Title of Invention

SUBSTITUTED DIPHENYLAMINE COMPOUNDS, PREPARATION METHOD AND USE THEREOF

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.   I
Full Text FORM 2
THE PATENTS ACT 1970
(39 of 1970)
&
The Patents Rules  2003
COMPLETE SPECIFICATION
(See section 10 and rule 13)



1. SUBSTITUTED DIPHENYLAMINE COMPOUNDS  PREPARATION METHOD AND USE THEREOF

2.

1. (A) SINOCHEM CORPORATION
(B) China
(C) 28 Fuxingmennei Dajie  Xicheng District Beijing 100031 China
2. (A) SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO.  LTD.
(B) China
(C) 8 Shenliaodong Road  Tiexi District Shenyang  Liaoning 110021 China


The following specification particularly describes the invention and the manner in which it is to be performed.



FIELD OF THE INVENTION
The invention relates to fungicide in agricultural fields  specifically to a kind of substituted diphenylamine compounds and the preparation methods and use thereof.

BACKGROUND OF THE INVENTION
Diphenylamine and fluazinam are known fungicides  the former is mainly used to control storage diseases of fruits and vegetables  and the latter is mainly used to control diseases of field crops.
The compounds having the following general formulas were reported as insecticides  acaricides  fungicides  herbicides  rodenticides or others in the prior art:

Such as patents BR7900462  CH626323  CN1188757  DE2509416  DE2642147  DE2642148  EP26743  EP60951  GB1544078  GB1525884  JP58113151  JP64001774  JP01186849  WO2002060878  WO2005035498  WO2009037707  US3948957  US3948990  US4041172  US4152460  US4187318  US4215145  US4304791  US4316988  US4407820  US4459304  US4670596 and so on  and ACS Symposium Series(1992)  504(Synth. Chem. Agrochem. ?)  336-48; Journal of the Chemical Society(1951)  110-15  etc. all reported the compounds having above general formulas.
In addition  the compounds of the following general formulas were mentioned in Chemische Berichte(1962)  95 1711-21; Chemische Berichte(1963)  96(7)  1936-44; Journal of Organic Chemistry(1954)  19  1641-5; Journal of the Chemical Society; Transactions(1913)  103 982-8 and Journal of the Chemical Society  Transactions(1921)  119  187-92 and so on  but without any bioactivity reported.

The preparation method of the following compound was published in patent US3107263:
.
The compounds having the structure of general formula I were not reported in the prior art.
SUMMARY OF THE INVENTION
New pesticides with novel structure and excellent property are needed by modern agricultural production. The object of the present invention is to provide a kind of substituted diphenylamine compounds to control a variety of plant pathogens/diseases at very low doses  which can be used to prepare substances to control pathogens in agricultural and other fields.
Detailed descriptions of the invention are as follows:
The present invention provides a kind of substituted diphenylamine compounds having general formula I:
I
Wherein:
R1 is selected from H  C1-C12alkyl  C3-C12cycloalkyl  C1-C12haloalkyl  C1-C12alkylcarbonyl  C1-C12haloalkylcarbonyl  C1-C12alkoxycarbonyl  C1-C12alkylaminocarbonyl  C1-C12alkylthio  C1-C12haloalkylthio  C1-C12alkylsulfonyl  C1-C12alkoxyC1-C12alkyl  C1-C12alkoxyC1-C12alkylcarbonyl  C1-C12alkoxycarbonylC1-C12alkyl  C1-C12alkylaminothio  C2-C12 dialkylaminothio or CO-X-CO2R9  in which X is selected from (CHR9)n  CR9=CR10 or C6H4  n=1-6;
R2 is selected from halogen  C1-C12haloalkyl  C1-C12alkoxy  C1-C12haloalkoxy  C1-C12alkylamino  C1-C12haloalkylamino  C1-C12alkylthio  C1-C12haloalkylthio  C1-C12alkylsulfonyl  C3-C12cycloalkyl  C2-C12dialkylamino  C3-C12alkenyloxy  C3-C12haloalkenyloxy  C3-C12alkynyloxy  C3-C12haloalkynyloxy  C1-C12alkylcarbonyloxy  C1-C12alkylcarbonylamino  C1-C12alkylsulfonyloxy  C1-C12alkoxyC1-C12alkoxy  C1-C12alkoxycarbonylC1-C12alkoxy  or the following groups unsubstituted or substituted with 1-5 R11: aryloxy  arylamino  arylmethoxy  arylmethylamino  heteroaryloxy or heteroarylamino  and when the number of the substitutes is more than 1  R11 may be the same or different;
R3 is selected from H  halogen  NO2  CN  C(=O)NR9R10  C(=S)NR9R10  C1-C12alkylaminocarbonyl  C1-C12alkoxycarbonyl  C1-C12haloalkyl or C1-C12alkylsulfonyl;
R4 and R8 may be the same or different  respectively selected from H  halogen  CN  NO2  OH  CO2H  C(=O)NR9R10  C1-C12alkyl  C1-C12haloalkyl  C1-C12alkoxy  C1-C12haloalkoxy  C2-C12alkenyl  C2-C12alkynyl  C1-C12alkylsulfonyl  C1-C12alkylcarbonyl  C1-C12alkoxycarbonyl  C1-C12alkoxyC1-C12alkyl  C1-C12alkoxycarbonylC1-C12alkyl  C1-C12alkylcarbonyloxy  or the following groups unsubstituted or substituted with 1-5 R11: aryl  arylmethyl  aryloxy  arylamino  arylcarbonyl  arylmethylcarbonyl  aryloxycarbonyl  arylaminocarbonyl or heteroaryloxy  and when the number of the substitutes is more than 1  R11 may be the same or different;
R5 and R7 may be the same or different  respectively selected from H  halogen  CN  NO2  OH  CO2H  C(=O)NR9R10  C1-C12alkyl  C1-C12haloalkyl  C1-C12alkoxy  C1-C12haloalkoxy  C1-C12alkylamino  C1-C12haloalkylamino  C1-C12alkylthio  C1-C12haloalkylthio  C2-C12alkenyl  C2-C12alkynyl  C1-C12alkylsulfonyl  C1-C12alkylcarbonyl  C1-C12alkoxycarbonyl  C1-C12alkoxyC1-C12alkyl  C1-C12alkoxycarbonylC1-C12alkyl  C1-C12alkylcarbonyloxy  C1-C12alkoxycarbonyloxy  C1-C12alkylaminocarbonyloxy  C1-C12alkylsulfonyloxy  C1-C12alkoxyC1-C12alkoxy  C1-C12haloalkoxyC1-C12haloalkoxy  C1-C12alkoxycarbonylC1-C12alkoxy  or the following groups unsubstituted or substituted with 1-5 R11: aryl  arylmethyl  aryloxy  arylamino  arylcarbonyl  arylmethylcarbonyl  aryloxycarbonyl  arylaminocarbonyl or heteroaryloxy  and when the number of the substitutes is more than 1  R11 may be the same or different;
R6 is selected from H  halogen  CN  NO2  OH  CO2H  C(=O)NR9R10  C1-C12alkyl  C1-C12haloalkyl  C1-C12alkoxy  C1-C12haloalkoxy  C2-C12alkenyl  C2-C12alkynyl  C1-C12alkylsulfonyl  C1-C12alkylcarbonyl  C1-C12alkoxycarbonyl  C1-C12alkoxyC1-C12alkyl  C1-C12alkoxycarbonylC1-C12alkyl  C1-C12alkoxyC1-C12alkoxy  C1-C12haloalkoxyC1-C12haloalkoxy  C1-C12alkylcarbonyloxy  or the following groups unsubstituted or substituted with 1-5 R11: aryl  arylmethyl  aryloxy  arylamino  arylcarbonyl  arylmethylcarbonyl  aryloxycarbonyl  arylaminocarbonyl or heteroaryloxy  and when the number of the substitutes is more than 1  R11 may be the same or different;
But R4  R5  R6  R7 and R8 can not be H simultaneously;
R9 and R10 may be the same or different  respectively selected from H or C1-C6alkyl;
R11 is selected from halogen  NO2  CN  C1-C6alkyl  C1-C6haloalkyl  C1-C6alkoxy  C1-C6haloalkoxy  C1-C6alkylthio  C1-C6alkylcarbonyl  C1-C6alkoxycarbonyl  C2-C6alkenyl  C2-C6haloalkenyl  C3-C6alkenyloxy  C3-C6haloalkenyloxy  C2-C6alkynyl  C2-C6haloalkynyl  C3-C6alkynyloxy  C3-C6haloalkynyloxy  C1-C6haloalkylthio  C1-C6haloalkylcarbonyl  C1-C6alkylamino  C1-C6haloalkylamino  C2-C8dialkylamino  C1-C6alkylcarbonylamino  C1-C6haloalkylcarbonylamino  C1-C6alkylaminocarbonyl or C1-C6haloalkylaminocarbonyl;
Or the salts of the compounds having general formula I.
The preferred compounds of general formula I of this invention are:
R1 is selected from H,C1-C6alkyl  C3-C6cycloalkyl  C1-C6alkylcarbonyl  C1-C6haloalkylcarbonyl  C1-C6alkoxycarbonyl  C1-C6alkylthio  C1-C6haloalkylthio  C1-C6alkylsulfonyl  C1-C6alkoxyC1-C6alkyl  C1-C6alkoxyC1-C6alkylcarbonyl  C1-C6alkoxycarbonylC1-C6alkyl  C1-C6alkylaminothio  C2-C6 dialkylaminothio or CO-X-CO2R9  in which X is selected from (CHR9)n  CR9=CR10 or C6H4  n=1-3;
R2 is selected from halogen  C1-C6alkoxy  C1-C6haloalkoxy  C1-C6alkylamino  C1-C6haloalkylamino  C1-C6alkylthio  C1-C6haloalkylthio  C1-C6alkylsulfonyl  C2-C6dialkylamino  C3-C6alkenyloxy  C3-C6haloalkenyloxy  C3-C6alkynyloxy  C1-C6alkylcarbonyloxy  C1-C6alkylcarbonylamino  C1-C6alkylsulfonyloxy  C1-C6alkoxyC1-C6alkoxy  C1-C6alkoxycarbonylC1-C6alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  benzyloxy  benzylamino  pyridyloxy or pyridylamino;
R3 is selected from Cl  Br  F  NO2  CN  C(=O)NR9R10  C(=S)NR9R10  CO2CH3?CF3 or SO2CH3;
R4 and R8 may be the same or different  respectively selected from H  halogen  CN  NO2  C(=O)NR9R10  C1-C6alkyl  C1-C6haloalkyl  C1-C6alkoxy  C1-C6haloalkoxy  C2-C6alkenyl  C2-C6alkynyl  C1-C6alkylsulfonyl  C1-C6alkylcarbonyl  C1-C6alkoxycarbonyl  C1-C6alkoxyC1-C6alkyl  C1-C6alkoxycarbonylC1-C6alkyl  or the following groups unsubstituted or substituted with 1-4 R11: phenoxy  anilino  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl  anilinocarbonyl or pyridyloxy;
R5 and R7 may be the same or different  respectively selected from H  halogen  CN  NO2  C(=O)NR9R10  C1-C6alkyl  C1-C6haloalkyl  C1-C6alkoxy  C1-C6haloalkoxy  C1-C6alkylamino  C1-C6haloalkylamino  C1-C6alkylthio  C1-C6haloalkylthio  C2-C6alkenyl  C2-C6alkynyl  C1-C6alkylsulfonyl  C1-C6alkylcarbonyl  C1-C6alkoxycarbonyl or C1-C6alkoxyC1-C6alkyl;
R6 is selected from H  halogen  CN  NO2  CO2H  C(=O)NR9R10  C1-C6alkyl  C1-C6haloalkyl  C1-C6haloalkoxy  C2-C6alkenyl  C2-C6alkynyl  C1-C6alkylsulfonyl  C1-C6alkylcarbonyl  C1-C6alkoxycarbonyl  C1-C6alkoxyC1-C6alkyl  C1-C6alkoxycarbonylC1-C6alkyl  C1-C6alkoxyC1-C6alkoxy  or the following groups unsubstituted or substituted with 1-4 R11: phenoxy  anilino  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl  anilinocarbonyl or pyridyloxy;
But R4  R5  R6  R7 and R8 can not be H simultaneously;
R9 and R10 may be the same or different  respectively selected from H or C1-C3alkyl;
R11 is selected from halogen  NO2  CN  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylthio  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkylamino  C2-C6dialkylamino  C1-C3alkylcarbonylamino or C1-C3alkylaminocarbonyl;
Or the salts of the compounds having general formula I.
Furthermore  the preferred compounds of general formula I of this invention are:
R1 is selected from H,C1-C3alkyl  C3-C6cycloalkyl  C1-C3alkylcarbonyl  C1-C3haloalkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C1-C3alkoxyC1-C3alkyl  C1-C3alkoxyC1-C3alkylcarbonyl  C1-C3alkoxycarbonylC1-C3alkyl  C1-C3alkylaminothio  C2-C6 dialkylaminothio or CO-X-CO2R9  in which X is selected from (CHR9)n  CR9=CR10 or C6H4  n=1-3;
R2 is selected from Cl  Br  F  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  C1-C3alkylthio  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C2-C6dialkylamino  C3-C4alkenyloxy  C3-C4haloalkenyloxy  C3-C4alkynyloxy  C1-C3alkylcarbonyloxy  C1-C3alkylcarbonylamino  C1-C3alkylsulfonyloxy  C1-C3alkoxyC1-C3alkoxy  C1-C3alkoxycarbonylC1-C3alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  benzyloxy  benzylamino  pyridyloxy or pyridylamino;
R3 is NO2;
R4 and R8 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C2-C3alkenyl  C2-C3alkynyl  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkoxyC1-C3alkyl  C1-C3alkoxycarbonylC1-C3alkyl  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl  anilinocarbonyl or pyridyloxy;
R5 and R7 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  C1-C3alkylthio  C1-C3haloalkylthio  C2-C3alkenyl  C2-C3alkynyl  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl or C1-C3alkoxyC1-C3alkyl;
R6 is selected from H  Cl  Br  F  CN  NO2  CO2H  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3haloalkoxy  C2-C3alkenyl  C2-C3alkynyl  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkoxyC1-C6alkyl  C1-C3alkoxycarbonylC1-C3alkyl  C1-C3alkoxyC1-C3alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl  anilinocarbonyl or pyridyloxy;
But R4  R5  R6  R7 and R8 can not be H simultaneously;
R9 and R10 may be the same or different  respectively selected from H or C1-C3alkyl;
R11 is selected from Cl  Br  F  NO2  CN  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylthio  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl or C1-C3alkylaminocarbonyl;
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.
Even more preferred compounds of general formula I of this invention are:
R1 is selected from H,C1-C3alkyl  C3-C6cycloalkyl  C1-C3alkylcarbonyl  C1-C3haloalkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C1-C3alkoxyC1-C3alkyl  C1-C3alkoxyC1-C3alkylcarbonyl  C1-C3alkoxycarbonylC1-C3alkyl  C1-C3alkylaminothio  C2-C6 dialkylaminothio  COCH2CO2R9  COCH2CH2CO2R9  COCHCH3CO2R9  COC6H4CO2R9 or COCH=CHCO2R9;
R2 is selected from Cl  Br  F  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  C1-C3alkylthio  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C2-C6dialkylamino  C3-C4alkenyloxy  C3-C4haloalkenyloxy  C3-C4alkynyloxy  C1-C3alkoxyC1-C3alkoxy  C1-C3alkoxycarbonylC1-C3alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  benzyloxy  benzylamino  pyridyloxy or pyridylamino;
R3 is NO2;
R4 and R8 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkoxyC1-C3alkyl  C1-C3alkoxycarbonylC1-C3alkyl  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  phenoxycarbonyl or anilinocarbonyl;
R5 and R7 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  C1-C3alkylthio  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl or C1-C3alkoxyC1-C3alkyl;
R6 is selected from H  Cl  Br  F  CN  NO2  CO2H  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3haloalkoxy  C2-C3alkenyl  C2-C3alkynyl  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkoxyC1-C6alkyl  C1-C3alkoxycarbonylC1-C3alkyl  C1-C3alkoxyC1-C3alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl or anilinocarbonyl;
But R4  R5  R6  R7 and R8 can not be H simultaneously;
R9 and R10 may be the same or different  respectively selected from H  CH3 or C2H5;
R11 is selected from Cl  Br  F  NO2  CN  CF3  CH3  OCH3  SCH3  formyl  CO2CH3 or CONHCH3;
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.
The most preferred compounds of formula I of this invention are:
R1 is selected from H,CH3  C2H5  cyclopropyl  formyl  COCH3  COCF3  CO2CH3  CO2C2H5  SCCl3  SO2CH3  SO2C2H5  CH2OCH3  CH2OC2H5  CH2CH2OCH3  COCH2OCH3  CH2COOCH3  SNHCH3  SN(CH3)2  COCH2CO2H  COCH2CO2CH3  COCH2CH2CO2H  COCH2CH2CO2CH3  COCHCH3CO2H  COCHCH3CO2CH3  COC6H4CO2H  COC6H4CO2CH3  COCH=CHCO2H or COCH=CHCO2CH3;
R2 is selected from Cl  Br  F  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  SCH3  SC2H5  N(CH3)2  N(C2H5)2  OCH2OCH3  OPh  NHPh  OCH2Ph  NHCH2Ph  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;
R3 is NO2;
R4 and R8 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NH2  C(=O)NHCH3  C(=O)N(CH3)2  CH3  C2H5  CF3  OCH3  OC2H5  OCF3  SO2CH3  SO2C2H5  COCH3  COC2H5  CO2CH3  CO2C2H5  OPh  NHPh  CO2Ph or CONHPh;
R5 and R7 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NH2  CH3  CF3  OCH3  OCF3  NHCH3  SCH3  SO2CH3  SO2C2H5  COCH3  COC2H5  CO2CH3  CO2C2H5 or CH2OCH3;
R6 is selected from H  Cl  Br  F  CN  NO2  CO2H  C(=O)NH2  C(=O)NHCH3  C(=O)N(CH3)2  CH3  CF3 ?CF(CF3)2?OCF3?OCH2CF3?OCF2CHFCF3?SO2CH3  SO2C2H5?COCH3  COC2H5  CO2CH3  CO2C2H5?OPh  NHPh ?COPh?COCH2Ph?CO2Ph?CONHPh?pyridinoxy or 3-chloro-5-(trifluoromethyl)pyridin-2-yloxy;
But R4  R5  R6  R7 and R8 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.
The terms used above to definite the compounds of general formula I represent substitutes as follow:
The “halogen” or “halo” is fluorine  chlorine  bromine or iodine.
The “alkyl” stands for straight or branched chain alkyl  such as methyl  ethyl  propyl  isopropyl or tert-butyl.
The “cycloalkyl” is substituted or unsubstituted cyclic alkyl  such as cyclopropyl  cyclopentyl or cyclohexyl. The substitute(s) is(are) methyl  halogen  etc.
The “haloalkyl” stands for straight or branched chain alkyl  in which hydrogen atoms can be all or partly substituted with halogen  such as chloromethyl  dichloromethyl  trichloromethyl  fluoromethyl  difluoromethyl  trifluoromethyl  etc.
The “alkoxy” refers to straight or branched chain alkyl  which is linked to the structure by oxygen atom.
The “haloalkoxy” refers to straight or branched chain alkoxy  in which hydrogen atoms may be all or partly substituted with halogen  such as chloromethoxy  dichloromethoxy  trichloromethoxy  fluoromethoxy  difluoromethoxy  trifluoromethoxy  chlorofluoromethoxy  trifluoroethoxy  etc.
The “alkylthio” refers to straight or branched chain alkyl  which is linked to the structure by sulfur atom.
The “haloalkylthio” refers to straight or branched chain alkylthio  in which hydrogen atoms may be all or partly substituted with halogen  such as chloromethylthio  dichloromethylthio  trichloromethylthio  fluoromethylthio  difluoromethylthio  trifluoromethylthio  chlorofluoromethylthio  etc.
The “alkylamino” refers to straight or branched chain alkyl  which is linked to the structure by nitrogen atom.
The “haloalkylamino” refers to straight or branched chain alkylamino  in which hydrogen atoms may be all or partly substituted with halogen.
The “alkenyl” refers to straight or branched chain alkenyl  such as ethenyl  1-propenyl  2-propenyl and different isomer of butenyl  pentenyl and hexenyl. Alkenyl also includes polyene  such as propa-1 2-dienyl and hexa-2 4-dienyl.
The “haloalkenyl” stands for straight or branched chain alkenyl  in which hydrogen atoms can be all or partly substituted with halogen.
The “alkynyl” refers to straight or branched chain alkynyl  such as ethynyl  1-propynyl  2-propynyl and different isomer of butynyl  pentynyl and hexynyl. Alkynyl also includes groups including more than one triple bonds  such as hexa-2 5-diynyl.
The “haloalkynyl” stands for straight or branched chain alkynyl  in which hydrogen atoms can be all or partly substituted with halogen.
The “aryl” and “aryl” in arylalkyl  aryloxy and aryloxyalkyl include phenyl or naphthyl, etc.
The “heteroaryl” stands for five member ring or six member ring containing one or more N  O  S hetero atoms. Such as furanyl  pyrazolyl  thiazolyl  pyridinyl  pyrimidinyl  pyrazinyl  pyridazinyl  triazinyl  quinolinyl  etc.
Part of the substitutes of R1  R2  R4  R5  R6  R7 and R8 in formula I are separately listed in table 1  table 2  table 3  table 4 and table 5  but without being restricted thereby.
I
Table 1 substitute R1
R1 R1 R1
H CO2CH2CH2CH3 CH2CO2CH2CH3
CH3 CONHCH3 COCH2OCH3
CH2CH3 CONHCH2CH3 COCH2OCH2CH3
CH2CH2CH3 SO2CH3 SNHCH3
CH2CH2CH2CH3 SO2CH2CH3 SNHCH2CH3
COCH3 SCCl3 SN(CH3)2
COCH2CH3 CH2OCH3 SN(CH2CH3)2
COCH2CH2CH3 CH2CH2OCH3 COCH2CO2H
CO2CH3 CH2CH2OCH2CH3 COCH2CH2CO2H
CO2CH2CH3 CH2CO2CH3 COCHCH3CO2H
COCH2CO2CH3 COCH2CH2CO2CH3 COCHCH3CO2CH3
CH2CH=CH2 CH2CH=CCl2 CH2CH=CF2
CH2CH2CH=CF2 CH2CH2CF=CF2 CH2CHF2
CH2C=CH CH2C=C-I CH2C=CCH3
COCH=CH2CO2H


