CN108069973B - Substituted six-membered heterocyclic compound containing pyrimido ring and preparation method and application thereof - Google Patents

Substituted six-membered heterocyclic compound containing pyrimido ring and preparation method and application thereof Download PDF

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CN108069973B
CN108069973B CN201611028153.2A CN201611028153A CN108069973B CN 108069973 B CN108069973 B CN 108069973B CN 201611028153 A CN201611028153 A CN 201611028153A CN 108069973 B CN108069973 B CN 108069973B
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CN108069973A (en
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李淼
杨吉春
赵杰
杨帆
张俊龙
孙金强
孙庚�
刘长令
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Abstract

The invention discloses a substituted six-membered heterocyclic compound containing pyrimido ring, which has a structure shown as a general formula I:

Description

Substituted six-membered heterocyclic compound containing pyrimido ring and preparation method and application thereof
Technical Field
The invention belongs to the field of agricultural bactericidal insecticides, and particularly relates to a novel substituted six-membered heterocyclic compound containing a pyrimido ring, and a preparation method and application thereof.
Background
JP 59036683A discloses the use of isoxazolopyrimidines of the general formula shown below as acaricides for agricultural use.
Figure GDA0002519959280000011
However, the structure of the substituted hexabasic heterocyclic compound is far from that of the substituted hexabasic heterocyclic compound containing pyrimido ring shown in the general formula I, and meanwhile, the compound shown in the general formula I is not reported.
Disclosure of Invention
The invention aims to provide a substituted six-membered heterocyclic compound containing pyrimido ring and capable of controlling various germs and pest mites, a preparation method thereof and application of the substituted six-membered heterocyclic compound in preparation of medicines for preventing and controlling germs and/or pests in agriculture or other fields.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a substituted six-membered heterocyclic compound containing pyrimido ring is a compound shown in a general formula I;
Figure GDA0002519959280000012
R1selected from hydrogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C3-C12Cycloalkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C1-C12Alkylthio, halo C1-C12Alkylthio radical, C1-C12Alkylsulfinyl radical, C1-C12Alkylsulfonyl radical, C2-C12Alkenyl, halo C2-C12Alkenyl radical, C2-C12Alkynyl, halo C2-C12Alkynyl, C3-C12Alkenyloxy, halogeno C3-C12Alkenyloxy radical, C3-C12Alkynyloxy, halo C3-C12Alkynyloxy, C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, C1-C12Alkylaminocarbonyl, halogeno C1-C12Alkylaminocarbonyl radical, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkylcarbonyl, haloGeneration C1-C12Alkylcarbonyl, unsubstituted or substituted by 1-5R11Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R2selected from hydrogen, halogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C3-C8Cycloalkyl radical, C1-C12Alkoxy radical, C1-C12Alkylthio or C1-C12An alkylsulfonyl group;
a is selected from NR3O or S;
x is selected from NR3O or S;
y is selected from NR3O or S;
R3selected from hydrogen, hydroxy, formyl, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylthio radical, C2-C12Alkenylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, halo C2-C12Alkenyl, halo C2-C12Alkynyl, C1-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;
R4、R5are the same or different and are respectively selected from hydrogen, halogen and C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy or halo C1-C12An alkoxy group;
wherein R is4、R5C which may also be linked to it constitutes C3-C8A ring of (a);
R6、R7are the same or different and are respectively selected from hydrogen, halogen and C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy radicalOr halo C1-C12An alkoxy group;
wherein R is6、R7C which may also be linked to it constitutes C3-C8A ring of (a);
m is an integer from 0 to 5;
q is selected from unsubstituted or substituted by 1-4R8A substituted six membered heteroaryl group;
R8selected from halogen, hydroxy, amino, cyano, nitro, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, halo-di (C)1-C12Alkyl) amino, C (═ O) NR9R10、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, halo C1-C12Alkoxy radical C1-C12Alkoxy, unsubstituted or substituted by 1 to 5R11Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R9、R10are the same or different and are respectively selected from hydrogen and C1-C12Alkyl or halo C1-C12An alkyl group;
R11selected from halogen, hydroxy, amino, cyano, nitro, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, 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-C12An alkoxycarbonyl group,C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl or C1-C12Alkoxycarbonyl radical C1-C12An alkyl group;
or a salt of a compound of formula I.
In the substituted six-membered heterocyclic compound containing pyrimido ring, optional compounds include those shown in general formula I:
R1selected from hydrogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio, halo C1-C6Alkylthio radical, C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl radical, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C2-C6Alkynyl, halo C2-C6Alkynyl, C3-C6Alkenyloxy, halogeno C3-C6Alkenyloxy radical, C3-C6Alkynyloxy, halo C3-C6Alkynyloxy, C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, C1-C6Alkylaminocarbonyl, halogeno C1-C6Alkylaminocarbonyl radical, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl, unsubstituted or substituted by 1-5R11Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonylHeteroarylmethylcarbonyl or heteroaryloxycarbonyl;
R2selected from hydrogen, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio or C1-C6An alkylsulfonyl group;
a is selected from NR3O or S;
x is selected from NR3O or S;
y is selected from NR3O or S;
R3selected from hydrogen, hydroxy, formyl, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylthio radical, C2-C6Alkenylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, halo C2-C6Alkenyl, halo C2-C6Alkynyl, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkylsulfinyl, halogeno C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylaminosulfonyl, di (C)1-C6Alkyl) aminosulfonyl, C1-C6Alkylsulfonylaminocarbonyl group, C1-C6Alkylcarbonylaminosulfonyl radical, C3-C6Cycloalkyloxycarbonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkyl carbonyl radical C1-C6Alkyl radical, C1-C6Alkoxycarbonyl radical C1-C6Alkyl radical, C1-C6Alkylaminocarbonyl, di (C)1-C6Alkyl) aminocarbonyl, C2-C6Alkenyloxycarbonyl radical, C2-C6Alkynyloxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkoxycarbonyl group, C1-C6Alkylaminosulfenyl, di (C)1-C6Alkyl) 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;
R4、R5are the same or different and are respectively selected from hydrogen, halogen and C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is4、R5C which may also be linked to it constitutes C3-C6A ring of (a);
R6、R7are the same or different and are respectively selected from hydrogen, halogen and C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is6、R7C which may also be linked to it constitutes C3-C6A ring of (a);
m is an integer from 0 to 4;
q is selected from unsubstituted or substituted by 1-4R8Substituted pyridyl, pyrimidinyl, pyridazinyl, piperazinyl;
R8selected from halogen, hydroxy, amino, cyano, nitro, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, halo-di (C)1-C6Alkyl) amino, C (═ O) NR9R10、C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, halo C2-C6Alkynyloxy, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkoxycarbonyl radical C1-C6Alkyl, halo C1-C6Alkoxycarbonyl radical C1-C6Alkyl radical, C1-C6Alkylthio carbonyl group C1-C6Alkyl, halo C1-C6Alkylthio carbonyl group C1-C6Alkyl radical, C1-C6Alkylcarbonyloxy, halo C1-C6Alkylcarbonyloxy, C1-C6Alkoxycarbonyloxy, halo C1-C6Alkoxycarbonyloxy, C1-C6Alkylsulfonyloxy, halo C1-C6Alkylsulfonyloxy, C1-C6Alkoxy radical C1-C6Alkoxy, halo C1-C6Alkoxy radical C1-C6Alkoxy, unsubstituted or substituted by 1 to 5R11Substituted aryl, arylmethyl, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, heteroaryl, heteroarylmethyl, heteroarylcarbonyl, heteroarylmethylcarbonyl, or heteroaryloxycarbonyl;
R9、R10are the same or different and are respectively selected from hydrogen and C1-C6Alkyl or halo C1-C6An alkyl group;
R11selected from halogen, hydroxy, amino, cyano, nitro, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, halo C2-C6Alkynyloxy, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl or halo C1-C6Alkylthio group C1-C6An alkyl group;
or a salt of a compound of formula I.
