IP Library › Granted Patent US 9,061,967

Granted Patent B2

US 9,061,967 · App. 13/578,787 · Granted Jun 23, 2015

Substituted diphenylamine compounds, preparation method and use thereof

Inventors: Changling Liu (Shenyang, CN); Huichao Li (Shenyang, CN); Zhinian Li (Shenyang, CN); Guang Huang (Shenyang, CN); Hong Zhang (Shenyang, CN)

Assignees: Shenyang Research Institute Of Chemical Industry Co., LTD.; Sinochem Corporation

C07C211/56 A01N33/18 A01N37/34 A01N37/44 A01N41/10 A01N43/40 C07C237/30 C07C237/40 C07C255/58 C07C317/36 C07C323/36 C07C327/48 C07D213/643 C07D213/70 A01N33/22

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Patent No.: US 9,061,967
App. No.: 13/578,787
Granted: Jun 23, 2015
Kind: B2

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Abstract

Substituted diphenylamine compounds of general formula I are provided, in which each substituted group is defined as in the description. The compounds of general formula I have broad-spectrum fungicidal activity in the field of agriculture. Furthermore, the preparation methods of the above compounds are simple.

Claims (55)

1. A substituted diphenylamine compound having general formula I:

wherein:

R 1 is selected from H, C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkylaminocarbonyl, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkoxyC 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylaminothio, C 2 -C 12 dialkylaminothio or CO—X—CO 2 R 9 , in which X is selected from (CHR 9 )n, CR 9 ═CR 10 or C 6 H 4 , n=1-6;

R 2 is selected from halogen, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylsulfonyl, C 3 -C 12 cycloalkyl, C 2 -C 12 dialkylamino, C 3 -C 12 alkenyloxy, C 3 -C 12 haloalkenyloxy, C 3 -C 12 alkynyloxy, C 3 -C 12 haloalkynyloxy, C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkylcarbonylamino, C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxyC 1 -C 12 alkoxy, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkoxy, or the following groups unsubstituted or substituted with 1-5 R 11 : aryloxy, arylamino, arylmethoxy, arylmethylamino, heteroaryloxy or heteroarylamino, and when the number of the substitutes is more than 1, R 11 may be the same or different;

R 3 is selected from H, halogen, NO 2 , CN, C(═O)NR 9 R 10 , C(═S)NR 9 R 10 , C 1 -C 12 alkylaminocarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 haloalkyl or C 1 -C 12 alkylsulfonyl;

R 4 and R 8 may be the same or different, respectively selected from H, halogen, CN, NO 2 , C(═O)NR 9 R 10 , C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, or the following groups unsubstituted or substituted with 1-5 R 11 : aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R 11 may be the same or different;

R 5 and R 7 may be the same or different, respectively selected from H, halogen, CN, NO 2 , C(═O)NR 9 R 10 , C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy, C 1 -C 12 alkylaminocarbonyloxy, C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxyC 1 -C 12 alkoxy, C 1 -C 12 haloalkoxyC 1 -C 12 haloalkoxy, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkoxy, or the following groups unsubstituted or substituted with 1-5 R 11 : aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R 11 may be the same or different;

R 6 is selected from H, halogen, CN, NO 2 , CO 2 H, C(═O)NR 9 R 10 , C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 alkoxyC 1 -C 12 alkoxy, C 1 -C 12 haloalkoxyC 1 -C 12 haloalkoxy, or the following groups unsubstituted or substituted with 1-5 R 11 : aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R 11 may be the same or different;

but R 4 , R 5 , R 6 , R 7 and R 8 can not be H simultaneously;

R 9 and R 10 may be the same or different, respectively selected from H or C 1 -C 6 alkyl;

R 11 is selected from halogen, NO 2 , ON, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 dialkylamino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 haloalkylcarbonylamino, C 1 -C 6 alkylaminocarbonyl or C 1 -C 6 haloalkylaminocarbonyl;

or the salts of the compounds having general formula I.

2. The compound according to the claim 1 , characterized in that wherein general formula I:

R 1 is selected from H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkoxyC 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 alkylaminothio, C 2 -C 6 dialkylaminothio or CO—X—CO 2 R 9 , in which X is selected from (CHR 9 )n, CR 9 ═CR 10 or C 6 H 4 , n=1-3;

R 2 is selected from halogen, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfonyl, C 2 -C 6 dialkylamino, C 3 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkoxyC 1 -C 6 alkoxy, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkoxy, or the following groups unsubstituted or substituted with 1-3 R 11 : phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino;

R 3 is selected from Cl, Br, F, NO 2 , CN, C(═O)NR 9 R 10 , C(═S)NR 9 R 10 , CO 2 CH 3 , CF 3 or SO 2 CH 3 ;

