# Patent

## Title
Substituted pyrimidine compound and uses thereof

## Abstract

Disclosed is a substituted pyrimidine compound having a structure as represented by formula PY.




See the description for the definition of each substituent in the formula. The compound of the present invention provides broad-spectrum bactericidal, pesticidal, and acaricidal activities, provides great control effects against plant diseases such as cucumber downy mildew, corn rust, wheat powdery mildew, rice blast, and cucumber gray mold, specifically provides improved control effects against cucumber downy mildew, corn rust, wheat powdery mildew, and rice blast, provides great control effects against aphid, carmine spider mite, diamondback moth, and armyworm, and acquires great effects at a minimal dosage. The compound of the present invention also provides characteristics such as a simplified preparation method.

## Background
FIELD OF THE INVENTION
The invention relates to fungicide, pesticide, and acaricide. Specifically to a novel substituted pyrimidine compounds and uses thereof.
BACKGROUND OF THE INVENTION
Compounds represented by following general formula and specific compound (No. 47 compound in Patent EP0370704 and No. A compound in Patent JP2009161472) were reported in Patent EP0370704 and JP2009161472, some compounds have some fungicidal and insecticidal activities. Known as a developed commercial fungicide, its English general name is diflumetorim, and Chinese name is Fumijunan. Specific compound (No. 5 compound in the literature) was also reported effective to wheat rust and barley powdery mildew in Pesticide Science. 1999 55: 896-902.




The preparation method of specific compound (No. 7 compound in Patent JP11012253) were reported in Patent JP11012253, JP11049759 and EP0665225, and its English general name is flufenerim, and Chinese name is Michongan.




The preparation method of specific pyrimidinamine compounds represented by following general formula CK1, CK2, CK3 and CK4 (No. 83, 87, 101 and 41 compounds in Patent EP0665225) were reported in Patent EP0665225, JP10036355 and U.S. Pat. No. 5,498,612, their fungicidal, insecticidal and acricidal activities were also reported.




Compounds represented by following general formula and specific compound (No. 447 compound) were reported in U.S. Pat. No. 5,925,644, some compounds have some fungicidal, acricidal and nematicidal activities.




Disclosed in Patent EP264217, DE3786390, U.S. Pat. No. 4,895,849, U.S. Pat. No. 4,985,426 and JP63225364 are substituted pyrimidine benzylamine compounds having a structure as represented by following formula and the specific compound CK6 and CK7 (No. 77 and 74 compounds in Patent EP264217) applied as fungicide, insecticide and acricide.




Disclosed in Patent WO9507278 is the compound having a structure as represented by following formula with application as fungicide, acricide and/or insecticide. Thereinto, the specific compound CK8, CK9 and CK10 were listed in No. 209 line of Table 1 without any biological activity reported.




Disclosed in U.S. Pat. No. 5,227,387 are the compound having a structure as represented by following formula and the specific compound CK11 (No. 81 compound in the patent) applied as nematicide.




Compound represented by following formula and the specific compound CK12 (No. 29 compound in the patent) with application as fungicide and insecticide were disclosed in U.S. Pat. No. 5,326,766.




Compound represented by following formula and the specific compound CK13 (No. 98 compound in the patent), CK14 (No. 271 compound in the patent) and CK15 (No. 117 compound in the patent) with application as fungicide and insecticide were disclosed in Patent EP534341.




Compound represented by following general formula and the specific compound CK16 (No. 26 compound in the patent) applied as fungicide, insecticide and acricide were disclosed in Patent WO9728133.




Compound represented by following general formula and the specific compound CK17 (No. 2.50 compound in U.S. Pat. No. 5,468,751) with application as fungicide, insecticide and acricide were disclosed in U.S. Pat. No. 5,468,751 and EP470600.




Compound represented by following general formula with application as inhibitor to treat HIV-1 was disclosed in Literature Bioorganic & Medicinal Chemistry Letters, 2007, 17: 260-265.




The following compound CK18 (No. 46 compound in the patent) and CK19 (No. 49 compound in the patent) were reported with good insectcidal activity at the concentration of 50 ppm and good fungicidal activity at the concentration of 400 and 100 ppm.




The following compound CK20 (CAS No. 203734-18-3) and CK21 (CAS No. 203734-22-9) were retrieved via Scifinder database without both specific literature and biological activity disclosed.




However, substituted pyrimidine compounds represented by general formula PY of the present invention have not been reported in prior literature.
SUMMARY OF THE INVENTION
The object of the present invention is to provide a novel substituted pyrimidine compounds, which can be used to prepare fungicides, pesticides, and acaricides against harmful fungus, bacteria, insects, and mites in agricultural or other fields.
Detailed descriptions of the invention are as follows:
The present invention provides a kind of substituted pyrimidine compounds having a structure as represented by general formula PY:




Wherein:
R1 is selected from H, halo, cyano, C1-C12alkyl, C3-C12cycloalkyl, haloC1-C12alkyl, cyanoC1-C12alkyl, cyanoC1-C12alkoxy, C2-C12alkenyl, haloC2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl or di(C1-C12alkyl)aminocarbonylC1-C12alkyl;
R2 is selected from H, halo, cyano, C3-C12cycloalkyl, C1-C12alkyl, C1-C12alkoxy or haloC1-C12alkoxy;
R3, R4 may be the same or different, selected respectively from H, halo, OH, amino, C1-C12alkyl, C1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, unsubstituted or further substituted arylC1-C6alkyl or heteroarylC1-C6alkyl by 1 to 5 following groups: halo, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy or haloC1-C6alkoxy; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, R5c may be the same or different, selected respectively from H, halo, OH, NO2, cyano, C1-C12alkyl, haloC1-C12alkyl, C3-C12cycloalkyl, C1-C12alkoxy, haloC1-C12alkoxy, C1-C12alkylthio, haloC1-C12alkylthio, C2-C12alkenyl, haloC2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkynyl, C3-C12alkenoxy, haloC3-C12alkenoxy, C3-C12alkynoxy, haloC3-C12alkynoxy, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkylcarbonyloxy, C1-C12alkylcarbonylamino, C1-C12alkylsulfonyloxy, C1-C12alkoxycarbonyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkoxycarbonylamino, C1-C12alkoxyC1-C12alkoxy or C1-C12alkoxycarbonylC1-C12alkoxy;
X1 is selected from N or CR6; X2 is selected from N or CR7; X3 is selected from N or CR8;
X4 is selected from N or CR9; X5 is selected from N or CR10; X6 is selected from N or CR11; however, X2, X3, X4, X5, X6 are not simultaneously selected from N;
R6, R7, R8, R9, R10, R11 may be the same or different, selected respectively from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, halodi(C1-C12alkyl)amino, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, di(C1-C12alkyl)amino(C1-C12alkyl), CONH2, CONHNH2, CON(C1-C12alkyl)NH2, CONHNH(C1-C12alkyl), CONHN(di(C1-C12alkyl)), CONHNHCO(C1-C12alkyl), CONHNHCO2(C1-C12alkyl), CONHNH(phenyl), C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, halodi(C1-C12alkyl)aminocarbonyl, C1-C12alkylsulfonylamino, C1-C12alkylsulfonyl(C1-C12alkyl)amino, haloC1-C12alkylsulfonylamino, C1-C12alkoxyamino, C1-C12alkoxycarbonylamino, C1-C12alkoxyaminocarbonyl, cyanoC1-C12alkyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, haloC1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl, di(C1-C12alkyl)aminocarbonylC1-C12alkyl, C1-C12alkylthiocarbonylC1-C12alkyl, haloC1-C12alkylthiocarbonylC1-C12alkyl, C1-C12alkylcarbonyloxy, haloC1-C12alkylcarbonyloxy, C1-C12alkoxycarbonyloxy, haloC1-C12alkoxycarbonyloxy, C1-C12alkylaminocarbonyloxy, haloC1-C12alkylaminocarbonyloxy, C1-C12alkylsulfonyloxy, haloC1-C12alkylsulfonyloxy, C1-C12alkoxyC1-C12alkoxy, haloC1-C12alkoxyC1-C2alkoxy, C1-C12alkoxycarbonylC1-C12alkoxy or haloC1-C12alkoxycarbonylC1-C12alkoxy;
W is selected from H, halo, C1-C2alkyl, C1-C2alkoxy, C1-C2alkylthio or C1-C12alkylsulfonyl;
A is selected from O, S or NR12;
B is selected from —CH2— or —CH2CH2—;
R12 is selected from H, OH, H(C)═O, C1-C12alkyl, haloC1-C12alkyl, C1-C2alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C1-C12alkylthio, C2-C12alkenylthio, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, di(C1-C12alkyl)aminosulfonyl, C1-C12alkylsulfonylaminocarbonyl, C1-C12alkylcarbonylaminosulfonyl, C3-C12cycloalkyloxycarbonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkylcarbonylC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C2-C12alkenoxycarbonyl, C2-C12alkynoxycarbonyl, C1-C12alkoxyC1-C12alkoxycarbonyl, C1-C12alkylaminothio, di (C1-C12alkyl) aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC1-C6alkyloxycarbonyl or (hetero)arylC1-C6alkyl by 1 to 5 following groups: halo, NO2, cyano, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy or haloC1-C6alkoxy;
Or the salts or complexes formed from the compounds represented by general formula PY.
The technical scheme of the present invention can be further subdivided into three optimization of technical schemes.
The first optimization of technical schemes is: the compounds represented by formula PY, wherein, X1 is selected from CR6, X2 is selected from N or CR7, X3 is selected from N or CR8, X4 is selected from CR9, X5 is selected from CR10, X6 is selected from N or CR11, within X2, X3 and X6, at least one of which is selected from N, other substituents are defined as above, the compound having a structure as represented by formula I is as fellows.
The second optimization of technical schemes is: the compounds represented by formula PY, wherein, X1 is selected from CR6, X2 is selected from CR7, X3 is selected from CR8, X4 is selected from CR9, X5 is selected from CR10, X6 is selected from CR11, other substituents are defined as above, the compound having a structure as represented by formula II is as fellows.
The third optimization of technical schemes is: the compounds represented by formula PY, wherein, X1 is selected from N, X2 is selected from N or CR7, X3 is selected from N or CR8, X4 is selected from N or CR9, X5 is selected from CR10, X6 is selected from N or CR11, within X2, X3, X4 and X6, at least one of which is selected from N, other substituents are defined as above, the compound having a structure as represented by formula III is as fellows.




Detailed descriptions of three technical schemes of present invention are respectively disclosed.
The first optimization of technical schemes is:
the compounds having a structure as represented by formula I are as fellows.




Wherein:
R1 is selected from cyano, C3-C12cycloalkyl, C1-C12alkyl, halomethyl, cyanoC1-C2alkyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl or di(C1-C12alkyl)aminocarbonylC1-C12alkyl;
R2 is selected from halo, cyano, C3-C12cycloalkyl, C1-C12alkyl or C1-C12alkoxy;
R3, R4 may be the same or different, selected respectively from H, halo, OH, amino, C1-C12alkyl or C1-C12alkoxy;
R5a, R5b, R5c may be the same or different, selected respectively from H, halo, OH, C1-C12alkyl or C1-C12alkoxy;
X2 is selected from N or CR7, X3 is selected from N or CR8, X6 is selected from N or CR11, within X2, X3, X6, at least one substituent is selected from N;
R9 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, C1-C12alkoxycarbonyl, di(C1-C12alkyl)amino(C1-C12alkyl), haloC1-C12alkoxycarbonyl, CONH2, CONHNH2, CON(C1-C12alkyl)NH2, CONHNH(C1-C12alkyl), CONHN(di(C1-C12alkyl)), CONHNHCO(C1-C12alkyl), CONHNHCO2(C1-C12alkyl), CONHNH(phenyl), C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C1-C12alkylsulfonylamino, C1-C12alkylsulfonyl(C1-C12alkyl)amino, haloC1-C12alkylsulfonylamino, C1-C12alkoxyamino, C1-C12alkoxycarbonylamino, C1-C12alkoxyaminocarbonyl, cyanoC1-C12alkyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl or di(C1-C12alkyl)aminocarbonylC1-C12alkyl;
R6, R7, R8, R10, R11 may be the same or different, selected respectively from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, C1-C12alkoxycarbonyl, CONH2, C1-C12alkylaminocarbonyl or di(C1-C12alkyl)aminocarbonyl;
W is selected from H or C1-C12alkyl;
A is selected from O, S or NR12;
B is selected from —CH2— or —CH2CH2—;
R12 is selected from H, OH, H(C)═O, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C1-C12alkylthio, C2-C12alkenylthio, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, di(C1-C12alkyl)aminosulfonyl, C1-C12alkylsulfonylaminocarbonyl, C1-C12alkylcarbonylaminosulfonyl, C3-C12cycloalkyloxycarbonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkylcarbonylC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C2-C12alkenoxycarbonyl, C2-C12alkynoxycarbonyl, C1-C12alkoxyC1-C12alkoxycarbonyl, C1-C12alkylaminothio, di(C1-C12alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC1-C6alkyloxycarbonyl or (hetero)arylC1-C6alkyl by 1 to 5 following groups: halo, NO2, cyano, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy or haloC1-C6alkoxy;
Or the salts or complexes formed from the compounds represented by general formula I.
The preferred compounds represented by general formula I of this invention are:
R1 is selected from cyano, C3-C6cycloalkyl, C1-C6alkyl, halomethyl, cyanoC1-C6alkyl, cyanoC1-C6alkoxy, C1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkylaminocarbonylC1-C6alkyl or di(C1-C6alkyl)aminocarbonylC1-C6alkyl;
R2 is selected from halo, cyano, C3-C6cycloalkyl, C1-C6alkylorC1-C6alkoxy;
R3, R4 may be the same or different, selected respectively from H, halo, OH, amino, C1-C6alkyl or C1-C6alkoxy;
R5a, R5b, R5c may be the same or different, selected respectively from H, halo, OH, C1-C6alkyl or C1-C6alkoxy;
X2 is selected from N or CR7, X3 is selected from N or CR8, X6 is selected from N or CR11, within X2, X3, X6, at least one substituent is selected from N;
R7 is selected from H, halo, cyano or C1-C6alkyl;
R6, R8 may be the same or different, selected respectively from H, halo, cyano, C1-C6alkyl or C1-C6alkoxy;
R9 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, haloC1-C6alkoxy, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6alkenoxy, haloC2-C6alkenoxy, C2-C6alkynoxy, haloC2-C6alkynoxy, C1-C6alkylthio, haloC1-C6alkylthio, C1-C6alkoxyC1-C6alkyl, haloC1-C6alkoxyC1-C6alkyl, C1-C6alkylthioC1-C6alkyl, haloC1-C6alkylthioC1-C6alkyl, C1-C6alkylsulfinyl, haloC1-C6alkylsulfinyl, C1-C6alkylsulfonyl, haloC1-C6alkylsulfonyl, C1-C6alkylaminosulfonyl, C1-C6alkylamino, haloC1-C6alkylamino, di(C1-C6alkyl)amino, C1-C6alkoxycarbonyl, CONH2, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, cyanoC1-C6alkoxy, C1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkylaminocarbonylC1-C6alkyl or di(C1-C6alkyl)aminocarbonylC1-C6alkyl;
R10 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, haloC1-C6alkoxy, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6alkenoxy, haloC2-C6alkenoxy, C2-C6alkynoxy, haloC2-C6alkynoxy, C1-C6alkylthio, haloC1-C6alkylthio, C1-C6alkoxyC1-C6alkyl, haloC1-C6alkoxyC1-C6alkyl, C1-C6alkylthioC1-C6alkyl, haloC1-C6alkylthioC1-C6alkyl, C1-C6alkylsulfinyl, haloC1-C6alkylsulfinyl, C1-C6alkylsulfonyl, haloC1-C6alkylsulfonyl, C1-C6alkylamino, haloC1-C6alkylamino, di(C1-C6alkyl)amino, C1-C6alkoxycarbonyl, CONH2, C1-C6alkylaminocarbonyl or di(C1-C6alkyl)aminocarbonyl;
R11 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, haloC1-C6alkoxy, C1-C6alkoxycarbonyl, CONH2, C1-C6alkylaminocarbonyl or di(C1-C6alkyl)aminocarbonyl;
W is selected from H or C1-C6alkyl;
A is selected from O, S or NR12;
B is selected from —CH2— or —CH2CH2—;
R12 is selected from H, OH, H(C)═O, C1-C6alkyl, C1-C6alkylcarbonyl or C1-C6alkylsulfonyl;
Or the salts formed from the compounds represented by general formula I with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid or citric acid.
In the general formula I, the preferred compounds represented by general formula I-A, I-B, I-C, I-D, I-E, I-F, I-G or I-H of this invention are:







Wherein:
R1 is selected from cyano, C1-C4alkyl or halomethyl;
R2 is selected from halo, cyano, C3-C4cycloalkyl, C1-C4alkyl or C1-C4alkoxy;
R3, R4 may be the same or different, selected respectively from H, halo, OH, amino, C1-C4alkyl or C1-C4alkoxy;
R5b is selected from H, halo, OH, C1-C4alkyl or C1-C4alkoxy;
R7 is selected from H, halo, cyano or C1-C4alkyl;
R8 is selected from H, halo, cyano, C1-C4alkyl or C1-C4alkoxy;
R9 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkylthio, haloC1-C4alkylthio, C1-C4alkoxyC1-C4alkyl, haloC1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, haloC1-C4alkylthioC1-C4alkyl, C1-C4alkylsulfinyl, haloC1-C4alkylsulfinyl, C1-C4alkylsulfonyl, haloC1-C4alkylsulfonyl, C1-C4alkylaminosulfonyl, C1-C4alkylamino, haloC1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, cyanoC1-C4alkoxy, C1-C4alkoxycarbonylC1-C4alkyl, C1-C4alkylaminocarbonylC1-C4alkyl or di(C1-C4alkyl)aminocarbonylC1-C4alkyl;
R10 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C3-C4cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, C2-C4alkenoxy, haloC2-C4alkenoxy, C2-C4alkynoxy, haloC2-C4alkynoxy, C1-C4alkylthio, haloC1-C4alkylthio, C1-C4alkoxyC1-C4alkyl, haloC1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, haloC1-C4alkylthioC1-C4alkyl, C1-C4alkylsulfinyl, haloC1-C4alkylsulfinyl, C1-C4alkylsulfonyl, haloC1-C4alkylsulfonyl, C1-C4alkylamino, haloC1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl or di(C1-C4alkyl)aminocarbonyl;
R11 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl or di(C1-C4alkyl)aminocarbonyl;
Or the salts formed from the compounds represented by general formula I-A, I-B, I-C, I-D, I-E, I-F, I-G or I-H with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, maleic acid, sorbic acid, malic acid or citric acid.
In the general formula I, further more, the preferred compounds represented by general formula I-A, I-B, I-C, I-D, I-E, I-F, I-G or I-H of this invention are:
R1 is selected from cyano, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, CH2Cl, CHCl2, CH2F, CHF2, CClF2, CCl3 or CF3;
R2 is selected from F, Cl, Br, cyano, CH3, C2H5, OCH3 or OC2H5;
R3, R4 may be the same or different, selected respectively from H, Cl, Br, OH, amino, CH3, C2H5, OCH3 or OC2H5;
R5b is selected from H, Cl, Br, OH, CH3, C2H5, OCH3 or OC2H5;
R7 is selected from H, Cl or cyano;
R8 is selected from H, Cl, Br, cyano, CH3 or OCH3;
R9 is selected from H, F, Cl, Br, cyano, HO(C═O), amino, NO2, CH3, C2H5, CF3, CClF2, OCH3, OC2H5, OCF3, COOCH3, COOC2H5, CONH2, CONHCH3, CONHC2H5, CON(CH3)2, SO2CH3 or SO2NHCH3;
R10 is selected from H, Cl, cyano, CH3, C2H5, OCH3 or OC2H5;
R11 is selected from H, F, Cl, Br, cyano, HO(C═O), amino, NO2, CH3, C2H5, CF3, CClF2, OCH3, OC2H5, OCF3, COOCH3, COOC2H5, CONH2, CONHCH3, CONHC2H5 or CON(CH3)2;
Or the salts formed from the compounds represented by general formula I-A, I-B, I-C, I-D, I-E, I-F, I-G or I-H with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid or benzoic acid.
Even more preferred compounds represented by general formula I of this invention are:
In the general formula I-A,
R1 is selected from CH3, C2H5, CH2Cl, CHF2, CClF2, CCl3 or CF3;
R2 is selected from Cl, Br or cyano;
R3, R4, R10 is selected from H;
R5b is selected from H, Cl, Br or OCH3;
R8 is selected from H or Cl;
R9 is selected from H, Cl, cyano, CF3, CClF2, COOCH3, COOC2H5 or CONH2;
R1 is selected from H, Cl, NO2, CF3, COOCH3 or CONHCH3;
Or, in the general formula I-B,
R1 is selected from CH3, C2H5 or CHF2;
R2 is selected from Cl, Br or cyano;
R9 is selected from Cl, Br, cyano or CF3;
R3, R4, R5b, R10, R11 is selected from H;
Or, in the general formula I-C,
R1 is selected from CH3, C2H5 or CHF2;
R2 is selected from Cl, Br or cyano;
R3, R4, R5b, R9 is selected from H;
R8, R10 is selected from CH3 or OCH3;
Or, in the general formula I-E,
R1 is selected from CH3, C2H5 or CHF2;
R2 is selected from Cl, Br or cyano;
R3, R4, R5b, R8, R10 is selected from H;
R9 is selected from H, Cl, cyano, CF3, COOCH3, COOC2H5 or CONH2;
R1 is selected from H, Cl or CF3;
Or the salts formed from the compounds represented by general formula I-A, I-B, I-C or I-E with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid or benzoic acid.
Most preferred compounds represented by general formula I of this invention are:
In the general formula I-A,
R1 is selected from CH3, C2H5, CH2Cl, CHF2 or CF3;
R2 is selected from Cl, Br or cyano;
R3, R4, R5b, R10 is selected from H;
R9 is selected from Cl, cyano or CF3;
R8, R11 is selected from H or Cl;
Or, in the general formula I-B,
R1 is selected from CH3, C2H5 or CHF2;
R2, R9 is selected from Cl, Br or cyano;
R3, R4, R5b, R10, R11 is selected from H;
Or the salts formed from the compounds represented by general formula I-A or I-B with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid or benzoic acid.
The second optimization of technical schemes is:
The compounds having a structure as represented by formula II are as fellows.




Wherein:
R1 is selected from C1-C12alkyl, C3-C8cycloalkyl or halomethyl;
R2 is selected from halo, cyano or C1-C4alkoxy;
R3, R4 may be the same or different, selected respectively from H, halo, C1-C12alkyl, C1-C12alkoxy or C3-C12cycloalkyl; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, R5c may be the same or different, selected respectively from H, halo, OH, C1-C12alkyl or C1-C12alkoxy;
R6, R7, R8, R9, R10, R11 may be the same or different, selected respectively from H, halo, OH, amino, cyano, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12 cycloalkyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, halodi(C1-C12alkyl)amino, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, halodi(C1-C12alkyl)aminocarbonyl, CONH2, C1-C12alkylthio, haloC1-C12alkylthio, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, haloC1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylthiocarbonylC1-C12alkyl, haloC1-C12alkylthiocarbonylC1-C12alkyl, C1-C12alkylcarbonyloxy, haloC1-C12alkylcarbonyloxy, C1-C12alkoxycarbonyloxy, haloC1-C12alkoxycarbonyloxy, C1-C12alkylaminocarbonyloxy, haloC1-C12alkylaminocarbonyloxy, C1-C12alkylsulfonyloxy, haloC1-C12alkylsulfonyloxy, C1-C12alkoxyC1-C12alkoxy, haloC1-C12alkoxyC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkoxy or haloC1-C12alkoxycarbonylC1-C12alkoxy;
W is selected from H or C1-C12alkyl;
A is selected from NR12;
B is selected from —CH2— or —CH2CH2—;
R12 is selected from H, OH, H(C)═O, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C1-C12alkylthio, C2-C12alkenylthio, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, di(C1-C12alkyl)aminosulfonyl, C1-C12alkylsulfonylaminocarbonyl, C1-C12alkylcarbonylaminosulfonyl, C3-C12cycloalkyloxycarbonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkylcarbonylC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C2-C12alkenoxycarbonyl, C2-C12alkynoxycarbonyl, C1-C12alkoxyC1-C12alkoxycarbonyl, C1-C12alkylaminothio, di (C1-C12alkyl) aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC1-C6alkyloxycarbonyl or (hetero)arylC1-C6alkyl by 1 to 5 following groups: halo, NO2, cyano, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy or haloC1-C6alkoxy;
Or the salts or complexes formed from the compounds of general formula II.
The preferred compounds represented by general formula II of this invention are:
R1 is selected from C1-C6alkyl, C3-C6cycloalkyl or halomethyl;
R2 is selected from halo, cyano or C1-C4alkoxy;
R3, R4 may be the same or different, selected respectively from H, halo, C1-C6alkyl, C1-C6alkoxy or C3-C6cycloalkyl; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, R5c, R6 may be the same or different, selected respectively from H, halo, OH, C1-C6alkyl or C1-C6alkoxy;
R7, R8, R9, R10, R11 may be the same or different, selected respectively from H, halo, OH, amino, cyano, NO2, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, haloC1-C6alkoxy, C3-C6cycloalkyl, C1-C6alkylamino, haloC1-C6alkylamino, di(C1-C6alkyl)amino, halodi(C1-C6alkyl)amino, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, halodi(C1-C6alkyl)aminocarbonyl, CONH2, C1-C6alkylthio, haloC1-C6alkylthio, C2-C6alkenyl, C2-C6alkynyl, C2-C6alkenoxy, haloC2-C6alkenoxy, C2-C6alkynoxy, haloC2-C6alkynoxy, C1-C6alkylsulfonyl, haloC1-C6alkylsulfonyl, C1-C6alkylcarbonyl, haloC1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, haloC1-C6alkoxycarbonyl, C1-C6alkoxyC1-C6alkyl, haloC1-C6alkoxyC1-C6alkyl, C1-C6alkylthioC1-C6alkyl, haloC1-C6alkylthioC1-C6alkyl, C1-C6alkoxycarbonylC1-C6alkyl, haloC1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkylthiocarbonylC1-C6alkyl, haloC1-C6alkylthiocarbonylC1-C6alkyl, C1-C6alkylcarbonyloxy, haloC1-C6alkylcarbonyloxy, C1-C6alkoxycarbonyloxy, haloC1-C6alkoxycarbonyloxy, C1-C6alkylaminocarbonyloxy, haloC1-C6alkylaminocarbonyloxy, C1-C6alkylsulfonyloxy, haloC1-C6alkylsulfonyloxy, C1-C6alkoxyC1-C6alkoxy, haloC1-C6alkoxyC1-C6alkoxy, C1-C6alkoxycarbonylC1-C6alkoxy or haloC1-C6alkoxycarbonylC1-C6alkoxy;
W is selected from H or C1-C3alkyl;
A is selected from NR12;
B is selected from —CH2— or —CH2CH2—;
R12 is selected from H, OH, H(C)═O, C1-C6alkyl, C1-C6alkylsulfonyl or C1-C6alkylcarbonyl;
Or the salts formed from the compounds represented by general formula II with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid or citric acid.
Further more, the preferred compounds represented by general formula II of this invention are:
R1 is selected from C1-C4alkyl, C3-C4cycloalkyl or halomethyl;
R2 is selected from F, Cl, Br or cyano;
R3, R4 may be the same or different, selected respectively from H, halo, C1-C4alkyl, C1-C4alkoxy or C3-C6cycloalkyl; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, R5c, R6 may be the same or different, selected respectively from H, halo, OH, C1-C4alkyl or C1-C4alkoxy;
R7, R8, R9, R10, R11 may be the same or different, selected respectively from H, halo, OH, amino, cyano, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C3-C4cycloalkyl, C1-C4alkylamino, haloC1-C4alkylamino, di(C1-C4alkyl)amino, halodi(C1-C4alkyl)amino, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, halodi(C1-C4alkyl)aminocarbonyl, CONH2, C1-C4alkylthio, haloC1-C4alkylthio, C2-C4alkenyl, C2-C4alkynyl, C2-C4alkenoxy, haloC2-C4alkenoxy, C2-C4alkynoxy, haloC2-C4alkynoxy, C1-C4alkylsulfonyl, haloC1-C4alkylsulfonyl, C1-C4alkylcarbonyl, haloC1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, haloC1-C4alkoxycarbonyl, C1-C4alkoxyC1-C4alkyl, haloC1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, haloC1-C4alkylthioC1-C4alkyl, C1-C4alkoxycarbonylC1-C4alkyl, haloC1-C4alkoxycarbonylC1-C4alkyl, C1-C4alkylthiocarbonylC1-C4alkyl, haloC1-C4alkylthiocarbonylC1-C4alkyl, C1-C4alkylcarbonyloxy, haloC1-C4alkylcarbonyloxy, C1-C4alkoxycarbonyloxy, haloC1-C4alkoxycarbonyloxy, C1-C4alkylaminocarbonyloxy, haloC1-C4alkylaminocarbonyloxy, C1-C4alkylsulfonyloxy, haloC1-C4alkylsulfonyloxy, C1-C4alkoxyC1-C4alkoxy, haloC1-C4alkoxyC1-C4alkoxy, C1-C4alkoxycarbonylC1-C4alkoxy or haloC1-C4alkoxycarbonylC1-C4alkoxy;
W is selected from H or CH3;
A is selected from NR12;
B is selected from —CH2— or —CH2CH2—;
R12 is selected from H, OH, H(C)═O, C1-C4alkyl, C1-C4alkylsulfonyl or C1-C4alkylcarbonyl;
Or the salts formed from the compounds represented by general formula II with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, maleic acid, sorbic acid, malic acid or citric acid.
Even more preferred compounds represented by formula II of this invention are:
R1 is selected from CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, cyclopropyl, cyclobutyl, CF3, CCl3, CH2F, CH2Cl, CH2Br, CClF2, CCl2F, CHF2 or CHCl2;
R2 is selected from F, Cl, Br or cyano;
R3, R4 may be the same or different, selected respectively from H, F, Cl, Br, I, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, OCH3, OC2H5, OC3H7-n, OC3H7-i, OC4H9-n, OC4H9-s, OC4H9-i or OC4H9-t;
R5a, R5b, R5c, R6 may be the same or different, selected respectively from H, F, Cl, Br, I, OH, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, OCH3, OC2H5, OC3H7-n, OC3H7-i, OC4H9-n, OC4H9-s, OC4H9-i or OC4H9-t;
R7, R8, R9, R10, R11 may be the same or different, selected respectively from H, F, Cl, Br, I, cyano, amino, NO2, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, CF3, CCl3, CClF2, CCl2F, CHCl2, CH2F, CHF2, OCH3, OC2H5, OC3H7-n, OC3H7-i, OC4H9-n, OC4H9-s, OC4H9-i, OC4H9-t, OCF3, OCH2CF3, COOCH3, COOC2H5, CONH2, CONHCH3, CONHC2H5, CONH(CH3)2, methylsulfonyl or trifluoromethylsulfonyl;
W is selected from H or CH3;
A is selected from NR12;
B is selected from —CH2— or —CH2CH2—;
R12 is selected from H;
Or the salts formed from the compounds represented by general formula II with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid or benzoic acid.
Even further more preferred compounds represented by formula II of this invention are:
R1 is selected from CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, cyclopropyl, cyclobutyl, CH2Cl, CHCl2, CH2F, CHF2, CClF2, CCl3 or CF3;
R2 is selected from F, Cl, Br or cyano;
R3, R4 may be the same or different, selected respectively from H, F, Cl, Br, I, CH3, C2H5, n-C3H7, i-C3H7, OCH3, OC2H5, OC3H7-n or OC3H7-i;
R5a, R5b, R5c, R6 may be the same or different, selected respectively from H, F, Cl, Br or OCH3;
R7, R8, R9, R10, R11 may be the same or different, selected respectively from H, F, Cl, Br, I, cyano, NO2, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, OCH3, OCF3, CF3, CCl3, CClF2, CCl2F, CHCl2, CH2F, CHF2, methylsulfonyl or trifluoromethylsulfonyl;
W is selected from H or CH3;
A is selected from NH;
B is selected from —CH2— or —CH2CH2—;
Or the salts formed from the compounds of general formula II with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid or benzoic acid.
Most preferred compounds represented by formula II of this invention are:
R1 is selected from CH3, C2H5, CHF2 or CF3;
R2 is selected from Cl or cyano;
R3, R4 is selected from H;
R5a, R5b, R5c, R6 may be the same or different, selected respectively from H, F, Cl, Br or OCH3;
W is selected from H or CH3;
R7, R8, R9, R10, R11 may be the same or different, selected respectively from H, F, Cl, cyano, NO2, CH3, OCH3, OCF3, CF3 or methylsulfonyl;
A is selected from NH;
B is selected from —CH2— or —CH2CH2—;
Or the salts formed from the compounds represented by general formula II with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or trifluoroacetic acid.
The third optimization of technical schemes is:
the compounds having a structure as represented by formula III are as fellows.




R1 is selected from halo, C1-C12alkyl, C3-C12cycloalkyl, haloC1-C12alkyl, C2-C12alkenyl, haloC2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl or haloC1-C12alkoxyC1-C12alkyl;
R2 is selected from halo, cyano, C1-C12alkyl, C1-C12alkoxy or haloC1-C12alkoxy;
W is selected from H, halo, C1-C12alkyl, C1-C12alkoxy, C1-C12alkylthio or C1-C12alkylsulfonyl;
R3, R4 may be the same or different, selected respectively from H, C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, unsubstituted or further substituted arylC1-C6alkyl or heteroarylC1-C6alkyl by 1 to 5 following groups: halo, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy or haloC1-C6alkoxy; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, R5c may be the same or different, selected respectively from H, halo, NO2, cyano, C1-C12alkyl, haloC1-C12alkyl, C3-C12cycloalkyl, C1-C12alkoxy, haloC1-C12alkoxy, C1-C12alkylthio, haloC1-C12alkylthio, C2-C12alkenyl, haloC2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkynyl, C3-C12alkenoxy, haloC3-C12alkenoxy, C3-C12alkynoxy, haloC3-C12alkynoxy, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkylcarbonyloxy, C1-C12alkylcarbonylamino, C1-C12alkylsulfonyloxy, C1-C12alkoxycarbonyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkoxycarbonylamino, C1-C12alkoxyC1-C12alkoxy or C1-C12alkoxycarbonylC1-C12alkoxy;
X2 is selected from N or CR7;
X3 is selected from N or CR8;
X4 is selected from N or CR9;
X6 is selected from N or CR11; however, X2, X3, X4, X6 are not simultaneously selected from N;
R7, R8, R9, R1 may be the same or different, selected respectively from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C1-C12alkoxycarbonyl, CONH2, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C1-C12alkylsulfonyl or haloC1-C12alkylsulfonyl;
R10 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, C1-C12alkoxycarbonyl, CONH2, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl or di(C1-C12alkyl)aminocarbonylC1-C12alkyl;
A is selected from O, S or NR12;
B is selected from is selected from —CH2— or —CH2CH2—;
R12 is selected from H, OH, H(C)═O, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C1-C12alkylthio, C2-C12alkenylthio, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, di(C1-C12alkyl)aminosulfonyl, C1-C12alkylsulfonylaminocarbonyl, C1-C12alkylcarbonylaminosulfonyl, C3-C12cycloalkyloxycarbonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkylcarbonylC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C2-C12alkenoxycarbonyl, C2-C12alkynoxycarbonyl, C1-C12alkoxyC1-C12alkoxycarbonyl, C1-C12alkylaminothio, di(C1-C12alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC1-C6alkyloxycarbonyl or (hetero)arylC1-C6alkyl by 1 to 5 following groups: halo, NO2, cyano, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy or haloC1-C6alkoxy;
Or the salts or complexes formed from the compounds represented by general formula III.
The preferred compounds represented by general formula III of this invention are:
R1 is selected from halo, C1-C8alkyl, C3-C8cycloalkyl, haloC1-C8alkyl, C2-C8alkenyl, haloC2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkynyl, C1-C8alkoxyC1-C8alkyl or haloC1-C8alkoxyC1-C8alkyl;
R2 is selected from halo, cyano, C1-C8alkyl, C1-C8alkoxy or haloC1-C8alkoxy;
W is selected from H, halo, C1-C8alkyl, C1-C8alkoxy, C1-C8alkylthio or C1-C8alkylsulfonyl;
R3, R4 may be the same or different, selected respectively from H, C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C1-C8alkoxyC1-C8alkyl, unsubstituted or further substituted arylC1-C4alkyl or heteroarylC1-C4alkyl by 1 to 3 following groups: halo, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy or haloC1-C4alkoxy; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, R5c may be the same or different, selected respectively from H, halo, NO2, cyano, C1-C8alkyl, haloC1-C8alkyl, C3-C6cycloalkyl, C1-C8alkoxy, haloC1-C8alkoxy, C1-C8alkylthio, haloC1-C8alkylthio, C2-C8alkenyl, haloC2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkynyl, C3-C8alkenoxy, haloC3-C8alkenoxy, C3-C8alkynoxy, haloC3-C8alkynoxy, C1-C8alkylsulfinyl, haloC1-C8alkylsulfinyl, C1-C8alkylsulfonyl, haloC1-C8alkylsulfonyl, C1-C8alkylcarbonyl, haloC1-C8alkylcarbonyl, C1-C8alkylcarbonyloxy, C1-C8alkylcarbonylamino, C1-C8alkylsulfonyloxy, C1-C8alkoxycarbonyl, C1-C8alkoxycarbonylC1-C8alkyl, C1-C8alkoxycarbonylamino, C1-C8alkoxyC1-C8alkoxy or C1-C8alkoxycarbonylC1-C8alkoxy;
X2 is selected from N or CR7;
X3 is selected from N or CR8;
X4 is selected from N or CR9;
X6 is selected from N or CR11; however, X2, X3, X4, X6 are not simultaneously selected from N;
R7, R8, R9, R11 may be the same or different, selected respectively from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxy, haloC1-C8alkoxy, C1-C8alkoxycarbonyl, CONH2, C1-C8alkylaminocarbonyl, di(C1-C8alkyl)aminocarbonyl, C1-C8alkylsulfonyl or haloC1-C8alkylsulfonyl;
R10 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxy, haloC1-C8alkoxy, C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkynyl, C2-C8alkenoxy, haloC2-C8alkenoxy, C2-C8alkynoxy, haloC2-C8alkynoxy, C1-C8alkylthio, haloC1-C8alkylthio, C1-C8alkoxyC1-C8alkyl, haloC1-C8alkoxyC1-C8alkyl, C1-C8alkylthioC1-C8alkyl, haloC1-C8alkylthioC1-C8alkyl, C1-C8alkylsulfinyl, haloC1-C8alkylsulfinyl, C1-C8alkylsulfonyl, haloC1-C8alkylsulfonyl, C1-C8alkylaminosulfonyl, C1-C8alkylamino, haloC1-C8alkylamino, di(C1-C8alkyl)amino, C1-C8alkoxycarbonyl, CONH2, C1-C8alkylaminocarbonyl, di(C1-C8alkyl)aminocarbonyl, cyanoC1-C8alkoxy, C1-C8alkoxycarbonylC1-C8alkyl, C1-C8alkylaminocarbonylC1-C8alkyl or di(C1-C8alkyl)aminocarbonylC1-C8alkyl;
A is selected from O, S or NR12;
B is selected from is selected from —CH2— or —CH2CH2—;
R12 is selected from H, OH, H(C)═O, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxy, haloC1-C8alkoxy, C3-C8cycloalkyl, C1-C8alkylthio, C2-C8alkenylthio, C2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C1-C8alkoxyC1-C8alkyl, haloC1-C8alkoxyC1-C8alkyl, C1-C8alkylthioC1-C8alkyl, haloC1-C8alkylthioC1-C8alkyl, C1-C8alkylsulfinyl, haloC1-C8alkylsulfinyl, C1-C8alkylsulfonyl, haloC1-C8alkylsulfonyl, C1-C8alkylaminosulfonyl, di(C1-C8alkyl)aminosulfonyl, C1-C8alkylsulfonylaminocarbonyl, C1-C8alkylcarbonylaminosulfonyl, C3-C8cycloalkyloxycarbonyl, C1-C8alkylcarbonyl, haloC1-C8alkylcarbonyl, C1-C8alkoxycarbonyl, haloC1-C8alkoxycarbonyl, C1-C8alkylcarbonylC1-C8alkyl, C1-C8alkoxycarbonylC1-C8alkyl, C1-C8alkylaminocarbonyl, di(C1-C8alkyl)aminocarbonyl, C2-C8alkenoxycarbonyl, C2-C8alkynoxycarbonyl, C1-C8alkoxyC1-C8alkoxycarbonyl, C1-C8alkylaminothio, di (C1-C8alkyl) aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC1-C6alkyloxycarbonyl or (hetero)arylC1-C6alkyl by 1 to 3 following groups: halo, NO2, cyano, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy or haloC1-C4alkoxy;
Or the salts formed from the compounds represented by general formula III.
Further more, the preferred compounds represented by general formula III of this invention are:
R1 is selected from halo, C1-C4alkyl, C3-C6cycloalkyl, haloC1-C4alkyl, C2-C4alkenyl, haloC2-C4alkenyl, C2-C4alkynyl, haloC2-C4alkynyl, C1-C4alkoxyC1-C4alkyl or haloC1-C4alkoxyC1-C4alkyl;
R2 is selected from halo or cyano;
W is selected from H or CH3;
R3, R4 is selected from H, CH3 or C2H5;
R5a, R5b, R5c may be the same or different, selected respectively from H, halo, NO2, cyano, C1-C4alkyl, haloC1-C4alkyl, C3-C6cycloalkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkylthio, haloC1-C4alkylthio, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylcarbonyl or C1-C4alkoxyC1-C4alkoxy;
X2 is selected from N or CR7;
X3 is selected from N or CR8;
X4 is selected from N or CR9;
X6 is selected from N or CR11; however, X2, X3, X4, X6 are not simultaneously selected from N;
R7, R8, R9, R11 may be the same or different, selected respectively from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl or C1-C4alkylsulfonyl or haloC1-C4alkylsulfonyl;
R10 is selected from H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C3-C4cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, C2-C4alkenoxy, haloC2-C4alkenoxy, C2-C4alkynoxy, haloC2-C4alkynoxy, C1-C4alkylthio, haloC1-C4alkylthio, C1-C4alkoxyC1-C4alkyl, haloC1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, haloC1-C4alkylthioC1-C4alkyl, C1-C4alkylsulfinyl, haloC1-C4alkylsulfinyl, C1-C4alkylsulfonyl, haloC1-C4alkylsulfonyl, C1-C4alkylaminosulfonyl, C1-C4alkylamino, haloC1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, cyanoC1-C12alkoxy, C1-C4alkoxycarbonylC1-C4alkyl, C1-C4alkylaminocarbonylC1-C4alkyl or di(C1-C4alkyl)aminocarbonylC1-C4alkyl;
A is selected from O, S or NH;
B is selected from —CH2— or —CH2CH2—;
Or the salts formed from the compounds represented by general formula III with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid or citric acid.
In the general formula III, even more preferred compounds represented by general formula III-A, III-B, III-C, III-D, III-E, III-F, III-G, III-H, III-I or III-J of this invention are:







Wherein:
R1 is selected from F, Cl, Br, I, C1-C4alkyl, C3-C6cycloalkyl, haloC1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkoxyC1-C4alkyl or haloC1-C4alkoxyC1-C4alkyl;
R2 is selected from halo or cyano;
W is selected from H or CH3;
R3, R4 is selected from H, CH3 or C2H5;
R5a, R5b, R5c may be the same or different, selected respectively from H, F, Cl, Br, I, NO2, cyano, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy or C1-C4alkylcarbonyl;
R7, R8, R9, R11 may be the same or different, selected respectively from H, F, Cl, Br, I, cyano, HO(C═O), NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkoxycarbonyl, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, C1-C4alkylsulfonyl or haloC1-C4alkylsulfonyl;
R10 is selected from H, F, Cl, Br, I, cyano, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkylsulfonyl or haloC1-C4alkylsulfonyl;
A is selected from O, S or NH;
Or the salts formed from the compounds represented by general formula III-A, III-B, III-C, III-D, III-E, III-F, III-G, III-H, III-I or III-J with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid or citric acid.
Even further more preferred compounds represented by formula III of this invention are:
R1 is selected from Cl, CH3, C2H5, CHCl2, CCl3, CH2F, CClF2, CHF2 or CF3;
R2 is selected from halo or cyano;
W is selected from H or CH3;
R3, R4 is selected from H;
R5a, R5c is selected from H;
R5b is selected from H, F, Cl, Br or OCH3;
R7, R8, R9, R11 may be the same or different, selected respectively from H, F, Cl, Br, cyano, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkoxycarbonyl, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, C1-C4alkylsulfonyl or haloC1-C4alkylsulfonyl;
R10 is selected from H, F, Cl, Br, I, cyano, NO2, methylsulfonyl, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy or haloC1-C4alkoxy;
A is selected from NH;
Or the salts formed from the compounds represented by general formula III-A with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid or citric acid.
Most preferred compounds represented by formula III of this invention are:
In the general formula III-A,
R1 is selected from Cl, CH3, C2H5, CHF2 or CF3;
R2 is selected from Cl or cyano;
W is selected from H or CH3;
R3, R4 is selected from H;
R5a, R5c is selected from H;
R5b is selected from H, Cl or OCH3;
R7, R8, R9, R may be the same or different, selected respectively from H, F, Cl, CH3, cyano, NO2, CF3, CClF2, CCl3, OCH3, OCF3, OCH2CF3, methylsulfonyl or trifluorosulfonyl;
R10 is selected from H, F, Cl, CH3, cyano, NO2, methylsulfonyl, CF3, CClF2, OCH3, OCF3 or OCH2CF3;
A is selected from NH;
Or the salts formed from the compounds represented by general formula III-A with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid or citric acid.
The terms of substitutes used above to definite the compounds represented by general formula PY are as follows:
The “halogen” or “halo” is fluorine, chlorine, bromine or iodine.
The “alkyl” stands for straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl or tert-butyl.
The “cycloalkyl” is substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. The substitute(s) is(are) methyl, halogen, etc.
The “haloalkyl” stands for straight or branched chain alkyl, in which hydrogen atoms can be all or partly substituted with halogen, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.
The “alkoxy” refers to straight or branched chain alkyl, which is linked to the structure by oxygen atom. The “haloalkoxy” refers to straight or branched chain alkoxy, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc. The “alkylthio” refers to straight or branched chain alkyl, which is linked to the structure by sulfur atom. The “haloalkylthio” refers to straight or branched chain alkylthio, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, etc.

