# US 9,006,265 B2 · Substituted fused pyrimidinones and dihydropyrimidinones

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- Number: US 9,006,265 B2
- Document ID: US9006265B2
- Status: Granted
- Kind: B2
- Application number: 13/224,375
- Filed: 2011-09-02
- Published: 2012-06-21
- Granted: 2015-04-14
- Earliest claimed: 2010-09-03
- Assignees: Bayer Intellectual Property GmbH
- Applicants: Jens Frackenpohl; Hans-Joachim Zeiβ; Ines Heinemann; Lothar Willms; Thomas Müller; Marco Busch; Pascal Von Koskull-Döring; Isolde Häuser-Hahn; Christopher Hugh Rosinger; Jan Dittgen; Martin Jeffrey Hills; Monika H. Schmitt
- Inventors: Jens Frackenpohl; Hans-Joachim Zeiβ; Ines Heinemann; Lothar Willms; Thomas Müller; Marco Busch; Pascal Von Koskull-Döring; Isolde Häuser-Hahn; Christopher Hugh Rosinger; Jan Dittgen; Martin Jeffrey Hills; Monika H. Schmitt
- Web page: https://patentgrep.com/patent/US9006265B2

## CPC

- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/12: containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N 47/38: containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- A01N 47/40: the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- C07D 239/90: with acyclic radicals attached in position 2 or 3
- C07D 239/91: with aryl or aralkyl radicals attached in position 2 or 3
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 471/10: Spiro-condensed systems
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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

### Claim 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 R6, R7, and R8 are each as defined below; and
where the arrow represents a bond to the N—R5 group;
W is oxygen or sulfur;
A is N (nitrogen) or a C—R4 moiety;
where R4 in the C—R4 moiety is in each case as defined below;
R1, R2, and R3 are each independently hydrogen or fluorine;
R4 is nitro, amino, hydroxyl, fluorine, chlorine, bromine, iodine, cyano, hydrothio, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, aryl, aryl-(C1-C4)-alkyl, aryl-(C2-C6)-alkenyl, aryl-(C2-C6)-alkynyl, heteroaryl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, heteroaryl-(C2-C6)-alkenyl, heteroaryl-(C2-C6)-alkynyl, (C1-C4)-haloalkyl, (C3-C6)-halocycloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkylalkynyl, (C1-C4)-trialkylsilyl-(C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-alkoxy (C1-C4)-haloalkoxy, (C2-C6)-alkenyloxy-(C1-C4)-alkyl, aryl-(C1-C4)-alkoxy, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, bis-(C1-C6)-alkylamino, (C3-C6)-cycloalkylamino, (C3-C6)-haloalkylamino, (C1-C6)-alkylcarbonylamino, (C3-C6)-cycloalkylcarbonylamino, (C1-C4)-haloalkylcarbonylamino, (C1-C4)-alkoxycarbonylamino, (C1-C4)-alkylaminocarbonylamino, (C1-C4)-alkylsulfonylamino, (C3-C6)-cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, (C3-C6)-haloalkylsulfonylamino, (C1-C4)-alkylsulfonyl, (C1-C6)-haloalkylsulfonyl, arylsulfonyl, (C1-C4)alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, arylsulfinyl, (C3-C6)-cycloalkyl-(C1-C4)-alkoxy, (C1-C6)-alkynyl-(C1-C4)-alkoxy, (C2-C6)-alkenyl-(C1-C4)-alkoxy, (C2-C6)-alkenyloxy-(C1-C4)-alkoxy, (C1-C4)-alkyloxy-(C1-C4)-alkoxy, (C1-C4)-alkylamino-(C1-C4)-alkoxy, bis-(C1-C6)-alkylamino-(C1-C4)-alkoxy, or (C3-C6)-cycloalkylamino-(C1-C4)-alkoxy;
R5 is hydrogen (C1-C6)-alkyl, (C2-C6)-alkenyl, (C3-C6)-alkynyl, (C3-C6)-cycloalkyl, (C1-C6)-alkylthio-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C4)-haloalkyl, (C1-C6)-cycloalkyl-(C1-C4)-alkyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylcarbonyl, (C3-C6)-cycloalkylcarbonyl, (C1-C6)-alkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, (C1-C4)-haloalkylaminocarbonyl, (C2-C6)-alkynylaminocarbonyl, cyano-(C1-C6)-alkylaminocarbonyl, (C1-C7)-heterocycloalkylcarbonyl, heteroaryl-(C1-C7)-alkylaminocarbonyl, (C2-C6)-alkenyloxycarbonyl, (C3-C7)-cycloalkyl-(C1-C4)-alkoxycarbonyl, (C3-C7)-cycloalkyl-(C1-C4)-alkylaminocarbonyl, aryl-(C1-C4)-alkylaminocarbonyl, cyano-(C1-C6)-alkyl, nitro-(C1-C6)-alkyl, (C1-C7)-alkylamino-(C1-C7)-alkyl, bis-(C1-C7)-alkylamino-(C1-C7)-alkyl, aminocarbonyl-(C1-C7)-alkyl, (C1-C7)-alkylaminocarbonyl-(C1-C7)-alkyl, bis-(C1-C7)-alkylaminocarbonyl-(C1-C7)-alkyl, or (C1-C7)-alkoxycarbonyl-(C1-C7)-alkyl;
R6 is hydrogen, formyl, hydroxyl, amino, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C1-C6)-alkylthio-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C4)-haloalkyl, aryl-(C1-C4)-alkyl, aryl-(C2-C6)-alkenyl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylcarbonyl, (C3-C6)-cycloalkylcarbonyl, (C1-C6)-alkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, (C1-C4)-haloalkylaminocarbonyl, (C2-C6)-alkynylaminocarbonyl, cyano-(C1-C6)-alkylaminocarbonyl, (C4-C7)-heterocycloalkylcarbonyl, heteroaryl-(C1-C7)-alkylaminocarbonyl, (C2-C6)-alkenyloxycarbonyl, (C3-C7)-cycloalkyl-(C1-C4)-alkoxycarbonyl, (C3-C7)-cycloalkyl-(C1-C4)-alkylaminocarbonyl, aryl-(C1-C4)-alkylaminocarbonyl, cyano-(C1-C6)-alkyl nitro-(C1-C6)-alkyl, heteroaryl-(C1-C4)-alkyl, (C1-C7)-alkylamino-(C1-C7)-alkyl, bis-(C1-C7)-alkylamino-(C1-C7)-alkyl, aminocarbonyl-(C1-C7)-alkyl, (C1-C7)-alkylaminocarbonyl-(C1-C7)-alkyl, bis-(C1-C7)-alkylaminocarbonyl-(C1-C7)-alkyl, or (C1-C7)-alkoxycarbonyl-(C1-C7)-alkyl;
R7 is aryl-(C2-C4)-alkenyl, aryl-(C2-C4)-haloalkenyl, heteroaryl-(C2-C4)-alkenyl, heteroaryl-(C2-C4)-haloalkenyl, (C3-C7)-heterocycloalkyl-(C2-C4)-alkynyl, (C3-C7)-heterocycloalkenyl-(C2-C4)-alkynyl, (C3-C7)-heterocycloalkyl-(C2-C4)-alkenyl, (C3-C7)-heterocycloalkenyl-(C2-C4)-alkenyl, (C3-C7)-heterocycloalkyl-(C1-C4)-alkyl, or (C3-C7)-heterocycloalkenyl-(C1-C4)-alkyl, where the heteroatom in the heteroaryl, heterocycloalkyl, and heterocycloalkenyl optionally bears a charge; and
R8 is hydrogen.

