US 5,008,261 AGrant
Agents for Repelling Insects and Mites
Issue Date:1991-04-16
•4 Claims
Abstract
It has been found that the substituted .alpha.,.omega.-amino-alcohol derivatives, some of which are known, of the formula I ##STR1## in which X represents hydrogen, COR.sup.11, COOR.sup.12 or R.sup.13, and wherein have a powerful insect- and mite-repelling action (repellent action). R.sup.1 represents optionally substituted alkyl, alkenyl or alkinyl radicals R.sup.2, R.sup.11, R.sup.12 and R.sup.13 are identical or different and represent optionally substituted alkyl or alkenyl radicals, R.sup.3 to R.sup.10 are identical or different and represent hydrogen, or represent optionally substituted alkyl radicals, R.sup.2 and R.sup.3 or R.sup.3 and R.sup.7 or R.sup.3 and R.sup.5 or R.sup.5 and R.sup.7, together with the atoms to which they are bonded, can also form an optionally substituted monocyclic ring, and n and m are identical or different and denote 0 or 1, with the proviso that X does not represent hydrogen or R.sup.13 if n and m represent 0,
Metadata
Assignee
- Bayer Aktiengesellschaft
Inventors
- Bernd-Wieland Kruger
- Klaus Sasse
- Franz-Peter Hoever
- Gunther Nentwig
- Wolfgang Behrenz
Application Information
Application Number:US 4230701
Filing Date:1989-10-18
Priority Date:1987-04-28
Art Unit:123
Classifications
IPC:
C07D21122A01N 4340
Field of Search:
546548540514564560562245;226531608212;315;423;330;625;626;578;919193;197;203160155
Patent Drawings
This patent does not have any drawings.
Description
PREPARATION EXAMPLES
EXAMPLE 1 ##STR36## 1-(8utoxycarhonyl)-2-(2-hydroxyethyl)-piperidine
6.5 g (0.05 mol) of 2-(2-hydroxyethyl)-piperidine and 10 ml of triethylamine are dissolved in 300 ml of tetrahydrofuran, and 7.5 g (0.55 mol) of butyl chloroformate are added at -20.degree. C.
The mixture is stirred at 20.degree. C. for 24 hours and then extracted with methylene chloride/water. After the organic phase has been dried using magnesium sulphate, the solvent is distilled off in vacuo and the residue is then distilled in a bulb tube oven.
Yield: 5.6 g (=49% of theory)
Boiling point (bulb tube): 120.degree.-130.degree. C./0.25 mbar
EXAMPLE 2 ##STR37## 1-(t-Butoxycarbonyl)-2-(2-methoxyethyl)-piperidine
1.1 ml of a % strength butyllithium solution in hexane are added to 0.5 g of 1-(t-butoxycarbonyl)-2-(2-hydroxyethyl)-piperidine (0.002 mol) in 50 ml of tetetra-hydrofuran at -78.degree. C.
The mixture is heated at 20.degree. C. for 1 hour and at 40.degree. C. for 4 hours and cooled to 20.degree. C., and 5 ml of methyl iodide (0.08 mol) are added to the reaction mixture. The mixture is heated at 40.degree. C. for a further 24 hours and is then poured onto 300 ml of ice-water. It is then extracted several times with methylene chloride. After the organic phase has been dried using magnesium sulphate and the solvent has been distilled off, the residue is chromatographed on about 200 g of silica gel (mobile phase: hexane : ethyl acetate =7:3). After the solvent has been distilled off, 0.3 g (=62% of theory) of 1-(butoxycarbonyl)-2-(2-methoxyethyl)piperidine is obtained with a refractive index n.sub.D.sup.20 of 1.4613.
EXAMPLE 3 ##STR38##
26 g (0.2 mol) of 1-amino-3-methoxycyclohexane and 35 ml of triethylamine (0.25 mol) are dissolved in 500 ml of tetrahydrofuran, and 30 ml (0.24 mol) of butyl chloroformate are added at 20.degree. C. The mixture is stirred at 20.degree. C. for 1 day, the solid is filtered off, the solvent is distilled off, the residue is taken up in methylene chloride and the mixture is filtered over silica gel. Renewed distillation of the solvent gives 36 g (78% of theory) of 1-(N-butoxycarbonyl-)amino-3-methoxycyclohexane.
