Substituted pyrimidine (thio) ester compounds and uses thereof

Abstract

The present invention discloses a substituted pyrimidine (thio) ester compound, the structure of which is shown in the general formula I: the definition of each substituent in the formula is shown in the specification. The compound of the present invention has excellent fungicidal activity and has excellent control effect on powdery mildew, downy mildew and the like.

Description

Technical Field

[0001] The invention belongs to the field of agricultural sterilization, and specifically relates to a novel substituted pyrimidine (thio) ester compound and its application. Background Art

[0002] Certain pyrimidine phenols and their sulfonates are known to have good biological activities.

[0003]

[0004] However, there are no reports on substituted pyrimidine (thio) ester compounds with the structure shown in the general formula I of the present invention.

[0005] Some known reference compounds are as follows:

[0006] Summary of the invention

[0007] The object of the present invention is to provide a substituted pyrimidine (thio) ester compound which can control harmful pathogens at very low dosage and is used as a drug for preventing and controlling pathogens in agriculture or other fields.

[0008] To achieve the above object, the technical solution of the present invention is as follows:

[0009] A substituted pyrimidine (thio) ester compound, wherein the (thio) ester-containing compound is a compound represented by the general formula I;

[0010]

[0011] Where:

[0012] R1 is selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, cyano C1-C 12 Alkyl, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio, C1-C 12 Alkylamino, halogenated C1-C 12 Alkylamino, di(C1-C 12 alkyl)amino, halogenated di(C1-C 12 Alkyl)amino, C1-C 12 Alkylsulfinyl, halogenated C1-C 12 Alkylsulfinyl, C1-C 12Alkylsulfonyl, halogenated C1-C 12 Alkylsulfonyl, C2-C 12 Alkenyl, halogenated C2-C 12 Alkenyl, C2-C 12 Alkynyl, halo C2-C 12 Alkynyl, C2-C 12 Alkenyloxy, halogenated C2-C 12 Alkenyloxy, C2-C 12 Alkynyloxy, halogenated C2-C 12 Alkynyloxy, C2-C 12 Alkenylamino, halogenated C2-C 12 Alkenylamino, C2-C 12 Alkynylamino, halo C2-C 12 Alkynylamino, C1-C 12 Alkylcarbonyl, halogenated C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, halogenated C1-C 12 Alkoxycarbonyl, C1-C 12 Alkylaminocarbonyl, halogenated C1-C 12 Alkylaminocarbonyl, C1-C 12 Alkylcarbonyloxy, halogenated C1-C 12 Alkylcarbonyloxy, C1-C 12 Alkylcarbonylamino, halogenated C1-C 12 Alkylcarbonylamino, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C 12 Alkylamino C1-C 12 Alkyl, halogenated C1-C 12 Alkylamino C1-C 12 alkyl;

[0013] R2 is selected from hydrogen, halogen, cyano, nitro, amino, carboxyl, formyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, cyano C1-C 12 Alkyl, C3-C 12 Cycloalkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy;

[0014] R1 and R2 can also form a five-membered, six-membered, seven-membered or eight-membered ring containing C, N, O or S with the connected pyrimidine ring;

[0015] W is selected from hydrogen, halogen, cyano, amino, hydroxyl, thiol, carboxyl, morpholinyl, piperazinyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, cyano C1-C 12 Alkyl, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio, NR3R4, C2-C 12 Alkenyloxy, halogenated C2-C 12 Alkenyloxy, C2-C 12 Alkynyloxy, halogenated C2-C 12 Alkynyloxy, C1-C 12 Alkylsulfinyl, halogenated C1-C 12 Alkylsulfinyl, C1-C 12 Alkylsulfonyl, halogenated C1-C 12 Alkylsulfonyl, C1-C 12 Alkylcarbonyloxy, halogenated C1-C 12 Alkylcarbonyloxy, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C 12 Alkylamino C1-C 12 Alkyl, halogenated C1-C 12 Alkylamino C1-C 12 Alkyl, unsubstituted or further substituted by 1 to 5 R5 groups which may be the same or different (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0016] X is selected from O or S;

[0017] Y is selected from O or S;

[0018] R3 and R4 may be the same or different and are selected from hydrogen, hydroxyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, cyano C1-C 12 Alkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl, C2-C 12 Alkenyl, C2-C 12 Alkynyl, halo C2-C12 Alkenyl, halogenated C2-C 12 Alkynyl, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C 12 Alkylthio C1-C 12 Alkyl, halogenated C1-C 12 Alkylthio C1-C 12 Alkyl, C1-C 12 Alkylcarbonyl, halogenated C1-C 12 Alkylcarbonyl, C1-C 12 Alkylsulfinyl, halogenated C1-C 12 Alkylsulfinyl, C1-C 12 Alkylsulfonyl, halogenated C1-C 12 Alkylsulfonyl, C1-C 12 Alkylaminosulfonyl, di(C1-C 12 Alkyl)aminosulfonyl, C1-C 12 Alkoxycarbonyl, halogenated C1-C 12 Alkoxycarbonyl, C1-C 12 Alkylaminocarbonyl, halogenated C1-C 12 Alkylaminocarbonyl;

[0019] R5 is selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, carboxyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, cyano C1-C 12 Alkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl, C1-C 12 Alkylamino, halogenated C1-C 12 Alkylamino, di(C1-C 12 alkyl)amino, halogenated di(C1-C 12 Alkyl)amino, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio, C2-C 12 Alkenyl, C2-C 12 Alkynyl, C2-C 12 Alkenyloxy, halogenated C2-C 12 Alkenyloxy, C2-C 12 Alkynyloxy, halogenated C2-C 12 Alkynyloxy, C1-C 12 Alkylsulfonyl, halogenated C1-C12 Alkylsulfonyl, C1-C 12 Alkylcarbonyl, halogenated C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, halogenated C1-C 12 Alkoxycarbonyl, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C 12 Alkylthio C1-C 12 Alkyl, halogenated C1-C 12 Alkylthio C1-C 12 Alkyl, C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, C1-C 12 Alkylcarbonyloxy, halogenated C1-C 12 Alkylcarbonyloxy, C1-C 12 Alkoxycarbonyloxy, halogenated C1-C 12 Alkoxycarbonyloxy, C1-C 12 Alkylsulfonyloxy, halogenated C1-C 12 Alkylsulfonyloxy, C1-C 12 Alkoxy C1-C 12 Alkoxy or halogenated C1-C 12 Alkoxy C1-C 12 Alkoxy;

[0020] Q is selected from a saturated or unsaturated five-membered ring, a five-membered fused (hetero) ring, a five-membered ring substituted with (hetero)aryl, a saturated or unsaturated six-membered heterocyclic ring or a six-membered fused (hetero) ring containing C, N, O or S which is unsubstituted or further substituted with 1 to 5 R5 which may be the same or different;

[0021] When Q is selected from unsubstituted or substituted pyridine and pyrazine, the substituents on pyridine and pyrazine are not simultaneously selected from hydrogen;

[0022] When Q is selected from unsubstituted or substituted pyridine, it does not include: 2-isopropyl-6-methyl-pyrimidin-4-yl-2,6-dichloro-5-fluoropyridine-3-carboxylate;

[0023] When Q is selected from unsubstituted or substituted furan, thiophene, and benzofuran, the substituents on the furan, thiophene, and benzofuran rings are not simultaneously selected from hydrogen;

[0024] When Q is selected from unsubstituted or substituted pyrrole, the following compounds are excluded: 4-(3,3-dimethylbutan-2-yl)-2-(pyrimidin-4-yl)-3-methyl-1H-pyrrole-2,4-dicarboxylate;

[0025] When Q is selected from unsubstituted or substituted isoxazole, the following compounds are excluded: S-(4H-purin-6-yl)-4-methylisoxazole-3-carbothioate, S-(4-quinazolinyl)-3-(2-chlorophenyl)-5-methylisoxazole-4-carbothioate, S-(6-methyl-2-mercapto-4-pyrimidinyl)-3-(2-chlorophenyl)-5-methylisoxazole-4-carbothioate;

[0026] When Q is selected from unsubstituted or substituted 1,2,3-thiadiazole, the following compounds are excluded: 5-fluoropyrimidin-4-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate;

[0027] When Q is selected from unsubstituted or substituted pyridine and pyrazine, the substituents on pyridine and pyrazine are not simultaneously selected from hydrogen;

[0028] When Q is selected from unsubstituted or substituted pyridine, it does not include: 2-isopropyl-6-methyl-pyrimidin-4-yl-2,6-dichloro-5-fluoropyridine-3-carboxylate;

[0029] Or a salt of the compound represented by general formula I.

[0030] Preferably, the (thio)ester-containing compound is a compound represented by general formula I;

[0031]

[0032] Where:

[0033] R1 is selected from C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl;

[0034] R2 is selected from C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl;

[0035] W is selected from NR3R4, unsubstituted or further substituted by 1 to 5 R5 groups which may be the same or different (hetero)arylamino;

[0036] X is selected from O or S;

[0037] Y is selected from O or S;

[0038] R3 and R4 may be the same or different and are selected from hydrogen, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, cyano C1-C 12 Alkyl, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl;

[0039] R5 is selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, carboxyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, cyano C1-C 12 Alkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl, C1-C 12 Alkylamino, halogenated C1-C 12 Alkylamino, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio;

[0040] Q is selected from one of Q1, Q2, Q3, Q4, Q5, Q6, Q9, Q11, Q12, Q13, Q14, Q15, Q16, Q17, Q18:

[0041] in:

[0042] R 6a , R 7a , R 8a are selected from hydrogen, hydroxy, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkylcarbonyl, halogenated C1-C4 alkylcarbonyl, C1-C C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, C1-C4 alkoxy C1-C4 alkyl, halogenated C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, halogenated C1-C4 alkylthio C1-C4 alkyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different (hetero)aryl;

[0043] R 6b , R 6c , R 7b , R 7c , R 8b , R 8c R5 may be the same or different and are selected from hydrogen, halogen, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, unsubstituted or substituted by 1-5 R5 which may be the same or different (hetero)aryl;

[0044] R 9a , R 9b , R 10a , R 10b , R 11a , R 11b R5, which may be the same or different, are independently selected from hydrogen, halogen, amino, cyano, nitro, C1-C4 alkyl, halo C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halo C3-C4 cycloalkyl, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkylthio, halo C1-C4 alkylthio, C1-C4 alkylamino, halo C1-C4 alkylamino, di(C1-C4 alkyl)amino, C3-C4 cycloalkylamino, C1-C4 carbonylamino, C1-C4 alkoxycarbonylamino, and (hetero)aryl which is unsubstituted or substituted by 1-5 R5 which may be the same or different;

[0045] R 14a , R 14b , R 14c may be the same or different, but are not selected from hydrogen at the same time, and are each selected from hydrogen, halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyloxy, halogenated C3-C4 cycloalkyloxy, C1-C4 alkylamino, halogenated C1-C4 alkylamino, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylsulfinyl, halogenated C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl or halogenated C1-C4 alkylsulfonyl;

[0046] R 16a , R 16b , R 16c , R 16dR5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0047] R 17a , R 17b , R 17c , R 17d R5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0048] R 18a , R 18b , R 18c , R 18d R5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0049] R 19a , R 19b , R 19cR5, which may be the same or different, are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylamino, halogenated C1-C4 alkylamino, di(C1-C4 alkyl)amino, halogenated di(C1-C4 alkyl)amino, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1-5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0050] R 20a , R 20b , R 20c R5, which may be the same or different, are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylamino, halogenated C1-C4 alkylamino, di(C1-C4 alkyl)amino, halogenated di(C1-C4 alkyl)amino, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1-5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0051] R 21a , R 21b , R 21c may be the same or different, and are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl;

[0052] R 22a , R 22b , R 22c may be the same or different, but are not selected from hydrogen at the same time, and are each selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl;

[0053] R 23a , R 23b , R 23c , R 23d , R 23e , R 23fmay be the same or different, and are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl;

[0054] Or a salt of the compound represented by general formula I.

