IP Library Granted Patent US 8,614,214
Granted Patent B2
US 8,614,214 · App. 13/883,146 · Granted Dec 24, 2013

Pyrazole amide compounds and uses thereof

Inventors: Changling Liu (Shenyang, CN); Lizeng Wang (Shenyang, CN); Zhinian Li (Shenyang, CN); Xufeng Sun (Shenyang, CN); Jie Lan (Shenyang, CN); Lanhui Ren (Shenyang, CN); Qiang Wu (Shenyang, CN); Huiwei Chi (Shenyang, CN)
Assignee: Sinochem Corporation
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Quick Facts
Patent No.
US 8,614,214
App. No.
13/883,146
Granted
Dec 24, 2013
Kind
B2
Abstract

Disclosed is a pyrazole amide compound having fungicidal activity, with a structure shown by the general formula (I): Each of the substituents of the compound being defined as in the description. The compound of the present invention has fungicidal activity, and excellent prevention and controlling effects on diseases, such as cucumber downy mildew, corn rust, wheat powdery mildew, rice blast, etc., and in particular, a better prevention and controlling effect on cucumber downy mildew and corn rust. Also disclosed is a process for preparing the compound, a fungicidal composition containing the compound of general formula (I) and the use thereof in preventing and controlling disease in crops.

Claims (117)

1. A pyrazole amide compound represented by the following formula (I):

wherein:

R 1 is selected from H, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 cyanoalkyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 haloalkoxycarbonyl, C 1 -C 12 alkylaminocarbonyl, C 1 -C 12 haloalkylaminocarbonyl, C 3 -C 6 cycloalkyl or R 8 ;

R 2 is selected from H, halogen, CN, C 1 -C 12 cyanoalkyl, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 cyanoalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylthioC 1 -C 12 alkyl, C 1 -C 12 haloalkylthioC 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 3 -C 6 cycloalkyl or R 8 ;

R 3 is selected from H or C 1 -C 12 alkyl; m is selected from 0 to 5;

R 4 is selected from halogen, CN, CONH 2 , CSNH 2 , NO 2 , C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylthioC 1 -C 12 alkyl, C 1 -C 12 haloalkylthioC 1 -C 12 alkyl, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 2 C 12 dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, C 2 -C 12 alkenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 alkenoxy, C 2 -C 12 haloalkenoxy, C 2 -C 12 alkynyl, C 2 -C 12 haloalkynyl, C 2 -C 12 alkynoxy, C 2 -C 12 haloalkynoxy, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl or R 8 ; n is selected from 0 to 4;

R 5 is selected from H, C 1 -C 12 alkyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 12 cyanoalkyl, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 2 -C 12 dialkylamino, C 2 -C 12 alkenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 alkynyl, C 2 -C 12 haloalkynyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylcarbonylamino,

 or R 8 ;

R 6 is selected from H, CN, SCN, H(C═O), C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 cyanoalkyl, C 1 -C 12 hydroxyalkyl, C 3 -C 6 cycloalkyl or R 8 ; p is selected from 0 to 5;

X 1 is selected from H, halogen, NO 2 , CN, SCN, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C r C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfinyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 haloalkylthio, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylthioC 1 -C 12 alkyl or C 1 -C 12 haloalkylthioC 1 -C 12 alkyl;

X 2 , X 3 , X 4 and X 5 may be the same or different, mutually independently selected from H, halogen, CN, NO 2 , OH, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio or C 1 -C 12 alkylsulfonyl;

Q 1 and Q 2 may be the same or different, mutually independently selected from H, NH 2 , OH, CN, SCN, C 1 -C 12 cyanoalkyl, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfinyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylamino, C 2 -C 12 dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, H(C═O), C 1 -C 12 alkylaminocarbonyl, C 1 -C 12 alkoxycarbonyl, C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylaminothio, C 2 -C 12 dialkylaminothio, C 3 -C 6 cycloalkyl or R 8 ;

Y is selected from O, S or NR 7 ;

Z is selected from O or S;

