IP Library Granted Patent US 7,396,939
Granted Patent B2
US 7,396,939 · App. 11/297,677 · Granted Jul 8, 2008

3-cyclopropyl-4-(3-amino-2-methylbenzoyl)pyrazoles and their use as herbicides

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Quick Facts
Patent No.
US 7,396,939
App. No.
11/297,677
Granted
Jul 8, 2008
Kind
B2
Abstract

What is described are 3-cyclopropyl-4-(3-amino-2-methylbenzoyl)pyrazoles of the formula (I) and their use as herbicides. In this formula (I), R 1 , R 2 , R 3 , R 4 and R 5 are various radicals.

Claims (30)

1. A compound of the formula (I) or salt thereof

in which

R 1 and R 2 independently of one another are hydrogen, furan-2-yl, tetrahydrofuran-2-yl-methyl,

or (C 1 -C 4 )-alkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl or (C 3 -C 6 )-cycloalkenyl-(C 1 -C 4 )-alkyl substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy, where R 1 and R 2 are not simultaneously hydrogen,

or

NR 1 R 2 is a 4- to 7-membered saturated, partially saturated, fully unsaturated or aromatic ring comprising as ring atoms n heteroatoms from the group consisting of nitrogen, oxygen and sulfur which ring is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, trifluoromethyl, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, fluoro-(C 1 -C 3 )-alkyl, fluoro-(C 1 -C 3 )-alkoxy or (C 1 -C 3 )-alkoxymethyl;

R 3 is methyl, ethyl or isopropyl;

R 4 is (C 1 -C 4 )-alkyl, (C 3 -C 4 )-alkenyl or (C 3 -C 4 )-alkynyl;

R 5 is hydrogen, (C 1 -C 4 )-alkylsulfonyl, (C 3 -C 4 )-alkenylsulfonyl, (C 3 -C 4 )-alkynylsulfonyl,

or phenylsulfonyl or benzyl substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, trifluoromethyl, nitro, methyl, ethyl, methoxy and ethoxy,

m is 0, 1, 2 or 3;

n is 1, 2 or 3.

2. The compound as claimed in claim 1 in which

R 1 and R 2 independently of one another are hydrogen,

or (C 1 -C 4 -alkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 -alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl or (C 3 -C 6 )-cycloalkenyl-(C 1 -C 4 )-alkyl substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy, where R 1 and R 2 are not simultaneously hydrogen,

or

NR 1 R 2 is a 4- to 7-membered saturated, partially saturated, fully unsaturated or aromatic ring comprising as ring atoms n heteroatoms from the group consisting of nitrogen, oxygen and sulfur which ring is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, fluoro-(C 1 -C 3 )-alkyl, fluoro-(C 1 -C 3 )-alkoxy or (C 1 -C 3 )-alkoxymethyl.

3. The compound as claimed in claim 1 in which

R 1 and R 2 independently of one another are hydrogen, methyl, butyl, ethyl, propyl, propenyl, propynyl, cyclopropyl, cyclopropylmethyl, methoxyethyl, methoxypropyl, 2-methoxy-1-methylethyl, 2-ethoxy-1-methylethyl, hydroxyethyl or ethoxyethyl,

or

NR 1 R 2 form a radical from the group consisting of 1-pyrrolyl, 1-pyrrolidinyl, 1-pyrazolyl, 1-piperidine, 1-morpholinyl and 1-piperazinyl which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy.

4. The compound as claimed in claim 1 in which

R 1 and R 2 independently of one another are hydrogen, methyl, butyl, ethyl, propyl, propenyl, propynyl, cyclopropyl, cyclopropylmethyl, methoxyethyl, methoxypropyl, 2-methoxy-1-methylethyl, 2-ethoxy-1-methylethyl, hydroxyethyl or ethoxyethyl,

or

NR 1 R 2 form a radical from the group consisting of 1-pyrrolyl, 1-pyrrolidinyl, 1-pyrazolyl, 1-piperidine, 1-morpholinyl and 1-piperazinyl and

R 5 is hydrogen, propylsulfonyl, tosyl or 2,6-difluorobenzyl.

5. The compound as claimed in claim 1 in which

R 3 is methyl or ethyl;

R 4 is methyl or ethyl, and

R 5 is hydrogen.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 15, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 036801/0914 →