[0055] Further preferably, the (thio)ester-containing compound is a compound represented by the general formula I;

[0056]

[0057] Where:

[0058] R1 is selected from C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0059] R2 is selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0060] W is selected from NR3R4, unsubstituted or further substituted by 1 to 5 R5 groups which may be the same or different (hetero)arylamino;

[0061] X is selected from O or S;

[0062] Y is selected from O or S;

[0063] R3 and R4 may be the same or different and are selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0064] R5 is selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, carboxyl, C1-C4 alkyl, halo-C1-C4 alkyl, cyano-C1-C4 alkyl, C1-C4 alkoxy, halo-C1-C4 alkoxy, C3-C4 cycloalkyl, halo-C3-C4 cycloalkyl, C1-C4 alkylamino, halo-C1-C4 alkylamino, C1-C4 alkylthio, halo-C1-C4 alkylthio;

[0065] Q is selected from one of Q1, Q2, Q3, Q4, Q5, Q6, Q9, Q11, Q12, Q13, Q14, Q15, Q16, Q17, Q18:

[0066] in:

[0067] R 6a , R 7a , R 8aare selected from hydrogen, hydroxy, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkylcarbonyl, halogenated C1-C4 alkylcarbonyl, C1-C C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, C1-C4 alkoxy C1-C4 alkyl, halogenated C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, halogenated C1-C4 alkylthio C1-C4 alkyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different (hetero)aryl;

[0068] R 6b , R 6c , R 7b , R 7c , R 8b , R 8c R5 may be the same or different and are selected from hydrogen, halogen, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, unsubstituted or substituted by 1-5 R5 which may be the same or different (hetero)aryl;

[0069] R 9a , R 9b , R 10a , R 10b , R 11a , R 11b R5, which may be the same or different, are independently selected from hydrogen, halogen, amino, cyano, nitro, C1-C4 alkyl, halo C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halo C3-C4 cycloalkyl, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkylthio, halo C1-C4 alkylthio, C1-C4 alkylamino, halo C1-C4 alkylamino, di(C1-C4 alkyl)amino, C3-C4 cycloalkylamino, C1-C4 carbonylamino, C1-C4 alkoxycarbonylamino, and (hetero)aryl which is unsubstituted or substituted by 1-5 R5 which may be the same or different;

[0070] R14a, R14b, R14c may be the same or different, but are not selected from hydrogen at the same time, and are each selected from hydrogen, halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyloxy, halogenated C3-C4 cycloalkyloxy, C1-C4 alkylamino, halogenated C1-C4 alkylamino, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylsulfinyl, halogenated C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl or halogenated C1-C4 alkylsulfonyl;

[0071] R 16a , R 16b , R 16c , R 16d R5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0072] R 17a , R 17b , R 17c , R 17d R5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0073] R 18a , R 18b , R 18c , R 18dR5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0074] R 19a , R 19b , R 19c R5, which may be the same or different, are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylamino, halogenated C1-C4 alkylamino, di(C1-C4 alkyl)amino, halogenated di(C1-C4 alkyl)amino, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1-5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0075] R 20a , R 20b , R 20c R5, which may be the same or different, are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylamino, halogenated C1-C4 alkylamino, di(C1-C4 alkyl)amino, halogenated di(C1-C4 alkyl)amino, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1-5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0076] R 21a , R 21b , R 21c may be the same or different, and are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl;

[0077] R 22a , R 22b , R 22cmay be the same or different, but are not selected from hydrogen at the same time, and are each selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl;

[0078] R 23a , R 23b , R 23c , R 23d , R 23e , R 23f may be the same or different, and are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl;

[0079] Or a salt of the compound represented by general formula I.

[0080] It is further preferred that in the compound of general formula I:

[0081] R1 is selected from C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0082] R2 is selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0083] W is selected from NR3R4, unsubstituted or further substituted by 1 to 5 R5 groups which may be the same or different (hetero)arylamino;

[0084] X is selected from O or S;

[0085] Y is selected from O or S;

[0086] R3 and R4 may be the same or different and are selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0087] R5 is selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, carboxyl, C1-C4 alkyl, halo-C1-C4 alkyl, cyano-C1-C4 alkyl, C1-C4 alkoxy, halo-C1-C4 alkoxy, C3-C4 cycloalkyl, halo-C3-C4 cycloalkyl, C1-C4 alkylamino, halo-C1-C4 alkylamino, C1-C4 alkylthio, halo-C1-C4 alkylthio;

[0088] Q is selected from Q selected from one of Q1, Q2, Q3, Q4, Q5, Q6, Q9, Q11, Q12, Q13;

[0089] Or a salt of the compound represented by general formula I.

[0090] The structure of the compound of formula I is: I-1, I-2, I-3, I-4, I-5, I-6, I-9, IV-1, IV-2 or IV-3;

[0091]

[0092] R1 is selected from C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0093] R2 is selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0094] W is selected from NR3R4, unsubstituted or further substituted by 1-5 identical or different R5 groups (hetero)arylamino;

[0095] X is selected from O or S;

[0096] Y is selected from O or S;

[0097] R3 and R4 may be the same or different and are selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl;

[0098] R5 is selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, carboxyl, C1-C4 alkyl, halo-C1-C4 alkyl, cyano-C1-C4 alkyl, C1-C4 alkoxy, halo-C1-C4 alkoxy, C3-C4 cycloalkyl, halo-C3-C4 cycloalkyl, C1-C4 alkylamino, halo-C1-C4 alkylamino, C1-C4 alkylthio, halo-C1-C4 alkylthio;

[0099] R 6a , R 7a , R 8aare selected from hydrogen, hydroxy, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkylcarbonyl, halogenated C1-C4 alkylcarbonyl, C1-C C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, C1-C4 alkoxy C1-C4 alkyl, halogenated C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, halogenated C1-C4 alkylthio C1-C4 alkyl, (hetero)aryl which is unsubstituted or substituted by the same or different 1-5 R5;

[0100] R 6b , R 6c , R 7b , R 7c , R 8b , R 8c may be the same or different and are independently selected from hydrogen, halogen, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, unsubstituted or substituted by the same or different 1-5 R5 (hetero)aryl;

[0101] R 9a , R 9b , R 10a , R 10b , R 11a , R 11b R5, C1-C4, halogen, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylamino, halogenated C1-C4 alkylamino, di(C1-C4 alkyl)amino, C3-C4 cycloalkylamino, C1-C4 carbonylamino, C1-C4 alkoxycarbonylamino, unsubstituted or substituted by the same or different 1-5 R5 (hetero)aryl;

[0102] R 14a , R 14b , R 14cmay be the same or different, but are not selected from hydrogen at the same time, and are each selected from hydrogen, halogen, cyano, nitro, hydroxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyloxy, halogenated C3-C4 cycloalkyloxy, C1-C4 alkylamino, halogenated C1-C4 alkylamino, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylsulfinyl, halogenated C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl or halogenated C1-C4 alkylsulfonyl;

[0103] R 16a , R 16b , R 16c , R 16d R5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0104] R 17a , R 17b , R 17c , R 17d R5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0105] R 18a , R 18b , R 18c , R 18dR5, which may be the same or different but are not selected from hydrogen at the same time, are selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkenyl, halogenated C1-C4 alkenyl, C1-C4 alkynyl, halogenated C1-C4 alkynyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, unsubstituted or substituted by 1 to 5 R5 which may be the same or different, (hetero)aryl, (hetero)arylamino, (hetero)aryloxy, (hetero)arylthio;

[0106] Or a salt of the compound represented by the above general formula.

[0107] Among the compounds of general formulas I-1, I-2, I-3, I-4, I-5, I-6, I-9, IV-1, IV-2 and IV-3:

[0108] R1 is selected from C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl;

[0109] R2 is selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl;

[0110] W is selected from NR3R4, unsubstituted or (hetero)arylamino further substituted by 1-5 R5 groups;

[0111] X is selected from O or S;

[0112] Y is selected from O or S;

[0113] R3 and R4 may be the same or different and are selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl, cyano C1-C4 alkyl, C3-C6 cycloalkyl;

[0114] R5 is selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, carboxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C1-C4 alkylamino, C1-C4 alkylthio, halogenated C1-C4 alkylthio;

[0115] R 6a , R 7a , R 8a are independently selected from hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkenyl, C1-C4 alkynyl, C1-C4 alkylcarbonyl, unsubstituted or (hetero)aryl substituted by 1-5 R5;

[0116] R 6b , R 6c , R 7b , R 7c , R8b , R 8c may be the same or different, and are independently selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C4 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, (hetero)aryl which is unsubstituted or substituted by 1-5 R5;

[0117] R 9a , R 9b , R 10a , R 10b , R 11a , R 11b may be the same or different, and are independently selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C4 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, (hetero)aryl which is unsubstituted or substituted by 1-5 R5;

[0118] R 14a , R 14b , R 14c may be the same or different, but are not selected from hydrogen at the same time, and are each selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C4 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy;

[0119] R 16a , R 16b , R 16c , R 16d may be the same or different, but not simultaneously selected from hydrogen, and are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by 1-5 R5 which may be the same or different;

[0120] R 17a , R 17b , R 17c , R 17d may be the same or different, but not simultaneously selected from hydrogen, and are independently selected from hydrogen, halogen, hydroxy, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by 1-5 R5 which may be the same or different;

[0121] R 18a , R 18b , R 18c , R 18dR5 may be the same or different, but not selected at the same time from hydrogen, and may be selected separately from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, C1-C4 alkylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by 1-5 R5 which may be the same or different;

[0122] Or a salt of the compound represented by the above general formula.

[0123] Among the compounds of general formula I-1, I-2, I-3, I-4, I-5, I-6, I-9, IV-1, IV-2 or IV-3:

[0124] R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, monofluoroethyl, monochloroethyl, monobromoethyl, monofluoroisopropyl, difluoromethyl, dibromomethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;

[0125] R2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-methylbutyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, monofluoromethyl, monochloromethyl, monofluoroethyl, monochloroethyl, monobromoethyl, monofluoropropyl, monochloropropyl, monobromopropyl, monofluorobutyl, monochlorobutyl, difluoromethyl, trifluoromethyl, trifluoroethyl, trifluoropropyl, heptafluoroisopropyl;

[0126] W is selected from methylamino, ethylamino, dimethylamino, methylethylamino, diethylamino, acetonitrileamino, cyclopropylamino, cyclopentylamino, cyclohexylamino, unsubstituted or further substituted by 1 to 5 identical or different R5 groups;

[0127] X is selected from O or S;

[0128] Y is selected from O or S;

[0129] R is selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropyloxy, trifluoromethoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylamino, ethylamino, dimethylamino, methylethylamino, diethylamino, methylthio, ethylthio, trifluoromethylthio;

[0130] R 6a , R 7a , R 8aSelected from hydrogen, methyl, ethyl, n-propyl, cyclopropyl, allyl, propargyl, phenyl which is unsubstituted or substituted by 1 to 5 identical or different R5, pyridyl;

[0131] R 6b , R 6c , R 7b , R 7c , R 8b , R 8c R5 may be the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylamino, dimethylamino, phenyl which is unsubstituted or substituted by the same or different 1-5 R5, and pyridyl;

[0132] R 9a , R 9b , R 10a , R 10b , R 11a , R 11b R5 may be the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylamino, dimethylamino, phenyl which is unsubstituted or substituted by the same or different 1-5 R5, and pyridyl;

[0133] R 14a , R 14b , R 14c may be the same or different, but not simultaneously selected from hydrogen, and are each selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy;

[0134] R 16a , R 16b , R 16c , R 16d R5, which may be the same or different but not simultaneously selected from hydrogen, are selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, cyclopropyl, methylsulfonyl, ethylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by the same or different 1-5 R5;

[0135] R 17a , R 17b , R 17c , R 17d R5, which may be the same or different but not simultaneously selected from hydrogen, are selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, cyclopropyl, methylsulfonyl, ethylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by the same or different 1-5 R5;

[0136] R 18a , R 18b , R 18c , R 18d R5, which may be the same or different but not simultaneously selected from hydrogen, are selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, cyclopropyl, methylsulfonyl, ethylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by the same or different 1-5 R5;

[0137] Or a salt of the compound represented by the above general formula.

[0138] In the compound of formula I-1, I-2, I-3, IV-1, IV-2 or IV-3:

[0139] R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, monofluoroethyl, monochloroethyl, monobromoethyl, monofluoroisopropyl, difluoromethyl, dibromomethyl, trifluoromethyl, trichloromethyl, trifluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;

[0140] R2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-methylbutyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, monofluoromethyl, monochloromethyl, monofluoroethyl, monochloroethyl, monobromoethyl, monofluoropropyl, monochloropropyl, monobromopropyl, monofluorobutyl, monochlorobutyl, difluoromethyl, trifluoromethyl, trifluoroethyl, trifluoropropyl, heptafluoroisopropyl;

[0141] W is selected from methylamino, ethylamino, dimethylamino, methylethylamino, diethylamino, acetonitrileamino, cyclopropylamino, cyclopentylamino, cyclohexylamino, unsubstituted or further substituted by 1 to 5 identical or different R5 groups;

[0142] X is selected from O or S;

[0143] Y is selected from O or S;

[0144] R is selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropyloxy, trifluoromethoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylamino, ethylamino, dimethylamino, methylethylamino, diethylamino, methylthio, ethylthio, trifluoromethylthio;

[0145] R 6a , R 7a , R 8a Selected from hydrogen, methyl, ethyl, n-propyl, cyclopropyl, allyl, propargyl, phenyl which is unsubstituted or substituted by 1 to 5 identical or different R5, pyridyl;

[0146] R 6b , R 6c , R 7b , R 7c , R 8b , R 8c R5 may be the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylamino, dimethylamino, phenyl which is unsubstituted or substituted by the same or different 1-5 R5, and pyridyl;

[0147] R 16a , R 16b , R 16c , R 16d R5, which may be the same or different but not simultaneously selected from hydrogen, are selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, cyclopropyl, methylsulfonyl, ethylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by the same or different 1-5 R5;

[0148] R 17a , R 17b , R 17c , R 17dR5, which may be the same or different but not simultaneously selected from hydrogen, are selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, cyclopropyl, methylsulfonyl, ethylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by the same or different 1-5 R5;

[0149] R 18a , R 18b , R 18c , R 18d R5, which may be the same or different but not simultaneously selected from hydrogen, are selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, amino, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, cyclopropyl, methylsulfonyl, ethylsulfonyl, phenyl, phenylamino, phenoxy which are unsubstituted or substituted by the same or different 1-5 R5;

[0150] Or a salt of the compound represented by the above general formula.

