Malononitrile oxime ether compound and use thereof

Abstract

Disclosed is a malononitrile oxime ether compound having a novel structure as shown in the general formula I. Respective substituents in the general formula I as defined in the specification. ##STR00001## The compound of the general formula I exhibits an excellent microbicidal activity, and can effectively prevent and treat plant diseases caused by bacteria and fungi. Also provided is a use of the compound of the general formula I as a microbicide in the agricultural and other fields.

Claims

1. A malononitrile oxime ether compound relates to compounds of formula I ##STR00215## wherein L is selected from the group consisting of: (CR.sup.1R.sup.2).sub.n, (CR.sup.1R.sup.2).sub.mCH.sub.2(CO)CH.sub.2(CR.sup.1R.sup.2).sub.P, (CR.sup.1R.sup.2).sub.m(CR.sup.1CR.sup.2)(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.m(CO)OCH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.m(CC)(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mO(CO)CH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mOCH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.m(CO)NHCH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mNHCH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mNH(CO)CH.sub.2(CR.sup.1R.sup.2).sub.p and (CR.sup.1R.sup.2).sub.mSCH.sub.2(CR.sup.1R.sup.2).sub.p, where n represents 1, 2, 3 or 4; m and p independently represent 0, 1, 2 or 3; R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, halogen, cyano, [C.sub.1-C.sub.4]-alkyl, [C.sub.1-C.sub.4]-haloalkyl, [C.sub.3-C.sub.5]-cycloalkyl, [C.sub.2-C.sub.4]-alkenyl, [C.sub.2-C.sub.4]-haloalkenyl, [C.sub.2-C.sub.4]-alkynyl, [C.sub.2-C.sub.4]-haloalkynyl, [C.sub.1-C.sub.4]-alkoxy, [C.sub.1-C.sub.4]-haloalkoxy, [C.sub.1-C.sub.4]-alkoxy-[C.sub.1-C.sub.4]-alkyl, [C.sub.1-C.sub.4]-alkoxy-[C.sub.1-C.sub.4]-alkoxy, and C.sub.1-C.sub.4 haloalkoxy C.sub.1-C.sub.4 alkyl; W is selected from non-substituted or substituted aryl or non-substituted or substituted aromatic heterocycle; and, when L is (CR.sup.1R.sup.2).sub.n, R.sup.1 and R.sup.2 are each hydrogen and n is 1, W is not benzene.