For further reaction, 11.5 g (0.05 mol) of this compound are dissolved in 150 ml of tetrahydrofuran, and 2.2 g (0.073 mol) of sodium hydride (80% strength in paraffin) are added at 20.degree. C. The mixture is heated under reflux for 4 hours and 10 ml (0.16 mol) of methyl iodide are then added to the reaction mixture at 20.degree. C. The mixture is heated under reflux for 1 hour, 50 ml of ammonium chloride solution are first added, followed by methylene chloride/water, the organic phase is dried using magnesium sulphate and the solvent is distilled off. The residue is then filtered over silica gel with hexane : acetone=1:1. 8.4 g (69% of theory) of 1-(N-butoxycarbonyl-N-methyl)-3-methoxycyclohexane with a refractive index n.sub.D.sup.20 of 1.4632 are obtained.
The following compounds are obtained analogously:
Preparation of compounds of the general formula (VIII) N-Butylamino-propanol-1,3
48 g (0.5 mol) of 1,3-dichloropropanol are added to 500 ml of butylamine and 1 g of potassium iodide and the mixture is heated under reflux for 2 days. It is then extracted with methylene chloride/water, the organic phase is dried using magnesium sulphate and concentrated on a rotary evaporator, and the residue is distilled. 52 g (=79% of theory) of N-butylamino-propanol-1,3 with a boiling point: bp. 125.degree. C./30 mbar are obtained.
Claims
We claim:
1. An insect and mite repellant composition comprising an effective amount of at least one substituted .alpha.,.omega.-aminoalcohol derivative of the formula (I) ##STR42## in which X represents hydrogen, COR.sup.11, COOr.sup.12 or R.sup.13, R.sup.1 represents an optionally substituted alkyl, alkenyl or alkinyl radical, R.sup.2, R.sup.11, R.sup.12 and R.sup.13 are identical or different and represent an optionally substituted alkyl or alkenyl radical, R.sup.3 to R.sup.10 are identical or different and represent hydrogen, or represent an optionally substituted alkyl radical, substituents in the case of said optionally substituted alkyl, alkenyl, and alkinyl radicals being selected from the group consisting of alkyl, cycloalkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, and cyano, and wherein R.sup.2 and R.sup.3 or R.sup.3 and R.sup.7 or R.sup.3 and R.sup.5 or R.sup.5 and R.sup.7, together with teh atoms to which they are bonded, can also form a 5 to 7-membered saturated monocyclic ring which is unsubstituted or substituted by alkyl, and n and m are identical or different and denote 0 or 1, with the proviso that X does not represent hydrogen or R.sup.13 if n and m represent 0.
2. An insect and mite repellant composition according to claim 11, in which X represents hydrogen, COr.sup.11 or R.sup.13, R.sup.1 represents C.sub.1 -C.sub.7 -alkyl, C.sub.3 -C.sub.7 -alkenyl or C.sub.2 -C.sub.7 -alkinyl, R.sup.2, R.sup.11 and R.sup.13 are identical or different and represent C.sub.1 -C.sub.5 -alkyl, R.sup.4 -R.sup.8 are identical or different and represent hydrogen or C.sub.1 -C.sub.6 -alkyl, and wherein R.sup.2 and R.sup.3 or R.sup.3 and R.sup.7 or R.sup.3 and R.sup.5 and R.sup.5 or R.sup.5 and R.sup.7, together with the atoms to which they are bonded, can also form a 5- or 6-membered saturated monocyclic ring, and n represents 1 and m represents 0.
3. In a method of repelling insects and mites the improvement wherein the insect and mite repellent composition comprises at least one substituted .alpha.,.omega.-aminoalcohol derivative of the formula (I) ##STR43## in which X represents hydrogen, COR.sup.11, COOR.sup.12 or R.sup.13, R.sup.1 represents an optionally substituted alkyl, alkenyl or alkinyl radical, R.sup.2, R.sup.11, R.sup.12 and R.sup.13 are identical or different and represent an optionally substituted alkyl or alkenyl radical, R.sup.3 to R.sup.10 are identical or different and represent hydrogen, or represent an optionally substituted alkyl radical, substitutents in the case of said optionally substituted alkyl, alkenyl, and alkinyl radicals being selected from the group consisting of alkyl, cycloalkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, and cyano, and wherein R.sup.2 and R.sup.3 or R.sup.3 and r.sup.7 or r.sup.3 and R.sup.5 and R.sup.7, together with the atoms to which they are bonded, can also form a 5 to 7-membered saturated monocyclic ring which is unsubstituted or substituted or substituted by alkyl, and n and m are identical or different and denote 0 or 1, with the proviso that X does not represent hydrogen or R.sup.13 if n and m represent 0.
4. An insect and mite repellant composition according to claim 1, further comprising a suitable extender or carrier.
Non-Patent Literature (2)
- Chemical Abstracts, vol. 103, Abstract 141,568y, p. 686 (1985).
- Coward et al., J. Org. Chem., 38(14), 2546-2548 (1973).