# US 2014/0194291 A1 · Substituted (3r,4r)-4-cyan-3,4-diphenylbutanoates, method for the production thereof and use thereof as herbicides and plant growth regulators

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- Number: US 2014/0194291 A1
- Document ID: US20140194291A1
- Status: Published application
- Kind: A1
- Application number: 14/005,379
- Filed: 2012-03-12
- Published: 2014-07-10
- Earliest claimed: 2011-03-18
- Assignees: Bayer Intellectual Property GmbH
- Inventors: Harald Jakobi; Marc Mosrin; Elmar Gatzweiler; Isolde Häuser-Hahn; Ines Heinemann; Christopher Hugh Rosinger; Alfred Angermann; Michael Gerhard Hoffmann; Stefan Schnatterer; Hans-Joachim Zeiß
- Web page: https://patentgrep.com/patent/US20140194291A1

## CPC

- A01N 43/20: three- or four-membered rings
- A01N 37/34: Nitriles
- A01N 37/38: having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N 37/48: Nitro-carboxylic acids; Derivatives thereof
- A01N 41/02: containing a sulfur-to-oxygen double bond
- A01N 41/10: Sulfones; Sulfoxides
- C07C 255/41: the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
- C07C 255/57: containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
- C07C 323/12: the carbon skeleton being acyclic and saturated
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Substituted (3R,4R)-4-cyano-3,4-diphenylbutanoates, processes for their preparation and their use as herbicides and plant growth regulators Compounds of the formula (I) or salts thereof and salts thereof, in each case in the optically active (3R,4R)-threo form, R1 is hydrogen or a hydrolyzable radical, and (R2)n, (R3)m, n and m are as defined in formula (I) according to claim 1, where the stereochemical configuration at the carbon atom in position 3 of the butanoic acid derivative has a stereochemical purity of 60 to 100% (R), preferably 70 to 100% (R), more preferably 80 to 100% (R), in particular 90 to 100% (R), based on the mixture of threo enantiomers present, and the stereochemical configuration at the carbon atom in position 4 of the butanoic acid derivative has a stereochemical purity of 60 to 100% (R), preferably 70 to 100% (R), more preferably 80 to 100% (R), in particular 90 to 100% (R), based on the mixture of threo enantiomers present, are suitable for use as herbicides and growth regulators, in particular for the selective use in plant crops, and can be prepared by the process of claim 9.

## Claims

### Claim 1

A compound of formula (I) and/or a salt thereof, in each case in the optically active (3R,4R)-threo form,
in which
R1 is hydrogen or a hydrolyzable radical,
(R2)n is n substituents R2,
where R2 (if n=1) or each of the substituents R2 (if n is greater than 1) independently of the others is halogen, cyano, nitro, (C1-C8)-alkyl, (C1-C8)-alkoxy, (C1-C8)-alkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C6)-haloalkyl, (C1-C6)-haloalkoxy, (C1-C6)-haloalkylthio, (C1-C6)-haloalkylsulfinyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, tri-[(C1-C4)-alkyl]-silyl or tri-[(C1-C4)-alkyl]-silyl-(C1-C4)-alkyl
or where in each case two groups R2 located ortho at the ring together are a group of the formula —Z1-A*-Z2 in which
A* is an alkylene group having from 1 to 4 carbon atoms which is optionally substituted by at least one radical selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy and (C1-C4)-haloalkoxy,
Z1 is a direct bond, O or S and
Z2 is a direct bond, O or S,
where the group —Z1-A*-Z2 together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, and
(R3)m is m substituents R3,
where R3 (if m=1) or each of the substituents R3 (if m is greater than 1) independently of the others is halogen, cyano, nitro, (C1-C8)-alkyl, (C1-C8)-alkoxy, (C1-C8)-alkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C6)-haloalkyl, (C1-C6)-haloalkoxy, (C1-C6)-haloalkylthio, (C1-C6)-haloalkylsulfinyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, NR*R**, where R* and R** are defined below, tri-[(C1-C4)-alkyl]-silyl or tri-[(C1-C4)-alkyl]-silyl-(C1-C4)-alkyl
or where in each case two groups R3 located ortho at the ring together are a group of the formula —Z3-A**-Z4 in which
A** is an alkylene group having from 1 to 4 carbon atoms which is optionally substituted by at least one radical selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy and (C1-C4)-haloalkoxy,
Z3 is a direct bond, O or S and
Z4 is a direct bond, O or S,
where the group —Z3-A**-Z4 together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, and
n, m are each independently of one another 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or 3, with the proviso that the two are not simultaneously 0,
where the stereochemical configuration at the carbon atom in position 3 of the butyric acid derivative has a stereochemical purity of from 60 to 100% (R), optionally from 70 to 100% (R), or optionally from 80 to 100% (R), or even optionally from 90 to 100% (R), based on a mixture of threo enantiomers present, and
the stereochemical configuration at the carbon atom in position 4 of the butyric acid derivative has a stereochemical purity of from 60 to 100% (R), optionally from 70 to 100% (R), or optionally from 80 to 100% (R), in or even optionally from 90 to 100% (R), based on a mixture of threo enantiomers present.

