Substituted pyrimidine ammonia compounds and uses thereof
The invention relates to substituted pyrimidine ammonia compounds. The structure of the compounds is represented as the general formula (I): The groups are as defined as specification. The compound represented by formula (I) can be used in the prevention of plants diseases caused by a plurality of pathogenic bacteria such as oomycota, basidiomycota, ascomycota, and fungi imperfecti, and due to these compounds have good bioactivity, which make them have very good effects at very low doses, especially more effective to powdery mildew of wheat. Therefore, the present invention relates to the use of the compounds having general formula I as fungicides, both in agriculture and other fields.
1. A substituted pyrimidine ammonia compounds having the general formula I:
Wherein:
R 1 is selected from halogen, CN, NO 2 , C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 1 -C 12 dialkylamino, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, 2,3-methylenedioxy, 3,4-methylenedioxy, 2,3-difluoromethylenedioxy or 3,4-difluoromethylenedioxy; n is selected from 0-5;
R 2 is selected from H or C 1 -C 6 alkyl;
R 3 is selected from H, halogen, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, (un)substituted phenyl, benzyl, or heteroaryl, in which the substituent(s) is(are) independently selected from 1 to 5 of halogen, NO 2 , CN, C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 1 -C 12 dialkylamino, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 2 haloalkylcarbonyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 1 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, 2,3-methylenedioxy, 3,4-methylenedioxy, 2,3-difluoromethylenedioxy or 3,4-difluoromethylenedioxy;
R 4 is selected from H, halogen, C 1 -C 12 alkyl or C 1 -C 12 haloalkyl;
or R 3 and R 4 join together with atoms linked on them to form (un)saturated 3 to 6-membered carbocyclic or heterocyclic ring, which is(are) unsubstituted or optionally substituted by halogen, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy or C 1 -C 12 haloalkoxy;
R 5 is selected from C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylaminoC 1 -C 12 alkyl, C 1 -C 12 dialkylaminoC 1 -C 12 alkyl, C 2 -C 12 alkenyl, (un)substituted phenyl, benzyl, furfuryl or heteroaryl, in which the substituent(s) is(are) independently selected from 1 to 5 of halogen, NO 2 , CN, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 12 alkylamino, C 1 -C 12 haloalkylamino, C 1 -C 12 dialkylamino, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 haloalkylcarbonyl, C 1 -C 12 alkoxyC 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxycarbonylC 1 -C 12 alkyl, C 1 -C 12 haloalkoxyC 1 -C 12 alkyl, 2,3-methylenedioxy, 3,4-methylenedioxy, 2,3-difluoromethylenedioxy or 3,4-difluoromethylenedioxy;
X and Y may be the same or different, selected from O or S.
2. The compounds according to the claim 1 , characterized in that wherein general formula I:
R 1 is selected from halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 haloalkoxyC 1 -C 6 alkyl, 2,3-methylenedioxy, 3,4-methylenedioxy, 2,3-difluoromethylenedioxy or 3,4-difluoromethylenedioxy; n is selected from 0-4;
R 2 is selected from H or C 1 -C 3 alkyl;
R 3 is selected from H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, (un)substituted phenyl, benzyl, or heteroaryl, in which the substituent(s) is(are) independently selected from 1 to 5 of halogen, NO 2 , CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 haloalkoxyC 1 -C 6 alkyl, 2,3-methylenedioxy, 3,4-methylenedioxy, 2,3-difluoromethylenedioxy or 3,4-difluoromethylenedioxy;
R 4 is selected from H, halogen, C 1 -C 8 alkyl or C 1 -C 8 haloalkyl;
or R 3 and R 4 join together with atoms linked on them to form (un)saturated 3 to 6-membered carbocyclic or heterocyclic ring, which is(are) unsubstituted or optionally substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;
R 5 is selected from C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylaminoC 1 -C 6 alkyl, C 1 -C 6 dialkylaminoC 1 -C 6 alkyl, C 2 -C 8 alkenyl, (un)substituted phenyl, benzyl, furfuryl or heteroaryl, in which the substituent(s) is(are) independently selected from 1 to 5 of halogen, NO 2 , CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 halo alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 haloalkoxyC 1 -C 6 alkyl, 2,3-methylenedioxy, 3,4-methylenedioxy, 2,3-difluoromethylenedioxy or 3,4-difluoromethylenedioxy;
X and Y may be the same or different, selected from O or S.
