IP Library Granted Patent US 7,314,958
Granted Patent B2
US 7,314,958 · App. 10/518,446 · Granted Jan 1, 2008

Phenylbenzamides

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Quick Facts
Patent No.
US 7,314,958
App. No.
10/518,446
Granted
Jan 1, 2008
Kind
B2
Abstract

This invention relates to novel phenylbenzamides of the formula (I) in which R 1 represents trifluoromethyl, chlorine, bromine or iodine and R 2 represents hydrogen, methyl or ethyl, to a process for preparing these substances and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.

Claims (27)

1. A phenylbenzamide of formula (I)

in which

R 1 represents trifluoromethyl, chlorine, bromine, or iodine, and

R 2 represents hydrogen, methyl, or ethyl.

2. A phenylbenzamide of formula (I) according to claim 1 in which R 2 represents hydrogen.

3. A phenylbenzamide of formula (I) according to claim 1 selected from the group consisting of

N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide,

N-[2-(1,3-dimethylbutyl)phenyl]-2-chlorobenzamide,

N-[2-(1,3-dimethylbutyl)phenyl]-2-bromobenzamide,

N-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide,

2-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide,

2-chloro-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide,

2-bromo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide, and

2-iodo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide.

4. A process for preparing a phenylbenzamide of formula (I) according to claim 1 comprising

(a) reacting aniline with an alkene of formula (II)

 in which R 2 represents hydrogen, methyl, or ethyl, in the presence of a base and in the presence of a Lewis acid to form an alkylphenylamine derivative of formula (III)

 in which R 2 represents hydrogen, methyl, or ethyl, and

(b) reacting the alkylphenylamine derivative of formula (III) with a benzoyl chloride of formula (IV)

 in which R 1 represents trifluoromethyl, chlorine, bromine or iodine, optionally in the presence of an acid binder and optionally in the presence of a diluent.

5. A composition for controlling fungi and bacteria in the protection of corps and materials comprising one or more phenylbenzamides of formula (I) according to claim 1 and one or more extenders and/or surfactants.

6. A method for controlling fungi and bacteria that infects crops and materials comprising applying an effective amount of one or more phenylbenzamides of formula (I) according to claim 1 to the fungi and bacteria and/or their habitat.

7. A process for preparing compositions for controlling fungi and bacteria that infects crops and materials comprising mixing one or more phenylbenzamides of formula (I) according to claim 1 with one or more extenders and/or surfactants.

8. A process for preparing a phenylamine derivative of formula (III)

in which R 2 represents hydrogen, methyl, or ethyl, comprising reacting aniline with an alkene of formula (II)

in which R 2 represents hydrogen, methyl, or ethyl, in the presence of a base and in the presence of a Lewis acid.

9. A method according to claim 6 wherein the fungi and bacteria are selected from Alternaria, Aspergillus, Chaetomium, Coniophora, Lentinus, Penicillium, Polyporus, Aureobasidium, Sclerophoma, Trichoderma, Escherichia, Pseudomonas, Staphylococcus, Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae, Streptomycetaceae, Xanthomonas, Pseudomonas, Erwinia, Pythium, Phytophthora, Pseudoperonospora, Plasmopara, Bremia, Peronospora, Erysiphe, Sphaerotheca, Podosphaera, Venturia, Pyrenophora, Cochliobolus, Uromyces, Puccinia, Sclerotinia, Tilletia, Ustilago, Pellicularia, Pyricularia, Fusarium, Botrytis, Septoria, Leptosphaeria, Cercospora, Alternaria , and Pseudocercosporella.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2018
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 045034/0468 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2005
From: ELBE, HANS-LUDWIG; RIECK, HEIKO; DUNKEL, RALF; REINECKE, PAUL; WACHENDORFF-NEUMANN, ULRIKE; MACHNIK, ASTRID MAULER; KUCK, KARL-HEINZ
To: BAYER CROPSCIENCE AG
Reel/Frame 017005/0022 →