CN109689644B - Pyridazinone compound and application thereof - Google Patents

Pyridazinone compound and application thereof Download PDF

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CN109689644B
CN109689644B CN201780051669.5A CN201780051669A CN109689644B CN 109689644 B CN109689644 B CN 109689644B CN 201780051669 A CN201780051669 A CN 201780051669A CN 109689644 B CN109689644 B CN 109689644B
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CN109689644A (en
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关爱莹
杨金龙
孙芹
孙旭峰
李志念
李慧超
夏晓丽
马森
杨帆
刘长令
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Abstract

The invention discloses a pyridazinone compound, which has a structure shown as a general formula I:

Description

Pyridazinone compound and application thereof
Technical Field
The invention belongs to the field of agricultural bactericides, and particularly relates to a pyridazinone compound and application thereof.
Background
Pyridaben [ test code: NC-129, NCI-129(both Nissan), BAS-300I (BASF), common names: pyridaben, trade name: sanmite (Nissan), agrimit (Sundat), Dinomite (Vapco), Pyrimite (Mobedco), Tarrantula (Baocheng) was reported by K.Hirata et al, and pyridazinone insecticidal and acaricidal agents were developed by Nissan chemical industry Co.
Figure GPA0000263312810000021
The chemical name is 2-tert-butyl-5- (4-tert-butyl benzylthio) -4-chloropyridazin-3(2H) -one. The English chemical name is 2-tert-butyl-5- (4-tert-butylbenzylthio) -4-chloropyridazin-3(2H) -one. CAS registry number [96489-71-3 ].
The crops are citrus, tea, cotton, vegetables, pear, hawthorn and ornamental plants. The pyridaben belongs to pyridazinone insecticide and acaricide, has no systemic property, and has the concentration of 5-20 g/hL or 100-300 kg/hm2The pesticide composition has excellent control effect on the pests of aleyrodids, aleyrodid, aphids, leafhopper and thysanoptera on fruit trees, vegetables, tea trees, tobaccos and ornamental plants. Effective against a series of mites including Tetranychus urticae, Tarsonemus tarsus and gall mite, and from egg, young mite, nymph mite to adult miteThe acaricide is effective in different growth periods, has a lasting period of 30-60 days, and has no cross resistance with common acaricides such as fenbutatin oxide, hexythiazox and the like.
In the prior art, the pyridazinone compound with the structure shown as the general formula I is not reported.
Disclosure of Invention
The invention aims to provide a pyridazinone compound and application thereof. The pyridazinone compound can effectively inhibit various germs, pests and mites, is particularly applied to preparation of medicines for preventing and treating germs, pests and mites in the agricultural field, and can improve the prevention and treatment effects of the medicines on plant germs, pests and mites.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a pyridazinone compound characterized by: the pyridazinone compound is a compound shown as a general formula I,
Figure GPA0000263312810000022
in the formula:
R1selected from hydrogen, C1-C12Alkyl radical, C3-C8Cycloalkyl, halo C1-C12Alkyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl, unsubstituted or substituted by 1-5R6Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R2、R3same or different and are respectively selected from hydrogen, hydroxyl, cyano, halogen and C1-C12Alkyl radical, C3-C8Cycloalkyl, haloC1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkylthio, halo C1-C12Alkylthio radical, C1-C12Alkylsulfinyl, halogeno C1-C12Alkylsulfinyl radical, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylcarbonyloxy, halo C1-C12Alkylcarbonyloxy, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R4selected from halogens;
R5selected from hydrogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy radical C1-C12Alkyl, hydroxy C1-C12Alkyl radical, C1-C12Alkenyl radical, C1-C12Alkynyl, C1-C12Alkoxycarbonyl radical C1-C12Alkyl or dimethylamino C1-C12An alkyl group;
R6selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, halo-di (C)1-C12Alkyl) amino, C (═ O) NR7R8、C1-C12Alkylthio, halo C1-C12Alkylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, C2-C12Alkenyloxy, halogeno C2-C12Alkenyloxy radical, C2-C12Alkynyloxy, halo C2-C12Alkynyloxy, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl, halo C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C1-C12Alkylthio carbonyl group C1-C12Alkyl, halo C1-C12Alkylthio carbonyl group C1-C12Alkyl radical, C1-C12Alkylcarbonyloxy, halo C1-C12Alkylcarbonyloxy, C1-C12Alkoxycarbonyloxy, halo C1-C12Alkoxycarbonyloxy, C1-C12Alkylsulfonyloxy, halo C1-C12Alkylsulfonyloxy, C1-C12Alkoxy radical C1-C12Alkoxy or halo C1-C12Alkoxy radical C1-C12An alkoxy group;
R7、R8same or different, are respectively selected from hydrogen and C1-C12Alkyl or halo C1-C12An alkyl group;
x is selected from NR9O or S;
l is a bond, C1-C2Straight saturated alkyl chain, C3-C12Straight saturated alkyl chain, C1-C12Straight unsaturated alkyl chain, C1-C12Branched saturated alkyl chain or C1-C12A branched unsaturated alkyl chain;
w is selected from the group consisting of a bond, NR9O, S or a carbonyl group; and when L and W are both selected from the group consisting of a bond, X is directly attached to the pyrazole ring;
R9selected from hydrogen, hydroxy, formyl, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C8Cycloalkyl radical, C1-C12Alkylthio radical, C2-C12Alkenylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, halo C2-C12Alkenyl, halo C2-C12Alkynyl, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkylsulfinyl, halogeno C1-C12Alkylsulfinyl radical, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylaminosulfonyl, di (C)1-C12Alkyl) aminosulfonyl, C1-C12Alkylsulfonylaminocarbonyl group, C1-C12Alkylcarbonylaminosulfonyl radical, C3-C12Cycloalkyloxycarbonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkyl carbonyl radical C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C1-C12Alkylaminocarbonyl, di (C)1-C12Alkyl) aminocarbonyl, C2-C12Alkenyloxycarbonyl radical, C2-C12Alkynyloxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkoxycarbonyl group, C1-C12Alkylaminosulfenyl, di (C)1-C12Alkyl) aminothio, arylcarbonyl C unsubstituted or substituted by 1 to 51-C6Alkyl, arylcarbonyl, aryloxycarbonyl, aryl C1-C6Alkyloxycarbonyl, aryl C1-C6Alkyl, heteroaryl carbonyl C1-C6Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, wherein the following groups are halogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group.
In the pyridazinone compounds of the present invention, more preferable compounds include: in the general formula I:
R1selected from hydrogen, C1-C8Alkyl radical, C3-C6Cycloalkyl, halo C1-C8Alkyl radical, C1-C8Alkylcarbonyl, halo C1-C8Alkylcarbonyl group, C1-C8Alkylsulfonyl, halo C1-C8Alkylsulfonyl radical, C1-C8Alkoxycarbonyl group, C1-C8Alkoxy radical C1-C8Alkyl radical, C1-C8Alkoxycarbonyl radical C1-C8Alkyl, unsubstituted or substituted by 1-5R6Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R2、R3same or different and are respectively selected from hydrogen, hydroxyl, cyano, halogen and C1-C8Alkyl radical, C3-C6Cycloalkyl, haloC1-C8Alkyl radical, C1-C8Alkoxy, halo C1-C8Alkoxy radical, C1-C8Alkylcarbonyl, halo C1-C8Alkylcarbonyl group, C1-C8Alkylthio, halo C1-C8Alkylthio radical, C1-C8Alkylsulfinyl, halogeno C1-C8Alkylsulfinyl radical, C1-C8Alkylsulfonyl, halo C1-C8Alkylsulfonyl radical, C1-C8Alkylcarbonyloxy, halo C1-C8Alkylcarbonyloxy, C1-C8Alkoxycarbonyl, halo C1-C8Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R4selected from halogens;
R5selected from hydrogen, C1-C8Alkyl, halo C1-C8Alkyl radical, C1-C8Alkoxy radical C1-C8Alkyl, hydroxy C1-C8Alkyl radical, C1-C8Alkenyl radical, C1-C8Alkynyl, C1-C8Alkoxycarbonyl radical C1-C8Alkyl or dimethylamino C1-C8An alkyl group;
R6selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C8Alkyl, halo C1-C8Alkyl radical, C1-C8Alkoxy, halo C1-C8Alkoxy radical, C3-C8Cycloalkyl radical, C1-C8Alkylamino, halogeno C1-C8Alkylamino radical, di (C)1-C8Alkyl) amino, halo-di (C)1-C8Alkyl) amino, C (═ O) NR7R8、C1-C8Alkylthio, halo C1-C8Alkylthio radical, C2-C8Alkenyl radical, C2-C8Alkynyl, C2-C8Alkenyloxy, halogeno C2-C8Alkenyloxy radical, C2-C8Alkynyloxy, halo C2-C8Alkynyloxy, C1-C8Alkylsulfonyl, halo C1-C8Alkylsulfonyl radical, C1-C8Alkylcarbonyl, halo C1-C8Alkylcarbonyl group, C1-C8Alkoxycarbonyl, halo C1-C8Alkoxycarbonyl group, C1-C8Alkoxy radical C1-C8Alkyl, halo C1-C8Alkoxy radical C1-C8Alkyl radical, C1-C8Alkylthio group C1-C8Alkyl, halo C1-C8Alkylthio group C1-C8Alkyl radical, C1-C8Alkoxycarbonyl radical C1-C8Alkyl, halo C1-C8Alkoxycarbonyl radical C1-C8Alkyl radical, C1-C8Alkylthio carbonyl group C1-C8Alkyl, halo C1-C8Alkylthio carbonyl group C1-C8Alkyl radical, C1-C8Alkylcarbonyloxy, halo C1-C8Alkylcarbonyloxy, C1-C8Alkoxycarbonyloxy, halo C1-C8Alkoxycarbonyloxy, C1-C8Alkylsulfonyloxy, halo C1-C8Alkylsulfonyloxy, C1-C8Alkoxy radical C1-C8Alkoxy or halo C1-C8Alkoxy radical C1-C8An alkoxy group;
R7、R8same or different, are respectively selected from hydrogen and C1-C8Alkyl or halo C1-C8An alkyl group;
x is selected from NR9O or S;
l is a bond, C1-C2Straight saturated alkyl chain, C3-C8Straight saturated alkyl chain, C1-C8A straight chain unsaturated alkyl chain,C1-C8Branched saturated alkyl chain or C1-C8A branched unsaturated alkyl chain;
w is selected from the group consisting of a bond, NR9O, S or a carbonyl group;
R9selected from hydrogen, hydroxy, formyl, C1-C8Alkyl, halo C1-C8Alkyl radical, C1-C8Alkoxy, halo C1-C8Alkoxy radical, C3-C6Cycloalkyl radical, C1-C8Alkylthio radical, C2-C8Alkenylthio radical, C2-C8Alkenyl radical, C2-C8Alkynyl, halo C2-C8Alkenyl, halo C2-C8Alkynyl, C1-C8Alkoxy radical C1-C8Alkyl, halo C1-C8Alkoxy radical C1-C8Alkyl radical, C1-C8Alkylthio group C1-C8Alkyl, halo C1-C8Alkylthio group C1-C8Alkyl radical, C1-C8Alkylsulfinyl, halogeno C1-C8Alkylsulfinyl radical, C1-C8Alkylsulfonyl, halo C1-C8Alkylsulfonyl radical, C1-C8Alkylaminosulfonyl, di (C)1-C8Alkyl) aminosulfonyl, C1-C8Alkylsulfonylaminocarbonyl group, C1-C8Alkylcarbonylaminosulfonyl radical, C3-C8Cycloalkyloxycarbonyl radical, C1-C8Alkylcarbonyl, halo C1-C8Alkylcarbonyl group, C1-C8Alkoxycarbonyl, halo C1-C8Alkoxycarbonyl group, C1-C8Alkyl carbonyl radical C1-C8Alkyl radical, C1-C8Alkoxycarbonyl radical C1-C8Alkyl radical, C1-C8Alkylaminocarbonyl, di (C)1-C8Alkyl) aminocarbonyl, C2-C8Alkenyloxycarbonyl radical, C2-C8Alkynyloxycarbonyl group, C1-C8Alkoxy radical C1-C8Alkoxycarbonyl group, C1-C8Alkylaminosulfenyl, di (C)1-C8Alkyl) aminothio, arylcarbonyl C unsubstituted or substituted by 1 to 51-C6Alkyl, arylcarbonyl, aryloxycarbonyl, aryl C1-C6Alkyloxycarbonyl, aryl C1-C6Alkyl, heteroaryl carbonyl C1-C6Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaryl C1-C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyl, wherein the following groups are halogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group.
Further optional compounds in the pyridazinone compounds of the present invention include: in the general formula I shown in the specification,
R1selected from hydrogen, C1-C4Alkyl radical, C3-C4Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, unsubstituted or substituted by 1-5R6Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R2、R3same or different and are respectively selected from hydrogen, hydroxyl, cyano, halogen and C1-C4Alkyl radical, C3-C4Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R4selected from halogens;
R5selected from hydrogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy radical C1-C4Alkyl, hydroxy C1-C4Alkyl radical, C1-C4Alkenyl radical, C1-C4Alkynyl, C1-C4Alkoxycarbonyl radical C1-C4Alkyl or dimethylamino C1-C4An alkyl group;
R6selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C2-C4Alkenyloxy, halogeno C2-C4Alkenyloxy radical, C2-C4Alkynyloxy, haloGeneration C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8same or different, are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
x is selected from NR9O or S;
l is a bond, C1-C2Straight saturated alkyl chain, C3-C4Straight saturated alkyl chain, C1-C4Straight unsaturated alkyl chain, C1-C4Branched saturated alkyl chain or C1-C4A branched unsaturated alkyl chain;
w is selected from the group consisting of a bond, NR9O, S orA carbonyl group;
R9selected from hydrogen, hydroxy, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylaminosulfonyl, di (C)1-C4Alkyl) aminosulfonyl, C1-C4Alkylsulfonylaminocarbonyl group, C1-C4Alkylcarbonylaminosulfonyl radical, C3-C4Cycloalkyloxycarbonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkyl carbonyl radical C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylaminocarbonyl, di (C)1-C4Alkyl) aminocarbonyl, C2-C4Alkenyloxycarbonyl radical, C2-C4Alkynyloxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkoxycarbonyl group, C1-C4Alkylaminosulfenyl, di (C)1-C4Alkyl) aminosulfanyl, unsubstituted or interrupted by 1 to 5One-step substituted arylcarbonyl group C1-C4Alkyl, arylcarbonyl, aryloxycarbonyl, aryl C1-C4Alkyloxycarbonyl, aryl C1-C4Alkyl, heteroaryl carbonyl C1-C4Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaryl C1-C4Alkyloxycarbonyl, heteroaryl C1-C4Alkyl, wherein the following groups are halogen, nitro, cyano, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group.
In the pyridazinone compounds, still further optional compounds are compounds shown as a general formula I, namely compounds shown as general formulas I-A, I-B, I-C, I-A ', I-B', I-C ', I-D, I-E, I-F, I-G, I-H, I-I, I-J, I-K, I-L, I-M, I-N, I-O, I-P, I-Q, I-R, I-S, I-T, I-U, I-V, I-W, I-X, I-Y, I-Z or I-Q',
Figure GPA0000263312810000051
Figure GPA0000263312810000061
Figure GPA0000263312810000071
wherein the content of the first and second substances,
R4selected from halogens;
R5selected from hydrogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy radical C1-C4Alkyl, hydroxy C1-C4Alkyl radical, C1-C4Alkenyl radical, C1-C4Alkynyl, C1-C4Alkoxycarbonyl radical C1-C4Alkyl or dimethylamino C1-C4An alkyl group;
R6selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio or halogeno C1-C4An alkylthio group; n is 0 to 3;
l is a bond, C1-C2Straight saturated alkyl chain, C3-C4Straight saturated alkyl chain or C1-C4A branched saturated alkyl chain;
R9selected from hydrogen, formyl, C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Alkoxy radical C1-C4Alkyl, benzoyl or benzyl;
y is selected from CH or N;
R10、R11each independently selected from hydrogen or C1-C4An alkyl group;
and in I-D, I-E, I-F, I-G, I-H, I-I, I-P, I-Q, I-R, I-V, I-W, I-X, I-Y and I-Z, R is1Selected from hydrogen, C1-C4Alkyl radical, C3-C4Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy radical C1-C4Alkyl, unsubstituted or substituted by 1-5R6Substituted aryl, heteroaryl, arylmethyl or heteroarylmethyl;
in I-A, I-B, I-C, I-A ', I-B', I-C ', I-G, I-H, I-I, I-J, I-K, I-L, I-M, I-N, I-O, I-P, I-Q, I-R, I-S, I-T, I-U, I-V, I-W, I-X, I-Y, I-Z and I-Q', R is2Selected from hydrogen, hydroxy, cyano, halogen, C1-C4Alkyl radical, C3-C4Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkylthio, haloC1-C4Alkylthio radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, heteroaryl, arylmethyl or heteroarylmethyl;
in I-A, I-B, I-C, I-A ', I-B', I-C ', I-D, I-E, I-F, I-J, I-K, I-L, I-M, I-N, I-O, I-S, I-T, I-U and I-Q', R is3Selected from hydrogen, hydroxy, cyano, halogen, C1-C4Alkyl radical, C3-C4Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, heteroaryl, arylmethyl or heteroarylmethyl.
In the pyridazinone compounds, further optional compounds are compounds shown as general formulas I-A, I-B, I-C, I-A ', I-B', I-C ', I-D, I-E, I-F, I-G, I-H, I-I, I-J, I-K, I-L, I-M, I-N, I-O, I-P, I-Q, I-R, I-S, I-T, I-U, I-V, I-W, I-X, I-Y, I-Z or I-Q':
R1selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, heptafluoroisopropyl, tert-butyl, trifluoromethyl, and mixtures thereof,Methoxymethyl, methoxyethyl, ethoxymethyl, unsubstituted or substituted by 1-5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R2、R3identical or different from hydrogen, hydroxy, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, heptafluoroisopropyl, methoxy, ethoxy, trifluoroethoxy, formyl, trifluoroacetyl, methylthio, ethylthio, trifluoromethylthio, methylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl, methoxycarbonyl, trifluoromethoxy carbonyl, unsubstituted or substituted by 1 to 5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R4selected from fluorine, chlorine, bromine or iodine;
R5selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, heptafluoroisopropyl, methoxymethyl, methoxyethyl, ethoxymethyl, hydroxyethyl, allyl, propargyl, methoxycarbonylmethyl or dimethylaminomethyl;
R6selected from fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, monofluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, heptafluoroisopropyl, methoxy, ethoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio or trifluoromethylthio; n is 0 to 3;
l is a bond, CH2、CH(CH3)、CH2CH2、CH(CH3)CH2、CH2CH2CH2、CH(CH3)CH2CH2、CH2CH＝CHCH2Or CH2C≡CCH2；
R9Selected from hydrogen;
y is selected from CH or N;
R10、R11each independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
In the pyridazinone compounds of the present invention, more optional compounds are those represented by the general formula I-A, I-B, I-C, I-A ', I-B', I-C ', I-K, I-L, I-N, I-O, I-Q, I-R or I-Q':
R1hydrogen, methyl, ethyl, isopropyl or tert-butyl;
R2、R3the same or different, are respectively selected from hydrogen, methyl or ethyl;
R4selected from chlorine or bromine;
R5selected from hydrogen, methyl, isopropyl or tert-butyl;
R6fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, trichloromethyl, methoxy or trifluoromethoxy; n is 0 to 3;
l is a bond, CH2、CH(CH3) Or CH2CH2；
R9Selected from hydrogen;
y is selected from CH or N;
R10、R11are all selected from hydrogen.
The most preferable compound in the pyridazinone compound of the present invention is the compound represented by the general formula I-A, I-B, I-C, I-N, I-O, I-Q or I-R:
R1hydrogen, methyl, ethyl, isopropyl or tert-butyl;
R2、R3the same or different, are respectively selected from hydrogen, methyl or ethyl;
R4selected from chlorine or bromine;
R5selected from hydrogen, methyl, isopropyl or tert-butyl;
R6fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, trichloromethyl, methoxy or trifluoromethoxy; n is 0 to 3;
l is a bond, CH2、CH(CH3) Or CH2CH2；
R9Selected from hydrogen;
y is selected from CH or N.
The application of the pyridazinone compound shown in the general formula I in preparing bactericides, insecticides and acaricides in agriculture or other fields.
The pyridazinone compound shown in the general formula I is used as an active component in the composition; wherein, the weight percentage of the active components in the composition is 0.1 to 99 percent.
