AU632400B2 - 4-(4-tert-butylphenyl)cyclohexylamines, and fungicides containing same - Google Patents

4-(4-tert-butylphenyl)cyclohexylamines, and fungicides containing same Download PDF

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AU632400B2
AU632400B2 AU72094/91A AU7209491A AU632400B2 AU 632400 B2 AU632400 B2 AU 632400B2 AU 72094/91 A AU72094/91 A AU 72094/91A AU 7209491 A AU7209491 A AU 7209491A AU 632400 B2 AU632400 B2 AU 632400B2
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ethyl
propyl
methyl
tert
propen
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Eberhard Ammermann
Gisela Lorenz
Bernhard Zipperer
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BASF SE
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    • C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
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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

-rcac- rwf 11: I I .I 632400 Form COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952-69 COMPLETE SPECIFICATION
(ORIGINAL)
Class Int. Class Application Number: Lodged: S Complete Specification Lodged: 0 Q Accepted: Published: Priority Relaled Art Name of Applicant Address of Applicant Actual Inventor: Address for Service BASF AKTIENGESELLSCHAFT D-6700 Ludwigshafen, Federal Republic of Germany BERNHARD ZIPPERER, EBERHARD AMMERMANN, GISELA LORENZ WATERMARK PATENT TRADEMARK ATTORNEYS.
LOCKED BAG NO. 5, HAWTHORN, VICTORIA 3122, AUSTRALIA Complete Specification for the invention entitled: 4- (4-TERT-BUTYLPHENYL)CYCLOHEXYLAMINES, AND FUNGICIDES CONAINING SAME The following statement is a full description of this invention, including the best method of performing it known to Wc MMMMMM9 O.Z. 0050/41443 4-tert-Butyiphenyl )cvclohexvlamines. and fung~icides containingi same The present invention relates to novel 4-(4-tertbutylphenyl)cyclohexylamines and acid-addition s~ilts and 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-benzylcyclohexylamine is known Org. Chem. 48 (1983) 3412-3422), 0000 but aothing is known on its fungicidal action.
4- (Cyclohexylmethyl)cyclchexylanine and its N,Ndiinethyl derivative are known as fungicides (US o 3,981,766), but their fungicidal action is unsatisfactory.
1- 4-tert-Butyiphenyl cycloheinvI 1-2, 6-dia 000 methylmorpholine has been described as a fungicide (EP 259 977), but its efficacy is poor in some areas of application, in particular at low applicat.i-on rates and 0000020 concentrations.
0 0 :0:0 Fungicidal cyclohexylamines are disclosed in DE 36 40 247. Their fungicidal action is good, but their 00 0 plant compatibility is unsatisfactory, particularly at relatively high application rates.
We have now found that 4-(4-tert-butylphenyl)cyclohoxylamines and the quaternary ammonium salts thereof, of the formulae R1
CH
3 N0.0 and 4 -ON R 2 Xe 1 2 where R" is hydrogen, CI-C.-aikyl or C 3 -Calkenyl,
R
2 'S C-C 2 -alkyl, C,-C 12 -haloalkyl, C,-C.-hydroxyalkyll
C
3 -C1 2 -c YC loalkyl, C 4 -C,2-alkylcyc loalkyl, C 7
-C,
2 -bicyc loalkyl, C-C 2 -alkenyl, unsubstituted, mono subs tituted, 2 O.Z. 0050/41443 disubstituted or trisubstituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl-
(C
1
-C
3 )alkyl, possible substituents in each case being identical or different Cl-C 4 -alkyl, C,-C 4 -alkoxy, C 1
-C
4 haloalkyl, C-C 4 -haloalkoxy, halogen, cyanQ, hydroxyl or nitro groups, with the proviso that R 1 and R 2 are not simultaneously Cl-C 4 -alkyl, X9 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 Cl-C 6 -alkyl, in particular Cl-C 4 -alkyl, such as 0 *coomethyl, 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 0 branched C 2 C.-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.
R
2 is, for example, straight-chain or branched o 0 Cl-C.-alkyl, in particular Cl-C.-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, ndecyl, n-undecyl or n-dodecyl; Cl-C, 2 -haloalkyl such as 0 000 chloromethyl, brornomethyl, iodomethyl, 2-chloroethyl, 4- 00~0 chloro-l-butyl, 3-chloro-1-butyl, 3-chloro-2-methyl-1propyl, 5-chloro-l-pentyl or 6-chloro-l-hexyl; C 1
-C
12 hydroxyalkyl, such as 2-hydroxyethyl, 2-hydroxy-l-propyl, 6-hydroxy-l-hexyl, 8-hydroxy-l-octyl or l0-hydroxy-ldecyl; C 3
-C
1 2 -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclodecyl or cyclododecyl; C 4
-C
12 -alkylcycloalkyl such as methylcyclopropyl,' methylcyclopentyl, 3- or 4-methylcyclohexyl, 3- or 4-ethylcyclohexyl, 4-isopropylc-T:ohexyl, 4tert-butylcyclohexyl, 3,3- or 4, 4-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl or 3,3,5, 0 -3 o.z. 0050/41443 cyclohexyl; C 7
-C,
2 -bicycloalkyl such as bicyclol2 hept-2-yl, 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl, bicyclo[4.4.0]ciec-2-ylorbicyclo[4.4.0]dec-3-yl; phenyl,
C
1
-C
4 -alkylpheiiyl, mono-, di- or trimethylpheftyl, ethylphenyl, isopropylphenyl, tert-butyiphenyl, Cl-C 4 -alkoxyphenyl, mono-, di- or trimethoxyphenyl, n- or tertbutoxyphenyl, C 1
-C
4 -haloalkylphenyl, Cl-C 4 -haloalkoxyphenyl, trifluoromethylphenyl, difluoromethoxyphenyl, trifluoromethoxyphenyl, tetrafluoroethoxyphenyl, cyanophenyl, nitrophenyl, mono-, di- or trichiorophenyl, mono-, di- or trifluorophenyl, chiorofluorophenyl, .0 00 bromophenyl, aryl (Cl-C 3 alkyl, such as benzyl, C 1
-C
4 alkylbenzyl, mono-, di- or trimethylbenzyl, tert-butyl- .0 benzyl, halobenzyl, fluorobenzyl, mono-, di- or tri- 15 chlorobenzyl, Cl-C 4 -alkoxybenzyl, mono-, di- or tri- CIO, methoxybenz yl, cyanobenzyl, nitrobenzyl, 2-phenylethyl, 04 2-(methoxyphenyl)ethyl,' 2-(chlorophenyl) ethyl, 2- (fluorophenyl)ethyl, 2- (tert-butyiphenyl) ethyl, 3-phenyipropyl, 3-(chlorophenyl )propyl or fluorophenyl)propyl.
Xe is an inorganic or or~ganic acid anion, for 00 example chloride, bromide, iodide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, nitrate, tetrafluoroborate; formate, acetate, 0 oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate or dodecylbenzenesulfonate.
0"0 Examples of acids for the preparation of the 0 64 0 acid-addition salts are mineral acids, hydrochloric acid, sulfuric acid, nitric acid, formic acid, alkylcarboxylic acids, such as acetic acid, propionic acid, oxalic acid, sulfonic acids, such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid and dodecylbenzeniesul fonic acid.
The novel compounds of the formulae 1 and 2 can exist in two diastereomeric forms, namely as cis-l,,4- and as trans-1,4-disubstituted cyclohexane. Depending on the preparation method, they are obtained either as pure diastereomers or as diastereomer mixtures. If desired, I_ 4 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.
In some of the radicals R 2 according to the invention, further isomers can occur in addition to the abovementioned cis/trans isomerism. Depending on the nature of R 2 these isomers may be enantiomers or diastereomers. Here too, the diastereomeric compounds can be resolved by conventional methods, for example by chromatography or crystallization. All isomeric compounds and Sooo mixtures thereof with one another are included in the present invention. The pure diastereomers or enantiomers So and the mixtures thereof are suitable for use of the novel amines as fungicides. Preference is given to S mixtures.
o 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 reacting an amine of the formula
RI
H-N 3 \2R2 0 0 where
R
1 is hydrogen, C 1
-C
6 -alkyl or C--C 6 -alkenyl and a o R 2 is Ci-C 1 z-alkyl, with the proviso that R 1 and R 2 are not simultaneously Ci-C 4 -alkyl, or is C-C 1 2 -haloalkyl, C 1
-C
1 zhydroxyalkyl, C 3
-C
2 -cyc loalkyl, C 4
-C
1 z-alkylcycloalkyl,
C-C
1 2 -bicycloalkyl,
C
3
-C
12 -alkenyl, unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl(Ci-C 3 )-alkyl, possible substituents being in each case identical or different Ci-C 4 -alkyl, C 1
C
4 -alkoxy, Ci-C 4 -haloalkyl, Ci-C 4 -haloalkoxy, halogen, cyano, hydroxyl or nitro groups, with 4- 4-tert-butylphenyl cyclohexanone, and reducing 5 O.Z. 0050/41443 the imine (in the case where R 1 is hydrogen) or enamine (in the case where R 1 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.
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 R 1 and R 2 are as defined above with 4-(4-tert-butylphenyl)cyclohexanone. This can be effected, for example, by adding a dehydrating agent 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 Ssulfate, zinc sulfate, calcium chloride or molecular o.o sieves. The reaction is carried out in the presence or 1.5 absence of an inert organic solvent and in the presence or absence of a catalytic amount of acid. Suitable .o0 solvents are hydrocarbons, such as cyclohexane, benzene, toluene or xylenes, chlorinated hydrocarbons, such as dichloromethane or 1,2-dichloroethane, or ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane. Examples of suitable acids are mineral acids, Ssuch as sulfuric acid or phosphoric acid, or sulfonic acids, such as methanesulfonic acid, benzenesulfonic acid 0 0 or p-toluenesulfonic acid. The amount of acid necessary is, for example, from 0 to 10 mol-%, preferably from 0 to o o, 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 is necessary cannot be achieved under atmospheric pressure 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 reaction produced is removed from the reaction mixture by azeotropic distillation, the reaction is carried out at the boiling point of the particular solvent. Preferred 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 3 where R 1 and R 2 are as defined above with 4-(4-tertbutylphenyl)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 borohydride or sodium cyanoborohydride. Particular preference is given to hydrogen in the presence of a metallic ,ooS catalyst. Examples of suitable catalysts are finely °o divided metals, such as Raney nickel or Raney cobalt, and ooo, 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 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 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 for example, 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 for example, C.F. Lane, Synthesis 1975, 135). The combination of sodium cyanoborohydride and anhydrous zinc chloride has proven particularly expedient (cf. S. Kim et al., J. Org. Chem. (1985) 1927).
