NZ237297A

NZ237297A - 4-(4-tertiarybutylphenyl)-cyclohexylamine derivatives, quaternary salts thereof and fungicides

Info

Publication number: NZ237297A
Application number: NZ237297A
Authority: NZ
Inventors: Bernhard Zipperer; Eberhard Ammermann; Gisela Lorenz
Original assignee: Basf Ag
Priority date: 1990-03-06
Filing date: 1991-03-04
Publication date: 1992-04-28
Also published as: HU910709D0; ES2053219T3; EP0447828A1; CA2037079A1; KR910016684A; JPH04211636A; EP0447828B1; ZA911588B; HU207032B; IL97349A0; DE4006937A1; HUT56811A; DK0447828T3; ATE105279T1; AU7209491A; DE59101532D1; AU632400B2

Abstract

4-(4-Tert.-butylphenyl)cyclohexylamines and their quaternary ammonium salts of the formulae <IMAGE> in which R<1> is hydrogen, alkyl or alkenyl, R<2> is alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, alkylcycloalkyl, bicycloalkyl, alkenyl, phenyl which is unsubstituted or optionally monosubstituted to trisubstituted or phenylalkyl which is unsubstituted or optionally monosubstituted to trisubstituted, and X<(-)> is an acid anion which is tolerated by plants, and their acid addition salts which are tolerated by plants, and fungicides containing these compounds.

Description

<div class="application article clearfix" id="description"> New Zealand Paient Spedficaiion for Paient Number £37297 237 2 9 7 Priority Oate(s): .C*?. | : Cornr?lpf9 PpecificsUcn Filed: fJ Class: ($).£.££?£.?:}.i.h-.Qf.If.'..j,.Mr.>?.i,.W.'.^.f. ' G.Vrr.j.CCO£-2r.J.5.|Lh~.f.Ijiic.jf.TJ.Co..^3.f.. | ,:'v:bficetion Date: U.MM ■ ■ : I 3..D.S I —. . - — _n —v- _ i-ui — ill ji —ij—- h<iiiii < ■ i i i i i nr \ " j Class Cont:<:vC?r7\^ »o <J&| NO DRm«* Patents Form No, TCrTtCE \ ! iSS'l «••• ! NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION 4-(4-TERT-BUTYLPHENYL)CYCLOHEXYLAMINES, AND FUNGICIDES CONTAINING SAME WE, BASF AKTIENGESELLSCHAFT, a German joint company under the laws of FEDERAL REPUBLIC OF GERMANY of 6700 Ludwigshafen, FEDERAL REPUBLIC OF GERMANY hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: - 1 - (followed by page la) - I a O.Z. 0050/41443 4-(4-tert-Butvlphenvl)cyclohexylamines, and fungicides containing same The present invention relates to novel 4-(4-tert-butylphenyl)cyclohexylamines and acid-addition salts and 5 quaternary salts thereof, to a process and intermediates for the preparation thereof, to the use thereof as fungicides, to fungicides, and to a method of controlling harmful fungi using these active ingredients. The compound trans-4-tert-butyl-N-benzylcyclo-10 hexylamine is known (J. Org. Chem. 48 (1983) 3412-3422), but nothing is known on its fungicidal action. 4-(Cyclohexylmethyl)eyelohexylamine and its N,N-dimethyl derivative are known as fungicides (US 3,981,766), but their fungicidal action is unsatisfac-15 tory. 1- [ 4- ( 4-tert-Butylphenyl) cyclohexyl ] -2 , 6-di-methylmorpholine has been described as a fungicide (EP 259 977), but its efficacy is poor in some areas of application, in particular at low application rates and 20 concentrations. Fungicidal cyclohexylamines are known in the orior art. Their fungicidal action is good, but their plant compatibility is unsatisfactory, particularly at relatively high application rates. 25 We have now found that 4-(4-tert-butylphenyl)- cyclohexylamines and the quaternary ammonium salts ^thereof, of the formulae x© -*-0—0-\ and 1 2 where 30 R1 is hydrogen, C1-Cs-al]cyl or C3-Csalkenyl, R2 is Ci-C^-alkyl, C^-C^-haloalkyl, C:-C12-hydroxyalkyl, Cj-C^-cycloalkyl, C4-C12-alkylcycloalkyl, C7-C12-bicyclo-alkyl, C3-C12-alkenyl, unsubstituted, monosubstituted, (followed by page 2) 237 2 9 7 - 2 - O.Z. 0050/41443 disubstituted or trisubstituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl-(C1-C3)alkyl/ possible substituents in each case being identical or different Cj-C^-alkyl, Cj-C^-alkoxy, Cj-C*,-haloalkyl, Cj-C^-haloalkoxy, halogen, cyano, hydroxyl or nitro groups, with the proviso that R1 and R2 are not simultaneously Cj-C^-alkyl, Xs is a plant-compatible acid anion, and the plant-compatible acid addition salts thereof, have a strong fungicidal action and surprisingly good plant compatibility. R1 is, for example, hydrogen, straight-chain or branched Ci-Cg-alkyl, in particular Ci-Ci.-alkyI, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, n-hexyl, isohexyl or neohexyl, or straight-chain or branched C2-C6-alkenyl, such as 2-propen-l-yl, cis- or trans-2-buten-l-yl, 2-methyl-2-propen-l-yl, 3-buten-2-yl or 3-methyl-2-buten-l-yl. R2 is, for example, straight-chain or branched Ci-C12-alkyl, in particular C1-CA-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl; Ci-C^-haloalkyl such as chloromethyl, bromomethyl, iodomethyl, 2-chloroethyl, 4-chloro-l-butyl, 3-chloro-l-butyl, 3-chloro-2-methyl-l-propyl, 5-chloro-l-pentyl or 6-chloro-l-hexyl; Ci-C12-hydroxyalkyl, such as 2-hydroxyethyl, 2-hydroxy-1-propyl, 6-hydroxy-1-hexyl, 8-hydroxy-1-octyl or 10-hydroxy-1-decyl; C3-C12-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclodecyl or cyclododecyl; C4-C12-alkylcycloalkyl such as methylcyclo-propyl, methylcyclopentyl, 2-, 3- or 4-methylcyclohexyl, 2-, 3- or 4-ethylcyclohexyl, 4-isopropylcyclohexyl, 4-tert-butylcyclohexyl, 2,2-, 3,3- or 4,4-dimethylcyclo-hexyl, 2,6-dimethylcyclohexyl or 3,3,5,5-tetramethyl- 237 2 9 7 P* - 3 - O.Z. 0050/41443 cyclohexyl; C7-C12-bicycloalkyl such as bicyclo[2.2.1]-hept-2-yl, 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl, bicyclo[4.4.0]dec-2-yl or bicyclo[4. 4.0]dec-3-yl; phenyl, C1-C4-alkylphenyl, mono-, di- or trimethylphenyl, ethyl-5 phenyl, isopropylphenyl, tert-butylphenyl, C^-C^-alkoxy- phenyl, mono-, di- or trimethoxyphenyl, n- or tert-butoxyphenyl, C^-C^-haloalkylphenyl, C^-C^-haloalkoxy-phenyl, trifluoromethylphenyl, difluoromethoxyphenyl, trifluoromethoxyphenyl, tetrafluoroethoxyphenyl, cyano-10 phenyl, nitrophenyl, mono-, di- or trichlorophenyl, mono-, di- or trifluorophenyl, chlorofluorophenyl, bromophenyl, aryl(C1-C3)alkyl, such as benzyl, C1-C4-alkylbenzyl, mono-, di- or trimethylbenzyl, tert-butyl-benzyl, halobenzyl, fluorobenzyl, mono-, di- or tri-15 chlorobenzyl, C^-C^-alkoxybenzyl, mono-, di- or tri- methoxybenzyl, cyanobenzyl, nitrobenzyl, 2-phenylethyl, 2-(methoxyphenyl)ethyl, 2-(chlorophenyl)ethyl,2-(fluorophenyl) ethyl, 2-(tert-butylphenyl)ethyl, 3-phenylpropyl, 3-(chlorophenyl)propyl or 3-(fluorophenyl)propyl. 2 0 Xs is an inorganic or organic acid anion, for example chloride, bromide, iodide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, nitrate, tetrafluoroborate; formate, acetate, oxalate, methanesulfonate, benzenesulfonate, p-toluene-25 sulfonate or dodecylbenzenesulfonate. Examples of acids for the preparation of the acid-addition salts are mineral acids, hydrochloric acid, sulfuric acid, nitric acid, formic acid, alkylcarboxylic acids, such as acetic acid, propionic acid, oxalic acid, 30 sulfonic acids, such as methanesulfonic acid, benzene- sulfonic acid, p-toluenesulfonic acid and dodecyl-benzenesulfonic acid. The novel compounds of the formulae 1 and 2 can exist in two diastereomeric forms, namely as cis-1,4- and 35 as trans-l,4-disubstituted cyclohexane. Depending on the preparation method, they are obtained either as pure diastereomers or as diastereomer mixtures. If desired, r - 4 - 23 7 2 O.Z. 0050/41443 the latter can be resolved to give pure diastereomers by generally known methods, for example by chromatography or fractional crystallization. The present invention relates both to the pure diastereomers and to mixtures thereof. 5 In some of the radicals R2 according to the invention, further isomers can occur in addition to the abovementioned cis/trans isomerism. Depending on the nature of R2, these isomers may be enantiomers or diastereomers. Here too, the diastereomeric compounds can be 10 resolved by conventional methods, for example by chroma tography or crystallization. All isomeric compounds and mixtures thereof with one another are included in the present invention. The pure diastereomers or enantiomers and the mixtures thereof are suitable for use of the 15 novel amines as fungicides. Preference is given to mixtures. The present invention also relates to a process for the preparation of the novel amines of the formula 1. a) These amines can be prepared, for example, by 20 reacting an amine of the formula Ri H-N 3 where R1 is hydrogen, C1-C6-alkyl or C3-C5-alkenyl and R2 is C^-Ctf-alkyl, with the proviso that R1 and R2 are not 25 simultaneously C1-CA-alkyl, or is Ci-C^-haloalkyl, Ci-C^-hydroxyalkyl, C3-C12-cycloalkyl, C<,-C12-alkylcycloalkyl, C7-C12-bicycloalkyl, C3-Cl2-alkenyl, unsubstituted, mono-substituted, disubstituted or trisubstituted phenyl, or unsubstituted, monosubstituted, disubstituted or tri-30 substituted phenyl(Ci-C^)-alkyl, possible substituents being in each case identical or different Ci-C^-alkyl, Cx-CValkoxy, Cx-C^-haloalkyl, C^-CVhaloalkoxy, halogen, cyano, hydroxyl or nitro groups, with 4-(4-tert-butylphenyl)cyclohexanone, and reducing 237297 - 5 - O.Z. 0050/41443 the imine (in the case where R1 is hydrogen) or enamine (in the case where R1 is not hydrogen) produced as a reaction product, either directly or after isolation, using a reducing agent to give an amine of the formula 1. 