CN107964007B - Pyridazinone compound and application thereof - Google Patents

Pyridazinone compound and application thereof Download PDF

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CN107964007B
CN107964007B CN201610915189.6A CN201610915189A CN107964007B CN 107964007 B CN107964007 B CN 107964007B CN 201610915189 A CN201610915189 A CN 201610915189A CN 107964007 B CN107964007 B CN 107964007B
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CN107964007A (en
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刘长令
关爱莹
孙芹
杨金龙
李志念
孙旭峰
夏晓丽
马森
杨帆
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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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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    • 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
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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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    • 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 BDA0001134738130000011
The chemical name is 2-tert-butyl-5- (4-tert-butylbenzylthio) -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. The acaricide is effective on a series of mites such as panonychus ulmi, tetranychus, small-paw mites, tetranychus urticae koch, tarsal mites and gall mites, is effective on mites in different growth periods from eggs, young mites, nymphs and adult mites, 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 BDA0001134738130000012
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, halo C1-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;
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;
x is selected from NR9O or S;
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) aminosulfuryl, unsubstituted or substitutedArylcarbonyl C further 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;
and when R is1＝CH3，R2＝R3When X is not H, L is not C2-C3A linear alkyl 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, halo C1-C8Alkyl radical, C1-C8Alkoxy, halo C1-C8Alkoxy radical, C1-C8Alkylcarbonyl, halo C1-C8Alkyl radicalCarbonyl 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;
l is a bond, C1-C2Straight saturated alkyl chain, C3-C8Straight saturated alkyl chain, C1-C8Straight unsaturated alkyl chain, C1-C8Branched saturated alkyl chain or C1-C8A branched unsaturated alkyl chain;
x is selected from NR9O or S;
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) aminosulfanyl, arylcarbonyl C which is unsubstituted or further substituted by 1 to 51-C6Alkyl, arylcarbonyl, aryloxycarbonyl, arylC1-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.
And when R is1＝CH3，R2＝R3When X is not H, L is not C2-C3A linear alkyl group.
Further optional compounds in the pyridazinone compounds of the present invention include: in the general formula I, 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, halo C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8same or different, are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
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;
x is selected from NR9O or S;
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, arylcarbonyl C which is unsubstituted or further substituted by 1 to 51-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.
And when R is1＝CH3，R2＝R3When X is not H, L is not C2-C3A linear alkyl group.
In the pyridazinone compounds of the present invention, still further optional compounds include: the compound of the general formula I is a compound shown in general formula I-A, I-B, I-C, I-A ', I-B ', I-C ', I-D, I-E, I-F, I-G, I-H or I-I,
Figure BDA0001134738130000041
Figure BDA0001134738130000051
in the above-mentioned general formula, the compound,
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;
l is a bond, C1-C2Straight saturated alkyl chain, C3-C4Straight saturated alkyl chain or C1-C4A branched saturated alkyl chain.
Y is selected from CH or N;
wherein, in the general formula I-A,
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-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, heteroaryl, arylmethyl or heteroarylmethyl;
R9selected from hydrogen, formyl, C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Alkoxy radical C1-C4Alkyl, benzoyl or benzyl;
R6selected from hydrogen, 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;
in the general formulae I-B and I-C,
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 group、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;
R6selected from hydrogen, 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;
in the general formula I-A',
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-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, heteroaryl, arylmethyl or heteroarylmethyl;
R9selected from hydrogen, formyl, C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Alkoxy radical C1-C4Alkyl, benzoyl or benzyl;
R6selected from hydrogen, 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;
R10、R11each independently selected from hydrogen or C1-C4 alkyl;
in the general formulas I-B 'and I-C',
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-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, heteroaryl, arylmethyl or heteroarylmethyl;
R6selected from hydrogen, 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;
R10、R11each independently selected from hydrogen or C1-C4An alkyl group;
in the general formula I-D, the compound,
R1selected 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;
R3selected 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;
R6selected from hydrogen, 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;
R9selected from hydrogen, formyl, C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Alkoxy radical C1-C4Alkyl, benzoyl or benzyl;
in the general formula I-E, I-F,
R1selected 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;
R3selected from hydrogenHydroxy, 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;
R6selected from hydrogen, 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;
in the general formula I-G,
R1selected 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;
R2selected 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-C4Alkyl sulfinyl radicalHalogen substituted 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;
R6selected from hydrogen, 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;
R9selected from hydrogen, formyl, C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Alkoxy radical C1-C4Alkyl, benzoyl or benzyl;
in the general formula I-H, I-I,
R1selected 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;
R2selected 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, haloGeneration C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, heteroaryl, arylmethyl or heteroarylmethyl;
R6selected from hydrogen, 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.
In the pyridazinone compounds of the invention, further optional compounds are compounds shown as the general formula I-A, I-B, I-C, I-A ', I-B ', I-C ', I-D, I-E, I-F, I-G, I-H or I-I, wherein in the general formula,
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;
l is a bond, CH2、CH2CH2、CH(CH3)CH2、CH2CH2CH2、CH(CH3)CH2CH2、CH2CH＝CHCH2Or CH2C≡CCH2；
Y is selected from CH or N;
wherein, in the general formula I-A,
R2、R3the same or different, are respectively selected from hydrogen, hydroxyl, 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, tris (trifluoromethyl)Fluoroethoxy, 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;
R9selected from hydrogen;
R6selected from hydrogen, fluoro, chloro, bromo, iodo, hydroxy, 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;
in the general formulae I-B and I-C,
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-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R6Substituted aryl, heteroaryl, arylmethyl or heteroarylmethyl;
R6selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butylCyclopropyl, cyclobutyl, monofluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, heptafluoroisopropyl, methoxy, ethoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio or trifluoromethylthio;
in the general formula I-A',
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;
R9selected from hydrogen;
R6selected from hydrogen, fluoro, chloro, bromo, iodo, hydroxy, 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;
R10、R11each independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl;
in the general formulas I-B 'and I-C',
R2、R3the same or different, are respectively selected from hydrogen, hydroxyl, cyano, halogen, methyl, ethyl, n-propyl, isopropyl and n-propylButyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, monofluoromethyl, 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;
R6selected from hydrogen, fluoro, chloro, bromo, iodo, hydroxy, 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;
R10、R11each independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl;
in the general formula I-D, the compound,
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, methoxymethyl, methoxyethyl, ethoxymethyl, unsubstituted or substituted with 1-5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R3selected from the group consisting of hydrogen, hydroxy, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, monofluoromethyl, chloromethyl, methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, trifluoromethyl,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 with 1-5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R6selected from hydrogen, fluoro, chloro, bromo, iodo, hydroxy, 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;
R9selected from hydrogen;
in the general formula I-E, I-F,
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, methoxymethyl, methoxyethyl, ethoxymethyl, unsubstituted or substituted with 1-5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R3selected from the group consisting of hydrogen, hydroxy, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, heptafluoroisopropyl, methoxy, ethoxy, trifluoroethoxy, formyl, trifluoroacetyl, methylthio, ethylthio, trifluoromethylthio, methylAlkylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl, methoxycarbonyl, trifluoromethylcarbonyl, unsubstituted or substituted by 1 to 5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R6selected from hydrogen, fluoro, chloro, bromo, iodo, hydroxy, 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;
in the general formula I-G,
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, methoxymethyl, methoxyethyl, ethoxymethyl, unsubstituted or substituted with 1-5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R2selected from the group consisting of 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 with 1-5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R6selected from hydrogen, fluoro, chloro, bromo, iodo, hydroxy, 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;
R9selected from hydrogen;
in the general formula I-H, I-I,
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, methoxymethyl, methoxyethyl, ethoxymethyl, unsubstituted or substituted with 1-5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R2selected from the group consisting of 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 with 1-5R6Substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzyl, picolyl;
R6selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, monofluoromethylA chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, heptafluoroisopropyl, methoxy, ethoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio or trifluoromethylthio group;
in the pyridazinone compounds of the invention, more optional compounds are compounds shown as the general formula I-A, I-B, I-C, I-A 'or I-B', wherein in the general formula,
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;
R6selected from fluoro, chloro, bromo, iodo, cyano, nitro, methyl, trifluoromethyl, trichloromethyl, methoxy or trifluoromethoxy; wherein n is 1-3;
l is a bond, CH2Or CH2CH2；
Y is selected from CH or N;
wherein, in the general formula I-A, I-A', R9Selected from hydrogen;
in the general formulas I-A 'and I-B',
R10、R11are all selected from hydrogen.
