# US 8,541,617 B2 · Cycloalkylphenyl substituted cyclic ketoenols

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- Number: US 8,541,617 B2
- Document ID: US8541617B2
- Status: Granted
- Kind: B2
- Application number: 13/181,202
- Filed: 2011-07-12
- Published: 2012-07-12
- Granted: 2013-09-24
- Earliest claimed: 2006-02-21
- Assignees: Bayer CropScience AG
- Applicants: Reiner Fischer; Thomas Bretschneider; Stefan Lehr; Dieter Feucht; Eva-Maria Franken; Olga Malsam; Alfred Angermann; Guido Bojack; Christian Arnold; Martin Jeffery Hills; Heinz Kehne; Christopher Hugh Rosinger
- Inventors: Reiner Fischer; Thomas Bretschneider; Stefan Lehr; Dieter Feucht; Eva-Maria Franken; Olga Malsam; Alfred Angermann; Guido Bojack; Christian Arnold; Martin Jeffery Hills; Heinz Kehne; Christopher Hugh Rosinger
- Web page: https://patentgrep.com/patent/US8541617B2

## CPC

- C07C 233/51: having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
- A01N 37/10: Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
- A01N 37/46: N-acyl derivatives
- A01N 43/16: with oxygen as the ring hetero atom
- A01N 43/36: five-membered rings
- A01N 43/38: condensed with carbocyclic rings
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/06: containing —O—CO—O— groups; Thio analogues thereof
- C07C 69/616: polycyclic
- C07D 207/36: Oxygen or sulfur atoms
- C07D 209/54: Spiro-condensed
- C07D 231/54: condensed with carbocyclic rings or ring systems
- C07D 307/60: Two oxygen atoms, e.g. succinic anhydride
- C07C 2601/02: with a three-membered ring
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to novel cycloalkylphenyl-substituted cyclic ketoenols of the formula (I) in which J, X, Y, m and CKE are as defined above, to processes and intermediates for their preparation and to their use as pesticides and/or herbicides. Moreover, the invention relates to selective herbicidal compositions comprising, firstly, the cycloalkylphenyl-substituted cyclic ketoenols and, secondly, a crop plant compatibility-improving compound. The invention furthermore relates to increasing the activity of crop protection compositions comprising compounds of the formula (I) by adding ammonium or phosphonium salts and, if appropriate, penetrants.

## Claims

### Claim 1

A compound of formula (XXVII)
in which
J represents cyclopropyl,
X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy,
Y represents hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy,
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen, and
Z represents a leaving group introduced by carboxylic acid-activating reagents, carbodiimides, phosphorylating agents, or halogenating agents.

### Claim 2 (depends on 1)

A compound of formula (XXVII) according to claim 1, in which
Z represents a leaving group introduced by carbonyldiimidazole, dicyclohexylcarbodiimide, POCL3, BOP-Cl, thionyl chloride, oxalyl chloride, phosgene, or chloroformic esters.

### Claim 3 (depends on 1)

A compound of formula (XXVII) according to claim 1 in which
J represents cyclopropyl,
X represents hydrogen, halogen, C1-C6-alkyl, C1-C4-haloalkyl, C1-C6-alkoxy or C1-C4-haloalkoxy,
Y represents hydrogen, C1-C6-alkyl, C1-C4-haloalkyl, halogen, C1-C6-alkoxy or C1-C4-haloalkoxy, and
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.

### Claim 4 (depends on 1)

A compound of formula (XXVII) according to claim 1 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, iodine, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy or trifluoromethoxy,
Y represents hydrogen, fluorine, chlorine, bromine, iodine, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy or trifluoromethoxy, and
m represents a number 1 or 2
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.

### Claim 5 (depends on 1)

A compound of formula (XXVII) according to claim 1 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,
Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns
where only in the phenyl substitution patterns (B), (K) and (L), X may also represent hydrogen.

### Claim 6 (depends on 1)

A compound of formula (XXVII) according to claim 1 in which
J represents cyclopropyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine, methyl, ethyl or hydrogen,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns

### Claim 7

A compound of formula (XXX)
in which
J represents cyclopropyl,
X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy,
Y represents hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy,
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen, and
with the proviso that the compound is not

### Claim 8 (depends on 7)

A compound of formula (XXX) according to claim 7 in which
J represents cyclopropyl,
X represents hydrogen, halogen, C1-C6-alkyl, C1-C4-haloalkyl, C1-C6-alkoxy or C1-C4-haloalkoxy,
Y represents hydrogen, C1-C6-alkyl, C1-C4-haloalkyl, halogen, C1-C6-alkoxy or C1-C4-haloalkoxy, and
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.

### Claim 9 (depends on 7)

A compound of formula (XXX) according to claim 7 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, iodine, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy or trifluoromethoxy,
Y represents hydrogen, fluorine, chlorine, bromine, iodine, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy or trifluoromethoxy, and
m represents a number 1 or 2
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.

### Claim 10 (depends on 7)

A compound of formula (XXX) according to claim 7 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,
Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns
where only in the phenyl substitution patterns (B), (K) and (L), X may also represent hydrogen.

### Claim 11 (depends on 7)

A compound of formula (XXX) according to claim 7 in which
J represents cyclopropyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine, methyl, ethyl or hydrogen,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns

### Claim 12

A compound of formula (XXXIV)
in which
J represents cyclopropyl,
X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy,
Y represents hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy,
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen, and
R8 represents alkyl.

### Claim 13 (depends on 12)

A compound of formula (XXXIV) according to claim 12, in which
R8 represents C1-C6 alkyl.

### Claim 14 (depends on 12)

A compound of formula (XXXIV) according to claim 12, in which
R8 represents C1-C8 alkyl.

### Claim 15 (depends on 12)

A compound of formula (XXXIV) according to claim 12 in which
J represents cyclopropyl,
X represents hydrogen, halogen, C1-C6-alkyl, C1-C4-haloalkyl, C1-C6-alkoxy or C1-C4-haloalkoxy,
Y represents hydrogen, C1-C6-alkyl, C1-C4-haloalkyl, halogen, C1-C6-alkoxy or C1-C4-haloalkoxy, and
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.

### Claim 16 (depends on 12)

A compound of formula (XXXIV) according to claim 12 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, iodine, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy or trifluoromethoxy,
Y represents hydrogen, fluorine, chlorine, bromine, iodine, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy or trifluoromethoxy, and
m represents a number 1 or 2
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.

### Claim 17 (depends on 12)

A compound of formula (XXXIV) according to claim 12 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,
Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns
where only in the phenyl substitution patterns (B), (K) and (L), X may also represent hydrogen.

### Claim 18 (depends on 12)

A compound of formula (XXXIV) according to claim 12 in which
J represents cyclopropyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine, methyl, ethyl or hydrogen,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns