Substituted pyrazole compounds containing pyrimidine and preparation method and use thereof

Abstract

Disclosed are substituted pyrazole compounds containing pyrimidinyl as shown in Formula I: ##STR00001##
The definitions of each of the substituents can be seen in the description. The compounds of present invention have a good spectrum of bactericidal, insecticidal and acaricidal activity, and have good control effect on downy mildew of cucumber, powdery mildew of wheat, corn rust, rice blast, cucumber anthracnosis and the like. The compounds of present invention also show good insecticidal activity.

Claims

1. A substituted pyrazole compound containing pyrimidinyl represented by formula I: ##STR00295## wherein R.sub.1 is H, halogen, cyano, nitro, amino, carboxyl, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.3-C.sub.12cycloalkyl, C.sub.1-C.sub.12alkoxy, haloC.sub.1-C.sub.12alkoxy, C.sub.1-C.sub.12alkylthio, haloC.sub.1-C.sub.12alkylthio, C.sub.1-C.sub.12alkylsulfinyl, C.sub.1-C.sub.12alkylsulfonyl, C.sub.2-C.sub.12alkenyl, haloC.sub.2-C.sub.12alkenyl, C.sub.2-C.sub.12alkynyl, haloC.sub.2-C.sub.12alkynyl, C.sub.3-C.sub.12alkenoxy, haloC.sub.3-C.sub.12alkenoxy, C.sub.3-C.sub.12alkynoxy, haloC.sub.3-C.sub.12alkynoxy, C.sub.1-C.sub.12alkylamino, di(C.sub.1-C.sub.12alkyl)amino, C.sub.1-C.sub.12alkylaminocarbonyl, haloC.sub.1-C.sub.12alkylaminocarbonyl, C.sub.1-C.sub.12alkoxycarbonyl, haloC.sub.1-C.sub.12alkoxycarbonyl, C.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkyl, or C.sub.1-C.sub.12alkylthioC.sub.1-C.sub.12alkyl; R.sub.2 is H, halogen, cyano, nitro, amino, carboxyl, CHO, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxy, or haloC.sub.1-C.sub.12alkoxy; R.sub.1, R.sub.2 and their conjoint pyrimidine ring can also form a five-membered ring, six-membered ring, seven-membered ring or eight-membered ring which contains carbon atom, nitrogen atom, oxygen atom, or sulphur atom; X is NR.sub.3, O, or S; Y is NR.sub.3, O, or S; R.sub.3 is H, OH, CHO, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxy, haloC.sub.1-C.sub.12alkoxy, C.sub.3-C.sub.12cycloalkyl, C.sub.1-C.sub.12alkylthio, C.sub.2-C.sub.12alkenylthio, C.sub.2-C.sub.12alkenyl, C.sub.2-C.sub.12alkynyl, haloC.sub.2-C.sub.12alkenyl, haloC.sub.2-C.sub.12alkynyl, C.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkylthioC.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkylthioC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkylsulfinyl, haloC.sub.1-C.sub.12alkylsulfinyl, C.sub.1-C.sub.12alkylsulfonyl, haloC.sub.1-C.sub.12alkylsulfonyl, C.sub.1-C.sub.12alkylaminosulfonyl, di(C.sub.1-C.sub.12alkyl)aminosulfonyl, C.sub.1-C.sub.12alkylsulfonylaminocarbonyl, C.sub.1-C.sub.12alkylcarbonylaminosulfonyl, C.sub.3-C.sub.12cycloalkyloxycarbonyl, C.sub.1-C.sub.12alkylcarbonyl, haloC.sub.1-C.sub.12alkylcarbonyl, C.sub.1-C.sub.12alkoxycarbonyl, haloC.sub.1-C.sub.12alkoxycarbonyl, C.sub.1-C.sub.12alkylcarbonylC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxycarbonylC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkylaminocarbonyl, di(C.sub.1-C.sub.12alkyl)aminocarbonyl, C.sub.2-C.sub.12alkenoxycarbonyl, C.sub.2-C.sub.12alkynoxycarbonyl, C.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkoxycarbonyl, C.sub.1-C.sub.12alkylaminothio, di(C.sub.1-C.sub.12alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC.sub.1-C.sub.6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC.sub.1-C.sub.6alkyloxycarbonyl, or (hetero)arylC.sub.1-C.sub.6alkyl by 1 to 5 following groups: halo, nitro, cyano, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, or haloC.sub.1-C.sub.6alkoxy; R.sub.4 and R.sub.5 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxy, or haloC.sub.1-C.sub.12alkoxy; or R.sub.4, R.sub.5 and their conjoint carbon can also form a C.sub.3-C.sub.8 cycle; R.sub.6 and R.sub.7 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxy, or haloC.sub.1-C.sub.12alkoxy; or R.sub.6, R.sub.7 and their conjoint carbon can also form a C.sub.3-C.sub.8 cycle; m is an integer selected from 0 to 5; R.sub.8 is H, cyano, halogen, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxycarbonyl, haloC.sub.1-C.sub.12alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.9 is H, cyano, halogen, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxycarbonyl, haloC.sub.1-C.sub.12alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.10 is C.sub.1-C.sub.12alkyl, C.sub.3-C.sub.8cycloalkyl, haloC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkylcarbonyl, haloC.sub.1-C.sub.12alkylcarbonyl, C.sub.1-C.sub.12alkylsulfonyl, haloC.sub.1-C.sub.12alkylsulfonyl, C.sub.1-C.sub.12alkoxycarbonyl, C.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxycarbonylC.sub.1-C.sub.12alkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.11 is halogen, OH, amino, cyano, nitro, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxy, haloC.sub.1-C.sub.12alkoxy, C.sub.3-C.sub.12cycloalkyl, C.sub.1-C.sub.12alkylamino, haloC.sub.1-C.sub.12alkylamino, di(C.sub.1-C.sub.12alkyl)amino, halodi(C.sub.1-C.sub.12alkyl)amino, C(═O)NR.sub.12R.sub.12, C.sub.1-C.sub.12alkylthio, haloC.sub.1-C.sub.12alkylthio, C.sub.2-C.sub.12alkenyl, C.sub.2-C.sub.12alkynyl, C.sub.2-C.sub.12alkenoxy, haloC.sub.2-C.sub.12alkenoxy, C.sub.2-C.sub.12alkynoxy, haloC.sub.2-C.sub.12alkynoxy, C.sub.1-C.sub.12alkylsulfonyl, haloC.sub.1-C.sub.12alkylsulfonyl, C.sub.1-C.sub.12alkylcarbonyl, haloC.sub.1-C.sub.12alkylcarbonyl, C.sub.1-C.sub.12alkoxycarbonyl, haloC.sub.1-C.sub.12alkoxycarbonyl, C.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkylthioC.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkylthioC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkoxycarbonylC.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkoxycarbonylC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkylthiocarbonylC.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkylthiocarbonylC.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12alkylcarbonyloxy, haloC.sub.1-C.sub.12alkylcarbonyloxy, C.sub.1-C.sub.12alkoxycarbonyloxy, haloC.sub.1-C.sub.12alkoxycarbonyloxy, C.sub.1-C.sub.12alkylsulfonyloxy, haloC.sub.1-C.sub.12alkylsulfonyloxy, C.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkoxy, or haloC.sub.1-C.sub.12alkoxyC.sub.1-C.sub.12alkoxy; R.sub.12 and R.sub.13 may be the same or different and are each independently H, C.sub.1-C.sub.12alkyl, or haloC.sub.1-C.sub.12alkyl; W is H, halogen, C.sub.1-C.sub.12alkyl, haloC.sub.1-C.sub.12alkyl, C.sub.3-C.sub.8cycloalkyl, C.sub.1-C.sub.12alkoxy, C.sub.1-C.sub.12alkylthio, or C.sub.1-C.sub.12alkylsulfonyl; and the position of Y linked to pyrazole ring is from 3-position, 4-position, or 5-position; when Y is linked to 3-position of pyrazole, R.sub.8 is at the 4-position R.sub.9 is at the 5-position; when Y is linked to 4-position of pyrazole, R.sub.8 is at the 3-position R.sub.9 is at the 5-position; when Y is linked to 5-position of pyrazole, R.sub.8 is at the 3-position R.sub.9 is at the 4-position; or a salt thereof.

2. The substituted pyrazole compound containing pyrimidinyl according to claim 1, wherein R.sub.1 is H, halogen, cyano, nitro, amino, carboxyl, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6alkoxy, haloC.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, haloC.sub.1-C.sub.6alkylthio, C.sub.2-C.sub.6alkenyl, haloC.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, haloC.sub.2-C.sub.6alkynyl, C.sub.3-C.sub.6alkenoxy, haloC.sub.3-C.sub.6alkenoxy, C.sub.3-C.sub.6alkynoxy, haloC.sub.3-C.sub.6alkynoxy, C.sub.1-C.sub.6alkylamino, di(C.sub.1-C.sub.6alkyl)amino, C.sub.1-C.sub.6alkylaminocarbonyl, haloC.sub.1-C.sub.6alkylaminocarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, haloC.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkyl, or C.sub.1-C.sub.6alkylthioC.sub.1-C.sub.6alkyl; R.sub.2 is H, halogen, cyano, nitro, amino, carboxyl, CHO, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, or haloC.sub.1-C.sub.6alkoxy; R.sub.1, R.sub.2 and their conjoint pyrimidine ring can also form a five-membered ring or six-membered ring which contains carbon atom, nitrogen atom, oxygen atom, or sulphur atom; X is NR.sub.3, O, or S; Y is NR.sub.3, O, or S; R.sub.3 is H, OH, CHO, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, haloC.sub.1-C.sub.6alkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6alkylthio, C.sub.2-C.sub.6alkenylthio, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, haloC.sub.2-C.sub.6alkenyl, haloC.sub.2-C.sub.6alkynyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkylthioC.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkylthioC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkylsulfinyl, haloC.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, haloC.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkylaminosulfonyl, di(C.sub.1-C.sub.6alkyl)aminosulfonyl, C.sub.1-C.sub.6alkylsulfonylaminocarbonyl, C.sub.1-C.sub.6alkylcarbonylaminosulfonyl, C.sub.3-C.sub.6cycloalkyloxycarbonyl, C.sub.1-C.sub.6alkylcarbonyl, haloC.sub.1-C.sub.6alkylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, haloC.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkylcarbonylC.sub.1C.sub.6alkyl, C.sub.1-C.sub.6alkoxycarbonylC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkylaminocarbonyl, di(C.sub.1-C.sub.6alkyl)aminocarbonyl, C.sub.2-C.sub.6alkenoxycarbonyl, C.sub.2-C.sub.6alkynoxycarbonyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkylaminothio, di(C.sub.1-C.sub.6alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC.sub.1-C.sub.6alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC.sub.1-C.sub.6alkyloxycarbonyl, or (hetero)arylC.sub.1-C.sub.6alkyl by 1 to 5 following groups: halogen, nitro, cyano, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, or haloC.sub.1-C.sub.6alkoxy; R.sub.4 and R.sub.5 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, or haloC.sub.1-C.sub.6alkoxy; or R.sub.4, R.sub.5 and their conjoint carbon can also form a C.sub.3-C.sub.6 cycle; R.sub.6 and R.sub.7 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, or haloC.sub.1-C.sub.6alkoxy; or R.sub.6, R.sub.7 and their conjoint carbon can also form a C.sub.3-C.sub.6 cycle; m is selected from 0 to 4; R.sub.8 is H, cyano, halogen, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxycarbonyl, haloC.sub.1-C.sub.6alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.9 is H, cyano, halogen, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxycarbonyl, haloC.sub.1-C.sub.6alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.10 is C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkylcarbonyl, haloC.sub.1-C.sub.6alkylcarbonyl, C.sub.1-C.sub.6alkylsulfonyl, haloC.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxycarbonylC.sub.1-C.sub.6alkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.11 is halogen, OH, amino, cyano, nitro, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, haloC.sub.1-C.sub.6alkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6alkylamino, haloC.sub.1-C.sub.6alkylamino, di(C.sub.1-C.sub.6alkyl)amino, halodi(C.sub.1-C.sub.6alkyl)amino, C(═O)NR.sub.12R.sub.13, C.sub.1-C.sub.6alkylthio, haloC.sub.1-C.sub.6alkylthio, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6alkenoxy, haloC.sub.2-C.sub.6alkenoxy, C.sub.2-C.sub.6alkynoxy, haloC.sub.2-C.sub.6alkynoxy, C.sub.1-C.sub.6alkylsulfonyl, haloC.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkylcarbonyl, haloC.sub.1-C.sub.6alkylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, haloC.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkylthioC.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkylthioC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxycarbonylC.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkoxycarbonylC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkylthiocarbonylC.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkylthiocarbonylC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkylcarbonyloxy, haloC.sub.1-C.sub.6alkylcarbonyloxy, C.sub.1-C.sub.6alkoxycarbonyloxy, haloC.sub.1-C.sub.6alkoxycarbonyloxy, C.sub.1-C.sub.6alkylsulfonyloxy, haloC.sub.1-C.sub.6alkylsulfonyloxy, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.6alkoxy, or haloC.sub.1-C.sub.6alkoxyC.sub.1C.sub.6alkoxy; R.sub.12 and R.sub.13 may be the same or different and are each independently H, C.sub.1-C.sub.6alkyl, or haloC.sub.1-C.sub.6alkyl; and W is H, halogen, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6alkylthio, or C.sub.1-C.sub.6alkylsulfonyl.