COCH=CH2CO2CH3



Table 2 substitute R2
R2 R2 R2 R2
F OCF3 SCH3 OCOCH2CH3
Cl OCH2CF3 SCH2CH3 NHCOCH3
Br NHCH3 SO2CH3 NHCOCH2CH3
I N(CH3)2 SO2CH2CH3 OPh
CF3 NHCH2CH3 OCH2CH=CH2 OPh-4-Cl
OCH3 NH(CH2)2CH3 OCH2CH=CCl2 OPh-2-Cl-4CF3
OCH2CH3 NHCH(CH3)2 OCH2C=CH OPh-2-Cl-4NO2
OCH(CH3)2 NHCH2CF3 OCOCH3 NHPh


OCH2Ph NHPh-4-Cl
NHCH2Ph NHPh-2-Cl-4CF3


Table 3 substitute R4(R8)
R4(R8) R4(R8) R4(R8) R4(R8)
H CH3 CH=CH2 Ph
F CH2CH3 CH2CH=CH2 CH2Ph
Cl (CH2)2CH3 C=CH OPh
Br CH(CH3)2 CH2C=CH NHPh
I CF3 SO2CH3 COPh
CN CHF2 SO2CH2CH3 CO2Ph
NO2 CH2F COCH3 CO2Ph-4-Cl
CONH2 CH2CF3 COCH2CH3 CO2Ph-2-Cl-4-CF3
CONHCH3 CF2CHF2 CO2CH3 CO2Ph-2-Cl-4-NO2
CON(CH3)2 CF2CF3 CO2CH2CH3 CONHPh
CONHCH2CH3 OCH3 CH2OCH3 CONHPh-4-Cl
CON(CH2CH3)2 OCH2CH3 CH2OCH2CH3 CONHPh-2-Cl-4-CF3
CONH(CH2)2CH3 O(CH2)2CH3 CH2CO2CH3 CONHPh-2-Cl-4-NO2
CONHCH(CH3)2 OCH(CH3)2 CH2CO2CH2CH3

OCF3 OCH2CF3 OCF2CF3
OH OCOCH3 CO2H

Table 4 substitute R5(R7)
R5(R7) R5(R7) R5(R7) R5(R7)
H CH3 OCF3 COCH3
F CH2CH3 OCH2CF3 COCH2CH3
Cl (CH2)2CH3 OCF2CF3 CO2CH3
Br CH(CH3)2 NHCH3 CO2CH2CH3
I CF3 NHCH2CH3 CH2OCH3
CN CHF2 NHCH2CF3 CH2OCH2CH3
NO2 CH2F SCH3 CH2CO2CH3
CONH2 CH2CF3 SCH2CH3 CH2CO2CH2CH3
CONHCH3 CF2CHF2 CH=CH2 OCOCH3
CON(CH3)2 CF2CF3 CH2CH=CH2 OCOCH2CH3
CONHCH2CH3 OCH3 C=CH OCO2CH3
CON(CH2CH3)2 OCH2CH3 CH2C=CH OCO2CH2CH3
CONH(CH2)2CH3 O(CH2)2CH3 SO2CH3 OCONHCH3
CONHCH(CH3)2 OCH(CH3)2 SO2CH2CH3 OCONHCH2CH3
OSO2CH2CH3 Ph CO2Ph OSO2CH3
OCH2OCH3 CH2Ph CO2Ph-4-Cl CONHPh-4-Cl
OCH2OCH2CH3 OPh CO2Ph-2-Cl-4-CF3 CONHPh-2-Cl-4-CF3
OCH2CO2CH3 NHPh CO2Ph-2-Cl-4-NO2

COPh CONHPh COCH2Ph
OH CO2H COCH2Ph-4-Cl

Table 5 substitute R6
R6 R6 R6 R6
H CONHCH(CH3)2 O(CH2)2CH3 CO2CH2CH3
F CH3 OCH(CH3)2 CH2OCH3
Cl CH2CH3 OCF3 CH2OCH2CH3
Br (CH2)2CH3 OCH2CF3 CH2CO2CH3
I CH(CH3)2 CH=CH2 CH2CO2CH2CH3
CN CF3 CH2CH=CH2 OCH2OCH3
NO2 CHF2 C=CH OCH2OCH2CH3
CONH2 CH2F CH2C=CH Ph
CONHCH3 CH2CF3 SO2CH3 CH2Ph
CON(CH3)2 CF2CHF2 SO2CH2CH3 OPh
CONHCH2CH3 CF2CF3 COCH3 NHPh
CON(CH2CH3)2 OCH3 COCH2CH3 COPh
CONH(CH2)2CH3 OCH2CH3 CO2CH3 COCH2Ph
CO2Ph CO2Ph-4-Cl CO2Ph-2-Cl-4-CF3

