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

Patent metadata

Field	Value
Publication number	US-9957248-B2
Application number	US-201515323260-A
Country	US
Kind code	B2
Filing date	Jun 30, 2015
Priority date	Jul 4, 2014
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

Primarily, the present invention relates to compounds of the formula (I) defined below and to their use 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 present invention also relates to herbicidal or plant growth-regulating compositions comprising one or more compounds of the formula (I). 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 (I) and/or salt thereof,

wherein
Q represents a mono- or bicyclic heteroaromatic radical with in total 1 to 9 carbon ring atoms, where the heteroatom or heteroatoms in the heteroaromatic ring are selected from the group consisting of N, O, S, P, B, Si, and Se, represents hydrogen or a hydrolyzable radical,
(R 2 ) n represent n substituents R 2 , where R 2 (if n=1) or each of the substituents R 2 (if n is greater than 1) independently of one another represents fluorine, chlorine, bromine, iodine, or methyl,
(R 3 ) m represents m substituents R 3 ,
where R 3 (if m=1) or each of the substituents R 3 (if m is greater than 1) independently of one another represents fluorine, chlorine, bromine, iodine, cyano, nitro, trifluoromethyl or trifluoromethoxy,

n represents 0, 1, 2, or 3, and
m represents 0, 1, 2, or 3.

2. The compound of formula (I) and/or salt thereof according to claim 1 ,
wherein
Q represents a mono- or bicyclic heteroaromatic radical having in total 2 to 9 carbon ring atoms, where the heteroaromatic radical Q contains 1, 2, 3 or 4 heteroatoms in the heteroaromatic ring and the heteroatom or the heteroatoms are selected from the group consisting of N, O, and S.

3. The compound of formula (I) and/or salt thereof as claimed in claim 1 ,
wherein
Q represents a mono- or bicyclic heteroaromatic radical selected from the group consisting of pyrimidinyl, pyridinyl, pyridazinyl, pyrazinyl, thienyl, furyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazinyl, quinolyl, isoquinolyl, cinnolinyl-, quinazolinyl, quinoxalinyl, pteridinyl, indolyl and phthalazinyl.

4. The compound of formula (I) and/or salt thereof as claimed in claim 1 , wherein the compound of the formula (I) corresponds to the formula (I-1), (I-2) or (I-3) defined below

5. The compound of formula (I) and/or salt thereof as claimed in claim 1 , wherein
R 1 represents hydrogen or a hydrolyzable radical having in total up to 30 carbon atoms.

6. The compound of formula (I) and/or salt thereof as claimed in claim 1 , wherein
R 1 represents hydrogen or a hydrolyzable radical having in total 1 to 24 carbon atoms, where the hydrolyzable radical
represents an optionally substituted hydrocarbon radical or an optionally substituted heterocyclyl radical, or
represents a radical of the formula SiR a R b R c , or —NR a R b ,
where each of the radicals R a and R b independently of the other represents hydrogen or an optionally substituted hydrocarbon radical and R c independently represents an optionally substituted hydrocarbon radical, or —NR a R b represents a 3- to 9-membered heterocycle which, in addition to this nitrogen atom, may contain one or two further ring heteroatoms selected from the group consisting of N, O and S and which is substituted or unsubstituted, or
represents a radical of the formula —C(═O)—R e or —P(═O)(R f ) 2 , where W and both radicals R f in each case independently of one another are selected from the group consisting of hydrogen, OH, unsubstituted or substituted (C 1 -C 8 )alkyl, unsubstituted or substituted (C 1 -C 4 )haloalkyl, unsubstituted or substituted (C 2 -C 8 )alkenyl, unsubstituted or substituted (C2-C 8 )alkynyl, unsubstituted or substituted (C 1 -C 6 )alkoxy, unsubstituted or substituted (C 1 -C 6 )alkoxy-(C 1 -C 8 )alkyl, unsubstituted or substituted (C 1 -C 4 )haloalkoxy, unsubstituted or substituted (C 1 -C 4 )haloalkoxy-(C 1 -C 8 )alkyl, unsubstituted or substituted (C 3 -C 8 )alkenyloxy, unsubstituted or substituted (C 3 -C 8 )alkenyloxy-(C 1 -C 8 )alkyl, unsubstituted or substituted (C 3 -C 8 )alkynyloxy, unsubstituted or substituted (C 3 -C 8 )alkynyloxy-(C 1 -C 8 )alkyl, unsubstituted or substituted —NR*R**, unsubstituted or substituted tri-[(C 1 -C 4 )alkyl]silyl, unsubstituted or substituted tri-[(C 1 -C 4 )alkyl]silyl-(C 1 -C 8 )alkyl, unsubstituted or substituted (C 3 -C 6 )cycloalkyl, unsubstituted or substituted (C 3 -C 6 )cycloalkyl-(C 1 -C 8 )alkyl, unsubstituted or substituted (C 5 -C 6 )cycloalkenyl, unsubstituted or substituted (C 5 -C 6 )cycloalkenyl-(C 1 -C 8 )alkyl, unsubstituted or substituted (C 5 -C 6 )cycloalkynyl, unsubstituted or substituted (C 5 -C 6 )cycloalkynyl-(C 1 -C 8 )alkyl, unsubstituted or substituted phenyl, unsubstituted or substituted phenyl-(C 1 -C 8 )alkyl, unsubstituted or substituted phenoxy, unsubstituted or substituted phenoxy-(C 1 -C 8 )alkyl, unsubstituted or substituted phenylamino, unsubstituted or substituted phenylamino(C 1 -C 8 )alkyl, unsubstituted or substituted Het, unsubstituted or substituted Het-(C 1 -C 6 )alkyl and unsubstituted or substituted Het-O—(C 1 -C 6 )alkyl, where

