JPS63201179A - 2-aminomethyltetrahydrofurans - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to new 2-aminomethyltetrahydrofurans, several processes for their preparation, and their use as pesticides.

Certain aminomethyltetrahydrofurans, e.g.
-(4-chlorophenyl)-5-(3゜5-dimethylpiperidin-1-yl-methyl)-tetrahydrofuran,
It has already been disclosed that it has bactericidal and fungicidal properties () Itsu Publication Specification 3, 4
13,996).

However, the activity of these hitherto known compounds was not completely satisfactory in all fields of application, especially at low application rates and concentrations.

General formula CI) [wherein R1 is in each case optionally substituted aryl, heteroaryl, cycloalkyl, tetrahydros
methyl or decahydronaphthyl, R1 represents hydrogen or methyl, and R1 and R
4 is, independently of each other, hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, dialkoxyalkyl, hydroxyalkyl, hydroxyalkoxyalkyl, dioxanylalkyl, oxolanylalkyl, dioxanylalkyl, or each represent optionally substituted cycloalkylalkyl, cycloalkyl, aralkyl, aralkenyl or aryl, or R3 and R4, together with the nitrogen atom to which they are attached, optionally represent [Representing an optionally substituted saturated heterocyclic ring which may contain a heteroatom]] and their plant-friendly acid-addition salts have been discovered. .

The compounds of formula (I) can also exist as geometric and/or optical isomers or as isomeric mixtures of varying composition. Pure isomers and isomer mixtures are also claimed according to the invention.

General formula CI) M'' [wherein R1 represents optionally substituted aryl, heteroaryl, cycloalkyl, decahydronaphthyl or tetrahydronaphthyl; Rs and R
' are, independently of each other, in each case mohydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, sialfukidialkyl, hydroxyalkyl, hydroxyalkoxyalkyl, dioxanylalkyl, oxolanylalkyl, dioxanylalkyl/lz , or in each case optionally substituted cycloalkylalkyl,
Cycloalkyno stands for aralkyl, aralkenyl or aryl, or R1 and R4, together with the nitrogen atom to which they are attached, may optionally contain another heteroatom. representing a saturated heterocyclic ring which may be an optional saturated heterocyclic ring] and their plant-friendly acid-addition salts, their geometric and/or optical isomers, and / or isomer mixtures comprising (a) substituted tetrahydrofurans of the formula (IF) in which R18 and R2 have the meanings given above and Xi represents an electron-withdrawing radical; when reacting with amines of the formula in which R3 and R6 have the meanings given above, optionally in the presence of a diluent and optionally an acid binder, or (b) process Ca') and/or or (C) of formula (Ia) in which R1, R1 and R3 have the abovementioned meanings, optionally in the presence of a diluent and optionally an acid binder. In the presence of the formula (IV) , oxolanylalkyl, dioxanylalkyl, or in each case optionally substituted cycloalkylalkyl, cycloalkyl, aralkyl or aralkenyl, and x2 represents an electron-withdrawing radical. (c) when reacting with a curing agent, or (c) method (a)
) obtained by formula (Ib) [wherein R1-1 represents an optionally substituted aryl, R2 represents hydrogen or methyl, R3-1 and R4-! are, independently of each other, in each case hydrogen, alkyl, alkoxyalkyl, dialkoxyalkyl, hydroxyalkyl, hydroxyalkoxyalkyl, dioxolanylalkyl, oxolanylalkyl, dioxanylalkyl, or in each case optionally substituted cycloalkyl, cycloalkylalkyl, aralkyl or aryl, or R3-1 and R4-1, together with the nitrogen atom to which they are attached, optionally represent another heteroatom represents an optionally substituted saturated heterocyclic ring which may contain] optionally in the presence of a diluent, optionally in the presence of a catalyst, and optionally under pressure, It has also been found that hydrogenation at the aryl substituent present and, if appropriate, subsequent addition of acid can be obtained.

Finally, the novel 2-aminomethyltetrahydrofurans of general formula (I) have the following properties against pests:
It was also found that it has activity, especially against fungal and fungal pests.

Surprisingly, the 2-aminomethyltetrahydrofurans of general formula (I) are chemically and with respect to their activity similar compounds to the aminomethyltetrahydrofurans known from the prior art, such as 2-(4-chlorophenyl)- 5-(3,5-dimethylpiperidin-1-yl-methyl)-tetrahydrofuran, showing better bactericidal and fungicidal activity.

Formula (I) provides a general definition of 2-aminomethyltetrahydrofurans according to the invention. Preferred compounds of formula (I) are those in which R1 represents phenyl, optionally mono- or polysubstituted by the same or different substituents, where suitable substituents are halogen, cyano, nitro, in each case The number of carbon atoms is 1-6 in each case, linear or branched.
and optionally having 1 to 9 identical or different halogen atoms, alkyl, alkoxy, alkylthio,
halogenoalkyl, halogenoalkoxymodi, halogenoalkylthio, amino, in each case linear or branched, in each case 1-4 carbon atoms in each alkyl moiety;
alkylamino, dialkylamino or alkoximinoalkyl, and R1 in each case represents σ-naphthyl or β-naphthyl optionally optionally mono- or polysubstituted with the same or different substituents, where appropriate The substituents are halogen, linear or branched alkyl or alkoxy having 1 to 4 carbon atoms in each case, and R1 is optionally monosubstituted with the same or different substituents in each case. represents a cycloalkyl group having 3 to 7 carbon atoms which may be optionally substituted or polysubstituted, in which suitable substituents are linear or branched cycloalkyl groups having 1 to 6 carbon atoms in each case, and optionally Alkyl, alkoxy, having 1-9 identical or different halogen atoms,
Halogenoalkyl or halogenoalkoxy,
Furthermore, R1 represents tetrahydros-7tyl or decahydronaphthyl, which may optionally be mono- or polysubstituted with the same or different substituents in each case;
Suitable substituents for the hydrogenated rings here are alkyl and alkoxy having 1 to 6 carbon atoms, in each case linear or branched, and furthermore suitable substituents for the aromatic rings are halogens. , and finally R1 in each case carries 1 or 2 heteroatoms, in particular nitrogen, oxygen or sulfur, which may optionally be mono- or polysubstituted by the same or different substituents. represents a membered heteroaryl radical, in which suitable substituents are in each case alkyl having 1 to 6 carbon atoms and/or halogen, R1 is hydrogen or methyl, and R3 and R
1 is, independently of each other, hydrogen in each case, linear or branched alkyl having 1 to 12 carbon atoms, alkenyl having 3 to 8 carbon atoms, alkynyl having 3 to 8 carbon atoms, hydroxyalkyl having 2 to 6 carbon atoms, in each case alkoxyalkyl or dialkoxyalkyl having 1 to 8 carbon atoms, or hydroxyalkoxyalkyl having 2 to 8 carbon atoms in the individual alkyl moiety; in each case straight chain or branched dioxanylalkyl, oxolanylalkyl or dioxanylalkyl having 1-4 carbon atoms in the alkyl moiety in each case, or 3-7 carbon atoms in the cycloalkyl moiety in each case and the number of carbon atoms in the linear or branched alkyl moiety is 1, as appropriate.
-4 and in each case represents cycloalkyl or cycloalkylalkyl which may be optionally mono- or polysubstituted in the cycloalkyl moiety by the same or different substituents, where the appropriate substituents are in each case halogen, in each case straight-chain or branched alkyl, alkoxy, halogenoalkyl or halogenoalkoxy, in each case with 1=6 carbon atoms and, where appropriate, from 1 to 9 identical or different halogen atoms; and R3 and R4 have 6 to 10 carbon atoms in the aryl moiety and up to 6 carbon atoms in the optional straight-chain or branched alkyl or alkenyl moiety, and in each case are optionally substituted with the same or different represents arylalkyl, arylalkenyl or aryl which may be mono- or polysubstituted by a group, where suitable substituents are halogen, cyano, nitro, linear or branched in each case; and alkyl having from 1 to 6 carbon atoms in the individual alkyl moieties and optionally from 1 to 9 identical or different halogen atoms;
alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or alkoximinoalkyl, or R3 and R4 together with the nitrogen atom to which they are attached optionally represent another heteroatom, especially nitrogen , oxygen or sulfur, optionally substituted 5- to 7-membered heterocyclic rings, in which suitable substituents are in each case straight-chain or branched. is an alkyl or hydroxyalkyl having 1 to 4 carbon atoms.