In the substituted six-membered heterocyclic compound containing pyrimido ring, the more optional compounds comprise the following compounds in a general formula I:
when Q is pyridine ring, the structural formula of the general formula I is shown as I-1, wherein n is an integer from 1 to 4, and when n is 1, R8Is not selected from methyl;
when Q is a pyridazine ring, the structural formula of the general formula I is shown as I-2, and n is selected from an integer from 0 to 3;
when Q is a pyrimidine ring, the structural formula of the general formula I is shown as I-3, and n is selected from an integer from 0 to 3;
when Q is pyrazine ring, the structural formula of the general formula I is shown as I-4, and n is selected from an integer from 0 to 3;
Figure GDA0002519959280000041
in the above-mentioned formula, the compound of formula,
R1selected from hydrogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio, halo C1-C6Alkylthio radical, C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl radical, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C2-C6Alkynyl, halo C2-C6Alkynyl, unsubstituted or substituted by 1-5R11Substituted phenyl, pyridyl, pyrimidinyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, furanyl, thienyl, thiazolyl, benzyl, picolyl, thienylmethyl, or thiazolylmethyl;
R2selected from hydrogen, halogen, C1-C6Alkyl, halo C1-C6Alkyl radical, C3-C6Cycloalkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio or C1-C6Alkyl radicalA sulfonyl group;
a is selected from NR3O or S;
x is selected from NR3O or S;
y is selected from NR3O or S;
R3selected from hydrogen, hydroxy, formyl, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylthio radical, C2-C6Alkenylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, halo C2-C6Alkenyl, halo C2-C6Alkynyl, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkylsulfinyl, halogeno C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylaminosulfonyl, di (C)1-C6Alkyl) aminosulfonyl;
R4、R5are the same or different and are respectively selected from hydrogen, halogen and C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is4、R5C which may also be linked to it constitutes C3-C6A ring of (a);
R6、R7are the same or different and are respectively selected from hydrogen, halogen and C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group;
wherein R is6、R7C which may also be linked to it constitutes C3-C6A ring of (a);
m is an integer from 0 to 4;
R8selected from halogen, hydroxy, amino, cyano, nitro, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, halo-di (C)1-C6Alkyl) amino, C (═ O) NR9R10、C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, halo C2-C6Alkynyloxy, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl, unsubstituted or substituted by 1-5R11Substituted phenyl, pyridyl, pyrimidinyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, furanyl, thienyl, thiazolyl, benzyl, picolyl, thienylmethyl, or thiazolylmethyl;
R9、R10are the same or different and are respectively selected from hydrogen and C1-C6Alkyl or halo C1-C6An alkyl group;
R11selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, 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 or halo C1-C4Alkylthio group C1-C4An alkyl group;
or salts of the compounds of the general formula I-1, I-2, I-3 or I-4 with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
In the substituted six-membered heterocyclic compound containing pyrimido ring, a further optional compound comprises that the structure of the compound shown in the general formula I-1 is as follows: I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G or I-1H;
the structure of the compound shown in the general formula I-2 is I-2A, I-2B, I-2C or I-2D;
the structure of the compound shown in the general formula I-3 is I-3A, I-3B, I-3C, I-3D, I-3E or I-3F;
the structure of the compound shown in the general formula I-4 is I-4A or I-4B;
Figure GDA0002519959280000051
Figure GDA0002519959280000061
in the formula:
R1selected from hydrogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C6Cycloalkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C2-C4Alkenyl, halo C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkynyl, unsubstituted or substituted by 1-5R11Substituted phenyl, pyridyl, pyrimidinyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, furanyl, thienyl, thiazolyl, benzyl, picolyl, thienylmethyl, or thiazolylmethyl;
R2selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C6Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio or C1-C4An alkylsulfonyl group;
R4、R5are the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is4、R5C which may also be linked to it constitutes C3-C6A ring of (a);
R6、R7are the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
wherein R is6、R7C which may also be linked to it constitutes C3-C6A ring of (a);
m is an integer from 0 to 4;
R8selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR9R10、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, unsubstituted or substituted by 1-5R11Substituted phenyl, pyridyl, pyrimidyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, furanyl, thienylThiazolyl, benzyl, pyridylmethyl, thienylmethyl or thiazolylmethyl;
R9、R10are the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
R11selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, 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 or halo C1-C4Alkylthio group C1-C4An alkyl group;
in the general formula I-1A, I-1B, I-1C, I-1E, I-1F, I-1G, I-2A, I-2B, I-2C, I-2D, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-4A or I-4B,
x is selected from NR3；
R3Selected from hydrogen, hydroxy, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl 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;
in the general formula I-1D or I-1H,
x is selected from O or S;
and in the above general formula I-1A, I-1B, I-1C or I-1D, n is selected from an integer of 1 to 4, and when n is 1, R is8Is not selected from methyl; in the general formula I-1E, I-1F, I-1G or I-1H, n is an integer from 0 to 4; in the general formula I-2A, I-2B, I-2C, I-2D, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-4A or I-4B, n is an integer from 0 to 3;
or salts of compounds represented by general formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-2A, I-2B, I-2C, I-2D, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-4A or I-4B with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
In the substituted six-membered heterocyclic compounds containing pyrimido rings, further optional compounds comprise compounds shown in general formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-2A, I-2B, I-2C, I-2D, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-4A or I-4B:
R1selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxymethyl, ethoxymethyl, trifluoroethoxymethyl, unsubstituted or substituted with 1-5R11Substituted phenyl, pyridyl, furyl, thienyl, thiazolyl or benzyl;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl;
R4、R5are the same or different and are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and tert-butoxy;
R6、R7are the same or different and are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and tert-butoxy;
m is an integer from 0 to 4;
R8selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, unsubstituted or substituted with 1-5R11Substituted phenyl, pyridyl, furyl, thienyl, thiazolyl or benzyl; r11Selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, or trifluoroethoxy;
in the general formula I-1A, I-1B, I-1C, I-1E, I-1F, I-1G, I-2A, I-2B, I-2C, I-2D, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-4A or I-4B,
x is selected from NR3；
R3Selected from the group consisting of hydrogen, hydroxy, formyl, acetyl, propionyl, butyryl, trifluoroacetyl, benzoyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoroethoxy, cyclopropyloxy, methylthio, ethylthio, allyl, propargyl, methylsulfonyl, ethylsulfonyl, trifluoroethylsulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methylsulfonylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, vinyloxycarbonyl, acetylenyloxycarbonyl, methylaminothio, ethylaminothio or dimethylaminosulfanyl;
in the general formula I-1D or I-1H,
x is selected from O or S;
and in the above general formula I-1A, I-1B, I-1C or I-1D, n is selected from an integer of 1 to 4, and when n is 1, R is8Is not selected from methyl; in the general formula I-1E, I-1F, I-1G or I-1H, n is an integer from 0 to 4; in the general formula I-2A, I-2B, I-2C, I-2D, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-4A or I-4B, n is an integer from 0 to 3;
or salts of compounds represented by general formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-2A, I-2B, I-2C, I-2D, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-4A or I-4B with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
In the substituted six-membered heterocyclic compounds containing pyrimido rings, further optional compounds comprise compounds shown as general formulas I-1A, I-1B, I-1C, I-1E, I-1F, I-1G, I-2A, I-2C, I-3A, I-3B, I-3D, I-3E, I-4A or I-4B:
R1selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, cyclopropyl, unsubstituted or substituted by 1-4R11Substituted phenyl, pyridyl;
R2selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl;
R3selected from hydrogen, methyl, acetyl, trifluoroacetyl, methoxy, methylthio, allyl, methylsulfonyl, methylaminosulfonyl, dimethylaminosulfonyl, methoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylaminothio or dimethylaminosulfanyl;
R4、R5are the same or different and are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R6、R7are all selected from hydrogen;
m is an integer from 0 to 4;
R8selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, unsubstituted or substituted with 1-4R11Substituted phenyl, pyridyl;
R11selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, methoxy or trifluoromethoxyA group;
and in formula I-1A, I-1B or I-1C, n is selected from an integer from 1 to 4, and when n is 1, R8Is not selected from methyl; in the general formula I-1E, I-1F or I-1G, n is selected from an integer of 0 to 4; in the general formula I-2A, I-2C, I-3A, I-3B, I-3D, I-3E, I-4A or I-4B, n is an integer from 0 to 3;
or salts of compounds represented by general formula I-1A, I-1B, I-1C, I-1E, I-1F, I-1G, I-2A, I-2C, I-3A, I-3B, I-3D, I-3E, I-4A or I-4B with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
In the substituted six-membered heterocyclic compounds containing pyrimido rings, more optional compounds comprise compounds shown in a general formula I-1A, I-1B, I-1C, I-1E, I-1F, I-1G, I-2A, I-2C, I-3A, I-3B, I-3D, I-3E, I-4A or I-4B:
R1selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, cyclopropyl;
R2selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl;
R3selected from hydrogen, methyl, acetyl, trifluoroacetyl, methoxy, methylthio, allyl, methylsulfonyl, methylaminosulfonyl, dimethylaminosulfonyl, methoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylaminothio or dimethylaminosulfanyl;
R4、R5are the same or different and are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R6、R7are all selected from hydrogen;
m is an integer from 0 to 3;
R8selected from fluoro, chloro, bromo, iodo, cyano, nitro, methyl, trifluoromethyl, methoxy, or trifluoromethoxy;
in formula I-1A, I-1B or I-1C, n is selected from an integer of 1 to 4, and when n is 1, R8Is not selected from methyl; general formula I-1E, I-1F or I-in 1G, n is selected from an integer from 0 to 4; in the general formula I-2A, I-2C, I-3A, I-3B, I-3D, I-3E, I-4A or I-4B, n is an integer from 0 to 3;
or salts of compounds represented by general formula I-1A, I-1B, I-1C, I-1E, I-1F, I-1G, I-2A, I-2C, I-3A, I-3B, I-3D, I-3E, I-4A or I-4B with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
Wherein, in A, X, Y, R is the same as R3The substituents are independently selected; r1And R8With respect to R11The substituents are independently selected.
A preparation method of the substituted six-membered heterocyclic compound containing the pyrimido ring comprises the following steps:
Figure GDA0002519959280000101
an application of substituted pyridine compounds containing isoxazolo-pyrimidine shown in a general formula I in preparing bactericides and pesticides in agriculture or other fields.
A bactericidal and insecticidal composition, which takes a pyrimidine-containing substituted pyrazole compound shown in the general formula I in claim 1 as an active component; wherein, the weight percentage of the active components in the composition is 0.1 to 99 percent.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl groups: straight-chain or branched alkyl groups, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl groups: substituted or unsubstituted cyclic alkyl groups, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, and the like. Halogenated alkyl groups: straight-chain or branched alkyl groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms, e.g. 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-. Haloalkoxyalkyl groups: the hydrogen atoms of the alkyl groups of alkoxyalkyl groups may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2OCH2-、CF3CH2OCH2-and the like. Alkoxycarbonylalkyl groups: alkoxycarbonyl-alkyl-, e.g. CH3OCOCH2-. Halogenated alkoxycarbonyl groupAlkyl groups: the hydrogen atoms of the alkyl group of the alkoxycarbonylalkyl group may be partially or fully substituted by halogen atoms, e.g. CF3CH2OCOCH2-. Alkylcarbonyloxy group: such as CH3COO-, etc. Haloalkylcarbonyloxy: the hydrogen atoms of the alkylcarbonyloxy group may be partially or fully substituted by halogen atoms, e.g. CF3COO-, etc. Alkoxycarbonyloxy: alkoxycarbonyl-oxy-, e.g. CH3OCOO-. Haloalkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF3OCOO-. Alkylthio-carbonylalkyl: alkylthiocarbonyl-alkyl-, e.g. CH3SCOCH2-. Haloalkylthiocarbonylalkyl: the hydrogen atoms of the alkyl group of the alkylthiocarbonylalkyl group may be partially or wholly substituted by halogen atoms, e.g. CF3CH2SCOCH2-. Alkoxyalkoxy group: such as CH3OCH2O-, etc. Haloalkoxyalkyl: the hydrogen atoms of the alkoxy groups being partially or wholly replaced by halogen atoms, e.g. CF3OCH2O-is formed. Alkoxy alkoxycarbonyl group: such as CH3OCH2CH2OCO-, etc. Alkylthio group: straight or branched chain alkyl groups attached to the structure via a sulfur atom. Haloalkylthio: straight-chain or branched alkylthio groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like. Alkylthioalkyl: alkyl-S-alkyl-, e.g. CH3SCH2-. Haloalkylthioalkyl: the hydrogen atoms of the alkyl group of an alkylthioalkyl group may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2SCH2-、CF3CH2SCH2-and the like. Alkylamino group: straight or branched chain alkyl, linked to the structure via a nitrogen atom. Haloalkylamino group: straight-chain or branched alkylamino groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms. Dialkylamino group: such as (CH)3)2N-，(CH3CH2)2N-is provided. Halogenated dialkylamino group: the hydrogen atoms on the alkyl groups may be partially orAll substituted 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: the hydrogen atoms of the alkyl group of the alkylcarbonyl group may be partially or fully substituted by halogen atoms, e.g. CF3CO-. Alkoxycarbonyl group: the alkoxy group is attached to the structure via a carbonyl group. Such as CH3OCO-，CH3CH2OCO-. Aminocarbonyl group: such as NH2CO-. Alkyl amino carbonyl: alkyl-NH-CO-, e.g. CH3NHCO-，CH3CH2NHCO-. Dialkylaminocarbonyl group: such as (CH)3)2NCO-，(CH3CH2)2NCO-. The aryl moiety in (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.
Tables 1,2, 3, 4, 5 and 6 show the R in the general formula I1、R2、R3(X＝NR3)、R4And R5、R6And R7、R8(substituents on Q) are specific substituents, but they are not limited to these substituents.