5 It is advantageous to remove from the reaction mixture the water of reaction liberated on reaction of an amine of the formula 3 in which R1 and R2 are as defined above with 4-(4-tert-butylphenyl)cyclohexanone. This can be effected, for example, by adding a dehydrating agent 10 or by azeotropic distillation. Examples of suitable dehydrating agents are salts which are free of or low in water of hydration, such as sodium sulfate, magnesium sulfate, zinc sulfate, calcium chloride or molecular sieves. The reaction is carried out in the presence or 15 absence of an inert organic solvent and in the presence or absence of a catalytic amount of acid. Suitable solvents are hydrocarbons, such as cyclohexane, benzene, toluene or xylenes, chlorinated hydrocarbons, such as dichloromethane or 1,2-dichloroethane, or ethers, such as 20 diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane. Examples of suitable acids are mineral acids, such as sulfuric acid or phosphoric acid, or sulfonic acids, such as methanesulfonic acid, benzenesulfonic acid or p-toluenesulfonic acid. The amount of acid necessary 25 is, for example, from 0 to 10 mol-%, preferably from 0 to 1 mol-%, based on the amine of the formula 3. The reaction can be carried out at room temperature or at elevated temperature, for example up to the boiling point of the particular solvent. If the reaction temperature which 30 is necessary cannot be achieved under atmospheric pres sure or if the reaction proceeds only slowly, the reaction can be carried out in an autoclave (with or without a solvent) at elevated temperature under the inherent pressure of the reaction mixture. If the water of reac-35 tion produced is removed from the reaction mixture by azeotropic distillation, the reaction is carried out at the boiling point of the particular solvent. Preferred 237297 6 - O.Z. 0050/41443 solvents here are aromatic hydrocarbons, such as benzene, toluene or xylenes. The unsaturated nitrogen compound (imine or enamine) produced on reaction of an amine of the formula 5 3 where R1 and R2 are as defined above with 4-(4-tert- butylphenyl)cyclohexanone can be reduced by conventional methods to give an amine of the formula 1. Specific examples of preferred reducing agents are hydrogen, formic acid, or complex hydrides such as sodium boro-10 hydride or sodium cyanoborohydride. Particular preference is given to hydrogen in the presence of a metallic catalyst. Examples of suitable catalysts are finely divided metals, such as Raney nickel or Raney cobalt, and noble metals, such as palladium or platinum, with or 15 without a solid carrier. The hydrogenation using hydrogen can be carried out with or without pressure (cf., for example, Houben-Weyl, Methoden der Organischen Chemie, Volume 11/1, pp. 602 ff, G. Thieme Verlag, Stuttgart, 1957). It is occasionally advantageous to prepare the 20 amine of the formula 1 in one step from an amine of the formula 3 and 4-(4-tert-butylphenyl)cyclohexanone. A known process for this purpose in which the reducing agent is formic acid is the reductive amination by the Leuckardt-Wallach method (cf., for example, 25 Houben-Weyl, Methoden der Organischen Chemie, Volume 11/1, pp. 648 ff, G. Thieme Verlag, Stuttgart, 1957). Another process, which is particularly advantageous for laboratory scale syntheses, uses sodium cyanoborohydride as the reducing agent (cf., for example, C.F. Lane, Syn-30 thesis 1975, 135). The combination of sodium cyanoborohydride and anhydrous zinc chloride has proven particularly expedient (cf. S. Kim et al., J. Org. Chem. 50 (1985) 1927). In this process, the NaBH3CN:ZnCl2 molar ratio can 35 be, for example, from 1:2 to 1:0.5, preferably 1:0.5. As far as the amount of NaBH3CN employed is concerned, either the amine component 3 or the ketone component can be used - 7 - 23 7 2 9 O.Z. 0050/41443 in an equimolar amount; an excess of the other component may occasionally be advantageous in order to accelerate or complete the reaction. The reaction is preferably carried out in a lower alcohol, such as methanol, 5 ethanol, n-propanol or isopropanol, particularly prefer ably in methanol, as solvent, at between 0°C and the boiling point of the particular solvent. The reaction is preferably carried out at room temperature. The 4-(4-tert-butylphenyl)cyclohexanone used as 10 starting material is novel. It can be prepared from known, commercially available 4-phenylcyclohexanone by Friedel-Crafts alkylation of the phenyl ring. Examples of alkylating agents are tert-butyl chloride or bromide, tert-butanol or 2-methylpropene (cf., for example, 15 Houben-Weyl, Methoden der Organischen Chemie, Vol. 5/2b, pp. 154 ff., pp. 179 ff., G. Thieme Verlag, Stuttgart, 1981). Preference is given to 2-methylpropene in the presence of a mineral acid, for example sulfuric acid or phosphoric acid, or in the presence of a Lewis acid, such 20 as aluminum trichloride, iron(III) chloride or boron trifluoride. Suitable solvents are in particular chlorinated hydrocarbons, especially dichloromethane, tetra-chloromethane, and 1,2-dichloroethane. The tert-butyla-tion of the 4-phenylcyclohexanone can be carried out at 25 room temperature or below, preferably at from 0 to 2 0°C. The amines of the formula 3 where R1 and R2 are as defined above are known compounds and those which are not commercially available can be prepared by known processes . 30 The amines prepared by the above-described process, where R1 and R2 are as defined above, are generally mixtures of the two possible stereoisomers containing a cis- or trans-1,4-disubstituted cyclohexane ring. These cis/trans mixtures may, if desired, be resolved 35 into their constituents by known methods, for example by chromatography or fractional crystallization, b) A further process allows the targeted preparation 23 7 2 - 8 - O.Z. 0050/41443 of cis- or trans-4-(4-tert-butylphenyl)cyclohexylamines of the formula 1 where R1 is hydrogen and R2 is C1-C12-alkyl, C^-C^-haloalkyl, C1-C12-hydroxyalkyl, 5 C3-C12-cycloalkyl, CA-C12-alkylcycloalkyl, C7-C12-bicyclo- alkyl, C3-C12-alkenyl, unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl-(Ci-CsJalkyl, possible substituents in each case being 10 identical or different Ci-C^-alkyl, C1-CJi-alkoxy, C1-CA- haloalkyl, Ci-C^-haloalkoxy, halogen, cyano, hydroxyl or nitro groups. This process comprises first converting 4-(4-tert-butylphenyl)cyclohexanone into 4-(4-tert-butyl-15 phenyl)cyclohexanone oxixae by conventional methods using hydroxylamine or a hydroxyl amine salt, and subsequently reducing this oxime using sodium in ethanol (cf., for example, Chem. Ind. (London) 1972, 683). The trans-4-(tert-butylphenyl)eyelohexylamine obtained is then 20 reacted in a further step with a carbonyl compound of the formula o R3-C-R* 4 where R3 and R4 are such that the radical R3 / -CH \ corresponds in its entirety to R2 as defined above, and 25 the inline formed is reduced, directly or after isolation, using a reducing agent to give the amine of the formula 1. If 4-(4-tert-butylphenyl)cyclohexanone oxime is reduced, for example, using hydrogen, a mixture of cis-30 and trans-4-(4-tert-butylphenyl)eyelohexylamine is obtained, which can be resolved into the pure cis- and trans-isoraers by conventional methods, for example by 23 7 2 - 9 - O.Z. 0050/41443 chromatography, distillation or fractional crystallization of an acid-addition salt with subsequent liberation of the base. The two isomers can then be reacted separately with a carbonyl compound of the 5 formula 0 II R3—C—R4 4 where R3 and R* are as defined above to give the pure cis-and trans-configured amines of the formula 1. It is of course also possible to react the 10 mixture of cis- and trans-4-(4-tert-butylphenyl)cyclohexylamines with a carbonyl compound of the formula 4 and to resolve the resultant isomer mixture of amines of the formula 1 into its constituents, for example by chromatography or crystallization. 