The application of the composition in preventing and controlling germs, pests and mites in agriculture or other fields.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
bond: means that two atoms or groups are directly linked (if L is selected from a bond, then X and W are directly linked together, and if L and W are both a bond, then X is directly linked to the pyrazole ring). When the halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl groups: straight-chain or branched alkyl groups, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl groups: substituted or unsubstituted cyclic alkyl groups, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, and the like. Halogenated alkyl groups: straight-chain or branched alkyl groups in which the hydrogen atoms may be partially or completely substituted with halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl and the like. 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 orA branched alkylsulfonyl group in which the hydrogen atoms of the alkyl group may be partially or completely substituted by halogen atoms. Alkylaminosulfenyl: such as CH3NHS-、C2H5NHS-. Dialkylaminosulfenyl: such as (CH)3)2NS-、(C2H5)2NS-. Alkylaminosulfonyl: alkyl-NH-SO2-. Dialkylaminosulfonyl: (alkyl group)2-N-SO2-. Alkylsulfonylaminocarbonyl group: alkyl-SO2-NH-CO-. Alkylcarbonylaminosulfonyl: alkyl-CO-NH-SO2-. Alkylcarbonylalkyl group: alkyl-CO-alkyl-. Alkylsulfonyloxy group: alkyl-S (O)2-O-. Haloalkylsulfonyloxy: the hydrogen atoms of the alkyl group of the alkylsulfonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF3-SO2-O. 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. ClCH2CH2OCO-、CF3CH2OCO-, etc. Alkoxyalkyl groups: alkyl-O-alkyl-, e.g. CH3OCH2-. Haloalkoxyalkyl groups: the hydrogen atoms of the alkyl groups of alkoxyalkyl groups may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2OCH2-、CF3CH2OCH2-and the like. Alkoxycarbonylalkyl groups: alkoxycarbonyl-alkyl-, e.g. CH3OCOCH2-. Haloalkoxycarbonylalkyl: the hydrogen atoms of the alkyl group of the alkoxycarbonylalkyl group may be partially or fully substituted by halogen atoms, e.g. CF3CH2OCOCH2-. Alkylcarbonyloxy group: such as CH3COO-, etc. Haloalkylcarbonyloxy: the hydrogen atoms of the alkylcarbonyloxy group may be partially or wholly replaced by halogen atomsSubstituted, e.g. CF3COO-, etc. Alkoxycarbonyloxy: alkoxycarbonyl-oxy-, e.g. CH3OCOO-. Haloalkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF3OCOO-. Alkylthio-carbonylalkyl: alkylthiocarbonyl-alkyl-, e.g. CH3SCOCH2-. Haloalkylthiocarbonylalkyl: the hydrogen atoms of the alkyl group of the alkylthiocarbonylalkyl group may be partially or wholly substituted by halogen atoms, e.g. CF3CH2SCOCH2-. Alkoxyalkoxy group: such as CH3OCH2O-, etc. Haloalkoxyalkyl: the hydrogen atoms of the alkoxy groups being partially or wholly replaced by halogen atoms, e.g. CF3OCH2O-is formed. Alkoxy alkoxycarbonyl group: such as CH3OCH2CH2OCO-, etc. Alkylthio group: straight or branched chain alkyl groups attached to the structure via a sulfur atom. Haloalkylthio: straight-chain or branched alkylthio groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like. Alkylthioalkyl: alkyl-S-alkyl-, e.g. CH3SCH2-. Haloalkylthioalkyl: the hydrogen atoms of the alkyl group of an alkylthioalkyl group may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2SCH2-、CF3CH2SCH2-and the like. Alkylamino group: straight or branched chain alkyl, linked to the structure via a nitrogen atom. Haloalkylamino group: straight-chain or branched alkylamino groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms. Dialkylamino group: such as (CH)3)2N-、(CH3CH2)2N-is provided. Halogenated dialkylamino group: the hydrogen atoms of the alkyl groups being partially or wholly replaced by halogen atoms, e.g. (CF)3)2N-、(CF3CH2)2N-is provided. Alkenyl: straight-chain or branched alkenes, for example ethenyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes, such as 1, 2-alleneAnd 2, 4-hexadienyl. Halogenated alkenyl groups: straight-chain or branched alkenes in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenyloxy: linear or branched alkenes linked to the structure via oxygen atoms. Haloalkenyloxy: straight-chain or branched alkenyloxy groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenylthio group: linear or branched alkenes linked to the structure via a sulfur atom bond. Such as CH2＝CHCH2S-. Alkenyloxycarbonyl radical: such as CH2＝CHCH2OCO-, etc. Alkynyl: straight-chain or branched alkynes, for example ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. Alkynyl also includes groups consisting of multiple triple bonds, such as 2, 5-hexadiynyl. Halogenated alkynyl group: straight-chain or branched alkynes, 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 ≡ CCH2OCO-, etc. An alkylsulfonyl group: straight or branched chain alkyl via sulfonyl (-SO)2-) is attached to a structure, such as a methylsulfonyl group. Haloalkylsulfonyl group: straight-chain or branched alkylsulfonyl wherein the hydrogen atoms of the alkyl group may be partially or wholly substituted by halogen atoms. An alkylcarbonyl group: the alkyl radical being bound to the structure via a carbonyl group, e.g. CH3CO-，CH3CH2CO-. Halogenated alkylcarbonyl group: the hydrogen atoms of the alkyl group of the alkylcarbonyl group may be partially or fully substituted by halogen atoms, e.g. CF3CO-. Alkoxycarbonyl group: the alkoxy group is attached to the structure via a carbonyl group. Such as CH3OCO-、CH3CH2OCO-. Aminocarbonyl group: such as NH2CO-. Alkyl amino carbonyl: alkyl-NH-CO-, e.g. CH3NHCO-、CH3CH2NHCO-. Dialkylaminocarbonyl group: such as (CH)3)2NCO-、(CH3CH2)2NCO-. (hetero) aryl, (hetero) arylalkyl, (hetero) arylcarbonyl, (hetero) arylmethylcarbonyl, (hetero) arylcarbonylalkyl, (hetero) aryloxycarbonyl, (hetero) arylalkyloxyThe aryl moiety in the carbonyl group includes phenyl, naphthyl, or the like. Heteroaryl is a five or six membered ring containing 1 or more heteroatoms N, O, S. Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and the like. (hetero) aryl group: such as phenyl, and the like. (hetero) arylalkyl: such as benzyl, phenethyl, p-chlorobenzyl, 2-chloropyridin-5-yl, 2-chloro-thiazol-5-yl, and the like. (hetero) arylcarbonyl group: such as benzoyl, 4-chlorobenzoyl and the like. (hetero) arylmethylcarbonyl: such as PhCH2CO-. (hetero) arylcarbonylalkyl: such as PhCOCH2-. (hetero) aryloxycarbonyl group: such as phenoxycarbonyl, 4-chlorophenoxycarbonyl, 4-nitrophenoxycarbonyl, naphthyloxycarbonyl, etc. Arylalkyloxycarbonyl group: such as benzyloxycarbonyl, 4-chlorobenzyloxycarbonyl, 4-trifluoromethylbenzyloxycarbonyl and the like. (hetero) arylalkyloxycarbonyl: such as PhCH2OCO-、4-Cl-PhCH2OCO-, etc.
The following tables 1, 2 and 3 respectively show R in the general formula I1、R2(R3)、R9The moiety (c) is not limited to these substituents.
Figure GPA0000263312810000101
TABLE 1R1Substituent group
Figure GPA0000263312810000111
Figure GPA0000263312810000121
TABLE 2R2(R3) Substituent group
Figure GPA0000263312810000122
Figure GPA0000263312810000131
TABLE 3R9Substituent group
Figure GPA0000263312810000132
Figure GPA0000263312810000141
Some of the compounds of the present invention can be illustrated by the specific compounds listed in tables 4 to 339, but are not intended to limit the present invention.
In the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝H，Y＝CH，R9When (R) is H6) The substituent of n is shown in Table 4, and represents the compound number of 4-1-4-279 in sequence.
Figure GPA0000263312810000142
TABLE 4
Figure GPA0000263312810000143
Figure GPA0000263312810000151
Figure GPA0000263312810000161
Figure GPA0000263312810000171
Table 5: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 5-1-5-279 in this order.
Table 6: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 6-1-6-279 in this order.
Table 7: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 7-1-7-279 in this order.
Table 8: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 8-1-8-279 in this order.
Table 9: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 9-1-9-279 in sequence.
Table 10: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 10-1-10-279 in this order.
Table 11: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 4 and represents a compound number of 1 in the order1-1-11-279。
Table 12: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 12-1-12-279 in this order.
Table 13: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 13-1-13-279 in sequence.
Table 14: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 14-1-14-279 in sequence.
Table 15: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 15-1-15-279 in this order.
Table 16: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 16-1-16-279 in this order.
Table 17: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 17-1-17-279 in sequence.
Table 18: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 18-1-18-279 in this order.
Table 19: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 19-1-19-279 in sequence.
Table 20: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 20-1-20-279 in sequence.
Table 21: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 21-1-21-279 in sequence.
Table 22: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 22-1-22-279 in this order.
Table 23: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 23-1-23-279 in sequence.
Table 24: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 24-1-24-279 in this order.
Table 25: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 25-1-25-279 in this order.
Table 26: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 26-1-26-279 in sequence.
Table 27: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 27-1-27-279 in this order.
Table 28: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 28-1-28-279 in this order.
Table 29: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 29-1-29-279 in this order.
Table 30: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 4 and representsThe compound numbers are 30-1-30-279 in sequence.
Table 31: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 31-1-31-279 in sequence.
Table 32: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 32-1-32-279 in this order.
Table 33: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 33-1-33-279 in this order.
Table 34: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 34-1-34-279 in sequence.
Table 35: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 35-1-35-279 in this order.
Table 36: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 36-1-36-279 in this order.
Table 37: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 37-1-37-279 in sequence.
Table 38: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 38-1-38-279 in this order.
Table 39: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 39-1-39-279 in sequence.
Table 40: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 40-1-40-279 in this order.
Table 41: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 41-1-41-279 in this order.
Table 42: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 42-1-42-279 in sequence.
Table 43: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 43-1-43-279 in this order.
Table 44: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 44-1-44-279 in this order.
Table 45: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 45-1-45-279 in this order.
Table 46: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 46-1-46-279 in this order.
Table 47: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 47-1-47-279 in sequence.
Table 48: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 48-1-48-279 in this order.
Table 49: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 49-1-49-279 in this order.
Table 50: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 50-1 to 50-279 in this order.
Table 51: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 51-1-51-279 in this order.
Table 52: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 52-1-52-279 in sequence.
Table 53: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 53-1-53-279 in this order.
Table 54: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 54-1-54-279 in sequence.
TABLE 55-1: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 55-1-1-55-1-279 in sequence.
In the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝H，Y＝N，R9When (R) is H6) The substituent n is shown in Table 55, and represents the compound number of 55-1-55-9 in sequence.
Figure GPA0000263312810000191
Watch 55
No. (R6)n No. (R6)n No. (R6)n
55-1 3-Cl 55-2 5-Cl 55-3 3，5-diCl
55-4 5-CF3 55-5 3-Cl-5-CF3 55-6 5-CH3
55-7 5-CN 55-8 5-Br 55-9 3，5，6-triCl
Table 56: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers in the order of 56-1 to 56-9.
Table 57: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 57-1 to 57-9 in this order.
Table 58: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 58-1 to 58-9 in this order.
Table 59: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝H，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 59-1 to 59-9 in this order.
Table 60: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 60-1 to 60-9 in this order.
Table 61: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 61-1 to 61-9 in this order.
Table 62: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝t-Bu，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 62-1 to 62-9 in this order.
Table 63: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝H，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 63-1 to 63-9 in this order.
Table 64: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 64-1 to 64-9 in this order.
Table 65: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 65-1 to 65-9 in this order.
Table 66: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers 66-1 to 66-9 in this order.
Table 67: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝H，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers 67-1 to 67-9 in this order.
Table 68: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 68-1 to 68-9 in this order.
Table 69: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 69-1 to 69-9 in this order.
Table 70: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝t-Bu，Y＝N，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 70-1 to 70-9 in this order.
In the general formula I-A', when R is10＝R11When H is used, some specific compounds can be shown in table 7-1, table 11-1, table 15-1, and table 19-1.
Figure GPA0000263312810000201
Table 7-1: in the general formula I-A', when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 4 and represents the compound number of7-1-1-7-1-279。
Table 11-1: in the general formula I-A', when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 11-1-1-11-1-279 in sequence.
Table 15-1: in the general formula I-A', when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 15-1-1-15-1-279 in sequence.
Table 19-1: in the general formula I-A', when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 19-1-1-19-1-279 in sequence.
In the general formula I-B, some specific compounds can be shown in tables 71-138.
Figure GPA0000263312810000202
Table 71: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 71-1-71-279 in sequence.
Table 72: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 72-1-72-279 in sequence.
Table 73: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 73-1-73-279 in sequence.
Table 74: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 74-1-74-279 in sequence.
Table 75: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 75-1-75-279 in this order.
Table 76: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 76-1-76-279 in this order.
Table 77: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 77-1-77-279 in this order.
Table 78: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 78-1-78-279 in this order.
Table 79: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 79-1-79-279 in sequence.
Table 80: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is in accordance with the substituents shown in table 4,the representative compound numbers are 80-1-80-279 in sequence.
Table 81: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 81-1-81-279 in sequence.
Table 82: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 82-1-82-279 in sequence.
Table 83: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When H, Y ═ CH substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 83-1-83-279 in sequence.
Table 84: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 84-1-84-279 in sequence.
Table 85: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 85-1-85-279 in sequence.
Table 86: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 86-1-86-279 in sequence.
Table 87: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When H, Y, CH, are substitutedRadical (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 87-1-87-279 in turn.
Table 88: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 88-1-88-279 in sequence.
Table 89: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound with the number of 89-1-89-279 in sequence.
Table 90: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 90-1 to 90-279 in this order.
Table 91: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 91-1-91-279 in sequence.
Table 92: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 92-1-92-279 in this order.
Table 93: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 93-1-93-279 in this order.
Table 94: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 94-1-94-279 in this order.
Table 95: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 95-1-95-279 in this order.
Table 96: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 96-1-96-279 in this order.
Table 97: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 97-1-97-279 in turn.
Table 98: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 98-1-98-279 in sequence.
Table 99: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 99-1-99-279 in sequence.
Table 100: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 100-1-100-279 in sequence.
Table 101: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 101-1-101-279 in sequence.
Table 102: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 102-1-102-279 in sequence.
Table 103: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 103-1-103-279 in sequence.
Table 104: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 104-1-104-279 in sequence.
Table 105: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 105-1-105-279 in sequence.
Table 106: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 106-1-106-279 in sequence.
Table 107: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When H, Y, CH,substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 107-1-107-279 in sequence.
Table 108: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 108-1-108-279 in sequence.
Table 109: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is the same as in Table 4 and represents the compound numbers 109-1-109-279 in this order.
Table 110: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 110-1-110-279 in sequence.
Table 111: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 111-1-111-279 in sequence.
Table 112: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 112-1-112-279 in sequence.
Table 113: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 113-1-113-279 in sequence.
Table 114: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 114-1-114-279 in sequence.
Table 115: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 115-1-115-279 in sequence.
Table 116: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 116-1-116-279.
Table 117: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 117-1-117-279 in sequence.
Table 118: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 118-1-118-279 in sequence.
Table 119: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 119-1-119-279 in sequence.
Table 120: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 120-1-120-279 in sequence.
Table 121: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 121-1-121-279 in sequence.
Table 122: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 122-1-122-279 in sequence.
Table 123: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When H, Y, N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 123-1 to 123-9 in this order.
Table 124: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers 124-1 to 124-9 in this order.
Table 125: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 125-1 to 125-9 in this order.
Table 126: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-N, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers 126-1 to 126-9 in this order.
Table 127: in the general formula I-BWhen R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, Y, N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers 127-1 to 127-9 in this order.
Table 128: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 128-1 to 128-9 in this order.
Table 129: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 129-1 to 129-9 in this order.
Table 130: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-N, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 130-1 to 130-9 in this order.
Table 131: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, Y, N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 131-1 to 131-9 in this order.
Table 132: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers 132-1 to 132-9 in this order.
Table 133: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 133-1 to 133-9 in this order.
Table 134:in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-N, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 134-1 to 134-9 in this order.
Table 135: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When H, Y, N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 135-1 to 135-9 in this order.
Table 136: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When Y is N, a substituent (R)6) n is in accordance with the substituent shown in Table 55 and represents the compound number of 136-1 to 136-9 in this order.
Table 137: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 137-1 to 137-9 in this order.
Table 138: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-N, the substituent (R)6) n is in accordance with the substituent shown in Table 55 and represents the compound number of 138-1 to 138-9 in this order.
In the general formula I-B', when R is10＝R11When H is used, some specific compounds can be shown in tables 74-1, 78-1, 82-1 and 86-1.
Figure GPA0000263312810000241
TABLE 74-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n and the substituents shown in Table 4Consistently, the representative compound numbers are 74-1-1-74-1-279 in order.
TABLE 78-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 78-1-1-78-1-279 in sequence.
TABLE 82-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 82-1-1-82-1-279 in sequence.
TABLE 86-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 86-1-1-86-1-279 in sequence.
In formulas I-C, some of the specific compounds can be illustrated in tables 139-206.
Figure GPA0000263312810000242
Table 139: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 139-1-139-279 in sequence.
Table 140: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 140-1-140-279 in sequence.
Table 141: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is as in Table 4The substituents are identical and represent the compounds with the numbers of 141-1-141-279 in sequence.
Table 142: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 142-1-142-279 in sequence.
Table 143: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 143-1-143-279 in sequence.
Table 144: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 144-1-144-279 in sequence.
Table 145: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent indicated in Table 4 and represents the compound number 145-1-145-279 in sequence.
Table 146: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 146-1-146-279 in sequence.
Table 147: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝H，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 147-1-147-279 in sequence.
Table 148: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n andthe substituents shown in Table 4 are identical and represent the compounds numbered 148-1-148-279 in sequence.
Table 149: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 149-1-149-279 in sequence.
Table 150: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound with the number of 150-1-150-279 in sequence.
Table 151: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 151-1-151-279 in sequence.
Table 152: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 152-1-152-279 in sequence.
Table 153: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 153-1-153-279 in sequence.
Table 154: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 154-1-154-279 in sequence.
Table 155: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 155-1-155-279 in sequence.
Table 156: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 156-1-156-279 in sequence.
Table 157: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 157-1-157-279 in sequence.
Table 158: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 158-1-158-279 in sequence.
Table 159: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 159-1-159-279 in sequence.
Table 160: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 160-1-160-279 in sequence.
Table 161: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 161-1-161-279 in sequence.
Table 162: general formula (VII)In I-C, when R is2＝R3＝H，L＝CH(CH3)，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 162-1-162-279 in sequence.
Table 163: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents 163-1-163-279 in the order of the compound number.
Table 164: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 164-1-164-279 in sequence.
Table 165: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 165-1-165-279 in sequence.
Table 166: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 166-1-166-279 in sequence.
Table 167: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 167-1-167-279 in sequence.
Table 168: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n and the substitutions shown in Table 4The radicals are consistent and represent the compounds with the numbers of 168-1-168-279 in sequence.
Table 169: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 169-1-169-279 in sequence.
Table 170: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 170-1-170-279 in sequence.
Table 171: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 171-1-171-279 in sequence.
Table 172: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered as 172-1-172-279 in sequence.
Table 173: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 173-1-173-279 in sequence.
Table 174: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 174-1-174-279 in sequence.
Table 175: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 175-1-175-279.
Table 176: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 176-1-176-279 in sequence.
Table 177: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 177-1-177-279 in sequence.
Table 178: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound with the number of 178-1-178-279 in sequence.
Table 179: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 179-1-179-279 in sequence.
Table 180: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 180-1-180-279 in sequence.
Table 181: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n and the substitutions shown in Table 4The groups are consistent, and represent the compounds with the numbers of 181-1-181-279 in sequence.
Table 182: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 182-1-182-279 in sequence.
Table 183: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 183-1-183-279 in sequence.
Table 184: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 184-1-184-279 in sequence.
Table 185: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents 185-1-185-279 in the order of the compound number.
Table 186: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 186-1-186-279 in sequence.
Table 187: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When H, Y ═ CH, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 187-1-187-279 in sequence.
Table 188: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the serial number of 188-1-188-279.