### Claim 2 (depends on 1)

The compound and/or a salt thereof as claimed in claim 1, wherein
R1 is hydrogen or an optionally substituted hydrocarbon radical or an optionally substituted heterocyclyl radical, where each of the two lastmentioned carbon-containing at least one radical including at least one substituent comprising from 1 to 30 carbon atoms, optionally from 1 to 24 carbon atoms, or optionally 1 to 20 carbon atoms, or
R1 is a radical of the formula SiRaRbRc, —NRaRb or —N═CRcRd,
where in the 3 lastmentioned formulae each of the radicals Ra, Rb, Rc and Rd independently of the others is hydrogen or an optionally substituted hydrocarbon radical, where, however, SiH3 for SiRaRbRc is excluded, or Ra and Rb together with the nitrogen atom are a 3- to 9-membered heterocycle which, in addition to the nitrogen atom, may contain one or two further ring heteroatoms selected from the group consisting of N, O and S and which is unsubstituted or substituted, or Rc and Rd together with the carbon atom are a 3- to 9-membered carbocyclic radical or a heterocyclic radical which may contain from 1 to 3 ring heteroatoms selected from the group consisting of N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted,
where each of the radicals Ra, Rb, Rc and Rd including substituents comprises not more than 30 carbon atoms, to optionally not more then 24 carbon atoms, or optionally not more than 20 carbon atoms, or
R1 is a radical of the formula —C(═O)—Re or —P(═O)(Rf)2, where Re and the Rf independently of one another are each hydrogen, OH, (C1-C8)-alkyl, (C1-C4)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C8)-alkyl, (C1-C4)-haloalkoxy, (C1-C4)-haloalkoxy-(C1-C8)-alkyl, (C3-C8)-alkenyloxy, (C3-C8)-alkenyloxy-(C1-C8)-alkyl, (C3-C8)-alkynyloxy, (C3-C8)-alkynyloxy-(C1-C8)-alkyl, —NR*R**, where R* and R** are defined below, tri-[(C1-C4)-alkyl]-silyl, tri-[(C1-C4)-alkyl]-silyl-(C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C8)-alkyl, (C5-C6)-cycloalkenyl, (C5-C6)-cycloalkenyl-(C1-C8)-alkyl, (C5-C6)-cycloalkynyl, (C5-C6)-cycloalkynyl-(C1-C8)-alkyl, phenyl, phenyl-(C1-C8)-alkyl, phenoxy, phenoxy-(C1-C8)-alkyl, phenylamino, phenylamino-(C1-C8)-alkyl, a radical Het1, Het1-(C1-C6)-alkyl or Het1-O—(C1-C6)-alkyl, where the heterocyclic radical Het1 is defined below,
where each of the 15 lastmentioned radicals is unsubstituted in the acyclic moiety or substituted by at least one identical or different radical RA and is unsubstituted in the cyclic moiety or substituted by at least one identical or different radical RB,
where in a radical mentioned above and in a radical below
Het1 in each case independently of the others is a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having from 3 to 9 ring atoms or a 9- or 10-membered bicyclic heterocycle, each containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S,
R*, R** are each independently of one another (and also independently of other radicals NR*R**) H, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-alkanoyl, [(C1-C4)-haloalkyl]-carbonyl, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, phenyl, phenyl-(C1-C4)-alkyl, where each of the 4 lastmentioned radicals is optionally substituted in the cycle by at least one identical or different radicals Rbb or