[0151] A use of the substituted pyrimidine (thio) ester compound for preparing a fungicide in agriculture or other fields.

[0152] In the definition of compounds of general formula I given above, the terms used are generally defined as follows:

[0153] Halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl: straight chain or branched alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, etc. Haloalkyl: straight chain or branched alkyl, the hydrogen atoms on these alkyl can be partially or completely replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc. Alkylsulfinyl: straight chain or branched alkyl is connected to the structure through a sulfinyl group (-SO-), such as methylsulfinyl. Haloalkylsulfinyl: straight chain or branched alkylsulfinyl, the hydrogen atoms on its alkyl can be partially or completely replaced by halogen atoms. Haloalkylsulfonyl: straight chain or branched alkylsulfonyl, the hydrogen atoms on its alkyl can be partially or completely replaced by halogen atoms. Alkylaminothio: such as CH3NHS-, C2H5NHS-. Dialkylaminothio: such as (CH3)2NS-, (C2H5)2NS-. Alkylaminosulfonyl: alkyl-NH-SO2-. Dialkylaminosulfonyl: (alkyl)2-N-SO2-. Alkylsulfonylaminocarbonyl: alkyl-SO2-NH-CO-. Alkylcarbonylaminosulfonyl: alkyl-CO-NH-SO2-. Alkylcarbonylalkyl: alkyl-CO-alkyl-. Alkylsulfonyloxy: alkyl-S(O)2-O-. Haloalkylsulfonyloxy: the hydrogen atoms on the alkyl group of the alkylsulfonyloxy group may be partially or completely replaced by halogen atoms, such as CF3-SO2-O. Cycloalkyloxycarbonyl: such as cyclopropyloxycarbonyl, cyclohexyloxycarbonyl, etc. Alkoxy: a straight or branched chain alkyl group connected to the structure via an oxygen atom bond. Halogenated alkoxy: straight or branched alkoxy, the hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc. Halogenated alkoxycarbonyl: the hydrogen atoms on the alkyl group of alkoxycarbonyl may be partially or completely replaced by halogen atoms, such as ClCH2CH2OCO-, CF3CH2OCO-, etc. Alkoxyalkyl: alkyl-O-alkyl-, such as CH3OCH2-. Halogenated alkoxyalkyl: the hydrogen atoms on the alkyl group of alkoxyalkyl may be partially or completely replaced by halogen atoms, such as ClCH2CH2OCH2-, CF3CH2OCH2-, etc. Alkoxycarbonylalkyl: alkoxycarbonyl-alkyl-, such as CH3OCOCH2-. Haloalkoxycarbonylalkyl: The hydrogen atoms on the alkyl group of alkoxycarbonylalkyl may be partially or completely replaced by halogen atoms, such as CF3CH2OCOCH2-. Alkylcarbonyloxy: such as CH3COO-, etc. Haloalkylcarbonyloxy: The hydrogen atoms on the alkylcarbonyloxy group may be partially or completely replaced by halogen atoms, such as CF3COO-, etc. Alkoxycarbonyloxy: Alkoxycarbonyl-oxy-, such as CH3OCOO-.Haloalkoxycarbonyloxy: The hydrogen atoms on the alkyl group of alkoxycarbonyloxy may be partially or completely replaced by halogen atoms, for example CF3OCOO-. Alkylthiocarbonylalkyl: Alkylthiocarbonyl-alkyl-, for example CH3SCOCH2-. Haloalkylthiocarbonylalkyl: The hydrogen atoms on the alkyl group of alkylthiocarbonylalkyl may be partially or completely replaced by halogen atoms, for example CF3CH2SCOCH2-. Alkoxyalkoxy: such as CH3OCH2O-, etc. Haloalkoxyalkoxy: The hydrogen atoms on the alkoxy group may be partially or completely replaced by halogen atoms, for example CF3OCH2O-. Alkoxyalkoxycarbonyl: such as CH3OCH2CH2OCO-, etc. Alkylthio: Straight or branched alkyl groups, connected to the structure via sulfur atom bonds. Haloalkylthio: Straight or branched alkylthio, the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, etc. Alkylthioalkyl: alkyl-S-alkyl-, such as CH3SCH2-. Haloalkylthioalkyl: The hydrogen atoms on the alkyl group of alkylthioalkyl can be partially or completely replaced by halogen atoms, such as ClCH2CH2SCH2-, CF3CH2SCH2-, etc. Alkylamino: Straight or branched chain alkyl, connected to the structure via a nitrogen atom bond. Haloalkylamino: Straight or branched chain alkylamino, the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms. Dialkylamino: such as (CH3)2N-, (CH3CH2)2N-. Halodialkylamino: The hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms, such as (CF3)2N-, (CF3CH2)2N-. Alkenyl: straight or branched alkenes, such as vinyl, 1-propenyl, 2-propenyl and different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. Haloalkenyl: straight or branched alkenes, the hydrogen atoms on these alkenyls may be partially or completely replaced by halogen atoms. Alkenyloxy: straight or branched alkenes, connected to the structure via an oxygen atom bond. Haloalkenyloxy: straight or branched alkenyloxy, the hydrogen atoms on these alkenyloxys may be partially or completely replaced by halogen atoms. Alkenylthio: straight or branched alkenes, connected to the structure via a sulfur atom bond. Such as CH2=CHCH2S-. Alkenyloxycarbonyl: such as CH2=CHCH2OCO-, etc. Alkynyl: straight or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl and different butynyl, pentynyl and hexynyl isomers. Alkynyl groups also include groups consisting of multiple triple bonds, such as 2,5-hexadiynyl. Haloalkynyl: Straight or branched alkynes, on which the hydrogen atoms can be partially or completely replaced by halogen atoms. Alkynyloxy: Straight or branched alkynes, connected to the structure via an oxygen atom bond. Haloalkynyloxy: Straight or branched alkynyloxy, on which the hydrogen atoms can be partially or completely replaced by halogen atoms. Alkynyloxycarbonyl: such as CH≡CCH2OCO-, etc.Alkylsulfonyl: A straight or branched alkyl group is connected to the structure via a sulfonyl group (-SO2-), such as methylsulfonyl. Haloalkylsulfonyl: A straight or branched alkylsulfonyl group, in which the hydrogen atoms on the alkyl group may be partially or completely replaced by halogen atoms. Alkylcarbonyl: An alkyl group is connected to the structure via a carbonyl group, such as CH3CO-, CH3CH2CO-. Haloalkylcarbonyl: The hydrogen atoms on the alkyl group of an alkylcarbonyl group may be partially or completely replaced by halogen atoms, such as CF3CO-. Alkoxycarbonyl: An alkoxy group is connected to the structure via a carbonyl group. Such as CH3OCO-, CH3CH2OCO-. Aminocarbonyl: Such as NH2CO-. Alkylaminocarbonyl: Alkyl-NH-CO-, such as CH3NHCO-, CH3CH2NHCO-. Dialkylaminocarbonyl: Such as (CH3)2NCO-, (CH3CH2)2NCO-. The aryl part in (hetero)aryl, (hetero)aryloxy, (hetero)arylamino, (hetero)arylthio includes phenyl or naphthyl, etc., and the heteroaryl is a five-membered ring or a six-membered ring containing one or more heteroatoms of N, O, and S. For example, furanyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, etc.

[0154] Table 1, Table 2 and Table 3 respectively list some specific substituents for R1, R2 and W in Formula I, but they are not limited to these substituents.

[0155]

[0156] Table 1 R1 Substituents

[0157]

[0158]

[0159] Table 2 R2 Substituents

[0160]

[0161] Table 3 W Substituents

[0162]

[0163]

[0164] Some of the compounds of the present invention can be illustrated by the specific compounds listed in Tables 4 to 32, but the present invention is not limited thereto.

[0165] In the general formula I-1,

[0166]

[0167] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R6a , R 6b , R 6c The substituents are shown in Table 4A, and the representative compounds are numbered 4A-1 to 4A-200.

[0168] Table 4A

[0169]

[0170]

[0171]

[0172]

[0173] Table 5A: In the general formula I-1, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 6a , R 6b , R 6c Consistent with Table 4A, the corresponding compounds are 4A-1 to 4A-200 in Table 4A, and the representative compound numbers are 5A-1 to 5A-200.

[0174] Table 6A: In the general formula I-1, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 6a , R 6b , R 6c Consistent with Table 4A, they correspond to 4A-1 to 4A-200 in Table 4A, and the representative compound numbers are 6A-1 to 6A-200.

[0175] Table 7A: In the general formula I-1, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 6a , R 6b , R 6c Consistent with Table 4A, the corresponding compounds are 4A-1 to 4A-200 in Table 4A, and the representative compound numbers are 7A-1 to 7A-200.

[0176] In the general formula I-2,

[0177]

[0178] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 7a , R 7b , R 7c The substituents are shown in Table 8A, and the representative compound numbers are 8A-1 to 8A-300.

[0179] Table 8A

[0180]

[0181]

[0182]

[0183]

[0184]

[0185] Table 9A: In the general formula I-2, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 7a , R 7b , R 7c Consistent with Table 8A, they correspond to 8A-1 to 8A-300 in Table 8A, and the representative compound numbers are 9A-1 to 9A-300.

[0186] Table 10A: In the general formula I-2, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 7a , R 7b , R 7c Consistent with Table 8A, they correspond to 8A-1 to 8A-300 in Table 8, and the representative compound numbers are 10A-1 to 10A-300.

[0187] Table 11A: In the general formula I-2, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 7a , R 7b , R 7c Consistent with Table 8A, they correspond to 8A-1 to 8A-300 in Table 8, and the representative compound numbers are 11A-1 to 11A-300.

[0188] In the general formula I-3,

[0189]

[0190] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 8a , R 8b , R 8c The substituents are shown in Table 12A, and the representative compound numbers are 12A-1 to 12A-284.

[0191] Table 12A

[0192]

[0193]

[0194]

[0195]

[0196] Table 13A: In the general formula I-3, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 8a , R 8b , R 8c Consistent with Table 12A, they correspond to 12A-1 to 12A-284 in Table 12A, and the representative compound numbers are 13A-1 to 13A-284.

[0197] Table 14A: In the general formula I-3, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 8a , R 8b , R 8c Consistent with Table 12A, they correspond to 12A-1 to 12A-284 in Table 12A, and the representative compound numbers are 14A-1 to 14A-284.

[0198] Table 15A: In the general formula I-3, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 8a , R 8b , R 8c Consistent with Table 12A, they correspond to 12A-1 to 12A-284 in Table 12A, and the representative compound numbers are 15A-1 to 15A-284.

[0199] In the general formula I-4,

[0200]

[0201] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 9a , R 9b The substituents are shown in Table 16A, and the representative compound numbers are 16A-1 to 16A-201.

[0202] Table 16A

[0203]

[0204]

[0205] Table 17A: In the general formula I-4, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R9a , R 9b Consistent with Table 16A, they correspond to 16A-1 to 16A-201 in Table 16A, and the representative compound numbers are 17A-1 to 17A-201.

[0206] Table 18A: In the general formula I-4, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 9A , R 9b , R 7c Consistent with Table 16A, they correspond to 16A-1 to 16A-201 in Table 16A, and the representative compound numbers are 18A-1 to 18A-201.

[0207] Table 19A: In the general formula I-4, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 9A , R 9b , R 7c Consistent with Table 16A, they correspond to 16A-1 to 16A-201 in Table 16A, and the representative compound numbers are 19A-1 to 19A-201.

[0208] In the general formula I-5,

[0209]

[0210] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 10a , R 10b The substituents are shown in Table 20A, and the representative compound numbers are 20A-1 to 20A-270.

[0211] Table 20A

[0212]

[0213]

[0214]

[0215]

[0216] Table 21A: In the general formula I-5, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 10a , R 10b Consistent with Table 20A, they correspond to 20A-1 to 20A-270 in Table 20A, and the representative compound numbers are 21A-1 to 21A-270.

[0217] Table 22A: In the general formula I-5, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 10a , R 10b Consistent with Table 20A, they correspond to 20A-1 to 20A-270 in Table 20A, and the representative compound numbers are 22A-1 to 22A-270.