Particularly preferred compounds of formula (I) are those in which R1 represents phenyl, optionally mono-, di- or trisubstituted in each case with the same or different substituents, where suitable substituents include fluorine; , chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-1i-1S- or t-butyl, n- or i-pentyl, n- or i-hexyl, methoxy, ethoxy , L-butoxy, trifluoromethyl, trifluoromethylthio, trifluoromethoxy, methoximinomethyl, dimethylamino and diethylamino, and R1 is optionally mono-, di- or tri-substituted in each case by the same or different substituents. a that may be substituted
-su7tyl or β-su7tyl, where suitable substituents are fluorine, chlorine, bromine, iodine, methyl, ethyl,
n- or i-propyl, n-1i-1S- or t-butyl, methoxy and ethoxy, even if R1 is optionally mono-, di- or tri-substituted in each case by the same or different substituents; cyclopentyl or cyclohexyl, in which suitable substituents are in each case methyl, ethyl, n- or i-propyl, n-1i-1S- or t-butyl,
n- or i-pentyl, methoxy, ethoxy, t-
butoxy, trifluoromethyl and difluoromethoxy, furthermore R1 in each case represents tetrahydros-7tyl optionally optionally mono-, di- or tri-substituted by the same or different substituents, where appropriate substitutions are made. The radicals are fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-1i-1S- or L-butyl, methoxy and ethoxy, in addition R1 in each case optionally being the same or different substituents. represents decahydronaphthyl which may be mono-, di- or trisubstituted, where suitable substituents are methyl, ethyl, n- or i-propyl, n-1i-
1S- or t-butyl, methoxy and ethoxy, and R1 may optionally be mono-, di- or tri-substituted in each case with the same or different substituents.
-53- or 4-pyridyl and 2- or 3-
represents chenyl, where suitable substituents are in each case fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-1i-1S- and L-butyl, and in which R2 is hydrogen or methyl and R3 and R
4 are, independently of each other, in each case hydrogen, methyl, ethyl, -n- or i-propyl, n-1i-1s- or t-butyl, n- or i-hentyl, n- or i-hexyl, n- or i-heptyl, n-
or i-octyl, allyl, n- or i-butenyl, n- or i-pentenyl, propargyl, n
- or i-butynyl, hydroxyethyl, hydroxypropyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, butoxypropyl, hydroxyethyldiethyl, dimethoxyethyl, dimethoxypropyl, jetoxyethyl , dioxanylethyl, dioxanylethyl, oxolanylmethyl, oxolanylethyl, dioxanylmethyl, dioxanylethyl, or in each case optionally monosubstituted or disubstituted with the same or different substituents. represents optionally substituted or trisubstituted cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl, in each case suitable substituents being fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-1i-1S- or L-butyl substituents, or in each case optionally mono-, di- or tri-substituted by the same or different substituents; represents phenyl, benzyl or phenylethyl which may be fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i
-propyl, n-1i-1S- or L-butyl, methoxy, ethoxy, methylthio, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl or methoximinomethyl, or R3 and R4 are Together with the nitrogen atom, it represents a heterocyclic ring of the formula, in which suitable substituents are in each case methyl, ethyl or hydroxymethyl.

In addition to the compounds mentioned in the Preparation Examples, the following 2-aminomethyltetrahydrofurans of the general formula (I) may be mentioned individually: NH(CHz)z-0-(CHi)z-O
For example, when using 2-bromomethyl-4-cyclohexyltetrahydro7rane and piperidine as starting materials, the reaction steps of process (a) according to the invention can be represented by the following reaction scheme.

For example, 2-cyclohexylaminomethyl-4-[4-
When using tert-butylcyclohexyl]-tetrahydrofuran and allyl bromide as starting materials, the reaction steps of process (b) according to the invention can be represented by the following reaction scheme.

(Base) For example, 2-(morpholin-4-yl-methyl)-4-
If (4-tert-butylphenyl)-tetrahydrofuran is used as starting material and hydrogen is used as hydrogenating agent, the reaction steps of process (C) according to the invention can be represented by the following reaction scheme: .

Formula (II) provides a general definition of the substituted tetrahydrofurans required as starting materials for carrying out process (a) according to the invention.

In this formula (TI), R1 and R2 preferably represent the groups already mentioned as being suitable for these substituents in connection with the description of the substances of formula (I) according to the invention.

XI preferably represents halogen, especially chlorine or bromine, or in each case optionally substituted alkylsulfonyloxy or arylsulfonyloxy, such as methanesulfonyloxy or p-toluenesulfonyloxy.

Are substituted tetrahydrofurans of formula (Il) known (e.g. European Publication 68°331 and The Journal of Organic Chemistry (J, Org, Chem), 49(9), 1)?
557-59) or by generally known methods, such as those of the formula (V) represents an optionally substituted aryl], for example by hydrogenation, at a temperature between -20°C and +80°C, optionally in the presence of a diluent such as diethyl ether. By reacting with a reducing agent such as aluminum lithium, the formula 1 thus obtained is
) in which RI and R2 have the meanings given above are then treated with e.g. or by general universal methods, such as reaction with hydrogen peroxide/formic acid, to form a compound of the formula (■) H in which R1 and R1 have the meanings given above. The hydroxy compound is converted to the hydroxy compound and this is heated between -10°C and 1°C, optionally in the presence of a diluent such as toluene, either in situ or after isolation of the intermediate by commonly known methods.
reacted with a water-removing agent such as sulfuric acid at a temperature between 20°C and the formula (■) thus obtained
RI R* [wherein R1 and R2 have the above meanings] is then optionally in the presence of a diluent such as dichloromethane and optionally an acid binder such as pyridine. , a common halogenating agent such as tribromide or the formula (II
) R' S O2-Ha l (II
) [wherein R'' represents in each case optionally substituted alkyl or aryl, in particular metinopetrifluoromethyl or p-tolyl, and Hal represents halogen, in particular chlorine, bromine or iodine. ] It can be obtained by the method of reacting with generally known sulfonyl halides.