2. The compound according to claim 1, wherein, L is selected from the group consisting of: (CR.sup.1R.sup.2).sub.n, (CR.sup.1R.sup.2).sub.mCH.sub.2(CO)CH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.m(CR.sup.1R.sup.2)(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.m(CO)OCH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.m(CC)(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mO(CO)CH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mOCH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.m(CO)NHCH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mNHCH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mNH(CO)CH.sub.2(CR.sup.1R.sup.2).sub.p and (CR.sup.1R.sup.2).sub.mSCH.sub.2(CR.sup.1R.sup.2).sub.p; n represents 1, 2, 3 or 4; m and p are each independently represent 0, 1, 2 or 3; R.sup.1 and R.sup.2 are each hydrogen; W is selected from one of the groups represented by W.sup.1-W.sup.84: ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## wherein: X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8 and X.sup.9 are each independently selected from the group consisting of hydrogen, halogen, cyano, nitro, SF.sub.5, [C.sub.1-C.sub.8]-alkyl, [C.sub.1-C.sub.8]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.2-C.sub.8]-alkenyl, [C.sub.2-C.sub.8]-haloalkenyl, [C.sub.2-C.sub.8]-alkynyl, [C.sub.2-C.sub.8]-haloalkynyl, [C.sub.1-C.sub.8]-alkoxy-[C.sub.1-C.sub.8]-alkyl, OR.sup.3, C(O)OR.sup.3, N(R.sup.4)S(O).sub.2R.sup.5, S(O).sub.2NR.sup.3R.sup.5, N(R.sup.4)C(O)OR.sup.3, CR.sup.4NOR.sup.3, CH.sub.2ONC(CN).sub.2, C(O)SR.sup.3C(S) OR.sup.3, C(S)SR.sup.3, CR.sup.4NR.sup.5, CR.sup.4NNR.sup.3R.sup.5, OSiR.sup.4R.sup.5R.sup.6, OC(O)R.sup.4, OC(O)OR.sup.3, OC(O)NR.sup.3R.sup.4, OC(S)NR.sup.3R.sup.4, NR.sup.3R.sup.4, N(R.sup.4)C(O)NR.sup.3R.sup.5, N(R.sup.4)C(S)NR.sup.3R.sup.5, NCR.sup.4R.sup.5, NCNR.sup.3R.sup.4, N(R.sup.4)C(NR.sup.5)NR.sup.3R.sup.6, N(R.sup.4)OR.sup.3, N(R.sup.4)NR.sup.3R.sup.5, NNR.sup.4, N(R.sup.4)S(O)R.sup.5, N(R.sup.4)S(O).sub.2OR.sup.3, N(R.sup.4)S(O)OR.sup.3, N(R.sup.4)S(O)NR.sup.3R.sup.5, N(R.sup.4)S(O).sub.2NR.sup.3R.sup.5, NR.sup.4C(O)R.sup.5, SR.sup.3, S(O).sub.2R.sup.4, S(O)R.sup.4, S(O)OR.sup.3, S(O)NR.sup.3R.sup.4, S(O).sub.2OR.sup.3, S(O)NR.sup.3R.sup.4, SiR.sup.3R.sup.4R.sup.5, non-substituted or substituted phenyl, non-substituted or substituted pyridyl, non-substituted or substituted pyrazolyl, non-substituted or substituted thiazolyl, non-substituted or substituted isothiazolyl, and non-substituted or substituted thiadiazolyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.8]-alkyl, [C.sub.1-C.sub.8]-haloalkyl, [C.sub.1-C.sub.8]-alkoxy, [C.sub.1-C.sub.8]-haloalkoxy, [C.sub.1-C.sub.8]-alkylthio and [C.sub.1-C.sub.8]-haloalkylthio; Z is selected from the group consisting of hydrogen, [C.sub.1-C.sub.8]-alkyl, [C.sub.1-C.sub.8]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.2-C.sub.8]-alkenyl, [C.sub.2-C.sub.8]-haloalkenyl, [C.sub.2-C.sub.8]-alkynyl, [C.sub.2-C.sub.8]-haloalkynyl, aryl, aryl-[C.sub.1-C.sub.8]alkyl, [C.sub.1-C.sub.8]-alkoxy-[C.sub.1-C.sub.8]-alkyl, C(O)R.sup.3 and C(O)OR.sup.3; K is selected from the group consisting of oxygen, sulfur, NR.sup.3, NOR.sup.4 and NNR.sup.3R.sup.4; R.sup.3 is selected from the group consisting of hydrogen, [C.sub.1-C.sub.8]alkyl, [C.sub.1-C.sub.8]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.8]-alkyloxycarbonyl, [C.sub.2-C.sub.8]-alkenyl, [C.sub.2-C.sub.8]-haloalkenyl, [C.sub.2-C.sub.8]-alkynyl, [C.sub.2-C.sub.8]-haloalkynyl, unsubstituted or substituted phenyl, non-substituted or substituted pyridyl non-substituted or substituted pyrazolyl, non-substituted or substituted thiazolyl, non-substituted or substituted isothiazolyl and non-substituted or substituted thiadiazolyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, CONH.sub.2, COOH, CHO, [C.sub.1-C.sub.4]-alkyl, [C.sub.1-C.sub.4]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]-haloalkylthio, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkoxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1-C.sub.3]-alkylaminocarbonyl and [C.sub.1-C.sub.3]-alkylaminosulfonyl; R.sup.4, R.sup.5 and R.sup.6 are each independently selected from hydrogen, [C.sub.1-C.sub.8]-alkane, [C.sub.1-C.sub.8]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.8]-alkoxy, [C.sub.1-C.sub.8]-haloalkoxy, [C.sub.1-C.sub.8]-alkoxycarbonyl, [C.sub.2-C.sub.8]-alkenyl, [C.sub.2-C.sub.8]-haloalkenyl, [C.sub.2-C.sub.8]-alkynyl, [C.sub.2-C.sub.8]-haloalkynyl, non-substituted or substituted phenyl, non-substituted or substituted pyridyl, non-substituted or substituted pyrazolyl, non-substituted or substituted thiazolyl, non-substituted or substituted isothiazolyl and non-substituted or substituted thiadiazolyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, hydroxyl mercapto, amino, CONH.sub.2, COOH, CHO, [C.sub.1-C.sub.4]-alkyl, [C.sub.1-C.sub.4]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]-haloalkylthio, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkoxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1 C.sub.3]-alkylaminocarbonyl and [C.sub.1-C.sub.3]-alkylaminosulfonyl; Q is selected from the group consisting of Q.sup.1-10, non-substituted or substituted phenyl, non-substituted or substituted pyridyl, non-substituted or substituted pyrazolyl, non-substituted or substituted thiazolyl, non-substituted or substituted isothiazolyl and non-substituted or substituted thiadiazolyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, CONH.sub.2, COOH, CHO, [C.sub.1-C.sub.4]-alkyl, [C.sub.1-C.sub.4]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]haloalkylthio, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkoxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1-C.sub.3]-alkylaminocarbonyl and [C.sub.1-C.sub.3]-alkylaminosulfonyl, and where Q.sup.1-10 are: ##STR00227## ##STR00228## and T is selected from the group consisting of cyano, [C.sub.1-C.sub.8]-alkyl, [C.sub.1-C.sub.8]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.2-C.sub.8]-alkenyl, [C.sub.2-C.sub.8]-haloalkenyl, [C.sub.2-C.sub.8]-alkynyl, [C.sub.2-C.sub.8]-haloalkynyl, non-substituted or substituted phenyl, non-substituted or substituted pyridyl, non-substituted or substituted pyrazolyl, non-substituted or substituted thiazolyl, non-substituted or substituted isothiazolyl and non-substituted or substituted thiadiazolyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, CONH.sub.2, COOH, CHO, [C.sub.1-C.sub.4]-alkyl, [C.sub.1-C.sub.4]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]-haloalkylthio, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkoxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1-C.sub.3]-alkylaminocarbonyl and [C.sub.1-C.sub.3]alkylaminosulfonyl.

3. The compound according to claim 2, wherein L is selected from the group consisting of (CR.sup.1R.sup.2).sub.n, (CR.sup.1R.sup.2).sub.mNH(CO)CH.sub.2(CR.sup.1R.sup.2), (CR.sup.1R.sup.2).sub.mOCH.sub.2(CR.sup.1R.sup.2).sub.p and (CR.sup.1R.sup.2).sub.mSCH.sub.2(CR.sup.1R.sup.2).sub.p; where n represents 1, 2, 3 or 4; m and p independently represent 0, 1, 2 or 3; R.sup.1 and R.sup.2 are selected from hydrogen; W is selected from the group consisting of W.sup.1, W.sup.2, W.sup.3, W.sup.4, W.sup.12, W.sup.16, W.sup.18, W.sup.21, W.sup.23, W.sup.48, W.sup.49, W.sup.67, W.sup.68, W.sup.69, W.sup.70, W.sup.71, W.sup.72, W.sup.73, W.sup.74, W.sup.75, W.sup.76, W.sup.77, W.sup.78, W.sup.79, W.sup.80, W.sup.81, W.sup.82, W.sup.83 and W.sup.84; X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8 and X.sup.9 are each independently selected from the group consisting of hydrogen, halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy[C.sub.1-C.sub.3]-alkyl, OR.sup.3, C(O)OR.sup.3, N(R.sup.4)S(O).sub.2R.sup.5, S(O).sub.2NR.sup.3R.sup.5, N(R.sup.4)C(O)OR.sup.3, CR.sup.4NOR.sup.3, CH.sub.2ONC(CN).sub.2, NR.sup.4C(O)R.sup.5, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio and [C.sub.1-C.sub.3]-haloalkylthio; Z is selected from the group consisting of hydrogen, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, phenylmethyl, C(O)R.sup.3 and C(O)OR.sup.3; K is selected from oxygen or sulfur; R.sup.3 is selected the group consisting of hydrogen, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxycarbonyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio and [C.sub.1-C.sub.3]-haloalkylthio; R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkoxycarbonyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl group, wherein the substituent is selected from the group consisting of halogen cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio and [C.sub.1-C.sub.3]-haloalkylthio; Q is selected from the group consisting of Q.sup.1-10, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, where the substituent group is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, CONH.sub.2, COOH, CHO, [C.sub.1-C.sub.3]alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]alkoxy, [C.sub.1-C.sub.3]haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkoxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1-C.sub.3]alkylaminocarbonyl and [C.sub.1-C.sub.3]-alkylaminosulfonyl and where Q.sup.1-10 are: ##STR00229## ##STR00230## and T is selected from cyano, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]-halo-alkylthio, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkoxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1-C.sub.3]-alkylaminocarbonyl and [C.sub.1-C.sub.3]-alkylaminosulfonyl.