The “cyanoalkyl” refers to straight or branched chain alkyl, in which hydrogen atoms may be all or partly substituted with cyano, such as —CH2CN, —CH2CH2CN, —CH2C(CH3)2 CN, —CH2CH(CN)2, etc. The “cyanoalkoxy” refers to alkoxy, in which hydrogen atoms may be all or partly substituted with cyano, such as —OCH2CN. The “haloalkylamino” refers to straight or branched chain alkylamino, in which hydrogen atoms may be all or partly substituted with halogen. The “dialkylamino” such as —N(CH3)2, —N(CH3CH2)2. The “dihaloalkylamino” such as —N(CF3)2, —N(CH2CCl3)2. The “dialkylaminoalkyl” such as —CH2N(CH3)2.

The “alkenyl” refers to straight or branched chain alkenyl, such as ethenyl, 1-propenyl, 2-propenyl and different isomer of butenyl, pentenyl and hexenyl. Alkenyl also includes polyene, such as propa-1,2-dienyl and hexa-2,4-dienyl. The “haloalkenyl” stands for straight or branched chain alkenyl, in which hydrogen atoms can be all or partly substituted with halogen. The “alkynyl” refers to straight or branched chain alkynyl, such as ethynyl, 1-propynyl, 2-propynyl and different isomer of butynyl, pentynyl and hexynyl. Alkynyl also includes groups including more than one triple bonds, such as hexa-2,5-diynyl. The “haloalkynyl” stands for straight or branched chain alkynyl, in which hydrogen atoms can be all or partly substituted with halogen.

The alkenoxyl refers to straight or branched chain alkynes is linked to the structure by oxygen, The haloalkenoxyl stands for a straight-chain or branched alkenoxyl, in which hydrogen atoms may be all or partly substituted with halogen. The alkynoxyl refers to straight or branched chain alkynes is linked to the structure by oxygen. The haloalkynoxyl stands for a straight-chain or branched alkynoxyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkylsulfinyl” means a straight-chain or branched alkyl is linked to the structure by (—SO—), such as methylsulfinyl.

The “haloalkylsulfinyl” stands for a straight-chain or branched alkylsulfinyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkylsulfonyl” means a straight-chain or branched alkyl is linked to the structure by (—SO2—), such as methylsulfonyl.

The “haloalkylsulfonyl” stands for a straight-chain or branched alkylsulfonyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkylcarbonyl” means alkyl is linked to the structure by carbonyl, such as —COCH3, —COCH2CH3. The “haloalkylcarbonyl” stands for a straight-chain or branched alkylcarbonyl, in which hydrogen atoms may be all or partly substituted with halogen, such as —COCF3. The “alkoxyalkyl” means alkyl-O-alkyl-, such as —CH2OCH3. The “haloalkoxyalkyl” refers to alkoxyalkyl, in which hydrogen atom may be all or partyl substituted with halogen, such as —CH2OCH2CH2Cl. The “alkylthioalkyl” means alkyl-S-alkyl-, such as —CH2SCH3. The “haloalkylthioalkyl” refers to alkylthioalkyl, in which hydrogen atom may be all or partyl substituted with halogen, such as —CH2SCH2CH2Cl, —CH2SCH2CF3.

The “alkoxycarbonyl” means alkoxy is linked to the structure by carbonyl, such as —COOCH3, —COOCH2CH3. The “haloalkoxycarbonyl” refers to straight or branched chain alkoxycarbonyl, in which hydrogen atoms can be all or partly substituted with halogen. The “alkylaminocarbonyl” means alkyl-NH—CO—, such as —CONHCH3, —CONHCH2CH3. The “dialkylaminocarbonyl” such as —CON(CH3)2, —CON(CH2CH3)2.

The “halodialkylaminocarbonyl” such as —CON(CF3)2, —CON(CH2CCl3)2.

The “alkoxycarbonylalkyl” such as —CH2COOCH3, —CH2COOCH2CH3. The “haloalkoxycarbonylalkyl” such as —CH2COOCF3, —CH2COOCH2CF3.

The “alkoxycarbonylamino” such as —NHCOOCH3, —NHCOOCH2CH3. The “alkoxyaminocarbonyl” such as —CONHOCH3, —CONHOCH2CH3. The “alkylaminocarbonylalkyl” such as —CH2CONHCH3, —CH2CONHCH2CH3. “dialkylaminocarbonylalkyl” such as —CH2CON(CH3)2, —CH2CON(CH2CH3)2.

The “alkenylthio” refers to straight or branched chain alkenyl, which is linked to the structure by sulfur atom. Such as —SCH2CH═CH2. The “cycloalkyloxycarbonyl” means cyclopropyloxycarbonyl, cyclohexyloxycarbonyl, etc.

The “alkenoxylcarbonyl” means CH2═CHCH2OCO—. The “alkynoxylcarbonyl” means —COOCH2C≡CH. The “alkoxyamino”: such as —NHOCH3. The “alkoxyalkoxycarbonyl”: such as —COOCH2CH2OCH3, etc. The “alkylaminothio” refers to —SNHCH3, —SNHC2H5. The “dialkylaminothio” refers to —SN(CH3)2, —SN(C2H5)2.

The “alkylcarbonylalkyl” refers to alkyl-CO-alkyl-. The “alkylsulfonylamino” refers to alkyl-SO2—NH—. The “haloalkylsulfonylamino” refers to straight or branched chain alkylsulfonylamino, in which hydrogen atoms can be all or partly substituted with halogen.

The “alkylsulfonylalkylamino” refers to alkyl-SO2-alkyl-NH—.

The “alkylaminosulfonyl” refers to alkyl-NH—SO2—. The“alkylcarbonylaminosulfonyl” refers to alkyl-CO—NH—SO2—. The “dialkylaminosulfonyl” refers to (alkyl)2-N—SO2—.

The “alkylthiocarbonylalkyl” refers to —CH2COSCH3, —CH2COSCH2CH3. The “haloalkylthiocarbonylalkyl” refers to —CH2COSCF3, —CH2COSCH2CF3.

The “alkylcarbonyloxy” such as —OCOCH3. The “haloalkylcarbonyloxy” such as —OCOCF3.

The “alkoxycarbonyloxy” such as —OCOOCH3. The “haloalkoxycarbonyloxy” such as —OCOOCF3. The “alkoxyalkoxy” stands for —OCH2OCH3. The “haloalkoxyalkoxy” stands for —OCH2OCF3. The “alkoxycarbonylalkoxy” stands for —OCH2COOCH3. The “alkylsulfonylaminocarbonyl” refers to alkyl-SO2—NH—CO—.

The “alkylcarbonylamino” refers to alkyl-CO—NH—. The “cycloalkyloxycarbonyl” means cyclopropyloxycarbonyl, cyclohexyloxycarbonyl. The “alkoxycarbonylalkoxy” stands for —OCH2COOCF3. The “alkylsulfonyloxy” such as alkyl-O—SO2CH3. The “haloalkylsulfonyloxy” such as —O—SO2CF3. The “alkylaminocarbonyloxy” such as —O—CONHCH3. The “haloalkylaminocarbonyloxy” such as —O—CONHCF3.

The “aryl” in (hetero)arylcarbonylalkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylalkyloxycarbonyl and (hetero)arylalkyl includes phenyl or naphthyl etc. The “heteroaryl” stands for five member ring or six member ring containing one or more N, O, S hetero atoms, such as furyl, pyrazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, etc.

(Hetero)arylcarbonylalkyl refers to —CH2COPh, etc. (Hetero)aryloxycarbonyl such as phenoxycarbonyl, p-chlorophenoxycarbonyl, p-nitrophenoxycarbonyl, naphthyloxycarbonyl, etc. Arylalkyloxycarbonyl means benzyloxycarbonyl, p-chlorobenzyloxycarbonyl, p-trifluoromethylbenzyloxycarbonyl, etc.

(Hetero)arylcarbonyl refers to benzoyl, 4-C1-benzoyl, etc. (Hetero)arylalkyloxycarbonyl refers to —COOCH2Ph, —COOCH2-4-Cl-Ph, etc.
(Hetero)arylalkyl means benzyl, phenylethyl, 4-chloro-benzyl, 2-chloro-5-picolyl, 2-chloro-5-methylthiazole, etc.
The present invention is also explained by the following compounds having a structure as represented by formula I listed in Table 1 to Table 118, but without being restricted thereby.
Table 1: in general formula I-A, R1=CH3, R2=Cl, R3=R4=R5b=R8=R10=R11=H, the substituent R9 refers to Table 1, the representative compounds are coded as I-1-I-58.














TABLE 1







No.
R9









I-1
H



I-2
F



I-3
Cl



I-4
Br



I-5
I



I-6
CH3



I-7
Et



I-8
n-Pr



I-9
i-Pr



I-10
n-Bu



I-11
s-Bu



I-12
t-Bu



I-13
CH2F



I-14
CH2Cl



I-15
CH2Br



I-16
CHF2



I-17
CHCl2



I-18
CHBr2



I-19
CClF2



I-20
CCl3



I-21
CBr3



I-22
CF3



I-23
CN



I-24
CH2OCH3



I-25
CH2OCH2CF3



I-26
CH2N(CH3)2



I-27
CH2CN



I-28
OCH3



I-29
OCF3



I-30
OCH2CF3



I-31
SCH3



I-32
SO2CH3



I-33
CO2H



I-34
CO2CH3



I-35
CO2C2H5



I-36
CO2CH2CF3



I-37
CO2-t-Bu



I-38
CONH2



I-39
CONHCH3



I-40
CON(CH3)2



I-41
CON(CH3)2



I-42
CONHNHCH3



I-43
CONHN(CH3)2



I-44
CONHOCH3



I-45
CONHNH2



I-46
CON(CH3)NH2



I-47
CONHNHCOCH3



I-48
CONHNHCO2CH3



I-49
CONHNH-Ph



I-50
NO2



I-51
NH2



I-52
NHCH3



I-53
NHCH2CH3



I-54
NHCOCH3



I-55
NHCO2CH3



I-56
NHSO2CH3



I-57
NHSO2CF3



I-58
N(CH3)SO2CH3










Table 2: in general formula I-A, R1=CH3, R2=R5b=Cl, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-59-I-116.
Table 3: in general formula I-A, R1=CH3, R2=Cl, R5b=Br, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-117-I-174.
Table 4: in general formula I-A, R1=CH3, R2=Cl, R5b=OCH3, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-175-I-232.
Table 5: in general formula I-A, R1=C2H5, R2=Cl, R3=R4=R5b=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-233-I-290.
Table 6: in general formula I-A, R1=C2H5, R2=R5b=Cl, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-291-I-348.
Table 7: in general formula I-A, R1=C2H5, R2=Cl, R5b=Br, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-349-I-406.
Table 8: in general formula I-A, R1=C2H5, R2=Cl, R5b=OCH3, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-407-I-464.
Table 9: in general formula I-A, R1=CH3, R2=R11=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-465-I-522.
Table 10: in general formula I-A, R1=CH3, R2=Cl, R11=NO2, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-523-I-580.
Table 11: in general formula I-A, R1=C2H5, R2=R11=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-581-I-638.
Table 12: in general formula I-A, R1=C2H5, R2=Cl, R11=NO2, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-639-I-696.
Table 13: in general formula I-A, R1=CH3, R2=R8=R11=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-697-I-754.
Table 14: in general formula I-A, R1=CH3, R2=R8=R10=R11=Cl, R3=R4=R5b=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-755-I-812.
Table 15: in general formula I-A, R1=C2H5, R2=R8=R1=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-813-I-870.
Table 16: in general formula I-A, R1=C2H5, R2=R8=R10=R11=Cl, R3=R4=R5b=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-871-I-928.
Table 17: in general formula I-A, R1=CH3, R2=Cl, R11=CF3, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-929-I-986.
Table 18: in general formula I-A, R1=C2H5, R2=Cl, R11=CF3, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-987-I-1044.
Table 19: in general formula I-A, R1=CH3, R2=Cl, R11=CO2CH3, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1045-I-1102.
Table 20: in general formula I-A, R1=CH3, R2=Cl, R11=CONH2, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1103-I-1160.
Table 21: in general formula I-A, R1=CH3, R2=Cl, R1=CONHCH3, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1161-I-1218.
Table 22: in general formula I-A, R1=C2H5, R2=Cl, R11=CO2CH3, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1219-I-1276.
Table 23: in general formula I-A, R1=C2H5, R2=Cl, R1=CONH2, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1277-I-1334.
Table 24: in general formula I-A, R1=C2H5, R2=Cl, R11=CONHCH3, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1335-I-1392.
Table 25: in general formula I-A, R1=CH3, R2=R5b=R11=Cl, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1393-I-1450.
Table 26: in general formula I-A, R1=C2H5, R2=R5b=R11=Cl, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1451-I-1508.
Table 27: in general formula I-A, R1=CH3, R2=R11=Cl, R5b=Br, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1509-I-1566.
Table 28: in general formula I-A, R1=C2H5, R2=R11=Cl, R5b=Br, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1567-I-1624.
Table 29: in general formula I-A, R1=CH3, R2=R1=Cl, R5b=OCH3, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1625-I-1682.
Table 30: in general formula I-A, R1=C2H5, R2=R1=Cl, R5b=OCH3, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1683-I-1740.
Table 31: in general formula I-A, R1=CH3, R2=Br, R3=R4=R5b=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1741-I-1798.
Table 32: in general formula I-A, R1=C2H5, R2=Br, R3=R4=R5b=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1799-I-1856.
Table 33: in general formula I-A, R1=CH3, R2=Br, R11=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1857-I-1914.
Table 34: in general formula I-A, R1=C2H5, R2=Br, R11=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1915-I-1972.
Table 35: in general formula I-A, R1=CH3, R2=Br, R5b=Cl, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-1973-I-2030.
Table 36: in general formula I-A, R1=C2H5, R2=Br, R5b=Cl, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2031-I-2088.
Table 37: in general formula I-A, R1=CH3, R2=R5b=Br, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2089-I-2146.
Table 38: in general formula I-A, R1=C2H5, R2=R5b=Br, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2147-I-2204.
Table 39: in general formula I-A, R1=CH3, R2=Br, R5b=OCH3, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2205-I-2262.
Table 40: in general formula I-A, R1=C2H5, R2=Br, R5b=OCH3, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2263-I-2320.
Table 41: in general formula I-A, R1=CF2H, R2=Cl, R3=R4=R5b=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2321-I-2378.
Table 42: in general formula I-A, R1=CF2H, R2=R5b=Cl, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2379-I-2436.
Table 43: in general formula I-A, R1=CF2H, R2=Cl, R5b=OCH3, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2437-I-2494.
Table 44: in general formula I-A, R1=CF2H, R2=Cl, R5b=Br, R3=R4=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2495-I-2552.
Table 45: in general formula I-A, R1=CF2H, R2=R11=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2553-I-2610.
Table 46: in general formula I-A, R1=CF2H, R2=Cl, R11=NO2, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2611-I-2668.
Table 47: in general formula I-A, R1=CF2H, R2=R11=Cl, R5b=OCH3, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2669-I-2726.
Table 48: in general formula I-A, R1=CF3, R2=Cl, R3=R4=R5b=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2727-I-2784.
Table 49: in general formula I-A, R1=CF3, R2=R11=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2785-I-2842.
Table 50: in general formula I-A, R1=CF3, R2=Cl, R11=NO2, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2843-I-2900.
Table 51: in general formula I-A, R1=CH2Cl, R2=Cl, R3=R4=R5b=R8=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2901-I-2958.
Table 52: in general formula I-A, R1=CH2Cl, R2=Cl, R11=NO2, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-2959-I-3016.
Table 53: in general formula I-A, R1=CH2Cl, R2=R11=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3017-I-3074.




Table 54: in general formula I-B, R1=CH3, R2=Cl, R3=R4=R5b=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3075-I-3132.
Table 55: in general formula I-B, R1=CH3, R2=R5b=Cl, R3=R4=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3133-I-3190.
Table 56: in general formula I-B, R1=CH3, R2=Cl, R5b=Br, R3=R4=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3191-I-3248.
Table 57: in general formula I-B, R1=CH3, R2=Cl, R5b=OCH3, R3=R4=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3249-I-3306.
Table 58: in general formula I-B, R1=C2H5, R2=Cl, R3=R4=R5b=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3307-I-3364.
Table 59: in general formula I-B, R1=C2H5, R2=R5b=Cl, R3=R4=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3365-I-3422.
Table 60: in general formula I-B, R1=C2H5, R2=Cl, R5b=Br, R3=R4=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3423-I-3480.
Table 61: in general formula I-B, R1=C2H5, R2=Cl, R5b=OCH3, R3=R4=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3481-I-3538.
Table 62: in general formula I-B, R1=CH3, R2=R11=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3539-I-3596.
Table 63: in general formula I-B, R1=CH3, R2=Cl, R11=NO2, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3597-I-3654.
Table 64: in general formula I-B, R1=C2H5, R2=R11=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3655-I-3712.
Table 65: in general formula I-B, R1=C2H5, R2=Cl, R11=NO2, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3713-I-3770.
Table 66: in general formula I-B, R1=CH3, R2=R10=Cl, R3=R4=R5b=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3771-I-3828.
Table 67: in general formula I-B, R1=CH3, R2=R10=R11=Cl, R3=R4=R5b=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3829-I-3886.
Table 68: in general formula I-B, R1=C2H5, R2=R11=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3887-I-3944.
Table 69: in general formula I-B, R1=C2H5, R2=R10=R11=Cl, R3=R4=R5b=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-3945-I-4002.
Table 70: in general formula I-B, R1=CH3, R2=Cl, R11=CF3, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4003-I-4060.
Table 71: in general formula I-B, R1=C2H5, R2=Cl, R11=CF3, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4061-I-4118.
Table 72: in general formula I-B, R1=CH3, R2=Br, R3=R4=R5b=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4119-I-4176.
Table 73: in general formula I-B, R1=C2H5, R2=Br, R3=R4=R5b=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4177-I-4234.




Table 74: in general formula I-C, R1=CH3, R2=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4235-I-4292.
Table 75: in general formula I-C, R1=CH3, R2=R5b=Cl, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4293-I-4350.
Table 76: in general formula I-C, R1=CH3, R2=Cl, R5b=Br, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4351-I-4408.
Table 77: in general formula I-C, R1=CH3, R2=Cl, R5b=Br, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4409-I-4466.
Table 78: in general formula I-C, R1=C2H5, R2=Cl, R3=R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4467-I-4524.
Table 79: in general formula I-C, R1=C2H5, R2=R5b=Cl, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4525-I-4582.
Table 80: in general formula I-C, R1=C2H5, R2=Cl, R5b=Br, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4583-I-4640.
Table 81: in general formula I-C, R1=C2H5, R2=Cl, R5b=OCH3, R3=R4=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4641-I-4698.
Table 82: in general formula I-C, R1=CH3, R2=Cl, R3=R4=R5b=H, R8=R10=CH3, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4699-I-4756.
Table 83: in general formula I-C, R1=CH3, R2=Cl, R3=R4=R5b=H, R8=R10=OCH3, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4757-I-4814.
Table 84: in general formula I-C, R1=CH3, R2=Cl, R3=R4=R5b=H, R8=R10=Cl, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4815-I-4872.
Table 85: in general formula I-C, R1=CH3, R2=Cl, R3=CH3, R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4873-I-4930.
Table 86: in general formula I-C, R1=CH3, R2=Cl, R3=CH3, R4=R5b=H, R8=R10=CH3, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4931-I-4988.
Table 87: in general formula I-C, R1=CH3, R2=Cl, R3=CH3, R4=R5b=H, R8=R10=OCH3, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-4989-I-5046.
Table 88: in general formula I-C, R1=CH3, R2=Cl, R3=CH3, R4=R5b=H, R8=R10=Cl, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5047-I-5104.
Table 89: in general formula I-C, R1=C2H5, R2=Cl, R3=CH3, R4=R5b=R8=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5105-I-5162.
Table 90: in general formula I-C, R1=C2H5, R2=Cl, R3=R4=R5b=H, R8=R10=CH3, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5163-I-5220.
Table 91: in general formula I-C, R1=C2H5, R2=Cl, R3=R4=R5b=H, R8=R10=OCH3, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5221-I-5278.
Table 92: in general formula I-C, R1=C2H5, R2=Cl, R3=R4=R5b=H, R8=R10=Cl, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5279-I-5336.
Table 93: in general formula I-C, R1=CH3, R2=R8=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5337-I-5394.
Table 94: in general formula I-C, R1=CH3, R2=Cl, R8=CH3, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5395-I-5452.
Table 95: in general formula I-C, R1=CH3, R2=Cl, R8=OCH3, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5453-I-5510.
Table 96: in general formula I-C, R1=C2H5, R2=R8=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5511-I-5568.
Table 97: in general formula I-C, R1=C2H5, R2=Cl, R8=CH3, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5569-I-5626.
Table 98: in general formula I-C, R1=C2H5, R2=Cl, R8=OCH3, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5627-I-5684.




Table 99: in general formula I-D, R1=CH3, R2=Cl, R3=R4=R5b=R7=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5685-I-5742.
Table 100: in general formula I-D, R1=CH3, R2=R5b=Cl, R3=R4=R7=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5743-I-5800.
Table 101: in general formula I-D, R1=CH3, R2=Cl, R5b=Br, R3=R4=R7=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5801-I-5858.
Table 102: in general formula I-D, R1=CH3, R2=Cl, R5b=OCH3, R3=R4=R7=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5859-I-5916.
Table 103: in general formula I-D, R1=C2H5, R2=Cl, R3=R4=R5b=R7=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5917-I-5974.
Table 104: in general formula I-D, R1=C2H5, R2=R5b=Cl, R3=R4=R7=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-5975-I-6032.
Table 105: in general formula I-D, R1=C2H5, R2=Cl, R5b=Br, R3=R4=R7=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6033-I-6090.
Table 106: in general formula I-D, R1=C2H5, R2=Cl, R5b=OCH3, R3=R4=R7=R10=R11=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6091-I-6148.
Table 107: in general formula I-D, R1=CH3, R2=R11=Cl, R3=R4=R5b=R7=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6149-I-6206.
Table 108: in general formula I-D, R1=CH3, R2=Cl, R11=NO2, R3=R4=R5b=R7=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6207-I-6264.
Table 109: in general formula I-D, R1=C2H5, R2=R11=Cl, R3=R4=R5b=R7=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6265-I-6322.
Table 110: in general formula I-D, R1=C2H5, R2=Cl, R11=NO2, R3=R4=R5b=R7=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6323-I-6380.
Table 111: in general formula I-D, R1=CH3, R2=R7=R11=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6381-I-6438.
Table 112: in general formula I-D, R1=CH3, R2=R7=R10=R11=Cl, R3=R4=R5b=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6439-I-6496.
Table 113: in general formula I-D, R1=C2H5, R2=R7=R11=Cl, R3=R4=R5b=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6497-I-6554.
Table 114: in general formula I-D, R1=C2H5, R2=R7=R10=R11=Cl, R3=R4=R5b=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6555-I-6612.
Table 115: in general formula I-D, R1=CH3, R2=Cl, R11=CF3, R3=R4=R5b=R7=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6613-I-6670.
Table 116: in general formula I-D, R1=C2H5, R2=Cl, R11=CF3, R3=R4=R5b=R7=R10=H, the substituent R9 are consistent with those in Table 1 and corresponding to I-1-I-58 in table 1 in turn, the representative compounds are coded as I-6671-I-6728.
Table 117: the salts of some compounds having a structure as represented by formula I of the present invention are listed in Table 117, but without being restricted thereby.







TABLE 117







the salts of some compounds








No.
structure





I-6729






 


I-6730






 


I-6731






 


I-6732






 


I-6733






 


I-6734






 


I-6735






 


I-6736






 


I-6737






 


I-6738






 


I-6739






 


I-6740






 


I-6741






 


I-6742






 


I-6743






 


I-6744






 


I-6745






 


I-6746






 


I-6747






 


I-6748






 


I-6749






 


I-6750






 


I-6751






 


I-6752






 


I-6753






 


I-6754






 


I-6755






 


I-6756






 


I-6757






 


I-6758






 


I-6759






 


I-6760






 


I-6761






 


I-6762






 


I-6763






 


I-6764






 


I-6765






 


I-6766






 


I-6767






 


I-6768






 


I-6769






 


I-6770






 


I-6771






 


I-6772






 


I-6773






 


I-6774






 


I-6775






 


I-6776






 


I-6777






 


I-6778






 


I-6779






 


I-6780






 


I-6781






 


I-6782













Some compounds represented by general formula I-E, I-F, I-G and I-H of the present invention are listed in Table 118, but without being restricted thereby.








TABLE 118





No.
structure







I-6783






 


I-6784






 


I-6785






 


I-6786






 


I-6787






 


I-6788






 


I-6789






 


I-6790






 


I-6791






 


I-6792






 


I-6793






 


I-6794






 


I-6795






 


I-6796






 


I-6797






 


I-6798






 


I-6799






 


I-6800






 


I-6801






 


I-6802






 


I-6803






 


I-6804






 


I-6805






 


I-6806






 


I-6807






 


I-6808






 


I-6809






 


I-6810






 


I-6811






 


I-6812






 


I-6813






 


I-6814






 


I-6815






 


I-6816






 


I-6817






 


I-6818






 


I-6819






 


I-6820






 


I-6821






 


I-6822






 


I-6823






 


I-6824






 


I-6825






 


I-6826






 


I-6827






 


I-6828






 


I-6829






 


I-6830






 


I-6831






 


I-6832






 


I-6833






 


I-6834






 


I-6835






 


I-6836






 


I-6837






 


I-6838






 


I-6839






 


I-6840






 


I-6841






 


I-6842






 


I-6843






 


I-6844






 


I-6845






 


I-6846













In the general formula I, A=NR12, R12≠H, part of preferred substituents of R12 are listed in table 119, but without being restricted thereby. The present invention is also explained by the following compounds in the general formula I listed in Table 120, but without being restricted thereby.







TABLE 119





R12 substituents


R12







OH


C2H5


i-C4H9


CHF2


CHCl2


OC2H5


OCH2CF3


SCH3


CH2CH═CH2


CH2C≡C—I


CH2CH2OCH2CH3


CH2SCH3


CH2SCH2Cl


SOC2H5


SO2C2H5


SO2NHCH3


COC2H5


CO-i-C4H9


COOCH3


COOCF3


CH2COOC2H5


CONHC2H5


COOCH2CH═CH2


SNHCH3


 








 








 








 








 








 








 








 








 








 








 








 


—C(═O)H


n-C3H7


t-C4H9


CHBr2


CCl3


OCH(CH3)2


OCF2CF3


SC2H5


CH2CH═CCl2


CH2OCH3


CH2OCH2Cl


CH2SCH2CH3


CH2SCH2CH2Cl


SOCF3


SO2CF3


SO2N(CH3)3


CO-n-C3H7


CO-t-C4H9


COOC2H5


COOCH2CH2Cl


CH2COCH3


CONH-t-C4H9


COOCH2C≡CH


SNHC2H5


 








 








 








 








 








 








 








 








 








 








 








 


CBr3


i-C3H7


CI3


CF3


CH2F


OC(CH3)3


OCH2F


SCH2CH═CH2


C≡CH


CH2OCH2CH3


CH2OCH2CH2Cl


CH2CH2SCH3


CH2CH2SCH2Cl


SOCH2CF3


SO2CH2CF3


CONHSO2CH3


CO-i-C3H7


COCF3


COO-n-C3H7


COOCH2CF3


CH2COC2H5


CON(CH3)2


COOCH2OCH3


SN(CH3)2


 








 








 








 








 








 








 








 








 








 








 








 


CH3


n-C4H9


CH2Br


CH2Cl


OCH3


OCF3


OCHF2


CH═CH2


CH2C≡CH


CH2CH2OCH3


CH2CH2OCH2Cl


CH2CH2SCH2CH3


SOCH3


SO2CH3


SO2NHCOCH3


COCH3


CO-n-C4H9


COCH2Cl


COO-t-C4H9


CH2COOCH3


CONHCH3


CON(C2H5)2


COOCH2CH2OCH3


SN(C2H5)2


 








 








 








 








 








 








 








 








 








 








 























TABLE 120





No.
structure







I-6847






 


I-6848






 


I-6849






 


I-6850






 


I-6851






 


I-6852






 


I-6853






 


I-6854






 


I-6855






 


I-6856






 


I-6857






 


I-6858






 


I-6859






 


I-6860






 


I-6861






 


I-6862






 


I-6863






 


I-6864






 


I-6865






 


I-6866






 


I-6867






 


I-6868






 


I-6869






 


I-6870






 


I-6871






 


I-6872






 


I-6873






 


I-6874






 


I-6875






 


I-6876






 


I-6877






 


I-6878






 


I-6879






 


I-6880






 


I-6881






 


I-6882






 


I-6883






 


I-6884






 


I-6885






 


I-6886






 


I-6887






 


I-6888






 


I-6889






 


I-6890






 


I-6891






 


I-6892






 


I-6893






 


I-6894













In the general formula II, part of preferred substituents of R1, R2, R3(R4), R5a(R5b, R5c), R6(R7, R8, R9, R10, R11) and R12 are separately listed in table 121, table 122, table 123, table 124, table 125 and table 126, but without being restricted thereby.











TABLE 121





R1 substituents


R1







CH3


n-C4H9


CF3


CH2Br


CF2H


 








 


C2H5


s-C4H9


CCl3


CClF2


CBr2H


 








 


n-C3H7


i-C4H9


CH2F


CFCl2


CBr3


 








 


i-C3H7


t-C4H9


CH2Cl


CCl2H


CClBr2


 






















TABLE 122







R2 substituents












R2
R2
R2
R2







F
Cl
Br
I



CN
OCH3
OC2H5
OC3H7-n



OC3H7-i
OC4H9-n
OC4H9-i
OC4H9-t

















TABLE 123





R3(R4) substituents







R3(R4)





H


i-C3H7


F


t-C4H9


OCH3


CH3


n-C4H9


Cl


 








 


OC2H5


C2H5


s-C4H9


Br


 








 


OC3H7-n


n-C3H7


i-C4H9


I


 








 


OC3H7-i





CR3(R4)











 








 








 






















TABLE 124







R5a (R5b, R5c) substituents










R5a (R5b, R5c)
R5a (R5b, R5c)
R5a (R5b, R5c)
R5a (R5b, R5c)





H
CH3
i-C4H9
OC4H9-n


F
C2H5
t-C4H9
OC4H9-i


Cl
n-C3H7
OCH3
OC4H9-t


Br
i-C3H7
OC2H5
OCF3


I
n-C4H9
OC3H7-n
OCH2CF3


OH
s-C4H9
OC3H7-i
OCF2CF3
















TABLE 125







R6 (R7, R8, R9, R10, R11) substituents











R6 (R7, R8,






R9, R10,
R6 (R7, R8,
R6 (R7, R8, R9,
R6 (R7, R8, R9,


R11)
R9, R10, R11)
R10, R11)
R10, R11)
R6 (R7, R8, R9, R10, R11)





H
4-CH3
3-CH2OCH3
2,6-2Cl-4-CONH2
2-CF3-4-Br-6-NO2


2-F
2,3-2CH3
4-CH2OCH3
2,4-2Cl-6-NO2
3-NO2-4-CF3


3-F
2,4-2CH3
2-OCOCH3
2,4-2Cl-6-CN
2-NO2-4-CN-5-CF3


4-F
2,5-2CH3
3-OCOCH3
2,4-2Cl-6-CF3
2-NO2-4-CF3-5-CN


2,3-2F
2,6-2CH3
4-OCOCH3
2,4-2F-6-NO2
4-OCF3-2,6-2Br


2,4-2F
3,4-2CH3
2-OCOCH2CH3
2,6-2F-4-NO2
2-CH3-4-Cl-5-CH2CO2C2H5


2,5-2F
3,5-2CH3
3-OCOCH2CH3
2-NO2-4-F
2,4-2Cl-3-CH3


2,6-2F
2-C2H5
4-OCOCH2CH3
2-NO2-4-Br
2,4-2Cl-3-CH3-6-NO2


3,4-2F
3-C2H5
2-OCO2CH3
2-NO2-4-CF3
2-Cl-3-CH3


3,5-2F
4-C2H5
3-OCO2CH3
2-NO2-4-CN
2-CH3-3-Cl


2,3,4-3F
2-CF3
4-OCO2CH3
2-NO2-4-COCH3
2-CH3-3-Cl-4,6-2NO2


2,3,5-3F
3-CF3
2-OCH2OCH3
2-NO2-4-CONH2
2-CH3-3-Cl-4-NO2


2,4,5-3F
4-CF3
3-OCH2OCH3
2-NO2-4-CH3
2-CH3-3-Cl-6-NO2


2,3,6-3F
2-OCH3
4-OCH2OCH3
2-NO2-4-OCH3
2-Cl-3-CH3-4,6-2NO2


2,4,6-3F
3-OCH3
2-OCF2OCF3
2-NO2-4-SCH3
2-Cl-3-CH3-4-NO2


3,4,5-3F
4-OCH3
3-OCF2OCF3
2-NO2-4-NCH3
2-Cl-3-CH3-6-NO2


2-Cl
2-SCH3
4-OCF2OCF3
2-F-4-NO2
2-Br-4-NO2-6-CN


3-Cl
3-SCH3
2-COPh
2-Br-4-NO2
3-Cl-4-CF3-2,6-2NO2


4-Cl
4-SCH3
3-COPh
2-CF3-4-NO2
2NO2-4,5-2Cl


2,3-2Cl
2-OCF3
4-COPh
2-CN-4-NO2
2-NO2-3,5-2Cl


2,4-2Cl
3-OCF3
2-COCH2Ph
2-COCH3-4-NO2
2,5-2Cl-4-NO2


2,5-2Cl
4-OCF3
3-COCH2Ph
2-CONH2-4-NO2
2,5-2Cl-6-NO2


2,6-2Cl
2-SCF3
4-COCH2Ph
2-CH3-4-NO2
2,3-2Cl-4-NO2


3,4-2Cl
3-SCF3
2-NHPh
2-Cl-4-F-6-NO2
2,3-2Cl-6-NO2


3,5-2Cl
4-SCF3
3-NHPh
2-Cl-4-Br-6-NO2
3,4-2Cl-2,6-2NO2


2,3,4-3Cl
2-OC2H5
4-NHPh
2-Cl-4-CH3-6-NO2
2,5-2Cl-4,6-2NO2


2,3,5-3Cl
3-OC2H5
2-OPh
2-Cl-4-CF3-6-NO2
2,4,5-3Cl-6-NO2


2,4,5-3Cl
4-OC2H5
3-OPh
2-Cl-4,6-2NO2
2,3,4-3Cl-5-NO2


2,3,6-3Cl
2-NHCH3
4-OPh
2-Cl-4-CN-6-NO2
2,3,4-3Cl-6-NO2


2,4,6-3Cl
3-NHCH3
2-CONHPh
2-Cl-4-OCF3-6-NO2
2,3,5-3Cl-4,6-2CN


3,4,5-3Cl
4-NHCH3
3-CONHPh
2-F-4-Cl-6-NO2
2,5-2Cl-4-OCF2OCF3


2-Br
2-N(CH3)2
4-CONHPh
2-Br-4-Cl-6-NO2
2,6-2Br-4-NO2


3-Br
3-N(CH3)2
2-CO2Ph
2-CH3-4-Cl-6-NO2
2-F-4-NO2-6-Cl


4-Br
4-N(CH3)2
3-CO2Ph
2-CF3-4-Cl-6-NO2
2-Cl-4-NO2-6-SCN


2,3-2Br
2-COCH3
4-CO2Ph
4-Cl-2,6-2NO2
2-Br-4-NO2-6-Cl


2,4-2Br
3-COCH3
2-CONH2
2-F-4-CN
2-Cl-4-NO2-6-OCH3


2,5-2Br
4-COCH3
3-CONH2
2-CN-4-CF3
2-Cl-4-NO2-6-SCH3


2,6-2Br
2-COC2H5
4-CONH2
4-CF3-2,6-2NO2
2-Cl-4-NO2-6-NHCH3


3,4-2Br
3-COC2H5
2-Cl-4-F
4-CN-2,6-2NO2
2-Cl-4-NO2-6-SO2CH3


3,5-2Br
4-COC2H5
2-Cl-4-Br
4-CH3-2,6-2NO2
2-Cl-4-SO2CH3


2,3,4-3Br
2-SO2CH3
2-Cl-4-CH3
4-OCF3-2,6-2NO2
2,6-2Cl-4-SO2CH3


2,3,5-3Br
3-SO2CH3
2-Cl-4-CF3
4-OCH3-2,6-2NO2
2,6-2Cl-4-CH3


2,4,5-3Br
4-SO2CH3
2-Cl-4-NO2
4-SCH3-2,6-2NO2
2,6-2Cl-4-CO2CH3


2,3,6-3Br
2-OCHF2
2-Cl-4-CN
4-NHCH3-2,6-2NO2
2,6-2Cl-4-CONHCH3


2,4,6-3Br
3-OCHF2
2-Cl-4-OCF3
4-F-2,6-2NO2
2,6-2Cl-4-CON(CH3)2


3,4,5-3Br
4-OCHF2
2-F-4-Cl
2-CF3-4,6-2NO2
2,6-2Cl-4-CF(CF3)2


2-CN
2-SO2C2H5
2-Br-4-Cl
2-CN-4,6-2NO2
2-Cl-4-CF(CF3)2-6-Br


3-CN
3-SO2C2H5
2-CH3-4-Cl
2-CH3-4,6-2NO2
2-F-4-CF(CF3)2-6-Br


4-CN
4-SO2C2H5
2-CF3-4-Cl
2-F-4,6-2NO2
2-F-4-CF(CF3)2-6-Cl


2-NO2
2-CO2CH3
2-NO2-4-Cl
2-OCF3-4,6-2NO2
2,4,5-3Cl-3,6-2CN


3-NO2
3-CO2CH3
2-CN-4-Cl
2-CF3-4-Br
2,3,5-3F-4,6-2CN


4-NO2
4-CO2CH3
2-OCF3-4-Cl
3-CF3-4-NO2
2-SO2NH2


2,4-2NO2
2-CO2C2H5
2,6-2Cl-4-NO2
2-CN-4-Cl-6-NO2
3-SO2NH2


2,4,6-3NO2
3-CO2C2H5
2,6-2Cl-4-CF3
2-OCF3-4-Cl-6-NO2
4-SO2NH2


2-CH3
4-CO2C2H5
2,6-2Cl-4-CN
3-CF3-4-CN


3-CH3
2-CH2OCH3
2,6-2Cl-4-COCH3
3-CN-4-CF3
















TABLE 126







R12 substituents












R12
R12
R12
R12







H
OH
CH3
C2H5



n-C3H7
i-C3H7
n-C4H9
s-C4H9



i-C4H9
t-C4H9
HCO
CH3CO



CH3CH2CO
n-C3H7CO
i-C3H7CO
CH3SO2



CH3CH2SO2
n-C3H7SO2
n-C4H9SO2










The present invention is also explained by the following compounds having a structure as represented by formula II listed in Table 127 to Table 202, Compounds having a structure as represented by formula II-A are listed in Table 127 to Table 190, Compounds having a structure as represented by formula II-B are listed in Table 191 to Table 201, but without being restricted thereby.