3. The substituted pyrazole compound containing pyrimidinyl according to claim 2, wherein R.sub.1 is H, halogen, cyano, nitro, amino, carboxyl, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4alkylthio, C.sub.1-C.sub.4alkylsulfinyl, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylthio, C.sub.2-C.sub.4alkenyl, haloC.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, haloC.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.4alkenoxy, haloC.sub.3-C.sub.4alkenoxy, C.sub.3-C.sub.4alkynoxy, haloC.sub.3-C.sub.4alkynoxy, C.sub.1-C.sub.4alkylamino, di(C.sub.1-C.sub.4alkyl)amino, C.sub.1-C.sub.4alkylaminocarbonyl, haloC.sub.1-C.sub.4alkylaminocarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, or C.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl; R.sub.2 is H, halogen, cyano, nitro, amino, carboxyl, CHO, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; R.sub.1, R.sub.2 and their conjoint pyrimidine ring can also form a five-membered ring, or six-membered ring which contains carbon atom, nitrogen atom, oxygen atom, or sulphur atom; X is NR.sub.3, O, or S; R.sub.3 is H, OH, CHO, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkylthio, C.sub.2-C.sub.4alkenylthio, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, haloC.sub.2-C.sub.4alkenyl, haloC.sub.2-C.sub.4alkynyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfinyl, haloC.sub.1-C.sub.4alkylsulfinyl, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4alkylaminosulfonyl, di(C.sub.1-C.sub.4alkyl)aminosulfonyl, C.sub.1-C.sub.4alkylsulfonylaminocarbonyl, C.sub.1-C.sub.4alkylcarbonylaminosulfonyl, C.sub.3-C.sub.4cycloalkyloxycarbonyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkylcarbonylC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonylC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylaminocarbonyl, di(C.sub.1-C.sub.4alkyl)aminocarbonyl, C.sub.2-C.sub.4alkenoxycarbonyl, C.sub.2-C.sub.4alkynoxycarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkylaminothio, di(C.sub.1-C.sub.4alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC.sub.1-C.sub.4alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC.sub.1-C.sub.4alkyloxycarbonyl, or (hetero)arylC.sub.1-C.sub.4alkyl by 1 to 5 following groups: halogen, nitro, cyano, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; R.sub.4 and R.sub.5 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; or R.sub.4, R.sub.5 and their conjoint carbon can also form a C.sub.3-C.sub.4 cycle; R.sub.6 and R.sub.7 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; or R.sub.6, R.sub.7 and their conjoint carbon can also form a C.sub.3-C.sub.4 cycle; m is selected from 0 to 3; R.sub.8 is H, cyano, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.9 is H, cyano, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.10 is C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonylC.sub.1-C.sub.4alkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.11 is halogen, OH, amino, cyano, nitro, C.sub.1C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1 -C.sub.4alkoxy, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkylamino, haloC.sub.1-C.sub.4alkylamino, di(C.sub.1-C.sub.4alkyl)amino, halodi(C.sub.1-C.sub.4alkyl)amino, C(═O)NR.sub.12R.sub.13, C.sub.1-C.sub.4alkylthio, haloC.sub.1-C.sub.4alkylthio, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, C.sub.2-C.sub.4alkenoxy, haloC.sub.2-C.sub.4alkenoxy, C.sub.2-C.sub.4alkynoxy, haloC.sub.2-C.sub.4alkynoxy, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonylC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkoxycarbonylC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthiocarbonylC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkylthiocarbonylC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylcarbonyloxy, haloC.sub.1-C.sub.4alkylcarbonyloxy, C.sub.1-C.sub.4alkoxycarbonyloxy, haloC.sub.1-C.sub.4alkoxycarbonyloxy, C.sub.1-C.sub.4alkylsulfonyloxy, haloC.sub.1-C.sub.4alkylsulfonyloxy, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkoxy; R.sub.12 and R.sub.13 may be the same or different and are each independently H, C.sub.1-C.sub.4alkyl, or haloC.sub.1-C.sub.4alkyl; W is H, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4alkylthio, or C.sub.1-C.sub.4alkylsulfonyl; and Y is O, the position of Y linked to pyrazole ring is from 3-position, 4-position, or 5-position; when Y is linked to 3-position of pyrazole, R.sub.8 is at the 4-position and R.sub.9 is at the 5-position, formula I is represented by formula I-1; when Y is linked to 4-position of pyrazole, R.sub.8 is at the 3-position and R.sub.9 is at the 5-position, formula I is represented by formula I-2; when Y is linked to 5-position of pyrazole, R.sub.8 is at the 3-position and R.sub.9 is at the 4-position, formula I is represented by formula I-3; ##STR00296##

4. A substituted pyrazole compound containing pyrimidinyl represented by formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-1J, I-1K, I-1L, I-1M, I-1N, I-2A, I-2B, I-2C, I-2D, I-2E, I-2F, I-2G, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-3G, I-4C, I-4F, I-4G, or a salt thereof: ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## wherein R.sub.1 is H, halogen, cyano, nitro, amino, carboxyl, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4alkylthio, haloC.sub.1-C.sub.4alkylthio, C.sub.1-C.sub.4alkylsulfinyl, C.sub.1-C.sub.4alkylsulfonyl, C.sub.2-C.sub.4alkenyl, haloC.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, haloC.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.4alkenoxy, haloC.sub.3-C.sub.4alkenoxy, C.sub.3-C.sub.4alkynoxy, haloC.sub.3-C.sub.4alkynoxy, C.sub.1-C.sub.4alkylamino, di(C.sub.1-C.sub.4alkyl)amino, C.sub.1-C.sub.4alkylaminocarbonyl, haloC.sub.1-C.sub.4alkylaminocarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, or C.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl; R.sub.2 is H, halogen, cyano, nitro, amino, carboxyl, CHO, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; R.sub.3 is H, OH, CHO, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkylthio, C.sub.2-C.sub.4alkenylthio, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, haloC.sub.2-C.sub.4alkenyl, haloC.sub.2-C.sub.4alkynyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfinyl, haloC.sub.1-C.sub.4alkylsulfinyl, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4alkylaminosulfonyl, di(C.sub.1-C.sub.4alkyl)aminosulfonyl, C.sub.1-C.sub.4alkylsulfonylaminocarbonyl, C.sub.1-C.sub.4alkylcarbonylaminosulfonyl, C.sub.3-C.sub.4cycloalkyloxycarbonyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkylcarbonylC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonylC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylaminocarbonyl, di(C.sub.1-C.sub.4alkyl)aminocarbonyl, C.sub.2-C.sub.4alkenoxycarbonyl, C.sub.2-C.sub.4alkynoxycarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkylaminothio, di(C.sub.1-C.sub.4alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC.sub.1-C.sub.4alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC.sub.1-C.sub.4alkyloxycarbonyl, or (hetero)arylC.sub.1-C.sub.4alkyl by 1 to 5 following groups: halogen, nitro, cyano, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; R.sub.4 and R.sub.5 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; or R.sub.4, R.sub.5 and their conjoint carbon can also form a C.sub.3-C.sub.4 cycle; R.sub.6 and R.sub.7 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; or R.sub.6, R.sub.7 and their conjoint carbon can also form a C.sub.3-C.sub.4 cycle; R.sub.8 is H, cyano, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.9 is H, cyano, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.11 is halogen, OH, amino, cyano, nitro, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkylamino, haloC.sub.1-C.sub.4alkylamino, di(C.sub.1-C.sub.4alkyl)amino, halodi(C.sub.1-C.sub.4alkyl)amino, C(═O)NR.sub.12R.sub.13, C.sub.1-C.sub.4alkylthio, haloC.sub.1-C.sub.4alkylthio, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, C.sub.2-C.sub.4alkenoxy, haloC.sub.2-C.sub.4alkenoxy, C.sub.2-C.sub.4alkynoxy, haloC.sub.2-C.sub.4alkynoxy, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkylthioC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonylC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkoxycarbonylC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthiocarbonylC.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkylthiocarbonylC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylcarbonyloxy, haloC.sub.1-C.sub.4alkylcarbonyloxy, C.sub.1-C.sub.4alkoxycarbonyloxy, haloC.sub.1-C.sub.4alkoxycarbonyloxy, C.sub.1-C.sub.4alkylsulfonyloxy, haloC.sub.1-C.sub.4alkylsulfonyloxy, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkoxy; n is an integer selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R.sub.11 may be the same or different; R.sub.12 and R.sub.13 may be the same or different and are each independently H, C.sub.1-C.sub.4alkyl, or haloC.sub.1-C.sub.4alkyl; R.sub.14 is C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4alkoxycarbonyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, or C.sub.1-C.sub.4alkoxycarbonylC.sub.1-C.sub.4alkyl; R.sub.15 and R.sub.16 may be the same or different and are each independently H, halogen, amino, cyano, nitro, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4alkylthio, haloC.sub.1-C.sub.4alkylthio, C.sub.3-C.sub.4cycloalkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.17, R.sub.18, R.sub.19, and R.sub.20 may be the same or different and are each independently H, halogen, cyano, nitro, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or haloC.sub.1-C.sub.4alkoxy; R.sub.21 and R.sub.22 may be the same or different and are each independently H, halogen, OH, cyano, nitro, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4alkylthio, haloC.sub.1-C.sub.4alkylthio, C.sub.3-C.sub.4cycloalkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.23, R.sub.24, R.sub.25, and R.sub.26 may be the same or different and are each independently H, halogen, OH, amino, cyano, nitro, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy or C.sub.3-C.sub.4cycloalkyl; R.sub.27 and R.sub.28 may be the same or different and are each independently H, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4alkylthio, haloC.sub.1-C.sub.4alkylthio, C.sub.3-C.sub.4cycloalkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.29 is C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.30 is H, cyano, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.31 is C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkylsulfonyl, haloC.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.32 is H, cyano, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.33 and R.sub.34 may be selected respectively from C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkylcarbonyl, haloC.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, haloC.sub.1-C.sub.4alkoxycarbonyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.35 and R.sub.36 may be selected respectively from H, cyano, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; and W is H, halogen, C.sub.1-C.sub.4alkyl, haloC.sub.1-C.sub.4alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4alkoxy, haloC.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4alkylsulfonyl; and wherein the salt is formed from a compound represented by formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-1J, I-1K, I-1L, I-1M, I-1N, I-2A, I-2B, I-2C, I-2D, I-2E, I-2F, I-2G, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-3G, I-4C, I-4F, or I-4G and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, fumaric acid, sorbic acid, malic acid, or citric acid.

