CN107540664B - Pyrazolyl pyrimidine ether compound and application thereof - Google Patents

Pyrazolyl pyrimidine ether compound and application thereof Download PDF

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CN107540664B
CN107540664B CN201610463158.1A CN201610463158A CN107540664B CN 107540664 B CN107540664 B CN 107540664B CN 201610463158 A CN201610463158 A CN 201610463158A CN 107540664 B CN107540664 B CN 107540664B
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CN107540664A (en
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刘长令
夏晓丽
王军锋
孙旭峰
兰杰
关爱莹
魏思源
杨金龙
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Abstract

The invention discloses a pyrazolyl pyrimidine ether compound, which has a structure shown in a general formula I:

Description

Pyrazolyl pyrimidine ether compound and application thereof
Technical Field
The invention belongs to the field of agricultural fungicides, and particularly relates to preparation and application of a novel pyrazolyl pyrimidine ether compound.
Background
The Journal of the Chinese Chemical Society (Weinheim, Germany) (2013),60(1),27-34, and WO 2006125370A each disclose the following 2 pyrazolylpyrimidine ethers, mainly as agricultural fungicides.
Figure BDA0001027375650000011
However, the pyrazolyl pyrimidine ether compounds with the structure shown in the general formula I are not reported.
Disclosure of Invention
The invention aims to provide a pyrazolyl pyrimidine ether compound capable of controlling various germs, which can be used for preparing medicines for preventing and treating germs in agriculture or other fields.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a pyrazolyl pyrimidine ether compound is shown as a general formula I:
Figure BDA0001027375650000012
R1is selected from C1-C12Alkyl radical, C3-C8Cycloalkyl, halo C1-C12Alkyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl or C1-C12Alkoxycarbonyl radical C1-C12An alkyl group; or R1 is selected from n R6Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R2selected from hydrogen, cyano, halogen, C1-C12Alkyl radical, C3-C8Cycloalkyl, halo C1-C12Alkyl radical, C1-C12Alkoxycarbonyl or halo C1-C12An alkoxycarbonyl group; or R2 is selected from n R6Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaromaticsAn oxycarbonyl group;
R3selected from hydrogen, cyano, halogen, C1-C12Alkyl radical, C3-C8Cycloalkyl, halo C1-C12Alkyl radical, C1-C12Alkoxycarbonyl or halo C1-C12An alkoxycarbonyl group; or R3 is selected from n R6Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
and when R is1Is C1-C4Alkyl or halo C1-C4When alkyl, R2And/or R3The substituent of (a) is aryl, heteroaryl, arylmethyl or heteroarylmethyl;
R4、R5selected from hydrogen, halogen, amino, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy radical, C1-C12Haloalkoxy, C3-C8Cycloalkyl radical, C1-C12Alkoxy radical, C1-C12Alkylthio radical, C1-C12Alkylsulfinyl radical, C1-C12Alkylsulfonyl radical, C1-C12Alkylamino radical, di (C)1-C6) Alkylamino radical, di (C)1-C6) Alkylamino carbonylamino group, C1-C12Alkylcarbonylamino, halo C1-C12Alkylcarbonylamino, C1-C12Alkoxycarbonyl carbonylamino group, C1-C12Alkoxy radical C1-C12Alkylamino radical, C1-C12Alkylsulfonylamino or C1-C12An alkylamino carbonylamino group;
x is selected from NR9O or S;
y is selected from NR10O or S;
q is selected from the group consisting of m R11Substituted aryl or heteroaryl; m is an integer from 0 to 5;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, halo-di (C)1-C12Alkyl) amino, C (═ O) NR7R8、C1-C12Alkylthio, halo C1-C12Alkylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, C2-C12Alkenyloxy, halogeno C2-C12Alkenyloxy radical, C2-C12Alkynyloxy, halo C2-C12Alkynyloxy, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkoxy radical C1-C12Alkyl, halo C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkylthio group C1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical C1-C12Alkyl, halo C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C1-C12Alkylthio carbonyl group C1-C12Alkyl, halo C1-C12Alkylthio carbonyl group C1-C12Alkyl radical, C1-C12Alkylcarbonyloxy, halo C1-C12Alkylcarbonyloxy, C1-C12Alkoxycarbonyloxy, halo C1-C12Alkoxycarbonyloxy, C1-C12Alkylsulfonyloxy, haloGeneration C1-C12Alkylsulfonyloxy, C1-C12Alkoxy radical C1-C12Alkoxy or halo C1-C12Alkoxy radical C1-C12An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C12Alkyl or halo C1-C12An alkyl group;
R9、R10can be the same or different and are respectively selected from hydrogen, hydroxyl, formyl and 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) aminosulfanyl; arylcarbonyl C unsubstituted or further substituted by 1 to 51-C6Alkyl, heteroaryl carbonyl C1-C6Alkyl, arylcarbonyl, heteroarylcarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, aryl C1-C6Alkyloxycarbonyl, heteroaryl C1-C6Alkyloxycarbonyl, aryl C1-C6Alkyl, heteroaryl C1-C6Alkyl groups: halogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy or halo C1-C6An alkoxy group.
The compounds preferred in the present invention are those of the general formula I
R1Is selected from C1-C6Alkyl radical, C3-C6Cycloalkyl, halo C1-C6Alkyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl or C1-C6Alkoxycarbonyl radical C1-C6An alkyl group; or R1 is selected from n R6Substituted aryl or heteroaryl;
R2selected from hydrogen, cyano, halogen, C1-C6Alkyl radical, C3-C6Cycloalkyl, halo C1-C6Alkyl radical, C1-C6Alkoxycarbonyl or halo C1-C6An alkoxycarbonyl group;or R2 is selected from n R6Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R3selected from hydrogen, cyano, halogen, C1-C6Alkyl radical, C3-C6Cycloalkyl, halo C1-C6Alkyl radical, C1-C6Alkoxycarbonyl or halo C1-C6An alkoxycarbonyl group; or R3 is selected from n R6Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
and when R is1Is C1-C4Alkyl or halo C1-C4When alkyl, R2And/or R3The substituent of (a) is aryl, heteroaryl, arylmethyl or heteroarylmethyl;
n is an integer from 0 to 5;
R4、R5selected from hydrogen, halogen, amino, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio radical, C1-C6Alkylsulfinyl radical, C1-C6Alkylsulfonyl radical, C1-C6Alkylamino radical, di (C)1-C4) Alkylamino radical, di (C)1-C4) Alkylamino carbonylamino group, C1-C6Alkylcarbonylamino, halo C1-C6Alkylcarbonylamino, C1-C6Alkoxycarbonyl carbonylamino group, C1-C6Alkoxy radical C1-C6Alkylamino radical, C1-C6Alkylsulfonylamino or C1-C6An alkylamino carbonylamino group;
x is selected from NR9O or S;
y is selected from NR10O or S;
q is selected from the group consisting of m R11Substituted phenyl, pyridyl, pyrimidinyl, or pyridazinyl; m is an integer from 0 to 5;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and 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) NR7R8、C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, halo C2-C6Alkynyloxy, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkoxy radical C1-C6Alkyl, halo C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylthio group C1-C6Alkyl, halo C1-C6Alkylthio group C1-C6Alkyl radical, C1-C6Alkoxycarbonyl radical C1-C6Alkyl, halo C1-C6Alkoxycarbonyl radical C1-C6Alkyl radical, C1-C6Alkylthio carbonyl group C1-C6Alkyl, halo C1-C6Alkylthio carbonyl group C1-C6Alkyl radical, C1-C6Alkylcarbonyloxy, halo C1-C6Alkylcarbonyloxy, C1-C6Alkoxycarbonyloxy, halo C1-C6Alkoxycarbonyloxy, C1-C6Alkylsulfonyloxy, halo C1-C6Alkylsulfonyloxy, C1-C6Alkoxy radical C1-C6Alkoxy or halo C1-C6Alkoxy radical C1-C6An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C6Alkyl or halo C1-C6An alkyl group;
R9、R10can be the same or different and are respectively selected from hydrogen, hydroxyl, formyl and 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) aminosulfanyl; arylcarbonyl C unsubstituted or further substituted by 1 to 51-C4Alkyl, heteroaryl carbonyl C1-C4Alkyl, arylcarbonyl, heteroarylcarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, aryl C1-C4Alkyloxycarbonyl, heteroaryl C1-C4Alkyloxycarbonyl, aryl C1-C4Alkyl, heteroaryl C1-C4Alkyl groups: halogen, nitro, cyano, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
x is attached to the 3, 4 or 5 position of the pyrazole ring; when X is attached to the 3-position of the pyrazole ring, then R2In the 4 position, R3At position 5; when X is attached to the pyrazole ring at the 4-position, then R2In the 3 position, R3At position 5; when X is attached to the 5-position of the pyrazole ring, then R2In the 3 position, R3At 4 bits.