Figure GDA0002519959280000111
TABLE 1R1Substituent group
Figure GDA0002519959280000112
Figure GDA0002519959280000121
TABLE 2R2Substituent group
Figure GDA0002519959280000122
TABLE 3R3Substituent group
Figure GDA0002519959280000123
Figure GDA0002519959280000131
TABLE 4R4(R5) Substituent group
Figure GDA0002519959280000132
Figure GDA0002519959280000141
TABLE 5R6(R7) Substituent group
Figure GDA0002519959280000142
TABLE 6R8Substituent group
Figure GDA0002519959280000143
Some of the compounds of the present invention can be illustrated by the specific compounds listed in tables 7 to 15, but are not intended to limit the present invention. In the general formula compound I-1A, I-1B, I-1C, I-1D, I-2A, I-2B, I-3A, I-3B, I-3C, I-4A or I-5A, R in the formula compound I-1A, I-1B, I-1C, I-1D, I-2A, I-4A or I-5A2＝R6＝R7＝H。
In the general formula I-1A,
Figure GDA0002519959280000151
when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, (R)8)nThe substituents are shown in Table 7, and represent the compound numbers of 7-1-7-69 in sequence.
TABLE 7
No. (R8)n No. (R8)n No. (R8)n
7-1 3-Cl 7-2 4-Cl 7-3 5-Cl
7-4 6-Cl 7-5 3-Br 7-6 4-Br
7-7 5-Br 7-8 6-Br 7-9 5-I
7-10 5-F 7-11 6-F 7-12 3-CH2CH3
7-13 4-CH2CH3 7-14 5-CH2CH3 7-15 6-CH2CH3
7-16 3-CF3 7-17 4-CF3 7-18 5-CF3
7-19 6-CF3 7-20 3-CN 7-21 4-CN
7-22 5-CN 7-23 6-CN 7-24 3-NO2
7-25 5-NO2 7-26 6-NO2 7-27 5-OCH3
7-28 6-OCH3 7-29 3,5-diCl 7-30 3,5-diBr
7-31 3,5,6-triCl 7-32 3-Cl-5-CH3 7-33 3-Cl-5-CF3
7-34 3-Cl-5-CN 7-35 3-Br-5-NO2 7-36 3-Br-5-CH3
7-37 3-OCH2Ph 7-38 3-CO2CH3 7-39 5-CO2CH3
7-40 5-Br-6-CH3 7-41 5-CF3-6-Cl 7-42 3-CN-6-Cl
7-43 3-CH3-5-Br 7-44 3-NO2-5-Cl 7-45 3-NO2-5-Br
7-46 3-NO2-4-CH3 7-47 3-CF3-6-Cl 7-48 3-CH3-5-NO2
7-49 4-NO2-6-CH3 7-50 4-CH3-5-NO2 7-51 3-NO2-5-CH3
7-52 5-CN-6-CH3 7-53 5-NO2-6-CH3 7-54 4-CH3-5-Br
7-55 5-CN-6-CF3 7-56 3-CN-4,6-diCl 7-57 3,5-diBr-6-CH3
7-58 3-CN-4-CH3-6-Cl 7-59 3-CN-4-CF3-6-Cl 7-60 4-CH3-5-CN-6-Cl
7-61 4-CF3-5-CN-6-Cl 7-62 3-CO2CH3-6-Cl 7-63 5-CO2CH3-6-Cl
7-64 3,6-diCl-5-CF3 7-65 3-CONH2-4,6-diCl 7-66 3-Br-4-CH3-5-NO2
7-67 3,5-diCl-6-OCH3 7-68 3,5-diCl-6-OCF3 7-69 3,5-diCl-6-(OPh-4-Cl)
8: in the general formula I-1A, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 8-1-8-69.
9: in the general formula I-1A, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 9-1-9-69.
10: in the general formula I-1A, when R is1＝H、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn from 10-1 to 10-69.
11: in the general formula I-1A, when R is1＝H、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn 11-1-11-69.
12: in the general formula I-1A, when R is1＝H、R3＝R4＝R5When H, m is equal to 3, takeSubstituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 12-1-12-69.
13: in the general formula I-1A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn 13-1-13-69.
14: in the general formula I-1A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn 14-1-14-69.
15: in the general formula I-1A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers 15-1-15-69 in turn.
16: in the general formula I-1A, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 1, a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 16-1-16-69.
17: in the general formula I-1A, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 2, a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 17-1-17-69.
18: in the general formula I-1A, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 3, a substituent (R)8)nIn accordance with the substituents in Table 7, the substituents correspond in turn to the substituents 7-1-7-69 of Table 7, and represent the compoundsThe numbers are 18-1 to 18-69 in sequence.
In the general formula I-1B,
Figure GDA0002519959280000161
when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, (R)8)nThe substituents are shown in Table 8, and represent the compound numbers of 19-1-19-33 in sequence.
TABLE 8
Figure GDA0002519959280000162
20: in the general formula I-1B, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers in turn from 20-1 to 20-33.
21: in the general formula I-1B, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers 21-1 to 21-33 in turn.
22: in the general formula I-1B, when R is1＝H、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compounds numbered in turn 22-1 to 22-33.
23: in the general formula I-1B, when R is1＝H、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers 23-1 to 23-33 in turn.
24: in the general formula I-1B, when R is1＝H、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compounds numbered in turn 24-1 to 24-33.
25: in the general formula I-1B, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers in turn 25-1 to 25-33.
26: in the general formula I-1B, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers in turn 26-1 to 26-33.
27: in the general formula I-1B, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers 27-1 to 27-33 in turn.
28: in the general formula I-1B, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 1, a substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers in turn 28-1 to 28-33.
29: in the general formula I-1B, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 2, a substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers in turn 29-1 to 29-33.
30: in the general formula I-1B, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 3, a substituent (R)8)nIn accordance with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8 and represent the compoundsThe numbers are 30-1 to 30-33 in sequence.
In the general formula I-1C,
Figure GDA0002519959280000171
when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, (R)8)nThe substituents are shown in Table 9, and represent the compound numbers 31-1-31-11 in sequence.
TABLE 9
No. (R8)n No. (R8)n No. (R8)n
31-1 2-Cl 31-2 3-Cl 31-3 2-OCH3
31-4 2-Br 31-5 2-I 31-6 2,6-diOCH3
31-7 2,6-diCl 31-8 2-CN 31-9 2-NHCH3-6-Cl
31-10 6-OPh 31-11 2-OCH3-6-Cl
32: in the general formula I-1C, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn accordance with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 in Table 9 and represent the compound numbers in turn 32-1 to 32-11.
33: in the general formula I-1C, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 in Table 9 and represent the compound numbers 33-1 to 33-11 in turn.
34: in the general formula I-1C, when R is1＝H、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn accordance with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 in Table 9 and represent the compound numbers in turn 34-1 to 34-11.
35: in the general formula I-1C, when R is1＝H、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn accordance with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 in Table 9 and represent compound numbers in turn 35-1 to 35-11.
36: in the general formula I-1C, when R is1＝H、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn accordance with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 of Table 9 and represent compound numbers in turn 36-1 to 36-11.
37: in the general formula I-1C, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 in Table 9 and represent the compound numbers in turn 37-1 to 37-11.
38: in the general formula I-1C, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn accordance with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 in Table 9 and represent the compound numbers 38-1 to 38-11 in turn.
39: in the general formula I-1C, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 in Table 9 and represent the compound numbers in turn 39-1 to 39-11.
40: in the general formula I-1C, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 1, a substituent (R)8)nIn accordance with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 of Table 9 and represent compound numbers in turn 40-1 to 40-11.
41: in the general formula I-1C, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 2, a substituent (R)8)nIn accordance with the substituents in Table 9, the substituents correspond in turn to those of Table 931-1-31-11, and the number of the representative compound is 41-1-41-11 in sequence.
42: in the general formula I-1C, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 3, a substituent (R)8)nIn accordance with the substituents in Table 9, the substituents correspond in turn to 31-1 to 31-11 in Table 9 and represent the compound numbers 42-1 to 42-11 in turn.
In the general formula I-1D,
Figure GDA0002519959280000181
43: in the general formula I-1D, when R is1＝CH3、R4＝R5When H, X-O, m-1, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn 43-1-43-69.
44: in the general formula I-1D, when R is1＝CH3、R4＝R5When H, X-O, m-2, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 44-1-44-69.
45: in the general formula I-1D, when R is1＝CH3、R4＝R5When H, X-O, m-3, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 45-1-45-69.
46: in the general formula I-1D, when R is1＝H、R4＝R5When H, X-O, m-1, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn 46-1-46-69.
47: in the general formula I-1D, when R is1＝H、R4＝R5When H, X-O, m-2, the substituent (R) is substituted with a substituent (R)8)nIn accordance with the substituents in Table 7, the substituents correspond in turn to the substituents 7-1 to 7-69 of Table 7, and the numbers of the representative compounds are in accordance withThe times are 47-1 to 47-69.
48: in the general formula I-1D, when R is1＝H、R4＝R5When H, X-O, m-3, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 48-1-48-69.
49: in the general formula I-1D, when R is1＝i-C3H7、R4＝R5When H, X-O, m-1, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers 49-1-49-69 in turn.
50: in the general formula I-1D, when R is1＝i-C3H7、R4＝R5When H, X-O, m-2, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn from 50-1 to 50-69.
51: in the general formula I-1D, when R is1＝i-C3H7、R4＝R5When H, X-O, m-3, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers 51-1-51-69 in turn.
52: in the general formula I-1D, when R is1＝CH3、R4＝R5When H, X-S, m-1, the substituent (R) is substituted with a substituent (R)8)nIn accordance with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent compound numbers in turn 521-52-69.
53: in the general formula I-1D, when R is1＝CH3、R4＝R5When H, X-S, m-2, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn 53-1-53-69.
54: in the general formula I-1D, when R is1＝CH3、R4＝R5When H, X-S, m-3, the substituent (R) is substituted with a substituent (R)8)nIn accordance with the substituents in Table 7,the substituents correspond in turn to 7-1-7-69 of Table 7, and the representative compound numbers are in turn 54-1-54-69.
55: in the general formula I-1D, when R is1＝H、R4＝R5When H, X-S, m-1, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn from 55-1 to 55-69.
56: in the general formula I-1D, when R is1＝H、R4＝R5When H, X-S, m-2, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 56-1-56-69.
57: in the general formula I-1D, when R is1＝H、R4＝R5When H, X-S, m-3, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 57-1-57-69.
58: in the general formula I-1D, when R is1＝i-C3H7、R4＝R5When H, X-S, m-1, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn 58-1-58-69.
59: in the general formula I-1D, when R is1＝i-C3H7、R4＝R5When H, X-S, m-2, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers 59-1-59-69 in turn.
60: in the general formula I-1D, when R is1＝i-C3H7、R4＝R5When H, X-S, m-3, the substituent (R) is substituted with a substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7, representing compound numbers in turn from 60-1-60-69.
In the general formula I-1E,
Figure GDA0002519959280000191
61: in the general formula I-1E, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn 61-1-61-69.
62: in the general formula I-1E, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers in turn 62-1-62-69.
63: in the general formula I-1E, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 7, the substituents correspond in turn to 7-1-7-69 of Table 7 and represent the compound numbers 63-1-63-69 in turn.
In the general formula I-1F,
Figure GDA0002519959280000192
64: in the general formula I-1F, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers in turn 64-1 to 64-33.
65: in the general formula I-1F, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 8, the substituents correspond in turn to 19-1 to 19-33 of Table 8, representing compound numbers in turn 65-1 to 65-33.