CONHPh CONHPh-4-Cl CONHPh-2-Cl-4-CF3
OH OCOCH3 CO2H

The present invention is also explained by the following compounds in Table 6  but without being restricted thereby.
I
Table 6
No. R1 R2 R3 R4 R5 R6 R7 R8
1 H Cl NO2 F H F H H
2 H Cl NO2 Cl H Cl H H
3 H Cl NO2 Cl Cl Cl H H
4 H Cl NO2 Cl H Cl Cl H
5 H Cl NO2 Cl H Cl H Cl
6 H Cl NO2 CN H H H H
7 H Cl NO2 H H CN H H
8 H Cl NO2 H H NO2 H H
9 H Cl NO2 NO2 H NO2 H H
10 H Cl NO2 NO2 H NO2 H NO2
11 H Cl NO2 CF3 H H H H
12 H Cl NO2 H H CF3 H H
13 H Cl NO2 OCH3 H H H H
14 H Cl NO2 H H OCH3 H H
15 H Cl NO2 SCH3 H H H H
16 H Cl NO2 H H SCH3 H H
17 H Cl NO2 OCF3 H H H H
18 H Cl NO2 H H OCF3 H H
19 H Cl NO2 COCH3 H H H H
20 H Cl NO2 H H COCH3 H H
21 H Cl NO2 SO2CH3 H H H H
22 H Cl NO2 H H SO2CH3 H H
23 H Cl NO2 CO2CH3 H H H H
24 H Cl NO2 H H CO2CH3 H H
25 H Cl NO2 CONHPh H H H H
26 H Cl NO2 H CONHPh H H H
27 H Cl NO2 H H CONHPh H H
28 H Cl NO2 CO2Ph H H H H
29 H Cl NO2 CONH2 H H H H
30 H Cl NO2 H H CONH2 H H
31 H Cl NO2 Cl H CF3 H H
32 H Cl NO2 Cl H NO2 H H
33 H Cl NO2 Cl H CN H H
34 H Cl NO2 CH3 H Cl H H
35 H Cl NO2 CF3 H Cl H H
36 H Cl NO2 NO2 H Cl H H
37 H Cl NO2 CN H Cl H H
38 H Cl NO2 Cl H Cl H NO2
39 H Cl NO2 Cl H Cl H CN
40 H Cl NO2 Cl H Cl H CF3
41 H Cl NO2 F H F H NO2
42 H Cl NO2 F H NO2 H F
43 H Cl NO2 Cl H NO2 H Cl
44 H Cl NO2 Cl H CF3 H Cl
45 H Cl NO2 Cl H CN H Cl
46 H Cl NO2 Cl H COCH3 H Cl
47 H Cl NO2 Cl H CONH2 H Cl
48 H Cl NO2 NO2 H F H H
49 H Cl NO2 NO2 H Br H H
50 H Cl NO2 NO2 H CF3 H H
51 H Cl NO2 NO2 H CN H H
52 H Cl NO2 NO2 H COCH3 H H
53 H Cl NO2 NO2 H CONH2 H H
54 H Cl NO2 NO2 H CH3 H H
55 H Cl NO2 CF3 H NO2 H H
56 H Cl NO2 CN H NO2 H H
57 H Cl NO2 COCH3 H NO2 H H
58 H Cl NO2 CONH2 H NO2 H H
59 H Cl NO2 CH3 H NO2 H H
60 H Cl NO2 Cl H F H NO2
61 H Cl NO2 Cl H CF3 H NO2
62 H Cl NO2 Cl H NO2 H NO2
63 H Cl NO2 Cl H CN H NO2
64 H Cl NO2 F H Cl H NO2
65 H Cl NO2 CH3 H Cl H NO2
66 H Cl NO2 CF3 H Cl H NO2
67 H Cl NO2 NO2 H Cl H NO2
68 H Cl NO2 CN H Cl H NO2
69 H Cl NO2 NO2 H CF3 H NO2
70 H Cl NO2 NO2 H CN H NO2
71 H Cl NO2 NO2 H CH3 H NO2
72 H Cl NO2 NO2 H F H NO2
73 H Cl NO2 CF3 H NO2 H NO2
74 H Cl NO2 CN H NO2 H NO2
75 H Cl NO2 CH3 H NO2 H NO2
76 H Cl NO2 F H NO2 H NO2
77 H Cl NO2 H CF3 CN H H
78 H Cl NO2 NO2 H CN CF3 H
79 H Cl NO2 Br H OCF3 H Br
80 H Cl NO2 CH3 H Cl CH2CO2C2H5 H
81 H Cl NO2 Cl CH3 Cl H H
82 H Cl NO2 Cl CH3 Cl H NO2
83 H Cl NO2 Cl CH3 H H H
84 H Cl NO2 CH3 Cl H H H
85 H Cl NO2 CH3 Cl NO2 H NO2
86 H Cl NO2 CH3 Cl NO2 H H
87 H Cl NO2 Cl CH3 NO2 H NO2
88 H Cl NO2 Br H NO2 H CN
89 H Cl NO2 NO2 Cl CF3 H NO2
90 H Cl NO2 NO2 H Cl Cl H
91 H Cl NO2 Cl H NO2 Cl H
92 H Cl NO2 Cl H H Cl NO2
93 H Cl NO2 Cl Cl NO2 H H
94 H Cl NO2 Cl Cl H H NO2
95 H Cl NO2 NO2 Cl Cl H NO2
96 H Cl NO2 Cl H NO2 Cl NO2
97 H Cl NO2 Cl H Cl Cl NO2
98 H Cl NO2 Cl Cl Cl NO2 H
99 H Cl NO2 Cl Cl Cl H NO2
100 H Cl NO2 Cl Cl NO2 Cl NO2
101 H Cl NO2 Cl H OCF2CHFCF3 Cl H
102 H Cl NO2 H Cl
Cl H
103 H Cl H F H F H H
104 H Cl H Cl H Cl H H
105 H Cl H Cl Cl Cl H H
106 H Cl H Cl H Cl Cl H
107 H Cl H Cl H Cl H Cl
108 H Cl H CN H H H H
109 H Cl H H H CN H H
110 H Cl H H H NO2 H H
111 H Cl H NO2 H NO2 H H
112 H Cl H NO2 H NO2 H NO2
113 H Cl H H H CF3 H H
114 H Cl H Cl H NO2 H H
115 H Cl H Cl H CN H H
116 H Cl H CH3 H Cl H H
117 H Cl H NO2 H Cl H H
118 H Cl H CN H Cl H H
119 H Cl H Cl H NO2 H Cl
120 H Cl H Cl H CF3 H Cl
121 H Cl H Cl H CN H Cl
122 H Cl H Cl H Cl H NO2
123 H Cl H Cl H Cl H CN
124 H Cl H Cl H Cl H CF3
125 H Cl H F H F H NO2
126 H Cl H NO2 H CN H H
127 H Cl H Cl H CF3 H NO2
128 H Cl H Cl H NO2 H NO2
129 H Cl H Cl H CN H NO2
130 H Cl H CH3 H Cl H NO2
131 H Cl H NO2 H Cl H NO2
132 H Cl H NO2 H CF3 H NO2
133 H Cl H NO2 H CN H NO2
134 H Cl H CF3 H NO2 H NO2
135 H Cl H CH3 H NO2 H NO2
136 H Cl H H CF3 CN H H
137 H Cl H NO2 H CN CF3 H
138 H Cl H Br H OCF3 H Br
139 H Cl H CH3 H Cl CH2CO2C2H5 H
140 H Cl H Cl CH3 Cl H H
141 H Cl H Cl CH3 Cl H NO2
142 H Cl H Cl CH3 H H H
143 H Cl H CH3 Cl H H H
144 H Cl H CH3 Cl NO2 H H
145 H Cl H Br H NO2 H CN
146 H Cl H NO2 Cl CF3 H NO2
147 H Cl H NO2 H Cl Cl H
148 H Cl H Cl H NO2 Cl H
149 H Cl H NO2 Cl Cl H NO2
150 H Cl H Cl H NO2 Cl NO2
151 H Cl H Cl H Cl Cl NO2
152 H Cl H Cl Cl CN Cl CN
153 H Cl H Cl H OCF2OCF3 Cl H
154 H Cl CN Cl H NO2 H Cl
155 H Cl CN Cl H CF3 H Cl
156 H Cl CN Cl H CN H Cl
157 H Cl CN NO2 H CF3 H NO2
158 H Cl CN Cl H Cl H Cl
159 H Cl CN NO2 H Cl H NO2
160 H Cl CN Br H NO2 H CN
161 H Cl CN NO2 H CN CF3 H
162 H Cl CN Cl H NO2 Cl H
163 H Cl CN Cl H NO2 Cl NO2
164 H Cl CN Cl H Cl Cl NO2
165 H Cl CN NO2 H NO2 H H
166 H Cl CN Cl H NO2 H NO2
167 H Cl CN Cl H CN H NO2
168 H Cl CN Cl H Cl H NO2
169 H Cl CN Cl H Cl H CN
170 H Cl CN Cl H Cl H CF3
171 H Cl Cl Cl H NO2 H Cl
172 H Cl Cl Cl H CF3 H Cl
173 H Cl Cl Cl H CN H Cl
174 H Cl Cl NO2 H CF3 H NO2
175 H Cl Cl Cl H Cl H Cl
176 H Cl Cl NO2 H Cl H NO2
177 H Cl Cl Br H NO2 H CN
178 H Cl Cl NO2 H CN CF3 H
179 H Cl Cl Cl H NO2 Cl H
180 H Cl Cl Cl H NO2 Cl NO2
181 H Cl Cl Cl H Cl Cl NO2
182 H Cl Cl NO2 H NO2 H H
183 H Cl Cl Cl H NO2 H NO2
184 H Cl Cl Cl H CN H NO2
185 H Cl Cl Cl H Cl H NO2
186 H Cl Cl Cl H Cl H CN
187 H Cl Cl Cl H Cl H CF3
188 H Cl C(=O)NH2 Cl H NO2 H Cl
189 H Cl C(=O)NH2 Cl H CF3 H Cl
190 H Cl C(=O)NH2 Cl H CN H Cl
191 H Cl C(=O)NH2 NO2 H CF3 H NO2
192 H Cl C(=O)NH2 Cl H Cl H Cl
193 H Cl C(=O)NH2 NO2 H Cl H NO2
194 H Cl C(=O)NH2 Br H NO2 H CN
195 H Cl C(=O)NH2 NO2 H CN CF3 H
196 H Cl C(=O)NH2 Cl H NO2 Cl H
197 H Cl C(=O)NH2 Cl H NO2 Cl NO2
198 H Cl C(=O)NH2 Cl H Cl Cl NO2
199 H Cl C(=O)NH2 NO2 H NO2 H H
200 H Cl C(=O)NH2 Cl H NO2 H NO2
201 H Cl C(=O)NH2 Cl H CN H NO2
202 H Cl C(=O)NH2 Cl H Cl H NO2
203 H Cl C(=O)NH2 Cl H Cl H CN
204 H Cl C(=O)NH2 Cl H Cl H CF3
205 H Cl C(=S)NH2 Cl H NO2 H Cl
206 H Cl C(=S)NH2 Cl H CF3 H Cl
207 H Cl C(=S)NH2 Cl H CN H Cl
208 H Cl C(=S)NH2 NO2 H CF3 H NO2
209 H Cl C(=S)NH2 Cl H Cl H Cl
210 H Cl C(=S)NH2 NO2 H Cl H NO2
211 H Cl C(=S)NH2 Br H NO2 H CN
212 H Cl C(=S)NH2 NO2 H CN CF3 H
213 H Cl C(=S)NH2 Cl H NO2 Cl H
214 H Cl C(=S)NH2 Cl H NO2 Cl NO2
215 H Cl C(=S)NH2 Cl H Cl Cl NO2
216 H Cl C(=S)NH2 NO2 H NO2 H H
217 H Cl C(=S)NH2 Cl H NO2 H NO2
218 H Cl C(=S)NH2 Cl H CN H NO2
219 H Cl C(=S)NH2 Cl H Cl H NO2
220 H Cl C(=S)NH2 Cl H Cl H CN
221 H Cl C(=S)NH2 Cl H Cl H CF3
222 H Cl CO2CH3 Cl H NO2 H Cl
223 H Cl CO2CH3 Cl H CF3 H Cl
224 H Cl CO2CH3 Cl H CN H Cl
225 H Cl CO2CH3 NO2 H CF3 H NO2
226 H Cl CO2CH3 Cl H Cl H Cl
227 H Cl CO2CH3 NO2 H Cl H NO2
228 H Cl CO2CH3 Br H NO2 H CN
229 H Cl CO2CH3 NO2 H CN CF3 H
230 H Cl CO2CH3 Cl H NO2 Cl H
231 H Cl CO2CH3 Cl H NO2 Cl NO2
232 H Cl CO2CH3 Cl H Cl Cl NO2
233 H Cl CO2CH3 NO2 H NO2 H H
234 H Cl CO2CH3 Cl H NO2 H NO2
235 H Cl CO2CH3 Cl H CN H NO2
236 H Cl CO2CH3 Cl H Cl H NO2
237 H Cl CO2CH3 Cl H Cl H CN
238 H Cl CO2CH3 Cl H Cl H CF3
239 H Cl CF3 Cl H NO2 H Cl
240 H Cl CF3 Cl H CF3 H Cl
241 H Cl CF3 Cl H CN H Cl
242 H Cl CF3 NO2 H CF3 H NO2
243 H Cl CF3 Cl H Cl H Cl
244 H Cl CF3 NO2 H Cl H NO2
245 H Cl CF3 Br H NO2 H CN
246 H Cl CF3 NO2 H CN CF3 H
247 H Cl CF3 Cl H NO2 Cl H
248 H Cl CF3 Cl H NO2 Cl NO2
249 H Cl CF3 Cl H Cl Cl NO2
250 H Cl CF3 NO2 H NO2 H H
251 H Cl CF3 Cl H NO2 H NO2
252 H Cl CF3 Cl H CN H NO2
253 H Cl CF3 Cl H Cl H NO2
254 H Cl CF3 Cl H Cl H CN
255 H Cl CF3 Cl H Cl H CF3
256 H Cl SO2CH3 Cl H NO2 H Cl
257 H Cl SO2CH3 Cl H CF3 H Cl
258 H Cl SO2CH3 Cl H CN H Cl
259 H Cl SO2CH3 NO2 H CF3 H NO2
260 H Cl SO2CH3 Cl H Cl H Cl
261 H Cl SO2CH3 NO2 H Cl H NO2
262 H Cl SO2CH3 Br H NO2 H CN
263 H Cl SO2CH3 NO2 H CN CF3 H
264 H Cl SO2CH3 Cl H NO2 Cl H
265 H Cl SO2CH3 Cl H NO2 Cl NO2
266 H Cl SO2CH3 Cl H Cl Cl NO2
267 H Cl SO2CH3 NO2 H NO2 H H
268 H Cl SO2CH3 Cl H NO2 H NO2
269 H Cl SO2CH3 Cl H CN H NO2
270 H Cl SO2CH3 Cl H Cl H NO2
271 H Cl SO2CH3 Cl H Cl H CN
272 H Cl SO2CH3 Cl H Cl H CF3
273 CH3 Cl NO2 Cl H NO2 H Cl
274 CH3 Cl NO2 Cl H CF3 H Cl
275 CH3 Cl NO2 Cl H CN H Cl
276 CH3 Cl NO2 NO2 H CF3 H NO2
277 CH3 Cl NO2 Cl H Cl H Cl
278 CH3 Cl NO2 NO2 H Cl H NO2
279 CH3 Cl NO2 Br H NO2 H CN
280 CH3 Cl NO2 NO2 H CN CF3 H
281 CH3 Cl NO2 Cl H NO2 Cl H
282 CH3 Cl NO2 Cl H NO2 Cl NO2
283 CH3 Cl NO2 Cl H Cl Cl NO2
284 CH3 Cl NO2 NO2 H NO2 H H
285 CH3 Cl NO2 Cl H Cl H H
286 CH3 Cl NO2 Cl H NO2 H NO2
287 CH3 Cl NO2 Cl H CN H NO2
288 CH3 Cl NO2 Cl H Cl H NO2
289 CH3 Cl NO2 Cl H Cl H CN
290 CH3 Cl NO2 Cl H Cl H CF3
291 CH3 Cl NO2 Br H NO2 H Br
292 CH3 Cl NO2 F H NO2 H F
293 CH3 Cl NO2 Cl H NO2 H Br
294 CH3 Cl NO2 F H NO2 H Cl
295 CH3 Cl NO2 F H NO2 H Br
296 COCH3 Cl NO2 Cl H NO2 H Cl
297 COCH3 Cl NO2 Cl H CF3 H Cl
298 COCH3 Cl NO2 Cl H CN H Cl
299 COCH3 Cl NO2 NO2 H CF3 H NO2
300 COCH3 Cl NO2 Cl H Cl H Cl
301 COCH3 Cl NO2 NO2 H Cl H NO2
302 COCH3 Cl NO2 Br H NO2 H CN
303 COCH3 Cl NO2 NO2 H CN CF3 H
304 COCH3 Cl NO2 Cl H NO2 Cl H
305 COCH3 Cl NO2 Cl H NO2 Cl NO2
306 COCH3 Cl NO2 Cl H Cl Cl NO2
307 COCH3 Cl NO2 NO2 H NO2 H H
308 COCH3 Cl NO2 Cl H NO2 H NO2
309 COCH3 Cl NO2 Cl H CN H NO2
310 COCH3 Cl NO2 Cl H Cl H NO2
311 COCH3 Cl NO2 Cl H Cl H CN
312 COCH3 Cl NO2 Cl H Cl H CF3
313 CO2CH3 Cl NO2 Cl H NO2 H Cl
314 CO2CH3 Cl NO2 Cl H CF3 H Cl
315 CO2CH3 Cl NO2 Cl H CN H Cl
316 CO2CH3 Cl NO2 NO2 H CF3 H NO2
317 CO2CH3 Cl NO2 Cl H Cl H Cl
318 CO2CH3 Cl NO2 NO2 H Cl H NO2
319 CO2CH3 Cl NO2 Br H NO2 H CN
320 CO2CH3 Cl NO2 NO2 H CN CF3 H
321 CO2CH3 Cl NO2 Cl H NO2 Cl H
322 CO2CH3 Cl NO2 Cl H NO2 Cl NO2
323 CO2CH3 Cl NO2 Cl H Cl Cl NO2
324 CO2CH3 Cl NO2 NO2 H NO2 H H
325 CO2CH3 Cl NO2 Cl H NO2 H NO2
326 CO2CH3 Cl NO2 Cl H CN H NO2
327 CO2CH3 Cl NO2 Cl H Cl H NO2
328 CO2CH3 Cl NO2 Cl H Cl H CN
329 CO2CH3 Cl NO2 Cl H Cl H CF3
330 SO2CH3 Cl NO2 Cl H NO2 H Cl
331 SO2CH3 Cl NO2 Cl H CF3 H Cl
332 SO2CH3 Cl NO2 Cl H CN H Cl
333 SO2CH3 Cl NO2 NO2 H CF3 H NO2
334 SO2CH3 Cl NO2 Cl H Cl H Cl
335 SO2CH3 Cl NO2 NO2 H Cl H NO2
336 SO2CH3 Cl NO2 Br H NO2 H CN
337 SO2CH3 Cl NO2 NO2 H CN CF3 H
338 SO2CH3 Cl NO2 Cl H NO2 Cl H
339 SO2CH3 Cl NO2 Cl H NO2 Cl NO2
340 SO2CH3 Cl NO2 Cl H Cl Cl NO2
341 SO2CH3 Cl NO2 NO2 H NO2 H H
342 SO2CH3 Cl NO2 Cl H NO2 H NO2
343 SO2CH3 Cl NO2 Cl H CN H NO2
344 SO2CH3 Cl NO2 Cl H Cl H NO2
345 SO2CH3 Cl NO2 Cl H Cl H CN
346 SO2CH3 Cl NO2 Cl H Cl H CF3
347 H OCH3 NO2 Cl H NO2 H Cl
348 H OCH3 NO2 Cl H CF3 H Cl
349 H OCH3 NO2 Cl H CN H Cl
350 H OCH3 NO2 NO2 H CF3 H NO2
351 H OCH3 NO2 Cl H Cl H Cl
352 H OCH3 NO2 NO2 H Cl H NO2
353 H OCH3 NO2 Br H NO2 H CN
354 H OCH3 NO2 NO2 H CN CF3 H
355 H OCH3 NO2 Cl H NO2 Cl H
356 H OCH3 NO2 Cl H NO2 Cl NO2
357 H OCH3 NO2 Cl H Cl Cl NO2
358 H OCH3 NO2 NO2 H NO2 H H
359 H OCH3 NO2 Cl H NO2 H NO2
360 H OCH3 NO2 Cl H CN H NO2
361 H OCH3 NO2 Cl H Cl H NO2
362 H OCH3 NO2 Cl H Cl H CN
363 H OCH3 NO2 Cl H Cl H CF3
364 H OCH3 NO2 Br H NO2 H Br
365 H OCH3 NO2 F H NO2 H F
366 H OCH3 NO2 Cl H NO2 H Br
367 H OCH3 NO2 F H NO2 H Cl
368 H OCH3 NO2 F H NO2 H Br
369 H SCH3 NO2 Cl H NO2 H Cl
370 H SCH3 NO2 Cl H CF3 H Cl
371 H SCH3 NO2 Cl H CN H Cl
372 H SCH3 NO2 NO2 H CF3 H NO2
373 H SCH3 NO2 Cl H Cl H Cl
374 H SCH3 NO2 NO2 H Cl H NO2
375 H SCH3 NO2 Br H NO2 H CN
376 H SCH3 NO2 NO2 H CN CF3 H
377 H SCH3 NO2 Cl H NO2 Cl H
378 H SCH3 NO2 Cl H NO2 Cl NO2
379 H SCH3 NO2 Cl H Cl Cl NO2
380 H SCH3 NO2 NO2 H NO2 H H
381 H SCH3 NO2 Cl H NO2 H NO2
382 H SCH3 NO2 Cl H CN H NO2
383 H SCH3 NO2 Cl H Cl H NO2
384 H SCH3 NO2 Cl H Cl H CN
385 H SCH3 NO2 Cl H Cl H CF3
386 H SCH3 NO2 Br H NO2 H Br
387 H SCH3 NO2 F H NO2 H F
388 H SCH3 NO2 Cl H NO2 H Br
389 H SCH3 NO2 F H NO2 H Cl
390 H SCH3 NO2 F H NO2 H Br
391 H NHCH3 NO2 Cl H NO2 H Cl
392 H NHCH3 NO2 Cl H CF3 H Cl
393 H NHCH3 NO2 Cl H CN H Cl
394 H NHCH3 NO2 NO2 H CF3 H NO2
395 H NHCH3 NO2 Cl H Cl H Cl
396 H NHCH3 NO2 NO2 H Cl H NO2
397 H NHCH3 NO2 Br H NO2 H CN
398 H NHCH3 NO2 NO2 H CN CF3 H
399 H NHCH3 NO2 Cl H NO2 Cl H
400 H NHCH3 NO2 Cl H NO2 Cl NO2
401 H NHCH3 NO2 Cl H Cl Cl NO2
402 H NHCH3 NO2 NO2 H NO2 H H
403 H NHCH3 NO2 Cl H NO2 H NO2
404 H NHCH3 NO2 Cl H CN H NO2
405 H NHCH3 NO2 Cl H Cl H NO2
406 H NHCH3 NO2 Cl H Cl H CN
407 H NHCH3 NO2 Cl H Cl H CF3
408 H NHCH3 NO2 Br H NO2 H Br
409 H NHCH3 NO2 F H NO2 H F
410 H NHCH3 NO2 Cl H NO2 H Br
411 H NHCH3 NO2 F H NO2 H Cl
412 H NHCH3 NO2 F H NO2 H Br
413 H N(CH3)2 NO2 Cl H NO2 H Cl
414 H N(CH3)2 NO2 Cl H CF3 H Cl
415 H N(CH3)2 NO2 Cl H CN H Cl
416 H N(CH3)2 NO2 NO2 H CF3 H NO2
417 H N(CH3)2 NO2 Cl H Cl H Cl
418 H N(CH3)2 NO2 NO2 H Cl H NO2
419 H N(CH3)2 NO2 Br H NO2 H CN
420 H N(CH3)2 NO2 NO2 H CN CF3 H
421 H N(CH3)2 NO2 Cl H NO2 Cl H
422 H N(CH3)2 NO2 Cl H NO2 Cl NO2
423 H N(CH3)2 NO2 Cl H Cl Cl NO2
424 H N(CH3)2 NO2 NO2 H NO2 H H
425 H N(CH3)2 NO2 Cl H NO2 H NO2
426 H N(CH3)2 NO2 Cl H CN H NO2
427 H N(CH3)2 NO2 Cl H Cl H NO2
428 H N(CH3)2 NO2 Cl H Cl H CN
429 H N(CH3)2 NO2 Cl H Cl H CF3
430 H N(CH3)2 NO2 Br H NO2 H Br
431 H N(CH3)2 NO2 F H NO2 H F
432 H N(CH3)2 NO2 Cl H NO2 H Br
433 H N(CH3)2 NO2 F H NO2 H Cl
434 H N(CH3)2 NO2 F H NO2 H Br
435 H OPh NO2 Cl H NO2 H Cl
436 H OPh NO2 Cl H CF3 H Cl
437 H OPh NO2 Cl H CN H Cl
438 H OPh NO2 NO2 H CF3 H NO2
439 H OPh NO2 Cl H Cl H Cl
440 H OPh NO2 NO2 H Cl H NO2
441 H OPh NO2 Br H NO2 H CN
442 H OPh NO2 NO2 H CN CF3 H
443 H OPh NO2 Cl H NO2 Cl H
444 H OPh NO2 Cl H NO2 Cl NO2
445 H OPh NO2 Cl H Cl Cl NO2
446 H OPh NO2 NO2 H NO2 H H
447 H OPh NO2 Cl H NO2 H NO2
448 H OPh NO2 Cl H CN H NO2
449 H OPh NO2 Cl H Cl H NO2
450 H OPh NO2 Cl H Cl H CN
451 H OPh NO2 Cl H Cl H CF3
452 H OPh NO2 Br H NO2 H Br
453 H OPh NO2 F H NO2 H F
454 H OPh NO2 Cl H NO2 H Br
455 H OPh NO2 F H NO2 H Cl
456 H OPh NO2 F H NO2 H Br
457 H OCH2CF3 NO2 Cl H NO2 H Cl
458 H OCH2CF3 NO2 Cl H CF3 H Cl
459 H OCH2CF3 NO2 Cl H CN H Cl
460 H OCH2CF3 NO2 NO2 H CF3 H NO2
461 H OCH2CF3 NO2 Cl H Cl H Cl
462 H OCH2CF3 NO2 NO2 H Cl H NO2
463 H OCH2CF3 NO2 Br H NO2 H CN
464 H OCH2CF3 NO2 NO2 H CN CF3 H
465 H OCH2CF3 NO2 Cl H NO2 Cl H
466 H OCH2CF3 NO2 Cl H NO2 Cl NO2
467 H OCH2CF3 NO2 Cl H Cl Cl NO2
468 H OCH2CF3 NO2 NO2 H NO2 H H
469 H OCH2CF3 NO2 Cl H NO2 H NO2
470 H OCH2CF3 NO2 Cl H CN H NO2
471 H OCH2CF3 NO2 Cl H Cl H NO2
472 H OCH2CF3 NO2 Cl H Cl H CN
473 H OCH2CF3 NO2 Cl H Cl H CF3
474 H OCH2CF3 NO2 Br H NO2 H Br
475 H OCH2CF3 NO2 F H NO2 H F
476 H OCH2CF3 NO2 Cl H NO2 H Br
477 H OCH2CF3 NO2 F H NO2 H Cl
478 H OCH2CF3 NO2 F H NO2 H Br
479 H NHCH2CF3 NO2 Cl H NO2 H Cl
480 H NHCH2CF3 NO2 Cl H CF3 H Cl
481 H NHCH2CF3 NO2 Cl H CN H Cl
482 H NHCH2CF3 NO2 NO2 H CF3 H NO2
483 H NHCH2CF3 NO2 Cl H Cl H Cl
484 H NHCH2CF3 NO2 NO2 H Cl H NO2
485 H NHCH2CF3 NO2 Br H NO2 H CN
486 H NHCH2CF3 NO2 NO2 H CN CF3 H
487 H NHCH2CF3 NO2 Cl H NO2 Cl H
488 H NHCH2CF3 NO2 Cl H NO2 Cl NO2
489 H NHCH2CF3 NO2 Cl H Cl Cl NO2
490 H NHCH2CF3 NO2 NO2 H NO2 H H
491 H NHCH2CF3 NO2 Cl H NO2 H NO2
492 H NHCH2CF3 NO2 Cl H CN H NO2
493 H NHCH2CF3 NO2 Cl H Cl H NO2
494 H NHCH2CF3 NO2 Cl H Cl H CN
495 H NHCH2CF3 NO2 Cl H Cl H CF3
496 H NHCH2CF3 NO2 Br H NO2 H Br
497 H NHCH2CF3 NO2 F H NO2 H F
498 H NHCH2CF3 NO2 Cl H NO2 H Br
499 H NHCH2CF3 NO2 F H NO2 H Cl
500 H NHCH2CF3 NO2 F H NO2 H Br
501 H Cl NO2 Cl H NO2 H Br
502 H Cl NO2 Br H NO2 H Br
503 H Cl NO2 Cl H CO2CH3 H Cl
504 H Cl NO2 F H NO2 H Cl
505 H Cl NO2 F H H H F
506 H Cl NO2 F H Cl H F
507 CH3 Cl NO2 NO2 H NO2 H NO2
508 H Cl NO2 Cl H CONHCH3 H Cl
509 H NHCH3 NO2 Cl H CONHCH3 H Cl
510 CH3 Cl NO2 Cl H CF3 H H
511 H Cl NO2 Cl H COOH H Cl
512 CH2CH=CH2 Cl NO2 Cl H NO2 H Cl
513 CH2CH=CCl2 Cl NO2 Cl H NO2 H Cl
514 CH2CH=CF2 Cl NO2 Cl H NO2 H Cl
515 (CH2)2CH=CF2 Cl NO2 Cl H NO2 H Cl
516 (CH2)2CF=CF2 Cl NO2 Cl H NO2 H Cl
517 CH2CHF2 Cl NO2 Cl H NO2 H Cl
518 CH2C=CH Cl NO2 Cl H NO2 H Cl
519 CH2C=C-I Cl NO2 Cl H NO2 H Cl
520 CH2C=CCH3 Cl NO2 Cl H NO2 H Cl
521 H Cl NO2 CH3 H H H Cl
522 H Cl NO2 CH3 H NO2 H Cl
523 H Cl NO2 CH3 H NO2 H Br
524 H Cl NO2 CH3 H NO2 H F