Further preferred compounds of the invention are: when Q is selected from the group consisting of m R in the formula I11Substituted phenyl group: x is attached to the 3, 4 or 5 position of the pyrazole ring; when X is attached to the 3-position of the pyrazole ring, then R2In the 4 position, R3At position 5, the structural formula is shown as I-1; when X is attached to the pyrazole ring at the 4-position, then R2In the 3 position, R3At position 5, the structural formula is shown as I-2; when X is attached to the 5-position of the pyrazole ring, then R2In the 3 position, R3At the 4-position, the structural formula is shown as I-3;
Figure BDA0001027375650000041
in the above formula:
R1is selected from C1-C4Alkyl radical, C3-C6Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl or C1-C4Alkoxycarbonyl radical C1-C4An alkyl group; or R1 is selected from n R6Substituted phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, s-triazinyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, or isothiazolyl;
R2selected from hydrogen, cyano, halogen, C1-C4Alkyl radical, C3-C6Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl or halo C1-C4An alkoxycarbonyl group; or R2 is selected from n R6Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
R3selected from hydrogen, cyano, halogen, C1-C4Alkyl radical, C3-C6Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl or halo C1-C4An alkoxycarbonyl group; or R3 is selected from n R6Substituted aryl, heteroaryl, arylmethyl, heteroarylmethyl, arylcarbonyl, heteroarylcarbonyl, arylmethylcarbonyl, heteroarylmethylcarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl;
and when R is1Is C1-C4Alkyl or halo C1-C4When alkyl, R2And/or R3The substituent of (a) is aryl, heteroaryl, arylmethyl or heteroarylmethyl;
n is an integer from 0 to 5;
R4、R5selected from hydrogen, halogen, amino, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C3-C6Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Alkylamino radical, di (C)1-C4) Alkylamino radical, di (C)1-C4) Alkylamino carbonylamino group, C1-C4Alkylcarbonylamino, halo C1-C4Alkylcarbonylamino, C1-C4Alkoxycarbonyl carbonylamino group, C1-C4Alkoxy radical C1-C4Alkylamino radical, C1-C4Alkylsulfonylamino or C1-C4An alkylamino carbonylamino group;
x is selected from O or S;
y is selected from NH, O or S;
q is selected from the group consisting of m R11Substituted phenyl, pyridyl, pyrimidinyl, or pyridazinyl; m is an integer from 0 to 5;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C2-C4Alkenyloxy, halogeno C2-C4Alkenyloxy radical, C2-C4Alkynyloxy, halo C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group.
Further preferred compounds of the invention are:
the structure of the compound shown in the general formula I-1 is as follows: I-1A, I-1B or I-1C;
the structure of the compound shown in the general formula I-2 is as follows: I-2A, I-2B or I-2C;
the structure of the compound shown in the general formula I-3 is as follows: I-3A, I-3B, I-3B-1, I-3B-2, I-3C, I-3C-1, I-3C-2, I-3C-3 or I-3C-4;
Figure BDA0001027375650000051
Figure BDA0001027375650000061
in the formula:
R1ais selected from C1-C4Alkyl radical, C3-C6Cycloalkyl or halo C1-C4An alkyl group;
R2selected from hydrogen, halogen, C1-C4Alkyl radical, C3-C6Cycloalkyl or halo C1-C4An alkyl group;
R3selected from hydrogen, halogen, C1-C4Alkyl radical, C3-C6Cycloalkyl or halo C1-C4An alkyl group;
and when R is1Is C1-C4Alkyl or halo C1-C4When alkyl, R2And/or R3The substituent of (a) is aryl, heteroaryl, arylmethyl or heteroarylmethyl;
n is an integer from 0 to 5;
R4selected from hydrogen, halogen, amino, C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylamino or di (C)1-C4) An alkylamino group;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl, aryl, heteroaryl, and heteroaryl,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) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
m is an integer from 0 to 5.
Still further preferred compounds of the invention are: compounds of general formula I-1B, I-2B, I-3B, I-3B-1, I-3B-2, I-1C, I-2C, I-3C, I-3C-1, I-3C-2, I-3C-3 or I-3C-4 wherein:
R1aselected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
R3selected from hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
n is an integer from 0 to 5;
R4selected from hydrogen, fluorine, chlorine, bromine, iodine, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, trifluoromethoxy, trifluoroethoxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec-butylamino, di-isobutylamino or di-tert-butylamino;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
m is an integer from 0 to 4.
Still further preferred compounds of the present invention are compounds of formula I-1, I-2 or I-3 wherein I-1B, I-2B, I-3B, I-3B-1 or I-3B-2
R1aSelected from methyl or ethyl;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, methyl or ethyl;
R3selected from hydrogen, fluoro, chloro, bromo, iodo, methyl or ethyl;
n is an integer from 0 to 5;
R4selected from hydrogen, fluorine, chlorine, bromine, iodine, amino, methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino, dimethylamino, diethylamino or di-n-propylamino;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (═ O) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyl radicalsOxy radical, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
m is an integer from 0 to 4.
The most preferred compounds of the present invention are those of the general formula I-1, I-2 or I-3 wherein I-1B, I-2B, I-3B, I-3B-1 or I-3B-2
R1aSelected from methyl or ethyl;
R2selected from hydrogen, fluoro, chloro, bromo, iodo, methyl or ethyl;
R3selected from hydrogen, fluoro, chloro, bromo, iodo, methyl or ethyl;
n is an integer from 0 to 3;
R4selected from hydrogen, fluorine, chlorine, bromine, iodine or amino;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
m is an integer from 0 to 3.
The application of the pyrazolyl pyrimidine ether compound in agriculture and other fields in preparing bactericide, insecticide and acaricide medicines.
A sterilization composition contains any one of the pyrazolyl pyrimidine ether compounds as an active component, and the weight percentage of the active component in the composition is 0.1-99%.
The application of the composition in preventing and treating germs in agriculture or other fields.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl groups: straight-chain or branched alkyl groups, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl groups: substituted or unsubstituted cyclic alkyl groups, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, and the like. Halogenated alkyl groups: straight-chain or branched alkyl groups in which the hydrogen atoms may be partially or completely substituted with halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl and the like. Alkylsulfinyl group: straight or branched chain alkyl groups are attached to the structure via a sulfinyl (-SO-) group, such as methylsulfinyl. Haloalkylsulfinyl group: straight-chain or branched alkylsulfinyl groups in which the hydrogen atoms of the alkyl group may be partially or fully substituted by halogen atoms. Haloalkylsulfonyl group: straight-chain 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-. Alkylsulfonylamino group: alkyl-SO2-NH-. 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, trifluoromethoxyChlorofluoromethoxy, trifluoroethoxy and the like. Halogenated alkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyl group may be partially or wholly replaced by halogen atoms, e.g. ClCH2CH2OCO-、CF3CH2OCO-, etc. Alkoxyalkyl groups: alkyl-O-alkyl-, e.g. CH3OCH2-. Haloalkoxyalkyl groups: the hydrogen atoms of the alkyl groups of alkoxyalkyl groups may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2OCH2-、CF3CH2OCH2-and the like. Alkoxycarbonylalkyl groups: alkoxycarbonyl-alkyl-, e.g. CH3OCOCH2-. Haloalkoxycarbonylalkyl: the hydrogen atoms of the alkyl group of the alkoxycarbonylalkyl group may be partially or fully substituted by halogen atoms, e.g. CF3CH2OCOCH2-. Alkylcarbonyloxy group: such as CH3COO-, etc. Haloalkylcarbonyloxy: the hydrogen atoms of the alkylcarbonyloxy group may be partially or fully substituted by halogen atoms, e.g. CF3COO-, etc. Alkoxycarbonyloxy: alkoxycarbonyl-oxy-, e.g. CH3OCOO-. Haloalkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF3OCOO-. Alkylthio-carbonylalkyl: alkylthiocarbonyl-alkyl-, e.g. CH3SCOCH2-. Haloalkylthiocarbonylalkyl: the hydrogen atoms of the alkyl group of the alkylthiocarbonylalkyl group may be partially or wholly substituted by halogen atoms, e.g. CF3CH2SCOCH2-. Alkoxyalkoxy group: such as CH3OCH2O-, etc. Haloalkoxyalkyl: the hydrogen atoms of the alkoxy groups being partially or wholly replaced by halogen atoms, e.g. CF3OCH2O-is formed. Alkoxy alkoxycarbonyl group: such as CH3OCH2CH2OCO-, etc. Alkylthio group: straight or branched chain alkyl groups attached to the structure via a sulfur atom. Haloalkylthio: straight-chain or branched alkylthio groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like. Alkylthioalkyl: alkane (I) and its preparation methodradical-S-alkyl-, e.g. CH3SCH2-. Haloalkylthioalkyl: the hydrogen atoms of the alkyl group of an alkylthioalkyl group may be partially or fully substituted by halogen atoms, e.g. ClCH2CH2SCH2-、CF3CH2SCH2-and the like. Alkylamino group: straight or branched chain alkyl, linked to the structure via a nitrogen atom. Haloalkylamino group: straight-chain or branched alkylamino groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms. Dialkylamino group: such as (CH)3)2N-，(CH3CH2)2N-is provided. Halogenated dialkylamino group: the hydrogen atoms of the alkyl groups being partially or wholly replaced by halogen atoms, e.g. (CF)3)2N-，(CF3CH2)2N-is provided. Alkenyl: straight-chain or branched alkenes, for example ethenyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1, 2-allenyl and 2, 4-hexadienyl. Halogenated alkenyl groups: straight-chain or branched alkenes in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenyloxy: linear or branched alkenes linked to the structure via oxygen atoms. Haloalkenyloxy: straight-chain or branched alkenyloxy groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenylthio group: linear or branched alkenes linked to the structure via a sulfur atom bond. Such as CH2＝CHCH2S-. Alkenyloxycarbonyl radical: such as CH2＝CHCH2OCO-, etc. Alkynyl: straight-chain or branched alkynes, for example ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. Alkynyl also includes groups consisting of multiple triple bonds, such as 2, 5-hexadiynyl. Halogenated alkynyl group: straight-chain or branched alkynes, 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 connected toStructurally, such as methylsulfonyl. 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-. Alkylamino carbonylamino group: alkyl-NH-CO-NH-, e.g. CH3NHCONH-，CH3CH2NHCO NH-. Alkoxycarbonylaminogroup: alkoxy-COCONH-, e.g. CH3OCOCONH-，CH3CH2OCOCO NH-. Alkoxyalkyl amino group: alkoxy-alkyl NH-, e.g. CH3OCH2NH-，CH3CH2OCH2NH-. Alkylamino carbonylamino group: alkyl-NH-CO-NH-, e.g. CH3NHCONH-，CH3CH2NHCONH-. 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. Aryl alkaneAn oxycarbonyl group: such as benzyloxycarbonyl, 4-chlorobenzyloxycarbonyl, 4-trifluoromethylbenzyloxycarbonyl and the like. (hetero) arylalkyloxycarbonyl: such as PhCH2OCO-、4-Cl-PhCH2OCO-, etc.