15 A further way of preparing a cis/trans mixture of 4-(4-tert-butylphenyl)cyclohexylamines comprises alkylating cis/trans-4-phenylcyclohexylamine using 2-methyl-propene in the presence of an at least equimolar amount of mineral acid, for example sulfuric acid. Preferred 20 solvents are chlorinated hydrocarbons, eg. dichloro- methane, tetrachloromethane or 1,2-dichloroethane. The alkylation can be carried out at room temperature or below, preferably at from 0 to 20°C. The 4-phenylcyclohexylamine used as a starting 25 material is known. It can be prepared, for example, by hydrogenating 4-aminobiphenyl (R. Egli, C.H. Eugster, Helv. Chim. Acta 58 (1975) 2321) or 4-phenylcyclohexanone oxime (Nightingale et al., J. Org. Chem. 17 (1952) 1017). The carbonyl compounds of the formula 4 which are 30 required for process b) are common chemicals, and those which are not commercially avaiable can be prepared by conventional methods. The reaction conditions described in detail for process a) also apply similarly to process b) . 35 The above-described process b) gives the amines 237297 - 10 - O.Z. 0050/41443 of the formula 1 where R1 is hydrogen. These secondary amines can, if desired, be converted into tertiary amines of the formula 1 where R1 is C^-Cg-alkyl or C3-C5-alkenyl by known alkylation reactions. If the alkylating agent used is a methyl compound of the formula CH3-A 5 where A is a nucleofugic leaving group, eg. chlorine, bromine, iodine, 0-S02-0CH3, 0-S02-CH3 or 0-S02-p-C6HA-CH3, and the alkylating agent is employed in excess, 4-(4-tert-butylphenyl)cyclohexylammonium salts of the formula 2 where R2 is as defined above are obtained. This quaternization can be carried out in the presence or absence of a diluent. Examples of suitable diluents are alcohols, such as methanol, ethanol, n- or isopropanol, n-butanol or cyclohexanol, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, esters, such as methyl acetate or ethyl acetate, nitriles, such as acetonitrile or propionitrile, nitro compounds, such as nitromethane or nitrobenzene, or other solvents which are inert in this reaction. The alkylation is preferably carried out using two to 6 times the molar amount of alkylating agent of the formula 5 and at from 20 to 200°C. The reaction is expediently carried out at the boiling point of the particular diluent, or, if none is used, of the particular alkylating agent. It is occasionally advantageous to carry out the quaternization in the presence of an auxiliary base, which can be added in excess or in an equimolar amount, based on the amine 1 to be alkylated. The use of a base which is insoluble in the reaction medium, for example sodium carbonate, potassium carbonate or calcium carbonate, is particularly advantageous. The reaction product obtained is a 4-(4-tert-butylphenyl)eyelohexylammonium salt of the formula - 11 - O.Z. 0050/41443 n®-r2 a© 2a I ch 3 where R2 and A are as defined above. If necessary, the anion A9 can be replaced by another, plant-compatible acid anion by conventional methods, for example by ion exchange chromatography. 237297 ?< iTttTi >" \ - 13 - O.Z. 0050/41443 The examples below are intended to illustrate the preparation of the compounds according to the invention in greater detail. EXAMPLE 1 5 4-(4-tert-Butylphenyl)cyclohexanone 170.5 g (1.74 mol) of concentrated sulfuric acid are added dropwise with stirring and cooling at from 0 to 5°C to a solution of 50 g (0.287 mol) of 4-phenylcyclohexanone in 600 ml of dichloromethane. 19.5 g (0.35 mol) 10 of isobutylene (2-methylpropene) gas are passed into this mixture over the course of 15 to 20 minutes at from 10 to 15°C. The mixture is stirred at room temperature (20°C) for a further one hour and 250 ml of water are then added dropwise with ice cooling. The organic phase is separated 15 off, washed neutral with water, 10% strength NaOH and again with water, dried over NaaSO*. and evaporated under reduced pressure. The residue is recrystallized from n-pentane, to give 50.7 g (7 6% of theory) of colorless crystals of melting point 80-82°C. 20 1H-NMR (CDC13) : 5 =7.35 (d, 2H), 7.18 (d, 2H), 3.00 (br, t, 1H) , 2.50 (m, 4H), 2.21 (m, 2H) , 1.95 (m, 2H), 1.30 (s, 9H). IR (KBr): 1/ = 2965, 2944, 2867, 1710, 1418, 1160, 832, 808, 570 cm'1. 25 EXAMPLE 2 4-trans-tert-Butyl-4'-cis/trans-(4-tert-butylphenyl)-N,N-dicyclohexylamine (Compound No. 62) 16.1 g (0.07 mol) of 4-(4-tert-butylphenyl)cyclohexanone, 21.7 g (0.14 mol) of trans-4-tert-butylcyclo-30 hexylamine and 4.8 g (0.035 mol) of anhydrous zinc chloride are dissolved in 250 ml of methanol. 4.4 g (0.07 mol) of sodium cyanoborohydride are introduced into the solution in portions. The mixture is stirred at room temperature for 24 hours, and the majority of the solvent 35 is then stripped off under reduced pressure. The residue taken up in water, rendered alkaline using concentrated NaOH and extracted several times with methyl tert-butyl 237297 - 14 - O.Z. 0050/41443 ether. The organic phase is dried over Na2SOA, freed from solvent and then distilled under reduced pressure. After an initial fraction comprising principally 4-tert-butyl-cyc lohexylamine, 19.3 g (75% of theory) of the title 5 compound are obtained at 210-212°C/0.2 mbar as a color less, viscous oil. According to GC and :H-NMR analysis, it is a cis/trans mixture in the ratio 2:3. C26HA3N (369.1) Calc. C 84.48 H 11.73 N 3.79 Found C 84.5 H 11.7 N3.6 10 EXAMPLE 3 Resolution of 4-trans-tert-butyl-4'-cis/trans-4-(tert-butylphenyl)-N,N-dicyclohexylamine 8.0 g of a cis/trans isomer mixture obtained as in Example 2 are resolved by chromatography on a 30 x 15 3 cm silica gel column (Macherey & Nagel, 0.04-0.06 mm) using cyclohexane/ethyl acetate (4:1) at 0.1 bar of nitrogen. The 4-trans-tert-butyl-4'-cis-(4-tert-butyl-phenyl)-N,N-dicyclohexylamine is eluted first as a colorless solid of melting point 54-56°C (ethanol). The 20 relative stereochemistry was determined by 1H- and 13C-NMR spectroscopy. ^-NMR (CDC13) : inter alia S = 3.00 (m, l'-Heq), 2.55 (m, l-Hax) , 2.40 (4 ' -H^) . 13C-NMR (CDCI3): inter alia 6 = 54.04 (C-l') , 43.69 (C-25 4'), 34.86 (C-2'(6'))/ 33.39 (C-3'(5')). After a mixed fraction (0.8 g), 4-trans-tert-butyl-4'-trans-(4 - tert-butylphenyl) -N, N-dicyc lohexy 1 amine is obtained, initially as a pale yellow oil, which crystallizes from acetonitrile. Colorless crystals, 30 melting point 112-113°C. ^-NMR (CDCI3): inter alia 5 = 2.67 (br.m, l'-H^), 2.50 (br. m, 1-H„ + 4'H^). 13C-NMR (CDCI3) : inter alia <5 = 48.42 (C-l'), 42.69 (C-4'), 30.98 (C-2'(6')), 28.30 (C-3'(5')). 35 EXAMPLE 4 N,N-Dimethyl-4-trans-tert-butyl-4'-cis/trans-(4-tert-butylphenyl)-N,N-dicyclohexylammonium iodide 237297 - 15 - O.Z. 0050/41443 7.4 g (0.02 mol) of 4-trans-tert-butyl-4'-cis/ trans-(4-tert-butylphenyl)-N,N-dicyclohexylamine (Example 2), 11.4 g (0.08 mol) of methyl iodide and 10.2 g of sodium carbonate (0.10 mol) are refluxed for 6 hours in 5 50 ml of ethanol. After cooling, the mixture is filtered, the filtrate is evaporated to dryness under reduced pressure, and the oily residue is boiled with 50 ml of ethyl acetate. The mixture is left to stand overnight, and the precipitate is filtered off with suction, washed 10 with ice-cold acetone and dried at 50°C under reduced pressure, to give 6.7 g (62% of theory) of quaternary salt as colorless crystals of melting point 184-185°C. EXAMPLE 5 cis/trans-4-(4-tert-Butylphenyl)eyelohexylamine 15 165 g of concentrated H2S04 (1.68 mol) are added dropwise to 52.5 g (0.30 mol) of well cooled 4-phenyl-cyclohexylamine (cis/trans ratio of about 2:3) at from 0 to 5°C. 1,000 ml of dichloromethane diluent are added, and 21.8 g (0.39 mol) of isobutylene gas are passed in 20 over the course of 20 minutes at from 10 to 15°C. After one hour at 20°C, 250 ml of water are added dropwise with ice cooling. The aqueous phase is extracted twice with CH2C12. The combined organic phases are stirred vigorously with 1 1 of 10 percent strength by weight NaOH, then 25 washed with water, dried over Na2S04 and evaporated under reduced pressure. The crude amine, which is about 70% pure according to gas chromatography, is dissolved in 500 ml of ether and precipitated as the hydrochloride by passing in HCl gas with ice cooling to give 35.3 g (44.5% 30 of theory) of a yellowish crystal powder which decomposes above 2 4 00 C, IR (KBr): i/ = 2956, 2932, 2868, 1607, 1510, 1448, 1362, 1268, 831, 574 cm"1. The free base is obtained therefrom by adding 35 aqueous ammonia solution, extracting the mixture with methyl tert-butyl ether, and drying and evaporating the organic phase to give a colorless oil (cis/trans 2 -- 4», - 16 - O.Z. 0050/41443 mixture). Characteristic NMR data (CDC13) : cis-4-(4-tert-butylphenyl) eye lohexylamine: 5 1-Heq = 3.19; 7 C-l = 45.3 ppm. trans-4-(4-tert-Butylphenyl)eyelohexylamine: 5 S 1-H^ = 2.70; S C-l = 50.2 ppm. EXAMPLE 6 N-Benzyl-N-4-(4-tert-butylphenyl)eyelohexylamine (Compound No. 104) A solution of 11.6 g (0.05 mol) of 4-(4-tert-10 butylphenyl)cyclohexylamine (cis/trans mixture) and 6.4 g (0.06 mol) of freshly distilled benzaldehyde in 200 ml of toluene is treated with 14.2 g (0.10 mol) of sodium sulfate and stirred at room temperature overnight. After filtration, the toluene is stripped off and replaced by 15 ethanol. 