In this process, the NaBH 3 CN:ZnCl 2 molar ratio can be, for example, from 1:2 to 1:0.5, preferably 1:0.5. As far as the amount of NaBH 3 CN employed is concerned, either the amine component 3 or the ketone component can be used 1
.IN-
_~liU_ 1 I 7 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, ethanol, n-propanol or isopropanol, particularly preferably 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 starting material is novel. It can be prepared from known, commercially available 4-phenylcyclohexanone by 000 ooo. Friedel-Crafts alkylation of the phenyl ring. Examples of oi"o alkylating agents are tert-butyl chloride or bromide, tert-butanol or 2-methylpropene for example, Houben-Weyl, Methoden der Organischen Chemie, Vol. 5/2b, 'pp. 154 ff., pp. 179 ff., G. Thieme Verlag, Stuttgart, 0 1981). Prefer:ence 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 as aluminum trichloride, iron(III) chloride or boron trifluoride. Suitable solvents are in particular chlorin- "0 o ated hydrocarbons, especially dichloromethane, tetra- 0 O, chloromethane, and 1,2-dichloroethane. The tert-butylation of the 4-phenylcyclohexanone can be carried out at room temperature or below, preferably at from 0 to The amines of the formula 3 where R 1 and R 2 are as defined above are known compounds and those which are not commercially available can be prepared by known processes.
The amines prepared by the above-described process, where R 1 and R 2 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 into their constituents by known methods, for example by chromatography or fractional crystallization.
b) A further process allows the targeted preparation L *j 8 o.Z. 0050/41443 of cis- or trans-4-(4-tert-butylphenyl)cyclohexylamines of the formula 1 where R1 is hydrogen and
R
2 is C 1
-C
12 -alkyl, C 1
-C
12 -haloalkyl, C 1
-C
12 -hydroxyalkyl,
C
3
-C
1 2 -cycloalkyl, C 4
-C
1 -alkylcycloalkyl, C 7
-C
1 -bicycloalky, C 3 ,-C-alkenyl, unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl- (Cl-C 3 )alkyl, possible substituents in each case being identical or different C-C 4 -alkyl, Ci-C 4 -alkoxy, C 1
-C
4 haloalkyl, C-C 4 -haloalkoxy, halogen, cyano, hydroxyl or nitro groups.
This process comprises first converting 4-(4tert-butylphenyl)cyclohexanone into 4-(4-tert-butylphenyl)cyclohexanone oxime by conventional methods using hydroxylamine or a hydroxylamine salt, and subsequently reducing this oxime using sodium in ethanol for example, Chem. Ind. (London) 1972, 683). The trans-4- (tert-butylphenyl)cyclohexylamine obtained is then reacted in a further step with a carbonyl compound of the formula 0 R3-C-R 4 0Q 09 where R 3 and R4 are such that the radical R3 06 -CH R4 corresponds in its entirety to R2 as defined above, and the imine 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 cisand trans-4-(4-tert-butylphenyl)cyclohexylamine is obtained, which can be resolved into the pure cis- and trans-isomers by conventional methods, for example by 9 O.Z. 0050/41443 chromatography, distillation or fractional crystallization of an acid-addition nalt with subsequent liberation of the base. The two isomers can then be reacted separately with a carbonyl compound of the formula 0
SII
R
3
-C-R
4 4 where R 3 and R 4 are as defined above to give the pure cisand 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)cycloo hexylamines with a carbonyl compound of the formula 4 and n to resolve the resultant isomer mixture of amines of the formula 1 into its constituents, for example by chromatography or crystallization.
A further way of preparing a cis/trans mixture of 4-(4-tert-butylphenyl)cyclohexylamines comprises alkylating cis/trans-4-phenylcyclohexylamine using 2-methylpropene in the presence of an at least equimolar amount of mineral acid, for example sulfuric acid. Preferred 0o :20 solvents are chlorinated hydrocarbons, eg. dichloromethane, tetrachloromethane or 1,2-dichloroethane. The o alkylation can be carried out at room temperature or below, preferably at from 0 to 20 0
C.
The 4-phenylcyclohexylamine used as a starting «25 material is known. It can be prepared, for example, by hydrogenating 4-aminobiphenyl 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 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).
The above-described process b) gives the amines
I/
I v 10 O.Z. 0050/41443 of the formula 1 where R 1 is hydrogen. These secondary amines can, if desired, be converted into tertiary amines of the formula 1 where R 1 is Ci-C 6 -alkyl or C 3
-C
6 -alkenyl by known alkylation reactions.
If the alkylating agent used is a methyl compound of the formula
CH
3 -A where A is a nucleofugic leaving group, eg. chlorine, bromine, iodine, O-SO 2
-OCH
3 O-SO2-CH 3 or O-SOz-p-CsH 4
-CH
3 o~o ooo 10 and the alkylating agent is employed in excess, 4-(4- °o0 tert-butylphenyl)cyclohexyl.ammonium salts of the formula 2 where R 2 is as defined above are obtained.
This quaternization can be carried out in the presence or absence of a diluent. Examples of suitable 15 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 0.0 00 0 o acetate, nitriles, such as acetonitrile or propionitrile, o ,20 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 25 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-tertbutylphenyl)cyclohexylammonium salt of the formula 01 11 005Q/41443
CH
3 NSR2 Ae 2a
CH
3 where R 2 and A are as def ined above. If necessary, the ainAe can be replaced by another, plant-compatible acid H anion by conventional methods, f or example by ion exchange chromatography.
toga 4 0 aQ~ 04 0 r ~o0 0 0 0 04 00 0 00 000 0 304 000 0 0 0 0 0 4 04 4 0- 400 90 0 SCHEME 1 Plylation 1 HNR1R2 2. Reduction
RI
R 2 H, CH 3
\)CH
3 1 NH 2 0H1 2. Reduction
I
3 CH 3 C NH2 0 11 Alkylation 1. R 3
-C-R
4 (4) 2 2. Reduction R2 4%j
"MMONNOW
1 13 O.Z. 0050/41443 Oor,.
4
C.
0 00L 4'(r 0 04 The examples below are intended to illustrate the preparation of the compounds according to the invention in greater detail.
EXAMPLE 1 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 to a solution of 50 g (0.287 mol) of 4-phenylcyclohexanone in 600 ml of dichloromethane. 19.5 g (0.35 mol) of isobutylene (2-methylpropene) gas are passed into this mixture over the course of 15 to 20 minutes at from 10 to The mixture is stirred at room temperature (20 0
C)
for a further one hour and 250 ml of water are then added dropwise with ice cooling. The organic phase is separated off, washed neutral with water, 10% strength NaOH and again with water, dried over Na 2
SO
4 and evaporated under reduced pressure. The residue is recrystallized from npentane,, to give 50.7 g (76% of theory) of colorless crystals of melting point 80-82 0
C.
H-NMR (CDCl 3 6 7.35 2H), 7.18 2H), 3.00 (br, t, 1H), 2.50 4H), 2.21 2H), 1.95 2H), 1.30 9H).
IR (KBr): 2965, 2944, 2867, 1710, 1418, 1160, 832, 808, 570 cm EXAMPLE 2 4-trans-tert-Butyl-4'-cis/trans- (4-tert-butylphenyl)- M,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-butylcyclohexylamine 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 is then stripped off under reduced pressure. The residue taken up in water, rendered alkaline using concentrated NaOH and extracted sev A-1 times with methyl tert-butyl 00a 00 0y 0 o) 0 0'" 00X 0 000 4' 14 O.Z. 0050/41443 ether. The organic phase is dried over Na 2 SO6, freed from solvent and then distilled under reduced pressure. After an initial fraction comprising principal.i7, 4-tert-butylcyclahexylanine, 19.3 g (75% of theory) of~ the title c ompaund are obtained at 210-212*C/0.2 mbar as a colorless, viscous oil. According to GC and 'H-NMR analysis, it is a cis/trans mixture in the ratio 2:3.
C
26
H
4 3 N (369.1) Calc. C 84.48 H 11.73 N 3.79 Found C 84.5 H 11.7 N 3.6 EXAMPLE 3 Resolution of 4-trans-tE.rt-butyl-4 '-cis/trans- 000 4- (tert-butylphenytl )-,N-dicyc lohexylamine 8.0 g of a cis/trans isomer mixture obtained as 00 0 :0o 15 in Example 2 are resclved by chromatography on a 30 x 3 cm silica gel culuxnn (Macherey Nagel, 0.04-0.06 mm) using cyc lohexane /ethyl acetate at 0.1 bar of nitrogen. The 4-trans-tert-butyl-4 '-ci-s-(4-tert-butylphenyl)-N,N-dioyclohexylamine is eluted first as a colorless solid of melting point 54-56 0 C (ethanol). The relative stereochemistry was determined by and 3
-M
0:00 spectroscopy.* 'H-NMR (CDCl 3 intcr alia 6 3.00 (in, IL'--Heq), 2.55 (in, 2.40 (4'-Hax)* 1 C-NMR (CDCl 3 intc-r alia J 54.04 43.69 (C- 4' 34.86 (2(6),33.39(C35).
Af ter a mixed f raction (0.8 4-trans-tertbutyl-4 '-trans- (4-tert-butylphenyl) N-dicyclohexylamine is obtained, initially as a pale yellow oil, which crystallizes from acetonitrile. Colorless crystals, melting point 112-113'C.
'H-NMR (CDCl 3 inter alia 6 =2.67 (br.m, 2.50 (br. m, 4'1H.
1 3 C -NMR (CDCl 3 inter alia 6 48.42 42.69 (C- 30.98 28.30 EXAMPLE 4 N,N-Dimethyl-4-trans-tert--butyl-4 '-cis/trans- (4-tert-butyiphenyl) -N,N-dicyclohexylammonium iodide 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 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 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 with ice-cold acetone and dried at 50.C under reduced pressure, to give 6.7 g (62% of theory) of quaternary o.s salt as colorless crystals of melting point 184-185"C.
EXAMPLE "o cis/trans-4-(4-tert-Butylphenyl)cyclohexylamine 3o0o15 165 g of concentrated HzSO (1.68 mol) are added Sdropwise to 52.5 g (0.30 mol) of well cooled 4-phenylcyclohexylamine (cis/trans ratio of about 2:3) at from 0 to 5 0 C. 1,000 ml of dichloromethane diluent are added, and 21.8 g (0.39 mol) of isobutylene gas are passed in over the course of 20 minutes at from l1 to 15 0 C. After oooo one hour at 20"C, 250 ml of water are added dropwise with ice cooling. The aqueous phase is extracted twice with CHC1 2 The combined organic phases are stirred vigorously with 1 1 of 10 percent strength by weight NaOH, then washed with water, dried over NazSO 4 and evaporated under reduced pressure. The crude amine, which is about b'o pure according to gas chromatography, is dissolved in 500 ml of ether and precipitated as the hydrochloride by passing in HC1 gas with ice cooling to give 35.3 g (44.5% of theory) of a yellowish crystal powder which decomposes above 240°C, IR (KBr): v 2956, 2932, 2868, 1607, 1510, 1448, 1362, 1268, 831, 574 cm 1 The free base is obtained therefrom by adding 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 16 O.Z. 0050/41443 mixture). Characteristic NMR data (CDC1 3 cis-4-(4-tertbutylphenyl)cyclohexylamine: 6 1-Heq 3.19; y C-1 45.3 ppm.
trans-4-(4-tert-Butylphenyl)cyclohexylamine: 6 1-H, 2.70; 6 C-1 50.2 ppm.