5. The substituted pyrazole compound containing pyrimidinyl according to claim 4 having formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-1J, I-1K, I-1L, I-1M, I-1N, I-2A, I-2B, I-2C, I-2D, I-2E, I-2F, I-2G, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-3G, I-4C, I-4F, or I-4G, wherein R.sub.1 is H, F, Cl, Br, I, CN, NO.sub.2, NH.sub.2, carboxyl, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CH.sub.2F, CH.sub.2Cl, CHF.sub.2, CF.sub.3, CH.sub.2CF.sub.3, CH.sub.2OCH.sub.3, CH.sub.2OCH.sub.2CH.sub.3, or CH.sub.2OCH.sub.2CF.sub.3; R.sub.2 is H, F, Cl, Br, I, CN, NO.sub.2, NH.sub.2, carboxyl, CHO, CH.sub.3, C.sub.2H.sub.5, OCH.sub.3, OC.sub.2H.sub.5, or OCH.sub.2CF.sub.3; R.sub.3 is H, OH, CHO, COCH.sub.3, COC.sub.2H.sub.5, COC.sub.3H.sub.7, COCF.sub.3, COPh, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CH.sub.2CF.sub.3, OCH.sub.3, OC.sub.2H.sub.5, OCH.sub.2CF.sub.3, ##STR00303## SCH.sub.3, SC.sub.2H.sub.5, CH.sub.2CH═CH.sub.2, CH.sub.2C≡CH, SO.sub.2CH.sub.3, SO.sub.2CH.sub.2CH.sub.3, SO.sub.2CH.sub.2CF.sub.3, SO.sub.2NHCH.sub.3, SO.sub.2NHC.sub.2H.sub.5, SO.sub.2N(CH.sub.3).sub.2, SO.sub.2N(C.sub.2H.sub.5).sub.2, CONHSO.sub.2CH.sub.3, COOCH.sub.3, COOC.sub.2H.sub.5, COOC.sub.3H.sub.7-n, COOC.sub.3H.sub.7-i, CONHCH.sub.3, CON(CH.sub.3).sub.2, COOCH═CH.sub.2, COOC≡CH, SNHCH.sub.3, SNHC.sub.2H.sub.5, or SN(CH.sub.3).sub.2; R.sub.4 and R.sub.5 may be the same or different and are each independently H, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, OCH.sub.3, OC.sub.2H.sub.5, n-C.sub.3H.sub.7O, i-C.sub.3H.sub.7O, n-C.sub.4H.sub.9O, s-C.sub.4H.sub.9O, i-C.sub.4H.sub.9O, or t-C.sub.4H.sub.9O; R.sub.6 and R.sub.7 may be the same or different and are each independently H, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, OCH.sub.3, OC.sub.2H.sub.5, n-C.sub.3H.sub.7O, i-C.sub.3H.sub.7O, n-C.sub.4H.sub.9O, s-C.sub.4H.sub.9O, i-C.sub.4H.sub.9O, or t-C.sub.4H.sub.9O; R.sub.8 is H, CN, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, or CF.sub.3; R.sub.9 is H, CN, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, or CF.sub.3; R.sub.11 is F, Cl, Br, I, CN, NH.sub.2, NO.sub.2, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, OCH.sub.3, OCH.sub.2CH.sub.3, n-C.sub.3H.sub.7O, i-C.sub.3H.sub.7O, n-C.sub.4H.sub.9O, s-C.sub.4H.sub.9O, i-C.sub.4H.sub.9O, t-C.sub.4H.sub.9O, OCF.sub.3, OCH.sub.2CF.sub.3, COOCH.sub.3, COOC.sub.2H.sub.5, CONH.sub.2, CONHCH.sub.3, CONHC.sub.2H.sub.5, or CON(CH.sub.3).sub.2; n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R.sub.11 may be the same or different; R.sub.14 is CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, cyclopropyl, cyclobutyl, CH.sub.2F, CH.sub.2Cl, CHF.sub.2, CF.sub.3 or CH.sub.2CF.sub.3; R.sub.15 and R.sub.16 may be the same or different and are each independently H, F, Cl, Br, I, NH.sub.2, CN, NO.sub.2, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, CH.sub.2CF.sub.3, OCH.sub.3, OCH.sub.2CH.sub.3, n-C.sub.3H.sub.7O, i-C.sub.3H.sub.7O, n-C.sub.4H.sub.9O, s-C.sub.4H.sub.9O, i-C.sub.4H.sub.9O, t-C.sub.4H.sub.9O, OCF.sub.3, OCH.sub.2CF.sub.3, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.17, R.sub.18, R.sub.19, and R.sub.20 may be the same or different and are each independently H, F, Cl, Br, I, CN, NO.sub.2, CH.sub.3, CF.sub.3, OCH.sub.3, or OCF.sub.3; R.sub.21 and R.sub.22 may be the same or different and are each independently H, F, Cl, Br, I, OH, CN, NO.sub.2, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, CH.sub.2CF.sub.3, OCH.sub.3, OCH.sub.2CH.sub.3, n-C.sub.3H.sub.7O, i-C.sub.3H.sub.7O, n-C.sub.4H.sub.9O, s-C.sub.4H.sub.9O, i-C.sub.4H.sub.9O, t-C.sub.4H.sub.9O, OCF.sub.3, OCH.sub.2CF.sub.3, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.23, R.sub.24, R.sub.25, and R.sub.26 may be the same or different and are each independently H, F, Cl, Br, I, NH.sub.2, CN, NO.sub.2, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, OCH.sub.3, OCH.sub.2CH.sub.3, n-C.sub.3H.sub.7O, i-C.sub.3H.sub.7O, n-C.sub.4H.sub.9O, s-C.sub.4H.sub.9O, i-C.sub.4H.sub.9O, t-C.sub.4H.sub.9O, OCF.sub.3, or OCH.sub.2CF.sub.3; R.sub.27 and R.sub.28 may be the same or different and are each independently H, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, CH.sub.2CF.sub.3, OCH.sub.3, OCH.sub.2CH.sub.3, n-C.sub.3H.sub.7O, i-C.sub.3H.sub.7O, n-C.sub.4H.sub.9O, s-C.sub.4H.sub.9O, i-C.sub.4H.sub.9O, t-C.sub.4H.sub.9O, OCF.sub.3, OCH.sub.2CF.sub.3, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.29 is CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, cyclopropyl, SO.sub.2CH.sub.3, SO.sub.2CH.sub.2CH.sub.3, COCH.sub.3, COC.sub.2H.sub.5, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.30 is H, CN, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.31 is CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, cyclopropyl, SO.sub.2CH.sub.3, SO.sub.2CH.sub.2CH.sub.3, COCH.sub.3, COC.sub.2H.sub.5, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.32 is H, CN, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.33 and R.sub.34 may be selected respectively from CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, cyclopropyl, COCH.sub.3, COC.sub.2H.sub.5, COOCH.sub.3, COOC.sub.2H.sub.5, COOCH.sub.2CF.sub.3, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; R.sub.35 and R.sub.36 may be selected respectively from H, CN, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CF.sub.3, CCl.sub.3, CF.sub.2Cl, CFCl.sub.2, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, or (hetero)aryloxycarbonyl by 1 to 5 R.sub.11; and W is H, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, i-C.sub.3H.sub.7, n-C.sub.4H.sub.9, s-C.sub.4H.sub.9, i-C.sub.4H.sub.9, t-C.sub.4H.sub.9, CH.sub.2F, CH.sub.2Cl, CHF.sub.2, CF.sub.3, CH.sub.2CF.sub.3, OCH.sub.3, OC.sub.2H.sub.5, SCH.sub.3, SC.sub.2H.sub.5, SO.sub.2CH.sub.3, or SO.sub.2CH.sub.2CH.sub.3; and wherein the salt is formed from a compound represented by formula I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-1G, I-1H, I-1I, I-1J, I-1K, I-1L, I-1M, I-1N, I-2A, I-2B, I-2C, I-2D, I-2E, I-2F, I-2G, I-3A, I-3B, I-3C, I-3D, I-3E, I-3F, I-3G, I-4C, I-4F, or I-4G and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, fumaric acid, sorbic acid, malic acid, or citric acid.

6. The substituted pyrazole compound containing pyrimidinyl according to claim 5 having formula I-1C, I-1F, I-1G, I-2C, I-2F, I-2G, I-4C, I-4F, or I-4G, wherein R.sub.1 is H, F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, or CHF.sub.2; R.sub.2 is H, F, Cl, Br, I, NO.sub.2, NH.sub.2, CHO, CH.sub.3, C.sub.2H.sub.5, OCH.sub.3, or OC.sub.2H.sub.5; R.sub.3 is H, CH.sub.3, COCH.sub.3, COCF.sub.3, OCH.sub.3, SCH.sub.3, CH.sub.2CH═CH.sub.2, SO.sub.2CH.sub.3, SO.sub.2NHCH.sub.3, SO.sub.2N(CH.sub.3).sub.2, COOCH.sub.3, CONHCH.sub.3, CON(CH.sub.3).sub.2, SNHCH.sub.3, or SN(CH.sub.3).sub.2; R.sub.4 and R.sub.5 may be the same or different and are each independently H, F, Cl, Br, or CH.sub.3; R.sub.6 and R.sub.7 are H; R.sub.8 is H; R.sub.9 is H; R.sub.11 is F, Cl, Br, I, CN, NO.sub.2, CH.sub.3, CF.sub.3, OCH.sub.3, or OCF.sub.3; n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R.sub.11 may be the same or different; R.sub.23, R.sub.24, R.sub.25, and R.sub.26 may be the same or different and are each independently H, F, Cl, Br, I, or CH.sub.3; R.sub.27 and R.sub.28 may be the same or different and are each independently H, F, Cl, Br, or I; and W is H, F, Cl, Br, I, or CH.sub.3; and wherein the salt is formed from a compound represented by formula I-1C, I-1F, I-1G, I-2C, I-2F, I-2G, I-4C, I-4F or I-4G and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, fumaric acid, sorbic acid, malic acid, or citric acid.

7. The substituted pyrazole compound containing pyrimidinyl according to claim 5 having formula I-1C, I-1F, I-1G, I-2C, I-2G, I-4C, I-4F, or I-4G, wherein R.sub.1 is F, Cl, Br, I, CH.sub.3, C.sub.2H.sub.5, or CHF.sub.2; R.sub.2 is F, Cl, Br, I, NO.sub.2, NH.sub.2, CHO, CH.sub.3, or OCH.sub.3; R.sub.3 is H, CH.sub.3, COCH.sub.3, OCH.sub.3, CH.sub.2CH═CH.sub.2, SO.sub.2CH.sub.3, COOCH.sub.3, CONHCH.sub.3, CON(CH.sub.3).sub.2, or SN(CH.sub.3).sub.2; R.sub.4 and R.sub.5 may be the same or different and are each independently H or CH.sub.3; R.sub.6 and R.sub.7 are H; R.sub.8 is H; R.sub.9 is H; R.sub.11 is F, Cl, Br, I, CN, NO.sub.2, CH.sub.3, CF.sub.3, OCH.sub.3, or OCF.sub.3; n is selected from 1 to 5, when n is more than 1, R.sub.11 may be the same or different; R.sub.23, R.sub.24, R.sub.25, and R.sub.26 are H; R.sub.27 is H; R.sub.28 is Cl; and W is H, F, Cl, Br, or I; and wherein the salt is formed from a compound represented by formula I-1C, I-1F, I-1G, I-2C, I-2G, I-4C, I-4F or I-4G and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, fumaric acid, sorbic acid, malic acid, or citric acid.

8. A preparation method of the substituted pyrazole compound containing pyrimidinyl according to claim 3, wherein the preparation method of the formula I-1 is as follows: ##STR00304## the preparation method of the formula I-2 is as follows: ##STR00305## the preparation method of the formula I-3 is as follows: ##STR00306##

9. A composition comprising a compound according to claim 1.

10. A fungicide, insecticide, or acaricide composition comprising a compound according to claim 1 as an active ingredient and an acceptable carrier.

11. The fungicide, insecticide, or acaricide composition of claim 10, wherein the amount of the compound in the composition is 0.1-99 wt % of the total weight of the composition.

12. A method of making a fungicide, insecticide, or acaricide, the method comprising adding an amount of a compound according to claim 1 to a composition, wherein the amount of the compound in the composition is 0.1-99 wt % of the total weight of the composition.

13. A composition comprising a compound according to claim 4.

14. A fungicide, insecticide, or acaricide composition comprising a compound according to claim 4 as an active ingredient and an acceptable carrier.

15. The fungicide, insecticide, or acaricide composition of claim 14, wherein the amount of the compound in the composition is 0.1-99 wt % of the total weight of the composition.

16. A method of making a fungicide, insecticide, or acaricide, the method comprising adding an amount of a compound according to claim 4 to a composition, wherein the amount of the compound in the composition is 0.1-99 wt % of the total weight of the composition.

Description

DETAILED DESCRIPTION OF THE INVENTION

(1) The present invention is illustrated by the following examples, but without being restricted thereby. (All raw materials are commercially available unless otherwise specified.)

PREPARATION EXAMPLES

Example 1

The Preparation of Intermediate 4,5-dichloro-6-methylpyrimidine

(2) 1) The Preparation of 4-hydroxyl-5-chloro-6-methylpyrimidine

(3) ##STR00284##

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

(5) 2) The Preparation of Intermediate 4,5-dichloro-6-methylpyrimidine

(6) ##STR00285##

(7) 50 ml of POCl.sub.3 was added dropwise to a solution of 14.5 g (0.1 mol) of 4-hydroxyl-5-chloro-6-methylpyrimidine in 50 mL of toluene, the mixture was refluxed for 5-7 h after addition. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure to remove toluene and extra POCl.sub.3, and then poured into ice water. The water phase was extracted with ethyl acetate (3×50 mL), the organic phases were merged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:5, as an eluent) to give14.43 g as yellow liquid with yield of 88.5%.

Example 2

The Preparation of Intermediate 4,5-dichlorothieno[2,3-d]pyrimidine

(8) ##STR00286##

(9) To a solution of2-amino-4-oxo-4,5-dihydrothiophene-3-carbonitrile (70 g, 0.5 mol) dissolved in 250 mL phosphoryl trichloridein an ice-bath was added38 ml DMF for about 30 min, and reacted for 1 h at the room temperature, then heated to 75° C. for 3 h. After the reaction was over by Thin-Layer Chromatography monitoring, the mixture was cooled to the room temperature and poured into ice-water, the water phase was extracted with ethyl acetate (3×80 mL), the organic phases were merged, filtered to get 89.1 g 4,5-dichlorothieno[2,3-d]pyrimidine as dark-gray solid with yield of 86.9%, the m.p. is 160-161° C. .

Example 3

The Preparation of Intermediate 4-chloroquinazoline

(10) 1) The Preparation of Intermediate quinazolin-4(3H)-one

(11) ##STR00287##

(12) 2-aminobenzoic acid (13.7 g, 0.1 mol) and formamide20 ml were placed in a 250 ml three-necked flask, then heated to 140° C. and reacted for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over. 80 ml water was added under the stirring condition when the solution was cooled to 100° C., then cooled to the room temperature, filtered and washed the solid with anhydrous diethyl ether to get 10.96 g quinazolin-4(3H)-one as brown solid with yield of 75.1%.

(13) 2) The Preparation of Intermediate 4-chloroquinazoline

(14) ##STR00288##

(15) Quinazolin-4(3H)-one(14.6 g, 0.1 mol) was dissolved in 50 mL sulfuryl dichloride, and then heated to reflux for 4-6 h. After the reaction was over by Thin-Layer Chromatography monitoring, the mixture was poured into ice water and stirred for about 30 min, filtered and washed the solid with anhydrous diethyl ether to get 10.96 g 4-chloroquinazoline as brown solid with yield of 92.7%.