Table 1, Table 2, Table 3 and Table 4 show the R in the general formula I1、R2And R3、R4And R5And Q are not limited to these substituents.
Figure BDA0001027375650000101
TABLE 1R1Substituent group
Figure BDA0001027375650000102
Figure BDA0001027375650000111
TABLE 2R2(R3) Substituent group
Figure BDA0001027375650000112
TABLE 3R4(R5) Substituent group
Figure BDA0001027375650000113
TABLE 4Q groups
Figure BDA0001027375650000114
Figure BDA0001027375650000121
Some of the compounds of the present invention can be illustrated by the specific compounds listed in tables 5-315, but are not intended to limit the present invention. The general formula compounds referred to in the table are compounds I-1A, I-2A, I-3A, I-1B, I-2B, I-3B, I-3B-1, I-3B-2, I-1C, I-2C, I-3C, I-3C-1, I-3C-2, I-3C-3 or I-3C-4.
In the general formula I-1A,
Figure BDA0001027375650000122
when R is2＝R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, and represent the compound numbers of 5-1-5-279 in sequence.
TABLE 5
Figure BDA0001027375650000123
Figure BDA0001027375650000131
Figure BDA0001027375650000141
Figure BDA0001027375650000151
Table 6: in the general formula I-1A, when R is2＝R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 6-1-6-279.
Table 7: in the general formula I-1A, when R is2＝R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is consistent with table 5 and corresponds to the table in sequence5, No. 5-1-5-279, which represents a compound number of 7-1-7-279 in that order.
Table 8: in the general formula I-1A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 8-1-8-279.
Table 9: in the general formula I-1A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 9-1-9-279 in turn.
Table 10: in the general formula I-1A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 10-1-10-279.
Table 11: in the general formula I-1A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, and correspond to No. 5-1-5-279 of Table 5 in sequence, and represent the compound numbers 11-1-11-279 in sequence.
Table 12: in the general formula I-1A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 12-1-12-279.
Table 13: in the general formula I-1A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 13-1-13-279 in turn.
Table 14: in the general formula I-1A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5, and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compound numbers 14-1-14-2 in this order79。
Table 15: in the general formula I-1A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 15-1-15-279 in turn.
Table 16: in the general formula I-1A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 16-1-16-279.
Table 17: in the general formula I-1A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 17-1-17-279 in turn.
Table 18: in the general formula I-1A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 18-1-18-279.
Table 19: in the general formula I-1A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 19-1-19-279 in turn.
Table 20: in the general formula I-1A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 20-1-20-279.
Table 21: in the general formula I-1A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5, and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbersIn the order of 21-1-21-279.
Table 22: in the general formula I-1A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 22-1-22-279.
Table 23: in the general formula I-1A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 23-1-23-279 in turn.
Table 24: in the general formula I-1A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 24-1-24-279 in turn.
Table 25: in the general formula I-1A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 25-1-25-279 in turn.
Table 26: in the general formula I-1A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 26-1-26-279.
Table 27: in the general formula I-1A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 27-1-27-279 in turn.
Table 28: in the general formula I-1A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds toNo. 5-1-5-279 of Table 5 represents the compound numbers 28-1-28-279 in this order.
Table 29: in the general formula I-1A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, and correspond to the substituents No. 5-1-5-279 of Table 5 in turn, and represent the compound numbers 29-1-29-279 in turn.
Table 30: in the general formula I-1A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 30-1-30-279.
Table 31: in the general formula I-1A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 31-1-31-279 in turn.
Table 32: in the general formula I-1A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 32-1-32-279.
Table 33: in the general formula I-1A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of the compound in sequence 33-1-33-279.
Table 34: in the general formula I-1A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 34-1-34-279.
Table 35: in the general formula I-1A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 35-1-35-279 in turn.
Table 36: in the general formula I-1A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 36-1-36-279 in turn.
Table 37: in the general formula I-1A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 37-1-37-279.
Table 38: in the general formula I-1A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 38-1-38-279 in turn.
Table 39: in the general formula I-1A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of the compound in sequence 39-1-39-279.
Table 40: in the general formula I-1A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 40-1-40-279 in turn.
In the general formula I-2A,
Figure BDA0001027375650000161
table 41: in the general formula I-2A,when R is2＝R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 41-1-41-279 in turn.
Table 42: in the general formula I-2A, when R is2＝R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 42-1-42-279 in turn.
Table 43: in the general formula I-2A, when R is2＝R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m corresponds to Table 5 in turn to Nos. 5-1-5-279 of Table 5 and represents compound numbers 43-1-43-279 in turn.
Table 44: in the general formula I-2A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 44-1-44-279 in turn.
Table 45: in the general formula I-2A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 45-1-45-279 in turn.
Table 46: in the general formula I-2A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 46-1-46-279 in turn.
Table 47: in the general formula I-2A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 47-1-47-279 in turn.
Table 48: in the general formula I-2A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 48-1-48-279 in turn.
Table 49: in the general formula I-2A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m corresponds to Table 5 in turn to Nos. 5-1-5-279 of Table 5 and represents compound numbers 49-1-49-279 in turn.
Table 50: in the general formula I-2A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 50-1-50-279.
Table 51: in the general formula I-2A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of the compound in sequence 51-1-51-279.
Table 52: in the general formula I-2A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 52-1-52-279 in turn.
Table 53: in the general formula I-2A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 53-1-53-279 in turn.
Table 54: in the general formula I-2A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 54-1-54-279 in turn.
Table 55: in the general formula I-2A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 55-1-55-279 in turn.
Table 56: in the general formula I-2A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 56-1-56-279.
Table 57: in the general formula I-2A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of the compound in sequence 57-1-57-279.
Table 58: in the general formula I-2A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 58-1-58-279.
Table 59: in the general formula I-2A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 59-1-59-279 in turn.
Table 60: in the general formula I-2A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 60-1-60-279 in turn.
Table 61: in the general formula I-2A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝CF3When (R) is substituted11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of the compound in sequence 61-1-61-279.
Table 62: in the general formula I-2A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 62-1-62-279 in turn.
Table 63: in the general formula I-2A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 63-1-63-279 in turn.
Table 64: in the general formula I-2A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 64-1-64-279 in turn.
Table 65: in the general formula I-2A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 65-1-65-279 in turn.
Table 66: in the general formula I-2A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m corresponds to Table 5 in turn to Nos. 5-1-5-279 of Table 5 and represents compound numbers 66-1-66-279 in turn.
Table 67: in the general formula I-2A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of the compound in sequence 67-1-67-279.
Table 68: in the general formula I-2A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 68-1-68-279 in turn.
Table 69: in the general formula I-2A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of the compound in sequence 69-1-69-279.
Table 70: in the general formula I-2A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 70-1-70-279.
Table 71: in the general formula I-2A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, and correspond to No. 5-1-5-279 of Table 5 in sequence, and represent the compound numbers 71-1-71-279 in sequence.
Table 72: in the general formula I-2A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 72-1-72-279 in turn.
Table 73: in the general formula I-2A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of the compound in sequence 73-1-73-279.
Table 74: in the general formula I-2A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m corresponds to Table 5 in turn to Nos. 5-1-5-279 of Table 5 and represents compound numbers 74-1-74-279 in turn.
Table 75: in the general formula I-2A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen being cyclopentylSubstituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 75-1-75-279 in turn.
Table 76: in the general formula I-2A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 76-1-76-279 in turn.
In the general formula I-3A,
Figure BDA0001027375650000181
table 77: in the general formula I-3A, when R is2＝R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 77-1-77-279 in turn.
Table 78: in the general formula I-3A, when R is2＝R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 78-1-78-279 in turn.
Table 79: in the general formula I-3A, when R is2＝R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 79-1-79-279 in turn.
Table 80: in the general formula I-3A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 80-1-80-279.
Table 81: in the general formula I-3A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5, and corresponds to Nos. 5-1-5-27 of Table 5 in this order9, representing the compound numbers of 81-1-81-279 in sequence.
Table 82: in the general formula I-3A, when R is2＝R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 82-1-82-279 in turn.
Table 83: in the general formula I-3A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 83-1-83-279 in turn.
Table 84: in the general formula I-3A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m corresponds to Table 5 in turn to Nos. 5-1-5-279 of Table 5, and represents the compound numbers 84-1-84-279 in turn.
Table 85: in the general formula I-3A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 85-1-85-279.
Table 86: in the general formula I-3A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 86-1-86-279 in turn.
Table 87: in the general formula I-3A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 87-1-87-279 in turn.
Table 88: in the general formula I-3A, when R is2＝Cl、R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in order, and represents compounds having numbers of 88-1-88 in order279。
Table 89: in the general formula I-3A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, which correspond to the substituents 5-1-5-279 of Table 5 in turn, and represent the compound numbers 89-1-89-279 in turn.
Table 90: in the general formula I-3A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers in turn 90-1-90-279.
Table 91: in the general formula I-3A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 91-1-91-279 in turn.
Table 92: in the general formula I-3A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 92-1-92-279 in turn.
Table 93: in the general formula I-3A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 93-1-93-279 in turn.
Table 94: in the general formula I-3A, when R is2＝CF3、R3＝R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 94-1-94-279 in turn.
Table 95: in the general formula I-3A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝CH3When (R)11) The substituents m are shown in Table 5, and correspond to Nos. 5-1-5-27 of Table 5 in sequence9, the number of the compound is 95-1-95-279 in sequence.
Table 96: in the general formula I-3A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 96-1-96-279 in turn.
Table 97: in the general formula I-3A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 97-1-97-279 in turn.