R 7 is selected from H, CN, NH 2 , OH, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 12 alkoxy, C 1 -C 12 haloalkoxy, C 3 -C 6 cycloalkyl, C 1 -C 12 cyanoalkyl, C 1 -C 12 cyanoalkoxy, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 2 -C 12 dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C 2 -C 12 alkenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 alkenoxy, C 2 -C 12 haloalkenoxy, C 2 -C 12 alkynyl, C 2 -C 12 haloalkynyl, C 2 -C 12 alkynoxy, C 2 -C 12 haloalkynoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylcarbonylamino,

 or R 8 ;

Or, when Y is selected from NR 7 , NR 7 and R 5 form a unsubstituted or substituted five-membered or six-membered ring with 1-4 substitutents selected independently from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 3 -C 6 cycloalkyl;

R 8 is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, phenylC 1 -C 6 alkyl, naphthyl, naphthylC 1 -C 6 alkyl, heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl or heteroarylC 1 -C 6 alkyl, which can be unsubstituted or further substituted with 1-5 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO 2 , CN, SH, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 3 -C 12 cycloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 2 -C 12 alkenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 alkynyl, C 2 -C 12 haloalkynyl, C 3 -C 12 alkenoxy, C 3 -C 12 haloalkenoxy, C 3 -C 12 alkynoxy, C 3 -C 12 haloalkynoxy, C 1 -C 12 alkylsulfinyl, C 1 -C 12 haloalkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkylcarbonylamino, C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxyC 1 -C 12 alkoxy, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonylamino, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkoxy, CHO, CO 2 H, CO 2 Na, CO 2 NH 4 , NR 9 R 10 , C(═O)NR 9 R 10 , OC(═O)NR 9 R 10 , C(═S)NR 9 R 10 or SO 2 NR 9 R 10 ;

R 9 and R 10 may be the same or different, mutually independently selected from H, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 3 -C 6 cycloalkyl or R 8 ;

(CHR 3 )mCON(Q 2 ) links with phenyl ring at the 2, 3 or 4-position.

2. The compound according to claim 1 , wherein:

R 1 is selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 haloalkylaminocarbonyl, C 3 -C 6 cycloalkyl or R 8 ;

R 2 is selected from H, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 cyanoalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 haloalkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 3 -C 6 cycloalkyl or R 8 ;

R 3 is selected from H or C 1 -C 4 alkyl; m is selected from 1 to 3;

R 4 is selected from halogen, CN, CONH 2 , CSNH 2 , NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 1 -C 4 haloalkoxyC 1 -C 4 alkyl, C 1 -C 4 alkylthioC 1 -C 4 alkyl, C 1 -C 4 haloalkylthioC 1 -C 4 alkyl, C 1 -C 4 alkylamino, C 1 -C 4 haloalkylamino, C 2 -C 4 dialkylamino, piperidyl, Pyrrolidyl, N-methyl piperazinyl, morpholinyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkenoxy, C 2 -C 4 haloalkenoxy, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 2 -C 4 alkynoxy, C 2 -C 4 haloalkynoxy, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl or R 8 ; n is selected from 0 to 3;

R 5 is selected from H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 cyanoalkyl, C 1 -C 4 alkylamino, C 1 -C 4 haloalkylamino, C 2 -C 6 dialkylamino, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 1 -C 4 alkyloxycarbonylC 1 -C 4 alkyl, C 1 -C 4 alkylcarbonylamino,

 or R 8 ;

R 6 is selected from H, CN, SCN, H(C═O), C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkyloxycarbonyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 cyanoalkyl, C 1 -C 4 hydroxyalkyl, C 3 -C 6 cycloalkyl or R 8 ; p is selected from 0 to 4;

X 1 is selected from H, halogen, NO 2 , CN, SCN, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 1 -C 4 haloalkoxyC 1 -C 4 alkyl, C 1 -C 4 alkylthioC 1 -C 4 alkyl or C 1 -C 4 haloalkylthioC 1 -C 4 alkyl;

X 2 , X 3 , X 4 and X 5 may be the same or different, mutually independently selected from H, halogen, CN, NO 2 , OH, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl;

Q 1 and Q 2 may be the same or different, mutually independently selected from H, NH 2 , OH, CN, SCN, C 1 -C 4 cyanoalkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, H(C═O), C 1 -C 4 alkylaminocarbonyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylaminothio, C 2 -C 4 dialkylaminothio, C 3 -C 6 cycloalkyl or R 8 ;

