl、R 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 3 ＝N(CH 3 ) 2 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 3 ＝HNOCH 3 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝R 5 (= H), substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 51-4-1-51-4-279.
Tables 51-5: in the general formula I-4B, when R is 3 ＝OC 2 H 5 、R 4 ＝R 5 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝N(CH 3 ) 2 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 52-2-1-52-2-279.
Table 52-3: in the general formula I-4B, when R is 3 ＝NOCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing the number of the compound in turn 52-4-1-52-4-279.
Tables 52 to 5: in the general formula I-4B, when R is 3 ＝OC 2 H 5 、R 4 ＝H、R 5 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 3 ＝NHCH 3 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 53-3-1-53-3-279 in turn.
TABLE 54-1: in the general formula I-4C, when R is 3 ＝OCH 3 、R 4 ＝R 5 ＝R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝R 5 ＝H，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝R 5 ＝H，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = Cl, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 (= Cl), substituent (R) 10 ) n Corresponding 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 is 3 ＝OCH 3 、R 4 ＝H、R 5 ＝CH 3 ，R 18 ＝CH 3 When (R) is substituted 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H、R 19 ＝CH 3 、R 20 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H、R 21 ＝CH 3 、R 22 (= H), substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H、R 23 When = H, substituent (R) 10 ) n Corresponding 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 is 3 ＝NHCH 3 、R 4 ＝R 5 ＝H、R 24 When = H, substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 in Table 10, the representative compound numbers are 60-1-60-279 in turn.
Table 61: in the general formula I-1H, when R 3 ＝NHCH 3 、R 4 ＝R 5 ＝H、R 25 (= H), substituent (R) 10 ) n Corresponding to Table 10 in turn to 10-1-10-279 of Table 10, representing a compound number of 61-1-61-279 in turn.
Table 62: in the general formula I-1I, when R 3 ＝NHCH 3 、R 4 ＝R 5 ＝H、R 26 When = H, substituent (R) 10 ) n Corresponding 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 4 ＝R 5 ＝H、(R 10 ) n When =4-Cl, the substituent R 3 (R 3 Not Cl, NHCH 3 、N(CH 3 ) 2 、HNOCH 3 、OCH 3 、OC 2 H 5 When) are different substituents as shown in Table 63, representing the compound numbers sequentially63-1—63-180。
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, the compounds of the general formula I are prepared according to the difference of the positions of the O and the pyrazole ring, i.e. the general formulas 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 R 3 And reacting the H in a proper solvent under the alkaline condition to obtain the compound shown in the general formula I-1.
Suitable bases can be selected from, for example, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium or 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 30 minutes to 20 hours, usually 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 according to the following method:
Figure BDA0002445325790000351
intermediate II is commercially available in part and can be prepared by known methods, for example, as described in documents 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 produce M-2, which is described in DE19652516, WO9703969 and Bulletin of the Korea Chemical Society (2010), 31 (11), 3341-3347; m-2 was reacted with the corresponding halide to produce III, a procedure which is described in U.S. Pat. No. 5, 20100158860, WO2011133444 and Bioorganic & Medicinal Chemistry,20 (20), 6109-6122,2012. The intermediates II and III are reacted under alkaline conditions to obtain F-1, the operation method of the step is referred to CN106167484 and EP3299366, and the F-1 is reacted with an acylating agent phosgene or solid phosgene to obtain T-1, and the operation method of the step is referred to WO 2015057963.
The intermediates were derived from: intermediates X-1, R 3 H is commercially available or can be prepared according to conventional methods.
The appropriate temperature for 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 R 3 And 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), 1370-1387; 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 are reacted under basic conditions to produce F-2, which is operated in the same manner as F-1 of I-1, and from F-2 to T-2 is operated in the same manner as F-1 to T-1 of I-1.
Suitable solvents may be selected from methanol, ethanol, tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetone, or butanone, and 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 R 3 And 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), 5061-5071, etc.; q-1 to V are prepared by the same method as M-2 to III in I-1. The intermediates II and V are reacted under basic conditions to produce F-3, which is carried out in the same manner as F-1 of I-1, and from F-3 to T-3 in the same manner as F-1 to T-1 of I-1.
(2) When Y = NR 3 Or 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.; <xnotran> , ( , , , , , , , , , , , , , , , ), ( , , , , , , ), ( , , , , ), ( , , , , , , 5363 zxft 5363 , , , , , , , , , , ), ( , , , , ), ( , , ), ( , , , , , , , ), ( , , , , , , , , , ), ( , </xnotran> Black spot of rape, black spot of sesame, black spot of sunflower, black spot of castor, black spot of tomato, black spot of pepper, black spot of eggplant, black spot of bean, black spot of cucumber, black spot of celery, black rot of carrot, black spot of apple, black spot of peanut), 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-breaking disease, rice blast, sheath blight, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem blight, soybean black spot, melon northern leaf spot, peanut net blotch, tea red leaf spot, pepper white spot, wax gourd leaf spot, celery black rot, spinach heart rot, kenaf leaf mold, kenaf spot, jute stem spot, soybean violet spot, sesame leaf spot, castor gray spot, tea brown leaf spot, brown round spot, kidney red spot, balsam pear white spot, watermelon spot, jute rot, sunflower root rot, kidney bean rot, soybean target, eggplant rod spore leaf spot, cucumber target spot, tomato leaf mold, eggplant leaf mold, broad bean red spot, etc.); 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.); ascomycetes 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, loofah powdery mildew, pumpkin powdery mildew, wax gourd powdery mildew, melon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia sclerotiorum (flax sclerotinia sclerotiorum, rape sclerotinia sclerotiorum, soybean sclerotinia sclerotiorum, peanut sclerotinia sclerotiorum, tobacco sclerotinia sclerotiorum, pepper sclerotinia sclerotiorum, eggplant sclerotinia sclerotiorum, bean sclerotinia sclerotiorum, pea sclerotiorum, cucumber sclerotiorum, bitter gourd sclerotinia sclerotiorum, wax gourd sclerotinia sclerotiorum, watermelon sclerotinia sclerotiorum, celery sclerotiorum), scab (scab of black star, pear scab) and the like.