Table 98: in the general formula I-3A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 98-1-98-279 in turn.
Table 99: in the general formula I-3A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compound numbers 99-1-99-279 in turn.
Table 100: in the general formula I-3A, when R is2＝R4＝H、R3＝CF3、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 100-1-100-279 in this order.
Table 101: in the general formula I-3A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝CH3When (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents the compound number of 101-1-101-279 sequentially.
Table 102: in the general formula I-3A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 102-1-102-279 in this order.
Table 103: in the general formula I-3A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 103-1-103-279 in turn.
Table 104: in the general formula I-3A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 104-1-104-279 in this order.
Table 105: in the general formula I-3A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 105-1-105-279 in turn.
Table 106: in the general formula I-3A, when R is2＝Cl、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 106-1-106-279 in this order.
Table 107: in the general formula I-3A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝CH3When (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is sequentially 107-1-107-279.
Table 108: in the general formula I-3A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝C2H5When (R) is substituted11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 108-1-108-279 in this order.
Table 109: general formula (VII)In I-3A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1a＝CF3When (R) is substituted11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 109-1-109-279 in this order.
Table 110: in the general formula I-3A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclopropyl, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 110-1-110-279 in this order.
Table 111: in the general formula I-3A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen being cyclopentyl, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds with numbers 111-1-111-279 in this order.
Table 112: in the general formula I-3A, when R is2＝CF3、R3＝CF3、R4＝H、Y＝O、R1aWhen cyclohexyl, substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 112-1-112-279 in this order.
In the general formula I-1B,
Figure BDA0001027375650000201
table 113: in the general formula I-IB, when R is6＝R2＝R3＝R4When H, Y is O, (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents the compound with the number of 113-1-113-279 sequentially.
Table 114: in the general formula I-IB, (R)6)n＝4-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 114-1-114-279 in this order.
Table 115: in the general formula I-IB, (R)6)n＝4-CH3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 115-1-115-279 in this order.
Table 116: in the general formula I-IB, (R)6)n＝4-OCH3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 116-1-116-279 in this order.
Table 117: in the general formula I-IB, (R)6)n＝4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 117-1-117-279 in turn.
Table 118: in the general formula I-IB, (R)6)n＝4-OCF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 118-1-118-279 in this order.
Table 119: in the general formula I-IB, (R)6)n＝2,4-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 119-1-119-279 in this order.
Table 120: in the general formula I-IB, (R)6)n＝2,5-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 120-1-120-279 in this order.
Table 121: in the general formula I-IB, (R)6)n＝2,6-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in order, and represents the compound numbers 121-1-121 in order279。
Table 122: in the general formula I-IB, (R)6)n＝3,5-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 122-1-122-279 in this order.
Table 123: in the general formula I-IB, (R)6)n＝2,4,6-3Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 123-1-123-279 in this order.
Table 124: in the general formula I-IB, (R)6)n＝2-CH3-4-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 124-1-124-279 in this order.
Table 125: in the general formula I-IB, (R)6)n＝2-Cl-4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 125-1-125-279 in this order.
Table 126: in the general formula I-IB, (R)6)n＝2-CN、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compound numbers 126-1-126-279 in this order.
Table 127: in the general formula I-IB, (R)6)n＝2-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 127-1-127-279 in turn.
Table 128: in the general formula I-IB, (R)6)n＝3-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5, and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing compoundsThe numbers are 128-1-128 and 279 in sequence.
Table 129: in the general formula I-IB, (R)6)n＝4-Cl、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m corresponds to the number 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number 129-1-129-279 in sequence.
Table 130: in the general formula I-IB, (R)6)n＝4-Cl、R2＝R3＝H、R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 130-1-130-279 in this order.
Table 131: in the general formula I-IB, (R)6)n＝2-CN、R2＝R3＝R4When H, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 131-1-131-279 in this order.
Table 132: in the general formula I-IB, (R)6)n＝4-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 132-1-132-279 in this order.
Table 133: in the general formula I-IB, (R)6)n＝4-CF3、R2＝R3＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 in turn of Table 5, and represents the compound numbers 133-1-133-279 in turn.
Table 134: in the general formula I-IB, (R)6)n＝4-Cl、R2＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 134-1-134-279 in this order.
Table 135: in the general formula I-IB, (R)6)n＝4-Cl、R3＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5,corresponding to the No. 5-1-5-279 in the sequence of Table 5, the representative compound numbers are 135-1-135-279 in the sequence.
Table 136: in the general formula I-IB, (R)6)n＝4-Cl、R2＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 136-1-136-279 in this order.
Table 137: in the general formula I-IB, (R)6)n＝2,6-2Cl-4-CF3、R2＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 137-1-137-279 in this order.
Table 138: in the general formula I-IB, (R)6)n＝3-F-4-CF3、R3＝CH3、R2＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 138-1-138-279 in this order.
Table 139: in the general formula I-IB, (R)6)n＝4-SO2NH2、R2＝R3＝CH3、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 139-1-139-279 in turn.
In the general formula I-2B,
Figure BDA0001027375650000221
table 140: in the general formula I-2B, when R is6＝R2＝R3＝R4When H, Y is O, (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is sequentially 140-1-140-279.
Table 141: in the general formula I-2B, (R) is6)n＝4-Cl、R2＝R3＝R4When H, Y is OSubstituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 141-1-141-279 in this order.
Table 142: in the general formula I-2B, (R) is6)n＝4-CH3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 142-1-142-279 in this order.
Table 143: in the general formula I-2B, (R) is6)n＝4-OCH3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 143-1-143-279 in this order.
Table 144: in the general formula I-2B, (R) is6)n＝4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 144-1-144-279 in this order.
Table 145: in the general formula I-2B, (R) is6)n＝4-OCF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 145-1-145-279 in sequence.
Table 146: in the general formula I-2B, (R) is6)n＝2,4-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 146-1-146-279 in this order.
Table 147: in the general formula I-2B, (R) is6)n＝2,5-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 147-1-147-279 in this order.
Table 148: in the general formula I-2B, (R) is6)n＝2,6-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 148-1-148-279 in this order.
Table 149: in the general formula I-2B, (R) is6)n＝3,5-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 149-1-149-279 in this order.
Table 150: in the general formula I-2B, (R) is6)n＝2,4,6-3Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 150-1-150-279 in this order.
Table 151: in the general formula I-2B, (R) is6)n＝2-CH3-4-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds numbered 151-1-151-279 in this order.
Table 152: in the general formula I-2B, (R) is6)n＝2-Cl-4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 152-1-152-279 in turn.
Table 153: in the general formula I-2B, (R) is6)n＝2-CN、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 153-1-153-279 in this order.
Table 154: in the general formula I-2B, (R) is6)n＝2-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 154-1-154-279 in turn.
Table 155: in the general formula I-2B, (R) is6)n＝3-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 155-1-155-279 in this order.
Table 156: in the general formula I-2B, (R) is6)n＝4-Cl、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 156-1-156-279 in sequence.
Table 157: in the general formula I-2B, (R) is6)n＝4-Cl、R2＝R3＝H、R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 157-1-157-279 in turn.
Table 158: in the general formula I-2B, (R) is6)n＝2-CN、R2＝R3＝R4When H, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 158-1-158-279 in this order.
Table 159: in the general formula I-2B, (R) is6)n＝4-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 159-1-159-279 in turn.
Table 160: in the general formula I-2B, (R) is6)n＝4-CF3、R2＝R3＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 160-1-160-279 in this order.
Table 161: in the general formula I-2B, (R) is6)n＝4-Cl、R2＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 161-1-161-279 in this order.
Table 162: in the general formula I-2BWhen (R)6)n＝4-Cl、R3＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 162-1-162-279 in this order.
Table 163: in the general formula I-2B, (R) is6)n＝4-Cl、R2＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in the order corresponding to the number of 163-1-163-279 in Table 5 in the order corresponding to the number of m.
Table 164: in the general formula I-2B, (R) is6)n＝2,6-2Cl-4-CF3、R2＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is consistent with Table 5 and sequentially corresponds to Nos. 5-1-5-279 of Table 5, and represents the compound numbers of 164-279 in sequence.
Table 165: in the general formula I-2B, (R) is6)n＝3-F-4-CF3、R3＝CH3、R2＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds whose numbers are 165-1-165-279 in this order.
Table 166: in the general formula I-2B, (R) is6)n＝4-CN、R2＝R3＝CH3、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 166-1-166-279 in this order.
In the general formula I-3B,
Figure BDA0001027375650000231
table 167: in the general formula I-3B, when R is6＝R2＝R3＝R4When H, Y is O, (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is 167-1-167-279 in sequence.
Table 168: in the general formula I-3B, (R)6)n＝4-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 168-1-168-279 in this order.
Table 169: in the general formula I-3B, (R)6)n＝4-CH3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 169-1-169-279 in this order.
Table 170: in the general formula I-3B, (R)6)n＝4-OCH3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 170-1-170-279 in this order.
Table 171: in the general formula I-3B, (R)6)n＝4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 171-1-171-279 in sequence.
Table 172: in the general formula I-3B, (R)6)n＝4-OCF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 172-1-172-279 in this order.
Table 173: in the general formula I-3B, (R)6)n＝2,4-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in the order corresponding to the number of 173-1-173-279 in Table 5 in the order corresponding to the number of m.
Table 174: in the general formula I-3B, (R)6)n＝2,5-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in order, and represents a compound number of 174-1—174-279。
Table 175: in the general formula I-3B, (R)6)n＝2,6-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 175-1-175-279 in this order.
Table 176: in the general formula I-3B, (R)6)n＝3,5-2Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds numbered 176-1-176-279 in this order.
Table 177: in the general formula I-3B, (R)6)n＝2,4,6-3Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 177-1-177-279 in sequence.