Table 189: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 189-1-189-279 in sequence.
Table 190: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 190-1-190-279 in sequence.
Table 191: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When H, Y, N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 191-1 to 191-9 in this order.
Table 192: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is N, a substituent (R)6) n is in accordance with the substituent shown in Table 55 and represents a compound number of 192-1 to 192-9 in this order.
Table 193: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 193-1 to 193-9 in this order.
Table 194: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-N, the substituent (R)6) n is the same as the substituent shown in Table 55, and represents the compound numberThe number of the particles is 194-1 to 194-9.
Table 195: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, Y, N, a substituent (R)6) n is in accordance with the substituent shown in Table 55 and represents a compound number of 195-1 to 195-9 in this order.
Table 196: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 196-1 to 196-9 in this order.
TABLE 197: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 197-1 to 197-9 in this order.
Table 198: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-N, the substituent (R)6) n is identical to the substituent shown in Table 55 and represents the compound number 198-1-198-9 in this order.
Table 199: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, Y, N, a substituent (R)6) n is identical to the substituent shown in Table 55 and represents the compound number of 199-1 to 199-9 in this order.
Table 200: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 200-1 to 200-9 in this order.
Table 201: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compoundThe serial numbers of the materials are 201-1-201-9 in sequence.
Table 202: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-N, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents a compound number of 202-1 to 202-9 in this order.
Table 203: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When H, Y, N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers 203-1 to 203-9 in this order.
Table 204: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound numbers 204-1 to 204-9 in this order.
Table 205: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When Y is N, a substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 205-1 to 205-9 in this order.
Table 206: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-N, the substituent (R)6) n is the same as the substituent shown in Table 55 and represents the compound number of 206-1 to 206-9 in this order.
In the general formula I-C', when R is10＝R11When H is satisfied, some specific compounds can be shown in tables 142-1, 146-1, 150-1, and 154-1.
Figure GPA0000263312810000271
Table 142-1: in the general formula I-C', when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 142-1-1-142-1-279 in sequence.
TABLE 146-1: in the general formula I-C', when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 146-1-1-146-1-279 in sequence.
TABLE 150-1: in the general formula I-C', when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound number of 150-1-1-150-1-279 in sequence.
TABLE 154-1: in the general formula I-C', when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 154-1-1-154-1-279 in sequence.
In formulas I-D, some specific compounds can be illustrated in tables 207-210.
Figure GPA0000263312810000281
Table 207: in the general formula I-D, when R is1＝CH3，R3＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 207-1-207-279 in sequence.
Table 208: in the general formula I-D, when R is1＝CH3，R3＝H，L＝CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 208-1-208-279 in sequence.
Table 209: in the general formula I-D, when R is1＝CH3，R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 209-1-209-279 in sequence.
Table 210: in the general formula I-D, when R is1＝CH3，R3＝H，L＝CH2CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 210-1-210-279 in sequence.
In the general formulas I to E, some specific compounds can be shown in tables 211 to 214.
Figure GPA0000263312810000282
Table 211: in the general formula I-E, when R1＝CH3，R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 211-1-211-279 in sequence.
Table 212: in the general formula I-E, when R1＝CH3，R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 212-1-212-279 in sequence.
Table 213: in the general formula I-E, when R1＝CH3，R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 213-1-213-279 in sequence.
Table 214: in the general formula I-E, when R1＝CH3，R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n and the substituents shown in Table 4Consistently, the representative compound is numbered 214-1-214-279 in sequence.
In formulas I-F, some of the specific compounds can be illustrated in tables 215-218.
Figure GPA0000263312810000283
Table 215: in the general formula I-F, when R is1＝CH3，R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 215-1-215-279 in sequence.
Table 216: in the general formula I-F, when R is1＝CH3，R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 216-1-216-279 in sequence.
Table 217: in the general formula I-F, when R is1＝CH3，R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 217-1-217-279 in sequence.
Table 218: in the general formula I-F, when R is1＝CH3，R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 218-1-218-279 in sequence.
In the general formulae I to G, some specific compounds can be shown in tables 219 to 222.
Figure GPA0000263312810000291
Table 219: in the general formula I-G, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 219-1-219-279.
Table 220: in the general formula I-G, when R is1＝CH3，R2＝H，L＝CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 220-1-220-279 in sequence.
Table 221: in the general formula I-G, when R is1＝CH3，R2＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 221-1-221-279 in sequence.
Table 222: in the general formula I-G, when R is1＝CH3，R2＝H，L＝CH2CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 222-1-222-279 in sequence.
In the general formulas I to H, some specific compounds can be shown in tables 223 to 226.
Figure GPA0000263312810000292
Table 223: in the general formula I-H, when R1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 223-1-223-279 in sequence.
Table 224: in the general formula I-H, when R1＝CH3，R2＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 224-1-224-279 in sequence.
Table 225: in the general formula I-H, when R1＝CH3，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 225-1-225-279 in sequence.
Table 226: in the general formula I-H, when R1＝CH3，R2＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 226-1-226-279 in sequence.
In the general formulas I-I, some specific compounds can be shown in tables 227-230.
Figure GPA0000263312810000301
Table 227: in the general formula I-I, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 227-1-227-279 in sequence.
Table 228: in the general formula I-I, when R is1＝CH3，R2＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 228-1-228-279 in sequence.
Table 229: in the general formula I-I, when R is1＝CH3，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 229-1-229-279 in sequence.
Table 230: in the general formula I-I, when R is1＝CH3，R2＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n and a substituent one shown in Table 4Thus, the representative compounds are numbered 230-1-230-279 in sequence.
In the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，n＝0，R9When it is a non-hydrogen substituent, the compound is shown in Table 231, and the number of the compound is 231-1-231-140 in sequence.
Table 231
Figure GPA0000263312810000302
Figure GPA0000263312810000311
Table 232: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，(R6) When n is 2-Cl, the substituent R9In accordance with the substituents shown in Table 231, the representative compound number is 232-1-232-140 in this order.
Table 233: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，(R6) When n is 3-Cl, the substituent R9In accordance with the substituents shown in Table 231, the representative compound number is 233-1-233-140 in this order.
Table 234: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，(R6) When n is 4-Cl, the substituent R9In accordance with the substituents shown in Table 231, the representative compound is numbered sequentially from 234-1 to 234-140.
Table 235: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，(R6) When n is 4-F, the substituent R9Corresponding to the substituents shown in Table 231, the representative compound number is 235-1-235-140。
Table 236: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，(R6) When n is 2, 6-diCl, the substituent R9In accordance with the substituents shown in Table 231, represents the compound having the number of 236-1-236-140 in this order.
Table 237: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，(R6) When n is 2, 4-diCl, the substituent R9In accordance with the substituents shown in Table 231, the representative compound is numbered in the order of 237-1-237-140.
In the general formulas I-J, some specific compounds can be shown in tables 238-241.
Figure GPA0000263312810000321
Table 238: in the general formulas I-J, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents 238-1-238-279 in the order of the compound number.
Table 239: in the general formulas I-J, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 239-1-239-279 in sequence.
Table 240: in the general formulas I-J, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 240-1-240-279 in sequence.
Table 241: in the general formulas I-J, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 241-1-241-279 in sequence.
In the general formulas I-K, some specific compounds can be shown in tables 242-245.
Figure GPA0000263312810000322
Table 242: in the general formula I-K, when R2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 242-1-242-279 in sequence.
Table 243: in the general formula I-K, when R2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 243-1-243-279 in sequence.
Table 244: in the general formula I-K, when R2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 244-1-244-279 in sequence.
Table 245: in the general formula I-K, when R2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 245-1-245-279 in sequence.
In the general formulae I to L, some specific compounds can be shown in tables 246 to 249.
Figure GPA0000263312810000331
Table 246: in the general formula I-L, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, the reaction is carried out,substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 246-1-246-279 in sequence.
Table 247: in the general formula I-L, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 247-1-247-279 in sequence.
Table 248: in the general formula I-L, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical with the substituent shown in Table 4 and represents a compound with the number of 248-1-248-279 in sequence.
Table 249: in the general formula I-L, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 249-1-249-279 in sequence.
In formulas I-M, some specific compounds can be illustrated in tables 250-259.
Figure GPA0000263312810000332
Table 250: in the general formula I-M, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 250-1-250-279 in sequence.
Table 251: in the general formula I-M, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 251-1-251-279 in sequence.
Table 252: in the general formula I-M, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 252-1-252-279 in sequence.
Table 253: in the general formula I-M, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 253-1-253-279 in sequence.
Table 254: in the general formula I-M, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 254-1-254-279 in sequence.
Table 255: in the general formula I-M, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents 255-1-255-279 in sequence.
Table 256: in the general formula I-M, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 256-1-256-279 in sequence.
Table 257: in the general formula I-M, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 257-1-257-279.
Table 258: in the general formula I-M, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 4 and represents the compound number of 258-1-258-279。
Table 259: in the general formula I-M, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 259-1-259-279 in this order.
In the general formulae I to N, some specific compounds can be shown in tables 260 to 269.
Figure GPA0000263312810000341
Table 260: in the general formula I-N, when R2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 260-1-260-279 in sequence.
Table 261: in the general formula I-N, when R2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 261-1-261-279 in sequence.
Table 262: in the general formula I-N, when R2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 262-1-262-279.
Table 263: in the general formula I-N, when R2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 263-1-263-279 in sequence.
Table 264: in the general formula I-N, when R2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is the same as the substituent shown in Table 4 and represents a compoundNumbered 264-1-264-.
Table 265: in the general formula I-N, when R2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 265-1-265-279 in sequence.
Table 266: in the general formula I-N, when R2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 266-1-266-279 in sequence.
TABLE 267: in the general formula I-N, when R2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 267-1-267-279 in sequence.
Table 268: in the general formula I-N, when R2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 268-1-268-279 in sequence.
Table 269: in the general formula I-N, when R2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 269-1-269-279 in sequence.
In formulas I-O, some of the specific compounds can be illustrated in tables 270-279.
Figure GPA0000263312810000342
Table 270: in the general formula I-O, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, substitutedRadical (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 270-1-270-279 in sequence.
Table 271: in the general formula I-O, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is consistent with the substituent shown in the table 4 and represents the compound number of 271-1-271-279 in sequence.
Table 272: in the general formula I-O, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 272-1-272-279 in sequence.
TABLE 273: in the general formula I-O, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, Y-CH, the substituent (R)6) n is identical with the substituent shown in the table 4 and represents the compound number of 273-1-273-279 in sequence.
Table 274: in the general formula I-O, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents 274-1-274-279 in turn.
Table 275: in the general formula I-O, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents a compound with the number of 275-1-275-279 in sequence.
Table 276: in the general formula I-O, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the serial number of 276-1-276-279.
Table 277: in the general formula I-O, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu and Y-CH, takeSubstituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 277-1-277-279 in sequence.
Table 278: in the general formula I-N, when R2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents 278-1-278-279 in the order of the compound number.
Table 279: in the general formula I-N, when R2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is consistent with the substituent shown in the table 4 and represents the compound with the serial number of 279-1-279-one.
Some of the specific compounds of formulas I-P can be illustrated in tables 280-283.
Figure GPA0000263312810000351
Table 280: in the general formula I-P, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 280-1-280-279 in sequence.
Table 281: in the general formula I-P, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical with the substituent shown in Table 4 and represents 281-1-281-279 in sequence.
Table 282: in the general formula I-P, when R is1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5＝CH3，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents 282-1-282-279 in sequence.
Table 283: general formula Iin-P when R is1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 283-1-283-279 in sequence.
In formulas I-Q, some specific compounds can be illustrated in tables 284-287.
Figure GPA0000263312810000352
Table 284: in the general formula I-Q, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents 284-1-284-279 in turn.
Table 285: in the general formula I-Q, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 285-1-285-279 in sequence.
Table 286: in the general formula I-Q, when R is1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the serial number of 286-1-286-279.
Table 287: in the general formula I-Q, when R is1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 287-1-287-279.
Some of the specific compounds of formulas I-R can be illustrated in tables 288-291.
Figure GPA0000263312810000361
Table 288: in the general formula I-R, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents 288-1-288-279 in the order of the compound number.
Table 289: in the general formula I-R, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical with the substituent shown in Table 4 and represents the compound number 289-1-289-279 in sequence.
Table 290: in the general formula I-R, when R is1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5＝CH3When Y is CH, a substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 290-1-290-.
Table 291: in the general formula I-R, when R is1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical with the substituent shown in the table 4 and represents the compound with the serial number of 291-1-291-279.
In the general formulae I to S, some specific compounds can be shown in tables 292 to 297.
Figure GPA0000263312810000362
Table 292: in the general formula I-S, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 292-1-292-279 in sequence.
Table 293: in the general formula I-S, when R is2＝CH3，R3＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is the same as the substituent shown in Table 4The representative compound number is 293-1-293-279 in sequence.
Table 294: in the general formula I-S, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents 294-1-294-279 in sequence.
Table 295: in the general formula I-S, when R is2＝CH3，R3＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 295-1-295-279 in sequence.
Table 296: in the general formula I-S, when R is2＝R3＝CH3，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 296-1-296-279 in sequence.
Table 297: in the general formula I-S, when R is2＝R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 297-1-297-279 in sequence.
In the general formulas I-T, some specific compounds can be illustrated in tables 298-303.
Figure GPA0000263312810000371
Table 298: in the general formula I-T, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents 298-1-298-279 in the order of the compound number.
Table 299: in the general formula I-T, when R is2＝CH3，R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 299-1-299-279 in sequence.
Table 300: in the general formula I-T, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 300-1-300-279 in sequence.
Table 301: in the general formula I-T, when R is2＝CH3，R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbers 301-1-301-279 in sequence.
Table 302: in the general formula I-T, when R is2＝R3＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 302-1-302-279 in sequence.
Table 303: in the general formula I-T, when R is2＝R3＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 303-1-303-279 in sequence.
In the general formulas I-U, some specific compounds can be shown in tables 304-309.
Figure GPA0000263312810000372
Table 304: in the general formula I-U, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 304-1-304-279 in sequence.
Table 305: in the general formula I-U, when R is2＝CH3，R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 305-1-305-279 in sequence.
Table 306: in the general formula I-U, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered as 306-1-306-279.
Table 307: in the general formula I-U, when R is2＝CH3，R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 307-1-307-279 in turn.
Table 308: in the general formula I-U, when R is2＝R3＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 308-1-308-279 in sequence.
Table 309: in the general formula I-U, when R is2＝R3＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 309-1-309-279 in sequence.
Some of the specific compounds of formulas I-V may be illustrated in tables 310-315.
Figure GPA0000263312810000381
Table 310: in the general formulas I-V, when R1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 310-1-310-279 in sequence.
Table 311: in the general formulas I-V, when R1＝CH3，R2＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 311-1-311-279 in sequence.
Table 312: in the general formulas I-V, when R1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 312-1-312-279 in sequence.
Table 313: in the general formulas I-V, when R1＝t-Bu，R2＝H，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 313-1-313-279 in sequence.
Table 314: in the general formulas I-V, when R1＝CH3，R2＝CH3，L＝CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 314-1-314-279 in sequence.
Table 315: in the general formulas I-V, when R1＝CH3，R2＝CH3，L＝CH2CH2，R4＝Cl，R5＝t-Bu，Y＝CH，R9When H, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 315-1-315-279 in sequence.
In the general formulas I to W, some specific compounds can be shown in tables 316 to 321.
Figure GPA0000263312810000382
Table 316: in the general formula I-W, when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 316-1-316-279 in sequence.
Table 317: in the general formula I-W, when R is1＝CH3，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 317-1-317-279 in turn.
Table 318: in the general formula I-W, when R is1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 318-1-318-279 in sequence.
Table 319: in the general formula I-W, when R is1＝t-Bu，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents 319-1-319-279 in the order of the compound number.
Table 320: in the general formula I-W, when R is1＝CH3，R2＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 320-1-320-279 in sequence.
Table 321: in the general formula I-W, when R is1＝CH3，R2＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 321-1-321-279 in sequence.
In formulas I-X, some of the specific compounds are shown in tables 322-327.
Figure GPA0000263312810000391
Table 322: general formula I-XIn when R is1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 322-1-322-279 in sequence.
Table 323: in the general formula I-X, when R is1＝CH3，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 323-1-323-279 in sequence.
Table 324: in the general formula I-X, when R is1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound numbered 324-1-324-279 in sequence.
Table 325: in the general formula I-X, when R is1＝t-Bu，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 325-1-325-279 in sequence.
Table 326: in the general formula I-X, when R is1＝CH3，R2＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 326-1-326-279 in turn.
TABLE 327: in the general formula I-X, when R is1＝CH3，R2＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 327-1-327-279 in sequence.
In the general formulas I-Y, some specific compounds can be shown in tables 328-333.
Figure GPA0000263312810000392
Table 328: in the general formula I-Y, when R1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 328-1-328-279 in sequence.
Table 329: in the general formula I-Y, when R1＝CH3，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 329-1-329-279 in sequence.
Table 330: in the general formula I-Y, when R1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 330-1-330-279 in sequence.
Table 331: in the general formula I-Y, when R1＝t-Bu，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 331-1-331-279 in sequence.
Table 332: in the general formula I-Y, when R1＝CH3，R2＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 332-1-332-279 in sequence.
Table 333: in the general formula I-Y, when R1＝CH3，R2＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 333-1-333-279 in sequence.
In the general formulae I to Z, some specific compounds can be shown in tables 334 to 339.
Figure GPA0000263312810000401
Table 334: in the general formula I-Y, when R1＝CH3，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 334-1-334-279 in sequence.
Table 335: in the general formula I-Y, when R1＝CH3，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 335-1-335-279 in sequence.
Table 336: in the general formula I-Y, when R1＝t-Bu，R2＝H，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 336-1-336-279 in sequence.
Table 337: in the general formula I-Y, when R1＝t-Bu，R2＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number 337-1-337-279 in sequence.
Table 338: in the general formula I-Y, when R1＝CH3，R2＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 338-1-338-279 in sequence.
Table 339: in the general formula I-Y, when R1＝CH3，R2＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, Y-CH, the substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound with the number of 339-1-339-279 in sequence.
In the general formula I-Q', some specific compounds can be shown in Table 340.
Figure GPA0000263312810000402
Table 340: in the general formula I-Q', when R is2＝R3H, L is a bond, R4＝Cl，R5When t-Bu, substituent (R)6) n is identical to the substituent shown in Table 4 and represents the compound number of 340-1-340-279 in sequence.
The compounds of the invention are prepared according to the following process, the reaction scheme being as follows, wherein the groups are as defined above unless otherwise stated:
according to the difference of X definition, the following two preparation methods are divided:
1) when X is NR9The preparation method of the general formula I-1 is as follows:
Figure GPA0000263312810000403
the intermediates II and III are reacted in a suitable solvent under basic conditions to give the compounds of formula I-1.
Suitable bases may be selected from, for example, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide, sodium tert-butoxide, etc.
The reaction is carried out in a suitable solvent, which may be selected from, for example, tetrahydrofuran, 1, 4-dioxane, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetone, or butanone.
The reaction temperature may be between room temperature and the boiling temperature of the solvent, and is generally from 20 to 100 ℃.
The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
Intermediate III is commercially available.
The preparation of intermediate II is described in reference to CN104710409A, WO2005060959a1, US5672715A, US5668088A, WO9640643a1, US 4099012A.
2) When X is O or S, the general formula I-2 is prepared as follows:
Figure GPA0000263312810000411
and reacting the intermediate IV and V 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, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide, sodium tert-butoxide, etc.
The reaction is carried out in a suitable solvent, which may be selected from, for example, tetrahydrofuran, 1, 4-dioxane, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetone, or butanone.
The reaction temperature may be between room temperature and the boiling temperature of the solvent, and is generally from 20 to 100 ℃.
The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
Intermediate V is commercially available.
The preparation of intermediate IV is described with reference to CN104710409A, WO2005060959a1, US5672715A, US5668088A, WO9640643a1, US 4099012A.
Although the compounds of the general formula I according to the invention also belong to the pyridazinone class of compounds with certain compounds disclosed in the prior art, there are still significant differences in structural features. And due to these structural differences, the compounds of the present invention have better bactericidal and/or insecticidal and acaricidal activity.
The compound of the general formula I shows excellent activity on various germs in agriculture or other fields, and also shows better activity on pests and mites. Therefore, the technical scheme of the invention also comprises the application of the compound shown in the general formula I in preparing bactericides, insecticides and acaricides in agriculture or other fields.