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:
halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl groups: straight-chain or branched alkyl radicals, e.g. 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 or branched alkylsulfonyl wherein the hydrogen atoms of the alkyl group may be partially or wholly substituted by halogen atoms. Alkylaminosulfenyl: such as CH3NHS-、C2H5NHS-. Dialkylaminosulfenyl: such as (CH)3)2NS-、(C2H5)2NS-. Alkylaminosulfonyl: alkyl-NH-SO2-. Dialkylaminosulfonyl: (alkyl group)2-N-SO2-. Alkylsulfonylaminocarbonyl group: alkyl-SO2-NH-CO-. Alkylcarbonylaminosulfonyl: alkyl-CO-NH-SO2-. Alkylcarbonylalkyl group: alkyl-CO-alkyl-. Alkylsulfonyloxy group: alkyl-S (O)2-O-. Haloalkylsulfonyloxy: the hydrogen atoms of the alkyl group of the alkylsulfonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF3-SO2-O. 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-. HalogenatedAlkoxyalkyl groups: the hydrogen atoms of the alkyl groups of alkoxyalkyl groups may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2OCH2-、CF3CH2OCH2-and the like. Alkoxycarbonylalkyl groups: alkoxycarbonyl-alkyl-, e.g. CH3OCOCH2-. Haloalkoxycarbonylalkyl: the hydrogen atoms of the alkyl group of the alkoxycarbonylalkyl group may be partially or fully substituted by halogen atoms, e.g. CF3CH2OCOCH2-. Alkylcarbonyloxy group: such as CH3COO-, etc. Haloalkylcarbonyloxy: the hydrogen atoms of the alkylcarbonyloxy group may be partially or fully substituted by halogen atoms, e.g. CF3COO-, etc. Alkoxycarbonyloxy: alkoxycarbonyl-oxy-, e.g. CH3OCOO-. Haloalkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF3OCOO-. Alkylthio-carbonylalkyl: alkylthiocarbonyl-alkyl-, e.g. CH3SCOCH2-. Haloalkylthiocarbonylalkyl: the hydrogen atoms of the alkyl group of the alkylthiocarbonylalkyl group may be partially or wholly substituted by halogen atoms, e.g. CF3CH2SCOCH2-. Alkoxyalkoxy group: such as CH3OCH2O-, etc. Haloalkoxyalkyl: the hydrogen atoms of the alkoxy groups being partially or wholly replaced by halogen atoms, e.g. CF3OCH2O-is formed. Alkoxy alkoxycarbonyl group: such as CH3OCH2CH2OCO-, etc. Alkylthio group: straight or branched chain alkyl groups attached to the structure via a sulfur atom. Haloalkylthio: straight-chain or branched alkylthio groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like. Alkylthioalkyl: alkyl-S-alkyl-, e.g. CH3SCH2-. Haloalkylthioalkyl: the hydrogen atoms of the alkyl group of an alkylthioalkyl group may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2SCH2-、CF3CH2SCH2-and the like. Alkylamino group: straight or branched chain alkyl radicals via nitrogenThe atomic bond is attached to the structure. Haloalkylamino group: straight-chain or branched alkylamino groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms. Dialkylamino group: such as (CH)3)2N-，(CH3CH2)2N-is provided. Halogenated dialkylamino group: the hydrogen atoms of the alkyl groups being partially or wholly replaced by halogen atoms, e.g. (CF)3)2N-，(CF3CH2)2N-is provided. Alkenyl: straight-chain or branched alkenes, for example ethenyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1, 2-allenyl and 2, 4-hexadienyl. Halogenated alkenyl groups: straight-chain or branched alkenes in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenyloxy: linear or branched alkenes linked to the structure via oxygen atoms. Haloalkenyloxy: straight-chain or branched alkenyloxy groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenylthio group: linear or branched alkenes linked to the structure via a sulfur atom bond. Such as CH2＝CHCH2S-. Alkenyloxycarbonyl radical: such as CH2＝CHCH2OCO-, etc. Alkynyl: straight-chain or branched alkynes, for example ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. Alkynyl also includes groups consisting of multiple triple bonds, such as 2, 5-hexadiynyl. Halogenated alkynyl group: straight-chain or branched alkynes, 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: alkyl of alkylcarbonylThe hydrogen atoms in (A) may be partially or wholly replaced by halogen atoms, e.g. CF3CO-. Alkoxycarbonyl group: the alkoxy group is attached to the structure via a carbonyl group. Such as CH3OCO-，CH3CH2OCO-. Aminocarbonyl group: such as NH2CO-. Alkyl amino carbonyl: alkyl-NH-CO-, e.g. CH3NHCO-，CH3CH2NHCO-. Dialkylaminocarbonyl group: such as (CH)3)2NCO-，(CH3CH2)2NCO-. The aryl moiety in (hetero) aryl, (hetero) arylalkyl, (hetero) arylcarbonyl, (hetero) arylmethylcarbonyl, (hetero) arylcarbonylalkyl, (hetero) aryloxycarbonyl, (hetero) arylalkyloxycarbonyl, and the like includes phenyl or naphthyl. 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 BDA0001134738130000111
TABLE 1R1Substituent group
Figure BDA0001134738130000121
Figure BDA0001134738130000131
TABLE 2R2(R3) Substituent group
Figure BDA0001134738130000132
Figure BDA0001134738130000141
TABLE 3R9Substituent group
Figure BDA0001134738130000142
Figure BDA0001134738130000151
Some of the compounds of the present invention are illustrated by specific compounds listed in tables 4 to 231, but are not intended to limit the present invention. In the general formula compounds I-A, I-B, I-C, I-D, I-E, I-F, I-G, I-H or I-I, R9＝H。
In general formula I-a, when Y ═ CH, some specific compounds can be illustrated in tables 4 to 55.