The compounds of the general formula I can be used for controlling the following pests:
coleoptera (coleoptitera) (beetles): leguminous species (Acanthoscelides spp.) (elephant), phaseolus vulgaris (Acanthoscelides obtectus) (common pisiform image), ceratophyllum album (Agrilus planipes) (Fraxinus variegatus) and Flammulina species (Agriotes spp.) (wireworm), anoplophora glabripennis (Asian longhorn longipedunculus), gothistle species (Anthonium spp.) (Arthobium family), gothistle (Anthonium grandis) (Cotton bollworm cocoon), apium mellea species (Aphidius spp.) (Aprionus spp.) (Anthonium spp.) (elephant), aconitum species (Apocynia spp.) (Holotrichia grub) black striped tortoise (atacinia pretzeriana), cryptogamic beet (atomys specularis), cryptogamic beet (atomura lineris) (small beet beetles (pygmy mangold beetles), cucurbita species (autolophore spp.), weevils (botynoderes punctinvaris) (beetroot weevils), pisiform species (Bruchus spp.) (weevils), pisiform weevils (Bruchus pisum) (pea weevils), cacosesia species (cacosesia spp.), pisum variegatus (callosoides maculoides) (southern cowpea weevils), yellow tail beetles (carpophillius hemiptera) (xerophycus ceras), beet beetles (casssida viteta), longipes (costa spp.), ccorooma species (Ccorooma spp.) (Jin Dichong (chrysomycis)), diabrotica (Cerotoma trifur cata) (Bulbophyllum tenesmus), costus species (Ceratorchus spp.) (weevil)), brassica alba boiss (deuteronchus assimilis) (cabbage weevil), brassica napus boiss (cabbage curried weevil)), brassica napus boiss (deuteronchus napi) (cabbage Curculio), genus jumping beetle (chaetocerema spp.) (Jin Dichong), genus Colaspis (Colaspis spp.) (beetle), condereus scaiaris, conderuus stigmosus, li Xiang (condrapolus nenurar) (Mei Zhui weevil), cotinus nitidis (greenflies June beetle), asparagus caterpillars (Crioceris aspalatus) (asparagus beetle), red beetles (cryptolepis ferrugineus) (rust Gu Jiachong), long horn beetles (cricotulis pusillus) (flat beetle), pseudopteris ferrugineus (cryptolepis ferrugineus) (turkey Gu Jiachong (turnbuckle beetle)), encochlamya species (Ctenoceps spp.) (nematode), elephant species (curriculus spp.) (ostrich), ostrinia species (ostrich spp. (ostrich), ostrinia spp. (ostrinia nubila spp.) (grub), white beetle larvae (sylvestris spp.) (ostrinia nigripes (ostrich), ostrinia nigrum spilus spp. (ostrinia spp.) (grub) (leucopteris), ostrinia nigrum (ostrinia nigrum spp.) (ostrinia fusca (ostrinia nigrum spp.) (grub) (leucopteris 26), ostrinia septemia spp (ostrinia septemia spp.) (ostrinia september) (ostrinia septemia spp. (ostrinia september) (sarum) The insect-eaten stem weevils (rautinus cubae), the Siberian white root neck weevils (Hyperbius palusts) (panopis panulii (pales weevil)), she Xiangshu species (Hypera spp.) (elephant), the alfalfa leaf weevils (Hypera pottica) (alfalfa weevil), the Hyperdoes species (Hyperdoes spp.) (Argentina stem weevil (Hyperodes wevil)), the coffee berry little ground beetle (Hyperthenemus hampeii) (coffee berry beetle), the Philippine species (Ippos spp.) (spinal sticus silvestis (Hyperodors)), the tobacco beetles (Lasioderma serricorne) (Nicotiana), the potato beetle (Leptospira decemlineea) (Colorado. Potatodes), the lipogynogenes sporus sp., the Lipogenes sporus sp., the Lipogenes sporus chinensis (Leptophycus sporus chinensis), the rice flour weevils sporus chinensis (Ligustinus sp.) (Ligustinus walrus sp.) (Leptophys sporus sp.), megascolelis species (Megascolelis spp.), corn beetles (Melanotus communis), meligamentia species (Meligethes spp.), rape pollen beetles (Meligethes aeneus) (blossom beetles), marigoni quinquefolia (Melolontha megacephala) (common European beetles), oberea brevica, obera graciliata (Oberea Linearis), rhinoceros coides (Oryces rhynchos) (date beetle), trade saw (Oryza sativa) (market saw beetle), saw (Oryza sativa), saw beetles (Oryza sativa) (sawtooth beetle 3262, saw 3262 (saw tooth beetle)), (Meleagle), weevil species (rotirrhynchus spp.) (weevil), black angle negative mudworm (Oulema melanopus) (orange foot negative mudworm (cereal leaf beetle)), rice negative mudworm (Oulema oryzae), rose short beak weevil species (pantomomus spp.) (weevil), phyllopodium species (Phyllophaga spp.) (pentacle/hexacle chafer), phvllophaga cuyabana, phyllotreta spp. (Jin Dichong), pinus horrida spp. (Phynchites spp.), popilia japonica (Popilia japonica) (Japanese chafer), stachys palustris (Prostephanis truncates) (large palustris), gu Chun (Rhizoperta dominica) (Gu Xiao moth (leiser grandis borer)), rhizopus spp. (Rhizogus grandis spp.) (European gold (European chafer)), cryptocarya spp. (Pharma purpurea), rhynchopus spp. (Pharma purpurea), rhynchophorrida spp. (elephant), leptophora, rhynchophorus spp.) (Phyllophora spp.) (Rhynchophorus spp.) (elephant) clods (stupid moth) species, species of genus shonophorus (Scolytus spp.) (elephant), elephant (sitonas linatus) (pea She Xiangjia (pca leaf weevil)), elephant species (Sitophilus spp.) (elephant nail), elephant (Sitophilus grandis) (maggot worm (gruney weevil)), rice weevil (Sitophilus oryzae) (rice weevil), stewartia (Stegobium panicum) (drumstick beetle), pseudogriseus sper (Tribolium spp.) (elephant worm) Red pseudogrits (Tribolium castaneum), tribolium confluens (Tribolium confluens), trogopterus variegates (trogopterus florus beetle), and zaberus teneboides.