R* and R**, independently of one another and independently of any other radicals —NR*R** present, are in each case selected from the group consisting of H, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 1 -C 6 )alkanoyl, [(C 1 -C 4 )haloalkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, [(C 1 -C 4 )haloalkoxy]carbonyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyl-(C 1 -C 4 )alkyl, phenyl and phenyl-(C 1 -C 4 )alkyl, where each of the specified radicals (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyl-(C 1 -C 4 )alkyl, phenyl and phenyl-(C 1 -C 4 )alkyl is substituted in the cycle optionally by one or more identical or different radicals R bb , where
R bb in each case represents halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy or (C 1 -C 4 )haloalkoxy and, in the case of (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyl-(C 1 -C 4 )alkyl, R bb may additionally represent oxo, or
—NR*R** represents a 3- to 8-membered heterocycle which, in addition to this nitrogen atom, optionally contains one or two further ring heteroatoms selected from the group consisting of N, O and S and which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl and oxo,
Het in each case represents a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered bicyclic heterocycle in each case containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the specified substituted radicals is substituted in the acyclic moiety by one or more identical or different radicals R A and/or where each of the specified substituted radicals is substituted in the cyclic moiety by one or more identical or different radicals R B , where
R A represents halogen, cyano, hydroxy or (C 1 -C 6 )alkoxy, and
R B independently of any further radicals R B present is selected from the group consisting of halogen, cyano, hydroxy, oxo, nitro, (C 1 -C 8 )alkyl, (C 1 -C 6 )haloalkyl, cyano-(C 1 -C 6 )alkyl, hydroxy-(C 1 -C 6 )alkyl, nitro-(C 1 -C 6 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )haloalkenyl, (C 2 -C 8 )alkynyl, (C 2 -C 8 )haloalkynyl, (C 1 -C 8 )alkoxy, (C 2 -C 8 )alkenyloxy, (C 2 -C 8 )alkinyloxy, (C 1 -C 8 )haloalkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 4 )alkoxy, (C 1 -C 6 )haloalkoxy-(C 1 -C 4 )alkyl, (C 1 -C 6 )haloalkoxy-(C 1 -C 4 )alkoxy, (C 1 -C 8 )alkylthio, (C 2 -C 6 )alkenylthio, (C 2 -C 6 )alkynylthio, (C 1 -C 8 )alkylsulfinyl, (C 1 -C 6 )haloalkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, (C 1 -C 6 )haloalkylsulfonyl, R aa —C(═O)—,

Assignees

• Bayer Cropscience Ag
• Bayer Cropscience Aktiengesellshaft

Inventors

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

Classifications

• C07D241/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• A01N43/10

  with sulfur as the ring hetero atom · CPC title

• A01N43/76

  1,3-Oxazoles; Hydrogenated 1,3-oxazoles · CPC title

• A01N43/50

  1,3-Diazoles; Hydrogenated 1,3-diazoles · CPC title

• C07D213/61

  Halogen atoms or nitro radicals · CPC title