Example 4

The Preparation of Intermediate 2-(1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)ethanamine hydrochloride

(16) 1) The Preparation of N-Boc-2-bromoethylamine

(17) ##STR00289##

(18) To a solution of 2-bromoethylamine hydrobromide 20.5 g (0.1 mol) and sodium bicarbonate10.08 g (0.12 mol) in 80 mL tetrahydrofuran and 50 ml water was dropwise added di-tert-butyl dicarbonate21.80 g (0.1 mol) at room temperature, then the reaction mixture was continued stirring for 4-10 hrs, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. Then the mixture was poured into (3×50 mL) of ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure to obtain 21.84 g target intermediate as colourless oil with yield of 97.5%.

(19) 2) The Preparation of tert-butyl 2-(1-(2-chlorophenyl)-1H-pyrazol-3-yloxy)ethylcarbamate

(20) ##STR00290##

(21) To a solution of 2.24 g (0.01 mol) tert-butyl 2-bromoethylcarbamate and 1.94 g (0.01 mol) 1-(2-chlorophenyl)-1H-pyrazol-3-ol (refer to Organic Preparations and Procedures International, 34(1), 98-102; 2002) in 50 mL butanone was added 2.76 g (0.02 mol) potassium carbonate. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. then the mixture was poured into (3 ×50 mL) ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether=1:6, as an eluent) to obtain 2.73 g tert-butyl 2-(1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)ethylcarbamate as yellow solid with yield of 81.1%.

(22) 3) The Preparation of 2-(1-(2-chlorophenyl)-1H-pyrazol-3-yloxy)ethanamine hydrochloride

(23) ##STR00291##

(24) To a solution of tert-butyl 2-(1-(2-chlorophenyl)-1H-pyrazol-3-yloxy)ethylcarbamate 3.37 g (0.01 mol) in 50 mL ethyl acetate was dropwise added 6 mL concentrated hydrochloric acid. The solid was dissolved, the reaction mixture stir for4-5 hours,and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. Then the mixture was poured into 10 mL of dichloromethane to stir for half an hour and filtered to give 2.16 g target intermediate as white solid.

Example 5

The Preparation of the Compound 31-19

(25) ##STR00292##

(26) To a solution of 1.62 g (0.01 mol) 4,5-dichloro-6-methylpyrimidine and 2.74 g (0.01 mol) 2-(1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)ethanaminehydrochloride in 50 mL toluene was added 4.45 g (0.022 mol) triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. then the mixture was poured into (3×50 mL) ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether=1:4, as an eluent, boiling range 60-90° C.) to obtain 2.90 g compound 31-19 as white solid with yield of 79.9%.

(27) .sup.1H-NMR (300 MHz, internal standard: TMS, solvent: CDCl.sub.3) δ(ppm):2.44(3H, s), 3.90-3.98(2H, q), 4.48(2H, t), 5.93(1H, d), 5.94(1H, t), 7.37(2H, dd), 7.52(2H, dd), 7.71(1H, d), 8.39(1H,s).

Example 6

The Preparation of the Compound 40-17

(28) ##STR00293##

(29) To a solution of 1.64 g (0.01 mol) 4-chloroquinazoline and 2.74 g (0.01 mol) 2-(1-(2-chlorophenyl)-1H-pyrazol-3-yloxy)ethanaminehydrochloride in 50 mL toluene was added 4.45 g (0.022 mol) triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. then the mixture was poured into (3×50 mL) ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether=1:4, as an eluent, boiling range 60-90° C.) to obtain 2.61 g compound 40-17 as white solid with yield of 70.1%. m.p. 186.6° C.

(30) .sup.1H-NMR (300 MHz, internal standard: TMS, solvent: CDCl.sub.3) δ(ppm): 8.65(s, 1H, Quinazoline-3-H), 7.73(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.40-7.72 (m, 5H, Ph-3,4,5,6-5H), 7.40-7.72(m, 4H, Quinazoline-5,6,7,8-4H), 5.97(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.90(s, 1H, NH), 4.63(t, 2H, O—CH.sub.2), 4.06(m, 2H, N—CH.sub.2).

Example 7

The Preparation of the Compound 44-19

(31) ##STR00294##

(32) To a solution of 0.41 g (0.002 mol) 4,5-dichlorothieno[2,3-d]pyrimidine and 0.51 g (0.002 mol) 1-(1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)propan-2-amine in 50 mL toluene was added 0.45 g (0.011 mol) triethylamine. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. then the mixture was poured into (3×50 mL) ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether=1:4, as an eluent, boiling range 60-90° C.) to obtain 0.53 g compound 44-19 as white solid with yield of 63.7%.

(33) .sup.1H-NMR (300 MHz, internal standard: TMS, solvent: CDCl.sub.3) δ(ppm): 1.48(3H, d), 4.40-4.46(2H, m), 4.85(1H, q), 5.95(1H, d), 7.03(1H, d), 7.26(1H, s), 7.48(2H, d), 7.51(2H, d), 7.90(1H, d), 8.47(1H, s).

(34) Other compounds of the present invention were prepared according to the above examples.

(35) Physical properties and .sup.1HNMR spectrum (.sup.1HNMR, 300 MHz, internal standard: TMS, ppm) of some compounds of this invention are as follows:

(36) Compound 30-1-4: m.p. 152.9° C. δ(CDCl.sub.3) 8.29(s, 1H, Pyrimidine-H), 7.68(d, J=2.4 Hz, 1H, Pyrazole-5-H),7.51-7.56(m, 2H, Ph-2,6-2H), 7.08-7.15(m, 2H, Ph-3,5-2H), 5.91(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.56(s, 1H, NH), 4.49(t, 2H, O—CH.sub.2), 3.91-3.96(m, 2H, N—CH.sub.2), 2.05(s, 3H, CH.sub.3).

(37) Compound 30-1-19: m.p. 156.1° C. δ(CDCl.sub.3) 8.30(s, 1H, Pyrimidine-H), 7.72(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.52 (d, J=9 Hz, 2H, Ph-2,6-2H), 7.39(d, J=9 Hz, 2H, Ph-3,5-2H), 5.93(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.50(s, 1H, NH), 4.49(t, 2H, O—CH.sub.2), 3.94(m, 2H, N—CH.sub.2), 2.06(s,3H, CH.sub.3).

(38) Compound 30-1-21: m.p. 126.8° C. δ(CDCl.sub.3) 8.28(s, 1H, Pyrimidine-H), 7.73(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.49-7.51 (m, 2H, Ph-3,6-H), 7.34(d, 1H, Ph-5-H), 5.94(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.64(s, 1H, NH), 4.47(t, 2H, O—CH.sub.2), 3.93(m, 2H, N—CH.sub.2), 2.04(s,3H, CH.sub.3).

(39) Compound 30-1-25: m.p. 172.7° C. δ(CDCl.sub.3) 8.31(s, 1H, Pyrimidine-H), 7.73(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.50(d, 2H, Ph-2,6-2H), 7.20(s, 1H, Ph-4-H), 5.96(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.40(s, 1H, NH), 4.50(t, 2H, O—CH.sub.2), 3.94-3.98(m, 2H, N—CH.sub.2), 2.11(s, 3H, CH.sub.3).

(40) Compound 30-1-30: m.p. 175.9° C. δ(CDCl.sub.3) 8.27(s, 1H, Pyrimidine-H), 7.47(s, 2H, Ph-3,5-2H), 7.34(d, J=2.7 Hz, 1H, Pyrazole-5-H), 5.96(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.70(s, 1H, NH), 4.45(t, 2H, O—CH.sub.2), 3.88-3.92(m, 2H, N—CH.sub.2), 2.06(s, 3H, CH.sub.3).

(41) Compound 30-1-49: m.p. 170.8° C. δ(CDCl.sub.3) 8.31(s, 1H, Pyrimidine-H), 7.82(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.65-7.73(d, 4H, PhH),6.00(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.34(s, 1H, NH), 4.51(t, 2H, O—CH.sub.2), 3.93-3.99(m, 2H, N—CH.sub.2), 2.09(s, 3H, CH.sub.3).

(42) Compound 30-1-57: m.p. 137.8° C. δ(CDCl.sub.3) 8.29(s, 1H, Pyrimidine-H), 7.70(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.45(d, J=8.4 Hz, 2H, Ph-2,6-2H), 7.22(d, J=8.4 Hz, 2H, Ph-3,5-2H), 5.89(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.70(s, 1H, NH), 4.51(t, 2H, O—CH.sub.2), 3.90-3.95(m, 2H, N—CH.sub.2), 2.37(s, 3H, PhCH.sub.3), 2.03(s, 3H, CH.sub.3).

(43) Compound 30-1-78: oil. δ(CDCl.sub.3) 8.30(s, 1H, Pyrimidine-H), 7.68(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.51-7.60(m, 2H, Ph-2,6-2H),7.26-7.33(m, 2H, Ph-3,5-2H), 5.93(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.46(s, 1H, NH),4.49(t, 2H, O—CH.sub.2), 3.92-3.97(m, 2H, N—CH.sub.2), 2.07(s, 3H, CH.sub.3).

(44) Compound 30-2-19: m.p. 111.9° C. δ(CDCl.sub.3) 8.17(s, 1H, Pyrimidine-H), 7.72(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.53 (d, J=6.9 Hz, 2H, Ph-2,6-2H), 7.38(d, J=7.9 Hz, 2H, Ph-3,5-2H), 6.07(s, 1H, NH), 5.92(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.48(t, 2H, O—CH.sub.2), 3.92(m, 2H, N—CH.sub.2), 3.74(s,3H, CH.sub.3).

(45) Compound 30-3-19: oil. δ(CDCl.sub.3) 10.35(s, 1H, CHO), 8.45(s, 1H, Pyrimidine-H), 7.70(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.51 (d, J=9.3 Hz, 2H, Ph-2,6-2H), 7.37(d, J=9.3 Hz, 2H, Ph-3,5-2H), 6.00(s, 1H, NH), 5.93(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.48(t, 2H, O—CH.sub.2), 4.05(m, 2H, N—CH.sub.2).

(46) Compound 30-4-19: m.p. 143.7° C. δ(CDCl.sub.3) 8.30(s, 1H, Pyrimidine-H), 7.72(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.52 (d, J=8.7 Hz, 2H, Ph-2,6-2H), 7.38(d, J=8.7 Hz, 2H, Ph-3,5-2H), 6.29(s, 1H, NH), 5.93(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.50(t, 2H, O—CH.sub.2), 3.94(m, 2H, N—CH.sub.2).

(47) Compound 31-4: m.p. 139.2° C. δ(CDCl.sub.3) 8.38(s, 1H, Pyrimidine-H), 7.67(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.51-7.56(m, 2H, Ph-2,6-2H),7.07-7.13(m, 2H, Ph-3,5-2H), 6.01(s, 1H, NH), 5.91(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.48(t, 2H, O—CH.sub.2), 3.93-3.95(m, 2H, N—CH.sub.2), 2.43(s,3H, CH.sub.3).

(48) Compound 31-18: m.p. 146.7° C. δ(CDCl.sub.3) 8.39(s, 1H, Pyrimidine-H), 7.73(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.63 (s, 1H, Ph-2-H), 7.43(d, 1H, Ph-6-H), 7.33(t, 1H, Ph-5-H), 7.19(d, 1H, Ph-4-H), 5.96(s, 1H, NH), 5.94(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.50(t, 2H, O—CH.sub.2), 3.95(m, 2H, N—CH.sub.2), 2.44(s,3H, CH.sub.3).

(49) Compound 31-21: m.p. 155.6° C. δ(CDCl.sub.3) 8.37(s, 1H, Pyrimidine-H), 7.73(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.53 (s, 1H, Ph-3-H), 7.50(d, J=1.8 Hz, 1H, Ph-6-H), 7.34(d, J=1.8 Hz, 1H, Ph-5-H), 6.09(s, 1H, NH), 5.94(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.46(t, 2H, O—CH.sub.2), 3.93(m, 2H, N—CH.sub.2), 2.44(s,3H, CH.sub.3).

(50) Compound 31-23: oil. δ(CDCl.sub.3) 8.37(s, 1H, Pyrimidine-H), 7.31-7.46(m, 4H, Pyrazole-5-H, PhH), 6.12(s, 1H, NH), 5.96(d, 1H, Pyrazole-4-H), 4.45(t, 2H, O—CH.sub.2), 3.89-3.95(m, 2H, N—CH.sub.2), 2.45(s, 3H, CH.sub.3).

(51) Compound 31-25: m.p. 144.1° C. δ(CDCl.sub.3) 8.40(s, 1H, Pyrimidine-H), 7.71(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.49-7.51(m, 2H, Ph-2,6-2H), 7.18(s, 1H, Ph-4-H),5.96(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.92(s, 1H, NH),4.49(t, 2H, O—CH.sub.2), 3.94-3.96(m, 2H, N—CH.sub.2), 2.45(s, 3H, CH.sub.3).

(52) Compound 31-30: oil. δ(CDCl.sub.3) 8.37(s, 1H, Pyrimidine-H), 7.46(s, 2H, Ph-3,5-2H), 7.33(d, J=2.4 Hz, 1H, Pyrazole-5-H), 6.06(s, 1H, NH), 5.96(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.43(t, 2H, O—CH.sub.2), 3.89-3.95(m, 2H, N—CH.sub.2), 2.46(s, 3H, CH.sub.3).

(53) Compound 31-49: m.p. 187.0° C. δ(CDCl.sub.3) 8.39(s, 1H, Pyrimidine-H), 7.80(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.69(s, 4H, PhH), 6.00(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.91(s, 1H, NH), 4.50(t, 2H, O—CH.sub.2), 3.92-3.98(m, 2H, N—CH.sub.2), 2.44(s, 3H, CH.sub.3).