4. The compound according to claim 2, wherein L is selected from the group consisting of: (CR.sup.1R.sup.2).sub.n, (CR.sup.1R.sup.2).sub.mNH(CO)CH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mOCH.sub.2(CR.sup.1R.sup.2).sub.p and (CR.sup.1R.sup.2).sub.mSCH.sub.2(CR.sup.1R.sup.2).sub.p; n represents 1 or 2; m and p independently represent 0, 1 or 2; R.sup.1 and R.sup.2 are selected from hydrogen; W is selected from the group consisting of W.sup.1, W.sup.2, W.sup.3, W.sup.4, W.sup.12, W.sup.16, W.sup.18, W.sup.21, W.sup.23, W.sup.48, W.sup.49, W.sup.67, W.sup.68, W.sup.69, W.sup.70, W.sup.71, W.sup.72, W.sup.73, W.sup.74, W.sup.75, W.sup.76, W.sup.77, W.sup.78, W.sup.79, W.sup.80, W.sup.81, W.sup.82, W.sup.83 and W.sup.84; X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8 and X.sup.9 are each independently selected from the group consisting of hydrogen, halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy-[C.sub.1-C.sub.3]-alkyl, OR.sup.3, C(O)OR.sup.3, N(R.sup.4)S(O).sub.2R.sup.5, S(O).sub.2NR.sup.3R.sup.5, N(R.sup.4)C(O)OR.sup.3, CR.sup.4NOR.sup.3, CH.sub.2ONC(CN).sub.2, NR.sup.4C(O)R.sup.5, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio and [C.sub.1-C.sub.3]-haloalkylthio; Z is selected from the group consisting of hydrogen, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, phenylmethyl, C(O)R.sup.3 and C(O)OR.sup.3; K is selected from the group consisting of oxygen and sulfur; R.sup.3 is selected from the group consisting of hydrogen, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxycarbonyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio and [C.sub.1-C.sub.3]haloalkylthio; R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkoxycarbonyl, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl group, where the substituent group is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio and [C.sub.1-C.sub.3]-haloalkylthio; Q is selected from the group consisting of Q.sup.1-10, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl group, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, CONH.sub.2, COOH, CHO, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3] haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]haloalkyl, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkoxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1-C.sub.3]alkylaminocarbonyl and [C.sub.1-C.sub.3]-alkylaminosulfonyl; T is selected from the group consisting of cyano, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkoxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1-C.sub.3]-alkylaminocarbonyl and [C.sub.1-C.sub.3]-alkylaminosulfonyl.

5. The compound according to claim 4, wherein L is selected from the group consisting of (CR.sup.1R.sup.2).sub.n, (CR.sup.1R.sup.2).sub.mNH(CO)CH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mOCH.sub.2(CR.sup.1R.sup.2).sub.p and (CR.sup.1R.sup.2).sub.mSCH.sub.2(CR.sup.1R.sup.2).sub.p; n represents 1 or 2; m represents 0 or 1; p represents 0, 1 or 2; R.sup.1, R.sup.2 are selected from hydrogen; W is selected from the group consisting of W.sup.1, W.sup.2, W.sup.3, W.sup.4, W.sup.12, W.sup.16, W.sup.18, W.sup.21, W.sup.23, W.sup.48, W.sup.49, W.sup.67, W.sup.69, W.sup.70, W.sup.71, W.sup.72, W.sup.73, W.sup.74, W.sup.75, W.sup.76, W.sup.77, W.sup.78, W.sup.79, W.sup.80, W.sup.81, W.sup.82, W.sup.83 and W.sup.84; X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8 and X.sup.9 are each independently selected from the group consisting of hydrogen, halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-alkyl, OR.sup.3, C(O)OR.sup.3, N(R.sup.4)S(O).sub.2R.sup.5, S(O).sub.2NR.sup.3R.sup.5, N(R.sup.4)C(O)OR.sup.3, CR.sup.4NOR.sup.3, CH.sub.2ONC(CN).sub.2, NR.sup.4C(O)R.sup.5, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent group is selected in from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, and [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, and [C.sub.1-C.sub.3]-haloalkoxy; Z is selected from the group consisting of hydrogen, methyl, phenylmethyl, C(O)R.sup.3 and C(O)OR.sup.3; K is oxygen; R.sup.3 is selected from the group consisting of hydrogen, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxycarbonyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio and [C.sub.1-C.sub.3]-haloalkylthio; R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkoxycarbonyl, a non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio and [C.sub.1-C.sub.3]-haloalkylthio; Q is selected from the group consisting of Q.sup.1-10, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, CONH.sub.2, COOH, CHO, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, [C.sub.1-C.sub.3] haloalkylthio, [C.sub.1-C.sub.3]-alkylamino, [C.sub.1-C.sub.3]-dialkylamino, [C.sub.3-C.sub.6]-cycloalkylamino, [C.sub.1-C.sub.3]-alkyloxycarbonyl, [C.sub.1-C.sub.3]-alkylsulfonyl, [C.sub.1-C.sub.3]-alkylaminocarbonyl and [C.sub.1-C.sub.3]-alkylaminosulfonyl; T is selected consisting of cyano, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, a non-substituted or substituted phenyl group and non-substituted or substituted pyridyl group, where the substituent is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]alkylthio, and [C.sub.1-C.sub.3]-haloalkylthio.

