Cyclohexylamino and cycloalkoxy nitrogen heterocycles, processes for their preparation, and their use as pesticides and fungicides

Cyclohexylamino and cycloalkoxy nitrogen heterocycles, processes for their preparation, and their use as pesticides and fungicides. The invention relates to compounds of the formula EQU Ar--X-E-Q in which Ar is substituted or unsubstituted 4-pyridyl or 4-pyrimidinyl; X is NH, O, S, SO or SO.sub.2 ; E is a bond or alkanediyl; and Q is a substituted cycloalkyl or 4-piperidyl. The invention also relates to processes and intermediates for their preparation, to compositions comprising them and to their use as pesticides and fungicide.

It is already known that certain 4-cycloalkylamino and 4-cycloalkoxy 
nitrogen heterocycles possess an insecticidal, acaricidal, ixodicidal and 
fungicidal action (WO 93 00536). 
Novel 4-amino- and 4-alkoxy-substituted nitrogen heterocycles have now been 
found of the formula I 
##STR1## 
in which the radicals and groups are as defined below, which, while 
showing good tolerance by plants and favorable toxicity toward 
warm-blooded animals, are highly suitable for controlling animal pests, 
such as insects, arachnids, nematodes, helminths and molluscs, for 
controlling endoparasites and ectoparasites in the veterinary field, and 
for controlling harmful fungi. 
The invention therefore relates to compounds of the formula I in which 
R.sup.1 is hydrogen, halogen, (C.sub.1 -C.sub.4)-alkyl or (C.sub.3 
-C.sub.5)-cycloalkyl; 
R.sup.2 and R.sup.3 are identical or different and are each hydrogen, 
(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.2 
-C.sub.4)-alkenyl, (C.sub.2 -C.sub.4)-haloalkenyl, (C.sub.2 
-C.sub.4)-alkynyl, (C.sub.2 -C.sub.4)-haloalkynyl, (C.sub.1 
-C.sub.8)-trialkylsilylalkynyl, preferably dimethyl-(C.sub.1 
-C.sub.8)-alkylsilylalkynyl, phenyl-(C.sub.1 
-C.sub.8)-dialkylsilylalkynyl, preferably phenyldimethylsilylalkynyl, 
aryl-(C.sub.1 -C.sub.2)-alkyl-(C.sub.1 -C.sub.8)-dialkylsilylalkynyl, 
preferably benzyldimethylsilylalkynyl, (C.sub.3 
-C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.8)-dialkylsilylalkynyl, preferably 
(C.sub.3 -C.sub.8)-cycloalkyldimethylsilylalkynyl, (1-methylsila-(C.sub.3 
-C.sub.8)-cycloalk-1-yl)alkynyl, preferably 
(1-methylsilacyclopent-1-yl)alkynyl or (1-methylsilacyclohex-1-yl)alkynyl, 
triphenylsilylalkynyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 
-C.sub.4)-haloalkoxy, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, 
(C.sub.1 -C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 
-C.sub.4)haloalkoxy-(C.sub.1 -C.sub.4)-haloalkyl, halogen, hydroxyl, 
(C.sub.1 -C.sub.4)-hydroxyalkyl, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.1 
-C.sub.4)-alkanoyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-haloalkanoyl, (C.sub.3 -C.sub.5)-cycloalkyl, (C.sub.3 
-C.sub.5)-halocycloalkyl, cyano, (C.sub.1 -C.sub.4)-cyanoalkyl, nitro, 
(C.sub.1 -C.sub.4)-nitroalkyl, thiocyano, (C.sub.1 
-C.sub.4)-thiocyanoalkyl, (C.sub.1 -C.sub.4)-alkoxycarbonyl, (C.sub.1 
-C.sub.4)-alkoxycarbonyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-haloalkoxycarbonyl, (C.sub.1 -C.sub.4)-alkanoyloxy-(C.sub.1 
-C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkylthio, (C.sub.1 
-C.sub.4)-alkylthio-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-haloalkylthio, (C.sub.1 -C.sub.4)-alkylsulfinyl, (C.sub.1 
-C.sub.4)-haloalkyl-sulfinyl, (C.sub.1 -C.sub.4)-alkylsulfonyl or (C.sub.1 
-C.sub.4)-haloalkylsulfonyl; where, if 
R.sup.2 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, halogen, (C.sub.1 
-C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 
-C.sub.4)-haloalkoxy, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, 
(C.sub.1 -C.sub.4)-alkylthio or (C.sub.1 -C.sub.4)-alkylthio-(C.sub.1 
-C.sub.4)-alkyl; 
R.sup.3 is not simultaneously hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-haloalkoxy, halogen or (C.sub.1 
-C.sub.4)-alkylthio; 
A is nitrogen and, if R.sup.2 or R.sup.3 is (C.sub.2 -C.sub.4)-alkynyl, 
(C.sub.1 -C.sub.8)-trialkylsilylalkynyl, preferably dimethyl-(C.sub.1 
-C.sub.8)-alkylsilylalkynyl, phenyl-(C.sub.1 
-C.sub.8)-dialkylsilylalkynyl, preferably phenyldimethylsilylalkynyl, 
aryl-(C.sub.1 -C.sub.2)-alkyl-(C.sub.1 -C.sub.8)-dialkylsilylalkynyl, 
preferably benzyldimethylsilylalkynyl, (C.sub.3 
-C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.8)-dialkylsilylalkynyl, preferably 
(C.sub.3 -C.sub.8)-cycloalkyldimethylsilylalkynyl, (1-methylsila-(C.sub.3 
-C.sub.8)-cycloalk-1-yl)alkynyl, preferably 
(1-methylsilacyclopent-1-yl)alkynyl or (1-methylsilacyclohex-1-yl)alkynyl, 
triphenylsilylalkynyl, (C.sub.2 -C.sub.4)-haloalkynyl, (C.sub.2 
-C.sub.4)-hydroxyalkyl, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.1 
-C.sub.4)-haloalkanoyl, (C.sub.1 -C.sub.4)-alkanoyl-(C.sub.1 
-C.sub.4)-alkyl, (C.sub.3 -C.sub.5)-cycloalkyl, (C.sub.3 
-C.sub.5)-halocycloalkyl, (C.sub.1 -C.sub.4)-cyanoalkyl, thiocyano, 
(C.sub.1 -C.sub.4)-thiocyanoalkyl, hydroxyl, (C.sub.1 
-C.sub.4)-alkylthio-(C.sub.1 -C.sub.4)-alkyl, nitro, (C.sub.1 
-C.sub.4)-nitroalkyl, (C.sub.1 -C.sub.4)-alkoxycarbonyl-(C.sub.1 
-C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkylthio, (C.sub.1 
-C.sub.4)-haloalkylsulfinyl, (C.sub.1 -C.sub.4)-haloalkylsulfonyl, 
(C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-haloalkoxy or (C.sub.1 
-C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-haloalkyl, is alternatively CH; 
X is NH, oxygen or S(O).sub.q where q is 0, 1 or 2; 
E is a direct bond or a straight-chain or branched (C.sub.1 
-C.sub.4)-alkanediyl group, preferably a direct bond; 
Q is as defined for Q.sup.1, and 
Q.sup.1 is a cycloalkyl group of the formula II or II' 
##STR2## 
