US2015173359A1PendingUtilityA1
Substituted fused pyrimidinones and dihydropyrimidinones
Est. expirySep 3, 2030(~4.1 yrs left)· nominal 20-yr term from priority
Inventors:Jens FrackenpohlHans-Joachim ZeiβInes HeinemannLothar WillmsThomas MüllerMarco BuschPascal Von Koskull-DöringIsolde Häuser-HahnChristopher Hugh RosingerJan DittgenMartin Jeffrey HillsMonika Schmitt
C07D 403/12C07D 239/91C07D 409/04A01N 43/54C07D 471/10A01N 43/90A01N 47/38C07D 405/04A01N 47/12A01N 43/82C07D 417/04C07D 403/04A01N 47/40C07D 239/90A01N 43/84C07D 401/06A01N 43/653A01N 43/56
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Claims
Abstract
The use of substituted fused pyrimidinones and dihydropyrimidinones of the formula (I) or salts thereof where the radicals of the formula (I) are each as defined in the description, for enhancing stress tolerance in plants to abiotic stress, and for invigorating plant growth and/or for increasing plant yield.
Claims
exact text as granted — not AI-modified1 . A substituted fused dihydropyrimidinone of the formula (I), or a salt thereof:
in which:
Q is 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 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 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 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, (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 H or (C 1 -C 6 )-alkyl.
2 . The substituted fused dihydropyrimidinone as claimed in claim 1 ;
wherein, in formula (I):
R 1 , R 2 , and R 3 are each 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 )-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, (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 H or one of the following groups:
G-1 to G-6, G-43, G-51 to G-54, G-69, G-71, G-89, G-197 to G-198, G-202 to G-210, G212 to G-216, and G-222 to G-236;
R 6 is one of the following groups:
G-1 to G-6, G-43, G-51 to G-54, G-69, G-71, G-72, G-89, G-163 to G-168, G-197 to G-198, G-202 to G-210, G212 to G-216, and G-222 to G-240;
R 7 is one of the following groups:
G-56, G-121 to G-132, G-138 to G-144, G-185, and G-247 to G-282; and
R 8 is H or one of the following groups:
G-1 to G-6;
where the aforementioned groups G-1 to G-282 are each defined as follows:
3 . A spray solution for treatment of plants, comprising an amount, effective for enhancing the resistance of plants to abiotic stress factors, of one or more of the substituted fused dihydropyrimidinones of the formula (I) or salts thereof as claimed in claim 13 .
4 . The spray solution of claim 3 ;
wherein, in formula (I):
R 1 , R 2 , and R 3 are each 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 )-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, (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 7 -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 H or one of the following groups:
G-1 to G-6, G-43, G-51 to G-54, G-69, G-71, G-89, G-197 to G-198, G-202 to G-210, G212 to G-216, and G-222 to G-236;
R 6 is one of the following groups:
G-1 to G-6, G-43, G-51 to G-54, G-69, G-71, G-72, G-89, G-163 to G-168, G-197 to G-198, G-202 to G-210, G212 to G-216, and G-222 to G-240;
R 7 is one of the following groups:
G-56, G-121 to G-132, G-138 to G-144, G-185, and G-247 to G-282; and
R 8 is H or one of the following groups defined:
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