Table 178: in the general formula I-3B, (R)6)n＝2-CH3-4-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds whose numbers are 178-1-178-279 in this order.
Table 179: in the general formula I-3B, (R)6)n＝2-Cl-4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in sequence, and represents the number of 179-1-179-279 in sequence.
Table 180: in the general formula I-3B, (R)6)n＝2-CN、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 180-1-180-279 in this order.
Table 181: in the general formula I-3B, (R)6)n＝2-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5, and corresponds in turn to Nos. 5-1-5-279 of Table 5, as representedThe compounds are numbered 181-1-181-279 in that order.
Table 182: in the general formula I-3B, (R)6)n＝3-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 182-1-182-279 in this order.
Table 183: in the general formula I-3B, (R)6)n＝4-Cl、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 183-1-183-279 in this order.
Table 184: in the general formula I-3B, (R)6)n＝4-Cl、R2＝R3＝H、R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 184-1-184-279 in this order.
Table 185: in the general formula I-3B, (R)6)n＝2-CN、R2＝R3＝R4When H, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds numbered 185-1-185-279 in this order.
Table 186: in the general formula I-3B, (R)6)n＝4-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in turn in accordance with Table 5, and represents the number of 186-1-186-279 in turn.
Table 187: in the general formula I-3B, (R)6)n＝4-CF3、R2＝R3＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, and represents the compound numbers 187-1-187-279 in turn.
Table 188: in the general formula I-3B, (R)6)n＝4-Cl、R2＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5, in turnThe numbers of the compounds represented by No. 5-1-5-279 in Table 5 are 188-1-188-279 in sequence.
Table 189: in the general formula I-3B, (R)6)n＝4-Cl、R3＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 189-1-189-279 in this order.
Table 190: in the general formula I-3B, (R)6)n＝4-Cl、R2＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 190-1-190-279 in this order.
Table 191: in the general formula I-3B, (R)6)n＝2,6-2Cl-4-CF3、R2＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 191-1-191-279 in this order.
Table 192: in the general formula I-3B, (R)6)n＝3-F-4-CF3、R3＝CH3、R2＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 192-1-192-279 in this order.
Table 193: in the general formula I-3B, (R)6)n＝4-CN、R2＝R3＝CH3、R4When F, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in the order corresponding to the number of 193-1-193-279 in Table 5 in the order corresponding to the number of m.
In the general formula I-3B-1,
Figure BDA0001027375650000251
table 194: in the general formula I-3B-1, when R is1a＝CH3、R6＝R3＝R4＝H、When Y is O, (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents the compound number of 194-1-194-279 in sequence.
Table 195: in the general formula I-3B-1, (R)6)n＝4-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 195-1-195-279 in this order.
Table 196: in the general formula I-3B-1, (R)6)n＝4-CH3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds numbered 196-1-196-279 in this order.
TABLE 197: in the general formula I-3B-1, (R)6)n＝4-OCH3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is consistent with Table 5 and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound numbers are 197-1-197-279 in sequence.
Table 198: in the general formula I-3B-1, (R)6)n＝4-CF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is identical to that in Table 5 and corresponds to Nos. 5-1-5-279 in turn in Table 5, and represents the compound numbers 198-1-198-279 in turn.
Table 199: in the general formula I-3B-1, (R)6)n＝4-OCF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 199-1-199-279 in turn.
Table 200: in the general formula I-3B-1, (R)6)n＝2,4-2Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 200-1-200-279 in this order.
Table 201: in the general formula I-3B-1, (R)6)n＝2,5-2Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 201-1-201-279 in this order.
Table 202: in the general formula I-3B-1, (R)6)n＝2,6-2Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 202-1-202-279 in this order.
Table 203: in the general formula I-3B-1, (R)6)n＝3,5-2Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 203-1-203-279 in this order.
Table 204: in the general formula I-3B-1, (R)6)n＝2,4,6-3Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 204-1-204-279 in this order.
Table 205: in the general formula I-3B-1, (R)6)n＝2-CH3-4-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 205-1-205-279 in this order.
Table 206: in the general formula I-3B-1, (R)6)n＝2-Cl-4-CF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 206-1-206-279 in this order.
Table 207: in the general formula I-3B-1, (R)6)n＝2-CN、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 207-1-207-279 in sequence.
Table 208: in the general formula I-3B-1, (R)6)n＝2-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 208-1-208-279 in this order.
Table 209: in the general formula I-3B-1, (R)6)n＝3-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 209-1-209-279 in this order.
Table 210: in the general formula I-3B-1, (R)6)n＝4-Cl、R1a＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 210-1-210-279 in this order.
Table 211: in the general formula I-3B-1, (R)6)n＝4-Cl、R1a＝CH3、R3＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 211-1-211-279 in this order.
Table 212: in the general formula I-3B-1, (R)6)n＝2-CN、R1a＝CH3、R3＝R4When H, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 212-1-212-279 in this order.
Table 213: in the general formula I-3B-1, (R)6)n＝4-CF3、R1a＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 213-1-213-279 in turn.
Table 214: in the general formula I-3B-1, (R)6)n＝2,6-2Cl-4-CF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 214-1-214-279 in this order.
Table 215: in the general formula I-3B-1, (R)6)n＝2,6-2Cl-4-CF3、R1a＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 215-1-215-279 in this order.
Table 216: in the general formula I-3B-1, (R)6)n＝4-Cl、R1a＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 216-1-216-279 in this order.
Table 217: in the general formula I-3B-1, when n is 0, R1a＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 217-1-217-279 in this order.
Table 218: in the general formula I-3B-1, (R)6)n＝3-F-4-CF3、R1a＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 218-1-218-279 in this order.
Table 219: in the general formula I-3B-1, (R)6)n＝4-CN、R1a＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 219-1-219-279 in this order.
Table 220: in the general formula I-3B-1, (R)6)n＝4-SO2NH2、R1a＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 220-1-220-279 in this order.
In the general formula I-3B-2,
Figure BDA0001027375650000261
table 221: in the general formula I-3B-2, when R is1a＝CH3、R6＝R2＝R4When H, Y is O, (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is 221-1-221-279 sequentially.
Table 222: in the general formula I-3B-2, (R)6)n＝4-Cl、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 222-1-222-279 in this order.
Table 223: in the general formula I-3B-2, (R)6)n＝4-CH3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 223-1-223-279 in this order.
Table 224: in the general formula I-3B-2, (R)6)n＝4-CF3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 224-1-224-279 in this order.
Table 225: in the general formula I-3B-2, (R)6)n＝4-OCF3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 225-1-225-279 in this order.
Table 226: in the general formula I-3B-2, (R)6)n＝2,4-2Cl、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 226-1-226-279 in this order.
Table 227: in the general formula I-3B-2, (R)6)n＝4-OCH3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 227-1-227-279 in sequence.
Table 228: in the general formula I-3B-2, (R)6)n＝4-Cl、R1a＝CH3、R2＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 228-1-228-279 in turn.
Table 229: in the general formula I-3B-2, (R)6)n＝4-Cl、R1a＝CH3、R2＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 229-1-229-279 in this order.
Table 230: in the general formula I-3B-2, (R)6)n＝4-CF3、R1a＝CH3、R2＝H、R4When F, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 230-1-230-279 in this order.
In the general formula I-1C,
Figure BDA0001027375650000271
table 231: in the general formula I-1C, when R is6＝R2＝R3＝R4When H, Y is O, (R)11) The substituents m are shown in Table 5, and correspond to No. 5-1-5-279 of Table 5 in turn, and represent the compound numbers 231-1-231-279 in turn.
Table 232: in the general formula I-1C, (R) is6)n＝3-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 232-1-232-279 in this order.
Table 233: in the general formula I-1C, (R) is6)n＝5-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds with numbers 233-1-233-279 in this order.
Table 234: in the general formula I-1C, (R) is6)n＝4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 234-1-234-279 in sequence.
Table 235: in the general formula I-1C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 235-1-235-279 in this order.
Table 236: in the general formula I-1C, (R) is6)n＝3-Cl-5-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 236-1-236-279 in this order.
Table 237: in the general formula I-1C, (R) is6)n＝5-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is consistent with Table 5 and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is 237-1-237-279 in sequence.
Table 238: in the general formula I-1C, (R) is6)n＝3-Cl-5-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5, and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers in accordance withFollowed by 238-1-238-.
Table 239: in the general formula I-1C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 239-1-239-279 in this order.
Table 240: in the general formula I-1C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 240-1-240-279 in this order.
Table 241: in the general formula I-1C, (R) is6)n＝5-CF3、R2＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 241-1-241-279 in this order.
Table 242: in the general formula I-1C, (R) is6)n＝5-CF3、R3＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 242-1-242-279 in this order.
Table 243: in the general formula I-1C, (R) is6)n＝5-CF3、R2＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 243-1-243-279 in this order.
In the general formula I-2C,
Figure BDA0001027375650000281
table 244: in the general formula I-2C, when R is6＝R2＝R3＝R4When H, Y is O, (R)11) The substituents m are shown in Table 5, and correspond to the substituents No. 5-1-5-279 of Table 5 in sequence, and representThe compound numbers are 244-1-244-279 in sequence.
Table 245: in the general formula I-2C, (R) is6)n＝3-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 245-1-245-279 in turn.
Table 246: in the general formula I-2C, (R) is6)n＝5-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of No. 5-1-5-279 in Table 5 in the order corresponding to Table 5, and represents the number of 246-1-246-279 in the order corresponding to Table 5.
Table 247: in the general formula I-2C, (R) is6)n＝4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds numbered 247-1-247-279 in this order.
Table 248: in the general formula I-2C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds whose numbers are 248-1-248-279 in this order.
Table 249: in the general formula I-2C, (R) is6)n＝3-Cl-5-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is consistent with Table 5 and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is 249-1-249-279 in sequence.