### Claim 2 (depends on 1)

The method of claim 1;
where, in formula (I):
R1, R2, and R3 are each independently hydrogen;
R4 is nitro, amino, hydroxyl, fluorine, chlorine, bromine, iodine, cyano, hydrothio, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, aryl, aryl-(C1-C4)-alkyl, aryl-(C2-C6)-alkenyl, aryl-(C2-C6)-alkynyl, heteroaryl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, heteroaryl-(C2-C6)-alkenyl, heteroaryl-(C2-C6)-alkynyl, (C1-C4)-haloalkyl, (C3-C6)-halocycloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkylalkynyl, (C1-C4)-trialkylsilyl-(C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C2-C6)-alkenyloxy-(C1-C4)-alkyl, aryl-(C1-C4)-alkoxy, (C1-C6)-alkylamino, (C2-C6)-alkynylamino, (C1-C6)-alkylthio, (C1-C4)-haloalkylthio, bis-(C1-C6)-alkylamino, (C3-C6)-cycloalkylamino, (C3-C6)-haloalkylamino, (C1-C6)-alkylcarbonylamino, (C3-C6)-cycloalkylcarbonylamino, (C1-C4)-halo-alkylcarbonylamino, (C1-C4)-alkoxycarbonylamino, (C1-C4)-alkylaminocarbonylamino, (C1-C4)-alkylsulfonylamino, (C3-C6)-cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, (C3-C6)-haloalkylsulfonylamino, (C1-C4)-alkylsulfonyl, (C1-C6)-haloalkylsulfonyl, arylsulfonyl, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C3-C6)-cycloalkyl-(C1-C4)-alkoxy, (C1-C6)-alkynyl-(C1-C4)-alkoxy, (C2-C6)-alkenyl-(C1-C4)-alkoxy, (C2-C6)-alkenyloxy-(C1-C4)-alkoxy, (C1-C4)-alkyloxy-(C1-C4)-alkoxy, (C1-C4)-alkylamino-(C1-C4)-alkoxy, bis-(C1-C6)-alkylamino-(C1-C4)-alkoxy, or (C3-C6)-cycloalkylamino-(C1-C4)-alkoxy;
R5 is hydrogen or one of the following groups:
R6 is hydrogen, hydroxyl, or one of the following groups:
R7 is one of the following groups:
R8 is hydrogen or one of the following groups:

### Claim 3 (depends on 1)

The method of claim 1;
wherein the substituted fused dihydropyrimidinone of the formula (I) or salt thereof is applied in a spray application.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 3)

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.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

The method of claim 1;
wherein the application is to the plants, the seed thereof or to the area on which the plants grow.

### Claim 8 (depends on 1)

The method of claim 1;
wherein the plants are selected from the group consisting of useful plants, ornamental plants, turfgrass types, and trees.

### Claim 9 (depends on 8)

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.

### Claim 10 (depends on 1)

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.

### Claim 11 (depends on 10)

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.