Figure BDA0001134738130000152
When R is2＝R3＝H，L＝CH2，R4＝Cl，R5When (R) is H6) The substituent n is shown in Table 4, and represents the compound number of 4-1-4-279 in sequence.
TABLE 4
Figure BDA0001134738130000161
Figure BDA0001134738130000171
Figure BDA0001134738130000181
Table 5: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 5-1-5-279.
Table 6: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered as 6-1-6-279.
Table 7: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are in the order of 7-1-7-279.
Table 8: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 8-1 to 8-279.
Table 9: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered in the order of 9-1 to 9-279.
Table 10: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 10-1 to 10-279.
Table 11: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 11-1 to 11-279.
Table 12: when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 12-1 to 12-279.
Table 13: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 13-1-13-279.
Table 14: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 14-1 to 14-279.
Table 15: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 15-1-15-279.
Table 16: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 16-1 to 16-279 in this order.
Table 17: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are in the order of 17-1-17-279.
Table 18: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 18-1-18-279.
Table 19: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 19-1 to 19-279.
Table 20: when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 20-1 to 20-279.
Table 21: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 21-1-21-279.
Table 22: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 22-1-22-279.
Table 23: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nThe representative compounds are shown in Table 4 in agreement with the substituentsNumbers are in order 23-1-23-279.
Table 24: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 24-1-24-279.
Table 25: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 25-1 to 25-279.
Table 26: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the symbols represent the numbers of the compounds in the order of 26-1 to 26-279.
Table 27: in the general formula I-A, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are 27-1-27-279 in the order of their numbers.
Table 28: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order 28-1 to 28-279.
Table 29: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered in the order of 29-1 to 29-279.
Table 30: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered in the order of 30-1 to 30-279.
Table 31: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 31-1-31-279.
Table 32: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 32-1 to 32-279.
Table 33: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 33-1-33-279 in that order.
Table 34: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 34-1-34-279, in that order.
Table 35: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 35-1 to 35-279.
Table 36: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 36-1 to 36-279.
Table 37: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 37-1 to 37-279.
Table 38: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 38-1 to 38-279.
Table 39: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 39-1-39-279 in that order.
Table 40: when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 40-1 to 40-279 in that order.
Table 41: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 41-1-41-279 in that order.
Table 42: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 42-1-42-279.
Table 43: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When the average value is t-Bu,substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are in the order of 43-1-43-279.
Table 44: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 44-1 to 44-279.
Table 45: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 45-1 to 45-279 in that order.
Table 46: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 46-1-46-279, in that order.
Table 47: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 47-1-47-279, in that order.
Table 48: when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 48-1 to 48-279 in that order.
Table 49: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 49-1-49-279.
Table 50: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 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，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds having the number of 51-1-51-279 in that order.
Table 52: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 52-1-52-279.
Table 53: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 53-1 to 53-279 in that order.
Table 54: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the symbols represent compounds 54-1 to 54-279.
TABLE 55-1: in the general formula I-A, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 55-1-55-1-279.
In general formula I-a', when Y ═ CH, some specific compounds can be illustrated in table 7-1, table 11-1, table 15-1, and table 19-1.
Figure BDA0001134738130000201
(wherein R is10＝R11＝H)
Table 7-1: in the general formula I-A', when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered as 7-1-7-1-279.
Table 11-1: in the general formula I-A', when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered as 11-1-1-11-1-279.
Table 15-1: in the general formula I-A', when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 15-1-15-1-279.
Table 19-1: in the general formula I-A', when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered as 19-1-19-1-279.
In general formula I-a, when Y ═ N, some specific compounds can be illustrated in tables 55 to 70.
In the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When (R) is H6) The substituents n are shown in Table 55 and represent the compound numbers 55-1-55-9 in sequence.
Watch 55
Figure BDA0001134738130000202
Figure BDA0001134738130000211
Table 56: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are, in order, 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)2When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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，R5When t-Bu, substituent (R)6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 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，R5When H, the substituent (R)6)nIn accordance with the substituents shown in Table 55, the representative compound numbers are, in order, 59-1 to 59-9.
Table 60: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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)2When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are, in order, 61-1 to 61-9.
Table 62: in the general formula I-A, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 62-1 to 62-9 in this order.
Table 63: when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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)2When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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，R5When H, the substituent (R)6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 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＝CH3When (R) is substituted6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 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)2When (R) is substituted6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 69-1 to 69-9 in that order.
Table 70: in the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 70-1 to 70-9 in this order.
In general formula I-B, when Y ═ CH, some specific compounds can be illustrated in tables 71 to 122.
Figure BDA0001134738130000212
Table 71: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are in the order of 71-1-71-279 in number.
Table 72: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 72-1-72-279.
Table 73: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound numbers are 73-1 to 73-279 in that order.
Table 74: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent the compounds numbered 74-1-74-279 in that order.
Table 75:in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 75-1-75-279.
Table 76: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent the compounds numbered 76-1-76-279 in that order.
Table 77: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are in the order of 77-1-77-279.
Table 78: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent the compounds numbered 78-1 to 78-279 in that order.
Table 79: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are, in order of number, 79-1-79-279.
Table 80: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered in the order of 80-1 to 80-279.
Table 81: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered as 81-1-81-279.
Table 82: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 82-1-82-279.
Table 83: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 83-1-83-279.
Table 84: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 84-1-84-279.
Table 85: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 85-1 to 85-279.
Table 86: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 86-1-86-279.
Table 87: when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 87-1 to 87-279 in that order.
Table 88: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nIn accordance with the substituents shown in table 4,the representative compound numbers are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are sequentially numbered 89-1-89-279.
Table 90: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 90-1 to 90-279.
Table 91: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order 91-1 to 91-279.
Table 92: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 92-1 to 92-279, in that order.
Table 93: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 93-1-93-279.
Table 94: in the general formula I-B, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 94-1 to 94-279 in that order.
Table 95: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered from 95-1 to 95-279 in that order.
Table 96: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered as 96-1-96-279.
Table 97: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds having the numbers of 97-1 to 97-279 in that order.
Table 98: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 98-1 to 98-279.
Table 99: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered in the order of 99-1 to 99-279.
Table 100: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered sequentially from 100-1 to 100-279.