The technical scheme of the present invention also includes the preparation method of the compounds  and the reaction formula is as follow:

? ? ?-a ?-b(R1?H)
Wherein: X and Y are different  separately selected from halogen atom or amino; Z is halogen atom; R2  R3  R4  R5  R6  R7 and R8 are defined respectively as mentioned before; R1 are defined as mentioned before  but R1?H.
According to the above preparation method  treatment of intermediate ? with intermediate ? at the presence of base gives compounds ?-a of general formula I (R1=H)  which react with Z-R1 to give compounds ?-b of general formula I (R1?H).
The proper base mentioned above may be selected from potassium hydroxide  sodium hydroxide  sodium carbonate  potassium carbonate  sodium bicarbonate  triethylamine  pyridine  sodium methoxide  sodium ethoxide  sodium hydride  potassium tert-butoxide or sodium tert-butoxide and so on.
The reaction can be carried out in proper solvent  and the proper solvent mentioned may be selected from tetrahydrofuran  acetonitrile  toluene  xylene  benzene  DMF  N-methylpyrrolidone  DMSO  acetone or butanone and so on.
The proper reaction temperature is from room temperature to boiling point of solvent  generally is 20-100°C.
The reaction time is in the range of 30 minutes to 20 hours  generally is 1-10 hours.
Intermediates ? are commercially available  or prepared according to the known methods  such as referring to Indian Journal of Chemistry  Section B: Organic Chemistry Including Medicinal Chemistry  45B(4)  972-975  2006; Tetrahedron Letters  44(21)  4085-4088  2003; PL174903  etc.
Intermediate ? can be prepared according to the known methods  such as referring to JP2003292476  US2010160695  etc.
The compounds of general formula I can also be prepared by other methods  for example  the nitration of substituted diphenylamine intermediate (general formula ?) can give compounds of general formula I with NO2 group  referring to US4041172 and so on.