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): aedes species (Aedes spp.) (mosquito), lucerne fly larvae (Agromyza frontella) (alfalfa blossom flies), agromyzis species ((Agromyza spp.) (leaf flies), trypetid species (Anastrepha spp.) (fruit flies), garlerthan trypetid flies (Anastrepha persica) (garlerthan trypetid flies), anopheles species (Anopheles spp.) (mosquito), fruit fly species (Bactrocera spp.) (fruit flies), melon flies (Bactrocera cubae) (melon flies), citrus fruit flies (Bactrocera dorsalis) (citrus fruit flies), small-stick fly species (ceitis spp.) (fruit flies), and sea fly larvae (sea fly) (sea flies). Deer fly species (Chrysops spp.), trypanosoma species (Cochliomyia spp.) (Calia spirifera larvae), mosquito species (Contarinia spp.) ( mosquito), culex species (Culex spp.) (mosquito), she mosquito species (Dasineura spp.) ( mosquito), oil leaf mosquito (Dasineura brassicae) (cabbage mosquito), seed fly species (Delia spp.), gray fly (Delia platura) (root maggot (seedcoat maggg)), fruit fly species (Drosophila spp.) (vinegar), seed species (Fannus spp.) (Farinia platura), yellow fly (3534) fly (yellow fly), etc. (Latifen webfly) (Kirius fasciola spp.) (Kishina fly) (Kishin.) (Kishin fly (3534 fly) (Latif.) (Latif fly (Latif.) (Latif) in Latif) lat Ashbya grisea (Fannia clavuliris) (Botrys griseus), sarcophagus megacephalus (Gasterophilus intestinalis) (Paget stomacha), gracillia persea, haematobia irutans (horn fly), musca melanophora species (Hylemia spp.) (root maggot)), dermabrasion (Hyenderma Lineatum) (common dermabrasion grub), musca maculatus species (Liriomyza spp.) (leaf miner), musca brassicae (Liriomyza brassica) (Serpentis leaf fly (serpen leaf miner)), musca ovis (Mephalus ovis (sheep tick)), musca species (Musca spp.) (Musca fly (fly), and autumn fly (Musca), musca domestica (Murray) (family fly (baby fly)), (Musca) housefly (Vusca domestica) (house fly), sheep fly (Oestrus ovis) (sheep nose fly), european straw fly (Oscinella frat) (Sweden straw fly), beet spring fly (Pegomyia beta) (spinach leaf fly (beet leaf), mycoplasma species (Phorbia spp.), carrot stem fly (Psila rosa (carrot rust fly)), cherry fruit fly (Rhagoletis cerasi), apple fruit fly (Rhagoletis pomonella) (apple (apple bug)), chinese red mud fly (Sitodiplis malassela) (orange wheat yellow rice), apple fruit fly (apple yellow rice fly)), (sheep nose fly (apple fly)), and the like, stable flies (stable flies), horsefly species (horse flies) and mosquito species (mosquito spp.).
Hemiptera (Hemiptera) (stinkbug): stinkbug (Acrosteronum hirae) (green stink bug), america Gu Changchun (Blissus leucopterus) (Long stink bug), potato Juncus nigrus (Calciosa norvegicus) (potato mirid), tropical bug (Cimex hemipterus) (tropical stink bug), bed bug (Cimex molecular) (bed bug), daghertus fasciatus, dichelops furcatus, gottus armyworm (Dysdercus sutureus) (Cotton stinus), edissa meditata, euonymus alatus (Euonymus), euonymus alatus (Brown stinus), euonymus alatus (Brown stink bug), euonymus alatus (Brown stinus)). Plant bugs (Helopeltis antonii), plant bugs (Helopeltis theivora) (tea bright plant), stinkbug species (Lagynomus spp.) (stinkbug), rice Lygus (Leptosporidium oryzae), oryza sativa (Leptosporidium oryzae), oridous heterophyllus (Leptosporidium varicornis), lygus (Lygus spp.) (Lygus bug), lygus hesperus (Lygus hesperus bug), lygus syriacus (horse germ bug), neurocarpus longus (horse germ stink bug), rice green (Nezara viridula) (southern bug), plant bug (Phytocassius), plant harzianum (Phytocrystictus), plant (Phytocytris), plant (Phytocytrium grandis), plant (Phytocalyx grandis), piezodorus guilidinggi, piezococapus lineus (fleuralineus plant bug), psallus vaccinicola, pseudophyta perseae, scaptocoris castanea and Tradelphia species (Triatoma spp.) (Blodsuctingconense bug)/Nephocorium sutent (kissing bug)).