Table 101: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nIn accordance with the substituents shown in Table 4, the numbers of the representative compounds are101-1—101-279。
Table 102: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the symbols represent the following compounds 102-1-102-279.
Table 103: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 103-1-103-279.
Table 104: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the symbols represent compounds numbered sequentially from 104-1 to 104-279.
Table 105: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the symbols represent compounds 105-1 to 105-279.
Table 106: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent the compounds with the numbers of 106-1-106-279.
Table 107: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered sequentially from 107-1 to 107-279.
Table 108: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the symbols represent compounds 108-1-108-279.
Table 109: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to 4-1-4-279 in Table 4 in sequence in accordance with Table 4, the representative compound numbers are 109-1-109-279 in sequence.
Table 110: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered sequentially from 110-1 to 110-279.
Table 111: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered from 111-1 to 111-279.
Table 112: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represents the compounds with the numbers of 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 (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered as 113-1-113-279.
Table 114: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nWatch and watch4 are identical and represent the compound numbers 114-1-114-279.
Table 115: when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 115-1-115-279.
Table 116: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represents compounds 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 (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered from 117-1 to 117-279.
Table 118: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the symbols of the representative compounds are 118-1-118-279.
Table 119: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 119-1-119-279.
Table 120: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered sequentially from 120-1 to 120-279.
Table 121: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered from 121-1 to 121-279.
Table 122: in the general formula I-B, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represents compounds numbered 122-1-122-279 in sequence.
In general formula I-B', when Y ═ CH, some specific compounds can be illustrated in tables 74-1, 78-1, 82-1 and 86-1.
Figure BDA0001134738130000241
(wherein R is10＝R11＝H)
TABLE 74-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 74-1-74-1-279.
TABLE 78-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 78-1-78-1-279.
TABLE 82-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered as 82-1-82-1-279.
TABLE 86-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 86-1-86-1-279.
In general formulae I to B, when Y ═ N, some specific compounds can be illustrated in tables 123 to 138.
Table 123: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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, substituent (R)6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 126-1 to 126-9 in this order.
Table 127: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, the substituent (R)6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 127-1 to 127-9 in that order.
Table 128: in the general formula I-B, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the representative compounds are numbered 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, substituent (R)6)nCorresponding to substituent 5 shown in Table 5, are in the order of 130-1 to 130-9 in accordance with the representative compound number.
Table 131: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the representative compounds are numbered in the order of 133-1 to 133-9.
Table 134: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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, the substituent (R)6)nCorresponding to the substituents shown in Table 55, are representedThe compounds are numbered in sequence 135-1 to 135-9.
Table 136: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the symbols represent compounds numbered in the order of 136-1 to 136-9.
Table 137: in the general formula I-B, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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, substituent (R)6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 138-1 to 138-9 in this order.
In general formulae I to C, when Y ═ CH, some specific compounds can be illustrated in tables 139 to 190.
Figure BDA0001134738130000251
Table 139: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 139-1-139-279.
Table 140: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered sequentially from 140-1 to 140-279.
Table 141: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5＝CH(CH3)2When the temperature of the water is higher than the set temperature,substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound number is 141-1-141-279 in this order.
Table 142: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is sequentially numbered 142-1-142-279.
Table 143: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represents the compounds with the numbers of 143-1-143-279.
Table 144: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 144-1-144-279.
Table 145: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nIn agreement with the substituents shown in Table 4, represent compounds numbered 145-1-145-279.
Table 146: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered from 146-1 to 146-279.
Table 147: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound number is 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 (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent the compounds with the numbers of 148-1-148-279.
Table 149: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 149-1-149-279.
Table 150: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound number is 150-1-150-279.
Table 151: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, represents compounds numbered sequentially from 151-1 to 151-279.
Table 152: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 152-1 to 152-279.
Table 153: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 153-1-153-279.
Table 154: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represents compounds numbered sequentially from 154-1 to 154-279.
Table 155: when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered in the order of 155-1-155-279.
Table 156: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 156-1-156-279.
Table 157: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 157-1-157-279.
Table 158: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 158-1-158-279.
Table 159: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 159-1-159-279.
Table 160: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered sequentially from 160-1 to 160-279.
Table 161: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nAnd take as shown in Table 4The substituents are identical, and represent the compounds with the numbers of 161-1-161-279 in sequence.
Table 162: in the general formula I-C, when R is2＝R3＝H，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 162-1-162-279.
Table 163: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is 163-1-163-279 in the order of the number.
Table 164: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 164-1-164-279.
Table 165: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds having the numbers of 165-1-165-279.
Table 166: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered as 166-1-166-279.
Table 167: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 167-1-167-279.
Table 168: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 168-1-168-279.
Table 169: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 169-1-169-279.
Table 170: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 170-1-170-279.
Table 171: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 171-1-171-279.
Table 172: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered as 172-1-172-279.
Table 173: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4 in turn to 4-1-4-279 in Table 4, represent the compounds having the numbers 173-1-173-279 in turn.
Table 174: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nAnd as shown in Table 4The substituents are identical and represent the compounds numbered in the order 174-1-174-279.
Table 175: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 175-1-175-279.
Table 176: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 176-1-176-279.
Table 177: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is 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, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 178-1-178-279 in this order.
Table 179: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 179-1-179-279.
Table 180: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered sequentially from 180-1 to 180-279.
Table 181:in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 181-1-181-279 in this order.
Table 182: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds with the numbers of 182-1-182-279 in sequence.
Table 183: when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 183-1-183-279.
Table 184: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 184-1-184-279.
Table 185: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5＝CH(CH3)2When (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound number is 185-1-185-279.
Table 186: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 186-1-186-279.
Table 187: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 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 (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 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 (R) is substituted6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 189-1-189-279.
Table 190: in the general formula I-C, when R is2＝H，R3＝CH3，L＝CH(CH3)CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent the compounds with the numbers of 190-1-190-279 in sequence.
In general formula I-C', when Y ═ CH, some specific compounds can be illustrated in tables 142-1, 146-1, 150-1 and 154-1.
Figure BDA0001134738130000281
(wherein R is10＝R11＝H)
Table 142-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represents the compound number of 142-1-142-1-279 in this order.
TABLE 146-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 146-1-146-1-279.
TABLE 150-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 150-1-150-1-279.
TABLE 154-1: in the general formula I-B', when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represents compounds numbered 154-1-154-1-279.
In general formulae I to C, when Y ═ N, some specific compounds can be illustrated in tables 191 to 206.
Table 191: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When H, the substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to substituent 5 shown in Table 5, represents a compound having a 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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, substituent (R)6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 194-1 to 194-9 in this order.
Table 195: general formula I-CIn when R is2＝R3＝H，L＝CH2，R4＝Br，R5When H, the substituent (R)6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 195-1 to 195-9 in that order.