Formula 1) gives a general definition of the additional amines required as starting materials for carrying out process (a) according to the invention. In this formula (III) Hz and R4 preferably represent the groups already mentioned as being suitable for these substituents in connection with the description of the substances of formula (I) according to the invention.

Amines of formula (II[) are generally known organic chemical compounds.

Formula (Ia) provides a general definition of the aminomethyltetrahydrofurans required as starting materials for carrying out process (b) according to the invention. This formula (Ia)
RI, R2 and R3 preferably represent the groups already mentioned as being suitable for these substituents with respect to the description of the substances of formula CI) according to the invention.

The aminomethyltetrahydrofurans of formula (I a) are compounds according to the invention and the process according to the invention (
Obtained by a).

Formula (IV) provides a general definition of the additional alkylating agents required as starting materials for carrying out process (b) according to the invention. In this formula (IV), R
'-' is preferably a linear or branched alkyl having 1 to 12 carbon atoms, alkenyl having 3 to 8 carbon atoms, alkynyl having 3 to 8 carbon atoms, or 2 to 6 carbon atoms. hydroxyalkyl, each alkyl moiety having 1-6 carbon atoms
alkoxyalkyl, dialkoxyalkyl or hydroxyalkoxyalkyl; in each case dioxanylalkyl, oxolanylalkyl or dioxanylalkyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, or In each case the number of carbon atoms in the cycloalkyl moiety is 3-7 and optionally in the straight or branched alkyl moiety the number of carbon atoms is 1-4 and in each case optionally the same in the cycloalkyl moiety. or cycloalkyl or cycloalkylalkyl which may be mono- or polysubstituted with different substituents, where suitable substituents are halogen in each case, carbon in each case linear or branched chain. number is 1
-4 and optionally has 1 to 9 identical or different halogen atoms, and is t6 alkyl, alkoxy, halogenoalkyl or halogenoalkoxy, and further has a carbon number of 6 to 10 in the aryl moiety and is optionally straight or branched. represents an arylalkyl or arylalkenyl in which the number of carbon atoms in the branched alkyl or alkenyl moiety is up to 6 and which may optionally be mono- or polysubstituted in each case with the same or different substituents; The substituents are in each case halogen, cyano, nitro, in each case linear or branched, in each case the number of carbon atoms in the individual alkyl moiety is 1-4 and, as appropriate, 1-9 the same or different. Alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkoxycarbonyl or alkoximinoalkyl having a halogen atom.

R4-1 is particularly preferably methyl, ethyl, n- or 1-propyl, n-1i-1S- or t-butyl,
n- or i-pentyl, n- or i-hexyl, n- or i-heptyl, n- or i-octyl, allyl, n- or i-butenyl, n- or i-pentenyl, propargyl, n- or i -butynyl, hydroxyethyl, hydroxypropyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl, ethoxyethyl, propoxypropyl, butoxypropyl, hydroxyethoxyethyl, dimethoxyethyl, dimethoxypropyl, jetoxyethyl, dioxanyl represents ethyl, dioxanylethyl, oxolanylmethyl, oxolanylethyl, dioxanylmethyl, dioxanylethyl, or in each case is optionally mono- or penta-substituted with the same or different substituents; Cyclopropyl, cyclopropylmethyl, cyclopropylethyl,
cyclopropylpropyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl, in each case suitable substituents being fluorine,
chlorine, bromine, methyl, ethyl, n- or i-propyl, n-1i-1S- or t-butyl, or in each case optionally mono-, di- or tri-substituted by the same or different substituents. represents benzyl or phenylethyl which may be fluorine, chlorine, hydrogen, cyano, nitro, in each case suitable substituents.
Methyl, ethyl, n- or i-propyl, n-1i
-1S- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl or methoximinomethyl.

R4-1 is very particularly preferably methyl, ethyl, n- or i-propyl, n-1i-1S- or t-butyl, n- or i-pentyl, n- or i-hexyl, allyl, n- or i-butenyl, n- or i-pentenyl, propargyl, n- or ]-
Butynyl, hydroxyethyl, hydroxypropyl, methoxyethyl, ethoxyethyl, ethoxypropyl, hydroxyethoxyethyl, dimethoxyethyl, jetoxyethyl, dioxanylmethyl, dioxanylmethyl,
represents dioxanylmethyl, cyclopropylmethyl, dichlorocyclopropylmethyl, dimethylcyclopropylmethyl, dichlorodimethylcyclopropylmethyl, cyclopentyl, cyclohexyl or cyclohexylmethyl; represents iodine or in each case optionally substituted alkylsulfonyloxy, alkoxysulfonyloxy or arylsulfonyloxy, such as methanesulfonyloxy, methoxysulfonyloxy or p-++-luenesulfonyloxy.

The alkylating agents of formula (■) are generally known organic chemical compounds or can be obtained analogously to generally known methods.

Formula (Ib) provides a general definition of the substituted aminomethyltetrahydro7ranes required as starting materials for carrying out process (c) according to the invention.

In this formula (Ib), R1-1 preferably represents phenyl which may optionally be mono- or polysubstituted with the same or different substituents, and suitable substituents here include halogen, cyano, nitro, etc. alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, in each case linear or branched, having 1 to 6 carbon atoms and optionally 1 to 9 identical or different halogen atoms; amino, in each case linear or branched, alkylamino, dialkylamino or alkoximinoalkyl having 1 to 4 carbon atoms in the individual alkyl moiety, and optionally the same or different in each case; represents α-naphthyl or β-naphthyl which may be mono- or polysubstituted by substituents, where suitable i substituents are halogen, in each case linear or branched chain, having 1 carbon number in each case; -4 alkyl or alkoxy, further R2 represents hydrogen or methyl, and RN-13 and R4-2 independently of each other are hydrogen, in each case linear or branched, having 1 carbon number; -12 alkyl, hydroxyalkyl having 2-6 carbon atoms, alkoxyalkyl or dialkoxyalkyl having 1-8 carbon atoms in each alkyl moiety, or hydroxy having 2-8 carbon atoms in each alkyl moiety Alkoxyalkyl; in each case linear or branched dioxanylalkyl, oxolanylalkyl or dioxanylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or in each case cycloalkyl moiety the number of carbon atoms in the cycloalkyl moiety is from 3 to 7 and the number of carbon atoms in the optionally linear or branched alkyl moiety is from 1 to 4 and in each case optionally monomer by the same or different substituents in the cycloalkyl moiety. Represents cycloalkyl or cycloalkylalkyl which may be substituted or polysubstituted, where suitable substituents are halogen in each case, linear or branched in each case and having 1 to 4 carbon atoms. and optionally having 1 to 9 identical or different halogen atoms,
alkoxy, halogenoalkyl or halogenoalkoxy, and the number of carbon atoms in the aryl moiety is 6-10 and the number of carbon atoms in the optionally straight-chain or branched alkyl or alkenyl moiety is up to 6, and in each case represents arylalkyl or aryl optionally mono- or polysubstituted with the same or different substituents, where suitable aryl substituents are the above-mentioned cycloalkyl substituents or R3-1 and R4- 2 together with the nitrogen atom to which they are attached preferably optionally another heteroatom,
represents a 5- to 7-membered saturated heterocyclic ring which may contain, in particular, nitrogen, oxygen or sulfur and may optionally be mono- or polysubstituted with the same or different substituents; Suitable substituents are in each case straight-chain or branched alkyl or hydroxyalkyl having from 1 to 4 carbon atoms.