in which n is an integer from 2 to 7; 
(R.sup.4).sub.p and UR.sup.5 are substituents of the isocyclic ring formed 
with the participation of (CH.sub.2).sub.n ; 
p is 1 or 2; 
R.sup.4 is hydrogen, halogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 
-C.sub.4)-alkylthio; 
U is a direct bond, oxygen or a group S(O).sub.m where m=0, 1 or 2; 
R.sup.5 is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, and, if Q.sup.1 
is a radical of the formula II and U is a direct bond, is furthermore 
hydroxyl, cyano, thiocyano, nitro or halogen, it being possible for the 
aryl or heterocyclyl radicals mentioned to be unsubstituted or to be 
substituted by up to three--and in the case of fluorine up to the maximum 
number of--identical or different radicals and for one or more, preferably 
up to three, nonadjacent saturated carbon units in the alkyl, alkenyl or 
alkynyl radicals mentioned to be replaced by a carbonyl group or by 
heteroatom units, such as oxygen, S(O).sub.x where x=0, 1 or 2, NR.sup.6 
or SiR.sup.7 R.sup.8, in which R.sup.6 is hydrogen, (C.sub.1 
-C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-alkanoyl 
and R.sup.7 and R.sup.8 are (C.sub.1 -C.sub.4)-alkyl, preferably methyl; 
and in which, furthermore, 3 to 12 atoms of these hydrocarbon radicals, 
which radicals are modified as above if desired, can form a ring and these 
hydrocarbon radicals, with or without the variations indicated, can if 
desired be substituted by one or more, preferably up to three--and in the 
case of fluorine up to the maximum number of--identical or different 
radicals from the series consisting of halogen, aryl, aryloxy, arylthio, 
cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, 
heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, 
arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, 
haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, 
arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, 
heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, 
cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocyclylalkanoyloxy, 
alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, it 
being possible for the cycloaliphatic, aromatic or heterocyclic ring 
systems among the substituents just mentioned to be unsubstituted or 
substituted by up to three--and in the case of fluorine up to the maximum 
number of--identical or different substituents, 
or Q is as defined for Q.sup.2 and Q.sup.2 is a radical of the formula III 
##STR3## 
in which R.sup.9 is aryl or heteroaryl and the aryl or heteroaryl group 
can be unsubstituted or substituted by up to three--and in the case of 
fluorine up to the maximum number of--identical or different substituents, 
and salts thereof, preferably acid addition salts; 
especially those compounds for which 
R.sup.5 is (C.sub.1 -C.sub.20)-alkyl, (C.sub.2 -C.sub.20)-alkenyl, (C.sub.2 
-C.sub.20)-alkynyl, aryl, heterocyclyl, and, if Q.sup.1 is a radical of 
the formula II and U is a direct bond, is furthermore hydroxyl, cyano, 
thiocyano, nitro or halogen, it being possible for the aryl or 
heterocyclyl radicals mentioned to be unsubstituted or to be substituted 
by up to three--and in the case of fluorine up to the maximum number 
of--identical or different radicals and for one or more, preferably up to 
three, nonadjacent saturated carbon units in the alkyl, alkenyl or alkynyl 
radicals mentioned to be replaced by a carbonyl group or by heteroatom 
units, such as oxygen, S(O).sub.x where x=0, 1 or 2, NR.sup.6 or SiR.sup.7 
R.sup.8, in which R.sup.6 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-alkanoyl and R.sup.7 and R.sup.8 
are (C.sub.1 -C.sub.4)-alkyl, preferably methyl, and in which, 
furthermore, 3 to 12 atoms of these hydrocarbon radicals, which radicals 
are modified as above if desired, can form a ring and these hydrocarbon 
radicals, with or without the variations indicated, can if desired be 
substituted by one or more, preferably up to three--and in the case of 
halogen up to the maximum number of--identical or different radicals from 
the series consisting of halogen, aryl, aryloxy, arylthio, (C.sub.3 
-C.sub.8)-cycloalkoxy, (C.sub.3 -C.sub.8)-cycloalkylthio, heterocyclyl, 
heterocyclyloxy, heterocyclylthio, (C.sub.1 -C.sub.12)-alkanoyl, (C.sub.3 
-C.sub.8)-cycloalkanoyl, (C.sub.1 -C.sub.12)-haloalkanoyl, aryl-(C.sub.1 
-C.sub.4)-alkanoyl, (C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 
-C.sub.4)-alkanoyl, heterocyclyl-(C.sub.1 -C.sub.4)-alkanoyl, (C.sub.1 
-C.sub.12)-alkoxycarbonyl, (C.sub.1 -C.sub.12)-haloalkoxycarbonyl, 
(C.sub.3 -C.sub.8)-cycloalkoxycarbonyl, (C.sub.3 
-C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.4)-alkoxycarbonyl, aryl-(C.sub.1 
-C.sub.4)-alkoxycarbonyl, heterocyclyl-(C.sub.1 -C.sub.4)-alkoxycarbonyl, 
aryloxycarbonyl, heterocyclyloxycarbonyl, (C.sub.1 -C.sub.12)-alkanoyloxy, 
(C.sub.2 -C.sub.12)-haloalkanoylalkoxy, (C.sub.3 
-C.sub.8)-cycloalkanoyloxy, (C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 
-C.sub.4)-alkanoyloxy, aroyloxy, aryl-(C.sub.1 -C.sub.4)-alkanoyloxy, 
heterocyclyl-(C.sub.1 -C.sub.4)-alkanoyloxy, (C.sub.1 
-C.sub.12)-alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano 
or nitro, it being possible for the cycloaliphatic, aromatic or 
heterocyclic ring systems among the substituents just mentioned to be 
unsubstituted or substituted by up to three--and in the case of fluorine 
up to the maximum number of--identical or different substituents, and, in 
addition, if Q is as defined for Q.sup.1, n is 5 and E is a direct bond, 
the groups -X-E and UR.sup.5 are preferably in the cis configuration 
relative to one another and take up positions 1 and 4 on the cyclohexane 
ring. 