In general formula II-A, W=H, R1=CH3, R2=Cl, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 refer to Table 127, the representative compounds are coded as II-1-II-2780












TABLE 127





No.
R7
R8
R9
R10
R11







II-1
H
H
H
H
H


II-2
F
H
H
H
H


II-3
H
F
H
H
H


II-4
H
H
F
H
H


II-5
F
F
H
H
H


II-6
F
H
F
H
H


II-7
F
H
H
F
H


II-8
F
H
H
H
F


II-9
H
F
F
H
H


II-10
H
F
H
F
H


II-11
F
F
F
H
H


II-12
F
F
H
F
H


II-13
F
H
F
F
H


II-14
F
F
H
H
F


II-15
F
H
F
H
F


II-16
H
F
F
F
H


II-17
Cl
H
H
H
H


II-18
H
Cl
H
H
H


II-19
H
H
Cl
H
H


II-20
Cl
Cl
H
H
H


II-21
Cl
H
Cl
H
H


II-22
Cl
H
H
Cl
H


II-23
Cl
H
H
H
Cl


II-24
H
Cl
Cl
H
H


II-25
H
Cl
H
Cl
H


II-26
Cl
Cl
Cl
H
H


II-27
Cl
Cl
H
Cl
H


II-28
Cl
H
Cl
Cl
H


II-29
Cl
Cl
H
H
Cl


II-30
Cl
H
Cl
H
Cl


II-31
H
Cl
Cl
Cl
H


II-32
Br
H
H
H
H


II-33
H
Br
H
H
H


II-34
H
H
Br
H
H


II-35
Br
Br
H
H
H


II-36
Br
H
Br
H
H


II-37
Br
H
H
Br
H


II-38
Br
H
H
H
Br


II-39
H
Br
Br
H
H


II-40
H
Br
H
Br
H


II-41
Br
Br
Br
H
H


II-42
Br
Br
H
Br
H


II-43
Br
H
Br
Br
H


II-44
Br
Br
H
H
Br


II-45
Br
H
Br
H
Br


II-46
H
Br
Br
Br
H


II-47
CN
H
H
H
H


II-48
H
CN
H
H
H


II-49
H
H
CN
H
H


II-50
NO2
H
H
H
H


II-51
H
NO2
H
H
H


II-52
H
H
NO2
H
H


II-53
NO2
H
NO2
H
H


II-54
NO2
H
NO2
H
NO2


II-55
CH3
H
H
H
H


II-56
H
CH3
H
H
H


II-57
H
H
CH3
H
H


II-58
CH3
CH3
H
H
H


II-59
CH3
H
CH3
H
H


II-60
CH3
H
H
CH3
H


II-61
CH3
H
H
H
CH3


II-62
H
CH3
CH3
H
H


II-63
H
CH3
H
CH3
H


II-64
C2H5
H
H
H
H


II-65
H
C2H5
H
H
H


II-66
H
H
C2H5
H
H


II-67
CF3
H
H
H
H


II-68
H
CF3
H
H
H


II-69
H
H
CF3
H
H


II-70
OCH3
H
H
H
H


II-71
H
OCH3
H
H
H


II-72
H
H
OCH3
H
H


II-73
SCH3
H
H
H
H


II-74
H
SCH3
H
H
H


II-75
H
H
SCH3
H
H


II-76
OCF3
H
H
H
H


II-77
H
OCF3
H
H
H


II-78
H
H
OCF3
H
H


II-79
SCF3
H
H
H
H


II-80
H
SCF3
H
H
H


II-81
H
H
SCF3
H
H


II-82
OC2H5
H
H
H
H


II-83
H
OC2H5
H
H
H


II-84
H
H
OC2H5
H
H


II-85
NHCH3
H
H
H
H


II-86
H
NHCH3
H
H
H


II-87
H
H
NHCH3
H
H


II-88
N(CH3)2
H
H
H
H


II-89
H
N(CH3)2
H
H
H


II-90
H
H
N(CH3)2
H
H


II-91
COCH3
H
H
H
H


II-92
H
COCH3
H
H
H


II-93
H
H
COCH3
H
H


II-94
COC2H5
H
H
H
H


II-95
H
COC2H5
H
H
H


II-96
H
H
COC2H5
H
H


II-97
SO2CH3
H
H
H
H


II-98
H
SO2CH3
H
H
H


II-99
H
H
SO2CH3
H
H


II-100
OCHF2
H
H
H
H


II-101
H
OCHF2
H
H
H


II-102
H
H
OCHF2
H
H


II-103
SO2C2H5
H
H
H
H


II-104
H
SO2C2H5
H
H
H


II-105
H
H
SO2C2H5
H
H


II-106
CO2CH3
H
H
H
H


II-107
H
CO2CH3
H
H
H


II-108
H
H
CO2CH3
H
H


II-109
CO2C2H5
H
H
H
H


II-110
H
CO2C2H5
H
H
H


II-111
H
H
CO2C2H5
H
H


II-112
CH2OCH3
H
H
H
H


II-113
H
CH2OCH3
H
H
H


II-114
H
H
CH2OCH3
H
H


II-115
OCOCH3
H
H
H
H


II-116
H
OCOCH3
H
H
H


II-117
H
H
OCOCH3
H
H


II-118
OCOCH2CH3
H
H
H
H


II-119
H
OCOCH2CH3
H
H
H


II-120
H
H
OCOCH2CH3
H
H


II-121
OCO2CH3
H
H
H
H


II-122
H H
OCO2CH3
H
H
H


II-123
H
H
OCO2CH3
H
H


II-124
OCH2OCH3
H
H
H
H


II-125
H
OCH2OCH3
H
H
H


II-126
H
H
OCH2OCH3
H
H


II-127
OCF2OCF3
H
H
H
H


II-128
H
OCF2OCF3
H
H
H


II-129
H
H
OCF2OCF3
H
H


II-130
COPh
H
H
H
H


II-131
H
COPh
H
H
H


II-132
H
H
COPh
H
H


II-133
COCH2Ph
H
H
H
H


II-134
H
COCH2Ph
H
H
H


II-135
H
H
COCH2Ph
H
H


II-136
NHPh
H
H
H
H


II-137
H
NHPh
H
H
H


II-138
H
H
NHPh
H
H


II-139
OPh
H
H
H
H


II-140
H
OPh
H
H
H


II-141
H
H
OPh
H
H


II-142
CONHPh
H
H
H
H


II-143
H
CONHPh
H
H
H


II-144
H
H
CONHPh
H
H


II-145
CO2Ph
H
H
H
H


II-146
H
CO2Ph
H
H
H


II-147
H
H
CO2Ph
H
H


II-148
CONH2
H
H
H
H


II-149
H
CONH2
H
H
H


II-150
H
H
CONH2
H
H


II-151
Cl
H
F
H
H


II-152
Cl
H
Br
H
H


II-153
Cl
H
CH3
H
H


II-154
Cl
H
CF3
H
H


II-155
Cl
H
NO2
H
H


II-156
Cl
H
CN
H
H


II-157
Cl
H
OCF3
H
H


II-158
F
H
Cl
H
H


II-159
Br
H
Cl
H
H


II-160
CH3
H
Cl
H
H


II-161
CF3
H
Cl
H
H


II-162
NO2
H
Cl
H
H


II-163
CN
H
Cl
H
H


II-164
OCF3
H
Cl
H
H


II-165
Cl
H
NO2
H
Cl


II-166
Cl
H
CF3
H
Cl


II-167
Cl
H
CN
H
Cl


II-168
Cl
H
COCH3
H
Cl


II-169
Cl
H
CONH2
H
Cl


II-170
Cl
H
Cl
H
NO2


II-171
Cl
H
Cl
H
CN


II-172
Cl
H
Cl
H
CF3


II-173
F
H
F
H
NO2


II-174
F
H
NO2
H
F


II-175
NO2
H
F
H
H


II-176
NO2
H
Br
H
H


II-177
NO2
H
CF3
H
H


II-178
NO2
H
CN
H
H


II-179
NO2
H
COCH3
H
H


II-180
NO2
H
CONH2
H
H


II-181
NO2
H
CH3
H
H


II-182
NO2
H
OCH3
H
H


II-183
NO2
H
SCH3
H
H


II-184
NO2
H
NCH3
H
H


II-185
F
H
NO2
H
H


II-186
Br
H
NO2
H
H


II-187
CF3
H
NO2
H
H


II-188
CN
H
NO2
H
H


II-189
COCH3
H
NO2
H
H


II-190
CONH2
H
NO2
H
H


II-191
CH3
H
NO2
H
H


II-192
Cl
H
F
H
NO2


II-193
Cl
H
Br
H
NO2


II-194
Cl
H
CH3
H
NO2


II-195
Cl
H
CF3
H
NO2


II-196
Cl
H
NO2
H
NO2


II-197
Cl
H
CN
H
NO2


II-198
Cl
H
OCF3
H
NO2


II-199
F
H
Cl
H
NO2


II-200
Br
H
Cl
H
NO2


II-201
CH3
H
Cl
H
NO2


II-202
CF3
H
Cl
H
NO2


II-203
NO2
H
Cl
H
NO2


II-204
F
H
CN
H
H


II-205
CN
H
CF3
H
H


II-206
NO2
H
CF3
H
NO2


II-207
NO2
H
CN
H
NO2


II-208
NO2
H
CH3
H
NO2


II-209
NO2
H
OCF3
H
NO2


II-210
NO2
H
OCH3
H
NO2


II-211
NO2
H
SCH3
H
NO2


II-212
NO2
H
NHCH3
H
NO2


II-213
NO2
H
F
H
NO2


II-214
CF3
H
NO2
H
NO2


II-215
CN
H
NO2
H
NO2


II-216
CH3
H
NO2
H
NO2


II-217
F
H
NO2
H
NO2


II-218
OCF3
H
NO2
H
NO2


II-219
CF3
H
Br
H
H


II-220
H
CF3
NO2
H
H


II-221
CN
H
Cl
H
NO2


II-222
OCF3
H
Cl
H
NO2


II-223
H
CF3
CN
H
H


II-224
H
CN
CF3
H
H


II-225
CF3
H
Br
H
NO2


II-226
H
NO2
CF3
H
H


II-227
NO2
H
CN
CF3
H


II-228
NO2
H
CF3
CN
H


II-229
Br
H
OCF3
H
Br


II-230
CH3
H
Cl
CH2CO2C2H5
H


II-231
Cl
CH3
Cl
H
OCF2OCF3


II-232
Cl
CH3
Cl
H
NO2


II-233
Cl
CH3
H
H
H


II-234
CH3
Cl
H
H
H


II-235
CH3
Cl
NO2
H
NO2


II-236
CH3
Cl
NO2
H
H


II-237
CH3
Cl
H
H
NO2


II-238
Cl
CH3
NO2
H
NO2


II-239
Cl
CH3
NO2
H
H


II-240
Cl
CH3
H
H
NO2


II-241
Br
H
NO2
H
CN


II-242
NO2
Cl
CF3
H
NO2


II-243
NO2
H
Cl
Cl
H


II-244
NO2
Cl
H
Cl
H


II-245
Cl
H
NO2
Cl
H


II-246
Cl
H
H
Cl
NO2


II-247
Cl
Cl
NO2
H
H


II-248
Cl
Cl
H
H
NO2


II-249
NO2
Cl
Cl
H
NO2


II-250
Cl
H
NO2
Cl
NO2


II-251
Cl
H
Cl
Cl
NO2


II-252
Cl
Cl
Cl
NO2
H


II-253
Cl
Cl
Cl
H
NO2


II-254
Cl
Cl
CN
Cl
CN


II-255
Cl
H
OCF2OCF3
Cl
H


II-256
Br
H
NO2
H
Br


II-257
F
H
NO2
H
Cl


II-258
Cl
H
NO2
H
SCN


II-259
Br
H
NO2
H
Cl


II-260
Cl
H
NO2
H
OCH3


II-261
Cl
H
NO2
H
SCH3


II-262
Cl
H
NO2
H
NHCH3


II-263
Cl
H
NO2
H
SO2CH3


II-264
Cl
H
SO2CH3
H
H


II-265
Cl
H
SO2CH3
H
Cl


II-266
Cl
H
CH3
H
Cl


II-267
Cl
H
CO2CH3
H
Cl


II-268
Cl
H
CONHCH3
H
Cl


II-269
Cl
H
CON(CH3)2
H
Cl


II-270
Cl
H
CF(CF3)2
H
Cl


II-271
Cl
H
CF(CF3)2
H
Br


II-272
F
H
CF(CF3)2
H
Br


II-273
F
H
CF(CF3)2
H
Cl


II-274
Cl
CN
Cl
Cl
CN


II-275
F
F
CN
F
CN


II-276
SO2NH2
H
H
H
H


II-277
H
SO2NH2
H
H
H


II-278
H
H
SO2NH2
H
H









Table 128: in general formula II-A, W=H, R1=C2H5, R2=Cl, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-279-II-556.
Table 129: in general formula II-A, W=H, R1=CH3, R2=R5b=Cl, R3=R4=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-557-II-834.
Table 130: in general formula II-A, W=H, R1=C2H5, R2=R5b=Cl, R3=R4=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-835-II-1112.
Table 131: in general formula II-A, W=H, R1=CH3, R2=Cl, R3=R4=H, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-1113-II-1390.
Table 132: in general formula II-A, W=H, R1=C2H5, R2=Cl, R3=R4=H, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-1391-II-1668.
Table 133: in general formula II-A, W=H, R1=CH3, R2=Cl, R3=R4=H, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-1669-II-1946.
Table 134: in general formula II-A, W=H, R1=C2H5, R2=Cl, R3=R4=H, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-1947-II-2224.
Table 135: in general formula II-A, W=H, R1=CH3, R2=Cl, R3=R5b=H, R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-2225-II-2502.
Table 136: in general formula II-A, W=H, R1=C2H5, R2=Cl, R3=R5b=H, R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-2503-II-2780.
Table 137: in general formula II-A, W=H, R1=CH3, R2=Cl, R3=H, R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-2781-II-3058.
Table 138: in general formula II-A, W=H, R1=C2H5, R2=Cl, R3=H, R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-3059-II-3336.
Table 139: in general formula II-A, W=H, R1=CH3, R2=Cl, R3=H, R4=CH3, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-3337-II-3614.
Table 140: in general formula II-A, W=H, R1=C2H5, R2=Cl, R3=H, R4=CH3, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-3615-II-3892.
Table 141: in general formula II-A, W=H, R1=CH3, R2=Cl, R3=H, R4=CH3, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-3893-II-4170.
Table 142: in general formula II-A, W=H, R1=C2H5, R2=Cl, R3=H, R4=CH3, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-4171-II-4448.
Table 143: in general formula II-A, W=CH3, R1=CH3, R2=Cl, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-4449-II-4726.
Table 144: in general formula II-A, W=CH3, R1=C2H5, R2=Cl, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-4727-II-5004.
Table 145: in general formula II-A, W=CH3, R1=CH3, R2=R5b=Cl, R3=R4=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-5005-II-5282.
Table 146: in general formula II-A, W=CH3, R1=C2H5, R2=R5b=Cl, R3=R4=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-5283-II-5560.
Table 147: in general formula II-A, W=CH3, R1=CH3, R2=Cl, R3=R4=H, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-5561-II-5838.
Table 148: in general formula II-A, W=CH3, R1=C2H5, R2=Cl, R3=R4=H, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-5839-II-6116.
Table 149: in general formula II-A, W=CH3, R1=CH3, R2=Cl, R3=R4=H, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-6117-II-6394.
Table 150: in general formula II-A, W=CH3, R1=C2H5, R2=Cl, R3=R4=H, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-6395-II-6672.
Table 151: in general formula II-A, W=CH3, R1=CH3, R2=Cl, R3=R5b=H, R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-6673-II-6950.
Table 152: in general formula II-A, W=CH3, R1=C2H5, R2=Cl, R3=R5b=H, R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-6951-II-7228.
Table 153: in general formula II-A, W=CH3, R1=CH3, R2=Cl, R3=H, R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-7229-II-7506.
Table 154: in general formula II-A, W=CH3, R1=C2H5, R2=Cl, R3=H, R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-7507-II-7784.
Table 155: in general formula II-A, W=CH3, R1=CH3, R2=Cl, R3=H, R4=CH3, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-7785-II-8062.
Table 156: in general formula II-A, W=CH3, R1=C2H5, R2=Cl, R3=H, R4=CH3, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-8063-II-8340.
Table 157: in general formula II-A, W=CH3, R1=CH3, R2=Cl, R3=H, R4=CH3, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-8341-II-8618.
Table 158: in general formula II-A, W=CH3, R1=C2H5, R2=Cl, R3=H, R4=CH3, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-8619-II-8896.
Table 159: in general formula II-A, W=H, R1=CHF2, R2=Cl, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-8897-II-9174.
Table 160: in general formula II-A, W=H, R1=CF3, R2=Cl, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-9175-II-9452.
Table 161: in general formula II-A, W=H, R1=CHF2, R2=R5b=Cl, R3=R4=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-9453-II-9730.
Table 162: in general formula II-A, W=H, R1=CF3, R2=R5b=Cl, R3=R4=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-9731-II-10008.
Table 163: in general formula II-A, W=H, R1=CHF2, R2=Cl, R3=R4=H, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-10009-II-10286.
Table 164: in general formula II-A, W=H, R1=CF3, R2=Cl, R3=R4=H, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-10287-II-10564.
Table 165: in general formula II-A, W=H, R1=CHF2, R2=Cl, R3=R4=H, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-10565-II-10842.
Table 166: in general formula II-A, W=H, R1=CF3, R2=Cl, R3=R4=H, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-10843-II-11120.
Table 167: in general formula II-A, W=H, R1=CHF2, R2=Cl, R3=R5b=H, R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-11121-II-11398.
Table 168: in general formula II-A, W=H, R1=CF3, R2=Cl, R3=R5b=H, R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-11399-II-11676.
Table 169: in general formula II-A, W=H, R1=CHF2, R2=Cl, R3=H, R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-11677-II-11954.
Table 170: in general formula II-A, W=H, R1=CF3, R2=Cl, R3=H, R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-11955-II-12232.
Table 171: in general formula II-A, W=H, R1=CHF2, R2=Cl, R3=H, R4=CH3, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-12233-II-12510.
Table 172: in general formula II-A, W=H, R1=CF3, R2=Cl, R3=H, R4=CH3, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-12511-II-12788.
Table 173: in general formula II-A, W=H, R1=CHF2, R2=Cl, R3=H, R4=CH3, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-12789-II-13066.
Table 174: in general formula II-A, W=H, R1=CF3, R2=Cl, R3=H, R4=CH3, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-13067-II-13344.
Table 175: in general formula II-A, W=CH3, R1=CHF2, R2=Cl, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-13345-II-13622.
Table 176: in general formula II-A, W=CH3, R1=CF3, R2=Cl, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-13623-II-13900.
Table 177: in general formula II-A, W=CH3, R1=CHF2, R2=R5b=Cl, R3=R4=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-13901-II-14178.
Table 178: in general formula II-A, W=CH3, R1=CF3, R2=R5b=Cl, R3=R4=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-14179-II-14456.
Table 179: in general formula II-A, W=CH3, R1=CHF2, R2=Cl, R3=R4=H, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-14457-II-14734.
Table 180: in general formula II-A, W=CH3, R1=CF3, R2=Cl, R3=R4=H, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-14735-II-15012.
Table 181: in general formula II-A, W=CH3, R1=CHF2, R2=Cl, R3=R4=H, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-15013-II-15290.
Table 182: in general formula II-A, W=CH3, R1=CF3, R2=Cl, R3=R4=H, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-15291-II-15568.
Table 183: in general formula II-A, W=CH3, R1=CHF2, R2=Cl, R3=R5b=H, R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-15569-II-15846.
Table 184: in general formula II-A, W=CH3, R1=CF3, R2=Cl, R3=R5b=H, R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-15847-II-16124.
Table 185: in general formula II-A, W=CH3, R1=CHF2, R2=Cl, R3=H, R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-16125-II-16402.
Table 186: in general formula II-A, W=CH3, R1=CF3, R2=Cl, R3=H, R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-16403-II-16680.
Table 187: in general formula II-A, W=CH3, R1=CHF2, R2=Cl, R3=H, R4=CH3, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-16681-II-16958.
Table 188: in general formula II-A, W=CH3, R1=CF3, R2=Cl, R3=H, R4=CH3, R5b=Br, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-16959-II-17236.
Table 189: in general formula II-A, W=CH3, R1=CHF2, R2=Cl, R3=H, R4=CH3, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-17237-II-17514.
Table 190: in general formula II-A, W=CH3, R1=C2H5, R2=Cl, R3=H, R4=CH3, R5b=OCH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 127 and corresponding to II-1-II-278 in table 127 in turn, the representative compounds are coded as II-17515-II-17792.




In general formula II-B, R1=CH3, R2=Cl, R7=R8=R10=R11=H, R9=CF3, the substituent R12 refers to Table 191, the representative compounds are coded as II-17793-II-17932.










TABLE 191







No.
R12









II-17793
S-i-C3H7



II-17794
OH



II-17795
—C(═O)H



II-17796
CBr3



II-17797
CH3



II-17798
C2H5



II-17799
n-C3H7



II-17800
i-C3H7



II-17801
n-C4H9



II-17802
i-C4H9



II-17803
t-C4H9



II-17804
CI3



II-17805
CH2Br



II-17806
CHF2



II-17807
CHBr2



II-17808
CF3



II-17809
CH2Cl



II-17810
CHCl2



II-17811
CCl3



II-17812
CH2F



II-17813
OCH3



II-17814
OC2H5



II-17815
OCH(CH3)2



II-17816
OC(CH3)3



II-17817
OCF3



II-17818
OCH2CF3



II-17819
OCH2F



II-17820
OCHF2



II-17821
SCH3



II-17822
SC2H5



II-17823
SCH2CH═CH2



II-17824
CH═CH2



II-17825
CH2CH═CH2



II-17826
CH2CH═CCl2



II-17827
C≡CH



II-17828
CH2C≡CH



II-17829
CH2C≡C—I



II-17830
CH2OCH3



II-17831
CH2OCH2CH3



II-17832
CH2CH2OCH3



II-17833
CH2CH2OCH2CH3



II-17834
CH2OCH2Cl



II-17835
CH2OCH2CH2Cl



II-17836
CH2CH2OCH2Cl



II-17837
CH2SCH3



II-17838
CH2SCH2CH3



II-17839
CH2CH2SCH3



II-17840
CH2CH2SCH2CH3



II-17841
CH2SCH2Cl



II-17842
CH2SCH2CH2Cl



II-17843
CH2CH2SCH2Cl



II-17844
SOCH3



II-17845
SOC2H5



II-17846
SOCF3



II-17847
SOCH2CF3



II-17848
SO2CH3



II-17849
SO2C2H5



II-17850
SO2CF3



II-17851
SO2CH2CF3



II-17852
SO2NHCOCH3



II-17853
SO2NHCH3



II-17854
SO2N(CH3)3



II-17855
CONHSO2CH3



II-17856
COCH3



II-17857
COC2H5



II-17858
CO—n-C3H7



II-17859
CO—i-C3H7



II-17860
CO—n-C4H9



II-17861
CO—i-C4H9



II-17862
CO—t-C4H9



II-17863
COCF3



II-17864
COCH2Cl



II-17865
COOCH3



II-17866
COOC2H5



II-17867
COO—n-C3H7



II-17868
COO—t-C4H9



II-17869
COOCF3



II-17870
COOCH2CH2Cl



II-17871
COOCH2CF3



II-17872
CH2COOCH3



II-17873
CH2COOC2H5



II-17874
CH2COCH3



II-17875
CH2COC2H5



II-17876
CONHCH3



II-17877
CONHC2H5



II-17878
CONH—t-C4H9



II-17879
CON(CH3)2



II-17880
CON(C2H5)2



II-17881
COOCH2CH═CH2



II-17882
COOCH2C≡CH



II-17883
COOCH2OCH3



II-17884
COOCH2CH2OCH3



II-17885
SNHCH3



II-17886
SNHC2H5



II-17887
SN(CH3)2



II-17888
SN(C2H5)2



 



II-17889







 



II-17890







 



II-17891







 



II-17892







 



II-17893







 



II-17894







 



II-17895







 



II-17896







 



II-17897







 



II-17898







 



II-17899







 



II-17900







 



II-17901







 



II-17902







 



II-17903







 



II-17904







 



II-17905







 



II-17906







 



II-17907







 



II-17908







 



II-17909







 



II-17910







 



II-17911







 



II-17912







 



II-17913







 



II-17914







 



II-17915







 



II-17916







 



II-17917







 



II-17918







 



II-17919







 



II-17920







 



II-17921







 



II-17922







 



II-17923







 



II-17924







 



II-17925







 



II-17926







 



II-17927







 



II-17928







 



II-17929







 



II-17930







 



II-17931







 



II-17932














Table 192: in general formula II-B, R1=C2H5, R2=Cl, R7=R8=R10=R11=H, R9=CF3, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-17933-II-18072.
Table 193: in general formula II-B, R1=CH3, R2=R9=Cl, R7=R8=R10=R11=H, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-18073-II-18212.
Table 194: in general formula II-B, R1=C2H5, R2=R9=Cl, R7=R8=R10=R1=H, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-18213-II-18352.
Table 195: in general formula II-B, R1=CH3, R2=R7=R9=Cl, R8=R10=R11=H, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-18353-II-18492.
Table 196: in general formula II-B, R1=C2H5, R2=R7=R9=Cl, R8=R10=R11=H, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-18493-II-18632.
Table 197: in general formula II-B, R1=CH3, R2=R7=R11=Cl, R8=R10=H, R9=NO2, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-18633-II-18772.
Table 198: in general formula II-B, R1=C2H5, R2=R7=R1=Cl, R8=R10=H, R9=NO2, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-18773-II-18912.
Table 199: in general formula II-B, R1=CHF2, R2=R9=Cl, R7=R8=R10=R11=H, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-18913-II-19052.
Table 200: in general formula II-B, R1=CHF2, R2=Cl, R7=R8=R10=R11=H, R9=CF3, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-19053-II-19192.
Table 201: in general formula II-B, R1=CHF2, R2=R7=R9=Cl, R8=R10=R11=H, the substituent R12 are consistent with those in Table 191 and corresponding to II-17793-II-17932 in table 191 in turn, the representative compounds are coded as II-19193-II-19332.
The salts of some compounds having a structure as represented by formula II of the present invention are listed in Table 202, but without being restricted thereby.







TABLE 202







the salts of some compounds








No.
structure





II-19333






 


II-19334






 


II-19335






 


II-19336






 


II-19337






 


II-19338






 


II-19339






 


II-19340






 


II-19341






 


II-19342






 


II-19343






 


II-19344






 


II-19345






 


II-19346






 


II-19347






 


II-19348






 


II-19349






 


II-19350






 


II-19351






 


II-19352






 


II-19353






 


II-19354






 


II-19355






 


II-19356






 


II-19357






 


II-19358






 


II-19359






 


II-19360






 


II-19361






 


II-19362






 


II-19363






 


II-19364






 


II-19365






 


II-19366






 


II-19367






 


II-19368






 


II-19369






 


II-19370






 


II-19371






 


II-19372






 


II-19373






 


II-19374






 


II-19375






 


II-19376






 


II-19377






 


II-19378






 


II-19379






 


II-19380






 


II-19381






 


II-19382






 


II-19383






 


II-19384






 


II-19385






 


II-19386






 


II-19387






 


II-19388






 


II-19389






 


II-19390






 


II-19391






 


II-19392






 


II-19393






 


II-19394






 


II-19395






 


II-19396






 


II-19397






 


II-19398






 


II-19399






 


II-19400






 


II-19401






 


II-19402






 


II-19403






 


II-19404






 


II-19405






 


II-19406






 


II-19407






 


II-19408






 


II-19409






 


II-19410






 


II-19411






 


II-19412






 


II-19413






 


II-19414






 


II-19415






 


II-19416






 


II-19417






 


II-19418






 


II-19419






 


II-19420






 


II-19421






 


II-19422






 


II-19423






 


II-19424






 


II-19425






 


II-19426






 


II-19427






 


II-19428






 


II-19429






 


II-19430






 


II-19431






 


II-19432






 


II-19433






 


II-19434






 


II-19435






 


II-19436













In the general formula III, part of preferred substituents of R1, R2, W, R3 and R4 are separately listed in table 203 to table 206, but without being restricted thereby. The definitions of other substituents are defined as above.







TABLE 203





R1 substituents


R1







H


F


Cl


Br


I


CH3


C2H5


n-C3H7


i-C3H7


n-C4H9


i-C4H9


t-C4H9


 








 








 








 


CH2Cl


CHCl2


CH2CH═CH2


CCl3


CHF2


CHBr2


CF3


CH(CH3)F


CH(CH3)Cl


CH(CH3)Br


C(CH3)2F


OCH3


OC2H5


OCF3


OCH2CH═CH2


OCH2CH═CHCl


OCH2C≡CH


OCH2C≡C—I


OCH2C≡CCH3


OSO2CH3


CH2C≡CH


SCH3


SOCH3


SO2CH3


COOH


COOCH3


COOC2H5


CONH2


CONHCH3


CONHCN


CONHCH2CN


CON(CH3)2


NH2


NHCH3


NHC2H5


N(CH3)2


N(C2H5)2


NHCH2CN


CH2OCH2Cl


NHOCH3


NHOC2H5


NHCOCH3


NHCOC2H5


NHCOOCH3


NHCOOC2H5


N(CH3)NH2


NHN(CH3)2


CH2OCH3


CH2OCH2CH3


CH2CH2OCH3


CH2CH2OCH2CH3


CH(CH3)SCH3


CH(CH3)SOCH3


CH(CH3)SO2CH3


CH(CH3)OH


CH(CH3)OCOCH3


CH2OCH2CH2Cl
















TABLE 204







R2 substituents












R2
R2
R2
R2







H
NO2
t-C4H9
OC4H9-i



F
CH3
OCH3
OC4H9-t



Cl
C2H5
OC2H5
OCH2F



Br
n-C3H7
OC3H7-n
OCHF2



I
i-C3H7
OC3H7-i
OCF3



CN
n-C4H9
OC4H9-n
OCH2CF3

















TABLE 205





W substituents


W







H


F


Cl


Br


I


CH3


C2H5


n-C3H7


i-C3H7


n-C4H9


t-C4H9


 








 








 








 


CHCl2


CCl3


CHF2


CHBr2


CF3


CH(CH3)F


CH(CH3)Cl


CH(CH3)Br


CH(n-C4H9)F


C(CH3)2F


OCH3


OC2H5


OC3H7-n


OC3H7-i


OC4H9-n


OC4H9-i


OC4H9-t


OCF3


OCH2CF3


SCH3


SC2H5


SC3H7-n


SC3H7-i


SC4H9-n


SC4H9-i


SC4H9-t
















TABLE 206





R3(R4)substituents







R3(R4)





H


CH3


C2H5


n-C3H7


i-C3H7


n-C4H9


i-C4H9


 








 








 








 


t-C4H9


CH═CH2


C≡CH


CH2CH═CH2


CH2C≡CH


CH2CH═CCl2


CH2C≡C—I


CH2OCH3


CH2OCH2CH3


CH2CH2OCH3


CH2CH2OCH2CH3


 








 








 








 








 








 











CR3R4











 








 








 















The present invention is also explained by the following compounds having a structure as represented by formula III listed in Table 207 to Table 304, but without being restricted thereby. The compounds having a structure as represented by formula III-A, III-B, III-C, III-D, III-E, III-F, III-G and III-H refer to Table 207 to Table 304, R5a=R5c=H.
In general formula III-A,




A=NH, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 refer to Table 207, the representative compounds are coded as III-1-III-180.












TABLE 207





No.
R7
R8
R9
R10
R11







III-1
H
H
H
H
H


III-2
F
H
H
H
H


III-3
H
F
H
H
H


III-4
H
H
F
H
H


III-5
Cl
H
H
H
H


III-6
H
Cl
H
H
H


III-7
H
H
Cl
H
H


III-8
Br
H
H
H
H


III-9
H
Br
H
H
H


III-10
H
H
Br
H
H


III-11
I
H
H
H
H


III-12
H
I
H
H
H


III-13
H
H
I
H
H


III-14
CH3
H
H
H
H


III-15
H
CH3
H
H
H


III-16
H
H
CH3
H
H


III-17
OCH3
H
H
H
H


III-18
H
OCH3
H
H
H


III-19
H
H
OCH3
H
H


III-20
CF3
H
H
H
H


III-21
H
CF3
H
H
H


III-22
H
H
CF3
H
H


III-23
OCF3
H
H
H
H


III-24
H
OCF3
H
H
H


III-25
H
H
OCF3
H
H


III-26
NO2
H
H
H
H


III-27
H
NO2
H
H
H


III-28
H
H
NO2
H
H


III-29
CN
H
H
H
H


III-30
H
CN
H
H
H


III-31
H
H
CN
H
H


III-32
CH(CH3)2
H
H
H
H


III-33
H
CH(CH3)2
H
H
H


III-34
H
H
CH(CH3)2
H
H


III-35
H
H
t-Bu
H
H


III-36
SCH3
H
H
H
H


III-37
H
SCH3
H
H
H


III-38
H
H
SCH3
H
H


III-39
SCF3
H
H
H
H


III-40
H
SCF3
H
H
H


III-41
H
H
SCF3
H
H


III-42
COCH3
H
H
H
H


III-43
H
COCH3
H
H
H


III-44
H
H
COCH3
H
H


III-45
SOCH3
H
H
H
H


III-46
H
SOCH3
H
H
H


III-47
H
H
SOCH3
H
H


III-48
SO2CH3
H
H
H
H


III-49
H
SO2CH3
H
H
H


III-50
H
H
SO2CH3
H
H


III-51
OCHF2
H
H
H
H


III-52
H
OCHF2
H
H
H


III-53
H
H
OCHF2
H
H


III-54
CO2CH3
H
H
H
H


III-55
H
CO2CH3
H
H
H


III-56
H
H
CO2CH3
H
H


III-57
N(CH3)2
H
H
H
H


III-58
H
N(CH3)2
H
H
H


III-59
H
H
N(CH3)2
H
H


III-60
N(C2H5)2
H
H
H
H


III-61
H
N(C2H5)2
H
H
H


III-62
H
H
N(C2H5)2
H
H


III-63
NHCOCH3
H
H
H
H


III-64
H
NHCOCH3
H
H
H


III-65
H
H
NHCOCH3
H
H


III-66
NHSO2CH3
H
H
H
H


III-67
H
NHSO2CH3
H
H
H


III-68
H
H
NHSO2CH3
H
H


III-69
OCH2CH═CH2
H
H
H
H


III-70
H
OCH2CH═CH2
H
H
H


III-71
H
H
OCH2CH═CH2
H
H


III-72
OCH2C≡CH
H
H
H
H


III-73
H
OCH2C≡CH
H
H
H


III-74
H
H
OCH2C≡CH
H
H


III-75
F
F
H
H
H


III-76
F
H
F
H
H


III-77
F
H
H
F
H


III-78
F
H
H
H
F


III-79
H
F
F
H
H


III-80
H
F
H
F
H


III-81
Cl
Cl
H
H
H


III-82
Cl
H
Cl
H
H


III-83
Cl
H
H
Cl
H


III-84
Cl
H
H
H
Cl


III-85
H
Cl
Cl
H
H


III-86
H
Cl
H
Cl
H


III-87
NO2
H
NO2
H
H


III-88
NO2
H
H
NO2
H


III-89
NO2
H
H
H
NO2


III-90
H
NO2
H
NO2
H


III-91
CN
H
CN
H
H


III-92
CN
H
H
CN
H


III-93
CN
H
H
H
CN


III-94
H
CN
H
CN
H


III-95
CH3
CH3
H
H
H


III-96
CH3
H
CH3
H
H


III-97
CH3
H
H
CH3
H


III-98
CH3
H
H
H
CH3


III-99
H
CH3
CH3
H
H


III-100
H
CH3
H
CH3
H


III-101
CF3
H
CF3
H
H


III-102
CF3
H
H
CF3
H


III-103
CF3
H
H
H
CF3


III-104
H
CF3
H
CF3
H


III-105
OCF3
H
OCF3
H
H


III-106
OCF3
H
H
OCF3
H


III-107
OCF3
H
H
H
OCF3


III-108
H
OCF3
H
OCF3
H


III-109
CH3
Cl
H
H
H


III-110
CH3
H
Cl
H
H


III-111
H
Cl
CH3
H
H


III-112
Cl
H
CH3
H
H


III-113
CH3
H
H
Cl
H


III-114
CH3
H
H
H
Cl


III-115
Br
CH3
H
H
H


III-116
H
CH3
Cl
H
H


III-117
CH3
NO2
H
H
H


III-118
CH3
H
NO2
H
H


III-119
CH3
H
OCH3
H
H


III-120
CH3
H
H
NO2
H


III-121
Cl
H
CF3
H
H


III-122
Cl
H
H
CF3
H


III-123
Cl
H
NO2
H
H


III-124
Cl
H
H
NO2
H


III-125
CF3
H
Br
H
H


III-126
CF3
H
NO2
H
H


III-127
H
CF3
NO2
H
H


III-128
H
CF3
Cl
H
H


III-129
CF3
H
CN
H
H


III-130
Cl
H
CN
H
H


III-131
NO2
H
CN
H
H


III-132
NO2
H
CH3
H
H


III-133
NO2
H
CF3
H
H


III-134
NO2
H
Cl
H
H


III-135
NO2
H
H
Cl
H


III-136
H
NO2
CH3
H
H


III-137
H
NO2
Cl
H
H


III-138
CN
F
H
H
H


III-139
CN
H
NO2
H
H


III-140
CN
H
Cl
H
H


III-141
CN
H
H
CH3
H


III-142
Cl
Cl
Cl
H
H


III-143
Cl
Cl
H
Cl
H


III-144
Cl
H
Cl
Cl
H


III-145
Cl
H
Cl
H
Cl


III-146
H
Cl
Cl
Cl
H


III-147
CH3
H
CH3
H
CH3


III-148
OCH3
H
OCH3
H
OCH3


III-149
Cl
Cl
Br
H
H


III-150
F
H
F
H
Cl


III-151
CH3
H
Br
H
Br


III-152
CF3
H
Cl
H
Cl


III-153
CF3
H
Br
H
Br


III-154
F
H
Cl
H
Br


III-155
Cl
H
NO2
H
Cl


III-156
Br
H
NO2
H
Br


III-157
Cl
H
CN
H
Cl


III-158
Cl
H
CF3
H
Cl


III-159
Br
H
CF3
H
Br


III-160
Cl
CH3
H
H
Cl


III-161
Cl
H
CONH2
H
Cl


III-162
Cl
H
CO2CH3
H
Cl


III-163
Cl
H
NHCOCH3
H
Cl


III-164
Cl
H
OCF3
H
Cl


III-165
Br
H
F
H
Br


III-166
Br
H
CH3
H
Br


III-167
Cl
H
COCH3
H
Cl


III-168
Cl
H
NO2
Cl
H


III-169
F
H
F
H
Cl


III-170
Cl
H
CF3
H
Br


III-171
CH3
H
NO2
H
Cl


III-172
CH3
H
NO2
H
Br


III-173
CH3
H
Cl
H
NO2


III-174
CH3
H
Br
H
NO2


III-175
NO2
H
CF3
H
Cl


III-176
NO2
H
CF3
H
Br


III-177
F
H
Br
H
Br


III-178
CN
H
Cl
H
Cl


III-179
CN
H
Br
H
Br


III-180
F
H
CN
H
H









Table 208: A=NH, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-181-III-360.
Table 209: A=NH, R1=CF3, R2=Cl, W=R3=R4=R5b=H, the s substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-361-III-540.
Table 210: A=NH, R1=CHF2, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-541-III-720.
Table 211: A=NH, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-721-III-900.
Table 212: A=NH, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-901-III-1080.
Table 213: A=NH, R1=CF3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-1081-III-1260.
Table 214: A=NH, R1=CHF2, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-1261-III-1440.
Table 215: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-1441-III-1620.
Table 216: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-1621-III-1800.
Table 217: A=NH, R1=CF3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-1801-III-1980.
Table 218: A=NH, R1=CHF2, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-1981-III-2160.
Table 219: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-2161-III-2340.
Table 220: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-2341-III-2520.
Table 221: A=NH, R1=Cl, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-2521-III-2700.
Table 222: A=NH, R1=CHF2, R2=Cl, W=CH3, R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-2701-III-2880.
Table 223: A=NH, R1=CH3, R2=Cl, W=R4=R5b=H, R3=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-2881-III-3060.
Table 224: A=NH, R1=C2H5, R2=Cl, W=R4=R5b=H, R3=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-3061-III-3240.
Table 225: A=NH, R1=CH3, R2=Cl, W=R4=H, R3=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-3241-III-3420.
Table 226: A=NH, R1=C2H5, R2=Cl, W=R4=H, R3=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-3421-III-3600.
Table 227: A=NH, R1=CH3, R2=Cl, W=R5b=H, R3=R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-3601-III-3780.
Table 228: A=NH, R1=C2H5, R2=Cl, W=R5b=H, R3=R4=CH3, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-3781-III-3960.
Table 229: A=NH, R1=CH3, R2=Cl, W=H, R3=R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-3961-III-4140.
Table 230: A=NH, R1=C2H5, R2=Cl, W=H, R3=R4=CH3, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-4141-III-4320.
Table 231: A=O, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-4321-III-4500.
Table 232: A=O, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-4501-III-4680.
Table 233: A=O, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-4681-III-4860.
Table 234: A=O, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-4861-III-5040.
Table 235: A=S, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-5041-III-5220.
Table 236: A=S, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-5221-III-5400.
Table 237: A=S, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-5401-III-5580.
Table 238: A=S, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R9, R10 and R11 are consistent with those in Table 207 and corresponding to III-1-III-180 in table 207 in turn, the representative compounds are coded as III-5581-III-5760.
In general formula III-B,




A=NH, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 refer to Table 239, the representative compounds are coded as III-5761-III-5802.













TABLE 239







No.
R8
R9
R10
R11









III-5761
H
H
H
H



III-5762
H
H
H
F



III-5763
H
H
H
Cl



III-5764
H
H
H
Br



III-5765
H
H
Cl
H



III-5766
H
Cl
H
H



III-5767
H
Br
H
H



III-5768
Cl
H
H
H



III-5769
H
H
H
NO2



III-5770
H
H
NO2
H



III-5771
H
NO2
H
H



III-5772
H
CN
H
H



III-5773
H
OCF3
H
H



III-5774
H
H
H
CH3



III-5775
H
H
CH3
H



III-5776
H
CH3
H
H



III-5777
CH3
H
H
H



III-5778
H
H
H
CF3



III-5779
H
H
CF3
H



III-5780
H
CF3
H
H



III-5781
H
H
H
OCH3



III-5782
H
H
OCH3
H



III-5783
H
OCH3
H
H



III-5784
OCH3
H
H
H



III-5785
H
Cl
H
Cl



III-5786
Cl
H
Cl
H



III-5787
H
NO2
H
Cl



III-5788
H
CN
H
Cl



III-5789
H
CF3
H
Cl



III-5790
H
NO2
H
Br



III-5791
H
H
Cl
NO2



III-5792
H
Cl
H
NO2



III-5793
H
CN
H
CH3



III-5794
H
Br
CH3
H



III-5795
H
NO2
CH3
H



III-5796
CH3
H
CH3
H



III-5797
H
Cl
H
CF3



III-5798
Cl
H
H
CF3



III-5799
CH3
Cl
CH3
Cl



III-5800
Cl
Cl
H
Cl



III-5801
Cl
CF3
H
Br



III-5802
H
Br
CH3
Br










Table 240: A=NH, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-5803-III-5844.
Table 241: A=NH, R1=CF3, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-5845-III-5886.
Table 242: A=NH, R1=CHF2, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-5887-III-5928.
Table 243: A=NH, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-5929-III-5970.
Table 244: A=NH, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-5971-III-6012.
Table 245: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-6013-III-6054.
Table 246: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-6055-III-6096.
Table 247: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-6097-III-6138.
Table 248: A=O, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-6139-III-6180.
Table 249: A=S, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-6181-III-6222.
Table 250: A=S, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 239 and corresponding to III-5761-III-5802 in table 239 in turn, the representative compounds are coded as III-6223-III-6264.
In general formula III-C,




A=NH, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R9, R10 and R11 refer to Table 251, the representative compounds are coded as III-6265-III-6282.