The examples of diseases mentioned below are intended only to illustrate the invention, but in no way limit it.
The compounds of the general formula I can be used for controlling the following diseases: oomycete diseases such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, loofah downy mildew, wax gourd downy mildew, melon downy mildew, Chinese cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, Chinese cabbage white rust), damping-off (rape damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cotton rot (hot pepper rot, loofah sponge rot, wax gourd blight), epidemic diseases (broad bean blight, cucumber blight, pumpkin blight, melon blight, hot pepper, leek blight, garlic blight, cotton blight, tomato blight, etc.; fungi imperfecti diseases such as wilt (sweet potato wilt, cotton wilt, sesame wilt, castor wilt, tomato wilt, bean wilt, cucumber wilt, pumpkin wilt, winter melon wilt, watermelon wilt, sweet melon wilt, hot pepper wilt, broad bean wilt, rape wilt, soybean wilt), root rot (hot pepper root rot, eggplant root rot, bean rot, cucumber root rot, bitter gourd root rot, cotton black root rot, broad bean root rot), damping off (seedling blight of cotton, sesame seedling blight, hot pepper seedling blight, cucumber damping off, cabbage stalk rot), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry leaf, hot pepper, bean disease, cucumber anthracnose, red sesame anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, eggplant disease, hot pepper anthracnose, vegetable bean disease, and cucumber blight, Balsam pear anthracnose, pumpkin anthracnose, wax gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, sunflower verticillium wilt, tomato verticillium wilt, hot pepper verticillium wilt, eggplant verticillium wilt), scab (pumpkin scab, wax gourd scab, melon scab), gray mold (boll gray mold, red ramie gray mold, tomato gray mold, hot pepper gray mold, bean gray mold, celery gray mold, spinach gray mold, kiwi gray mold), brown spot (cotton brown spot, jute brown spot, beet brown spot, peanut brown spot, pepper brown spot, wax gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot, broad bean brown spot), black spot (flax brown spot, rape black spot, sesame black spot, sunflower black spot, castor black spot, tomato black spot, tomato black spot, tomato black spot, tomato black spot, tomato black spot, tomato, Pepper black spot, eggplant black spot, bean black spot, cucumber black spot, celery black spot, carrot black rot, carrot black spot, apple black spot, peanut black spot), spot blight (tomato spot blight, pepper spot blight, celery spot blight), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean ring spot, sesame ring spot, bean ring spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), stem base rot (tomato stem base rot, bean stem base rot), and others (corn round spot, kenaf waist fold, rice blast, black sheath blight, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem blight, soybean black spot, melon big spot, peanut net spot, tea leaf spot, red leaf spot, black leaf spot, peanut net spot, tea leaf spot, tomato black spot, potato leaf spot, potato black spot, tomato leaf spot, etc, Pepper white spot disease, white gourd leaf spot disease, celery black rot disease, spinach heart rot disease, kenaf leaf mold disease, kenaf spot disease, jute stem spot disease, soybean purple spot disease, sesame leaf spot disease, castor gray spot disease, tea brown leaf spot disease, eggplant brown orbicular spot disease, kidney bean red spot disease, bitter gourd leukoderma, watermelon spot disease, jute bottom rot disease, sunflower root stem rot disease, kidney bean carbon rot disease, soybean target spot disease, eggplant rod spore leaf spot disease, cucumber target spot disease, tomato leaf mold, eggplant leaf mold, broad bean red spot disease and the like); basidiomycete diseases such as rust (wheat stripe rust, wheat stalk rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut (maize head smut, maize smut, sorghum head smut, sorghum loose smut, sorghum stalk smut, chestnut kernel smut, sugarcane head smut, kidney bean rust) and others (such as wheat sharp eyespot, rice sheath blight, etc.); ascomycetous diseases, such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, towel gourd powdery mildew, pumpkin powdery mildew, wax gourd powdery mildew, melon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia rot (flax sclerotinia rot, rape sclerotinia rot, soybean sclerotinia rot, peanut sclerotinia rot, tobacco sclerotinia rot, pepper sclerotinia rot, eggplant sclerotinia rot, kidney bean sclerotinia rot, pea sclerotinia rot, cucumber sclerotinia rot, bitter gourd sclerotinia rot, wax gourd sclerotinia rot, watermelon sclerotinia rot, celery sclerotinia rot), scab (apple scab, pear scab) and the like.
The compounds of formula I are useful for controlling the following pests:
coleoptera (Coleoptera) (beetle): bean species (Acanthoscelides spp.) (elephant), phaseolus vulgaris (Acanthoscelides obtectus) (common pisiform), Ceratoptera alba (Agrilus planipes) and Ceratopteris versicolor (Quadrifolia narrow Germin), Flammulina species (Agriotes spp.) (wireworm), Anoplophora glabripennis (Aphis longipes), Gomphytus species (Anthonoma spp.) (Arthrobacter flavidus), Gomphytus grandis (Anthronus grandis) (Arthrobacter asiaticus), Gomphytus species (Aphidius spp.) (Aprionus spp.) (Arthrospora), Cochlothiaoma sp. (Anacardia), Cochlothiajaponica (Aponia spp.) (grub), Cochlothuroides (Atacys specularis) (Black piss specula (Atanthus spec), Pieris versicolor (Pieris indica) (Pieris indica), Pieris indica (Pieris indica) (Pieris) and Pieris (Pieris indica) (Pieris chinensis (Pieris) of (Pieris) variety (Pieris illustrates (Pieris) and Pieris (Pieris) such as Pieris (Pieris sinensis (Pieris variety (Pieris) and Pieris (Pieris) such as (Pieris) A variety (Pieris) such as Pieris variety (Pieris) and Pieris variety (Pieris) including Pieris variety (Pieris) such, Pieris variety (Pieris) such as Pieris (Pieris variety (Pieris) such, Pieris (Pieris variety (Pieris) including Pieris) such as Pieris (Pieris variety, Pieris) and Pieris variety (Pieris) such), Pieris (Pieris) including Pieris variety (Pieris) and Pieris (Pieris) such), Pieris) such (Pieris) such), Pieris) such as (Pieris variety (Pieris) and Pieris variety (Pieris) such), Pieris variety (Pieris) variety (Pieris variety, Pieris (Pieris) and Pieris) including Pieris (Pieris) variety (Pieris) such) including Pieris variety (Pieris) such (Pieris variety (Pieris) including Pieris (Pieris variety, Pieris (Pieris variety (Pieris) including Pieris variety (Pieris) including Pieris, Cacoesia species (Cacoesia spp.), Callosobruchus maculatus (Callosobruchus maculatus) (southern cowpea weevil), yellow spot dew beetle (Carpophilus hemiptera) (stemona), testudina caragana (Cassida vittata), longicorn species (ccroscrna spp.), cerrotoma species (Ccrotoma spp.), trichomonas sp (chrysomella), leuconychus (ceromorpha trifoliatus) (setaria viridis), chlorophyta species (ceromorpha spp.), elephantopus (ceromorpha spp.), Chinese cabbage turtle species (ceromorphus assius) (cabbage caterpillar), turnip elephant species (ceromorphus purpureus), western cabbage beetle (ceromorphus), western red beetle (collybia), western red beetle (ceromorphus flavus), red beetle (collybia), red beetle (collygus purpurea), red beetle (collygus purpurea), red beetle (collygus), red beetle (red beetle), red beetle (collygus), red beetle (red beetle) and red beetle (red beetle), red beetle (red beetle), red beetle (red beetle), red beetle (red beetle, red beetle (red beetle) and red beetle (red beetle) are (red beetle, red beetle (red beetle), red beetle), red beetle (red beetle, red beetle (red beetle, red, Examples of such plants include, but are not limited to, Cryptolepis pusillus (Cryptolepis pulillus) (Aphelenchus fasciatus), Rhynchophyllus (Cryptolepis grain beetle), Ctenodera species (Ctenodera spp.) (nematodes), elephant species (Curculio spp.) (weevil), Rhinocephalus species (Cycleephora spp.) (Holotrichia dioides), Rhinocephalus degraphus (Hyponella fasciata) (Trichophyllus fasciatus), Rhinocephalus (Deporus marginatus) (Margarita fasciatus), Rhizophora paragua (Mesorus paraphyllus), Rhizophora paragua (Mesorus) (Pharmanopsis paraphyllus), Rhizophora striatus (Hypoglaucus) and Rhizophora leucotrichia (Meadora), Rhizophora leucotrichia (Piropis leucotrichia), Rhizophora leucotrichia (Piropis fasciata (Meadowrue), Rhizophora leucotrichia fasciata (Pilus) and Rhizophora) species (Meadowraenophora), Rhizophora fascicularia), Rhizophora (Piropis sp. (Pirophus fascicularis) and Rhizophyllus (Piropis) or Piropis sp. (Meadonis (Pirophus fascicularia) or Piropis (Piropis) or Pirophus fasciatus (Piropis) or A) or Piropis) or Pirophus fasciatus (Piropis) or Piropis (Pirophus fasciatus), Piropis fasciatus (Piropis) or Piropis fasciatus (Piropis L. hamus) or Piropis (Piropis L. hamus) and Piropis (Piropis) of Piropis (Pirops) of Piropis (Piropis of Pirops) of Pirops, Pirophus fasciatus (Piropis (Pirophus fasciatus), Pirophus fasciatus (Pirophus fasciatus), Piropis of Pirophus fasciatus (Pirophus fasciatus), Pirophus fasciatus (Pirophus fasciatus), Piropis (Pirophus fasciatus), Piropis of Piropis) of Pirophus fasciatus (Piropis ) of Piropis, Pirophus fasciatus (Pirophus fasciatus), Piropis) of Pirophus fasciatus (Piropis of Piropis, Piropis of Pirop, Lucerne medicago sativa (hyperbaric) (medicago sativa), medicago species (hyperboes spp.) (argentina stem weevil (Hyperodes weevil)), coffee chervil (polyphnemus hamperei) (coffee chervil), scotland species (Ips spp.) (echinacea purpurea), tobacco beetle (Lasioderma serricorne) (tobacco beetle), potato beetle (leptotarsa decemlata) (colorado potato beetle), lipoglorys fuscus, lipogynys suturalis, rice water weevil (lisurena oryzophilus) (rice water weevil), silphigus species (lycospera spellensis), meldonia sp.) (meclizia purpurea/tenera), meldonia terrestris (meldonia), meldonia spp (meldonia spp.) (Mewlela spp.) (Mewlera), Mesorrel louse beetle (Mewlela spp.) (Messoides), Mesorrel louse beetle sporulata (Mewlela spp. (Messochloes sporea), Mewless beetle spp. (Messel beetle spruce) Rhinoceros rhynchophylla (oriycetes rhinoceros) (date palm beetle), ceremony saw beetle (oryzaephiulus mercator) (market saw beetle), cercaria terrestris (elephant), cercaria terrestris (odontobrama), cercaria species (oxytrophus spp), cercaria nigripes (auricle melas mellea) (orange leaf beetle), cercaria terrestris (auricle oryzae), cerbrotica rosea (purpureus), cercaria species (panomyopis p), panopis palustris (ostrinia nubilalis), cercaria terrestris (purpurea), cercaria macrotrichia (peruvignonensis), cercaria terrestris (purpurea), cercaria macrotrichia (pernya), cercaria stris (purpurea), cercaria macrotrichia terrestris (purpurea), cercaria terrestris (bullosa) (common beetle species), cercaria stringta (bullosa) (common beetle species (pink) (common beetle species), cerifera), cerbrotica striga (mangle), cerifera), cerbrotica striga (mangle), cercospinus mangle), cerifera (mangle) and cerifera) including rhizopus mangle (mangle) and cerifera (mangle, cerifera) including rhizopus mangle, cerifera, mangle, cerifera, cerbrotica, kayas, cerbrotica, and eugles, cerbrotica, and eugles (mange, kayas, and eugles (mangle, chaeta, kayas (mange, picea (mangle, picea (mangle, picea mangle, picea mange, picea mangle, picea (mangle, picea mange, picea mange, picea mangle, picea mange, picea mange, picea mangle, picea mange, picea, pic, Root gill species (rhizomorphous spp.) (european scarab (european chafer)), cryptorhynchophorus species (ryophorus spp.) (elephant), silly species (Scolytus spp.) (wooddull moth), shonophorus species (shonophorus spp.) (cereal elephant), pisum sativum leaf (Sitona linkuntze) (pea leaf weevil (pca leaf weevil)), rice weevil species (Sitophilus spp.) (cereal weevil), rice elephant (Sitophilus grandis) (paddy insect (granavirus), rice elephant (Sitophilus oryzae) (rice weevil), rice paneum (stewartum), triphyllum sativum (triborum), and red beetle (Tribolium), red beetle (Tribolium sativum), red beetle (Tribolium), red beetle (red beetle), red beetle (red beetle, red beetle.
Dermaptera (Dcrmaptcra) (earwigs).
Vein winged order (Dictyoptera) (cockroach): german cockroach (Blattella germanica) (German cockroach), blattaria orientalis (Blatta orientalis), Blatta palustris (Blatta cockroach), Blatta australiana (parcoblata penylvanica), Periplaneta americana (perilanta americana) (austria americana), Blatta australiana (australia cockroach)), Periplaneta fusca (pcripa rubra) (australia cockroach), Periplaneta fuliginosa (brown cockroach), Periplaneta smokosa (perilanta fuliginosa) (Periplaneta fuliginosa (cockroach)), and Periplaneta fuliginosa (brown cockroach) (Periplaneta subcapium (brown cockroach)), and Periplaneta fuligina (brown cockroach) (Periplaneta rubra americana (brown cockroach)).
Diptera (Diptera) (flies): mosquito species (Aedes spp.) (mosquito), lucerne fly larvae (Agromyza frontella) (alfa blotch), agromyzis species ((Agromyza spp.) (leaf miner), trypetid species (anastrep spp.) (fruit fly), garleria persica (anastrepa subsp.) (fruit fly), garleria persica (garleria persica) (garleria persica (tail fly)), mosquito species (anophes spp.) (mosquito), fruit fly species (batrachta spp.) (fruit fly), melon fly (Bactrocera bitrae) (melon), citrus fruit fly (Bactrocera persica), mosquito species (ceitis spp.) (mosquito), mosquito fly larvae (sea fly larvae) (sea fly), sea fly larvae (sea fly larvae) (deer spp.) (moth), sea fly larvae (sea fly larvae) (moth larvae) (bilus persica spp.) (fruit fly) (moth larvae) (mosquito larvae) (deer spp.) (fruit fly) (garrisb) (mosquito larvae) (sea fly) (moth) Leaf of rape mosquito (Dasineura brassicae) (cabbage mosquito), Dimochi species (Delia spp.), Gray fly (Delia platura) (root maggot (seedcom bug)), Drosophila species (Drosophila spp.) (vinegar fly), Musca species (Fannia spp.) (housefly), yellow belly fly (Fannia canicillila) (summer fly (little fly), Grey belly fly (Fannia salaris) (Grey fly), Large belly fly (Gastrophania intestinalis) (horse stomach fly), Gracillia persea, sheep bloody fly (Haematobia irritans) (horn fly), Black fly species (Hylemia sp.) (root maggot)), Musca fly (common cabbage fly) (cabbage fly)), Musca fly (housefly) (leaf fly), Musca fly (cabbage fly) (Meristius spp.) (Meristius (cabbage fly), Musca fly (cabbage fly) (fly), Musca fly (cabbage fly) (fly (leaf), Musca fly (fly), Musca fly (cabbage fly) (fly), Musca fly (cabbage fly) (fly (leaf fly), Musca fly (cabbage fly) (fly) and Musca fly (leaf fly) (fly), Musca fly (cabbage fly) (fly) and leaf fly) and Musca fly (fly), Musca fly (cabbage fly (fly) (fly), Musca fly (fly) and Musca fly (fly), Musca fly (fly) and Musca fly (fly), Musca fly (fly) and Musca fly (fly) and Musca fly (fly), Musca) and Musca fly (fly) and Musca) variety, fly (fly), Musca) and Musca) variety, fly (fly), and Musca) variety, Musca) and Musca) variety, Musca) and Musca variety (fly (leaf, and Musca) and Musca variety (leaf, and Musca) and Musca variety (leaf, which are included in, and Musca variety, and Musca) including the same) and Musca variety, and Musca variety (leaf, and Musca variety, and Mu, The plant includes, but is not limited to, the species fall houseflies (Musca australis) (face flies), houseflies (Vusca domestica) (house flies), sheep houseflies (oesteurs) (sheep nose flies), european stem flies (ostrich flies), beet spring flies (pegmybia beta) (spinach leaf miner), phomopsis sp (Phorbia spp.), carrot stem flies (psilla rosa sativa) (carrot rust flies), cherry fruit flies (rhagophylla cerasi) (cherry fruit flies)), apple fruit flies (rhapontia pompona) (apple maggots), red mud fly (Sitodiplosis mossamara) (horse flies (stable flies)), and cattle fly (stable flies) (cattle yellow flies).
Hemiptera (Hemiptera) (stinkbug): apolygus lucorum (Acrosteronum hieron) (green stink bug), Oryza sativa (Blissus leucopterus) (long stink bug), Oryza sativa (Caloris norvegicus) (potato stink bug), Tropical stink bug (Cimex hemipterus) (tropical stink), stinkbug (Cimex leucopterus) (bed bug), Daghertus fasciatus, Dichelops furcatus, Oryza sativa (Eucotton stainer), Edestabunda (Oryza sativa), Oryza sativa (Lepidorum), Oryza sativa (Oryza sativa) and Oryza sativa (Oryza sativa) by (Oryza sativa) and/or Oryza sativa (Oryza sativa) for treating plant (Oryza sativa) and/Oryza sativa (Oryza sativa) for treating plant, Lygus hesperus (Lygus hesperus) (western tarnished plant bug), hibiscus syriacus linnaeus (macrocytoericcus hirsutus), neuroolpus longirostris, rice green bugs (Nezara viridula) (southern green stink bug), Lygus planterum (phytolocoris spp.) (Lygus), california planterus (phytoorius californicus), phytoorius relatus, piezocoritus guilidingdinggi, tetrad bugs (podocarpus utilis linus) (folulated plant bug), psycaninum vaccicola, pseudophyceae, scorpiona, streptococcus and trypanosoma (trypanosoma) species (nose cone).
Homoptera (Homoptera) (aphid, scale, whitefly, leafhopper): piper pisum (Acrythosiphopkinsum) (pea aphid)), Coccinum species (Adelges spp.) (adelgids), Beeuglena brassicae (Aleurodes proteella) (Beeuglena cabbage whitefly), Aleurodicus disperses (Aleurodicus disperses), Aleurothrix striatus (Aleurothrix luteus) (gloomy whitley), Begoniothyria albonensis species (Aluaspis spp.) (Aluraceae biguella), Pectinatus species (Aphrophola sp.) (Aphrophophora spp.) (leafhopper), Rhodococcus rhododendron (Aoniella natura), Begoniothrix gloeosporioides (Begonioth), Begoniothrix gloeosporus (Begoniothrix), Begoniothrix aphid (Begoniothrix), Begoniothrix) aphid (Begoniothrix), Begoniothrix sp (Begoniothrix) and Begoniothrix aphid (Begoniothrix) Aphis (Begonioth), Begonioth (Aphis) Aphis sp), Begonioth (Begonia), Begonioth (Aphis sp), Begonioth (Begonioth) Aphis sp), Begonia), Begonioth (Begonia), Begoniothrix) and Begoniothrix) species (Begoniothrix) of Aphis, Begoniothrix, Aphis, asparagus tubular aphid (Brachyryyncria asparagi) (Asparagus aphid), Brevennia rehi, cabbage aphid (Brevicornus brassicae) (cabbage aphid), Lecanicillium species (Ceroplastes spp.) (scale), Ceriporiococcus rubens (Ceroplastes rubens) (red wax scale), Cestrum species (Chionastis spp.) (Iceltica), Lecanicillium species (Chrysomophagus spp.) (scale), Ceriporiococcus species (Coccus spp.) (scale), apple pink aphid (Dysapphigenia plantaginea) (sysplex aphid), Phyllopsis viridis (apple aphid) and Lecanicola (apple aphid) plant (apple aphid), Phyllospora major (apple aphid), Phyllospora (apple aphid) and Lecanicola (apple aphid), Phyllospora grandis (apple aphid), Phyllophora gossypium (apple aphid), Leonicola (apple aphid (apple), and Leonicola (apple aphid), Phyllophora variety (apple aphid) and Leonicola (apple aphid) of Leonicola (apple aphid (apple), Leonicola (apple aphid), and leaf, apple aphid (apple), and leaf, leaf strain (apple stem) (maize) plant, leaf strain (apple stem, leaf, Leaf of the species Mylopharyngodium (Macrosiphum grandium) (English grandis)), Long pipe aphid (Macrosiphum rosae) (Rose aphid (rose aphid)), four-leaf hopper (Macrosteles quadratus) (purple leaf hopper (ash leaf hopper)), Mahanarva frimbiola, Meopodium diricum (wheat germ) aphid (rose aphid), Midis Longicornis, peach aphid (Myzus persicae) (peach aphid (green apple aphid)), Nephophylum spruce (Nephotettix spreng) (leaf hopper), Nephotettix cinctix (green leaf hopper), Phosphaera (brown apple aphid) (Phosphaera), Phosphaera (brown apple aphid) (leaf hopper), Phosphaera (leaf hopper), Phosphaericoides) (leaf hopper) (leaf hopper), leaf hopper (leaf hopper) (leaf hopper (leaf), leaf hopper (leaf hopper (leaf hopper) and leaf hopper (leaf hopper) (leaf hopper (leaf hopper) leaf, leaf hopper (leaf hopper) Pygeum sp (mealybugs), pygeus sp (mealybugs), begecky sp (Pseudococcus spp), mealybugs (Pseudococcus brcvps) (pink apple), pernicia pelyridis (quadrspididatus) (saint josephse), pygecky sp (Rhapalosiphum sp.) (aphid), corn leaf aphid (rhaalophilus maida) (corn aphid), corn leaf aphid (bitter orange apple tree), red apple wax apple tree (white apple tree) (black apple tree) (black apple tree), white apple tree (white apple tree) (black apple tree), apple tree) (black apple tree) (black apple, Whitefly species (Trialeurodes spp.) (whitefly), greenhouse whitefly (Trialeurodes vaporariorum) (greenhouses whitefly), brown wing whitefly (Trialeurodes abutiloneus) (bandtwing whitefly), cupula species (Unaspis spp.) (scale), arrowhead (Unaspis yanonensis) (arrowhead scale), and Zulia entreriana.