Homoptera (Homoptera) (aphids, scale, whiteflies, leafhoppers): <xnotran> (Acrythosiphonpisum) ( (pea aphid)), (Adelges spp.) (adelgids), (Aleurodes proletella) ( ), (Aleurodicus disperses), (Aleurothrixus flccosus) ( (woolly whitefly)), (Aluacaspis spp.), amrasca bigutella bigutella, (Aphrophora spp.) ( (leafhopper)), (Aonidiella aurantii) ( (California red scale)), (Aphis spp.) (), (Aphis gossypii) (cotton aphid), (Aphis pomi) (apple aphid), (Aulacorthitm solani) ( (foxglove aphid)), (Bemisia spp.) (), (Bemisia argentifolii), (Bemisia tabaci) (sweetpotato whitefly), (Brachycolus noxius) ( (Russian aphid)), (Brachycorynclia asparagi) ( (asparagus aphid)), brevennia rehi, (Brevicoryne brassicae) ( ), (Ceroplastes spp.) (), (Ceroplastes rubens) (red wax scale), (Chionaspis spp.) (), (Chrysomphalus spp.) (), </xnotran> Genus Ericerus pela (Coccus spp.) (Lecanirus), genus Malus pinkis (Dysaphis plantaginacea) (rosy apple aphid), genus Empoasca (Empoasca spp.) (leafhopper), genus Aphis gossypii (Eriosoma lanigerum) (woolly apple aphid), genus Lecanis (Icerya purchasi) (cottony cushien scale), genus Iris mangifera (Idiosphaeus nidulanus) (mangeafhhopper) Laodelphax striatellus (small brown planthopper), the species of the genus Endocarpium (Lepidosaphs spp.), the species of the genus Long pipe aphid (Macrosiphum spp.), the species of the genus Euphorbia pekinensis (Macrosiphum tupelagi), the species of the genus Euphorbia pekinensis (Macrosiphum eupatoria major) (potato aphid (potatoto aphid)), the species of the genus Myzus praecox (Macrophum grandis) (English aphid (English grain aphid)), (Laodelphax striatellus) (Lepidotis major (Lepidotis spp.)), and (Lepidotis major) of the genus Myzus praecox) of the family England, wherein Long pipe aphid (Macrosiphum rosae) (rose aphid), quilamentus quartus (Macrosteminus tetragonoloba) (purple pipe aphid (aster leafhopper)), mahanarva fribiolata, meanophys sanguinea (Metholophilum dirhodium) (rose aphid (rose grandis)), midis longicornis, myzus persicae (Myzus persicae) (green peach aphid), nephophora nigricans (Nephotektropp), nephophora nigricans (leaf hopper), nephophora nigricans (Paraphylla nigra), and Nilaparvata nigra (brancho plantula), piper nigra (Paraphylla grandis) (Perphaleria cornua), and Nilaparvata nigra (maize grandis), nilapathifolia (corn aphid grandis) (maize grandis), nilapathiocarpus nigra (corn aphid), nilapathiocarpus nigra (Periple), and Periplaneta nigra officinalis (maize grandis) are provided by the family of the genus Nippocastales, plant species of the genus Laoderma (Philaenus spp.) (Lawsonia inermis), rhizopus viticola (Phylloxera viticola) (graptophyllera), lepidogra cunea (Phyllokermes pise) (spercebud scale), lepidogra pellucida (Planococcus spp.) (Lepidogra), lepidogra sp (Pseudococcus spp.) (Lepidogra), lepidogra pelagi (Pseudococcus brcves) (Pinc apple & lt & gt & ltmcalylbu & gt) & ltd & gt the diseases of the pear garden include the balanophora (quadriceps persicae) (San Jose scale), the genus of aphid (Rhapalacium spp.) (aphid), the leaf aphid of maize (Rhapalacium maida) (maize leaf aphid), the leaf aphid of cereal (Rhapalacium padi) (opatibid-cherry aphid), the leaf aphid of maize (Rhapalacium papyridis) (apple aphid-cherry aphid) the species lecanicillium (sausetia spp.) (scale), elegans lecanicillium (sausetia oleae) (black scale), schizaphis graminum (Schizaphis graminum) (greenfly), siganus canaliculatus (Sitobion avengense) (british wheat aphid), whitefly (Sogatella furcifera) (white-backed plant), cercosphaera species (Therioaphis spp.) (aphid), ceroplasma species (tomeyyella spp.) (scale), green-house sound species (toxoplasma spp.) (green-house), whitefly species (Trialeurodes vaporariorum) (white-house), white-house whitefly (Trialeurodes vaporariorum) (white-house wing), white-house white-fly (white-house) species (Trialeurodes (whitefly), white-house (white-house) plant (white-house greenfly (white-wing greenfly) The genus Tocopaia (Unaspis spp.) (Lecanis), tocopperas acutus (Unaspis yanonensis) (Arrowhead scale), and Zulia entreriana.
Hymenoptera (Hymenoptera) (ants, wasps and bees): incised leaf ant species (Acromyrrmex spp.), sinkiang leafminer (Athalia rosea), she Yishu species (Atta spp.), ieafcuting ants, black ant species (Camponotus spp.), wooden ant (carpenter ant), pine leaf bee species (Diprion spp.), sawfly (sawfly), ant species (Formica spp.), ant species (Formica spp.), argentina ant (Iridonomax) (Argentintinent), cocotiana subspecies (Monomorium spp.), little house (Monomorium blake.) ant, monomorium nitrate) (Phanera farreri (Solenopsis), new pine leaf ant species (Neocarinatus spp.), and young wasp species (Queensis spp.), wooden ant species (Queenum spp.), and wooden ant species (Queensis spp.), wooden ant species (Queenslang bee species (Queensis spp.), wooden ant species (Queensis spp.), queensis spp.).