EXAMPLE 6 N-Benzyl-N-4-(4-tert-butylphenyl)cyclohexylamine (Compound No. 104) A solution of 11.6 g (0.05 mol) of 4-(4-tertbutylphenyl)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 o filtration, the toluene is stripped off and replaced by 15 ethanol. 2.7 g (0.07 mol) of sodium borohydride ar- then 'E 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 sodi. sulfate and evaporated, an the residue is subjecte to incipient distillation at 2 mbar up to 200 C to give 9 g (56% of theory) of aoo^ a pale reddish resin, a 2:1 trans/cis isomer mixture according to 'H-NMR and gas chromatography.
IR (film): v 2961, 2927, 2862, 1461, 1452, 1362, 827, 736, 698, 572 cm 1
C
23
H
31 N (321.1) Lo° Calc. C 85.92 H 9.72 N 4.36 Found C 85.5 H 9.9 N 4.1 The following compounds are prepared by measures simil to these Examples: i r c0o a 000 0 0 0 000 00 ~0 00 0 00 dO S00 0 0 900031 0.Z. 0050/41443 No. R Physical data Methyl EthylI 1-Propyl 2-P ropy I 1 -Butyl 2-Buty 1 tent. -Buty 1 2-Methyl-1-propyl 1-Pentyl 2-Methyl-1-butyl 2-Methy 1-l-pentyl 2-Ethyl-i -buty I 2, 2-Dimethyl-i-propyl 3, 3-Diniethyl-1-butyi 3-Methyl-i-butyl 1-Hexyl 2-Methyl-l-hexyl 2,4, 4-Trimethyl-i-pentyl 1-Heptyl 1 -Oc ty 1 1-Nonyl 1-Decyl i-Un decy I 1-Dodecyl 2-Propen-i-yl 2-Buten-1-yl bp. 220-224 0 C/2 mbar (cis/trans=i:2) resin (cis/trans=1:2) 000 0 4 0 0 0 04 0 0 4 0 04 4 9 4 0 4 00 0*0 000 0 0 0 0 0 0 00 0 0 0 4 0 000 0 0 4 0 0 0 0 0 ~0 400 0 0 0 a 0 000 0 0 0 900Cf31 O.Z. 0050/41443 No. R Physical data 2-Penten-1-yl 2-Hexen-1-yl 3-Methy l-2-buten-l -y 1 2, 3-Dimethyl-2-buten-1-yl 2-Hydroxyethyl 6-H-ydroxy-1-hexyl 3-Ch loro-1 -buty 1 4-Chloro-1--butyl 3-Chloro-2-methyl-l-propy 1 Cyclopropy 1 Cyclobutyl Cyclopenty I Cyclohexyl Cycloheptyl Cy ciooc ty l Cyclodecyl Cyclododecyl I-Methylcyclopropy I 1-Methylcyclopentyl 1-Methyl cyc lohexyl 2-Methylcyclohexyl 3-Methylcyclohexyl 4-Methylcyclohexyl 2, 2-Dimethylcyclohexyl 3, 3-Dimethylcyclohexyl 4, 4-Dimethylcyclohexyl 2, 6-Dimethylcyclohexyl bp. 180-186 0 C/0.5 mbar (cis/trans=1:2) bp. 167-170 0 C/0.4 mbar (cis/trans=l:2) IR: 2949,2923,2865,2851,1447,1363,1112,826,571 S S a a 0@ 0 0 0 00 0 00 0 0 00 000 a p 0 0 0 0 P 0 0 0 0 0 0 0 0 0 0 a a 0 0 04 GOp 0 0 0 0 0 0 0 000 4 04 0 900031 o.z. 0050/41443 No. R Physical data 3,3, 3,5,5, 4-Ethylcyclohexyl 4-Propylcyclohexyl 4-Isopropylcyclohex, I 4-tert Butylcyclohexyl c is-4-tert.-Butylcyclohexyl trans-4-tert. -Butylcyclohexyl 4-tert.-Arnylcyclohexyl Bicyclo[2.2. 1]-hept-2-y1 1,7, 7-Trimethyl-bicyclo[2. 2.1 Bicyclo 0]dec-2-y I Bicyclo[4.4.0]dec-3-yl Hydrochloride: IR:2951, 2865, 2794 2734, 1462, 1385, 1363, 827, 572 4'-cis: Fp. 54-56 0 C; 4'-trans: mp. 112-113 0
C
]-hept-2-y 1 IR: 2923,2856,1464,1447,1362,1269,1111,826,571 resin (cis/trans=1:2) 2,6, 6-Trimethylbicyclo[3.1 1-hept-3-yl Phenyl IR:2960,2928,2863,1602,1503,1362,1312,827,746, 691 2-Methyl pheny 1 3-Methylpheryl 4-Methyl pheny 1 2, 4-Dimethylphenyl 4-Isopropy iphenyl 4-te rt Butyl1pheny 1 IR: 2961,2928,2864,1615,1519,1460,1445,1363, 1269, 1193, 819 r 008 9 9 0 9 00 r' 0 0 0 '0 0 o 0 0 0 e 00 009 000 0 0 0 0 0 0 0 0 0 0 0 C 0 0 0 0 0 0 CC9 0 0 0 0 0 0 0 9O00~l 0.Z. 0050/41443 No. R Physical data 76 H 77 H 2-Methoxypheny 1 4-Methoxypheny 1 3, 4-Dimethoxyphenyl 4-tert. -Butoxyphenyl 2-Trifluoromethylphenyl 3-Trifluoromethylphenyl 4-Tri1fluoromethyiphenyl 4-Trifluoromethoxyphenyl 2-Fluorophenyl 3-Fluorophenyl 4-Fluoropheny I 2, 4-Di fluorophenyl 2-Chlorophenyl 2-Chi oro-4-f1 uorpheny 1 3-Chlorophenyl 4-Chlorophenyl 2, 4-Dichlorophenyl IR: 2960,2931,2863,1602,1519,1512,1456,1247, 1222, 734 IR: 2952, 2925, 2863, 1512, 1461, 1458, 1255, 1248, 1031, 823 IR: 2961,2930,286,4,1620,1521,1512,1449,1249, 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 92 H 2, 6-Dichiorophenyl 3, 2-Cy anopheny 1 3-Cy anopheny l r, 000 000 0 0 0 0 0 0 00 0' 0 a 0 0 0 0 0.
00d 0 0 00 0 C C 0 0 9000351 0.Z. 0050/41443 No. R Physical data 4-Cyanophenyl 2-H-ydroxypheiiy I 3-Hydroxypheny I 4-H-ydroxypheny 1 2-Nitrophenyl 3-N it ropheny 1 4-Nitrophenyl Benzyl 2-Methyl benzy I 4-Methy lbenzy 1 2, 4-Dimethylbenzyl 4-Isopropylbenzy 1 4-tert Buty lbenzy 1 2-Methoxybenzy 1 3-Methoxybenzy l 4-Methoxybenzy I 3, 4-!imethoxybenzyl 4-tert Butoxybenzyl 2-Trifluorornethylbenzyl 3-Trifluoromethylbenzyl 4-Trifluoromethylbenzyl 4-Tifluoromethoxybenzyl 2-Fluorobenzy 1 IR: 2961,2927,2862,1461,1452,1362,827,736, 698, 572 2961,2925,2863,1509,1460,1448,1362, 825, 571 IR: 2961,2927,28 64,1508,1490,1456,1363, 1229, 828, 756 120 H 10 H3-Fluorobenzyl r 000 0 0 0 0 0 00 0 0 0 0 0 00 0 0 0 0 0 0 00 000 op0 0 0 0 0 V 0 0 00 O 000 0 90063 1 0.Z. 0010/41443 No. R 121 H Physical data 4-Fl uorobenzy 1 2, 4-Oifluorobenzyl 2-Chloro-4-fl uorobenzyl 2-Chlorobenzyl 3-Chlorobenzyl 4-Chlorobenzyl 2, 4-DichlorobenzyI 2, 6-Dichlorobenzyl 3, 2-Cyanobenzy 1 4-Cyanobenzy 1 2-Hydroxybenzy I 3-Hydroxybenzy 1 4-Hydroxybenzy 1 2-Ni trobenzy I 3-Ni trobenzy I 4-Ni trobenzy 1 2, 4-Dinitrobenzyl 2-Phenylethyl 2-(4-Methylphenyl )ethyl 2-(4-tert.-Butylphenyl )ethyl 2-(2-Methoxyphenyl)ethyl 2- (4-Methoxyphenyl )ethyl 4-Dimethoxyphenyl )ethyl 2- (4-tent Butoxyphenyl )ethyl IR: 2960,2927, 2864,1509,1462,1449,1362, 1221, 827, 572 Hydrochloride: IR: 2955,2863,2766,2721, 2574, 1478, 1469, 825 0 0 0 0 0 0 C 0 C 0 0 0 00900031 23 o.Z. 0050/41443 No. RIR 2 Physical data 146 H 2-(4-Trifluoromethoxyphel)ethyI 147 H 2-(3-Trifluoromethylphenyl)ethyl 148 H 2-(2-Fluorophenyl)ethyl 149 H 2-(4-Fluorophenyl)ethyl 150 H 2-(2-Chlor-ophenyl)ethyl 151 H 2-(4-Chlorophenyl)ethyl 52 H 2-(2,4-Dichlorophenyl)ethyl 153 H 2-(2-Chloro-4-fluorophel)ethyl 154 H 2-(4-Cyanophenyl)ethyl 155 H 2-(4-Hydroxyphenyl)ethyl 156 H 2-(4-Nitrophenyl)ethyl 157 H 3-Phenyipropyl 158 H 3-(4-Methylphenyl)propyl 159 H 3-(4-tert.-Butylphenyl)propyl 160 H 3-(2-Methoxyphenyl)propyl 161 H 3-(4-Methoxyphenyl)propyl 162 H 4-Oimethoxyphenl)propyl 163 H 3-(4-tert.-Butoxyphenyl)propyl 164 H 3-(3-Trifluoromethylphenyl)propyI 165 H 3-(4-Tri fluoromethoxyphenyl )propyl 166 H 3-(2-Fluorophenyl)propyl 167 H 3-(4-Fluorophenyl)propyl 168 H 3-(2-Chlorophenyl)propyl 169 H 3-(4-Chlorophenyl)propyl 170 H 3-(2,4-Dichlorophefl)propyl 171 H 3-(2-Chloro-4-fluorophenyl)propyl 172 H 3-(4-Cyanophenyl)propyl C 0 0 0 04 ooO 000 0 0 C C 2 0 0 0 2: :0 COo 2: C 2. C 000 00900031 0.Z. 0050/41443 No. R Physical data~ 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199
H
H
