Substituted fused pyrimidinones and dihydropyrimidinones

1. A method for increasing tolerance to abiotic stress in plants, comprising:

applying, to the plants, the seed thereof, or to the area on which the plants grow, or to genetically modified cultivars, the seed thereof, or to cultivated areas on which these cultivars grow, an effective, non-toxic amount of at least one substituted fused dihydropyrimidinone of the formula (I) or a salt thereof:

where:

Q represents the moiety:

where R 6 , R 7 , and R 8 are each as defined below; and

where the arrow represents a bond to the N—R 5 group;

W is oxygen or sulfur;

A is N (nitrogen) or a C—R 4 moiety;

where R 4 in the C—R 4 moiety is in each case as defined below;

R 1 , R 2 , and R 3 are each independently hydrogen or fluorine;

R 4 is nitro, amino, hydroxyl, fluorine, chlorine, bromine, iodine, cyano, hydrothio, (C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, aryl, aryl-(C 1 -C 4 )-alkyl, aryl-(C 2 -C 6 )-alkenyl, aryl-(C 2 -C 6 )-alkynyl, heteroaryl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl, heteroaryl-(C 2 -C 6 )-alkenyl, heteroaryl-(C 2 -C 6 )-alkynyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkylalkynyl, (C 1 -C 4 )-trialkylsilyl-(C 2 -C 6 )-alkynyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy (C 1 -C 4 )-haloalkoxy, (C 2 -C 6 )-alkenyloxy-(C 1 -C 4 )-alkyl, aryl-(C 1 -C 4 )-alkoxy, (C 1 -C 6 )-alkylamino, (C 2 -C 6 )-alkenylamino, (C 2 -C 6 )-alkynylamino, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, bis-(C 1 -C 6 )-alkylamino, (C 3 -C 6 )-cycloalkylamino, (C 3 -C 6 )-haloalkylamino, (C 1 -C 6 )-alkylcarbonylamino, (C 3 -C 6 )-cycloalkylcarbonylamino, (C 1 -C 4 )-haloalkylcarbonylamino, (C 1 -C 4 )-alkoxycarbonylamino, (C 1 -C 4 )-alkylaminocarbonylamino, (C 1 -C 4 )-alkylsulfonylamino, (C 3 -C 6 )-cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, (C 3 -C 6 )-haloalkylsulfonylamino, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, arylsulfonyl, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )-haloalkylsulfinyl, arylsulfinyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkoxy, (C 1 -C 6 )-alkynyl-(C 1 -C 4 )-alkoxy, (C 2 -C 6 )-alkenyl-(C 1 -C 4 )-alkoxy, (C 2 -C 6 )-alkenyloxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkyloxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylamino-(C 1 -C 4 )-alkoxy, bis-(C 1 -C 6 )-alkylamino-(C 1 -C 4 )-alkoxy, or (C 3 -C 6 )-cycloalkylamino-(C 1 -C 4 )-alkoxy;

R 5 is hydrogen (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, (C 3 -C 6 )-cycloalkylcarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, (C 3 -C 6 )-cycloalkylaminocarbonyl, (C 1 -C 4 )-haloalkylaminocarbonyl, (C 2 -C 6 )-alkynylaminocarbonyl, cyano-(C 1 -C 6 )-alkylaminocarbonyl, (C 1 -C 7 )-heterocycloalkylcarbonyl, heteroaryl-(C 1 -C 7 )-alkylaminocarbonyl, (C 2 -C 6 )-alkenyloxycarbonyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 4 )-alkoxycarbonyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 4 )-alkylaminocarbonyl, aryl-(C 1 -C 4 )-alkylaminocarbonyl, cyano-(C 1 -C 6 )-alkyl, nitro-(C 1 -C 6 )-alkyl, (C 1 -C 7 )-alkylamino-(C 1 -C 7 )-alkyl, bis-(C 1 -C 7 )-alkylamino-(C 1 -C 7 )-alkyl, aminocarbonyl-(C 1 -C 7 )-alkyl, (C 1 -C 7 )-alkylaminocarbonyl-(C 1 -C 7 )-alkyl, bis-(C 1 -C 7 )-alkylaminocarbonyl-(C 1 -C 7 )-alkyl, or (C 1 -C 7 )-alkoxycarbonyl-(C 1 -C 7 )-alkyl;

R 6 is hydrogen, formyl, hydroxyl, amino, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-haloalkyl, aryl-(C 1 -C 4 )-alkyl, aryl-(C 2 -C 6 )-alkenyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, (C 3 -C 6 )-cycloalkylcarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, (C 3 -C 6 )-cycloalkylaminocarbonyl, (C 1 -C 4 )-haloalkylaminocarbonyl, (C 2 -C 6 )-alkynylaminocarbonyl, cyano-(C 1 -C 6 )-alkylaminocarbonyl, (C 4 -C 7 )-heterocycloalkylcarbonyl, heteroaryl-(C 1 -C 7 )-alkylaminocarbonyl, (C 2 -C 6 )-alkenyloxycarbonyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 4 )-alkoxycarbonyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 4 )-alkylaminocarbonyl, aryl-(C 1 -C 4 )-alkylaminocarbonyl, cyano-(C 1 -C 6 )-alkyl nitro-(C 1 -C 6 )-alkyl, heteroaryl-(C 1 -C 4 )-alkyl, (C 1 -C 7 )-alkylamino-(C 1 -C 7 )-alkyl, bis-(C 1 -C 7 )-alkylamino-(C 1 -C 7 )-alkyl, aminocarbonyl-(C 1 -C 7 )-alkyl, (C 1 -C 7 )-alkylaminocarbonyl-(C 1 -C 7 )-alkyl, bis-(C 1 -C 7 )-alkylaminocarbonyl-(C 1 -C 7 )-alkyl, or (C 1 -C 7 )-alkoxycarbonyl-(C 1 -C 7 )-alkyl;