Wherein: R1  R2  R4  R5  R6  R7 and R8 are defined respectively as mentioned before; R3 is selected from H or NO2.
The nitration of compounds of general formula I  in which at least one of R4  R6 or R8 is H  can add one or two NO2 groups to these compounds of general formula I.
The halogenation of substituted diphenylamine compounds of general formula I  in which R4  R6 or R8 is not halogen atom  can add one or two halogen atoms to these compounds of general formula I.
The compounds of general formula I  in which R2 is alkylamino  alkoxy or alkylthio and so on  can be prepared from the reaction of compounds of general formula I whose R2 is halogen atom with amine  alcohol or mercaptan (or their salts).
The salts of compounds having general formula I can be prepared from the reaction of the compounds of general formula I with corresponding acid according to routine method. The proper acid may be selected from hydrochloric acid  sulfuric acid  phosphoric acid  trifluoroacetic acid  methylsulfonic acid  p-toluenesulfonic acid  etc.
Although the compounds having general formula I of the present invention and some compounds reported in the prior art are all diphenylamine compounds  there are significant differences between their structural characteristics. And because of the structural differences  the compounds of the present invention show much better fungicidal activity. Meanwhile  the raw materials to prepare these compounds are cheap and the methods are simple and convenient  therefore the compounds of the present invention have lower costs and broader application prospect compared with known fungicides.
The compounds of general formula I show excellent activity against many plant pathogens/diseases in agricultural and other fields. Therefore the technical scheme of the present invention also include the uses of the compounds having general formula I to control plant pathogens/diseases in agricultural and other fields  such as using the compounds of general formula I to prepare substances to control plant pathogens/diseases.
The present invention is explained by the following examples of plant disease  but without being restricted thereby.
The compounds of general formula I can be used to control these plant diseases: Oomycete diseases  such as downy mildew (cucumber downy mildew  rape downy mildew  soybean downy mildew  downy mildew of beet  downy mildew of sugarcane  tobacco downy mildew  pea downy mildew  vegetable sponge downy mildew  chinese wax gourd downy mildew  muskmelon downy mildew  chinese cabbage downy mildew  spinach downy mildew  radish downy mildew  grape downy mildew  onion downy mildew)  white rust (rape white rust  chinese cabbage white rust)  damping-off disease (rape damping-off  tobacco damping-off  tomato damping-off  pepper damping-off  eggplant damping-off  cucumber damping-off  cotton damping-off)  pythium rot (pepper soft stale disease  vegetable sponge cottony leak  chinese wax gourd cottony leak)  blight (broad bean phytophthora blight  cucumber phytophthora blight  pumpkin phytophthora rot  chinese wax gourd phytophthora blight  watermelon phytophthora blight  muskmelon phytophthora blight  pepper phytophthora blight  chinese chives phytophthora blight  carlic phytophthora blight  cotton phytophthora blight)  late blight (potato late blight  tomato late blight) and so on; diseases caused by Deuteromycotina  such as wilt disease (sweet potato fusarium wilt  cotton fusarium wilt disease  sesame wilt disease  fusarium wilt disease of costarbean  tomato fusarium wilt  bean fusarium wilt  cucumber fusarium wilt  vegetable sponge fusarium wilt  pumpkin fusarium wilt  chinese wax gourd fusarium wilt  watermelon fusarium wilt  muskmelon fusarium wilt  pepper fusarium wilt  broad bean fusarium wilt  fusarium wilt disease of rape  fusarium wilt disease of soybean)  root rot (pepper root rot  eggplant root rot  bean fusarium root-rot  cucumber fusarium root rot  balsam pear fusarium root rot  cotton black root rot  broad bean thielaviopsis root rot)  drooping disease (cotton soreshin  sesame soreshin  pepper rhizoctonia rot  cucumber rhizoctonia rot  chinese cabbage rhizoctonia rot)  anthracnose (sorghum anthracnose  cotton anthracnose  kenaf anthracnose  jute anthracnose  flax anthracnose  tobacco anthracnose  mulberry anthracnose  pepper anthracnose  eggplant anthracnose  bean anthracnose  cucumber anthracnose  balsam pear anthracnose  summer squash anthracnose  chinese wax gourd anthracnose  watermelon anthracnose  muskmelon anthracnose  litchi anthracnose)  verticillium wilt (cotton verticillium wilt  verticillium wilt of sunflower  tomato verticillium wilt  pepper verticillium wilt  eggplant verticillium wilt)  scab (summer squash scab  chinese wax gourd scab  muskmelon scab)  gray mold (cotton boll gray mold  kenaf gray mold  tomato gray mold  pepper gray mold  bean gray mold  celery gray mold  spinach gray mold  kiwi fruit gray mold rot)  brown spot (cotton brown spot  jute brown spot  beet sercospora leaf spot  peanut brown spot  pepper brown leaf spot  chinese wax gourd corynespora leaf spot  soybean brown spot  sunflower brown spot  pea ascochyta blight  broad bean brown spot)  black spot (flax black spot  rape alternaria leaf spot  sesame black spot  sunflower alternaria leaf spot  costarbean alternaria leaf spot  tomato nail head spot  pepper black fruit spot  eggplant black spot  bean leaf spot  cucumber alternaria blight  celery alternaria black leaf spot  carrot alternaria black rot  carrot leaf blight  apple alternaria rot  peanut brown spot)  spot blight (tomato septoria leaf spot  pepper septoria leaf spot  celery late blight)  early blight (tomato early blight  pepper early blight  eggplant early blight  potato early blight  celery early blight)  ring spot (soybean zonate spot  sesame ring spot  bean zonate spot)  leaf blight (sesame leaf blight  sunflower leaf blight  watermelon alternaria blight  muskmelon alternaria spot)  basal stem rot (tomato basal stem rot  bean rhizoctonia rot)  and others (corn northern leaf spot  kenaf damping-off  rice blast  millet black sheath  sugarcane eye spot  cotton aspergillus boll rot  peanut crown rot  soybean stem blight  soybean black spot  muskmelon alternaria leaf blight  peanut web blotch  tea red leaf spot  pepper phyllosticta blight  chinese wax gourd phyllosticta leaf spot  celery black rot  spinach heart rot  kenaf leaf mold  kenaf brown leaf spot  Jute stem blight soybean cercospora spot  sesame leaf spot  costarbean gray leaf spot  tea brown leaf spot  eggplant cercospora leaf spot  bean cercospora leaf spot  balsam pear cercospora leaf spot  watermelon cercospora leaf spot  jute dry rot  sunflower root and stem rot bean charcoal rot  soybean target spot  eggplant corynespora leaf spot  cucumber corynespora target leaf spot  tomato leaf mold  eggplant fulvia leaf mold  broad bean chocolate spot) and so on; diseases caused by Basidiomycete  such as rust (wheat stripe rust  wheat stem rust  wheat leaf rust  peanut rust  sunflower rust  sugarcane rust  chinese chives rust  onion rust  millet rust  soybean rust)  smut (corn head smut  corn smut  sorghum silk smut  sorghum loose kernel smut  sorghum hard smut  sorghum smut  millet kernel smut  sugarcane smut  bean rust)  and others (for example  wheat sheath blight and rice sheath blight) and so on; diseases caused by Ascomycete  such as powdery mildew (wheat powdery mildew  rape powdery mildew  powdery mildew of sesame  powdery mildew of sunflower  beet powdery mildew  eggplant powdery mildew  pea powdery mildew  vegetable sponge powdery mildew  pumpkin powdery mildew  summer squash powdery mildew  chinese wax gourd  muskmelon powdery mildew  grape powdery mildew  broad bean powdery mildew)  sclerotinia rot (flax sclertiniose  rape sclertiniose  soybean sclertiniose  peanut sclertiniose  tobacco sclerotinia rot  pepper sclerotinia rot  eggplant sclerotinia rot  bean sclerotinia rot  pea sclerotinia rot  cucumber sclerotinia rot  balsam pear sclerotinia rot  chinese wax gourd sclerotinia rot  watermelon sclerotinia disease  celery stem rot)  scab (apple scab  pear scab) and so on. Especially  the compounds of the present invention exhibit very good control against cucumber downy mildew  rice blast and gray mold of vegetables at very low doses.
Thanks to their positive characteristics  the compounds mentioned above can be advantageously used in protecting crops of farming and gardening  domestic and breeding animals  as well as environments frequented by human beings  from pathogens.
In order to obtain desired effect  the dosage of the compound to be applied can vary with various factors  for example  the used compound  the protected crop  the type of harmful organism  the degree of infestation  the climatic conditions  the application method and the adopted formulation.
The dosage of compounds in the range of 10 g to 5 kg per hectare can provide a sufficient control.
An another object of the present invention also relates to a method for controlling phytopathogenic fungi in crops of farming and gardening and/or on domestic and breeding animals and/or environments frequented by human beings  by application of the compounds having general formula I. In particular  the dosage of compounds to be applied varies from 10 g to 5 kg per hectare.
For practical application in agriculture  it is usually beneficial to use compositions containing one or more compounds of general formula I.
Therefore  a further technical scheme of the present invention relates to fungicidal compositions containing one or more compounds having general formula I as active ingredient and acceptable carrier in agriculture  the weight percentage of the active ingredient in the compositions is 0.5-90%.
Compositions can be used in the form of dry powders  wettable powders  emulsifiable concentrates  microemulsions  pastes  granulates  solutions  suspensions  etc..The selection of the type of compositions depends on the specific application.
The compositions are prepared in the known method  for example by diluting or dissolving the active substance with a solvent medium and/or a solid diluent  optionally in the presence of surface-active agents.
Solid diluents or carriers which can be used are  for example: silica  kaolin  bentonite  talc  diatomite  dolomite  calcium carbonate  magnesia  chalk  clays  synthetic silicates  attapulgite  sepiolite.
Liquid diluents which can be used are  for example  besides water  aromatic organic solvents (xylols or mixtures of alkylbenzols  chlorobenzene  etc.)  paraffins (petroleum fractions)  alcohols (methanol  propanol  butanol  octanol  glycerin  etc.)  esters (ethyl acetate  isobutyl acetate  etc.)  ketones (cyclohexanone  acetone  acetophenone  isophorone  ethylamylketone  etc.)  amides (N  N-dimethylformamide  N-methylpyrrolidone  etc.).
Surface-active agents which can be used are salts of sodium  calcium  triethylamine or triethanolamine of alkylsulfonates  alkylarylsulfonates  polyethoxylated alkylphenols  polyethoxylated esters of sorbitol  ligninsulfonates  etc.
The compositions can also contain special additives for particular purposes  for example adhesion agents such as Arabic gum  polyvinyl alcohol  polyvinyl-pyrrolidone  etc.
The concentration of active ingredient in the above compositions can vary within a wide range depending on the active compound  the applications for which they are destined  the environmental conditions and the type of adopted formulation. In general the concentration of active ingredient ranges from 1% to 90%  preferably from 5% to 50%.
If required  other active ingredients being compatible with the compounds having general formula I can be added to the compositions  such as  other acaricides/insecticides  fungicides  plant growth regulators  antibiotics  herbicides  fertilizers.
The preparation methods of several common formulation examples in the present invention are as follows:
The preparation of suspension concentrate: the common active component in formula is 5% -35%. With water as the medium  the compound in the invention  dispersing agent  suspending agent and antifreeze are added to sanding machine for grinding to make suspension concentrate.
The preparation of water emulsion: the compound in the invention  solvent and emulsifier are mixed together to make a homogeneous oil phase. The water is mixed with antifreeze to make a homogeneous aqueous phase. In the high-speed stirring  the aqueous phase is added to the oil phase or oil phase is added to the aqueous phase  forming the water emulsion with good dispersity. The active component of water emulsions is generally 5% -15% in this invention. For the production of concentrated emulsions  the compounds of this invention are dissolved in one or more of the mixed solvent  and then emulsifier was added to enhance dispersion effects in the water.
The preparation of wettable powder: according to formulation requirements  the compound in the invention  surfactants and solid diluents are mixed well  after smashing through ultrafine pulverizer  that is the wettable powder products (for example  10%-40%). To prepare the spraying wettable powder  the compounds of this invention can form a mixture with solid powder  such as clay  inorganic silicates  carbonates  as well as wetting agents  adhesives and/or dispersant agent.
The preparation of water dispersible granules: the compound in the invention and powdered solid diluents  wetting agents and adhesives are mixed to smash  kneading together with water  added to the granulation machine with 10 to 100 mesh for granulation  then by drying and sieving (at the scope screen). Also  the compound of the invention  dispersants  disintegrants  wetting agents and solid diluent are added to sanding machine  grinding in water to produce suspension and then spray-drying granulation  usually the content of the prepared granular products is 20% -30%.