Preferred compounds of the formula I are those in which 
R.sup.1 is hydrogen or fluorine; 
R.sup.2 and R.sup.3 are (C.sub.1 -C.sub.4)-alkyl, (C.sub.2 
-C.sub.4)-alkenyl, (C.sub.2 -C.sub.4)-alkynyl, trimethylsilylethynyl, 
methoxycarbonyl, (C.sub.1 -C.sub.4)-haloalkyl, halogen, methoxymethyl or 
cyano; 
A is CH or N; 
X is NH or oxygen; 
U is oxygen or a direct bond; 
E is a direct bond; 
n is 5; the radicals X and UR.sup.5 or NOR.sup.5 take up positions 1 and 4 
on the cyclohexane ring and X and UR.sup.5 are in the cis configuration 
relative to one another; 
R.sup.4 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, trifluoromethyl or (C.sub.1 
-C.sub.4)-alkoxy; 
especially those compounds of the formula I in which 
R.sup.1 is hydrogen; 
R.sup.2 and R.sup.3 are methyl, ethyl, propyl, (C.sub.2 -C.sub.3)-alkenyl, 
(C.sub.2 -C.sub.3)-chloro- or fluoroalkenyl, (C.sub.2 -C.sub.3)-alkynyl, 
trimethylsilylethynyl, (C.sub.1 -C.sub.3)-chloro- or fluoroalkyl, 
methoxymethyl, halogen or cyano; 
A is CH; 
X is NH; 
R.sup.4 is hydrogen. 
Compounds of the formula I which are most preferred are those for which 
R.sup.1 is hydrogen; 
R.sup.2 is methyl, ethyl, vinyl, ethynyl, trimethylsilylethynyl, (C.sub.1 
-C.sub.2)-fluoroalkyl or methoxymethyl; 
R.sup.3 is vinyl, ethynyl, trimethylsilylethynyl, methyl, ethyl, (C.sub.1 
-C.sub.2)-fluoroalkyl, cyano or halogen; 
A is nitrogen; 
X is NH; 
E is a direct bond; 
R.sup.4 is hydrogen; 
n is 5; 
Q is a radical of the formula II in which the substituents X and UR.sup.5 
take up positions 1 and 4 on the cyclohexane ring and are in each case in 
the cis configuration relative to one another, or 
Q is a radical of the formula II' in which the substituent X and the oxime 
ether group take up positions 1 and 4 on the cyclohexane ring; 
R.sup.5 is (C.sub.1 -C.sub.12)-alkyl, (C.sub.2 -C.sub.12)-alkenyl, (C.sub.2 
-C.sub.12)-alkynyl, aryl or heterocyclyl, it being possible for the aryl 
or heterocyclyl radicals to be unsubstituted or to be substituted by up to 
three--and in the case of fluorine up to the maximum number of--identical 
or different radicals and for one, two or three, preferably one, carbon 
unit in the alkyl radicals mentioned to be replaced by heteroatom units, 
such as oxygen, sulfur or SiR.sup.7 R.sup.8, and R.sup.7 and R.sup.8 are 
preferably methyl, and in which, furthermore, 3 to 12 atoms of these 
hydrocarbon radicals, which radicals can if desired be modified as above, 
can form a ring and these hydrocarbon radicals, with or without the 
variations indicated, can if desired be substituted by one or more, 
preferably up to three--and in the case of halogen up to the maximum 
number of--identical or different radicals from the series consisting of 
aryl, aryloxy, arylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio 
and alkoxycarbonyl, it being possible for the aromatic or heterocyclic 
ring systems among the substituents just mentioned to be unsubstituted or 
to be substituted by up to three--and in the case of fluorine up to the 
maximum number of--identical or different substituents, 
especially those compounds for which 
Q is a radical of the formula II in which 
U is a direct bond; 
R.sup.5 is (C.sub.1 -C.sub.12)-alkyl or phenyl, and in the alkyl radicals 
one carbon unit can be replaced by Si(CH.sub.3).sub.2 and/or oxygen and, 
furthermore, 3 to 6 atoms of this carbon chain, which chain can if desired 
be modified as above, can form a ring and the phenyl radical can be 
unsubstituted or substituted by up to three--and in the case of fluorine 
up to the maximum number of--identical or different radicals. 
In the above formula, "halogen" ("halo") means a fluorine, chlorine, 
bromine or iodine atom, preferably a fluorine, chlorine or bromine atom; 
"(C.sub.1 -C.sub.4)-alkyl" means an unbranched or branched hydrocarbon 
radical having 1 to 4 carbon atoms, for example the methyl, ethyl, propyl, 
isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical; 
"(C.sub.1 -C.sub.20)-alkyl" means the abovementioned alkyl radicals, for 
example the pentyl, 2-methylbutyl or 1,1-dimethylpropyl radical, or the 
hexyl, heptyl, octyl, 1,1,3,3-tetramethylbutyl, nonyl, 1-decyl, 2-decyl, 
undecyl, dodecyl, pentadecyl or eicosyl radical; 
"(C.sub.1 -C.sub.4)-haloalkyl" means an alkyl group as specified for 
"(C.sub.1 -C.sub.4)-alkyl", in which one or more hydrogen atoms have been 
replaced by the abovementioned halogen atoms, preferably chlorine or 
fluorine, for example the trifluoromethyl group, the 1-fluoroethyl group, 
the 2-fluoroethyl group, the 2,2,2-trifluoroethyl group, the chloromethyl, 
fluoromethyl or difluoromethyl group, or the 1,1,2,2-tetrafluoroethyl 
group; 
"(C.sub.1 -C.sub.2)-fluoroalkyl" means for example the 1-fluoroethyl, 
2-fluoroethyl, 2,2-difluoroethyl, 1,1,-difluoroethyl or the 
2,2,2-trifluoroethyl group; 
"cycloalkyl" means preferably (C.sub.3 -C.sub.8)-cycloalkyl; 
"cycloalkoxy" means preferably (C.sub.3 -C.sub.8)-cycloalkoxy; 
"cycloalkylthio" means preferably (C.sub.3 -C.sub.8)-cycloalkylthio; 
"(C.sub.3 -C.sub.5)-cycloalkyl" means the cyclopropyl, cyclobutyl or 