[0218] Table 23A: In the general formula I-5, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 10a , R 10b Consistent with Table 20A, they correspond to 20A-1 to 20A-270 in Table 20A, and the representative compound numbers are 23A-1 to 23A-270.

[0219] In the general formula I-6,

[0220]

[0221] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 11a , R 11b The substituents are shown in Table 24A, and the representative compound numbers are 24A-1 to 24A-150.

[0222] Table 24A

[0223]

[0224]

[0225] Table 24B: In the general formula I-6, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 11a , R 11b Consistent with Table 24A, they correspond to 24A-1 to 24A-150 in Table 24A, and the representative compound numbers are 24B-1 to 24B-150.

[0226] Table 24C: In the general formula I-6, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 11a , R 11b Consistent with Table 24A, they correspond to 24A-1 to 24A-150 in Table 24A, and the representative compound numbers are 24C-1 to 24C-150.

[0227] Table 24D: In the general formula I-6, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 11a, R 11b Consistent with Table 24A, they correspond to 24A-1 to 24A-150 in Table 24A, and the representative compound numbers are 24D-1 to 24D-150.

[0228] In the general formula I-9,

[0229]

[0230] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 14a , R 14b , R 14c The substituents are shown in Table 25A, and the representative compound numbers are 25A-1 to 25A-240.

[0231] Table 25A

[0232]

[0233]

[0234]

[0235]

[0236] Table 26A: In the general formula I-9, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 14a , R 14b , R 14c Consistent with Table 25A, they correspond to 25A-1 to 25A-240 in Table 25A, and the representative compound numbers are 26A-1 to 26A-240.

[0237] Table 27A: In the general formula I-9, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 14a , R 14b , R 14c Consistent with Table 25A, they correspond to 25A-1 to 25A-240 in Table 25A, and the representative compound numbers are 27A-1 to 27A-240.

[0238] Table 28A: In the general formula I-9, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 14a , R 14b , R 14c Consistent with Table 25A, they correspond to 25A-1 to 25A-240 in Table 25A, and the representative compound numbers are 28A-1 to 28A-240.

[0239] In the general formula IV-1,

[0240]

[0241] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 16a , R 16b , R 16c , R 16d The substituents are shown in Table 29A, and the representative compound numbers are 29A-1 to 29A-171.

[0242] Table 29A

[0243]

[0244]

[0245]

[0246] Table 29B: In the general formula IV-1, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 16a , R 16b , R 16c , R 16d Consistent with Table 29A, they correspond to 29A-1 to 29A-171 in Table 29A, and the representative compound numbers are 29B-1 to 29B-171.

[0247] Table 29C: In the general formula IV-1, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 16a , R 16b , R 16c , R 16d Consistent with Table 29A, they correspond to 29A-1 to 29A-171 in Table 29A, and the representative compound numbers are 29C-1 to 29C-171.

[0248] Table 29D: In the general formula IV-1, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 16a , R 16b , R 16c , R 16d Consistent with Table 29A, they correspond to 29A-1 to 29A-171 in Table 29A, and the representative compound numbers are 29D-1 to 29D-171.

[0249] In the general formula IV-2,

[0250]

[0251] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 17a , R 17b , R 17c The substituents are shown in Table 30A, and the representative compound numbers are 30A-1 to 30A-300.

[0252] Table 30A

[0253]

[0254]

[0255]

[0256]

[0257] Table 30B: In the general formula IV-2, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 17a , R 17b , R 17c Consistent with Table 30A, they correspond to 30A-1 to 30A-300 in Table 30A, and the representative compound numbers are 30B-1 to 30B-300.

[0258] Table 30C: In the general formula IV-2, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 17a , R 17b , R 17c Consistent with Table 30A, they correspond to 30A-1 to 30A-300 in Table 30A, and the representative compound numbers are 30C-1 to 30C-300.

[0259] Table 30D: In the general formula IV-2, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 17a , R 17b , R 17c Consistent with Table 30A, they correspond to 30A-1 to 30A-300 in Table 30A, and the representative compound numbers are 30D-1 to 30D-300.

[0260] Table 30E: In the general formula IV-2, when R1=CH3, R2=n-C4H9, W=4-CF3OPhNH, X=Y=O, the substituent R 17a , R 17b , R 17cConsistent with Table 30A, they correspond to 30A-1 to 30A-300 in Table 30A, and the representative compound numbers are 30E-1 to 30E-300.

[0261] Table 30F: In the general formula IV-2, when R1=CHF2, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 17a , R 17b , R 17c Consistent with Table 30A, they correspond to 30A-1 to 30A-300 in Table 30A, and the representative compound numbers are 30F-1 to 30F-300.

[0262] Table 30G: In the general formula IV-2, when R1=CH3, R2=H, W=PhNH, X=Y=O, the substituent R 17a , R 17b , R 17c Consistent with Table 30A, they correspond to 30A-1 to 30A-300 in Table 30A, and the representative compound numbers are 30G-1 to 30G-300.

[0263] In the general formula IV-3,

[0264]

[0265] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 18a , R 18b , R 18c , R 18d The substituents are shown in Table 31A, and the representative compound numbers are 31A-1 to 31A-300.

[0266] Table 31A

[0267]

[0268]

[0269]

[0270]

[0271] Table 31B: In the general formula IV-3, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 18a , R 18b , R 18c , R 18dConsistent with Table 31A, they correspond to 31A-1 to 31A-300 in Table 31A, and the representative compound numbers are 31B-1 to 31B-300.

[0272] Table 31C: In the general formula IV-3, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 18a , R 18b , R 18c , R 18d Consistent with Table 31A, they correspond to 31A-1 to 31A-300 in Table 31A, and the representative compound numbers are 31C-1 to 31C-300.

[0273] Table 31D: In the general formula IV-3, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 18a , R 18b , R 18c , R 18d Consistent with Table 31A, they correspond to 31A-1 to 31A-300 in Table 31A, and the representative compound numbers are 31D-1 to 31D-300.

[0274] In the general formula IV-4,

[0275]

[0276] When R1=CH3、R2=n-C4H9、W=NHCH2CH3、X=Y=O, R 19a , R 19b , R 19c The substituents are shown in Table 32A, and the representative compound numbers are 32A-1 to 32A-200.

[0277] Table 32A

[0278]

[0279]

[0280]

[0281] Table 32B: In the general formula IV-4, when R1=CH3, R2=n-C4H9, W=N(CH3)2, X=Y=O, the substituent R 19a , R 19b , R 19c Consistent with Table 32A, they correspond to 32A-1 to 32A-200 in Table 32A, and the representative compound numbers are 32B-1 to 32B-200.

[0282] Table 32C: In the general formula IV-4, when R1=CF3, R2=H, W=2,4-2ClPhNH, X=Y=O, the substituent R 19a , R 19b , R 19c Consistent with Table 32A, they correspond to 32A-1 to 32A-200 in Table 32A, and the representative compound numbers are 32C-1 to 32C-200.

[0283] Table 32D: In the general formula IV-4, when R1=CH3, R2=n-C4H9, W=PhNH, X=Y=O, the substituent R 19a , R 19b , R 19c Consistent with Table 32A, they correspond to 32A-1 to 32A-200 in Table 32A, and the representative compound numbers are 32D-1 to 32D-200.

[0284] The compounds of the present invention are prepared according to the following method, and the reaction formula is as follows, wherein the groups have the same definitions as above unless otherwise specified:

[0285] The preparation of the compound of formula I is carried out by the following method:

[0286]

[0287] Intermediates II and III react under basic conditions in a suitable solvent to obtain a compound of formula I.

[0288] Suitable bases can 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, etc.

[0289] The reaction is carried out in a suitable solvent, which can be selected from dichloromethane, chloroform, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, 1,4-dioxane, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, acetone or butanone.

[0290] The reaction temperature may be between -30°C and the boiling point of the solvent, usually -10 to 80°C.

[0291] The reaction time is 30 minutes to 10 hours, usually 1 to 3 hours.

[0292] The intermediate III part is commercially available or can be prepared by a known method, for example, by the method described in reference CN106243027, WO2018055640, WO9511905, EP2008996, JP02300173, DE102005031348, US4437875, DE2940189, JP03056478, and CN101851197.

[0293] Intermediate II is a key intermediate for preparing the compound of formula I of the present invention, and is prepared by the following method:

[0294]

[0295] The substituted or unsubstituted substituted formamidine M-1 and the substituted or unsubstituted ethyl acetoacetate M-2 are reacted in a suitable solvent at a suitable temperature for 30 minutes to 20 hours, usually 1 to 10 hours, to obtain intermediate II. The operation method of this step refers to EP302311, WO2013123401 and DE3620841.

[0296] The sources of intermediates are as follows: Intermediates M-1 and M-2 are commercially available or prepared according to conventional methods.

[0297] The suitable reaction temperature is preferably 0 to 100°C; the reaction time is 30 minutes to 20 hours, preferably 1 to 10 hours.

[0298] Suitable solvents are selected from methanol, ethanol, ethyl acetate, benzene, toluene, xylene, chloroform, dichloromethane, water, tetrahydrofuran, acetonitrile, acetone, butanone, dioxane, N,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.

[0299] Suitable bases can 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, etc.

[0300] Although the compounds of general formula I of the present invention and some compounds disclosed in the prior art also belong to pyrimidine-containing ester compounds, their structural features are still significantly different. And due to these structural differences, the compounds of the present invention have better fungicidal activity.

[0301] The compound of general formula I shows excellent activity against a variety of pathogens in agriculture or other fields. Therefore, the technical scheme of the present invention also includes the use of the compound of general formula I in agriculture or other fields for preparing fungicides.

[0302] The examples of diseases mentioned below are only used to illustrate the present invention, but they are by no means limiting.

[0303] The compounds of general formula I can be used to control the following diseases: Oomycete diseases, such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, loofah downy mildew, wax gourd downy mildew, melon downy mildew, cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, cabbage white rust), damping-off disease (rapeseed damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cotton rot (pepper cotton rot, loofah cotton rot, wax gourd cotton rot), blight (broad bean blight, cucumber blight, pumpkin blight, wax gourd blight, watermelon blight, melon blight, pepper blight, leek blight, garlic blight, cotton blight), late blight (potato late blight, tomato late blight), etc.;Deuteromycin diseases, such as wilt (sweet potato wilt, cotton wilt, sesame wilt, castor wilt, tomato wilt, kidney bean wilt, cucumber wilt, loofah wilt, pumpkin wilt, wax gourd wilt, watermelon wilt, melon wilt, pepper wilt, broad bean wilt, rapeseed wilt, soybean wilt), root rot (pepper root rot, eggplant root rot, kidney bean root rot, cucumber root rot, bitter melon root rot, cotton black root rot, broad bean root rot), damping-off (cotton seedling damping-off, sesame damping-off, pepper damping-off, cucumber damping-off, cabbage damping-off), anthracnose (sorghum anthracnose, cotton anthracnose, hemp anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry anthracnose Disease, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, bitter gourd anthracnose, zucchini anthracnose, wax gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), Verticillium wilt (cotton wilt, sunflower wilt, tomato wilt, pepper wilt, eggplant wilt), black spot (zucchini black spot, wax gourd black spot, melon black spot), gray mold (cotton boll gray mold, hemp gray mold, tomato gray mold, pepper gray mold, kidney bean gray mold, celery gray mold, spinach gray mold, kiwifruit gray mold), brown spot (cotton brown spot, jute brown spot, beet brown spot, peanut brown spot, pepper brown spot, wax gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot Black spot (false black spot of flax, black spot of rape, black spot of sesame, black spot of sunflower, black spot of castor, black spot of tomato, black spot of pepper, black spot of eggplant, black spot of kidney bean, black spot of cucumber, black spot of celery, black rot of carrot, black spot of carrot, black spot of apple, black spot of peanut), spot blight (spot blight of tomato, spot blight of pepper, spot blight of celery), early blight (early blight of tomato, early blight of pepper, early blight of eggplant, early blight of potato, early blight of celery), ring rot (soybean ring rot, sesame ring rot, kidney bean ring rot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), stem base rot (stem base rot of tomato, vegetable Bean stem base rot), and others (corn round spot, jute waist break disease, rice blast, chestnut black sheath disease, sugarcane eye spot disease, cotton boll Aspergillus disease, peanut crown rot, soybean stem blight, soybean black spot disease, melon large spot disease, peanut web spot disease, tea red leaf spot disease, pepper white star disease, wax gourd leaf spot disease, celery black rot, spinach heart rot, jute leaf mold, jute spot disease, jute stem spot disease, soybean purple spot disease, sesame leaf spot disease, castor gray spot disease, tea brown leaf spot disease, eggplant brown round star disease, kidney bean red spot disease, bitter melon white spot disease, watermelon spot disease, jute blight rot, sunflower root and stem rot disease, kidney bean charcoal rot, soybean target spot disease, eggplant coryneform leaf spot disease, cucumber target spot disease, tomato leaf mold disease, eggplant leaf mold disease, broad bean red spot disease, etc.);Basidiomycete diseases, such as rust (wheat stripe rust, wheat stem rust, wheat leaf rust, flower rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut (corn silk smut, corn powdery mildew, sorghum silk smut, sorghum loose smut, sorghum hard smut, sorghum column powdery mildew, chestnut kernel smut, sugarcane smut, bean rust) and others (such as wheat sheath blight, rice sheath blight, etc.); Ascomycete diseases, such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, Powdery mildew of sunflower, beet, eggplant, pea, loofah, pumpkin, zucchini, wax gourd, melon, grape, broad bean), sclerotinia (flax, rape, soybean, peanut, tobacco, pepper, eggplant, bean, pea, cucumber, bitter melon, wax gourd, watermelon, celery), scab (apple scab, pear scab), etc. ;

[0304] Due to their positive properties, the abovementioned compounds can be advantageously used for protecting agriculturally and horticulturally important crops, domestic and breeding animals, and the environment frequented by humans from pathogens.