Isoptera (Isoptera) (termites): coptotermes spp, qu E termites (Coptotermes curcignatus), france termites (Coptotermes frenchi), coptotermes formosanus (Coptotermes formosanus) (Formosan subcontrainers termities), corniteus spp (Corniteus spp), sanders spp (Cryptotermes spp), heterotermes spp (Heterotermes spp), sanremoter subcontractor (Desert subcotermities), golden yellow heterotrimes ((IIetertermes aureus), wood termites spp (Kalomtermes spp) (Dry Wood termite), white termites spp (Incasts spp), and Coptotermes spp (Coptotermes spp). Serratia species (Microceromes spp.) (grass termites (harvetter termites)), tripterocephalus oryzae (Microtermes obesi), procornierames species (Procornitermes spp.), (subterranean termites), reticulitermes batens, spongilla fructicola (Reticulitermes spp.) (subterranean termites), reticulitermes banyuensis, spongilla fructicola (Reticulitermes grasseei), blastoma lutescens (Reticulitermes flavipes) (Oriental soil termites), blastoma lutescens (Reticulitermes hagei), west Cantonella (Reticulitermes spertus) (West soil termites), sang Tesan termites (Reticulitermes saurus), blastomerus suturensis (Reticulitermes spp.), blastomerus nigripes punctatus (Reticulitermes), blastoma nigritermes termites spilus (Reticulitermes), blastoma termites punctatus (Reticulitermes punctatus), blastoma punctatus (Reticulitermes termes punctatus), blastoma punctatus) Blastus punctatus (North punctatus), blastus punctatus), blastoma punctatus (Reticulitermes termites) and Blastus punctatus) The genus Reticulitermes spp (Schedorrhiotomes spp.) and the genus archaebacteria spp (Zootermopsis spp.) (Pythium species).
Lepidoptera (Lepidoptera) (moths and butterflies): achoea janata, trichinella fusca (Adoxophyes spp.), trichinella gossypii (Adoxophyes orana), gekko sp (Agrotis spp.), cutworm (Agrotis ipsilon) (Black cutworm), trichinella gossypii (Alabama argillacea) (Cotton leafworm)), amorbia cuneana, amylolosis transistera (novel orangework), anacamptodes defectecta, spodoptera littoralis (Anarsia lineatella) (peach twig borer), jute bridge nightmare (Anomis sabulijeria) (jute looper), cladosporus mucida (Anarsia gemmatalis) (epidermal caterpillar), arcostaphyllus armatus (Arcostaphyllus armatus) (fruited butterpeller), arcostaphyllus testiferus (Arcostaphyllus regia) (fruited curler), arcostaphyllus roseus (Arcostaphyla) walker (rose leaf roller), plectophyceae species (Ar gyroannia spp.) (Tricrid) and Arcostaphyllus citri (Argyena cirana, athyraphyllus citri) walker (orange roller), atomophyceae gypsy gamma, boynada japonica, boynada crispa, and Atomophyma citrifolia (orange roller), and Atomophyma grandis tetrada (orange roller) moth (orange roller). Rice leaf rollers (Borbo cinnara) (rice leaf folder), cotton leaf miner (burcula trifoliata), cotton leaf miner (moth) (cotton leaf performer), diamondback moth (Caloptilia spp.), carpula reticulalis, peach fruit moth (peach fruit moth), corn borer (chinos spp.), mango transverse wire tail moth (Chlumetia transversa) (rice stem moth), rose leaf roller (oriental fruit moth) (rice leaf roller), noctuid moth (chrysodelia mula) and rice leaf rollers (cnaphaloides medinalis (cnaphaloides) are used as a raw material for the production of rice leaf rollers (rice leaf rollers), rice leaf rollers (cnaphaloides medinalis (grassland)) (rice leaf rollers), rice leaf rollers (cnaphaloides medinalis (grassland) and rice leaf rollers (rice leaf rollers)) (rice leaf rollers), <xnotran> (Colias spp.), (Conpomorpha cramerella), (Cossus cossus) ( ), (Crambus spp.) (Sod webworms), (Cydia funebrana) ( (plum fruit moth)), (Cydia molesta) ( (oriental fruit moth)), (Cydia nignicana) (pea moth), (Cydia pomonella) ( (codling moth)), darna diducta, (Diaphania spp.) ( (stem borer)), (Diatr aea spp.) ( (stalk bor er)), (Diatraea saccharalis) (sugarcane borer), (Diatraea graniosella) (southwester corn borer), (Earias spp.) (), (Earias insulata) (Egyptian bollworm), (Earias vit.ella) (rough northern bollworm), ecdytopopha aurantianum, (Elasmopalpus lignosellus) (lesser cornstalk borer), (Epiphysias postruttana) (light brown apple moth), (Ephestia spp.) (), (Ephestia cautella) (almond moth), (Ephestia elutella) ( (tobbaco moth)), </xnotran> <xnotran> (Ephestia kuehniella) (Mediterranean flour moth), epimeces (Epimeces spp.), (Epinotia aporema), (Erionota thrax) (banana skipper), (Eupoecilia ambiguella) ( (grape berry moth)), (Euxoa auxiliaris) (army cutworm), (Feltia spp.) (), (Gortyna spp.) (), (Grapholita molesta) ( () (oriental fruit moth)), (Hedylepta indicata) ( (bean leaf webber)), (Helicoverpa spp.) (), (Helicoverpa armigera) (cotton bollworm), (Helicoverpa zea) ( ( /)), (Heliothis spp.) (), (Heliothis virescens) (tobacco budworm), (Hellula undalis) (cabbage webworm), indarbela (Indarbela spp.) ( ), (Keiferia lycopersicella) (tomato pinworm), 8978 zxft 8978 (Leucinodes orbonalis) (eggplant fruit borer), (Leucoptera malifoliella), (Lithocollectis spp.), (Lobesia botrana) (grape fruit moth), </xnotran> Loxagrotis species (Loxagrotis spp.) (Noctuida), clanis bilineata (Loxagrotis albicostata) (western bean cuprum), lymantria dispar (Lymantria dispar) (gypsy moth), lyonectinatus (Lyonectinatus persica) (apple leaf miner), oil palm bag moth (Mahansera corbeti) (oil palm batum), astrotrichum species (Maliosoma spp.) (tent caterpillar), cabbage looper (Mahasen brassicus) (cabbage caterpillar (acanthaceae), bean pod moth (Maruca testula) (Bean webworm)), bean leaf moth (Metaplana platana) (Mesorethria