2.7 g (0.07 mol) of sodium borohydride are then added, the mixture is refluxed for one hour and evaporated to dryness, and the residue is partitioned between water and methyl tert-butyl ether. The organic phase is washed with water, dried over sodium sulfate and evapor-20 ated, and the residue is subjected to incipient distillation at 2 mbar up to 200°C to give 9 g (56% of theory) of a pale reddish resin, a 2:1 trans/cis isomer mixture according to XH-NMR and gas chromatography. IR (film): 1/ = 2961, 2927, 2862, 1461, 1452, 1362, 827, 25 736, 698, 572 cm"1. C23H31N (321.1) Calc. C 85.92 H 9.72 N 4.36 Found C 85.5 H9.9 N4.1 The following compounds are prepared by measures 30 similar to these Examples: No. R1 , R2 1 H Methyl 2 H Ethyl 3 H 1-PropyI 4 H 2-Propy1 5 H 1-Butyl 6 H 2-Butyl 7 H tert.-Butyl 8 H 2-Methyl-l-propyl 9 H 1-Penty1 10 H 2-Methy1-1-butyl 11 H 2-Methy1-1-pentyl 12 H 2-Ethy1-1-butyl 13 H 2,2-Dimethy1-1-propy1 14 H 3,3-Dimethy1-1-butyl 15 H 3-Methy1-1-butyl 16 H 1-Hexy1 17 H 2-Methy1-1-hexyl 18 H 2-Ethy1-1-hexy1 19 H 2,4,4-Trimethyl-l-pentyl 20 H 1-Hepty1 21 H 1-Octyl 22 H 1-Nony1 23 H 1-Decy1 24 H 1-Undecy 1 25 H 1-Dodecy 1 26 H 2-Propen-l-y 1 27 H 2-Buten-l-y1 900031 17 o.Z. 0050/41443 Physical data bp. 220-224°C/2 mbar (cis/trans=l:2) resin (cis/trans=l:2) ro CM ro CO No. R1 28 H 2-Penteri-l-y 1 29 H 2-Hexen-l-yl 30 H 3-Methyl-2-buten-l-y1 31 H 2,3-Dimethy1-2-buten-l-y1 32 H 2-Hydroxyethyl 33 H 6-Hydroxy-l-hexy1 34 H 3-Chloro-l-buty1 35 H 4-Chloro-l-buty1 36 H 3-Chloro-2-methy1-1-propyI 37 H Cyclopropyl 38 H Cyclobutyl 39 H Cyclopentyl 40 H Cyclohexyl 41 H Cycloheptyl 42 H Cyclooctyl 43 H Cyclodecyl 44 H Cyclododecyl 45 H 1-Methylcyclopropyl 46 H 1-Methylcycloperityl 47 H 1-Methylcyclohexyl 48 H 2-MethyIcyclohexyl 49 H 3-Methylcyclohexyl 50 H 4-Methylcyclohexyl 51 H 2, 2-DimethyIcyclohexy1 52 H 3,3-DimethyIcyclohexyl 53 H 4,4-Dimethylcyclohexyl 54 H 2, 6-DimethyIcyclohexy1 18 Physical data 900031 O.Z. 0050/41443 •3 bp. 180-186°C/0.5 mbar (cis/trans=l:2) bp. 167-170°C/0.4 mbar (cis/trans=l:2) IR: 2949,2923,2865,2851,1447, 1363,1112, 826, 571 TO* CO 19 900031 O.Z. 0050/41443 r2 Physical data 3.3.5-Trimethylcyclohexyl 3, 3,5,5-TetramethyIcyclohexy1 4-Ethylcyclohexyl 4-Propylcyclohexyl 4-Isopropylcyclohexyl Hydrochloride: IR:2951,2865,2794 2734,1462,1385,1363,827,572 4-tert.-ButyIcyclohexy1 c is-4-tert.-ButyIcyclohexyl trans-4-tert.-Butylcyclohexyl 4'-cis: Fp. 54-56°C; 4'-trans: mp. 112-113°C 4-tert.-AmyIcyclohexyl Bicyclo[2.2.1]-hept-2-yl 1,7,7-Trimethyl-bicyclo[2.2.1]-hept-2-y1 Bicyclo[4.4.0]dec-2-yl Bicyclo[4.4.0]dec-3-yl IR: 2923,2856,1464,1447,1362,1269,1111,826,571 resin (cis/trans=l:2) 2.6.6-Trimethylbicyclo[3.1.1]-hept-3-yl Phenyl IR:2960, 2928,2863,1602,1503, 1362,1312,827,746, 691 2-Methy1 phenyl 3-MethyIphenyl 4-Methylphenyl 2,4-Dimethylphenyl 4-lsopropylphenyl 4-tert.-ButyIphenyl IR: 2961, 2928, 2864,1615,1519, 1460,1445,1363, 1269,1193,819 No. Rl , R2 76 H 2-Methoxypheny1 77 H 4-Methoxypheny1 78 H 3,4-Dimethoxyphenyl 79 h 4-tert.-Butoxypheny1 80 H 2-TrifluoromethyIphenyl 81 H 3-TrifluoromethyIphenyl 82 H 4-TrifluoromethyIphenyl 83 H 4-Trifluoromethoxyphenyl 84 H 2-Fluorophenyl 85 H 3-Fluoropheny1 86 H 4-Fluoropheny1 87 H 2,4-Difluorophenyl 88 H 2-Chloropheny1 89 H 2-Chloro-4-fluorphenyl 90 H 3-Chloropheny1 91 h 4-Chloropheny1 92 H 2,4-Dichloropheny1 93 h 2,6-Dichloropheny1 94 H 3,5-Dichlorophenyl 95 H 2-Cyanopheny1 96 H 3-Cyanophenyl 20 900031 O.Z. 0050/41443 Physical data IR: 2960,2931,2863,1602,1519,1512,1456,1247, 1222,734 IR: 2952,2925,2863,1512,1461,1458,1255,1248, 1031,823 IR: 2961,2930,2864,1620,1521,1512, 1449, 1249, 1185,820,740 IR: 2960,2931,2865,1508,1540, 1220,1211,823, 711,571 IR: 2960,2929,2863,1600,1498,1448,1362, 1314, 826,814 IR: 2960,2929,2864,1592,1505,1461,1449,1362, 1321,827 No. R1 , R2 97 H 4-Cyanophenyl 98 H 2-Hydroxypheny1 99 H 3-Hydroxypheny1 100 H 4-Hydroxypheny1 101 H 2-Nitrophenyl 102 H 3-Nitrophenyl 103 H 4-Nitrophenyl 104 H Benzyl 105 H 2-Methylbenzy1 106 H 4-Methylbenzy1 107 H 2,4-Dimethylbenzy1 108 H 4-Isopropylbenzyl 109 H 4-tert.-Butylbenzy1 110 H 2-Methoxybenzy1 111 H 3-Methoxybenzy1 112 H 4-Methoxybenzy1 113 H 3,4-Dimethoxybenzy1 114 H 4-tert.-Butoxybenzy1 115 H 2-Trifluoromethylbenzy\ 116 H 3-Trifluoromethylbenzy1 117 H 4-Trifluoromethylbenzy1 118 H 4-Trif1uoromethoxybenzy1 119 H 2-Fluorobenzy1 120 H 3-Fluorobenzy1 21 900031 O.Z. 0050/41443 Physical data IR: 2961,2927,2862,1461,1452,1362, 827, 736, 698,572 IR: 2961,2925, 2863, 1509,1460, 1448, 1362, 825,571 IR: 2961,2927,28 64,1508,1490,1456,1363, 1229,828, 756 22 900031 O.Z. 0050/41443 R2 Physical data 4-Fluorobenzy1 IR: 2960,2927,2864, 1509,1462, 1449, 1362, 1221,827,572 2,4-Di fluorobenzyl 2-Chloro-4-fluorobenzyl 2-Chlorobenzy1 3-Chlorobenzy1 4-Chlorobenzyl 2.4-Dichlorobenzy1 Hydrochloride: IR: 2955,2863,2766,2721, 2574,1478,1469,825 2,6-Dichlorobenzy1 3.5-Dichlorobenzy1 2-Cyanobenzyl 4-Cyanobenzy1 2-Hydroxybenzy1 3-Hydroxybenzy1 4-Hydroxybenzy1 2-Nitrobenzy1 3-Nitrobenzy1 4-Ni trobenzy1 2,4-Dinitrobenzy1 2-Phenylethy1 2-(4-MethyIphenyl)ethyl 2-(4-tert.-ButyIphenyl)ethyl 2-(2-Methoxypheny1)ethy1 2-(4-Methoxyphenyl)e thy 1 2—(3,4-Dimethoxyphenyl)ethyl 2-(4-tert.-ButoxyphenylJethyl 23 No. R* , R2 Physical data 146 H 2- 4-Tri fluoromethoxyphenyl)ethyl 147 H 2- 3-Tri fluoromethyIphenyl)ethy 1 148 H 2- 2-FluorophenyI)ethyl 149 H 2- 4-Fluoropheny1)ethyl 150 H 2- 2-Chloropheny1)ethyl 151 H 2- 4-Chloropheny1)ethy1 152 H 2- 2,4-Dichloropheny1)ethyl 153 H 2- 2-Chloro-4-fluorophenyl)ethyl 154 H 2- 4-Cyanopheny1)ethyl 155 H 2- 4-Hydroxyphenyl)ethy 1 156 H 2- 4-Nitrophenyl)ethyl 157 H 3- henylpropy1 158 H 3- 4-MethyIphenyI)propy1 159 H 3- 4-tert.-ButyIpheny1Jpropyl 160 H 3- 2-Methoxyphenyl)propyl 161 H 3- 4-Methoxypheny1Jpropyl 162 H 3- 3,4-Dimethoxypheny1Jpropyl 163 H 3- 4-tert.-Butoxypheny1)propy1 164 H 3- 3-TrifluoromethylphenylJpropyl 165 H 3- 4-TrifluoromethoxyphenylJpropyl 166 H 3- 2-Fluoropheny1J propyl 167 H 3- 4-Fluoropheny1Jpropyl 168 H 3- 2-Chloropheny1J propy1 169 H 3- 4-Chloropheny1J propy1 170 H 3- 2,4-DichlorophenylJpropyl 171 H 3- 2-Chloro-4-fluorophenyIJ propy1 172 H 3- 4-Cyanopheny1Jpropyl 900031 O.Z. 0050/41443 3 ro <x ro CO ^>1 No. R1 R2 173 H 3-(4-hydroxyphenyl)propyl 174 H 3-(4-Ni trophenyl)propyl 175 Methyl 1-Penty1 176 Methy 1 2-Methy1-1-butyl 177 Methyl 2-Methy1-1-penty1 178 Methy 1 2-Ethy1-1-butyl 179 Methyl 2,2-Dimethy1-1-propy1 180 Methyl 3,3-Dimethyl-l-buty1 181 Methyl 3-Methy1-1-butyl 182 Methyl 1-Hexy1 183 Methyl 2-Methy1-1-hexy1 184 Methyl 2-Ethy1-1-hexyl 185 Methyl 2,4,4-Trimethyl-l-penty1 186 Methyl 1-Hepty1 187 Methyl 1-Octyl 188 Methy1 1-Nony1 189 Methyl 1-Decy1 190 Methy1 1-Uridecy 1 191 Methy 1 1-Dodecy1 192 Methyl 2-Propen-l-y1 193 Methy1 2-Buten-l-y1 194 Methy 1 2-Penten-l-yI 195 Methyl 2-Hexen-l-y1 196 Methy 1 3-Methy1-2-buten-l-y1 197 Methy1 2,3-Dimethy1-2-buten-l-y1 198 Methy 1 2-Hydroxyethy1 199 Methyl 6-Hydroxy-l-hexy1 900031 24 O.Z. 0050/41443 Physical data oil (cis/trans=l:3) 25 No. r! , R2 Physical data 200 Methy1 3-Chloro-l-buty1 201 Methyl 4-Chloro-l-buty1 202 Methyl 3-Chloro-2-methy1-1-propy1 203 Methyl Cyclopropyl 204 Methyl Cyclobutyl 205 Methyl Cyclopenty1 206 Methyl Cyclohexy1 207 Methyl Cycloheptyl 208 Methyl Cyclooctyl 209 Methyl Cyclodecy1 210 Methyl Cyclododecy1 211 Methyl 1-Methy1cyclopropyl 212 Methyl 1-MethyIcyc1 openty1 213 Methyl 1-MethyIcyclohexy1 214 Methy1 2-MethyIcyclohexyl 215 Methyl 3-MethyIcyclohexy1 216 Methyl 4-MethyIcyclohexyl 217 Methyl 2,2-Dimethylcyclohexyl 218 Methyl 3,3-DimethyIcyclohexyl 219 Methyl 4,4-Dimethylcyclohexyl 220 Methyl 2,6-DimethyIcyclohexyl 221 Methyl 3,3,5-Trimethy1 eye 1ohexy1 222 Methyl 3,3,5,5-TetramethyIcyclohexyl 223 Methy1 4-EthyIcyclohexyl 224 Methyl 4-PropyIcyclohexy1 225 Methy 1 4-IsopropyIcyclohexy1 226 Methyl 4-tert.-ButyIcyclohexyl 900031 O.Z. 0050/41443 o ro cm ro CO ->4 26 No. r! , r2 Physical data 227 Methyl cis-4-tert.-ButyIcyclohexy1 228 Methyl trans-4-tert.-ButyIcyc1ohexyI 229 Methyl 4-tert.-AmyIcyclohexyl 230 Methyl Bicyclo[2.2.1]-hept-2-yl 231 Methyl 1,7,7-Trimethyl-bicyclo[2.2.1]-hept-2-yl 232 Methyl Bicyclo[4.4.0]dec-2-yI 233 Methyl Bicyclo[4.4.0]dec-3-yl 234 Methyl 2,6,6-Trimethylbicyclo[3.1.1]-hept-3-yl 235 Methyl Phenyl 236 Methyl 2-MethyIphenyl 237 Methyl 3-MethyIpheny1 238 Methyl 4-MethyIphenyl 239 Methyl 2,4-DimethyIpheny1 240 Methyl 4-IsopropyIpheny1 241 Methy 1 4-tert.-ButyIpheny1 242 Methyl 2-MethoxyphenyI 243 Methyl 4-MethoxyphenyI 244 Methy1 3,4-Dimethoxypheny1 245 Methy 1 4-tert.