[0305] To obtain the desired effect, the amount of compound used will vary depending on factors such as the compound used, the crop to be protected, the type of pest, the degree of infestation, climatic conditions, the method of application, and the formulation employed.

[0306] Doses of 10 g to 5 kg of compound per hectare provide adequate control.

[0307] It should be understood that various changes and modifications can be made within the scope of the present invention as defined by the claims.

[0308] The advantages of the present invention are:

[0309] Compared with the prior art, the present invention has significant novelty in structure, may have a different action target from the prior art, has significant activity against many fungal diseases, especially downy mildew and powdery mildew, has a simple synthesis process, and is easy to industrialize. DETAILED DESCRIPTION

[0310] The following specific examples are used to further illustrate the present invention, but the present invention is by no means limited to these examples (unless otherwise noted, all raw materials used are commercially available).

[0311] Synthesis Example

[0312] Example 1: Preparation of intermediate 2-(2,4-dichlorophenylamino)-6-trifluoromethyl-4-pyrimidinol

[0313]

[0314] In a 250mL three-necked reaction bottle equipped with a mechanical stirrer and a condenser, 2,4-dichlorophenylguanidine (0.05mol, 10.15g) was dissolved in 100mL of anhydrous ethanol, and ethyl trifluoroacetoacetate (0.05mol, 9.2g) was added. The reaction was refluxed for 5h, the reaction was stopped, cooled to room temperature, 300mL of ice water was added, stirred for 30min, filtered, the filter cake was washed with water, and dried to obtain 13.24g of a white solid with a yield of 81.7%. The melting point was >300℃.

[0315] Example 2: Preparation of intermediate 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxylic acid

[0316] 1) Preparation of ethyl 3-ethyl-1-methyl-1H-pyrazole-5-carboxylate

[0317]

[0318] In a 250mL three-necked flask, add 28.1g (0.4mol) of sodium ethoxide and 160mL of anhydrous ethanol, stir at room temperature to completely dissolve the sodium ethoxide, cool to -5-0°C, drop a mixture of 58.4g (0.4mol) of diethyl oxalate and 28.8g (0.4mol) of butanone, drop for about 1h, and continue to react at this temperature for 2h. In another three-necked flask, add 57.5g (0.5mol) of 40% methylhydrazine, drop 10g of ethanol solution, control the temperature below 30°C, and drop for 0.5h. Add the prepared methylhydrazine solution dropwise to the reaction solution, control the temperature at 0-5°C, drop for about 1.5h, and continue to react at this temperature for 0.5h. The solvent was evaporated under reduced pressure, 180 mL of water and 180 mL of toluene were added, the pH was adjusted to 5-6 with hydrochloric acid, and the mixture was allowed to stand for stratification after stirring for 0.5 h. The upper layer was extracted twice with toluene (2×50 mL), the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain 3-ethyl-1-methyl-1H-pyrazole-5-carboxylic acid ethyl ester as a viscous liquid.

[0319] 2) Preparation of ethyl 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxylate

[0320]

[0321] In a 500mL three-necked flask, add ethyl 3-ethyl-1-methyl-1H-pyrazole-5-carboxylate obtained in the first step and 200mL of chloroform. Add 64.8g (0.5mol) of sulfuryl chloride dropwise under water bath conditions. After the addition is complete, heat to reflux and react for 6h. Cool and evaporate the solvent to obtain 83.1g of a viscous liquid crude product. The yield is 74.1%.

[0322] 3) Preparation of 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxylic acid

[0323]

[0324] In a 250mL three-necked flask, add 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxylic acid ethyl ester, 25.3g (0.6mol) of sodium hydroxide, and 100mL of water, and heat to reflux until the reaction is complete, about 2h. Add 100mL of water, cool to 100℃, adjust pH to 1-2 with hydrochloric acid, and a large amount of yellow solid precipitates. Continue stirring at this temperature for 2h, filter, and dry to obtain 47.7g of crude product, with a yield of 86.2%. Melting point 163-165℃.

[0325] Example 3: Preparation of 3,6-dichloro-6-pyridinecarbonyl chloride

[0326]

[0327] In a 250mL three-necked flask, add 21.1g (0.1mol) of 2-methyl-4-trifluoromethyl-5-thiazolecarboxylic acid, 15mL (0.2mol) of thionyl chloride, and 2-3 drops of DMF, heat to reflux, and react for about 2h. Distill off the excess thionyl chloride under reduced pressure to obtain 2-methyl-4-trifluoromethyl-5-thiazolecarbonyl chloride with a yield of 96.2%.

[0328] Example 4: Preparation of 3-methyl-1-ethyl-1H-pyrazole-5-carbonyl chloride

[0329]

[0330] In a 250mL three-necked flask, add 15.4g (0.1mol) of 3-methyl-1-ethyl-1H-pyrazole-5-carboxylic acid, 15mL (0.2mol) of thionyl chloride, and 2-3 drops of DMF, heat to reflux, and react for about 2h. Distill off the excess thionyl chloride under reduced pressure to obtain 3-methyl-1-ethyl-1H-pyrazole-5-carbonyl chloride with a yield of 95.3%.

[0331] Example 5: Preparation of Compound 8A-200

[0332]

[0333] In a 100mL three-necked flask, add 0.97g (0.003mol) of 2-(2,4-dichlorophenylamino)-6-trifluoromethyl-4-pyrimidinol, 0.36g (0.0036mol) of triethylamine and 10mL of tetrahydrofuran, and add a mixture of 0.54g (0.0032mol) of 3-methyl-1-ethyl-1H-pyrazole-5-carbonyl chloride and 4mL of tetrahydrofuran at room temperature, control the temperature below 20°C, add for 20min, and continue stirring for 2h. After the reaction is completed by TLC monitoring, the solvent is evaporated under reduced pressure, and (3×50ml) ethyl acetate is added for extraction. The organic phase is washed with 50ml of saturated brine, and the residue after desolventization is subjected to column chromatography (the eluent is ethyl acetate and petroleum ether, the volume ratio is 1:5) to obtain 1.21g of white solid, with a yield of 87.8%. Melting point 135~137°C.

[0334] 1 H-NMR (600MHz, internal standard TMS, solvent CDCl3) δ (ppm): 8.42 (d, J=8.9Hz, 1H, phenyl-3-H), 7.81 (s, 1H, pyrimidyl-5-H), 7.42 (t, J=2.5Hz, 1H, phenyl-6-H), 7.29 (dd, J=8.9, 2.4Hz, 1H,phenyl-5-H),7.06(s,1H,NH),6.86(s,1H,pyrazolyl-4-H),4.57(q,J=7.2Hz,2 H,pyrazolyl-CH2),2.33(d,J=3.1Hz,3H,pyrazolyl-CH3),1.53–1.40(m,3H,CH3).

[0335] Example 6: Preparation of Compound 20A-84

[0336]

[0337] In a 100mL three-necked flask, add 0.63g (0.003mol) of 5-n-butyl-2-ethylamino-6-methyl-4-pyrimidinol, 0.36g (0.0036mol) of triethylamine and 10mL of tetrahydrofuran, and add a mixture of 0.73g (0.0032mol) of 2-methyl-4-trifluoromethyl-5-thiazolecarbonyl chloride and 4mL of tetrahydrofuran at room temperature, control the temperature below 20°C, add for 20min, and continue stirring for 2h. After the reaction is completed by TLC monitoring, the solvent is evaporated under reduced pressure, and (3×50ml) ethyl acetate is added for extraction. The organic phase is washed with 50ml of saturated brine, and the residue after desolventization is subjected to column chromatography (the eluent is ethyl acetate and petroleum ether, the volume ratio is 1:5) to obtain 1.11g of yellow solid, with a yield of 92.3%. Melting point 174~176°C.

[0338] 1 H-NMR (600 MHz, internal standard TMS, solvent CDCl3) δ (ppm): 4.98 (s, 1H, NH), 3.46–3.29 (m, 2H, N-CH2), 2.82 (d, J = 3.0 Hz, thiazyl-CH3), 2.43–2.37 (m, 5H, pyrimidyl-CH2, pyrimidyl-CH3), 1.42 (tt, J = 7.9, 6.4 Hz, 2H, CH2), 1.37–1.28 (m, 2H, CH2), 1.23–1.16 (m, 3H, CH3), 0.93–0.84 (m, 3H, CH3).

[0339] Example 7: Preparation of Compound 26A-231

[0340]

[0341] In a 100mL three-necked flask, add 0.63g (0.003mol) of 5-n-butyl-2-dimethylamino-6-methyl-4-pyrimidinol, 0.36g (0.0036mol) of triethylamine and 10mL of tetrahydrofuran, and add a mixture of 0.51g (0.0032mol) of 3-methyl-2-thiophenecarbonyl chloride and 4mL of tetrahydrofuran at room temperature, control the temperature below 20°C, add for 20min, and continue stirring for 2h. After the reaction is completed by TLC monitoring, the solvent is evaporated under reduced pressure, and (3×50ml) ethyl acetate is added for extraction, the organic phase is washed with 50ml of saturated brine, and the residue after desolventization is subjected to column chromatography (the eluent is ethyl acetate and petroleum ether, the volume ratio is 1:5) to obtain 0.91g of colorless oily liquid, with a yield of 90.9%.

[0342] 1 H-NMR (600MHz, internal standard TMS, solvent CDCl3) δ (ppm): 7.52 (d, J=5.0Hz, 1H, thienyl-5-H), 7.00 (d, J=5.0Hz, 1H, thienyl-4-H), 3.14 (m, 6H, N (CH3)2), 2.58 (s, 3H,thienyl-3-CH3),2.48–2.25(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.51–1.37(m,2H,CH2),1.38–1.26(m,2H,CH2),0.92–0.81(m,3H,CH3).

[0343] Example 8: Preparation of Compound 30B-32

[0344]

[0345] In a 100mL three-necked flask, add 0.63g (0.003mol) of 5-n-butyl-2-dimethylamino-6-methyl-4-pyrimidinol, 0.36g (0.0036mol) of triethylamine and 10mL of dichloromethane, and add a mixture of 0.67g (0.0032mol) of 4-trifluoromethyl-3-pyridinecarbonyl chloride and 4mL of dichloromethane dropwise at room temperature, control the temperature below 20°C, add dropwise for 20min, and continue stirring for 2h. After the reaction is completed by TLC monitoring, the solvent is evaporated under reduced pressure, and (3×50ml) ethyl acetate is added for extraction, and the organic phase is washed with 50ml of saturated brine. After desolventization, the residue is subjected to column chromatography (the eluent is ethyl acetate and petroleum ether, the volume ratio is 1:10) to obtain 1.05g of white solid, with a yield of 92%. Melting point 59~61°C.

[0346] 1 H-NMR (600MHz, internal standard TMS, solvent CDCl3) δ (ppm): 9.35 (s, 1H, pyridyl-2-H), 9.00 (d, J = 5.1Hz, 1H, pyridyl-6-H), 7.72 (d, J = 5.1Hz, 1H, pyridyl-5-H), 3.12 (s, 6 H,N(CH3)2),2.47–2.39(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.46–1.38(m,2H,CH2),1.31(dd,J=14.9,7.3Hz,2H,CH2),0.86(t,J=7.3Hz,3H,CH3).

[0347] Example 9: Preparation of Compound 30G-12

[0348]

[0349] In a 100mL three-necked flask, add 0.60g (0.003mol) of 2-phenylamino-6-methyl-4-pyrimidinol, 0.36g (0.0036mol) of triethylamine and 10mL of dichloromethane, and add a mixture of 0.67g (0.0032mol) of 2-trifluoromethyl-3-pyridinecarbonyl chloride and 4mL of dichloromethane dropwise at room temperature, control the temperature below 20°C, add dropwise for 20min, and continue stirring for 2h. After the reaction is completed by TLC monitoring, the solvent is evaporated under reduced pressure, and (3×50ml) ethyl acetate is added for extraction, the organic phase is washed with 50ml of saturated brine, and the residue after desolventization is subjected to column chromatography (the eluent is ethyl acetate and petroleum ether, the volume ratio is 1:5) to obtain 1.02g of yellow solid, with a yield of 91%. Melting point 183-185°C.