66: in the general formula I-1F, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn accordance with the substituents in Table 8, the substituents correspond in turn to19-1 to 19-33 in Table 8 represent the numbers of the compounds in the order of 66-1 to 66-33.
In the general formula I-2A,
Figure GDA0002519959280000201
when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, (R)8)nThe substituents are shown in Table 10, and represent the numbers of the compounds which are 67-1-67-11 in sequence.
Watch 10
No. (R8)n No. (R8)n No. (R8)n
67-1 H 67-2 6-Cl 67-3 6-Br
67-4 6-CH3 67-5 6-NH2 67-6 6-OCH3
67-7 6-CF3 67-8 6-OPh 67-9 6-SCH3
67-10 4-CH3-6-Cl 67-11 6-NHCH3
68: in the general formula I-2A, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn accordance with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent the compound numbers in turn 68-1 to 68-11.
69: in the general formula I-2A, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn accordance with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent compound numbers 69-1 to 69-11 in turn.
70: in the general formula I-2A, when R is1＝H、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn accordance with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10, and represent the compound numbers in turn 70-1 to 70-11.
71: in the general formula I-2A, when R is1＝H、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10, and represent the compound numbers in turn 71-1 to 71-11.
72: in the general formula I-2A, when R is1＝H、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn accordance with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent the compound numbers 72-1 to 72-11 in turn.
73: in the general formula I-2A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent the compound numbers 73-1 to 73-11 in turn.
74: in the general formula I-2A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent the compound numbers 74-1 to 74-11 in turn.
75: in the general formula I-2A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent the compound numbers in turn 75-1 to 75-11.
76: in the general formula I-2A, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 1, a substituent (R)8)nIn accordance with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent the compound numbers 76-1 to 76-11 in turn.
77: in the general formula I-2A, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 2, a substituent (R)8)nIn agreement with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent the compound numbers in turn 77-1 to 77-11.
78: in the general formula I-2A, when R is1＝CH3、R3＝R4＝H、R5＝CH3When m is 3, a substituent (R)8)nIn accordance with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10 and represent the compound numbers 78-1 to 78-11 in turn.
In the general formula I-2C,
Figure GDA0002519959280000211
79: in the general formula I-2C, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 in Table 10 and represent the compound numbers 79-1 to 79-11 in turn.
80: in the general formula I-2C, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn accordance with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 of Table 10, and represent the compound numbers in turn 80-1 to 80-11.
81: in the general formula I-2C, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 10, the substituents correspond in turn to 67-1 to 67-11 in Table 10 and represent the compound numbers in turn 81-1 to 81-11.
In the general formula I-3A,
Figure GDA0002519959280000212
when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, (R)8)nThe substituents are shown in Table 11, and represent the compound numbers in turnIs 82-1 to 82-48.
TABLE 11
No. (R8)n No. (R8)n No. (R8)n
82-1 H 82-2 2-CN-6-CH3 82-3 2-SCH3-6-CH3
82-4 6-C3H7 82-5 2-SCH3-5-Br 82-6 2-CN-5,6-diCH3
82-7 6-Cl 82-8 5-NH2-6-Cl 82-9 2-PhNH-6-CF3
82-10 2-Cl 82-11 2-SCH3-5-Cl 82-12 2-SO2CH3-6-CF3
82-13 6-OH 82-14 2-SCH3-6-Cl 82-15 2-SO2CH3-6-CH3
82-16 5-CH3 82-17 2-Ph-4-CH3 82-18 2-CF3-5,6-diCH3
82-19 2-NH2 82-20 2-NH2-6-CH3 82-21 2-CF3-5-CO2C2H5
82-22 2-Ph 82-23 6-Cl-2-PhCH2 82-24 2-CN-5-CH3-6-Cl
82-25 2,6-diNH2 82-26 2-NH2-6-CF3 82-27 2-SCH3-5-OH-6-Cl
82-28 2-CN-6-Cl 82-29 2-NH2-6-OCH3 82-30 2-(3-CH3-Ph)-6-OH
82-31 2-CN-6-CF3 82-32 2-SCH3-6-NH2 82-33 2-CONH2-6-CH3
82-34 5-Cl-2-NH2 82-35 2-SCH3-6-CF3 82-36 2-CONH2-6-CF3
82-37 2-(Cyclopropyl)NH-6-CF3 82-38 2-(3,4-diCl-Ph)NH-6-CF3 82-39 2-(4-Cl-Ph)NH-6-CF3
82-40 2-(2-Cl-Ph)NH-6-CF3 82-41 2-(2,4-diF-Ph)NH-6-CF3 82-42 2-(2,3,4-triCl-Ph)NH-6-CF3
82-43 2-(2,3-diCl-Ph)NH-6-CF3 82-44 2-(4-F-Ph)NH-6-CF3 82-45 2-(2,6-diCl-Ph)NH-6-CF3
82-46 2-(2,4-diCl-Ph)NH-6-CF3 82-47 2-(2-F-Ph)NH-6-CF3 82-48 2-(2,6-diF-Ph)NH-6-CF3
83: in the general formula I-3A, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11 and represent the compound numbers 83-1 to 83-48 in turn.
84: in the general formula I-3A, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11 and represent the compound numbers in turn 84-1 to 84-48.
85: in the general formula I-3A, when R is1＝H、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11, representing compound numbers in turn 85-1 to 85-48.
86: in the general formula I-3A, when R is1＝H、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11 and represent the compound numbers 86-1 to 86-48 in turn.
87: in the general formula I-3A, when R is1＝H、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11 and represent the compound numbers 87-1 to 87-48 in turn.
88: in the general formula I-3A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11, representing compound numbers in turn 88-1 to 88-48.
89: in the general formula I-3A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11 and represent the compound numbers in turn 89-1 to 89-48.
90: in the general formula I-3A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11, representing compound numbers in turn from 90-1 to 90-48.
In the general formula I-3B,
Figure GDA0002519959280000221
when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, (R)8)nThe substituents are shown in Table 12, and represent the compound numbers of 91-1-91-20 in sequence.
TABLE 12
No. (R8)n No. (R8)n No. (R8)n
91-1 H 91-2 4,6-diCH3 91-3 4-CO2CH3
91-4 5-Br 91-5 4-thienyl 91-6 4,6-diOCH3
91-7 4-CH3 91-8 4,6-diCl 91-9 4,5,6-triCl
91-10 4-furyl 91-11 6-Ph 91-12 4-Cl-5-Br
91-13 4-(4-Cl-Ph) 91-14 4-NH2-5-CN 91-15 4-CH3-6-CO2C2H5
91-16 5-CO2CH3 91-17 4-Cl-6-CH3 91-18 4-CF3-5-CO2CH3
91-19 4-CH3-6-CO2CH3 91-20 2-Pyridyl-5-Cl-6-CH3
92: in the general formula I-3B, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12, representing compound numbers in turn 92-1 to 92-20.
93: in the general formula I-3B, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12 and represent the compound numbers in turn 93-1 to 93-201.
94: in the general formula I-3B, when R is1＝H、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12 and represent the compound numbers 94-1 to 94-20 in turn.
95: in the general formula I-3B, when R is1＝H、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12, and represent the compound numbers in turn 95-1 to 95-20.
96: in the general formula I-3B, when R is1＝H、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12, and represent the compound numbers in turn 96-1 to 96-20.
97: in the general formula I-3B, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12, and represent the compound numbers in turn 97-1 to 97-20.
98: in the general formula I-3B, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12, and represent the compound numbers in turn 98-1 to 98-20.
99: in the general formula I-3B, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12, and represent the compound numbers in turn 99-1 to 99-20.
In the general formula I-3D,
Figure GDA0002519959280000231
100: in the general formula I-3D, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11 and represent the compound numbers in turn from 100-1 to 100-48.
101: in the general formula I-3D, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn accordance with the substituents in Table 11, the substituents correspond in turn to 82-1 of Table 1182-48, representing the compound numbers 101-1-101-48 in sequence.
102: in the general formula I-3D, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 11, the substituents correspond in turn to 82-1 to 82-48 of Table 11 and represent the compound numbers in turn 102-1 to 102-48.
In the general formula I-3E,
Figure GDA0002519959280000232
103: in the general formula I-3E, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12 and represent the compound numbers in turn 103-1 to 103-20.
104: in the general formula I-3E, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 of Table 12 and represent the compound numbers in turn 104-1 to 104-20.
105: in the general formula I-3E, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 12, the substituents correspond in turn to 91-1 to 91-20 in Table 12 and represent the compounds having the numbers in turn from 105-1 to 105-201.
In the general formula I-4A,
Figure GDA0002519959280000233
when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, (R)8)nThe substituents are shown in Table 13, and represent the numbers of the compounds as 106-1-106-16 in sequence.
Watch 13
No. (R8)n No. (R8)n No. (R8)n
106-1 H 106-2 5-Cl 106-3 6-Cl
106-4 5-NH2 106-5 5-CN 106-6 6-CN
106-7 3-Cl 106-8 5-CH3 106-9 6-OCH3
106-10 5-OCH3 106-11 5-SCH3 106-12 6-SCH3
106-13 6-OPh 106-14 5-OPh 106-15 5-SPh
106-16 5,6-(CH＝CCl-CH＝CH-)
107: in the general formula I-4A, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 of Table 13 and represent the compounds having the numbers in turn from 107-1 to 107-16.
108: in the general formula I-4A, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 in Table 13 and represent the compounds having in turn 108-1 to 108-16 in number.
109: in the general formula I-4A, when R is1＝H、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 in Table 13 and represent the compound numbers 109-1 to 109-16 in turn.
110: in the general formula I-4A, when R is1＝H、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 of Table 13 and represent the compound numbers in turn 110-1 to 110-16.
111: in the general formula I-4A, when R is1＝H、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 in Table 13 and represent the compounds having the numbers in turn from 111-1 to 111-16.
112: in the general formula I-4A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 in Table 13 and represent the compound numbers in turn 112-1 to 112-16.
113: in the general formula I-4A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 of Table 13 and represent the compounds numbered in turn 113-1 to 113-16.
114: in the general formula I-4A, when R is1＝i-C3H7、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 of Table 13 and represent the compound numbers in turn 114-1 to 114-16.
In the general formula I-4B
Figure GDA0002519959280000241
115: in the general formula I-4B, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 1, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 of Table 13 and represent the compounds numbered in turn 115-1 to 115-16.
116: in the general formula I-4B, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 2, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 of Table 13 and represent the compound numbers in turn 116-1 to 116-16.
117: in the general formula I-4B, when R is1＝CH3、R3＝R4＝R5When H, m is equal to 3, the substituent (R)8)nIn agreement with the substituents in Table 13, the substituents correspond in turn to 106-1 to 106-16 of Table 13 and represent the compound numbers 117-1 to 117-16 in turn.
In the general formula I-1A, when R is1＝CH3、R4＝R5＝H、m＝1、(R8)n＝3-Cl-5-CF3When the substituent R is3(in the case of hydrogen) are different substituents as shown in Table 14, and represent the compounds with the numbers 118-1-118-140 in sequence.
TABLE 14
Figure GDA0002519959280000251
Figure GDA0002519959280000261
The salts of some of the compounds of the present invention are illustrated by the salts of the specific compounds listed in Table 15, but are not intended to limit the present invention.