cyclopentyl group; 
"(C.sub.3 -C.sub.8)-cycloalkyl" means the radicals mentioned above under 
"(C.sub.3 -C.sub.5)-cycloalkyl" plus the cyclohexyl, cycloheptyl and 
cyclooctyl radicals; 
"(C.sub.3 -C.sub.5)-halocycloalkyl" means one of the abovementioned 
(C.sub.3 -C.sub.5)-cycloalkyl radicals in which one or more--and in the 
case of fluorine possibly all--of the hydrogen atoms have been replaced by 
halogen, preferably fluorine or chlorine, for example the 2,2-difluoro- or 
2,2-dichlorocyclopropane group or the fluorocyclopentane radical; 
"(C.sub.2 -C.sub.4)-alkenyl" means for example the vinyl, allyl, 
2-methyl-2-propenyl or 2-butenyl group; 
"(C.sub.2 -C.sub.20)-alkenyl" means the abovementioned radicals plus for 
example the 2-pentenyl, 2-decenyl or 2-eicosenyl group; 
"(C.sub.2 -C.sub.4)-haloalkenyl" means a (C.sub.2 -C.sub.4)-alkenyl group 
in which some--and in the case of fluorine possibly all--of the hydrogen 
atoms have been replaced by halogen, preferably fluorine or chlorine; 
"(C.sub.2 -C.sub.4)-alkynyl" means for example the ethynyl, propargyl, 
1-butynyl, 2-butynyl or 3-butynyl group; 
"(C.sub.2 -C.sub.20)-alkynyl" means the abovementioned radicals plus for 
example the 2-pentynyl or 2-decynyl group; 
"(C.sub.2 -C.sub.4)-haloalkynyl" means a (C.sub.2 -C.sub.4)-alkynyl group 
in which some--and in the case of fluorine possibly all--of the hydrogen 
atoms have been replaced by halogen atoms, preferably fluorine or 
chlorine, or else means the iodoethynyl group; 
"dimethyl-(C.sub.1 -C.sub.8)-alkylsilylethynyl" means for example the 
trimethylsilylethynyl or the tert-butyldimethylsilylethynyl group; 
"(C.sub.1 -C.sub.4)-hydroxyalkyl" means for example the hydroxymethyl, 
1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-1-methylethyl or the 
1-hydroxypropyl group; 
"(C.sub.1 -C.sub.4)-alkanoyl" means for example the formyl, acetyl, 
propionyl, 2-methylpropionyl or butyryl group; 
"(C.sub.1 -C.sub.4)-haloalkanoyl" means a (C.sub.1 -C.sub.4)-alkanoyl group 
in which some--and in the case of fluorine possibly all--of the hydrogen 
atoms have been replaced by halogen atoms, preferably fluorine or 
chlorine; 
"cyano-(C.sub.1 -C.sub.4)-alkyl" means a cyanoalkyl group whose hydrocarbon 
radical is as defined under "(C.sub.1 -C.sub.4)-alkyl"; 
"(C.sub.1 -C.sub.4)-alkoxycarbonyl" means for example the methoxycarbonyl, 
ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonyl 
group; 
"(C.sub.1 -C.sub.12)-alkoxycarbonyl" means the abovementioned radicals plus 
for example the hexyloxycarbonyl, 2-methylhexyloxycarbonyl, 
decyloxycarbonyl or dodecyloxycarbonyl group; 
"(C.sub.1 -C.sub.4)-haloalkoxycarbonyl" means a (C.sub.1 
-C.sub.4)-alkoxycarbonyl group in which one or more--and in the case of 
fluorine possibly all--of the hydrogen atoms have been replaced by 
halogen, preferably fluorine or chlorine; 
"(C.sub.1 -C.sub.4)-alkylthio" means an alkylthio group whose hydrocarbon 
radical is as defined for "(C.sub.1 -C.sub.4)-alkyl"; 
"(C.sub.1 -C.sub.4)-haloalkylthio" means a (C.sub.1 -C.sub.4)-alkylthio 
group in which one or more--and in the case of fluorine possibly all--of 
the hydrogen atoms of the hydrocarbon moiety have been replaced by 
halogen, especially chlorine or fluorine; 
"(C.sub.1 -C.sub.4)-alkylsulfinyl" means for example the methyl-, ethyl-, 
propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl 
group; 
"(C.sub.1 -C.sub.4)-alkylsulfonyl" means for example the methyl-, ethyl-, 
propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl 
group; 
"(C.sub.1 -C.sub.4)-haloalkylsulfinyl" and "(C.sub.1 
-C.sub.4)-haloalkylsulfonyl" mean (C.sub.1 -C.sub.4)-alkylsulfinyl and 
-sulfonyl radicals as defined above in which one or more--and in the case 
of fluorine possibly all--of the hydrogen atoms of the hydrocarbon moiety 
have been replaced by halogen, especially chlorine or fluorine; 
"(C.sub.1 -C.sub.4)-alkoxy" means an alkoxy group whose hydrocarbon radical 
is as defined under "(C.sub.1 -C.sub.4)-alkyl"; 
"(C.sub.1 -C.sub.4)-haloalkoxy" means a haloalkoxy group whose halogenated 
hydrocarbon radical is as defined under "(C.sub.1 -C.sub.4)-haloalkyl"; 
"(C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl" means for example a 
1-methoxyethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 
methoxymethyl or ethoxymethyl group, a 3-methoxypropyl group or a 
4-butoxybutyl group; 
"(C.sub.1 -C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-alkyl", "(C.sub.1 
-C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-haloalkyl" and "(C.sub.1 
-C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-haloalkyl" mean (C.sub.1 
-C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl radicals as defined above in 
which one or more--and in the case of fluorine possibly all--of the 
hydrogen atoms of the corresponding hydrocarbon moieties have been 
replaced by halogen, preferably chlorine or fluorine; 
"(C.sub.1 -C.sub.4)-alkylthio-(C.sub.1 -C.sub.4)-alkyl" means for example 
methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 
2-ethylthioethyl or 3-methylthiopropyl; 
"aryl" means an isocyclic aromatic radical having preferably 6 to 14, 