Table 196: in the general formula I-C, when R is2＝R3＝H，L＝CH2，R4＝Br，R5＝CH3When (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds were 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 (R) is substituted6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 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, substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 198-1 to 198-9 in this order.
Table 199: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When H, the substituent (R)6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nIn accordance with the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are, in order, 201-1 to 201-9.
Table 202: in the general formula I-C, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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, the substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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 (R) is substituted6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 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, substituent (R)6)nCorresponding to the substituents shown in Table 55, the numbers of the representative compounds are 206-1 to 206-9 in this order.
In general formulas I to D, when Y ═ CH, some specific compounds can be illustrated in tables 207 to 210.
Figure BDA0001134738130000291
Table 207: in the general formula I-D, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nAnd shown in Table 4The substituents are identical and represent the compounds with the serial numbers 207-1-207-279.
Table 208: in the general formula I-D, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represents the compounds with the numbers of 208-1-208-279.
Table 209: in the general formula I-D, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds having the numbers of 209-1-209-279 in this order.
Table 210: in the general formula I-D, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered sequentially from 210-1 to 210-279.
In general formulae I to E, when Y ═ CH, some specific compounds can be illustrated in tables 211 to 214.
Figure BDA0001134738130000292
Table 211: in the general formula I-E, when R2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are sequentially 211-1-211-279.
Table 212: in the general formula I-E, when R2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent the compounds with the numbers of 212-1-212-279 in sequence.
Table 213: in the general formula I-E, when R2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered from 213-1 to 213-279 in this order.
Table 214: in the general formula I-E, when R2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the symbols represent the numbers of 214-1-214-279.
In general formulae I to F, when Y ═ CH, some specific compounds can be shown in tables 215 to 218.
Figure BDA0001134738130000293
Table 215: in the general formula I-F, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered from 215-1 to 215-279.
Table 216: in the general formula I-F, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 216-1 to 216-279.
Table 217: in the general formula I-F, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 217-1-217-279.
Table 218: in the general formula I-F, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 218-1-218-279.
In general formulae I to G, when Y ═ CH, some specific compounds can be described in tables 219 to 222.
Figure BDA0001134738130000301
Table 219: in the general formula I-G, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 219-1-219-279.
Table 220: in the general formula I-G, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compounds are numbered 220-1-220-279.
Table 221: in the general formula I-G, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds with the numbers 221-1-221-279 in sequence.
Table 222: in the general formula I-G, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 222-1-222-279.
In general formulae I to H, when Y ═ CH, some specific compounds can be illustrated in tables 223 to 226.
Figure BDA0001134738130000302
Table 223: in the general formula I-H, when R2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is 223-1-223-279 in the order of the numbers.
Table 224: in the general formula I-H, when R2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent the compounds with the numbers of 224-1-224-279 in sequence.
Table 225: in the general formula I-H, when R2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound number is 225-1-225-279.
Table 226: in the general formula I-H, when R2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered from 226-1 to 226-279.
In general formula I-I, when Y ═ CH, some specific compounds can be illustrated in tables 227 to 230.
Figure BDA0001134738130000311
Table 227: in the general formula I-I, when R is2＝R3＝H，L＝CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the representative compound is numbered 227-1-227-279.
Table 228: in the general formula I-I, when R is2＝R3＝H，L＝CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, the symbols represent compounds 228-1-228-279.
Table 229: in the general formula I-I, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered 229-1-229-279 in sequence.
Table 230: in the general formula I-I, when R is2＝R3＝H，L＝CH2CH2，R4＝Br，R5When t-Bu, substituent (R)6)nCorresponding to the substituents shown in Table 4, represent compounds numbered sequentially from 230-1 to 230-279.
In the general formula I-A, when R is2＝R3＝H，L＝CH2CH2，R4＝Cl，R5When t-Bu, the substituent R9(in the case of other than hydrogen) are different substituents as shown in Table 231, representing compounds with numbers 231-1-231-140 in sequence.
Table 231
Figure BDA0001134738130000312
Figure BDA0001134738130000321
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 BDA0001134738130000331
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, WO 2005060959 a1, US 5672715A, US 5668088A, WO 9640643 a1, US 4099012 a.
2) When X is O or S, the general formula I-2 is prepared as follows:
Figure BDA0001134738130000332
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 in reference to CN104710409A, WO 2005060959 a1, US 5672715A, US 5668088A, WO 9640643 a1, US 4099012 a.
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, 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, 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), 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, 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 fasci, 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, 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.
Dermaptera (Dcrmaptcra) (earwigs).
Vein winged order (Dictyoptera) (cockroach): german cockroach (Blattella germanica) (German cockroach), blattaria orientalis (Blatta orientalis), Blatta palustris (Blatta cockroach), Blatta australiana (parcoblata penylvanica), Periplaneta americana (perilanta americana) (austria americana), Blatta australiana (australia cockroach)), Periplaneta fusca (pcripa rubra) (australia cockroach), Periplaneta fuliginosa (brown cockroach), Periplaneta smokosa (perilanta fuliginosa) (Periplaneta fuliginosa (cockroach)), and Periplaneta fuliginosa (brown cockroach) (Periplaneta subcapium (brown cockroach)), and Periplaneta fuligina (brown cockroach) (Periplaneta rubra americana (brown cockroach)).
Diptera (Diptera) (flies): mosquito species (Aedes spp.) (mosquito), lucerne fly larvae (Agromyza frontella) (alfa blotch), agromyzis species ((Agromyza spp.) (leaf miner), trypetid species (anastrep spp.) (fruit fly), garleria persica (anastrepa subsp.) (fruit fly), garleria persica (garleria persica) (garleria persica (tail fly)), mosquito species (anophes spp.) (mosquito), fruit fly species (batrachta spp.) (fruit fly), melon fly (Bactrocera bitrae) (melon), citrus fruit fly (Bactrocera persica), mosquito species (ceitis spp.) (mosquito), mosquito fly larvae (sea fly larvae) (sea fly), sea fly larvae (sea fly larvae) (deer spp.) (moth), sea fly larvae (sea fly larvae) (moth larvae) (bilus persica spp.) (fruit fly) (moth larvae) (mosquito larvae) (deer spp.) (fruit fly) (garrisb) (mosquito larvae) (sea fly) (moth) Leaf of rape mosquito (Dasineura brassicae) (cabbage mosquito), Dimochi species (Delia spp.), Grapholitha platura (root maggot (seed corn bug)), Drosophila species (Drosophila spp.) (vinegar fly), Musca species (Fannia spp.) (housefly), yellow belly fly (Fannia canthus) (summer fly (litter house fly)), Grey belly fly (grey belly fly) (Grey belly fly), Gasterophilus intestinalis (Gasterophilus intestinalis) (horse bot), Gracillia persea, Haematobia irritani (Haematobia irrita) (fly), Black fly species (Hymenea spp.) (root maggot) (root fly), Musca (cabbage fly), Musca fly (seedling fly), Musca fly (leaf fly), Musca fly (cabbage fly) (fly), Musca fly (leaf fly), Musca fly (cabbage fly (leaf fly) (fly), Musca fly (leaf fly) (fly, cabbage fly (leaf fly) (fly), Musca fly (leaf fly) (fly), Musca fly (leaf fly) (fly) and Musca fly (leaf fly) (fly) of Musca fly), Musca fly (leaf, Musca fly) (fly) of Musca fly), Musca fly (fly) (fly, Musca fly) (fly, The plant includes, but is not limited to, the species fall houseflies (Musca australis) (face fly), houseflies (Vusca domestica) (house fly), sheep houseflies (oesteurs ovis) (sheep nose fly (sheet boot fly)), european stem flies (ostrinia fructicosa) (carrot rust fly (carrotr fly)), cherry fruit flies (rhagopetis cerasi) (cherry fruit fly)), apple fruit flies (rhapontella pomonella) (apple maggot)), red mud fly (Sitodiplosis mossambucus) (cattle yellow fly (stable fly)), and cattle fly (stable fly)).