Table 15 partial compound salts
Figure GDA0002519959280000262
Figure GDA0002519959280000271
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: the compound of the general formula I is prepared by the following method:
Figure GDA0002519959280000281
in formula VI, M is a leaving group selected from chlorine or bromine; the other groups are as defined above.
Intermediate IV forms intermediate V which is then reacted with intermediate VI in a suitable solvent under basic conditions, or intermediates IV and VII are reacted in a suitable solvent under basic conditions to give the compound of formula I.
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 IV is a key intermediate for preparing the compound of the general formula I, and is prepared by the following method:
Figure GDA0002519959280000282
taking II as a raw material to synthesize an intermediate III, and further synthesizing an intermediate IV, and referring to the following documents: WO2008057402, WO2004087056 and the like.
Intermediates VI and VII are commercially available and can also be prepared by known methods, for example as described in references US20100158860, WO2011133444 and Bioorganic & Medicinal Chemistry,20(20),6109-6122,2012.
Although the compounds of the general formula I belong to the substituted pyrazoles containing pyrimidine, the structural characteristics of the compounds are still significantly different from those of the compounds disclosed in the prior art. 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 (Agrimonia spp.) (wireworm), Anoplophora glabripes (Anopyra glabripennis) (Asian longhorn beetle), Gongosia species (Anthonoma spp.) (Arthrobacter flavidus), Gongosia grandis (Anthonomonus grandis) (Cotton bollworm), Cochloa species (Aphidius spp.), Arthrospora sp.) (Anoloides), Cochloa spp. (Anacardia) and Cochloa sinensis (Aponina spp.) (grub), Cochlothuroptera nigra (Atacnniphyllosporus spilus) (Black beetle) (Pieris), Pieris versicolor (Pieris versicolor) (Pieris indica (Pieris) and Pieris indica (Pieris grandis) and Pieris sinensis (Pieris) species (Pieris sinensis (Pieris) and Pieris variety (Pieris sinensis (Pieris) Pieris variety (Pieris sinensis (Pieris) and Pieris) Pieris (Pieris) such as Pieris (Pieris sinensis (Pieris) and Pieris (Pieris sinensis (Pieris variety (Pieris) and Pistospos) such as, Cacoesia species (Cacoesiaspp.), Callosobruchus maculatus (Callosobruchus maculatus) (southern cowpea weevil), yellow spot dew nail (carpophilus humilis) (xerophys), tortoise shell (Cassida witta), longicorn species (ccystcrna spp.), Ceratoma species (Ccrotoma spp.) (chrysomella (chromycosis), bean leaf beetle (Ceratoma trifoliata) (Bean leaf beetle), Chlorophyta species (Ceratophycus spp.) (elephant), Chinese cabbage turtle species (Ceratophycus nigra) (Chinese cabbage weevil (cabbage sepedoid), turnip beetle (Ceratophycus) and western cabbage beetle (cabbage caterpillar), European red cabbage beetle (cabbage beetle), Japanese cabbage beetle (cabbage beetle), Japanese beetle (Colostrinia), Japanese beetle (Coleus) and Japanese beetle (Colostrinia), Japanese beetle (Coleus) species (Coleus, red beetle), red beetle (Coleus, red beetle), Green beetle), red beetle (corn beetle), Green beetle (corn beetle, red beetle (corn beetle), red beetle (corn beetle, red beetle (corn beetle), Green beetle, red beetle, Examples of such plants include, but are not limited to, croplanus longicornis (cromolis), trustees terrestris (cromoptes turcicus) (Turkish grainbetile), ctenicira species (ctencerra spp.) (nematode), elephant species (cululio spp.) (weevil), rhinoceros species (cycleephora spp.) (grub), caryophyllus microphyllus (cylindrus spabesseyi), mangoes leucotrichum (parapherum marginatus) (coprinus), mangoes leucotrichum (mangifera leucotrichum-cutting weevil) (coprinus), hamus pelargonium (dermestoides) (coprinus leucotrichum), leucotrichum (leucotrichum) (coprinus), leucotrichum (leucotrichum-cornutum), leucotrichum (leucotrichum), leucotrichum (leucotrichum (leucotrichum), cucurbitacearum (leucotrichum (leucotrichum), cucurbitacearum (leucotrichum (leucotrichum) and leucotrichum (leucotrichum (leucotrichum leuco, Hyperdos species (Hyperdos spp.) (argentine stem weevil (Hyperodes weevil)), coffee berry silly (Hyperthenemus hampeii) (coffee berry beetle), carinatus species (Ips spp.) (thorn silly (engers)), tobacco beetle (Lasioderma serricorn), potato beetle (Leptinotarsa decemlineata) (Colorado potato beetle), Liogenys fuscus, Liogenys sururalis, rice water weevil (Lissopterus oryzae) and Pinctada species (Lyctus spp.) (wood louse/whitefly beetle (powder nest beetrole), Messostrea sepala (Messochloes.) (Mexerosis), Mexeromyces roetherus sporus (Mexerosis), Mexerosis chinensis, Mexerophthalmus spp. (Mexerosis spp.) (Mexerosis chinensis), Mexerosis chinensis, Mexerophthalmus beetle (Mexerosis beetle), Mexerosis spp. (Mexerosis) and Mexerosis spp. (Mexerosis) can, Mexerosis spp Traded saw beetles (oryzaephius mercator) (market saw beetles (merchant grain beetles)), larval beetles (oryzaephius surrinamensis) (sabothothiaca terrestris (ceratoyomyces reticulatus)), rhynchophorus rostratus (oidhyalomyces spp.) (elephant), black horned mud worm (oculema melanus) (orange-foot mud worm (cerealeppee)), mud worm (oculema oryzae), rhynchophorus oryzae (oculomorpha), rhynchophorus roseus sp. (elephant), gill-leaf gill. sp. (phyllopharia spp.) (phakomare/judaisiella), phvlyphopharia cuyana, striped beetle (phyllothria spp.) (chrysosporium), rhabdoviride (chrysopharia striatus) (bellina), rhabdoviride (chrysopharia striatus) (gore), rhabdo (chrysopharia), rhabdophora), rhabdo (chrysopharia striatum (cornus spp. (gore) (european beetles), rhabditis (cornus) (european carthamia (purpurea (cornus), rhabditis (cornus), rhabditis sp. (rhabditis), rhabditis (cornus sp.) (rha. benthamalis (cornus) (gore), rhabdus) (gore (cornus) (european grub.) (rha. benth.) (rha), rhabdus) (euonymus) (eudragons), rha. benth.) (rha The plant is selected from the group consisting of cryptorhynchus species (Rhynchophorus spp.) (weevils), silly species (Scolytus spp.) (woodchuck moths), Shonophorus species (Shenophorus spp.) (elephant), pea leaf elephant (Sinynana lincatalytic us) (pea leaf weevil), rice weevil species (Sinopophilius spp.) (grain weevil), grain elephant (Sinopophilius grandis) (millworm (graneveril)), rice weevil (Sinopophilius oryzae) (rice weevil), grain steatites (Stegobobium panicum) (drug A (drug substance)), grain quasi grain plant (Tribolium spp.) (grain surface), grain steatile (Tribolium), and red beetle (pseudoflorum), grain steatile (pseudoflorum), red beetle (red beetle), red beetle (red beetle) and red beetle (red beetle) are obtained by using a red beetle.
Dermaptera (Dcrmaptcra) (earwigs).
Vein winged order (Dictyoptera) (cockroach): german cockroach (Blattella germanica) (German cockroach), Blatta orientalis (Blatta orientalis), Blatta palustris (cocitria pennymannica), Periplaneta americana (peri americana) (americana), Blatta australiana (peri australiana), Blatta australiana (australian cockroach), Periplaneta fusca (pcripta rubra) (brown cockroach)), Periplaneta fumosa (peri fuliginosa) (black chest cockroach (cockowbrin), and Periplaneta fuliginosa (brown cockroach)), and Periplaneta fuliginosa (brown cockroach) (brown cockroach).
Diptera (Diptera) (flies): mosquito species (Aedes spp.) (mosquito), lucerne fly larvae (Agromyza front) (alfa blooms), agromyzis species ((Agromyza spp.) (leaf miner), trypetid species (anastrep spp.) (fruit fly), garleria persica (anastrep persica), garleria persica (garleria persica) (garleria persica (Caribbean front fly)), mosquito species (anophes spp.) (mosquito), fruit fly species (batrachia spp.) (fruit fly), melon fly (Bactrocera curbitae) (melon), citrus fruit fly (Bactrocera dorsalis), mosquito seed (ceitis spp.) (mosquito), mosquito fly larvae (sea fly larvae) (sea fly), sea fly larvae (deer flies), sea fly larvae (sea fly) (grubs), sea fly larvae (sea fly) (moth), sea fly larvae (mangosteria spp.) (mangostema spp.) (fruit fly) (moth), mosquito seed fly larvae (deer sp.) (fruit fly, sea fly) (mosquito seed of garrisflavus sp.) (mangifera) (mosquito seed) (moth. sp.) (moth), mosquito larvae (sea fly) (moth), sea fly) (moth larvae (sea fly) (biles sp.) (368652) Leaf of rape mosquito (Dasineura brassicae) (cabbage mosquito), Dimochi species (Delia spp.), Gray fly (Delia platura) (root maggot (seed corn trap)), Drosophila species (Drosophila spp.) (vinegar fly), Musca species (Fannia spp.) (housefly), yellow belly fly (Fannia canicillila) (summer fly (litter fly), Grey belly fly (Fannia salacia), Large belly fly (Gastrophilus intestinalis) (horse stomach fly), Gracillia persea, sheep bloody fly (Haematobia irritanis) (horn fly), Black fly species (Hylemia sp.) (root maggot) (root fly)), Musca fly (common fly) (Meedonia fly (leaf fly)), Musca fly (cabbage fly), Musca fly (cabbage fly) (fly), Musca fly (cabbage fly), Musca fly (leaf fly) (fly), Musca fly (leaf fly (cabbage fly) (fly), Musca fly (leaf fly) (fly), Musca fly (leaf fly (cabbage fly) (fly), Musca fly (leaf fly) (fly) and Musca fly (leaf fly) (fly), Musca fly (leaf, leaf fly) (fly) and Musca fly (leaf fly) (fly), Musca fly (fly) of Musca fly, Musca fly) (fly, Musca fly) (, The plant includes, but is not limited to, the species fall houseflies (Musca australis) (face flies), houseflies (Vuscadomestica) (house flies), sheep houseflies (oesteurs) (sheep nose flies), european stem flies (ostrich flies), beet spring flies (pegmyia beta) (spinach leaf flies), medflies (phophora spp.), carrot stem flies (psilla rosella (carrotrythrix), cherry fruit flies (cherry fruit flies), apple fruit flies (rhapontia pompona) (apple maggots), red mud flies (sitodiplosis mosellana) (orange flies), and cattle fly (horsefly larvae) (stable flies).