6. The compound according to claim 5, wherein L is selected from the group consisting of (CR.sup.1R.sup.2).sub.n, (CR.sup.1R.sup.2).sub.mNH(CO)CH.sub.2(CR.sup.1R.sup.2).sub.p, (CR.sup.1R.sup.2).sub.mOCH.sub.2(CR.sup.1R.sup.2).sub.p and (CR.sup.1R.sup.2).sub.mSCH.sub.2(CR.sup.1R.sup.2).sub.p; n represents 1 or 2; m represents 0; p represents 0 or 1; R.sup.1 and R.sup.2 are each hydrogen; and W is selected from the group consisting of W.sup.1, W.sup.2, W.sup.3, W.sup.4, W.sup.12, W.sup.16, W.sup.18, W.sup.21, W.sup.23, W.sup.48, W.sup.49, W.sup.67, W.sup.68, W.sup.69, W.sup.70, W.sup.71, W.sup.72, W.sup.74, W.sup.79, W.sup.80, W.sup.81, W.sup.82 and W.sup.83; X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, and X.sup.9 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, heptafluoroisopropyl, OR.sup.3, C(O)OR.sup.3, N(R.sup.4)S(O).sub.2R.sup.5, S(O).sub.2NR.sup.3R.sup.4, N(R.sup.4)C(O)OR.sup.3, CR.sup.4NOR.sup.3, CH.sub.2ONC(CN).sub.2, NR.sup.4C(O)R.sup.5, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl group, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxy, and trifluoromethoxy; Z is selected from the group consisting of hydrogen, methyl, and phenylmethyl; K is oxygen; R.sup.3 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, difluoromethyl, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxycarbonyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, and trifluoromethyl; R.sup.4, R.sup.5 are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, difluoromethyl, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxy, trifluoromethoxy, methoxycarbonyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, methyl, ethyl, propyl, chloromethyl, bromomethyl, trifluoromethyl, heptafluoroisopropyl, methoxy, and trifluoromethoxy; Q is selected from the group consisting of Q.sup.1-10, non-unsubstituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3] haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, and [C.sub.1-C.sub.3]-haloalkylthio; T is selected from the group consisting of cyano, [C.sub.1-C.sub.3]-alkyl group, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl group, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, [C.sub.1-C.sub.3]-alkyl, [C.sub.1-C.sub.3]-haloalkyl, [C.sub.3-C.sub.6]-cycloalkyl, [C.sub.1-C.sub.3]-alkoxy, [C.sub.1-C.sub.3]-haloalkoxy, [C.sub.1-C.sub.3]-alkylthio, and [C.sub.1-C.sub.3]-alkylthio.

7. The compound according to claim 6, wherein, L is selected from CH.sub.2, CH.sub.2CH.sub.2, NH(CO)CH.sub.2 or OCH.sub.2CH.sub.2; W is selected from the group consisting of W.sup.1, W.sup.2, W.sup.3, W.sup.4, W.sup.12, W.sup.16, W.sup.18, W.sup.21, W.sup.23, W.sup.48, W.sup.49, W.sup.67, W.sup.68, W.sup.69, W.sup.70, W.sup.71, W.sup.72, W.sup.74, W.sup.79, W.sup.80, W.sup.81, W.sup.82 and W.sup.83; X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, and X.sup.9 are each independent selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, heptafluoroisopropyl, OR.sup.3, C(O)OR.sup.3, N(R.sup.4)S(O).sub.2R.sup.5, S(O).sub.2NR.sup.3R.sup.4, N(R.sup.4)C(O)OR.sup.3, CR.sup.4NOR.sup.3, CH.sub.2ONC(CN).sub.2, NR.sup.4C(O)R.sup.5, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxy, trifluoromethoxy; Z is selected from the group consisting of hydrogen, methyl, phenylmethyl; K is oxygen; R.sup.3 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, difluoromethyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, trifluoromethyl; R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, difluoromethyl, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxy, trifluoromethoxy, methoxycarbonyl, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, methyl, ethyl, propyl, chloromethyl, bromomethyl, trifluoromethyl, heptafluoroisopropyl, methoxy, trifluoromethoxy; Q is selected from the group consisting of Q.sup.1-10, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, heptafluoroisopropyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethoxy, methylthio, ethylthio, trifluoromethylthio, and trifluoroethylthio; T is selected from the group consisting of cyano, methyl, ethyl, propyl, isopropyl, cyclopropyl, trifluoroethyl, difluoroethyl, cyclopropyl, cyclobutanyl, a cyclopentyl, cyclohexyl, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl, wherein the substituent is selected from the group consisting of halogen, cyano, nitro, methyl, ethyl, propyl, isopropyl, chloromethyl, bromomethyl, trifluoromethyl, heptafluoroisopropyl, cyclopropyl, cyclobutanyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethoxy, methylthio, ethylthio, trifluoromethylthio, and trifluoroethylthio; when L represents CH.sub.2, W is not benzene.

8. The compound according to claim 7, wherein, L is selected from the group consisting of CH.sub.2, CH.sub.2CH.sub.2, NH(CO)CH.sub.2 and OCH.sub.2CH.sub.2; W is selected from the group consisting of W.sup.1, W.sup.2, W.sup.3 and W.sup.4; X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, and X.sup.9 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, heptafluoroisopropyl, OR.sup.3, C(O)OR.sup.3, N(R.sup.4)S(O).sub.2R.sup.5, S(O).sub.2NR.sup.3R.sup.4, N(R.sup.4)C(O)OR.sup.3, CR.sup.4NOR.sup.3, CH.sub.2ONC(CN).sub.2, NR.sup.4C(O)R.sup.5, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl group wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxy, trifluoromethoxy; R.sup.3 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, and cyclopropyl, difluoromethyl, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxycarbonyl, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl group, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, and trifluoromethyl; R.sup.4, R.sup.5 are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, difluoromethyl, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxy, triflouromethoxy, methoxycarbonyl, non-substituted or substituent phenyl and non-substituted or substituent pyridyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, methyl, ethyl, and propyl, chloromethyl, bromomethyl, trifluoromethyl, heptafluoroisopropyl, methoxy and trifluoromethoxy.