especially 6 to 12, carbon atoms, for example phenyl, naphthyl or 
biphenylyl, preferably phenyl; 
"heterocyclyl" means a heteroaromatic or heteroaliphatic ring system, where 
"heteroaromatic ring system" means an aryl radical in which at least one 
CH group is replaced by N and/or at least two adjacent CH groups are 
replaced by S, NH or O, for example a radical of thiophene, furan, 
pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 
1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 
1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, 
benzob!thiophene, benzob!furan, indole, benzoc!thiophene, 
benzoc!furan, isoindole, benzoxazole, benzothiazole, benzimidazole, 
benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, 
benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, 
pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 
quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 
1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 
1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine or 
4H-quinolizine; 
and "heteroaliphatic ring system" means a (C.sub.3 -C.sub.8)-cycioalkyl 
radical in which at least one carbon unit has been replaced by O, S or a 
group NR.sup.11, and R.sup.11 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, 
(C.sub.1 -C.sub.4)-alkoxy or aryl; 
"arylthio" means for example the phenylthio group or the 1- or 
2-naphthylthio group; 
"aryloxy" means for example the phenoxy group or 1- or 2-naphthyloxy group; 
"heterocyclyloxy" or "heterocyclylthio" means one of the abovementioned 
heterocyclic radicals which is linked via an oxygen or sulfur atom; 
"(C.sub.3 -C.sub.8)-cycloalkoxycarbonyl" means for example the 
cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or 
the cycloheptyloxycarbonyl group; 
"(C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.4)-alkoxycarbonyl" means for 
example the cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, 
cyclopentyloxymethylcarbonyl, cyclohexyloxymethylcarbonyl, 
1-(cyclohexyl)ethoxycarbonyl or the 2-(cyclohexyl)ethoxycarbonyl group; 
"aryl-(C.sub.1 -C.sub.4)-alkoxycarbonyl" means for example the 
benzyloxycarbonyl, 1-naphthylmethoxycarbonyl, 2-naphthylmethoxycarbonyl, 
1-phenylethoxycarbonyl or the 2-phenylethoxycarbonyl group; 
"aryloxycarbonyl" means for example the phenoxycarbonyl, naphthoxycarbonyl 
or the biphenyloxycarbonyl group; 
"heterocyclyl-(C.sub.1 -C.sub.4)-alkanoyl" means for example the thenoyl, 
furoyl, tetrahydrofurfurylcarbonyl, thienylacetyl or the pyridylacetyl 
group; 
"heterocyclyl-(C.sub.1 -C.sub.4)-alkoxycarbonyl" means for example the 
thienylmethoxycarbonyl, furylmethoxycarbonyl, pyridylmethoxycarbonyl or 
the thienylethoxycarbonyl group; 
"(C.sub.1 -C.sub.12)-alkanoyloxy" means for example the formyloxy, acetoxy, 
propionyloxy, butyryloxy, pivaloyloxy, valeroyloxy or the decanoyloxy 
group; 
"(C.sub.2 -C.sub.12)-haloalkanoyloxy" means a (C.sub.2 
-C.sub.12)-alkanoyloxy group in which one or more--and in the case of 
fluorine possibly all--of the hydrogen atoms of the hydrocarbon moiety 
have been replaced by halogen, especially fluorine or chlorine; 
"(C.sub.3 -C.sub.8)-cycloalkanoyloxy" means for example the 
cyclopropanoyloxy, cyclobutanoyloxy, cyclopentanoyloxy, cyclohexanoyloxy 
or the cycloheptanoyloxy group; 
"(C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.4)-alkanoyloxy" means for 
example the cyclopropylcarbonyloxy, cyclopropylacetoxy, 
cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, 
cyclohexylacetoxy or the 4-cyclohexylbutyryloxy group; 
"aroyloxy" means for example the benzoyloxy or the naphthoyloxy group; 
"heterocyclyl-(C.sub.1 -C.sub.4)-alkanoyloxy" means for example the 
thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or the 
pyrimidinylcarbonyloxy group; 
"aryl-(C.sub.1 -C.sub.4)-alkanoyloxy" means for example the benzoyloxy, 
naphthoyloxy or the phenylacetoxy group; 
"(C.sub.1 -C.sub.20)-alkylsulfonyloxy" means for example the methane-, 
ethane-, butane- or hexanesulfonyloxy group; 
"arylsulfonyloxy" means for example the phenylsulfonyloxy or the 
toluenesulfonyloxy group. 
Examples of the possible substituents for the various aliphatic, aromatic 
and heterocyclic ring systems include halogen, nitro, cyano, di-(C.sub.1 
-C.sub.4)-alkylamino, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-trialkylsilyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 
-C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.2)-alkoxy-CH.sub.2 CH.sub.2 !.sub.1,2 -ethoxy, (C.sub.1 
-C.sub.4)-alkylthio, (C.sub.1 -C.sub.4)-alkylsulfinyl, (C.sub.1 
-C.sub.4)-alkylsulfonyl, phenyl, benzyl, phenoxy, phenylthio, halophenoxy, 
(C.sub.1 -C.sub.4)-alkylphenoxy, (C.sub.1 -C.sub.4)-alkoxyphenoxy, 
(C.sub.1 -C.sub.4)-alkylthiophenoxy, phenylthio, heterocyclyl, 
heterocyclylthio, heterocyclyloxy, haloheterocyclyloxy, 
alkylheterocyclyloxy or alkoxyheterocyclyloxy, where in the alkyl radicals 
and the radicals derived therefrom one or more--and in the case of 
fluorine up to the maximum number of--hydrogen atoms can be replaced by 
halogen, preferably chlorine or fluorine. 