Hemiptera (Hemiptera) (stinkbug): apolygus lucorum (Acrosteronum hieron) (green stink bug), Oryza sativa (Blissus leucopterus) (long stink bug), Oryza sativa (Caloris norvegicus) (potato stink bug), Tropical stink bug (Cimex hemipterus) (tropical stink), stinkbug (Cimex leucopterus) (bed bug), Daghertus fasciatus, Dichelops furcatus, Oryza sativa (Eucotton stainer), Edestabunda (Oryza sativa), Oryza sativa (Lepidorum), Oryza sativa (Oryza sativa) and Oryza sativa (Oryza sativa) by (Oryza sativa) and/or Oryza sativa (Oryza sativa) for treating plant (Oryza sativa) and/Oryza sativa (Oryza sativa) for treating plant, Lygus hesperus (Lygus hesperus) (western tarnished plant bug), hibiscus syriacus linnaeus (macrocytoericcus hirsutus), neuroolpus longirostris, rice green bugs (Nezara viridula) (southern green stink bug), Lygus planterum (phytolocoris spp.) (Lygus), california planterus (phytoorius californicus), phytoorius relatus, piezocoritus guilidingdinggi, tetrad bugs (podocarpus utilis linus) (folulated plant bug), psycaninum vaccicola, pseudostellaria persica, scorpio corina and trypanosoma (trypanosoma) seed (nose cone).
Homoptera (Homoptera) (aphid, scale, whitefly, leafhopper): piper pisum (Acrythosiphopkinsum) (pea aphid)), Coccinum species (Adelges spp.) (adelgids), Beeuglena brassicae (Aleurodes proteella) (Beeuglena cabbage whitefly), Aleurodicus disperses (Aleurodicus disperses), Aleurothrix striatus (Aleurothrix luteus) (gloomy whitley), Begoniothyria albonensis species (Aluaspis spp.) (Aluraceae biguella), Pectinatus species (Aphrophola sp.) (Aphrophophora spp.) (leafhopper), Rhodococcus rhododendron (Aoniella natura), Begoniothrix gloeosporioides (Begonioth), Begoniothrix gloeosporus (Begoniothrix), Begoniothrix aphid (Begoniothrix), Begoniothrix) aphid (Begoniothrix), Begoniothrix sp (Begoniothrix) and Begoniothrix aphid (Begoniothrix) Aphis (Begonioth), Begonioth (Aphis) Aphis sp), Begonioth (Begonia), Begonioth (Aphis sp), Begonioth (Begonioth) Aphis sp), Begonia), Begonioth (Begonia), Begoniothrix) and Begoniothrix) species (Begoniothrix) of Aphis, Begoniothrix, Aphis, Asparagus tubular aphid (Brachyryyncria asparagi) (Asparagus aphid), Brevennia rehi, cabbage aphid (Brevicornus brassicae) (cabbage aphid), Lecanicillium species (Ceroplastes spp.) (scale), Ceriporiococcus rubens (Ceroplastes rubens) (red wax scale), Cestrum species (Chionastis spp.) (Iceltica), Lecanicillium species (Chrysomophagus spp.) (scale), Ceriporiococcus species (Coccus spp.) (scale), apple pink aphid (Dysapphigenia plantaginea) (sysplex aphid), Phyllopsis viridis (apple aphid) and Lecanicola (apple aphid) plant (apple aphid), Phyllospora major (apple aphid), Phyllospora (apple aphid) and Lecanicola (apple aphid), Phyllospora grandis (apple aphid), Phyllophora gossypium (apple aphid), Leonicola (apple aphid (apple), and Leonicola (apple aphid), Phyllophora variety (apple aphid) and Leonicola (apple aphid) of Leonicola (apple aphid (apple), Leonicola (apple aphid), and leaf, apple aphid (apple), and leaf, leaf strain (apple stem) (maize) plant, leaf strain (apple stem, leaf, Leaf of the species Mylopharyngodium (Macrosiphum grandium) (English grandis)), Long pipe aphid (Macrosiphum rosae) (Rose aphid (rose aphid)), four-leaf hopper (Macrosteles quadratus) (purple leaf hopper (ash leaf hopper)), Mahanarva frimbiola, Meopodium diricum (wheat germ) aphid (rose aphid), Midis Longicornis, peach aphid (Myzus persicae) (peach aphid (green apple aphid)), Nephophylum spruce (Nephotettix spreng) (leaf hopper), Nephotettix cinctix (green leaf hopper), Phosphaera (brown apple aphid) (Phosphaera), Phosphaera (brown apple aphid) (leaf hopper), Phosphaera (leaf hopper), Phosphaericoides) (leaf hopper) (leaf hopper), leaf hopper (leaf hopper) (leaf hopper (leaf), leaf hopper (leaf hopper (leaf hopper) and leaf hopper (leaf hopper) (leaf hopper (leaf hopper) leaf, leaf hopper (leaf hopper) Pygeum sp (mealybugs), pygeus sp (mealybugs), begecky sp (Pseudococcus spp), mealybugs (Pseudococcus brcvps) (pink apple), pernicia pelyridis (quadrspididatus) (saint josephse), pygecky sp (Rhapalosiphum sp.) (aphid), corn leaf aphid (rhaalophilus maida) (corn aphid), corn leaf aphid (bitter orange apple tree), red apple wax apple tree (white apple, 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 formotermes spp, Heterotermes spp, Coptotermes formotermes formosanus, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes, 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 (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 nubilalis (ostrinia nubilalis, 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.) (Helicover, Tomato moth (Keifera lycopersicella) (tomato pinum), white-fin webworm (Leucinodes orbornata) of Solanum, egg plant fruit moth (egg plant fruit borrelia), leaf miner (Leucoptera malinella), the species Plutella xylostella (Lithocollectis spp.), grape leaf moth (Lobesia borrelia) (grape fruit mot), the species Loxagrus (Loxagrus spp.), the species Laurella punctata (Laurella punctata), the species Laurella cerifera (Loxagrus alburena), the species Laurella punctata (Bean white-leaf diculus (Bean) of Leguminosae), the species Lymantria (Lymantria disparis) (grape fruit bud), the species Lymantria dispar) (gypsylla), the species (Lyonetia punctifera), the species Lyonella (apple leaf moth (apple leaf miner), the oil bag (cabbage), the species (cabbage moth) (cabbage leaf borer), the species (leaf moth (Lymantria), the species (Lyonetia punctifera), the species (Lyoneura) of Plutella (Plutella), the species (Plutella) of Plutella (Plutella), the species (Plutella) of Spinacea brueckea fructia (Spinacea), the species of Spinacea (Spodophylla) of Plutella (Spinacea), the species of Spinacea (Spinea), the genus (Spinacea) of Spinacea (Spinaceus), 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, 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 Spodo, 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, 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 (, 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 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. The residue was separated by column chromatography (eluent ethyl acetate and petroleum ether at 1:10 by volume) to give 18.06g of a 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. The residue was chromatographed (eluent ethyl acetate and petroleum ether, volume ratio 1:5) to give 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. The residue was separated by column chromatography (eluent ethyl acetate and petroleum ether at 1:2 volume ratio) to yield 23.38g of white solid with 96.2% yield.