Hemiptera (Hemiptera) (stinkbug): apolygus lucorum (Acrosteronum hieron) (green stink bug), Oryza sativa (Black leucopterus), Oryza sativa (Black stink bug), Dicheliopus furcata, Oryza sativa (Black stink bug) (Eudrags), Oryza sativa (Lepidus), Oryza sativa (Lepidorhinus), Oryza sativa (Missis (Black stink bug), Oryza sativa (Black stink bug (Black stink, Oryza), Oryza sativa (Missi), Oryza) and Missi variety (L. A, Oryza variety (L) and A. A, Oryza variety (L. A, Oryza variety (C. A) and A, Oryza variety (C. variety (Oryza variety of Oryza variety (C Hibiscus syriacus linnaeus (macrocytococcus hirsutus), neuroolpus longirostris, lygus lucorum (Nezara viridula) (southern green stink bug), lygus lucorum species (PhyLocoris spp.) (lygus), california lygus lucorum (phytooriforus), phytoorius relatus, pisodours guildingding, lygus tetragonorrhalis (poecillatus) (fleurled plant bug), pseudomonas vaccinicola, pseudacosta perseae, scaptococcus siraitia, and trypanosoma species (atoma spp.) (blood-sucking nose conus)/hunting).
Homoptera (Homoptera) (aphid, scale, whitefly, leafhopper): pea aphid (Acrythosiphopkinsum) (pea aphid), Globius species (Adelsges spp.), Beelaphus sp (adelgids), Aleurodersoproplella brassicae (Aleurodersoproplella cabbage), Aleurodicus disperses (Aleurodersonius), Aleurotricha velutinus (Aleurothrix striatus), Aluraria albizius (Aleurothrix striatus), Aluraria biguella, Laticaria species (Aphrophola sp.), Alrasla bisporus (Leaffiphora), Pyrococcus erythraea (Aphio), Rhodococcus rhodochrous (Amaranthus pratus), Aleuryphylla (Aphyllus flavus), Aleuryphylla (Bethes flavus), Aleuropa nilaparvata (Beyphylla aphid), Aleuryphylla sp (Beyphylla), Aleuropa nilaparvata (Beyphylla flavus), Aleuropa nilla indica (Beethra), Aleuryphylla nilapa (Bectonia) and Bectonia aphid (Beyphylla), Bectonia aphid (Bectonia solani), Bectonia solani (Beyphylla, Bectonia solani (Bectonia solani), Benothophyllum aphid, Beartii (Bectonia solani), Bectonia solani (Bectonia solani), Benothophyllum, Beartii (Benothophyllum, Beartii), Beartii (Bectonia solani), Benothophyta, Beyphylla, Benothophyta, Beyphylla, Benapus (, Brevennia rehi, cabbage aphid (Brevicornus brassicae) (cabbage aphid), Ceroplastes sp (Ceroplastes spp.) (scale), red Ceroplastes rubens (red wax scale), Scedosporium sp (Chionasp. spp.) (scale), Scedosporium sp. peltatus (Chrymophilus spp.) (scale), Ceripostes sp. donovani (Coccusp.) (scale), Phyllosporium carotovora sp.) (Coccusp.) (scale), Pinctada pink (Dysapphigenis planigeana) (roy apple aphid), Phyllosporium viridis (Empoasca spp.) (leafhopper), Phyllosporium aurantiacum (Ersolomophys) (Graphophys aphid), Phyllo persicaria (Lephysallow) (Graphophora aphid), Phyllophora gossypii (Gray), Phyllospora sp. oryzae (Lephysum), Phyllophora grandis (Lephysallow) (Gray) and Phyllophora grandis (Lephysallow) (Gray) aphid) (Lephysallow) (Lephys) (Lephysallow) of Phyllo Long-tube aphids (Macrosiphum rosae) (rose aphid), Quilamenta quadrangularis (Macrostes quadratus) (purple leaf aphid), Mahanarva fribiolata, Meanophys sanguinea (Metolophys dirhodium), Midis longicornis, Myzus persicae (Myzus persicae) (green leaf aphid), Nephophys species (Nephophyx spp.) (leaf hopper), Nephophycticeps nigra (Nephophys nigra), Paracoccus (Paraphyceae), Phytophthora melanosporus (Phosphaera), Phosphaera melanophora (leaf aphid), Phosphaera melanophora (leaf), Phosphaera melanophora (leaf), Phosphaera (leaf beetle grandis), Phosphaera (Phosphaera) and Phosphaera (Phosphaera) variety (Phosphaera), Phosphaera (Phosphaera grandis) Mealybugs pineapple (pseudococcus brcvpcs) (pink apple mcalybug), pernicia viridis (quadrspiodicus persicus) (San Jose scale), aphid species (Rhapalosiphum spp.) (aphid), corn leaf aphid (Rhapalosiphum maida) (corn leaf aphid), green pipe aphid (Rhapalosiphum padi) (opard-cherry aphid), pearl wax beetle species (issetia spp.) (scale), olive wax beetle (issetiaoleayeolegrass) (black binary aphid), Schizaphis graminis (schinopsis grandis) (wheat pipe aphid), green leaf aphid (green leaf aphid), green leaf aphid (green leaf aphid) of green leaf, green leaf aphid (green leaf aphid) of green leaf, green leaf aphid (green leaf aphid, green leaf aphid (green leaf aphid) of green leaf aphid (green leaf aphid), green leaf aphid (green leaf aphid) of green leaf aphid (green leaf) of green leaf, green leaf aphid, trialeurodes albugineus (Bandedwing whitefly), Aceris spp (scale), Ascophyllum yanonensis (scale), Ascophyllum sagittatum (scale), and Zulia entreriana.
Hymenoptera (Hymenoptera) (ants, wasps and bees): incised leaf ant species (Acrommerx spp.), Sinkiang Blastemid (Athalia rosae), leaf ant species (Atta spp.) (Ieafcutting ants), black ant species (Camponotus spp.) (carpenter ant)), pine leaf bee species (Diprion spp.) (Blastemid (sawfly)), ant species (Formica spp.) (Ant), Argentina ant species (Iridogyrmex pollicis) (Argentina), Carcinia subnata (Monorium spp.) (Mongolium Formica.) (Mongolicum frit), Carnitium microphyllum (Meliotica), Meliotica (Meliotica swamp.) (Meliotica), Meliotica (Melothrix spp.) (Melothrix), Melothrix (Melothrix spp.) (Melothrix), Melothria spp. (Melothrix), and Melothrix (Polaris (Solomonus spp.) (Polaris), Melothrix spp. (Melothrix spp.) (Melothrix), and (Solomon) (Melothria spp.) (Polaris), Sinapis spp (Melothrix spp.) (Melastemid (Melasto spp.) (Melasto) and Melasto wasp) species (Melasto wasp) are harvested, Wasp species (vespela spp.) (yellow jack) and trichogramma species (Xylocopa spp.) (carpenter bee).
Isoptera (Isoptera) (termites): coptotermes spp, Coptotermes curcus, Coptotermes curcumine, France termite, Coptotermes formosanus, Formosan subcoternier, Corniteus spp, Sanicular termite, Chrysopotermes spp, Sanicular termite, Meliottermes spp, Coptotermes formosanus, Formosan subcotermes ternitus, Heterotermes spp, Coptotermes formosanus, Coptotermes spp, Coptotermes formotermes spp, Coptotermes formosanus spp, Coptotermes formosanus spp, Coptotermes termes spp, Coptotermes termes spp, Reticulitermes banyulensis, Spodoptera frugiperda (Reticulitermes grassei), Reticulitermes flavipes (Reticulitermes flavipes) (eastern soil-dwelling termites), Reticulitermes speginis (Reticulitermes shaginis), West Scopolia (Reticulitermes heperuus) (West soil-dwelling termites), Moraxella (Reticulitermes santonensis), Norterex (Reticulitermes speratus), Reticulitermes spicatalis (Reticulitermes tibialis), Reticulitermes virginicus (Reticulitermes virginicus), Reticulitermes species (Schedorthomes spp.) and Zootes spp (Zooter spp.).
Lepidoptera (Lepidoptera) (moths and butterflies): achoea janata, Trichoides fusca (Adoxophyesspp.), Trichoides gossypii (Adoxophyceae orana), Gekko sp (Agrotis spp.), cutworm (Agrotis ipsilon) (Black cutworm), Trichoides gossypii (Alabama arginata) (Cotton leaf worm (cottonleaf worm)), Amorbia cuneata, Amylosis trastucena (Na orange), Anacoptida defluvignosa (Antarctica Linatella) (peach twigs), Melothria cocephala (Anomis sabulifera) (J. benth), Trichoides punctata (Antarctica), Trichoides punctata (Anthoides punctata), Trichoides punctata (Boilota), Trichoides punctata (Bombycina) and leaf moth (leaf) of Trichoides (Boilona), Trichoides punctifera punctata (leaf) of Ostrinia (Boilota), Trichoides punctifera (leaf) and leaf moth (leaf) (tobacco leaf) (apple leaf) of Ostrinia (leaf), Sporita (leaf), Sporinoctuina) of Ostrinia (Bodinaria), Sporina (leaf moth (leaf), Sporina) of Ostrinia (leaf, Sporidonta), Sporicanephora (leaf moth of Sporina, Sporicanula (leaf moth of Sporina) of Sporicanula (leaf, Sporinocarpa), Sporidinifera, Sporina, Sporidinifer (leaf, Sporina, Sporiganella) of Sporina, Spori, Sporina, Capua reticulana, peach moth (Carposina niponensis) (peach fruit moth)), Phlebia species (Chilo spp.), mango lateral tail moth (Chuumetia transsa) (mango shoot bolt bor), rose leaf moth (Choristoneura rosea) (arbor stem moth (Choristoneura pallida) (obesity barrel), Spodoptera species (Chromodeis spp.), Spodoptera grisea (Chromodendron griseofulensis), Spodoptera griseola (Grass leaf moth), Spodoptera species (Coliasspp), Pleurotus litura punctatus (Spodoptera), Spodoptera odorata (Spodoptera), Spodoptera litura (apple leaf moth) (apple moth), Spodoptera ostrinia (apple moth), Spodoptera granulosa (apple moth (moth), Spodoptera ostrinia (apple stem moth (moth), Spodoptera granulophila ostrinia punctifera (moth), Spodoptera (apple moth (apple moth), Spodoptera fructia), Spodoptera (moth), Spodoptera fructia (moth), Spodoptera (moth), Spodoptera fructia), Spodoptera (moth), Spodoptera) and Spodoptera (moth), Spodoptera) insect (moth, Spodoptera) insect (moth, borer species (Diatraea spp.) (stem borer (stamp bor)), sugarcane borer (Diatraea saccharalis) (sugaranee borre), southwestern corn borer (Diatraea grandiosella) (soutware cornbor), diamond-like carbon seed (Earias spp.) (cotton bollworm), diamond-like carbon (earia grandis) (egyptiana borealis), diamond-like carbon (earbud), diamond-like carbon (earwax), corn borer (Elasmopa) and yellow meadow (yellow meadow moth) (september), apple moth (epirubia punctifera), black leaf moth (yellow meadow moth) (Epstein), black leaf moth (yellow borer), black meadow (yellow meadow moth), black meadow moth (black meadow moth), black meadow moth (black meadow moth), black meadow (black meadow moth), black meadow moth (black meadow moth), black meadow moth (black meadow, meadow moth), black meadow (e (black meadow (e, meadow moth), black meadow (e, meadow moth), black meadow (e, meadow (meadow moth), black meadow, The plant may be selected from the group consisting of primary cutworms (Euxoa auricularis) (armychus), cutworm species (felia spp.) (cutworms), hornworm species (Gortyna spp.) (stem borers), oriental moth (Grapholita molesta) (peach (apricot) fruit borer (original fruit moth)), trilobata (hedylella indica) (bean leaf borer (bean leaf webber)), cyan worm species (heliotropina