Aminomethyltetrahydroctaranes of formula (Ib) are substances according to the invention and are obtained according to process (a).

Suitable diluents for carrying out processes (a) and (b) according to the invention are inert organic solvents or aqueous systems.

These include in particular aliphatic and aromatic optionally halogenated hydrocarbons, such as benzine, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride. , ethers such as diethyl ether, dioxane, tetrahydroctane or ethylene glycol dimethyl or diethyl ether, ketones such as acetone or butanone, nitriles,
For example, acetonitrile or propionitrile, amides such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, esters,
Included are, for example, ethyl acetate, or sulfoxides such as dimethyl sulfoxide.

Processes (a) and (b) according to the invention can also optionally be carried out in a two-phase system such as water/toluene or water/dichloromethane, optionally in the presence of a phase-transfer catalyst. Examples of such catalysts include: tetrabutylammonium iodide, tetrabutylammonium bromide, tributyl-methylphosphonium bromide, trimethyl-Crs/C+s-alkylammonium chloride, dibenzyldimethyl-ammonium methylsulfate. , dimethyl-〇 It/Cl 4-alkyl-benzylammonium chloride, tetrabutylammonium hydroxide, 15-crown-5,18-crown-6, triethylbenzylammonium chloride and trimethylbenzylammonium chloride. Processes (a) and (b) according to the invention can also be carried out without adding a solvent.

Acid binders suitable for carrying out processes (a) and (b) according to the invention are all commonly used inorganic and organic bases. alkali metal hydroxides, carbonates or bicarbonates, such as sodium hydroxide, sodium carbonate or sodium bicarbonate, or tertiary amines, such as triethylamine, N,N-dimethylaniline, pyridine, 4-(N, N-dimethylamino)-pyridine, diazabicyclooctane (DAB
CO), diazabicyclonone 7 (DBN) or diazabicycloundecene (D B U) are preferably used.

Formula (III) or (Ia) used as reaction precipitant
) can also be used at the same time as acid binder in a suitable excess.

The reactions when carrying out processes (a) and (b) according to the invention can in turn be varied within a relatively wide range. Generally, the process is carried out at a temperature between -20°C and +180°C, preferably at a temperature between 20°C and +150°C.

To carry out process (a) according to the invention, 1.0 per mole of substituted tetrahydro7 run of formula (n)
-3.0 mol, preferably 1.0-1.5 mol of formula 1
) of an amine, and optionally 1.0-3.0 mol, preferably 1.0-1.5 mol, of an acid binder, and optionally 0.1
-1.0 mol of phase-transfer catalyst is used.

To carry out the process (b) according to the invention, 1 mole of aminomethyltetrahydrofuran of formula (Ia)
．． 0-5.0 mol, preferably 1.0-2.0 mol,
1 of the alkylating agent of formula (■) and 1.0-5.0 mol, preferably 1. 0-2.0 mol of acid binder and optionally 0.1-1.0 mol of phase transfer catalyst are used.

The reaction is carried out and the reaction products of formula (I) are worked up and isolated in both cases by customary methods.

Diluents that can be used when carrying out process (C) according to the invention are all solvents which are inert under the hydrogenation conditions. Hydrocarbons such as petroleum ether, pentane, hexane,
heptane and cyclohexane, alcohols such as methanol, ethanol, n-propanol and i-
Proper tools or ethers such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether can be suitably used. However, the process can also be carried out without diluent.

Suitable hydrogenating agents when carrying out process (c) according to the invention are compounds which are also capable of hydrogenating aromatics. Molecular hydrogen is preferably used.

Hydrogenation catalysts that can be used in process (c) according to the invention are all catalysts commonly used for such reactions.

Raney nickel or noble metal catalysts such as palladium, ruthenium, optionally on a suitable support such as charcoal, etc.
Palladium oxide, platinum or platinum oxide are preferably used.

The reactions when carrying out process (c) according to the invention can in turn be varied within a relatively wide range. Generally, the method is carried out at a temperature between 50°C and 250°C, preferably 80°C.
It is carried out at temperatures between -200<0>C.

Process (c) according to the invention can be carried out under atmospheric pressure or under pressure. The process is preferably carried out under pressure in the presence of hydrogen. Generally between 5 and 300 atmospheres, preferably 1
Pressure ratios between 0 and 200 atmospheres are used.

When carrying out process (c) according to the invention, 3.0% per mole of aminomethyltetrahydrofuran of formula (Ib).
0-30 mol of hydrogenating agent and 0.001-0.1 mol, preferably 0.01-0.1 mol of catalyst are generally used.

When carrying out the method (C) according to the invention, the formula (Ib)
is generally carried out in an autoclave, in each case at the desired temperature, with hydrogen in the presence of a diluent. Processing is carried out using conventional methods.

The following acids are suitable for the preparation of acid addition salts of compounds of formula (I): hydrohalic acids, such as hydrochloric acid and hydrobromic acid, especially hydrochloric acid, as well as phosphoric acid, nitric acid, sulfuric acid, -
Mono-, di- and tri-functional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, and sulfonic acids such as p-toluenesulfonic acid and 1.5-naphthalenedisulfonic acid, as well as saccharin.

Acid-addition salts of compounds of formula (I) can be prepared simply by conventional salt-forming methods, e.g. by dissolving compounds of formula (I) in a suitable solvent and adding an acid such as hydrochloric acid. and can be isolated by known methods such as filtration and optionally purified by washing with an inert organic solvent.

The active compounds according to the invention have a strong activity against pests and can be used in practice for controlling unwanted microorganisms. The active compounds are particularly suitable for use as plant protection agents, in particular as fungicides.

In plant protection, the fungicides are used to treat Plasmodiophoromycetes (Plasmodiophoromycetes).
es), Oomycetes, Chytridiomycetes, Zygomycetes, Gygomycetes (A
scomycetes), Basidiomycetes (Basidomycetes)
mycetes), and Deuteromycetes (Deutee
romycetes).