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 were added to 50ml of DMF, 4.45g (0.022mol) of triethylamine was added at room temperature with stirring, the reaction was carried out at 80 to 100 ℃ for 2 to 4 hours, after the completion of the TLC monitoring, water (100ml) and (3X 100ml) of ethyl acetate were added to extract the mixture, the organic phase was washed with 50ml of saturated saline, and after the precipitation, column chromatography was carried out on the residue (eluent, ethyl acetate and petroleum ether, in a volume ratio of 1:2) to obtain 15 to 21, 3.42g of the brown oil-like compound in 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 to monitor the reaction, decompressing and distilling to remove the solvent, adding (3 multiplied by 50ml) ethyl acetate for extraction, washing an organic phase by 50ml saturated saline, 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 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 ℃) with the volume ratio of 1:4) to obtain 1.53g of white solid with the yield of 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 an 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 ℃) and the volume ratio is 1:4) to obtain 1.55g of brown solid with the yield of 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. 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 2.59g of yellow solid with yield of 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 (3X 50ml) ethyl acetate for extraction, washing an organic phase by using 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 3.51g 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), obtaining 4.11g of white solid with the yield of 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 ℃) with the volume ratio of 1:4), so 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, and the 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 with 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, cooling the reaction liquid after the reaction is monitored by TLC, 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 white liquid as a column layer after exsolution, in 58.0% yield. 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,Py-5-H),8.39(s,1H,Py-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, then 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 (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, 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 ℃) and the volume ratio is 1:4) to obtain 1.71g of white solid with the yield of 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, 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 1.68g (0.03mol) of 30% NaSH, stirring for reacting for 2 hours, cooling the reaction liquid, pouring the cooled reaction liquid 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 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 3.44g 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 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 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 ℃) and 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 was put into a 100ml single-neck flask, 35ml of dichloromethane was added, stirring was carried out in an ice bath, 1.43g (0.012mol) of thionyl chloride was added dropwise, an apparatus for collecting off-gas was installed, after the TLC monitoring reaction was completed, the solvent was distilled off under reduced pressure, 3X 50ml of ethyl acetate was added for extraction, the organic phase was washed with 50ml of saturated saline solution, and column chromatography was carried out on the residue after the elution (eluent was ethyl acetate and petroleum ether (boiling range: 60-90 ℃ C.), volume ratio was 1:4) to obtain 1.93g of brown solid with a yield of 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 for 4 hr, monitoring by TLC, adding (3 × 50ml) ethyl acetate for extraction, washing organic phase with 50ml saturated saline solution, removing solvent, and performing column chromatography to residue(eluent is ethyl acetate and petroleum ether (boiling range 60-90 deg.C), volume ratio is 1:3) to obtain compound 194-4, 1.75g red solid, melting point 141 deg.C. The yield thereof was found to be 39.6%.1H-NMR (300MHz, internal standard TMS, solvent CDCl3)δ(ppm):δ8.70(s,1H),8.1(d,J＝2.1Hz,1H),7.9(s,1H),7.78(s,1H),7.69(d,J＝2.1Hz,1H),4.32(s,2H),1.63(s,9H)。
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: 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. m.p.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.m.p.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. m.p.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-H J＝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.m.p.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. m.p.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. m.p.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. m.p.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. m.p.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. melting point 129.4 ℃.1H NMR(300MHz,CDCl3):δ1.30(dd,6H,J＝3.0Hz,NCHCH3),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,Py-H,J＝4.5Hz),7.82(dd,2H,Py-H,J＝3Hz),8.12(s,1H,Pyrida-H).
Compound 74-4: brown solid.m.p.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: white solid.m.p.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-H J＝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. m.p.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. m.p.136.5 ℃.1H NMR(300MHz,CDCl3):δ8.00(s,1H),7.80(s,1H),7.78(s,1H),7.63(d,J＝9.0Hz,2H),7.43(d,J＝9.0Hz,2H),5.32(s,2H),1.63(s,9H).
Compounds 74-20: 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. m.p.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. m.p.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. m.p.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.m.p.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. m.p.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: 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. Melting point 129.3 ℃.1H NMR(300MHz,CDCl3):δ1.65(s,9H,NCCH3),5.32(s,2H,CH2),7.72(s,1H,Pyrazol-3-H),7.75(s,Pyrazol-5-H),7.81(dd,4H,Py-H,J＝4.5Hz),8.10(s,1H,Pyrida-H).
Compounds 74-72: yellow solid. m.p.133 deg.C.1H NMR(300MHz,CDCl3):δ8.02(s,1H),7.81(s,1H),7.78(s,1H),7.63(d,J＝9.0Hz,2H),7.43(d,J＝9.0Hz,2H),5.24(s,2H),1.62(s,9H).
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: a white solid. Melting point 148.6 ℃.1H NMR(300MHz,CDCl3):δ8.70(s,1H),8.1(d,J＝2.1Hz,1H),7.9(s,1H),7.78(s,1H),7.69(d,J＝2.1Hz,1H),5.32(s,2H),1.65(s,9H).
Compound 126-3: white solid.m.p.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,Ph-5-H,J＝2.1Hz),8.25(s,1H,Ph-3-H),8.40(d,1H,Ph-6-H,J＝2.1Hz).