DETAILED DESCRIPTION OF THE INVENTION
The present invention is illustrated by the following examples  but without being restricted thereby. (All raw materials are commercially available unless otherwise specified.)
PREPARATION EXAMPLES
Example 1: The preparation of compound 2

0.81 g (0.005mol) of 2 4-dichloroaniline was added in portions to a suspension of 0.4g (0.01mol) of NaH (60%) and 20 mL of THF  the mixture was stirred for 30 min after addition  1.56 g (0.006mol) of 2 6-dichloro-3 5-dinitrotulune in 30 mL of THF was added within 30 min  then stirred for another 5 h. After the reaction was over by Thin-Layer Chromatography monitoring  the reaction mixture was filtered. The filtrate was concentrated under reduced pressure  then the residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90°C) = 1/20  as an eluent) to give 1.37 g of compound 2 as yellow solid  m.p. 136-137°C.
1H-NMR spectrum(300MHz,internal standard: TMS,solvent CDCl3) d(ppm): 2.14(s  3H)  6.53(d  1H)  7.17(d  1H)  7.49(s  1H)  8.68(s  1H)  8.93(s  1H).
Example 2: The preparation of compound 38

0.56 g (0.0015mol) of compound 2 was dissolved in 5 mL of concentrated sulfuric acid (96%  the same below) and cooled to 0°C  0.15 g of fuming nitric acid (95%) and 3mL of concentrated sulfuric acid was mixed evenly and added to the flask  then the reaction mixture was stirred for another 5 min. After the reaction was over by Thin-Layer Chromatography monitoring  the reaction mixture was poured into ice water  the solid precipitated was filtered  and the filter mass was washed with water and dried to give 0.59 g of compound 38 as brown solid  m.p. 156-158°C.
1H-NMR spectrum(300MHz,internal standard: TMS,solvent CDCl3) d(ppm): 2.09(s  3H)  7.66(s  1H)  8.01(s  1H)  8.60(s  1H)  9.75(s  1H).
Example 3: The preparation of compound 43

0.83 g (0.004mol) of 2 6-dichloro-4-nitroaniline was added in portions to a suspension of 0.32g (0.008mol) of NaH (60%) and 10 mL of DMF  the mixture was stirred for 30 min after addition  1.20 g (0.0048mol) of 2 6-dichloro-3 5-dinitrotulune was added in portions within 30 min  then stirred for another 3 h. After the reaction was over by Thin-Layer Chromatography monitoring  the reaction mixture was poured into 50 mL of saturated brine and extracted with ethyl acetate  the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90°C) = 1/10  as an eluent) to give 1.20 g of compound 43 as yellow solid  m.p. 157-158°C.
1H-NMR spectrum(300MHz,internal standard: TMS,solvent CDCl3) d(ppm): 2.02(s  3H)  8.29(s  2H)  8.65(s  1H)  8.95(s  1H).
Example 4: The preparation of compound 89

The intermediate M prepared by the procedure of Example 3 was nitrated according to Example 2 to give compound 89 as reddish-brown solid  m.p. 136-137°C.
1H-NMR spectrum(300MHz,internal standard: TMS,solvent CDCl3) d(ppm): 2.41(s  3H)  8.50(s  1H)  8.72(s  1H)  10.10(s  1H).
Example 5: The preparation of compound 285

0.38 g (0.001mol) of compound 2 was added to a suspension of 0.10g (0.0025mol) of NaH (60%) and 10 mL of DMF  the mixture was stirred for 1 h and then added thereto 0.43 g (0.003mol) of CH3I  the resulting mixture was allowed to react for 5 h. After the reaction was over by Thin-Layer Chromatography monitoring  the reaction mixture was poured into 50 mL of saturated brine and extracted with ethyl acetate  the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90°C) = 1/10  as an eluent) to give 0.15 g of compound 285 as yellow solid  m.p. 142-144°C.
1H-NMR spectrum(300MHz,internal standard: TMS,solvent CDCl3) d(ppm): 2.54(s  3H)  3.31(s  3H)  7.09(d  1H)  7.25(d  2H)  8.04(s  1H).
Example 6: The preparation of compound 391


0.42 g of compound 43 (0.001mol) was added to a microwave vial and dissolved with 2.5 mL of DMSO  1 mL of methylamine aqueous solution (25%) was added  the vial was lidded and put into the microwave reactor  then the reaction was carried out at 150°C for 40 min. The reaction mixture was poured into 50 mL of saturated brine and extracted with ethyl acetate  the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90°C) = 1/20  as an eluent) to give 0.25 g of compound 391 as yellow solid  m.p. 218-219°C.
1H-NMR spectrum(300MHz,internal standard: TMS,solvent CDCl3) d(ppm): 1.70(s  3H)  3.09(d  3H)  8.25(d  1H)  8.31(s  2H)  9.12(s  1H)  9.58(s  1H).
Other compounds of the present invention were prepared according to the above examples.
Physical properties and 1HNMR spectrum (1HNMR,300MHz,internal standard: TMS,ppm) of some compounds of this invention are as follows:
Compound 1: m.p. 136-138°C. d(CDCl3): 2.12(s  3H)  7.21(m  2H)  7.26(m  1H)  8.72(s  1H)  9.00(s  1H).
Compound 4: m.p. 142-143°C. d(CDCl3): 2.20(s  3H)  6.59(s  1H)  7.58(s  1H)  8.67(s  1H)  8.80(s  1H).
Compound 5: m.p. 160-162°C. d(CDCl3): 1.95(s  3H)  7.41(s  2H)  8.72(s  1H)  9.19(s  1H).
Compound 7: m.p. 184-186°C. d(CDCl3): 2.22(s  3H)  6.87(d  2H) 7.62(d  2H)  8.66(s  1H)  8.93(s  1H).
Compound 8: m.p. 172-174°C. d(DMSO): 2.34(s  3H)  6.83(d  2H) 8.06(d  2H)  8.64(s  1H)  9.49(s  1H).
Compound 9: m.p. 185-186°C. d(CDCl3): 2.41(s  3H)  6.56(d  1H) 8.31(d  1H)  8.52(s  1H)  9.23(s  1H)  10.59(s  1H).
Compound 10: a red oil. d(CDCl3): 2.27(s  3H)  8.52(s  1H)  9.09(s  2H)  10.93(s  1H).
Compound 12: m.p. 91-94°C. d(CDCl3): 2.14(s  3H)  6.91(d  2H) 7.21(d  2H)  8.71(s  1H)  9.20(s  1H).
Compound 28: m.p. 158-160°C. d(CDCl3): 2.10(s  3H)  6.83(d  4H) 7.12(m  2H)  7.34(m  4H)  8.56(s  1H).
Compound 31: m.p. 106-108°C. d(CDCl3): 2.22(s  3H)  6.55(d  1H)  7.43(d  1H)  7.75(s  1H)  8.65(s  1H)  8.87(s  1H).
Compound 32: m.p. 191-193°C. d(CDCl3): 2.29(s  3H)  6.48(d  1H)  8.06(d  1H)  8.41(s  1H)  8.62(s  1H)  8.79(s  1H).
Compound 33: m.p. 206-208°C. d(CDCl3): 2.25(s  3H)  6.48(d  1H)  7.47(d  1H)  7.77(s  1H)  8.62(s  1H)  8.80(s  1H).
Compound 34: m.p. 121-123°C. d(CDCl3): 2.02(s  3H)  2.40(s  3H)  6.53(d  1H) 7.10(d  1H)  7.27(s  1H)  8.74(s  1H)  9.03(s  1H).
Compound 36: m.p. 204-205°C. d(CDCl3): 2.31(s  3H)  6.48(d  1H) 7.43(d  1H)  8.26(s  1H)  8.54(s  1H)  10.36(s  1H).
Compound 39: m.p. 148-150°C. d(CDCl3): 2.07(s  3H)  7.53(s  1H)  7.72(s  1H)  8.71(s  1H)  8.97(s  1H).
Compound 41: m.p. 154-156°C. d(CDCl3): 2.21(s  3H)  7.20(m  1H)  7.80(m  1H)  8.59(s  1H)  9.94(s  1H).
Compound 42: m.p. 140-142°C. d(CDCl3): 2.17(s  3H)  7.19(d  2H)  8.71(s  1H)  8.94(s  1H).
Compound 44: m.p. 143-144°C. d(CDCl3): 1.98(s  3H)  7.66(s  2H)  8.70(s  1H)  9.10(s  1H).
Compound 45: m.p. 180-182°C. d(CDCl3): 1.99(s  3H)  7.69(s  2H)  8.67(s  1H)  9.00(s  1H).
Compound 47: m.p. 241-243°C. d(CDCl3): 1.97(s  3H)  7.83(s  2H)  8.69(s  1H)  9.11(s  1H).
Compound 51: m.p. 259-261°C. d(CDCl3): 2.38(s  3H)  6.54(d  1H)  7.70(d  1H)  8.50(s  1H)  8.62(s  1H)  10.51(s  1H).
Compound 61: m.p. 160-162°C. d(CDCl3): 2.18(s  3H)  7.88(d  1H)  8.32(d  1H)  8.55(s  1H)  9.97(s  1H).
Compound 62: m.p. 169-171°C. d(CDCl3): 2.26(s  3H)  8.50(d  2H)  8.99(s  1H)  10.14(s  1H).
Compound 63: m.p. 204-206°C. d(CDCl3): 2.23(s  3H)  7.87(s  1H)  8.38(s  1H)  8.51(s  1H)  10.00(s  1H).
Compound 67: m.p. 187-190°C. d(CDCl3): 2.18(s  3H)  8.23(s  2H)  8.57(s  1H)  10.39(s  1H).
Compound 69: m.p. 93-95°C. d(CDCl3): 2.19(s  3H)  8.14(s  2H)  8.56(s  1H)  10.42(s  1H).
Compound 77: an orange oil. d(DMSO): 2.33(s  3H)  6.92(d  1H)  7.26(s  1H)  7.78(d  1H)  8.63(s  1H)  9.54(s  1H).
Compound 78: m.p. 204-206°C. d(DMSO): 2.32(s  3H)  7.03(s  1H)  8.73(s  1H)  8.86(s  1H)  10.40(s  1H).
Compound 79: m.p. 125-127°C. d(CDCl3): 1.94(s  3H)  7.53(s  2H)  8.75(s  1H)  9.29(s  1H).
Compound 81: m.p. 160-161°C. d(CDCl3): 2.13(s  3H)  2.54(s  3H)  6.40(d  1H)  7.19(d  1H)  8.68(s  1H)  8.96(s  1H).
Compound 83: m.p. 110-112°C. d(CDCl3): 2.03(s  3H)  2.50(s  3H)  6.50(d  1H)  7.05(t  1H)  7.24(d  1H)  8.73(s  1H)  9.06(s  1H).
Compound 84: m.p. 133-135°C. d(CDCl3): 2.03(s  3H)  2.50(s  3H)  6.53(d  1H)  7.06(t  1H)  7.21(d  1H)  8.74(s  1H)  9.08(s  1H).
Compound 86: m.p. 158-161°C. d(CDCl3): 2.16(s  3H)  2.61(s  3H)  6.47(d  1H)  7.67(d  1H)  8.69(s  1H)  8.85(s  1H).
Compound 88: m.p. 172-175°C. d(DMSO): 2.32(s  3H)  8.49(s  1H)  8.68(s  2H)  9.50(s  1H).
Compound 90: m.p. 127-129°C. d(CDCl3): 2.36(s  3H)  6.55(s  1H)  8.40(s  1H)  8.54(s  1H)  10.31(s  1H).
Compound 91: m.p. 169-171°C. d(CDCl3): 2.32(s  3H)  6.42(s  1H)  8.20(s  1H)  8.60(s  1H)  8.62(s  1H).
Compound 96: m.p. 159-162°C. d(CDCl3): 2.16(s  3H)  8.23(s  1H)  8.63(s  1H)  8.91(s  1H).
Compound 97: m.p. 133-135°C. d(CDCl3): 2.07(s  3H)  7.70(s  1H)  8.69(s  1H)  9.22(s  1H).
Compound 101: m.p. 96-97°C. d(CDCl3): 2.21(s  3H)  5.08(m  1H)  6.59(s  1H)  7.49(s  1H)  8.66(s  1H)  8.78(s  1H).
Compound 102: m.p. 192-194°C. d(CDCl3): 2.20(s  3H)  7.05(s  2H)  8.04(s  1H)  8.22(s  1H)  9.07(s  1H)  9.43(s  1H).
Compound 106: m.p. 112-114°C. d(CDCl3): 2.18(s  3H)  6.38(s  1H)  7.38(d  1H)  7.50(s  1H)  7.97(d  1H)  8.11(s  1H).
Compound 109: m.p. 146-148°C. d(CDCl3): 2.19(s  3H)  6.70(d  2H)  7.36(d  1H)  7.53(d  2H)  7.96(d  1H)  8.20(s  1H).
Compound 110: m.p. 136-138°C. d(CDCl3): 2.22(s  3H)  6.70(d  2H)  7.41(d  1H)  8.00(d  1H)  8.16(d  2H)  8.22(s  1H).
Compound 113: m.p. 72-74°C. d(CDCl3): 2.12(s  3H)  6.75(d  2H)  7.12(d  2H)  7.25(d  1H)  7.98(d  1H)  8.46(s  1H).
Compound 116: a red oil. d(CDCl3): 2.02(s  3H)  2.38(s  3H)  6.34(d  1H)  7.00(d  1H)  7.18(m  2H)  7.98(d  1H)  8.30(s  1H).
Compound 120: a brown oil. d(CDCl3): 1.92(s  3H)  7.22(d  1H)  7.58(s  2H)  7.93(d  1H)  8.39(s  1H).
Compound 126: m.p. 158-160°C. d(CDCl3): 2.30(s  3H)  6.47(d  1H)  7.59(m  2H)  7.94(d  1H)  8.60(s  1H)  10.21(s  1H).
Compound 136: m.p. 136-138°C. d(CDCl3): 2.22(s  3H)  6.75(d  1H)  7.03(s  1H)  7.45(d  1H)  7.67(d  1H)  7.99(d  1H)  8.16(s  1H).
Compound 347: m.p. 134-136°C. d(CDCl3): 1.79(s  3H)  3.96(s  3H)  8.29(s  2H)  8.74(s  1H)  9.18(s  1H).
Compound 369: m.p. 132-134°C. d(CDCl3): 2.11(s  3H)  2.39(s  3H)  8.29(s  2H)  8.47(s  1H)  8.95(s  1H).
Compound 413: m.p. 178-180°C. d(CDCl3): 1.71(s  3H)  2.86(s  6H)  8.29(s  2H)  8.66(s  1H)  9.45(s  1H).
Compound 457: m.p. 126-128°C. d(CDCl3): 1.83(s  3H)  4.42(q  2H)  8.30(s  2H)  8.85(s  1H)  9.20(s  1H).
Compound 501: m.p. 151-153°C. d(CDCl3): 1.99(s  3H)  8.31(d  1H)  8.47(d  1H)  8.66(s  1H)  9.00(s  1H).
Compound 502: m.p. 151-154°C. d(CDCl3): 1.97(s  3H)  8.49(s  2H)  8.68(s  1H)  9.03(s  1H).
Compound 503: m.p. 132-134°C. d(CDCl3): 1.95(s  3H)  3.96(s  3H)  8.05(s  2H)  8.70(s  1H)  9.13(s  1H).
Compound 504: m.p. 135-137°C. d(CDCl3): 2.16(s  3H)  7.95(dd  1H)  8.26(t  1H)  8.63(s  1H)  8.82(s  1H).
Compound 505: m.p. 131-132°C. d(CDCl3): 2.10(s  3H)  6.99(t  2H)  7.17(m  1H)  8.72(s  1H)  8.98(s  1H).
Compound 506: m.p. 148-150°C. d(CDCl3): 2.12(s  3H)  7.04(d  2H)  8.70(s  1H)  8.87(s  1H).
Compound 507: m.p. 140-142°C. d(CDCl3): 2.58(s  3H)  3.30(s  3H)  8.38(s  1H)  8.57(s  2H).
Compound 508: d(CDCl3): 1.94(s  3H)  3.03(d  3H)  7.78(s  2H)  8.70(s  1H)  9.14(s  1H).
Compound 509: m.p. 216-218°C. d(CDCl3): 1.56(s  3H)  3.04(m  6H)  7.80(s  2H)  8.18(s  1H)  9.13(s  1H)  9.58(s  1H).
Compound 510: m.p. 138-140°C. d(CDCl3): 2.58(s  3H)  3.37(s  3H)  7.23(d  1H)  7.48(s  1H)  7.57(d  1H)  8.08(s  1H).
Compound 511: m.p. 216-219°C. d(CDCl3): 2.30(s  3H)  7.88(s  2H)  8.48(s  1H)  8.85(s  1H).
Compound 521: m.p. 146-148°C. d(CDCl3): 1.86(s  3H)  2.40(s  3H)  7.18(m  2H)  7.28(m  1H)  8.80(s  1H)  9.52(s  1H).
Compound 522: m.p. 137-139°C. d(CDCl3): 1.91(s  3H)  2.31(s  3H)  8.10(s  1H)  8.21(s  1H)  8.73(s  1H)  9.20(s  1H).
FORMULATION EXAMPLES
The active ingredient can be selected from any compound of general formula I of the present invention  base on 100% active ingredient (Weight/Weight %).
Example 7: 30% wettable powders
Compound 43 30%
Sodium dodecyl sulfate 2%
Lignin sulfonate 3%
Naphthalene sulfonic acid formaldehyde condensate 5%
Precipitated calcium carbonate Make up to 100%
The compound and other components are fully mixed  after smashing through ultrafine pulverizer  30% wettable powder products were obtained.
Example 8: 40% suspension concentrate
Compound 38 40%
Glycol 10%
Nonylphenols polyethylene glycol ether 6%
Lignin sulfonate 10%
Carboxymethyl cellulose 1%
37% of formaldehyde aqueous solution 0.2%
75% of silicone oil water emulsion 0.8%
Water Make up to 100%
Fully mixing the compound and other components  suspension concentrate can be obtained,and then any required dilution can be obtained by diluting the above suspension concentrate with water.
Example 9: 60% water dispersible granules
Compound 38 60%
Naphthalene sulfonate formaldehyde condensate 12%
N-methyl-N-oil acyl - bovine sodium 8%
Polyvinylpyrrolidone 2%
Carboxymethyl cellulose 2%
Kaolin Make up to 100%
The compound and other components were mixed and smashed  then kneaded together with water  added to the granulation 10-100 mesh machine for granulation  finally dried and sieved (at the scope screen).
BIOLOGICAL TESTING
The compounds of the present invention showed excellent activity against a variety of plant pathogens/diseases in agricultural field  but didn’t exhibit any herbicidal activity so far. The tests of compounds of the present invention against many kinds of plant diseases caused by fungi were carried out in vitro or in vivo. The results of fungicidal activity are listed in the following examples.
Example 10: Determination of the activity in vitro
The method is as follow:
High Through Put is used in the test. The compound is dissolved in a proper solvent to become a testing solution whose concentration is designed. The solvent is selected from acetone  methanol  DMF and so on according to their dissolving capability to the sample. In a no 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  pathogen germination or growth can be investigated by eyeballing  and the activity in vitro of the compound is evaluated based on germination or growth of control treatment.
The activities in vitro (inhibition rate) of parts of the compounds are as follows:
The inhibition rate against rice blast (Magnaporthe grisea):
At the dose of 25 mg/L  the inhibition rate of compounds 2  4  5  7  8  9  10  12  28  32  36  38  39  41  42  43  44  45  47  51  62  63  67  69  77  78  79  83  84  86  88  89  90  91  96  97  102  109  110  116  126  136  347  369  413  457  501  502  503  504  506  507 and so on was 100%;
At the dose of 2.8 mg/L  the inhibition rate of compounds 5  9  12  32  38  39  41  42  43  44  45  51  62  63  67  69  77  78  86  89  90  91  96  97  126  347  369  413  457  501  502  503  504  506 was 100%  and that of compounds 2  4  8  36  79  88 was 80%;
At the dose of 0.3 mg/L  the inhibition rate of compounds 38  39  42  43  44  45  67  91  97  347  369  457  501  502  504 was 100%  and that of compound 413 was 80%;
At the dose of 0.03 mg/L  the inhibition rate of compounds 42  369  504 was 100%  and that of compounds 43  45  347  501 was 80%.
The inhibition rate against cucumber gray mold (Botrytis cinerea):
At the dose of 25 mg/L  the inhibition rate of compounds 38  39  42  43  44  45  62  63  67  69  78  88  89  90  91  96  97  457 was 100%;
At the dose of 2.8 mg/L  the inhibition rate of compounds 38  39  42  43  44  45  62  63  67  69  78  89  91  97  457 was 100%  and that of compounds 88  96 was 80%;
At the dose of 0.3 mg/L  the inhibition rate of compounds 42  43  45  457 was 100%  and that of compounds 38  39  67  97 was 80%;
At the dose of 0.03 mg/L  the inhibition rate of compound 42 was 100%.
Example 11 The determination of protectant activity in vivo
The method is as follow:
The whole plant is used in this test. The compound is dissolved in a proper solvent to get mother solution. The proper solvent is selected from acetone  methanol  DMF and so on according to their dissolving capability to the sample. The rate of solvent and testing solution (v/v) is equal to or less than 5%. The mother solution is diluted with water containing 0.1% tween-80 to get the testing solution whose concentration is designed. The testing solution is sprayed to the host plant by a special plant sprayer. The plant is inoculated with fungus after 24 hours. According to the infecting characteristic of fungus  the plant is stored in a humidity chamber and then transferred into greenhouse after infection is finished. And the other plants are placed in greenhouse directly. The activity of compound is obtained by eyeballing after 7days in common.
The protectant activities in vivo of parts of the compounds are as follows:
The protectant activity against cucumber downy mildew (Pseudoperonospora cubensis) in vivo:
At the dose of 400 mg/L  the protectant activity of compounds 5  9  10  32  38  39  43  44  45  62  63  67  69  77  78  88  89  91  96  413  501  522 was 100%  and that of compounds 41  86  391  502  503  504  507 was more than 90%;
At the dose of 100 mg/L  the protectant activity of compounds 5  9  10  32  38  39  43  44  45  62  63  67  69  78  88  89 was 100%  that of compounds 77  91  96 was more than 95% and that of compounds 41  86  504 was no less than 85%;
At the dose of 50 mg/L  the protectant activity of compounds 9  38  39  43  44  63  67  69  78  88 was 100%  that of compound 62 was 98% and that of compounds 32  45  91 was no less than 70%;
At the dose of 12.5 mg/L  the protectant activity of compounds 43  63  78 was 100%  and that of compounds 38  44  67  91 was no less than 80%.
The protectant activity against corn rust (Puccinia sorghi) in vivo:
At the dose of 400 mg/L  the protectant activity of compounds 2  12  32  34  38  41  42  43  44  63  67  78  84  89  102  347  502 was 100%  that of compounds 36  88  136  369  413  501  503  504  505 was no less than 95% and that of compounds 4  39  69  81  110  116  120  391 was no less than 80%;
At the dose of 100 mg/L  the protectant activity of compounds 43  44  78  347  369  502 was 100%  and that of compounds 34  67  84  88  413  501was no less than 80%;
At the dose of 25 mg/L  the protectant activity of compounds 347  369 was 100%  and that of compounds 34  44  88  502 was no less than 60%;
At the dose of 6.25 mg/L  the protectant activity of compound 347 was 100%  and that of compound 369 was 85%.
The protectant activity against wheat powdery mildew (Blumeria graminis) in vivo:
At the dose of 400 mg/L  the protectant activity of compound 63 was 100%  and that of compounds 43  45  67  90 was no less than 80%.
The protectant activity against cucumber anthracnose (Colletotrichum lagenarium) in vivo:
At the dose of 400 mg/L  the protectant activity of compounds 43  44  78 was 100%.
Example 12: The test results of parts of compounds and contrasts
Contrastive tests were carried out between parts of compounds  contrasts and intermediates. The test results are listed in table 7-table 11 (“/” in the following tables means no test).
Table 7 The protectant activity against cucumber downy mildew in vivo
Compd. No. Protectant activity (%)
50 mg/L 12.5 mg/L 3.125mg/L
38 100 80 65
43 100 100 90
44 100 85 45
45 80 65 55
67 100 80 40
69 100 70 40
78 100 100 60
91 95 80 75
intermediate B 0 0 0
intermediate C 0 0 0
diphenylamine 0 0 0
fluazinam 100 95 40
dimethomorph 100 80 35
contrast ACS 0 0 0