Y is selected from O, S or NR 7 ;

Z is O;

R 7 is selected from H, CN, NH 2 , OH, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyl, C 1 -C 4 cyanoalkyl, C 1 -C 4 cyanoalkoxy, C 1 -C 4 alkylamino, C 1 -C 4 haloalkylamino, C 2 -C 4 dialkylamino, piperidyl, pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkenoxy, C 2 -C 4 haloalkenoxy, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 2 -C 4 alkynoxy, C 2 -C 4 haloalkynoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 1 -C 4 alkoxycarbonylC 1 -C 4 alkyl, C 1 -C 4 alkylcarbonylamino,

 or R 8 ;

Or, when Y is selected from NR 7 , NR 7 and R 5 form a unsubstituted or substituted five-membered or six-membered ring with 1-2 substitutents selected independently from C 1 -C 3 alkyl;

R 8 is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, benzyl, phenethyl, naphthyl, pyridyl, picolyl, pyridylethyl, pyrimidyl, pyridazinyl, pyrazinyl, cyanuro, unsym-triazinyl, furanyl, thienyl, pyrrolyl, thiazolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadizolyl, benzofuryl, benzothiophenyl, benzothiazolyl, benzoxazolyl, benzoxazolylmethyl, benzopyranyl, benzopyronyl, benzopyridazinyl, indolyl, quinolyl, quinoxalinyl, triazolopyrimidinyl, imidazopyridinyl, imidazothiazolyl, purinyl, pyridylformoxyl, pyrimidinylformoxyl, pyridyloxycarbonyl, pyrimidinyloxycarbonyl, pyridylaminocarbonyl, pyrimidinylaminocarbonyl or thiazolylmethyl, which can be unsubstituted or further substituted with 1-3 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO 2 , CN, SH, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 3 -C 6 alkenoxy, C 3 -C 6 haloalkenoxy, C 3 -C 6 alkynoxy, C 3 -C 6 haloalkynoxy, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 1 -C 4 alkylcarbonyloxy, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkoxyC 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonylC 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonylamino, C 1 -C 4 alkoxycarbonylC 1 -C 4 alkoxy, CHO, CO 2 H, CO 2 Na, CO 2 NH 4 , NR 9 R 10 , C(═O)NR 9 R 10 , OC(═O)NR 9 R 10 , C(═S)NR 9 R 10 or SO 2 NR 9 R 10 ;

R 9 and R 10 may be the same or different, mutually independently selected from H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 3 -C 6 cycloalkyl or R 8 ;

(CHR 3 )mCON(Q 2 ) links with phenyl ring at the 2, 3 or 4-position.

3. The compound according to claim 2 , wherein:

R 1 is selected from H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or R 8 ;

R 2 is selected from H, chloride, bromine, fluorine, iodine, CN, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 cyanoalkoxy, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 1 -C 4 haloalkoxyC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or R 8 ;

R 3 is selected from H, methyl or ethyl; m is selected from 1, 2 or 3;

R 4 is selected from fluorine, chloride, bromine, iodine, CN, NO 2 , C 1 -C 3 alkyl, C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylamino, C 2 -C 4 dialkylamino or C 1 -C 3 alkylsulfonyl; n is selected from 0, 1, 2 or 3;

R 5 is selected from H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxyC 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 cyanoalkyl, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl or R 8 ;

R 6 is selected from H, CN, SCN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio or C 1 -C 3 hydroxyalkyl; p is selected from 0, 1, 2 or 3;

X 1 is selected from H, fluorine, chloride, bromine, iodine, NO 2 , CN, SCN, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

X 2 , X 3 , X 4 and X 5 may be the same or different, mutually independently selected from H, fluorine, chloride, bromine, iodine, CN, NO 2 , OH, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;

Q 1 and Q 2 may be the same or different, mutually independently selected from H, CN, SCN, C 1 -C 3 alkyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxyC 1 -C 2 alkyl or H(C═O);

Y is selected from O or NR 7 ;

Z is O;