Methyl Methyl Methyl MethylI Methyl Methyl MethylI Methyl MethylI Methyl Methyl Methyl MethylI Methyl Methyl Methyl Methyl Methyl Methy 1 MethylI MethylI Methyl Methyl MethylI Methyl 3-(4-Hydroxyphenyl )propy 1 3-(4-Nitrophenyl )propyl 1-Pernty 1 2-Methyl-1-butyl 2-Methyl-1-pentyl 2-Ethyl-1-butyl 2, 2-Dimethyl-1-propyl 3, 3-Dimethyl-1-butyl 3-Methy 1-1-buty 1 1-H-exy I 2-Methy 1-1-hexy 1 2-Ethyl-1-hexyl 2,4, 4-Trimethyl-1-pentyl 1-Heptyl 1-Octyl 1-Nony 1 1-Decy I 1-Un decy 1 1-Dodecyl 2-Propen-1-yl 2-Buten-1-yl 2-Penten-1-yl 2-Hexe n-i -y 3-Methyl -2-buten-1-yl 2, 3-Dimethyl-2-buten-1-yl 2-Hydroxye-thy 1 6-Hydroxy-I-hexy 1 oil (cis/trans=1:3)
C,
000~~. 0400 0 0 0 0 0 0 0 0 00 ~'9006~1 o.z. 0050/41443 No. RIR 2 Physical data 200 Methyl 3-Chloro-l-butyl 201 Methyl 4-Chloro-1-butyl 202 Methyl 3-Chloro-2-methyl-1-propyl 203 Methyl Cyclopropyl 204 Methyl Cyclobutyl 205 methyl Cyclopentyl 206 Methyl Cyclohexyl 207 methyl Cycloheptyl 208 methyl Cyclooctyl 209 Methyl Cyclodecyl 210 Methyl Cyclododecyl 211 Methyl 1-Methylcyclopropyl 212 Methyl 1-Methylcyclopentyl 213 Methyl 1-Methylcyclohexyl 214 Methyl 2-Methylcyclohexyl 215 methyl 3-Methylcyclohexyl 216 methyl 4-Methylcyclohexyl 217 methyl 2,2-Dimethylcyclohexyl 218 Methy. 3,3-Dimethylcyclohexyl 219 Methyl 4,4-Diniethylcyclohexyl 220 Methyl 2,6-Dimethylcyclohexyl 221 methyl 3,3,5-Trimethylcyclohexyl 222 methyl, 3,3,5, 223 methyl 4-Ethylcyclohexyl 224 Methyl 4-Propylcyclohexyl 225 Methyl 4-Isopropylcyclohexyl 226 Methyl 4-tert.--Butylcyclohexyl bo a 0 0 T3 1 26 o.z. 0050/41443 No. RI R Physical data 227 Methyl cis-4-tert.-Butylcyclohexyl 228 Methyl trans-4-tert,.-Butylcyclohexy 1 229 Methyl 4-tert.-Amylcyclohexyl 230 Methyl Bicyclo[2.2,l]-hept-2-yl 231 Methyl 1,7,7-Trimethyl-bicyclo[2.2.l' hept-2-yl 232 Methyl Bicyclo[4.4-Oldec-2-y! 233 Methyl Bicyclo[4.4.0Cjdec-3-yl 234 Methyl 2,6,6-Triniethylbicyclo[3.1.l1-hept-3-yl 235 Methyl Phenyl 236 Methyl 2-Methyviphenyl 237 Methyl 3-Methyiphenyl 238 Methyl 4-Methylphenyl 239 Methyl 2,4-Dimethylphenyl 240 Methyl 4-Isopropylphenyl 241 Methyl 4-tert.-Butylphenyl 242 Methyl 2-Metho;(ypheny',, 243 Methyl 4-Methoxyphenyl 244 Methyl 3,4-Dimethoxyphenyl 245 Methyl 4-tert.--Butcxyphenyl 246 Methyl 2-Trifluorornethylphenyl 247 Methyl 3-Trifluorornethylphenyl 248 Methyl 4-Tr ifi uoromethylIpheny 1 249 Methyl 4-Trifluoromethoxyphenyl 250 Methyl 2-Fluorophenyl 251. Methyl 3-Fluorophenyl 252 Methyl 4-Fluot-ophenyl 253 Methyl 2,4-Difluorophenyl 9000 31 27 o.Z. 0050/411,43 No. RI R2 Physical data 254 Methyl 2-Chlorophenyl 255 Methyl 2-Chloro-4-fluorphenyl 256 Methyl 3-Chiorophenyl 257 Methyl 4-Chlorophenyl 258 Methyl 2,4-Bichlorophenyl 259 Methyl 2,6-Dichlorophenlvl 260 Methyl 261 Methyl 2-Cyanophenyl 262 Methyl 3-Cyanophenyl 263 Methyl 4-Cyanophenyl 264 Methyl 2-Hydroxyphenyl 265 Methyl 3-Hydroxyphenyl 266 Methyl 4-Hydroxyphenyl 267 Methyl 2-Nitrophenyl 268 Methyl 3-Nitrophenyl 269 Methyl 4-Nitrophenyl 270 Methyl Benzyl 271 Methyl 2-Methylbenzyl 272 Methyl 4-Methylbenzyl 273 Methyl 2,4-DimethylbenzyI 274 Methyl 4-Isopropyflbenzyl 275 Methyl 4-tert.-Butylbenzyl 276 Methyl 2-Methoxybenzyl 277 Methyl 3-Methoxybenzyl 278 Methyl 4-Methoxybenzyl 279 Methyl 3,4-Dimethoxybenzyl 280 Methyl 4-tert.-Butoxybenzyl .300P0OO ?0 0 a o 0 00 0 0 0 o0o 0) 0 0 00 30. 0 C 0 0 b0 00 0 0v 000 900031 28 0.2. 0050/41443 NC' R 2 Physical data 281 Methyl 2-Trifluoromethylbenzyl 282 Methyl 3-Trifluoromethylbenzyl 283 Methyl 4-1Yri fluoromethylbenzyl 284 M; hyl 4-Trifluorornethoxybenzyl 285 Methyl 2-Fluorobenzyl 286 methyl 3-Fluorobenzyl 287 Methyl 4-Fluorobenzyl 288 Methyl 2,4-Difluorobenzyl 289 Methyl 2-Chloro-4-fluorobenzyl 290 Methyl 2-Chlorobenzyl 291 methyl 3-Chlorobenzyl 292 Methyl 4-Chlorobenzyl 293 Methyl 2,4-Dichlorobenzyl 294 Methyl 2,6-Dichlorobenzyl 295 Methyl 296 Methyl 2-Cyanobenzyl 297 Methyl 4-Cy anobenzy 1 298 methyl 2-Hydroxybenzy 1 299 Methyl 3-Hydroxybenzyl 300 lethy1 4-Hydroxybenzyl Methyl 2-Nitrobenzyl 302 Methyl 3-Nitrobenzyl 303 Methyl 4-Nitrobenzyl 304 Methyl 2 1 4-Dinitrobenzyl 305 Methyl 2-Phenylethyl 306 Methyl 2-(4-Methylphenyl)ethyl 307 Methyl 2-(4-tert -Butylphenyl)ethyl 000 00 0 0 00 0 003 29 O.Z. 0050/41443 No. RIR 2 Physical data 308 Methyl 2-(2-Methoxyphenyl)ethyl 309 Methyl 2-(4-Methoxyphenyl)ethyl 310 Methyl 2-(3,4-Dimethoxyphelyl)ethyl 311 Methyl 2-(4-tert.-Butoxypheflyl)ethyl 312 Methyl 2-(4-Trifluoromethoxyphelyl)ethyI 313 Methyl 2-(3-Trifluoromethylphenyl)ethyI 314 Methyl 2-(2-Fluorophenyl)ethyl 315 Methyl 2-(4-Fluorophenyl)ethyl 316 Methyl 2-(2-Chlorophenyl)ethyl 317 Methyl 2-(4--Chlorophenyl)ethyl 318 Methyl 2-(2,4-Dichlorophenyl)ethyl 319 Methyl 2-(2-Chloro--4-fluorophenyl)ethyI 320 Methyl 2-(4-Cyanophenyl)ethyl 321 Methyl 2-(4-Hydroxyphenyl )ethyl 322 Methyl 2-(4-Nitrophenyl)ethyl 323 methyl 3-Phenylpropyl 324 Methyl 3-(4-Methylpheflyl)propyl 325 Methyl 3-(4-tert.-Butylphenyl)propyl 326 Methyl 3-(2-Methoxypheflyl)propyl 327 Methyl 3-(4-Methoxypheflyl)propyl 328 methyl 3-(3,4-DimethoxyphenyI)propyl 329 Methyl 3-(4-tert.-Butoxyphenyl)propyl 330 Methyl 3-(3-Trifluoromethylphenyl)propyI 331 Methyl 3-(4-Trifluoromethoxyphenyl)propyI 332 Methyl 3-(2-Fluorophelyl )propyl 333 Methyl 3-(4-FluorophenyI )propyl 334 Methyl 3-(2-Chlorophenyl)propyl 000000 0 0000 0 900 3 0.Z. 0050/41443 No. RR2Physical data 335 Methyl 3-(4--Chlorophenyl)propyl 336 Methyl 3-(2,4-Dichlorophenyl)propyl 337 Methyl 3-(2-Chloro-4-tluorophenyl)propyI 338 Methyl 3-(4-Cyanophenyl )propyl 339 Methyl 3-(4-Hydroxyphenyl)propyl 340 Methyl 3-(4-Nitrophenyl)propyl 341 Ethyl 1-Pentyl 342 Ethyl 2-Methyl-1-butyl 343 Ethyl 2-Methyl-l-pentyl 344 Ethyl 2-Ethyl-l-butyl 345 Ethyl 2,2-Dimethyl-l-propyl 346 Ethyl 3,3-Diniethyl-l-butyl 347 Ethyl 3-Methyl-l-butyl 348 Ethyl 1-Hexyl 349 Ethyl 2-Methyl-l-hexyl 350 Ethyl 2-Ethyl-l-hexyl 351 Ethyl 2,4,4-Trimethyl-l-pentyl 352 Ethyl 1-Heptyl 353 Ethyl 1-Octyl 354 Ethyl 1-Nonyl 355 Ethyl 1-Decyl 356 Ethyl 1-Undecyl 357 Ethyl 1-Dodecyl 358 Ethyl 2-Propen-1-yl 359 Ethyl 2-Buten-1-yl 360 Ethyl 2-Penten-i-yl 361 Ethyl 2-Hexen-1-yl
W,