R 7 is aryl-(C 2 -C 4 )-alkenyl, aryl-(C 2 -C 4 )-haloalkenyl, heteroaryl-(C 2 -C 4 )-alkenyl, heteroaryl-(C 2 -C 4 )-haloalkenyl, (C 3 -C 7 )-heterocycloalkyl-(C 2 -C 4 )-alkynyl, (C 3 -C 7 )-heterocycloalkenyl-(C 2 -C 4 )-alkynyl, (C 3 -C 7 )-heterocycloalkyl-(C 2 -C 4 )-alkenyl, (C 3 -C 7 )-heterocycloalkenyl-(C 2 -C 4 )-alkenyl, (C 3 -C 7 )-heterocycloalkyl-(C 1 -C 4 )-alkyl, or (C 3 -C 7 )-heterocycloalkenyl-(C 1 -C 4 )-alkyl, where the heteroatom in the heteroaryl, heterocycloalkyl, and heterocycloalkenyl optionally bears a charge; and

R 8 is hydrogen.

2. The method of claim 1 ;

where, in formula (I):

R 1 , R 2 , and R 3 are each independently hydrogen;

R 4 is nitro, amino, hydroxyl, fluorine, chlorine, bromine, iodine, cyano, hydrothio, (C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, aryl, aryl-(C 1 -C 4 )-alkyl, aryl-(C 2 -C 6 )-alkenyl, aryl-(C 2 -C 6 )-alkynyl, heteroaryl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl, heteroaryl-(C 2 -C 6 )-alkenyl, heteroaryl-(C 2 -C 6 )-alkynyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkylalkynyl, (C 1 -C 4 )-trialkylsilyl-(C 2 -C 6 )-alkynyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 2 -C 6 )-alkenyloxy-(C 1 -C 4 )-alkyl, aryl-(C 1 -C 4 )-alkoxy, (C 1 -C 6 )-alkylamino, (C 2 -C 6 )-alkynylamino, (C 1 -C 6 )-alkylthio, (C 1 -C 4 )-haloalkylthio, bis-(C 1 -C 6 )-alkylamino, (C 3 -C 6 )-cycloalkylamino, (C 3 -C 6 )-haloalkylamino, (C 1 -C 6 )-alkylcarbonylamino, (C 3 -C 6 )-cycloalkylcarbonylamino, (C 1 -C 4 )-halo-alkylcarbonylamino, (C 1 -C 4 )-alkoxycarbonylamino, (C 1 -C 4 )-alkylaminocarbonylamino, (C 1 -C 4 )-alkylsulfonylamino, (C 3 -C 6 )-cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, (C 3 -C 6 )-haloalkylsulfonylamino, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, arylsulfonyl, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-haloalkylsulfinyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkoxy, (C 1 -C 6 )-alkynyl-(C 1 -C 4 )-alkoxy, (C 2 -C 6 )-alkenyl-(C 1 -C 4 )-alkoxy, (C 2 -C 6 )-alkenyloxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkyloxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylamino-(C 1 -C 4 )-alkoxy, bis-(C 1 -C 6 )-alkylamino-(C 1 -C 4 )-alkoxy, or (C 3 -C 6 )-cycloalkylamino-(C 1 -C 4 )-alkoxy;

R 5 is hydrogen or one of the following groups:

R 6 is hydrogen, hydroxyl, or one of the following groups:

R 7 is one of the following groups:

R 8 is hydrogen or one of the following groups:

3. The method of claim 1 ;

wherein the substituted fused dihydropyrimidinone of the formula (I) or salt thereof is applied in a spray application.

4. The method of claim 1 ;

wherein the substituted fused dihydropyrimidinone of the formula (I) or salt thereof is applied in a spray application in combination with at least one active ingredients selected from the group consisting of insecticides, attractants, acaricides, fungicides, nematicides, herbicides, growth regulators, safeners, substances which influence plant maturity, and bactericides.

5. The method of claim 3 ;

wherein the substituted fused dihydropyrimidinone of the formula (I) or salts thereof is applied in a spray application to plants and plant parts and applied in combinations with at least one fertilizer.

6. The method of claim 1 ;

wherein the application is to genetically modified cultivars, the seed thereof, or to cultivated areas on which these cultivars grow.

7. The method of claim 1 ;

wherein the application is to the plants, the seed thereof or to the area on which the plants grow.

8. The method of claim 1 ;

wherein the plants are selected from the group consisting of useful plants, ornamental plants, turfgrass types, and trees.

9. The method as claimed in claim 8 ;

wherein the resistance of the plants thus treated to abiotic stress has been increased by at least 3% compared to untreated plants under otherwise identical physiological conditions.

10. The method of claim 1 ;

wherein the amount of substituted fused dihydropyrimidinone of the formula (I) or salt thereof applied is an amount effective for enhancing the resistance of plants to abiotic stress factors.

11. The method of claim 10 ;

wherein the abiotic stress factors comprise at least one condition selected from the group consisting of drought, cold and hot conditions, drought stress, osmotic stress, waterlogging, elevated soil salinity, elevated exposure to minerals, ozone conditions, strong light conditions, limited availability of nitrogen nutrients, and limited availability of phosphorus nutrients.