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-2016113277-A1
Application number	US-201414895343-A
Country	US
Kind code	A1
Filing date	Jun 2, 2014
Priority date	Jun 7, 2013
Publication date	Apr 28, 2016
Grant date	—

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

1 . A compound of formula (I) and/or a salt thereof

in which
R 1 represents hydrogen or a hydrolyzable radical,
(R 2 ) n represents 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 the others represents halogen, cyano, nitro, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-alkylsulphinyl, (C 1 -C 8 )-alkylsulphonyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-haloalkylsulphinyl, (C 1 -C 6 )-haloalkylsulphonyl, (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 to one another at the ring together represent a group of the formula —Z 1 -A*-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, O or S and
Z 2 represents a direct bond, O or S,
where the group —Z 1 -A*-Z 2 together with the carbon atoms, attached to this group, of the phenyl ring 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 the others represents halogen, cyano, nitro, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-alkylsulphinyl, (C 1 -C 8 )-alkylsulphonyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-haloalkylsulphinyl, (C 1 -C 6 )-haloalkylsulphonyl, (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 further 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 )-alkoxyl]-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 (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 radicals mentioned is optionally substituted in the cycle 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, may optionally contain 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 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 to one another at 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, O or S,
where the group —Z 3 -A**-Z 4 together with the carbon atoms, attached to this group, of the phenyl ring form a 5- or 6-membered ring, and

n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3,
m represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3,
capable of being used as a herbicide and/or plant growth regulator, preferably optionally in one or more crops of one or more useful plants and/or one or more ornamental plants.

2 . A compound according to claim 1 , wherein
R 1 represents hydrogen or a hydrolyzable radical having a total of up to 30 carbon atoms, optionally a hydrolyzable radical having a total of 1 to 24 carbon atoms, optionally having a total of 1 to 20 carbon atoms.

3 . A compound according to claim 1 , wherein
R 1 represents hydrogen or a hydrolyzable radical having a total of 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 the two radicals R f each 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 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
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 substituted radicals mentioned is substituted in the acyclic moiety by one or more identical or different radicals R A and/or where

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• C07C255/36

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

• C07C253/30

  by reactions not involving the formation of cyano groups · CPC title

• C07C255/53

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

• A01N53/00

  Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof · 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