Contrast ACS was reported in ACS Symposium Series(1992)  504(Synth. Chem. Agrochem. ?)  341-48  its structure is as follow:

Table 8 The protectant activity against corn rust in vivo:
Compd. No. Protectant activity (%)
100 mg/L 25 mg/L 6.25 mg/L
34 80 75 20
38 70 20 0
44 75 60 15
84 90 30 0
88 90 60 0
347 100 100 100
369 100 100 85
413 85 30 0
501 85 50 30
502 100 60 20
fluazinam 90 30 10
contrast ACS 0 0 0

Table 9 The activity against rice blast and cucumber gray mold in vitro
Compd. No. Inhibition rate against rice blast (%) Inhibition rate against cucumber gray mold (%)
0.3 mg/L 0.03 mg/L 0.3 mg/L 0.1 mg/L 0.03 mg/L
38 / / 80 50 0
39 / / 80 50 0
42 100 100 100 100 100
43 100 80 100 100 50
45 100 80 100 100 0
347 100 80 / / /
369 100 100 / / /
457 100 50 100 80 0
501 100 80 / / /
502 100 50 / / /
504 100 100 / / /
fluazinam 100 50 100 80 0
contrast ACS 0 0 0 0 0

Table 10 Contrastive results of compound 43 and contrast ACS
Compd. No. Protectant activity against cucumber downy mildew in vivo (%) Activity against rice blast in vitro (%)
100 mg/L 50 mg/L 25 mg/L 25 mg/L 8.3 mg/L 2.8 mg/L 0.9 mg/L
5 100 40 30 100 100 100 100
contrast ACS / 0 0 0 0 0 0

Table 11 Contrastive results of compound 43 and fluazinam
Target fungus Compound Activity in vitro (%)
10 mg/L 1 mg/L 0.1 mg/L
rice sheath blight (Rhizoctonia solani Palo) compound 43 100 95 74
fluazinam 97 83 69
corn southern leaf blight (Helminthosporium maydis) compound 43 100 100 54
fluazinam 100 92 41
cucumber fusarium wilt (Fusarium oxysporum f. sp.) compound 43 99 91 79
fluazinam 92 85 56
pear scab (Fusicladium pirina) compound 43 100 99 87
fluazinam 94 89 47
cotton nthracnose (Colletotrichum gossypii Southw.) compound 43 100 100 94
fluazinam 100 97 71
cotton verticillium wilt (Verticillium dahliae Kleb) compound 43 100 100 82
fluazinam 100 96 46
rape sclertiniose (Sclerotinia sclerotiorum) compound 43 100 100 88
fluazinam 100 97 57