TABLE 251







No.
R7
R9
R10
R11









III-6265
H
H
H
H



III-6266
Cl
H
H
H



III-6267
OCH3
H
H
H



III-6268
OCH2CF3
H
H
H



III-6269
H
H
H
CH3



III-6270
H
H
H
CF3



III-6271
H
Br
H
H



III-6272
H
CF3
H
H



III-6273
H
OCH3
H
H



III-6274
Cl
H
Cl
H



III-6275
Cl
Cl
H
H



III-6276
H
Cl
Cl
H



III-6277
Cl
H
H
CH3



III-6278
Cl
H
CH3
H



III-6279
Cl
CH3
H
H



III-6280
Cl
Cl
H
CF3



III-6281
H
NHCH3
Cl
H



III-6282
H
SO2CH3
Cl
H










Table 252: A=NH, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R9, R10 and R11 are consistent with those in Table 251 and corresponding to III-6265-III-6282 in table 251 in turn, the representative compounds are coded as III-6283-III-6300.
Table 253: A=NH, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R9, R10 and R11 are consistent with those in Table 251 and corresponding to III-6265-III-6282 in table 251 in turn, the representative compounds are coded as III-6301-III-6318.
Table 254: A=NH, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R9, R10 and R11 are consistent with those in Table 251 and corresponding to III-6265-III-6282 in table 251 in turn, the representative compounds are coded as III-6319-III-6336.
Table 255: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R9, R10 and R11 are consistent with those in Table 251 and corresponding to III-6265-III-6282 in table 251 in turn, the representative compounds are coded as III-6337-III-6354.
Table 256: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R9, R10 and R11 are consistent with those in Table 251 and corresponding to III-6265-III-6282 in table 251 in turn, the representative compounds are coded as III-6355-III-6372.
In general formula III-D,




A=NH, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R10 and R11 refer to Table 257, the representative compounds are coded as III-6373-III-6380.













TABLE 257







No.
R7
R8
R10
R11









III-6373
H
H
Cl
H



III-6374
H
H
H
Br



III-6375
Cl
H
H
Cl



III-6376
H
H
OCH3
H



III-6377
H
OCH3
OCH3
H



III-6378
H
Cl
OCH3
H



III-6379
H
Cl
NHCH3
H



III-6380
Cl
Cl
Cl
Cl










Table 258: A=NH, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R8, R10 and R11 are consistent with those in Table 257 and corresponding to III-6373-III-6380 in table 257 in turn, the representative compounds are coded as III-6381-III-6388.
Table 259: A=NH, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R10 and R11 are consistent with those in Table 257 and corresponding to III-6373-III-6380 in table 257 in turn, the representative compounds are coded as III-6389-III-6396.
Table 260: A=NH, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R8, R10 and R11 are consistent with those in Table 257 and corresponding to III-6373-III-6380 in table 257 in turn, the representative compounds are coded as III-6397-III-6404.
Table 261: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R8, R10 and R11 are consistent with those in Table 257 and corresponding to III-6373-III-6380 in table 257 in turn, the representative compounds are coded as III-6405-III-6412.
Table 262: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R8, R10 and R11 are consistent with those in Table 257 and corresponding to III-6373-III-6380 in table 257 in turn, the representative compounds are coded as III-6413-III-6420.
In general formula III-E,




A=NH, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 refer to Table 263, the representative compounds are coded as III-6421-III-6424.












TABLE 263







No.
R8
R9
R10









III-6421
H
H
H



III-6422
CH3
H
CH3



III-6423
OCH3
H
OCH3



III-6424
CO2C2H5
H
CF3










Table 264: A=NH, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 263 and corresponding to III-6421-III-6424 in table 263 in turn, the representative compounds are coded as III-6425-III-6428.
Table 265: A=NH, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R8, R9, R10 and R11 are consistent with those in Table 263 and corresponding to III-6421-III-6424 in table 263 in turn, the representative compounds are coded as III-6429-III-6432.
Table 266: A=NH, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R8, R9, R10 and R11 are consistent with those in Table 263 and corresponding to III-6421-III-6424 in table 263 in turn, the representative compounds are coded as III-6433-III-6436.
Table 267: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 263 and corresponding to III-6421-III-6424 in table 263 in turn, the representative compounds are coded as III-6437-III-6440.
Table 268: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R8, R9, R10 and R11 are consistent with those in Table 263 and corresponding to III-6421-III-6424 in table 263 in turn, the representative compounds are coded as III-6441-III-6444.
In general formula III-F,




A=NH, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R10 and R refer to Table 269, the representative compounds are coded as III-6445-III-6448.












TABLE 269







No.
R8
R10
R11









III-6445
H
H
H



III-6446
H
Cl
H



III-6447
CH3
Cl
H



III-6448
H
Cl
Cl










Table 270: A=NH, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R8, R10 and R11 are consistent with those in Table 269 and corresponding to III-6445-III-6448 in table 269 in turn, the representative compounds are coded as III-6449-III-6452.
Table 271: A=NH, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R8, R10 and R11 are consistent with those in Table 269 and corresponding to III-6445-III-6448 in table 269 in turn, the representative compounds are coded as III-6453-III-6456.
Table 272: A=NH, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R8, R10 and R11 are consistent with those in Table 269 and corresponding to III-6445-III-6448 in table 269 in turn, the representative compounds are coded as III-6457-III-6460.
Table 273: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R8, R10 and R11 are consistent with those in Table 269 and corresponding to III-6445-III-6448 in table 269 in turn, the representative compounds are coded as III-6461-III-6464.
Table 274: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R8, R10 and R11 are consistent with those in Table 269 and corresponding to III-6445-III-6448 in table 269 in turn, the representative compounds are coded as III-6465-III-6468.
In general formula III-G,




A=NH, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R9 and R10 refer to Table 275, the representative compounds are coded as III-6469-III-6470.












TABLE 275







No.
R7
R9
R10









III-6469
H
H
H



III-6470
H
H
Cl










Table 276: A=NH, R1=C2H5, R2=Cl, W=R3=R4=R5b=H, the substituents R7, R9 and R10 are consistent with those in Table 275 and corresponding to III-6469-III-6470 in table 275 in turn, the representative compounds are coded as III-6471-III-6472.
Table 277: A=NH, R1=CH3, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R9 and R10 are consistent with those in Table 275 and corresponding to III-6469-III-6470 in table 275 in turn, the representative compounds are coded as III-6473-III-6474.
Table 278: A=NH, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R7, R9 and R10 are consistent with those in Table 275 and corresponding to III-6469-III-6470 in table 275 in turn, the representative compounds are coded as III-6475-III-6476.
Table 279: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R9 and R10 are consistent with those in Table 275 and corresponding to III-6469-III-6470 in table 275 in turn, the representative compounds are coded as III-6477-III-6478.
Table 280: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R7, R9 and R10 are consistent with those in Table 275 and corresponding to III-6469-III-6470 in table 275 in turn, the representative compounds are coded as III-6479-III-6480.
In general formula III-H,




A=NH, R1=CH3, R2=Cl, W=R3=R4=R5b=H, the substituents R9, R10 and R refer to Table 281, the representative compounds are coded as III-6481-III-6482.












TABLE 281







No.
R9
R10
R11









III-6481
H
H
H



III-6482
Cl
H
H










Table 284: A=NH, R1=C2H5, R2=Cl, W=R3=R4=H, R5b=Cl, the substituents R9, R10 and R11 are consistent with those in Table 281 and corresponding to III-6481-III-6482 in table 281 in turn, the representative compounds are coded as III-6487-III-6488.
Table 285: A=NH, R1=CH3, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R9, R10 and R11 are consistent with those in Table 281 and corresponding to III-6481-III-6482 in table 281 in turn, the representative compounds are coded as III-6489-III-6490
Table 286: A=NH, R1=C2H5, R2=Cl, W=CH3, R3=R4=R5b=H, the substituents R9, R10 and R11 are consistent with those in Table 281 and corresponding to III-6481-III-6482 in table 281 in turn, the representative compounds are coded as III-6491-III-6492.
In general formula III-A, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R7=R8=R10=R11=H, R9=Cl, the substituents R12 refer to Table 287, the representative compounds are coded as III-6493-III-6632.










TABLE 287







No.
R12









III-6493
S—i-C3H7



III-6494
OH



III-6495
—C(═O)H



III-6496
CBr3



III-6497
CH3



III-6498
C2H5



III-6499
n-C3H7



III-6500
i-C3H7



III-6501
n-C4H9



III-6502
i-C4H9



III-6503
t-C4H9



III-6504
CI3



III-6505
CH2Br



III-6506
CHF2



III-6507
CHBr2



III-6508
CF3



III-6509
CH2Cl



III-6510
CHCl2



III-6511
CCl3



III-6512
CH2F



III-6513
OCH3



III-6514
OC2H5



III-6515
OCH(CH3)2



III-6516
OC(CH3)3



III-6517
OCF3



III-6518
OCH2CF3



III-6519
OCH2F



III-6520
OCHF2



III-6521
SCH3



III-6522
SC2H5



III-6523
SCH2CH═CH2



III-6524
CH═CH2



III-6525
CH2CH═CH2



III-6526
CH2CH═CCl2



III-6527
C≡CH



III-6528
CH2C≡CH



III-6529
CH2C≡C—I



III-6530
CH2OCH3



III-6531
CH2OCH2CH3



III-6532
CH2CH2OCH3



III-6533
CH2CH2OCH2CH3



III-6534
CH2OCH2Cl



III-6535
CH2OCH2CH2Cl



III-6536
CH2CH2OCH2Cl



III-6537
CH2SCH3



III-6538
CH2SCH2CH3



III-6539
CH2CH2SCH3



III-6540
CH2CH2SCH2CH3



III-6541
CH2SCH2Cl



III-6542
CH2SCH2CH2Cl



III-6543
CH2CH2SCH2Cl



III-6544
SOCH3



III-6545
SOC2H5



III-6546
SOCF3



III-6547
SOCH2CF3



III-6548
SO2CH3



III-6549
SO2C2H5



III-6550
SO2CF3



III-6551
SO2CH2CF3



III-6552
SO2NHCOCH3



III-6553
SO2NHCH3



III-6554
SO2N(CH3)3



III-6555
CONHSO2CH3



III-6556
COCH3



III-6557
COC2H5



III-6558
CO—n-C3H7



III-6559
CO—i-C3H7



III-6560
CO—n-C4H9



III-6561
CO—i-C4H9



III-6562
CO—t-C4H9



III-6563
COCF3



III-6564
COCH2Cl



III-6565
COOCH3



III-6566
COOC2H5



III-6567
COO—n-C3H7



III-6568
COO—t-C4H9



III-6569
COOCF3



III-6570
COOCH2CH2Cl



III-6571
COOCH2CF3



III-6572
CH2COOCH3



III-6573
CH2COOC2H5



III-6574
CH2COCH3



III-6575
CH2COC2H5



III-6576
CONHCH3



III-6577
CONHC2H5



III-6578
CONH—t-C4H9



III-6579
CON(CH3)2



III-6580
CON(C2H5)2



III-6581
COOCH2CH═CH2



III-6582
COOCH2C≡CH



III-6583
COOCH2OCH3



III-6584
COOCH2CH2OCH3



III-6585
SNHCH3



III-6586
SNHC2H5



III-6587
SN(CH3)2



III-6588
SN(C2H5)2



 



III-6589







 



III-6590







 



III-6591







 



III-6592







 



III-6593







 



III-6594







 



III-6595







 



III-6596







 



III-6597







 



III-6598







 



III-6599







 



III-6600







 



III-6601







 



III-6602







 



III-6603







 



III-6604







 



III-6605







 



III-6606







 



III-6607







 



III-6608







 



III-6609







 



III-6610







 



III-6611







 



III-6612







 



III-6613







 



III-6614







 



III-6615







 



III-6616







 



III-6617







 



III-6618







 



III-6619







 



III-6620







 



III-6621







 



III-6622







 



III-6623







 



III-6624







 



III-6625







 



III-6626







 



III-6627







 



III-6628







 



III-6629







 



III-6630







 



III-6631







 



III-6632














Table 288: in general formula III-A, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R8=R10=R11=H, R7=R9=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-6633-III-6772.
Table 289: in general formula Ill-A, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R7=R8==R10=R11=H, R9=CF3, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-6773-III-6912.
Table 290: in general formula III-B, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R8=R10=R11=H, R9=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-6913-III-7052.
Table 291: in general formula III-B, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R8=R10=R11=H, R9=CF3, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-7053-III-7192.
Table 292: in general formula III-B, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R8=R10=H, R9=CF3, R11=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-7193-III-7332.
Table 293: in general formula III-B, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R8=R10=H, R9=R11=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-7333-III-7472.
Table 294: in general formula III-C, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R9=R10=R11=H, R7=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-7473-III-7612.
Table 295: in general formula III-D, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R7=R11=H, R8=R10=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-7613-III-7752.
Table 296: in general formula III-E, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R9=H, R8=R10=OCH3, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-7753-III-7892.
Table 297: in general formula III-E, A=NR12, R1=C2H5, R2=Cl, W=R3=R4=R5b=R9=H, R8=R10=CH3, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-7893-III-8032.
Table 298: in general formula III-F, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R8=H, R10=CH3, R11=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-8033-III-8172.
Table 299: in general formula III-G, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R7=R9=H, R10=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-8173-III-83122.
Table 300: in general formula Ill-H, A=NR12, R1=CH3, R2=Cl, W=R3=R4=R5b=R10=R11=H, R7=Cl, the substituent R12 are consistent with those in Table 287 and corresponding to III-6493-III-6632 in table 287 in turn, the representative compounds are coded as III-8313-III-8452.
The salts of some compounds having a structure as represented by formula III of the present invention are listed in Table 301, but without being restricted thereby.







TABLE 301







the salts of some compounds








No.
structure





III-8453






 


III-8454






 


III-8455






 


III-8456






 


III-8457






 


III-8458






 


III-8459






 


III-8460






 


III-8461






 


III-8462






 


III-8463






 


III-8464






 


III-8465






 


III-8466






 


III-8467






 


III-8468






 


III-8469






 


III-8470






 


III-8471






 


III-8472






 


III-8473






 


III-8474






 


III-8475






 


III-8476






 


III-8477






 


III-8478






 


III-8479






 


III-8480






 


III-8481






 


III-8482






 


III-8483






 


III-8484






 


III-8485






 


III-8486






 


III-8487






 


III-8488






 


III-8489






 


III-8490






 


III-8491






 


III-8492






 


III-8493






 


III-8494






 


III-8495






 


III-8496













The compounds represented by general formula PY of the invention can be prepared according to three schemes in which Substituent A can be defined as different substituents, the definitions of each substituent is defined as above:
Scheme 1 to prepare the compounds represented by general formula PY: when A=NH, the compounds represented by general formula PY-1 can be prepared according to the following two schemes.
Method 1: the compounds represented by general formula PY-1 can be prepared by reaction of intermediates i and ii in the presence of proper base, the preparation methods are shown as follows.




The reaction was carried out in proper solvent and the proper solvent mentioned may be selected from benzene, toluene, xylene, acetone, butanone, methylisobutylketone, tetrahydrofuran, acetonitrile, 1,4-dioxane, DMF, N-methyl pyrrolidone, DMSO, pyridine, dichloromethane, chloroform, dichloroethane, methyl acetate or ethyl acetate and so on.
The reaction above can be carried out in the presence or absence of base, the reaction is promoted in the presence of base. Proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali metal carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine.
The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20 to 100° C.
The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours.
The detailed operation refers to the methods described in EP0370704, EP0356158, EP0264217, EP0665225, JP10036355 or U.S. Pat. No. 4,985,426.
Intermediates I are commercially available, or prepared according to the methods described in JP2000007662, U.S. Pat. No. 4,977,264, U.S. Pat. No. 6,090,815, US20040092402, JP09124613, U.S. Pat. No. 5,468,751, U.S. Pat. No. 4,985,426, U.S. Pat. No. 4,845,097, Recueil des Travaux Chimiques des Pays-Bas (1978), 97(11), Pages 288-92, Journal of the American Chemical Society, 79, 1455(1957) or Journal of Chemical Society, p. 3478-3481 (1955).
Intermediates ii are commercially available, or prepared according to the methods described in U.S. Pat. No. 4,895,849, JP10036355, EP665225, US20070093498, WO2007046809, U.S. Pat. No. 5,783,522A, WO02083647A1, CN1927860A, WO9404527, US20110054173, WO2011025505, WO2004093800A, WO 2012075917, US20050648509, US2002082454, Organic Syntheses, Coll. Vol. 10, p. 501 (2004); Vol. 75, p. 61 (1998) or Organic Syntheses, Coll. Vol. 10, p. 102 (2004); Vol. 75, p. 53 (1998).
Method 2: the compounds represented by general formula iv can be prepared by reaction of intermediates i and iii in proper solvent, then the compounds represented by general formula PY-1 can be prepared by reaction of intermediates iv and v in the presence of proper base, the preparation methods are shown as follows. Wherein, L is a leaving group, selected from halogen, boric acid, methyl methanesulfonate or p-toluenesulfonates.




The reaction was carried out between the intermediates represented by general formula i and iii in proper solvent and the proper solvent mentioned may be selected from benzene, toluene, xylene, acetone, butanone, methylisobutylketone, tetrahydrofuran, acetonitrile, 1,4-dioxane, DMF, N-methyl pyrrolidone, DMSO, pyridine, dichloromethane, chloroform, dichloroethane, methyl acetate or ethyl acetate and so on. The reaction above can be carried out in the presence or absence of base, the reaction is promoted in the presence of base. Proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali metal carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine.
The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20 to 100° C. The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours.
The reaction was carried out between the intermediates represented by general formula iv and v in proper solvent and the proper solvent mentioned may be selected from benzene, toluene, xylene, acetone, butanone, methylisobutylketone, tetrahydrofuran, acetonitrile, 1,4-dioxane, DMF, N-methyl pyrrolidone, DMSO, pyridine, dichloromethane, chloroform, dichloroethane, methyl acetate or ethyl acetate and so on. The reaction above can be carried out in the presence of base. Proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali metal carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine.
The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20 to 200° C. The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours.
The detailed operation refers to the methods described in JP11049759, EP0370704, EPO 196524 or U.S. Pat. No. 4,895,849.
Other materials, such as the compounds represented by general formula iii and v, used to prepare the compounds represented by general formula PY-1, are commercially available.
The intermediate represented by general formula ii is one of key intermediate, some compounds are commercially available, or are prepared according to the known method described above, also can be prepared according to the following two schemes in which Substituent X1 can be defined as different substituents.
Method 1: when X1=CR6, the intermediate ii used to prepare the compounds represented by the general formula I and II (wherein A=NH) can be prepared according to the following two schemes. Relevant intermediates are commercially available, or prepared according to the methods described in U.S. Pat. No. 4,895,849, JP10036355, EP665225, US20070093498, WO2007046809, U.S. Pat. No. 5,783,522A, WO02083647A1, CN1927860A, Organic Syntheses, Coll. Vol. 10, p. 501 (2004); Vol. 75, p. 61 (1998) or Organic Syntheses, Coll. Vol. 10, p. 102 (2004); Vol. 75, p. 53 (1998).
(1) Reduction of Cyano:




Wherein, L is a leaving group, selected from halogen, boric acid, methyl methanesulfonate or p-toluenesulfonates. B is a alkyl chain with one more carbon than M.

The compounds represented by general formula ii-c can be prepared by reaction of intermediates ii-a and ii-b in proper solvent in the presence of proper base. The detailed operation refers to the methods described in US2002082454 and Fine Chemicals, 2005, 22(12): 944-960. The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20 to 100° C. The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours. The proper solvent mentioned may be selected from acetone, butanone, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, DMF, DMSO, methanol or ethanol and so on. Proper base mentioned may be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine or sodium hydride.
When L refers to boric acid group, the compounds represented by general formula ii-c can also be prepared by reaction of intermediates ii-a and ii-b at 0-100° C. in proper solvent in the presence of proper base and catalyst. The proper solvent mentioned may be selected from benzene, toluene, xylene, chloroform, dichloromethane, acetone, butanone, tetrahydrofuran, acetonitrile, 1,4-dioxane, DMF, N-methyl pyrrolidone or DMSO and so on. Proper base mentioned may be selected from pyridine or triethylamine and so on. Proper catalyst mentioned may be selected from copper acetate, copper chloride or copper sulfate and so on.
The intermediates represented by general formula ii-1 can be prepared by reaction of intermediates represented by general formula ii-c and ammonia water in the presence of proper catalyst by using hydrogenation reduction. The detailed operation refers to the methods described in J. Am. Chem. Soc, 70, 3788 (1948); 82, 681 (1960); 82, 2386 (1960); Can. J. Chem, 49, 2990 (1971); J. Org. Chem, 37, 335 (1972); Organic Syntheses, Coll. Vol. 3, p. 229, p. 720 (1955), Vol. 23, p. 71 (1943) or Vol. 27, p. 18 (1947). The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20 to 100° C. The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours. The proper solvent mentioned may be selected from methanol, ethanol, isopropanol, benzene, toluene, xylene, acetone, butanone, methylisobutylketone, chloroform, dichloroethane, methyl acetate, ethyl acetate, tetrahydrofuran, 1,4-dioxane, DMF, N-methyl pyrrolidone or DMSO, etc. The proper catalysts mentioned may be selected from Raney-nickel, palladium carbon or platinum oxide, etc.
(2) The method to prepare the substituted amine and its salts by reaction of the substituted 4-hydroxyphenylalkyl amine




Wherein, Boc2O refers to di-tert-butyl dicarbonate.
Firstly, the compounds represented by general formula ii-e can be prepared by reaction of intermediates ii-d and di-tert-butyl dicarbonate at 0-100° C. in proper solvent in the presence of proper base. The preferred temperature is 0-50° C. The reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. The proper solvent mentioned may be selected from benzene, toluene, xylene, chloroform, dichloromethane, tetrahydrofuran, acetonitrile, 1,4-dioxane, DMF, N-methyl pyrrolidone or DMSO and so on. Proper base mentioned may be selected from alkali metal carbonate such as sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate.
Then the compounds represented by general formula ii-f can be prepared by reaction of intermediates ii-e and ii-b at 0-100° C. in proper solvent in the presence of proper base. The reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. The proper solvent mentioned may be selected from benzene, toluene, xylene, chloroform, dichloromethane, acetone, butanone, tetrahydrofuran, acetonitrile, 1,4-dioxane, DMF, N-methyl pyrrolidone or DMSO and so on. Proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine.
When L refers to boric acid group. The method to prepare the compounds represented by general formula ii-f refers to the method to prepare the compounds represented by general formula ii-c with method of cyano reduction.
The salts represented by general formula ii-g can be prepared by deprotection reaction of intermediates represented by general formula ii-f and proper acid in proper solvent, and then alkalized to obtain ii-1. The preferred temperature is 0-50° C. The reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. The proper solvent mentioned may be selected from ethyl acetate, methyl acetate, methyl formate, benzene, toluene, xylene, chloroform, dichloromethane, water, tetrahydrofuran, acetonitrile, 1,4-dioxane, DMF, N-methyl pyrrolidone or DMSO and so on, the proper acid mentioned may be selected from hydrochloric acid, trifluoroacetic acid, sulfuric acid, acetic acid, propionic acid, butyric acid, oxalic acid,
adipic acid, dodecanedioic acid, lauric acid, stearic acid, fumaric acid, maleic acid, benzoic acid or phthalic acid, etc. the proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali carbonate, such as sodium carbonate or potassium carbonate; organic amine, such as pyridine or triethylamine. The detailed operation refers to the methods described in WO2004093800A and US20050096485.
Other materials mentioned above, such as the compounds represented by general formula ii-a, ii-b, ii-d and Boc2O, used to prepare the compounds represented by general formula ii-1, are commercially available.
Method 2: when X1=N, the intermediate ii used to prepare the compounds represented by the general formula III (wherein A=NH) can be prepared according to the following two schemes in which B is selected from different substituent.
(1) When B=—CH2—, the detailed operation refers to the methods described in WO9404527, US20110054173 or WO2011025505. The compounds also can be prepared according to the following method.




Wherein, U is a leaving group, selected from halogen or hydroxy, etc.
The intermediates represented by general formula ii-j can be prepared by reaction of intermediates represented by general formula ii-h and ii-i in proper solvent and temperature in the presence of proper base. The reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. The intermediates represented by general formula ii-k can be prepared by reduction reaction of intermediates represented by general formula ii-j and Red-Al, the detailed operation refers to the methods described in EP1840128. The intermediates represented by general formula ii-L can be prepared by reaction of intermediates represented by general formula ii-k and sulfoxide chloride according to known methods. The intermediates represented by general formula ii-m can be prepared by reaction of intermediates represented by general formula ii-L and sodium cyanide according to the methods described in WO2007045989 and WO2009115257. According to the methods described in Journal of Organic Chemistry, 71(21), 8023-8027; 2006, Synthesis, (24), 4242-4250, 2010, Heterocycles, 56(1-2), 443-455, 2002 or ARKIVOC (Gainesville, Fla., United States) [online computer file], (10), 40-51, 2002, The intermediates represented by general formula ii-n can be prepared via intermediate ii-m. Finally, the intermediates represented by general formula ii-2 can be prepared by reaction of intermediates represented by general formula ii-n and ammonia water in the presence of proper catalyst by using hydrogenation reduction. The detailed operation refers to the methods described in J. Am. Chem. Soc, 70, 3788(1948); 82, 681(1960); 82, 2386(1960); Can. J. Chem, 49, 2990(1971); J. Org. Chem, 37, 335(1972); Organic Syntheses, Coll. Vol. 3, p. 229, p. 720 (1955), Vol. 23, p. 71 (1943) or Vol. 27, p. 18 (1947). The proper catalysts mentioned may be selected from Raney-nickel, palladium carbon or platinum oxide, etc.
The sources of intermediates are as follows: the intermediate represented by general formula ii-h and ii-I are commercially available, or can be prepared according to the conventional method.
The proper base mentioned may be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide and so on.
The reaction was carried out in proper solvent and the proper solvent mentioned may be selected from tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, DMF, N-methyl pyrrolidone, DMSO, acetone or butanone and so on.
The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20 to 100° C.
The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours.
(2) When B=—CH2CH2—, the preparation method is as follows:




The compounds represented by general formula ii-o can be prepared by reaction of the compounds represented by general formula ii-n according to the methods described in Synthesis, (9), 727-9; 1983 or Tetrahedron Letters, 39(51), 9455-9456; 1998; the compounds having general formula ii-3 can be prepared by reaction of the compounds having general formula ii-o according to the methods in which B=—CH2—.
The second method to prepare the compounds represented by general formula PY: when A=NR12 (R12≠H), the compounds represented by general formula PY-2 can be prepared by reaction of the compounds represented by general formula PY-1 with U-R1 according to the conventional method (U defined as above); or can be prepared according to the methods described in JP08269021, JP3543411, JP1995-72621, JP1995-96669, JP3511729, JP08291149, EP530149, WO9208704 and WO2004093800A.
The third method to prepare the compounds represented by general formula PY: when A=O or S, the compounds represented by general formula PY-3, PY-4 can be prepared according to the methods described in WO2012075917 and EP534341.
The structural formula of the compounds represented by general formula PY-2, PY-3 and PY-4 are shown as follows




In general formula PY, the corresponding salts represented by general formula PY-5A can be prepared by reaction of the compounds represented by general formula PY-5 (when A=NR12) with corresponding organic acids or inorganic acids, as shown in the following.




In addition, in general formula PY, the salts can also formed based on nitrogen atom of pyrimidine ring, the preparation method refers to DE19647317, JP2001504473, U.S. Pat. No. 5,925,644, WO9822446 and ZA9710187, etc.
The reaction forming salts of compounds represented by general formula PY-5 with organic acids or inorganic acids can be carried out at room temperature to boiling point of the solvent, normal temperature is from 20 to 100° C. The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours. The proper solvent mentioned may be selected from water, methanol, ethanol, isopropanol, benzene, toluene, xylene, acetone, ethyl methyl ketone, methyl isobutyl ketone, chloroform, dichloromethane, methyl acetate, ethyl acetate, tetrahydrofuran, 1,4-dioxane, DMF, N-methyl pyrrolidone or DMSO and so on.
The acids, which can be used to form salts with compounds represented by general formula PY-5, includes carboxylic acid, such as formic acid, acetic acid, propanoic acid, butyric acid, oxalic acid, trifluoroacetic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, fumaric acid, maleic acid, sorbic acid, malic acid, citric acid, benzoic acid, p-toluylic acid or phthalic acid, etc. sulfonic acid, such as methanesulfonic acid, 1, 3-propylene sulfonic acid, p-toluenesulfonic acid or dodecylbenzene sulfonic acid, etc. inorganic acid, such as hydrochloric acid, sulphuric acid, nitric acid, phosphorous acid or carbonic acid, etc. The further preferred acids are hydrochloric acid, sulphuric acid, nitric acid, phosphorous acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid or benzoic acid.
Although the compounds represented by general formula PY and some compounds reported in prior art are both belong to substituted pyrimidine compounds, there are still some obvious differences in structure between them. It is due to these differences in structure that lead to compounds of present invention with better fungicidal and/or insecticidal/acaricidal activities.
The compounds represented by general formula PY show excellent activity against both many plant pathogens/diseases in agricultural and other fields, and insects/mites. Therefore the technical scheme of the present invention also includes the uses of the compounds represented by general formula PY or their salts/complexes to prepare fungicides, insecticides/acaricides in agricultural, forestry or public health fields. The further preferred technical scheme of the present invention also includes the uses of the compounds represented by general formula I, II or III or their salts/complexes to prepare fungicides, insecticides/acaricides in agricultural, forestry or public health fields.
The present invention is explained by the following examples of plant disease and insect pests, but without being restricted thereby.
The compounds represented by general formula PY can be used to control these plant diseases: Oomycete diseases, such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, downy mildew of beet, downy mildew of sugarcane, tobacco downy mildew, pea downy mildew, vegetable sponge downy mildew, chinese wax gourd downy mildew, muskmelon 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 disease (rape damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton damping-off), pythium rot (pepper soft stale disease, vegetable sponge cottony leak, chinese wax gourd cottony leak), blight (broad bean phytophthora blight, cucumber phytophthora blight, pumpkin phytophthora rot, chinese wax gourd phytophthora blight, watermelon phytophthora blight, muskmelon phytophthora blight, pepper phytophthora blight, chinese chives phytophthora blight, carlic phytophthora blight, cotton phytophthora blight), late blight (potato late blight, tomato late blight) and so on; diseases caused by Deuteromycotina, such as wilt disease (sweet potato fusarium wilt, cotton fusarium wilt disease, sesame wilt disease, fusarium wilt disease of costarbean, tomato fusarium wilt, bean fusarium wilt, cucumber fusarium wilt, vegetable sponge fusarium wilt, pumpkin fusarium wilt, chinese wax gourd fusarium wilt, watermelon fusarium wilt, muskmelon fusarium wilt, pepper fusarium wilt, broad bean fusarium wilt, fusarium wilt disease of rape, fusarium wilt disease of soybean), root rot (pepper root rot, eggplant root rot, bean fusarium root-rot, cucumber fusarium root rot, balsam pear fusarium root rot, cotton black root rot, broad bean thielaviopsis root rot), drooping disease (cotton soreshin, sesame soreshin, pepper rhizoctonia rot, cucumber rhizoctonia rot, chinese cabbage rhizoctonia rot), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry anthracnose, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, balsam pear anthracnose, summer squash anthracnose, chinese wax gourd anthracnose, watermelon anthracnose, muskmelon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, verticillium wilt of sunflower, tomato verticillium wilt, pepper verticillium wilt, eggplant verticillium wilt), scab (summer squash scab, chinese wax gourd scab, muskmelon scab), gray mold (cotton boll gray mold, kenaf gray mold, tomato gray mold, pepper gray mold, bean gray mold, celery gray mold, spinach gray mold, kiwi fruit gray mold rot), brown spot (cotton brown spot, jute brown spot, beet sercospora leaf spot, peanut brown spot, pepper brown leaf spot, chinese wax gourd corynespora leaf spot, soybean brown spot, sunflower brown spot, pea ascochyta blight, broad bean brown spot), black spot (flax black spot, rape alternaria leaf spot, sesame black spot, sunflower alternaria leaf spot, costarbean alternaria leaf spot, tomato nail head spot, pepper black fruit spot, eggplant black spot, bean leaf spot, cucumber alternaria blight, celery alternaria black leaf spot, carrot alternaria black rot, carrot leaf blight, apple alternaria rot, peanut brown spot), spot blight (tomato septoria leaf spot, pepper septoria leaf spot, celery late blight), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean zonate spot, sesame ring spot, bean zonate spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon alternaria blight, muskmelon alternaria spot), basal stem rot (tomato basal stem rot, bean rhizoctonia rot), and others (corn northern leaf spot, kenaf damping-off, rice blast, millet black sheath, sugarcane eye spot, cotton aspergillus boll rot, peanut crown rot, soybean stem blight, soybean black spot, muskmelon alternaria leaf blight, peanut web blotch, tea red leaf spot, pepper phyllosticta blight, chinese wax gourd phyllosticta leaf spot, celery black rot, spinach heart rot, kenaf leaf mold, kenaf brown leaf spot, Jute stem blight, soybean cercospora spot, sesame leaf spot, costarbean gray leaf spot, tea brown leaf spot, eggplant cercospora leaf spot, bean cercospora leaf spot, balsam pear cercospora leaf spot, watermelon cercospora leaf spot, jute dry rot, sunflower root and stem rot, bean charcoal rot, soybean target spot, eggplant corynespora leaf spot, cucumber corynespora target leaf spot, tomato leaf mold, eggplant fulvia leaf mold, broad bean chocolate spot) and so on; diseases caused by Basidiomycete, such as rust (wheat stripe rust, wheat stem rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, chinese chives rust, onion rust, millet rust, soybean rust), smut (corn head smut, corn smut, sorghum silk smut, sorghum loose kernel smut, sorghum hard smut, sorghum smut, millet kernel smut, sugarcane smut, bean rust), and others (for example, wheat sheath blight and rice sheath blight) and so on; diseases caused by Ascomycete, such as powdery mildew (wheat powdery mildew, rape powdery mildew, powdery mildew of sesame, powdery mildew of sunflower, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, vegetable sponge powdery mildew, pumpkin powdery mildew, summer squash powdery mildew, chinese wax gourd, muskmelon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia rot (flax sclertiniose, rape sclertiniose, soybean sclertiniose, peanut sclertiniose, tobacco sclerotinia rot, pepper sclerotinia rot, eggplant sclerotinia rot, bean sclerotinia rot, pea sclerotinia rot, cucumber sclerotinia rot, balsam pear sclerotinia rot, chinese wax gourd sclerotinia rot, watermelon sclerotinia disease, celery stem rot), scab (apple scab, pear scab) and so on. Especially, the compounds of the present invention exhibit very good control against corn southern rust, rice blast, cucumber gray mold and cucumber downy mildew at very low doses.
The compounds represented by general formula PY can be used to control these insect pests: Coleoptera, such as Acanthoscelides spp., Acanthoscelides obtectus, Agrilus planipennis, Agriotes spp., Anoplophora glabripennis, Anthonomus spp., Anthonomus grandis, Aphidius spp., Apion spp., Apogonia spp., Atacnius sprctulus, Atomaria linearis, pygmy mangold beetle, Aulacophore spp., Bothynoderes punctiventris, Bruchus spp., Bruchus pisorum, Cacoesia, Cacoesia spp., Callosobruchus maculatus, Carpophilus hemipteras, Cassida vittata, Cerosterna spp., Ccrotoma, Ccrotoma spp., Cerotoma trifur cata, Ceutorhynchus spp., Ceutorhynchus assimilis, cabbage seedpod weevil, Ceutorhynchus napi, cabbage curculio, Chaetocnema spp., Colaspis spp., Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar, Cotinus nitidis, Green June beetle, Crioceris asparagi, Cryptolestes ferrugincus, rusty grainbeetle, Cryptolestes pusillus, Cryptolestes turcicus Turkish grain beetle, Ctenicera spp., Curculio spp., Cyclocephala spp., Cylindrocpturus adspersus, sunflower stem weevil, Deporaus marginatus, mango leaf-cutting weevil, Dermestes lardarius, Dermestes maculates, Diabrotica spp., Epilachna varivcstis, raustinus cubae, Hylobius pales, pales weevil, Hypera spp., Hypera postica, Hyperdoes spp., Hyperodes weevil, Hypothenemus hampei, Ips spp., engravers, Lasioderma serricorne, Leptinotarsa decemlineata, Liogenys fuscus, Liogenys suturalis, Lissorhoptrus oryzophilus, Lyctus spp., powder post beetles, Maecolaspis joliveti, Megascelis spp., Melanotus communis, Meligethes spp., Meligethes aeneus, blossom beetle, Melolontha melolontha, Oberea brevis, Oberea linearis, Oryctes rhinoceros, date palm beetle, Oryzaephilus mercator, merchant grain beetle, Oryzaephilus surinamensis, sawtoothed grain beetle, Otiorhynchus spp., Oulema melanopus, cereal leafbeetle, Oulema oryzae, Pantomorus spp., Phyllophaga spp., Phyllophaga cuyabana, Phyllotreta spp., Phynchites spp., Popillia japonica, Prostephanus truncates, larger grain borer, Rhizopertha dominica, lesser grain borer, Rhizotrogus spp., Eurpoean chafer, Rhynchophorus spp., Scolytus spp., Shenophorus spp. Sitona lincatus, pca leaf weevil, Sitophilus spp., Sitophilus granaries, granary weevil, Sitophilus oryzae, rice weevil, Stegobium paniceum, drugstore beetle, Tribolium spp., Tribolium castaneum, red flour beetle, Tribolium confusum, confused flour beetle, Trogoderma variabile, warehouse beetle and Zabrus tenebioides. 
Dermaptera.
Dictyoptera, such as Blattella germanica, German cockroach, Blatta orientalis, Parcoblatta pennylvanica, Periplaneta americana, American cockroach, Periplaneta australoasiae, Australian cockroach, Periplancta brunnca, brown cockroach, Periplaneta fuliginosa, smokybrown cockroach, Pyncoselus suninamensis, Surinam cockroach and Supella longipalpa, brownbanded cockroach.
Diptera, such as Aedes spp., Agromyza frontella, alfalfa blotch leafminer, Agromyza spp., Anastrepha spp., Anastrepha suspensa, Caribbean fruit fly, Anopheles spp., Batrocera spp., Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis spp., Ceratitis capitata, Chrysops spp., Cochliomyia spp., Contarinia spp., Culex spp., Dasineura spp., Dasineura brassicae, Delia spp., Delia platura, seedcom maggot, Drosophila spp., Fannia spp., Fannia canicularis, little house fly, Fannia scalaris, Gasterophilus intestinalis, Gracillia perseae, Haematobia irritans, Hylemyia spp., root maggot, Hypoderma lineatum, common cattle grub, Liriomyza spp., Liriomyza brassica, serpentine leafminer, Melophagus ovinus, Musca spp., muscid fly, Musca autumnalis, face fly, Vusca domestica, house fly, Oestrus ovis, sheep bot fly, Oscinella frit, Pegomyia betae, beet leafminer, Phorbia spp., Psila rosae, carrotrust fly, Rhagoletis cerasi, cherry fruit fly, Rhagoletis pomonella, apple maggot, Sitodiplosis mosellana, orange wheat blossom midge, stomoxys calcitruns, stable fly, Tahanus spp. and Tipula spp.
Hemiptera, such as Acrosternum hilare, green stink bug, Blissus leucopterus, chinch bug, Calocoris norvegicus, potato mirid, Cimex hemipterus, tropical bed bug, Cimex lectularius, bed hug, Daghertus fasciatus, Dichelops furcatus, Dysdercus suturellus, cotton stainer, Edessa meditabunda, Eurygaster maura, cereal bug, Euschistus heros, Euschistus servus, brown stink bug, Helopeltis antonii, Helopeltis theivora, tea blight plantbug, Lagynotomus spp., Leptocorisa oratorius, Leptocorisa varicomi, Lygus spp., plant bug, Lygus hesperus, western tarnished plant bug, Maconellicoccus hirsutus, Neurocolpus longirostris, Nezara viridula, southern green stink bug, PhyLocoris spp., Phytocoris californicus, Phytocoris relativus, Piezodorus guildingi, Poecilocapsus lineatus, fourlined plant bug, Psallus vaccinicola, Pseudacysta perseae, Scaptocoris castanea and Triatoma spp., bloodsuckingconenose bug, kissing bug.
Homoptera, such as Acrythosiphonpisum, pea aphid, Adelges spp., adelgids, Aleurodes proletella, Aleurodicus disperses, Aleurothrixus flccosus, woolly whitefly, Aluacaspis spp., Amrasca bigutella bigutella, Aphrophora spp., leafhopper, Aonidiella aurantii, California red scale, Aphis spp., Aphis gossypii, cotton aphid, Aphis pomi, apple aphid, Aulacorthitm solan, foxglove aphid, Bemisia spp., Bemisia argentifolii, Bemisia tabaci, sweetpotato whitefly, Brachycolus noxius, Russian aphid, Brachycorynclia asparagi, asparagus aphid, Brevennia rehi, Brevicoryne brassicae, Ceroplastes spp., Ceroplastes rubens, red wax scale, Chionaspis spp., Chrysomphalus spp., Coccus spp., Dysaphis plantaginea, rosy apple aphid, Empoasca spp., Eriosoma lanigerum, woolly apple aphid, Icerya purchasi, cottony cushion scale, Idioscopus nitidulus, mango leafhopper, Laodelphax striatellus, smaller brown planthopper, Lepidosaphes spp., Macrosiphum spp., Macrosiphum euphorbiae, potato aphid, Macrosiphum granarium, English grain aphid, Macrosiphum rosae, rose aphid, Macrosteles quadrilineatus, aster leafhopper, Mahanarva frimbiolata, Metopolophium dirhodum, rose grain aphid, Midis longicornis, Myzus persicae, green peach aphid, Nephotettix spp., Nephotettix cinctipes, green leafhopper, Nilaparvata lugens, brown planthopper, Parlatoria pergandii, chaff scale, Parlatoria ziziphi, ebony scale, Peregrinus maidis, corn delphacid, Philaenus spp., Phylloxera vitifoliae, grape phylloxera, Physokermes piceae, spruce bud scale, Planococcus spp., Pseudococcus spp., Pseudococcus brevipes, pine apple mealybug, Quadraspidiotus perniciosus, San Jose scale, Rhapalosiphum spp., Rhapalosiphum maida, corn leaf aphid, Rhapalosiphum padi, oatbird-cherry aphid, Saissetia spp., Saissetia oleae, Schizaphis graminum, greenbug, Sitobion avenge, Sogatella furcifera, white-backed planthopper, Therioaphis spp., Toumeyella spp., Toxoptera spp., Trialeurodes spp., Trialeurodes vaporariorum, greenhouse whitefly, Trialeurodes abutiloneus, bandedwing whitefly, Unaspis spp., Unaspis yanonensis, arrowhead scale and Zulia entreriana. 
Hymenoptera, such as Acromyrrmex spp., Athalia rosae, Atta spp., leafcutting ants, Camponotus spp., carpenter ant, Diprion spp., sawfly, Formica spp., Iridomyrmex humilis, Argentineant, Monomorium ssp., Monomorium minumum, little black ant, Monomorium pharaonis, haraoh ant, Neodiprion spp., Pogonomyrmex spp., Polistes spp., paper wasp, Solenopsis spp., Tapoinoma sessile, odorous house ant, Tetranomorium spp., pavement ant, Vespula spp., yellow jacket and Xylocopa spp., carpenter bee.
Isoptera, such as Coptotermes spp., Coptotermes curvignathus, Coptotermes frenchii, Coptotermes formosanus, Formosan subterranean termite, Cornitermes spp., nasute termite, Cryptotermes spp., Heterotermes spp., desert subterranean termite, Ileterotermes aureus, Kalotermes spp., Incistitermes spp., Macrotermes spp., fungus growing termite, Marginitermes spp., Microcerotermes spp., harvester termite, Microtermes obesi, Procornitermes spp., Reticulitermes spp., Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermes flavipes, Reticulitermes hageni, Reticulitermes hesperus, Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes tibialis, Reticulitermes virginicus, Schedorhinotermes spp. and Zootermopsis spp.
Lepidoptera, such as Achoea janata, Adoxophyes spp., Adoxophyes orana, Agrotis spp., Agrotis ipsilon, Alabama argillacea, cotton leafworm, Amorbia cuneana, Amyelosis transitella, navel orangeworm, Anacamptodes defectaria, Anarsia lineatella, peach twig borer, Anomis sabulijera, jute looper, Anticarsia gemmatalis, velvetbean caterpillar, Archips argyrospila)(fruit tree leafroller, Archips rosana, rose leaf roller, Ar gyrotaenia spp., tortricid moths, Argyrotaenia citrana, orange tortrix, Autographa gamma, Bonagota cranaodcs, Borbo cinnara, rice leaf folder, Bucculatrix thurberiella, cotton leafperforator, Caloptilia spp., Capua reticulana, Carposina niponensis, peach fruit moth, Chilo spp., Chlumetia transversa, mango shoot borer, Choristoneura rosaceana, oblique banded leaf roller, Chrysodeixis spp., Cnaphalocerus medinalis, grass leafroller, Colias spp., Conpomorpha cramerella, Cossus cossus, Crambus spp., Sod webworms, Cydia funebrana, plum fruit moth, Cydia molesta, oriental fruit moth, Cydia nignicana, pea moth, Cydia pomonella, codling moth, Darna diducta, Diaphania spp., stem borer, Diatr aea spp., stalk bor er, Diatraea saccharalis, sugarcane borer, Diatraea graniosella, southwester corn borer, Earias spp., Earias insulata, Egyptian bollworm, Earias vit.ella, rough northern bollworm, Ecdytopopha aurantianum, Elasmopalpus lignosellus, lesser cornstalk borer, Epiphysias postruttana, light brown, apple moth, Ephestia spp., Ephestia cautella, almond moth, Ephestia elutella, tobbaco moth, Ephestia kuehniella, Mediterranean flour moth, Epimeces spp, Epinotia aporema, Erionota thrax, banana skipper, Eupoecilia ambiguella, grape berry moth, Euxoa auxiliaris, army cutworm, Feltia spp., Gortyna spp., Grapholita molesta, oriental fruit moth, Hedylepta indicata, bean leaf webber, Helicoverpa spp., Helicoverpa armigera, cotton bollworm, Helicoverpa zea, Heliothis spp., Heliothis virescens, tobacco budworm, Hellula undalis, cabbage webworm, Indarbela spp. Keiferia lycopersicella, tomato pinworm, Leucinodes orbonalis, eggplant fruit borer, Leucoptera malifoliella, Lithocollectis spp., Lobesia botrana, grape fruit moth, Loxagrotis spp., Loxagrotis albicosta, western bean cutworm, Lymantria dispar, gypsy moth, Lyonetiaclerkella, apple leafminer, Mahasena corbetti, oil palm bagworm, Malacosoma spp., tent caterpillars, Mamestra brassicae, cabbage armyworm, Maruca testulalis, Metisa plana, Mythimna unipuncta, true armyworm, Neoleucinodes elegantalis, small tomato borer, Nymphula depunctalis, rice caseworm, Operophthera brumata, winter moth, Ostrinia nubilalis, European corn borer, Oxydia vesulia, Pandemis cerasana, common currant tortrix, Pandemis heparana, brown apple tortrix, Papilio demodocus, Pectinophora gossypiella, pink bollworm, Peridroma spp., Peridroma saucia, variegated cutworm, Perileucoptera coffeella, white coffee leafminer, Phthorimaea operculella, potato tuber moth, Phyllocnisitis citrella, Phyllonorycter spp., Pieris rapae, imported cabbageworm, Plathypena scabra, Plodia interpunctella, Indian meal moth, Plutella xylostella, diamondback moth, Polychrosis viteana, grape berry moth, Prays endocarps, Prsys oleae, olive moth, Pseudaletia spp., Pseudaletia unipunctata, Pseudoplusia includens, soybean looper, Rachiplusia nu, Scirpophaga incertulas, Sesamia spp., Sesamia inferens, pink rice stemborer, Sesamia nonagrioides, Setora nitens, Sitotroga cerealella, Angoumois grain moth, Sparganothis pilleriana, Spodoptera spp., Spodoptera exigua, beet armyworm, Spodoptera fugiperda, fall armyworm, Spodoptera oridania, southern armyworm, Synanthedon spp., Thecla basilides, Thermisia gemmatalis, Tineola bisselliella, webbing clothes moth, Trichoplusia ni, cabbage looper, Tuts absoluta, Yponomeuta spp., Zeuzeracoffeae, red branch borer and Zeuzera pyrina, eopard moth.
Mallophaga, chewing lice, such as Bovicola ovis, sheep biting louse, Menacanthus stramineus, chicken body louse and Menopon gallinea, common hen house,
Orthoptera, such as Anabrus simplex, Mormon cricket, Gryllotalpidae, mole cricket, Locusta migratoria, Melanoplus spp., Microcentrum retinerve, angular winged katydid, Pterophylla spp., histocerca gregaria, Scudderia furcata, fork tailed bush katydid and Valanga nigricorni, sucking louse, such as Haematopinus spp., Linognathus ovillus, sheep louse, Pediculus humanus capitis, Pediculus humanus humanus and Pthirus pubis, crab louse.
Siphonaptera, such as Ctenocephal ides canis, dog flea, Ctenocephalides felis, cat flea and Pulex irritanshuman flea.
Thysanoptera, such as Frankliniella fusca, tobacco thrip, Frankliniella occidentalis, western flower thrips, Frankliniella shultzei, Frankliniella williamsi, corn thrip, IIeliothrips haemorrhaidalis, greenhouse thrip, Riphiphorothrips cruentatus, Scirtothrips spp, Scirtothrips cirri, citrus thrip, Scirtothrips dorsalis, yellow tea thrips, Taeniothrips rhopalantennalis and Thrips spp.
Thysanura, bristletail, such as Lepisma spp, silverfish and Thermobia spp.
Acarina, mite and tick, such as Acarapsis woodi, tracheal mite of honeybee, Acarus spp., Acarus siro, grain mite, Aceria mangiferae, mango bud mite, Aculops spp., Aculops lycopersici, tomato russet mite, Aculops pelekasi, Aculus pelekassi, Aculus schlechtendali, apple rust mite, Amblyomma americanum, lone star tick, Boophilus spp., Brevipalpus obovatus, privet mite, Brevipalpus phoenicis, red and black flat mite, Demodex spp., mange mites, Dermacentor spp., Dermacentor variabilis, american dog tick, Dermatophagoides pteronyssinus, house dust mite, Eotetranycus spp., Eotetranychus carpini, yellow spider mite, Epitimerus spp., Eriophyes spp.,  ; odes spp., Metatetranycus spp., Notoedres cati, Oligonychus spp., Oligonychus coffee, Oligonychus ilicus, southernred mite, anonychus spp., Panonychus cirri, citrus red mite, Panonychus ulmi, European red mite, Phyllocoptruta oleivora, citrus rust mite, Polyphagotarsonemun latus, broad mite, Rhipicephalus sanguineus, brown dog tick, Rhizoglyphus spp., bulb mite, Sarcoptes scabiei, itch mite, Tegolophus perseaflorae, Tetranychus spp., Tetranychus urticae, twospotted spider mite and Varroa destructor. 
Nematoda, such as Aphelenchoides spp., bud and leaf & pine wood nematode, Belonolaimus spp., sting nematodes, Criconemella spp., ring nematodes, Dirofilaria immitis, dog heartworm, Ditylenchus spp., Heterodera spp., cyst nematode, Heterodera zeae, corn cyst nematode, Hirschmanniella spp., root nematodes, Hoplolaimus spp., lance nematodes, Meloidogyne spp., Meloidogyne incognita, Onchocerca volvulus, hook-tail worm, PraLylenchus spp., lesion nematode, Radopholus spp., burrowing nematode and Rotylenchus reniformis, kidney-shaped nematode.
Symphyla, such as Scutigerella immaculata. 
Especially, the compound represented by the present invention provides great control effects against peach aphid, diamondback moth, armyworm, and carmine spider mite, and acquires great effects at a minimal dosage.
Due to their positive characteristics, the compounds mentioned above can be advantageously used in protecting crops of farming and gardening, domestic and breeding animals, as well as environments frequented by human beings, from pathogens, insects and pest mites.
In order to obtain desired effect, the dosage of the compound to be applied can vary with various factors, for example, the used compound, the protected crop, the type of harmful organism, the degree of infestation, the climatic conditions, the application method and the adopted formulation.
The dosage of compounds in the range of 10 g to 5 kg per hectare can provide a sufficient control.
A further object of the present invention also includes fungicidal, insecticidal/acaricidal compositions containing the compounds having general formula PY as active ingredient, and the weight percentage of the active ingredient in the composition is 0.1-99%. The fungicidal, insecticidal/acaricidal compositions also include the carrier being acceptable in agriculture, forestry, public health.
Especially, a preferred object of the present invention also includes fungicidal, insecticidal/acaricidal compositions containing the compounds and its salts/complexes having general formula I, II or III as active ingredient, wherein the weight percentage of the active ingredient in the composition is 0.1-99%.
The compositions of the present invention can be used in the form of various formulations. Usually, the compounds having general formula PY as active ingredient can be dissolved in or dispersed in carriers or made to a formulation so that they can be easily dispersed as an fungicide or insecticide. For example: these chemical formulations can be made into wettable powder, oil miscible flowable, aqueous suspension, aqueous emulsion, aqueous solution or emulsifiable concentrates. Therefore, in these compositions, at least a liquid or solid carrier is added, and usually suitable surfactant(s) can be added when needed.
Still also provided by the present invention are the application methods for controlling phytopathogenic fungi, insects, pest mites: which is to apply the compositions of the present invention to the phytopathogenic fungi, insects, pest mites as mentioned above or their growing loci. The suitable effective dosage of the compounds of the present invention is usually within a range of 10 g/ha to 1000 g/ha, preferably from 20 g/ha to 500 g/ha. For some applications, one or more other fungicides, insecticides/acaricides, herbicides, plant growth regulators or fertilizer can be added into the fungicidal, insecticidal/acaricidal compositions of the present invention to make additional merits and effects.
It should be noted that variations and changes are permitted within the claimed scopes in the present invention.


