Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-08-11
2000-02-29
Chang, Ceila
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514256, 514318, 544333, 546193, 546207, 546208, 546209, 546210, 546211, A01N 4340, A01N 4354, C07D40110, C07D41710
Patent
active
060309873
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to methods for controlling insects. In particular, it relates to control by the application of certain novel N-(substituted arylmethyl)-4-[bis(substituted phenyl or pyridyl)methyl]piperidines to the locus where insect control is needed.
It has now been found that compounds of the following structure and their corresponding N-oxides, as well as their agriculturally acceptable salts, are active as insecticides: ##STR3## in which U is --(CH.sub.2).sub.n ; ##STR4## in which V, W, Y, and Z are each hydrogen; halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, haloalkoxyalkyl, or aminocarbonyl; and the heterocycle is optionally connected to the phenyl ring through a --O--, --S--, --(CH.sub.2).sub.p, --C(O)--, or --O--(CR.sup.3 R.sup.4).sub.q linkage; substituted with haloalkyl or haloalkoxy; the para position of the phenyl ring or the 5-position of a 2-pyridyl ring; no more than two of R.sup.3 and R.sup.4 are methyl; each aliphatic moiety contains not more than 4 carbon atoms; halogen means bromine, chlorine, or fluorine; each heterocycle contains from 1 to 4 nitrogen atoms, or 1 or 2 oxygen or sulfur atoms, or 1 or 2 nitrogen atoms and an oxygen or sulfur atom;
Preferred are those compounds in which pyridazinyl, pyrazinyl, pyrazolyl, pyridyl, pyrimidinyl, pyrolyl, 2H-tetrazol-5-yl, 1,2,3-thiadiazolyl, 1,3,5-triazinyl, and 1,2,4-triazolyl, optionally substituted with halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, or haloalkoxyalkyl, and the optional linkage is selected from --O--, --(CH.sub.2).sub.p, or --O--(CHR.sup.3).sub.q ;
R.sup.1 and R.sup.2 are independently selected from trifluoromethylphenyl, trifluoromethoxyphenyl, trifluoromethylpyridyl, and trifluoromethoxypyridyl;
Particularly preferred are those compounds in which pyrazol-3-yl, pyrid-2-yl, pyrimidin-2-yl, pyrol-3-yl, 2H-tetrazol-5yl, 1,2,3-thiadiazol-4-yl, 1,2,4-triazol-3-yl, optionally substituted with halogen, cyano, alkyl, haloalkyl, or alkoxyalkyl, and the optional linkage is selected from --O--, --O--CH.sub.2 --, or --O--CH(CH3); p-trifluoromethoxyphenyl, p-trifluoromethylphenyl, 5-trifluoromethylpyrid-2-yl, and 5-trifluoromethoxy-pyrid-2-yl;
The N-oxides include the piperidine N-oxides, the pyridine N-oxides, or both.
The compounds of the present invention were prepared by methods generally known to those skilled in the art. In the method shown in Schema 1, where R.sup.1 and R.sup.2 are the same, ethyl piperidin-4-ylcarboxylate was reacted with either an appropriately substituted alkyl halide, for example, 4-methoxyphenylmethyl bromide, or with an appropriately substituted aldehyde under reductive conditions, for example, 4-phenoxybenzaldehyde, affording the corresponding ethyl N-substituted alkylpiperidin-4-ylcarboxylate (A). Intermediate (A) was then treated with more than two molar equivalents of the Grignard reagent of an appropriately substituted halide, for example, 4-trifluoromethoxyphenyl magnesium bromide, yielding the desired N-(substituted alkyl)-4-[bis(substituted)hydroxymethyl]piperidine (I), for example, N-(4-methoxyphenylmethyl)-4-[bis(4-trifluoromethoxyphenyl)-hydroxymethyl]p iperidine (Compound 1). Example 1 provides a detailed description of how these reactions are conducted.
Another method, again for cases where R.sup.1 and R.sup.2 are the same, is shown in Schema 2. In this method ethyl piperidin-4-ylcarboxylate is reacted with diethyl carbamoyl chloride, under basic conditions, affording the corresponding intermediate, ethyl N-diethylaminocarbonylpiperidin-4-ylcarboxylate (B). Intermediate (B) is treated with more than two molar equivalents of the Grignard reagent of an appropriately substituted halide, yielding the corresponding N-diethylaminocarbonyl-4-[bis(substituted phenyl or pyridyl)hydroxymethyl]piperidine (C). Intermediate (C) is then treated with lithium aluminum hydride, affording the 4-[bis(substituted phenyl or pyridyl)hydroxymethyl]piperidine (II), for example, 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. As depicted in Schema 2a, i
REFERENCES:
patent: 3920442 (1975-11-01), Albert et al.
patent: 4632925 (1986-12-01), Mullin et al.
Ali Syed F.
Cohen Daniel H.
Cullen Thomas G.
Henrie II Robert N.
Lyga John W.
Chang Ceila
FMC Corporation
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