Compound 140-1: yellow solid. m.p.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. m.p.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.m.p.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.m.p.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. m.p.129 ℃.1H NMR(300MHz,CDCl3):δ7.95(s,1H),7.80(s,1H),7.78(s,1H),7.63(d,J＝9.0Hz,2H),7.23(d,J＝9.0Hz,2H),5.32(s,2H),1.63(s,9H).
Compound 142-6: yellow solid. m.p.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: 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.m.p.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. m.p.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).
Chemical combinationSubstance 142-57: red oil.1H NMR(300MHz,CDCl3):δ1.63(s,9H,t-Bu-H),2.38(s,2H,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. m.p.134.5 ℃.1H NMR (300MHz, CDCl3): δ 8.02(s,1H),7.81(s,1H),7.78(s,1H),7.63(d, J ═ 9.0Hz,2H),7.43(d, J ═ 9.0Hz,2H),5.24(s,2H),1.62(s,9H).
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).
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 25ppm dosage, 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, 74-158, 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%.
Inhibition rate of cucumber botrytis cinerea:
at a dosage of 25ppm, the inhibition rate of the compounds such as 126-2 on cucumber botrytis cinerea is more than 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:
at a dose of 400ppm, such as 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, 73-69, 74-1, 74-4, 74-6, 74-1-19, 74-21, 74-23, 74-25, 74-31, 74-52, 74-57, 74-72, 74-158, 124-3, 126-2, 126-3, 140-1, 140-21, 142-1, 142-4, 142-6, 142-19, 142-23, 142-57, 142-72, 194-4 and the like have the control effect on cucumber downy mildew of over 80 percent;
at the dosage of 100ppm, the control effect of compounds such as 15-23, 15-158, 73-69, 74-1, 74-6, 74-19, 74-21, 74-23, 74-52, 74-57, 74-72, 74-158, 126-2, 126-3, 142-1, 142-4, 142-6, 142-19, 142-23, 194-4 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, the control effect of compounds such as 15-21, 73-69, 74-4, 74-6, 74-19, 74-23, 74-72, 142-1, 142-19, 142-21, 142-23, 142-158 and the like on wheat powdery mildew is more than 80 percent;
at a dose of 100ppm, the control effect of compounds such as 73-69, 142-158 and the like on wheat powdery mildew is more than 80 percent.
In vivo protective activity against corn rust:
under the dosage of 400ppm, the control effect of compounds such as 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, 74-158, 126-2, 126-3, 140-1, 142-4, 142-6, 142-19, 142-23, 142-72, 142-158, 194-4 and the like on the corn rust is more than 80 percent;
at the dosage of 100ppm, the control effect of compounds such as 15-18, 15-158, 73-69, 74-4, 74-6, 74-23, 74-158, 126-2, 142-1, 142-6, 142-72, 142-158 and the like on the corn rust is more than 80 percent.
In vivo protective activity against cucumber anthracnose:
at the dose of 400ppm, the control effect of 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 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.

Claims (9)

1. A pyridazinone compound characterized by: the pyridazinone compound is shown as a general formula I-A, I-B or I-C,
Figure FDA0002883387170000011
in the formula:
R2、R3same or different and are respectively selected from hydrogen, hydroxyl, cyano, halogen and C1-C12Alkyl radical, C3-C8Cycloalkyl, halo C1-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 or halo C1-C12An alkoxycarbonyl group;
R4selected from halogens;
R5is selected from 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, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl, halo C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C1-C12Alkylthio carbonyl group C1-C12Alkyl, halo C1-C12Alkylthio carbonyl group C1-C12Alkyl radical, C1-C12Alkylcarbonyloxy, halo C1-C12Alkylcarbonyloxy, C1-C12Alkoxycarbonyloxy, halo C1-C12Alkoxycarbonyloxy, C1-C12Alkylsulfonyloxy, halo C1-C12Alkylsulfonyloxy, C1-C12Alkoxy radical C1-C12Alkoxy or halo C1-C12Alkoxy radical C1-C12An alkoxy group; n is 1-3;
R7、R8same or different, are respectively selected from hydrogen and C1-C12Alkyl or halo C1-C12An alkyl group;
l is a bond, C1-C2Straight saturated alkyl chain, C1-C12Straight unsaturated alkyl chain, C1-C12Branched saturated alkyl chain or C1-C12A branched unsaturated alkyl chain;
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;
y is selected from CH or N.
2. The pyridazinone-based compound according to claim 1, characterized in that:
R2、R3same or different and are respectively selected from hydrogen, hydroxyl, cyano, halogen and C1-C8Alkyl radical, C3-C6Cycloalkyl, halo C1-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 or halo C1-C8An alkoxycarbonyl group;
R4selected from halogens;
R5is selected from 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, 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;
l is a bond, C1-C2Straight saturated alkyl chain, C1-C8Straight unsaturated alkyl chain, C1-C8Branched saturated alkyl chain or C1-C8A branched unsaturated alkyl chain;
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.
3. The pyridazinone-based compound according to claim 2, characterized in that:
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 or halo C1-C4An alkoxycarbonyl group;
R4selected from halogens;
R5is selected from 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, 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;
l is a bond, C1-C2Straight saturated alkyl chain, C1-C4Straight unsaturated alkyl chain, C1-C4Branched saturated alkyl chain or C1-C4A branched unsaturated alkyl chain;
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, arylcarbonyl C which is unsubstituted or further substituted by 1 to 51-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.
4. The pyridazinone-based compound according to claim 3, characterized in that:
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, C1-C4Alkylthio or halogeno C1-C4An alkylthio group;
l is a bond, C1-C2Straight 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.
5. The pyridazinone-based compound according to claim 4, wherein:
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 or trifluoromethoxy carbonyl;
R4selected from fluorine, chlorine, bromine or iodine;
R5selected from 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 hydrogen, fluoro, chloro, bromo, iodo, hydroxy, 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;
l is a bond, CH2、CH2CH2、CH(CH3)CH2、CH(CH3)CH2CH2、CH2CH＝CHCH2Or CH2C≡CCH2；
R9Selected from hydrogen.
6. The pyridazinone compound according to claim 5, wherein:
R2、R3the same or different, are respectively selected from hydrogen, methyl or ethyl;
R4selected from chlorine or bromine;
R5selected from methyl, isopropyl or tert-butyl;
R6selected from hydrogen, fluoro, chloro, bromo, iodo, cyano, nitro, methyl, trifluoromethyl, trichloromethyl, methoxy or trifluoromethoxy; n is 1-3;
l is a bond, CH2Or CH2CH2；
R9Selected from hydrogen.
7. Use of a compound of formula I-A, I-B or I-C according to any one of claims 1 to 6 in the agricultural field for the preparation of a fungicide medicament.
8. A germicidal composition, characterized by: comprising as active ingredient in a composition a compound of formula I-A, I-B or I-C as defined in any one of claims 1 to 6; wherein, the weight percentage of the active components in the composition is 0.1 to 99 percent.
9. Use of a composition according to claim 8 for controlling germs in the agricultural field.
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