We Claim:
1. A kind of substituted diphenylamine compounds having general formula I:
I
Wherein:
R1 is selected from H,C1-C12alkyl  C3-C12cycloalkyl  C1-C12haloalkyl  C1-C12alkylcarbonyl  C1-C12haloalkylcarbonyl  C1-C12alkoxycarbonyl  C1-C12alkylaminocarbonyl  C1-C12alkylthio  C1-C12haloalkylthio  C1-C12alkylsulfonyl  C1-C12alkoxyC1-C12alkyl  C1-C12alkoxyC1-C12alkylcarbonyl  C1-C12alkoxycarbonylC1-C12alkyl  C1-C12alkylaminothio  C2-C12 dialkylaminothio or CO-X-CO2R9  in which X is selected from (CHR9)n  CR9=CR10 or C6H4  n=1-6;
R2 is selected from halogen  C1-C12haloalkyl  C1-C12alkoxy  C1-C12haloalkoxy  C1-C12alkylamino  C1-C12haloalkylamino  C1-C12alkylthio  C1-C12haloalkylthio  C1-C12alkylsulfonyl  C3-C12cycloalkyl  C2-C12dialkylamino  C3-C12alkenyloxy  C3-C12haloalkenyloxy  C3-C12alkynyloxy  C3-C12haloalkynyloxy  C1-C12alkylcarbonyloxy  C1-C12alkylcarbonylamino  C1-C12alkylsulfonyloxy  C1-C12alkoxyC1-C12alkoxy  C1-C12alkoxycarbonylC1-C12alkoxy  or the following groups unsubstituted or substituted with 1-5 R11: aryloxy  arylamino  arylmethoxy  arylmethylamino  heteroaryloxy or heteroarylamino  and when the number of the substitutes is more than 1  R11 may be the same or different;
R3 is selected from H  halogen  NO2  CN  C(=O)NR9R10  C(=S)NR9R10  C1-C12alkylaminocarbonyl  C1-C12alkoxycarbonyl  C1-C12haloalkyl or C1-C12alkylsulfonyl;
R4 and R8 may be the same or different  respectively selected from H  halogen  CN  NO2  C(=O)NR9R10  C1-C12alkyl  C1-C12haloalkyl  C1-C12alkoxy  C1-C12haloalkoxy  C2-C12alkenyl  C2-C12alkynyl  C1-C12alkylsulfonyl  C1-C12alkylcarbonyl  C1-C12alkoxycarbonyl  C1-C12alkoxyC1-C12alkyl  C1-C12alkoxycarbonylC1-C12alkyl  or the following groups unsubstituted or substituted with 1-5 R11: aryl  arylmethyl  aryloxy  arylamino  arylcarbonyl  arylmethylcarbonyl  aryloxycarbonyl  arylaminocarbonyl or heteroaryloxy  and when the number of the substitutes is more than 1  R11 may be the same or different;
R5 and R7 may be the same or different  respectively selected from H  halogen  CN  NO2  C(=O)NR9R10  C1-C12alkyl  C1-C12haloalkyl  C1-C12alkoxy  C1-C12haloalkoxy  C1-C12alkylamino  C1-C12haloalkylamino  C1-C12alkylthio  C1-C12haloalkylthio  C2-C12alkenyl  C2-C12alkynyl  C1-C12alkylsulfonyl  C1-C12alkylcarbonyl  C1-C12alkoxycarbonyl  C1-C12alkoxyC1-C12alkyl  C1-C12alkoxycarbonylC1-C12alkyl  C1-C12alkylcarbonyloxy  C1-C12alkoxycarbonyloxy  C1-C12alkylaminocarbonyloxy  C1-C12alkylsulfonyloxy  C1-C12alkoxyC1-C12alkoxy  C1-C12haloalkoxyC1-C12haloalkoxy  C1-C12alkoxycarbonylC1-C12alkoxy  or the following groups unsubstituted or substituted with 1-5 R11: aryl  arylmethyl  aryloxy  arylamino  arylcarbonyl  arylmethylcarbonyl  aryloxycarbonyl  arylaminocarbonyl or heteroaryloxy  and when the number of the substitutes is more than 1  R11 may be the same or different;
R6 is selected from H  halogen  CN  NO2  CO2H  C(=O)NR9R10  C1-C12alkyl  C1-C12haloalkyl  C1-C12alkoxy  C1-C12haloalkoxy  C2-C12alkenyl  C2-C12alkynyl  C1-C12alkylsulfonyl  C1-C12alkylcarbonyl  C1-C12alkoxycarbonyl  C1-C12alkoxyC1-C12alkyl  C1-C12alkoxycarbonylC1-C12alkyl  C1-C12alkoxyC1-C12alkoxy  C1-C12haloalkoxyC1-C12haloalkoxy  or the following groups unsubstituted or substituted with 1-5 R11: aryl  arylmethyl  aryloxy  arylamino  arylcarbonyl  arylmethylcarbonyl  aryloxycarbonyl  arylaminocarbonyl or heteroaryloxy  and when the number of the substitutes is more than 1  R11 may be the same or different;
But R4  R5  R6  R7 and R8 can not be H simultaneously;
R9 and R10 may be the same or different  respectively selected from H or C1-C6alkyl;
R11 is selected from halogen  NO2  CN  C1-C6alkyl  C1-C6haloalkyl  C1-C6alkoxy  C1-C6haloalkoxy  C1-C6alkylthio  C1-C6alkylcarbonyl  C1-C6alkoxycarbonyl  C2-C6alkenyl  C2-C6haloalkenyl  C3-C6alkenyloxy  C3-C6haloalkenyloxy  C2-C6alkynyl  C2-C6haloalkynyl  C3-C6alkynyloxy  C3-C6haloalkynyloxy  C1-C6haloalkylthio  C1-C6haloalkylcarbonyl  C1-C6alkylamino  C1-C6haloalkylamino  C2-C8dialkylamino  C1-C6alkylcarbonylamino  C1-C6haloalkylcarbonylamino  C1-C6alkylaminocarbonyl or C1-C6haloalkylaminocarbonyl;
Or the salts of the compounds having general formula I.
2. The compounds according to the claim 1  characterized in that wherein general formula I:
R1 is selected from H,C1-C6alkyl  C3-C6cycloalkyl  C1-C6alkylcarbonyl  C1-C6haloalkylcarbonyl  C1-C6alkoxycarbonyl  C1-C6alkylthio  C1-C6haloalkylthio  C1-C6alkylsulfonyl  C1-C6alkoxyC1-C6alkyl  C1-C6alkoxyC1-C6alkylcarbonyl  C1-C6alkoxycarbonylC1-C6alkyl  C1-C6alkylaminothio  C2-C6 dialkylaminothio or CO-X-CO2R9  in which X is selected from (CHR9)n  CR9=CR10 or C6H4  n=1-3;
R2 is selected from halogen  C1-C6alkoxy  C1-C6haloalkoxy  C1-C6alkylamino  C1-C6haloalkylamino  C1-C6alkylthio  C1-C6haloalkylthio  C1-C6alkylsulfonyl  C2-C6dialkylamino  C3-C6alkenyloxy  C3-C6haloalkenyloxy  C3-C6alkynyloxy  C1-C6alkylcarbonyloxy  C1-C6alkylcarbonylamino  C1-C6alkylsulfonyloxy  C1-C6alkoxyC1-C6alkoxy  C1-C6alkoxycarbonylC1-C6alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  benzyloxy  benzylamino  pyridyloxy or pyridylamino;
R3 is selected from Cl  Br  F  NO2  CN  C(=O)NR9R10  C(=S)NR9R10  CO2CH3?CF3 or SO2CH3;
R4 and R8 may be the same or different  respectively selected from H  halogen  CN  NO2  C(=O)NR9R10  C1-C6alkyl  C1-C6haloalkyl  C1-C6alkoxy  C1-C6haloalkoxy  C2-C6alkenyl  C2-C6alkynyl  C1-C6alkylsulfonyl  C1-C6alkylcarbonyl  C1-C6alkoxycarbonyl  C1-C6alkoxyC1-C6alkyl  C1-C6alkoxycarbonylC1-C6alkyl  or the following groups unsubstituted or substituted with 1-4 R11: phenoxy  anilino  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl  anilinocarbonyl or pyridyloxy;
R5 and R7 may be the same or different  respectively selected from H  halogen  CN  NO2  C(=O)NR9R10  C1-C6alkyl  C1-C6haloalkyl  C1-C6alkoxy  C1-C6haloalkoxy  C1-C6alkylamino  C1-C6haloalkylamino  C1-C6alkylthio  C1-C6haloalkylthio  C2-C6alkenyl  C2-C6alkynyl  C1-C6alkylsulfonyl  C1-C6alkylcarbonyl  C1-C6alkoxycarbonyl  C1-C6alkoxyC1-C6alkyl;
R6 is selected from H  halogen  CN  NO2  CO2H  C(=O)NR9R10  C1-C6alkyl  C1-C6haloalkyl  C1-C6haloalkoxy  C2-C6alkenyl  C2-C6alkynyl  C1-C6alkylsulfonyl  C1-C6alkylcarbonyl  C1-C6alkoxycarbonyl  C1-C6alkoxyC1-C6alkyl  C1-C6alkoxycarbonylC1-C6alkyl  C1-C6alkoxyC1-C6alkoxy  or the following groups unsubstituted or substituted with 1-4 R11: phenoxy  anilino  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl  anilinocarbonyl or pyridyloxy;
But R4  R5  R6  R7 and R8 can not be H simultaneously;
R9 and R10 may be the same or different  respectively selected from H or C1-C3alkyl;
R11 is selected from halogen  NO2  CN  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylthio  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkylamino  C2-C6dialkylamino  C1-C3alkylcarbonylamino or C1-C3alkylaminocarbonyl;
Or the salts of the compounds having general formula I.
3. The compounds according to the claim 2  characterized in that wherein general formula I:
R1 is selected from H,C1-C3alkyl  C3-C6cycloalkyl  C1-C3alkylcarbonyl  C1-C3haloalkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C1-C3alkoxyC1-C3alkyl  C1-C3alkoxyC1-C3alkylcarbonyl  C1-C3alkoxycarbonylC1-C3alkyl  C1-C3alkylaminothio  C2-C6 dialkylaminothio or CO-X-CO2R9  in which X is selected from (CHR9)n  CR9=CR10 or C6H4  n=1-3;
R2 is selected from Cl  Br  F  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  C1-C3alkylthio  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C2-C6dialkylamino  C3-C4alkenyloxy  C3-C4haloalkenyloxy  C3-C4alkynyloxy  C1-C3alkylcarbonyloxy  C1-C3alkylcarbonylamino  C1-C3alkylsulfonyloxy  C1-C3alkoxyC1-C3alkoxy  C1-C3alkoxycarbonylC1-C3alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  benzyloxy  benzylamino  pyridyloxy or pyridylamino;
R3 is NO2;
R4 and R8 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C2-C3alkenyl  C2-C3alkynyl  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkoxyC1-C3alkyl  C1-C3alkoxycarbonylC1-C3alkyl  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl  anilinocarbonyl or pyridyloxy;
R5 and R7 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  C1-C3alkylthio  C1-C3haloalkylthio  C2-C3alkenyl  C2-C3alkynyl  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl or C1-C3alkoxyC1-C3alkyl;
R6 is selected from H  Cl  Br  F  CN  NO2  CO2H  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3haloalkoxy  C2-C3alkenyl  C2-C3alkynyl  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkoxyC1-C6alkyl  C1-C3alkoxycarbonylC1-C3alkyl  C1-C3alkoxyC1-C3alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl  anilinocarbonyl or pyridyloxy;
But R4  R5  R6  R7 and R8 can not be H simultaneously;
R9 and R10 may be the same or different  respectively selected from H or C1-C3alkyl;
R11 is selected from Cl  Br  F  NO2  CN  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylthio  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  or C1-C3alkylaminocarbonyl;
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 compounds according to the claim 3  characterized in that wherein general formula I:
R1 is selected from H,C1-C3alkyl  C3-C6cycloalkyl  C1-C3alkylcarbonyl  C1-C3haloalkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C1-C3alkoxyC1-C3alkyl  C1-C3alkoxyC1-C3alkylcarbonyl  C1-C3alkoxycarbonylC1-C3alkyl  C1-C3alkylaminothio  C2-C6 dialkylaminothio  COCH2CO2R9?COCH2CH2CO2R9?COCHCH3CO2R9?COC6H4CO2R9 or COCH=CHCO2R9;
R2 is selected from Cl  Br  F  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  C1-C3alkylthio  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C2-C6dialkylamino  C3-C4alkenyloxy  C3-C4haloalkenyloxy  C3-C4alkynyloxy  C1-C3alkoxyC1-C3alkoxy  C1-C3alkoxycarbonylC1-C3alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  benzyloxy  benzylamino  pyridyloxy or pyridylamino;
R3 is NO2;
R4 and R8 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkoxyC1-C3alkyl  C1-C3alkoxycarbonylC1-C3alkyl  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  anilino  phenoxycarbonyl or anilinocarbonyl;
R5 and R7 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  C1-C3alkylthio  C1-C3haloalkylthio  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl or C1-C3alkoxyC1-C3alkyl;
R6 is selected from H  Cl  Br  F  CN  NO2  CO2H  C(=O)NR9R10  C1-C3alkyl  C1-C3haloalkyl  C1-C3haloalkoxy  C2-C3alkenyl  C2-C3alkynyl  C1-C3alkylsulfonyl  C1-C3alkylcarbonyl  C1-C3alkoxycarbonyl  C1-C3alkoxyC1-C6alkyl  C1-C3alkoxycarbonylC1-C3alkyl  C1-C3alkoxyC1-C3alkoxy  or the following groups unsubstituted or substituted with 1-3 R11: phenoxy  phenylcarbonyl  benzylcarbonyl  phenoxycarbonyl or anilinocarbonyl;
But R4  R5  R6  R7 and R8 can not be H simultaneously;
R9 and R10 may be the same or different  respectively selected from H  CH3 or C2H5;
R11 is selected from Cl  Br  F  NO2  CN  CF3  CH3  OCH3  SCH3  formyl  CO2CH3 or CONHCH3;
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.
5. The compounds according to the claim 4  characterized in that wherein general formula I:
R1 is selected from H,CH3  C2H5  cyclopropyl  formyl  COCH3  COCF3  CO2CH3  CO2C2H5  SCCl3  SO2CH3  SO2C2H5  CH2OCH3  CH2OC2H5  CH2CH2OCH3  COCH2OCH3  CH2COOCH3  SNHCH3  SN(CH3)2  COCH2CO2H  COCH2CO2CH3  COCH2CH2CO2H  COCH2CH2CO2CH3  COCHCH3CO2H  COCHCH3CO2CH3  COC6H4CO2H  COC6H4CO2CH3  COCH=CHCO2H or COCH=CHCO2CH3;
R2 is selected from Cl  Br  F  C1-C3alkoxy  C1-C3haloalkoxy  C1-C3alkylamino  C1-C3haloalkylamino  SCH3  SC2H5  N(CH3)2  N(C2H5)2  OCH2OCH3  OPh  NHPh  OCH2Ph  NHCH2Ph  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;
R3 is NO2;
R4 and R8 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NH2  C(=O)NHCH3  C(=O)N(CH3)2  CH3  C2H5  CF3  OCH3  OC2H5  OCF3  SO2CH3  SO2C2H5  COCH3  COC2H5  CO2CH3  CO2C2H5  OPh  NHPh  CO2Ph or CONHPh;
R5 and R7 may be the same or different  respectively selected from H  Cl  Br  F  CN  NO2  C(=O)NH2  CH3  CF3  OCH3  OCF3  NHCH3  SCH3  SO2CH3  SO2C2H5  COCH3  COC2H5  CO2CH3  CO2C2H5 or CH2OCH3;
R6 is selected from H  Cl  Br  F  CN  NO2  CO2H  C(=O)NH2  C(=O)NHCH3  C(=O)N(CH3)2  CH3  CF3 ?CF(CF3)2?OCF3?OCH2CF3?OCF2CHFCF3?SO2CH3  SO2C2H5?COCH3  COC2H5  CO2CH3  CO2C2H5?OPh  NHPh ?COPh?COCH2Ph?CO2Ph?CONHPh?pyridinoxy or 3-chloro-5-(trifluoromethyl)pyridin-2-yloxy;
But R4  R5  R6  R7 and R8 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. According to the claim 1  a use of the compounds having general formula I to control plant pathogens/diseases in agricultural and other fields.
7. A composition of fungicides  characterized in containing the compounds having general formula I as an active ingredient and acceptable carrier in agriculture  wherein the weight percentage of the active ingredient in the composition is 0.5-90%.

Dated this 3rd day of July  2012.

Documents:

http://ipindiaonline.gov.in/patentsearch/GrantedSearch/viewdoc.aspx?id=zbou3IUbKENrJwP9trrqUA==&loc=vsnutRQWHdTHa1EUofPtPQ==


Patent Number 277113
Indian Patent Application Number 1666/MUMNP/2012
PG Journal Number 47/2016
Publication Date 11-Nov-2016
Grant Date 10-Nov-2016
Date of Filing 03-Jul-2012
Name of Patentee SINOCHEM CORPORATION
Applicant Address 28 Fuxingmennei Dajie Xicheng District Beijing 100031 China
Inventors:
# Inventor's Name Inventor's Address
1 LIU Changling 8 Shenliaodong Road Tiexi District Shenyang Liaoning 110021 China
2 LI Huichao 8 Shenliaodong Road Tiexi District Shenyang Liaoning 110021 China
3 LI Zhinian 8 Shenliaodong Road Tiexi District Shenyang Liaoning 110021 China
4 HUANG Guang 8 Shenliaodong Road Tiexi District Shenyang Liaoning 110021 China
5 ZHANG Hong 8 Shenliaodong Road Tiexi District Shenyang Liaoning 110021 China
PCT International Classification Number C07C 211/56
PCT International Application Number PCT/CN2011/071983
PCT International Filing date 2011-03-21
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 201010129005. 6 2010-03-22 China