(54) Compound 31-57: m.p. 127.3° C. δ(CDCl.sub.3) 8.38(s, 1H, Pyrimidine-H), 7.69(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.46 (d, J=8.7 Hz, 2H, Ph-2,6-2H), 7.19(d, J=8.7 Hz, 2H, Ph-3,5-2H), 6.04(s, 1H, NH), 5.89(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.48(t, 2H, O—CH.sub.2), 3.91-3.96(m, 2H, N—CH.sub.2), 2.43(s, 3H, CH.sub.3), 2.36(s, 3H, PhCH.sub.3).

(55) Compound 31-69: m.p. 171.0° C. δ(CDCl.sub.3) 8.39(s, 1H, Pyrimidine-H), 7.81(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.62-7.70 (m, 4H, Ph-2,3,5,6-4H), 5.98(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.95(s, 1H, NH), 4.50(t, 2H, O—CH.sub.2), 3.96(m, 2H, N—CH.sub.2), 2.43(s,3H, CH.sub.3).

(56) Compound 31-78: m.p. 134.7° C. δ(CDCl.sub.3) 8.39(s, 1H, Pyrimidine-H), 7.72(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.58-7.62(m, 2H, Ph-2,6-2H),7.26-7.29(m, 2H, Ph-3,5-2H), 5.96(s, 1H, NH)5.94(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.49(t, 2H, O—CH.sub.2), 3.92-3.98(m, 2H, N—CH.sub.2), 2.44(s, 3H, CH.sub.3).

(57) Compound 32-1: m.p. 92.2° C. δ(CDCl.sub.3) 8.43(s, 1H, Pyrimidine-H), 7.75(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.59 (d, J=8.4 Hz, 2H, Ph-2,6-2H), 7.41(m, 2H, Ph-3,5-2H), 7.22(m, 1H, Ph-4-H), 6.05(s, 1H, NH), 5.92(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.50(t, 2H, O—CH.sub.2), 3.95(m, 2H, N—CH.sub.2), 2.76(m, 2H, CH.sub.2), 1.24(t,3H, CH.sub.3).

(58) Compound 32-4: m.p. 123.9° C. δ(CDCl.sub.3) 8.43(s, 1H, Pyrimidine-H), 7.67(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.51-7.56 (m, 2H, Ph-2,6-2H), 7.07-7.13(m, 2H, Ph-3,5-2H), 6.01(s, 1H, NH), 5.91(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.78(t, 2H, O—CH.sub.2), 3.91-3.96(m, 2H, N—CH.sub.2), 2.73-2.80(m, 2H, CH.sub.2), 1.24(t,3H, CH.sub.3).

(59) Compound 32-17: m.p. 75.4° C. δ(CDCl.sub.3) 8.42(s, 1H, Pyrimidine-H), 7.74(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.57 (d, 1H, Ph-6-H), 7.48(d, J=1.5 Hz, 1H, Ph-3-H), 7.26-7.36(m, 2H, Ph-4,5-2H), 6.09(s, 1H, NH), 5.94(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.47(t, 2H, O—CH.sub.2), 3.93(m, 2H, N—CH.sub.2), 2.77(m, 2H, CH.sub.2), 1.25(t,3H, CH.sub.3).

(60) Compound 32-18: m.p. 100.9° C. δ(CDCl.sub.3) 8.44(s, 1H, Pyrimidine-H), 7.73(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.64 (s, 1H, Ph-2-H), 7.45(d, 1H, Ph-6-H), 7.33(t, 1H, Ph-5-H), 7.18(d, 1H, Ph-4-H), 5.99(s, 1H, NH), 5.94(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.49(t, 2H, O—CH.sub.2), 3.95(m, 2H, N—CH.sub.2), 2.77(m, 2H, CH.sub.2), 1.27(t,3H, CH.sub.3).

(61) Compound 32-19:m.p. 138.6° C. δ(CDCl.sup.3) 1.24(3H, t), 2.71-2.82(2H, q), 3.90-3.98(2H, q), 4.49(2H, t), 5.93(1H, d), 6.01(1H, t), 7.37(2H, d), 7.53(2H, d), 7.72(1H, d), 8.44(1H, s).

(62) Compound 32-21: m.p. 97.6° C. δ(CDCl.sub.3) 8.41(s, 1H, Pyrimidine-H), 7.73(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.51 (s, 1H, Ph-3-H), 7.49(d, 1H, Ph-6-H), 7.28(d, 1H, Ph-5-H), 6.09(s, 1H, NH), 5.95(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.46(t, 2H, O—CH.sub.2), 3.94(m, 2H, N—CH.sub.2), 2.76(m, 2H, CH.sub.2), 1.25(t,3H, CH.sub.3).

(63) Compound 32-23: oil. δ(CDCl.sub.3) 8.41(s, 1H, Pyrimidine-H), 7.27-7.46(m, 4H, Pyrazole-5-H, PhH), 6.12(s, 1H, NH), 5.96(d, 1H, Pyrazole-4-H), 4.45(t, 2H, O—CH.sub.2), 3.90-3.95(m, 2H, N—CH.sub.2), 2.73-2.82(m, 2H, CH.sub.2), 1.22-1.28(m, 3H, CH.sub.3).

(64) Compound 32-25: m.p. 104.9° C. δ(CDCl.sub.3) 8.46(s, 1H, Pyrimidine-H), 7.71(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.49(s, 2H, Ph-2,6-2H), 7.17(s, 1H, Ph-4-H), 5.98(s, 1H, NH), 5.96(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.49(t, 2H, O—CH.sub.2), 3.93-3.96(m, 2H, N—CH.sub.2), 2.77-2.80(m, 2H, CH.sub.2), 1.25(t, 3H, CH.sub.3).

(65) Compound 32-30: oil. δ(CDCl.sub.3) 8.42(s, 1H, Pyrimidine-H), 7.46(s, 2H, Ph-3,5-2H), 7.33(d, J=2.4 Hz, 1H, Pyrazole-5-H), 6.05(s, 1H, NH), 5.96(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.43(t, 2H, O—CH.sub.2), 3.89-3.95(m, 2H, N—CH.sub.2), 2.74-2.82(m, 2H, CH.sub.2), 1.26(t, 3H, CH.sub.3).

(66) Compound 32-49: m.p. 145.1° C. δ(CDCl.sub.3) 8.44(s, 1H, Pyrimidine-H), 7.80(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.69(s, 4H, PhH), 6.00(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.91(s, 1H, NH), 4.51(t, 2H, O—CH.sub.2), 3.93-3.98(m, 2H, N—CH.sub.2), 2.72-2.78(m,2H, CH.sub.2), 1.21-1.28(m,3H, CH.sub.3).

(67) Compound 32-57: m.p. 112.5° C. δ(CDCl.sub.3) 8.43(s, 1H, Pyrimidine-H), 7.69(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.46 (d, J=8.7 Hz, 2H, Ph-2,6-2H), 7.19(d, J=8.7 Hz, 2H, Ph-3,5-2H), 6.04(s, 1H, NH), 5.89(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.48(t, 2H, O—CH.sub.2), 3.91-3.97(m, 2H, N—CH.sub.2), 2.72-2.80(m,2H, CH.sub.2), 2.36(s, 3H, CH.sub.3), 1.24(t,3H, CH.sub.3).

(68) Compound 32-69: m.p. 119.9° C. δ(CDCl.sub.3) 8.44(s, 1H, Pyrimidine-H), 7.81(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.64-7.68 (m, 4H, Ph-2,3,5,6-4H), 5.98(d, J=2.4 Hz, 1H, Pyrazole-4-H), 5.95(s, 1H, NH), 4.51(t, 2H, O—CH.sub.2), 3.96(m, 2H, N—CH.sub.2), 2.77(m, 2H, CH.sub.2), 1.24(t,3H, CH.sub.3).

(69) Compound 32-78: m.p. 102.1° C. δ(CDCl.sub.3) 8.45(s, 1H, Pyrimidine-H), 7.66(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.52-7.62(m, 2H, Ph-2,6-2H),7.28-7.33(m, 2H, Ph-3,5-2H), 5.98(s, 1H, NH), 5.94(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.49(t, 2H, O—CH.sub.2), 3.94-3.96(m, 2H, N—CH.sub.2), 2.75-2.78(m, 2H, CH.sub.2), 1.24(t, 3H, CH.sub.3).

(70) Compound 33-1: m.p. 73.6° C. δ(CDCl.sub.3) 8.23(s, 1H, Pyrimidine-H), 7.75(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.59 (d, J=8.4 Hz, 2H, Ph-2,6-2H), 7.42(m, 2H, Ph-3,5-2H), 7.23(m, 1H, Ph-4-H), 6.70(t,1H, CHF.sub.2), 6.22(s, 1H, NH), 5.90(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.36(t, 2H, O—CH.sub.2), 3.75(m, 2H, N—CH.sub.2).

(71) Compound 33-4: m.p. 115.2° C. δ(CDCl.sub.3) 8.56(s, 1H, Pyrimidine-H), 7.67(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.51-7.56(m, 2H, Ph-2,6-2H), 7.07-7.14(m, Ph-3,5-2H), 6.69(t, J=5 3.4 Hz, 1H, CF.sub.2H), 6.43(s, 1H, NH), 5.91(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.52(t, 2H, O—CH.sub.2), 3.95-4.01(m, 2H, N—CH.sub.2).

(72) Compound 33-18: m.p. 99.3° C. δ(CDCl.sub.3) 8.56(s, 1H, Pyrimidine-H), 7.74(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.64 (s, 1H, Ph-2-H), 7.44(d, 1H, Ph-6-H), 7.33(t, 1H, Ph-5-H), 7.18(d, 1H, Ph-4-H), 6.70(t, 1H, CHF.sub.2), 6.37(s, 1H, NH), 5.94(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.53(t, 2H, O—CH.sub.2), 3.99(m, 2H, N—CH.sub.2).

(73) Compound 33-19:m.p. 142.8° C. δ(CDCl.sub.3) 4.00-4.05(2H, q), 4.56(2H, t), 5.96(1H, s), 6.50(1H, s), 6.75(1H, t), 7.40(2H, d), 7.51(2H, d), 7.75(1H, s), 8.60(1H, s).

(74) Compound 33-21: m.p. 136.5° C. δ(CDCl.sub.3) 8.55(s, 1H, Pyrimidine-H), 7.72(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.51 (s, 1H, Ph-3-H), 7.49(d, 1H, Ph-6-H), 7.35(d, 1H, Ph-5-H), 6.70(t,1H, CHF.sub.2), 6.39(s, 1H, NH), 5.94(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.49(t, 2H, O—CH.sub.2), 3.97(m, 2H, N—CH.sub.2).

(75) Compound 33-25: m.p. 126.5° C. δ(CDCl.sub.3) 8.58(s, 1H, Pyrimidine-H), 7.72(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.49-7.51(m,2H, Ph-2,6-2H), 7.19(d,1H, Ph-4-H), 6.72(t, J=53.40 Hz, 1H, CF.sub.2H), 6.30(s, 1H, NH), 5.96(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.53(t, 2H, O—CH.sub.2), 3.97-4.03(m, 2H, N—CH.sub.2).

(76) Compound 33-30: m.p. 132.9° C. δ(CDCl.sub.3) 8.54(s, 1H, Pyrimidine-H), 7.47(s,2H, Ph-3,5-2H), 7.34(d, J=2.4 Hz, 1H, Pyrazole-5-H), 6.73(t, J=53.7 Hz, 1H, CF.sub.2H), 6.52(s, 1H, NH)5.96(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.46(t, 2H.sub.2O—CH.sub.2), 3.94-3.99(m, 2H, N—CH.sub.2).

(77) Compound 33-49: m.p. 151.7° C. δ(CDCl.sub.3) 8.57(s, 1H, Pyrimidine-H), 7.82(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.70(s,4H, PhH), 6.70(t, J=53.70 Hz, 1H, CF.sub.2H), 6.52(s, 1H, NH), 6.01(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.54(t, 2H, O—CH.sub.2), 3.98-4.03(m, 2H, N—CH.sub.2).

(78) Compound 33-57: m.p. 106.6° C. δ(CDCl.sub.3) 8.56(s, 1H, Pyrimidine-H), 7.71(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.46(d, J=8.4 Hz, 2H, Ph-2,6-2H), 7.21(d, J=8.4 Hz, 2H, Ph-3,5-2H), 6.69(t, J=54.00 Hz, 1H, CF.sub.2H), 6.52(s, 1H, NH), 5.89(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.53(t, 2H, O—CH.sub.2), 3.95-4.00(m, 2H, N—CH.sub.2), 2.37(s, 3H, CH.sub.3).

(79) Compound 33-69: m.p. 122.3° C. δ(CDCl.sub.3) 8.57(s, 1H, Pyrimidine-H), 7.81(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.01-7.64 (m, 4H, Ph-2,3,5,6-4H), 6.70(t,1H, CHF.sub.2), 6.31(s, 1H, NH), 5.98(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.54(t, 2H, O—CH.sub.2), 4.00(m, 2H, N—CH.sub.2).