Table 250: in the general formula I-2C, (R) is6)n＝5-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 250-1-250-279 in this order.
Table 251: in the general formula I-2C, (R) is6)n＝3-Cl-5-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 251-1-251-279 in turn.
Table 252: in the general formula I-2C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 252-1-252-279 in this order.
Table 253: in the general formula I-2C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 253-1-253-279 in turn.
Table 254: in the general formula I-2C, (R) is6)n＝5-CF3、R2＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 254-1-254-279 in this order.
Table 255: in the general formula I-2C, (R) is6)n＝5-CF3、R3＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 255-1-255-279 in this order.
Table 256: in the general formula I-2C, (R) is6)n＝5-CF3、R2＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compound numbers 256-1-256-279 in this order.
In the general formula I-3C,
Figure BDA0001027375650000291
table 257: in the general formula I-3C, when R is6＝R2＝R3＝R4When the value of H, Y is equal to O,(R11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents a compound with the number of 257-1-257-279 in sequence.
Table 258: in the general formula I-3C, (R) is6)n＝3-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is consistent with Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is 258-1-258-279 in sequence.
Table 259: in the general formula I-3C, (R) is6)n＝5-Cl、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 259-1-259-279 in turn.
Table 260: in the general formula I-3C, (R) is6)n＝4-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 260-1-260-279 in this order.
Table 261: in the general formula I-3C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compounds numbered 261-1-261-279 in this order.
Table 262: in the general formula I-3C, (R) is6)n＝3-Cl-5-CF3、R2＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 262-1-262-279 in this order.
Table 263: in the general formula I-3C, (R) is6)n＝5-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compound numbers 263-1-263-279 in this order.
Table 264: in the general formula I-3C, (R) is6)n＝3-Cl-5-CF3、R2＝R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 264-1-264-279 in this order.
Table 265: in the general formula I-3C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 265-1-265-279 in this order.
Table 266: in the general formula I-3C, (R) is6)n＝5-CF3、R2＝R3＝R4When H, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 266-1-266-279 in this order.
TABLE 267: in the general formula I-3C, (R) is6)n＝5-CF3、R2＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 267-1-267-279 in this order.
Table 268: in the general formula I-3C, (R) is6)n＝5-CF3、R3＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 268-1-268-279 in sequence.
Table 269: in the general formula I-3C, (R) is6)n＝5-CF3、R2＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m corresponds to the number 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number 269-1-269-279 in sequence.
In the general formula I-3C-1,
Figure BDA0001027375650000292
table 270: in the general formula I-3C-1,when R is1a＝CH3、R6＝R3＝R4When H, Y is O, (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is sequentially 270-1-270-279.
Table 271: in the general formula I-3C-1, (R)6)n＝3-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is consistent with Table 5 and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound numbers are 271-1-271-279 in sequence.
Table 272: in the general formula I-3C-1, (R)6)n＝5-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 272-1-272-279 in this order.
TABLE 273: in the general formula I-3C-1, (R)6)n＝4-CF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 273-1-273-279 in this order.
Table 274: in the general formula I-3C-1, (R)6)n＝5-CF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 274-1-274-279 in this order.
Table 275: in the general formula I-3C-1, (R)6)n＝3-Cl-5-CF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 275-1-275-279 in turn.
Table 276: in the general formula I-3C-1, (R)6)n＝5-CF3、R1a＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5Sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound numbers are 276-1-276-279 sequentially.
Table 277: in the general formula I-3C-1, (R)6)n＝3-Cl-5-CF3、R1a＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 277-1-277-279 in turn.
Table 278: in the general formula I-3C-1, (R)6)n＝5-CF3、R1a＝CH3、R3＝R4When H, Y is NH, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 278-1-278-279 in this order.
Table 279: in the general formula I-3C-1, (R)6)n＝5-CF3、R1a＝CH3、R3＝R4When H, Y is S, the substituent (R)11) m is consistent with Table 5 and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is 279-1-279 in sequence.
Table 280: in the general formula I-3C-1, (R)6)n＝5-CF3、R1a＝R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 280-1-280-279 in this order.
Table 281: in the general formula I-3C-1, when n is 0, R1a＝R3＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 281-1-281-279 in this order.
Table 282: in the general formula I-3C-1, when n is 0, R1a＝R3＝CH3、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compound numbers 282-1-282-279 in this order.
In the general formula I-3C-2,
Figure BDA0001027375650000301
table 283: in the general formula I-3C-2, when R is1a＝CH3、R6＝R2＝R4When H, Y is O, (R)11) The m substituents are shown in Table 5, which correspond to No. 5-1-5-279 of Table 5 in turn, and represent 283-1-283-279 in turn.
Table 284: in the general formula I-3C-2, (R)6)n＝3-Cl、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 284-1-284-279 in this order.
Table 285: in the general formula I-3C-2, (R)6)n＝5-Cl、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 285-1-285-279 in this order.
Table 286: in the general formula I-3C-2, (R)6)n＝4-CF3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 286-1-286-279 in this order.
Table 287: in the general formula I-3C-2, (R)6)n＝5-CF3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m corresponds to the number 5-1-5-279 in Table 5 in turn and represents the compound number 287-1-287-279 in turn.
Table 288: in the general formula I-3C-1, (R)6)n＝3-Cl-5-CF3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 288-1-288-279 in sequence.
Table 289: tong (Chinese character of 'tong')In the formula I-3C-2, (R)6)n＝5-CF3、R1a＝CH3、R2＝H、R4When F, Y is O, the substituent (R)11) m is identical to that in Table 5 and corresponds to Nos. 5-1-5-279 in turn in Table 5, and represents the compound numbers 289-1-289-279 in turn.
Table 290: in the general formula I-3C-2, (R)6)n＝3-Cl-5-CF3、R1a＝CH3、R2＝H、R4When F, Y is O, the substituent (R)11) m is consistent with Table 5 and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is sequentially 290-1-290-279.
Table 291: in the general formula I-3C-2, (R)6)n＝5-CF3、R1a＝CH3、R2＝R4When H, Y is NH, the substituent (R)11) m is consistent with Table 5, sequentially corresponds to No. 5-1-5-279 of Table 5, and sequentially represents 291-1-291-279 of the compound number.
Table 292: in the general formula I-3C-2, (R)6)n＝5-CF3、R1a＝CH3、R2＝R4When H, Y is S, the substituent (R)11) m is consistent with Table 5 and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents that the compound number is 292-1-292-279 sequentially.
Table 293: in the general formula I-3C-2, (R)6)n＝5-CF3、R1a＝R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 293-1-293-279 in this order.
Table 294: in the general formula I-3C-2, when n is 0, R1a＝R2＝CH3、R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 294-1-294-279 in this order.
Table 295: in the general formula I-3C-2, when n is 0, R1a＝R2＝CH3、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds toNo. 5-1-5-279 of Table 5 represents the compound numbers 295-1-295-279 in this order.
In the general formula I-3C-3,
Figure BDA0001027375650000311
table 296: in the general formula I-3C-3, when R is1a＝CH3、R6＝R3＝R4When H, Y is O, (R)11) The substituents m are shown in Table 5, and correspond to Nos. 5-1-5-279 of Table 5 in turn, and represent the compounds with numbers 296-1-296-279 in turn.
Table 297: in the general formula I-3C-3, (R)6)n＝2-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound number 297-1-297-279 in this order.
Table 298: in the general formula I-3C-3, (R)6)n＝6-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 298-1-298-279 in turn.
Table 299: in the general formula I-3C-3, (R)6)n＝6-OCF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 299-1-299-279 in this order.
Table 300: in the general formula I-3C-3, (R)6)n＝6-OCH2CF3、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents compound numbers 300-1-300-279 in this order.
Table 301: in the general formula I-3C-3, (R)6)n＝5,6-2Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 301-1-301-279 in this order.
Table 302: in the general formula I-3C-3, (R)6)n＝2-Cl、R1a＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 302-1-302-279 in this order.
Table 303: in the general formula I-3C-3, (R)6)n＝6-Cl、R1a＝CH3、R3＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 303-1-303-279 in turn.
Table 304: in the general formula I-3C-3, (R)6)n＝2-Cl、R1a＝CH3、R3＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 304-1-304-279 in this order.
Table 305: in the general formula I-3C-3, (R)6)n＝6-Cl、R1a＝CH3、R3＝R4When H, Y is S, the substituent (R)11) m corresponds to the number of 5-1-5-279 in Table 5 in sequence in accordance with Table 5, and represents the number of 305-1-305-279 in sequence.
In the general formula I-3C-4,
Figure BDA0001027375650000321
table 306: in the general formula I-3C-4, when R is1a＝CH3、R6＝R2＝R4When H, Y is O, (R)11) The substituent m is shown in Table 5, and sequentially corresponds to No. 5-1-5-279 of Table 5, and represents the compound with the number of sequentially 306-1-306-279.
Table 307: in the general formula I-3C-4, (R) is6)n＝2-Cl、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 307-1-307-279 in this order.
Table 308: in the general formula I-3C-4, (R) is6)n＝6-Cl、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is consistent with Table 5, sequentially corresponds to Nos. 5-1-5-279 of Table 5, and represents the compound numbers 308-1-308-279 in sequence.
Table 309: in the general formula I-3C-4, (R) is6)n＝6-OCF3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds in turn to Nos. 5-1-5-279 of Table 5, representing the compound numbers 309-1-309-279 in turn.
Table 310: in the general formula I-3C-4, (R) is6)n＝6-OCH2CF3、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 310-1-310-279 in this order.
Table 311: in the general formula I-3C-4, (R) is6)n＝5,6-2Cl、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 311-1-311-279 in this order.
Table 312: in the general formula I-3C-4, (R) is6)n＝2-Cl、R1a＝CH3、R2＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 312-1-312-279 in this order.