R* and R** together with the nitrogen atom are a 3- to 8-membered heterocycle which, in addition to the nitrogen atom, may contain one or two further ring heteroatoms selected from the group consisting of N, O and S and which may be unsubstituted or substituted by at least one radical from the group consisting of (C1-C4)-alkyl, (C1-C4)-haloalkyl and oxo,
RA is halogen, cyano, hydroxyl or (C1-C6)-alkoxy,
RB is halogen, cyano, hydroxyl, oxo, nitro, (C1-C8)-alkyl, (C1-C6)-haloalkyl, cyano-(C1-C6)-alkyl, hydroxy-(C1-C6)-alkyl, nitro-(C1-C6)-alkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (C1-C8)-alkoxy, (C2-C8)-alkenyloxy, (C2-C8)-alkynyloxy, (C1-C8)-haloalkoxy, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C4)-alkoxy, (C1-C6)-haloalkoxy-(C1-C4)-alkyl, (C1-C6)-haloalkoxy-(C1-C4)-alkoxy, (C1-C8)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C8)-alkylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C6)-haloalkylsulfonyl, a radical of the formula Raa—C(═O)—, Raa—C(═O)—(C1-C6)-alkyl, where the Raa are defined below, —NR*R**, where R* and R** are defined below, tri-[(C1-C4)-alkyl]-silyl, tri-[(C1-C4)-alkyl]-silyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkoxy, phenyl, phenyl-(C1-C8)-alkyl, phenoxy, phenoxy-(C1-C8)-alkyl, phenylamino, phenylamino-(C1-C8)-alkyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the 11 lastmentioned radicals is optionally substituted in the cyclic moiety by at least one identical or different radical Rbb,
Raa in each case independently of the others is hydrogen, OH, (C1-C8)-alkyl, (C1-C6)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyloxy, (C1-C6)-haloalkoxy, (C1-C6)-haloalkoxy-(C1-C6)-alkyl, (C1-C6)-haloalkoxy-(C1-C6)-alkoxy, (C3-C8)-alkenyloxy, (C3-C8)-alkenyloxy-(C1-C6)-alkyl, (C3-C8)-alkenyloxy-(C1-C6)-alkoxy, (C3-C8)-alkynyloxy, (C3-C8)-alkynyloxy-(C1-C6)-alkyl, (C3-C8)-alkynyloxy-(C1-C6)-alkoxy, —NR*R*, where R* and R** are as defined above, tri-[(C1-C4)-alkyl]-silyl, tri-[(C1-C4)-alkyl]-silyl-(C1-C6)-alkyl, tri-[(C1-C4)-alkyl]-silyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkoxy, (C5-C8)-cycloalkenyl, (C5-C8)-cycloalkenyl-(C1-C6)-alkyl, (C5-C8)-cycloalkenyloxy, (C5-C8)-cycloalkynyl, (C5-C8)-cycloalkynyl-(C1-C6)-alkyl, (C5-C8)-cycloalkynyl-(C1-C6)-alkoxy, phenyl, phenyl-(C1-C8)-alkyl, phenyl-(C1-C8)-alkoxy, phenoxy, phenoxy-(C1-C8)-alkyl, phenoxy-(C1-C8)-alkoxy, phenylamino, phenylamino-(C1-C8)-alkyl, phenylamino-(C1-C8)-alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which is optionally attached via an alkylene group or alkoxy group and contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the 20 lastmentioned radicals is optionally substituted in the cyclic moiety by at least one identical or different radical Rbb, and
Rbb in each case independently of the others is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy or in the case of saturated or partially unsaturated cyclic base groups is also oxo.