punctata), mythimna unicolor (cabbage caterpillar), nepetula punctatus (tomato borer), cabbage caterpillar (Metaplexis) and tomato borer (tomato borer) in the genus stem borers (Nymphula deputylis) (rice leaf rollers (rice caseworms)), winter loopers (Operphthora brumata) (winter mood), european corn borers (Ostrinia nubilalis) (European corn borers (European corn borner)), oxydia vesulia, sinkiang brown moth (Pandemia cerasa) (common grape leaf moth (common currant trinx)), (ii) and (iii) the extract thereof apple leaf rollers (Pandemia (pandemic apple tritrix), african brake butterflies (Papilio demodicus), red bell moths (Pectinophora gossypiella) (pink bollworm), arctidium species (Peridroma spp.) (root cutting insects), mottled tigers (Peridroma saucia) (variegated cutworm), coffee leaf miners (Periluroptera coffealla) (white coffee leaf rollers), potato tuber moth (Phthalmia opuercula) (potatoo tuber moth), citrus leaf latent moth (Phylocnidis citrella), phylonica spp (Phylonoryces spp.) (leaf miner), cabbage butterfly (Pieri rapae) (imported cabbage worm (insect)), spodoptera frugiperda (Platyphana scabra), indian Gu Bane (Plodia interpunctella) (Indian meal moth), cabbage moth (Plutella xylostella) (diamondback moth), grape berry moth (polychloris virosa) (grape berry moth) (soybean meal moth), orange fruit moth (Prays endocarps), olive leaf moth (Prunus oleaudus) (olive moth), armyworm (Spodoptera), soybean leaf moth (soybean meal moth). Inchworm (Rachiplusia nu), borer (Scorpia incertulas), heliothis virescens (Heliothis pomonella spp.), heliothis virescens (stem borer), heliothis virescens (Sesamia infestans) (pink rice stem borer), heliothis virescens (Sesamia nonagrioides), heliothis virescens (Setora nitens), heliothis virescens (Sitotrogycephalella cerealis) (Angous grandiflora molh), graptopetra virescens (Spannothritis Pillera), heliothis virescens (Spodoptera spp.), spodoptera sp.Spodoptera (Spodoptera spp.), spodoptera exigua (Spodoptera armyworm) (northern armyworm), spodoptera frugiperda (southern armyworm) (southern armyworm (Spodoptera)) The species Spodoptera (Synanthondon spp.) (rootworm), therla basilides, thermia gemmatalis, chlamydia armyworm (Teneola bisseliella) (webbings moth), trichoplusia ni (cab looper), tephrosia lycopersicae (Tuts absoluta), phlebia species (Yonomeuta spp.), cochloae coffee moth (Zeuzeracoreae) (red branch borer) and Zeuzera pyrina (Leopard moths).
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) (mormons grasshopper (Mormon cricket)), mole cricket (Gryllotalpidae) (mole cricket), locusta migratoria (Locusta migratoria), grasshopper species (Melanoplus spp) (grasshopper), class wing spurs (Microcentrum retrierve) (angular wing species (Pterophylla) Pterophyta spp.) (Pterophyta spp.), stetoga vestocephala, scuder fusta (Scuder furdata) (forked tail bush (fork tailed bustympand)) and black corner locust (Vanilla ridge).
Phthiraptera (Phthiraptera) (sucking lice): the blood sucking lice species (haematoponus spp.) (cattle and pig lice), sheep jaw lice (linogluchus ovilus) (sheep lice), head lice (pediluus humanus capitis) (body lice), human body lice (pediluus humanus) (body lice) and crab lice (Pthirus pubis) (crab lice louse).
Siphonaptera (daphnaptera) (fleas): ctenocephalides canis (dog flea), ctenocephalides felis (cat flea) and human flea (Pulex irutans) (human flea).
Thysanoptera (thrips): tobacco brown Thrips (Frankliniella fusca) (tobaco third), frankliniella occidentalis (western flower), frankliniella shultzii (Frankliniella occidentalis), frankliniella wilsonii (Frankliniella williamsii) (corn Thrips), frankliniella glasshouse Thrips (IIelothrips haemopralidis) (grenenhouse third), riphithothrips cruentus, scirpus sp (Scrtothrips spp), platycodon grandiflorum (Scrtothricis) (citrus Thrips), tea yellow thistle (Scirnothia) (yellow tea leaf third), taennoththrips and Thrips (Thripp).
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)): <xnotran> 4736 zxft 4736 (Acarapsis woodi) ( (tracheal mite of honeybee)), (Acarus spp.) ( ), (Acarus siro) (8978 zxft 8978 (grain mite)), (Aceria mangiferae) (mango bud mite), (Aculops spp.), (Aculops lycopersici) (tomato russet mite), aculops pelekasi, (Aculus pelekassi), (Aculus schlechtendali) ( (apple rust mite)), (Amblyomma amcricanum) (lone star tick), (Boophilus spp.) (), (Brevipalpus obovatus) (privet mite), (Brevipalpus phoenicis) (red and black flat mite), (Demodex spp.) (mange mites), (Dermacentorspp.) ( ), (Dermacentor variabilis) (american dog tick), (Dermatophagoides pteronyssinus) (house dust mite), (Eotetranycus spp.), (Eotetranychus carpini) ( (yellow spider mite)), (Epitimerus spp.), (Eriophyes spp.), (; odes spp.) (), ((Metatetranycus spp.), (Notoedres cati), </xnotran> The species Pediobolus species (Oligonychus spp.), pediobolus coformis (Oligonychus coffee), pediobolus wintergreen (Oligonychus ilicalis (mites), pediobolus species (Panychus spp.), panonychus citri (Panychus citri) (citrus red mite), panonychus ulmi (Panychus ulmi) (European red mite), phyllostachys Purpurens (Phylloptera), rhynchophylla (Chlorococcus flavus) (citrus mite), tarsonemus laterosus (Polygonatum) (Tetranychus urticae (mite)), rhipicephalus rhynchophyllus (Rhipicus sanguineus) (brown mite), tetranychus urticae (Tetranychus urticae) (Tetranychus urticae (mite), tetranychus urticae (Tetranychus urticae), tetranychus urticae (Tetranychus urticae) and Tetranychus urticae (Tetranychus urticae) (Tetranychus urticae (Tetranychus sp).