Hymenoptera (Hymenoptera) (ants, wasps and bees): incised leaf ant species (Acrommerx spp.), Sinkiang leaf bees (Athalia rosae), leaf ant species (Atta spp.), Ieafcutting ants, Black ant species (Camponus spp.), wooden ants (carpenter ant), pine leaf bee species (Diprion spp.), leaf bees (sawfly), Formica spp. (Formica spp.), Argentina argentea (Iridogyrmex pollicis) (Argentintinentant), Coccinum subspecies (Monorium spp.), little termites (Monoformium nigrum) (littlet lake ant), Japanese termites (Pharmanye Solenopsis), New pine leaf bee species (Neomerium spp.), family bee species (Meliotica spp.), family bee species (Melisseria meleagle bee), genus Melissa (Melisseria meleagiensis (Solomon), and species of Melissa bee (Solomon spp.) (Polionus spp.), Quadrature, Melissus spp. (Solomone spp.) (Solidanus spp.), and the like), and the species of Melisseria meldonsis (Solomonas, Wasp species (vespela spp.) (yellow jack) and trichogramma species (Xylocopa spp.) (carpenter bee).
Isoptera (Isoptera) (termites): coptotermes spp, Coptotermes curcus, Coptotermes flavus, Coptotermes formosanus, Coptotermes spp, Coptotermes formosanus, Coptotermes spp, Coptotermes formosanus, Coptotermes spp, Coptotermes formosanus sp, Coptotermes spp, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes termes spp, Coptotermes formosanus spp, Coptotermes termes, Coptotermes spp, Coptotermes termes, Coptotermes formosanus spp, Coptotermes termes, Coptotermes termes formosanus spp, Coptotermes termes, Coptotermes termes formosanus termes, Coptotermes termes formosanus termes, Coptotermes, Copto, Reticulitermes banyulensis, Spodoptera grassland (Reticulitermes grassei), Reticulitermes flavipes (Reticulitermes flavipes) (eastern soil-dwelling termites), Reticulitermes flavipes (Reticulitermes hagenii), West Scleropectium (Reticulitermes heperus) (West soil-dwelling termites), Moraxeticles sanguineus (Reticulitermes santonensis), Norterex benthamoides (Reticulitermes speratus), Reticulitermes nigripes (Reticulitermes tibialis), Reticulitermes virginicus (Reticulitermes virginicus), Reticulitermes formosanus species (Schedorthes spp.) and Zootes spp (Zooter termite spp.).
Lepidoptera (Lepidoptera) (moths and butterflies): achoea janata, Trichosporon species (Adoxophyceae spp.), Trichosta gossypii (Adoxophyceae orana), Gekko sp (Agrotis spp.), cutworm ((Agrotis ipsilon) (Black cutter), Trichosta gossypii (Alabama argillacea) (Cotton leaf worm), Amorbia cuneata (Amomum cubensis), Amorbia cuneata, Amylosis trastuella (Na orange) Teng, Anacoptida, Spodoptera fortunei (Na orange), Anacoptids degelata, Spodoptera cuneata (Anarctia lineata) (peach twigs borrer), Athiophylla (Anomyia sanguinea), Trichosta (Boomula japonica) (Boyloptera), Trichosta niponica (Boyloptera), Spodoptera (Ostrinia), Spodoptera (Boyloptera), Spodoptera fructicola (Boyloides kura), Spodoptera (Boyloptera) variety (Boyloptera), Spodopterocarpus (Boyloptera), Spodoptera (Boyloptera) and Boylophyta (Boylopterocarpus (Boylophysa) variety (Boylophysa) including Boylophysa, Spodopterocarpus (Boylophysa) and Boylophysa (Boylophysa) can, The species of the genus Spodoptera (Caloptilia spp.) (Spodoptera exigua), Capua reticulana, peach fruit moth (Carposina niponensis) (peach fruit moth)), Bombycis (Chilo spp.), mango lateral-thread Philippine moth (Chuumetia transversa) (mango shoot front borner), rose leaf roller (Choristeura rosaria) (oblitera rosea) (oblitera), noctuid barrel (noctuid roller), Spodoptera species (Chrysodexis p.), Ostrinia punctata (Cnaphaloceras medialis) (Spodoptera grasses (Spodoptera)), Spodoptera litura (Spodoptera), Coprinus litura (apple leaf moth) (apple moth (Cypress), Spirochaeta (Spirochaeta), Plutella xylostella (Spirocha), Spirochalia xylostella), Spirochalia striata (Conemonorhala), Spirochalia xylostella (Spodoptera), Spirochalia xylostella (Sporina), Spirochada (Sporina), Spirocha (Sporina), Sporina (Sporidina (Sporina), Sporina) and Sporina) species (Sporina) of the family, Sporina (Sporina) and Sporina (Sporina) in the family, Sporina (Sporina) of the family, Sporina (Sporina) and Sporina (Sporina) of the family, Sporigana (Sporigana) of the genus Sporigana, Sporigana (Sporigana, Sporigana (Sporigana) of the family, Sporigana (Sporigana, Sporigana (Sporigana) of the family, Sporigana, Spiritis (Sporigana, Sporigana (Sporigana, Sp, the species Darna diducta, Diaphania sp (Diaphania spp.) (stem borer)), borer sp (Diaphania spp.) (stem borer (staged borer)), borer (Diaphania saccharalis) (sungar borer), southwestern corn stalk (Diaphania grandiflora) (southwestern corn borer), diamond-back seed (eared diamond-back) eared (eared diamond-back), cotton bollworm (eared bollworm), and diamond-back (earia insulata) (egyptiana boreworm), diamond-back (eared diamond-back) (roughh northern pink bollworm), dynastigma (apple stem borer), ostrinia (ostrinia), ostrinia nubila (ostrinia nubila), ostrinia nubilalis (ostrinia nubilalis), ostrinia nubilalis) (ostrinia nubilalis), ostrinia nubilalis (ostrinia nubilalis) (ostrinia nubila nubilalis), ostrinia nubilalis (ostrinia nubilalis), ostrinia nubilalis) (ostrinia nubilalis (ostrinia nubila nubilalis) (ostrinia nubilalis), ostrinia nubilalis (ostrinia nubila nubilalis), ostrinia nubila nubilalis (ostrinia nubilalis), ostrinia nubila nubilalis (ostrinia nubila, ostrinia nubila nubilalis), ostrinia nubila, ostrinia nubila (ostrinia nubila, ostrinia nubila (ostrinia nubila, ostrinia (ostrinia nubila, ostrinia nubila, ostrinia nubila, ostrinia nubila, ostrinia nubila (ostrinia, ostrinia nubila, ostrinia nubila, ostrinia nubila, Noctuid (epiotia aporema), scolyptera bananas (eriodictyon x) (banana skipper), euglenopsis lucida (Eupoecilia ambiguella) (grape berry moth (grape berry moth)), Euxoa auricularia (Euxoa auricularis) (army cutworm), cutworm (ferula sp.) (cutworm), hornworm (gorworm sp.) (moth), oriental moth (grapholitta molesta) (peach (apricot) seed heart worm (original fruit moth)), borer (moth) (soybean leaf moth (cabbage leaf moth)), budworm sp.) (Helicoverpa sp.) (Helicoverpa sp.)), cotton bollworm (corn earworm) (Helicoverpa punctifera), Helicoverpa punctifera (Helicoverpa punctifera) (Helicosa (Helicoverpa sp.)), Helicoverpa sp.) (Helicosa (Helicoverpa sp.)) and Helicoverpa sp.) (Helicoverpa sp.))), Tomato moth (Keifera lycopersicella) (tomato pinum), white-fin webworm (Leucinodes orbornata) (egg plant front borer), leaf miner (Leuconostoc maliella), leaf miner (Lobesia borna) (grape fruit moth), leaf miner (Loxagrus sp.) (noctuid), leaf white-line root cutting (Loxagrus albicostata) (western tea fruit word), leaf moth (Lymantria disparis) (gypsylla moly)), leaf miner (Lyonetherella) and leaf miner (apple leaf miner) (apple leaf cabbage leaf borer), leaf miner (cabbage leaf miner) (cabbage leaf borer), leaf miner (Lyonetherella), leaf miner (apple leaf miner)) Winter loopers (Operphthora briata) (winter moth)), European corn borer (Ostrinia nubilalis) (European corn borer (European corn borner)), Oxydia vesula, Ostrinia fructicola (Pandemia cerosa) (common grape leaf moth (common currant torax)), apple leaf moth (Pandemia hepiali) (brown apple pitridix), African damascena (Papilio demodula), Red wheat moth (Pectinophora gossypiella) (red bell (pink bollworm)), Arctia species (Peridroma spp.) (Rhizopus), European red tiger (Peridroma sacchrina) (cabbage caterpillar (cabbage)), European red cabbage looper (Peripleria punctatus), European red cabbage moth (cabbage caterpillar), European red cabbage caterpillar (Peripleria spodoptera), European red cabbage caterpillar (cabbage caterpillar), European red cabbage caterpillar (cabbage caterpillar), European cabbage caterpillar (cabbage caterpillar), cabbage caterpillar (cabbage caterpillar) (cabbage caterpillar variety of the species (cabbage caterpillar), cabbage caterpillar (cabbage caterpillar) of the species (cabbage caterpillar, cabbage caterpillar (cabbage caterpillar), cabbage caterpillar (cabbage caterpillar ) of the species of the genus of, Cabbage moth (Plutella xylostella) (diamondback moth), grape berry moth (polychrosia virosa) (grapple berry mountain moth), orange fruit moth (Prays endocarps), olive moth (prasys oleae) (olive moth), armyworm species (pseudotales spp.) (noctuid), pseudolitea unipicta (marcescens), soybean looper (pseudolitea includens) (soybe looper), looper (raphanus nu), tryporyza incertulas (scirphaga incertulas), stem borer (Sesamia fischeri), stem moth (Sesamia infusoriana) and Spirospongia armyworm (Spodoptera), cabbage looper (Spirochaetes), cabbage looper (Spirocha spongiosa), cabbage looper (Spodoptera spongiosa), cabbage looper (Spodopterocarpus niponensis) (Spodoptera spongiosa), cabbage looper (Spodopterocarpus niponaria), cabbage looper (Spodopterocarpus nipona), cabbage looper) (Spodoptera), Spodopterocarpus (Spodoptera), Spodoptera) moth (Spodopterocarpus (Spodoptera), Spodoptera) and Spodopterocarpus (Spodopterocarpa) are) species (Spodopterocarpus (Spodopterocarpa) including Spodoptera) and Spodoptera) including Spodopterocarpus (Spodoptera) and Spodoptera) including rice stem moth (Spodopterocarpus (Spodoptera) and Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) including rice stem moth (Spodoptera variety, Spodoptera variety (Spodoptera) and Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) and Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) and Spodoptera) including rice stem moth (Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) and rice stem moth (Spodoptera) such as well, Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera) and rice stem moth (Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera variety, Spodoptera) and rice stem moth (Spodoptera) including rice stem moth (Spodoptera) and rice stem moth (Spodoptera variety (Spodoptera) and rice stem moth (Spodoptera) including rice stem moth (Spodoptera variety (Spodoptera) including rice stem moth (Spodoptera variety (Spodoptera) including rice moth (Spodoptera variety, Southern Spodoptera oridania (southern armyworm), athetosis species (synanthondon spp.) (root borer), Therla basilides, Thermia gemmatalis, Chlamydomonas (tienola bisselella) (webbings moth.), Trichoplusia ni (Trichoplusia ni) (camera bbeller), Tolyta domestica (Tuts absoluta), Nematoda species (Yponomeuta spp.), Coffeta (Zeuzeracow corn), and Zeuzera pyrina (Pleurotus parviensis).
Mallophaga ((Mallophaga) feather louse (chewing lice)): sheep feather louse (Bovicola ovis) (sheet biting louse), turkey short horn feather louse (chicken body louse), and chicken feather louse (Menopon gallina) (common henhouse).
Orthoptera (Orthoptera) (grasshopper, locust and cricket): arana nigra (anacrus simplex) (Mormon horns (Mormon cricket)), mole cricket (Gryllotalpidae) (mole cricket)), eastern asia migratory locust (Locusta migratoria), grasshopper species (Melanoplus spp.) (grasshopper), acephalus wing slender thorns (Microcentrum rethreshold) (angular wing broad katydid)), pterophyces species (pterophyces spp.) (pterophyces sp.) (grasshopper), steleophaga egr, pterygrasus furcifera (scudderis) (harlequin bushy bush (fork tailed bustydidid)), and tuberous ridge (vani.
Phthiraptera (Phthiraptera) (sucking lice): the blood sucking lice species (haemattopinus spp.) (cattle and pig lice), sheep jaw lice (sheep lice), head lice (pedigree capitis) (body lice), human body lice (pedigree humanus (body lice) and crab lice (crab lice)).
Siphonaptera (daphnaptera) (fleas): ctenocephalides canis (dog flea), Ctenocephalides felis (cat flea) and human flea (Pulex irutans) (human flea).
Thysanoptera (thrips): frankliniella fusca (Frankliniella fusca) (tobaco third), Frankliniella occidentalis (western flower) Frankliniella hultrias (western flower), Frankliniella shultzii (Frankliniella williamsii) (corn Thrips), Frankliniella glasshouse Thrips (IIelothrips hamoralidis) (greenhous third), Riphisprothrips cruentus, Scirpus sp (Sciroththrips spp), Platycodon grandiflorum (Scirthricirris) (citrus trough), Frankliniella tabacum (Scirthrips spp), Talothriparia (yellow Thrips spp), and Throughthrips (Thripus spp).
Thysanoptera (Thysanura) (bristletail): chlamydomonas species (Lepisma spp.) (silverfish) and locusta species (Thermobia spp.) (locusta spp.).
From the order of Acarina (Acarina) (mites (mite) and cicadas (tick)): woodbee scutellariae (acarapis woodi) (parasitic mites in the trachea of bees), dermatophagoides farinae (Acarus spp.), dermatophagoides farinae (food mites), Acarus macrorhizus (Acarus sriro) (corn mite (grain mite)), mangifera gemini (Aceria mangifera) (mango bud mite), acanthophyrus stictus (Acarus spp.), acanthophycus solani (acanthophyrus sp.), acanthophysalis lycopersici (acanthophyrus sp.), tomaticus setosum (tomatophysus) tomatin (tomatophyceae), acanthophycus purpureus (acanthophyceae), acanthophyrus stictus (acanthophyceae) (apple pythium sp.), procumbens (acanthophyrus sp.), procumbens (mangiferus sp.), rhipifera (mangiferus sp.), rhynchopus sp.), euonymus (bracteus sp.), rhynchopus sp.), euonymus (mangiferus sp.), and mangiferus sp (mangiferus sp.), euonymus sp (mangiferus sp.), euonymus sp (mangiferus sp.), euonymus sp (mangiferus sp.), euonymus sp (mangiferus sp.), euonymus (mangiferus sp.), euonymus (mangiferus sp.), euonymus (mangiferus sp.) A (mangiferus sp.), euonymus (mangiferus sp.), gra (mangiferus sp.), euonymus (mangiferus sp.), gra (mangiferus sp.), euonymus (mangiferus sp.), gra. sp.), euonymus (mangiferus sp.), gra (mangifer (mangiferus sp.), gra, House dust mite (Dermatophagoides pteronyssinus) (house dust mite), Tetranychus sp (Eototryanus spp.), Carpinus horneri sp (Eototryanus carpini (yellow spider mite), Tetranychus sp.), Acarinus sp (Eriophenous spp.), Stephania sp (hard tick sp.; es sp.), ticks (tick), Tetranychus sp. (Tetranychus sp.), Acarinus sp. (Notoedressi spec), Acarinus sp. (Notoerdorhycus sp.), Acarinus gracilis (Notoedressi. sp.), Acarinus parvus (Oligonychus spyricus sp.), Acarinus gracilis (Ocigonurus), Acarinus wintergreen (Oligonychus (Oligonus) (sorred mite), Acarinus fuliginosus (Tetranychus), Acarinus pallidus (Tetranychus), Acarinus fuliginosus (Tetranychus), Acarinus tetranychus (Tetranychus urticae), Acarinus (Tetranychus urticae), Acarinus) (Tetranychus urticae (Tetranychus), Acarinus) (Tetranychus) or Tetranychus urticae), Acarinus (Tetranychus) (Phoenii (Tetranychus) and Tetranychus (Tetranychus) or Tetranychus (Tetranychus) or (Tetranychus) or Tetranychus (Tetranychus) or Tetranychus (Tetrasticus) or (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus) or Tetrasticus (Tetrasticus), Rhizomorpha species (rhizomorph spp.) (root mite (bulb mite)), Sarcoptes scabies (Sarcoptes scabies) (itch mite), coronaria avocado (tetragonophys perseafarae), Tetranychus species (Tetranychus spp.), Tetranychus urticae (Tetranychus urticae) (twospoked spider mite)) and Varroa destructor (Varroa destructor) (honey bee mite).
Nematoda (nematodes): the species Aphelenchoides (Aphelenchoides spp.) (bud and leaf and pine wood nematodes (bud and leaf & pine wood nematodes)), the species nematodiasis (Belonolaevis spp.) (sting nematodes), the species Cyclotella minor (Criconella spp.) (ring nematodes), the species Dirofilaria immitis (dog heartword), the species Ditylenchus spp. (stem and bulb nematodes), the species Trichophythora (Heterodera spp.) (Cytospora spp.), the species Heterocladia (Heterocladia zeae) (maize nematodides), the species Melilodinia spp. (Hichlamyella spp.) (Melilotus spp.)), the species Heterocladospora spp.) (Melilotus spp.)), the species Melilotus spp.) (Melilotus spp.)), the species (Melilotus spp.)), the species), Melilotus spp.) (Melilotus) and Melilotus spp.) (Melilotus, Melilotus spp.) (Melilotus) and Melilotus spp.) (Melilotus, Melilotus spp.) (Melilotus) and Melilotus, Melilotus spp.) (Melilotus, Melilotus spp.) (Melilotus, Melilotus spp.) (Melilotus ) and Melilotus, Melilotus spp.) (Melilotus, Melilo, The species of the genus Rapholus (Rapholus spp.) (Burrowing nematode) and the species of the Leptochloa (Rotylenchus reniformis) (kidney-shaped nematode).
General class (general classes of insects): white pine worm (Scutigerella immaculata).
Owing to their positive properties, the abovementioned compounds can be used advantageously for protecting crops, domestic animals and breeding animals of agricultural and horticultural importance, as well as the environment in which humans are often exposed, against harmful germs, pests and mites.