Table 313: in the general formula I-3C-4, (R) is6)n＝6-Cl、R1a＝CH3、R2＝H、R4When F, Y is O, the substituent (R)11) m is in accordance with Table 5, and corresponds in turn to Nos. 5-1-5-279 of Table 5, which representThe compound numbers are 313-1-313-279 in sequence.
Table 314: in the general formula I-3C-4, (R) is6)n＝2-Cl、R1a＝CH3、R2＝R4When H, Y is O, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 314-1-314-279 in this order.
Table 315: in the general formula I-3C-4, (R) is6)n＝6-Cl、R1a＝CH3、R2＝R4When H, Y is S, the substituent (R)11) m is in accordance with Table 5 and corresponds to Nos. 5-1-5-279 of Table 5 in this order, and represents the compound numbers 315-1-315-279 in this order.
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 compounds of formula I can be prepared according to the following two routes:
route one: the preparation method comprises the following steps:
Figure BDA0001027375650000331
and reacting the intermediates II-1 and III in a proper solvent at a proper temperature under a basic condition to obtain the compound shown in the general formula I.
The intermediate II-1 is prepared by the following method:
Figure BDA0001027375650000332
and reacting the intermediate IV with the intermediate V under alkaline conditions at a proper temperature in a proper solvent to obtain an intermediate II-1.
Suitable bases may be selected from, for example, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide, sodium tert-butoxide, etc.
The reaction is carried out in a suitable solvent, which may be selected from, for example, tetrahydrofuran, 1, 4-dioxane, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetone, or butanone.
The reaction temperature may be between room temperature and the boiling temperature of the solvent, and is generally from 20 to 100 ℃.
The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
The intermediates were derived from: the intermediate III is commercially available and can also be prepared by a conventional method; intermediate IV, partially commercially available, or referred to CN 104059020A, Pest Management Science (2010),66(1), 107-112; JP 60155160, Organic Preparations and products International,34(1), 98-102; 2002; CN 104211641, European Journal of Organic Chemistry,2011(27),5323-5330, S5323/1-S5323/48; 2011; tetrahedron,65(42),8690 and 8696; 2009; advanced Synthesis & Catalysis,356(14-15), 3135-; 2014; preparation of JP 08301854; intermediate V, in part, is commercially available or can be prepared according to conventional methods.
And a second route: the preparation method comprises the following steps:
Figure BDA0001027375650000333
and reacting the intermediate IV and II-2 in a proper temperature and a proper solvent under basic conditions to obtain the compound shown in the general formula I.
The intermediate II-2 is prepared by the following method:
Figure BDA0001027375650000334
the intermediate III reacts with the intermediate V under the alkaline condition at a proper temperature and in a proper solvent to prepare an intermediate II-2
Suitable bases may be selected from, for example, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide, sodium tert-butoxide, etc.
The reaction is carried out in a suitable solvent, which may be selected from, for example, tetrahydrofuran, 1, 4-dioxane, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetone, or butanone.
The reaction temperature may be between room temperature and the boiling temperature of the solvent, and is generally from 20 to 100 ℃.
The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
The source of the intermediates is consistent with that described in scheme one above.
Although the compounds of the general formula I of the present invention also belong to pyrazolyl pyrimidine ethers as well as some compounds disclosed in the prior art, the structural features still differ significantly. And the compound of the present invention has better bactericidal activity due to the difference in these structures.
The compound of the general formula I shows excellent activity on various pathogenic bacteria in agriculture or other fields. Therefore, the technical scheme of the invention also comprises the application of the compound shown in the general formula I in preparing bactericides 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. Particularly has better control effect on cucumber downy mildew, wheat powdery mildew and corn rust.
Owing to their positive properties, the abovementioned compounds can be used advantageously for protecting crops, livestock and breeding animals of agricultural and horticultural importance, as well as the environment which is frequently encountered by humans, against harmful bacteria.
The amount of the compound used to achieve the desired effect will vary depending on factors such as the compound used, the crop to be protected, the type of pest, the extent of infection, the climatic conditions, the method of application, and the dosage form employed.
A dose of 10 g to 5 kg of compound per hectare provides adequate control.
The invention also discloses a sterilization, disinsection and acaricidal composition which takes the compound shown in the general formula I as an active component. The weight percentage of the active components in the composition for killing bacteria, insects and mites is between 0.5 and 99 percent. The composition also comprises a carrier acceptable in agriculture, forestry and sanitation.
The compositions of the present invention may be administered in the form of a formulation. The compounds of formula I are dissolved or dispersed as active ingredients in carriers or formulated so as to be more easily dispersed for use as fungicides. 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, which comprises the following steps: the bactericidal composition of the invention is applied to the germs 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, agriculture, one or more other fungicides, insecticides, acaricides, herbicides, plant growth regulators or fertilizers, etc., can be added to the fungicidal compositions of the present invention, thereby providing additional advantages and effects.
It should be understood that various changes and modifications may be made within the scope of the present invention as defined by the claims.
Detailed Description
The following specific examples are intended to further illustrate the invention, but the invention is in no way limited to these examples (all materials are commercially available unless otherwise indicated).
Synthetic examples
Example 1: preparation of intermediate 4-chloro-6- ((1- (4-chlorophenyl) -1H-pyrazol-3-yl) oxy) pyrimidine
Figure BDA0001027375650000351
1- (4-chlorophenyl) -1H-pyrazol-3-ol (19.45g, 0.1mol), potassium carbonate (27.6g, 0.2mol) and 250mL of N, N-dimethylformamide were added to a reaction flask, 4, 6-dichloropyrimidine (14.9g, 0.1mol) was added to the solution while stirring at room temperature, the temperature was raised to 100 ℃ to react for about 4 hours, the solution gradually became yellow during the reaction, ethyl acetate and water were added to extract after the completion of the reaction as monitored by TLC, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and desolventized under reduced pressure. Column chromatography of the residue gave a pale yellow solid (25.7g, 0.084mol), yield: 83.7 percent.
1H-NMR (300MHz, internal standard TMS, solvent CDCl3)δ(ppm):8.66(s,1H,Pyrimidine-2-H),7.91(d,J＝3.0Hz,1H,Pyrazole-5-H),7.60(d,2H,Ph-2,6-2H),7.43(d,2H,Ph-3,5-2H),7.13(s,1H,Pyrimidine-5-H),6.38(d,J＝2.7Hz,1H,Pyrazole-4-H)。
Example 2: preparation of Compounds 114-72
Figure BDA0001027375650000361
4-chloro-6- ((1- (4-chlorophenyl) -1H-pyrazol-3-yl) oxy) pyrimidine (0.31g, 1mmol) and potassium carbonate (0.28g, 2mmol) were added to a 50ml reaction flask containing 15ml of N, N-dimethylformamide, stirred and dissolved, p-methoxyphenol (0.12g, 1m mol) was added to the solution, and the temperature was raised to 90 ℃ to react for 2 hours. After completion of the reaction monitored by TLC, ethyl acetate and water were added for extraction, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and desolventized under reduced pressure. Column chromatography of the residue gave a white solid (0.27g, 0.69mmol), mp 165.3 ℃ in 68.7% yield.
Example 3: preparation of Compounds 130-57
Figure BDA0001027375650000362
4-chloro-6- ((1- (4-chlorophenyl) -1H-pyrazol-3-yl) oxy) pyrimidine (0.31g, 1mmol) and potassium carbonate (0.28g, 2mmol) were added to a 50ml reaction flask containing 15ml of N, N-dimethylformamide, and after stirring and dissolving, p-toluidine (0.11g, 1mmol) was added to the solution, and the temperature was raised to 90 ℃ to react for 2 hours. After completion of the reaction monitored by TLC, ethyl acetate and water were added for extraction, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and desolventized under reduced pressure. Column chromatography of the residue gave a white solid (0.16g, 0.5mmol), m.p. 181.6 ℃ in 50% yield.
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 114-19: yield: 41.7 percent. Yellow solid. Melting point 115 ℃ and 116 ℃. Delta (CDCl3):8.42(s,1H, Pyrimidine-2-H),7.39-7.42(m,5H, Pyrazole-5-H, N-Ph-2,6-2H, O-Ph-3,5-2H),7.09-7.12(m,5H, Pyrazole-4-H, N-Ph-3,5-2H, O-Ph-2,6-2H),6.37(s,1H, Pyrimidine-5-H).
Compounds 114-21: yield: and (4) 64.6%. Yellow solid. Melting point 175-. δ (CDCl3):8.45(s,1H, Pyrimidine-2-H),7.89(s, J ═ 2.4Hz,1H, Pyrazole-5-H),7.60(d,2H, Cl-Ph-2,6-2H),7.51(s,1H, Ph-3-H),7.42(d,2H, Cl-Ph-3,5-2H),7.33(d,1H, Ph-5-H),7.17(d,1H, Ph-6-H),6.67(s,1H, Pyrimidine-5-H),6.38(d, J ═ 1.8Hz,1H, Pyrazole-4-H).
Compounds 114-22: yield: 56.9 percent. A white solid. Melting point 146-.
Compounds 114-24: yield: 49.5 percent. Brown solid. Melting point 132-.
Compounds 114-25: yield: and (5) 59.6%. Brown solid. Melting point 114-.
Compounds 114-30: yield: 52.7 percent. A white solid. Melting point 167-.
Compounds 114 to 34: yield: 36.1 percent. Yellow solid. Melting point 126-.
Compounds 114-52: yield: and (5) 59.2%. Brown solid. Melting point 126-.