-Butoxyphenyl 246 Methy 1 2-Tri fluoromethyIphenyI 247 Methy 1 3-Tri fluoromethyIpheny1 248 Methyl 4-Tri fluoromethyIpheny1 249 Methyl 4-Tri fluoromethoxyphenyl 250 Methyl 2-Fluoropheny1 251 Methy 1 3-Fluoropheny1 252 Methyl 4-Fluorophenyl 253 Methyl 2,4-Di fluoropheny1 900031 O.Z. 0050/41443 3 he om f\D CO 27 No. Rl , R2 Physical data 254 Methyl 2-Chlorophenyl 255 Methyl 2-Chloro-4-fluorpheny1 256 Methyl 3-Chloropheny1 257 Methyl 4-Chloropheny1 258 Methyl 2,4-Dichlorophenyl 259 Methyl 2,6-0ichlorophenyI 260 Methyl 3,5-Dichloropheny1 261 Methyl 2-Cyanophenyl 262 Methyl 3-Cyanophenyl 263 Methyl 4-Cyanophenyl 264 Methyl 2-Hydroxypheny1 265 Methyl 3-Hydroxyphenyl 266 Methyl 4-Hydroxypheny1 267 Methyl 2-Nitrophenyl 268 Methyl 3-Nitrophenyl 269 Methyl 4-Nitropheny1 270 Methyl Benzyl 271 Methyl 2-Methylbenzyl 272 Methy1 4-Methylbenzyl 273 Methyl 2,4-Dimethylbenzyl 274 Methyl 4-lsopropylbenzy1 275 Methyl 4-tert.-Butylbenzy1 276 Methy1 2-Methoxybenzy1 277 Methyl 3-Methoxybenzy1 278 Methy1 4-Methoxybenzy1 279 Methyl 3,4-Dimethoxybenzyl 280 Methyl 4-tert.-Butoxybenzyl 900031 O.Z. 0050/41443 3 rv> CM ro CO ■^4 28 No. r! , r2 Physical data 281 Methyl 2-Trifluoromethylbenzy1 282 Methyl 3-Tri fluoromethylbenzyl 283 Methyl 4-Tri fluoromethylbenzy1 284 Methyl 4-Tri fluoromethoxybenzyl 285 Methy I 2-Fluorobenzyl 286 Methy 1 3-Fluorobenzy1 287 Methy 1 4-Fluorobenzyl 288 Methy 1 2,4-Di fluorobenzy1 289 Methy 1 2-Chloro-4-fluorobenzy1 290 Methyl 2-Chlorobenzy1 291 Methyl 3-Chlorobenzy1 292 Methyl 4-Chlorobenzy1 293 Methy1 2,4-Dichlorobenzy1 294 Methyl 2,6-Dichlorobenzy1 295 Methyl 3,5-Dichlorobenzy1 296 Methy 1 2-Cyanobenzy1 297 Methy1 4-Cyanobenzy1 298 Methy1 2-Hydroxybenzy 1 299 Methy 1 3-HydroxybenzyI 300 Methyl 4-Hydroxybenzy I 301 Methy1 2-Nitrobenzy1 302 Methyl 3-Ni trobenzyl 303 Methy1 4-Nitrobenzyl 304 Methy1 2,4-Dinitrobenzyl 305 Methy1 2-Phenylethy1 306 Methyl 2-(4-MethyIphenyl)ethyl 307 Methy1 2-(4-tert.-ButyIpheny1)ethyl 900031 O.Z. 0050/41443 0 ro to CO 29 No. r! , R2 Physical data 308 Methyl 2- 2-Methoxypheny1)ethyI 309 Methy1 2- 4-Methoxypheny1)ethyl 310 Methyl 2- 3,4-DimethoxyphenyI)ethyl 311 Methyl 2- 4-tert.-Butoxypheny1)ethy1 312 Methyl 2- 4-Tri fluoromethoxypheny1)ethyl 313 Methyl 2- 3-Tri fluoromethyIphenyl)ethyl 314 Methyl 2- 2-Fluoropheny1)ethyl 315 Methyl 2- 4-Fluoropheny1)ethyl 316 Methyl 2- 2-Chlorophenyl)ethyl 317 Methyl 2- 4-Chloropheny1)ethyl 318 Methyl 2- 2,4-Dichlorophenyl)ethy1 319 Methyl 2- 2-Chloro-4-fluorophenyl)ethyl 320 Methyl 2- 4-Cyanopheny1)ethy1 321 Methyl 2- 4-Hydroxyphenyl)ethyl 322 Methyl 2- 4-Ni tropheny1)ethy1 323 Methyl 3- henyIpropyl 324 Methy I 3- 4-MethyIphenylJpropyl 325 Methyl 3- 4-tert.-ButylphenylJpropyl 326 Methy1 3- 2-Methoxypheny1Jpropyl 327 Methyl 3- 4-Methoxypheny1Jpropyl 328 Methyl 3- 3,4-Dimethoxypheny1Jpropyl 329 Methy1 3- 4-tert.-Butoxypheny1Jpropyl 330 Methy1 3- 3-Tri fluoromethyIpheny1Jpropyl 331 Methyl 3- 4-Tri fluoromethoxyphenylJpropyl 332 Methyl 3- 2-FluorophenylJpropyl 333 Methyl 3- 4-Fluoropheny1Jpropyl 334 Methyl 3- 2-ChlorophenylJpropyl 900031 O.Z. 0050/41443 3 rv> CM ro co 30 No. Rl , R2 Physical data 335 Methyl 3-(4-Ch1oropheny1)propy1 336 Methyl 3-(2,4-DichlorophenylJpropyl 337 Methyl 3-(2-Chloro-4-fluorophenylJpropyl 338 Methyl 3-(4-CyanophenylJpropyl 339 Methyl 3-(4-HydroxyphenylJpropyl 340 Methyl 3-(4-NitrophenylJpropyl 341 Ethyl 1-Pentyl 342 Ethyl 2-Methyl-l-buty1 343 Ethyl 2-Methyl-l-pentyl 344 Ethyl 2-Ethy1-1-butyl 345 Ethyl 2,2-Dimethyl-l-propyl 346 Ethyl 3,3-Dimethyl-l-buty1 347 Ethyl 3-Methyl-l-butyI 348 Ethyl 1-Hexy1 349 Ethy 1 2-Methy1-1-hexy1 350 Ethyl 2-Ethy1-1-hexyl 351 Ethyl 2,4,4-Trimethy1-1-pentyl 352 Ethyl 1-Hepty1 353 Ethyl 1-Octyl 354 Ethyl 1-Nony1 355 Ethyl 1-Decyl 356 Ethyl 1-Undecy1 357 Ethyl 1-Dodecy1 358 Ethyl 2-Propen-l-y1 359 Ethyl 2-Buten-l-y1 360 Ethy 1 2-Penten-l-yl 361 Ethyl 2-Hexen-l-y1 900031 O.Z. 0050/41443 3 rv> CM ro CO 31 No. r! , R2 Physical data 362 Ethyl 3-Methy1-2-buten-1-y1 363 Ethyl 2,3-Dimethy1-2-buten-l-y1 364 Ethyl 2-Hydroxyethy1 365 Ethyl 6-Hydroxy-l-hexy1 366 Ethyl 3-Chloro-l-butyl 367 Ethyl 4-Chloro-1-buty1 368 Ethyl 3-Chloro-2-methy1-1-propy1 369 Ethyl Cyclopropyl 370 Ethyl Cyclobutyl 371 Ethyl Cyc lopenty1 372 Ethyl Cyclohexy1 373 Ethyl Cycloheptyl 374 Ethyl Cycloocty1 375 Ethyl Cyclodecy1 376 Ethyl Cyclododecyl 377 Ethyl 1-MethyIcyclopropyl 378 Ethyl 1-MethyIcyclopenty1 379 Ethyl 1-MethyIcyclohexy1 380 Ethyl 2-MethyIcyclohexyl 381 Ethyl 3-MethyIcyclohexyl 382 Ethyl 4-MethyIcyclohexy1 383 Ethyl 2,2-Dimethylcyclohexyl 384 Ethyl 3,3-DimethyIcyclohexyl 385 Ethyl 4,4-Dimethylcyclohexyl 386 Ethyl 2,6-0imethyIcyclohexyl 387 Ethyl 3,3,5-TrimethyIcyclohexy1 388 Ethyl 3,3,5,5-Tetramethylcyclohexyl 900031 O.Z. 0050/41443 3 ro Cm ro co ^4 32 900031 O.Z. 0050/41443 3 No. R1 , R^ Physical data 389 Ethyl , 4-EthyIcyclohexy1 390 Ethyl 4-PropyIcyclohexyl 391 Ethyl 4-IsopropyIcyclohexy1 392 Ethyl 4-tert.-ButyIcyclohexy1 393 Ethyl c is-4-tert.-ButyIcyclohexy1 394 Ethyl trans-4-tert.-Butylcyclohexyl H 395 Ethyl 4-tert.-AmyIcyclohexy1 396 Ethyl Bicyclo[2.2.1j-hept—2-y1 397 Ethyl 1,7,7-Trimethyl-bicyclo[2.2.1]-hept-2-yl 398 Ethyl Bicyclo[4.4.0]dec-2-yl 399 Ethyl Bicyclo[4.4.0]dec-3-yl 400 Ethyl 2,6,6-Trimethylbicyclo[3.1.1]-hept-3-y1 401 Ethyl Phenyl 402 Ethyl 2-MethyIpheny1 403 Ethyl 3-MethyIpheny1 404 Ethyl 4-MethyIphenyl 405 Ethyl 2,4-DimethyIphenyl 406 Ethyl 4-Isopropylphenyl 407 Ethyl 4-tert.-ButyIphenyl 408 Ethyl 2-Methoxypheny1 409 Ethyl 4-Methoxypheny1 410 Ethyl 3,4-Dimethoxypheny1 411 Ethyl 4-tert.-Butoxypheny1 412 Ethyl 2-Tri fluoromethylphenyl 413 Ethyl 3-Tri fluoromethyIphenyl 414 Ethyl 4-Tri fluoromethylphenyl 415 Ethyl 4-Tri fluoromethoxyphenyl Hydrochloride mp. 185-186°C rv> oj ro co 33 r2 Physical data 416 Ethyl 2-Fluoropheny1 417 Ethyl 3-Fluoropheny1 418 Ethyl 4-Fluoropheny1 419 Ethyl 2,4-Di fluoropheny1 420 Ethyl 2-Chlorophenyl 421 Ethyl 2-Chloro-4-fluoropheny1 422 Ethyl 3-Chloropheny1 423 Ethyl 4-Chloropheny1 424 Ethyl 2,4-Dichlorophenyl 425 Ethyl 2,6-DichlorophenyI 426 Ethyl 3,5-Dichloropheny1 427 Ethyl 2-Cyanophenyl 428 Ethyl 3-Cyanopheny1 429 Ethyl 4-Cyanopheny1 430 Ethyl 2-Hydroxypheny1 431 Ethyl 3-Hydroxypheny1 432 Ethyl 4-Hydroxypheny1 433 Ethyl 2-Nitrophenyl 434 Ethyl 3-Nitropheny1 435 Ethyl 4-Ni tropheny1 436 Ethyl Benzyl 437 Ethyl 2-Methylbenzy1 438 Ethyl 4-Methylbenzy1 439 Ethyl 2,4-DimethylbenzyI 440 Ethyl 4-Isopropylbenzy1 441 Ethyl 4-tert.-Butylbenzyl 442 Ethyl 2-Methoxybenzy1 900031 O.Z. 0050/41443 3 CM ro co 34 No. r! , R2 Physical data 443 Ethyl 3-Methoxybenzy1 444 Ethyl 4-Methoxybenzy1 445 Ethyl 3,4-Dimethoxybenzy1 446 Ethyl 4-tert.-Butoxybenzyl • 447 Ethyl 2-Tri fluoromethylbenzy1 448 Ethyl 3-Tri fluoromethylbenzy1 449 Ethyl 4-Tri fluoromethylbenzy1 450 Ethyl 4-Tri fluoromethoxybenzy1 451 Ethyl 2-Fluorobenzy1 452 Ethyl 3-FluorobenzyI 453 Ethyl 4-Fluorobenzy1 454 Ethyl 2,4-Difluorobenzyl 455 Ethyl 2-Chloro-4-fluorobenzy1 456 Ethyl 2-Chlorobenzy1 457 Ethyl 3-Chlorobenzy1 458 Ethyl 4-Chlorobenzy1 459 Ethyl 2,4-Dichlorobenzy1 460 Ethyl 2,6-Dichlorobenzy1 461 Ethyl 3,5-Dichlorobenzyl 462 Ethyl 2-Cyanobenzy1 463 Ethyl 4-Cyanobenzy1 464 Ethyl 2-Hydroxybenzy1 465 Ethyl 3-Hydroxybenzy1 466 Ethyl 4-HydroxybenzyI 467 Ethyl 2-Nitrobenzyl 468 Ethyl 3-Nitrobenzyl 469 Ethyl 4-Nitrobenzyl 900031 O.Z. 0050/41443 3 ho €w ^<J ro CO "VJ 35 No. R* , R2 Physical data 470 Ethyl 2, 4-Dinitrobenzyl 471 Ethyl 2- Phenylethyl 472 Ethyl 2- (4-MethyIpheny1)ethy1 473 Ethyl 2- (4-tert.-Butylpheny1)ethy1 474 Ethyl 2- (2-Methoxypheny1)ethyl 475 Ethyl 2- (4-Methoxypheny1)ethyl 476 Ethyl 2- (3,4-Dimethoxypheny1)ethyl 477 Ethyl 2- (4-tert.-Butoxyphenyl)ethyl 478 Ethyl 2- (4-Tri fluoromethoxyphenyl)ethy1 479 Ethyl 2- (3-Tri fluoromethyIpheny1)ethyl 480 Ethyl 2- (2-Fluoropheny1)ethy1 481 Ethyl 2- (4-Fluoropheny1)ethyl 482 Ethyl 2- (2-Chlorophenyl)ethyl 483 Ethyl 2- (4-Chlorophenyl)ethyl 484 Ethyl 2- (2,4-Dichlorophenyl)ethy1 485 Ethyl 2- (2-Chloro-4-fluoropheny1jethyl 486 Ethyl 2- (4-Cyanopheny1)ethyl 487 Ethyl 2- (4-Hydroxypheny1)ethyI 488 Ethyl 2- (4-Nitropheny1Jethyl 489 Ethyl 3- Pheny1propy1 490 Ethyl 3- (4-MethyIphenylJpropyl 491 Ethyl 3- (4-tert.-ButyIphenylJpropyl 492 Ethyl 3- (2-Methoxypheny1Jpropyl 493 Ethy! 3- (4-Methoxypheny1Jpropyl 494 Ethyl 3- (3,4-Dimethoxypheny1Jpropyl 495 Ethyl 3- (4-tert.