The amount of the compound used to achieve the desired effect will vary depending on factors such as the compound used, the crop to be protected, the type of pest, the extent of infection, the climatic conditions, the method of application, and the dosage form employed.
A dose of 10g to 5 kg of compound per hectare provides adequate control.
The invention also discloses a bactericidal, insecticidal and acaricidal composition which takes the compound shown as 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 compound shown in the general formula I is used as an active component to be dissolved or dispersed in a carrier or prepared into a preparation so as to be easier to disperse when being used for sterilization and disinsection. 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 10g to 1000 g per hectare is selected, and an effective amount of 20g to 500 g per hectare is selected.
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 Compounds 15-21
1) Preparation of 1- (2, 4-dichlorophenyl) -1H-pyrazole
Taking 21.35g (0.1mol) of 2, 4-dichlorophenylhydrazine hydrochloride and 16.4g (0.1mol) of 1, 1, 3, 3-tetramethoxypropane in a 250ml three-necked bottle, taking 100ml of 95% ethanol water solution as a solvent, and heating to reflux for reaction for 3-5 hours. After completion of the TLC monitoring reaction, most of the ethanol was distilled off under reduced pressure, an aqueous solution of sodium carbonate was added to the residue, the aqueous phase was extracted with (3X 100ml) ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and desolventized. Column chromatography of the residue (eluent ethyl acetate and petroleum ether in a volume ratio of 1: 10) gave 18.06g of yellow solid in 84.8% yield.
2) Preparation of 1- (2, 4-dichlorophenyl) -1H-pyrazole-4-carbaldehyde
185ml (2.4mol) of N, N-dimethylformamide is taken in a 1000ml three-necked bottle, and mechanical stirring is carried out under ice bath to ensure that the temperature of the reaction system is maintained at-5 ℃ to 0 ℃. 225ml (2.4mol) of phosphorus oxychloride are added dropwise after 10 min. After the dropwise addition, the reaction was continued for 30 min. Then, 127.8g (0.6mol) of 1- (2, 4-dichlorophenyl) -1H-pyrazole was added thereto, and the mixture was reacted at 90 ℃ for 15 hours. After TLC monitoring reaction, the reaction solution was poured into ice water and stirred, made alkaline with aqueous sodium carbonate solution, the aqueous phase was extracted with (3X 150ml) ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and desolventized. Chromatography of the residue (eluent ethyl acetate and petroleum ether in a volume ratio of 1: 5) gave 98.33g of a white solid.
3) Preparation of (1- (2, 4-dichlorophenyl) -1H-pyrazol-4-yl) methanol
24.1g (0.1mol) of 1- (2, 4-dichlorophenyl) -1H-pyrazole-4-carbaldehyde are dissolved in 150ml of absolute ethanol and stirred in an ice bath. After 5 minutes, 9.5g (0.25mol) of sodium borohydride was added in portions to the reaction flask, followed by reaction at room temperature for 4 to 6 hours. After completion of the TLC monitoring reaction, most of the anhydrous ethanol was distilled off under reduced pressure, the reaction was poured into water with stirring, the aqueous phase was extracted with (3X 50ml) ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and desolventized. Chromatography of the residue (eluent ethyl acetate and petroleum ether in a volume ratio of 1: 2) gave 23.38g of a white solid with a yield of 96.2%.
4) Preparation of 4- (chloromethyl) -1- (2, 4-dichlorophenyl) -1H-pyrazole
24.3g (0.1mol) of (1- (2, 4-dichlorophenyl) -1H-pyrazol-4-yl) methanol was dissolved in 120ml of a toluene solution, 14.28g (0.12mol) of thionyl chloride was added dropwise to a flask with stirring at room temperature, and after completion of the addition, the reaction was refluxed for 3 to 4 hours. After the completion of the TLC monitoring reaction, 25.7g of light red brown oil-like liquid was obtained by desolventizing, with a yield of 98.3%.
5) Preparation of 2- (1- (2, 4-dichlorophenyl) -1H-pyrazol-4-yl) acetonitrile
5.88g (0.12mol) of sodium cyanide were taken in a 250ml three-necked flask and 100ml of dimethyl sulfoxide was used as a solvent, and the mixture was stirred at 80 ℃ to be completely dissolved. After 30 minutes, a solution of 22.7g (0.1mol) of 4- (chloromethyl) -1- (2, 4-dichlorophenyl) -1H-pyrazole in N, N-dimethylformamide was added dropwise, followed by reaction for 1 to 3 hours. After completion of the TLC monitoring reaction, the reaction was poured into water with stirring, the aqueous phase was extracted with (3X 80ml) ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulphate, filtered and desolventized. Chromatography of the residue (eluent ethyl acetate and petroleum ether in a volume ratio of 1: 5) gave 23.91g of a white solid with a yield of 94.9%.
6)2- (1- (2, 4-dichlorophenyl) -1H-pyrazol-4-yl) ethylamine
A mixture of 2.52g (0.01mol) of intermediate 2- (1- (2, 4-dichlorophenyl) -1H-pyrazol-4-yl) acetonitrile, Raney nickel (1.0g) and 100ml of a 10% ammonia solution in methanol was reacted under high-pressure hydrogenation conditions at room temperature for 3 hours. After the TLC monitoring reaction, Raney nickel is filtered, and the solvent is removed by evaporation under reduced pressure to obtain 2.52g of light reddish brown viscous liquid with the yield of 98.6 percent.
7) 2.20g (0.01mol) of 2-tert-butyl-4, 5-dichloropyridazinone and 2.55g (0.01mol) of 2- (1- (2, 4-dichlorophenyl) -1H-pyrazol-4-yl) ethylamine hydrochloride are added into 50ml of DMF, 4.45g (0.022mol) of triethylamine is added at room temperature under stirring, the reaction is carried out at 80 to 100 ℃ for 2 to 4 hours, after the completion of the TLC monitoring reaction, water (100ml) and (3X 100ml) of ethyl acetate are added for extraction, the organic phase is washed with 50ml of saturated saline, and after desolventization, column chromatography is carried out on the residue (eluent is ethyl acetate and petroleum ether in a volume ratio of 1: 2) to obtain 15 to 21, 3.42g of brown oil-like compounds with a yield of 78.0%.
1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，2.88(t，2H，CH2)，3.56(m，2H，NCH2)，7.34(dd，1H，Ph-5-H，J＝8.4Hz，J＝2.1Hz)，7.49(d，1H，Ph-6-H，J＝8.4Hz)，7.57(d，1H，Ph-3-H，J＝2.1Hz)，7.63(s，1H，Pyrazole-3-H)，7.66(s，1H，Pyrazole-5-H)，7.72(s，1H，Pyridazinone-H).
Example 2: preparation of Compound 74-1
1) 2.89g (0.02mol) of phenylhydrazine hydrochloride and 3.28g (0.02mol) of 1, 1, 3, 3-tetramethoxypropane are added to 50ml of 95% ethanol. Heating to 80 ℃ for reflux, reacting for 3-6 hours, performing TLC monitoring after the reaction is finished, performing reduced pressure distillation to remove the solvent, adding (3 multiplied by 50ml) ethyl acetate for extraction, washing an organic phase by 50ml of saturated saline solution, performing column chromatography on a residue after desolventization (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃) at a volume ratio of 1: 6) to obtain 2.45g of oily liquid, wherein the yield is 85.0%.
2) Adding 7.3g (0.1mol) of DMF into a 250ml three-necked flask, stirring under an ice salt bath, dropwise adding 15.4g (0.1mol) of phosphorus oxychloride, dropwise adding 2.88g (0.02mol) of N-phenylpyrazole after 1h, heating to 100 ℃, refluxing, reacting for 3-6 h, after TLC monitoring reaction, adding the reaction liquid into ice water, adjusting to neutrality by using sodium carbonate, adding (3 x 50ml) of ethyl acetate for extraction, washing an organic phase by using 50ml of saturated saline, and performing column chromatography on residues after desolventization (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃) at the volume ratio of 1: 5) to obtain 3.10g of white solid with the yield of 90.0%.
3) 1.72g (0.01mol) of 1-phenyl-4-pyrazole formaldehyde is put into a 100ml single-neck bottle, 35ml of ethanol is added, stirring is carried out under ice bath, 0.95g (0.025mol) of sodium borohydride is added in batches, after TLC monitoring reaction is finished, the solvent is evaporated under reduced pressure, 3X 50ml of ethyl acetate is added for extraction, an organic phase is washed by 50ml of saturated saline solution, and after desolventization, column chromatography is carried out on a residue (eluent is ethyl acetate and petroleum ether (boiling range is 60-90 ℃), volume ratio is 1: 4) to obtain 1.53g of white solid, and yield is 88.0%.
4) Adding 1.74g (0.01mol) of 1-phenyl-4-hydroxymethyl pyrazole into a 100ml single-neck bottle, adding 35ml of dichloromethane, stirring in ice bath, dropwise adding 1.43g (0.012mol) of thionyl chloride, arranging a tail gas collecting device, after TLC monitoring reaction is finished, evaporating the solvent under reduced pressure, adding (3 x 50ml) ethyl acetate for extraction, washing an organic phase by 50ml of saturated saline solution, and performing column chromatography on a residue after desolventization (the eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃), the volume ratio is 1: 4) to obtain 1.55g of brown solid, wherein the yield is 81.0%.
5) Adding 2.21g (0.01mol) of dichloropyridazinone and 1.68g (0.03mol) of KOH into 40ml of ethylene glycol, heating to 130 ℃ for refluxing, reacting for 5 hours, cooling the reaction liquid after the TLC monitoring reaction is finished, pouring the reaction liquid into water, adding 20ml of concentrated hydrochloric acid, and acidifying to obtain 1.66g of white solid with the yield of 82.0%.
6) 1.78g (0.01mol) of 1-phenyl-4-chloromethylpyrazole and 2.02g (0.01mol) of 4-hydroxypyridazinone are added to 50ml of DMF. 1.66g (0.012mol) of potassium carbonate is added, the temperature is raised to 90 ℃ for reaction, the reaction is carried out for 4 hours, after the TLC monitoring reaction is finished, ethyl acetate (3 multiplied by 50ml) is added for extraction, an organic phase is washed by 50ml of saturated saline, and after exsolution, column chromatography is carried out on a residue (eluent is ethyl acetate and petroleum ether (boiling range is 60-90 ℃) and the volume ratio is 1: 3) to obtain 2.59g of yellow solid, and the yield is 75.0%. Melting Point 113.4 ℃.
1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.30(s，2H，OCH2)，7.31-7.35(m，1H，Ph-4-H)，7.40-7.50(m，2H，Ph-3，5-H)，7.67(s，1H，Pyrazole-3-H)，7.70(s，1H，Pyrazole-5-H)，7.79(d，2H，Ph-2，6-H，J＝8.1Hz)，8.04(s，1H，Pyridazinone-H).
Example 3: preparation of Compound 124-3
1) 4.29g (0.02mol) of 4, 6-dichloropyridylazine hydrochloride and 3.28g (0.02mol) of 1, 1, 3, 3-tetramethoxypropane are added to 50ml of 95% ethanol. Heating to 80 ℃ for reflux, reacting for 3-6 hours, performing TLC monitoring after the reaction is finished, performing reduced pressure distillation to remove the solvent, adding (3 multiplied by 50ml) ethyl acetate for extraction, washing an organic phase by 50ml saturated saline solution, performing column chromatography on a residue after desolventization (eluent is ethyl acetate and petroleum ether (boiling range is 60-90 ℃) at a volume ratio of 1: 6) to obtain 3.51g of oily liquid, wherein the yield is 82.0%.
2) Adding 7.3g (0.1mol) of DMF into a 250ml three-necked flask, stirring under an ice salt bath, dropwise adding 15.4g (0.1mol) of phosphorus oxychloride, dropwise adding 4.28g (0.02mol) of 4, 6-dichloropyridine-1H-pyrazole after 1H, heating to 100 ℃, refluxing, reacting for 3-6H, monitoring by TLC, adding the reaction liquid into ice water, adjusting to neutrality by using sodium carbonate, adding (3 multiplied by 50ml) of ethyl acetate, extracting, washing an organic phase by using 50ml of saturated saline water, performing column chromatography on a residue after exsolution (eluent is ethyl acetate and petroleum ether (boiling range is 60-90 ℃) and the volume ratio is 1: 5) to obtain 4.11g of white solid, wherein the yield is 85.0%.
3) 2.42g (0.01mol) of N- (4, 6-dichloropyridine) -4-pyrazolecarboxaldehyde is put into a 100ml single-neck bottle, 35ml of ethanol is added, stirring is carried out in ice bath, 0.95g (0.025mol) of sodium borohydride is added in batches, after TLC monitoring reaction is finished, the solvent is evaporated under reduced pressure, 3X 50ml of ethyl acetate is added for extraction, an organic phase is washed by 50ml of saturated saline, and chromatography is carried out on a residue after exsolution (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃), the volume ratio is 1: 4), 2.20g of white solid is obtained, and the yield is 90.2%.
4) 2.44g (0.01mol) of N- (4, 6-dichloropyridine) -4-hydroxymethyl pyrazole is put into a 100ml single-neck bottle, 35ml of dichloromethane is added, stirring is carried out under ice bath, 1.43g (0.012mol) of thionyl chloride is dripped, a tail gas collecting device is arranged, after TLC monitoring reaction is finished, a solvent is evaporated under reduced pressure, 3X 50ml of ethyl acetate is added for extraction, an organic phase is washed by 50ml of saturated saline solution, and residue after exsolution is subjected to column chromatography (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃) and the volume ratio is 1: 4), 2.17g of brown solid is obtained, and the yield is 82.7%.
5) Adding 1.65g (0.02mol) of methylhydrazine into a mixed solution of toluene and water (9: 1) containing 0.08g (0.02mol) of NaOH, adding 3.38g (0.02mol) of furoic acid after reacting for half an hour at room temperature for 1 hour, adding 0.12g (0.02mol) of glacial acetic acid, heating to 45 ℃, reacting for 6-8 hours, adding (3X 50ml) of ethyl acetate after TLC monitoring reaction, extracting, washing an organic phase by 50ml of saturated saline solution, and performing column chromatography on a residue after desolventization (eluent is ethyl acetate and petroleum ether (boiling range is 60-90 ℃) and the volume ratio is 1: 6) to obtain 2.67g of oily liquid with the yield of 75.0 percent.
6) Adding 1.78g (0.01mol) of 4, 6-dichloro-N-methylpyridazinone and 1.68g (0.03mol) of KOH into 40ml of ethylene glycol, heating to 130 ℃, refluxing, reacting for 5 hours, after the reaction is monitored by TLC, cooling the reaction liquid, pouring into water, adding 20ml of concentrated hydrochloric acid, and acidifying to obtain 1.27g of white solid with the yield of 79.6%.
7) 0.24g (0.001mol) of N- (4, 6-dichloropyridine) -4-chloromethylpyrazole and 0.16g (0.001mol) of 4-hydroxy-6-chloro-N-methylpyridazinone are added to 50ml of DMF. 0.17g (0.0012mol) of potassium carbonate was added, the mixture was heated to 90 ℃ to react for 4 hours, after completion of the TLC monitoring, ethyl acetate was added to extract the mixture, the organic phase was washed with 50ml of saturated brine, and the residue was a yellow solid in the column layer after exsolution, yielding 58.0%. Melting point 181.8 ℃.
1H NMR(300MHz，CDCl3)：δ3.81(s，3H，CH3)，5.33(s，2H，OCH2)，7.81(s，1H，Pyrazole-3-H)，7.87(s，1H，Pyridazinone-H)，7.94(s，1H，Pyrazole-5-H)，8.24(s，1H，Pyridine-5-H)，8.39(s，1H，Pyridine-3-H).
Example 4: preparation of Compounds 142-19
1) 3.56g (0.02mol) of p-chlorophenylhydrazine hydrochloride and 3.28g (0.02mol) of 1, 1, 3, 3-tetramethoxypropane are added to 50ml of 95% ethanol. Heating to 80 ℃ for reflux, reacting for 3-6 hours, performing TLC to monitor the reaction, decompressing and distilling to remove the solvent, adding (3X 50ml) ethyl acetate for extraction, washing an organic phase by 50ml of saturated saline solution, performing column chromatography on a residue after desolventization (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃) at a volume ratio of 1: 6) to obtain 3.14g of oily liquid, wherein the yield is 87.9%.
2) Adding 7.3g (0.1mol) of DMF into a 250ml three-necked flask, stirring under an ice salt bath, dropwise adding 15.4g (0.1mol) of phosphorus oxychloride, dropwise adding 3.57g (0.02mol) of N- (4-chlorophenyl) pyrazole after 1h, heating to 100 ℃, refluxing, reacting for 3-6 h, after TLC monitoring reaction, adding the reaction liquid into ice water, adjusting to neutrality by using sodium carbonate, adding (3 x 50ml) of ethyl acetate for extraction, washing an organic phase by using 50ml of saturated saline solution, and performing column chromatography on a residue after desolventization (eluent is ethyl acetate and petroleum ether (boiling range is 60-90 ℃) at a volume ratio of 1: 5) to obtain 3.75g of white solid with the yield of 90.8%.
3) 2.06g (0.01mol) of N- (4-chlorophenyl) -4-pyrazolecarboxaldehyde are placed in a 100ml single-neck flask, 35ml of ethanol are added, stirring is carried out in an ice bath, 0.95g (0.025mol) of sodium borohydride is added in portions, after the TLC monitoring reaction is finished, the solvent is evaporated under reduced pressure, 3X 50ml of ethyl acetate is added for extraction, the organic phase is washed by 50ml of saturated saline, and after exsolution, column chromatography is carried out on the residue (the eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃), the volume ratio is 1: 4) to obtain 1.71g of white solid, and the yield is 82.0%.
4) 2.08g (0.01mol) of N- (4-chlorophenyl) -4-hydroxymethyl pyrazole is put into a 100ml single-neck bottle, 35ml of dichloromethane is added, stirring is carried out in ice bath, 1.43g (0.012mol) of thionyl chloride is added dropwise, a tail gas collecting device is arranged, after TLC monitoring reaction is finished, a solvent is evaporated under reduced pressure, 3X 50ml of ethyl acetate is added for extraction, an organic phase is washed by 50ml of saturated saline solution, and column chromatography is carried out on a residue after desolvation (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃), the volume ratio is 1: 4) to obtain 1.84g of brown solid, and the yield is 81.0%.
5) Adding 2.21g (0.01mol) of dichloropyridazinone into 40ml of ethanol, stirring in an ice bath, dropwise adding 30% NaSH1.68g (0.03mol), stirring for reacting for 2 hours, cooling the reaction liquid, pouring into water after TLC monitoring reaction is finished, adding 20ml of concentrated hydrochloric acid, and acidifying to obtain 1.92g of white solid with the yield of 88.0%.
6) 2.27g (0.01mol) of N- (4-chlorophenyl) -4-chloromethylpyrazole and 2.21g (0.01mol) of 4-mercaptopyridazinone were added to 50ml of DMF. Adding 1.66g (0.012mol) of potassium carbonate, heating to 90 ℃ for reaction, reacting for 4 hours, monitoring the reaction by TLC, adding (3X 50ml) of ethyl acetate for extraction after the reaction is finished, washing an organic phase by 50ml of saturated saline solution, and performing column chromatography on a residue after exsolution (eluent is ethyl acetate and petroleum ether (boiling range is 60-90 ℃), volume ratio is 1: 3) to obtain 142-19, 3.56g of orange solid, and yield is 86.6%. Melting point 153.6 ℃.
1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，4.23(s，2H，SCH2)，7.30-7.35(m，2H，Ph-3，5-H)，7.43(d，2H，Ph-3，5-H，J＝8.7Hz)，7.61(d，2H，Ph-2，6-H，J＝8.7Hz)，7.64(s，1H，Pyrazole-3-H)，7.72(s，1H，Pyrazole-5-H)，7.92(s，1H，Pyridazinone-H).
Example 5: preparation of Compound 194-4
1) 3.54g (0.02mol) of 4-trifluoromethylpyridylhydrazine hydrochloride and 3.28g (0.02mol) of 1, 1, 3, 3-tetramethoxypropane were added to 50ml of 95% ethanol. Heating to 80 ℃ for reflux, reacting for 3-6 hours, performing TLC monitoring after the reaction is finished, performing reduced pressure distillation to remove the solvent, adding (3 multiplied by 50ml) ethyl acetate for extraction, washing an organic phase by 50ml of saturated saline solution, performing column chromatography on a residue after desolventization (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃) at a volume ratio of 1: 6) to obtain 3.44g of oily liquid, wherein the yield is 80.7%.