### Claim 3 (depends on 1)

The compound and/or a salt thereof as claimed in claim 1, wherein
R1 is hydrogen, (C1-C18)-alkyl, (C2-C18)-alkenyl or (C2-C18)-alkynyl,
where each of the 3 lastmentioned radicals is unsubstituted or substituted by at least one radical selected from the group consisting of the radicals [subgroups (a)-(d)]
(a) halogen, cyano, thio, nitro, hydroxyl, carboxyl, (C1-C8)-alkoxy, (C2-C8)-alkenyloxy, (C2-C8)-alkynyloxy, (C1-C8)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C8)-alkylthio, (C2-C8)-alkenylthio, (C2-C8)-alkynylthio, (C1-C8)-haloalkylthio, (C2-C8)-haloalkenylthio, (C2-C8)-haloalkynylthio, (C1-C8)-alkylsulfinyl, (C2-C8)-alkenylsulfinyl, (C2-C8)-alkynylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C2-C8)-haloalkenylsulfinyl, (C2-C8)-haloalkynylsulfinyl, (C1-C8)-alkylsulfonyl, (C2-C8)-alkenylsulfonyl, (C2-C8)-alkynylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C2-C8)-haloalkenylsulfonyl, (C2-C8)-haloalkynylsulfonyl, radicals of the formula —NR*R**, where R* and R** are defined below, and
(C3-C8)-cycloalkyl, (C5-C8)-cycloalkenyl, (C5-C8)-cycloalkynyl, (C3-C8)-cycloalkyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl-(C1-C6)-alkyl-S(O)p—, (C5-C8)-cycloalkenyl-(C1-C6)-alkoxy, (C5-C8)-cycloalkenyl-(C1-C6)-alkyl-S(O)p—, (C5-C8)-cycloalkynyl-(C1-C6)-alkoxy, (C5-C8)-cycloalkynyl-(C1-C6)-alkyl-S(O)p—, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-S(O)p—, (C5-C8)-cycloalkenyloxy, (C5-C8)-cycloalkenyl-S(O)p—, (C5-C8)-cycloalkynyloxy, (C5-C8)-cycloalkynyl-S(O)p—, (C3-C8)-cycloalkoxy-(C1-C6)-alkoxy, (C3-C8)-cycloalkoxy-(C1-C6)-alkyl-S(O)p—, phenyl, phenyl-(C1-C6)-alkoxy, phenoxy, phenyl-S(O)p—, phenyl-(C1-C6)-alkyl-S(O)p—, phenoxy-(C1-C6)-alkoxy, phenoxy-(C1-C6)-alkyl-S(O)p—, a radical Het1, Het1-S(O)p—, Het1-(C1-C6)-alkoxy, Het1-O—, Het1-O—(C1-C6)-alkoxy, where the heterocyclic radical Het1 is defined below,
where each of the 29 lastmentioned radicals is unsubstituted in the acyclic moiety or substituted by at least one identical or different radical RA and is unsubstituted in the cyclic moiety or substituted by at least one identical or different radical RB and p is in each case independently of the others 0, 1 or 2,
(b) radicals of the formulae —C(═O)—RC, —C(═O)—O—RC, —O—C(═O)—RC, —O—C(═O)—O—RC, —C(═O)—S—RC, —C(═S)—S—RC, —C(═S)—S—RC, —C(═O)—NR*R**, —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—RC, —N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—RC, —P(═O)(RC)(RD), —P(═O)(ORC)(RD), P(═O)(ORC)(ORD) or —O—P(═O)(ORC)(ORD),
where R*, R**, RC and RD are as defined below,
(c) radicals of the formulae —SiR′3, —O—SiR′3, (R′)3Si—(C1-C6)-alkoxy, —CO—O—NR′2, —O—N═CR′2, —N═CR′2, —O—NR′2, —CH(OR′)2 and —O—(CH2)q—CH(OR′)2,
in which each of the radicals R′ independently of the others is H, (C1-C4)-alkyl or phenyl, which is unsubstituted or substituted by at least one radical selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy and nitro or at two adjacent positions by a (C2-C6)-alkylene bridge, and q is an integer from 0 to 6, and
(d) radicals of the formula R″O—CHR′″CH(OR″)—(C1-C6)-alkoxy,
in which each of the radicals R″ independently of the others is H or (C1-C4)-alkyl or together the radicals are a (C1-C6)-alkylene group and R′″ is H or (C1-C4)-alkyl,
or
R1 is (C3-C9)-cycloalkyl, (C5-C9)-cycloalkenyl, (C5-C9)-cycloalkynyl or phenyl,
where each of the 4 lastmentioned radicals is unsubstituted or substituted by at least one radical selected from the group consisting of radicals [subgroups (a′)-(e′)]
(a′) halogen, cyano, thio, nitro, hydroxyl, carboxyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (C1-C8)-alkoxy, (C2-C8)-alkenyloxy, (C2-C8)-alkynyloxy, (C1-C8)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C8)-alkylthio, (C2-C8)-alkenylthio, (C2-C8)-alkynylthio and radicals of the formula —NR*R**, where the radicals R* and R** are defined below,
