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Substituted benzamides for treating arthropodes

A technology of compounds and oxides, applied in the field of arachnids and nematodes, insects

Active Publication Date: 2016-08-17
BAYER CROPSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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In addition, resistant

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  • Substituted benzamides for treating arthropodes
  • Substituted benzamides for treating arthropodes
  • Substituted benzamides for treating arthropodes

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[0138] The definition of collective terms also applies to these collective terms for composite substituents, unless defined otherwise. Example: C LL -C UL - The definition of alkyl also applies to C LL -C UL -Alkyl as compound substituent such as (C LL -C UL )-Cycloalkyl-(C LL -C UL )-part of an alkyl group.

[0139] It will be appreciated by those skilled in the art that the examples cited in this application should not be considered in a limiting manner, but merely to describe some embodiments in detail.

[0140] In the definitions of symbols given in the above formulas, general designations generally representing the following substituents are used:

[0141] Halogen relates to elements of the seventh main group, preferably fluorine, chlorine, bromine and iodine, more preferably fluorine, chlorine and bromine, and even more preferably fluorine and chlorine.

[0142] Examples of heteroatoms are N, O, S, P, B, Si. Preferably, the term "heteroatom" relates to N, S and...

Embodiment I-T2-1

[1295]

[1296] 710 mg (2.24 mmol) of 1-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]ethanone was added to 401 mg (3.36 mmol) of N,N-dimethylformamide dimethyl acetal, and the mixture was heated to reflux for 5 hours. For work-up, the mixture was cooled slightly and all volatile components were evaporated off with a rotary evaporator under reduced pressure. The residue was chromatographed using a column containing 40 g of silica gel with a cyclohexane / ethyl acetate gradient from 90:10 to 50:50 (v / v). 675 mg of 3-(dimethylamino)-1-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(tetrafluoromethyl)ethyl]phenyl were obtained ] prop-2-en-1-one.

[1297]

[1298] 1.2g (3.23mmol) of 3-(dimethylamino)-1-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(tetrafluoromethyl) Ethyl]phenyl]prop-2-en-1-one was added to 15.5 ml of ethanol, and 170 mg (3.39 mmol) of hydrazine hydrate and 192 mg (3.2 mmol) of glacial acetic acid were added. The resulting mixture was stirred at r...

Embodiment I-T3-1

[1316]

[1317] The preparation of the precursor [2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]hydrazine is described in the literature (US 2003 / 187233).

[1318]

[1319] First, 3.41 g (11.2 mmol) of [2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] in 13 ml of ethanol Phenyl]hydrazine (free base) was charged into a 25ml flask. Then 1.84 g (11.2 mmol) of tetramethoxypropane were added, followed by 0.55 g (5.6 mmol) of 96% sulfuric acid. The reaction mixture was heated to reflux for 2h. Ethanol was distilled off on a rotary evaporator under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was removed, dried over sodium sulfate and concentrated under reduced pressure on a rotary evaporator. The residue was distilled under reduced pressure in a Kugelrohr at 1 mbar and 150° C. to obtain 2.5 g of 1-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethane ...

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Abstract

The invention relates to compounds of general formula (I), in which the groups A1-A4, T, n, W, Q, R1 and B1-B4 are defined as cited in the description. Further disclosed are methods for producing the compounds of formula (I). The compounds according to the invention are in particular suitable for controlling insects, arachnids and nematodes in agricultural applications and for controlling ectoparasites in veterinary medicine.

Description

Background technique [0001] The present application relates to novel trifluorocompounds, to processes for the preparation of said compounds and to their use for controlling animal pests, in particular arthropods and especially insects, arachnids and nematodes. [0002] It is known that certain halogen-substituted compounds have insecticidal activity (EP 1 911 751, WO2012 / 069366, WO2012 / 080376, WO2012 / 107434 and WO2012 / 175474). [0003] WO 2011 / 113756 discloses triazole derivatives with insecticidal activity. [0004] It is known that certain halogen-substituted compounds possess cytokine-inhibitory activity (WO2000 / 07980). [0005] Modern crop protection compositions must meet many requirements, for example regarding efficacy, persistence and spectrum of action as well as possible uses. Issues of toxicity and combinability with other active ingredients or formulation auxiliaries play a role, as do the costs involved in synthesizing the active ingredients. Additionally, resi...

Claims

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Application Information

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IPC IPC(8): C07D231/12A01N43/56A01N43/72C07D261/08A01P7/00C07D401/04C07D207/337A01N43/80
CPCA01N43/80C07D401/04C07D403/04C07D261/08C07D207/337A01N43/40C07D231/00C07D413/04C07D261/00A01N43/56C07D231/12A61P33/02A61P33/10A61P33/14A01N43/82A01N43/72A01N43/36A01N43/54
Inventor W·哈伦巴赫H-G·施瓦茨K·伊尔格U·高根斯J·考博灵A·特伯格N·伯恩克M·毛厄R·维尔坦T·哈施内克J·J·哈恩S·霍斯特曼
Owner BAYER CROPSCIENCE AG
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