R 4 and R 8 may be the same or different, respectively selected from H, halogen, CN, NO 2 , C(═O)NR 9 R 10 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, or the following groups unsubstituted or substituted with 1-4 R 11 : phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy;

R 5 and R 7 may be the same or different, respectively selected from H, halogen, CN, NO 2 , C(═O)NR 9 R 10 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl;

R 6 is selected from H, halogen, CN, NO 2 , CO 2 H, C(═O)NR 9 R 10 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 alkoxyC 1 -C 6 alkoxy, or the following groups unsubstituted or substituted with 1-4 R 11 : phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy;

but R 4 , R 5 , R 6 , R 7 and R 8 can not be H simultaneously;

R 9 and R 10 may be the same or different, respectively selected from H or C 1 -C 3 alkyl;

R 11 is selected from halogen, NO 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkylamino, C 2 -C 6 dialkylamino, C 1 -C 3 alkylcarbonylamino or C 1 -C 3 alkylaminocarbonyl;

or the salts of the compounds having general formula I.

3. The compound according to the claim 2 , characterized in that wherein general formula I:

R 1 is selected from H, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkoxyC 1 -C 3 alkyl, C 1 -C 3 alkoxyC 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, C 1 -C 3 alkylaminothio, C 2 -C 6 dialkylaminothio or CO—X—CO 2 R 9 , in which X is selected from (CHR 9 )n, CR 9 ═CR 10 or C 6 H 4 , n=1-3;

R 2 is selected from Cl, Br, F, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylamino, C 1 -C 3 haloalkylamino, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylsulfonyl, C 2 -C 6 dialkylamino, C 3 -C 4 alkenyloxy, C 3 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 3 alkylcarbonyloxy, C 1 -C 3 alkylcarbonylamino, C 1 -C 3 alkylsulfonyloxy, C 1 -C 3 alkoxyC 1 -C 3 alkoxy, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkoxy, or the following groups unsubstituted or substituted with 1-3 R 11 : phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino;

R 3 is NO 2 ,

R 4 and R 8 may be the same or different, respectively selected from H, Cl, Br, F, CN, NO 2 , C(═O)NR 9 R 10 , C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkoxyC 1 -C 3 alkyl, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, or the following groups unsubstituted or substituted with 1-3 R 11 : phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy;

R 5 and R 7 may be the same or different, respectively selected from H, Cl, Br, F, CN, NO 2 , C(═O)NR 9 R 10 , C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylamino, C 1 -C 3 haloalkylamino, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl or C 1 -C 3 alkoxyC 1 -C 3 alkyl;

R 6 is selected from H, Cl, Br, F, CN, NO 2 , CO 2 H, C(═O)NR 9 R 10 , C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkoxyC 1 -C 6 alkyl, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, C 1 -C 3 alkoxyC 1 -C 3 alkoxy, or the following groups unsubstituted or substituted with 1-3 R 11 : phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy;

but R 4 , R 5 , R 6 , R 7 and R 8 can not be H simultaneously;

R 9 and R 10 may be the same or different, respectively selected from H or C 1 -C 3 alkyl;

R 11 is selected from Cl, Br, F, NO 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, or C 1 -C 3 alkylaminocarbonyl;

or the salts formed from the compounds of general formula I with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methylsulfonic acid, p-toluenesulfonic acid, malic acid or citric acid.

4. The compound according to the claim 3 , characterized in that wherein general formula I:

R 1 is selected from H, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkoxyC 1 -C 3 alkyl, C 1 -C 3 alkoxyC 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, C 1 -C 3 alkylaminothio, C 2 -C 6 dialkylaminothio, COCH 2 CO 2 R 9 COCH 2 CH 2 CO 2 R 9 COCHCH 3 CO 2 R 9 COC 6 H 4 CO 2 R 9 or COCH═CHCO 2 R 9 ;

R 2 is selected from Cl, Br, F, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylamino, C 1 -C 3 haloalkylamino, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylsulfonyl, C 2 -C 6 dialkylamino, C 3 -C 4 alkenyloxy, C 3 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 3 alkoxyC 1 -C 3 alkoxy, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkoxy, or the following groups unsubstituted or substituted with 1-3 R 11 : phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino;

R 3 is NO 2 ,

R 4 and R 8 may be the same or different, respectively selected from H, Cl, Br, F, CN, NO 2 , C(═O)NR 9 R 10 , C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkoxyC 1 -C 3 alkyl, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, or the following groups unsubstituted or substituted with 1-3 R 11 : phenoxy, anilino, phenoxycarbonyl or anilinocarbonyl;

R 5 and R 7 may be the same or different, respectively selected from H, Cl, Br, F, CN, NO 2 , C(═O)NR 9 R 10 , C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylamino, C 1 -C 3 haloalkylamino, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl or C 1 -C 3 alkoxyC 1 -C 3 alkyl;