(b′) radicals of the formulae —C(═O)—RC, —C(═O)—O—RC, —O—C(═O)—RC, —O—C(═O)—O—RC, —C(═O)—S—RC, —C(═S)—S—RC, —C(═S)—S—RC, —C(═O)—NR*R**, —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—RC, —N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—RC, —P(═O)(RC)(RD), —P(═O)(ORC)(RD), P(═O)(ORC)(ORD) or —O—P(═O)(ORC)(ORD),
where R*, R**, Rc and RD are as defined below,
(c′) radicals of the formulae —SiR′3, —O—SiR′3, (R′)3Si—(C1-C6)-alkoxy, —CO—O—NR′2, —O—N═CR′2, —N═CR′2, —O—NR′2, —CH(OR′)2 and —O—(CH2)q—CH(OR′)2,
in which each of the radicals R′ independently of the others is H, (C1-C4)-alkyl or phenyl, which is unsubstituted or substituted by at least one radical selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy and nitro or at two adjacent positions by a (C2-C6)-alkylene bridge, and q is an integer from 0 to 6, and
(d′) radicals of the formula R″O—CHR′″CH(OR″)—(C1-C6)-alkoxy,
in which each of the radicals R″ independently of the others is H or (C1-C4)-alkyl or together the radicals are a (C1-C6)-alkylene group and R′″ is H or (C1-C4)-alkyl, and
(e′) a radical of the formula Het1 which is unsubstituted or substituted by at least one identical or different radical RB,
or
R1 is a polycyclic radical based on (C3-C9)-cycloalkyl, (C5-C9)-cycloalkenyl, (C5-C9)-cycloalkynyl or phenyl, where the base ring is fused with a carbocyclic or heterocyclic ring, optionally a 5- or 6-membered ring having 0 or from 1 to 3 ring heteroatoms selected from the group consisting of N, O and S, optionally benzo-fused, and where the base ring or the polycyclic system is unsubstituted or substituted by at least one identical or different radical RB, optionally unsubstituted or substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, hydroxyl, carboxyl, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy, [(C1-C8)-alkoxy]-carbonyl, [(C1-C6)-haloalkoxy]-carbonyl and oxo,
or
R1 is a heterocyclic radical Het1 which is unsubstituted in the ring or in the polycyclic system or substituted by at least one identical or different radical RB, optionally unsubstituted or substituted by at least one radical selected from the group consisting of halogen, cyano, thio, nitro, hydroxyl, carboxyl, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy, [(C1-C8)-alkoxy]-carbonyl, [(C1-C6)-haloalkoxy]-carbonyl and oxo,
where in a radical mentioned above and in a radical below
Het1 in each case independently of the others is a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having from 3 to 9 ring atoms, optionally having 5 or 6 ring atoms, or a 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, optionally a 5- or 6-membered heterocycle having from 1 to 3 ring heteroatoms selected from the group consisting of N, O and S which is optionally also fused to a carbocyclic or heterocyclic ring, optionally a carbocyclic ring having from 3 to 6 carbon atoms or a heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring heteroatoms selected from the group consisting of N, O and S, optionally benzo-fused,
R*, R** are each independently of one another (i.e. also of other groups NR*R**) H, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-alkanoyl, [(C1-C4)-haloalkyl]-carbonyl, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, phenyl, phenyl-(C1-C4)-alkyl, where each of the 4 lastmentioned radicals in the cycle is optionally substituted by at least one identical or different radicals Rbb, or
R* and R** together with the nitrogen atom are a 3- to 8-membered heterocycle which, in addition to the nitrogen atom, may contain one or two further ring heteroatoms selected from the group consisting of N, O and S and which may be unsubstituted or substituted by at least one radical selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-haloalkyl and oxo,
RA is halogen, cyano, hydroxyl or (C1-C6)-alkoxy,