DETAILED DESCRIPTION OF THE INVENTION
The present invention is illustrated by the following examples, but without being restricted thereby. (All raw materials are commercially available unless otherwise specified.)
PREPARATION EXAMPLES
Example 1: The Preparation of Intermediate 4,5-dichloro-6-methylpyrimidine
1) The Preparation of 4-hydroxyl-5-chloro-6-methylpyrimidine




8.80 g (0.16 mol) of CH3ONa in methanol was added slowly to a solution of 11.30 g (0.11 mol) of formimidamide in 50 mL of methanol at room temperature under stirring, the mixture was stirred for another 2 hrs after addition at room temperature. Followed by addition of 11.17 g (0.068 mol) of ethyl 2-chloro-3-oxobutanoate, the mixture was continued stirring for another 5-7 hrs at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure and pH was adjusted to 5-6 with HCl, and then filtered to afford orange-yellow solid, the water phase was extracted with ethyl acetate (3×50 mL), dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was dissolved to 50 ml of ethyl acetate, stand overnight to obtain 6.48 g as orange-yellow solid with yield of 66%. m.p. 181-184° C.
2) The Preparation of Intermediate 4,5-dichloro-6-methylpyrimidine




50 ml of POCl3 was added dropwise to a solution of 14.5 g (0.1 mol) of 4-hydroxyl-5-chloro-6-methylpyrimidine in 50 mL of toluene, the mixture was refluxed for 5-7 hrs after addition. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure to remove toluene and extra POCl3, and then poured into ice water. The water phase was extracted with ethyl acetate (3×50 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column to give 14.43 g as yellow liquid with yield of 88.5%.
Example 2: The Preparation of Intermediate 4,5-dichloro-6-(difluoromethyl)pyrimidine
1) The Preparation of 2-dichloro-4,4-difluoro-3-oxobutanoate




177.46 g (1.33 mol) of sulfonyl chloride in 200 mL dichloromethane was added slowly to a solution of 200.00 g (1.20 mol) of ethyl 4,4-difluoro-3-oxobutanoate in 300 mL of dichloromethane at room temperature under stirring for 3 hrs, then a lot of gas released out after addition, the mixture was continued stirring for another 5-7 hrs at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the excess solvent and sulfonyl chloride were concentrated under reduced pressure to obtain 240 g as faint yellow liquid.
2) The Preparation of 4-hydroxyl-5-chloro-6-(difluoromethyl)pyrimidine




A solution of 71.9 g (0.70 mol) of formimidamide in 150 mL of methanol was stirred at 5-10° C., 64.6 g (1.20 mol) of CH3ONa in methanol prepared and cooled to room temperature ahead of time was added slowly to the above solution under stirring, followed by addition of 100 g (0.50 mol) of ethyl 2-chloro-4,4-difluoro-3-oxobutanoate in 100 ml of methanol, the mixture was continued stirring for another 3-4 hrs at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure and pH was adjusted to 5-6 with HCl, and then filtered to afford 65 g as white solid with yield of 73%. m.p. 204-206° C.
3) The Preparation of 4,5-dichloro-6-(difluoromethyl)pyrimidine




100 ml of POCl3 was added dropwise to a solution of 65.0 g (0.36 mol) of 4-hydr oxyl-5-chloro-6-(difluoromethyl)pyrimidin in 150 mL of toluene, the mixture was refluxed for 3-5 hrs after addition. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure to remove toluene and extra POCl3, and then poured into ice water. The water phase was extracted with ethyl acetate (3×50 mL), the organic phases were emerged, washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column to give 64.5 g as yellow liquid, cooled to be solid in refrigerator with yield of 9 0%.
Example 3: The Preparation of 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethanamine
1) The Preparation of 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)acetonitrile




To a solution of 2-chloro-5-(trifluoromethyl)pyridine 18.15 g (0.1 mol) and 2-(4-hydroxyphenyl)acetonitrile 15.96 g (0.12 mol) in 200 mL butanone was added potassium carbonate 27.60 g (0.2 mol). The reaction mixture was continued stirring and heating to reflux for 4-10 hrs, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. Then the mixture was poured into 200 mL of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of 5% aqueous solution of NaOH, and 50 mL of brine successively, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:5, as an eluent) to obtain 22.50 g target intermediate as white solid with yield of 81.5%, m.p. 48-49 □.
2) The Preparation of 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethanamine




To a solution of 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)acetonitrile 2.78 g (0.01 mol), Raney nickel (1.0 g) and 10 mL of 25% aqueous ammonia in 50 mL ethanol was filled with hydrogen, then the reaction mixture was continued stirring at room temperature for 3-15 hrs and monitored by TLC until the reaction was over, Raney nickel was filtered, the solution was concentrated under reduced pressure to give sticky oil cooled to obtain 2.20 g target intermediate as white solid with yield of 78%, m.p. 82-83° C.
Example 4: The Preparation of 4-(2-(5-chloro-6-methylpyrimidin-4-ylamino)ethyl)phenol




To a solution of 4-(2-aminoethyl)phenol 1.13 g (0.01 mol) and triethylamine 2.02 g (0.02 mol) in 50 mL toluene was dropwise added 4,5-dichloro-6-methylpyrimidine 1.63 g (0.01 mol). The reaction mixture was continued stirring for 4-10 hrs, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to obtain 2.10 g target intermediate as white solid with yield of 88%, m.p. 177-179° C.
Example 5: The Preparation of Intermediate 2-(4-(3,5,6-trichloropyridin-2-yloxy)phenyl)ethanamine
1) tert-butyl 4-hydroxyphenethylcarbamate




To a solution of 4-(2-aminoethyl)phenol 11.3 g (0.1 mol) and sodium bicarbonate 10.08 g (0.12 mol) in 80 mL tetrahydrofuran was dropwise added di-tert-butyl dicarbonate 21.80 g (0.1 mol) at room temperature, then the reaction mixture was continued stirring for 4-10 hrs, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. Then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 17.15 g target intermediate as white solid with yield of 81%, m.p. 48-49° C.

    
    
        2) The Preparation of tert-butyl 4-(3,5,6-trichloropyridin-2-yloxy)phenethylcarbamate
    
    






To a solution of tert-butyl 4-hydroxyphenethylcarbamate 2.37 g (0.01 mol) and 2,3,5,6-tetrachloropyridine 2.17 g (0.01 mol) in 50 mL butanone was added potassium carbonate 2.76 g (0.02 mol). The reaction mixture was continued stirring and heating to reflux for 4-10 hrs, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:5, as an eluent) to obtain 3.55 g target intermediate as white solid with yield of 82%, m.p. 48-49° C.
3) The Preparation of 2-(4-(3,5,6-trichloropyridin-2-yloxy)phenyl)ethanamine hydrochloride




To a solution of tert-butyl 4-(3,5,6-trichloropyridin-2-yloxy)phenethylcarbamate 4.17 g (0.01 mol) in 50 mL ethyl acetate was dropwise added 15 mL concentrated hydrochloric acid. The reaction mixture was Gradually dissolved and continued stirring for 4-5 hrs, then a large amount of solid was precipitated and filtered, the filter cake was washed with 50 mL ethyl acetate to obtain 3.0 g target intermediate as white solid with yield of 88%, m.p. 48-49° C.
Example 6: The Preparation of Compound I-22




To a solution of 4,5-dichloro-6-methylpyrimidine 1.63 g (0.01 mol) and 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethanamine 2.82 g (0.01 mol) in 50 mL toluene was added triethylamine 2.02 g (0.02 mol) after the reaction mixture was dissolved. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to obtain 3.25 g compound I-22 as white solid with yield of 80%, m.p. 98-99° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ(ppm): 2.46 (3H, s), 2.97 (2H, t), 3.79 (2H, q), 5.47 (1H, t), 7.01 (1H, d), 7.12 (2H, d), 7.29 (2H, d), 7.90 (1H, d), 8.40 (1H, d), 8.44 (1H, s).
Example 7: The Preparation of Compound I-254




To a solution of 1.77 g (0.01 mol) 4,5-dichloro-6-ethylpyrimidine (the preparation refers to Example 1, the difference is replacing ethyl 2-chloro-3-oxobutanoate to ethyl 2-chloro-3-oxopentanoate) and 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethanamine 2.82 g (0.01 mol) in 50 mL toluene was added triethylamine 2.02 g (0.02 mol). The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to obtain 3.56 g compound I-254 as white solid with yield of 83%, m.p. 76 ̃78° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ(ppm): 1.26 (3H, t), 2.79 (2H, q), 2.77 (4H, m), 2.97 (2H, t), 3.79 (2H, q), 5.51 (1H, t), 7.00 (1H, d), 7.11 (2H, d), 7.29 (2H, d), 7.89 (1H, d), 8.44 (2H, m).
Example 8: The Preparation of Compound I-483




To a solution of 4-(2-(5-chloro-6-methylpyrimidin-4-ylamino)ethyl)phenol 2.64 g (0.01 mol) and 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethanamine 2.33 g (0.01 mol) in 30 mL N,N-dimethyl formamide was added potassium carbonate 2.76 g (0.02 mol). The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 3.77 g compound I-483 as colorless oil with yield of 82%.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.45 (3H, s), 2.96 (2H, t), 3.72-3.84 (2H, q), 5.45 (1H, t), 7.13 (2H, d), 7.29 (2H, d), 7.99 (1H, d), 8.27 (1H, s), 8.40 (1H, s).
Example 9: The Preparation of Compound I-583




To a solution of 2.78 g (0.01 mol) 4-(2-(5-chloro-6-ethylpyrimidin-4-ylamino)ethyl)phenol (the preparation refers to Example 3, the difference is replacing 4,5-dichloro-6-methylpyrimidine to 4,5-dichloro-6-ethylpyrimidine) and 2,3,5-trichloropyridine 1.83 g (0.01 mol) in 30 mL N,N-dimethyl formamide was added potassium carbonate 2.76 g (0.02 mol). The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to obtain 3.50 g compound I-583 as colorless oil with yield of 83%, m.p. 53-54° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 1.26 (3H, t), 2.79 (2H, q), 2.96 (2H, q), 3.77 (2H, q), 5.47 (1H, t), 7.11 (2H, d), 7.28 (2H, d), 7.77 (1H, s), 8.45 (1H, s).
Example 10: The Preparation of Compound I-2342




To a solution of 4,5-dichloro-6-(difluoromethyl)pyrimidine 1.99 g (0.01 mol) and 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethanamine 2.82 g (0.01 mol) in 50 mL toluene was added triethylamine 2.02 g (0.02 mol) after the reaction mixture was dissolved. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 3.82 g compound I-2342 as white solid with yield of 86%, m.p. 102-103° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 8.581 (s, 1H, pyrimidine-H), 8.439 (s, 1H, pyridine-6-H), 7.891-7.927 (d, 1H, pyridine-4-H), 7.008-7.037 (d, 1H, pyridine-3-H), 7.111-7.310 (dd, 4H, Ar—H), 6.547-6.904 (t, 1H, F2C—H, 5.747 (s, 1H, NH), 3.815-3.882 (q, 2H, N—CH2—C), 2.964-3.010 (t, 2H, C—CH2—Ar).
Example 11: The Preparation of Compound I-2574




To a solution of 1.99 g (0.01 mol) 4,5-dichloro-6-(difluoromethyl)pyrimidine and 2.82 g (0.01 mol) 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethanamine (the preparation refers to Example 3) in 50 mL toluene was added triethylamine 2.02 g (0.02 mol) after the reaction mixture was dissolved. The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 4.16 g compound I-2574 as white solid with yield of 84%.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): δ 8.577 (s, 1H, pyrimidine-H), 8.270 (s, 1H, pyridine-6-H), 7.981-7.987 (d, 1H, pyridine-4-H), 7.128-7.319 (dd, 4H, Ar—H), 6.716 (t, 1H, F2C—H), 3.843-3.864 (q, 2H, N—CH2—C), 2.970-3.016 (t, 2H, C—CH2—Ar).
Example 12: The Preparation of Compound I-2748




To a solution of 2.17 g (0.01 mol) 4,5-dichloro-6-(trifluoromethyl)pyrimidine (the preparation refers to Example 1) and 3.19 g (0.01 mol) 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethanamine in 50 mL toluene was added triethylamine 2.02 g (0.02 mol). The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 4.07 g compound I-2748 as white solid with yield of 88%, m.p. 96-97° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 8.577 (s, 1H, pyrimidine-H), 8.436 (s, 1H, pyridine-6-H), 7.892-7.920 (d, 1H, pyridine-4-H), 7.010-7.039 (d, 1H, pyridine-3-H), 7.115-7.313 (dd, 4H, Ar—H), 5.898 (s, 1H, NH), 3.825-3.890 (q, 2H, N—CH2—C), 2.966-3.014 (t, 2H, C—CH2—Ar).
Example 13: The Preparation of Compound I-3309




To a solution of 1.77 g (0.01 mol) 4,5-dichloro-6-ethylpyrimidine and 2.50 g (0.01 mol) 2-(4-(6-chloropyridazin-3-yloxy)phenyl)ethanamine (the preparation refers to Example 3, the difference is replacing 2-chloro-5-(trifluoromethyl)pyridine to 3,6-dichloropyridazine) in 50 mL toluene was added 2.02 g (0.02 mol)triethylamine after the reaction mixture was dissolved. The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to obtain 3.40 g compound I-3309 as white solid with yield of 87%, m.p. 138-140° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 1.25 (3H, t), 2.79 (2H, q), 2.96 (2H, t), 3.78 (2H, q), 5.50 (1H, s), 7.16 (3H, m), 7.26 (2H, m), 7.50 (1H, d), 8.45 (1H, s).
Example 14: The Preparation of Compound I-4757




To a solution of 1.63 g (0.01 mol) 4,5-dichloro-6-methylpyrimidine and 2.75 g (0.01 mol) 2-(4-(4,6-dimethoxypyrimidin-2-yloxy)phenyl)ethanamine (the preparation refers to Example 3, the difference is replacing 2-chloro-5-(trifluoromethyl)pyridine to 4,6-dimethoxy-2-(methylsulfonyl)pyrimidine) in 50 mL toluene was added 2.02 g (0.02 mol)triethylamine after the reaction mixture was dissolved. The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 3.24 g compound I-4757 as white solid with yield of 81%, m.p. 119-120° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.46 (3H, s), 2.95 (2H, t), 3.82 (2H, m), 3.84 (6H, s), 5.43 (1H, s), 5.78 (1H, s), 7.26 (4H, m), 8.40 (1H, s).
Example 15: The Preparation of Compound I-6730




To a solution of compound I-22 0.41 g (0.01 mol) in 20 mL ethanol was dropwise added 10 mL of concentrated hydrochloric acid at room temperature, The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, the brown residue was washed with (3×50 mL) of acetone to obtain 0.33 g compound I-6730 as white solid with yield of 75%, m.p. 108-110° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ(ppm): 2.49 (3H, s), 2.88 (2H, t), 3.64 (2H, m), 7.08 (2H, d), 7.17 (1H, d), 7.35 (2H, d), 7.37 (1H, m), 8.16 (1H, d), 8.25 (1H, s), 8.50 (1H, s).
Example 16: The Preparation of 2-(4-(2-chloro-4-(trifluoromethyl)phenoxy)phenyl)ethanamine
1) The Preparation of 2-(4-(2-chloro-4-(trifluoromethyl)phenoxy)phenyl)acetonitrile




To a solution of 150 mL N,N-dimethyl formamide was added 1,2-dichloro-4-(trifluoromethyl)benzene 25.8 g (0.12 mol), 2-(4-hydroxyphenyl)acetonitrile 13.3 g (0.1 mol) and potassium carbonate 27.60 g (0.2 mol). The reaction mixture was continued stirring and heating to reflux overnight, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. Then the mixture was poured into 300 mL of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of 5% aqueous solution of NaOH, and 50 mL of brine successively, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 14.55 g target intermediate as white solid with yield of 46.2%, m.p. 66.2° C.
2) The Preparation of 2-(4-(2-chloro-4-(trifluoromethyl)phenoxy)phenyl)ethanamine hydrochloride




To a solution of 2-(4-(2-chloro-4-(trifluoromethyl)phenoxy)phenyl)acetonitrile 3.12 g (0.01 mol), Raney nickel (1.0 g) and 10 mL of 25% aqueous ammonia in 50 mL ethanol was filled with hydrogen at high pressure, then the reaction mixture was continued stirring at room temperature for 3 hours and monitored by TLC until the reaction was over, Raney nickel was filtered, the solution was concentrated under reduced pressure to give sticky liquid. To a solution of the residue was dropwise added 5 mL of concentrated hydrochloric acid and stirred for half an hour at room temperature until target intermediate precipitated, filtered to obtain 3.45 g white solid with yield of 97.9%, m.p. 155.7° C.
Example 17: The Preparation of 2-(4-(2,6-dichloro-4-nitrophenoxy)phenyl)ethanamine hydrochloride
1) The Preparation of tert-butyl 4-(2,6-dichloro-4-nitrophenoxy)phenethylcarbamate




To a solution of tert-butyl 4-hydroxyphenethylcarbamate 2.10 g (0.01 mol) and 1,3-dichloro-2-fluoro-5-nitrobenzene 2.33 g (0.01 mol) in 50 mL butanone was added potassium carbonate 2.76 g (0.02 mol). The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 3.73 g target intermediate as white solid with yield of 87.3%, m.p. 149-151° C.
2) The Preparation of 2-(4-(2,6-dichloro-4-nitrophenoxy)phenyl)ethanamine




To a solution of tert-butyl 4-(2,6-dichloro-4-nitrophenoxy)phenethylcarbamate 4.27 g (0.01 mol) in 50 mL ethyl acetate was dropwise added 6 mL trifluoroacetic acid until the solid was dissolved at room temperature for 4-5 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure to give 3.03 g target intermediate as white solid with yield of 92.8%, m.p. 107-109° C.
Example 18: The Preparation of 2-(4-(4-(trifluoromethyl)phenoxy)phenyl)ethanamine
1) The Preparation of tert-butyl 4-(4-(trifluoromethyl)phenoxy)phenethylcarbamate




To a solution of 4-(trifluoromethyl)phenylboronic acid 4.56 g (0.024 mol) in 50 mL dichloromethane was added 4A molecular sieve powder, Cupric Acetate Anhydrous 3.82 g (0.021 mol), triethylamine 10.1 g (0.1 mol), and pyridine 7.9 g (0.1 mol) successively; The reaction mixture was continued to react overnight, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, filtered and the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 5.95 g target intermediate as white solid with yield of 65.1%.
2) The Preparation of 2-(4-(4-(trifluoromethyl)phenoxy)phenyl)ethanamine hydrochloride




To a solution of tert-butyl 4-(4-(trifluoromethyl)phenoxy)phenethylcarbamate 3.81 g (0.01 mol) in 50 mL ethyl acetate was dropwise added 12 mL concentrated hydrochloric acid. The reaction mixture was continued to stir for 4-5 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to react for half an hour and filtered to give 2.92 g target intermediate as white solid with yield of 91.9%.
Example 19: The Preparation of Compound II-69




To a solution of 1.63 g (0.01 mol) 4,5-dichloro-6-methylpyrimidine and 3.18 g (0.01 mol) 2-(4-(4-(trifluoromethyl)phenoxy)phenyl)ethanamine hydrochloride in 50 mL toluene was added 4.45 g (0.022 mol)triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:2, as an eluent) to obtain 2.76 g compound II-69 as colourless oil with yield of 72.6%.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.46 (3H, s), 2.94 (2H, t), 3.77 (2H, q), 5.42 (1H, s), 702 (4H, m), 7.25 (2H, m), 7.56 (2H, d), 8.39 (1H, s).
Example 20: The Preparation of Compound II-165




To a solution of 1.63 g (0.01 mol) 4,5-dichloro-6-methylpyrimidine and 3.26 g (0.01 mol) 2-(4-(2,6-dichloro-4-nitrophenoxy)phenyl)ethanamine in 50 mL toluene was added 4.45 g (0.022 mol)triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. Then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:2, as an eluent) to obtain 3.23 g compound II-165 as rufous solid with yield of 71.2%, m.p. 118-120° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.45 (3H, s), 2.91 (2H, t), 3.70-3.85 (2H, q), 5.42 (1H, t), 6.80 (2H, d), 7.18 (2H, d), 8.31 (2H, s), 8.38 (1H, s).
Example 21: The Preparation of Compound II-297




To a solution of 1.77 g (0.01 mol) 4,5-dichloro-6-ethylpyrimidine (the preparation refers to Example 1, the difference is replacing ethyl 2-chloro-3-oxobutanoate to ethyl 2-chloro-3-oxopentanoate) and 2.84 g (0.01 mol) 2-(4-(4-chlorophenoxy)phenyl)ethanamine hydrochloride (the preparation refers to Example 18, the difference is replacing 4-(trifluoromethyl)phenylboronic acid to 4-chlorophenylboronic acid) in 50 mL toluene was added 4.45 g (0.022 mol)triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:2, as an eluent) to obtain 3.16 g compound II-297 as rufous solid with yield of 81.6%, m.p. 84.7° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 1.26 (3H, t), 2.78 (2H, dd), 2.92 (2H, t), 3.75 (2H, dd), 5.45 (1H, t), 6.84-7.00 (4H, m), 7.20 (2H, d), 7.29 (2H, d), 8.44 (1H, s).
Example 22: The Preparation of Compound II-303




To a solution of 1.77 g (0.01 mol) 4,5-dichloro-6-ethylpyrimidine and 3.19 g (0.01 mol) 2-(4-(3,5-dichlorophenoxy)phenyl)ethanamine hydrochloride (the preparation refers to Example 18, the difference is replacing 4-(trifluoromethyl)phenylboronic acid to 3,5-dichlorophenylboronic acid) in 50 mL toluene was added 4.45 g (0.022 mol)triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:2, as an eluent) to obtain 3.17 g compound II-303 as pale rufous oil with yield of 75.1%.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 1.26 (3H, t), 2.78 (2H, dd), 2.95 (2H, t), 3.72-3.84 (2H, q), 5.45 (1H, t), 6.85 (2H, d), 7.00 (2H, d), 7.25 (2H, d), 8.45 (1H, s).
Example 23: The Preparation of Compound II-347




To a solution of 1.77 g (0.01 mol) 4,5-dichloro-6-ethylpyrimidine and 3.18 g (0.01 mol) 2-(4-(4-(trifluoromethyl)phenoxy)phenyl)ethanamine hydrochloride in 50 mL toluene was added 4.45 g (0.022 mol)triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:2, as an eluent) to obtain 3.15 g compound II-347 as white solid with yield of 74.8%, m.p. 52.6° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 1.27 (3H, t), 2.78 (2H, q), 2.95 (2H, t), 3.78 (2H, q), 5.42 (1H, s), 7.01 (4H, m), 7.24 (2H, m), 7.58 (2H, d), 8.45 (1H, s).
Example 24: The Preparation of Compound II-8915




To a solution of 1.98 g (0.01 mol) 4,5-dichloro-6-(difluoromethyl)pyrimidine (the preparation refers to Example 1, the difference is replacing ethyl 2-chloro-3-oxobutanoate to ethyl 2-chloro-4,4-difluoro-3-oxobutanoate) and 2.84 g (0.01 mol) 2-(4-(4-chlorophenoxy)phenyl)ethanamine hydrochloride in 50 mL toluene was added 4.45 g (0.022 mol)triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:2, as an eluent) to obtain 2.89 g compound II-8915 as white solid with yield of 70.5%, m.p. 98.5° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.94 (2H, t), 3.76-3.86 (2H, q), 5.71 (1H, s), 6.72 (1H, t), 6.90-7.05 (4H, m), 7.17-7.32 (4H, m), 8.57 (1H, s).
Example 25: The Preparation of Compound II-10583




To a solution of 1.98 g (0.01 mol) 4,5-dichloro-6-(difluoromethyl)pyrimidine (the preparation refers to Example 1, the difference is replacing ethyl 2-chloro-3-oxobutanoate to ethyl 2-chloro-4,4-difluoro-3-oxobutanoate) and 3.14 g (0.01 mol) 2-(4-(4-chlorophenoxy)-3-methoxyphenyl)ethanamine hydrochloride in 50 mL toluene was added 4.45 g (0.022 mol)triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:2, as an eluent) to obtain 2.89 g compound II-10583 as rufous oil with yield of 76.8%.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.95 (2H, t), 3.80-3.92 (5H, m), 5.72 (1H, s), 6.72 (1H, t), 6.75-6.97 (5H, m), 7.20-7.26 (2H, m), 8.58 (1H, s).
Example 26: The Preparation of Compound II-19334




To a solution of compound II-347 0.42 g (0.01 mol) in 20 mL ethanol was dropwise added 10 mL of concentrated hydrochloric acid at room temperature. The reaction mixture was heated to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, the brown residue was washed with (3×10 mL) of ethyl acetate to obtain 0.36 g compound II-19334 as white solid with yield of 78.1%, m.p. 120.5° C.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 1.27 (3H, t), 2.80-3.09 (4H, m), 3.80 (2H, d), 6.92-7.18 (4H, d), 7.31 (2H, d), 7.67 (2H, d), 8.71 (1H, d), 9.28 (1H, s).
Example 27: The Preparation of 2-(6-(4-chlorophenoxy)pyridin-3-yl)ethanamine
1) The Preparation of methyl 6-(4-chlorophenoxy)nicotinate




To a solution of 25.6 g (0.2 mol) 4-chlorophenol in 350 mL N,N-dimethylformamide was added 70% sodium hydride 103 g (3.0 mol) in batches. The reaction mixture was stirred for 4 hours at room temperature, then 34.2 g (0.2 mol) methyl 6-chloronicotinate was added in batches, then the reaction temperature was raised to 100° C. to react for 10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the solution was poured into water, extracted with ethyl acetate, the organic phase was washed with water, saturated brine successively, dried, filtered and evaporated under reduced pressure, the cooled residual was filtered and washed with petroleum ether, to obtain 42.0 g air dried target intermediate as brown solid, m.p. 64-66° C. 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ(ppm): 3.92 (3H, s), 6.75 (1H, d), 6.96 (1H, d), 7.11 (2H, d), 7.37 (2H, d), 8.30 (1H, d), 8.81 (1H, s).
2) The Preparation of (6-(4-chlorophenoxy)pyridin-3-yl)methanol




To a solution of 52.6 g (0.2 mol) methyl 6-(4-chlorophenoxy)nicotinate in 500 mL anhydrous ether was dropwise added 65% Red-Al 74.5 g (0.24 mol) in toluene at 0□. then the reaction mixture was stirred for 4 hours at room temperature, then at 0□, 10% sodium hydroxide solution prepared beforehand was dropwise added until the reaction solution was clarified, then the reaction temperature was raised to 35 □ to react for 2 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the solution was poured into water, extracted with ethyl acetate, the organic phase was washed with water, saturated brine successively, dried, filtered and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to obtain 42.2 g target intermediate as white solid, m.p. 100-102° C. 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 3.20 (1H, bs), 4.56 (2H, s), 6.87 (1H, d), 7.04 (2H, d), 7.33 (2H, d), 7.69 (1H, d), 8.06 (1H, s).
3) The Preparation of 5-(chloromethyl)-2-(4-chlorophenoxy)pyridine




To a solution of 23.5 g (0.1 mol) (6-(4-chlorophenoxy)pyridin-3-yl)methanol in 350 mL dichloromethane was dropwise added 17.9 g (0.15 mol) sulfoxide chloride at 0° C. then the reaction mixture was stirred for 4 hours at room temperature, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive sulfoxide chloride was evaporated and the residual was poured into water, extracted with ethyl acetate, the organic phase was washed with water, saturated sodium bicarbonate solution, and saturated brine successively, dried, filtered and evaporated under reduced pressure, to obtain 22.8 g target intermediate as white solid, m.p. 78-80° C. 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ(ppm): 4.55 (2H, s), 6.94 (1H, d), 7.09 (2H, d), 7.36 (2H, d), 7.75 (1H, d), 8.15 (1H, s).
4) The Preparation of 2-(6-(4-chlorophenoxy)pyridin-3-yl)acetonitrile




To a solution of 2.69 g (55 mmol) sodium cyanide dissolved in 300 mL dimethyl sulfoxide was added 13.9 g (50 mmol) 5-(chloromethyl)-2-(4-chlorophenoxy)pyridine and the catalytic amount of 18-Crown-6 at 40° C. then the reaction mixture was raised to 80° C. to react for 2 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the residual was poured into water, extracted with toluene, the organic phase was washed with water, and saturated brine successively, dried, filtered and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to obtain 11.2 g target intermediate as white solid, m.p. 100-102° C. 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 3.70 (2H, s), 6.97 (1H, d), 7.08 (2H, d), 7.37 (2H, d), 7.71 (1H, d), 8.10 (1H, s).
5) The Preparation of 2-(6-(4-chlorophenoxy)pyridin-3-yl)ethanamine




To a solution of 2-(6-(4-chlorophenoxy)pyridin-3-yl)acetonitrile 2.44 g (0.01 mol), Raney nickel (1.0 g) and 10 mL of 25% aqueous ammonia in 50 mL ethanol was filled with hydrogen, then the reaction mixture was continued stirring at room temperature for 3-15 hours and monitored by TLC until the reaction was over, Raney nickel was filtered, the solution was concentrated under reduced pressure to give 2.30 g jade-green sticky liquid with yield of 95.0%, colourless oil. 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ(ppm): 1.46 (2H, bs), 2.70 (2H, t), 2.94 (2H, t), 6.87 (1H, d), 7.07 (2H, dd), 7.34 (2H, dd), 7.55 (1H, dd), 8.02 (1H, d).
Example 28: The Preparation of Compound III-7




To a solution of 0.25 g (1.0 mmol) 2-(6-(4-chlorophenoxy)pyridin-3-yl)ethanamine and 0.21 g (1.5 mmol) potassium carbonate in 10 mL N,N-dimethylformamide was added 0.16 g (1.0 mmol) 4,5-dichloro-6-methylpyrimidine, then the reaction mixture was raised to 80° C. to react for 2 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the residual was poured into water, extracted with ethyl acetate, the organic phase was washed with water, and saturated brine successively, dried, filtered and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 0.28 g compound III-7 as colourless oil. 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.46 (3H, t), 2.91 (2H, t), 3.75 (2H, m), 5.43 (1H, bs), 6.89 (1H, d), 7.07 (2H, d), 7.35 (2H, d), 7.58 (1H, dd), 8.03 (1H, d), 8.39 (1H, s).
Example 29: The Preparation of Compound III-202




To a solution of 0.28 g (1.0 mmol) 2-(6-(4-(trifluoromethyl)phenoxy)pyridin-3-yl)ethanamine (the preparation refers to Example 27, the difference is replacing 4-chlorophenol to 4-(trifluoromethyl)phenol) and 0.21 g (1.5 mmol) potassium carbonate in 10 mL N,N-dimethylformamide was added 0.18 g (1.0 mmol) 4,5-dichloro-6-ethylpyrimidine (the preparation refers to Example 1, the difference is replacing ethyl 2-chloro-3-oxobutanoate to ethyl 2-chloro-3-oxopentanoate). then the reaction mixture was raised to 80° C. to react for 2 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the residual was poured into water, extracted with ethyl acetate, the organic phase was washed with water, and saturated brine successively, dried, filtered and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 0.30 g compound III-202 as colourless oil.
1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 1.28 (3H, t), 2.78 (2H, m), 2.93 (2H, t), 3.76 (2H, m), 5.43 (1H, bs), 6.96 (1H, d), 7.20-7.23 (2H, m), 7.61-7.66 (3H, m), 8.06 (1H, d), 8.44 (1H, s).
Example 30: The Preparation of Compound III-622




To a solution of 0.28 g (1.0 mmol) 2-(6-(2,4-dichlorophenoxy)pyridin-3-yl)ethanamine (the preparation refers to Example 27, the difference is replacing 4-chlorophenol to 2,4-dichlorophenol) and 0.21 g (1.5 mmol) potassium carbonate in 10 mL N,N-dimethylformamide was added 4,5-dichloro-6-(difluoromethyl)pyrimidine 0.20 g (1.0 mmol). then the reaction mixture was raised to 80° C. to react for 2 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the residual was poured into water, extracted with ethyl acetate, the organic phase was washed with water, and saturated brine successively, dried, filtered and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 0.32 g compound III-622 as colourless oil. 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.92 (2H, t), 3.80 (2H, m), 5.72 (1H, bs), 6.54, 6.72, 6.90 (1H, t), 6.89 (1H, s), 6.98 (1H, d), 7.14 (1H, d), 7.27-7.31 (2H, m), 7.48 (1H, d), 7.61 (1H, dd), 7.98 (1H, d), 8.56 (1H, s).
Example 31: The Preparation of Compound III-2630