[0350] 1H-NMR (600MHz, internal standard TMS, solvent CDCl3) δ (ppm): 8.90 (d, J = 4.5Hz, 1H, pyridyl-6-H), 8.33 (d, J=7.8Hz,1H,pyridyl-4-H),7.67(dd,J=7.8,4.8Hz,1H,pyridyl-5-H),7.61(dd,J=15 .4,8.0Hz,2H,phenyl-2,6-2H),7.33(t,J=7.8Hz,2H,phenyl-3,5-2H),7.25(s,1H,NH ), 7.06 (t, J = 7.4Hz, 1H, phenyl-4-H), 6.56 (s, 1H, pyrimidyl-5-H), 2.50 (s, 3H, CH3).

[0351] Other compounds of the present invention can be prepared by referring to the above examples.

[0352] Physical properties and NMR data of some compounds ( 1 HNMR, 600 MHz, internal standard TMS, ppm) is as follows:

[0353] Compound 4A-146: colorless oily liquid. δ(CDCl3)8.05(s,1H,pyrazolyl-5-H),7.23–7.02(m,1H,CHF2),4.92(s,1H,NH),4.05–3.98(m,3H,pyrazolyl-1-CH3),3.45–3.32(m,2H,NCH2),2.41–2.37(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.46–1.35(m,2H,CH2),1.35–1.28(m,2H,CH2),1.19(t,J=7.2Hz,3H,CH3),0.89–0.85(m,3H,CH3).

[0354] Compound 4A-148: white solid, melting point 91-93° C. δ(CDCl3)7.09(dd, J=56.4,50.9Hz,1H,CHF2),4.91(s,1H,NH),3.98(s,pyrazolyl-CH3),3.48–3.31(m,2H,NCH2),2.45–2.29(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.41(ddd,J=37.6,19.8,14.0Hz,2H,CH2),1.31(dt,J=23.1,8.0Hz,2H,CH2),1.19(t,J=7.2Hz,3H,CH3),0.88(t,J=7.3Hz,3H,CH3).

[0355] Compound 4A-175: colorless solid, melting point 115-117°C. δ(CDCl3)8.13(s,1H,pyrazolyl-4-H),4.92(t,J=5.1Hz,1H,NH),4.02(s,3H,pyrazolyl-1-CH3),3.46–3.33(m,2H,NCH2),2.44–2.37(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.47–1.37(m,2H,CH2),1.31(dd,J=14.8,7.4Hz,2H,CH2),1.19(t,J=7.2Hz,3H,CH3),0.87(dd,J=10.7,3.9Hz,3H,CH3).

[0356] Compound 5A-148: white solid, melting point 80-82° C. δ(CDCl3)7.10(dd, J=76.6,30.8Hz,1H,CHF2),3.95(s,pyrazolyl-CH3),3.13(m,6H,N(CH3)2),2.51–2.29(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.47-1.26(m,4H,CH2CH2),0.95–0.82(m,3H,CH3).

[0357] Compound 7A-175: colorless solid, melting point 99-101°C. δ(CDCl3)8.13(s,1H,pyrazolyl-4-H),7.58(dt,J=8.9,1.7Hz,2H,phenyl-2,6-2H),7.31–7.26(m,2H,phenyl-3,5-2H),7.03(s,1H,NH),7.02–6.96(m,1H,phenyl-4-H),4.03(s,3H,pyrazolyl-1-CH3),2.53–2.44(m,2H,CH2),1.49–1.41(m,2H,CH2),1.39–1.31(m,3H,CH3),0.88–0.85(m,3H,CH3).

[0358] Compound 8A-41: white solid, melting point 81-83°C. δ(CDCl3) 5.34 (d, 1H, NH), 4.15 (s, 3H, pyrazolyl-1-CH3), 3.44–3.36 (m, 2H, NCH2), 2.72–2.66 (m, 2H, pyrazolyl-3-CH2), 2.46–2.42 (m, 2H, pyrimidyl-CH2), 2.41 (s, 3H, pyrimidyl-CH3), 1.49–1.42 (m, 2H, CH2), 1.34 (dd, J=14.9, 7.4 Hz, 2H, CH2), 1.29–1.26 (m, 3H, CH3), 1.20 (t, J=7.2 Hz, 3H, CH3), 0.91–0.86 (m, 3H, CH3).

[0359] Compound 8A-200: colorless oily liquid. δ(CDCl3)6.79(s,1H,pyrazolyl-4-H),5.04(s,1H,NH),4.56(q,J=7.2Hz,2H,pyrazolyl-CH2),3.46–3.33(m,2H,NCH2),2.45–2.37(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),2.33(d,J=2.7Hz,3H,pyrazolyl-CH3),1.47–1.39(m,5H,CH2,CH3),1.36–1.28(m,2H,CH2),1.20(dd,J=9.3,5.1Hz,3H,CH3),0.88(dd,J=9.4,5.2Hz,3H,CH3).

[0360] Compound 8A-300: white solid, melting point 141-143°C. δ(CDCl3)8.49(dd,J=4.8,1.7Hz,1H,pyridyl-6-H),7.93–7.84(m,1H,pyridyl-4-H),7 .45–7.38(m,1H,pyridyl-5-H),7.22–7.19(m,1H,pyrazolyl-4-H),4.89(d,J=19.7Hz, 1H,NH),3.34(dt,J=13.5,7.5Hz,2H,NCH2),2.40–2.29(m,5H,pyrimidyl-CH2,pyrimid yl-CH3), 1.41–1.23(m,4H,CH2CH2), 1.16(t,J=7.3Hz,3H,CH3), 0.94–0.85(m,3H,CH3).

[0361] Compound 9A-41: white solid, melting point 75-77°C. δ(CDCl3)4.15(s,3H,pyrazolyl-1-CH3),3.13(s,6H,N(CH3)2),2.74–2.63(m,2H,pyrazolyl-3-CH2),2.47–2.43(m,2H,pyrimidyl-CH2),2.41(s,3H,pyrimidyl-CH3),1.50–1.38(m,2H,CH2),1.38-1.29(m,2H,CH2),1.30–1.20(m,3H,CH3),0.94–0.81(m,3H,CH3).

[0362] Compound 9A-200: colorless oily liquid. δ(CDCl3)6.80(s,1H,pyrazolyl-4-H),4.56(q,J=7.2Hz,2H,pyrazolyl-CH2),3.13(m,6H,N(CH3)2),2.45–2.37(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),2.33(d,J=2.7Hz,3H,pyrazolyl-CH3),1.49–1.39(m,5H,CH2,CH3),1.31(m,2H,CH2),0.87(dd,J=9.4,5.2Hz,3H,CH3).

[0363] Compound 10A-41: white solid, melting point 86-88°C. δ(CDCl3)8.45(dd,J=8.9Hz,1H,phenyl-3-H),7.83(s,1H,pyrimidyl-5-H),7.42(d,J=2.4Hz,1H,phenyl-6-H),7.33–7.27(m,1H,phenyl-5-H),7.04(s,1H,NH),4.17(s,3H,pyrazolyl-1-CH3),2.76–2.65(m,2H,pyrazolyl-3-CH2),1.30–1.26(m,3H,CH3).

[0364] Compound 10A-200: white solid, melting point 135-137°C. δ(CDCl3)8.42(d, J=8.9Hz,1H,phenyl-3-H),7.81(s,1H,pyrimidyl-5-H),7.42(t, J=2.5Hz,1H,phenyl-6-H),7.29(dd, J=8.9,2.4Hz,1H,phenyl-5-H),7.06(s,1H,NH),6.86(s,1H,pyrazolyl-4-H),4.57(q, J=7.2Hz,2H,pyrazolyl-CH2),2.33(d, J=3.1Hz,3H,pyrazolyl-CH3),1.53–1.40(m,3H,CH3).

[0365] Compound 11A-41: white solid, melting point 147-149°C. δ(CDCl3)7.59(dt,J=8.9,1.6Hz,2H,phenyl-2,6-2H),7.33–7.27(m,2H,phenyl-3,5-2H),7.01(ddd,J=7.4,4.8,1.1Hz,3H,phenyl-4-H,NH),4.17(s,3H,pyrazolyl-1-CH3),2.70(q,J =7.6Hz,2H,pyrazolyl-3-CH2),2.59–2.44(m,5H,pyrimidyl-CH2,,3H,pyrimidyl-CH3),1. 54–1.43(m,2H,CH2),1.44–1.30(m,2H,CH2),1.32–1.26(m,3H,CH3),0.95–0.87(m,3H,CH3).

[0366] Compound 11A-200: colorless oily liquid. δ(CDCl3)7.59(m,phenyl-2,6-2H),7.33–7.27(m,2H,phenyl-3,5-2H),7.04(s,1H,NH),7 .02–6.98(m,1H,phenyl-4-H),6.80(s,1H,pyrazolyl-4-H),4.58(q,J=7.2Hz,2H,pyrazo lyl-1-CH2),2.53–2.45(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),2.36–2.29(m,3H,pyraz olyl-3-CH3), 1.53–1.43(m,5H,CH2,CH3), 1.40–1.29(m,2H,CH2), 0.95–0.86(m,3H,CH3).

[0367] Compound 11A-300: white solid, melting point 152-154°C. δ(CDCl3)8.58–8.40(m,1H,pyridyl-6-H),7.97–7.80(m,1H,pyridyl-4-H),7.56–7.51(m,2H,phenyl-2,6-2H),7.46–7.40(m,1H,pyridyl-5-H),7.31–7.26(m,2H,phenyl-3,5-2H),7.22(d,J=1. 6Hz,1H,pyrazolyl-4-H),7.00(ddt,J=8.4,7.4,1.1Hz,1H,phenyl-4-H),5.30(s,1H,NH),2.46– 2.39(m,5H,pyrimidyl-CH2,pyrimidyl-CH3), 1.46–1.29(m,4H,CH2CH2), 0.95–0.89(m,3H,CH3).

[0368] Compound 12A-237: colorless solid, melting point 109-111°C. δ(CDCl3)6.68(s,1H,pyrazolyl-4-H),4.89(s,1H,NH),4.22(q,J=7.3Hz,2H,pyrazo lyl-CH2),3.46–3.30(m,2H,NCH2),2.43(dd,J=17.0,9.2Hz,2H,pyrimidyl-CH2),2.3 7(d,J=16.3Hz,3H,pyrimidyl-CH3),1.48–1.40(ddd,J=15.1,13.8,7.2Hz,5H,CH2,C H3),1.34–1.27(m,2H,CH2),1.21–1.09(m,3H,CH3),0.86(dd,J=9.6,5.0Hz,3H,CH3).

[0369] Compound 15A-237: white solid, melting point 103-105°C. δ(CDCl3)7.68–7.59(m,2H,phenyl-2,6-2H),7.36–7.28(m,2H,phenyl-3,5-2H),7.2 5(s,1H,NH),7.07–6.99(m,1H,phenyl-4-H),6.71(s,1H,pyrazolyl-4-H),6.56(d,J =5.0Hz,1H,pyrimidyl-5-H),4.23(q,J=7.3Hz,1H,pyrazolyl-1-CH2),2.46(s,3H,p yrazolyl-5-CH3), 2.35 (d, J = 9.8 Hz, 3H, pyrimidyl-5-CH3), 1.52–1.45 (m, 3H, CH3).

[0370] Compound 16A-33: white solid, melting point 183-185° C. δ(CDCl3) 3.38 (dt, J=14.8, 7.4 Hz, 2H, NCH2), 2.50–2.29 (m, 5H, pyrimidyl-CH2, pyrimidyl-CH3), 1.45–1.30 (m, 4H, CH2CH2), 1.20–1.16 (m, 3H, CH3), 0.91–0.75 (m, 3H, CH3).

[0371] Compound 17A-33: brown solid, melting point 83-85° C. δ(CDCl3)3.11(s,6H,N(CH3)2),2.59–2.20(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.45–1.30(m,4H,CH2CH2),0.98–0.77(m,3H,CH3).

[0372] Compound 19A-33: yellow solid, melting point 160-162° C. δ(CDCl3)7.53(t, J=7.5Hz,2H,phenyl-2,6-2H),7.45(dd, J=12.5,5.1Hz,1H,phenyl-4-H),7.32(d, J=7.4Hz,2H,phenyl-3,5-2H),4.12(s,1H,NH),2.46–2.36(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.40(dd,4H,CH2CH2),0.97–0.90(m,3H,CH3).