9. The compound according to claim 7, wherein L is selected from the group consisting of CH.sub.2, CH.sub.2CH.sub.2, NH(CO)CH.sub.2 and OCH.sub.2CH.sub.2; W is selected from the group consisting of W.sup.12, W.sup.16, W.sup.18, W.sup.23, W.sup.49, W.sup.67, W.sup.68, W.sup.69 and W.sup.82; X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, and X.sup.9 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, heptafluoroisopropyl, OR.sup.3, C(O)OR.sup.3, N(R.sup.4)S(O).sub.2R.sup.5, S(O).sub.2NR.sup.3R.sup.4, N(R.sup.4)C(O)OR.sup.3, CR.sup.4NOR.sup.3, CH.sub.2ONC(CN).sub.2, NR.sup.4C(O)R.sup.5, non-substituted or substituted phenyl and non-substituted or substituted pyridyl, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxy, and trifluoromethoxy; Z is selected from the group consisting of hydrogen, methyl, and phenylmethyl; K is oxygen; R.sup.3 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, difluoromethyl, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxycarbonyl, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl group, wherein substituent group is selected from the group consisting of halogen, cyano group, nitro group and trifluoromethyl; and R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen and methyl groups, Ethyl, propyl, isopropyl, cyclopropyl, difluoromethyl, trifluoromethyl, heptafluoropropyl, heptafluoroisopropyl, methoxy, trifluoromethoxy, methoxycarbonyl, non-substituted or substituted phenyl group and non-substituted or substituted pyridyl group, wherein the substituent group is selected from the group consisting of halogen, cyano, nitro, methyl, ethyl, propyl, chloromethyl, bromomethyl, trifluoromethyl, heptafluoroisopropyl, methoxy, and trifluoromethoxy.

10. The compound according to claim 7, wherein L is selected from the group consisting of CH.sub.2, CH.sub.2CH.sub.2, NH(CO)CH.sub.2 and OCH.sub.2CH.sub.2; W is selected from the group consisting of W.sup.21, W.sup.48, W.sup.70, W.sup.71, W.sup.72, W.sup.74, W.sup.79, W.sup.80, W.sup.81 and W.sup.83; and X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, and X.sup.9 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, heptafluoroisopropyl, methoxy, and trifluoromethoxy; Z is hydrogen or methyl; K is oxygen; Q is selected from the group consisting of Q.sup.1-10, non-substituted or substituted phenyl group and a non-substituted or substituted pyridyl group wherein a substituent group is selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, amino, chloromethyl, bromomethyl, difluoromethyl Base, trifluoromethyl, heptafluoroisopropyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethoxy, methylthio, ethylthio, trifluoromethylthio, or trifluoroethylthio; T is cyano, methyl, ethyl, propyl, isopropyl, cyclopropyl, trifluoroethyl, difluoroethyl, cyclopropyl, cyclobutane, cyclopentane, alkyl, a cyclohexane group, a phenyl group or a pyridyl group, unsubstituted or substituted by halogen, cyano, nitro, methyl, ethyl, propyl, Isopropyl, chloromethyl, bromomethyl, trifluoromethyl, heptafluoroisopropyl, cyclopropyl, cyclobutane, cyclopentyl, cyclohexane, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethoxy, methylthio, ethylthio, trifluoromethylthio, trifluoroethylthio.

11. A fungicidal or bactericidal composition comprising an effective amount of the malonitrile oxime ether compound according to claim 1.

12. A fungicidal composition comprising the compound according to claim 1 and an acceptable carrier, wherein the weight percentage of the compound in the composition is 0.1-99%.

13. A method for controlling diseases of plants, comprising applying an effective quantity of a composition according to claim 12 to the said plants or to the soil where the said plants grow or are capable of growing.

Description

DETAILED DESCRIPTION OF THE INVENTION

(1) The following examples are illustrative of the present invention, but without being restricted thereby.

PREPARATION EXAMPLE

Example 1: The Preparation of Compound 4

(2) ##STR00192##

(3) To a solution of malononitrile oxime ether sodium salt (0.22 g, 1.86 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added p-chlorobenzyl chloride (0.3 g, 1.86 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 4 (0.21 g) as yellow oil with yield of 51%.

Example 2: The Preparation of Compound 25

(4) ##STR00193##

(5) To a solution of malononitrile oxime ether sodium salt (0.12 g, 0.98 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 1-(bromomethyl)-4-(trifluoromethoxy)benzene (0.25 g, 0.98 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 25 (0.16 g) as white solid with yield of 61%.

Example 3: The Preparation of Compound 37

(6) ##STR00194##

(7) To a solution of malononitrile oxime ether sodium salt (0.18 g, 1.53 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 4-(bromomethyl)benzonitrile (0.3 g, 1.53 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 37 (0.18 g) as white solid with yield of 56%.

Example 4: The Preparation of Compound 53

(8) ##STR00195##

(9) To a solution of malononitrile oxime ether sodium salt (0.25 g, 2.16 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 2-chloro-5-(chloromethyl)pyridine (0.35 g, 2.16 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 53 (0.21 g) as yellow solid with yield of 44%.

Example 5: The Preparation of Compound 59

(10) ##STR00196##

(11) To a solution of malononitrile oxime ether sodium salt (0.18 g, 1.53 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 1,2-dichloro-4-(chloromethyl)benzene (0.3 g, 1.53 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 59 (0.22 g) as yellow solid with yield of 56%.

Example 6: The Preparation of Compound 96

(12) ##STR00197##

(13) A mixture of 2-methyl-1,1-biphenyl (0.8 g, 4.76 mmol), NBS (0.85 g, 4.76 mmol), AIBN (0.02 g) and tetrachloromethane (25 ml) was refluxed and monitored by Thin-Layer Chromatography until the reaction was over. The excessive tetrachloromethane was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain 2-(bromomethyl)-1,1-biphenyl (0.81 g) with yield of 69%.

(14) To a solution of malononitrile oxime ether sodium salt (0.24 g, 2.02 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 2-(bromomethyl)-1,1-biphenyl (0.5 g, 2.02 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 96 (0.31 g) as yellow oil with yield of 59%.