To a solution of 0.26 g (1.0 mmol) 2-(6-(4-chloro-2-methylphenoxy)pyridin-3-yl)ethanamine (the preparation refers to Example 27, the difference is replacing 4-chlorophenol to 4-chloro-2-methylphenol) and 0.21 g (1.5 mmol) potassium carbonate in 10 mL N,N-dimethylformamide was added 0.18 g (1.0 mmol) 4,5,6-trichloropyrimidine (the preparation refers to Example 1, the difference is replacing ethyl 2-chloro-3-oxobutanoate to diethyl 2-chloromalonate). then the reaction mixture was raised to 80° C. to react for 2 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the residual was poured into water, extracted with ethyl acetate, the organic phase was washed with water, and saturated brine successively, dried, filtered and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:4, as an eluent) to obtain 0.32 g compound III-2630 as colourless oil. 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 2.15 (3H, s), 2.89 (2H, t), 3.73-3.79 (2H, m), 5.62 (1H, bs), 6.87 (1H, d), 6.98 (1H, d), 7.18-7.22 (2H, m), 7.54 (1H, dd), 8.00 (1H, d), 8.29 (1H, s).
Other compounds represented by the general formula PY of the present invention were prepared according to the above examples.
Physical properties and 1HNMR spectrum (1HNMR, 300 MHz, internal standard: TMS, ppm) of some compounds of this invention are as follows:
Compound I-23: m.p. 147.5° C. δppm 2.46 (3H, s), 2.97 (2H, t), 3.78 (2H, q), 5.42 (1H, m), 7.01 (1H, d), 7.10 (2H, d), 7.30 (2H, d), 7.92 (1H, d), 8.40 (1H, s), 8.47 (1H, s).
Compound I-34: m.p. 109.0° C. δppm 2.46 (3H, s), 2.96 (2H, t), 3.79 (2H, q), 3.92 (3H, s), 5.43 (1H, m), 6.94 (1H, d), 7.12 (2H, d), 7.28 (2H, d), 8.28 (1H, d), 8.40 (1H, s), 8.82 (1H, s).
Compound I-35: yellow oil. δppm 1.38 (3H, t), 2.46 (3H, s), 2.96 (2H, t), 3.79 (2H, q), 4.38 (2H, q), 5.43 (1H, m), 6.93 (1H, d), 7.12 (2H, d), 7.28 (2H, d), 8.28 (1H, d), 8.40 (1H, s), 8.83 (1H, s).
Compound I-80: δppm 2.47 (3H, s), 2.95 (2H, t), 3.79 (2H, q), 5.55 (1H, m), 7.09 (1H, d), 7.18 (2H, m), 7.37 (1H, s), 7.93 (1H, m), 8.41 (2H, m).
Compound I-196: δppm 2.46 (3H, t), 2.96 (2H, t), 3.75 (3H, s), 3.80 (2H, dd), 5.49 (1H, t), 6.87 (2H, s), 7.02 (1H, d), 7.09 (1H, d), 7.88 (1H, d), 8.41 (2H, s).
Compound I-255: yellow oil. δppm 1.27 (3H, t), 2.79 (2H, q), 2.97 (2H, t), 3.80 (2H, q), 5.48 (1H, m), 7.02 (1H, d), 7.10 (2H, d), 7.30 (2H, d), 7.92 (1H, d), 8.46 (1H, s), 8.47 (1H, s).
Compound I-266: m.p. 102.2° C. δppm 1.26 (3H, t), 2.79 (2H, q), 2.97 (2H, t), 3.79 (2H, q), 3.92 (3H, s), 5.44 (1H, m), 6.94 (1H, d), 7.12 (2H, d), 8.29 (2H, d), 8.27 (1H, d), 8.45 (1H, s), 8.82 (1H, s).
Compound I-267: yellow oil. δppm 1.26 (3H, t), 1.38 (3H, t), 2.79 (2H, t), 2.98 (2H, t), 3.79 (2H, q), 4.38 (2H, q), 5.43 (1H, m), 6.93 (1H, d), 7.12 (2H, d), 7.29 (2H, d), 8.27 (1H, d), 8.45 (1H, s), 8.83 (1H, s).
Compound I-312: δppm 1.27 (3H, t), 2.80 (3H, q), 2.96 (2H, t), 3.80 (2H, q), 5.51 (1H, m), 7.09 (1H, d), 7.18 (2H, m), 7.37 (1H, s), 7.93 (1H, m), 8.40 (1H, s), 8.46 (1H, s).
Compound I-428: δppm 1.26 (3H, t), 2.79 (2H, dd), 2.96 (2H, t), 3.75 (3H, s), 3.81 (2H, dd), 5.50 (1H, t), 6.87 (2H, d), 7.02 (1H, d), 7.10 (1H, d), 7.88 (1H, s), 8.40 (1H, s), 8.45 (1H, s).
Compound I-467: m.p. 102-103° C. δppm 2.46 (3H, s), 2.96 (2H, t), 3.78 (2H, q), 5.43 (1H, s), 7.11 (2H, d), 7.27 (2H, d), 7.78 (1H, s), 7.97 (1H, s), 8.40 (1H, s).
Compound I-486: m.p. 92-93° C. δppm 2.47 (3H, s), 2.98 (2H, t), 3.80 (2H, q), 5.44 (1H, s), 7.13 (2H, d), 7.30 (2H, d), 7.98 (1H, s), 8.28 (1H, s), 8.41 (1H, s).
Compound I-502: m.p. 128.5° C. δppm 2.49 (3H, s), 2.89 (2H, t), 3.63 (2H, q), 5.34 (1H, m), 7.06 (2H, d), 7.28 (2H, d), 7.72 (2H, s), 8.24 (1H, s), 8.38 (1H, s), 8.46 (1H, s).
Compound I-602: colourless oil. Δppm 2.88 (2H, t), 4.06 (2H, q), 5.49 (s, 1H), 7.21 (4H, m,), 8.28 (1H, d), 8.28 (1H, s), 68.450 (1H, s).
Compound I-618: m.p. 168.9° C. δppm 1.26 (3H, t), 2.79 (2H, q), 2.97 (2H, t), 3.80 (2H, q), 5.47 (1H, m), 5.83 (2H, s), 7.13 (2H, d), 7.30 (2H, d), 8.28 (1H, s), 8.40 (1H, s), 8.44 (1H, s).
Compound I-699: m.p. 146-147° C. δppm 2.45 (3H, s), 2.96 (2H, t), 3.78 (2H, q), 5.45 (1H, s), 7.11 (2H, d), 7.28 (2H, d), 7.84 (1H, s), 8.41 (1H, s).
Compound I-815: m.p. 98-100° C. δppm 1.26 (3H, t), 2.79 (2H, q), 2.96 (2H, t), 3.79 (2H, q), 5.43 (1H, s), 7.11 (2H, d), 7.27 (2H, d), 7.84 (1H, s), 8.46 (1H, s).
Compound I-929: yellow oil. δppm 2.46 (3H, s), 2.96 (2H, t), 3.87 (2H, q), 5.47 (1H, m), 7.09 (1H, m), 7.14 (2H, d), 7.28 (2H, d), 7.98 (1H, d), 8.29 (1H, d), 8.40 (1H, s).
Compound I-987: yellow oil. δppm 1.26 (3H, t), 2.79 (2H, q), 2.96 (2H, t), 3.78 (2H, q), 5.46 (1H, m), 7.13 (1H, q), 7.15 (2H, d), 7.29 (2H, d), 8.00 (1H, d), 8.30 (1H, d), 8.45 (1H, s).
Compound I-1045: m.p. 80-83° C. δppm 1.39 (3H, t), 2.46 (3H, s), 2.94 (2H, t), 3.77 (2H, q), 5.47 (1H, s), 7.06 (1H, m), 7.12 (2H, d), 7.26 (2H, d), 8.27 (1H, m), 8.40 (1H, s).
Compound I-1199: m.p. 147-149° C. δppm 2.47 (3H, s), 2.97 (2H, t), 3.06 (3H, d), 3.62-3.79 (2H, q), 5.50 (1H, t), 7.12 (2H, d), 7.16 (1H, dd), 7.32 (2H, d), 7.86 (1H, s), 8.20 (1H, dd), 8.41 (1H, s), 8.64 (1H, dd).
Compound I-1219: m.p. 113-114° C. δppm 1.39 (3H, t), 2.79 (3H, s), 2.95 (2H, t), 3.78 (2H, q), 4.41 (2H, q), 5.49 (1H, t), 7.09 (3H, m), 7.27 (2H, m), 8.26 (2H, m), 8.45 (1H, s).
Compound I-1414: δppm 2.47 (3H, s), 2.96 (2H, t), 3.80 (2H, q), 5.46 (1H, m), 7.20 (2H, s), 7.37 (1H, s), 8.00 (1H, d), 8.24 (1H, d), 8.41 (1H, s).
Compound I-1472: δppm 1.27 (3H, t), 2.80 (2H, q), 2.97 (2H, t), 3.80 (2H, q), 5.47 (1H, m), 7.21 (2H, s), 7.37 (1H, s), 8.00 (1H, d), 8.25 (1H, d), 8.46 (1H, s).
Compound I-1646: δppm 2.46 (3H, t), 2.96 (2H, t), 3.74 (3H, s), 3.81 (2H, dd), 5.48 (1H, t), 6.89 (2H, t), 7.11 (1H, d), 7.96 (1H, d), 8.23 (1H, t), 8.41 (1H, s).
Compound I-1704: δppm 1.26 (3H, t), 2.79 (2H, dd), 2.96 (2H, t), 3.73 (3H, s), 3.79 (2H, dd), 5.48 (1H, t), 6.88 (2H, d), 7.12 (1H, d), 7.96 (1H, d), 8.23 (1H, s), 8.45 (1H, s).
Compound I-1762: δppm 2.50 (3H, s), 2.96 (2H, t), 3.78 (2H, q), 5.54 (1H, m), 7.01 (1H, d), 7.12 (1H, d), 7.30 (2H, d), 7.90 (1H, m), 8.41 (1H, s), 8.44 (1H, s).
Compound I-1820: δppm 1.26 (3H, t), 2.81 (3H, q), 2.97 (2H, t), 3.78 (2H, q), 5.55 (1H, m), 7.01 (1H, d), 7.11 (2H, d), 7.30 (2H, d), 7.90 (1H, m), 8.44 (1H, s).
Compound I-1878: δppm 2.50 (3H, s), 2.97 (2H, t), 3.79 (2H, q), 5.53 (1H, m), 7.14 (2H, d), 7.30 (3H, m), 7.99 (1H, s), 8.27 (1H, s), 8.40 (1H, s).
Compound I-1936: δppm 1.26 (3H, t), 2.81 (3H, q), 2.97 (2H, t), 3.79 (2H, q), 5.54 (1H, m), 7.13 (2H, d), 7.31 (2H, d), 7.98 (1H, m), 8.27 (1H, s), 8.44 (1H, s).
Compound I-2052: δppm 1.30 (3H, t), 2.83 (2H, q), 2.95 (2H, t), 3.79 (2H, q), 5.61 (1H, m), 7.09 (1H, d), 7.18 (2H, m), 7.33 (1H, s), 7.93 (1H, m), 8.43 (1H, d).
Compound I-2400: δppm 2.98 (3H, t), 3.85 (2H, q), 5.77 (1H, m), 6.73 (1H, m), 7.10 (1H, d), 7.19 (2H, m), 7.38 (1H, s), 7.94 (1H, m), 8.40 (1H, s), 8.59 (1H, s).
Compound I-2458: δppm 2.98 (2H, t), 3.75 (3H, s), 3.87 (2H, dd), 5.77 (1H, t), 6.72 (1H, t), 6.89 (2H, t), 7.03 (1H, d), 7.10 (1H, t), 7.88 (1H, dd), 8.40 (1H, s), 8.59 (1H, s).
Compound I-2555: brown oil. δppm 8.576 (s, 1H, pyrimidine-H), 7.965-7.972 (d, 1H, pyridine-6-H), 7.776-7.783 (d, 1H, pyridine-4-H), 7.128-7.294 (dd, 4H, Ar—H), 6.726-7.100 (t, 1H, F2C—H), 3.828-3.849 (q, 2H, N—CH2—C), 2.951-2.999 (t, 2H, C— CH2—Ar).
Compound I-2611: m.p. 156-157° C. δppm 8.583 (s, 1H, pyrimidine-H), 8.337-8.393 (m, 3H, pyridine-H), 7.164-7.322 (dd, 4H, Ar—H), 6.550-6.909 (t, 1H, F2C—H), 5.739 (s, 1H, NH), 3.816-3.883 (q, 2H, N—CH2—C), 2.968-3.015 (t, 2H, C—CH2—Ar).
Compound I-2690: δppm 2.98 (2H, t), 3.74 (3H, s), 3.86 (2H, dd), 5.76 (1H, t), 6.72 (1H, t), 6.88 (2H, d), 7.13 (1H, d), 7.96 (1H, d), 8.23 (1H, s), 8.58 (1H, s).
Compound I-2787: δppm 8.575 (s, 1H, pyrimidine-H), 7.965-7.972 (d, 1H, pyridine-6-H), 7.775-7.782 (d, 1H, pyridine-4-H), 7.105-7.295 (dd, 4H, Ar—H), 5.882 (s, 1H, NH), 3.815-3.881 (q, 2H, N—CH2—C), 2.955-3.001 (t, 2H, C—CH2—Ar).
Compound I-2843: m.p. 123-124° C. δppm 8.577 (s, 1H, pyrimidine-H), 8.336-8.394 (m, 3H, pyridine-H), 7.152-7.325 (dd, 4H, Ar—H), 5.917 (s, 1H, NH), 3.826-3.917 (q, 2H, N—CH2—C), 2.972-3.020 (t, 2H, C—CH2—Ar).
Compound I-3077: m.p. 130-132° C. δppm 2.46 (3H, s), 2.95 (2H, t), 3.77 (2H, q), 5.50 (1H, s), 7.16 (3H, m), 7.27 (2H, m), 7.48 (1H, d), 8.40 (1H, s).
Compound I-4121: δppm 2.50 (3H, s), 2.95 (2H, t), 3.77 (2H, q), 5.57 (1H, m), 7.16 (3H, m), 7.29 (2H, m), 7.49 (1H, d), 8.40 (1H, s).
Compound I-5221: m.p. 121-124° C. δppm 1.26 (3H, t), 2.78 (2H, q), 2.95 (2H, t), 3.78 (2H, m), 3.84 (6H, s), 5.44 (1H, s), 5.78 (1H, s), 7.20 (4H, m), 8.45 (1H, s).
Compound I-6729: m.p. 102.8° C. δppm 2.49 (3H, s), 2.88 (2H, t), 3.81 (2H, m), 7.11 (2H, d), 18 (1H, d), 7.30 (2H, d), 7.52 (1H, d), 8.17 (1H, d), 8.50 (1H, s), 8.78 (1H, s), 9.40 (1H, s).
Compound I-6731: m.p. 148.6° C. δppm 2.30 (3H, s), 2.49 (3H, s), 2.93 (2H, t), 3.81 (2H, m), 7.27-7.05 (8H, m), 7.29 (2H, d), 7.51 (1H, d), 8.14 (1H, d), 8.47 (1H, s), 8.77 (1H, s), 9.33 (1H, s).
Compound I-6732: m.p. 164.6° C. δppm 2.50 (3H, s), 2.94 (2H, t), 3.81 (2H, m), 7.09 (2H, d), 7.18 (1H, d), 7.30 (2H, d), 8.18 (1H, d), 8.50 (1H, s), 8.81 (1H, s), 9.28 (1H, s).
Compound I-6733: m.p. 113.7° C. δppm 2.35 (3H, s), 2.89 (2H, t), 3.64 (2H, m), 7.09 (2H, d), 7.16 (1H, d), 7.30 (2H, d), 7.37 (1H, m), 8.15 (1H, d), 8.19 (1H, s), 8.51 (1H, s).
Compound I-6734: m.p. 56.9° C. δppm 2.37 (3H, s), 2.90 (2H, t), 3.66 (2H, m), 7.09 (2H, d), 7.16 (1H, d), 7.29 (2H, d), 7.49 (1H, m), 8.16 (1H, d), 8.30 (1H, s), 8.50 (1H, s).
Compound I-6735: m.p.>300° C. δppm 2.35 (3H, s), 2.88 (2H, t), 3.62 (2H, m), 7.08 (2H, d), 7.15 (1H, d), 7.36 (1H, m), 8.15 (1H, d), 7.32 (2H, d), 8.20 (1H, s), 8.48 (1H, s).
Compound I-6790: δppm 1.23 (3H, t), 2.51 (3H, s), 2.74 (2H, q), 2.94 (2H, t), 3.77 (2H, q), 5.40 (1H, m), 7.11 (2H, d), 7.26 (2H, d), 7.84 (1H, s).
Compound I-6791: yellow oil. δppm 1.23 (3H, t), 2.50 (3H, s), 2.74 (2H, q), 2.96 (2H, t), 3.79 (2H, q), 5.39 (1H, m), 5.83 (2H, s), 7.13 (2H, d), 7.30 (2H, d), 8.26 (1H, s), 8.40 (1H, s).
Compound I-6793: m.p. 116.0° C. δppm 1.23 (3H, t), 2.51 (3H, s), 2.74 (2H, q), 2.94 (2H, t), 3.77 (2H, q), 5.40 (1H, m), 7.10 (1H, m), 7.14 (2H, d), 7.29 (2H, d), 8.00 (1H, d), 8.31 (1H, d).
Compound I-6795: yellow oil. δppm 1.24 (3H, t), 2.46 (3H, s), 2.74 (2H, q), 2.96 (2H, t), 3.78 (2H, q), 5.40 (1H, m), 7.01 (1H, d), 7.10 (2H, d), 7.30 (2H, d), 7.91 (1H, d), 8.47 (1H, s).
Compound I-6796: m.p. 90.8° C. δppm 1.23 (3H, t), 1.38 (3H, t), 2.51 (3H, s), 2.74 (2H, q), 2.95 (2H, t), 3.78 (2H, q), 4.38 (2H, q), 5.38 (1H, m), 6.93 (1H, d), 7.11 (2H, d), 7.29 (2H, d), 8.28 (1H, d), 8.83 (1H, s).
Compound I-6797: yellow oil. δppm 1.23 (3H, t), 2.49 (3H, s), 2.74 (2H, q), 2.95 (2H, t), 3.78 (2H, q), 3.92 (3H, s), 5.39 (1H, m), 6.93 (1H, d), 7.11 (2H, d), 7.29 (2H, d), 8.28 (1H, d), 8.82 (1H, s).
Compound I-6806: δppm 1.24 (3H, t), 2.51 (3H, s), 2.75 (2H, q), 2.94 (2H, t), 3.79 (2H, q), 5.40 (1H, m), 7.09 (1H, d), 7.17 (2H, m), 7.33 (1H, s), 7.93 (1H, m), 8.41 (1H, s).
Compound II-19: δppm 2.52 (3H, s), 2.92 (2H, t), 3.75 (2H, dd), 5.43 (1H, t), 6.81-7.01 (4H, m), 7.19 (2H, d), 7.28 (2H, d), 8.39 (1H, s).
Compound II-21: δppm 2.46 (3H, s), 2.92 (2H, t), 3.75 (2H, dd), 5.42 (1H, t), 6.89 (1H, d), 6.92 (2H, d), 7.15-7.22 (3H, m), 7.47 (1H, d), 8.39 (1H, s).
Compound II-25: δppm 2.45 (3H, s), 2.95 (2H, t), 3.70-3.83 (2H, q), 5.44 (1H, t), 6.84 (2H, d), 7.00 (2H, d), 7.06 (1H, s), 7.26 (2H, d), 8.40 (1H, s).
Compound II-53: m.p. 140-142° C. δppm 2.65 (3H, s), 3.13 (2H, t), 3.65-3.76 (2H, q), 6.93 (1H, d), 7.17 (2H, d), 7.35 (2H, d), 8.31 (1H, d), 8.47 (1H, s), 8.62 (1H, t), 9.14 (1H, d).
Compound II-154: δppm 2.46 (3H, s), 2.95 (2H, t), 3.77 (2H, dd), 5.42 (1H, t), 6.92 (1H, d), 7.00 (2H, d), 7.25 (2H, d), 7.43 (1H, d), 7.75 (1H, s), 8.39 (1H, s).
Compound II-204: δppm 2.47 (3H, s), 2.96 (2H, t), 3.77 (2H, dd), 5.43 (1H, t), 6.93 (1H, t), 7.02 (2H, d), 7.26 (2H, d), 7.37 (1H, dd), 7.48 (1H, dd), 8.40 (1H, s).
Compound II-235: m.p. 140-142° C. δppm 1.25 (3H, s), 2.45 (3H, s), 2.86 (2H, t), 3.72 (2H, q), 5.41 (1H, s), 6.79 (2H, d), 7.08 (2H, d), 8.39 (2H, m).
Compound II-236: δppm 2.25 (3H, s), 2.45 (3H, s), 2.90 (2H, t), 3.62-3.81 (2H, q), 5.43 (1H, t), 6.74 (2H, d), 7.14 (2H, d), 7.40 (1H, d), 7.77 (1H, d), 8.38 (1H, s).
Compound II-254: m.p. 183-185° C. δppm 2.45 (3H, s), 2.86 (2H, t), 3.66-3.83 (2H, q), 5.43 (1H, t), 6.80 (2H, d), 7.08 (2H, d), 8.39 (1H, s).
Compound II-274: m.p. 130-132° C. δppm 2.929-2.953 (t, 2H), 3.744-3.765 (q, 2H), 5.65 (s, 1H), 6.830-7.230 (dd, 4H), 8.392 (s, 1H).
Compound II-299: δppm 1.23 (3H, t), 2.78 (2H, dd), 2.92 (2H, t), 3.75 (2H, dd), 5.44 (1H, t), 6.85 (1H, d), 6.91 (2H, d), 7.17-7.23 (3H, m), 7.46 (1H, d), 8.44 (1H, s).
Compound II-432: δppm 1.26 (3H, t), 2.78 (2H, dd), 2.95 (2H, t), 3.77 (2H, dd), 5.44 (1H, t), 6.92 (1H, d), 7.00 (2H, d), 7.25 (2H, d), 7.42 (1H, d), 7.73 (1H, s), 8.44 (1H, s).
Compound II-443: m.p. 101.0° C. δppm 1.25 (3H, t), 2.77 (2H, dd), 2.92 (2H, t), 3.74 (2H, dd), 5.42 (1H, t), 6.79 (2H, d), 7.18 (2H, d), 8.32 (2H, s), 8.43 (1H, s).
Compound II-482: δppm 1.26 (3H, t), 2.78 (2H, dd), 2.98 (2H, t), 3.78 (2H, dd), 5.44 (1H, t), 6.93 (1H, t), 7.08 (2H, d), 7.27 (2H, d), 7.37 (1H, dd), 7.48 (1H, dd), 8.44 (1H, s).
Compound II-1687: δppm 2.46 (3H, s), 2.93 (2H, t), 3.75-3.96 (5H, m), 5.43 (1H, t), 6.77-6.87 (4H, m), 6.93 (1H, d), 7.23 (2H, d), 8.40 (1H, s).
Compound II-1737: δppm 2.47 (3H, s), 2.95 (2H, t), 3.75-3.91 (5H, m), 5.42 (1H, t), 6.80-7.04 (5H, m), 7.53 (2H, d), 8.41 (1H, s).
Compound II-1965: δppm 1.26 (3H, t), 2.79 (2H, dd), 2.95 (2H, t), 3.72-3.95 (5H, m), 5.45 (1H, t), 6.78-6.90 (4H, m), 6.94 (1H, d), 7.24 (2H, d), 8.45 (1H, s).
Compound II-2015: δppm 1.26 (3H, t), 2.79 (2H, dd), 2.95 (2H, t), 3.75-3.95 (5H, m), 5.48 (1H, t), 6.80-6.88 (2H, q), 6.93 (2H, d), 7.01 (1H, d), 7.53 (2H, d), 8.45 (1H, s).
Compound II-8917: m.p. 93.3° C. δppm 2.94 (2H, t), 3.81 (2H, dd), 5.70 (1H, t), 6.72 (1H, t), 6.90-6.97 (3H, q), 7.16-7.23 (3H, q), 7.47 (1H, d), 8.57 (1H, s).
Compound II-8921: m.p. 106-107° C. δppm 2.945-2.992 (2H, t), 3.797-3.864 (2H, q), 5.717 (1H, s), 6.549-6.848 (1H, t), 6.854-7.237 (7H, m), 8.583 (1H, s).
Compound II-8965: m.p. 109-110° C. δppm 2.944-2.990 (2H, t), 3.798-3.865 (2H, q), 5.717 (1H, s), 6.542-6.900 (1H, t), 7.010-7.588 (8H, m), 8.574 (1H, s).
Compound II-9058: δppm 2.938-2.984 (2H, t), 3.790-3.858 (2H, q), 6.545-6.903 (1H, t), 6.992-7.458 (4H, dd), 6.930-6.959 (1H, d), 7.478-7.487 (1H, d), 7.952-7.960 (1H, s), 8.571 (1H, s).
Compound II-9073: m.p. 77-78° C. δppm 2.970-3.016 (2H, t), 3.812-3.878 (2H, q), 5.738 (1H, s), 6.549-6.906 (1H, t), 7.061-7.319 (4H, dd), 7.005-7.035 (1H, d), 7.698-7.727 (1H, d), 8.233 (1H, s), 8.575 (1H, s).
Compound  II-9170: m.p. 154-158° C. δppm 2.951-2.975 (2H, t), 3.800-3.821 (2H, q), 6.714-6.874 (1H, t), 6.844-7.233 (4H, dd), 8.569 (1H, s).
Compound II-9336: m.p. 130-131° C. δppm 2.942-2.989 (2H, t), 3.799-3.866 (2H, q), 6.994-7.459 (4H, dd), 6.936-6.965 (1H, d), 7.480-7.488 (1H, d), 7.593-7.961 (1H, d), 8.571 (1H, s).
Compound II-9351: m.p. 128-129° C. δppm 2.975-3.021 (2H, t), 3.820-3.887 (2H, q), 5.875 (1H, s), 7.066-7.322 (4H, dd), 7.009-7.039 (1H, d), 7.704-7.731 (1H, d), 8.238 (1H, s), 8.580 (1H, s).
Compound II-10633: δppm 2.98 (2H, t), 3.79 (3H, t), 3.86 (2H, dd) 5.74 (1H, s), 6.72 (1H, t), 6.84-7.05 (5H, m), 7.53 (2H, d), 8.58 (1H, s).
Compound III-1: colourless oil. δppm 2.50 (3H, s), 2.88 (2H, t), 3.74 (2H, m), 5.45 (1H, bs), 6.87 (1H, d), 7.09-7.22 (3H, m), 7.36-7.42 (2H, m), 7.56 (1H, dd), 8.05 (1H, d), 8.38 (1H, s).
Compound III-5: colourless oil.
Compound III-6: colourless oil. δppm 2.46 (3H, s), 2.92 (2H, t), 3.75 (2H, m), 5.42 (1H, bs), 6.90 (1H, d), 7.03 (1H, dd), 7.13-7.18 (2H, m), 7.29 (1H, d), 7.59 (1H, dd), 8.05 (1H, d), 8.39 (1H, s).
Compound III-16: colourless oil. δppm 2.35 (3H, s), 2.52 (3H, s), 2.88 (2H, t), 3.70-3.77 (2H, m), 5.42 (1H, bs), 6.85 (1H, d), 7.01 (2H, d), 7.19 (2H, d), 7.53 (1H, dd), 8.03 (1H, d), 8.38 (1H, s).
Compound III-19: colourless oil. δppm 2.46 (3H, s), 2.89 (2H, t), 3.70-3.77 (2H, m), 3.82 (3H, s), 5.42 (1H, bs), 6.83 (1H, d), 6.92 (2H, d), 7.06 (2H, d), 7.53 (1H, dd), 8.03 (1H, d), 8.38 (1H, s).
Compound III-21: colourless oil.
Compound III-22: colourless oil. δppm 2.46 (3H, t), 2.93 (2H, t), 3.76 (2H, m), 5.43 (1H, bs), 6.95 (1H, d), 7.20-7.28 (2H, m), 7.60-7.66 (3H, m), 8.06 (1H, d), 8.39 (1H, s).
Compound III-82: colourless oil. δppm 2.46 (3H, s), 2.90 (2H, t), 3.74 (2H, m), 5.42 (1H, bs), 6.97 (1H, d), 7.14 (1H, d), 7.28 (1H, d), 7.49 (1H, d), 7.62 (1H, dd), 7.97 (1H, d), 8.38 (1H, s).
Compound III-83: colourless oil. δppm 2.46 (3H, s), 2.91 (2H, t), 3.75 (2H, m), 5.42 (1H, bs), 6.97 (1H, d), 7.16 (1H, dd), 7.22 (1H, d), 7.40 (1H, d), 7.61 (1H, dd), 7.99 (1H, d), 8.39 (1H, s).
Compound III-110: colourless oil. δppm 2.14 (3H, t), 2.46 (3H, t), 2.89 (2H, t), 3.73 (2H, m), 5.42 (1H, bs), 6.86 (1H, d), 6.97 (1H, d), 7.17-7.25 (2H, m), 7.56 (1H, dd), 7.99 (1H, d), 8.38 (1H, s).
Compound III-121: colourless oil.
Compound III-181: colourless oil. δppm 1.26 (3H, t), 2.78 (2H, m), 2.90 (2H, t), 3.75 (2H, m), 5.45 (1H, bs), 6.87 (1H, d), 7.11-7.22 (3H, m), 7.36-7.42 (2H, m), 7.56 (1H, dd), 8.05 (1H, d), 8.43 (1H, s).
Compound III-185: colourless oil. δppm 1.26 (3H, t), 2.78 (2H, m), 2.88 (2H, t), 3.74 (2H, m), 5.43 (1H, bs), 6.94 (1H, d), 7.20 (2H, d), 7.28-7.32 (1H, m), 7.47 (1H, d), 7.59 (1H, dd), 8.00 (1H, d), 8.43 (1H, s).
Compound III-186: colourless oil. δppm 1.26 (3H, t), 2.75-2.83 (2H, m), 2.89-2.96 (2H, m), 3.72-3.79 (2H, m), 5.47 (1H, bs), 6.91 (1H, d), 7.03 (1H, d), 7.13-7.19 (2H, m), 7.29-7.34 (1H, m), 7.60 (1H, dd), 8.06 (1H, s), 8.44 (1H, s).
Compound III-187: colourless oil. δppm 1.26 (3H, t), 2.79 (2H, m), 2.91 (2H, t), 3.75 (2H, m), 5.43 (1H, bs), 6.89 (1H, d), 7.07 (2H, d), 7.35 (2H, d), 7.58 (1H, dd), 8.03 (1H, dd), 8.43 (1H, s).
Compound III-196: colourless oil. δppm 1.23 (3H, t), 2.35 (3H, s), 2.74-2.91 (5H, m), 3.70-3.77 (2H, m), 5.46 (1H, bs), 6.85 (1H, d), 6.99 (2H, d), 7.19 (2H, d), 7.54 (1H, dd), 8.03 (1H, d), 8.43 (1H, s).
Compound III-199: colourless oil. δppm 1.26 (3H, t), 2.75-2.82 (2H, m), 2.88 (2H, t), 3.70-3.77 (2H, m), 3.82 (3H, s), 5.42 (1H, bs), 6.83 (1H, d), 6.92 (2H, d), 7.06 (2H, d), 7.54 (1H, dd), 8.03 (1H, d), 8.43 (1H, s).
Compound III-201: colourless oil.
Compound III-262: colourless oil. δppm 1.26 (3H, t), 2.79 (2H, m), 2.90 (2H, t), 3.74 (2H, m), 5.42 (1H, bs), 6.97 (1H, d), 7.14 (1H, d), 7.29 (1H, d), 7.48 (1H, d), 7.61 (1H, dd), 7.97 (1H, d), 8.43 (1H, s).
Compound III-263: colourless oil. δppm 1.26 (3H, t), 2.81 (2H, m), 2.91 (2H, t), 3.75 (2H, m), 5.43 (1H, bs), 6.98 (1H, d), 7.14-7.22 (2H, m), 7.40 (2H, d), 7.63 (1H, dd), 7.99 (1H, s), 8.44 (1H, s).
Compound III-290: colourless oil. δppm 1.26 (3H, t), 2.14 (3H, s), 2.78 (2H, m), 2.89 (2H, t), 3.74 (2H, m), 5.42 (1H, bs), 6.86 (1H, d), 6.97 (1H, d), 7.19 (1H, dd), 7.25 (1H, d), 7.57 (1H, dd), 8.00 (1H, d), 8.43 (1H, s).
Compound III-301: colourless oil.
Compound III-541: colourless oil. δppm 2.91 (2H, t), 3.81 (2H, m), 5.73 (1H, bs), 6.54, 6.71, 6.83 (1H, t), 6.88 (1H, d), 7.09-7.18 (2H, m), 7.22 (1H, t), 7.36-7.42 (2H, m), 7.56 (1H, dd), 8.07 (1H, d), 8.56 (1H, s).
Compound III-545: colourless oil. δppm 2.92 (2H, t), 3.80 (2H, m), 5.71 (1H, bs), 6.53, 6.71, 6.89 (1H, t), 6.95 (1H, d), 7.18-7.32 (3H, m), 7.47 (1H, d), 7.59 (1H, dd), 8.00 (1H, d), 8.56 (1H, s).
Compound III-546: colourless oil. δppm 2.94 (2H, t), 3.77-3.82 (2H, m), 5.74 (1H, bs), 6.54, 6.72, 6.89 (1H, t), 6.91 (1H, d), 7.02 (1H, d), 7.13-7.18 (2H, m), 7.29-7.35 (1H, m), 7.61 (1H, dd), 8.06 (1H, d), 8.61 (1H, s).
Compound III-547: colourless oil. δppm 2.93 (2H, t), 3.80 (2H, m), 5.72 (1H, bs), 6.53, 6.72, 6.89 (1H, t), 6.92 (1H, d), 7.07 (2H, d), 7.35 (2H, d), 7.58 (1H, dd), 8.03 (1H, s), 8.56 (1H, s).
Compound III-556: colourless oil. δppm 2.35 (3H, t), 2.91 (2H, t), 3.76-3.84 (2H, m), 5.73 (1H, bs), 6.54, 6.72, 6.84 (1H, t), 6.89 (1H, d), 7.01 (1H, d), 7.19 (1H, d), 7.55 (1H, dd), 8.04 (1H, d), 8.56 (1H, s).
Compound III-559: colourless oil. δppm 2.91 (2H, t), 3.76-3.81 (5H, m), 5.73 (1H, bs), 6.54, 6.72, 6.84 (1H, t), 6.91 (1H, d), 6.94 (1H, dd), 7.06 (1H, dd), 7.54 (1H, dd), 8.03 (1H, d), 8.56 (1H, s).
Compound III-561: colourless oil. δppm 2.95 (2H, t), 3.81 (2H, m), 5.74 (1H, bs), 6.54, 6.72, 6.89 (1H, t), 6.95 (1H, d), 7.32 (1H, d), 7.39 (1H, s), 7.44-7.54 (2H, m), 7.62 (1H, dd), 8.05 (1H, d), 8.57 (1H, s).
Compound III-562: colourless oil. δppm 2.95 (2H, t), 3.81 (2H, m), 5.74 (1H, bs), 6.54, 6.72, 6.89 (1H, t), 6.97 (1H, d), 7.21-7.24 (2H, m), 7.61-7.67 (3H, m), 8.06 (1H, d), 8.57 (1H, s).
Compound III-623: colourless oil. δppm 2.92 (2H, t), 3.80 (2H, m), 5.72 (1H, bs), 6.54, 6.72, 6.89 (1H, t), 6.91 (1H, s), 6.99 (1H, d), 7.15-7.22 (2H, m), 7.40 (1H, d), 7.61 (1H, dd), 8.00 (1H, d), 8.57 (1H, s).
Compound III-650: colourless oil. δppm 2.13 (3H, s), 2.91 (2H, t), 3.79 (2H, m), 5.66 (1H, bs), 6.53, 6.72, 6.86 (1H, t), 6.89 (1H, s), 6.97 (1H, d), 7.17-7.25 (2H, m), 7.57 (1H, dd), 8.01 (1H, d), 8.56 (1H, s).
Compound III-661: colourless oil.
Compound III-2521: colourless oil. δppm 2.90 (2H, t), 3.74-3.81 (2H, m), 5.60 (1H, bs), 6.83-6.89 (1H, m), 7.09-7.11 (2H, m), 7.13-7.22 (1H, m), 7.37-7.42 (2H, m), 7.49-7.56 (1H, m), 8.15 (1H, d), 8.29 (1H, s).
Compound III-2526: colourless oil. δppm 2.92 (2H, t), 3.74-3.81 (2H, m), 5.62 (1H, bs), 6.91 (1H, d), 7.02 (1H, d), 7.14-7.18 (2H, m), 7.29-7.34 (1H, m), 7.57-7.60 (1H, m), 8.05 (1H, d), 8.32 (1H, s).
Compound III-2527: colourless oil. δppm 2.91 (2H, t), 3.74-3.81 (2H, m), 5.60 (1H, bs), 6.90 (1H, d), 7.07 (2H, dd), 7.35 (2H, dd), 7.54 (1H, dd), 8.03 (1H, d), 8.29 (1H, s).
Compound III-2536: colourless oil. δ(CDCl3): 2.36 (3H, s), 2.89 (2H, t), 3.73-3.79 (2H, m), 5.62 (1H, bs), 6.85 (1H, d), 6.98-7.02 (2H, m), 7.20 (2H, d), 7.54 (1H, dd), 8.03 (1H, d), 8.29 (1H, s).
Compound III-2539: colourless oil. δppm 2.89 (2H, t), 3.73-3.79 (2H, m), 3.81 (3H, t), 5.61 (1H, bs), 6.83 (1H, d), 6.92 (2H, dd), 7.05 (2H, dd), 7.52 (1H, dd), 8.03 (1H, d), 8.29 (1H, s).
Compound III-2541: colourless oil. δppm 2.93 (2H, t), 3.75-3.82 (2H, m), 5.62 (1H, bs), 6.94 (1H, d), 7.32 (1H, d), 7.40-7.51 (3H, m), 7.60 (1H, dd), 8.04 (1H, d), 8.30 (1H, s).
Biological Testing
The compounds of the present invention exhibit both excellent fungicidal activity against many fungi in agricultural field and better insecticidal and acaricidal activities.
Except for the controls CK1-CK21 (known compounds illustrated in background technology) listed in following Table 303-310, according to the prior art, the following compounds CK22-CK84, diflumetorim and flufenerim were also prepared as controls, all the controls were self-made, they are listed in Table 302.