R 7 is selected from H, CN, NH 2 , OH, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyl, C 1 -C 3 cyanoalkyl, C 1 -C 3 cyanoalkoxy, C 1 -C 3 alkylamino, C 1 -C 3 haloalkylamino, C 2 -C 4 dialkylamino, piperidyl, pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C 3 -C 4 alkenyl, C 3 -C 4 haloalkenyl, C 3 -C 4 alkenoxy, C 3 -C 4 haloalkenoxy, C 3 -C 4 alkynyl, C 3 -C 4 haloalkynyl, C 3 -C 4 alkynoxy, C 3 -C 4 haloalkynoxy, C 1 -C 3 alkylsulfonyl, C 1 -C 3 haloalkylsulfonyl or R 8 ;

Or, when Y is selected from NR 7 , NR 7 and R 5 form piperidine, tetrahydropyrrole, N-methylpiperazine, morpholine or 2,6-dimethylmorpholine;

R 8 is selected from phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-methylphenyl, trifluoromethylphenyl, 4-methoxylphenyl, 2,6-dichloro-4-trifluoromethylphenyl, benzoyl, 4-chlorobenzoyl, 2,4-dichlorobenzoyl, 4-trifluoromethylbenzoyl, phenoxycarbonyl, chlorophenoxycarbonyl, 2,4-dichlorophenoxycarbonyl, 4-trifluoromethylphenoxycarbonyl, phenylaminocarbonyl, 4-chlorophenylaminocarbonyl, 2,4-dichlorophenylaminocarbonyl, 4-trifluoromethyphenylaminocarbonyl, benzyl, 4-chlorobenzyl, 4-tert-butylbenzyl, 4-trifluoromethylbenzyl, phenethyl, 2-pyridyl, 3-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3,5,6-trichloro-2-pyridyl, 5-trifluoromethyl-2-pyridyl, 5-methyl-2-pyridyl, 3-chloro-5-cyano-2-pyridyl, 3-chloro-5-trifluoromethyl-2-pyridyl, 2-picolyl, 2-chloro-5-picolyl, 3-chloro-5-trifluoro-2-picolyl, 2-pyridinylethyl, 3-chloro-5-trifluoromethyl-2-pyridinylethyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, thiazole-2-yl, 2-chloro-5-thiazolylmethyl, 3-pyridylformoxyl, 2-chloro-3-pyridylformoxyl, 2-chloro-5-pyridylformoxyl, 2-pyrimidinylformoxyl, 5-trifluoromethyl-2-pyrimidinylformoxyl, 2-pyridyloxycarbonyl, 3-chloro-2-pyridyloxycarbonyl, 3,5-dichloro-2-pyridyloxycarbonyl, 5-trifluoromethyl-2-pyridyloxycarbonyl, 5-methyl-2-pyridyloxycarbonyl, 3-chloro-5-cyano-2-pyridyloxycarbonyl, 3-chloro-5-trifluoromethyl-2-pyridyloxycarbonyl, 2-pyrimidinyloxycarbonyl, 5-trifluoromethyl-2-pyrimidinyloxycarbonyl, 2-pyridylaminocarbonyl, 3-chloro-2-pyridylaminocarbonyl or 2-pyrimidinylaminocarbonyl;

(CHR 3 )mCON(Q 2 ) links with phenyl ring at the 2, 3 or 4-position.

4. The compound according to claim 3 , wherein:

R 1 is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or R 8 ;

R 2 is selected from H, chloride, bromine, fluorine, CN, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyl, trifluoroethoxyl, fluoromethoxyl, cyanomethoxyl, methoxymethyl, trifluoromethoxymethyl, trifluoroethoxymethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or R 8 ;

R 3 is selected from H or methyl; m is 1;

R 4 is selected from fluorine, chloride, bromine, iodine, CN, methyl, ethyl, trifluoromethyl, methoxyl, trifluoromethoxyl or methylsulfonyl; n is selected from 0, 1, 2 or 3;

R 5 is selected from H, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclohexyl, cyanomethyl, allyl, propargyl or R 8 ;

R 6 is selected from H, CN, SCN, methyl or ethyl; p is selected from 0, 1, 2 or 3;

X 1 is selected from H, fluorine, chloride, bromine, iodine, NO 2 , methyl or chloromethyl;

X 2 , X 3 , X 4 and X 5 may be the same or different, mutually independently selected from H, chloride, bromine or methoxyl;

Q 1 and Q 2 are H;