spp.) (noctuid), cotton bollworm (helicopterpa armigera) (cotton bollworm), Helicoverpa armyworm (Helicoverpa armyworm) (helicoptera), corn borer (Helicoverpa armyworm) (ostrinia nubilalis/cotton worm)), Helicoverpa species (helicopteroth spp.) (helicopteris spp.) (helicopterocarpa sp.) (helicopterocarpa punctata), tobacco bud (helicopterocarpa), cabbage moth (cabbage leaf borer), seedling borer (cabbage moth, cabbage moth (cabbage moth, moth (moth, grape leaf borer (Lobesia botana) (grapple fruit moth), Loxagrotis species (Loxagrotissp.), noctuid (noctuid), soybean wireworm (Loxagrotis albicostata) (western bean cucumber), gypsy moth (Lymantria dispar) (gypsy moly), peach leaf miner (Lyonetherkella) (apple leaf miner), oil palm bag moth (Mahasena corteoti) (oima palmatum), broad leaf beetle (Maliosoma spp.) (tent caterpillar), cabbage leaf moth (Mamestraba assica) (cabbage armyworm)), soybean stem borer (Maruca), cabbage leaf borer (cabbage caterpillar) (ostrinia nubilalis), European cabbage leaf borer (ostrinia borer) (ostrinia moth (cabbage armyworm), European cabbage leaf borer (cabbage caterpillar), European cabbage leaf borer (ostrinia nubila), European cabbage moth (cabbage caterpillar) (ostrinia nubila nubilalis (ostrinia moth (ostrinia nubila nubilalis)), European cabbage (ostrinia nubilalis), European cabbage moth (ostrinia nubila nubilalis), European cabbage moth (ostrinia nubila nubilalis) (ostrinia nubilalis) (ostrinia nubila (ostrinia nubilalis), European (ostrinia nubila nubilalis (ostrinia nubila (ostrinia) or (ostrinia nubila), European (ostrinia (ostr, Apple leaf rollers (Pandemis heparama) (brown apple tortrix), african reach (Papilio demodulus), red bell moth (Pectinophora gossypiella) (pink bollworm), Spodoptera species (Peridroma spp.) (root cutting), hybrid old tiger (Peridroma saucia) (variegated cutworm), coffee leaf miner (Perilurera flavedola) (white coffee leaf miner), potato leaf miner (Phorimaea operculella) (potato leaf miner), orange leaf miner (Phyllanthus fructicola) (cabbage leaf miner), Plutella xylostella (Plutella xylostella), Plutella xylostella (Plutella), Plutella xylostella) A (Plutella) A) and Plutella xylostella (Plutella) A), Pseudoplusia unipunctata (armyworm), Spodoptera exigua (Spodoptera frugiperda), Ectropicalis inchworm (Rachiplusia nu), Sciphoridia pomifera (Scorporea inctoria), Heliothis virescens (Sesamia spp.) (Phoma punctifera), Heliothis oryzae (Sesamia incensis) (Pink rice stem miner), Heliothis punctifera (Sesamia agglrioides), Helicoverpa zea (Sesamia punctata (Sesamara punctata), Heliothis virescens (Sitoglosoma punctata) (Antomophaga graciliata (Sesami), Helicoverpa punctata (Spodoptera), Spodoptera frugiella punctata (Spodoptera), Spodopterocarpus punctifera (Spodoptera), Spodoptera frugium frugiperda (Spodoptera), Spodoptera frugiperda (Spodoptera) species (Spodoptera), Spodoptera frugiperda (Spodoptera), Spodoptera) Spodoptera (Spodoptera), Spodoptera frugiperda (Spodoptera), Spodoptera) and Spodoptera (Spodoptera) including Spodoptera (Spodoptera) and Spodoptera (Spodoptera) including Spodoptera spp (Spodoptera), Spodoptera) including Spodoptera, Spodoptera (Spodoptera) and Spodoptera (Spodoptera) including Spodoptera variety (Spodoptera, The species Nephra (Yponomeuta spp.), the dull coffee leopard moth (Zeuzeracoffeee) (red branchborer) and the stupid pear pyrina (leopard moth).
Mallophaga ((Mallophaga) feather louse (chewing lice)): ovine feather louse (Bovicola ovis) (sheeppbiting louse), turkey short horn feather louse (chicken feather 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), acephala wing spurs (microcentrumretrierve) (angular winged katylid), pterophyces spp species (pterophyceps spp.) (pteropis), stetocera eggria, pteroderma furcifera (scuddermata) (fork tailed bush (fork tailed bustydidid)), and branchionus nigra (planicornia).
Phthiraptera (Phthiraptera) (sucking lice): the blood sucking lice species (haemattopinnus spp.) (bovine lice and swine lice), sheep jaw lice (linogluchus ovilus) (sheep lice), head lice (pediluus humanus capitis) (body lice), human body lice (pediluus humanus (body lice) and crab lice (Pthirus pubis) (crab lice).
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 (Acarus spp.) (food mites), dermatophagoides pteronyssinus (Acarus sroro) (grain mite), mango bud mite (Aceria mangifera) (mango bud mite), dermanyssus spinosus (Acarus spp.), tomato septoria spinosa (Acarus lycopersici) (tomato septemesis), aculopsis pellegelikasi (Acarus septemfasciatus), citrus septemfasciatus (Acarus pellekas), dermanyssus spinosus (Acarus schoenlus) (apple septorius), american cottus (Acarus schoenleus), american cottus (Acarus schoenoprasus), american Acarus schoenoprashii) (mangostis sp.), mangium sp.), mangium (Acarus sp.), mangium sp.), or mangium sp (mangium sp.), and mangrove (mangrove sp (mangrove sp. (insect tick (mangrove sp.) (mangrove) and mangrove sp (mangrove sp. (mange), mangrove sp. (mangrove sp.) (mangrove) and (mange (mangrove sp.) (mange), mangrove) variety (mange (mangrove sp.), or mangrove sp.), Acarus sp. (mangrove sp. (mange (mangrove, House dust mite (Dermatophagoides pteronyssinus) (house dust mite), Tetranychus sp (Eotetranus spp.), hornbeam Tetranychus sp (Eotetranychus carpini (yellow spider mite), Tetranychus sp.), Gephytylus sp (Epimedium sp.), Gephytylus sp (Eriophenopterus sp.), hard tick sp (I.D.; es sp.), ticks (tick), Tetranychus sp.) (Notopterygium sp.), Micropterus species (Ochronychus sp.), Calonychus (Notoedrechsi), Microphytylus sp. (Oligonychus sp.), Calonychus (Ocynonella), Tetranychus wintergreen (Ochrotus) (Tetranychus urticae (Ochrotus), Tetranychus urticae (Tetranychus urticae), Tetranychus urticae (Tetranychus urticae) (Tetranychus urticae (Tetranychus), Tetranychus (Tetranychus) and Tetranychus urticae) (Tetranychus) or Tetranychus) and Tetranychus (Tetranychus) or Tetranychus (Tetrastictus (Tetrasticus) or Tetrastictus (Tetrastictus) or, Rhizomorpha species (rhizomorph spp.) (root mite (bulbmite)), Sarcoptes (Sarcoptes scabies) (itch mite), coronaria avocado (tetragonophus perseafarae), Tetranychus species (Tetranychus spp.), Tetranychus urticae (Tetranychus urticae) (twospoked spider mite (twospotted spider mite)) and Varroa destructor (Varroa destructor) (honey bee mite).
Nematoda (nematodes): the species strongyloides (Aphelenchoides spp.) (bud and leaf and pine wood nematodes (budand leaf & pine wood nematodes)), the species strongyloides (Belololaimus spp.) (sting nematodes), the species strongyloides (Criconema spp.) (ring nematodes), the species Dirofilaria immitis (Dirofilaria immitis) (dog heartword), the species Ditylenchus spp. (stem and bulb nematodes), the species strongyloides (Heterodera spp.) (Cytospora nematodes), the species strongyloides (Heterodera zeae) (nematode), the species strongyloides (Heterocladia nematodes), the species strongyloides (Heterodera pinus) (nematode), the species (Hichlornyloides spp.) (Melilotus spp.)), the species (Melilotus spp.)), the species (Melilotus roses (Melilotus, Melilotus spp.) (Melilotus ), the species (Melilotus roses (Melilotus) and Mel kidney-shaped neural).
General class (general classes of insects): white pine worm (Scutigerella immaculata).
Owing to their positive properties, the abovementioned compounds can be used advantageously for protecting crops, domestic animals and breeding animals of agricultural and horticultural importance, as well as the environment in which humans are often exposed, against harmful germs, pests and mites.
The amount of the compound used to achieve the desired effect will vary depending on factors such as the compound used, the crop to be protected, the type of pest, the extent of infection, the climatic conditions, the method of application, and the dosage form employed.
A dose of 10 g to 5 kg of compound per hectare provides adequate control.
The invention also discloses a 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 10 to 1000 grams per hectare is generally selected, with an effective amount of 20 to 500 grams per hectare being preferred.
For certain applications, for example in agriculture, one or more other fungicides, insecticides, acaricides, herbicides, plant growth regulators or fertilizers and the like can be added to the fungicidal, insecticidal and acaricidal compositions of the present invention, whereby additional advantages and effects can be produced.
It should be understood that various changes and modifications may be made within the scope of the present invention as defined by the claims.
Detailed Description
The following specific examples are intended to further illustrate the invention, but the invention is in no way limited to these examples (all materials are commercially available unless otherwise indicated).
Synthetic examples
Example 1: preparation of intermediate 2- ((3-methylisoxazolo [5,4-d ] pyrimidin-4-yl) amino) ethanol
1) Preparation of 5-amino-3-methylisoxazole-4-cyano
Figure GDA0002519959280000361
14g (0.2 mol) of hydroxylamine hydrochloride was dissolved in 80mL of 10% sodium hydroxide, 27.2g (0.2 mol) of (1-ethoxyethylene) malononitrile was added, a small amount of ice was added to keep the temperature at 50 ℃ or lower, stirring was continued at room temperature for 1.5 hours, and the solid was filtered, washed with water, and recrystallized from absolute ethanol to obtain 16.5g of a solid product.
2) Preparation of 4-chloro-3-methylisoxazolo [5,4-d ] pyrimidine
Figure GDA0002519959280000362
Phosphorus oxychloride (POCl)3)40mL and 1mL of N, N-dimethylformamide were added to a reaction flask, and stirred at room temperature for 1 hour, 5-amino-3-methylisoxazole-4-cyano (451mg, 3.66mmol) was added thereto, the mixture was heated to 160 ℃ to react for 15 to 36 hours, and the reaction mixture was distilled under reduced pressure to give a pale yellow solid having a melting point of 110.5 ℃.