RB is halogen, cyano, hydroxyl, oxo, nitro, (C1-C6)-alkyl, (C1-C4)-haloalkyl, cyano-(C1-C4)-alkyl, hydroxy-(C1-C4)-alkyl, nitro-(C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkoxy, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-haloalkylsulfonyl, a radical of the formula Raa—C(═O)— or Raa—C(═O)—(C1-C6)-alkyl, where the Raa are defined below, —NR*R**, where R* and R** are defined below, tri-[(C1-C4)-alkyl]-silyl, tri-[(C1-C4)-alkyl]-silyl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C3-C6)-cycloalkyl-(C1-C8)-alkoxy, phenyl, phenyl-(C1-C6)-alkyl, phenoxy, phenoxy-(C1-C6)-alkyl, phenylamino, phenylamino-(C1-C6)-alkyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the 11 lastmentioned radicals is optionally substituted in the cyclic moiety by at least one identical or different radical Rbb,
RC, RD are each independently of one another (also independently of radicals RC, RD in other groups)
hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl or (C2-C8)-alkynyl,
where each of the 3 lastmentioned radicals is unsubstituted or substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, hydroxyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C8)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl and tri-[(C1-C4)-alkyl]-silyl,
or
(C3-C8)-cycloalkyl, (C5-C8)-cycloalkenyl, (C5-C8)-cycloalkynyl, phenyl, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C5-C8)-cycloalkenyl-(C1-C6)-alkyl, (C5-C8)-cycloalkynyl-(C1-C6)-alkyl, phenyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C6)-alkyl, (C3-C8)-cycloalkyl-S(O)p—(C1-C6)-alkyl, (C5-C8)-cycloalkenyloxy-(C1-C6)-alkyl, (C5-C8)-cycloalkynyloxy-(C1-C6)-alkyl, phenoxy-(C1-C6)-alkyl, phenyl-S(O)p—(C1-C6)-alkyl, (C3-C8)-cycloalkylamino-(C1-C6)-alkyl, (C5-C8)-cycloalkenylamino-(C1-C6)-alkyl, (C5-C8)-cycloalkynylamino-(C1-C6)-alkyl, phenylamino-(C1-C6)-alkyl, Het1, Het1-(C1-C6)-alkyl, Het1-O—(C1-C6)-alkyl or Het1-S(O)p—(C1-C6)-alkyl, where Het1 has the meaning mentioned,
where each of the 22 lastmentioned radicals is unsubstituted in the acyclic moiety or substituted by at least one identical or different radicals RA and is unsubstituted in the cyclic moiety or substituted by at least one identical or different radicals RB and p is in each case independently of the others 0, 1 or 2,
Raa in each case independently of the others is hydrogen, OH, (C1-C6)-alkyl, (C1-C4)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyloxy, (C1-C4)-haloalkoxy, (C1-C4)-haloalkoxy-(C1-C6)-alkyl, (C1-C4)-haloalkoxy-(C1-C6)-alkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkenyloxy-(C1-C6)-alkyl, (C3-C6)-alkenyloxy-(C1-C6)-alkoxy, (C3-C6)-alkynyloxy, (C3-C6)-alkynyloxy-(C1-C6)-alkyl, (C3-C6)-alkynyloxy-(C1-C6)-alkoxy, —NR*R*, where R* and R** are as defined above, tri-[(C1-C4)-alkyl]-silyl, tri-[(C1-C4)-alkyl]-silyl-(C1-C6)-alkyl, tri-[(C1-C4)-alkyl]-silyl-(C1-C6)-alkoxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy, (C3-C6)-cycloalkyl-(C1-C8)-alkyl, (C3-C6)-cycloalkyl-(C1-C8)-alkoxy, (C5-C6)-cycloalkenyl, (C5-C6)-cycloalkenyl-(C1-C6)-alkyl, (C5-C6)-cycloalkenyloxy, (C5-C6)-cycloalkynyl, (C5-C6)-cycloalkynyl-(C1-C6)-alkyl, (C5-C6)-cycloalkynyl-(C1-C6)-alkoxy, phenyl, phenyl-(C1-C6)-alkyl, phenyl-(C1-C6)-alkoxy, phenoxy, phenoxy-(C1-C6)-alkyl, phenoxy-(C1-C6)-alkoxy, phenylthio, phenyl-S(O)p—(C1-C6)-alkyl, phenyl-S(O)p—(C1-C6)-alkoxy, where p in each case independently of the others is 0, 1 or 2, phenylamino, phenylamino-(C1-C6)-alkyl, phenylamino-(C1-C6)-alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which is optionally attached via an alkylene group or alkoxy group and contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the 20 lastmentioned radicals is optionally substituted in the cyclic moiety by at least one identical or different radicals Rbb, and
Rbb in each case independently of the others is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy.