(80) Compound 35-19:δ(CDCl.sub.3) 1.42(3H, d), 4.38(2H, d), 4.65(1H, s), 5.93(1H, d), 6.06-6.08(1H, m), 7.38(2H, d), 7.51(2H, d), 7.71(1H, d), 8.28(1H,s).

(81) Compound 36-19:m.p. 80-82° C. δ(CDCl.sub.3) 1.42(3H, d), 2.42(3H, s), 4.37(2H, d), 4.65-4.67(1H, m), 5.91(1H, s), 5.93(1H, d), 7.36(2H, d), 7.53(2H, d), 7.70(1H, d), 8.40(1H, s).

(82) Compound 37-19:δ(CDCl.sub.3) 1.24(3H, t), 1.42(3H, d), 2.73-2.77(2H, q), 4.37(2H, d), 4.39(1H, s), 5.78-5.82(1H, m), 5.93(1H, d), 7.38(2H, d), 7.52(2H, d), 7.70(1H, d), 8.43(1H,s).

(83) Compound 40-1: oil. δ(CDCl.sub.3) 8.66(s, 1H, Quinazoline-3-H), 7.76(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.72-7.75 (m, 5H, Ph-2,3,4,5,6-5H), 7.72-7.75 (m, 4H, Quinazoline-5,6,7,8-4H), 6.22(s, 1H, NH), 5.90(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.36(t, 2H, O—CH.sub.2), 3.75(m, 2H, N—CH.sub.2).

(84) Compound 40-4: m.p. 155.7° C. δ(CDCl.sub.3) 8.67(s, 1H, Quinazoline-3-H), 7.82(d, 1H, Quinazoline-6-H), 7.67(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.53-7.65(m, 4H, Ph-2,6-2H, Quinazoline-7,8-H), 7.10-7.19(m, 3H, Ph-3,5-2H, Quinazoline-9-H), 6.95(s, 1H, NH), 5.94(d, J=2.7 Hz, 1H, ═CH), 4.62(t, 2H, CH.sub.2), 4.05-4.10(m, 2H, CH.sub.2).

(85) Compound 40-18:m.p. 146.1° C. δ(CDCl.sub.3) 8.68(s, 1H, Quinazoline-3-H), 7.74(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.63-7.71 (m, 4H, Ph-2, 4,5,6-4H), 7.31-7.54 (m, 4H, Quinazoline-5,6,7,8-4H), 6.78(s, 1H, NH), 5.96(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.63(t, 2H, O—CH.sub.2), 4.10(m, 2H, N—CH.sub.2).

(86) Compound 40-19: m.p. 176.4° C. δ(CDCl.sub.3) 4.10-4.15(2H, q), 4.67(2H, t),5.99(1H, s), 7.11(1H, s), 7.44(2H, d), 7.58(2H, d), 7.66(1H, d), 7.71-7.76(2H, d), 7.90(1H, d), 8.70(1H, s).

(87) Compound 40-21: m.p. 141.7° C. δ(CDCl.sub.3) 8.66(s, 1H, Quinazoline-3-H), 7.72(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.80-7.83 (m, 3H, Ph-3,5,6-3H), 7.51-7.58 (m, 4H, Quinazoline-5,6,7,8-4H), 6.90(s, 1H, NH), 5.97(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.59(t, 2H, O—CH.sub.2), 4.08(m, 2H, N—CH.sub.2).

(88) Compound 40-25: m.p. 199.9° C. δ(CDCl.sub.3) 8.69(s, 1H, Quinazoline-3-H), 7.83(d,1H, Quinazoline-6-H),7.73(d, J=3.0 Hz, 1H, Pyrazole-5-H), 7.65-7.66(m, 2H, Quinazoline-7,8-H), 7.51-7.52(m, 2H, Ph-2,6-2H), 7.30-7.36(m, 1H, Quinazoline-7,8-H), 7.21-7.22(m, 1H, Ph-4-H), 6.56(s, 1H, NH), 5.99(d, J=3.0 Hz, 1H, Pyrazole-4-H), 4.62(t, 2H.sub.2O—CH.sub.2), 4.09-4.14(m, 2H, N—CH.sub.2).

(89) Compound 40-30: m.p. 170.5° C. δ(CDCl.sub.3) 8.66(s, 1H, Quinazoline-3-H), 7.52-7.84(m, 3H, Quinazoline-6,7,9-3H), 7.46(s, 2H, Ph-3,5-2H), 7.35(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.24(t, 1H, Quinazoline-8-1H), 5.99(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.57(t, 2H, O—CH.sub.2), 4.04-4.09(m, 2H, N—CH.sub.2).

(90) Compound 40-49:oil. δ(CDCl.sub.3) 8.68(s, 1H, Quinazoline-3-H), 7.83(d, 1H, Quinazoline-6-H), 7.81(d, J=3.0 Hz, 1H, Pyrazole-5-H), 7.64-7.76(m, 5H, Quinazoline-7,8,9-H, Ph-2,6-2H), 7.31(d, 2H, Ph-3,5-2H), 6.47(s, 1H, NH), 6.02(d, J=3.0 Hz, 1H, Pyrazole-4-H), 4.62(t, 2H, O—CH.sub.2), 4.09-4.15(m, 2H, N—CH.sub.2).

(91) Compound 40-57: m.p. 178.7° C. δ(CDCl.sub.3) 8.66(s, 1H, Quinazoline-3-H), 7.78(d, 1H, Quinazoline-6-H), 7.70(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.58-7.67(m, 3H, Quinazoline-7,8,9-H), 7.50(d, J=8.4 Hz, 2H, Ph-2,6-2H), 7.10(d, J=8.4 Hz, 2H, Ph-3,5-2H), 5.92(d, J=2.4 Hz, 1H, Pyrazole-4-H),4.64(t, 2H, O—CH.sub.2), 4.05-4.10(m, 2H, N—CH.sub.2), 2.40(s, 3H, CH.sub.3).

(92) Compound 40-69: m.p. 170.1° C. δ(CDCl.sub.3) 8.68(s, 1H, Quinazoline-3-H), 7.81(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.62-7.71 (m, 4H, Ph-2,3,5,6-4H), 7.62-7.71 (m, 4H, Quinazoline-5,6,7,8-4H), 6.62(s, 1H, NH), 6.00(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.64(t, 2H, O—CH.sub.2), 4.11(m, 2H, N—CH.sub.2).

(93) Compound 42-1: m.p. 129.7° C. δ(CDCl.sub.3) 8.48(s, 1H, Pyrimidine-H), 7.74(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.57 (d, J=8.4 Hz, 2H, Ph-2,6-2H), 7.40(m, 2H, Ph-3,5-2H), 7.19(m, 1H, Ph-4-H), 7.03(s,1H, Thieno-H), 6.98(s, 1H, NH), 5.92(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.55(t, 2H, O—CH.sub.2), 4.08(m, 2H, N—CH.sub.2).

(94) Compound 42-4: m.p. 132.2° C. δ(CDCl.sub.3) 8.48(s, 1H, Pyrimidine-H), 7.67(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.49-7.55(m, 2H, Ph-2,6-2H), 7.04-7.13(m, 2H, Ph-3,5-2H), 6.97(s, 1H, Thiophene-H), 6.92(s, 1H, NH), 5.92(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.53(t, 2H, O—CH.sub.2), 4.04-4.10(m, 2H, N—CH.sub.2).

(95) Compound 42-17: m.p. 122.4° C. δ(CDCl.sub.3) 8.47(s, 1H, Pyrimidine-H), 7.74(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.54 (d, J=7.5 Hz, 1H, Ph-6-H), 7.48(d, J=7.5 Hz, 1H, Ph-3-H), 7.31-7.36(m, 2H, Ph-4,5-2H), 7.05(s,1H, Thieno-H), 7.01(s, 1H, NH), 5.94(d, J=2.1 Hz, 1H, Pyrazole-4-H), 4.53(t, 2H, O—CH.sub.2), 4.07(m, 2H, N—CH.sub.2).

(96) Compound 42-18: m.p. 100.1° C. δ(CDCl.sub.3) 8.48(s, 1H, Pyrimidine-H), 7.72(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.61 (s, 1H, Ph-2-H), 7.43(d, 1H, Ph-6-H), 7.31(t, 1H, Ph-5-H), 7.17(d, 1H, Ph-4-H), 7.04(s,1H, Thieno-H), 6.95(s, 1H, NH), 5.94(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.55(t, 2H, O—CH.sub.2), 4.08(m, 2H, N—CH.sub.2).

(97) Compound 42-21:m.p. 123.1° C. δ(CDCl.sub.3) 8.47(s, 1H, Pyrimidine-H), 7.73(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.48-7.51 (m, 2H, Ph-3,6-2H), 7.32(d, 1H, Ph-5-H), 7.05(s,1H, Thieno-H), 6.97(s, 1H, NH), 5.94(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.51(t, 2H, O—CH.sub.2), 4.06(m, 2H, N—CH.sub.2).

(98) Compound 42-25:oil. δ(CDCl.sub.3) 8.49(s, 1H, Pyrimidine-H), 7.71(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.43-7.49(m, 2H, Ph-2,6-2H), 7.14-7.19(m, 1H, Ph-4-H), 7.06(s, 1H, Thiophene-H), 6.94(s, 1H, NH), 5.96(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.55(t, 2H, O—CH.sub.2), 4.05-4.11(m, 2H, N—CH.sub.2).

(99) Compound 42-30: oil. δ(CDCl.sub.3) 8.46(s, 1H, Pyrimidine-H), 7.45(s, 2H, Ph-3,5-2H), 7.32(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.06(s, 1H, Thiophene-H), 6.98(s, 1H, NH), 5.96(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.47(t, 2H, O—CH.sub.2), 4.04-4.07(m, 2H, N—CH.sub.2).

(100) Compound 42-49: m.p. 164.9° C. δ(CDCl.sub.3) 8.49(s, 1H, Pyrimidine-H), 7.80(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.63-7.67(m, 4H, PhH), 7.04(s, 1H, Thiophene-H), 6.90(s, 1H, NH), 6.01(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.57(t, 2H, O—CH.sub.2), 4.07-4.10(m, 2H, N—CH.sub.2).

(101) Compound 42-57: m.p. 113.4° C. δ(CDCl.sub.3) 8.48(s, 1H, Pyrimidine-H), 7.68(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.44(d, J=8.4 Hz, 2H, Ph-2,6-2H), 7.19(d, J=8.4 Hz, 2H, Ph-3,5-2H), 7.03(s, 1H, Thiophene-H), 6.03(s, 1H, NH), 5.89(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.54(t, 2H, O—CH.sub.2), 4.04-4.10(m, 2H, N—CH.sub.2), 2.36(s, 3H, CH.sub.3).

(102) Compound 42-69: m.p. 149.7° C. δ(CDCl.sub.3) 8.48(s, 1H, Pyrimidine-H), 7.79(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.65 (m, 4H, Ph-2,3,5,6-4H), 7.03(s,1H, Thieno-H), 6.92(s, 1H, NH), 5.98(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.57(t, 2H, O—CH.sub.2), 4.09(m, 2H, N—CH.sub.2).

(103) Compound 42-78: oil. δ(CDCl.sub.3) 8.49(s, 1H, Pyrimidine-H), 7.96(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.71-7.74(m, 2H, Ph-2,6-2H),7.29-7.33(m, 2H, Ph-3,5-2H), 7.16(s, 1H, Thiophene-H), 6.96(s, 1H, NH), 5.94(d, J=2.4 Hz, 1H, Pyrazole-4-H), 4.55(t, 2H, O—CH.sub.2), 4.07-4.09(m, 2H, N—CH.sub.2).

(104) Compound 57-4:δ(CDCl.sub.3) 2.47(3H, s), 3.92(2H, d), 4.14(2H, t), 5.78(1H, s), 7.13(2H, t), 7.55(1H, s), 7.56-7.59(3H, m), 8.39(1H, s).

(105) Compound 57-19: m.p. 130.0° C. δ(CDCl.sub.3):8.41(s,1H, Pyrimidine-H), 7.58(s,1H, Pyrazole-5-H),7.56(d, J=9.0 Hz, 2H, Ph-2,6-2H), 7.50(s,1H, Pyrazole-3-H),7.40(d, J=9.0 Hz, 2H, Ph-3,5-2H), 5.85(s, 1H, NH), 4.14(t, 2H, O—CH.sub.2),3.95-3.90(m, 2H, N—CH.sub.2), 2.46(t, 3H, CH.sub.3).

(106) Compound 58-19: m.p. 134.7° C. δ(CDCl.sub.3):8.45(s,1H, Pyrimidine-H), 7.60(s,1H, Pyrazole-5-H),7.56(d, J=9.0 Hz, 2H, Ph-2,6-2H), 7.50(s,1H, Pyrazole-3-H),7.40(d, J=9. 0 Hz, 2H, Ph-3,5-2H), 5.82(s, 1H, NH), 4.15(t, 2H, O—CH.sub.2),3.95-3.90(m, 2H, N—CH.sub.2),2.84-2.77(m, 2H, CH.sub.2),1.27(t, 3H, CH.sub.3).

(107) Compound 59-19: m.p. 125.7° C. δ(CDCl.sub.3):8.58(s,1H, Pyrimidine-H), 7.58(s,1H, Pyrazole-5-H),7.56(d, J=9.0 Hz, 2H, Ph-2,6-2H), 7.50(s,1H, Pyrazole-3-H),7.40(d, J=9.0 Hz, 2H, Ph-3,5-2H),6.74(t, J=54 Hz, 1H, CF.sub.2H), 6.08(s, 1H, NH), 4.16(t, 2H, O—CH.sub.2), 4.01-3.96(m, 2H, N—CH.sub.2).