3) Preparation of 2- ((3-methylisoxazolo [5,4-d ] pyrimidin-4-yl) amino) ethanol
Figure GDA0002519959280000363
1.69g (0.01mol) of 4-chloro-3-methylisoxazolo [5,4-d ] pyrimidine and 1.22g (0.02mol) of aminoethanol were added to 50ml of tetrahydrofuran, 4.45g (0.022mol) of triethylamine was added, the reaction was carried out at room temperature for 4 to 10 hours, after completion of the reaction monitored by TLC, the solvent was distilled off under reduced pressure, water was added to precipitate a solid, and the mixture was filtered to obtain an intermediate.
Example 2: preparation of Compounds 7-33
Figure GDA0002519959280000364
0.16g of 60% sodium hydride was put into a reaction flask, washed with petroleum ether, and then 5ml of N, N-dimethylformamide was added, 0.39g (2mmol) of 2- ((3-methylisoxazolo [5,4-d ] pyrimidin-4-yl) amino) ethanol was added thereto, and after stirring at room temperature for 2 minutes, 0.43g (2mmol) of intermediate 2, 3-dichloro-5-trifluoromethylpyridine was added thereto, and the reaction was stirred at 60 ℃ for 2 hours. After completion of the reaction monitored by TLC, the reaction mixture was poured into 50ml of saturated brine, extracted three times with 100 ml of ethyl acetate, and dried. After desolventizing, the product is purified by column chromatography to obtain 0.36 g of oily product, namely the compound 7-33.
1H-NMR (300MHz, internal standard TMS, solvent CDCl3)(ppm):8.51(s,1H),8.34(s,1H),7.90(d,1H),5.83(s,1H),4.71(t,2H),4.16(q,2H),2.64(s,3H)。
Other compounds of the invention may be prepared by reference to the above examples.
Physical property data and nuclear magnetic data of some of the compounds (1HNMR, 300MHz, internal standard TMS, ppm) as follows:
compounds 7-18: (CDCl)3)8.51(s,1H),8.43(s,1H),7.81-7.85(dd,1H),6.86-6.90(d,1H),6.02(s,1H),4.69(t,2H),4.09(q,2H),2.61(s,3H)。
Compounds 8-18: melting point 125.8 ℃. (CDCl)3)8.49(s,1H),8.42(s,1H),7.80-7.84(dd,1H),6.82-6.86(d,1H),5.87(s,1H),4.57(t,2H),3.83(q,2H),2.67(s,3H),2.18(m,2H)。
Compounds 8-33: melting point 126.8 ℃. (CDCl)3)8.47(s,1H),8.31(s,1H),7.87(d,1H),5.83(s,1H),4.61(t,2H),3.87(q,2H),2.64(s,3H),2.26(m,2H)。
9-18 melting Point 132.4 ℃. (CDCl)3)8.47(s,1H),8.42(s,1H),7.79-7.83(dd,1H),6.83-6.86(d,1H),5.63(d,1H),4.78(m,2H),4.52-4.68(m,2H),2.59(s,3H),1.78-1.87(m,2H),1.07(m,2H).
Compounds 9-33 melting point 161.9 ℃.
Compounds 62-18: melting point 197.5 ℃. (CDCl)3)8.44(s,1H),8.32(s,1H),7.76-7.84(dd,1H),6.81-6.87(d,1H),4.57(t,2H),3.95(s,3H),3.72(q,2H),2.65(s,3H),2.20(m,2H)。
Compounds 62-33: melting Point 123.1 ℃. (CDCl)3)8.36(s,1H),8.31(s,1H),7.86(d,1H),5.49(s,1H),4.65(t,2H),3.95(s,3H),3.72(q,2H),2.63(s,3H),2.27(m,2H)。
The other compounds of the present invention represented by the general formula I can also be prepared according to the above-mentioned preparation method. In addition, the salt of the compound shown in the general formula I can be prepared by reacting the compound shown in the general formula I with the corresponding acid according to the conventional prior art. 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 3: 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 the dosage of 25ppm, the inhibition rate of compounds such as 7-33, 8-33, 9-18 and the like on rice blast is more than 80 percent;
at the dosage of 8.3ppm, such as compounds 7-33, the inhibition rate on the rice blast is more than 80 percent;
inhibition rate of cucumber botrytis cinerea:
at the dosage of 25ppm, such as compounds 7-33, the inhibition rate of the cucumber botrytis cinerea is above 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:
under the dosage of 400ppm, such as compounds 7-18, 7-33, 8-18, 8-33, 9-18 and the like, the control effect on cucumber downy mildew is more than 80 percent;
under the dosage of 100ppm, such as compounds 7-33, 8-18, 8-33, 9-18 and the like, the control effect on cucumber downy mildew is more than 80 percent;
at the dosage of 25ppm, such as compounds 7-33, the control effect on cucumber downy mildew is more than 80 percent;
in vivo protective activity against wheat powdery mildew:
under the dosage of 400ppm, such as compounds 7-33, 8-18, 8-33, 9-18 and the like, the control effect on wheat powdery mildew is more than 80 percent;
under the dosage of 100ppm, such as compounds 9-18, the control effect on wheat powdery mildew is more than 80 percent;
in vivo protective activity against corn rust:
under the dosage of 400ppm, such as compounds 9-18, the control effect on the corn rust is more than 80 percent;
in vivo protective activity against cucumber anthracnose:
under the dosage of 400ppm, such as compounds 7-33, 8-18 and the like, the control effect on cucumber anthracnose is more than 80 percent;
under the dosage of 100ppm, such as compounds 7-33, the control effect on cucumber anthracnose is more than 80 percent;
under the dosage of 25ppm, such as compounds 7-33, the control effect on cucumber anthracnose is more than 80 percent;
example 4: determination of insecticidal and acaricidal Activity
Several insects were tested for insecticidal activity using the compounds of the present invention. The measurement method is as follows:
after dissolving a test compound in a mixed solvent of acetone/methanol (1: 1), the test compound was diluted with water containing 0.1% (wt) Tween 80 to a desired concentration.
Taking the green peach aphids as targets, and determining the insecticidal activity by adopting an airbrush spraying method.
The determination method comprises the following steps: a culture dish with the diameter of 6cm is taken, a layer of filter paper is covered on the bottom of the culture dish, and a proper amount of tap water is dripped for moisturizing. And (3) shearing cabbage leaves with proper size (the diameter is about 3cm) and 15-30 heads of aphids from the cabbage plants for culturing the myzus persicae, removing the aphids with the wing aphids and the front sides of the leaves, and placing the leaves in a culture dish with the back sides upward. The airbrush spray treatment was carried out at a pressure of 10psi (approx. 0.7kg/cm2) and a liquid spray volume of 0.5ml, with 3 repetitions of the treatment. And (3) after treatment, placing the treated mixture into an observation room with the temperature of 25 ℃ and the relative humidity of 60-70% for culture, investigating the number of the survival insects after 48 hours, and calculating the mortality.
At a dose of 600ppm, such as compounds 7-18, the lethality rate to the myzus persicae is more than 80%.
The other compounds represented by the general formula I of the invention obtained by the preparation method of the invention are detected according to the determination method, and have corresponding activity effects.

Claims (7)

1. A substituted six-membered heterocyclic compound containing pyrimido ring is characterized in that: the substituted six-membered heterocyclic compound containing pyrimido ring is a compound shown as a general formula I-1A;
Figure FDA0002519959270000011
in the formula:
R1selected from hydrogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C6Cycloalkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C2-C4Alkenyl, halo C2-C4Alkenyl radical, C2-C4Alkynyl or halo C2-C4An alkynyl group;
R2selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C6Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio or C1-C4An alkylsulfonyl group;
R4、R5are the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R6、R7are the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
m is an integer from 0 to 4;
R8selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkyl ammoniaRadical, halo C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR9R10、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 or halo C1-C4Alkylthio group C1-C4An alkyl group;
and in the general formula I-1A, n is selected from integers from 1 to 4, and when n is 1, R8Is not selected from methyl;
or salts of the compounds of the general formula I-1A with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
2. The pyrimido ring-containing substituted six-membered heterocyclic compound according to claim 1, wherein: in the compounds of the general formula I-1A:
R1selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxymethyl, ethoxymethyl or trifluoroethoxymethyl;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl;
R4、R5are the same or different and are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and tert-butoxy;
R6、R7are the same or different and are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and tert-butoxy;
m is an integer from 0 to 4;
R8selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl;
and in the above general formula I-1A, n is selected from an integer of 1 to 4, and when n ═ 1, R is8Is not selected from methyl;
or salts of the compounds of the general formula I-1A with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
3. The pyrimido ring-containing substituted six-membered heterocyclic compound according to claim 2, wherein: in the compounds of the general formula I-1A:
R1selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, cyclopropyl;
R2selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl;
R3selected from hydrogen, methyl, acetyl, trifluoroacetyl, methoxy, methylthio, allyl, methylsulfonyl, methylaminosulfonyl, dimethylaminosulfonyl, methoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylaminothio or dimethylaminosulfanyl;
R4、R5are the same or different and are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R6、R7are all selected from hydrogen;
m is an integer from 0 to 4;
R8selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, trifluoromethoxy, trifluoroethoxy;
and in the general formula I-1A, n is selected from integers from 1 to 4, and when n is 1, R8Is not selected from methyl;
or salts of the compounds of the general formula I-1A with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
4. The pyrimido ring-containing substituted six-membered heterocyclic compound according to claim 3, wherein: in the compounds of the general formula I-1A:
R1selected from hydrogen, methyl, ethyl, n-propyl, isopropylN-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, cyclopropyl;
R2selected from hydrogen, fluorine, chlorine, bromine, iodine or methyl;
R3selected from hydrogen, methyl, acetyl, trifluoroacetyl, methoxy, methylthio, allyl, methylsulfonyl, methylaminosulfonyl, dimethylaminosulfonyl, methoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylaminothio or dimethylaminosulfanyl;
R4、R5are the same or different and are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R6、R7are all selected from hydrogen;
m is an integer from 0 to 3;
R8selected from fluoro, chloro, bromo, iodo, cyano, nitro, methyl, trifluoromethyl, methoxy, or trifluoromethoxy;
formula I-1A, n is selected from integers from 1 to 4, and when n is 1, R8Is not selected from methyl;
or salts of the compounds of the general formula I-1A with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid or citric acid.
5. A process for the preparation of substituted six-membered heterocyclic compounds containing a pyrimido ring according to claim 1, which comprises: the preparation method of the compound shown in the general formula I comprises the following steps:
Figure FDA0002519959270000031
m is selected from chlorine or bromine, the structure of the general formula I is shown in a general formula I-1A in claim 1, and other groups except for other groups indicated in the reaction formula are defined in claim 1.
6. Use of substituted six-membered heterocyclic compounds containing pyrimido rings, represented by general formula I-1A according to claim 1, in the agricultural field for the preparation of fungicides, insecticides.
7. The bactericidal and insecticidal composition is characterized in that: the composition takes a substituted six-membered heterocyclic compound containing pyrimido ring shown in the general formula I-1A as the active component according to claim 1; wherein, the weight percentage of the active components in the composition is 0.1 to 99 percent.
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