a 8 0 80 00 88 900 3 31 O.Z. 0050/41443 No. RR2Physical data 362 Ethyl 3-Methyl-2-buten-l-yl 363 Ethyl 2,3-D)imethyl-2-butcen-l-yl 364 Ethyl 2-H-ydroxyethyl 365 Ethyl 6-Hydroxy-l-hexyl 366 Ethyl 3-Chloro-1-butyl 367 Ethyl 4-Chloro-l-butyl 368 Ethyl 3-Chloro-2-methyl-l-propyl 369 Ethyl Cyclopropyl 370 Ethyl Cyclobutyl 371 Ethyl Cyclopentyl 372 Ethyl Cyclohexyl 373 Ethyl Cycloheptyl 374 Ethyl Cyclooctyl 375 Ethyl Cyclodecyl 376 Ethyl Cyclododecyl 377 Ethyl 1-Methylcyclopropyl 378 Ethyl 1-Methylcyclopentyl 379 Ethyl 1-Methylcyclohexyl 380 Ethyl 2-Methylcyclohexyl 381 Ethyl 3-Methylcyclohexyl 382 Ethyl 4-Methylcyclohexyl 383 Ethyl 2,2-Dimethylcyclohexyl 384 Ethyl 3,3-Dimethylcyclohexyl 385 Ethyl 4,4-Dimethylcyclohexyl 386 Ethyl 2,6-Dimethylcyclohexyl 387 Ethyl 3,3,5-Trimethylcyclohexyl 388 Ethyl 3,3,5, o o 00 0 0 00 0 0 0 00 000 0 o0 0 0 S 0 900031 0O.Z. 0050/41443 No. R Physical data Ethyl EthylI Ethyl Ethyl Ethyl EthylI EthylI EthylI EthylI EthylI Ethyl EthylI Ethyl Ethyl EthylI EthylI Ethyl EthylI Ethyl EthylI Ethyl Ethyl Ethyl EthylI EthylI Ethyl EthylI 4-Ethylcyclohexyl 4-Propylcyclohexy I 4-Isopropylcyclohexyl 4-tert.-Butylcyclohexyl c is-4-tert Butylcyclohexyl trans-4-tert.-Butylcyclohexy 1 Hydrochloride mp. 185-186 0 c 4-tert Amylcyclohexyl Bicyclo[2.2. l]-hept-2-yl 1, 7,7-Trimethyl--bicyclo[2.2.11-hept-2-yl Bicyclo[4. 4. 0]dec-2-yl Bicyclo[4.4.Ol]dec-3-yl 2,6, 6-Trimethylbicyclo[3. 1.1 ]-hept-3-yl Phenyl 2-Methylphenyl 3-Methyl pheny I 4-Methylphenyl 2, 4-Dimethylphenyl 4-Isopropylphenyl 4-tert.-Butylphenyl 2-Methoxyphenyl 4-Methoxyphenyl 3, 4-Dimethoxyphenyl 4-tert Butoxyphenyl 2-Tn fluoromethylphenyl 3-Trifluoramethylphenyl 4-Trifluoromethylphenyl 4-Trifluoromethoxyphenyl a. a 00 0 0 a 9aa0 093 33 0.z. 0050/41443 No. RR2Physical data 416 Ethyl 2-Fluorophenyl 417 Ethyl 3-Fluorophenyl 418 Ethyl 4-Fluorophenyl 419 Ethyl 2,4-Difluorophenyl 420 Ethyl 2-Chiorophenyl 421 Ethyl 2-Chloro-4-fluorophenyl 422 Ethyl 3-Chiorophenyl 423 Ethyl 4-Chlorophenyl 424 Ethyl 2,4-Dichlorophenyl 425 Ethyl 2,6-Dichlorophenyl 426 Ethyl 427 Ethyl 2-Cyanophenyl 428 Ethyl 3-Cyanophenyl 429 Ethyl 4-Cyanophenyl 430 Ethyl 2-Hydroxyphenyl 431 Ethyl 3-Hydroxyphenyl 432 Ethyl 4-H-ydroxyphenyl 433 Ethyl 2-Nitrophenyl 434 Ethyl 3-Nitrophenyl 435 Ethyl 4-Nitrophenyl 436 Ethyl Benzyl 437 Ethyl 2-Methylbenzyl 439 Ethyl 24-iMethybenzy 438 Ethyl 24-Dmethylbenzyl 440 Ethyl 4-Isopropylbenzyl 441 Ethyl 4-tert.--Butylbenzyl 442 Ethyl 2-Methoxybenzyl 0 00080 00 a 0 0 8 80 0 0 0 8 0 900031 34 0.Z. 0050/41443 No. R 1 R2Physical data 443 Ethyl 3-Methoxybenzyl 444 Ethyl 4-Methoxybenzyl 445 Ethyl 3,4-Dimethoxybenzyl 446 Ethyl 4-tert.-Butoxybenzyl 447 Ethyl 2-Trifluoromethylbenzyl 448 Ethyl 3-Trifluoromethulbenzyl 449 Ethyl 4-Trifluoromethylbenzyl 450 Ethyl 4-Trifluoromethoxybenzyl 451 Ethyl 2-Fluorobenzyl 452 Ethyl 3-Fluorobenzyl 453 Ethyl 4-Fluorobenzyl 454 Ethyl 2,4-Difluorobenzyl 455 Ethyl 2-Chloro-4-fluorobenzyl 456 Ethyl 2-Chlorobenzyl 457 Ethyl 3-Chlorobenzyl 458 Ethyl 4-Chlorobenzyl 459 Ethyl 2,4-flichlorobenzyl 460 Ethyl 2.6-Dichlorobenzyl 461 Ethyl 462 Ethyl 2-Cyanobenzyl 463 Ethyl 4-Cyanobenzyl 464 Ethyl 2-Hydroxyhenzyl 465 Ethyl 3-Hydroxybenzyl 466 Ethyl 4-Hydroxybenzyl 467 Ethyl 2-Nitrobenzyl 468 Ethyl 3-Nitrobenzyl 469 Ethyl 4-Nitrobenzyl 0 a 0 00 0 0900031 0.Z. 0050/41443 No. R 1 R2 Physical data 470 Ethyl 2,4-Dinitrobenzyl 471 Eth~yl 2-Phenylethyl 472 Ethyl 2-(4-Methylphenyl)ethyl 473 Ethyl 2-(4-tert.-Butylphenyl)ethyl 474 Ethyl 2-(2-Methoxyphenyl)ethyl 475 Ethyl 2-(4-Methoxyphenyl)ethyl 476 Ethyl 4-Dimethoxyphenyl)ethyl 477 Ethyl 2-(4-tert.-Butoxyphenyl)ethyl 478 Ethyl 2-(4-Trifluoromethoxyphenyl)ethyl 479 Ethyl 2-(3-Trifluoromethyliphenyl)ethyl 480 Ethyl 2-(2-Fluorophenyl)ethyl 481 Ethyl 2-(4-Fluorophenyl)ethyl 482 Ethyl 2-(2-Ch'orophenyl)ethyl 483 Ethyl 2-(4-Cr ,crophenyl)ethyl 484 Ethyl 2-(2,4-Dichlorophenlyl)ethyl 485 Ethyl 2-(2-Chloro-4-fluorophenyl )ethyl 486 Ethyl 2-(4-Cyanophenyl)ethyl 487 Ethyl 2-(4-Hydroxyphenyl)ethyl 488 Ethyl 2-(4-Nitrophenyl)ethyl 489 Ethyl 3-Phenylpropyl 490 Ethyl 3-(4--Methylphenyl)prODY1 491 Ethyl 3-(4-tert.-Butylphenyl)propyl 492 Ethyl 3-(2-Methoxyphenl )propyl 493 Ethyl 3-(4-Methoxyphenyl)propyl 494 Ethyl 3-(3,4-Dimethoxyphenyl)propyl 495 Ethyl 3-(4-tert.-Butoxyphenyl)propyl 496 Ethyl 3-(3-Trifluoromethylphenyl)propyI 00 0O0 0 0 900031 36 0.Z. 0050/41443 No. RI R Physical data 497 Ethyl 3-(4-Trifluoromethoxyphel)propyl 498 Ethyl 3-(2--Fluorophenyl)propyl 499 Ethyl 3-(4-Fluorophenyl)propyl 500 Ethyl 3-(2-Chlorophenyl)propyl 501 Ethyl 3-(4-Chlorophenyl)propyl 502 Ethyl 3-(2,4-Dichlor~tphenyl)propyl 503 Ethyl 3-(2-Chloro-4-fluorophelyl)propyI 504 Ethyl 3-(4-Cyanophenyl)propyl 505 Ethyl 3-(4-Hydroxyphenyl)propyl 506 Ethyl 3-(4-Nitrophenyl)propyl 507 1-Propyl I-Pentyl 508 1-Propyl 2-Methyl-l-butyl 509 1-Propyl 2-Methyl-l-pentyl 510 1-Propyl 2-Ethyl-l-butyl 511 1-Propyl 2, 2-Diniethyl-l-propyl 512 1-Propyl 3,3-Dimethyl-l-butyl 513 1-Propyl 3-Methyl--1-butyl 514 1-Propyl 1-Hexyl 515 1-Propyl 2-methyl-l-hexyl 516 1-Propyl 2-Ethyl-1-hexyl 517 1-Propyl 2,4,4-Trimethyl-l-pentyl 518 1-Propyl 1-Heptyl 519 1-Propyl 1-Octyl 520 1-Propyl I-Nonyl 521 1-Propyl 1-Decyl 522 1-Propyl 1-Undecyl 523 l-Pr'opyl 1-Dodecyl 4 900031 37 0.Z. 0050/41443 No. RI R Physical data No. R 524 1-Propyl 2-Propen-1-yl 146 H 525 1-Propyl 2-Buten-1-yl 147 H 526 1-Propyl 2-Penten-1-yl 148 H 527 1-Propyl 2-Hexen-1-yl 4 528 1-Propyl 3-Methyl-2-buten-1-Yl 150 H 529 1-Propyl 2,3-Dimethyl-2-buten-1-yl 151 H 530 1-Prapyl 2-Hydroxyethyl 152 H 531 1-Propyl 6-Hydroxy-1-hexyl 153 H 532 1-Propyl 3-Chloro-1--butyl 154 H 533 1-Propyl 4-Chloro-1-butyl 155 H 534 1-Propyl 3-Chloro-2-methyl-1-propyl 156 H 535 1-Propyl Cyclopropy! 157 H 536 1-Propyl Cyclobutyl 158 H 537 1-Propyl Cyclopentyl 159 H 538 1-Propyl Cyclohexyl 160 H 539 1-Propyl Cycloheptyl 161 H 540 1-Propyl Cyciooctyi 162 H 541 1-Propyl C~clodecyl 6 542 1-Propyl Cyclododecyl 164 H 543 1-Propyl 1-Methylcyclopropyl 165 H 544 I-roy 1-Methylcyclopentyl16
H
545 1-Propyl 1-Methylcyclohexyl 167 H 546 1-Propyl 2-Methylcyclohexyl 168 H 547 1-Popy 3-eth~cylohxyl169
H
548 1-Propyl 4-Methylcyclohexyl 170 H 549 1-Propyl 2, -DMethylcyclohexyl 171 H 550 1-Propyl 3,3-Dimethylcyclohexyl 172 H 00000 0 0 0 *0 000 90003 38 O.Z. 0050/41443 No. RR2Physical data 551 1-Propyl 4, 4-Dimethylcyclohexyl 552 I-Propyl 2,6-Dimethylcyc-' exyl 553 1-Propyl 3,3, 554 1-Propyl 3, 3,5, 555 1-Propyl 4-Ethylcyclohexyl 556 1-Propyl 4-Propy icyclohexy 1 557 1-Propyl 4-Isopropylcyclohexyl 558 1-Propyl 4-tert.-Butylcyclohexyl 559 1-Propyl cis-4-tert.-Butylcyclohexyl 560 1-Propyl trans-4-tert.-Butylcyclohexyl bp 230-236 0 C/0.2 mbar 561 1-Propyl 4-tert.-Amylcyclohexyl 562 1-Propyl Bicyclo[2.2.1]-hept-2-yl 563 1-Propyl 1,7,7-Trimethyl-bicyclo[2.2-1]-hept-2-yl 564 1-Propyl Bicyclof4-4.0]dec-2-yl 565 1-Propyl Bicyclo[4.4.Q]dec-3-yl 566 1-Propyl 4,6, 6-Trimethylbicyclo[3.1 .1i-hept-3-yl 567 1-Propyl Phenyl 568 1-Propyl 2-Methyiphenyl 569 1-Propyl 3-Methyiphenyl 570 1-PropyI 4-Methyiphenyl 571 1-Propyl 2,4-Dimethylphenyl 572 1-Propyl 4-Isopropylphenyl 573 1-Propyl 4-tert.-Butylphenyl 574 1-Propyl 2-Methoxyphenyl 575 1-Propyl 4-Methoxyphenyl 576 1-Propyl 3,4-flimethoxyphenyl 577 1-Propyl 4-ter+t.-Butoxyphenyl F 000 0900C0 1.