By way of example, but without intending to be limited to, several microorganisms that cause fungal and bacterial diseases that fall under the above synonyms include: Pythium (Pythium)
ium) species, such as Pythium ultimum (Pythi
um ultimum; phytophthora
ophthora) species, such as Phytophthora infestans
tans); Pseudoperonospora (P5eudo
peronospora) species, such as Pseudoperonospora humuli (P.
hun+uli) or Pseudoperonospora cubens (P 5eudoperonospora c
ubense); Plasmopara (Plasmopa)
ra) species, such as Plasmovara vichicola (P la
smopara viticola); Peronospora species, such as Peronospora posi or P-brassicaa;
Erysiphe species, such as Erysiphe gramin
is); Sphaerothec
a) Species, e.g.
erotheca ful 1g1nea); Podosphaera species, such as Podosphaera leucotoricha
a 1eucotricha); Venturia (V
enturia) species, such as V enturia 1naequali
s) ; Pyrenophora species, such as Pyrenophora "teres";
ra tarsS) or P, gramine (P,, g
ramine); (Conidia)
Type: Drechslera,
sy n: Helmintsporium (Helmint)
hosporium) ; Cochliobolus (Coc
hliob.

1us) species, such as Cochliobolus sativus (Coc
hliobolus 5ativus) (Canidia type: D re
chslera).

syn: Helminthosporium (Helminthos)
porium); Uromyce
s) species, Chromyces 0 appendiculatus (U rom
yces appendicutatus; Puccinia species, such as Puccinia recondita
ita); T 1lletia species, such as T 1lletia cari
es) ; U stilago species, such as U stilago nud
a) or Ustilago avenae
avenae); Pellic
ularia) species, such as Pericularia sasakii (P
Pyricularia species, such as Pyricularia oryzas (Pyricularia 5asakii);
oryzae); pusarium
species, such as Fusasium curmorum (Fusariu
m culn + orum); gray mold (B o
trytis) species, such as Potulinas cinerea (B
otrytis cinerea); Septoria (Sept.

ria) species, such as Septoria nodorum (Septria nodorum).
oria nodorum) ; Leptosphaeria (
L eptosphaeria) species, such as L eptosphaeria nodorum
nodorum); Cercospora
ora) species, such as Cercospora canescens (Ce
rcospora canescens; Alternaria species, such as Alternaria brassica (A 1ternaria br);
assicae); and Pseudocercosporella (
For example, Pseudocercosporella herpotrifides (P.
5eudocercosporella herp
otrichoides).

The good tolerability by plants of single active compounds at the concentrations required in controlling plant diseases makes it possible to treat the above-ground parts of plants, the growing stems and seeds, as well as the soil.

The novel active compounds according to the invention can be used to combat cereal diseases, such as Erysiphe graminis.
minis), Septoria nodorum (Septor
ianodorum), Cochliobolus sativus (
Cochliobolus 5ativus) and Pyrenophora teres (Pyricularia o
ryzae) can be used with particular success for pest control. Furthermore, the compounds of formula (I) can be used to treat rice diseases such as Pyricularia oryzae.
It also shows good activity against S. oryzae and broad fungicidal and fungicidal activity in vitro.

Depending on the specific physical/chemical properties, the active compounds may be prepared in the usual formulations, e.g. solutions, emulsions, suspensions, powders, foams, liniments, granules, aerosols, impregnated with the active compounds. Natural and synthetic materials, as well as very fine capsules in polymeric materials and coating compositions, and for use with combustion devices such as canister cartridges, canisters, canisters, coils, etc. formulations,
It can also be changed to ULV cold mist or warm mist.

These formulations are prepared in a known manner, for example by combining the substances with liquid solvents and/or optionally using surfactants, i.e. emulsifiers and/or dispersants and/or blowing agents. It can be manufactured by mixing with solid carriers. When using water as extender, organic solvents can be used as co-solvents, for example.

The following are mainly suitable as liquid solvents:
aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane, or paraffins, for example mineral oil distillates, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water. Suitable liquefied gaseous solvents which are gases at normal temperature and pressure are, for example, halogenated hydrocarbons and aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Solid carriers include, for example, ground natural minerals such as kaolin,
Clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silicic acid, alumina and silicates are suitable. Solid carriers for granules include, for example, crushed and fractionated natural rocks such as calcite, marble,
Pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic powders, and granules of organic substances, such as sawdust, coconut husks, corncobs and tobacco stalks, are suitable. Emulsifiers and/or blowing agents include nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates. and arylsulfonates, as well as albumin hydrolysis products. As a dispersant,
For example, lignin-sulphate waste liquors and methylcellulose are suitable.

Containers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules and latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate can be used in the formulations. Other additives are mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as iron, manganese,
Salts of boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain 0.1-95% by weight, preferably 0.5-95% by weight.
90% by weight of active compound.

The active compounds according to the invention, in their commercially available type formulations and in the use forms prepared from these formulations, are free from other active compounds, such as fungicides, insecticides, It can be present as a mixture with acaricides and herbicides, as well as with fertilizers and growth regulators.

The active compounds can be used as such or in the form of their preparations or in the use forms prepared from them, for example in the form of prepared solutions, suspensions, aqueous solutions, liniments, soluble powders, powders and granules. can. They are used in the customary manner, for example in liquid dispersion, atomization, atomization, granulation, dusting, foam application, brushing, etc. Furthermore, it is also possible to apply the active compounds in an ultra-low-dose manner or to inject the active compound preparations or the active compounds themselves into the soil. Plant seeds can also be treated.

In the partial treatment of plants, the active compound concentration of the use forms can be varied within a substantial range. They are generally between 1-0.0001% by weight, preferably between 0.5 and 0.0001% by weight.
Between 0.001% by weight.

For seed treatment, 0.001-50 per kg of seed light
g, preferably 0.01-Log, of active compound is generally required.

For soil treatment, 0.00001-
An active compound concentration of 0.1% by weight, preferably 0.0001-0.02% by weight is required.

Preparation Examples Example I CI lCl2O, 073 mol) of 2-bromomethyl-4-(
3-chlorophenyl)-tetrahydrofuran and 17
g (0,147 mol) of cis-3°5-dimethylpiperidine were stirred for 16 hours at a bath temperature of 120° C., cooled and added into a mixture of diethyl ether and water,
The organic phase was separated, dried over sodium sulfate, concentrated in vacuo, and the residue was chromatographed on silica gel.

8.3 g (37% of theory) of 2-(3,5-cis-dimethylpiperidin-1-yl-methyl)-4-(3-chlorophenyl)-tetrahydrofuran with refractive index n r:, -1,5548 was gotten.

Preparation of the Starting Compound 46.3 g (0.26 mol) of N-bromosuccinimide are added in portions with stirring to 51 g (0.26 mol) of 2-(3-chlorophenyl)-2-allyl-ethanol. Add to 400 ml of solution in anhydrous chloroform,
In the meantime the reaction mixture was to be warmed to 40°C. After the addition was complete, the mixture was stirred at room temperature for 16 hours, washed twice with water, dried over sodium sulfate, and the solvent was removed in vacuo.