Nematoda (nematodes): the species Aphelenchoides spp (bud and leaf and pine wood nematodes), the species Trichinella (Belolaimus spp.) (sting nematodes), the species Trichinella (Criconema spp.) (ring nematdes), dirofilaria immitis (dog heartworm), the species Dictylenchus spp.) (stem and bulb nematodes), the species Trichinella (Heterodera spp.) (Cytos nematodes), the species Heterodera (Heterodera cyst) (corn nematodes), the species Meloidogyne spp. (Hirschnella spp.) (Rotenodes) the species neozontalgia (endoplasmius spp.) (surface nematodes), meloidogyne species (Meloidogyne spp.) (root-knot nematodes), meloidogyne incognita (root-knot nematodes), circumflex (oncomelania volvulus) (hook-tail work), praLylenchus (pralylenus spp.) (decay nematodes), perforation (root-knot) species (perforation) and helicobactor (rotilenus reniformis) (kit-shaped-knot nematodes).
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 livestock of agricultural and horticultural importance, as well as the environment customary for humans, 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 (0.11 mol) formamidine acetate in 50mL of methanol was slowly added dropwise, while stirring at room temperature, a solution of 8.80g (0.16 mol) of sodium methoxide in methanol, and stirring was continued for 2 hours at room temperature after completion of the addition. Then, 11.17g (0.068 mol) 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 to remove the solvent, adjusting pH = 5-6 with hydrochloric acid, obtaining orange solid by suction filtration, extracting the water phase with (3X 50 ml) 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 (0.1 mol) 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 50 mL), the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and desolventized. The residue was chromatographed (eluent ethyl acetate and petroleum ether, vol. 1:5) to give 14.43g of yellow liquid in 88.5% yield.
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 phosphorus oxychloride (POCl) 3 ) 38ml of N, N-dimethylformamide was slowly dropped into the reaction flask at room temperature for about 30 minutes, and the dropping was completed. 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 mixture was poured into crushed ice and filtered to give 89.1g of a dark gray solid, 86.9% yield, 160-161 ℃ melting point.
Example 3: preparation of intermediate 4-chloroquinazoline
1) Preparation of quinazolin-4 (3H) -ones
Figure BDA0002445325790000471
13.7g (0.1 mol) 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 (0.1 mol) 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 (0.1 mol) of bromoethylamine bromate is put into 80mL of tetrahydrofuran, 10.08g (0.12 mol) of sodium bicarbonate and 50mL of water are sequentially added, 21.80g (0.1 mol) of di-tert-butyl dicarbonate is added dropwise under stirring at room temperature, and the reaction is continued for 4 to 10 hours after the dropwise addition is finished. After completion of the reaction, the solvent was distilled off under reduced pressure, ethyl acetate (3X 50 mL) was added for extraction, and the organic phase was washed with 50mL of saturated brine and then desolventized to give 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 (0.01 mol) of N-Boc-2-bromoethylamine and 1.94g (0.01 mol) of 1- (4-chlorophenyl) -1H-3-hydroxypyrazole (preparation method is referred to Organic Preparations and products International,34 (1), 98-102 2002) were added to 50mL of butanone, 2.76g (0.02 mol) of potassium carbonate was added, the mixture was heated to reflux with stirring, the reaction was carried out for 4-10 hours, after the completion of the TLC monitoring reaction, 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 the residue after the precipitation (eluent, ethyl acetate and petroleum ether, volume ratio 1:6) was obtained as a yellow solid, 2.73g, yield 81.1%.