TABLE 302







the structure of controls








No.
Structure





CK22






 


CK23






 


CK24






 


CK25






 


CK26






 


CK27






 


CK28






 


CK29






 


CK30






 


CK31






 


CK32






 


CK33






 


CK34






 


CK35






 


CK36






 


CK37






 


CK38






 


CK39






 


CK40






 


CK41






 


CK42






 


CK43






 


CK44






 


CK45






 


CK46






 


CK47






 


CK48






 


CK49






 


CK50






 


CK51






 


CK52






 


CK53






 


CK54






 


CK55






 


CK56






 


CK57






 


CK58






 


CK59






 


CK60






 


CK61






 


CK62






 


CK63






 


CK64






 


CK65






 


CK66






 


CK67






 


CK68






 


CK69






 


CK70






 


CK71






 


CK72






 


CK73






 


CK74






 


CK75






 


CK76






 


CK77






 


CK78






 


CK79






 


CK80






 


CK81






 


CK82






 


CK83






 


CK84













Example 32: Fungicidal Testing
(1) The Determination of Protectant Activity In Vivo
The method is as followed: The whole plant is used in this test. The compound is dissolved in a proper solvent to get mother solution. The proper solvent is selected from acetone, methanol, DMF and so on according to their dissolving capability to the sample. The volume rate of solvent and testing solution (v/v) is equal to or less than 5%. The mother solution is diluted with water containing 0.1% tween-80 to get the testing solution whose concentration is designed. The testing solution is sprayed to the host plant by a special plant sprayer. The plant is inoculated with fungus after 24 hours. According to the infecting characteristic of fungus, the plant is stored in a humidity chamber and then transferred into greenhouse after infection is finished. And the other plants are placed in greenhouse directly. The activity of compound is obtained by eyeballing after 7 days in common.
The protectant activities in vivo of some compounds are as follows:
The protectant activity against cucumber downy mildew in vivo:
At the dosage of 400 ppm, the protectant activity of compounds I-22, I-35, I-254, I-255, I-467, I-483, I-486, I-502, I-583, I-602, I-699, I-815, I-987, I-1762, I-1878, I-2555, I-2574, I-2748, I-2611, I-3077, I-3309, I-4757, I-5221, I-6730, I-6732, I-6740, I-6765, I-6790, I-6796, II-21, II-25, II-69, II-154, II-204, II-236, II-254, II-297, II-299, II-303, II-347, II-432, II-482, II-1687, II-1965, II-8915, II-8917, II-8921, II-8965, II-9058, II-10583, III-1, III-5, III-7, III-16, III-19, III-22, III-82, III-110, III-121, III-181, III-187, III-196, III-199, III-201, II-202, III-262, III-263, III-290, III-301, III-541, III-547, III-556, III-562, III-622, III-623, III-650, III-2521, III-2526, III-2527, III-2536, III-2539, III-2541, III-2630 and so on was 100%, the protectant activity of compounds I-618, I-1199, I-2787, I-2843, I-6793, I-6797, II-235, II-274, II-9073, II-9170, II-9336, II-19334 and so on was between 80%-99%;
At the dosage of 100 ppm, the protectant activity of compounds I-22, I-254, I-255, I-467, I-583, I-602, I-699, I-987, I-1199, I-2748, I-3077, I-4757, I-6730, I-6732, I-6740, I-6765, II-21, II-204, II-236, II-297, II-299, II-482, II-1687, II-8915, II-8917, II-8921, II-8965, II-10583, III-1, III-5, III-7, III-16, III-19, III-22, III-82, III-110, III-121, III-181, III-187, III-196, III-199, III-201, III-202, III-262, III-263, III-301, III-541, III-547, III-556, III-562, III-622, III-623, III-650, III-2521, III-2526, III-2527, III-2536, III-2539, III-2541 and so on was 100%, the protectant activity of compounds I-35, I-502, I-987, I-2555, I-2611, I-3309, I-5221, I-6790, I-6796, II-25, II-69, II-303, II-347, II-9058, III-290, III-2630 and so on was between 80%-99%;
At the dosage of 50 ppm, the protectant activity of compounds I-22, I-254, I-255, I-467, I-2748, I-3077, I-6730, I-6765, II-21, II-204, II-236, II-297, II-482, II-1687, II-8917, II-8965, III-1, III-5, III-7, III-16, III-19, III-22, III-82, III-110, III-121, III-181, III-187, III-196, III-201, III-202, III-262, III-263, III-301, III-541, III-547, III-556, III-562, III-622, III-623, III-650, III-2521, III-2526, III-2527, III-2536, III-2539, III-2541 and so on was 100%, the protectant activity of compounds I-583, I-602, I-699, I-987, I-1199, I-2611, I-3309, I-5221, I-6790, I-6796, II-25, II-299, II-8915, II-8921, II-9058, II-10583, III-199, III-2630 and so on was between 80%-99%;
At the dosage of 25 ppm, the protectant activity of compounds I-22, I-255, I-467, I-583, I-699, I-3077, I-6730, I-6732, I-6765, II-204, II-236, II-297, II-482, II-8917, III-1, III-5, III-7, III-16, III-19, III-22, III-82, III-110, III-121, III-181, III-187, III-196, III-201, III-202, III-262, III-263, III-301, III-541, III-547, III-556, III-562, III-622, III-623, III-2521, III-2526, III-2527, III-2539 and so on was 100%, the protectant activity of compounds I-602, I-699, I-3309, I-6790, II-25, II-1687, II-8915, II-8921, II-8965, II-10583, III-199, III-650, III-2536, III-2541 and so on was between 80%-99%;
At the dosage of 12.5 ppm, the protectant activity of compounds I-22, III-1, III-7, III-16, III-22, III-187, III-202, III-301, III-541, III-556, III-562, III-622, III-2521, III-2527 and so on was 100%, the protectant activity of compounds I-255, I-3077, I-6765, II-204, II-482, II-8915, II-8917, II-10583, III-19, III-82, III-196, III-201, III-263, III-623, III-650, III-2536, III-2539 and so on was between 80%-99%;
At the dosage of 6.25 ppm, the protectant activity of compounds I-22, III-7, III-16, III-22, III-187, III-202, III-301, III-541, III-562 and so on was 100%, the protectant activity of compounds I-6765, II-8915, II-8917, II-10583, III-19, III-196, III-556, III-622 and so on was between 80%-99%.
The protectant activity against wheat powdery mildew in vivo:
At the dosage of 400 ppm, the protectant activity of compounds I-22, I-23, I-34, I-35, I-254, I-255, I-266, I-267, I-467, I-486, I-502, I-602, I-815, I-929, I-987, I-1219, I-1414, I-1472, I-1762, I-2342, I-2555, I-2574, I-3309, I-4121, I-4757, I-6729, I-6730, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, I-6790, I-6793, I-6795, I-6796, II-19, II-25, II-69, II-154, II-204, II-297, II-299, II-303, II-347, II-432, II-482, II-1687, II-1965, II-8917, II-8921, II-8965, II-9058, II-9073, II-10583, II-19334, III-1, III-5, III-6, III-7, III-16, III-19, III-21, III-22, III-82, III-83, III-110, III-121, III-181, III-185, III-186, III-187, III-196, III-199, III-201, III-202, III-262, III-263, III-301, III-541, III-545, III-546, III-547, III-556, III-559, III-561, III-562, III-622, III-623, III-650, III-2536, III-2541 and so on was 100%; compounds I-483, I-583, I-2748, I-2787, I-2922, I-3077, I-5221, I-6797, II-53, II-9351, III-2539 and so on was between 80%-99%.
At the dosage of 100 ppm, the protectant activity of compounds I-22, I-254, I-255, I-267, I-467, I-486, I-602, I-987, I-1414, I-1472, I-2342, I-2555, I-2574, I-6729, I-6730, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, I-6793, II-154, II-204, II-297, II-303, II-347, II-432, II-482, II-1687, II-8921, II-8965, II-10583, II-19334, III-121, III-202, III-301 and so on was 100%; compounds I-23, I-483, I-502, I-583, I-6731, I-6732, I-6733, I-6735, II-19, II-25, II-299, II-8917, II-9058, II-9073, III-1, III-5, III-7, III-22, III-82, III-110, III-181, III-541, III-545, III-562, III-2541 and so on was between 80%-99%.
At the dosage of 25 ppm, the protectant activity of compounds I-22, I-254, I-255, I-2342, I-2555, I-2574, I-6730, I-6739, I-6740, I-6742, I-6765, I-6793, II-204, II-297, II-303, II-347, II-432, II-482, II-1687, II-8921, II-10583, II-19334, III-202 and so on was 100%; compounds I-23, I-254, I-502, I-602, I-987, I-6729, I-6731, I-6732, I-6733, I-6735, I-6756, I-6763, II-19, II-299, II-8917, II-8965, II-9058, II-9073, III-121, III-301 and so on was between 80%-99%.
At the dosage of 6.25 ppm, the protectant activity of compounds I-22, I-2342, I-2574, I-6765, II-204, II-432, II-10583 and II-19334 and so on was 100%; compounds I-23, I-255, I-502, I-2555, I-6730, I-6739, I-6742, II-19, II-297, II-303, II-482, II-1687, II-8921, III-202 and so on was between 80%-99%.
The protectant activity against corn rust in vivo:
At the dosage of 400 ppm, the protectant activity of compounds I-22, I-35, I-254, I-266, I-267, I-467, I-483, I-486, I-583, I-815, I-929, I-987, I-1045, I-1199, I-1219, I-1472, I-1762, I-1878, I-2342, I-2555, I-2574, I-2922, I-3077, I-4121, I-4757, I-5221, I-6729, I-6730, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, I-6790, I-6791, I-6793, I-6795, I-6796, II-19, II-21, II-53, II-69, II-154, II-165, II-204, II-297, II-299, II-303, II-347, II-432, II-482, II-1687, II-1965, II-8915, II-8917, II-8921, II-8965, II-10583, II-19334, III-1, III-6, III-7, III-16, III-19, III-21, III-82, III-83, III-110, III-181, III-185, III-186, III-196, III-199, III-201, III-202, III-262, III-301, III-541, III-545, III-546, III-547, III-556, III-559, III-561, III-622, III-623, III-661, III-2521, III-2526, III-2536, III-2539, III-2630 and so on was 100%; compounds I-1627, I-2748, II-25, II-236, II-254, III-5, III-22, III-650, III-2527, III-2541 and so on was between 80%-99%.
At the dosage of 100 ppm, the protectant activity of compounds I-22, I-35, I-254, I-467, I-486, I-583, I-987, I-2342, I-2574, I-2922, I-4757, I-5221, I-6729, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, I-6796, II-21, II-69, II-154, II-204, II-297, II-299, II-303, II-347, II-432, II-482, II-1687, II-8915, II-8917, II-8965, II-10583, III-6, III-7, III-21, III-110, III-201, III-202, III-262, III-301, III-545, III-546, III-559, III-561, III-622, III-661 and so on was 100%; compounds I-267, I-815, I-1199, I-1219, I-3077, I-3309, I-6730, I-6791, II-19, II-165, II-8921, II-19334, III-19, III-82, III-181, III-185, III-186, III-196, III-199, III-547, III-556, III-623, III-2526 and so on was between 80%-99%.
At the dosage of 25 ppm, the protectant activity of compounds I-22, I-254, I-583, I-2342, I-6729, I-6742, II-69, II-154, II-204, II-303, II-432, II-482, II-8915, II-8917, II-8965, III-7, III-262, III-561, III-622 and so on was 100%; compounds I-35, I-266, I-467, I-987, I-1219, I-2574, I-4757, I-5221, I-6730, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6765, I-6757, I-6796, II-21, II-297, II-299, II-347, II-8921, II-10583, III-199, III-201, III-545, III-546, III-559 was between 80%-99%.
At the dosage of 6.25 ppm, the protectant activity of compounds I-22, I-254, I-2342, I-6742, II-154, II-303, II-432, II-482, II-8915, II-8917 and so on was 100%; compounds I-266, I-987, I-2574, I-6732, I-6733, I-6796, II-21, II-204, II-297, II-299, II-347, II-8921, II-8965, III-262, III-559, III-561, III-622 was between 80%-99%.
(2) Determination of Fungicidal Activity In Vitro
The method is as followed: High Through Put is used in the test. The compound is dissolved in a proper solvent to become a testing solution whose concentration is designed. The solvent is selected from acetone, methanol, DMF and so on according to their dissolving capability to the sample. In a no animalcule condition, the testing solution and pathogens suspension are added into the cells of 96 cells culture board, which then should be placed in the constant temperature box. 24 hours later, pathogen germination or growth can be investigated by eyeballing, and the activity in vitro of the compound is evaluated based on germination or growth of control treatment.
The activities in vitro (inhibition rate) of some compounds are as follows:
The inhibition rate against rice blast:
At the dosage of 25 ppm, the inhibition rate of compounds I-22, I-483, I-929, I-987, I-1762, I-2574, I-2922, I-6757, I-6758, I-6763, II-53, II-165, II-274, II-1965, III-7, III-121, III-301, III-661 and so on was 100%; compounds I-23, I-35, I-254, I-255, I-266, I-618, I-1199, I-1219, I-1878, I-2342, I-3077, I-3309, I-4121, I-4757, I-5221, I-6729, I-6730, I-6731, I-6732, I-6733, I-6734, I-6735, I-6742, I-6758, I-6791, I-6793, I-6795, I-6796, I-6797, II-19, II-25, II-69, II-204, II-347, II-482, II-1687, II-9336, II-10583, III-1, III-5, III-6, III-7, III-16, III-19, III-21, III-22, III-82, III-83, III-110, III-181, III-186, III-187, III-196, III-199, III-201, III-202, III-262, III-541, III-545, III-546, III-547, III-556, III-559, III-561, III-562, III-622, III-623, III-661, III-2521, III-2526, III-2536, III-2539, III-2541, III-2630 was between 80%-99%, contrast compounds CK4, CK5, CK6, CK10, CK20, CK32, CK33, CK35, CK37, CK40, CK41, CK43, CK46, CK47, CK48, CK49, CK50, CK55, CK56 and CK58 was less than 50%, contrast compounds CK1, CK2, CK3, CK7, CK11, CK13, CK15, CK16, CK21, CK38, CK39, CK44, CK45, CK59, CK60, CK61 and CK63 was all 0;
At the dosage of 8.3 ppm, the inhibition rate of compounds I-483, I-2574, I-2922, II-53, II-165, III-7, III-661 and so on was 100%; compounds I-22, I-929, I-987, I-6758 and II-274 was between 80%-99%, contrast compound CK17 was 50%; contrast compounds CK5, CK6, CK14, CK18, CK19, CK46, CK47, CK48, CK49, CK50, CK51, CK52 and diflumetorim was all 0;
At the dosage of 2.8 ppm, the inhibition rate of compounds I-483, I-2922, II-53, II-165, III-7 and so on was 100%; compound II-274 was between 80%-99%, contrast compound CK17 was 0;
At the dosage of 0.9 ppm, the inhibition rate of compounds I-483, I-2922, II-53, II-165, III-7 and so on was 100%;
At the dosage of 0.3 ppm, the inhibition rate of compounds I-483, I-2922, II-53, II-165 and III-7 was 100%;
At the dosage of 0.1 ppm, the inhibition rate of compounds I-483, I-2922, II-165 and III-7 was 100%;
The inhibition rate against cucumber gray mold:
At the dosage of 25 ppm, the inhibition rate of compounds I-486, I-1045, I-2342, I-4757, II-303, II-1965, II-8921, III-82 and so on was 100%; compounds I-1199, I-3309, II-69, II-347, III-7, III-199, III-202, III-262, III-545, III-547, III-559, III-622 was between 80%-99%, contrast compounds CK20, CK21, CK24, CK25, CK44, CK45, CK56, CK57, CK62 was less than 50%, contrast compounds CK1, CK2, CK3, CK4, CK6, CK7, CK8, CK9, CK10, CK13, CK14, CK15, CK16, CK17, CK22, CK26, CK32, CK33, CK34, CK35, CK46, CK47, CK48, CK51, CK52, CK53, CK54, CK55, CK58, CK59, CK60, CK61, CK63, CK67, CK68, CK70, CK73, CK74, CK75, CK76, CK77, CK78, CK79, CK80, CK81, CK82, CK83, CK84, diflumetorim and flufenerim was all 0;
(2) The Contrastive Test Results of Some Compounds and Contrasts
Contrastive tests were carried out between some compounds and contrasts. The test results are listed in table 303-table 305 (“///” in the following tables means no test).







TABLE 303







The comparative test of protectant activity against cucumber 


downy mildew









control effect against cucumber downy mildew (%)














Compound
400 
100 
50 
25 
12.5 
6.25 
3.125 


No.
mg/L
mg/L
mg/L
mg/L
mg/L
mg/L
mg/L

















I-22
100
100
100
100
100
100
85


I-3309
100
90
90
90
70
60
50


II-236
100
100
100
100
///
///
///


II-297
100
100
100
100
///
///
///


II-8915
100
100
100
99
95
90
20


II-8917
100
100
100
100
95
85
///


II-10583
100
100
100
95
95
95
///


III-1
100
100
100
100
100
///
///


III-5
100
100
100
100
///
///
///


III-7
100
100
100
100
100
100
100


III-16
100
100
100
100
100
100
///


III-19
100
100
100
100
98
95
///


III-22
100
100
100
100
100
100
///


III-82
100
100
100
100
98
///
///


III-110
100
100
100
100
///
///
///


III-121
100
100
100
100
///
///
///


III-181
100
100
100
100
///
///
///


III-187
100
100
100
100
100
100
///


III-196
100
100
100
100
85
85
///


III-201
100
100
100
100
98
///
///


III-202
100
100
100
100
100
100
///


III-262 
100
100
100
100
///
///
///


III-263
100
100
100
100
98
70
///


III-301
100
100
100
100
100
100
///


III-541
100
100
100
100
100
100
95


III-547
100
100
100
100
///
///
///


III-556
100
100
100
100
100
95
///


III-562
100
100
100
100
100
100
///


III-622
100
100
100
100
100
98
///


III-623
100
100
100
100
98
70
///


III-650 
100
100
100
98
95
///
///


III-2521
100
100
100
100
100
///
///


III-2527
100
100
100
100
100
75
///


III-2536
100
100
100
98
90
///
///


III-2539
100
100
100
100
85
///
///


CK1
100
100
100
100
50
30
20


CK3
80
///
///
///
///
///
///


CK6
70
///
///
///
///
///
///


CK7
70
30
0
0
///
///
///


CK8
98
95
80
75
///
///
///


CK9
100
98
90
70
///
///
///


CK10
100
82
40
20
///
///
///


CK11
85
30
0
0
///
///
///


CK13
85
25
0
0
///
///
///


CK14
98
40
0
0
///
///
///


CK15
95
15
0
0
///
///
///


CK16
85
///
///
///
///
///
///


CK17
100
40
10
0
///
///
///


CK20
100
10
0
0
///
///
///


CK22
100
98
75
60
///
///
///


CK23
100
0
0
0
///
///
///


CK25
100
0
0
0
///
///
///


CK26
100
60
40
0
///
///
///


CK27
100
0
0
0
///
///
///


CK28
100
40
20
0
///
///
///


CK29
98
98
90
25
///
///
///


CK32
60
///
///
///
///
///
///


CK33
0
///
///
///
///
///
///


CK34
85
///
///
///
///
///
///


CK35
60
///
///
///
///
///
///


CK37
100
20
10
0
///
///
///


CK42
100
100
100
20
0
0
0


CK43
100
40
20
0
///
///
///


CK52
100
98
90
70
///
///
///


CK53
100
90
85
60
///
///
///


CK54
100
90
80
65
///
///
///


CK55
100
0
0
0
///
///
///


CK56
100
10
0
0
///
///
///


CK57
50
///
///
///
///
///
///


CK58
0
///
///
///
///
///
///


CK59
80
///
///
///
///
///
///


CK60
100
10
0
0
///
///
///


CK61
100
90
85
30
///
///
///


CK62
80
///
///
///
///
///
///


CK63
70
///
///
///
///
///
///


CK65
0
///
///
///
///
///
///


CK66
0
///
///
///
///
///
///


CK67
100
60
20
0
///
///
///


CK68
0
///
///
///
///
///
///


CK69
100
100
98
50
///
///
///


CK70
100
60
30
0
///
///
///


CK71
80
///
///
///
///
///
///


CK72
100
100
40
20
///
///
///


CK73
98
98
95
60
///
///
///


CK74
50
///
///
///
///
///
///


CK75
60
///
///
///
///
///
///


CK76
0
///
///
///
///
///
///


CK77
0
///
///
///
///
///
///


CK78
0
///
///
///
///
///
///


CK79
85
///
///
///
///
///
///


CK80
85
///
///
///
///
///
///


CK83
100
100
98
85
///
///
///


CK84
100
100
100
85
///
///
///


diflumetorim
100
100
100
70
15
0
///


flufenerim
0
///
///
///
///
///
///
















TABLE 304







The comparative test of protectant activity against wheat 


powdery mildew









control effect against wheat powdery mildew (%)













Compound 
400 
100 
25 
6.25 
1.6 
0.4 


No.
mg/L 
mg/L 
mg/L 
mg/L
mg/L 
mg/L
















I-22
100
100
100
100
15
///


I-254
100
100
100
100
20
///


I-2342
100
100
100
100
95
60


I-2574
100
100
100
100
75
20


I-6765
100
100
100
100
///
///


II-204
100
100
100
100
///
///


II-297
100
100
100
90
40
30


II-303
100
100
100
90
80
25


II-432
100
100
100
100
80
50


II-482
100
100
100
98
///
///


II-8921
100
100
100
90
40
///


II-10583
100
100
100
100
///
///


II-19334
100
100
100
100
60
///


III-1
100
98
98
98
///
///


III-202 
100
100
100
95
///
///


CK1
100
100
100
80
///
///


CK2
100
100
80
0
///
///


CK4
40
0
///
///
///
///


CK6
100
100
90
85
0
0


CK8
0
///
///
///
///
///


CK9
100
0
0
0
///
///


CK10
50
///
///
///
///
///


CK11
100
60
40
0
///
///


CK12
80
30
0
0
///
///


CK13
40
0
0
0
///
///


CK14
85
10
0
0
///
///


CK15
95
85
10
0
///
///


CK16
70
///
///
///
///
///


CK17
100
75
70
50
///
///


CK19
50
0
///
///
///
///


CK20
100
30
0
0
///
///


CK21
0
///
///
///
///
///


CK22
100
90
50
0
///
///


CK23
100
0
0
0
///
///


CK24
0
0
///
///
///
///


CK25
0
///
///
///
///
///


CK26
70
///
///
///
///
///


CK27
80
///
///
///
///
///


CK29
100
80
50
40
///
///


CK30
100
80
20
0
///
///


CK31
0
0
0
0
///
///


CK32
0
///
///
///
///
///


CK33
0
///
///
///
///
///


CK34
0
///
///
///
///
///


CK35
0
///
///
///
///
///


CK36
100
80
60
0
///
///


CK37
0
///
///
///
///
///


CK41
100
70
50
0
///
///


CK42
100
70
60
50
///
///


CK43
20
///
///
///
///
///


CK44
0
///
///
///
///
///


CK45
0
///
///
///
///
///


CK48
30
0
0
0
///
///


CK51
100
80
40
0
///
///


CK53
100
80
0
0
///
///


CK52
0
///
///
///
///
///


CK55
60
///
///
///
///
///


CK56
70
///
///
///
///
///


CK57
0
///
///
///
///
///


CK58
0
///
///
///
///
///


CK59
0
///
///
///
///
///


CK60
0
///
///
///
///
///


CK61
70
///
///
///
///
///


CK63
50
///
///
///
///
///


CK65
0
///
///
///
///
///


CK66
0
///
///
///
///
///


CK67
0
///
///
///
///
///


CK68
0
///
///
///
///
///


CK69
100
0
0
0
///
///


CK70
98
0
0
0
///
///


CK71
100
///
///
///
///
///


CK72
100
70
60
50
///
///


CK73
40
///
///
///
///
///


CK74
0
///
///
///
///
///


CK75
0
///
///
///
///
///


CK76
75
///
///
///
///
///


CK77
100
100
80
70
///
///


CK78
0
///
///
///
///
///


CK79
0
///
///
///
///
///


CK80
100
80
0
0
///
///


CK81
40
///
///
///
///
///


CK82
100
80
0
0
///
///


CK83
100
100
70
40
///
///


diflumetorim
100
95
95
90
///
///
















TABLE 305







The comparative test of protectant activity against corn rust









control effect against corn rust (%)













Compound
400
100
25
6.25
1.6
0.4


No.
mg/L 
mg/L 
mg/L 
mg/L 
mg/L
mg/L
















I-22
100
100
100
100
50
20


I-254
100
100
100
100
95
40


II-154
100
100
100
100
50
///


II-303
100
100
100
100
80
50


II-432
100
100
100
100
75
15


II-482
100
100
100
100
///
///


II-8915
100
100
100
100
80
30


II-8917
100
100
100
100
60
10


II-8965
100
100
100
95
85
30


III-7
100
100
100
///
///
///


III-262
100
100
100
90
90
60


III-561
100
100
100
95
80
40


CK2
100
100
100
85
///
///


CK4
0 
0
///
///
///
///


CK5
95
98
40
30
///
///


CK6
100
100
100
80
30 
0


CK8
50
///
///
///
///
///


CK9
100
100
20
0
///
///


CK10
50
///
///
///
///
///


CK12
100
100
85
75
///
///


CK13
100
0
0
0
///
///


CK14
100
20
0
0
///
///


CK15
95 
85
30
0
///
///


CK16
0
///
///
///
///
///


CK17
100
0
0
0
////
///


CK18
80
30
0
///
///
///


CK19
70
0
///
///
///
///


CK20
100
70
0
0
///
///


CK21
85
///
///
///
///
///


CK22
100
100
40
0
///
///


CK23
100
0
0 
0
///
///


CK24
100
50
20 
0
///
///


CK25
0
///
///
///
///
///


CK26
100
0
0
0
///
///


CK27
100
100
90
30
///
///


CK28
100
100
100
95
0
0


CK29
100
95
85
30
///
///


CK30
0
0
0
0
///
///


CK31
0 
0
0
0
///
///


CK33
0
///
///
///
///
///


CK34
0 
///
///
///
///
///


CK35
0
///
///
///
///
///


CK36
100
60
40
0
///
///


CK37
0
///
///
///
///
///


CK38 
0
///
///
///
///
///


CK39
100
100
80
50
10 
0


CK40
100
100
90
70
30 
0


CK41
100
100
90
80
20 
0


CK42
70
///
///
///
///
///


CK43
85
///
///
///
///
///


CK44
85
///
///
///
///
///


CK45
80
///
///
///
///
///


CK46
40
0
0
0
///
///


CK47
80
30
0
0
///
///


CK48
60 
20
0
0
///
///


CK49
85
30
0
0
///
///


CK50
80
0
0
0
///
///


CK51
80
20
0
0
///
///


CK52
85
///
///
///
///
///


CK53
0
///
///
///
///
///


CK54
100
60
30
0
///
///


CK55
0
///
///
///
///
///


CK56
70
///
///
///
///
///


CK57
0
///
///
///
///
///


CK58
0
///
///
///
///
///


CK59
0
///
///
///
///
///


CK60
0
///
///
///
///
///


CK61
0
///
///
///
///
///


CK63
100
30
0
0
///
///


CK65
0
///
///
///
///
///


CK66
0
///
///
///
///
///


CK67
0
///
///
///
///
///


CK68
0
///
///
///
///
///


CK69
100
90
50
0
///
///


CK70
100
30
10
0
///
///


CK71
0
///
///
///
///
///


CK72
100
80
20
0
///
///


CK73
100
90
10
0
///
///


CK74
100
100
90
85
///
///


CK75
0
///
///
///
///
///


CK76
70
///
///
///
///
///


CK77
100
60
40
0
///
///


CK78
0
///
///
///
///
///


CK79
0
///
///
///
///
///


CK80
100
85
20
0
///
///


CK81
80
///
///
///
///
///


CK82
100
30
0
0
///
///


CK83
30
///
///
///
///
///


CK84
100
90
60
0
///
///


diflumetorim
100
80
10
0
///
///









Example 33: Bioactivity Test Against Insects and Mites
Determination of insecticidal activity of compounds of the present invention against a few insects were carried out by the following procedures:
Compounds were dissolved in mixed solvent (acetone:methanol=1:1), and diluted to required concentration with water containing 0.1% of tween 80.
Diamond back moth, armyworm, peach aphid and carmine spider mite were used as targets and the method of spraying by airbrush was used for determination of insecticidal biassays.
(1) Bioactivity Test Against Diamond Back Moth
(1) Determination of Insecticidal Activity Against Diamond Back Moth
The method of spraying by airbrush: The cabbage leaves were made into plates of 2 cm diameter by use of punch. A test solution (0.5 ml) was sprayed by airbrush at the pressure of 0.7 kg/cm2 to both sides of every plate. 10 Second instar larvae were put into the petri-dishes after the leaf disc air-dried and 3 replicates were set for each treatment. Then the insects were maintained in observation room (25° C., 60 ̃70% R.H.). Scores were conducted and mortalities were calculated after 72 hrs.
Part of Test Results Against Diamond Back Moth:
At the dosage of 600 ppm, compounds I-22, I-254, I-255, I-467, I-583, I-815, I-3077, I-3309, I-4121, I-6729, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6742, I-6756, I-6757, I-6758, I-6765, II-19, II-154, II-204, II-297, II-347, II-482, II-1687, II-1965, II-8915, II-8965, II-10583, II-19334, III-1, III-6, III-7, III-16, III-19, III-21, III-22, III-110, III-181, III-185, III-187, III-196, III-199, III-201, III-202, III-541, III-546, III-547, II-556, III-559, III-562, III-622 and III-2527 showed 100% control against carmine spider mite; compounds II-21, II-274, II-303, II-432, II-8917, II-9170, III-83, III-262, III-545, II-561, III-2526 and III-2539 showed 80%-99% control.
At the dosage of 100 ppm, compounds I-254, I-255, I-6739, I-6740, I-6742, I-6756, I-6757, I-6758, I-6765, I-3309, II-19, II-204, II-482, II-19334, III-196, III-546, III-547 and III-556 showed 100% control against carmine spider mite; compounds II-1965, II-8965, II-9170, III-7, III-22, III-187 and III-202 showed 80%-99% control.
(2) Bioactivity Test Against Armyworm
The method of spraying by airbrush: The corn leaves were made into plates of 2 cm diameter by use of punch. A test solution (0.5 ml) was sprayed by airbrush at the pressure of 0.7 kg/cm2 to both sides of every plate. 10 Second instar larvae were put into the petri-dishes after the leaf disc air-dried and 3 replicates were set for each treatment. Then the insects were maintained in observation room (25□, 60 ̃70% R.H.). Scores were conducted and mortalities were calculated after 72 h.
Part of Test Results Against Armyworm:
At the dosage of 600 ppm, compounds I-255, I-467, I-486, I-583, I-1472, I-2342, I-3309, I-4121, I-6729, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6756, I-6757, I-6758, I-6763, I-6765, II-19, II-21, II-69, II-204, II-297, II-299, II-347, II-482, II-1965, II-8915, II-8917, II-8965, II-10583, II-19334, III-1, III-6, III-7, III-16, III-19, III-21, III-22, III-181, III-187, III-196, III-199, III-201, III-202, III-541, III-546, III-547, III-556, II-559, III-561, III-562 and III-2527 showed 100% control against carmine spider mite; compounds I-254, I-1762, I-2748, I-6742, II-303, II-432, III-110, III-650 and III-2541 showed 80%-99% control.
At the dosage of 100 ppm, compounds I-255, I-3309, I-6739, I-6740, I-6741, I-6756, I-6757, I-6758, I-6763, I-6765, II-204, II-482, II-8965, III-22, III-187, III-199, III-202, III-547, III-559, III-561 and III-562 showed 100% control against carmine spider mite; compounds I-1472, II-69, II-297, II-1965, II-8915, II-19334, III-196, III-201 and III-650 showed 80%-99% control.
At the dosage of 10 ppm, compounds II-482, III-187, III-547 and III-562 showed 80%-99% control.
(3) Bioactivity Test Against Green Peach Aphid
Method: Filter papers were put in culture dishes (Diameter=6 cm), and water was dripped on filter papers for preserving moisture. Green peach aphids (Myzus Persicae Sulzer) were maintained on cabbage. Leaves (Diameter=3 cm) of approximately 15-30 aphids were put in the culture dishes. Bioactivity tests were used the method of Airbrush Foliar Spray, pressure=10 psi (0.7 kg/cm2), spray volume=0.5 mL. The studies were conducted at three constant temperatures 25±1 C in incubator cabinets with 60±5% RH. Survey the survival aphids after 48 hrs and calculate the death rates.
Part of Test Results Against Green Peach Aphid:
At the dosage of 600 ppm, compounds I-22, I-23, I-34, I-35, I-254, I-255, I-266, I-267, I-467, I-483, I-486, I-502, I-583, I-602, I-815, I-929, I-987, I-1414, I-1472, I-1762, I-1878, I-2342, I-2555, I-2748, I-3077, I-3309, I-4121, I-6729, I-6730, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, I-6790, I-6793, I-6795, I-6796, I-6797, II-19, II-21, II-25, II-69, II-154, II-204, II-236, II-297, II-299, II-303, II-347, II-432, II-443, II-482, II-1687, II-1965, II-8915, II-8917, II-8921, II-8965, II-9073, II-10583, II-19334, III-1, III-5, III-6, III-7, III-16, III-19, III-21, III-22, III-82, III-83, III-110, III-121, III-181, III-185, III-186, III-187, III-196, III-199, III-201, III-202, III-262, III-263, III-301, III-541, III-545, III-546, III-547, III-556, III-559, III-561, III-562, III-622, III-623, III-650, III-661, III-2527, III-2536 and III-2539 showed 100% control against carmine spider mite; compounds I-699, I-1199, I-5221, III-2526 and III-2541 showed 80%-99% control.
At the dosage of 100 ppm, compounds I-22, I-23, I-34, I-35, I-254, I-255, I-266, I-267, I-483, I-486, I-583, I-602, I-815, I-987, I-1414, I-1472, I-1762, I-1878, I-2342, I-2555, I-3077, I-3309, I-4121, I-6729, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, I-6793, I-6796, I-6797, II-19, II-69, II-154, II-204, II-297, II-299, II-303, II-347, II-432, II-443, II-482, II-1687, II-1965, II-8915, II-8917, II-8965, II-10583, II-19334, III-7, III-16, III-22, III-110, III-121, III-181, III-185, III-186, III-187, III-196, III-199, III-201, III-202, III-262, III-301, III-541, III-547, III-556, III-559, III-561, III-562, III-650 and III-661 showed 100% control against carmine spider mite; compounds I-467, I-5221, II-21, II-25, II-8921, II-9073, III-1, III-5, III-6, III-21, III-545 and III-546 showed 80%-99% control.
At the dosage of 10 ppm, compounds I-22, I-34, I-35, I-254, I-255, I-266, I-267, I-987, I-1472, I-1762, I-1878, I-2342, I-3309, I-4121, I-6729, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, I-6796, II-19, II-69, II-204, II-297, II-347, II-482, II-1687, II-1965, II-8915, II-8917, II-8965, II-10583, II-19334, III-22, III-181, III-187, III-202, III-301, III-547 and III-562 showed 100% control against carmine spider mite; compounds I-23, I-583, I-602, I-3077, I-6793, I-6797, II-21, II-299, III-7, III-186, III-196 and III-541 showed 80%-99% control.
At the dosage of 5 ppm, compounds I-254, I-1762, I-6731, I-6735, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, II-69, II-204, II-297, II-347, II-482 and II-8915 showed 100% control against carmine spider mite; compounds II-299, II-8917, II-8965 and II-19334 showed 80%-99% control.
At the dosage of 2.5 ppm, compounds I-254, I-6739, I-6756, I-6757, I-6758, I-6765, II-297, II-347, II-482 and II-8915 showed 100% control against carmine spider mite; compounds II-69, II-204 and II-19334 showed 80%-99% control.
(4) Bioactivity Test Against Carmine Spider Mite
The method: Broadbean shoots with two true leaves in pot were taken, the healthy adults of carmine spider mite were inoculated to the leaves. The adults were counted and then sprayed with airbrush at the pressure of 0.7 kg/cm2 and at dose of 0.5 ml. 3 replicates were set for each treatment. And then they were maintained in standard observation room. Scores were conducted and mortalities were calculated after 72 hrs.
Parts of the Test Results Against Carmine Spider Mite are as Follows:
At the dosage of 600 ppm, compounds I-22, I-23, I-254, I-255, I-266, I-267, I-483, I-583, I-602, I-929, I-987, I-1472, I-1762, I-2342, I-6729, I-6730, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6742, I-6756, I-6757, I-6758, I-6763, I-6765, I-6795, I-6797, II-19, II-21, II-69, II-154, II-204, II-297, II-299, II-303, II-347, II-432, II-443, II-482, II-1687, II-1965, II-8915, II-8917, II-8965, II-10583, II-19334, III-1, III-5, III-7, III-16, III-19, III-21, III-22, III-110, III-181, III-185, III-187, III-196, III-199, III-201, III-202, III-541, III-545, III-547, III-556, III-559, III-561, III-562 and III-2539 showed 100% control against carmine spider mite; compounds I-1414, I-2555, I-3077, I-3309, I-6796, II-165, III-83, III-546 and III-623 showed 80%-99% control.
At the dosage of 100 ppm, compounds I-22, I-254, I-255, I-266, I-987, I-1762, I-2342, I-6729, I-6731, I-6732, I-6733, I-6734, I-6735, I-6739, I-6740, I-6741, I-6756, I-6757, I-6758, I-6763, I-6765, I-6795, I-6797, II-19, II-21, II-69, II-154, II-204, II-297, II-299, II-347, II-432, II-443, II-482, II-1965, II-8915, II-8917, II-8965, II-19334, III-7, III-16, III-22, III-181, III-187, III-199, III-202, III-547, III-556, III-559 and III-562 showed 100% control against carmine spider mite; compounds I-23, I-483, I-602, I-3309, III-1, III-19, III-196, III-541 and III-2539 showed 80%-99% control.
At the dosage of 10 ppm, compounds I-254, I-6739, I-6756, I-6765, II-204, II-347, II-482, II-8965 and II-19334 showed 100% control against carmine spider mite; compounds I-6740, I-6741, I-6757, I-6758, II-69, II-443, III-199 and III-562 showed 80%-99% control.
At the dosage of 5 ppm, compounds II-482 and II-19334 showed 100% control against carmine spider mite; compounds II-204, II-347 and II-8965 showed 80%-99% control.
At the dosage of 2.5 ppm, compounds II-482, II-8965 and II-19334 showed 80%-99% control.
(5) The Contrastive Test Results of Some Compounds and Contrasts
Contrastive tests were carried out between some compounds and contrasts. The test results are listed in table 306 to table 310 (“///” in the following tables means no test).







TABLE 306







contrastive tests against diamond back moth









Insecticidal activity against



diamond back moth (%)












Compound No.
600 mg/L
100 mg/L
10 mg/L
















I-255
100
100
43



I-3309
100
100
60



I-6733
100
68
40



I-6734
100
52
40



I-6742
100
75
47



II-19
100
100
50



II-204
100
100
20



II-347
100
70
65



II-482
100
100
60



II-8965
100
80
40



III-196
100
100
///



III-546
100
100
///



III-547
100
100
57



III-556
100
100
77



CK4
0
///
///



CK6
86
16
0



CK7
85
16
0



CK8
33
///
///



CK9
100
45
25



CK10
33
///
///



CK11
86
55
5



CK12
100
35
0



CK13
67
16
0



CK14
67
10
0



CK15
17
15
0



CK16
0
///
///



CK17
0
///
///



CK20
57
///
///



CK21
80
25
10



CK22
0
///
///



CK23
0
///
///



CK25
0
///
///



CK26
0
///
///



CK27
0
///
///



CK28
0
///
///



CK29
0
///
///



CK30
0
///
///



CK32
0
///
///



CK33
29
///
///



CK34
0
///
///



CK35
0
///
///



CK36
20
0
0



CK37
0
///
///



CK38
100
21
5



CK39
80
20
0



CK40
100
29
13



CK41
86
53
0



CK42
0
///
///



CK43
0
///
///



CK44
80
25
10



CK45
86
12
0



CK46
100
10
0



CK48
40
///
///



CK51
57
///
///



CK52
20
///
///



CK53
0
///
///



CK55
0
///
///



CK56
0
///
///



CK57
0
///
///



CK58
0
///
///



CK59
57
///
///



CK60
86
25
15



CK61
0
///
///



CK63
57
///
///



CK65
86
35
5



CK66
0
///
///



CK67
14
///
///



CK68
14
///
///



CK69
100
5
0



CK70
0
///
///



CK71
0
///
///



CK72
0
///
///



CK74
0
///
///



CK75
0
///
///



CK76
0
///
///



CK77
0
///
///



CK78
0
///
///



CK79
0
///
///



CK80
0
///
///



CK81
0
///
///



CK82
17
///
///



CK83
17
///
///



CK84
0
///
///



diflumetorim
0
///
///

















TABLE 307







contrastive tests against armyworm









Insecticidal activity against



armyworm (%)












Compound No.
600 mg/L
100 mg/L
10 mg/L
















I-255
100
100
25



I-3309
100
100
60



I-6756
100
100
28



I-6757
100
100
28



II-204
100
100
47



II-297
100
95
30



II-482
100
100
80



II-8915
100
95
44



II-8965
100
100
69



II-19334
100
84
44



III-22
100
100
71



III-187
100
100
95



III-199
100
100
64



III-202
100
100
65



III-547
100
100
95



III-556
100
75
45



III-562
100
100
83



CK4
40
///
///



CK5
100
56
0



CK6
29
///
///



CK7
100
0
0



CK8
17
///
///



CK9
40
///
///



CK10
0
///
///



CK11
29
///
///



CK12
86
20
0



CK13
86
0
0



CK14
0
///
///



CK15
0
///
///



CK16
0
///
///



CK17
0
///
///



CK18
100
43
14



CK19
86
25
7



CK20
///
///
0



CK21
0
///
///



CK22
0
///
///



CK23
0
///
///



CK24
///
///
0



CK25
0
///
///



CK26
0
///
///



CK27
29
///
///



CK28
29
///
///



CK29
14
///
///



CK30
57
///
///



CK32
0
///
///



CK33
100
0
0



CK34
0
///
///



CK35
0
///
///



CK36
0
///
///



CK37
0
///
///



CK38
0
///
///



CK39
0
///
///



CK40
43
6
0



CK41
100
0
0



CK42
0
///
///



CK43
0
///
///



CK44
0
///
///



CK45
0
///
///



CK46
71
0
0



CK47
86
25
0



CK48
50
///
///



CK49
17
///
///



CK51
43
///
///



CK52
0
///
///



CK53
0
///
///



CK54
67
///
///



CK55
0
///
///



CK56
0
///
///



CK57
0
///
///



CK58
0
///
///



CK59
14
///
///



CK60
0
///
///



CK61
0
///
///



CK63
71
///
///



CK64
0
///
///



CK65
0
///
///



CK66
0
///
///



CK67
0
///
///



CK68
0
///
///



CK70
0
///
///



CK71
86
///
///



CK72
71
///
///



CK73
100
50
0



CK74
0
///
///



CK75
0
///
///



CK76
0
///
///



CK77
0
///
///



CK78
0
///
///



CK79
0
///
///



CK80
0
///
///



CK81
14
///
///



CK82
0
///
///



CK83
29
///
///



CK84
0
///
///



diflumetorim
0
///
///

















TABLE 308







contrastive tests against peach aphid









Insecticidal activity against peach aphid (%)













Compound
600 
100 
10 
5
2.5
1.25


No.
mg/L 
mg/L 
mg/L 
mg/L 
mg/L 
mg/L
















I-22
100
100
100
100
100
100


I-254
100
100
100
100
100
100


I-3309
100
100
100
100
96
48


I-6731
100
100
100
100
93
60


I-6735
100
100
100
100
80
67


I-6739
100
100
100
100
100
100


I-6756
100
100
100
100
100
100


I-6757
100
100
100
100
100
100


I-6758
100
100
100
100
100
89


I-6765
100
100
100
100
100
84


II-19
100
100
100
///
///
///


II-69
100
100
100
100
81
///


II-204
100
100
100
100
97
60


II-297
100
100
100
100
100
93


II-347
100
100
100
100
100
81


II-482
100
100
100
100
100
100


II-1687
100
100
100
///
///
///


II-1965
100
100
100
///
///
///


II-8915
100
100
100
100
100
100


II-8917
100
100
100
83
///
///


II-8965
100
100
100
91
///
///


II-10583
100
100
100
///
///
///


II-19334
100
100
100
96
83
67


III-7
100
100
90
88
///
///


III-22 
100
100
100
100
98
67


III-181
100
100
100 
///
///
///


III-187 
100
100
100
///
///
///


III-202
100
100
100
100
100
94


III-301 
100
100
100 
///
///
///


III-547
100
100
100
///
///
///


III-562
100
100
100
///
///
///


CK2
100
100
95
37
23
0


CK4
100
100
64
41
0
///


CK6
100
76
0
///
///
///


CK7
100
100
59
///
///
///


CK8
0
///
/// 
///
///
///


CK9
100
79
23
///
///
///


CK10
100
91
23
///
///
///


CK11
100
98
85
25
0
///


CK12
100
100
73
///
///
///


CK13
100
98
83
0
///
///


CK14
100
70
0
///
///
///


CK15
69
40
0
///
///
///


CK16
64
///
/// 
///
///
///


CK17
0
///
///
///
///
///


CK18
100
71
51
7
0
///


CK19
100
86
33
///
///
///


CK21
100
98
35
19
0
///


CK22
0
///
///
///
///
///


CK23
0
///
/// 
///
///
///


CK24
100
100
89
28
0
///


CK25
0
///
///
///
///
///


CK26
100
48
45
///
///
///


CK27
0
///
/// 
///
///
///


CK28
100
100
43
///
///
///


CK29
0
///
///
///
///
///


CK30
93
50
0
///
///
///


CK32
0
///
///
///
///
///


CK33
0
///
///
///
///
///


CK34
65
///
/// 
///
///
///


CK35
0
///
/// 
///
///
///


CK36
90
14
0
///
///
///


CK37
100
16
0
///
///
///


CK38
100
24
0
///
///
///


CK39
100
86
2
0
///
///


CK40
100
100
72
27
0
///


CK41
100
97
23
15
0
///


CK42
100
67
20
17
0
///


CK43
0
///
///
///
///
///


CK44
100
98
35
19
0
///


CK45
100
98
55
39
26
0


CK46
100
5
0
///
///
///


CK48
100
87
0
///
///
///


CK51
100
50
0
///
///
///


CK52
88
0
0
///
///
///


CK53
84
66
34
///
///
///


CK54
100
100
34
///
///
///


CK55
0
///
///
///
///
///


CK56
100
0
0
///
///
///


CK57
61
///
///
///
///
///


CK58
100
0
0
///
///
///


CK59
75
15
0
///
///
///


CK60
81
0
0
///
///
///


CK61
88
0
0
///
///
///


CK63
100
0
0
///
///
///


CK65
0
///
///
///
///
///


CK66
0
///
///
///
///
///


CK67
86
54
0
///
///
///


CK68
0
///
///
///
///
///


CK69
100
100
70
///
///
///


CK70
81
0
0
///
///
///


CK72
55
///
///
///
///
///


CK73
100
100
0
///
///
///


CK74
100
100
26
///
///
///


CK75
100
0
0
///
///
///


CK76
52
///
///
///
///
///


CK77
72
///
///
///
///
///


CK78
0
///
///
///
///
///


CK79
100
16
0
///
///
///


CK80
87
40
16
///
///
///


CK81
75
///
///
///
///
///


CK82
86
130
0
///
///
///


CK83
100
100
11
///
///
///


CK84
100
43
7
///
///
///


diflumetorim
100
35
0
///
///
///


flufenerim
100
100
100
100
90
37
















TABLE 309







contrastive tests against carmine spider mite











Insecticidal activity against



Compound
carmine spider mite (% )












No.
600 mg/L 
100 mg/L 
10 mg/L
















I-22
100
100
74



I-254
100
100
97



I-255
100
100
85



I-987
100
100
80



I-6729
100
100
87



I-6734
100
100
82



I-6757
100
100
97



I-6758
100
100
99



I-6739
100
100
100



I-6756
100
100
100



I-6741
100
100
85



I-6765
100
100
100



I-6740
100
100
85



II-69
100
100
90



II-204
100
100
100



II-297
100
100
74



II-299
100
100
72



II-347
100
100
100



II-432
100
100
76



II-443
100
100
83



II-482
100
100
100



II-8965
100
100
100



II-19334
100
100
100



III-7
100
100
///



III-16
100
100
///



III-22
100
100
72



III-181
100
100
///



III-199
100
100
87



III-547
100
100
///



III-556
100
100
///



III-559
100
100
///



III-562
100
100
88



CK2
100
100
32



CK4
75
///
///



CK6
100
53
5



CK7
100
96
36



CK8
54
///
///



CK12
100
41
///



CK13
100
0
0



CK14
100
33
6



CK15
59
0
0



CK16
0
///
///



CK17
40
///
///



CK20
100
72
///



CK21
0
///
///



CK23
64
///
///



CK24
100
100
85



CK25
0
///
///



CK26
0
///
///



CK27
100
100
18



CK28
100
100
22



CK30
100
100
28



CK32
91
22
0



CK33
41
///
///



CK34
0
///
///



CK35
0
///
///



CK36
0
///
///



CK37
0
///
///



CK38
99
37
14



CK39
100
37
16



CK41
100
99
0



CK43
74
29
16



CK44
0
///
///



CK45
0
///
///



CK46
100
63
28



CK52
44
///
///



CK53
100
100
12



CK55
0
///
///



CK56
32
25
0



CK57
33
///
///



CK58
0
///
///



CK59
0
///
///



CK60
0
///
///



CK61
0
///
///



CK62
0
///
///



CK63
0
///
///



CK64
56
///
///



CK65
0
///
///



CK66
0
///
///



CK67
61
///
///



CK68
4
///
///



CK69
100
100
4



CK70
13
///
///



CK72
13
///
///



CK73
100
85
24



CK74
0
///
///



CK75
0
///
///



CK76
41
///
///



CK77
56
///
///



CK78
17
///
///



CK79
27
///
///



CK80
6
///
///



CK81
0
///
///



CK82
23
///
///



CK84
100
0
0



diflumetorim
100
100
73



flufenerim
100
100
72










Further contrastive tests were carried out between the compounds with better activities, such as compound I-22, I-254, I-255, I-6729, I-6734, I-6739, I-6756, I-6757, I-6758, II-204, II-347, II-482, II-8965 and II-19334, and the contrast CK24 at a low dosage. The test results are listed in table 310.