Example 7: The Preparation of Compound 102

(15) ##STR00198##

(16) To a solution of (2-methyl-[1,1-biphenyl]-3-yl)methanol (1 g, 5.04 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added slowly thionyl chloride (10 mL). The reaction was stirred overnight, and monitored by Thin-Layer Chromatography until the reaction was over, and the poured into water (100 mL). The water phase was extracted with ethyl acetate (250 mL), the organic phase were washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to get pure 3-(chloromethyl)-2-methyl-1,1-biphenyl (0.95 g) with yield of 87%.

(17) To a solution of malononitrile oxime ether sodium salt (0.27 g, 2.31 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 3-(chloromethyl)-2-methyl-1,1-biphenyl (0.5 g, 2.31 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:5) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:5; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 102 (0.31 g) as yellow solid with yield of 60%.

Example 8: The Preparation of Compound 114

(18) ##STR00199##

(19) A mixture of phenyl(o-tolyl)methanone (0.8 g, 4.08 mmol), NBS (0.73 g, 4.76 mmol), AIBN (0.01 g) and tetrachloromethane (25 ml) was refluxed and monitored by Thin-Layer Chromatography until the reaction was over. The excessive tetrachloromethane was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain (2-(bromomethyl)phenyl)(phenyl)methanone (0.95 g) with yield of 85%.

(20) To a solution of malononitrile oxime ether sodium salt (0.26 g, 2.18 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added (2-(bromomethyl)phenyl)(phenyl)methanone (0.6 g, 2.18 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:3) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:5; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 114 (0.42 g) as yellow solid with yield of 67%.

Example 9: The Preparation of Compound 115

(21) ##STR00200##

(22) A mixture of benzothioamide (1.5 g, 10.93 mmol), 1,3-dichloropropan-2-one (0.64 g, 10.93 mmol) and ethanol (50 ml) was refluxed in a 100 mL reaction flask and monitored by Thin-Layer Chromatography until the reaction was over. The excessive ethanol was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain 4-(chloromethyl)-2-phenylthiazole (1.9 g) with yield of 83%.

(23) To a solution of malononitrile oxime ether sodium salt (0.28 g, 2.38 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added 4-(chloromethyl)-2-phenylthiazole (0.5 g, 2.38 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:5) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:5; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 115 (0.35 g) as yellow solid with yield of 55%.

Example 10: The Preparation of Compound 119

(24) ##STR00201##

(25) A mixture of 2-methylbenzo[d]thiazole (0.8 g, 5.36 mmol), NBS (0.95 g, 5.36 mmol), AIBN (0.01 g) and tetrachloromethane (25 ml) was refluxed and monitored by Thin-Layer Chromatography until the reaction was over. The excessive tetrachloromethane was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain 2-(bromomethyl)benzo[d]thiazole (0.75 g) with yield of 61%.

(26) To a solution of malononitrile oxime ether sodium salt (0.26 g, 2.19 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 2-(bromomethyl)benzo[d]thiazole (0.5 g, 2.19 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:5) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:5; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 119 (0.31 g) as red solid with yield of 58%.

Example 11: The Preparation of Compound 142

(27) ##STR00202##

(28) 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (2 g, 11.36 mmol) was dissolved in 20 mL sulfuryl dichloride, and then heated to reflux for 3 h, the excessive sulfuryl dichloride was evaporated under reduced pressure to get 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride, and then the carbonyl chloride was dissolved in 30 mL dichloromethane for the following reaction. To a cooled solution of (3-aminophenyl)methanol (1.4 g, 11.36 mmol) dissolved in 20 mL dichloromethane and 5 mL triethylamine was added slowly the solution of the carbonyl chloride at 0-5 C. After the reaction was stirred for 6 h at room temperature, analysis by Thin-Layer Chromatography showed complete conversion to product, the excessive solvent was evaporated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain 3-(difluoromethyl)-N-(3-(hydroxymethyl)phenyl)-1-methyl-1H-pyrazole-4-carboxamide (2.32 g) as white solid with yield of 73%. .sup.1H NMR (300 MHz, CDCl.sub.3) (ppm): 4.11 (s, 3H), 4.73 (s, 2H), 7.16-7.81 (m, 6H).

(29) ##STR00203##

(30) To a solution of 3-(difluoromethyl)-N-(3-(hydroxymethyl)phenyl)-1-methyl-1H-pyrazole-4-carboxamide (1 g, 3.56 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added slowly thionyl chloride (10 mL). The reaction was stirred overnight, and monitored by Thin-Layer Chromatography until the reaction was over, and the poured into water (100 mL). The water phase was extracted with ethyl acetate (250 mL), the organic phase were washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to get N-(3-(chloromethyl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (0.83 g) with yield of 78%.

(31) To a solution of malononitrile oxime ether sodium salt (0.20 g, 1.67 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added N-(3-(chloromethyl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (0.5 g, 1.67 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:2) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 142 (0.21 g) as yellow solid with yield of 35%.

Example 12: The Preparation of Compound 167

(32) ##STR00204##

(33) To 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (1.5 g, 8.52 mmol) was added dropwise 20 mL sulfuryl dichloride, and then heated to reflux for 3 h, the excessive sulfuryl dichloride was evaporated under reduced pressure to get 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride, and then the carbonyl chloride was dissolved in 30 mL dichloromethane for the following reaction. To a cooled solution of (3-(aminomethyl)phenyl)methanol (1.17 g, 8.52 mmol) dissolved in 20 mL dichloromethane and 5 mL triethylamine was added dropwise the solution of the carbonyl chloride at 0-5 C. After the reaction was stirred for 6 h at room temperature, analysis by Thin-Layer Chromatography showed complete conversion to product, the excessive solvent was evaporated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain 3-(difluoromethyl)-N-(3-(hydroxymethyl)benzyl)-1-methyl-1H-pyrazole-4-carboxamide (1.8 g) as white solid with yield of 72%.