3. The compounds according to the claim 2 , characterized in that wherein general formula I:
R 1 is selected from halogen, CN, NO 2 , 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 dialkylamino, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 3 alkoxyC 1 -C 3 alkyl, C 1 -C 3 alkoxycarbonyl, 2,3-methylenedioxy, 3,4-methylenedioxy, 2,3-difluoromethylenedioxy or 3,4-difluoromethylenedioxy; n is selected from 0-4;
R 2 is selected from H or C 1 -C 3 alkyl;
R 3 is selected from H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or phenyl;
R 4 is selected from H, halogen, C 1 -C 8 alkyl or C 1 -C 8 haloalkyl;
or R 3 and R 4 join together with atoms linked on them to form (un)saturated 3 to 6-membered carbocyclic or heterocyclic ring, which is(are) unsubstituted or optionally substituted by halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;
R 5 is selected from C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 3 alkylaminoC 1 -C 6 alkyl, C 1 -C 3 dialkylaminoC 1 -C 6 alkyl, C 2 -C 8 alkenyl, (un)substituted phenyl, benzyl, furfuryl, pyridyl, pyrimidyl, thienyl, thiazolyl or benzothiazolyl, in which the substituent(s) is(are) independently selected from 1 to 3 of 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 alkylamino, C 1 -C 3 dialkylamino, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, 2,3-methylenedioxy, 3,4-methylenedioxy, 2,3-difluoromethylenedioxy or 3,4-difluoromethylenedioxy;
X and Y may be the same or different, selected from O or S.
4. The compounds according to the claim 3 , characterized in that wherein general formula I:
R 1 is selected from halogen, CN, NO 2 , CH 3 , C 2 H 5 , CF 3 , OCH 3 or OCF 3 ; n is selected from 0-3;
R 2 is selected from H or CH 3 ;
R 3 is selected from CH 3 , CF 3 or phenyl;
R 4 is selected from H, CH 3 or n-Bu;
or R 3 and R 4 join together with atoms linked on them to form saturated 5 or 6-membered carbocyclic ring;
R 5 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 2 -C 8 alkenyl, (un)substituted phenyl, benzyl or furfuryl, in which the substituent(s) is(are) independently selected from 1 to 3 of halogen, NO 2 , CN, CH 3 , OCH 3 , CF 3 , OCF 3 or CO 2 CH 3 ;
X and Y may be the same or different, selected from O or S.
5. The compounds according to the claim 4 , characterized in that wherein general formula I:
R 1 is selected from F, Cl or OCF 3 ; n is selected from 0-3;
R 2 is selected from H;
R 3 is selected from CH 3 , CF 3 or phenyl;
R 4 is selected from H, CH 3 or n-Bu;
or R 3 and R 4 join together with atoms linked on them to form saturated 5 or 6-membered carbocyclic ring;
R 5 is selected from CH 3 , C 2 H 5 , CH(CH 3 ) 2 , n-Bu, CH 2 CH 2 OCH 3 , CH 2 CH═CH 2 , benzyl or furfuryl;
X is selected from O;
Y is selected from O or S.
6. The compounds according to the claim 5 , characterized in that wherein general formula I:
n is selected from 0;
R 2 is selected from H;
R 3 is selected from CH 3 ;
R 4 is selected from n-Bu;
or R 3 and R 4 join together with atoms linked on them to form saturated 5 or 6-membered carbocyclic ring;
R 5 is selected from CH 3 , C 2 H 5 , CH(CH 3 ) 2 , n-Bu, CH 2 CH 2 OCH 3 , benzyl or furfuryl;
X and Y are selected from O.
7. A method of controlling fungi which comprises applying the compound having general formula I according to claim 1 to agricultural and other fields.
8. A fungicidal composition comprising the compound having general formula I according to the claim 1 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is in the range of 0.1-99%.