[0373] Compound 20A-46: white solid, melting point 124-126° C. δ(CDCl3)8.28(s,1H,thiazyl-4-H),3.39(dt,J=15.1,7.5Hz,2H,NCH2),2.59–2.30(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.49–1.25(m,4H,CH2CH2),1.22–1.00(m,3H,CH3),0.96–0.69(m,3H,CH3).

[0374] Compound 20A-84: yellow solid, melting point 174-176°C. δ(CDCl3)4.98(s,1H,NH),3.46–3.29(m,2H,N-CH2),2.82(d,thiazyl-CH3),2.43–2.37(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.42(m,2H,CH2),1.37–1.28(m,2H,CH2),1.23–1.16(m,3H,CH3),0.93–0.84(m,3H,CH3).

[0375] Compound 21A-46: white solid, melting point 104-106° C. δ(CDCl3)8.28(s,1H,thiazyl-4-H),3.19(s,6H,N(CH3)2),2.59–2.30(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.49–1.25(m,4H,CH2CH2),1.05–0.70(m,3H,CH3).

[0376] Compound 21A-84: white solid, melting point 81-83° C. δ(CDCl3)3.13(s,6H,N(CH3)2),2.82(d,J=3.0Hz,thiazyl-CH3),2.49–2.32(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.47-1.36(m,2H,CH2),1.36–1.27(m,2H,CH2),0.87(m,3H,CH3).

[0377] Compound 24A-6: white solid, melting point 142-144° C. δ(CDCl3) 6.59 (d, J=0.8 Hz, 1H, oxazolyl-4-H), 4.98 (d, J=36.8 Hz, 1H, NH), 3.59–3.28 (m, 2H, NCH2), 2.54 (d, J=0.8 Hz, 1H, oxazolyl-CH3), 2.42 (s, 2H, pyrimidyl-CH2), 2.40 (s, 3H, pyrimidyl-CH3), 1.49–1.29 (m, 4H, CH2CH2), 1.23–1.13 (m, 3H, CH3), 0.96–0.84 (m, 3H, CH3).

[0378] Compound 24B-6: white solid, melting point 98-100° C. δ(CDCl3)6.53(d, J=0.8Hz,1H,oxazolyl-4-H),3.13(s,6H,N(CH3)2),2.54(d, J=0.8Hz,1H,oxazolyl-CH3),2.45–2.36(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.43(tt, J=7.9,6.5Hz,2H,CH2),1.31(dt, J=14.7,7.3Hz,2H,CH2),0.87(t, J=7.3Hz,3H,CH3).

[0379] Compound 25A-1: white solid, melting point 102-104°C. δ(CDCl3)7.98(dd,J=3.7,1.0Hz,1H,thienyl-5-H),7.68(dd,J=4.9,1.0Hz,1H,thieny l-3-H),7.18(dd,J=4.9,3.9Hz,1H,thienyl-4-H),4.95(s,1H,NH),3.46–3.32(m,2H,NC H2),2.42(dd,J=14.4,6.5Hz,2H,pyrimidyl-CH2),2.39(s,3H,pyrimidyl-CH3),1.51–1 .41(m,2H,CH2),1.37–1.29(m,2H,CH2),1.22–1.16(m,3H,CH3),0.90–0.85(m,3H,CH3).

[0380] Compound 25A-231: colorless oily liquid. δ(CDCl3)7.51(d,J=5.0Hz,1H,thienyl-5-H),6.99(d,J=5.0Hz,1H,thienyl-4-H),4.91(s,1H,NH),3.50–3.30(m,2H,NCH2),2.61(s,3H,thienyl-3-CH3),2.46–2.32(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.51–1.37(m,2H,CH2),1.38–1.26(m,2H,CH2),1.23–1.11(m,3H,CH3),0.92–0.81(m,3H,CH3).

[0381] Compound 26A-1: white solid, melting point 69-71° C. δ(CDCl3)7.98(dd, J=3.9,1.4Hz,1H,thienyl-5-H),7.75–7.60(m,1H,thienyl-3-H),7.22–7.06(m,1H,thienyl-4-H),3.12(s,6H,N(CH3)2),2.50–2.34(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.50–1.25(m,4H,CH2CH2),1.00–0.82(m,3H,CH3).

[0382] Compound 26A-231: colorless oily liquid. δ(CDCl3)7.52(d,J=5.0Hz,1H,thienyl-5-H),7.00(d,J=5.0Hz,1H,thienyl-4-H),3.14(m,6H,N(CH3)2),2.58(s,3H,thienyl-3-CH3),2.48–2.25(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.51–1.37(m,2H,CH2),1.38–1.26(m,2H,CH2),0.92–0.81(m,3H,CH3).

[0383] Compound 27A-1: white solid, melting point 116-118°C. δ(CDCl3)8.45(d, J=8.9Hz,1H,phenyl-3-H),8.05(td, J=4.1,1.0Hz,1H,thienyl-5-H),7.85–7.79(s,1H,NH),7.79–7.75(m,1H,thienyl-3-H),7.42(d, J=2.4Hz,1H,phenyl-5-H),7.30(dd, J=9.0,2.4Hz,1H,phenyl-6-H),7.25–7.20(m,1H,thienyl-4-H),7.10(s,1H,pyrimidyl-5-H).

[0384] Compound 29A-21: yellow solid, melting point 129-131° C. δ(CDCl3)8.72(d, J=5.4Hz,1H,pyridyl-6-H),8.23(d, J=2.4Hz,1H,pyridyl-3-H),7.55(dd, J=5.4,2.4Hz,1H,pyridyl-5-H),4.97(m,1H,NH),3.38(dd,2H,N-CH2),2.44–2.28(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.44(m,2H,CH2),1.28(m,2H,CH2),1.17(t,3H,CH3),0.84(t,3H,CH3).

[0385] Compound 29A-164: yellow oily liquid. δ(CDCl3)7.83–7.79(d,1H,pyridyl-4-H),7.47–7.43(d,1H,pyridyl-5-H),5.03(s,1H,NH),3.42–3.30(m,2H,NCH2),2.54–2.45(m,2H,pyrimidyl-CH2),2.40(s,3H,pyrimidyl-CH3),1.53–1.43(m,2H,CH2),1.39(ddt,J=22.4,14.9,7.5Hz,2H,CH2),1.18(t,J=7.2Hz,3H,CH3),0.97–0.87(m,3H,CH3).

[0386] Compound 29B-164: yellow solid, melting point 83-85°C. δ(CDCl3)7.83–7.77(d,1H,pyridyl-4-H),7.47–7.41(d,1H,pyridyl-5-H),3.10(s,6H,N(CH3)2),2.55–2.32(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.54–1.41(m,2H,CH2),1.43–1.31(m,2H,CH2),0.94–0.80(m,3H,CH3).

[0387] Compound 30A-12: yellow solid, melting point 128-130°C. δ(CDCl3)8.89(d,J=4.2Hz,1H,pyridyl-6-H),8.38(d,J=7.7Hz,1H,pyridyl-4-H),7 .69(dd,J=7.8Hz,1H,pyridyl-5-H),4.99(s,1H,NH),3.47–3.29(m,2H,N-CH2),2.48 –2.42(m,2H,pyrimidyl-CH2),2.40(d,J=12.5Hz,3H,pyrimidyl-CH3),1.48–1.38(m ,3H,CH3),1.38–1.29(m,2H,CH2),1.20(t,J=7.2Hz,2H,CH2),0.90–0.85(m,3H,CH3).

[0388] Compound 30A-32: yellow solid, melting point 91-93°C. δ(CDCl3)9.37(s,1H,pyridyl-2-H),9.02(d,J=5.1Hz,1H,pyridyl-6-H),7.74(d, J=5.1Hz,1H,pyridyl-5-H),4.96(s,1H,NH),3.48–3.34(m,2H,NCH2),2.47–2.38(m ,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.44(ddd,J=12.0,8.8,6.5Hz,2H,CH2),1. 33(dq,J=14.7,7.3Hz,2H,CH2),1.20(t,J=7.2Hz,3H,CH3),0.90–0.85(m,3H,CH3).

[0389] Compound 30A-49: yellow solid, melting point 77-79° C. δ(CDCl3) 9.52 (d, J=1.7 Hz, 1H, pyridyl-2-H), 9.12 (d, J=1.7 Hz, 1H, pyridyl-6-H), 8.65 (s, 1H, pyridyl-4-H), 4.95 (s, 1H, NH), 3.46–3.30 (m, 2H, NCH2), 2.46–2.37 (m, 5H, pyrimidyl-CH3, pyrimidyl-CH2), 1.44 (m, 2H, CH2), 1.31 (m, 2H, CH2), 1.19 (t, 3H, CH3), 0.85 (t, 3H, CH3).

[0390] Compound 30A-58: white solid, melting point 150-152°C. δ(CDCl3)9.15(d,J=2.1Hz,1H,pyridyl-2-H),8.37(dd,J=8.3,2.4Hz,1H,pyridyl-4-H),7.50(d,J=8.3Hz,1H,pyridyl-5-H),4.93(s,1H,NH),3.49–3.30(m,2 H,N-CH2),2.48–2.32(m,2H,pyrimidyl-CH2),1.44(dt,J=15.3,7.5Hz,2H,CH2) ,1.35–1.27(m,2H,CH2),1.20(t,J=7.2Hz,3H,CH3),0.86(t,J=7.3Hz,3H,CH3).

[0391] Compound 30A-300: white solid, melting point 137-139° C. δ(CDCl3)8.17(d,1H,pyridyl-4-H),6.57(d,1H,pyridyl-5-H),4.99(s,1H,NH),3.41(dt,,2H,NCH2),2.45(s,3H,CH3),2.43–2.20(m,5H,pyrimidyl-CH3,pyrimidyl-CH2),1.44(m,2H,CH2),1.31(m,2H,CH2),1.20(t,3H,CH3),0.89–0.85(t,3H,CH3).

[0392] Compound 30B-49: white solid, melting point 70-72° C. δ(CDCl3)9.53(d, J=1.8Hz,1H,pyridyl-2-H),9.12(d, J=1.7Hz,1H,pyridyl-6-H),8.66(s,1H,pyridyl-4-H),3.12(s,6H,N(CH3)2),2.43–2.36(m,5H,pyrimidyl-CH3,pyrimidyl-CH2),1.43(m,2H,CH2),1.33–1.28(m,2H,CH2),0.84(t,3H,CH3).

[0393] Compound 30B-300: white solid, melting point 146-148°C. δ(CDCl3)8.23–8.18(m,1H,pyridyl-4-H),6.57(d,1H,pyridyl-5-H),3.14(s,6H,N(CH3)2),2.45(s,3H,CH3),2.41(s,3H,CH3),2.40–2.35(m,2H,CH2),1.42(m,2H,CH2),1.36–1.32(m,2H,CH2),0.84(t,3H,CH3).

[0394] Compound 30D-32: white solid, melting point 121-123°C. δ(CDCl3)9.36(s,1H,pyridyl-2-H),9.03(d,J=5.1Hz,1H,pyridyl-6-H),7.75(d,J=5 .1Hz,1H,pyridyl-5-H),7.58(d,J=7.7Hz,2H,phenyl-2,6-2H),7.32–7.26(m,2H,phe nyl-3,5-2H),7.03(s,1H,NH),7.00(t,J=7.4Hz,1H,phenyl-4-H),2.56–2.47(m,5H,p yrimidyl-CH2,pyrimidyl-CH3),1.46(m,2H,CH2),1.35(m,2H,CH2),0.89(t,3H,CH3).

[0395] Compound 30D-58: white solid, melting point 159-161°C. δ(CDCl3)9.17(d,J=2.1Hz,1H,pyridyl-2-H),8.39(dd,J=8.3,2.4Hz,1H,pyridyl-4-H),7.60-7.58(t,J=7.5Hz,2H,phenyl-2,6-2H),7.53(d,J=8.3Hz,1H,pyridyl-5-H),7.45(dd,J=12.5,5.1 Hz,1H,phenyl-4-H),7.31-7.29(d,J=7.4Hz,2H,phenyl-3,5-2H),2.51–2.48(m,5H,pyrimidyl- CH2,pyrimidyl-CH3),1.49-1.32(ddd,J=21.5,15.1,7.9Hz,4H,CH2CH2),0.90–0.87(m,3H,CH3).

[0396] Compound 30E-12: yellow solid, melting point 142-144°C. δ(CDCl3)8.92(d,J=3.7Hz,1H,pyridyl-6-H),8.36(d,J=7.8Hz,1H,pyridyl-4-H),7.70(dd,J=7.8,4.7Hz,1H,pyridyl-5-H),7.62(d,J=9.0Hz,2H,phenyl-2,6-2H),7.16(d,J=8.7Hz,2 H,phenyl-3,5-2H),7.08(s,1H,NH),2.56–2.47(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.4 7(dt,J=12.4,7.6Hz,2H,CH2), 1.36(dd,J=14.8,7.3Hz,2H,CH2), 0.90(t,J=7.3Hz,3H,CH3).