39 o.z. 0050/41443 No. RR2Physical data 578 I-Propyl 2-Trifluoromethylphelyl 579 1-Propyl 3-Tn fluoromethylphelyl 580 1-P *opyl 4-Trifluoromethylphenl 581 1-Propyl 4-Trifluoromethoxyphenyl 582 1-Propyl 2-Fluorophenyl 583 1-Propyl 3-Fl uorophenyl 584 1-Propyl 4-Fluorophenyl 585 1-Propyl 2,4-Difluorophenyl 586 1-Propyl 2-Chlorophenyl 587 1-Propyl 2-Chloro-4-fluorophenyl 588 I-Propyl 3-Chlorophenyl 589 1-Propyl 4-Chlorophenyl 590 1-Propyl 2,4-Dichlorophenyl 591 1-Propyl 2,6-Dichlorophenyl 592 1-Prapyl 593 1-Propyl 2-Cyanophenyl 594 1-Propyl 3-Cyanophenyl 595 I-Propyl 4-Cyanophenyl 596 1-Propyl 2-H-ydroxyphenyl
I
597 1-Propyl 3-Hydroxyihenyl 598 1-Propyl 4-Hydroxyphenyl 600 1-Propyl 3-Nlitrophenyl 599 1-iPropyl 2-Nitrophenyl 601 1-Propyl 4-Nitrophenyl 602 1-Propyl Benzyl 603 1-Propyl 2-methylbenzyl 604 1-Propyl 4-Methylbenzyl 0 E. a a 0.Z. 0050/41443 No. RI R F-mysical data N. R 227 Me 605 1-Propyl 2,4-Dimethylbenzyl 606 1P~ 1228 Me -Prap 1 4-Isopropylbenzyl 607 1-Propyl 4-tert.-Butylbenzyl I229 Me- 608 1-Propyl 2-Methoxybenzyl 230 Me- 609 1-Propyl 3-Methoxybenzyl 231 Mel 610 1-Propyl 4-Methoxybenzyl 232 Mel 6i1 1-Propyl 3,4-Dimethoxybenzyl 233 Mel 612 I-Propyl 4-tert.-Butoxybenzyl 234 Me, 613 I-P opy 2- ri luo onzthy ben yl235 Mel 613 1-Propyl 2-Trifluoromrethylbenzyl23 Me 614 1-Propyl 4-Trifluoromethylbenzyl 236 Mel 615 1-Propyl 4-TrifluoromTethoybenzyl 237 Mel 617 I-Propyl 4-TrFluororhxbenzyl 238 Mel 617 1-Prpyl 3-,FLuorobenzyl 239 Mel 618 1-Propyl 4-Fiiiorobenzyl 240 Mel 619 '-Propyl 24-Difuorobenzy l 241 Mel 620 1-Propyl 2,-Dior4fluorobenz 242 Mel 621 1-Propyl 2-Chloro-4-eurobnz. 243 Mel 622 1-Propyl 2-Chlorobenzyl 244 Mel 623 1-Prpyl 3-Chlorobenzyl 245 Mel 624 1-Propyl 24-Dchlorobenzyl 246 Mel 6Z6 i -P opy 2, -Di hl o obt zyl247 Mel 625 1-Propyl 3,5-Dic~hlorobenzyl25 Me 628 1-Propyl 2-Cyanobenzyl25 Me 629 1-Propyl 4-Cyanobenzy1 251 Mel 630 1-Propyl 2-l-ydroxybenzyl 252 Mel 631 I-Propyl 3-Hydroxybenzy! 5 e 0 9 'b0 00 0 v 0 0 6C 000 S c0oo 0 9000l31 41 0.Z. 0050/41443 '1o. R1R 2 Physical data 632 1-Propyl 4-iydroxybenzyl 633 1-P-opyl 2-NitrobenzyI 634 1-Propyl 3-Nitrobenzi, ,535 1-Propyl 4-Nitrobenzyl 636 1-Propyl 2,4-Dinitrobenzyl 637 1-PopL 2-Phenylethyl 638 1-Propyl 2-(4-Methylpheanyl)ethyl 639 1-Propyl 2-(4-tert.-Butylphenyflethyl 640 1-Propyl 2-(2-tmethoxyphenyl )ethyl 641 1-Propyl 2-(4-Methoxyphenyl )ethyl 642 1-Propyl 4-Dimethoxyphenyl)ethyl 643 1-Propyl 2-(4-tert.-Butoxyphenyl)ethyl 644 1-Propyl 2-(4 Trifluoromethoxyphefylth.fi 645 1-Propyl 2-(3-Tri fluoromnethylph-,fly l)ethiyi 646 1-Propyl 2-(2-Fluorophenyl)ethyl 647 1-Propyl 2-(4-Fluorophenyl)ethyl 648 1-Propyl 2-(2-ChIorophenyl)ethyI 649 1-Propyl 2-(4--Chloropheflyl ethyl 650 1-Propyl 4-Dichlorophenyl)ethyl 651 I-Propyl 2-(2-Chloro-4-fluorophenyl)ethyI 652 1-Propyl 2-(4-Cyanopheny ethyl 653 1-Propyl 2-(4-HydroxyphenyI )ethyl 654 1-Propyl 2-(4-Nitrophenyl)ethyl 655 1-Propyl 3-Phenyipropyl 656 1-Propyl 2l-(4-Methylphenyl )propyl 657 1-Propyl 3-14-tert.-But-ylphel)propyl 658 1-Propyl 3-(2-Methoxypheny1 )propyl f, 000 a a a a CO a 0 0 0 a 0~ C 0 0 0 0 0 00 000 000 0 0 0 0 0 0 00 0 0 0 0 p 0 0 0 0 000 0 0 0 0 0 0 0 00.~ 0 900031 o.z. 0050/41443 No. R Physical data 659 660 661 662 663 664 665 666 667 668 669 670 671 672 673 674 675 676 677 678 679 680 681 682 683 684 685 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 1-Propyl 2-P ropen-1 -y1 2-P ropen-l-y 1 2-Propen-1-yl 2-Propert-1-yl 2-Propen- 1-y 1 2-P ropen-1-y 1 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-y 1 2-Propen-1-yl 2-Propen- 1-y 1 2-Propen-1-yl 3- (4-Methoxyphenyl )propyl 4-Dimethoxyphenyl)propyl 3-(4-tert.-Butoxyphenyl )propyl 3-(3-Tri fluorornethylphenyl )propyl 3- (4-Trifluoromethc.xyphenyl)propyI 3-(?-Fluorophenyl)propyl 3-(4-Fluoropheny1 )propyl 3-(2-Chlorophenyl )propyl 3- (4-Chlorophenyl )propyl 4-Dichlorophenyl)propyl 3- (2-Chloro-4-fluorophenyl ropyl 3- (4-Cyanophenyll)propyl 3- (4-Hydroxyphenyl )propy! 3- (4-Nitrophenyl )propyl Methyl Ethyl 1-Pro py I 2-P ropy 1 1-Buty 1 2-Butyl tert Butyl 2-Methyl-l-propyl 1-Pentyl 2-Methyl-l-butyl 2-Methyl-1-penty 1 2-Ethyl-1-buty 1 2, 2-Dimethyl-l-propyl Vr~' r 0 40 o 0 C, 00 060 .00 0 0 0 C' 0 0 0 C 0 0 0 0 0 0 0 0 0 0 0 0 000 0 0 0 0 0 0 0 0.0 00 0 900031 o.z. 0050/41443 No. R Physical data 686 687 688 689 690 691 692 693 694 695 696 697 698 699 700 701 702 703 704 705 706 707 708 709 710 711 712 2-Pro 'pen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2-P ropen-1 -yl* 2-Propen-1-yl 2-P ropen-1-y 1 2-Propen-1-y 1 2-Propen-1-y 1 2-Propen-1-y 1 2-Propen-1-yl 2-P ropen-1 -yl 2-P ropen-1-y 1 2-P ropen-1-y I 2-P ropen-1-y 1 2-Propen-1-y 1 2-Propen-1-yl 2-P rope n-1-y I 2-P ropen-1 -yl 2-P ropen-1-y I 2-Propen-1-yl 2-P ropen-1-y 1 2-P ropen-1-y 1 2-P ropen-1-y 1 2-Propen-1-yl 2-P ropen- 1-yl 2-Propen-1-yl 2-Propen-1-y l 3, 3-Dimethyl-l-butyl 3-Methyl-1-butyl 1-Hexyl 2-Methyl -1-hexy 1 2-Ethyl -1-hexy l 2,4, 4-Trimethyl-1-pentyl 1-Heptyl 1-Octyl 1-Nonyl I-Decyl 1-Undecy I 1-Dodecy 1 2-Propen-1-y 1 2-Buten-1-yl 2-Penten-1-y 1 2-Hexen-1-yl 3-Methy l-2-buten-1-y 1 2, 3-Dimethyl-2-buten-1-yl 2-Hydroxyethy I 6-Hydroxy-1-hexy I 3-Chloro-1-butyl 4-Chloro-1-buty 1 3-Chloro-2-niethyl-1-propyl Cyclopropyl Cyclobutyl Cyclopentyl Cyclohexyl r 000 0 0 0 0 S 000 00 0 0 00 0 00 0 0 C' 0 0 0 qO 00~ o 0 0 0 0 0 C 000 0 00 0 44 ~~T1 900031 0.7. 0050/41443 No. R Physical data 713 714 715 716 717 718 719 720 721 722 723 724 725 726 727 728 729 730 731 732 733 734 735 736 737 738 739 2-Propen-1-yl 2-P ropen-1 -yl 2-P ropen-l-y 1 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-y 1 2-Propen-1-yl 2-Propen-1-y 1 2-Propen-1 -yl 2-Propen-1-y 1 2-Propen-1-y 1 2-Propen-1-yl 2-Propen-1-yl 2-P ropen-1-y 1 2-Propen-1-yl 2-Propen-1-y I 2-Propen-1-y 1 2-Propen-1-y I 2-Propen-1-yl 2-P ropen-1-y 1 2-Propen-1-y 1 2-Propen-1-yl 2-P rope n-i -yl 2-Propen-1-y 1 2-Propen-1-y1 2-Propen-1-y I Cycloheptyl Cyclooctyl Cyclodecyl Cyclododecyl 1-Methylcyclopropyl I-Methylcyclopenty 1 I-Methylcyclohexyl 2-Methylcyclohexyl 3-Methylcyc lohexyl 4-Methylcyclohexyl 2, 2-Dimethylcyclohexyl 3, 3-Dimethylcyclohexyl 4, 4-Dimethylcyclohexyl 2, 6-Dimethylcyclohexyl 3,3, 3,3,5, 4-Ethylcyclohexyl 4-Propylcyclohexyl 4-Isopropylcycloh-<vl 4-tert Butylcyc lohexyl cis-4-tert. -Butylcyclohexyl trans-4-tert.-BUtylcyclohexyl resin (cis/trans =2:3) 4-tert.-AmylcyclohexyI Bicyclo[2.2. I]-hept-2-yl 1,7, 7-Trimethyl-bicyclo[2.2. 1]-hept-2-yI Bicyclo[4.4.0]dec-2-yl Bicyclo[4.4.0]dec-3-yl r 000 0 0 0 0 0 000 0 0 0 0 p 0 0 0 0 0 0 O 0 0 0 0~ 000 o 0 0 0 0 600 0 00 0 4- 900031 0.Z. 0050/41443 No. R Physical data 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2-P ropen-1-y I 2-Propen-1 -yl 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-y-i 2-Propen-1-:yt 2-Propen-1-y I 2-Propen-1-yl 2-Propen-1-y 1 2-Propen-1-yl 2-Propen-1-y 1 2-Propen-1-yl 2-Propen-1-y1 2-Propen-1-yl 2-Propen-1 -y 1 2-P ropen-1-y l :-Propen-1-y I 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-y I 2-Pr-open-i -yl 2,6, 6-Trimethylbicycloll3.1.1]-hept-3-yl Phenyl 2-Methyiphenyl 3-Methyl pheny l 4-Methyl pheny l 2, 4-Dimethylpheny1 4-Isopropylphenyl 4-tert ButylIpheny 1 2-Methoxyphenyl 4-Methoxyphenyl 3, 4-Di'methoxyphenyl 4-tert.--Butoxypheny l 2-Trifluoromethylphenyl 3-TrifluoromethylIphenyl 4-Trifluoromethylphenyl 4-TrifI uoromethoxypheny l 2-Fl1uorophenyl 3- Fluorophenyl 4-Fluorophenyl 2, 4-Di fluorophenyl 2-Chiorophenyl 2-Chloro-4-fI uoropheny l 3-Chlorophenyl 4-Chioropheny I 2, 4-Dichlorophenyl 2, 6-Dichiorophenyl 3,