-Butoxypheny1Jpropyl 496 Ethyl 3- (3-Tri fluoromethylphenyljpropyl 900031 O.Z. 0050/41443 3 fo Cm f\3 CO 36 No. R* , R2 Physical data 497 Ethyl , 3-(4-Tri fluoromethoxypheny1)propyl 498 Ethyl 3-(2-FluorophenylJpropyl 499 Ethyl 3-(4-Fluoropheny1Jpropyl 500 Ethyl 3-(2-Chloropheny1Jpropyl 501 Ethyl 3-(4-Chloropheny1Jpropyl 502 Ethyl 3-(2,4-DichlorophenylJpropyl 503 Ethyl 3-(2-Chloro-4-fluoropheny1Jpropyl 504 Ethyl 3-(4-Cyanopheny1Jpropyl 505 Ethyl 3-(4-HydroxyphenylJpropyl 506 Ethyl 3-(4-NitrophenylJpropyl 507 1-Propy1 1-Penty1 508 1-Propy1 2-Methyl-l-buty1 509 1-PropyI 2-Methy1-1-penty1 510 1-Propy1 2-Ethy1-1-butyl 511 1-Propy1 2, 2-Dimethy1-1-propyI 512 1-Propyl 3,3-Dimethyl-l-buty1 513 1-Propy1 3-Methyl-l-buty1 514 1-Propyl 1-Hexyl 515 1-Propyl 2-Methy1-1-hexy1 516 1-Propyl 2-Ethy1-1-hexyl 517 1-Propyl 2,4,4-Trimethyl-l-penty1 518 1-Propyl 1-HeptyI 519 1-Propyl l-0cty1 520 1-Propyl 1-Nony1 521 1-Propyl 1-Decy1 522 1-Propyl 1-Undecy1 523 1-Propyl 1-Dodecy1 900031 O.Z. 0050/41443 3 ro Osl ro CO 37 Physical data 524 1-Propyl 2-Propen-l-y1 525 1-Propyl 2-Buten-l-y1 526 1-Propyl 2-Penten-l-y1 527 1-Propyl 2-Hexen-l-y1 528 1-Propyl 3-Methy1-2-buten-l-y1 529 1-Propy1 2,3-Dimethy1-2-buten-l-y1 530 1-Propyl 2-Hydroxyethy1 531 1-Propyl 6-Hydroxy-l-hexy1 532 1-Propyl 3-Chloro-l-buty1 533 1-Propyl 4-Chloro-l-buty1 534 1-PropyI 3-Chloro-2-methy1-1-propyI 535 1-Propyl Cyclopropyl 536 1-Propyl Cyclobuty 1 537 1-Propy1 Cyclopenty1 538 1-Propyl Cyclohexy 1 539 1-Propyl Cyclohepty 1 540 1-Propyl Cyclooctyl 541 1-Propyl Cyclodecy 1 542 1-Propyl Cyclododecy1 543 1-Propyl 1-Methylcyclopropyl 544 1-Propy1 1-MethyIcyclopenty 1 545 1-Propyl 1-MethyIcyclohexyl 546 1-Propyl 2-MethyIcyclohexy1 547 1-Propyl 3-Methy1cyc1ohexy 1 548 1-Propyl 4-MethyIcyclohexy1 549 1-Propyl 2,2-DimethyIcyclohexyl 550 1-Propyl 3,3-DimethyIcyclohexy1 900031 O.Z. 0050/41443 3 rv> CM ro co 38 900031 O.Z. 0050/41443 0 NO. Physical data 551 1-Propyl 4,4-Dimethylcyclohexyl 552 1-Propyl 2,6-Dimethylcyclohexyl 553 1-Propyl 3,3,5-Trimethylcyclohexyl 554 1-Propyl 3,3,5,5-TetramethyIcyclohexy1 555 1-Propyl 4-EthyIcyclohexyl 556 1-Propyl 4-PropyIcyclohexyl 557 1-Propyl 4-1 sopropyIcyclohexy1 558 1-Propyl 4-tert.-ButyIcyclohexyl 559 1-Propyl cis-4-tert.-ButyIcyclohexyl 560 1-Propyl trans-4-tert.-ButyIcyclohexy1 bp 230-236°C/0.2 mbar 561 1-Propyl 4-tert.-AmyIcyclohexyl 562 1-Propyl Bicyclo[2.2.1]-hept-2-yl 563 1-Propyl 1,7,7-Trimethy1-bicyclo[2.2.1]-hept-2-yl 564 1-Propyl Bicyclo[4.4.0]dec-2-yl 565 1-Propyl Bicyclo[4.4.0]dec-3-yl 566 1-Propyl 2,6,6-Trimethylbicyclo[3.1.1]-hept-3-y1 567 1-Propyl Phenyl 568 1-Propyl 2-MethyIpheny1 569 1-Propyl 3-Methylphenyl 570 1-Propyl 4-MethyIpheny1 571 1-Propyl 2,4-Dimethylpheny1 572 1-Propyl 4-IsopropyIphenyl 573 1-Propyl 4-tert.-ButyIpheny1 574 1-Propyl 2-Methoxypheny1 575 1-Propyl 4-Methoxyphenyl 576 1-Propyl 3,4-Dimethoxypheny1 577 1-Propyl 4-tert.-Butoxyphenyl Cm ro CO 39 No. R1 578 1-Propyl 579 1-Propyl 580 1-Propyl 581 1-Propyl 582 1-Propyl 583 1-Propyl 584 1-Propyl 585 1-Propyl 586 1-Propyl 587 1-Propyl 588 1-Propyl 589 1-Propyl 590 1-Propyl 591 1-Propyl 592 1-Propyl 593 1-Propyl 594 1-Propyl 595 1-Propyl 596 1-Propyl 597 1-Propyl 598 1-Propy1 599 1-Propyl 600 1-Propyl 601 1-Propyl 602 1-Propyl 603 1-Propyl 604 1-Propyl R2 2-Tri fluoromethyIpheny1 3-Tri fluoromethylphenyl 4-Tri fluoromethyIpheny1 4-Tri fluoromethoxyphenyl 2-Fluorophenyl 3-Fluoropheny1 4-F1uoropheny1 2,4-Di fluorophenyI 2-Chlorophenyl 2-Chloro-4-fluoropheny1 3-Chlorophenyl 4-Chloropheny1 2.4-Dichlorophenyl 2,6-Dichloropheny1 3.5-Dichlorophenyl 2-Cyanopheny1 3-Cyanopheny1 4-Cyanopheny1 2-Hydroxypheny1 3-Hydroxypheny 1 4-Hydroxypheny1 2-Ni tropheny1 3-Nitropheny1 4-Nitrophenyl Benzyl 2-Methylbenzyl 4-Methylbenzy1 Physical data 900031 O.Z. 0050/41443 3 ro CM ro CO 40 Physical data 605 1-Propyl 2,4-Dimethylbenzy1 606 1-PropyI 4-Isopropylbenzy1 607 1-Propyl 4-tert.-Butylbenzy1 608 1-Propyl 2-Methoxybenzyl 609 1-Propyl 3-Methoxybenzyl 610 1-Propyl 4-Methoxybenzy1 611 1-Propyl 3,4-Dimethoxybenzy1 612 1-Propyl 4-tert.-Butoxybenzy1 613 1-Propyl 2-Tri fluoromethylbenzy1 614 1-Propyl 3-Tri fluoromethylbenzy1 615 1-Propyl 4-Tri fluoromethy I benzyl 616 1-Propyl 4-Tri fluoromethoxybenzyl 617 1-Propyl 2-Fluorobenzy1 618 1-Propyl 3-Fluorobenzyl 619 1-Propyl 4-Fluorobenzy1 620 1-Propy1 2,4—D ifluorobenzyI 621 1-Propyl 2-Chloro-4-fluorobenzy1 622 1-Propyl 2-Chlorobenzy1 623 1-Propyl 3-Chlorobenzy1 624 1-Propyl 4-Chlorobenzy1 625 1-Propyl 2,4-DichlorobenzyI 626 1-Propyl 2,6-Dichlorobenzy1 627 1-Propyl 3,5-Dichlorobenzy1 628 1-Propyl 2-Cyanobenzy1 629 1-Propyl 4-Cyanobenzy1 630 1-Propyl 2-Hydroxybenzy1 631 1-Propyl 3-Hydroxybenzyl 900031 O.Z. 0050/41443 3 Cn t\J CO *vj 41 No. r! t R2 Physical data 632 1-Propyl 4-Hydroxybenzy1 633 1-Propyl 2- Ni trobenzy1 634 1-Propyl 3- Nitrobenzy1 635 1-Propyl 4- Nitrobenzy1 636 1-Propy1 2, 4-Di n i trobenzy1 637 1-Propyl 2- Phenylethyl 638 1-Propyl 2- (4-MethyIpheny1)ethyl 639 1-Propyl 2- (4-tert.-ButyIpheny1)ethy1 640 1-Propyl 2~ (2-Methoxypheny1)ethy1 641 1-Propyl 2- (4-Methoxypheny1)ethyl 642 1-Propyl 2- (3,4-Dimethoxypheny1)ethy1 643 1-Propyl 2- (4-tert .-Butoxypheny1)ethy1 644 1-Propyl 2- (4-Tri fluoromethoxyphenyl)ethyl 645 1-Propyl 2- (3-Tri fluoromethyIpheny1)ethyl 646 1-Propy1 2- (2-Fluorophenyl)ethy1 647 1-Propyl 2- (4-Fluorophenyl)ethyI 648 1-Propy1 2- -(2-Ch1 oropheny1)ethy1 649 1-Propyl 2- -(4-Chlorophenyl)ethy1 650 1-Propyl 2- -(2,4-Dichlorophenyl)ethy1 651 1-Propyl 2- (2-Chloro-4-fluorophenyl)ethyl 652 1-Propyl 2- -(4-Cyanopheny1)ethyl 653 1-Propyl 2- -(4-Hydroxypheny1)ethyl 654 1-Propyl 2- (4-Ni tropheny1)ethyl 655 1-Propyl 3- -Phenylpropyl 656 1-Propyl 3- -(4-Methy 1pheny1)propyl 657 1-Propyl 3- -(4-tert.-ButyIphenylJpropyl 658 1-Propyl 3- -(2-Methoxypheny1)propy1 900031 O.Z. 0050/41443 3 ro Cm ro co ^4 • . 42 No. R1 r2 Physic 659 1- -Propy1 3- (4-Methoxypheny1Jpropyl 660 1- -Propyl 3- (3, 4-Dimethoxypheny1}propyI 661 1- -Propyl 3- (4-tert.-ButoxyphenylJpropyl 662 1- -Propyl 3- (3-Tri fluoromethyIpheny1Jpropyl 663 1- -Propyl 3- (4-Tri fluoromethoxyphenylJpropyl 664 1- -Propyl 3- (2-Fluoropheny1Jpropyl 665 1- -Propyl 3- (4-Fluoropheny1Jpropyl 666 1- -Propyl 3- (2-ChlorophenylJpropyl 667 1- -Propyl 3- (4-Chloropheny1Jpropyl 668 1- -Propyl 3- (2, 4-DichlorophenylJpropyl 669 1- -Propyl 3- (2-Chloro-4-fluorophenylJpropyl 670 1- -Propyl 3- (4-Cyanopheny1Jpropyl 671 1- -Propyl 3- (4-HydroxyphenylJpropyl 672 1- -Propyl 3- (4-NitrophenylJpropyl 673 2- -Propen- -y! Methyl 674 2- -Propen- -yi Ethyl 675 2- -Propen- -yi 1- Propyl 676 2- -Propen- -yi 2- Propyl 677 2- -Propen- -yi 1- Butyl 678 2- -Propen- 2- Butyl 679 2- -Propen- -yi tert.-Buty1 680 2- -Propen- -yi 2- Methyl-l-propyl 681 2- -Propen- -yi 1- Penty1 682 2- -Properi- -yi 2- Methyl-l-buty1 683 2- -Propen- -yi 2-Methy1-1-penty1 684 2- -Propen- -yi 2- Ethy1-1-butyl 685 2- -Propen- -yi 2, 2-Dimethyl-l-propyl 900031 O.Z. 0050/41443 3 data r>o CM ro CO 43 No. r! R2 Physical data 686 2-Propen- -yi 3,3-Dimethyl-l-buty1 687 2-Propen- -yi 3-Methy1-1-butyl 688 2-Propen- -yi 1-Hexy1 689 2-Propen- -yi 2-Methy1-1-hexy1 690 2-Propen- ~y i 2-Ethy1-1-hexy1 691 2-Propen- -yi 2,4,4-Trimethy1-1-penty1 692 2-Propen- -yi 1-Hepty1 693 2-Propen- -yi 1-Octy1 694 2-Propen- -yi 1-Nonyl 695 2-Propen- -yi 1-Decy1 696 2-Propen- -yl 1-Undecyl 697 2-Propen- -yi 1-Dodecy1 698 2-Propen- -yi 2-Propen-l-y1 699 2-Propen- -yi 2-Buten-l-y1 700 2-Propen- -yi 2-Penten-l-y1 701 2-Propen- -yi 2-Hexen-l-y1 702 2-Propen- -yi 3-Methy1-2-buten-l-y1 703 2-Propen- -yi 2,3-Dimethy1-2-buten-l-y1 704 2-Propen- -yi 2-Hydroxyethy1 705 2-Propen- -yi 6-Hydroxy-l-hexy1 706 2-Propen- -yi 3-Chloro-l-buty1 707 2-Propen- -yi 4-Chloro-l-buty1 708 2-Propen- -yt 3-Chloro-2-methy 1-1-propy1 709 2-Propen- -yi Cyclopropyl 710 2-Propen- -yi Cyclobuty1 711 2-Propen- -yi Cyclopentyl 712 2-Propen- -yi Cyclohexyl 900031 O.Z. 0050/41443 3 ro cm ro <o 44 No. r! , r2 Physical data 713 2-Propen-l-y1 Cycloheptyl 714 2-Propen-l-y1 Cyclooctyl 715 2-Propen-l-y1 Cyclodecyl 716 2-Propen-l-y1 Cyclododecyl 717 2-Propen-l-y1 1-Methylcyclopropyl 718 2-Propen-l-y1 1-Methylcyclopentyl 719 2-Propen-l-y1 1-MethyIcyclohexy1 720 2-Propen-l-y1 2-MethyIcyclohexyl 721 2-Propen-l-y1 3-MethyIcyclohexyl 722 2-Propen-l-y1 4-Methylcyclohexy1 723 2-Propen-l-y1 2,2-DimethyIcyclohexyl 724 2-Propen-l-y1 3,3-DimethyIcyclohexyl 725 2-Propen-l-y1 4,4-DimethyIcyclohexyl 726 2-Propen-l-y1 2,6-DimethyIcyclohexyl 727 2-Propen-l-y1 3,3,5-TrimethyIcyclohexyl 728 2-Propen-l-yI 3,3, 5, 5-TetramethyIcyclohexyI 729 2-Propen-l-yI 4-Ethylcyclohexyl 730 2-Propen-l-y1 4-Propylcyclohexy1 731 2-Propen-l-y1 4-IsopropyIcyclohexy1 732 2-Propen-l-y1 4-tert.-ButyIcyclohexy1 733 2-Propen-l-y1 cis-4-tert.-ButyIcyclohexy1 734 2-Propen-l-y1 trans-4-tert.-ButyIcyc1ohexy1 resin (cis/trans 735 2-Propen-l-y1 4-tert.-Amylcyclohexyl 736 2-Propen-l-y1 Bicyclo[2.2.1]-hept-2-yl 737 2-Propen-l-y1 1,7, 7-Trimethy1-bicyclo[2.2.1]-hept-2-y1 738 2-Propen-l-y1 Bicyclo[4.4.0]dec-2-yl 739 2-Propen-l-y1 Bicyclo[4.4.0]dec-3-yl 900031 O.Z. 0050/41443 3 2:3) ro CM ro co 45 No. R1 r2 Physical 740 2-Propen- -yi 2,6,6-Trimethylbicyclo[3.1•1]-hept-3-y1 741 2-Propen- -yi Phenyl 742 2-Propen- -yi 2-MethyIpheny1 743 2-Propen- -yi 3-MethyIpheny1 744 2-Propen- -yi 4-MethyIphenyl 745 2-Propen- -yl 2,4-DimethyIphenyl 746 2-Propen- -y\ 4-lsopropyIpheny1 747 2-Propen- -yi 4-tert.-ButyIphenyl 748 2-Propen- -yl 2-Methoxypheny1 749 2-Propen- -yi 4-Methoxypheny1 750 2-Propen- -yi 3,4-Dimethoxypheny1 751 2-Propen- -yi 4-tert.