Substituted benzamides for treating arthropodes
A technology of compounds and oxides, applied in the field of arachnids and nematodes, insects
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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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