47 g (66% of theory) of 2-bromomethyl-4-(
3-chlorophenyl)-tetrahydro7rane is obtained,
and it was directly subsequently reacted without purification and isolation.

6 g (0,15 mol) of lithium aluminum hydride in portions and 76 g (0,32 mol) of 2-(3-chlorophenyl)-2-allyl-ethyl acetate in 250 mG
in anhydrous ether, the mixture was then stirred at reflux temperature for 16 hours, and then hydrolyzed using prepared ammonium chloride solution. The organic phase was separated, dried over sodium sulphate and the solvent was removed in vacuo.

51 g (81% of theory) of 2-(3-chlorophenyl)-2-allyl-ethanol (IR: 3200-330
0) was obtained and was directly subsequently reacted without purification and isolation.

01 CHz -CH= CHt l 50 g of concentrated 1iIE acid are added dropwise to a solution of 114 g (0,597 mol) of 2-allyl-3-chlorophenylacetonitrile in 150 mQ of ethanol and after the addition is complete the mixture is heated to 110 °C. Stirred at bath temperature for 16 hours. After cooling, the mixture was poured onto ice and extracted with petroleum ether. The organic phase was washed with sodium bicarbonate solution until neutral, dried over sodium sulfate and the solvent was removed in vacuo. The residue was distilled in vacuo.

The boiling point of 84g (59% of the theoretical value) is 120℃10.11
-Ethyl 2-allyl-3-chlorophenylacetate was obtained.

28.7 g (I mol) of sodium hydride (80%) is cooled in portions to 151 g (I mol) at 0°C.
of 3-chlorobenzyl cyanide in 500 mff of dimethylformamide while the temperature was maintained at between 0°C and 10°C by cooling. Upon completion of hydrogen evolution, 122 g (1 mol) of allyl bromide were added dropwise at a temperature of 30° C., and the mixture was then stirred for a further 16 hours at 45° C. The reaction mixture was diluted with water and extracted with ether. The organic phase was dried over sodium sulfate, the solvent was removed, and the residue was distilled in vacuo.

The boiling point of 114g (60% of theoretical value) is 91-95℃10
．． 1 Torr of 2-allyl-3-chlorophenylacetonitrile was obtained.

In a similar manner and according to the general information on preparation, the following 2-aminomethyltetrahydrofurans of general formula (I) were obtained:
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■? 'Q?
V) To Lotto
to ey ev
C%Jz × Q E
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×Use Examples In the use examples below, the following compounds were used as comparison substances: 2-(4-chlorophenyl)-5-(3,5-dimethylpiperidin-1-yl-methyl)- Tetrahydrofuran (cf. DE 3,413,996).

Example A Erys 1phe test (barley)/protective solvent 210
0 parts by weight of dimethylformamide emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent and the above amount of emulsifier. , and the concentrate was diluted with water to the desired concentration.

To test the protective activity, young plants were sprayed with the active compound preparation until dripping wet. After the spray coating has dried, the plants are coated with Erysiphe gramis f, s.
P. hordei (Erysiphe gramini5
hordei).

To encourage powdery mildew pus growth, plants should be
It was placed in a greenhouse at a temperature of 0° C. and a relative atmospheric humidity of approximately 80%.

Evaluation was performed 7 days after inoculation.

In this test, for example Preparation Example 3.4.9 and lO
Compounds according to the present invention showed clearly superior activity compared to the prior art.

Table A Erys 1phe-Test (Barley) Protection Example B Pyricularia Test (Rice)/Protection Solvent: 12
．． To prepare a suitable formulation of 5 parts by weight of acetone emulsifier and 0.3 parts by weight of alkylaryl polyglycol ether active compound, 1 part by weight of active compound is mixed with the above amount of solvent and the above amount of emulsifier; The concentrate was then diluted with water to the desired concentration.

To test the protective activity, young plants were sprayed with the active compound preparation until dripping.

After the spray coating has dried, the plants are coated with Pyricularia oryzae.
inoculated with an aqueous spore suspension. The plants were then placed in a greenhouse at 100% relative atmospheric humidity and 25°C.

Disease infection was evaluated 4 days after inoculation.

In this test, the compounds according to Preparation Examples 5.6 and 8, for example, showed clearly superior activity compared to the prior art.

Table B Pyricularia test (rice) Protection Example C Pyricularia test (rice)/systemic solvent: 12.5 parts by weight of acetone emulsifier 20.3 parts by weight of alkylaryl polyglycol ether of the active compound To prepare the formulations, 1 part by weight of active compound is mixed with the above amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test the systemic activity, a preparation of 400+1 active compounds was liquid sprayed onto a standard soil in which young plants were growing. Seven days after treatment, plants were inoculated with Pyricularia oryzae.
inoculated with an aqueous spore suspension. The plants were then placed in a greenhouse at a temperature of 25° C. and 100% relative atmospheric humidity until they were evaluated.

Disease infection was evaluated 4 days after inoculation.

In this test, the compounds according to Preparation Examples 5.6 and 8, for example, showed clearly superior activity compared to the prior art.

Table C

Claims (1)