### Claim 4 (depends on 1)

The compound and/or a salt thereof as claimed in claim 1, wherein
(R2)n is n substituents R2,
where R2 (if n=1) or each of the substituents R2 (if n is greater than 1) independently of the others is halogen, cyano, nitro, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkylthio, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-haloalkyl, (C1-C6)-haloalkoxy, (C1-C6)-haloalkylthio, (C1-C6)-haloalkylsulfinyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, tri-[(C1-C4)-alkyl]-silyl or tri-[(C1-C4)-alkyl]-silyl-(C1-C4)-alkyl
or where in each case two groups R2 located ortho at the ring together are a group of the formula —Z1-A*-Z2 in which
A* is an alkylene group having from 1 to 4 carbon atoms which is optionally substituted by at least one radical selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy and (C1-C4)-haloalkoxy,
Z1 is a direct bond, O or S and
Z2 is a direct bond, O or S,
where the group —Z1-A*-Z2 together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring, and
(R3)m is m substituents R3,
where R3 (if m=1) or each of the substituents R3 (if m is greater than 1) independently of the others is halogen, cyano, nitro, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkylthio, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-haloalkyl, (C1-C6)-haloalkoxy, (C1-C6)-haloalkylthio, (C1-C6)-haloalkylsulfinyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, NR*R**, tri-[(C1-C4)-alkyl]-silyl or tri-[(C1-C4)-alkyl]-silyl-(C1-C4)-alkyl
or where in each case two groups R3 located ortho at the ring together are a group of the formula —Z3-A**-Z4 in which
A** is an alkylene group having from 1 to 4 carbon atoms which is optionally substituted by at least one radical selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy and (C1-C4)-haloalkoxy,
Z3 is a direct bond, O or S and
Z4 is a direct bond, O or S,
where the group —Z3-A**-Z4 together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring,
R*, R** each independently of one another or together with the nitrogen atom have the meaning mentioned and
n, m are each independently of one another 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or 3, with the proviso that the two are not simultaneously 0.

### Claim 5 (depends on 1)

The compound and/or a salt thereof as claimed in claim 1, wherein
(R2)n is n substituents R2,
where, in the case that n=1, the substituent R2 or, in the case that n is greater than 1, each of the substituents R2 independently of the others is
halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C1-C4)-haloalkylthio, (C1-C4)-haloalkylsulfinyl, (C1-C4)-haloalkylsulfonyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, tri-[(C1-C4)-alkyl]-silyl or tri-[(C1-C4)-alkyl]-silyl-(C1-C4)-alkyl and
n is 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or 3, optionally 0, 1 or 2, with the proviso that n and m are not both simultaneously 0.

### Claim 6 (depends on 1)

The compound and/or a salt thereof as claimed in claim 1, wherein
(R3)m is m substituents R3,
where, in the case that m=1, the substituent R3 or, in the case that m is greater than 1, each of the substituents R3 independently of the others is halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C1-C4)-haloalkylthio, (C1-C4)-haloalkylsulfinyl, (C1-C4)-haloalkylsulfonyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or tri-[(C1-C4)-alkyl]silyl-Zb—, where Zb=a covalent bond or (C1-C4)-alkylene, or
in each case two groups R3 located ortho at the ring together are a group of the formula —Z3-A**-Z4,
where
A** is an alkylene group which is optionally substituted by at least one radical selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy and (C1-C4)-haloalkoxy,
Z3 is O or S and
Z4 is O or S, where the group —Z3-A**-Z4 together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring,
m is 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2, 3 or 4, or optionally 0, 1, 2 or 3, with the proviso that n and m in formula (I) are not both simultaneously 0.

### Claim 7 (depends on 1)

The compound and/or a salt thereof as claimed in claim 1, wherein
(R2)n is n substituents R2,
where, in the case that n=1, the substituent R2 or, in the case that n is greater than 1, each of the substituents R2 independently of the other is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and
(R3)m is m substituents R3,
where, in the case that m=1, the substituent R3 or, in the case that m is greater than 1, each of the substituents R3 independently of the other is halogen, cyano, nitro, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and
m is 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2, 3 or 4, or optionally 0, 1, 2 or 3 and
n is 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or 3, or optionally 0, 1 or 2,
with the proviso, that n and m are not simultaneously 0.

