Substituted 5-hydroxy-2-phenyl-3-heteroaryl pentanenitrile derivatives, method for the production thereof and use thereof as herbicides and/or plant growth regulators

Patent metadata

Field	Value
Publication number	US-10172350-B2
Application number	US-201515516738-A
Country	US
Kind code	B2
Filing date	Oct 5, 2015
Priority date	Oct 8, 2014
Publication date	Jan 8, 2019
Grant date	Jan 8, 2019

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 the formula (I) or salt thereof,

in which
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,
R 1 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 halogen, cyano, nitro, (C 1 -C 8 )alkyl, (C 1 -C 8 )alkoxy, (C 1 -C 8 )alkylthio, (C 1 -C 8 )alkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )haloalkenyl, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )haloalkylsulfinyl, (C 1 -C 6 )haloalkylsulfonyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, tri-[(C 1 -C 4 )alkyl]silyl or tri-[(C 1 -C 4 )alkyl]silyl-(C 1 -C 4 )alkyl,
or in each case two R 2 directly adjacent on the heteroaromatic radical Q are together a group of the formula —Z 1 -A* 1 —Z 2 —, in which
A* represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy,
Z 1 represents a direct bond, 0 or S and
Z 2 represents a direct bond, 0 or S,
where the group —Z 1 -A*-Z 2 — together with the atoms of the heteroaromatic radical Q bonded to this group Q form a 5- or 6-membered ring, and

(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 halogen, cyano, nitro, (C 1 -C 8 )alkyl, (C 1 -C 8 )alkoxy, (C 1 -C 8 )alkylthio, (C 1 -C 8 )alkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )haloalkenyl, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )haloalkylsulfinyl, (C 1 -C 6 )haloalkylsulfonyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, tri-[(C 1 -C 4 )alkyl]silyl, tri-[(C 1 -C 4 )alkyl]silyl-(C 1 -C 4 )alkyl or —NR*R**, 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,
or where in each case two groups R 3 directly adjacent on the ring together represent a group of the formula —Z 3 -A**-Z 4 —, in which
A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )haloalkoxy,
Z 3 represents a direct bond, O or S and
Z 4 represents a direct bond, 0 or S,
where the group —Z 3 -A**-Z 4 together with the carbon atoms, bonded to this group, of the phenyl ring form a 5- or 6-membered ring,

n represents 0, or an integer in the range from 1 to 5, and
m represents 0, 1, 2, 3, 4 or 5.

2. The compound of the formula (I) 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 the formula (I) 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 the formula (I) 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

where
R 1 , R 2 , R 3 , m and n have the meaning defined in claim 1 .

5. The compound of the formula (I) 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 the formula (I) 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 R 1
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 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 R e 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 (C 2 -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**, where R* and R** are as defined above, 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

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• A01N43/60

  1,4-Diazines; Hydrogenated 1,4-diazines · CPC title

• A01N43/76

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

• C07D241/16

  Halogen atoms; Nitro radicals · CPC title

• C07D211/80

  having two double bonds between ring members or between ring members and non-ring members · CPC title

• C07C211/01

  having amino groups bound to acyclic carbon atoms · CPC title