R 6 is selected from H, Cl, Br, F, CN, NO 2 , CO 2 H, C(═O)NR 9 R 10 , C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkoxyC 1 -C 6 alkyl, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, C 1 -C 3 alkoxyC 1 -C 3 alkoxy, or the following groups unsubstituted or substituted with 1-3 R 11 : phenoxy, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl or anilinocarbonyl;

but R 4 , R 5 , R 6 , R 7 and R 8 can not be H simultaneously;

R 9 and R 10 may be the same or different, respectively selected from H, CH 3 or C 2 H 5 ;

R 11 is selected from Cl, Br, F, NO 2 , CN, CF 3 , CH 3 , OCH 3 , SCH 3 , formyl, CO 2 CH 3 or CONHCH 3 ;

5. The compound according to the claim 4 , characterized in that wherein general formula I:

R 1 is selected from H, CH 3 , C 2 H 5 , cyclopropyl, formyl, COCH 3 , COCF 3 , CO 2 CH 3 , CO 2 C 2 H 5 , SCCl 3 , SO 2 CH 3 , SO 2 C 2 H 5 , CH 2 OCH 3 , CH 2 OO 2 H 5 , CH 2 CH 2 OCH 3 , COCH 2 OCH 3 , CH 2 COOCH 3 , SNHCH 3 , SN(CH 3 ) 2 , COCH 2 CO 2 H, COCH 2 CO 2 CH 3 , COCH 2 CH 2 CO 2 H, COCH 2 CH 2 CO 2 CH 3 , COCHCH 3 CO 2 H, COCHCH 3 CO 2 CH 3 , COC 6 H 4 CO 2 H, COC 6 H 4 CO 2 CH 3 , COCH═CHCO 2 H or COCH═CHCO 2 CH 3 ;

R 2 is selected from Cl, Br, F, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylamino, C 1 -C 3 haloalkylamino, SCH 3 , SC 2 H 5 , N(CH 3 ) 2 , N(C 2 H 5 ) 2 , OCH 2 OCH 3 , OPh, NHPh, OCH 2 Ph, NHCH 2 Ph, 4-chlorophenoxy, 4-chlorophenylamino, 2-chloro-4-(trifluoromethyl)phenoxy, 2-chloro-4-(trifluoromethyl)phenylamino, 3-chloro-5-(trifluoromethyl)pyridin-2-yloxy or 3-chloro-5-(trifluoromethyl)pyridin-2-ylamino;

R 3 is NO 2 ,

R 4 and R 8 may be the same or different, respectively selected from H, Cl, Br, F, CN, NO 2 , C(═O)NH 2 , C(═O)NHCH 3 , C(═O)N(CH 3 ) 2 , CH 3 , C 2 H 5 , CF 3 , OCH 3 , OC 2 H 5 , OCF 3 , SO 2 CH 3 , SO 2 C 2 H 5 , COCH 3 , COC 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 , OPh, NHPh, CO 2 Ph or CONHPh;

R 5 and R 7 may be the same or different, respectively selected from H, Cl, Br, F, CN, NO 2 , C(═O)NH 2 , CH 3 , CF 3 , OCH 3 , OCF 3 , NHCH 3 , SCH 3 , SO 2 CH 3 , SO 2 C 2 H 5 , COCH 3 , COC 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 or CH 2 OCH 3 ;

R 6 is selected from H, Cl, Br, F, CN, NO 2 , CO 2 H, C(═O)NH 2 , C(═O)NHCH 3 , C(═O)N(CH 3 ) 2 , CH 3 , CF 3 , CF(CF 3 ) 2 OCF 3 OCH 2 CF 3 OCF 2 CHFCF 3 SO 2 CH 3 , SO 2 C 2 H 5 COCH 3 , COC 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 OPh, NHPh, COPh COCH 2 Ph CO 2 Ph CONHPh pyridinoxy or 3-chloro-5-(trifluoromethyl)pyridin-2-yloxy;

but R 4 , R 5 , R 6 , R 7 and R 8 can not be H simultaneously;

or the salts formed from the compounds of general formula I with hydrochloric acid, sulfuric acid, phosphoric acid, trifluoroacetic acid, methylsulfonic acid or p-toluenesulfonic acid.

6. A fungicidal composition comprising the compound according to claim 1 as an active ingredient and an acceptable carrier in agriculture, wherein the weight percentage of the active ingredient in the composition is 0.5-90%.

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 Aug 14, 2012

From: HUANG, GUANG; ZHANG, HONG

To: SINOCHEM CORPORATION

Reel/Frame 028784/0039 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 14, 2012

From: LIU, CHANGLING; LI, HUICHAO; LI, ZHINIAN

To: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.

Reel/Frame 028784/0783 →

Priority Claims (1)

CN 2010 1 0129005 · Mar 22, 2010 · national

Continuity (1)

Related Publication 20120309844A1 · Dec 6, 2012