### Claim 8 (depends on 1)

The compound and/or a salt thereof as claimed in claim 1, wherein
(R2)n is 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-CF3, 3-CF3, 4-CF3, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulfinyl, 3-methylsulfinyl, 4-methylsulfonyl, 2-methylsulfonyl, 3-methylsulfonyl, 4-methylsulfonyl, 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 or 3,4,5-trichloro and
(R3)m is 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-CF3, 3-CF3, 4-CF3, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulfinyl, 3-methylsulfinyl, 4-methylsulfonyl, 2-methylsulfonyl, 3-methylsulfonyl, 4-methylsulfonyl, 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-NO2-3-F), (4-OMe-3-F), (3-CN-4-F), (3-NO2-4-F), (3-CN-4-Cl), (3-NO2-4-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 or 3,4,5-trichloro.

### Claim 9 (depends on 1)

A process for preparing a compound of formula (I) as defined in claim 1, and/or a salt thereof comprising
[A] reacting a compound of formula (II)
with a compound of formula (III) and/or a salt thereof
to give a compound of formula (I′)
where R1, R2, R3, m and n in the compounds (II), (III) and (I′) are as defined in the respective compound of formula (I) to be prepared, and the (3R,4R)-threo isomer is isolated from an isomer mixture (I′) analogously to a general separating method
or
(b) reacting a compound of formula (I″)
in which R is a radical selected from the group of radicals possible for R1, but different from the radical R1 in the compound (I′) to be prepared,
with a compound of formula R1—OH in which R1 is defined as in the compound of formula (I) to be prepared, to give compound (I′), where R2, R3, m and n in the compound (I″) are as defined in the compound of formula (I) to be prepared in each case, and the (3R,4R)-threo isomer is isolated from the isomer mixture (I′) analogously to a general separating method
or
(c) stereochemically enriched reacting a compound of the (3R,4R)-threo isomers of formula (I′″)
in which R is a radical selected from the group of the radicals possible for R1, but different from the radical R1 in the compound (I) to be prepared,
with a compound of formula R1—OH in which R1 is defined as in the compound of formula (I) to be prepared, to give compound (I), where R2, R3, m and n in the compound (I′″) are as defined in the compound of formula (I) to be prepared.

### Claim 10 (depends on 1)

A herbicidal and/or a plant growth-regulating composition which comprises at least one compound of formula (I) and/or a salt thereof as defined in claim 1, and at least one formulation auxiliary said auxiliary being customary in crop protection.

### Claim 11 (depends on 1)

A method for controlling a harmful plant and/or for regulating the growth of a plant which comprises applying an effective amount of at least one compound of formula (I) and/or a salt thereof as defined in claim 1, onto a plant, a plant seed, soil in which and/or on which a plant grows and/or an area under cultivation.

### Claim 12 (depends on 11)

The method as claimed in claim 11, wherein a compound of formula (I) and/or a salt thereof is employed for controlling a harmful plant and/or for regulating growth in a crop of a useful plant and/or an ornamental plant.

### Claim 13 (depends on 12)

The method as claimed in claim 12, wherein the crop plant is a transgenic crop plant.

### Claim 14 (depends on 1)

A compound of formula (I) and/or a salt thereof as claimed in claim 1, capable of being used as a herbicide and/or a plant growth regulator.

### Claim 15 (depends on 14)

A compound of the formula (I) and/or a salt thereof capable of being used as claimed in claim 14, wherein the compound and/or salt is capable of being applied in a crop of a useful and/or an ornamental plant.

### Claim 16 (depends on 1)

A method for regulating the growth of a plant which comprises applying an effective amount of at least one compound of formula (I) and/or a salt thereof as defined in claim 1, onto a plant, a plant seed, soil in which and/or on which a plant grows and/or an area under cultivation.

### Claim 17 (depends on 16)

The method as claimed in claim 16, wherein the compound of formula (I) and/or a salt thereof is employed for regulating growth in a crop of a useful plant and/or an ornamental plant.

### Claim 18 (depends on 1)

A method for controlling a harmful plant which comprises applying an effective amount of at least one compound of formula (I) and/or a salt thereof as defined in claim 1, onto a plant, a plant seed, soil in which and/or on which a plant grows and/or an area under cultivation.

### Claim 19 (depends on 18)

The method as claimed in claim 18, wherein the compound of formula (I) and/or a salt thereof is employed for controlling a harmful plant in a crop of a useful plant and/or an ornamental plant.