2) Adding 7.3g (0.1mol) of DMF into a 250ml three-necked flask, stirring under an ice salt bath, dropwise adding 15.4g (0.1mol) of phosphorus oxychloride, dropwise adding 2.13g (0.02mol) of N- (4-trifluoromethylpyridine) pyrazole after 1h, heating to 100 ℃ for refluxing, reacting for 3-6 h, monitoring by TLC, adding the reaction liquid into ice water, adjusting to neutrality by using sodium carbonate, adding 3 x 50ml of ethyl acetate for extraction, washing an organic phase by using 50ml of saturated saline, performing column chromatography on the residue after desolventization (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃) at the volume ratio of 1: 5) to obtain 4.02g of white solid with the yield of 83.4%.
3) 2.41g (0.01mol) of N- (4-trifluoromethylpyridine) -4-pyrazolecarboxaldehyde are put into a 100ml single-neck flask, 35ml of ethanol is added, stirring is carried out in ice bath, 0.95g (0.025mol) of sodium borohydride is added in portions, after TLC monitoring reaction is finished, the solvent is evaporated under reduced pressure, 3X 50ml of ethyl acetate is added for extraction, the organic phase is washed by 50ml of saturated saline, and after desolventization, column chromatography is carried out on the residue (the eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃), the volume ratio is 1: 4) to obtain 1.71g of white solid with the yield of 82.0%.
4) 2.43g (0.01mol) of N- (4-trifluoromethylpyridine) -4-hydroxymethylpyrazole is added into a 100ml single-neck bottle, 35ml of dichloromethane is added, stirring is carried out under ice bath, 1.43g (0.012mol) of thionyl chloride is dropwise added, a tail gas collecting device is arranged, after TLC monitoring reaction is finished, a solvent is evaporated under reduced pressure, 3X 50ml of ethyl acetate is added for extraction, an organic phase is washed by 50ml of saturated saline, and column chromatography is carried out on a residue after desolventization (eluent is ethyl acetate and petroleum ether (the boiling range is 60-90 ℃), the volume ratio is 1: 4) to obtain 1.93g of brown solid, and the yield is 73.9%.
5) Adding 2.21g (0.01mol) of dichloropyridazinone into 40ml of ethanol, stirring in an ice bath, dropwise adding 30% NaSH1.68g (0.03mol), stirring for reacting for 2 hours, cooling the reaction liquid, pouring into water after TLC monitoring reaction is finished, adding 20ml of concentrated hydrochloric acid, and acidifying to obtain 1.92g of white solid with the yield of 88.0%.
6) 2.61g (0.01mol) of N- (4-trifluoromethylpyridine) -4-chloromethylpyrazole and 2.21g (0.01mol) of 4-mercaptopyridazinone were added to 50ml of DMF. Adding 1.66g (0.012mol) potassium carbonate, heating to 90 deg.C for reaction, reacting for 4 hr, monitoring by TLC, adding (3 × 50ml) ethyl acetate for extraction, washing the organic phase with 50ml saturated saline solution, removing solvent, and performing column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90 deg.C), volume ratio is 1: 3) to obtain the final productCompound 194-4, 1.75g red solid, mp 141 ℃. The yield thereof was found to be 39.6%. 1H-NMR (300MHz, internal standard TMS, solvent CDCl3)δ(ppm)：δ1.63(s，9H)，4.32(s，2H)，7.69(d，J＝2.1Hz，1H)，7.78(s，1H)，7.9(s，1H)，8.1(d，J＝2.1Hz，1H)，8.70(s，1H)。
Other compounds of the invention may be prepared by reference to the above examples.
Physical property data and nuclear magnetic data of some of the compounds (1HNMR, 300MHz, internal standard TMS, ppm) as follows:
compounds 15-18: brown oil.1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，2.88(t，2H，CH2)，3.56(m，2H，NCH2)，7.36-7.38(m，2H，Ph-2，6-H)，7.52-7.54(m，2H，Ph-4，5-H)，7.61(s，1H，Pyrazole-3-H)，7.71(s，1H，Pyrazole-5-H)，7.75(s，1H，Pyridazinone-H)。
Compounds 15-1-19: brown oil.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，2.79(t，2H，CH2)，3.47(m，2H，NCH2)，5.23(s，2H，CH2)，7.14(d，2H，Ph-2，6-H，J＝8.4Hz)，7.21(s，1H，Pyrazole-3-H)，7.32(d，2H，Ph-3，5-H，J＝8.4Hz)，7.42(s，1H，Pyrazole-5-H)，7.51(s，1H，Pyridazinone-H)。
Compounds 15-23: a white solid.
Compounds 15-69: brown oil.1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，2.91(t，2H，CH2)，2.91(m，2H，NCH2)，7.55(s，1H，Pyrazole-3-H)，7.65(s，1H，Pyrazole-5-H)，7.71(d，2H，Ph-3，5-H，J＝9.0Hz)，7.78(d，2H，Ph-2，6-H，J＝9.0Hz)，7.82(s，1H，Pyridazinone-H)。
15-70 of compounds: brown oil.1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，2.89(t，2H，CH2)，3.55(m，2H，NCH2)，3.89(s，3H，OCH3)，7.02-7.06(m，2H，Ph-3，5-H)，7.54(s，1H，Pyrazole-3-H)，7.58(s，1H，Pyrazole-5-H)，7.64-7.66(m，2H，Ph-4，6-H)，7.89(s，1H，Pyridazinone-H)。
Compounds 15-72: brown oil.1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，2.88(t，2H，CH2)，3.54(m，2H，NCH2)，3.84(s，3H，OCH3)，6.97(d，2H，Ph-3，5-H，J＝9.3Hz)，7.53(d，2H，Ph-2，6-H，J＝9.3Hz)，7.55(s，1H，Pyrazole-3-H)，7.57(s，1H，Pyrazole-5-H)，7.66(s，1H，Pyridazinone-H)。
Compounds 15-158: brown oil.1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，2.89(t，2H，CH2)，3.55(m，2H，NCH2)，7.24-7.28(m，2H，Ph-5，6-H)，7.54(s，1H，Pyrazole-3-H)，7.62(s，1H，Pyrazole-5-H)，7.83(m，1H，Ph-3-H)，7.84(s，1H，Pyridazinone-H)。
Compound 71-6: brown oil.1H NMR(300MHz，CDCl3)：δ5.29(s，2H，OCH2)，6.96-7.03(m，2H，Ph-3，5-H)，7.76(s，1H，Pyrazole-3-H)，7.83(s，1H，Pyrazole-5-H)，7.82-7.85(m，1H，Ph-6-H)，8.10(s，1H，Pyridazinone-H)。
Compounds 71-158: yellow solid, mp 113.4 ℃.1H NMR(300MHz，CDCl3)：δ5.08(s，2H，OCH2)，7.23-7.27(m，1H，Ph-3-H)，7.66(s，1H，Pyrazole-3-H)，7.72(d，1H，Ph-5-H，J＝8.4Hz)，7.80(s，1H，Pyrazole-5-H)，7.85(d，1H，Ph-6-H，J＝8.4Hz)，8.00(s，1H，Pyridazinone-H)。
Compound 72-1: white solid, melting point 252 ℃.1H NMR(300MHz，CDCl3)：δ3.80(s，3H，CH3)，5.33(s，2H，OCH2)，7.34(d，1H，Ph-4-H，J＝7.2Hz)，7.47(dd，2H，Ph-3，5-H，J＝7.2Hz，J＝8.4Hz)，7.78(s，1H，Pyrazole-3-H)，7.82(s，1H，Pyrazole-5-H)，7.67(d，2H，Ph-2，6-H，J＝8.4Hz)，8.03(s，1H，Pyridazinone-H)。
Compound 72-6: yellow solid, mp 171.4 ℃.1H NMR(300MHz，CDCl3)：δ3.81(s，3H，CH3)，5.32(s，2H，OCH2)，6.95(s，1H，Ph-3-H)，7.03(d，1H，Ph-5-HJ＝5.1Hz)，7.80(s，1H，Pyrazole-3-H)，7.85(s，1H，Pyrazole-5-H)，7.88(d，1H，Ph-6-H，J＝5.1Hz)，8.04(s，1H，Pyridazinone-H)。
Compounds 72-19: white solid, mp 186.5 ℃.1H NMR(300MHz，CDCl3)：δ3.81(s，3H，CH3)，5.32(s，2H，OCH2)，7.44(d，2H，Ph-3，5-H，J＝6.9Hz)，7.63(d，2H，Ph-2，6-H，J＝6.9Hz)，7.78(s，1H，Pyrazole-3-H)，7.82(s，1H，Pyrazole-5-H)，8.00(s，1H，Pyridazinone-H)。
Compound 72-21: yellow solid, melting point 203 ℃.1H NMR(300MHz，CDCl3)：δ3.81(s，3H，NHCH3)，5.33(s，2H，OCH2)，7.39-7.55(m，2H，Ph-5，6-H)，7.57(s，1H，Pyrazole-3-H)，7.80(s，1H，Ph-3-H)，7.81(s，1H，Pyrazole-5-H)，7.97(s，1H，Pyridazinone-H)。
Compounds 72-49: yellow solid, mp 154.9 ℃.1H NMR(300MHz，CDCl3)：δ3.80(s，3H，CH3)，5.36(s，2H，OCH2)，6.49(s，1H，Pyrazole-3-H)，7.51(d，2H，Ph-3，5-H，J＝8.4Hz)，7.76(d，2H，Ph-2，6-H，J＝8.4Hz)，7.95(s，1H，Pyrazole-5-H)，8.00(s，1H，Pyridazinone-H)。
Compounds 72-69: yellow solid, melting point 112.8 ℃.1H NMR(300MHz，CDCl3)：δ3.77(s，3H，CH3)，5.69(s，2H，OCH2)，7.65(d，2H，Ph-3，5-H，J＝6.9Hz)，7.75(d，2H，Ph-2，6-H，J＝6.9Hz)，7.81(s，1H，Pyrazole-3-H)，8.00(s，1H，Pyrazole-5-H)，8.02(s，1H，Pyridazinone-H)。
Compounds 72-72: brown oil.1H NMR(300MHz，CDCl3)：δ3.81(s，3H，OCH3)，5.32(s，2H，OCH2)，6.97(d，2H，Ph-3，5-H，J＝9.3Hz)，7.56(d，2H，Ph-2，6-H，J＝9.3Hz)，7.71(s，1H，Pyrazole-3-H)，7.89(s，1H，Pyrazole-5-H)，8.00(s，1H，Pyridazinone-H)。
Compounds 72-158: yellow solid, mp 155.4 ℃.1H NMR(300MHz，CDCl3)：δ3.77(s，3H，CH3)，5.69(s，2H，OCH2)，7.23-7.27(m，1H，Ph-3-H)，7.66(s，1H，Pyrazole-3-H)，7.72(d，1H，Ph-5-H，J＝8.4Hz)，7.80(s，1H，Pyrazole-5-H)，7.85(d，1H，Ph-6-H，J＝8.4Hz)，8.07(s，1H，Pyridazinone-H)。
Compounds 73-69: yellow solid, mp 129.4 ℃.1H NMR(300MHz，CDCl3)：δ1.30(dd，6H，J＝3.0Hz，NCH(CH3)2)，5.26(q，H，CH，J＝4.5Hz)，5.66(s，2H，CH2)，7.70(s，1H，Pyrazol-3-H)，7.73(s，Pyrazol-5-H)，7.74(dd，2H，Ph-2，6-H)，7.82(dd，2H，Ph-3，5-H)，8.12(s，1H，Pyridazinome-H)。
Compound 74-4: brown solid, melting point 102 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，5.30(s，2H，OCH2)，7.16-7.19(m，2H，Ph-2，6-H)，7.62-7.65(m，2H，Ph-3，5-H)，7.77(s，1H，Pyrazole-3-H)，7.80(s，1H，Pyrazole-5-H)，7.97(s，1H，Pyridazinone-H)。
Compounds 74-6: yellow solid, mp 127.5 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.30(s，2H，OCH2)，6.95(s，1H，Ph-3-H)，7.03(d，1H，Ph-5-HJ＝5.1Hz)，7.80(s，1H，Pyrazole-3-H)，7.85(s，1H，Pyrazole-5-H)，7.88(d，1H，Ph-6-H，J＝5.1Hz)，8.04(s，1H，Pyridazinone-H)。
Compounds 74-1-19: yellow solid, mp 140.4 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，5.21(s，2H，OCH2)，5.27(s，2H，NCH2)，7.17(d，2H，Ph-2，6-H，J＝7.5Hz)，7.31(d，2H，Ph-3，5-H，J＝7.5Hz)，7.49(s，1H，Pyrazole-3-H)，7.60(s，1H，Pyrazole-5-H)，7.75(s，1H，Pyridazinone-H)。
Compounds 74-19: yellow solid, mp 136.5 ℃.1H NMR(300MHz，CDCl3)：δ1.63(s，9H)，5.32(s，2H)，7.43(d，J＝9.0Hz，2H)，7.63(d，J＝9.0Hz，2H)，7.78(s，1H)，7.80(s，1H)，8.00(s，1H)。
Compounds 74-20: a yellow oil.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.33(s，2H，OCH2)，7.31-7.34(m，1H，Ph-5-H)，7.47(d，1H，Ph-6-H，J＝6.0Hz)，7.54(d，1H，Ph-4-H，J＝6.0Hz)，7.66(s，1H，Pyrazole-3-H)，7.75(s，1H，Pyrazole-5-H)，7.96(s，1H，Pyridazinone-H)。
Compounds 74-21: yellow solid, mp 165.9 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.32(s，2H，OCH2)，7.39-7.55(m，2H，Ph-5，6-H)，7.57(s，1H，Pyrazole-3-H)，7.80(s，1H，Ph-3-H)，7.81(s，1H，Pyrazole-5-H)，7.97(s，1H，Pyridazinone-H)。
Compounds 74-23: yellow solid, melting point 160.4 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，5.36(s，2H，OCH2)，7.39-7.48(m，3H，Ph-3，4，5-H)，7.64(s，1H，Pyrazole-3-H)，7.77(s，1H，Pyrazole-5-H)，7.86(s，1H，Pyridazinone-H)。
Compounds 74-25: yellow solid, mp 153.8 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.30(s，2H，OCH2)，7.31(s，1H，Pyrazole-3-H)，7.63(s，1H，Pyrazole-5-H)，7.64(s，1H，Ph-4-H)，7.80(s，2H，Ph-2，6-H)，8.02(s，1H，Pyridazinone-H)。
Compounds 74-31: white solid, melting point 151.9 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.29(s，2H，OCH2)，7.30(s，1H，Pyrazole-3-H)，7.79(s，1H，Pyrazole-5-H)，7.63(s，2H，Ph-2，6-H)，8.01(s，1H，Pyridazinone-H)。
Compounds 74-52: yellow solid, mp 178.7 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.32(s，2H，OCH2)，7.79(s，1H，Pyrazole-3-H)，7.86(s，1H，Pyrazole-5-H)，7.89(d，2H，Ph-2，6-H，J＝9.3Hz)，8.15(s，1H，Pyridazinone-H)，8.35(d，2H，Ph-3，5-H，J＝9.3Hz)。
Compounds 74-57: a red oil.1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，2.38(s，2H，CH3)，5.29(s，2H，OCH2)，7.25(d，2H，Ph-3，5-H，J＝8.4Hz)，7.55(d，2H，Ph-2，6-H，J＝8.4Hz)，7.76(s，1H，Pyrazole-3-H)，7.80(s，1H，Pyrazole-5-H)，7.99(s，1H，Pyridazinone-H)。
Compounds 74-69: yellow solid, mp 129.3 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，NCH3)，5.32(s，2H，CH2)，7.72(s，1H，Pyrazol-3-H)，7.75(s，Pyrazol-5-H)，7.81(dd，4H，Ph-H，J＝4.5Hz)，8.10(s，1H，Pyridazinone-H)。
Compounds 74-72: yellow solid, mp 133 ℃.1H NMR(300MHz，CDCl3)：δ1.62(s，9H)，5.24(s，2H)，7.43(d，J＝9.0Hz，2H)，7.63(d，J＝9.0Hz，2H)，7.78(s，1H)，7.81(s，1H)，8.02(s，1H)。
Compounds 74-158: brown solid, m.p. 175.8 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.30(s，2H，OCH2)，7.28(s，1H，Pyrazole-3-H)，7.79(s，1H，Pyrazole-5-H)，7.80(d，1H，Ph-5-H，J＝2.1Hz)，7.83(s，1H，Ph-3-H)，8.08(d，1H，Ph-6-H，J＝2.1Hz)。
Compound 126-2: white solid, melting point 148.6 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H)，5.32(s，2H)，7.69(d，J＝2.1Hz，1H)，7.78(s，1H)，7.9(s，1H)，8.1(d，J＝2.1Hz，1H)，8.70(s，1H)。
Compound 126-3: yellow solid, mp 127.5 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，5.33(s，2H，OCH2)，7.79(s，1H，Pyrazole-3-H)，7.88(s，1H，Pyrazole-5-H)，7.94(d，1H，Pyridine-4-H，J＝2.1Hz)，8.25(s，1H，Pyridazinone-H)，8.40(d，1H，Pyridine-6-H，J＝2.1Hz)。
Compound 140-1: yellow solid, mp 85.3 ℃.1H NMR(300MHz，CDCl3)：δ4.15(s，3H，CH3)，5.37(s，2H，SCH2)，7.31-7.34(m，1H，Ph-4-H)，7.44-7.49(m，2H，Ph-3，5-H)，7.67(s，1H，Pyrazole-3-H)，7.70(m，2H，Ph-2，6-H)，7.83(s，1H，Pyrazole-5-H)，8.07(s，1H，Pyridazinone-H)。
Compound 140-4: brown oil.1H NMR(300MHz，CDCl3)：δ3.77(s，3H，CH3)，4.46(s，2H，SCH2)，7.44(d，2H，Ph-3，5-H，J＝6.9Hz)，7.63(d，2H，Ph-2，6-H，J＝6.9Hz)，7.81(s，1H，Pyrazole-3-H)，7.88(s，1H，Pyrazole-5-H)，8.02(s，1H，Pyridazinone-H)。
Compound 140-6: white solid, melting point 98.1 ℃.1H NMR(300MHz，CDCl3)：δ4.15(s，3H，CH3)，5.36(s，2H，SCH2)，7.37(dd，1H，Ph-5-H，J＝8.4Hz，J＝2.1Hz)，7.44(s，1H，Pyrazole-3-H)，7.50(d，1H，Ph-6-H，J＝8.4Hz)，7.50(d，1H，Ph-3-H，J＝2.1Hz)，7.85(s，1H，Pyrazole-5-H)，8.08(s，1H，Pyridazinone-H)。
Compounds 140-19: brown solid, m.p. 89.6 ℃.1H NMR(300MHz，CDCl3)：δ4.15(s，3H，CH3)，5.36(s，2H，SCH2)，7.44(d，2H，Ph-3，5-H，J＝6.9Hz)，7.63(d，2H，Ph-2，6-H，J＝6.9Hz)，7.78(s，1H，Pyrazole-3-H)，7.82(s，1H，Pyrazole-5-H)，8.02(s，1H，Pyridazinone-H)。
Compounds 140-21: brown solid, melting point 110.3 ℃.1H NMR(300MHz，CDCl3)：δ4.15(s，3H，CH3)，5.37(s，2H，SCH2)，7.37(dd，1H，Ph-5-H，J＝8.4Hz，J＝2.1Hz)，7.44(s，1H，Pyrazole-3-H)，7.50(d，1H，Ph-6-H，J＝8.4Hz)，7.58(d，1H，Ph-3-H，J＝2.1Hz)，7.85(s，1H，Pyrazole-5-H)，8.03(s，1H，Pyridazinone-H)。
Compounds 140-69: brown oil。1H NMR(300MHz，CDCl3)：δ3.77(s，3H，CH3)，4.48(s，2H，SCH2)，7.65(d，2H，Ph-3，5-H，J＝6.9Hz)，7.75(d，2H，Ph-2，6-H，J＝6.9Hz)，7.81(s，1H，Pyrazole-3-H)，8.00(s，1H，Pyrazole-5-H)，8.02(s，1H，Pyridazinone-H)。
Compound 142-1: orange solid, melting point 129.8 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，4.24(s，2H，SCH2)，7.30-7.35(m，2H，Ph-3，5-H)，7.46(t，1H，Ph-4-H，J＝7.2Hz)，7.65(s，1H，Pyrazole-3-H)，7.67(d，2H，Ph-2，6-H，J＝7.2Hz)，7.73(s，1H，Pyrazole-5-H)，7.96(s，1H，Pyridazinone-H)。
Compound 142-4: yellow solid, melting point 129 ℃.1H NMR(300MHz，CDCl3)：δ1.63(s，9H)，5.32(s，2H)，7.23(d，J＝9.0Hz，2H)，7.63(d，J＝9.0Hz，2H)，7.78(s，1H)，7.80(s，1H)，7.95(s，1H)。
Compound 142-6: yellow solid, mp 124.9 ℃.1H NMR(300MHz，CDCl3)：δ1.61(s，9H，t-Bu-H)，4.55(s，2H，SCH2)，6.96(s，1H，Ph-3-H)，7.00(d，1H，Ph-5-H)，7.74(s，1H，Pyrazole-5-H)，7.84(s，1H，Ph-5-H)，7.93(s，1H，Pyrazole-3-H)。
Compounds 142-20: a yellow oil.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，4.25(s，2H，SCH2)，7.31-7.34(m，1H，Ph-5-H)，7.47(d，1H，Ph-6-H，J＝6.0Hz)，7.54(d，1H，Ph-4-H，J＝6.0Hz)，7.66(s，1H，Pyrazole-3-H)，7.75(s，1H，Pyrazole-5-H)，7.85(s，1H，Pyridazinone-H)。
Compounds 142-21: brown solid, melting point 152 ℃.1H NMR(300MHz，CDCl3)：δ1.65(s，9H，t-Bu-H)，4.55(s，2H，SCH2)，7.39-7.55(m，2H，Ph-5，6-H)，7.57(s，1H，Pyrazole-3-H)，7.80(s，1H，Ph-3-H)，7.81(s，1H，Pyrazole-5-H)，7.97(s，1H，Pyridazinone-H)。
Compounds 142-23: brown solid, m.p. 170.5 ℃.1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，4.26(s，2H，SCH2)，7.36-7.47(m，3H，Ph-3，4，5-H)，7.54(s，1H，Pyrazole-3-H)，7.63(s，1H，Pyrazole-5-H)，7.81(s，1H，Pyridazinone-H)。
Compounds 142-25: yellow solid, melting point 145.4 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，4.22(s，2H，SCH2)，7.28(s，1H，Ph-4-H，J＝1.8Hz)，7.61(d，2H，Ph-2，6-H，J＝1.8Hz)，7.62(s，1H，Pyrazole-3-H)，7.74(s，1H，Pyrazole-5-H)，7.94(s，1H，Pyridazinone-H)。
Compounds 142-57: a red oil.1H NMR(300MHz，CDCl3)：δ1.63(s，9H，t-Bu-H)，2.38(s，3H，CH3)，4.43(s，2H，OCH2)，7.25(d，2H，Ph-3，5-H，J＝8.4Hz)，7.55(d，2H，Ph-2，6-H，J＝8.4Hz)，7.76(s，1H，Pyrazole-3-H)，7.80(s，1H，Pyrazole-5-H)，7.99(s，1H，Pyridazinone-H)。
Compounds 142-72: yellow solid, mp 134.5 ℃.1H NMR(300MHz，CDCl3)：δ1.62(s，9H)，5.24(s，2H)，7.43(d，J＝9.0Hz，2H)，7.63(d，J＝9.0Hz，2H)，7.78(s，1H)，7.81(s，1H)，8.02(s，1H)。
Compound 142-158: brown solid, m.p. 115.5 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，4.23(s，2H，SCH2)，7.24-7.29(m，2H，Ph-5，6-H)，7.65(s，1H，Pyrazole-3-H)，7.74(s，1H，Pyrazole-5-H)，7.85(s，1H，Ph-3-H)，8.00(s，1H，Pyridazinone-H)。
Compound 162-4: yellow solid, melting point 116.1 ℃.1H NMR(300MHz，CDCl3)：δ1.62(s，9H，t-Bu-H)，1.78(d，J＝6.9Hz，3H，CH3)，4.75(q，J＝6.9Hz，1H，CH)，7.14-7.26(m，2H，Ph-3，5-H)，7.60-7.64(m，3H，Ph-2，6-H+Pyridazinone-H)，7.72(s，1H，Pyrazole-3-H)，7.87(s，1H，Pyrazole-5-H)。
Compound 247-4: yellow solid, mp 163.6 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，4.26(s，2H，SCH2)，7.18-7.24(m，2H，Ph-3，5-H)，7.67-7.71(m，2H，Ph-2，6-H)，7.73(s，1H，Pyridazinone-H)，8.18(s，1H，Pyrazole-3-H)，8.47(s，1H，Pyrazole-5-H)。