Furthermore, the definition that "possible for! one or more, preferably up 
to three, nonadjacent saturated carbon units in the alkyl, alkenyl or 
alkynyl radicals mentioned to be replaced by a carbonyl group or by 
heteroatom units, such as oxygen, S(O).sub.x where x=0, 1 or 2, NR.sup.6 
or SiR.sup.7 R.sup.8, in which R.sup.6 is hydrogen, (C.sub.1 
-C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-alkanoyl 
and R.sup.7 and R.sup.8 are (C.sub.1 -C.sub.4)-alkyl, preferably methyl; 
and in which, furthermore, 3 to 12 atoms of these hydrocarbon radicals, 
which radicals are modified as above if desired, can form a ring and these 
hydrocarbon radicals, with or without the variations indicated, can if 
desired be substituted by one or more, preferably up to three--and in the 
case of fluorine up to the maximum number of--identical or different 
radicals from the series consisting of halogen, aryl, aryloxy, arylthio, 
cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, hetero- 
cyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, 
cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, 
haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, 
arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, 
alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, 
aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, 
arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, it being possible 
for the cycloaliphatic, aromatic or heterocyclic ring systems among the 
substituents just mentioned to be unsubstituted or substituted by up to 
three--and in the case of fluorine up to the maximum number of--identical 
or different substituents" means for example: 
alkoxyalkyl radicals, for example the methoxymethyl, methoxyethyl or 
ethoxyethyl group; or 
alkoxyalkoxyalkyl radicals, for example the methoxy- or the 
ethoxyethoxyethyl group; or 
alkylthioalkyl radicals, for example the methyl- or the ethylthioethyl 
group; or 
alkylsulfinylalkyl radicals, for example the methyl- or ethylsulfinylethyl 
group; or 
alkylsulfonylalkyl radicals, for example the methyl- or ethylsulfonylethyl 
group; or 
alkyldialkylsilylalkyl, preferably alkyldimethylsilylalkyl, radicals, for 
example the trimethylsilylmethyl or the trimethylsilylethyl group; or 
trialkylsilyl, preferably alkyldimethylsilyl, radicals, for example the 
trimethylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl or the 
octyidimethylsilyl group; or 
cycloalkyldialkylsilyl, preferably cycloalkyldimethylsilyl, radicals, for 
example the cyclohexyldimethylsilyl group; or 
aryldialkylsilyl, preferably aryldimethylsilyl, radicals, for example the 
phenyldimethylsilyl group; or 
arylalkyldialkylsilyl, preferably aryldimethylsilyl, radicals, for example 
the benzyldimethylsilyl or the phenylethyldimethylsilyl group; or 
dimethylalkoxyalkylsilyl, for example the dimethylethoxypropylsilyl group; 
alkanoylalkyl radicals, for example the acetylmethyl or the pivaloylmethyl 
group; or 
cycloalkanoylalkyl radicals, for example the cyclopropylcarbonylmethyl or 
the cyclohexylcarbonylmethyl group; or 
haloalkanoylalkyl radicals, for example the trifluoro- or 
trichloroacetylmethyl group; or 
aroylalkyl radicals, for example the benzoyl- or naphthoylalkyl radicals, 
for example the phenylacetylmethyl group; or 
heterocyclylcarbonylalkyl radicals, for example the thienyl- or 
pyridylacetylmethyl group; or 
arylalkyl radicals, for example the benzyl, the 2-phenylethyl, the 
1-phenylethyl, the 1-methyl-1-phenylethyl group, the 3-phenylpropyl, the 
4-phenylbutyl group, the 2-methyl-2-phenylethyl group or the 1-methyl- or 
2-methylnaphthyl group; or 
heterocyclylalkyl radicals, for example the thienylmethyl, pyridylmethyl, 
furfuryl, tetrahydrofurfuryl, tetrahydropyranylmethyl or the 
1,3-dioxolan-2-methyl group; or 
aryloxyalkyl radicals, for example the phenoxymethyl or naphthoxymethyl 
group; or 
cycloalkyl radicals, both monocyclic examples such as the cyclopropyl, 
cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical, or 
bicyclic radicals such as, for example, the norbornyl radical or the 
bicyclo2.2.2!octane radical, or condensed radicals such as the 
decahydronaphthyl radical; 
alkylcycloalkyl radicals, for example the 4-methyl- or tne 
4-tert-butylcyclohexyl group or the 1-methylcyclopropyl, 
1-methylcyclobutyl, 1-methylcyclopentyl or 1-methylcyclohexyl group; 
cycloalkylalkyl radicals, for example the cyclohexylmethyl or 
cyclohexylethyl group; 
or else haloalkyl derivatives of the corresponding groups, for example 
haloalkyl radicals, haloalkoxyalkyl radicals, alkoxyhaloalkyl radicals, 
haloalkylcycloalkyl radicals or halocycloalkyl radicals. 
The explanation given above applies correspondingly to homologs and to 
radicals derived therefrom. 
The present invention relates to compounds of the formula I in the form of 
the free base or an acid addition salt. Acids which can be used to form 
salts are inorganic acids, such as hydrochloric acid, hydrobromic acid, 
nitric acid, sulfuric acid or phosphoric acid, or organic acids, such as 
formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, 
fumaric acid, adipic acid, stearic acid, oleic acid, methanesulfonic acid, 
benzenesulfonic acid or toluenesulfonic acid. 
In addition to the abovementioned cis/trans isomerism about the cycloalkyl 
group, some of the compounds of the formula I have one or more asymmetric 
carbon atoms or stereoisomers on double bonds. Enantiomers or 
diastereomers may therefore occur. The invention embraces both the pure 
isomers and mixtures thereof. The mixtures of diastereomers can be 
separated into the components by customary methods, for example by 
selective crystallization from appropriate solvents or by chromatography. 
Racemates can be resolved into the enantiomers by customary methods, for 
example by forming a salt with an optically active acid, separating the 
diastereomeric salts and liberating the pure enantiomers by means of a 
base. 
The invention additionally relates to a process for the preparation of 
compounds of the formula I, which comprises reacting a compound of the 
formula IV 
##STR4## 
in which A, R.sup.1, R.sup.2 and R.sup.3 are as defined under formula I 
and L is a leaving group, for example halogen, alkylthio, 
alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, with 
a nucleophile of the formula V 
EQU H--X-E-Q (V) 
in which X, E and Q are as defined above for formula I and, if desired, 
subjecting the compounds of the formula I which have been obtained in this 
or a different manner to further derivatization at positions 5 or 6 of the 
pyrimidine system or, respectively, positions 2 and 3 of the pyridine 
system (radicals R.sup.2 and R.sup.3) or on the radical Q. 
The above-described substitution reaction is known in principle. The 
leaving group L can be varied within wide limits and can, for example, be 
a halogen atom such as fluorine, chlorine, bromine or iodine, or 
alkylthio, such as methylthio or ethylthio, or alkanesulfonyloxy, such as 
methane-, trifluoromethane- or ethanesulfonyloxy, or arylsulfonyloxy, such 
as benzenesulfonyloxy or toluenesulfonyloxy, or alkylsulfonyl, such as 
methylsulfonyl or ethylsulfonyl, or arylsulfonyl, such as phenylsulfonyl 
or toluenesulfonyl. 
The abovementioned reaction is carried out in a temperature range from 
20.degree. to 150.degree. C., expediently in the presence of a base and, 
if appropriate, in an inert organic solvent, such as 
N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 
N-methyl-2-pyrrolidinone, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, 
methanol, ethanol, butanol, ethylene glycol, ethylene glycol dimethyl 
ether, toluene, chlorobenzene or xylene. Mixtures of the solvents 
mentioned can also be used. 
If X is oxygen, examples of suitable bases are alkali metal or alkaline 
earth metal carbonates, hydrogen carbonates, amides or hydrides, such as 
sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium 
amide or sodium hydride; if X is NH, suitable examples are alkali metal or 
alkaline earth metal carbonates, hydrogen carbonates, hydroxides, amides 
or hydrides, such as sodium carbonate, sodium hydrogen carbonate, 
potassium carbonate, sodium hydroxide, sodium amide or sodium hydride, or 
organic bases, such as triethylamine or pyridine. A second equivalent of 
an amine of the formula III can also be employed as auxiliary base. 