(108) Compound 68-19: m.p. 119.2° C. δ(CDCl.sub.3):8.49(s, 1H, Pyrimidine-H), 7.60(s, 1H, Pyrazole-5-H), 7.55(d, J=8.7 Hz, 2H, Ph-2,6-2H), 7.51(s, 1H, Pyrazole-3-H), 7.39(d, J=8.7 Hz, 2H, Ph-3,5-2H), 7.01(s, 1H, Thiophene-H), 6.97(s, 1H, NH), 4.22(t, 2H, O—CH.sub.2), 4.07-4.02(m, 2H, N—CH.sub.2).

(109) Compound 59-21: oil.δ(CDCl.sub.3) 8.54(s, 1H, Pyrimidine-H), 8.01(s,1H, Ph-3-H),7.57(s, 1H, Pyrazole-5-H), 7.49-7.52(m, 2H, Ph-6-H, Pyrazole-3-H), 7.35(dd, 1H, Ph-5-H), 6.73(t, J=53.7 Hz, 1H, CF.sub.2H), 6.25(s, 1H, NH), 4.11(t, 2H, O—CH.sub.2), 3.75-3.81(m, 2H, N—CH.sub.2), 2.13-2.18(m, 2H, CH.sub.2).

(110) Compound 68-4:δ(CDCl.sub.3) 4.03-4.04(2H, q), 4.20(2H, t), 7.10(1H, s), 7.12-7.15(2H, m), 7.25(1H, d), 7.52-7.58(4H, m), 8.48(1H,s).

(111) Compound 116-5:δ(CDCl.sub.3) 8.43(s, 1H, Pyrimidine-H), 7.68(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.49-7.54(m, 2H, Ph-2,6-2H), 7.34-7.39(m, 2H, Ph-3,5-2H), 5.86(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.56(t, 2H, O—CH.sub.2), 4.03(t, 2H, N—CH.sub.2), 3.22(s, 3H, NCH.sub.3), 2.79-2.87(m, 2H, CH.sub.2), 1.26(t, 3H, CH.sub.3).

(112) Compound 118-69: m.p. 83.5° C. δ(CDCl.sub.3) 8.28(s, 1H, Pyrimidine-H), 7.81(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.65-7.72 (m, 4H, Ph-2,3,5,6-4H), 6.15(s, 1H, NH), 5.97(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.44(t, 2H, O—CH.sub.2), 3.75(m, 2H, N—CH.sub.2), 2.16(m,2H, CH.sub.2).

(113) Compound 119-69: oil. δ(CDCl.sub.3) 8.07(s, 1H, Pyrimidine-H), 7.81(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.65-7.72 (m, 4H, Ph-2,3,5,6-4H), 5.98(d, J=3 Hz, 1H, Pyrazole-4-H), 5.43(s, 1H, NH), 4.43(t, 2H, O—CH.sub.2), 3.72(m, 2H, N—CH.sub.2), 3.44(s, 2H, NH.sub.2), 2.17(m,2H, CH.sub.2).

(114) Compound 120-69: oil. δ(CDCl.sub.3) 8.10(s, 1H, Pyrimidine-H), 7.80(d, J=3 Hz, 1H, Pyrazole-5-H), 7.64-7.72 (m, 4H, Ph-2,3,5,6-4H), 6.03(d, J=3 Hz, 1H, Pyrazole-4-H), 5.99(s, 1H, NH), 4.43(t, 2H, O—CH.sub.2), 3.84(m, 2H, N—CH.sub.2), 2.17(m,2H, CH.sub.2).

(115) Compound 121-69: m.p. 96.0° C. δ(CDCl.sub.3) 10.38(s, 1H, CHO), 9.47(s, 1H, NH), 8.42(s, 1H, Pyrimidine-H), 7.81(d, 1H, Pyrazole-5-H), 7.65-7.73 (m, 4H, Ph-2,3,5,6-4H), 6.03(d, 1H, Pyrazole-4-H), 4.41(t, 2H, O—CH.sub.2), 3.84(m, 2H, N—CH.sub.2), 2.18(m,2H, CH.sub.2).

(116) Compound 122-69: m.p. 94.1° C. δ(CDCl.sub.3) 8.28(s, 1H, Pyrimidine-H), 7.82(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.65-7.72 (m, 4H, Ph-2,3,5,6-4H), 5.95(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.35(s, 1H, NH), 4.44(t, 2H, O—CH.sub.2), 3.74(m, 2H, N—CH.sub.2), 2.18(m, 2H, CH.sub.2), 2.14(s,3H, CH.sub.3).

(117) Compound 123-69: oil. δ(CDCl.sub.3) 8.15(s, 1H, Pyrimidine-H), 7.81(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.68-7.73 (m, 4H, Ph-2,3,5,6-4H), 5.96(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.89(s, 1H, NH), 4.41(t, 2H, O—CH.sub.2), 3.85(s,3H, CH.sub.3), 3.71(m, 2H, N—CH.sub.2), 2.16(m,2H, CH.sub.2).

(118) Compound 124-19:m.p. 140.1° C. δ(CDCl.sub.3) 8.36(s, 1H, Pyrimidine-H), 7.70(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.53 (d, J=9.0 Hz, 2H, Ph-2,6-2H), 7.37(d, J=9.3 Hz, 2H, Ph-3,5-2H), 5.91(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.87(s, 1H, NH), 4.41(t, 2H, O—CH.sub.2), 3.70-3.75(m, 2H, N—CH.sub.2), 2.45(s, 3H), 2.12-2.17(m, 2H, CH.sub.2).

(119) Compound 125-19:δ(CDCl.sub.3) 8.42(s, 1H, Pyrimidine-H), 7.70(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.51-7.55(m, 2H, Ph-2,6-2H), 7.35-7.39(m, 2H, Ph-3,5-2H), 5.91(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.88(s, 1H, NH), 4.41(t, 2H, O—CH.sub.2), 3.69-3.75(m, 2H, N—CH.sub.2), 2.75-2.80(m, 2H, CH.sub.3—CH.sub.2), 2.12-2.18(m, 2H, CH.sub.2), 1.26(t, 3H, CH.sub.3).

(120) Compound 125-69: m.p. 94.3° C. δ(CDCl.sub.3) 8.42(s, 1H, Pyrimidine-H), 7.81(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.65-7.73 (m, 4H, Ph-2,3,5,6-4H), 5.97(d, J=2.7 Hz, 1H, Pyrazole-4-H), 5.89(s, 1H, NH), 4.43(t, 2H, O—CH.sub.2), 3.73(m, 2H, N—CH.sub.2), 2.78(m, 2H, CH.sub.2CH.sub.3), 2.17(m, 2H, CH.sub.2), 1.26(t,3H, CH.sub.3).

(121) Compound 126-19:m.p. 132.9° C. δ(CDCl.sub.3) 8.54(s, 1H, Pyrimidine-H), 7.70(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.51-7.55(m, 2H, Ph-2,6-2H), 7.35-7.40(m, 2H, Ph-3,5-2H), 6.71(t, 1H, CHF.sub.2), 6.23(s, 1H, NH), 5.91(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.43(t, 2H, O—CH.sub.2), 3.73-3.79(m, 2H, N—CH.sub.2), 2.13-2.19(m, 2H, CH.sub.2).

(122) Compound 126-69: oil. δ(CDCl.sub.3) 8.54(s, 1H, Pyrimidine-H), 7.82(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.65-7.73 (m, 4H, Ph-2,3,5,6-4H), 6.74(t,1H, CHF.sub.2), 6.29(s, 1H, NH), 5.97(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.45(t, 2H, O—CH.sub.2), 3.79(m, 2H, N—CH.sub.2), 2.18(m, 2H, CH.sub.2).

(123) Compound 127-19: m.p. 165.7° C. δ(CDCl.sub.3) 8.66(s, 1H, Quinazoline-3-H), 7.81(d, J=2.7 Hz, 1H, Pyrazole-5-H),7.70-7.78(m, 4H, Quinazoline-5,6,7,8-4H), 7.52 (dd, 2H, Ph-2H),7.37 (dd, 2H, Ph-2H),6.07(s, 1H, NH), 5.92(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.31(t, 2H, O—CH.sub.2), 3.43-3.53 (m, 2H, N—CH.sub.2), 2.02-2.08 (m, 2H, CH.sub.2).

(124) Compound 127-69: m.p. 149.7° C. δ(CDCl.sub.3) 8.67(s, 1H, Quinazoline-3-H), 7.82(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.65-7.81 (m, 4H, Ph-2,3,5,6-4H), 7.65-7.81 (m, 4H, Quinazoline-5,6,7,8-4H), 6.50(s, 1H, NH), 5.98(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.50(t, 2H, O—CH.sub.2), 3.89(m, 2H, N—CH.sub.2), 2.26(m, 2H, CH.sub.2).

(125) Compound 128-19:δ(CDCl.sub.3) 8.46(s, 1H, Pyrimidine-H), 7.70(d, J=2.7 Hz, 1H, Pyrazole-5-H), 7.50-7.54(m, 2H, Ph-2,6-2H), 7.34-7.40(m, 2H, Ph-3,5-2H), 7.05(s, 1H, Thiazole-H), 6.92(s, 1H, NH), 5.91(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.43(t, 2H, O—CH.sub.2), 3.82-3.90(m, 2H, N—CH.sub.2), 2.17-2.27(m, 2H, CH.sub.2).

(126) Compound 128-69: m.p. 123.5° C. δ(CDCl.sub.3) 8.46(s, 1H, Pyrimidine-H), 7.81(d, J=2.4 Hz, 1H, Pyrazole-5-H), 7.64-7.71 (m, 4H, Ph-2,3,5,6-4H), 7.06(s,1H, Thieno-H), 6.92(s, 1H, NH), 5.96(d, J=2.7 Hz, 1H, Pyrazole-4-H), 4.46(t, 2H, O—CH.sub.2), 3.86(m, 2H, N—CH.sub.2), 2.23(m, 2H, CH.sub.2).

(127) Test of Biological Activity

(128) The compounds of the present invention showed good activity against many pathogens, insects and pest mites in agricultural field.

Example 8

Fungicidal Testing

(129) The compound samples of the present invention were tested in fungicidal activity in vitro or protective activity in vivo. The results of the fungicidal testing are as follows.

(130) (1) Determination of Fungicidal Activity In Vitro

(131) The method is as follows: High Through Put is used in the test. The compound is dissolved in a proper solvent to become a testing solution whose concentration is designed. The solvent is selected from acetone, methanol, DMF and so on according to their dissolving capability to the sample. In a no animal cule condition, the testing solution and pathogens suspension are added into the cells of 96 cells culture board, which then should be placed in the constant temperature box. 24 hours later, pathogengermination or growth can be investigated by eyeballing, and the activity in vitro of the compound is evaluated based on germination or growth of control treatment.

(132) The activities in vitro (inhibition rate) of some compounds are as follows:

(133) The inhibition rate against rice blast:

(134) At the dosage of 25 ppm, the inhibition rate of compounds 30-1-4, 31-4, 31-78, 32-1, 32-4, 32-21, 32-57, 32-78, 33-4, 33-18, 35-19, 36-19, 37-19, 40-4, 40-18, 40-57, 40-69, 42-1,42-4, 42-18, 42-21, 42-57, 42-69, 42-78, 44-19, 57-4, 59-21, 68-4 and so on was more than 80% against rice blast. The contrast inhibition rate of compounds CK1, CK2, CK3, CK4 and CK5 was 0; At the dosage of 8.3 ppm, the inhibition rate of compounds 31-4, 36-19, 40-4, 40-18, 40-57, 42-1, 42-18, 42-21, 42-57, 42-69, 44-19, 57-4, 59-21, 68-4, 128-69 and so on was more than 80% against rice blast; At the dosage of 2.8 ppm, the inhibition rate of compounds 36-19, 42-1, 42-18, 42-21, 42-69, 44-19, 57-4, 59-21, 68-4 and so on was more than 80% against rice blast.

(135) The inhibition rate against cucumber gray mold:

(136) At the dosage of 25 ppm, the inhibition rate of compounds 36-19, 40-19, 44-19, 57-4, 59-21, 68-4 and so on was more than 80% against cucumber gray mold. The contrast inhibition rate of compounds CK1, CK2, CK3, CK4 and CK5 was 0.

(137) (2) The Determination of Protective Activity In Vivo

(138) The method is as followed: The whole plant is used in this test. The compound is dissolved in a proper solvent to get mother solution. The proper solvent is selected from acetone, methanol, DMF and so on according to their dissolving capability to the sample. The volume rate of solvent and testing solution (v/v) is equal to or less than 5%. The mother solution is diluted with water containing 0.1% tween-80 to get the testing solution whose concentration is designed. The testing solution is sprayed to the host plant by a special plant sprayer. The plant is inoculated with fungus after 24 hours. According to the infecting characteristic of fungus, the plant is stored in a humidity chamber and then transferred into greenhouse after infection is finished. And the other plants are placed in greenhouse directly. The activity of compound is obtained by eyeballing after 7 days in common.