Y is selected from O or NR 7 ;

Z is O;

R 7 is selected from H, CN, NH 2 , OH, methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyanomethyl, methylamino, dimethylamino, methylsulfonyl or R 8 ;

Or, when Y is selected from NR 7 , NR 7 and R 5 form piperidine, tetrahydropyrrole, N-methylpiperazine, morpholine or 2,6-dimethylmorpholine;

R 8 is selected from phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxylphenyl, 2,6-dichloro-4-trifluoromethylphenyl, benzyl, 4-chlorobenzyl, 4-tert-butylbenzyl, 4-trifluoromethylbenzyl, phenethyl, 2-pyridyl, 3-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3,5,6-trichloro-2-pyridyl, 5-trifluoromethyl-2-pyridyl, 5-methyl-2-pyridyl, 3-chloro-5-cyano-2-pyridyl, 3-chloro-5-trifluoromethyl-2-pyridyl, 2-picolyl, 2-chloro-5-picolyl, 3-chloro-5-trifluoromethyl-2-picolyl, 2-pyridinylethyl, 3-chloro-5-trifluoromethyl-2-pyridinylethyl, thiazole-2-yl, 2-chloro-5-thiazolylmethyl or 2-pyrimidinyl;

(CHR 3 )mCON(Q 2 ) links with phenyl ring at the 2, 3 or 4-position.

5. The compound according to claim 4 , wherein:

R 2 is selected from bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, cyclopropyl or 4-chlorophenyl;

R 3 is selected from H or methyl; m is 1;

R 4 is selected from fluorine, chloride, bromine, iodine, CN or methyl; n is selected from 0, 1 or 2;

R 6 is selected from H or methyl; p is selected from 0, 1, 2 or 3;

X 1 is selected from H, chloride or methyl;

X 2 , X 3 , X 4 , X 5 , Q 1 , Q 2 are H;

Z is O;

YR 5 is selected from amino, methylamino, ethylamino, dimethylamino, methoxyl, ethoxyl or morpholinyl;

(CHR 3 )mCON(Q 2 ) links with phenyl ring at the 2, 3 or 4-position.

6. A method of preparation of a compound of general formula (I) (when Q 1 =H) according to claim 1 , according to the following reaction routes:

Wherein:

R 1 is selected from H, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 cyanoalkyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 haloalkoxycarbonyl, C 1 -C 12 alkylaminocarbonyl, C 1 -C 12 haloalkylaminocarbonyl, C 3 -C 6 cycloalkyl or R 8 ;

R 2 is selected from H, halogen, CN, C 1 -C 12 cyanoalkyl, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 cyanoalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylthioC 1 -C 12 alkyl, C 1 -C 12 haloalkylthioC 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 3 -C 6 cycloalkyl or R 8 ;

R 3 is selected from H or C 1 -C 12 alkyl; m is selected from 0 to 5;

R 4 is selected from halogen, CN, CONH 2 , CSNH 2 , NO 2 , C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylthioC 1 -C 12 alkyl, C 1 -C 12 haloalkylthioC 1 -C 12 alkyl, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 2 -C 12 dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, C 2 -C 12 alkenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 alkenoxy, C 2 -C 12 haloalkenoxy, C 2 -C 12 alkynyl, C 2 -C 12 haloalkynyl, C 2 -C 12 alkynoxy, C 2 -C 12 haloalkynoxy, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl or R 8 ; n is selected from 0 to 4;

R 5 is selected from H, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 12 cyanoalkyl, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 2 -C 12 dialkylamino, C 2 -C 12 alkenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 alkynyl, C 2 -C 12 haloalkynyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylcarbonylamino,

 or R 8 ;

R 6 is selected from H, CN, SCN, H(C═O), C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 cyanoalkyl, C 1 -C 12 hydroxyalkyl, C 3 -C 6 cycloalkyl or R 8 ; p is selected from 0 to 5;

X 1 is selected from H, halogen, NO 2 , CN, SCN, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfinyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 haloalkylthio, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylthioC 1 -C 12 alkyl or C 1 -C 12 haloalkylthioC 1 -C 12 alkyl;