Compounds 265-19: yellow solid, mp 121.2 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，4.61(t，J＝6.0Hz，1H，OCH2)，4.65(t，J＝6.0Hz，1H，OCH2)，5.93(s，1H，Pyrazole-4-H)，7.39(d，J＝6.0Hz，2H，Ph-3，5-H)，7.53(d，J＝6.0Hz，2H，Ph-2，6-H)，7.71(s，1H，Pyrazole-5-H)，7.84(s，1H，Pyridazinone-H)。
Compounds 275-19: yellow solid, mp 131.5 ℃.1H NMR(300MHz，CDCl3)：δ1.64(s，9H，t-Bu-H)，3.48(t，J＝6.0Hz，1H，SCH2)，4.53(t，J＝6.0Hz，1H，OCH2)，5.90(s，1H，Pyrazole-4-1H)，7.39(d，J＝6.0Hz，2H，Ph-3，5-2H)，7.56(d，J＝6.0Hz，2H，Ph-2，6-2H)，7.71(s，1H，Pyrazole-5-1H)，8.09(s，1H，Pyridazinone-H)。
Compound 287-4: white solid, melting point 159.9 ℃.1H NMR(300MHz，CDCl3)：δ1.44(s，9H，t-Bu-H)，1.65(s，9H，t-Bu-H)，5.31(s，2H，OCH2)，6.25(s，1H，Pyrazole-4-H)，7.08(t，2H，Ph-3，5-H)，7.31(t，2H，Ph-2，6-H)，8.08(s，1H，Pyridazinone-6-H)。
Compound 291-4: pink solid, melting point 109.0 ℃.1H NMR(300MHz，CDCl3)：δ1.41(s，9H，t-Bu-H)，1.64(s，9H，t-Bu-H)，4.25(s，2H，OCH2)，6.12(s，1H，Pyrazole-4-H)，7.07(t，2H，Ph-3，5-H)，7.29(t，2H，Ph-2，6-H)，8.02(s，1H，Pyridazinone-6-H)。
Compounds 240-21: yellow solid.
Meanwhile, other compounds shown in the general formula I of the invention can be obtained by replacing corresponding raw materials according to the contents described in the above synthetic examples or by the preparation method described in the contents 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 6: measurement of fungicidal Activity
The compound sample of the invention is used for carrying out in vitro bacteriostatic activity or in vivo protection effect tests on various fungal diseases of plants. The results of the bactericidal activity measurement are shown in the following examples.
(1) In vitro bactericidal activity assay
The measurement method is as follows: the high-throughput screening method is adopted, i.e. a compound sample to be detected is dissolved by using a proper solvent (the type of the solvent is acetone, methanol, DMF, and the like, and is selected according to the dissolving capacity of the solvent on the sample), and a liquid to be detected with the required concentration is prepared. Under an ultraclean working environment, adding a solution to be detected into micropores of a 96-hole culture plate, adding a pathogen propagule suspension into the micropore, and placing the treated culture plate in a constant-temperature incubator for culture. And (4) after 24 hours, carrying out investigation, visually observing the germination or growth condition of the pathogen propagules during the investigation, and evaluating the bacteriostatic activity of the compound according to the germination or growth condition of the control treatment.
The results of the in vitro bacteriostatic activity (expressed as inhibition) test of some compounds are as follows:
inhibition rate against rice blast germs:
at a dosage of 25ppm, the inhibition rate of compounds such as 15-18, 15-21, 15-69, 15-72, 15-1-19, 15-158, 72-49, 74-1, 74-4, 74-19, 74-23, 74-52, 74-57, 74-72, 74-158, 126-3, 140-1, 140-4, 140-19, 140-21, 142-1, 142-6, 142-19, 142-23 and the like on rice blast is more than 80%.
At a dose of 8.3ppm, the inhibition rate of rice blast by compounds such as 15-69, 15-158, 126-3, etc. was 80%.
(2) Living body protecting Activity assay
The measurement method is as follows: the living potted plant determination method is adopted, i.e. a sample of the compound to be tested is dissolved by a small amount of solvent (the type of the solvent is acetone, methanol, DMF, etc., and is selected according to the dissolving capacity of the solvent to the sample, and the volume ratio of the solvent amount to the liquid spraying amount is equal to or less than 0.05), and diluted by water containing 0.1 percent of Tween 80 to prepare the liquid to be tested with the required concentration. The solution to be tested is sprayed on diseased host plants (the host plants are standard potted seedlings cultured in a greenhouse) on a crop sprayer, and disease inoculation is carried out after 24 hours. According to the characteristics of diseases, inoculating the disease plants needing temperature and moisture control culture, then culturing in an artificial climate chamber, transferring into a greenhouse for culture after the diseases are infected, and directly inoculating and culturing the disease plants without moisture control culture in the greenhouse. The compound disease control effect evaluation is carried out after the control is sufficiently ill (usually, one week).
The results of the in vivo protective activity test of some compounds are as follows:
in vivo protective activity against cucumber downy mildew:
such as compounds 15-18, 15-21, 15-23, 15-69, 15-70, 15-72, 15-158, 15-1-19, 71-158, 72-1, 72-19, 72-49, 72-72, 72-158, 74-1, 74-4, 74-19, 74-20, 74-21, 74-23, 74-25, 74-31, 74-52, 74-57, 74-69, 74-72, 74-158, 126-2, 126-3, 140-1, 140-21, 142-1, 142-4, 142-6, 142-19, 142-23, 142-57, 162-4, 194-4, 74-6, 124-3, at a dose of 400ppm, 73-69, 74-1-19, 142-72, 240-21 and the like, and the control effect on cucumber downy mildew is more than 80 percent.
At a dose of 100ppm, the control effect of the compounds such as 15-23, 74-6, 74-19, 74-72, 126-2, 126-3, 142-1, 142-4, 142-19, 142-23, 162-4, 194-4, 74-21, 74-52, 74-158, 15-158, 73-69, 74-1, 74-23, 74-57, 74-69, 142-6 and the like on cucumber downy mildew is more than 80 percent.
At the dose of 6.25ppm, the control effect of the compounds such as 74-19, 74-72, 126-2, 142-19 and the like on cucumber downy mildew is more than 80 percent.
In vivo protective activity against wheat powdery mildew:
at a dose of 400ppm, for example, compounds 15-21, 73-69, 74-4, 74-6, 74-19, 74-23, 74-72, 142-1, 142-19, 142-21, 142-23, 142-158 showed a control effect of more than 80% on wheat powdery mildew.
At the dose of 100ppm, the control effect of the compounds 73-69, 142-158 and the like on the wheat powdery mildew is more than 80 percent.
In vivo protective activity against corn rust:
at a dose of 400ppm, for example, the compounds 15-18, 15-21, 15-23, 15-158, 71-158, 72-19, 72-158, 73-69, 74-4, 74-6, 74-19, 74-23, 74-25, 74-69, 74-72, 74-158, 126-2, 126-3, 140-1, 142-4, 142-6, 142-19, 142-23, 142-72, 142-158, 162-4 and 194-4 have more than 80% of the effect on corn rust.
At the dosage of 100ppm, the control effect of the compounds such as 15-18, 15-158, 73-69, 74-4, 74-6, 74-23, 74-69, 74-158, 126-2, 142-1, 142-6, 142-72, 142-158, 162-4 and the like on the corn rust is more than 80 percent.
At the dose of 6.25ppm, the control effect of the compounds such as 74-4, 74-6, 74-69, 74-158, 142-6, 142-158 and the like on the corn rust is more than 80 percent.
In vivo protective activity against cucumber anthracnose:
at a dose of 400ppm, the control effect of the compounds such as 72-6, 73-69, 74-1, 74-6, 74-19, 74-25, 74-31, 74-57, 74-158, 124-3, 140-1, 140-19, 142-4, 142-6, 142-72, 194-4, 240-21 and the like on cucumber anthracnose is more than 80 percent.
At a dose of 100ppm, the control effect of the compounds such as 74-1, 74-6, 74-57, 74-158, 142-4 and the like on cucumber anthracnose is more than 80 percent.
The other compounds of the general formula I of the present invention obtained according to the contents described in the above synthetic examples all have the corresponding effect of controlling pathogenic bacteria.
Example 7: determination of insecticidal Activity
Several insects were tested for insecticidal activity using the compounds of the present invention. The measurement method is as follows:
after dissolving a test compound in a mixed solvent of acetone/methanol (1: 1), the test compound was diluted with water containing 0.1% (wt) Tween 80 to a desired concentration.
The insecticidal activity is determined by taking diamondback moth, armyworm, aphid and tetranychus cinnabarinus as targets and adopting an airrbrush spraying method.
(1) Activity assay for killing diamondback moth
The determination method comprises the following steps: the cabbage leaves were punched out into a 2 cm-diameter disk by a punch, and the pressure of airbrush spray treatment was 10psi (approximately 0.7 kg/cm)2) Spraying on the front and back sides of each leaf disc, wherein the liquid spraying amount is 0.5 ml. After drying in the shade, 10 test insects of 2 years old are inoculated in each treatment, and the treatment is repeated for 3 times. And (4) after treatment, placing the treated mixture into an observation room with the temperature of 25 ℃ and the relative humidity of 60-70% for culture, investigating the number of the survival insects after 72 hours, and calculating the mortality.
The results of the activity of some compounds on diamond back moth are as follows:
when the concentration of the liquid medicine is 600mg/L, the lethality of the compounds 15-72, 15-158, 72-6, 74-1, 74-4, 74-6, 74-72, 74-158, 142-1, 142-72, 194-4 and the like to the plutella xylostella is higher than 80%.
(2) Activity assay for armyworm killing
The determination method comprises the following steps: the corn leaves were cut into 2cm long sections and the airbrush spray treatment pressure was 10psi (approx. 0.7 kg/cm)2) Spraying on the front and back sides of each leaf segment, wherein the liquid spraying amount is 0.5 ml. After drying in the shade, 10 test insects of 2 years old are inoculated in each treatment, and the treatment is repeated for 3 times. And (4) after treatment, placing the treated mixture into an observation room with the temperature of 25 ℃ and the relative humidity of 60-70% for culture, investigating the number of the survival insects after 72 hours, and calculating the mortality.
The activity results of some compounds against armyworm are as follows:
when the concentration of the liquid medicine is 600mg/L, the fatality rate of the compounds 74-1, 74-4, 74-19, 74-158, 126-2, 142-19, 142-72, 194-4 and the like to armyworms is higher than 80%.
(3) Determination of aphid-killing Activity
The determination method comprises the following steps: a culture dish with the diameter of 6cm is taken, a layer of filter paper is covered on the bottom of the culture dish, and a proper amount of tap water is dripped for moisturizing. And (3) shearing cabbage leaves with proper size (the diameter is about 3cm) and 15-30 heads of aphids from the cabbage plants for culturing the myzus persicae, removing the aphids with the wing aphids and the front sides of the leaves, and placing the leaves in a culture dish with the back sides upward. The pressure of the airbrush spray treatment was 10psi (approximately 0.7 kg/cm)2) The amount of the sprayed solution was 0.5ml, and the treatment was repeated 3 times. And (3) after treatment, placing the treated mixture into an observation room with the temperature of 25 ℃ and the relative humidity of 60-70% for culture, investigating the number of the survival insects after 48 hours, and calculating the mortality.
The results of aphid activity of some compounds are as follows:
when the concentration of the liquid medicine is 600mg/L, the lethality of the compounds 74-1, 74-4, 74-6, 74-19, 74-158 and the like to aphids is higher than 80%.
(4) Activity measurement for killing tetranychus cinnabarinus
The determination method comprises the following steps: collecting two bean seedlings of true leaf vegetable, inoculating Tetranychus cinnabarinus, examining the base number, and treating with airrbrush sprayer under 10psi (about 0.7 kg/cm)2) The amount of the sprayed liquid was 0.5 ml. Each treatment was repeated 3 times, and after treatment, the treated mites were placed in a standard observation room, and after 72 hours, the number of live mites was investigated, and the mortality was calculated.
The results of the activity of some compounds on tetranychus cinnabarinus are as follows:
when the concentration of the liquid medicine is 600mg/L, the lethality of the compounds 15-158, 74-1, 74-4, 74-6, 74-19, 74-21, 74-31, 74-72, 74-158, 126-2, 126-3, 142-1, 142-4, 142-19, 142-21, 142-23, 142-57, 142-72, 142-158 and 194-4, etc. to Tetranychus cinnabarinus is higher than 80%.
When the concentration of the liquid medicine is 100mg/L, the lethality of the compounds 74-1, 74-4, 74-6, 74-19, 74-21, 74-72, 74-158, 126-2, 126-3, 142-4, 142-72, 142-158 and the like to tetranychus cinnabarinus is higher than 80 percent.
When the concentration of the liquid medicine is 10mg/L, the lethality of the compounds 74-21, 74-158, 126-2, 142-4 and the like to tetranychus cinnabarinus is high by 80 percent.

Claims (5)

1. A pyridazinone compound characterized by: the pyridazinone compound is a compound shown as a general formula I,
Figure 702618DEST_PATH_IMAGE002
in the formula:
R1selected from unsubstituted or substituted by 1-5R6Substituted phenyl or pyridyl;
R2、R3are respectively selected from hydrogen;
R4selected from halogens;
R5selected from hydrogen or C1-C12An alkyl group;
R6selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, C1-C12Alkylthio, halo C1-C12Alkylthio radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12An alkyl group;
x is selected from NR9O or S;
l is C1-C2A linear saturated alkyl chain;
w is selected from a bond, O or S;
R9selected from hydrogen;
when X is NH and W is a bond, R1Is not unsubstituted phenyl.
2. The pyridazinone-based compound according to claim 1, characterized in that: the compound of the general formula I is shown in the general formula
Figure 150917DEST_PATH_IMAGE003
-A、
Figure 727392DEST_PATH_IMAGE003
-B、I-C、
Figure 653759DEST_PATH_IMAGE003
-B’、
Figure 202552DEST_PATH_IMAGE003
A compound represented by the formula-J,
Figure 556173DEST_PATH_IMAGE005
Figure 619944DEST_PATH_IMAGE006
Figure DEST_PATH_IMAGE007
wherein the content of the first and second substances,
R4selected from halogens;
R5selected from hydrogen or C1-C4An alkyl group;
R6selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio or halogeno C1-C4An alkylthio group; n = 0-3;
l is C1-C2A linear saturated alkyl chain;
R9selected from hydrogen;
y is selected from CH or N;
R10、R11each independently selected from hydrogen or C1-C4An alkyl group;
in that
Figure 84424DEST_PATH_IMAGE003
-A、
Figure 550040DEST_PATH_IMAGE003
-B、I-C、
Figure 573097DEST_PATH_IMAGE003
-B’、
Figure 61848DEST_PATH_IMAGE003
-J, in, R2Selected from hydrogen;
in that
Figure 330018DEST_PATH_IMAGE003
-A、
Figure 650141DEST_PATH_IMAGE003
-B、I-C、
Figure 814406DEST_PATH_IMAGE003
-B’、
Figure 587190DEST_PATH_IMAGE003
-J, in, R3Selected from hydrogen;
in that
Figure 659051DEST_PATH_IMAGE003
In A, when Y is selected from CH, n is not 0.
3. Use of pyridazinone compounds of the general formula I as claimed in claim 1 or of the general formula I-A, I-B, I-C, I-B', I-J as claimed in claim 2 for the preparation of fungicides, insecticides and acaricides in the agricultural field.
4. The bactericidal, insecticidal and acaricidal composition is characterized by comprising the following components in parts by weight: pyridazinone compounds represented by the general formula I as claimed in claim 1 or the general formula I-A, I-B, I-C, I-B', I-J as claimed in claim 2 as an active ingredient in the composition; wherein, the weight percentage of the active components in the composition is 0.1 to 99 percent.
5. Use of a composition according to claim 4 for controlling germs, pests and mites in the agricultural field.
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