[Claims] 1. General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) [In the formula, R^1 is optionally substituted aryl, heteroaryl, cycloalkyl, tetrahydronaphthyl or decahydronaphthyl; R^2 represents hydrogen or methyl; and R^3 and R^4, independently of each other, in each case hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl; , dialkoxyalkyl, hydroxyalkyl, hydroxyalkoxyalkyl, dioxolanylalkyl, oxolanylalkyl, dioxanylalkyl, or in each case optionally substituted cycloalkylalkyl, cycloalkyl, aralkyl, aralkenyl or R^3 and R^4 may represent aryl or optionally substituted, and together with the nitrogen atom to which they are attached, may optionally contain another heteroatom 2-aminomethyltetrahydrofurans representing a saturated heterocyclic ring, acid-addition salts thereof, geometric and optical isomers thereof,
and isomeric mixtures thereof. 2. In formula (I), R^1 represents phenyl which may be optionally mono- or polysubstituted with the same or different substituents,
Suitable substituents here include halogen, cyano, and nitro, in each case linear or branched, and in each case having 1-carbon number.
6 and optionally having 1 to 9 identical or different halogen atoms, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, amino, in each case straight-chain or branched, in each case individual The number of carbon atoms in the alkyl moiety is 1
-4 alkylamino, dialkylamino or alkoximinoalkyl, and R^1 in each case represents α-naphthyl or β-naphthyl which may be optionally mono- or polysubstituted with the same or different substituents; , where suitable substituents are halogen, in each case linear or branched, and in each case having 1 to 4 carbon atoms.
is alkyl or alkoxy, and R^1 in each case represents cycloalkyl having 3 to 7 carbon atoms, which may be optionally mono- or polysubstituted with the same or different substituents, where appropriate substitution The group is in each case linear or branched and in each case has 1 to 6 carbon atoms.
and optionally is alkyl, alkoxy, halogenoalkyl or halogenoalkoxy having 1 to 9 identical or different halogen atoms, and R^1 is optionally mono- or polysubstituted in each case with the same or different substituents. represents tetrahydronaphthyl or decahydronaphthyl which may be hydrogenated, in which suitable substituents for the hydrogenated ring are straight-chain or branched alkyl and alkoxy having from 1 to 6 carbon atoms in each case; Furthermore, suitable substituents for aromatic rings are halogen and R^1 furthermore carries in each case 1 or 2 heteroatoms, which may optionally be mono- or polysubstituted by the same or different substituents. represents a 5- or 6-membered heteroaryl radical, in which suitable substituents are in each case alkyl having 1 to 6 carbon atoms and/or halogen, R^2 is hydrogen or methyl, and R ^3 and R^4 are, independently of each other, hydrogen in each case, linear or branched alkyl having 1 to 12 carbon atoms, alkenyl having 3 to 8 carbon atoms, or alkynyl having 3 to 8 carbon atoms, hydroxyalkyl having 2 to 6 carbon atoms, alkoxyalkyl or dialkoxyalkyl having 1 to 8 carbon atoms in each case, or hydroxyalkoxyalkyl having 2 to 8 carbon atoms in the individual alkyl moiety; ; in each case linear or branched dioxolanylalkyl, oxolanylalkyl or dioxanylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or in each case in the cycloalkyl moiety; having 3 to 7 carbon atoms and 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, as appropriate, and in each case optionally monosubstituted or substituted with the same or different substituents in the cycloalkyl moiety; represents optionally polysubstituted cycloalkyl or cycloalkylalkyl, where suitable substituents are in each case halogen, in each case linear or branched, and in each case having 1 to 4 carbon atoms; And as appropriate 1-
Alkyl, alkoxy, halogenoalkyl or halogenoalkoxy having 9 same or different halogen atoms, and R^3 and R^4 have 6-1 carbon atoms in the aryl moiety.
0 and where appropriate the number of carbon atoms in the straight-chain or branched alkyl or alkenyl moiety is up to 6 and in each case optionally mono- or polysubstituted by the same or different substituents; , arylalkenyl or aryl, in which suitable aryl substituents are in each case halogen, cyano, nitro, in each case straight-chain or branched, in each case in which the number of carbon atoms in the individual alkyl moiety is 1- 6 and optionally is alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or alkoximinoalkyl having 1 to 9 identical or different halogen atoms. Methyltetrahydrofurans, their acid-addition salts, their geometric and optical isomers, and their isomeric mixtures. 3. In formula (I), R^1 represents phenyl which may be optionally mono- or polysubstituted with the same or different substituents,
Suitable substituents here include halogen, cyano, and nitro, in each case linear or branched, and in each case having 1-carbon number.
6 and optionally having 1 to 9 identical or different halogen atoms, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, amino, in each case straight-chain or branched, in each case individual The number of carbon atoms in the alkyl moiety is 1
-4 alkylamino, dialkylamino or alkoximinoalkyl, and R^1 in each case represents α-naphthyl or β-naphthyl which may be optionally mono- or polysubstituted with the same or different substituents; , where suitable substituents are halogen, in each case linear or branched alkyl or alkoxy having 1 to 4 carbon atoms, or R^1 is optionally the same or different in each case. Represents a cycloalkyl group having 3 to 7 carbon atoms which may be mono- or polysubstituted by a substituent, where the appropriate substituent is a linear or branched cycloalkyl group having 1 carbon number in each case. -6 and optionally is alkyl, alkoxy, halogenoalkyl or halogenoalkoxy having 1 to 9 identical or different halogen atoms, and R^1 is in each case optionally mono- or polysubstituted by the same or different substituents. represents optionally substituted tetrahydronaphthyl or decahydronaphthyl, where suitable substituents for the hydrogenated ring are straight-chain or branched alkyl and alkoxy having 1 to 6 carbon atoms; Suitable substituents for aromatic rings are and furthermore halogen and in addition one or two heteroatoms where R^1 may optionally be mono- or polysubstituted in each case by the same or different substituents. represents a 5- or 6-membered heteroaryl group having , in which suitable substituents are in each case alkyl having 1 to 6 carbon atoms and/or halogen, and R^2 is hydrogen or methyl; and R^3 and R^4, taken together with the nitrogen atom to which they are attached, represent an optionally substituted saturated heterocyclic ring which may optionally contain another heteroatom. 2-aminomethyltetrahydrofurans according to claim 1, wherein the appropriate substituent is in each case a linear or branched alkyl or hydroxyalkyl having 1 to 4 carbon atoms. , their acid-addition salts, their geometric and optical isomers, and their isomeric mixtures. 4. In formula (I), R^1 represents phenyl which may be optionally mono-, di- or tri-substituted with the same or different substituents in each case, and suitable substituents here include fluorine, chlorine, ,
Bromine, iodine, cyano, nitro, methyl, ethyl, n-
or i-propyl, n-, i-, s- or t-
Butyl, n- or i-pentyl, n- or i-
hexyl, methoxy, ethoxy, t-butoxy, trifluoromethyl, trifluoromethylthio, trifluoromethoxy, methoximinomethyl, dimethylamino and diethylamino, and R^1 is optionally in each case the same or different substituents. represents α-naphthyl or β-naphthyl which may be mono-, di- or trisubstituted, where suitable substituents are fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, methoxy and ethoxy, in addition cyclopentyl or cyclohexyl, in each case optionally mono-, di- or tri-substituted by the same or different substituents; , in which suitable substituents are in each case methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, methoxy, ethoxy, t