(139) The protective activities in vivo of some compounds are as follows:

(140) The protective activity against cucumber downy mildew in vivo:

(141) At the dosage of 400 ppm, the compounds 30-1-4, 30-1-49, 30-1-57, 31-4, 31-19, 31-18, 31-21, 31-49, 31-57, 31-69, 32-4, 32-18, 32-19, 32-21, 32-49, 33-18, 33-19, 33-21, 35-19, 36-19, 40-4, 40-18, 40-19, 40-21, 40-57, 42-1, 42-18, 42-21, 42-49, 42-57, 42-69, 42-78, 44-19, 57-4, 57-19, 58-19, 59-19, 66-19, 68-19, 68-4 and so on showed more than 80% control against cucumber downy mildew; At the dosage of 100 ppm, the compounds 30-1-19, 30-1-21, 30-1-30, 30-2-19, 31-4, 31-18, 31-19, 31-21, 31-23, 31-30, 31-69, 32-4, 32-17, 32-18, 32-19, 32-21, 32-30, 33-18, 33-19, 33-21, 33-30, 33-49, 33-57, 35-19, 36-19, 40-1, 40-4, 40-17, 40-18, 40-19, 40-21, 40-30, 42-1, 42-17, 42-18, 42-21, 42-69, 44-19, 123-69, 125-69, 126-69, 127-69, 128-69 and so on showed more than 80% control against cucumber downy mildew; At the dosage of25 ppm, the compounds 30-1-19, 30-1-21, 30-1-30, 30-2-19, 31-18, 31-19, 31-21, 31-23, 31-30, 31-69, 32-4, 32-19, 32-30, 33-18, 33-19, 33-21, 33-30, 33-49, 33-57, 35-19, 36-19, 40-4, 40-17, 40-18, 40-19, 40-21, 40-30, 42-1, 42-17, 42-18, 42-21, 42-69, 44-19 and so on showed more than 80% control against cucumber downy mildew; At the dosage of12.5 ppm, the compounds 30-2-19, 31-23, 32-19, 32-30, 33-21, 33-30, 33-49, 33-57, 35-19, 36-19, 40-4, 40-18, 40-19, 42-21 and so on showed more than 80% control against cucumber downy mildew; At the dosage of6.25 ppm, the compounds 30-2-19, 31-23, 32-19, 32-30, 33-21, 33-30, 33-49, 33-57, 36-19, 40-4, 40-18, 40-19, 42-21 and so on showed more than 80% control against cucumber downy mildew.

(142) The protective activity against wheat powdery mildew in vivo:

(143) At the dosage of 400 ppm,the compounds 30-1-57, 30-1-21, 30-2-19, 31-18, 31-21, 31-30, 31-49, 31-57, 31-69, 31-78, 32-1, 32-17, 32-18, 32-19, 32-21, 32-30, 32-49, 32-69, 32-78, 33-4, 33-19, 33-21, 33-30, 33-49, 33-57, 33-69, 35-19, 36-19, 37-19, 40-19, 40-21, 40-69, 42-4, 42-17, 42-18, 42-21, 42-49, 42-57, 42-69, 42-78, 44-19, 57-19, 58-19, 59-19, 66-19, 68-19, 59-21, 118-69, 119-69, 122-69, 123-69, 125-69, 126-69, 127-69, 128-69 and so on showed more than 80% control against wheat powdery mildew; At the dosage of 100 ppm, the compounds 30-1-21, 30-2-19, 31-30, 31-69, 32-17, 32-19, 32-21, 32-30, 32-49, 32-69, 33-4, 33-19, 33-30, 33-49, 33-57, 33-69, 36-19, 37-19, 42-17, 42-57, 42-69, 44-19, 59-21, 118-69, 119-69, 122-69, 123-69, 125-69, 126-69, 127-69, 128-69 and so on showed more than 80% control against wheat powdery mildew; At the dosage of 25 ppm, the compounds 30-2-19, 31-30, 31-69, 32-21, 32-30, 32-69, 33-4, 33-19, 33-30, 33-49, 33-57, 33-69, 36-19, 37-19, 42-69, 44-19, 118-69, 119-69, 122-69, 123-69, 125-69, 126-69, 127-69, 128-69 and so on showed more than 80% control against wheat powdery mildew; At the dosage of 6.25 ppm, the compounds 30-2-19, 31-69, 32-69, 33-4, 33-19, 33-49, 33-57, 33-69, 36-19, 37-19, 42-69, 44-19, 118-69, 123-69, 126-69, 128-69 and so on showed more than 80% control against wheat powdery mildew.

(144) The protective activity against corn rust in vivo:

(145) At the dosage of400 ppm, the compounds 31-49, 31-57, 31-69, 32-4, 32-18, 32-19, 32-49, 32-57, 32-69, 32-78, 33-4, 33-19, 33-69, 36-19, 37-19, 40-18, 40-21, 42-18, 42-21, 42-4, 42-69, 42-78, 44-19, 57-4, 59-21, 68-4 and so on showed more than 80% control against corn rust; At the dosage of 100 ppm, the compounds 31-69, 31-57, 32-49, 32-57, 32-69, 33-4, 33-69, 37-19, 42-18, 42-69, 44-19, 57-4 and so on showed more than 80% control against corn rust; At the dosage of 25 ppm, the compounds 32-49, 32-57, 32-69, 37-19, 42-69 and so on showed more than 80% control against corn rust; At the dosage of 6.25 ppm, the compounds 32-49, 37-19, 42-69 and so on showed more than 80% control against corn rust.

(146) The protective activity against cucumber anthracnose in vivo:

(147) At the dosage of 400 ppm,the compounds 31-4, 31-19, 31-49, 31-57, 32-4, 32-18, 32-19, 32-49, 33-4, 33-19, 40-4, 40-19, 40-57, 42-1, 42-49, 42-69 and so on showed more than 80% control against cucumber anthracnose; At the dosage of 100 ppm, the compounds 31-19, 31-49, 31-57, 32-4, 32-18, 32-19, 32-49, 33-4, 33-19, 40-4, 40-19, 40-57, 42-1, 42-49, 118-69, 122-69, 123-69, 126-69, 127-69 and so on showed more than 80% control against cucumber anthracnose; At the dosage of 25 ppm, the compounds 31-19, 31-49, 31-57, 32-4, 32-49, 33-4, 32-19, 40-19, 40-57, 42-1, 42-49, 42-69, 122-69, 123-69, 126-69, 127-69 and so on showed more than 80% control against cucumber anthracnose; At the dosage of 6.25 ppm, the compound 31-57, 32-19, 32-49, 40-57 and 42-1showed 90% control against cucumber anthracnose.

(148) (3) The Contrastive Test Results of Some Compounds and Contrasts

(149) Contrastive tests were carried out between some compounds and contrasts. The test results are listed in table 129-table 132 (“///” in the following tables means no test).

(150) TABLE-US-00015 TABLE 129 The comparative test of protective activity against cucumber downy mildewat 25 mg/L Compound No. protective activity (%) 30-1-19 95 30-1-21 100 30-1-30 98 30-2-19 98 31-18 95 31-19 100 31-21 90 31-23 100 31-30 100 31-69 100 32-4 95 32-17 70 32-18 60 32-19 100 32-21 70 32-30 100 33-18 85 33-19 95 33-21 100 33-30 100 33-49 100 33-57 100 35-19 100 36-19 100 40-1 70 40-4 100 40-17 70 40-18 100 40-19 96 40-21 100 40-30 100 42-1 100 42-17 100 42-18 100 42-21 100 42-69 80 44-19 100 126-69 70 127-69 70 CK1 20 CK2 20 CK3 0 CK4 0 CK5 0

(151) TABLE-US-00016 TABLE 130 The comparative test of protective activity against wheat powdery mildew at 100 mg/L protective Compound activity No. (%) 30-2-19 100 31-30 98 31-69 100 32-19 100 32-21 100 32-30 100 32-69 100 33-4  100 33-19 100 33-30 100 33-49 100 33-57 100 33-69 100 35-19 70 36-19 100 37-19 95 42-69 100 44-19 100 118-69  100 119-69  100 122-69  100 123-69  100 125-69  100 126-69  100 127-69  100 128-69  100 CK2 50 CK3 0 CK4 0 CK5 0

(152) TABLE-US-00017 TABLE 131 The comparative test of protective activity against corn rust control effect against corn rust (%) Compound No. 100 mg/L 25 mg/L 32-57 98 85 32-69 90 85 37-19 100 90 42-69 90 85 CK3 20 0 CK4 0 0 CK5 70 60

(153) TABLE-US-00018 TABLE 132 The comparative test of protective activity against cucumber anthracnose at 100 mg/L  (%) Com- protective protective protective pound activity Compound activity Compound activity No. (%) No. (%) No. (%) 31-19 90 33-4  85 122-69 85 31-49 85 33-19 100 123-69 90 31-57 98 40-19 100 126-69 95 32-4  90 40-57 98 127-69 92 32-18 85 42-1  95 CK3 0 32-19 100 42-69 95 CK4 0 32-49 100 118-69  80 CK5 0

Example 9

Bioactivity Test Against Insects and Mites

(154) Determination of insecticidal activity of compounds of the present invention against a few insects were carried out by the following procedures:

(155) Compounds were dissolved in mixed solvent (acetone:methanol=1:1), and diluted to required concentration with water containing 0.1% of tween 80.

(156) Diamond back moth, armyworm, peach aphid and carmine spider mite were used as targets and the method of spraying by airbrush was used for determination of insecticidal biassays.

(157) (1) Bioactivity Test Against Diamond Back Moth

(158) The method of spraying by airbrush: The cabbage leaves were made into plates of 2 cm diameter by use of punch. A test solution (0.5 ml) was sprayed by airbrush at the pressure of 0.7 kg/cm.sup.2 to both sides of every plate. 10 Second instar larvae were put into the petri-dishes after the leaf disc air-dried and 3 replicates were set for each treatment. Then the insects were maintained in observation room (25° C., 60˜70% R.H.). Scores were conducted and mortalities were calculated after 72 h.

(159) Some of test results against diamond back moth:

(160) At the dosage of 600 ppm, the compounds 33-19, 37-19 and so on showed 100% control against diamond back moth.

(161) (2) Bioactivity Test Against Green Peach Aphid

(162) Method: Filter papers were put in culture dishes (Diameter=6 cm), and water was dripped on filter papers for preserving moisture. Green peach aphids (Myzus Persicae Sulzer) were maintained on cabbage. Leaves (Diameter=3 cm) of approximately 15-30 aphids were put in the culture dishes. Bioactivity tests were used the method of Airbrush Foliar Spray, pressure=10 psi (0.7 kg/cm2), spray volume=0.5 mL. The studies were conducted at three constant temperatures 25±1 C in incubator cabinets with 60±5% RH. Survey the survival aphids after 48 h and calculate the death rates.

(163) At the dosage of 600 ppm, the compounds 31-49, 32-17, 32-21, 32-30, 32-33, 32-57, 33-21, 33-57, 37-19, 42-1, 42-57, 59-21 and so on showed more than 80% control against Green Peach Aphid; At the dosage of 100 ppm, the compounds 32-21, 33-21, 37-19 and so on showed more than 80% control against Green Peach Aphid; At the dosage of 5 ppm,the compound 33-21 showed 100% control against Green Peach Aphid.

(164) (3) Bioactivity Test Against Carmine Spider Mite

(165) The method: Broadbean shoots with two true leaves in pot were taken, the healthy adults of carmine spider mite were inoculated to the leaves. The adults were counted and then sprayed with airbrush at the pressure of 0.7 kg/cm.sup.2 and at dose of 0.5 ml. 3 replicates were set for each treatment. And then they were maintained in standard observation room. Scores were conducted and mortalities were calculated after 72 hrs.

(166) Bioactivity Test Against Carmine Spider Mite:

(167) At the dosage of 600 ppm,the compounds 30-1-57, 30-2-19, 31-23, 32-17, 32-21, 32-23, 32-30, 32-57, 32-78, 33-4, 33-57, 36-19, 37-19, 40-4, 42-17, 42-57, 42-78, 44-19, 59-21 and so on showed more than 80% control against carmine spider mite; At the dosage of 100 ppm, the compounds 32-21, 32-57, 36-19, 37-19, 42-57, 44-19 and so on showed more than 80% control against carmine spider mite; At the dosage of 10 ppm, both compounds 32-57 and 37-19showed more than 80% control against carmine spider mite.

(168) (4) The Contrastive Test Results of Some Compounds and Contrasts

(169) Contrastive tests were carried out between some compounds and contrasts. The test results are listed in table 133 to table 135 (“///” in the following tables means no test).

(170) TABLE-US-00019 TABLE 133 contrastive tests againstdiamond back moth Insecticidal activity against Compound diamond back moth (%) No. 600 mg/L 33-19 100 37-19 100 CK1 43 CK2 20 CK3 0 CK4 0 CK5 0

(171) TABLE-US-00020 TABLE 134 contrastive tests against peach aphid Insecticidal activity against peach aphid (%) Compound No. 100 mg/L 33-21 100 37-19 84 CK1 0 CK3 30 CK4 0 CK5 22

(172) TABLE-US-00021 TABLE 135 contrastive tests againstcarmine spider mite Insecticidal activity against carmine spider mite (%) Compound No. 600 mg/L 100 mg/L 32-57 100 100 36-19 100 98 37-19 100 100 44-19 100 100 CK3 56 /// CK4 59 /// CK5 58 ///