Compounds 114-59: yield: and (3.8). Yellow colourAnd (3) a solid. Melting point 127-. δ (CDCl3):8.48(s,1H, Pyrimidine-2-H),7.88(s, J ═ 3Hz,1H, Pyrimidine-5-H), 7.59(d, J ═ 9Hz,2H, Cl-Ph-2,6-2H),7.41(d, J ═ 8.7Hz,2H, Cl-Ph-3,5-2H),7.10(d,1H, Ph-6-H),7.05(d,1H, Ph-5-H),6.97(s,1H, Ph-3-H),6.49(s,1H, Pyrimidine-5-H),6.36(d, J ═ 2.4Hz,1H, Pyrimidine-4-H), 2.34(s,3H, Ph-4-CH-H, p-5-H), and (d, J ═ 9-H)3),2.14(s,3H,Ph-2-CH3)。
Compounds 114-60: yield: 52.1 percent. Yellow solid. Melting point 91-92 ℃. δ (CDCl3):8.49(s,1H, Pyrimidine-2-H),7.87(s, J ═ 2.7Hz,1H, Pyrimidine-5-H), 7.58(d,2H, Cl-Ph-2,6-2H),7.41(d,2H, Cl-Ph-3,5-2H),7.17(d, J ═ 8.1Hz,1H, Ph-3-H),7.01(d, J ═ 7.5Hz,1H, Ph-4-H),6.89(s,1H, Ph-6-H),6.47(s,1H, Pyrimidine-5-H),6.36(d, J ═ 2.4Hz,1H, Pyrimidine-4-H), 2.34(s,3H, Ph-5-CH-H)3),2.13(s,3H,Ph-2-CH3)。
Compounds 114-69: yield 57.8%: yellow solid. Melting point 157-. Delta (CDCl3):8.49(s,1H, Pyrimidine-2-H),7.89(s, J ═ 2.7Hz,1H, Pyrazole-5-H),7.71(d,2H, Cl-Ph-2,6-2H),7.60(d,2H, CF-Ph-2, 6-2H)3-Ph-3,5-2H),7.42(d,2H,CF3-Ph-2,6-2H),7.28(d,2H,Cl-Ph-3,5-2H),6.64(s,1H,Pyrimidine-5-H),6.38(d,J＝2.7Hz,1H,Pyrazole-4-H)。
Compounds 114-72: yield: 68.7 percent. Brown solid. Melting point 165-. Delta (CDCl3):8.50(s,1H, Pyrimidine-2-H),7.87(s, J ═ 2.4Hz,1H, Pyrazole-5-H),7.58(d,2H, Cl-Ph-2,6-2H),7.41(d,2H, Cl-Ph-3,5-2H),7.09(d,2H, CH-H-Ph-3, 5-2H),7.09(d,2H, CH)3O-Ph-2,6-2H),6.95(d,2H,CH3O-Ph-3,5-2H),6.52(s,1H,Pyrimidine-5-H),6.35(d,J＝2.7Hz,1H,Pyrazole-4-H),3.83(s,3H,CH3)。
Compounds 130-57: delta (CDCl3):8.38(s,1H, Pyrimidine-2-H),7.85(s, J ═ 2.7Hz,1H, Pyrazole-5-H),7.58(d,2H, Cl-Ph-2,6-2H),7.38-7.41(m,4H, Cl-Ph-3,5-2H, CH)3-Ph-2,6-2H),7.20(d,2H,CH3-Ph-3,5-2H),6.82(s,1H,NH),6.40(s,1H,Pyrimidine-5-H),6.32(d,1H,Pyrazole-4-H),2.36(s,3H,CH3)。
Compound 114-154: yield: 78.6 percent. Yellow solid. Melting point 126-. Delta (CDCl3):8.45(s,1H, Pyrimidine-2-H),7.90(s, J ═ 2.1Hz,1H, Pyrazole-5-H),7.78(s,1H, Ph-3-H),7.61(d,2H, Cl-Ph-2,6-2H),7.42(d,2H, Cl-Ph-3,5-2H),7.38(d,1H, Ph-5-H),7.35(d,1H, Ph-6-H),6.72(s,1H, Pyrimidine-5-H),6.38(d, J ═ 2.1Hz,1H, Pyrazole-4-H).
Examples of measurement of biological Activity
The compound of the invention has good activity on various germs in the agricultural field.
Example 4: measurement of fungicidal Activity
The compound sample of the invention is used for carrying out the test of the living body protection effect on various fungal diseases of plants. The results of the bactericidal activity measurement are shown in the following examples.
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:
(1) in vivo protective activity against cucumber downy mildew:
at a dose of 400ppm, the compounds with more than 80 percent of control effect on cucumber downy mildew comprise: 114-19, 114-21, 114-34, 130-57, 114-59, 114-60, 114-69, 114-72, 114-154, etc.;
at a dose of 100ppm, the compounds with more than 80 percent of control effect on cucumber downy mildew comprise: 130-57, 114-69, etc.
(2) In vivo protective activity against wheat powdery mildew:
at a dose of 400ppm, the compounds with the control effect on wheat powdery mildew of more than 80 percent comprise: 114-19, 114-34, 130-57, etc.
(3) In vivo protective activity against corn rust:
at a dose of 400ppm, the compounds with the corn rust prevention effect of more than 80 percent comprise: 114, 154, etc.

Claims (8)

1. A pyrazolyl pyrimidine ether compound is characterized in that: the compound is shown as the general formula
Figure DEST_PATH_IMAGE002
-1B:
Figure DEST_PATH_IMAGE004
R2selected from hydrogen, cyano, halogen, C1-C4Alkyl radical, C3-C6Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4An alkoxycarbonyl group;
R3selected from hydrogen, cyano, halogen, C1-C4Alkyl radical, C3-C6Cycloalkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4An alkoxycarbonyl group;
n is an integer from 0 to 5;
R4selected from hydrogen, halogen, amino, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C3-C6Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio radical, C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl radical, C1-C4Alkylamino radical, di (C)1-C4) Alkylamino radical, di (C)1-C4) Alkylamino carbonylamino group, C1-C4Alkylcarbonylamino, halo C1-C4Alkylcarbonylamino, C1-C4Alkoxycarbonyl carbonylamino group, C1-C4Alkoxy radical C1-C4Alkylamino radical, C1-C4Alkylsulfonylamino or C1-C4An alkylamino carbonylamino group;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (= O) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4An alkylcarbonyloxy group,C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
m is an integer from 0 to 5.
2. The pyrazolylpyrimidine ether compound according to claim 1, wherein:
R2selected from hydrogen, halogen, C1-C4Alkyl radical, C3-C6Cycloalkyl or halo C1-C4An alkyl group;
R3selected from hydrogen, halogen, C1-C4Alkyl radical, C3-C6Cycloalkyl or halo C1-C4An alkyl group;
n is an integer from 0 to 5;
R4selected from hydrogen, halogen, amino, C1-C4Alkyl radical, C1-C4Alkoxy radical, C1-C4Haloalkoxy, C1-C4Alkylamino or di (C)1-C4) An alkylamino group;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di（C1-C4Alkyl) amino, C (= O) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
m is an integer from 0 to 5.
3. The compound of claim 2, wherein:
R2selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl and isopropylAlkyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
R3selected from hydrogen, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
n is an integer from 0 to 5;
R4selected from hydrogen, fluorine, chlorine, bromine, iodine, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, trifluoromethoxy, trifluoroethoxy, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec-butylamino, di-isobutylamino or di-tert-butylamino;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (= O) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
m is an integer from 0 to 4.
4. A compound according to claim 3, characterized in that:
R2selected from hydrogen, fluoro, chloro, bromo, iodo, methyl or ethyl;
R3selected from hydrogen, fluoro, chloro, bromo, iodo, methyl or ethyl;
n is an integer from 0 to 5;
R4selected from hydrogen, fluorine, chlorine, bromine, iodine, amino, methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino, dimethylamino, diethylamino or di-n-propylamino;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C6Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C (= O) NR7R8、C1-C4Alkylthio, halo C1-C4Alkylthio radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group;
R7、R8can be the same or different and are respectively selected from hydrogen and C1-C4Alkyl or halo C1-C4An alkyl group;
m is an integer from 0 to 4.
5. The compound of claim 4, wherein:
R2selected from hydrogen, fluoro, chloro, bromo, iodo, methyl or ethyl;
R3selected from hydrogen, fluoro, chloro, bromo, iodo, methyl or ethyl;
n is an integer from 0 to 3;
R4selected from hydrogen, fluorine, chlorine, bromine, iodine or amino;
y is selected from NH, O or S;
R6、R11can be the same or different and are respectively selected from hydrogen, halogen, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
m is an integer from 0 to 3.
6. Use of the pyrazolylpyrimidine ether compound according to any one of claims 1 to 5 for producing a fungicide, insecticide, acaricide, or the like in agriculture or in other fields.
7. A germicidal composition, characterized by: contains the pyrazolyl pyrimidine ether compound as defined in any one of claims 1-6 as active component in the amount of 0.1-99 wt%.
8. Use of a composition according to claim 7 for controlling pathogens in agriculture or other fields.
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CN1117293A (en) * 1993-01-29 1996-02-21 希巴-盖吉股份公司 Pyrazolyl acrylic acid derivatives, intermediates thereto, and their use as microbicides
WO2000071536A1 (en) * 1999-05-20 2000-11-30 E.I. Du Pont De Nemours And Company Heteroaryloxypyrimidine insecticides and acaricides
CN1869034A (en) * 2005-05-26 2006-11-29 沈阳化工研究院 An arylether kind compound and its preparation and application

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Publication number Priority date Publication date Assignee Title
CN1117293A (en) * 1993-01-29 1996-02-21 希巴-盖吉股份公司 Pyrazolyl acrylic acid derivatives, intermediates thereto, and their use as microbicides
WO2000071536A1 (en) * 1999-05-20 2000-11-30 E.I. Du Pont De Nemours And Company Heteroaryloxypyrimidine insecticides and acaricides
CN1869034A (en) * 2005-05-26 2006-11-29 沈阳化工研究院 An arylether kind compound and its preparation and application

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