-butoxy, trifluoromethyl and difluoromethoxy, furthermore R^1 represents tetrahydronaphthyl, optionally mono-, di- or tri-substituted in each case with the same or different substituents, where appropriate Substituents are fluorine, chlorine, bromine, methyl, ethyl, n- or i-
propyl, n-, i-, s- or t-butyl, methoxy and ethoxy, furthermore R^1 may optionally be mono-, di- or tri-substituted in each case by the same or different substituents. represents decahydronaphthyl, where suitable substituents are methyl, ethyl, n- or i-propyl, n-, i-
, s- or t-butyl, methoxy and ethoxy, and 2-, 3- or 4 in which R^1 may optionally be mono-, di- or tri-substituted in each case by the same or different substituents. -pyridyl and 2- or 3
-thienyl, in which suitable substituents are in each case fluorine, chlorine, bromine, methyl, ethyl, n- or i-
propyl, n-, i-, s- and t-butyl;
Furthermore, R^2 represents hydrogen or methyl, and R^3 and R^4, independently of each other, are in each case hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s
- or t-butyl, n- or i-pentyl, n
- or i-hexyl, n- or i-heptyl,
n- or i-octyl, allyl, n- or i-
butenyl, n- or i-pentenyl, propargyl, n- or i-butynyl, hydroxyethyl, hydroxypropyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl,
Ethoxypropyl, propoxypropyl, butoxypropyl, hydroxyethoxyethyl, dimethoxyethyl,
dimethoxypropyl, diethoxyethyl, dioxolanylmethyl, dioxolanylethyl, oxolanylmethyl, oxolanylethyl, dioxanylmethyl, dioxanylethyl, or in each case optionally the same or different substitutions cyclopropyl, cyclopropylmethyl, which may be mono-substituted or penta-substituted by groups;
cyclopropylethyl, cyclopropylpropyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl, in each case suitable substituents being fluorine, chlorine, bromine, methyl, ethyl,
n- or i-propyl, n-, i-, s- or t-butyl substituents, or in each case optionally mono-, di- or tri-substituted by the same or different substituents. represents phenyl, benzyl or phenylethyl, in each case suitable substituents being fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t. -butyl, methoxy, ethoxy, methylthio, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl or methoximinomethyl, the 2-aminomethyltetrahydrofurans according to claim 1, their acid-addition salts, geometric and optical isomers of and isomeric mixtures thereof. 5. In formula (I), R^1 represents phenyl which may be optionally mono-, di- or tri-substituted with the same or different substituents in each case, and suitable substituents here include fluorine, chlorine, ,
Bromine, iodine, cyano, nitro, methyl, ethyl, n-
or i-propyl, n-, i-, s- or t-
Butyl, n- or i-pentyl, n- or i-
hexyl, methoxy, ethoxy, t-butoxy, trifluoromethyl, trifluoromethylthio, trifluoromethoxy, methoximinomethyl, dimethylamino and diethylamino, and R^1 is optionally in each case the same or different substituents. represents α-naphthyl or β-naphthyl which may be mono-, di- or trisubstituted, where suitable substituents are fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, methoxy and ethoxy, in addition cyclopentyl or cyclohexyl, in each case optionally mono-, di- or tri-substituted by the same or different substituents; , in which suitable substituents are in each case methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, methoxy, ethoxy, t
-butoxy, trifluoromethyl and difluoromethoxy, furthermore R^1 represents tetrahydronaphthyl, optionally mono-, di- or tri-substituted in each case with the same or different substituents, where appropriate Substituents are fluorine, chlorine, bromine, methyl, ethyl, n- or i-
propyl, n-, i-, s- or t-butyl, methoxy and ethoxy, furthermore R^1 may optionally be mono-, di- or tri-substituted in each case by the same or different substituents. represents decahydronaphthyl, where suitable substituents are methyl, ethyl, n- or i-propyl, n-, i-
, s- or t-butyl, methoxy and ethoxy, and 2-, 3- or 4 in which R^1 may optionally be mono-, di- or tri-substituted in each case by the same or different substituents. -pyridyl and 2- or 3
-thienyl, in which suitable substituents are in each case fluorine, chlorine, bromine, methyl, ethyl, n- or i-
propyl, n-, i-, s- and t-butyl;
Furthermore, R^2 represents hydrogen or methyl, and R^3 and R^4 together with the nitrogen atom to which they are bonded, there is a formula ▲ mathematical formula, chemical formula, table, etc. ▼; ▲ mathematical formula, Chemical formula,
There are tables, etc.▼；▲There are mathematical formulas, chemical formulas, tables, etc.▼
; ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ represents a heterocyclic ring, which is optionally mono-substituted, di-substituted, or 2-Aminomethyltetrahydrofurans, their acid-addition salts, as claimed in claim 1, which may be tri-substituted, where suitable substituents are in each case methyl, ethyl or hydroxymethyl. geometric and optical isomers of and isomeric mixtures thereof. 6. General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 is optionally substituted aryl, heteroaryl, cycloalkyl, decahydronaphthyl or tetrahydronaphthyl, R^2 represents hydrogen or methyl, and R^3 and R^4 are, independently of each other, in each case hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, dialkoxyalkyl, hydroxy represents alkyl, hydroxyalkoxyalkyl, dioxolanylalkyl, oxolanylalkyl, dioxanylalkyl, or in each case optionally substituted cycloalkylalkyl, cycloalkyl, aralkyl, aralkenyl or aryl; R^3 and R^4, taken together with the nitrogen atom to which they are attached, represent an optionally substituted saturated heterocyclic ring which may optionally contain another heteroatom. 2-aminomethyltetrahydrofurans, their acid-addition salts, their geometric and optical isomers,
and their isomer mixtures, (a) Formula (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) [In the formula, R^1 and R^2 have the above meanings. , and X^1
represents an electron-withdrawing free radical] Substituted tetrahydrofurans of the formula (III), optionally in the presence of a diluent and optionally in the presence of an acid binder, are prepared by formula (III) ▲Mathematical formula, chemical formula, table, etc. III) in which R^3 and R^4 have the abovementioned meanings; or (b) formula (Ia) obtained by process (a) and/or (c). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Aminomethyltetrahydrofurans [in the formula, R^1, R^2 and R^3 have the above meanings] in the presence of an appropriate diluent and an appropriate acid bond In the presence of the agent, the formula (IV) R^4^-^1-X^2 (IV) [wherein R^4^-^1 is alkyl, alkenyl, alkynyl,
Alkoxyalkyl, dialkoxyalkyl, hydroxyalkyl, hydroxyalkoxyalkyl, dioxolanylalkyl, oxolanylalkyl, dioxanylalkyl, or in each case optionally substituted cycloalkylalkyl, cycloalkyl, aralkyl or aralkenyl and X^2 represents an electron-withdrawing radical] or (c) the formula (I b) obtained by method (a) ▲ formula,
There are chemical formulas, tables, etc. ▼ (I b) [In the formula, R^1^-^1 represents an optionally substituted aryl, R^3 represents hydrogen or methyl, and R^3^- ^1 and R^4^-^2 each independently represent hydrogen, alkyl, alkoxyalkyl,
represents dialkoxyalkyl, hydroxyalkyl, hydroxyalkoxyalkyl, dioxolanylalkyl, oxolanylalkyl, dioxanylalkyl, or in each case optionally substituted cycloalkyl, cycloalkylalkyl, aralkyl or aryl; or R^4^-^1 and R^4^-^2, together with the nitrogen atom to which they are attached, are optionally substituted which may optionally contain another heteroatom. [representing a saturated heterocyclic ring which may be and optionally then adding an acid. 7. A pest control agent containing at least one 2-aminomethyltetrahydrofuran of the formula (I) according to claims 1 and 6. 8. Claim 1 for controlling pests
and the use of 2-aminomethyltetrahydrofurans of formula (I) as described in Section 6. 9. Formula (I) described in claims 1 and 6
A method for controlling pests, which comprises applying 2-aminomethyltetrahydrofuran to pests and/or their habitats. 10, Formula ( I
1. A method for producing a pesticide, which comprises mixing the 2-aminomethyltetrahydrofurans of ) with an extender and/or a surfactant.