T,
r 900031 O.Z. 0050/41443 No. R Physical data 767 768 769 770 771 772 773 774 775 776 777 778 779 780 781 782 783 784 785 786 787 788 789 790 791 792 793 2- Ipn-- 2-P ropen-1-y 1 2-Propen-1-y I 2-P ropen-1 -yl 2-Pro pen-1-y 1 2-Propen-1-y 1 2-P ropen-1-y 1 2-Propen-1-y 1 2-Propen-1-y 1 2-P ropen-1-y 1 2-Prope n-i -yl 2-P ropen-1-y 1 2-Propen-1-yl 2-Propen-1-y 1 2-Propen-1-y 1 2-Propen-1-y 1 2-P ropen-1 -y 1 2-P ropen-1-y 1 2-P ropen-1-y I 2-P ropen-1 -yl 2-P ropen-1-y 1 2-Propen-1-y I 2-Propen-1 -yl 2-Propen-1-yl 2-Propen-1-y 1 2-Propen-I-y 1 2-Propen-1-yl 2-Cy anopheny 1 3-Cyanopheny 1 4-Cyanophenyl 2-Hydroxypheny I 3-Hydroxy pheny 1 4-H-ydroxypheny 1 2-Nitrophenyl 3-Nitrophenyl 4-Nitrophenyl Benzyl 2-Methylbenzyl 4-Methy lbenzy 1 2, 4-Dimethylbenzyl 4-Isopropylbenzyl 4-tert.-Butylbenzyl 2-Methoxybenzy 1 3-Methoxybenzy 1 4-Methoxybenzy 1 3, 4-Dimethoxybenzyl 4-tert Butoxybenzyl 2-Tn fluoromethylbenzyl 3-Trifluoromethylbenzyl 4-Tn fluoromethylbenzyl 4-T i fluoromethoxybenzyl 2-Fluorobenzyl 3-Fluorobenzyl 4-Fluorobenzyl
V
4 4 4 0 *0 9 9 4 0 9 94 004 0 0 0 D 900031 Q.z. 0050/41443 No. R Physical data 2-P ropen-l -yl 2-Propen-1-y 1 2-Propen-l-yl 2-Propen-1-yl 2-Propen-1-yl 2-Pro pen-i -yi 2-Propen-l-y 1 2-Propen-1-y l 2-P ropen-1-y 1 2-Propen-1-yl 2-Propen-1-y l 2-P ropen-1 -y I 2-Propen-1-y l 2-Propen-1-yl 2-Propen-1-yl 2-Propen-l-y 1 2-Propen-1-y l 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2-Propen-l-y I 2-Propen-1 -yl 2-Pro pen- l-yl 2-Propen-l-y 1 2-Propen-1-yl 2-Propen-1-yl 2-Propen-1-yl 2, 4-Di fluorobenzyl 2-Chi oro-4-fluorobenzyI 2-Chlorobenzyl 3-Chl1orobenzy l 4-Chi orobenzy 1 2, 4-Dichlorobenzyl 2, 6-Dichlorobenzyl 3, 2-Cy anobenzy 1 4-Cy anobenzy l 2-H-ydroxybenzy 1 3-Iydroxybenzy I 4-Hydroxybenzy 1 2-Ni trobenzyl 3-Ni trobenzy l 4-Ni trobenzy! 2, 4-Oinitrobenzyl 2-Ph enylIethyl 2-(4-Methylphenyl )ethyl 2-(4-tert.-Butylphenyl )ethyl 2-(2-methoxyphenyl )ethyl 2-(4-Methoxyphenyl )ethyl 4-Dimethoxyphenyl)ethyl 2-(4-tert.-Butoxyphenyl) ethyl 2-(4-Tr luoromethoxyphenyl)ethyl 2-(3-Tri tluoromethylphenyl )ethyl 2-(2-Fluorophenyl )ethyl r SO. 0 t~ 0 0 0* 00 000 S 000 0~ 0 oa sot 0 0 0 00 9 48 900031 0.Z. 0050/41443 No. R Physical data 821 822 823 824 825 826 827 828 829 830 831 832 833 834 835 836 837 838 839 840 841 842 843 844 845 846 2-Prope n-i -yl 2-P rope n-i -y 2-P ropen-1-y 1 2-Prope n-i -yl 2-P ropen-1 -y 1 2-P ropen-1-y 1 2-Propen-1-y 1 2-Propen-1-y I 2-Propen-1-y I 2-P ropen-1 -yl 2-Propen-1-y 1 2-Propen-1 -yl 2-Propen-1 -yl 2-Propen-I-yl 2-Propen-1-yi 2-Propen-1-yl 2-Propen-1-y 1 2-P ropen-1 -yl 2-Propen-1 -y1 2-Propen-1-yl 2-Propen-1-yl 2-P ropen-1 -yl 2-Prope n-I -yl 2-Propen-1-yl 2-Propen-1-y 1 2-Propen-1-y I 2-(4-Fluorophenyl )ethyl 2-(2-Chlorophenyl )ethyl 2- (4-Chloropheny1) ethyl 4-Dichiorophenyl )ethyl 2-(2-Chloro-4-fluorophenyl )ethyl 2-(4-Cyanophenyl )ethyl 2-(4-Hydroxyphenyl )ethyl 2-(4-Nitrophenyl )ethyl 3-PhenylIpropy I 3-(4-Methylphenyl )propyl 3-(4-tert.-Butylphenyl )propyl 3-(2-Methoxyphenyl )propyl 3-(4-Methoxyphenyl )propyl 4-Dinethoxyphenyl)propyl 3-(4-tert.-Butoxyphenyl )propyl 3-(3-Tri fluoromethyiphenyl )propyI 3-(4-Tri fluoromethoxyphenyl )propyl 3- (2-Fluorophenyl )propyl 3-(4-Fluorophen~yl )propyl 3-(2-Chlorophenyl )propyl 3- (4-Chiorophenyl )propyl 4-Dichlorophenyl)propyl 3- (2-Chloro-4-fluorophenyl )propyl 3- (4-Cyanophenyl )propyl 3-(4-Hydroxyphenyl )propyl 3-(4-Nitrophenyl )propyl 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.
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 vegetables such as cucumbers, beans and cucurbits.
The novel compounds are particularly useful for controlling the following plant diseases: Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, ooa Uncinula necator in vines, Puccinia species in cereals, °ca 20 Rhizoctonia solani in cotton, S Ustilago species in cereals and sugar cane, Venturia inaequalis (scab) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, 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, Fusarium and Verticillium species in various plants, o- plasmopara viticola in grapes, S Alternaria species in fruit and vegetables.
SThe compounds are applied by spraying or dusting the plants with the o °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.
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 emulsifiers and dispersants; if water 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 xylene), chlorinated aromatics chlorobenzenes), paraffins crude oil fractions), alcohols methanol, butanol), ketones cyclohexanone), amines ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals kaolins, aluminas, talc and chalk) and ground synthetic minerals highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as ligninsulfite waste liquors and methylcellulose.
The fungicides generally contain from 0.1 to 95, and preferably from to 0, wt% of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting °"i 0 materials (timber), on Paecilomyces variotii. When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and o o preferably from 0.01 to 20, g per kg of seed are generally required.
o o The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, o "Bso 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-methyl-a-pyrrolidone, which is suitable for application in the 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 cleic acid-N-monoethanolamide, 5 parts by weight of 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. 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 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.
f 51 O.Z. 0050/41443 IV. An aqueous dispersion of 20 parts by weight of compound no. 39, 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 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 acid, 10 parts by weight of the sodium salt of a lignin-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.
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 S active ingredient.
S VII. An intimate mixture of 30 parts by weight of compound no. 59, 92 o "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 a active ingredient exhibits good adherence.
VIII. A stable aqueous dispersion of 40 parts by weight of compound no.
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.
*o ao f 4 IX. A stable oily dispersion of 20 parts by weight of compound no. 67, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, S 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-fornaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
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.
52 0.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.