(34) ##STR00205##

(35) To a solution of 3-(difluoromethyl)-N-(3-(hydroxymethyl)benzyl)-1-methyl-1H-pyrazole-4-carboxamide (0.5 g, 1.69 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added slowly thionyl chloride (8 mL). The reaction was stirred overnight, and monitored by Thin-Layer Chromatography until the reaction was over, and the poured into water (100 mL). The water phase was extracted with ethyl acetate (250 mL), the organic phase were washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to get N-(3-(chloromethyl)benzyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (0.39 g) with yield of 73%.

(36) To a solution of malononitrile oxime ether sodium salt (0.1 g, 0.85 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added N-(3-(chloromethyl)benzyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (0.25 g, 0.8 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:2) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 167 (0.15 g) as yellow oil with yield of 51%.

Example 13: The Preparation of Compound 185

(37) ##STR00206##

(38) 4-methylbenzoic acid (1.5 g, 11.02 mmol) was dissolved in 20 mL sulfuryl dichloride, and then heated to reflux for 3 h, the excessive sulfuryl dichloride was evaporated under reduced pressure to get 4-methylbenzoyl chloride, and then the carbonyl chloride was dissolved in 30 mL dichloromethane for the following reaction. To a cooled solution of N-methylaniline (1.18 g, 11.02 mmol) dissolved in 20 mL dichloromethane and 5 mL triethylamine was added slowly the solution of the carbonyl chloride at 0-5 C. After the reaction was stirred for 4 h at room temperature, analysis by Thin-Layer Chromatography showed complete conversion to product, the excessive solvent was evaporated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain N,4-dimethyl-N-phenylbenzamide (1.8 g) as white solid with yield of 73%. .sup.1H NMR (300 MHz, CDCl.sub.3) (ppm): 2.25 (s, 3H), 3.49 (s, 3H), 6.94-7.05 (m, 4H), 7.14-7.26 (m, 5H).

(39) ##STR00207##

(40) A mixture of N,4-dimethyl-N-phenylbenzamide (0.8 g, 3.55 mmol), NBS (0.64 g, 3.56 mmol), AIBN (0.01 g) and tetrachloromethane (25 ml) was refluxed and monitored by Thin-Layer Chromatography until the reaction was over. The excessive tetrachloromethane was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:5; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain 4-(bromomethyl)-N-methyl-N-phenylbenzamide (0.79 g) with yield of 73%.

(41) To a solution of malononitrile oxime ether sodium salt (0.16 g, 1.37 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 4-(bromomethyl)-N-methyl-N-phenylbenzamide (0.4 g, 1.32 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:3) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 185 (0.25 g) as yellow solid with yield of 60%.

Example 14: The Preparation of Compound 202

(42) ##STR00208##

(43) To a cooled solution of 6-methoxybenzo[d]thiazol-2-amine (2.0 g, 11.10 mmol) dissolved in 30 mL dichloromethane and 5 mL triethylamine was added slowly the solution of chloroacetyl chloride (2.0 g, 11.10 mmol) in dichloromethane (10 mL) at 0-5 C. After the reaction was stirred for 4 h at room temperature, analysis by Thin-Layer Chromatography showed complete conversion to product, the excessive solvent was evaporated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:2; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain 2-chloro-N-(6-methoxybenzo[d]thiazol-2-yl)acetamide (2.42 g) with yield of 85%.

(44) To a solution of malononitrile oxime ether sodium salt (0.92 g, 7.79 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added 2-chloro-N-(6-methoxybenzo[d]thiazol-2-yl)acetamide (2.0 g, 7.79 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:1) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:1; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 202 (1.14 g) as yellow solid with yield of 46%.

Example 15: The Preparation of Compound 203

(45) ##STR00209##

(46) To a solution of quinolin-6-ylmethanol (1 g, 6.28 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added slowly thionyl chloride (5 mL). The reaction was stirred overnight, and monitored by Thin-Layer Chromatography until the reaction was over, and the poured into water (100 mL). The water phase was extracted with ethyl acetate (250 mL), the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to get 6-(chloromethyl)quinoline (0.75 g) with yield of 67%.

(47) To a solution of malononitrile oxime ether sodium salt (0.33 g, 2.81 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 6-(chloromethyl)quinoline (0.5 g, 2.81 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:3) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 203 (0.35 g) as brown oil with yield of 53%.

Example 16: The Preparation of Compound 210

(48) ##STR00210##

(49) To a solution of malononitrile oxime ether sodium salt (0.29 g, 2.48 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added 1-(2-chloroethoxy)-4-nitrobenzene (0.5 g, 2.48 mmol). The reaction was stirred at 80 C., and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:5) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:5; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 210 (0.26 g) as white solid with yield of 40%.

Example 17: The Preparation of Compound 222

(50) ##STR00211##

(51) To a cooled solution of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (1 g, 5.15 mmol) dissolved in 25 mL tetrahydrofuran and triethylamine (0.63 g, 6.18 mmol) in a 50 mL reaction flask, ethyl chloroformate (0.67 g, 6.18 mmol) was added slowly. After the reaction was stirred at room temperature, analysis by Thin-Layer Chromatography showed complete conversion to product. Sodium borohydride (1.95 g, 51.52 mmol) was added and then methanol (10 mL) was added slowly at 00. The mixture was stirred at 0-5 C. for 30 min, the reaction was stirred overnight, and monitored by Thin-Layer Chromatography until the reaction was over, and the poured into water (100 mL). The water phase was extracted with ethyl acetate (250 mL), the organic phase were washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to get N-(3-(chloromethyl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (0.53 g) with yield of 57%.

(52) ##STR00212##

(53) To a solution of N-(3-(chloromethyl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (0.3 g, 1.67 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added slowly thionyl chloride (5 mL). The reaction was stirred overnight, and monitored by Thin-Layer Chromatography until the reaction was over, and the poured into water (100 mL). The water phase was extracted with ethyl acetate (250 mL), the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. the residual was purified by column chromatography on silica gel to get 4-(chloromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole (0.25 g) with yield of 76%.

(54) To a solution of malononitrile oxime ether sodium salt (0.13 g, 1.11 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 4-(chloromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole (0.2 g, 1.11 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:2) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:3; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 222 (0.13 g) as yellow oil with yield of 46%.