[0397] Compound 30F-12: white solid, melting point 165-167°C. δ(CDCl3)8.94(d, J=4.2Hz,1H,pyridyl-6-H),8.42(d, J=8.9Hz,1H,pyridyl-4-H),8.36(d, J=7.8Hz,1H,phenyl-3-H),7.74(d, J=18.7Hz,1H,pyridyl-5-H),7.74–7.66(m,1H,phenyl-6-H),7.42(d, J=12.9Hz,1H,NH),7.29(d, J=9.0Hz,1H,phenyl-5-H),7.03(s,1H,pyrimidyl-5-H),6.50(t, J=54.8Hz,1H,CHF2).

[0398] Compound 31A-12: yellow solid, melting point 171-173° C. δ(CDCl3)8.98(d, J=4.9Hz,1H,pyridyl-6-H),8.34(s,1H,pyridyl-3-H),8.17(dd, J=4.9,0.9Hz,1H,pyridyl-5-H),4.95(s,1H,NH),3.42–3.33(m,2H,N-CH2),2.44–2.36(m,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.48–1.40(m,2H,CH2),1.30(dd,2H,CH2),1.19(t,J=7.2Hz,3H,CH3),0.87–0.84(t,3H,CH3).

[0399] Compound 31B-12: white solid, melting point 74-76° C. δ(CDCl3)8.97(d, J=4.9Hz,1H,pyridyl-6-H),8.36(s,1H,pyridyl-3-H),8.18(dd, J=4.9,0.9Hz,1H,pyridyl-5-H),3.12(s,6H,N(CH3)2),2.42(s,3H,pyrimidyl-CH3),2.41–2.36(m,2H,pyrimidyl-CH2),1.46–1.39(m,2H,CH2),1.29(dd,2H,CH2),0.85(t,3H,CH3).

[0400] Compounds 32A-33: 1 H-NMR (600MHz, internal standard TMS, solvent CDCl3) δ (ppm): 9.09 (s, 1H, pyrimidyl-2-H), 4.35 (q, J = 7.3Hz, 2H, NCH2), 2.75–2.48 (m, 2H, pyr imidyl-CH2),2.30(s,3H,pyrimidyl-CH3),1.51(m,2H,CH2),1.46–1.36(m,2H,CH2),1.32(t,3H,CH3),0.94(t,3H,CH3).

[0401] Compound 32B-156: yellow solid, melting point 144-146°C. δ(CDCl3)9.23(s,1H,pyrimidyl-6-H),7.70–7.59(m,3H,phenyl-3,4,5-3H),7.36(d,J=8.8Hz,2H,phenyl-2,6-2H),3.12(s,6H,N(CH3)2),2.39(d,J=10.9Hz,5H,pyrimidyl-CH2,pyrimidyl-CH3),1.41(m,2H,CH2),1.30(m,2H,CH2),0.86(t,3H,CH3).

[0402] Compound 32B-200: white solid, melting point 110-112°C. δ(CDCl3)9.56(s,2H,pyrimidyl-4,6-2H),3.13(s,6H,N(CH3)2),2.74–2.16(m,5H,pyrimidyl-CH3,pyrimidyl-CH2),1.42(m,2H,CH2),1.30(m,2H,CH2),0.86(t,3H,CH3).

[0403] Biological Activity Assay Example

[0404] The compound of the invention exhibits good activity against various pathogens in the agricultural field.

[0405] Example 10: Bactericidal activity assay

[0406] The samples of the compounds of the present invention were used to test the protective effect of the compounds on various fungal diseases of plants. The results of the fungicidal activity test are shown in the following examples.

[0407] (1) In vivo protective activity assay

[0408] The determination method is as follows: adopt the living potted plant determination method, that is, the sample of the compound to be tested is dissolved with a small amount of solvent (the type of solvent is such as acetone, methanol, DMF, etc., and is selected according to its solubility for the sample, and the volume ratio of the amount of solvent to the amount of spraying liquid is equal to or less than 0.05), and diluted with water containing 0.1% Tween 80 to prepare the required concentration of the test solution. On the crop sprayer, the test solution is sprayed on the disease host plant (the host plant is a standard potted seedling cultivated in a greenhouse), and the disease is inoculated 24 hours later. According to the characteristics of the disease, the diseased plants that need to be cultivated with temperature control and moisture retention are inoculated and placed in an artificial climate chamber for cultivation. After the disease infection is completed, they are moved to the greenhouse for cultivation. The diseased plants that do not need moisture retention cultivation are directly inoculated and cultivated in the greenhouse. After the control is fully diseased (usually one week), the disease prevention effect of the compound is evaluated.

[0409] The in vivo protective activity test results of some compounds are as follows:

[0410] In vivo protective activity against cucumber downy mildew:

[0411] At a dosage of 400 ppm, the compounds with a control effect of more than 85% on cucumber downy mildew include: 4A-175, 5A-148, 7A-175, 8A-200, 8A-300, 11A-200, 11A-300, 15A-237, 19A-33, 20A-46, 25A-1, 26A-1, 27A-1, etc.;

[0412] At a dosage of 100 ppm, the compounds with an efficacy of more than 85% against cucumber downy mildew are: 5A-148, 8A-200, 8A-300, 11A-200, 11A-300, 20A-46;

[0413] In vivo protective activity against cucumber powdery mildew:

[0414] At a dosage of 400 ppm, the compounds with an efficacy of more than 85% against cucumber powdery mildew are: 4A-148, 4A-175, 5A-148, 7A-175, 8A-41, 8A-200, 8A-300, 9A-41, 9A-200, 11A-41, 11A-200, 12A-237, 16A-33, 17A-33 , 20A-46, 20A-84, 21A-46, 21A-84, 24A-6, 24B-6, 25A-1, 25A-231, 26A-1, 26A-231, 29A-32, 29A-164, 29B-237, 30A-49, 30B-32, 30B-300, 31A-12, 31B-12, etc.;

[0415] At a dosage of 100 ppm, the compounds with a control effect of more than 85% on cucumber powdery mildew include: 4A-148, 5A-148, 8A-41, 8A-200, 8A-300, 9A-200, 9A-41, 11A-41, 11A-200, 12A-237, 16A-33, 17A-33, 20A-46, 21A-46, 24A-6, 24B-6, 25A-231, 26A-231, 29A-32, 29A-164, 29B-237, 30A-49, 30B-32, 31A-12, 31B-12, etc.

[0416] In vivo protective activity against corn rust:

[0417] At a dosage of 400ppm, the compounds with an efficacy of more than 85% against corn rust include: 8A-200, 10A-200, 11A-200, 24B-6, etc.

[0418] In vivo protective activity against cucumber anthracnose:

[0419] At a dosage of 400 ppm, the compounds with an efficacy of more than 85% against cucumber anthracnose include: 4A-148, 16A-33, 17A-33, 19A-33, 20A-46, 21A-46, etc.;

[0420] In vivo protective activity against wheat powdery mildew:

[0421] At a dosage of 400ppm, the compounds with a control effect of more than 85% on wheat powdery mildew include: 4A-146, 4A-148, 5A-148, 8A-41, 8A-200, 11A-200, 9A-41, 12A-237, 19A-33, 20A-84, 25A-231, 29A-21, 29A-32, 30A-12, 30A-49, 30A-58, 30B-32, 30B-49, 30B-300, 30D-32, 30E-12, 30F-12, 30G-12, 31A-12, 31B-12, 32B-200, etc.

[0422] At a dosage of 100 ppm, the compounds with a control effect of more than 85% on wheat powdery mildew include: 4A-146, 4A-148, 5A-148, 8A-41, 8A-200, 11A-200, 9A-41, 12A-237, 20A-84, 25A-231, 29A-21, 29A-32, 30A-12, 30A-49, 30A-58, 30B-32, 30B-49, 30B-300, 30D-32, 30E-12, 30F-12, 31A-12, 31B-12, 32B-200, etc.

[0423] (2) Test results of some compounds and control drugs

[0424] Activity comparison tests were conducted on some compounds and control drugs, and the test results are shown in Tables 33 to 35 (" / / / " in the table means not tested).

[0425] Table 33 In vivo protective activity against cucumber downy mildew

[0426]

[0427] Table 34 In vivo protective activity against cucumber powdery mildew

[0428]

[0429] Table 35 In vivo protective activity against wheat powdery mildew

[0430]

Claims

1. A substituted pyrimidine ester compound, characterized in that: The substituted pyrimidine ester compounds are Compounds described in general formulas I-1, I-2, I-3, I-4, I-5, I-6, I-9, IV-1, IV-2 and IV-3: R1 is selected from C1-C4 alkyl, halogenated C1-C4 alkyl; R2 is selected from C1-C6 alkyl, halogenated C1-C6 alkyl; W is selected from NR3R4, unsubstituted aniline; X is selected from O; Y is selected from O; R3 and R4 may be the same or different and are selected from hydrogen, C1-C4 alkyl; R5 is selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, R 6a , R 7a , R 8a are independently selected from hydrogen, C1-C4 alkyl, pyridyl substituted by 1-5 R5; R 6b , R 6c , R 7b , R 7c , R 8b , R 8c may be the same or different, and are independently selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl; R 9a , R 9b , R 10a , R 10b , R 11a , R 11b may be the same or different, and are selected from hydrogen, halogen C1-C4 alkyl, halogenated C1-C4 alkyl; R 14a , R 14b , R 14c may be the same or different, but are not simultaneously selected from hydrogen, and are each selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl; R 16a , R 16b , R 16c , R 16d may be the same or different, but are not simultaneously selected from hydrogen, and are each selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy,; R 17a , R 17b , R 17c , R 17d may be the same or different, but are not simultaneously selected from hydrogen, and are each selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl; R 18a , R 18b , R 18c , R 18d may be the same or different, but are not selected from hydrogen at the same time, and are selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl; Or a salt of the compound represented by the above general formula.

2. The compound according to claim 1, characterized in that: Among the compounds of general formula I-1, I-2, I-3, I-4, I-5, I-6, I-9, IV-1, IV-2 or IV-3: R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, monofluoroethyl, monochloroethyl, monobromoethyl, monofluoroisopropyl, difluoromethyl, dibromomethyl, trifluoromethyl, trichloromethyl, trifluoroethyl; R2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-methylbutyl, n-hexyl, monofluoromethyl, monochloromethyl, monofluoroethyl, monochloroethyl, monobromoethyl, monofluoropropyl, monochloropropyl, monobromopropyl, monofluorobutyl, monochlorobutyl, difluoromethyl, trifluoromethyl, trifluoroethyl, trifluoropropyl, heptafluoroisopropyl; W is selected from methylamino, ethylamino, dimethylamino, methylethylamino, diethylamino, and unsubstituted anilino; X is selected from O; Y is selected from O; R5 is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl; R 6a , R 7a , R 8a is selected from hydrogen, methyl, ethyl, n-propyl, cyclopropyl, allyl, propargyl, pyridyl substituted with 1-5 R5; R 6b , R 6c , R 7b , R 7c , R 8b , R 8c may be the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl; R 9a , R 9b , R 10a , R 10b , R 11a , R 11b may be the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl; R 14a , R 14b , R 14c may be the same or different, but not simultaneously selected from hydrogen, and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl; R 16a , R 16b , R 16c , R 16d may be the same or different, but not simultaneously selected from hydrogen, and are respectively selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, methoxy, ethoxy,; R 17a , R 17b , R 17c , R 17d may be the same or different, but not simultaneously selected from hydrogen, and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl; R 18a , R 18b , R 18c , R 18d may be the same or different, but not simultaneously selected from hydrogen, and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, monofluoromethyl, monochloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl; Or a salt of the compound represented by the above general formula.

3. The compound according to claim 2, characterized in that: In the compound of formula I-1, I-2, I-3, IV-1, IV-2 or IV-3: R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl; R2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl; W is selected from methylamino, ethylamino, dimethylamino, methylethylamino, diethylamino, and unsubstituted anilino; X is selected from O; Y is selected from O; R5 is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, difluoromethyl, trifluoromethyl, trifluoroethyl; R 6a , R 7a , R 8a is selected from hydrogen, methyl, ethyl, n-propyl, pyridyl substituted by 1-5 R5; R 6b , R 6c , R 7b , R 7c , R 8b , R 8c may be the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, difluoromethyl, trifluoromethyl, trifluoroethyl; R 16a , R 16b , R 16c , R 16d may be the same or different, but not simultaneously selected from hydrogen, and are each selected from hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, methoxy, ethoxy; R 17a , R 17b , R 17c , R 17d may be the same or different, but not simultaneously selected from hydrogen, and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl; R 18a , R 18b , R 18c , R 18d may be the same or different, but not simultaneously selected from hydrogen, and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl; Or a salt of the compound represented by the above general formula.

4. Use of the substituted pyrimidine ester compound according to any one of claims 1 to 3 for preparing a fungicide in agriculture or other fields; the diseases are cucumber downy mildew, powdery mildew, corn rust, and cucumber anthracnose.

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