-Butoxypheny1 752 2-Propen- -yi 2-Tri fluoromethyIpheny1 753 2-Propen- -yi 3-Tri fluoromethyIphenyl 754 2-Propen- -yi 4-Tri fluoromethyIpheny1 755 2-Propen- -yi 4-Tri fluoromethoxyphenyl 756 2-Propen- -yi 2-Fluoropheny1 757 2-Propen- -yi 3-Fluoropheny1 758 2-Propen- -yi 4-Fluoropheny1 759 2-Propen- -yi 2,4-Di fluoropheny 1 760 2-Propen- -yi 2-Chloropheny1 761 2-Propen- -yi 2-Chloro-4-fluoropheny 1 762 2-Propen- -yi 3-Chloropheny1 763 2-Propen- -yi 4-Chloropheny1 764 2-Propen- -yi 2, 4-Dichi oropheny1 765 2-Propen- -yi 2, 6-Dichlorophenyl 766 2-Propen- -yl 3,5-Dichlorophenyl 900031 O.Z. 0050/41443 0 !>0 Oi ro CO 46 Physical data 767 2- -Propen- -yi 2-Cyanophenyl 768 2- -Propen- -y I 3-Cyanopheriy 1 769 2- -Properi- -yi 4-Cyanopheny1 770 2- -Propen- -yi 2-Hydroxypheny1 771 2- ■Propen- -yi 3-Hydroxypheny1 772 2- -Propen- -y l 4-Hydroxypheny1 773 2- -Propen- -yl 2-Ni tropheny1 774 2- -Propen- -yi 3-Nitropheny1 775 2- -Propen- -yl 4-Nitrophenyl 776 2- -Propen- -yi Benzyl 777 2- -Propen- -yl 2-Methylbenzy1 778 2- -Properi- -yi 4-Methylbenzyl 779 2- -Propen- -yl 2,4-Dimethylbenzyl 780 2- -Propen- -yi 4-isopropylbenzyl 781 2- -Propen- -yi 4-tert.-Butylbenzyl 782 2- -Propen- -yl 2-Methoxybenzy1 783 2- -Propen- -yi 3-Methoxybenzy1 784 2- -Propen- -yi 4-Methoxybenzyl 785 2- -Propen- -yi 3,4-Dimethoxybenzy1 786 2- -Propen- -yl 4-tert.-Butoxybenzy1 787 2- -Propen- -yi 2-Tri fluoromethylbenzy1 788 2- -Propen- -yi 3-Tri fluoromethylbenzyl 789 2- -Propen- -yi 4-Tri fluoromethylbenzyl 790 2- -Propen- -yi 4-Tri fluoromethoxybenzyl 791 2- -Propen- -yi 2-Fluorobenzy1 792 2- -Propen- -yi 3-Fluorobenzy1 793 2 -Propen- -yi 4-Fluorobenzy1 900031 O.Z. 0050/41443 3 no CM no <o 47 No. R1 R2 Physical data 794 2-Propen- -yi 2,4-Di fluorobenzyl 795 2-Propen- -yi 2-Chloro-4-fluorobenzy1 796 2-Propen- -yi 2-Chlorobenzy1 797 2-Propen- -yi 3-Chlorobenzy1 798 2-Propen- -yi 4-Chlorobenzy1 799 2-Propen- -yi 2,4-Dichlorobenzyl 800 2-Propen- -yi 2,6-Dichlorobenzy1 801 2-Propen- -yi 3,5-Dichlorobenzyl 802 2-Propen- -yi 2-Cyanobenzy1 803 2-Propen- -yi 4-Cyanobenzy1 804 2-Propen- -yi 2-Hydroxybenzy1 805 2-Propen- -yi 3-Hydroxybenzy1 806 2-Propen- -yi 4-Hydroxybenzy1 807 2-Propen- -yi 2-Nitrobenzyl 808 2-Propen- -yi 3-Nitrobenzyl 809 2-Propen- -yl 4-Ni trobenzy1 810 2-Propen- -yi 2,4-Dinitrobenzyl 811 2-Propen- -yi 2-Pheny lethyl 812 2-Propen- -yi 2-(4-MethyIpheny1)ethyl 813 2-Propen- -yi 2-(4-tert.-ButyIpheny1)ethy1 814 2-Properi- -yi 2-(2-Methoxypheny1)ethy1 815 2-Propen- -yi 2-(4-Methoxypheny1)ethyl 816 2-Propen- -yl 2-(3,4-Dimethoxypheny1jethy1 817 2-Propen- -yi 2-(4-tert.-Butoxypheny1)ethy1 818 2-Propen- -yi 2-(4-Tri fluoromethoxyphenyl)ethy1 819 2-Propen- -yi 2-(3-Tri fluoromethyIpheny1)ethyl 820 2-Propen- -yi 2-(2-Fluorophenyl)ethyl 900031 O.Z. 0050/41443 3 ro CM vj ro co 48 No. r1 R2 Physical data 821 2- Propen- -yl 2- 4-Fluoropheny1)ethy1 822 2- Propen- -yi 2- 2-Ch1oropheny1)ethy1 823 2- Propen- -yi 2- 4-Chloropheny1)ethy1 824 2- Propen- -yi 2- 2,4-Dichloropheny1)ethy1 825 2- Propen- -yi 2- 2-Chloro-4-fluorophenyl)ethy1 826 2- Propen- -yi 2- 4-Cyanopheny1)ethy1 827 2- propen- -yi 2- 4-Hydroxypheny1)ethy1 828 2- Propen- -yi 2- 4-Nitrophenyl)ethyl 829 2- -Propen- -yl 3-Phenylpropyl 830 2- -Propen- -yi 3- 4-MethyIphenylJpropyl 831 2- -Properi- -yi 3- 4-tert.-ButyIpheny1Jpropyl 832 2- -Propen- -yi 3- 2-MethoxyphenylJpropyl 833 2- -Propen- -yi 3- 4-Methoxypheny1Jpropyl 834 2- -Propen- -yi 3- 3,4-Dimethoxypheny1Jpropyl 835 2- -Propen- -yi 3- 4-tert.-Butoxypheny1J propy1 836 2- -Propen- -yi 3- 3-Tri fluoromethyIpheny1J propyl 837 2 -Properi- -yi 3- 4-Tri fluoromethoxyphenylJpropyl 838 2- -Propen- -yi 3- 2-FluorophenylJpropyl 839 2 -Propen- -yi 3- 4-FluorophenylJ propyl 840 2 -Propen- -yi 3- 2-ChlorophenylJpropyl 841 2 -Propen- -yi 3- 4-Chloropheny1Jpropyl 842 2 -Propen- -yi 3- 2,4-DichlorophenylJ propyl 843 2 -Properi- -yi 3- 2-Chloro-4-fluoropheny1Jpropyl 844 2 -Properi- -yi 3- 4-Cyanopheny1J propy1 845 2 -Propen- -yi 3- 4-Hydroxypheny1Jpropyl 846 2 -Propen- -yl 3- 4-NitrophenylJpropyl 900031 O.Z. 0050/41443 ""V J ro CNf ro CO VI 2372 9 7 49 O.Z. 0050/41443 In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides. 5 The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in 10 vegetables such as cucumbers, beans and cucurbits. The novel compounds are particularly useful for controlling the following plant diseases: 15 Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, Uncinula necator in vines, Puccinia species in cereals, 20 Rhizoctonia solani in cotton, Ustilago species in cereals and sugar cane, venturia inaequalis (scab) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, 25 Botrytis cinerea (gray mold) in strawberries and grapes, Cercospora arachidicola in groundnuts, Pseudocercosporella herpotrichoides in wheat and barley, Pyricularia oryzae in rice, Phytophthora infestans in potatoes and tomatoes, 30 Fusarium and Verticillium species in various plants, Plasmopara viticola in grapes, Alternaria species in fruit and vegetables. The compounds are applied by spraying or dusting the plants with the 35 active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi themselves, or the plants, seeds, materials or the soil to be protected against fungus attack are treated with a fungicidally effective amount of the active ingredient. 40 The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of eraulsifiers and dispersants; if water 23 7 2 50 O.Z. 0050/41443 is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chloro-benzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., 5 methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethy 1-10 ene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) ; and dispersants such as 1igninsulfite waste liquors and methyIcellulose. The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt% of active ingredient. The application rates are from 0.02 to 3 15 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials (timber), e.g., on Paecilomyces variotii. When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 20, g per kg of seed are generally required. 20 25 The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering. Examples of formulations are given below. I. A solution of 90 parts by weight of compound no. 62 and 10 parts by weight of N-methy1-a-pyrrolidone, which is suitable for application in the 30 form of very fine drops. II. A mixture of 20 parts by weight of compound no. 5, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of 35 the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained. III. An aqueous dispersion of 20 parts by weight of compound no. 15, 40 40 parts "by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing this mixture in water, an aqueous dispersion of the active ingredient is obtained. 23 7 2 51 O.Z. 0050/41443 IV. Art aqueous dispersion of 20 parts by weight of compound no. 39, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280°C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor 5 oil. By finely distributing this mixture in water, an aqueous dispersion is obtained. V. A hammer-milled mixture of 80 parts by weight of compound no. 123, 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic 10 acid, 10 parts by weight of the sodium salt of a 1ignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained. 15 VI. An intimate mixture of 3 parts by weight of compound no. 50 and 97 parts by weight of particulate kaolin. The dust contains 3wt% of the active ingredient. VII. An intimate mixture of 30 parts by weight of compound no. 59, 92 20 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence. VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 25 61, 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water, which dispersion can be further diluted. IX. A stable oily dispersion of 20 parts by weight of compound no. 67, 30 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. 35 In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum. 40 237 7 52 O.Z. 0050/41443 The following list of fungicides with which the novel compounds may be combined is intended to illustrate possible combinations but not to impose any restrictions. 