Example 18: The Preparation of Compound 230

(55) ##STR00213##

(56) To a cooled solution of (3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanamine (0.45 g, 2.12 mmol) dissolved in 30 mL dichloromethane and 5 mL triethylamine in a 100 mL reaction flask was added slowly the solution of 4-(chloromethyl)benzoyl chloride (0.4 g, 2.12 mmol) in dichloromethane (10 mL). After the reaction was stirred at room temperature, analysis by Thin-Layer Chromatography showed complete conversion to product, the reaction mixture was concentrated under reduced pressure. the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:2; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to get N-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)methyl)-4-(chloromethyl)benzamide (0.52 g) with yield of 68%.

(57) ##STR00214##

(58) To a solution of malononitrile oxime ether sodium salt (0.1 g, 0.85 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added N-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)methyl)-4-(chloromethyl)benzamide (0.3 g, 0.83 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:5) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:5; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 230 (0.19 g) as yellow solid with yield of 55%.

(59) Biological Testing

Example 19: Rice Blast and Gray Mold Testing

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

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

(62) At the dosage of 25 mg/L, the inhibition rate of compounds 5, 7, 23, 57, 59, 65, 69, 85, 91, 93, 99, 102, 106, 107, 109, 112, 113, 114, 119, 122, 142, 168, 189, 194, 201, 203, 205, 207, 208, 209, 210, 213, 214, 215, 216, 218, 220, 221, 222, 224, 225, 228, 229, 230, 231, 232, 233 was 100% against rice blast

(63) At the dosage of 25 mg/L, the inhibition rate of compounds 4, 7, 22, 36, 53, 59, 60, 69, 86, 96, 99, 102, 105, 107, 109, 112, 113, 115, 116, 118, 120, 150, 159, 167, 185, 187, 202, 203, 204, 205, 206, 208, 209, 210, 214, 215, 216, 218, 220, 221, 228, 230, 231, 232 was 100% against gray mold.

Example 20: The Determination Method of Protective Activity In Vivo

(64) The method is as followed: The compound is dissolved in a proper solvent to get mother solution. The 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. Plants are sprayed on leaves with the preparation of active compound according to the invention and spray application is repeated 3 times. Plants, used as controls, are treated with an aqueous solution not containing the active material. The plants are inoculated one day after treating the plants with the compounds of this invention. The plants are stored in a humidity chamber (25 C. (day), 20 C. (night), 95-99% humidity) and then transferred into greenhouse after 24 hours. The activity of compound is obtained by eyeballing after 7 days according to the A Manual of Assessment Keys for Plant Diseases published by American Phytopathological Society. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

(65) At the dosage of 400 ppm, the compounds 86, 91, 94, 103, 109, 110, 114, 115, 142, 187, 188, 189, 233 showed more than 80% control against corn rust

Example 21: The Determination of Controlling Plant Bacterial Disease

(66) The compounds of the present invention have been tested for the control of various plant bacterial diseases. The test procedure is as follows:

(67) Melon bacterial fruit blotch: The testing compound is dissolved in a small amount of DMF and diluted with water to the desired concentration. The pathogenic bacteria in the stable growth phase is mixed with the testing solution. After melon seeds (accelerating germination) soaked in the solution containing pathogenic bacteria and compound for 0.5 hour, the seeds are sown in earthworm soil cup and then transferred into a greenhouse to allow disease to develop. After 2 weeks, The activity of the compound is evaluated based on germination or growth of control treatment

(68) Soft rot of chinese cabbage: Chinese cabbage leaves are cut into 2 cm square and placed on the double filter paper in a petri dish. The testing compound is dissolved in DMF and diluted with water to the desired concentration. The testing solution is sprayed onto the surface of the cabbage leaf and dried in a fume hood. The surface of cabbage leaf is pierced using inoculation needle. A spore suspension (5 l) of the chinese cabbage soft rot bacteria in the stable growth phase is inoculated onto the breakage of leaves, disease development is allowed to progress in a growth cabinet under dark condition for 48 hours. The activity of the compound is evaluated based on germination or growth of control treatment.

(69) Bacterial leaf spot of cucumber, bacterial leaf spot of tomato, bacterial leaf streak of rice, bacterial blight of rice: The testing compound is dissolved in DMF and diluted with water to the desired concentration. The testing solution is sprayed to the host plant by a special plant sprayer. After air drying in cool place, the plant is inoculated with pathogen in the stable growth phase, and then transferred into a greenhouse and incubated for 10 days under a humid atmosphere in common. Grading is carried out, in comparison with the control plants.

(70) The test results are as follows:

(71) At the dosage of 800 mg/L, the compounds 9, 59, 83 and 115 showed 100% control against melon bacterial fruit blotch.

(72) At the dosage of 600 mg/L, the compounds 9, 19, 34, 37, 59, 83 and 115 showed 100% control against bacterial leaf spot of cucumber, bacterial leaf streak of rice and bacterial blight of rice.

(73) At the dosage of 400 mg/L, the compounds 9, 19, 34, 36, 37, 59, 83 and 115 showed 100% control against soft rot of chinese cabbage and bacterial leaf spot of tomato.

Example 22: Field Trial

(74) Compounds 59 and 115 were selected from the above compounds for field trial to control bacterial leaf streak of rice (Xanthomonas oryzae pv. oryzicola) at dosage of 400 g a.i./hm.sup.2. The check (thiazole zinc and kocide 3000, commercially available) was set at one dose (400 g a.i./hm.sup.2). The plot size was 15 m.sup.2 and treatments were assigned to plots randomly. Spray applications on leaves and stems were made on 7-day intervals and each application was repeated 3 times. A week after 3 spray applications, five random points of each plot were investigated to calculate the effectiveness of the testing compounds in controlling disease according to pesticide guidelines for the field efficacy trials

(75) TABLE-US-00003 TABLE 3 Field trial results for test compounds against bacterial leaf streak of rice Concentrations Disease control (%) compound (g a.i./hm.sup.2) repeat I repeat II repeatIII average 115 400 61.08 53.23 66.00 60.10 59 400 56.96 58.37 51.24 55.52 kocide 3000 400 34.91 33.29 39.72 35.97 thiazole zinc 400 39.21 37.24 37.88 38.11