Substituted 5-hydroxy-2,3-diphenylpentanonitrile derivatives, processes for their preparation and their use as herbicides and/or plant growth regulators

Patent metadata

Field	Value
Publication number	US-10021877-B2
Application number	US-201414895343-A
Country	US
Kind code	B2
Filing date	Jun 2, 2014
Priority date	Jun 7, 2013
Publication date	Jul 17, 2018
Grant date	Jul 17, 2018

Abstract

Primarily, the present invention relates to the use of substances of the formula (I) as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The invention furthermore relates to the novel herbicidal substances of the formulae (Ib) and (Ia). The present invention also relates to corresponding compositions comprising one or more of the herbicides of the formula (I) and further agrochemically active substances, and also to plant growth-regulating or herbicidal compositions comprising one or more of these compounds. Moreover, the present invention relates to processes for preparing the compounds of the formula (I).

First claim

The invention claimed is:

1. A compound of formula (Ib) and/or a salt and/or ester thereof,

wherein

R 1 represents —C(═O)—O—R C or —C(═O)—R C , where R C is in each case selected from the group consisting of:
(i) unsubstituted (C 1 -C 6 )-alkyl, unsubstituted (C 2 -C 6 )-alkenyl, unsubstituted (C 2 -C 6 )-alkynyl, substituted (C 1 -C 6 )-alkyl, substituted (C 2 -C 6 )-alkenyl and substituted (C 2 -C 6 )-alkynyl, where each of these substituted radicals is substituted by one or more radicals from the group consisting of methyl, hydroxyl, fluorine and chlorine,
(ii) (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyloxy-(C 1 -C 4 )-alkyl, phenyl, where each of these radicals is unsubstituted in the cyclic moiety or substituted by one or more identical or different radicals R B , where R B is independently of any other radicals R B present selected from the group consisting of halogen (optionally fluorine, chlorine, bromine), cyano, nitro and (C 1 -C 4 )-alkyl (optionally methyl),
where R C optionally comprises a total of 1 to 12 carbon atoms, optionally a total of 1 to 10 carbon atoms,

R 2 represents 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-cyano, 3-cyano, 4-cyano, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF 3 , 3-CF 3 , 4-CF 3 , 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulphinyl, 3-methylsulphinyl, 4-methylsulphinyl, 2-methylsulphonyl, 3-methylsulphonyl, 4-methylsulphonyl, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, (2-Cl-3-F), (2-Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-3-F), (3-Br-4-F), (3-Br-5-F), (4-Br-3-Cl), (3-Br-4-Cl), (4-CN-3-F), (3-CN-4-F), (3-CN-5-F), (4-CN-3-Cl), (3-CN-4-Cl), 2,3,4-trifluoro, 2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro, 2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro or (2,6-F 2 -4-Cl),
and

R 3 represents 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-cyano, 3-cyano, 4-cyano, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF, 2-methoxy, 3-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulphinyl, 3-methylsulphinyl, 4-methylsulphinyl, 2-methylsulphonyl, 3-methylsulphonyl, 4-methylsulphonyl, 2-nitro, 3-nitro, 4-nitro, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2,5-dicyano, 2,6-dicyano, (2-Cl-3-F), (2-Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F), (4-Br-3-F), (4-CN-3-F), (4-NO 2 -3-F), (4-OMe-3-F), (3-CN-4-F), (3-NO 2 -4-F), (3-CN-4-Cl), (3-NO 2 -4-Cl), (5-CN-2-F), 2,3,4-trifluoro, 2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro, 2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro or (2,6-F 2 -4-Cl),
m represents 1, 2, or 3 and
n represents 1, 2, or 3.

2. The compound of formula (Ib) of claim 1 and/or a salt and/or ester thereof, wherein
m represents 0, and
n represents 0.

3. The compound of formula (Ib) of claim 1 and/or a salt and/or ester thereof, wherein
m represents 1, 2, or 3 and
n represents 1, 2, or 3.

4. Herbicidal or plant growth-regulating composition, comprising one or more compounds of formula (Ib) and/or salt thereof as defined in claim 1 and one or more further substances selected from groups (i) and/or (ii):
(i) one or more further agrochemically active substances, selected from one or more of the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and further growth regulators,
(ii) one or more formulation auxiliaries customary in crop protection.

5. The composition of claim 4 , wherein
m represents 0, and
n represents 0.

6. The composition of claim 4 , wherein
m represents 1, 2, or 3 and
n represents 1, 2, or 3.

7. Method for controlling broad-leaved weeds and/or weed grasses and/or sedge weeds or for regulating plant growth in crops of useful plants, comprising applying an effective amount of one or more compounds of formula (Ib) and/or a salt thereof, as defined in claim 1 .

Assignees

• Bayer Cropscience Ag

Inventors

• Mosrin Marc
• Jakobi Harald
• Dietrich Hansjoerg
• Gatzweiler Elmar
• Rosinger Christopher
• Schmutzler Dirk

Classifications

• C07C255/37

  the carbon skeleton being further substituted by etherified hydroxy groups · CPC title

• A01N37/36 Primary

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids · CPC title

• C07C255/36

  the carbon skeleton being further substituted by hydroxy groups · CPC title

• A01N37/34

  Nitriles · CPC title

• C07C255/53

  containing cyano groups and hydroxy groups bound to the carbon skeleton · CPC title