3) Preparation of 2- (1- (4-chlorophenyl) -1H-pyrazol-3-oxy) ethylamine hydrochloride
Figure BDA0002445325790000475
3.37g (0.01 mol) 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 completion of the TLC monitoring reaction, the solvent was distilled off under reduced pressure, 10mL of dichloromethane was added with stirring 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 (0.01 mol) of 4-chloroquinazoline and 2.74g (0.01 mol) of 2- (1- (4-chlorophenyl) -1H-pyrazol-3-yloxy) ethylamine hydrochloride were added to 50ml of toluene. Adding 4.45g (0.022 mol) triethylamine, heating to reflux, reacting for 4-10 hr, monitoring by TLC, distilling off solvent under reduced pressure, adding (3X 50 mL) ethyl acetate for extraction, washing organic phase with 50mL saturated saline solution, subjecting to column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60)-90 ℃) in a volume ratio of 1:4) to yield 2.56g of a white solid with a yield of 70.1%. Melting point 176.4 ℃. 1 H NMR(600MHz,CDCl 3 )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 (0.002 mol) and triethylamine (0.004 mol) were added to 30mL of dichloromethane. Triphosgene (0.0024 mol) is added into the mixture in portions under stirring at room temperature, the reaction mixture is continuously heated and refluxed for 5 hours, after TLC monitoring the reaction is finished, the solvent is evaporated under reduced pressure, ethyl acetate (3X 30 mL) is added for extraction, an organic phase is washed by 50mL saturated saline solution, anhydrous magnesium sulfate is dried, and the residue after exsolution is subjected to column chromatography (eluent is ethyl acetate and petroleum ether (60-90 ℃) with the volume ratio of 1:4) to obtain 0.69g of light yellow liquid with the yield of 81.0 percent. Melting point 114.6 ℃. 1 H NMR(600MHz,CDCl 3 )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 (0.001 mol) and triethylamine (0.002 mol) were added to 30mL of dichloromethane. To this was added dropwise a solution of 20mL of 20-19 (0.001 mol) in dichloromethane with stirring at room temperature, the reaction mixture was allowed to react at room temperature for 3 hours, after completion of the reaction as monitored by TLC, the solvent was distilled off under reduced pressure, and ethyl acetate (3X 30 mL) was addedThe ester was extracted, and the organic phase was washed with 50mL of saturated brine, dried over anhydrous magnesium sulfate, and subjected to column chromatography (eluent composed of ethyl acetate and petroleum ether (60-90 ℃ C.) at a volume ratio of 1:4) to give 0.34g of a pale yellow liquid, with a yield of 79.5%. Melting Point 147.0 ℃. 1 H NMR(600MHz,CDCl 3 )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 ( 1 HNMR,300MHz, internal standard TMS, ppm) as follows:
compounds 12-2-19: 1 H NMR(600MHz,CDCl 3 )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: 1 H NMR(600MHz,CDCl 3 )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: 1 H NMR(600MHz,CDCl 3 )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: 1 H NMR(600MHz,CDCl 3 )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: 1 H NMR(600MHz,CDCl 3 )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: 1 H NMR(600MHz,CDCl 3 )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: 1 H NMR(600MHz,CDCl 3 )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: 1 H NMR(600MHz,CDCl 3 )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 ℃. 1 H 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 ℃. 1 H 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, melting point 144.1 ℃. 1 H 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 ℃. 1 H 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, mp 124.5 ℃. 1 H 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 ℃. 1 H 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 ℃. 1 H 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: 1 H NMR(600MHz,CDCl 3 )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: 1 H NMR(600MHz,CDCl 3 )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: a high-throughput screening method is adopted, namely 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) to prepare a liquid to be detected with the required concentration. Under an ultra-clean 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 dosage of 25ppm, the compounds with the inhibition rate of more than 80 percent on the rice blast comprise: 20-19, 20-1-19, 20-2-19, etc. The inhibition ratios of control agents 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 agents CK1, CK2, CK3, CK4 and CK5 on cucumber 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 compound sample to be detected 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, the volume ratio of the solvent amount to the liquid spraying amount is equal to or less than 0.05), and the solution to be detected is prepared by diluting with water containing 0.1 percent of Tween 80. The solution to be tested is sprayed on disease 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, the disease plants needing temperature control and moisture preservation culture are inoculated and then placed in an artificial climate chamber for culture, after the diseases are infected, the plants are moved into the greenhouse for culture, and the disease plants needing no moisture preservation culture are directly inoculated and cultured in the greenhouse. The compound disease control effect evaluation is carried out after the control is sufficiently ill (usually, one week).
The in vivo protective activity test results 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 and the like;
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 on 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:
the test compound was dissolved in a mixed solvent of acetone/methanol (1:1) and then diluted with water containing 0.1% (wt) tween 80 to the desired concentration.
The insecticidal activity is determined by taking diamondback moth and tetranychus cinnabarinus as targets and adopting an airrbrush spraying method.
(1) Activity measurement 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 ) The front and back of each leaf dishSpraying with a liquid spraying amount of 0.5ml. 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. After treatment, the mixture is placed into an observation room with the temperature of 25 ℃ and the relative humidity of 60-70% for culture, the number of the survival insects is investigated after 72 hours, and the death rate is calculated.
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 comprise: 20-1-19, 63-15, and the like.
(2) Activity measurement for killing tetranychus cinnabarinus
The measuring 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 0.5ml. 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.
The results of the partial tests 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 fatality 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 (7)

1. A substituted pyrazole compound containing pyrimidinamine is characterized in that: the compound is
Figure DEST_PATH_IMAGE001
-1B is represented by the general formula,
Figure 590065DEST_PATH_IMAGE002
in the formula:
R 3 selected from halogen, amino, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, di (halo C) 1 -C 4 Alkyl) amino, pyrazolyl;
R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 13 、R 14 、R 15 、R 16 are all selected from hydrogen;
R 10 selected from halogens;
n is an integer from 0 to 5;
w is selected from hydrogen.
2. The compound of claim 1, wherein: said general formula
Figure 635381DEST_PATH_IMAGE001
A compound represented by the formula (I) -1B, wherein
R 3 Selected from the group consisting of chloro, amino, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylaminoButylamino, isobutylamino, tert-butylamino, trifluoromethylamino, trifluoroethylamino, dimethylamino, diethylamino, pyrazolyl;
R 10 selected from fluorine, chlorine, bromine, iodine.
3. The compound of claim 2, wherein: a compound of the general formula I-1B, wherein
R 3 Selected from the group consisting of chloro, amino, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, dimethylamino, diethylamino, pyrazolyl.
4. A compound according to claim 3, characterized in that: a compound of the general formula I-1B, wherein
R 3 Selected 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, and pyrazolyl.
5. Use of the pyrimidine amine-containing substituted pyrazole compounds according to any one of claims 1 to 4 in the preparation of fungicides, insecticides and acaricides in agriculture or other fields.
6. 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-1B according to any one of claims 1 to 4, the composition containing 0.1 to 99% by weight of active ingredient.
7. Use of the composition according to claim 6 for the preparation of a medicament for controlling germs, pests and mites in agriculture or other fields.
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