5 Examples of fungicides which may be combined with the novel compounds are: su1 fur, dithiocarbamates and their derivatives, such as ferric dimethyIdithiocarbamate, 10 zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfides, 15 ammonia complex of zinc N,N'-ethylenebisdithiocarbamate, ammonia complex of zinc N,N'-propylenebi sdi thiocarbamate, zinc N,N'-propylenebisdithioccarbamate and N,n'-polypropylenebi s(thiocarbamy1) di sulfide ; 20 nitro derivatives, such as di nitro(1-methylhepty1)-pheny1 crotonate, 2-sec-buty1-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-buty1-4,6-dinitrophenyl isopropylcarbonate and diisopropyl 5-nitroisophthalate ; 25 heterocyclic substances, such as 2-heptadecy1imidazol-2-y1 acetate, 2,4-dichloro-6-(o-chloroani1ino)-s-tri az ine, O,O-diethy1 phthalimidophosphonothioate, 30 5-amino-l-[-bis-(dimethylamino)-phosphinyl]-3-pheny1-1,2,4-triazole, 2.3-dicyano-l,4-dithioanthraquinone, 2-thio-l,3-dithio[4, 5-b]quinoxaline, methyl 1-(butylcarbamy1)-2-benz imidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 35 2-(fur-2-y1)-benzimidazole, 2-(thiazol-4-yI)benzimidazole, N—(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, N-trichloromethylthi otetrahydrophthalimi de, N-trichloromethylthiophthalimide, 40 N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide, 5-ethoxy-3-trichloromethyl-l,2,3-thiadiazole, 2-th iocyanatomethylthi obenzothi azole, 1.4-dichloro-2,5-dimethoxybenzene, 237 2 53 O.Z. 0050/41443 4- (2-chloropheny1 hydrazono)-3-methy 1-5-i soxazolone, 2-thiopyridine 1-oxide, 8-hydroxyquinoline and its copper salt, 2,3-di hydro-5-carboxani1ido-6-methy1-1,4-oxathiyne, 5 2,3-dihydro-5-carboxani1ido-6-methy1-1,4-oxathiyne 4,4-dioxide, 2-methyl-5, 6-dihydro-4H-pyran-3-carboxani1ide, 2-methylfuran-3-carboxani1i de, 2.5-dimethylfuran-3-carboxani1ide, 2,4,5-trimethylfuran-3-carboxanilide, 10 2,5-dimethyl-N-cyclohexylfuran-3-carboxamide, N-cyc1ohexyl-N-methoxy-2, 5-diethylfuran-3-carboxamide, 2-methy1benzani1ide, 2-iodobenzani1ide, N-formy1-N-morpholine-2, 2, 2-trichloroethylacetal, 15 piperazine-1,4-diylbis-(l-(2,2,2-trichloroethy1)-formamide), 1-(3, 4-dichloroani1ino)-1-formylamino-2, 2, 2-trichloroethane, 2.6-dimethyl-N-tridecylmorpholine and its salts, 2, 6-dimethy1-N-cyclododecyImorpholine and its salts, N-[3-(p-tert.-butyIpheny1)-2-methy1propy1]-c is-2,6-dimethyImorpholi ne, 20 N-[3-(p-tert.-butyIpheny1)-2-methy1propy1]-piperidine, 1-[2-(2, 4-dichloropheny1)-4-ethy1-1,3-dioxolan-2-y1ethy1]-1H-1, 2, 4--tri azole, 1- [2-(2, 4-di chloropheny1)-4-n-propy1-1,3-dioxolan-2-ylethylJ-1H-1, 2, 4--triazole, 25 N-(n-propyl)-N-(2, 4, 6-trichlorophenoxyethy1)-N'-imidazolyl-urea, 1-(4-chlorophenoxy)—3, 3-dimethy1—1 — (1H—1,2,4-triazol-l-y1)-butan-2-one, 1-(4-chlorophenoxy)—3, 3-dimethy1 — 1 — (1H—1,2,4-triazol-l-y1)-butan~2-ol, a-(2-chIoropheny1)-a-(4-chloropheny1)-5-pyrimidinemethanol, 5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimi dine, 30 bis-(p-chloropheny1)-3-pyridinemethanol, 1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene, 1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene, and various fungicides, such as 35 dodecylguanidine acetate, 3-[3-(3, 5-dimethy1-2-oxycyclohexyl)-2-hydroxyethy1]-glutaramide, hexachlorobenzene, DL-methyl-N-(2,6-dimethyIphenyl)-N-fur-2-yl alanate, methy1 DL-N-(2,6-dimethy1pheny1)-N-(2'-methoxyacety1)-alanate, 40 N-{2,6-dimethyIpheny1)-N-chloroacetyl-DL-2-aminobutyrolactone, methyl DL-N-(2,6-dimethyIphenyl)-N-(phenylacetyl)-alanate, 5-methy1-5-viny1-3-(3,5-dichlorophenyl)-2,4-dioxo-l,3-oxazolidine, 3-[3, 5-dichloropheny1]-5-methy1-5-methoxymethy1-1,3-oxazolidine-2, 4-dione, 3-(3,5-dichlorophenyl)-l-isopropylcarbamylhydantoin, N-(3, 5-dichlorophenyl)-l,2-dimethylcyclopropane-l,2-dicarboximide, 237 2 9 54 O.Z. 0050/41443 2-cyano-[N-(ethyl aminocarbony1)-2-methoximino]-acetamide, 1-[2-(2,4-dichloropheny1)-pentyl]-lH-l,2,4-triazole, 2,4-di fluoro-a-(1H-1,2,4-tri azol-1-yImethy1)-benzhydry1 alcohol, N-(3-chloro-2,6-d i ni tro-4-tri f 1uoromethyIphenyI)-5-trifluoromethy1-3-5 chloro-2-aminopyridine, and 1-((bi s-(4-fluoropheny1)-methyl silyI)-methy1) — 1H—1,2,4-triazole. Use examples For comparison purposes, 1-(4-(4-tert-butyIpheny1)-cyclohexy1)-2, 6-10 dimethyImorpholine (A) disclosed in EP 259,977, N,N-dimethyl-4-(cyclo-hexylmethyl)-cyclohexylamine (B) and 4(cyclohexylmethyl)-cyclohexylamine (C), both disclosed in U.S. 3,981,766, and trans-4-tert-buty1-N-benzy1-cyclohexylamine (D) disclosed in Journal of Organic Chemistry, 48 (1983), pp. 3412-3422. 15 Use Example 1 Action on Plasmopara viticola 20 Leaves of potted vines of the Miiller-Thurgau variety were sprayed with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action, the plants were set up, after the sprayed-on layer had dried, for 8 days in the greenhouse. Then the leaves were infected with a zoospore suspension of Plasmopara 25 viticola. The plants were first placed for 48 hours in a water vapor-saturated chamber at 24°C and then in a greenhouse for 5 days at from 20 to 30°C. To accelerate and intensify the sporangiophore discharge, the plants were then again placed in the moist chamber for 16 hours. The extent of fungus attack was then assessed on the undersides of the leaves. 30 The results show that active ingredients 5, 15, 39, 40, 50, 59, 61, 62 and 67, applied as 0.025wt% spray liquors, have a better fungicidal action (100%) than prior art comparative agents A and C (75%). 35 use Example 2 Action on Botrytis cinerea in paprika Paprika seedlings of the "Neusiedler Ideal Elite" variety were sprayed, 40 after 4 to 5 leaves were well developed, to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were sprinkled with a conidial suspension of the fungus Botrytis cinerea, and placed at 22 to 24°C in a chamber of high humidity. After 5 days, the disease had spread to such a great extent on the untreated plants that the necroses covered the major portion of the leaves. </div>

Claims

<div class="application article clearfix printTableText" id="claims"> 23 7 2 55 O.Z. 0050/41443 The results show that active ingredients 5, 15, 59, 61, 62 and 67, applied as 0.05% spray liquors, have a better fungicidal action (90%) than prior art active ingredients B, C and D (60%). 10 15 20 25 30 J 35 40 56 O.Z. 0050/41443 What We Claim Is: 1.
A 4-(4-tert-butyIpheny1)-cyclohexy1 amine and quaternary ammonium salts thereof of the formulae 5 Rl CH3 / | —<^3—(Z)~\ and —C=3—( V~n®-r2 xQ R2 CH 3 1 2 where R* is hydrogen, C^-Cg-alky! or C3~Cg-alkeny1, 10 R2 is Ci-Ci2-hal°3lky 1, Ci-Ci2-hydroxyalky 1/ C3-C12— cycloalkyl, C^-C^-alkylcycloatkyl/ Cy-C^-bicyctoalkyU c3-c12~ alkenyl, unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted pheny1-(Cj-C3)alky1, the substituents in each case 15 being identical or different and being C^-C^-alkyl, C^-C^-alkoxy, Cj-C^-haloalky1, Cj-C^-haloa1koxy, halo, cyano, hydroxyl or nitro groups, with the proviso that Ri and R2 are not simultaneously Ci-C^-alkyl, and 20 x© is a plant-tolerated acid anion, and plant-tolerated acid addition salts of a compound of formula 1. 2.
A fungicidal agent containing an inert carrier and a fungicidally 25 effective amount of a 4-(4-tert-butyIpheny1)-cyclohexy1 amine or a quaternary ammonium salt thereof of the formulae zRi ?H3 -K3—0-\ and x® - o| R2 CH' FEB 1992 yj/ 1 2 where 30 is hydrogen, Cj-Cg-alkyl or C3-Cg-alkenyl, R2 is Cj-C^-alkyl, Ci-C\2-ha\oa\)f.y\, (^-C^-hydroxyalky 1, c3-c 12~ cycloalkyl, C4-C12-alkyIcyc 1 oalky 1, Cy-C^-bicycloalkyl, C3-C!2~ alkenyl, unsubstituted, monosubstituted, disubstituted or tri- 35 ^ —<' —* —. <:j 7297 57 O.Z. 0050/41443 substituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted pheny1 -(Cj-C3)alkyl, the substituents in each case being identical or different and being Cj-C^alkyl, -C^-a1koxy, C1-C^-ha1oalky1, Cj-C4-haloalkoxy, halo, cyano, hydroxyl or nitro 5 groups, with the proviso that Rl and r2 are not simultaneously Cj-C^.-a 1 ky 1, and x© is a plant-tolerated acid anion, 10 or a plant-tolerated acid addition salt of a compound of formula 1. 3.
A process for combating fungi, wherein the fungi or the plants, seed, materials or the soil to be protected against fungus attack are treated with a fungicidally effective amount of a 4-(4-tert-buty1-15 pheny1)-cyclohexy1 amine or a quaternary ammonium salt thereof of the formulae Rl CHj +oo< and <( N©-R 2 x® R 2 CH 3 1 2 where R* is hydrogen, Ci~Cg-alkyl or C3-Cg-alkeny 1, 20 r2 is Ci-Ci2~a1ky I» C|-Cj2-haloalkyl, C}-Cj 2-hyclroxy a^ ky ^ » c3~c12~ cycloalkyl, Cy-C^-bicycloalkyl, c3-c12~ alkenyl, unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl, or unsubstituted, monosubstituted, disubstituted 25 or trisubstituted phenyl-(Ci~C3)alkyl, the substituents in each case being identical or different and being C^-C^alky!, Ci-C^-alkoxy, C1-C^-haloa!ky1, Cj-C^-haloalkoxy, halo, cyano, hydroxyl or nitro groups, with the proviso that rl and r2 are not simultaneously C1-C4-alkyl, and 30 X© is a plant-tolerated acid anion, or a plant-tolerated acid addition salt of a compound of formula 1. 35 4. a compound of the formula 1 as set forth in claim 1, where rl is hydrogen and r2 is 4-tert-butylcyclohexy1. . .xfi'TN 'r
5. A compound of .the formula 2 as set forth in claim 1, where R2 i.s<4 q. v. 4-tert-butylcyclohexyl and X© is iodide. "f 237291 58 O.Z. 0050/41443
6. A compound of the formula 1 as set forth in claim 1, where Rl is hydrogen and R2 is cyclohexyl.
7. A compound as claimed in claim 1 specifically set forth herein.
8. A process for producing a compound as claimed in claim 1 substantially as herein described with reference to any one of Examples 2, 3, 4 and 6. BASF AKTIENGESELLSCHAFT By »ys BAL lREY 20 25 30 35 </div>