Examples of fungicides which may be combined with the novel compounds are: sul fur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebi sdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc N,N'-ethylenebisdithiocarbamate, ammonia complex of zinc N,N'-propylenebisdithiocarbamate, 0: zinc N,N'-propylenebisdithioccarbamate and N, N-polypropylenebis(thiocarbamyl) disulfide; 060 20 nitro derivatives, such as 'Doc C dinitro(l-methylheptyl)-phenyl crotonate, 0 or' 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethyl,-.rylate, 0 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and diisopropyl heterocyclic substances, such es 2-heptadecylimidazol-2-yl acetate, o 2,4-dichloro-6-(o-chloroanilino)-s-triazine, C 0,0-diethyl phthalimidophosphonothioate, 5-amino-1- [-bi s-(d imethyl amino) -phosphi ny I I-3-pheny 1-1, 2, 4-tri azole, o 0 2,3-dicyano-1,4-dithioanthraquinone, 2-th jo-i, 3-dithio 5-b] quinoxaline, methyl l-(butylcarbamyl )-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)-benzimidazole, 2-(thiazol-4-yl )benzimidazole, N-(1,l,2,2-tetrachloroethylthio)-tetrahydrophthalilide, N-trichloromethylthi otetrahydrophtha imid, N-trichloromethylthlophthai mide, N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1, 2, 3-thi adi azole, 2-thiocyanatomethylthiobenzothi azole, 1, 4-dichloro-2, 53 O.Z. 0050/41443 4- (2-ch Ioropheny I hydrazono) -3-methy 1-5-i sox azo Ione, 2-thiopyridine 1-oxide, 8-hydroxyquinoline and its copper salt, 2, 3-di hydro-5-carboxanilIido-6-methy 1-1, 4-oxathiyne, 2, 3-dihydro-5-c arbox an i Iido-6-me thy 1-1, 4-ox at hiyne 4,4-dioxide, 2-methyl1-5, 6-dihydr'o-4H-pyr an -3-carbox an i I ide, 2-methylfuran-3-carboxanilide, 2, 5-dimethylfuran-3-carboxanilIide, 2, 4, 5-tr ime thyIf ur an-3-c arbox anilide, 2, 5-dimethyl-N-cyclohexylfuran-3-carboxamide, N-cyc lohexyl-N-methoxy-2, 5-diethyl furan-3-,..rboxamide, 2-methylbenzanilide, 2-iodobenzanil1ide, N-f ormy I -N-morpholIine-2, 2, 2-trich IoroethylIac etalI, piperazine-l,4-diylbis-(1-(2, 2,2-trichloroethyl)-formamide), 1-(3,4-dichloroanilino)-l-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine and its salts, 2,6-dimethyl-N-cyclododecylmorpholine and its salts, N-13-(p-tert.-butylphenyl)-2-Hethylpropyl]-cis-2,6-dimethylmorpholine, V 20 N-(3-(p-tert.-bUtylphenyl )-2-methylpropyl]-piperidine, V 1-f2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl1-lH-1,2,4ii -triazole, 4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-IH-1, 2,4- -triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazoIl-lurea, 1-(4-chlorophenoxy)-3,3--dimethyl-l-(lH-1,2,4-triazol-1-yl)-butan-2-ole, 1-(4-chlorophenoxy)-3,3-dimethyl-l-(1H-1,2,4-triazol-1-yl)-butal-2-ol, c-(2-chlorophenyl)-ci-(4-chlorophenyl)-5-pyrimidinemethanol, I- (2-d I'methy I am ino-4-hydroxy-6-methy-i yrimidinie, bLs-(p-chlorophenyl)-3-pyridinemethanol, 1, 4-bis- (3-ethoxyc arbonylI-2-thiourei do) -benzene, 4 1, 2-bis-(3-methoxyc arbony I-2-thiourei do) -benzene, and various fungicides, such as 3dodecylguanidine acetate, 5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide, hexachlorobenzene, DL-methyl-N-(2, 6-dimethylphenyl)-N-fur-Z-yI alanate, methyl OL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate, 6-dfmethylphenyl)-N-chloroacetyl-OL-2-aminobutyrolactone, methyl OL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate, I-5-viny 5-dich Iorophefy 4-dioxo-1, 3-oxazoIidia'i 5-dichilorophenyl]-5-methyl-5-methoXymethyl-1, 3-oxazol idine-2, 4--i'ine, dichlorophenyl)-l-isopropylcarbalylhydaltoin, N-3,5dclrpey)12dmthlylpoae12dcroiie 54 0.Z. 0050/41443 2--cyano-[N- (ethy IaminocarbonyI) -2-methoximi no)]-acetamide, 1- 4-d ic hlIorophenylI-penty 1 lH- 1,2, iazolIe, 2, 4-di uoro-ct-(lH-1, 2, azoI-1-y IiethylI)-benzhy drylI alIcoho, N-(3-ch Ioro-2, 6-dinitro- +-tri flIuoromethy IphenylI)-5-trif Iuoromethyl-3chloro-2-ami nopyri dine, and 1-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-H-1,2,4-triazole.
Ut'e examples For comparison purposes, l-(4-(4-tert--butylphenyl) cyclohexi'i)-2,6dimethylmorpholine (IA) disclosed in EP 259,977, N,N-dim~th1yl-4-(cyclohexylmethyl)-cyclolexylamine and 4(cyclohexylmethyl)-cyclohexylamine both disclosed in U.S. 3,981,766, and trans-4--tert-butyl-N-benzylcy';Aohexy~cvmine disclosed in Journal of Organic Chemistry, 48 (1983), pp. 3412-3422 Use Example 1 Action on Plasmopara viticola Leaves of potted v'ines of the M~ller-Thurgauj variety were sprayed with 6queous suspensions contain~qg (dry basis) 60%. of active ingredient and 2(j% of emulsifier. To assess duration of action, trie plants were set 4 isp, after the sprayed-on layer had dried, for 8 days in the greenhouse.
Then the leaves were infected with a zoospore suspension oi" rF-asmopara viticola. The plants were first placed for 48 hours in a water vaporsaturated chamber at 24 0 C and then in a greenhouse for 5 days at from Ii to 30 0 C. To accelerate and intensify the sporangiophore discharge, the plantc were then again placed in the moist chamber for 16 hours. The extent of fungus attaick was then assessed on the undersides of the leaves.
d 30 The results show th active ingredients 5, 15, 39, 40, 50, 59, 61, 62 and it 67, applied as 0.025vt% spray liquors, have a better fungicidal action (1006) than prior art comparative agents A and C Use Example 2 Action on Botrytis cinerea in paprika Paprika seedlings of the "Neusiodler Ideal Elite" variety were sprayed, after 4 to 5 leaves were well developed, to runoff with aqueous suspensions containing -(dry basis) 80%6 of active ingredient and 20% of emul- After che sprayed-on layer had dried, the plants were sprinkled with a coriidial suspension of the fungus Botrytis cinerea, and placed at 22 to 24 0 C in a chamber of high humidity. After 5 days, the disease hi spread to sitzh a great axtent on the untreated plants that the necroses covered the major portion of the leaves.
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 than prior art active ingredients B, C and 0 235 0

Claims (4)

  1. 2. A fungicidal agent containing an inert carrier and a fungicidally effective amount of a 4-(4-tert-butylphenyl)-cyclohexylamine or a quaternary ammonium salt thereof of the formulae Ri CH 3 I R2 LCH 3 where R 1 is- hydrogen, Cl-C 6 -alkyl or C 3 -C 6 -alkenyl, R 2 is Cl-C 12 -alkyl, C 1 -C 12 haloalkyl, Cl-C 12 -hydroxyalkyl, C 3 -C 12 cycloalkyl, C 4 -C 1 2 -alkylcycloalkyl, C 7 -C 12 -bicycloalkyl, C 3 -C 12 alkenyl, unsubstituted, monosubstituted, disubstituted or tri- a' *4& 57 0.Z. 0050/41443 substituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl-(Cl-C 3 )alkyl, the substituents in each case being identical or different and being Cl-C 4 alkyl, C 1 -C 4 -alkoxy, Cl-C 4 -haloalkyl, Cl-C 4 -haloalkoxy, halogen, cyano, hydroxyl or nitro groups, with the proviso that RI and R 2 are not simultaneously Cl-C 4 alkyl, Xe) is a plant-tolerated acid anion, or a plant-tolerated acid addition salt thereof.
  2. 3. A process for combating fungi, wherein the fungi or thf plants, seed, materials or the soil to be protected against fungus attack are treated with a fungicidally effective amount of a 4-(4-tert-butyl- phenyl)-cyclohexylamine or a quat6rnary ammonium salt thereof of the formulae RI CH 3 Nand N-2 xe 1 2 where R 1 is hydrogen, Cl-C 6 -alkyl &r C 3 -C 6 -alkenyl, R 2 is Cl-C 12 -alkyl, Cl-C 12 -haloalkyl, G 1 -Cl 2 -hydroxyalkyl, C 3 -C 12 cycloalkyl. C 4 Cl 2 -alkylcycloalkyl, C 7 -C 1 2 -bicycloalkyl, C 3 -C 12 a alkenyl, unsubstituted, monosubstituted, disubstituted or tri- Goa 1 substituted phenyl, or unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl-(Cl-C3)alkyl, the substituents in each case being identical or different and being CI-4akl C 1 -C-loy Cl-C 4 -haloalkyl, C 1 -C4-haloalkoxy, halogen, cyano, hydroxyl or nitro groups, with the proviso that R1 R 2 are not simultaneously Cl-C 4 alkyl, x9 is a plant-tolerat acid anion, or a plant-tolerated acid addition salt thereof.
  3. 4. A compound of the formula 1 as set forth in claim 1, where RI is hydrogen and R 2 is 4-tert-butylcyclohexyl. A compound of the formula 2 as set forth in claim 1, where R 2 is 4-tert-butylcycloh~exyl and Xe is iodide. 0.Z. 0050/41443
  4. 6. A comrpound of the formula 1 as set forth in claim 1, where R1 is hydrogen and R 2 is cyclohexyl. DATED this 4th day of March 1991. BASF AKTIENGESELLSCHAFT WATERMARK PATENT TRADEMARK ATTORNEYS 'THE ATRIUM" 290 BURW(XJD ROAD HAWTHORN. VIC. 3222. OG 0 0 0 *000,A 000- 00 0 0 00 0~35
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Citations (3)

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EP0258853A1 (en) * 1986-09-05 1988-03-09 BASF Aktiengesellschaft 4-Substituted cyclohexylamine derivatives, fungicides containing them and process for combating fungi
EP0259977A2 (en) * 1986-09-10 1988-03-16 Imperial Chemical Industries Plc Tertiary amine compounds
EP0269041A2 (en) * 1986-11-25 1988-06-01 BASF Aktiengesellschaft Fungicidal cyclohexylamines

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US2967125A (en) * 1958-10-13 1961-01-03 Velsicol Chemical Corp Phenylcyclopentylamine fungicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0258853A1 (en) * 1986-09-05 1988-03-09 BASF Aktiengesellschaft 4-Substituted cyclohexylamine derivatives, fungicides containing them and process for combating fungi
EP0259977A2 (en) * 1986-09-10 1988-03-16 Imperial Chemical Industries Plc Tertiary amine compounds
EP0269041A2 (en) * 1986-11-25 1988-06-01 BASF Aktiengesellschaft Fungicidal cyclohexylamines

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