X 2 , X 3 , X 4 and X 5 may be the same or different, mutually independently selected from H, halogen, CN, NO 2 , OH, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio or C 1 -C 12 alkylsulfonyl;

Q 2 is selected from H, NH 2 , OH, CN, SCN, C 1 -C 12 cyanoalkyl, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfinyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylamino, C 2 -C 12 dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, H(C═O), C 1 -C 12 alkylaminocarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylaminothio, C 2 -C 12 dialkylaminothio, C 3 -C 6 cycloalkyl or R 8 ;

Y is selected from O, S or NR 7 ;

Z is selected from O or S;

R 7 is selected from H, CN, NH 2 , OH, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 3 -C 6 cycloalkyl, C 1 -C 12 cyanoalkyl, C 1 -C 12 cyanoalkoxy, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 2 -C 12 dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C 2 -C 12 alkenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 alkenoxy, C 2 -C 12 haloalkenoxy, C 2 -C 12 alkynyl, C 2 -C 12 haloalkynyl, C 2 -C 12 alkynoxy, C 2 -C 12 haloalkynoxy,

C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylcarbonylamino,

 or R 8 ;

Or, when Y is selected from NR 7 , NR 7 and R 5 form a unsubstituted or substituted five-membered or six-membered ring with 1-4 substitutents selected independently from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 3 -C 6 cycloalkyl;

R 8 is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, phenylC 1 -C 6 alkyl, naphthyl, naphthylC 1 -C 6 alkyl, heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl or heteroarylC 1 -C 6 alkyl, which can be unsubstituted or further substituted with 1-5 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO 2 , CN, SH, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 3 -C 12 cycloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 2 -C 12 alkenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 alkynyl, C 2 -C 12 haloalkynyl, C 3 -C 12 alkenoxy, C 3 -C 12 haloalkenoxy, C 3 -C 12 alkynoxy, C 3 -C 12 haloalkynoxy, C 1 -C 1 -C 12 haloalkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkylcarbonylamino, C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxyC 1 -C 12 alkoxy, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonylamino, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkoxy, CHO, CO 2 H, CO 2 Na, CO 2 NH 4 , NR 9 R 10 , C(═O)NR 9 R 10 , OC(═O)NR 9 R 10 , C(═S)NR 9 R 10 or SO 2 NR 9 R 10 ;

R 9 and R 10 may be the same or different, mutually independently selected from H, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 3 -C 6 cycloalkyl or R 8 ;

(CHR 3 )mCON(Q 2 ) links with phenyl ring at the 2, 3 or 4-position.

7. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 1 to agricultural fields.

8. A fungicidal composition comprising the compound having general formula (I) of claim 1 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.

9. A method of controlling fungi which comprises applying the composition according to claim 8 to agricultural fields.

10. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 2 to agricultural fields.

11. A fungicidal composition comprising the compound having general formula (I) of claim 2 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.

12. A method of controlling fungi which comprises applying the composition according to claim 11 to agricultural fields.

13. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 3 to agricultural fields.

14. A fungicidal composition comprising the compound having general formula (I) of claim 3 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.

15. A method of controlling fungi which comprises applying the composition according to claim 14 to agricultural fields.

16. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 4 to agricultural fields.

17. A fungicidal composition comprising the compound having general formula (I) of claim 4 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.

18. A method of controlling fungi which comprises applying the composition according to claim 17 to agricultural fields.

19. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 5 to agricultural fields.

20. A fungicidal composition comprising the compound having general formula (I) of claim 5 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.

21. A method of controlling fungi which comprises applying the composition according to claim 20 to agricultural fields.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2016
From: SINOCHEM CORPORATION; SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO. LTD
To: SHENYANG SINOCHEM AGROCHEMICALS R&D CO., LTD.
Reel/Frame 037812/0366 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2013
From: WU, QIANG; CHI, HUIWEI
To: SINOCHEM CORPORATION
Reel/Frame 030344/0904 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2013
From: LIU, CHANGLING; WANG, LIZENG; LI, ZHINIAN; SUN, XUFENG; LAN, JIE; REN, LANHUI
To: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.
Reel/Frame 030344/0914 →
Priority Claims (1)
CN 2010 1 0535131 · Nov 3, 2010 · national
Continuity (1)
Related Publication 20130225585A1 · Aug 29, 2013