The nucleophiles of the formula III which are required as starting 
materials can if X is oxygen be prepared by known methods, for example by 
reducing a carbonyl group with a suitable reducing agent, for example a 
complex metal hydride or else, in the case of an aldehyde or ketone, with 
hydrogen and a hydrogenation catalyst. To prepare the cis-cyclohexanols, 
the starting materials for the particularly preferred cis-cyclohexyloxy 
derivatives, the catalytic hydrogenation of suitably substituted phenols 
or the reduction of suitably substituted cyclohexanone derivatives using 
complex hydrides which carry sterically bulky substituents, for example 
L-Selectride.RTM., is particularly appropriate. 
The nucleophiles of the formula III which are required as starting 
materials can if X is NH be prepared by known methods, for example by 
reduction of an oxime, an azide or a nitrile with an appropriate reducing 
agent, for example a complex metal hydride or hydrogen in the presence of 
a hydrogenation catalyst, reductive amination or Leuckart-Wallach reaction 
of an aldehyde or ketone, or Gabriel reaction of an alkyl halide or alkyl 
tosylate. For the preparation of the cyclohexylamines, the starting 
materials for the particularly preferred cis-1,4-cyclohexylamino 
derivatives, the reductive amination of suitably substituted 
cyclohexanones with ammonium salts and sodium cyanoborohydride or with 
ammonia and hydrogen in the presence of metal catalysts, such as nickel, 
ruthenium, rhodium or palladium, the proportion of desired cis-amine being 
particularly high in the case of this method, is appropriate. A further 
method is the hydrogenation of anilines in the presence of hydrogenation 
catalysts. 
The invention furthermore relates to a process for the preparation of 
compounds of the formula VI 
##STR5## 
in which R.sup.1, R.sup.2 and X are as defined above for formula I and, if 
R.sup.9 is (C.sub.1 -C.sub.4)-alkoxy, R.sup.2 can also be (C.sub.1 
-C.sub.4)-alkyl, 
A is nitrogen 
R.sup.9 is (C.sub.1 -C.sub.4)-perfluoroalkyl, trifluoromethylthio, cyano or 
(C.sub.1 -C.sub.4)-alkoxy 
R.sup.10 is the unit EQ from formula I and, furthermore, is a (C.sub.1 
-C.sub.20)-alkyl radical in which one or more, preferably up to three, 
nonadjacent saturated carbon units can be replaced by heteroatom units, 
such as oxygen, S(O).sub.x where x=0, 1 or 2, NR.sup.6' or SiR.sup.7' 
R.sup.8', where R.sup.6' is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-alkanoyl or (C.sub.1 -C.sub.4)-alkoxy, and where R.sup.7' and 
R.sup.8' are (C.sub.1 -C.sub.4)-alkyl, and in which furthermore these 
alkyl radicals, with or without the variations indicated, can if desired 
be substituted by one or more, preferably up to three--and in the case of 
halogen up to the maximum number of--identical or different radicals from 
the series consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, 
cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, 
cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, 
heterocyclyl- alkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, 
cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, 
heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, 
alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, 
aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, 
arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, it being possible 
for the cycloaliphatic, aromatic or heterocyclic ring systems among the 
substituents just mentioned to be unsubstituted or substituted by up to 
three--and in the case of fluorine up to the maximum number of--identical 
or different substituents, 
which comprises reacting a compound of the formula VII 
##STR6## 
for which R.sup.1, R.sup.2, A, X and R.sup.10 are as defined for formula 
VI and, if R.sup.9 is (C.sub.1 -C.sub.4)-alkoxy, R.sup.2 can also be 
(C.sub.1 -C.sub.4)-alkyl, and L is a leaving group which is as defined for 
formula IV, preferably bromine or iodine, with a compound MR.sup.9, 
preferably in the presence of a copper(I) salt, where M is an alkali metal 
or alkaline earth metal and the copper(I) salt used is for example 
copper(I) chloride, bromide or iodide, or reacting the radical R.sup.9 in 
the form of the copper(I) salt. 
The reactions are carried out in an inert organic solvent or else in bulk 
in a temperature range from 80.degree. to 250.degree. C., preferably from 
70.degree. to 200.degree. C. 
The compounds of the formula VI for which R.sup.9 is alkoxy are expediently 
prepared by reacting the compound MR.sup.9, preferably the sodium or 
potassium salt, in an inert organic solvent, for example isopropanol, 
dimethylformamide, dimethylacetamide, N-methylpyrrolidone, 
1,3-dimethyltetrahydro-2-(1H)-pyrimidinone, or else in the very alcohol on 
which the radical R.sup.9 is based, with the compound of the formula VII, 
preferably in the presence of a copper(I) salt and, if desired, of an 
aliphatic carboxylic ester, preferably ethyl acetate. 
The compounds of the formula VI for which R.sup.9 is perfluoroalkyl, 
trifluoromethylthio or cyano are expediently prepared by reacting the 
copper(I) salts of the radicals R.sup.9 in an inert organic solvent, for 
example dimethylformamide, dimethylacetamide, N-methylpyrrolidinone, 
1,3-dimethyltetrahydro-2-(1H)-pyrimidinone or hexamethylphosphoric 
triamide, or else in bulk, with a compound of the formula VII, in a 
temperature range from 50.degree. to 250.degree. C., preferably from 
100.degree. to 200.degree. C. A method of preparing compounds of the 
formula VI for which R.sup.9 is cyano from a starting material of the 
formula VII for which L is iodine has been described (WO 93/22291). The 
process described therein, however, requires the use of a costly palladium 
reagent, whereas in the process claimed above inexpensive copper(I) 
cyanide is employed. 
The starting materials of the formula VII for which L is iodine can be 
prepared by analogy with EP-A-470 600. 
The preparation of the starting materials R.sup.9 Cu is known from the 
literature (cf. e.g. J. C. S. Perkin I, 1980, 2755; Synthesis, 1975, 721). 