TABLE 310









Insecticidal activity




against carmine



spider mite (%)











Compound No.
5 mg/L
2.5 mg/L















I-22
59
///



I-254
93
79



I-255
84
72



I-6729
78
64



I-6734
57
51



I-6739
93
76



I-6756
88
71



I-6757
80
75



I-6758
82
79



II-204
80
60



II-347
90
75



II-482
100
93



II-8965
92
82



II-19334
100
87



CK24
15
5

## Claims

1. A substituted pyrimidine compound represented by formula PY:



wherein
R1 is cyano, C1-C12alkyl, C3-C12cycloalkyl, cyanoC1-C12alkyl, cyanoC1-C12alkoxy, C2-C12alkenyl, haloC2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl, or di(C1-C12alkyl)aminocarbonylC1-C12alkyl;
R2 is halo, cyano, C3-C12cycloalkyl, C1-C12alkyl, or haloC1-C12alkoxy;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, amino, C1-C12alkyl, C1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, unsubstituted or further substituted arylC1-C6alkyl or heteroarylC1-C6alkyl by 1 to 5 following groups: halo, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, and haloC1-C6alkoxy; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, and R5c, may be the same or different, and are each selected independently from the group consisting of H, OH, C3-C12cycloalkyl, C1-C12alkylthio, haloC1-C12alkylthio, C3-C12alkenoxy, haloC3-C12alkenoxy, C3-C12alkynoxy, haloC3-C12alkynoxy, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkylcarbonyloxy, C1-C12alkylcarbonylamino, C1-C12alkylsulfonyloxy, C1-C12alkoxycarbonyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkoxycarbonylamino, C1-C12alkoxyC1-C12alkoxy, and C1-C12alkoxycarbonylC1-C12alkoxy;
X1 is N or CR6; X2 is N or CR7; X3 is N or CR8; X4 is N or CR9; X5 is N or CR10; X6 is N or CR11; however, X2, X3, X4, X5, X6 are not simultaneously N;
R6 is selected from H, OH, HO(C═O), amino, C3-C12cycloalkyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, halodi(C1-C12alkyl)amino, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, di(C1-C12alkyl)amino(C1-C12alkyl), CONH2, CONHNH2, CON(C1-C12alkyl)NH2, CONHNH(C1-C12alkyl), CONHN(di(C1-C12alkyl)), CONHNHCO(C1-C12alkyl), CONHNHCO2(C1-C12alkyl), CONHNH(phenyl), C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, halodi(C1-C12alkyl)aminocarbonyl, C1-C12alkylsulfonylamino, C1-C12alkylsulfonyl(C1-C12alkyl)amino, haloC1-C12alkylsulfonylamino, C1-C12alkoxyamino, C1-C12alkoxycarbonylamino, C1-C12alkoxyaminocarbonyl, cyanoC1-C12alkyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, haloC1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl, di(C1-C12alkyl)aminocarbonylC1-C12alkyl, C1-C12alkylthiocarbonylC1-C12alkyl, haloC1-C12alkylthiocarbonylC1-C12alkyl, C1-C12alkylcarbonyloxy, haloC1-C12alkylcarbonyloxy, C1-C12alkoxycarbonyloxy, haloC1-C12alkoxycarbonyloxy, C1-C12alkylaminocarbonyloxy, haloC1-C12alkylaminocarbonyloxy, C1-C12alkylsulfonyloxy, haloC1-C12alkylsulfonyloxy, C1-C12alkoxyC1-C12alkoxy, haloC1-C12alkoxyC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkoxy or haloC1-C12alkoxycarbonylC1-C12alkoxy;
R7, R8, R9, R10, and R11, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, halodi(C1-C12alkyl)amino, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, di(C1-C12alkyl)amino(C1-C12alkyl), CONH2, CONHNH2, CON(C1-C12alkyl)NH2, CONHNH(C1-C12alkyl), CONHN(di(C1-C12alkyl)), CONHNHCO(C1-C12alkyl), CONHNHCO2(C1-C12alkyl), CONHNH(phenyl), C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, halodi(C1-C12alkyl)aminocarbonyl, C1-C12alkylsulfonylamino, C1-C12alkylsulfonyl(C1-C12alkyl)amino, haloC1-C12alkylsulfonylamino, C1-C12alkoxyamino, C1-C12alkoxycarbonylamino, C1-C12alkoxyaminocarbonyl, cyanoC1-C12alkyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, haloC1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl, di(C1-C12alkyl)aminocarbonylC1-C12alkyl, C1-C12alkylthiocarbonylC1-C12alkyl, haloC1-C12alkylthiocarbonylC1-C12alkyl, C1-C12alkylcarbonyloxy, haloC1-C12alkylcarbonyloxy, C1-C12alkoxycarbonyloxy, haloC1-C12alkoxycarbonyloxy, C1-C12alkylaminocarbonyloxy, haloC1-C12alkylaminocarbonyloxy, C1-C12alkyl sulfonyloxy, haloC1-C12alkyl sulfonyloxy, C1-C12alkoxyC1-C12alkoxy, haloC1-C12alkoxyC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkoxy, and haloC1-C12alkoxycarbonylC1-C12alkoxy;
W is H, halo, C1-C12alkyl, C1-C12alkylthio, or C1-C12alkylsulfonyl;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H, OH, H(C)═O, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C1-C12alkylthio, C2-C12alkenylthio, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, di(C1-C12alkyl)aminosulfonyl, C1-C12alkylsulfonylaminocarbonyl, C1-C12alkylcarbonylaminosulfonyl, C3-C12cycloalkyloxycarbonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkylcarbonylC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C2-C12alkenoxycarbonyl, C2-C12alkynoxycarbonyl, C1-C12alkoxyC1-C12alkoxycarbonyl, C1-C12alkylaminothio, di(C1-C12alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, or (hetero)arylC1-C6alkyloxycarbonyl by 1 to 5 following groups: halo, NO2, cyano, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, or haloC1-C6alkoxy;
or a salt thereof formed with an acid selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, and citric acid.

2. The substituted pyrimidine compound according to claim 1, wherein the substituted pyrimidine compound is represented by formula I:



wherein
R1 is cyano, C3-C12cycloalkyl, C1-C12alkyl, cyanoC1-C12alkyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl, or di(C1-C12alkyl)aminocarbonylC1-C12alkyl;
R2 is halo, cyano, C3-C12cycloalkyl, or C1-C12alkyl;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, amino, C1-C12alkyl, and C1-C12alkoxy;
R5a, R5b, and R5c, may be the same or different, and are each selected independently from the group consisting of H or OH;
X2 is N or CR7, X3 is N or CR8, X6 is N or CR11, within X2, X3, X6, at least one substituent is N;
R9 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, C1-C12alkoxycarbonyl, di(C1-C12alkyl)amino(C1-C12alkyl), haloC1-C12alkoxycarbonyl, CONH2, CONHNH2, CON(C1-C12alkyl)NH2, CONHNH(C1-C12alkyl), CONHN(di(C1-C12alkyl)), CONHNHCO(C1-C12alkyl), CONHNHCO2(C1-C12alkyl), CONHNH(phenyl), C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C1-C12alkylsulfonylamino, C1-C12alkylsulfonyl(C1-C12alkyl)amino, haloC1-C12alkylsulfonylamino, C1-C12alkoxyamino, C1-C12alkoxycarbonylamino, C1-C12alkoxyaminocarbonyl, cyanoC1-C12alkyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl, or di(C1-C12alkyl)aminocarbonylC1-C12alkyl;
R6 is selected from H, OH, HO(C═O), amino, C3-C12cycloalkyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, C1-C12alkoxycarbonyl, CONH2, C1-C12alkylaminocarbonyl or di(C1-C12alkyl)aminocarbonyl;
R7, R8, R10, and R11, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, C1-C12alkoxycarbonyl, CONH2, C1-C12alkylaminocarbonyl, and di(C1-C12alkyl)aminocarbonyl;
W is H or C1-C12alkyl;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H, OH, H(C)═O, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C1-C12alkylthio, C2-C12alkenylthio, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, di(C1-C12alkyl)aminosulfonyl, C1-C12alkylsulfonylaminocarbonyl, C1-C12alkylcarbonylaminosulfonyl, C3-C12cycloalkyloxycarbonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkylcarbonylC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C2-C12alkenoxycarbonyl, C2-C12alkynoxycarbonyl, C1-C12alkoxyC1-C12alkoxycarbonyl, C1-C12alkylaminothio, di(C1-C12alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, or (hetero)arylC1-C6alkyloxycarbonyl by 1 to 5 following groups: halo, NO2, cyano, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, or haloC1-C6alkoxy;
or a salt thereof formed with an acid selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, and citric acid.

3. The substituted pyrimidine compound according to claim 2, wherein
R1 is cyano, C3-C6cycloalkyl, C1-C6alkyl, cyanoC1-C6alkyl, cyanoC1-C6alkoxy, C1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkylaminocarbonylC1-C6alkyl, or di(C1-C6alkyl)aminocarbonylC1-C6alkyl;
R2 is halo, cyano, C3-C6cycloalkyl, or C1-C6alkyl;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, amino, C1-C6alkyl, and C1-C6alkoxy;
R5a, R5b, and R5c, may be the same or different, selected independently from H or OH;
X2 is N or CR7, X3 is N or CR8, X6 is N or CR11, within X2, X3, X6, at least one substituent is N;
R6 is H;
R7 is H, halo, cyano, or C1-C6alkyl;
R8 is selected from the group consisting of H, halo, cyano, C1-C6alkyl, and C1-C6alkoxy;
R9 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, haloC1-C6alkoxy, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6alkenoxy, haloC2-C6alkenoxy, C2-C6alkynoxy, haloC2-C6alkynoxy, C1-C6alkylthio, haloC1-C6alkylthio, C1-C6alkoxyC1-C6alkyl, haloC1-C6alkoxyC1-C6alkyl, C1-C6alkylthioC1-C6alkyl, haloC1-C6alkylthioC1-C6alkyl, C1-C6alkylsulfinyl, haloC1-C6alkylsulfinyl, C1-C6alkylsulfonyl, haloC1-C6alkylsulfonyl, C1-C6alkylaminosulfonyl, C1-C6alkylamino, haloC1-C6alkylamino, di(C1-C6alkyl)amino, C1-C6alkoxycarbonyl, CONH2, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, cyanoC1-C6alkoxy, C1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkylaminocarbonylC1-C6alkyl, or di(C1-C6alkyl)aminocarbonylC1-C6alkyl;
R10 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, haloC1-C6alkoxy, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6alkenoxy, haloC2-C6alkenoxy, C2-C6alkynoxy, haloC2-C6alkynoxy, C1-C6alkylthio, haloC1-C6alkylthio, C1-C6alkoxyC1-C6alkyl, haloC1-C6alkoxyC1-C6alkyl, C1-C6alkylthioC1-C6alkyl, haloC1-C6alkylthioC1-C6alkyl, C1-C6alkylsulfinyl, haloC1-C6alkylsulfinyl, C1-C6alkylsulfonyl, haloC1-C6alkylsulfonyl, C1-C6alkylamino, haloC1-C6alkylamino, di(C1-C6alkyl)amino, C1-C6alkoxycarbonyl, CONH2, C1-C6alkylaminocarbonyl, or di(C1-C6alkyl)aminocarbonyl;
R11 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, haloC1-C6alkoxy, C1-C6alkoxycarbonyl, CONH2, C1-C6alkylaminocarbonyl, or di(C1-C6alkyl)aminocarbonyl;
W is H or C1-C6alkyl;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H, OH, H(C)═O, C1-C6alkyl, C1-C6alkylcarbonyl, or C1-C6alkylsulfonyl;
or wherein the salt of formula I is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, or citric acid.

4. The substituted pyrimidine compound according to claim 3, wherein the substituted pyrimidine compound is represented by formula I-A, I-B, I-C, I-D, I-E, I-F, I-G, or I-H:






wherein
R1 is cyano or C1-C4alkyl;
R2 is halo, cyano, C3-C4cycloalkyl, or C1-C4alkyl;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, amino, C1-C4alkyl, and C1-C4alkoxy;
R5b is H or OH;
R7 is H, halo, cyano, or C1-C4alkyl;
R8 is H, halo, cyano, C1-C4alkyl, or C1-C4alkoxy;
R9 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkylthio, haloC1-C4alkylthio, C1-C4alkoxyC1-C4alkyl, haloC1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, haloC1-C4alkylthioC1-C4alkyl, C1-C4alkylsulfinyl, haloC1-C4alkylsulfinyl, C1-C4alkylsulfonyl, haloC1-C4alkylsulfonyl, C1-C4alkylaminosulfonyl, C1-C4alkylamino, haloC1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, cyanoC1-C4alkoxy, C1-C4alkoxycarbonylC1-C4alkyl, C1-C4alkylaminocarbonylC1-C4alkyl, or di(C1-C4alkyl)aminocarbonylC1-C4alkyl;
R10 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C3-C4cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, C2-C4alkenoxy, haloC2-C4alkenoxy, C2-C4alkynoxy, haloC2-C4alkynoxy, C1-C4alkylthio, haloC1-C4alkylthio, C1-C4alkoxyC1-C4alkyl, haloC1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, haloC1-C4alkylthioC1-C4alkyl, C1-C4alkylsulfinyl, haloC1-C4alkylsulfinyl, C1-C4alkylsulfonyl, haloC1-C4alkylsulfonyl, C1-C4alkylamino, haloC1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl, or di(C1-C4alkyl)aminocarbonyl; and
R11 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl, or di(C1-C4alkyl)aminocarbonyl;
or the salt of formula I-A, I-B, I-C, I-D, I-E, I-F, I-G, or I-H is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, maleic acid, sorbic acid, malic acid, or citric acid.

5. The substituted pyrimidine compound according to claim 4, wherein
R1 is cyano, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, or t-C4H9;
R2 is F, Cl, Br, cyano, CH3, or C2H5;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, Cl, Br, OH, amino, CH3, C2H5, OCH3, and OC2H5;
R5b is H or OH;
R7 is H, Cl, or cyano;
R8 is H, Cl, Br, cyano, CH3, or OCH3;
R9 is H, F, Cl, Br, cyano, HO(C═O), amino, NO2, CH3, C2H5, CF3, CClF2, OCH3, OC2H5, OCF3, COOCH3, COOC2H5, CONH2, CONHCH3, CONHC2H5, CON(CH3)2, SO2CH3, or SO2NHCH3;
R10 is H, Cl, cyano, CH3, C2H5, OCH3, or OC2H5; and
R11 is H, F, Cl, Br, cyano, HO(C═O), amino, NO2, CH3, C2H5, CF3, CClF2, OCH3, OC2H5, OCF3, COOCH3, COOC2H5, CONH2, CONHCH3, CONHC2H5, or CON(CH3)2;
or the salt of formula I-A, I-B, I-C, I-D, I-E, I-F, I-G, or I—H is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid, or benzoic acid.

6. The substituted pyrimidine compound according to claim 5, wherein the substituted pyrimidine compound is represented by formula I-A and wherein
R1 is CH3 or C2H5;
R2 is Cl, Br, or cyano;
R3, R4, and R10 are H;
R5b is H;
R8 is H or Cl;
R9 is H, Cl, cyano, CF3, CClF2, COOCH3, COOC2H5, or CONH2; and
R11 is H, Cl, NO2, CF3, COOCH3, or CONHCH3;

or wherein the substituted pyrimidine compound is represented by formula I-B and
R1 is CH3, C2H5, or CHF2;
R2 is Cl, Br, or cyano;
R9 is Cl, Br, cyano, or CF3; and
R3, R4, R5b, R10, and R11 are H;

or wherein the substituted pyrimidine compound is represented by formula I-C and
R1 is CH3, C2H5, or CHF2;
R2 is Cl, Br, or cyano;
R3, R4, R5b, and R9 are H; and
R8 and R10 are CH3 or OCH3;

or wherein the substituted pyrimidine compound is represented by formula I-D and
R1 is CH3, C2H5, or CHF2;
R2 is Cl, Br, or cyano;
R3, R4, R5b, R8, and R10 are H;
R9 is H, Cl, cyano, CF3, COOCH3, COOC2H5, or CONH2; and
R11 is H, Cl, or CF3;

or wherein the salt of formula I-A, I-B, I-C, or I-D is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid, or benzoic acid.

7. The substituted pyrimidine compound according to claim 6, wherein
the substituted pyrimidine compound is represented by formula I-A and wherein
R1 is CH3 or C2H5;
R2 is Cl, Br, or cyano;
R3, R4, R5b, and R10 are H;
R9 is Cl, cyano, or CF3; and
R8 and R11 are H or Cl;

or wherein the substituted pyrimidine compound is represented by formula I-B and
R1 is CH3, C2H5, or CHF2;
R2 and R9 are Cl, Br, or cyano; and
R3, R4, R5b, R10, and R11 are H;

or wherein the salt of formula I-A or I-B is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid, or benzoic acid.

8. A substituted pyrimidine compound represented by formula II:



wherein
R1 is C1-C12alkyl or C3-C8cycloalkyl;
R2 is halo or cyano;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, halo, C1-C12alkyl, C1-C12alkoxy, and C3-C12cycloalkyl; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, and R5c, may be the same or different, and are each selected independently from the group consisting of H or OH;
R6 is selected from H, OH, amino, C3-C12 cycloalkyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, halodi(C1-C12alkyl)amino, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, halodi(C1-C12alkyl)aminocarbonyl, CONH2, C1-C12alkylthio, haloC1-C12alkylthio, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, haloC1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylthiocarbonylC1-C12alkyl, haloC1-C12alkylthiocarbonylC1-C12alkyl, C1-C12alkylcarbonyloxy, haloC1-C12alkylcarbonyloxy C1-C12alkoxycarbonyloxy, haloC1-C12alkoxycarbonyloxy, C1-C12alkylaminocarbonyloxy, haloC1-C12alkylaminocarbonyloxy, C1-C12alkylsulfonyloxy, haloC1-C12alkylsulfonyloxy, C1-C12alkoxyC1-C12alkoxy, haloC1-C12alkoxyC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkoxy or haloC1-C12alkoxycarbonylC1-C12alkoxy;
R7, R8, R9, R10, and R11, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, amino, cyano, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12 cycloalkyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, halodi(C1-C12alkyl)amino, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, halodi(C1-C12alkyl)aminocarbonyl, CONH2, C1-C12alkylthio, haloC1-C12alkylthio, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, haloC1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylthiocarbonylC1-C12alkyl, haloC1-C12alkylthiocarbonylC1-C12alkyl, C1-C12alkylcarbonyloxy, haloC1-C12alkylcarbonyloxy, C1-C12alkoxycarbonyloxy, haloC1-C12alkoxycarbonyloxy, C1-C12alkylaminocarbonyloxy, haloC1-C12alkylaminocarbonyloxy, C1-C12alkyl sulfonyloxy, haloC1-C12alkyl sulfonyloxy, C1-C12alkoxyC1-C12alkoxy, haloC1-C12alkoxyC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkoxy, and haloC1-C12alkoxycarbonylC1-C12alkoxy;
W is H or C1-C12alkyl;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H, OH, H(C)═O, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C1-C12alkylthio, C2-C12alkenylthio, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, di(C1-C12alkyl)aminosulfonyl, C1-C12alkylsulfonylaminocarbonyl, C1-C12alkylcarbonylaminosulfonyl, C3-C12cycloalkyloxycarbonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkylcarbonylC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C2-C12alkenoxycarbonyl, C2-C12alkynoxycarbonyl, C1-C12alkoxyC1-C12alkoxycarbonyl, C1-C12alkylaminothio, di(C1-C12alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, or (hetero)arylC1-C6alkyloxycarbonyl by 1 to 5 following groups: halo, NO2, cyano, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, or haloC1-C6alkoxy;
or a salt thereof formed with an acid selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, and citric acid.

9. The substituted pyrimidine compound according to claim 8, wherein
R1 is C1-C6alkyl or C3-C6cycloalkyl;
R2 is halo or cyano;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, halo, C1-C6alkyl, C1-C6alkoxy, and C3-C6cycloalkyl; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, and R5c, may be the same or different, selected independently from H or OH;
R6 is H or OH;
R7, R8, R9, R10, and R11, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, amino, cyano, NO2, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, haloC1-C6alkoxy, C3-C6cycloalkyl, C1-C6alkylamino, haloC1-C6alkylamino, di(C1-C6alkyl)amino, halodi(C1-C6alkyl)amino, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, halodi(C1-C6alkyl)aminocarbonyl, CONH2, C1-C6alkylthio, haloC1-C6alkylthio, C2-C6alkenyl, C2-C6alkynyl, C2-C6alkenoxy, haloC2-C6alkenoxy, C2-C6alkynoxy, haloC2-C6alkynoxy, C1-C6alkylsulfonyl, haloC1-C6alkylsulfonyl, C1-C6alkylcarbonyl, haloC1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, haloC1-C6alkoxycarbonyl, C1-C6alkoxyC1-C6alkyl, haloC1-C6alkoxyC1-C6alkyl, C1-C6alkylthioC1-C6alkyl, haloC1-C6alkylthioC1-C6alkyl, C1-C6alkoxycarbonylC1-C6alkyl, haloC1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkylthiocarbonylC1-C6alkyl, haloC1-C6alkylthiocarbonylC1-C6alkyl, C1-C6alkylcarbonyloxy, haloC1-C6alkylcarbonyloxy, C1-C6alkoxycarbonyloxy, haloC1-C6alkoxycarbonyloxy, C1-C6alkylaminocarbonyloxy, haloC1-C6alkylaminocarbonyloxy, C1-C6alkylsulfonyloxy, haloC1-C6alkylsulfonyloxy, C1-C6alkoxyC1-C6alkoxy, haloC1-C6alkoxyC1-C6alkoxy, C1-C6alkoxycarbonylC1-C6alkoxy, and haloC1-C6alkoxycarbonylC1-C6alkoxy;
W is H or C1-C3alkyl;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H, OH, H(C)═O, C1-C6alkyl, C1-C6alkylsulfonyl or C1-C6alkylcarbonyl;
or wherein the salt is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, or citric acid.

10. The substituted pyrimidine compound according to claim 9, wherein
R1 is C1-C4alkyl or C3-C4cycloalkyl;
R2 is F, Cl, Br, or cyano;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, halo, C1-C4alkyl, C1-C4alkoxy, and C3-C6cycloalkyl; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, and R5c, may be the same or different, selected independently from H or OH;
R6 is H or OH;
R7, R8, R9, R10, and R11, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, amino, cyano, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C3-C4cycloalkyl, C1-C4alkylamino, haloC1-C4alkylamino, di(C1-C4alkyl)amino, halodi(C1-C4alkyl)amino, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, halodi(C1-C4alkyl)aminocarbonyl, CONH2, C1-C4alkylthio, haloC1-C4alkylthio, C2-C4alkenyl, C2-C4alkynyl, C2-C4alkenoxy, haloC2-C4alkenoxy, C2-C4alkynoxy, haloC2-C4alkynoxy, C1-C4alkylsulfonyl, haloC1-C4alkylsulfonyl, C1-C4alkylcarbonyl, haloC1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, haloC1-C4alkoxycarbonyl, C1-C4alkoxyC1-C4alkyl, haloC1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, haloC1-C4alkylthioC1-C4alkyl, C1-C4alkoxycarbonylC1-C4alkyl, haloC1-C4alkoxycarbonylC1-C4alkyl, C1-C4alkylthiocarbonylC1-C4alkyl, haloC1-C4alkylthiocarbonylC1-C4alkyl, C1-C4alkylcarbonyloxy, haloC1-C4alkylcarbonyloxy, C1-C4alkoxycarbonyloxy, haloC1-C4alkoxycarbonyloxy, C1-C4alkylaminocarbonyloxy, haloC1-C4alkylaminocarbonyloxy, C1-C4alkylsulfonyloxy, haloC1-C4alkylsulfonyloxy, C1-C4alkoxyC1-C4alkoxy, haloC1-C4alkoxyC1-C4alkoxy, C1-C4alkoxycarbonylC1-C4alkoxy, and haloC1-C4alkoxycarbonylC1-C4alkoxy;
W is H or CH3;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H, OH, H(C)═O, C1-C4alkyl, C1-C4alkylsulfonyl, or C1-C4alkylcarbonyl;
or wherein the salt is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, maleic acid, sorbic acid, malic acid, or citric acid.

11. The substituted pyrimidine compound according to claim 10, wherein
R1 is CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, cyclopropyl or cyclobutyl;
R2 is F, Cl, Br, or cyano;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, F, Cl, Br, I, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, OCH3, OC2H5, OC3H7-n, OC3H7-i, OC4H9-n, OC4H9-s, OC4H9-i, and OC4H9-t;
R5a, R5b, and R5c, may be the same or different, selected independently from H or OH;
R6 is H or OH;
R7, R8, R9, R10, and R11, may be the same or different, and are each selected independently from the group consisting of H, F, Cl, Br, I, cyano, amino, NO2, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, CF3, CCl3, CClF2, CCl2F, CHCl2, CH2F, CHF2, OCH3, OC2H5, OC3H7-n, OC3H7-i, OC4H9-n, OC4H9-s, OC4H9-i, OC4H9-t, OCF3, OCH2CF3, COOCH3, COOC2H5, CONH2, CONHCH3, CONHC2H5, CONH(CH3)2, methylsulfonyl, and trifluoromethylsulfonyl;
W is H or CH3;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H;
or wherein the salt is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid, or benzoic acid.

12. The substituted pyrimidine compound according to claim 11, wherein
R1 is CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, cyclopropyl or cyclobutyl;
R2 is F, Cl, Br, or cyano;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, F, Cl, Br, I, CH3, C2H5, n-C3H7, i-C3H7, OCH3, OC2H5, OC3H7-n, and OC3H7-i;
R5a, R5b, and R5c, are H;
R6 is H;
R7, R8, R9, R10, and R11, may be the same or different, and are each selected independently from the group consisting of H, F, Cl, Br, I, cyano, NO2, CH3, C2H5, n-C3H7, i-C3H7, n-C4H9, s-C4H9, i-C4H9, t-C4H9, OCH3, OCF3, CF3, CCl3, CClF2, CCl2F, CHCl2, CH2F, CHF2, methylsulfonyl, and trifluoromethylsulfonyl;
W is H or CH3;
A is NH;
B is —CH2— or —CH2CH2—; and
or wherein the salt is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, maleic acid, or benzoic acid.

13. The substituted pyrimidine compound according to claim 12, wherein
R1 is CH3 or C2H5;
R2 is Cl or cyano;
R3 and R4 are H;
R5a, R5b, and R5c, are H;
R6 is H;
W is H or CH3;
R7, R8, R9, R10, and R11, may be the same or different, and are each selected independently from the group consisting of H, F, Cl, cyano, NO2, CH3, OCH3, OCF3, CF3, and methylsulfonyl;
A is NH; and
B is —CH2— or —CH2CH2—;
or wherein the salt is formed with hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, or trifluoroacetic acid.

14. A substituted pyrimidine compound represented by formula III:




wherein
R1 is C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl, haloC2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, or haloC1-C12alkoxyC1-C12alkyl;
R2 is halo, cyano, C1-C12alkyl, or haloC1-C12alkoxy;
W is H, halo, C1-C12alkyl, C1-C12alkylthio, or C1-C12alkylsulfonyl;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, C1-C12alkyl, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, unsubstituted or further substituted arylC1-C6alkyl or heteroarylC1-C6alkyl by 1 to 5 following groups: halo, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, and haloC1-C6alkoxy; or R3, R4 and conjoint carbon can also form a C3-C58 cycle;
R5a, R5b, and R5c, may be the same or different, and are each selected independently from the group consisting of H, C3-C12cycloalkyl, C1-C12alkylthio, haloC1-C12alkylthio, C3-C12alkenoxy, haloC3-C12alkenoxy, C3-C12alkynoxy, haloC3-C12alkynoxy, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkylcarbonyloxy, C1-C12alkylcarbonylamino, C1-C12alkylsulfonyloxy, C1-C12alkoxycarbonyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkoxycarbonylamino, C1-C12alkoxyC1-C12alkoxy, and C1-C12alkoxycarbonylC1-C12alkoxy;
X2 is N or CR7;
X3 is N or CR8;
X4 is N or CR9;
X6 is N or CR11; however, X2, X3, X4, and X6 are not simultaneously N;
R7, R8, R9, and R11, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C1-C12alkoxycarbonyl, CONH2, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C1-C12alkylsulfonyl, and haloC1-C12alkylsulfonyl;
R10 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C12alkenoxy, haloC2-C12alkenoxy, C2-C12alkynoxy, haloC2-C12alkynoxy, C1-C12alkylthio, haloC1-C12alkylthio, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, C1-C12alkylamino, haloC1-C12alkylamino, di(C1-C12alkyl)amino, C1-C12alkoxycarbonyl, CONH2, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, cyanoC1-C12alkoxy, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonylC1-C12alkyl, or di(C1-C12alkyl)aminocarbonylC1-C12alkyl;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H, OH, H(C)═O, C1-C12alkyl, haloC1-C12alkyl, C1-C12alkoxy, haloC1-C12alkoxy, C3-C12cycloalkyl, C1-C12alkylthio, C2-C12alkenylthio, C2-C12alkenyl, C2-C12alkynyl, haloC2-C12alkenyl, haloC2-C12alkynyl, C1-C12alkoxyC1-C12alkyl, haloC1-C12alkoxyC1-C12alkyl, C1-C12alkylthioC1-C12alkyl, haloC1-C12alkylthioC1-C12alkyl, C1-C12alkylsulfinyl, haloC1-C12alkylsulfinyl, C1-C12alkylsulfonyl, haloC1-C12alkylsulfonyl, C1-C12alkylaminosulfonyl, di(C1-C12alkyl)aminosulfonyl, C1-C12alkylsulfonylaminocarbonyl, C1-C12alkylcarbonylaminosulfonyl, C3-C12cycloalkyloxycarbonyl, C1-C12alkylcarbonyl, haloC1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, haloC1-C12alkoxycarbonyl, C1-C12alkylcarbonylC1-C12alkyl, C1-C12alkoxycarbonylC1-C12alkyl, C1-C12alkylaminocarbonyl, di(C1-C12alkyl)aminocarbonyl, C2-C12alkenoxycarbonyl, C2-C12alkynoxycarbonyl, C1-C12alkoxyC1-C12alkoxycarbonyl, C1-C12alkylaminothio, di(C1-C12alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, or (hetero)arylC1-C6alkyloxycarbonyl by 1 to 5 following groups: halo, NO2, cyano, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxy, or haloC1-C6alkoxy;
or a salt thereof formed with an acid selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, and citric acid.

15. The substituted pyrimidine compound according to claim 14, wherein
R1 is C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl, haloC2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkynyl, C1-C8alkoxyC1-C8alkyl, or haloC1-C8alkoxyC1-C8alkyl;
R2 is halo, cyano, C1-C8alkyl, or haloC1-C8alkoxy;
W is H, halo, C1-C8alkyl, C1-C8alkylthio, or C1-C8alkylsulfonyl;
R3 and R4, may be the same or different, and are each selected independently from the group consisting of H, C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C1-C8alkoxyC1-C8alkyl, unsubstituted or further substituted arylC1-C4alkyl or heteroarylC1-C4alkyl by 1 to 3 following groups: halo, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, and haloC1-C4alkoxy; or R3, R4 and conjoint carbon can also form a C3-C8 cycle;
R5a, R5b, and R5c, may be the same or different, and are each selected independently from the group consisting of H, C3-C6cycloalkyl, C1-C8alkylthio, haloC1-C8alkylthio C3-C8alkenoxy, haloC3-C8alkenoxy, C3-C8alkynoxy, haloC3-C8alkynoxy, C1-C8alkylsulfinyl, haloC1-C8alkylsulfinyl, C1-C8alkylsulfonyl, haloC1-C8alkylsulfonyl, C1-C8alkylcarbonyl, haloC1-C8alkylcarbonyl, C1-C8alkylcarbonyloxy, C1-C8alkylcarbonylamino, C1-C8alkylsulfonyloxy, C1-C8alkoxycarbonyl, C1-C8alkoxycarbonylC1-C8alkyl, C1-C8alkoxycarbonylamino, C1-C8alkoxyC1-C8alkoxy, and C1-C8alkoxycarbonylC1-C8alkoxy;
X2 is N or CR7;
X3 is N or CR8;
X4 is N or CR9;
X6 is N or CR11; however, X2, X3, X4, and X6 are not simultaneously N;
R7, R8, R9, and R11, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxy, haloC1-C8alkoxy, C1-C8alkoxycarbonyl, CONH2, C1-C8alkylaminocarbonyl, di(C1-C8alkyl)aminocarbonyl, C1-C8alkylsulfonyl, and haloC1-C8alkylsulfonyl;
R10 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxy, haloC1-C8alkoxy, C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkynyl, C2-C8alkenoxy, haloC2-C8alkenoxy, C2-C8alkynoxy, haloC2-C8alkynoxy, C1-C8alkylthio, haloC1-C8alkylthio, C1-C8alkoxyC1-C8alkyl, haloC1-C8alkoxyC1-C8alkyl, C1-C8alkylthioC1-C8alkyl, haloC1-C8alkylthioC1-C8alkyl, C1-C8alkylsulfinyl, haloC1-C8alkylsulfinyl, C1-C8alkylsulfonyl, haloC1-C8alkylsulfonyl, C1-C8alkylaminosulfonyl, C1-C8alkylamino, haloC1-C8alkylamino, di(C1-C8alkyl)amino, C1-C8alkoxycarbonyl, CONH2, C1-C8alkylaminocarbonyl, di(C1-C8alkyl)aminocarbonyl, cyanoC1-C8alkoxy, C1-C8alkoxycarbonylC1-C8alkyl, C1-C8alkylaminocarbonylC1-C8alkyl, and di(C1-C8alkyl)aminocarbonylC1-C8alkyl;
A is NR12;
B is —CH2— or —CH2CH2—; and
R12 is H, OH, H(C)═O, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxy, haloC1-C8alkoxy, C3-C8cycloalkyl, C1-C8alkylthio, C2-C8alkenylthio, C2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C1-C8alkoxyC1-C8alkyl, haloC1-C8alkoxyC1-C8alkyl, C1-C8alkylthioC1-C8alkyl, haloC1-C8alkylthioC1-C8alkyl, C1-C8alkylsulfinyl, haloC1-C8alkylsulfinyl, C1-C8alkylsulfonyl, haloC1-C8alkylsulfonyl, C1-C8alkylaminosulfonyl, di(C1-C8alkyl)aminosulfonyl, C1-C8alkylsulfonylaminocarbonyl, C1-C8alkylcarbonylaminosulfonyl, C3-C8cycloalkyloxycarbonyl, C1-C8alkylcarbonyl, haloC1-C8alkylcarbonyl, C1-C8alkoxycarbonyl, haloC1-C8alkoxycarbonyl, C1-C8alkylcarbonylC1-C8alkyl, C1-C8alkoxycarbonylC1-C8alkyl, C1-C8alkylaminocarbonyl, di(C1-C8alkyl)aminocarbonyl, C2-C8alkenoxycarbonyl, C2-C8alkynoxycarbonyl, C1-C8alkoxyC1-C8alkoxycarbonyl, C1-C8alkylaminothio, di(C1-C8alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC1-C6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, or (hetero)arylC1-C6alkyloxycarbonyl by 1 to 3 following groups: halo, NO2, cyano, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, or haloC1-C4alkoxy;
or a salt thereof formed with an acid selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, and citric acid.

16. The substituted pyrimidine compound according to claim 15, wherein
R1 is C1-C4alkyl, C3-C6cycloalkyl, C2-C4alkenyl, haloC2-C4alkenyl, C2-C4alkynyl, haloC2-C4alkynyl, C1-C4alkoxyC1-C4alkyl, or haloC1-C4alkoxyC1-C4alkyl;
R2 is halo or cyano;
W is H or CH3;
R3 and R4 are H, CH3, or C2H5;
R5a, R5b, and R5c, may be the same or different, and are each selected independently from the group consisting of H, C3-C6cycloalkyl, C1-C4alkylthio, haloC1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylcarbonyl, and C1-C4alkoxyC1-C4alkoxy;
X2 is N or CR7;
X3 is N or CR8;
X4 is N or CR9;
X6 is N or CR11; however, X2, X3, X4, and X6 are not simultaneously N;
R7, R8, R9, and R11, may be the same or different, and are each selected independently from the group consisting of H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, C1-C4alkylsulfonyl, and haloC1-C4alkylsulfonyl;
R10 is H, halo, OH, cyano, HO(C═O), amino, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C3-C4cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, C2-C4alkenoxy, haloC2-C4alkenoxy, C2-C4alkynoxy, haloC2-C4alkynoxy, C1-C4alkylthio, haloC1-C4alkylthio, C1-C4alkoxyC1-C4alkyl, haloC1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, haloC1-C4alkylthioC1-C4alkyl, C1-C4alkylsulfinyl, haloC1-C4alkylsulfinyl, C1-C4alkylsulfonyl, haloC1-C4alkylsulfonyl, C1-C4alkylaminosulfonyl, C1-C4alkylamino, haloC1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkoxycarbonyl, CONH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, cyanoC1-C12alkoxy, C1-C4alkoxycarbonylC1-C4alkyl, C1-C4alkylaminocarbonylC1-C4alkyl, or di(C1-C4alkyl)aminocarbonylC1-C4alkyl;
A is NH; and
B is —CH2— or —CH2CH2—;
or wherein the salt is formed with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, or citric acid.

17. The substituted pyrimidine compound according to claim 16, wherein the substituted pyrimidine compound is represented by formula III-A, III-B, III-C, III-D, III-E, III-F, III-G, III-H, III-I, or III-J:






wherein
R1 is C1-C4alkyl, C3-C6cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkoxyC1-C4alkyl, or haloC1-C4alkoxyC1-C4alkyl;
R2 is halo or cyano;
W is H or CH3;
R3 and R4 is H, CH3, or C2H5;
R5a, R5b, and R5c, may be the same or different, and are each selected independently from the group consisting of H and C1-C4alkylcarbonyl;
R7, R8, R9, and R11, may be the same or different, and are each selected independently from the group consisting of H, F, Cl, Br, I, cyano, HO(C═O), NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkoxycarbonyl, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, C1-C4alkylsulfonyl, and haloC1-C4alkylsulfonyl;
R10 is H, F, Cl, Br, I, cyano, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkylsulfonyl, or haloC1-C4alkylsulfonyl; and
A is NH;
or wherein the salt of formula III-A, III-B, III-C, III-D, III-E, III-F, III-G, III-H, III-I, or III-J is formed with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, or citric acid.

18. The substituted pyrimidine compound according to claim 17, wherein
the substituted pyrimidine compound is represented by formula III-A and wherein
R1 is CH3, or C2H5;
R2 is halo or cyano;
W is H or CH3;
R3 and R4 are H;
R5a and R5c are H;
R5b is H;
R7, R8, R9, and R11, may be the same or different, and are each selected independently from the group consisting of H, F, Cl, Br, cyano, NO2, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, haloC1-C4alkoxy, C1-C4alkoxycarbonyl, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, C1-C4alkylsulfonyl, and haloC1-C4alkylsulfonyl;
R10 is H, F, Cl, Br, I, cyano, NO2, methylsulfonyl, C1-C4alkyl, haloC1-C4alkyl, C1-C4alkoxy, or haloC1-C4alkoxy; and
A is NH;
or wherein the salt of formula III-A is formed with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, or citric acid.

19. The substituted pyrimidine compound according to claim 18, wherein R1 is Cl, CH3 or C2H5;
R2 is cyano;
W is H or CH3;
R3 and R4 are H;
R5a and R5c are H;
R5b is H;
R7, R8, R9, and R11, may be the same or different, and are each selected independently from the group consisting of H, F, Cl, CH3, cyano, NO2, CF3, CClF2, CCl3, OCH3, OCF3, OCH2CF3, methylsulfonyl, and trifluorosulfonyl;
R10 is H, F, Cl, CH3, cyano, NO2, methylsulfonyl, CF3, CClF2, OCH3, OCF3, or OCH2CF3; and
A is NH;
or wherein the salt of formula III-A is formed with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid, or citric acid.

20. A fungicidal, insecticidal, or acaricidal composition comprising one or more compounds according to claim 1 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is 0.1-99%.

21. A fungicidal, insecticidal, or acaricidal composition comprising one or more compounds according to claim 2 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is 0.1-99%.

22. A method to control fungus, insects, and/or mites which comprises contacting an effective dose of the composition of claim 20 with the fungus, insects, and/or mites, or its growth medium.

23. A method to control fungus, insects, and/or mites which comprises contacting an effective dose of the composition of claim 21 with the fungus, insects, and/or mites, or its growth medium.

24. A fungicidal, insecticidal, or acaricidal composition comprising one or more compounds according to claim 8 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is 0.1-99%.

25. A method to control fungus, insects, and/or mites which comprises contacting an effective dose of the composition of claim 24 with the fungus, insects, and/or mites, or its growth medium.

26. A fungicidal, insecticidal, or acaricidal composition comprising one or more compounds according to claim 14 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is 0.1-99%.

27. A method to control fungus, insects, and/or mites which comprises contacting an effective dose of the composition of claim 26 with the fungus, insects, and/or mites, or its growth medium.