The compounds of the formula VI, synthesized by the method described above, 
for which R.sup.10 is a (C.sub.1 -C.sub.20)-alkyl radical in which one or 
more, preferably up to three, nonadjacent saturated carbon units can be 
replaced by heteroatom units, such as oxygen, S(O).sub.x where x=0, 1 or 
2, NR.sup.6' or SiR.sup.7' R.sup.8', where R.sup.6' is hydrogen, 
(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkanoyl or (C.sub.1 
-C.sub.4)-alkoxy, and where R.sup.7' and R.sup.8' are (C.sub.1 
-C.sub.4)-alkyl, and in which furthermore these alkyl radicals, with or 
without the variations indicated, can if desired be substituted by one or 
more, preferably up to three--and in the case of halogen up to the maximum 
number of--identical or different radicals from the series consisting of 
halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, 
heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, 
haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, 
heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, 
cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, 
heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, 
alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, 
aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, 
arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, it being possible 
for the cycloaliphatic, aromatic or heterocyclic ring systems among the 
substituents just mentioned to be unsubstituted or to be substituted by up 
to three--and in the case of fluorine up to the maximum number 
of--identical or different substituents, also exhibit very good 
insecticidal, acaricidal, ixodicidal and fungicidal action. The invention 
therefore additionally relates to compounds of the formula VI for which 
R.sup.1, R.sup.2, R.sup.9, A and X are as defined for formula VI and 
R.sup.10 is (C.sub.1 -C.sub.20)-alkyl and, in this alkyl radical, one or 
more, preferably up to three, nonadjacent saturated carbon units can be 
replaced by a carbonyl group or by heteroatom units, such as oxygen, 
S(O).sub.x where x=0, 1 or 2, NR.sup.6' or SiR.sup.7' R.sup.8', where 
R.sup.6', R.sup.7' and R.sup.8' are as defined above for formula VI, and 
this hydrocarbon radical, with or without the variations indicated, can if 
desired be substituted by one or more, preferably up to three--and in the 
case of halogen up to the maximum number of--identical or different 
radicals from the series consisting of halogen, cycloalkyl, cycloalkoxy, 
aryloxy, arylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, 
alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, 
cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, 
haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, 
arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, 
heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, 
cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloalkanoyloxy, 
alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, it 
being possible for the cycloaliphatic, aromatic or heterocyclic ring 
systems among the substituents just mentioned to be unsubstituted or to be 
substituted by up to three--and in the case of fluorine up to the maximum 
number of--identical or different substituents, 
in particular those compounds of the formula VI for which R.sup.10 is 
(C.sub.1 -C.sub.20)-alkyl, preferably (C.sub.4 -C.sub.15)-alkyl, 
aryl-(C.sub.1 -C.sub.4)-alkyl, phenoxyphenyl-(C.sub.1 -C.sub.4)-alkyl, in 
which the aryl group or the phenoxy group is unsubstituted or is 
substituted by one, two or three substituents which are identical or 
different and are in each case halogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 
-C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 
-C.sub.4)-haloalkoxy or (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 
-C.sub.4)-alkyl. 
Examples of further methods of preparing compounds of the formula I are 
##STR7## 
Regarding the above reactions: L. S. Hegedus in Organometallic Synthesis, 
ed. M. Schlosser, Wiley, Chichester 1994. 
The compounds of the formula Ic for which R' is hydrogen are expediently 
prepared by reacting the compounds VIIa with a silyl-protected acetylene, 
preferably trimethylsilylacetylene, and eliminating the silyl group from 
the product Ic for which R' is, for example, trimethylsilyl, using 
hydroxide or fluoride. 
The compounds obtained according to Scheme 1 can be subjected to further 
derivatization: 
##STR8## 
Examples of halogenating agents are SOCl.sub.2, HBr, HI, DAST 
##STR9## 
The alcohol Id can be oxidized by various methods (Swern, Pfitzner-Moffat 
or CrO.sub.3 oxidation) to the aldehyde Ig, from which in turn alkenyl or 
haloalkenyl derivatives Ib can be obtained by Wittig reaction (cf. 
Houben-Weyl, E1, Organic phosphorus compounds, p. 720). 
##STR10## 
Addition of halogen onto the alkenyl derivatives Ib and the alkynyl 
derivatives Ic leads respectively to haloalkyl or haloalkenyl derivatives. 
Hydrogen halide can be eliminated from the former using bases to give 
haloalkenyl derivatives. 
The alkynyl derivatives Ic for which R' is hydrogen can be further modified 
in accordance with Scheme 4: 
##STR11## 
Regarding the preparation of the iodoalkynyl derivatives: Houben-Weyl, 
Volume 5/2a, 604. 
The alkynyl derivatives Ic for which R' is alkyl or hydrogen can be further 
modified in accordance with Scheme 5: 
##STR12## 
In analogy with Scheme 2, the compounds Ij can be reacted further to give 
(1-haloalkyl)-, (1-cyanoalkyl)-, (1-alkoxyalkyl)- and (1-alkylthioalkyl)- 
derivatives. 
Alternatively, the compounds Ii and Ij can be prepared as follows: 
##STR13## 
Using appropriate halogenating agents, the carbonyl derivatives Ig and Ii 
can be converted into geminal dihalo compounds. 
______________________________________ 
Scheme 7 R' = H, alkyl 
R.sup.2,R.sup.3 = haloalkyl, Hal = F, Cl 
______________________________________ 
Examples of suitable halogenating agents are SF.sub.4, DAST or PCl.sub.5 
(Cf. J. Org. Chem. 40, 574 (1975), Org. React. 21, 1 (1974), J. Chem. Soc. 
1958, 3742). 
Alkenyl derivatives Ib, furthermore, can be obtained by elimination 
reactions from suitably substituted precursors I' or I": 
##STR14## 
L is a leaving group, for example halogen, hydroxyl or alkyl- or 
arylsulfinyl. It is eliminated under basic (where L=halogen) or acidic 
(where L=OH) conditions or thermally (where L=alkyl- or arylsulfinyl). 
Precursors I' with L .alpha. to the heterocycle are, for example, the 
compounds Ij and Ik and the sulfoxide derivatives which are obtainable 
from Ik by reaction with alkane- or arenethiols followed by per-acid 
oxidation. Precursors I" with L .beta. to the heterocycle can be prepared, 
for the particularly preferred pyrimidine derivatives, for example, as 
follows (Scheme 8, Scheme 9): 
##STR15## 
While being tolerated well by plants and having favorable toxicity toward 
warm-blooded animals, the active substances are suitable for controlling 
animal pests, especially insects, arachnids, helminths and molluscs, and 
very preferably for controlling insects and arachnids, which are 
encountered in agriculture, in animal breeding, in forestry, in the 
protection of stored products and materials, and in the hygiene sector. 
They are active against normally sensitive and resistant species and 
against all or certain stages of development. The abovementioned pests 
include: 
From the order of the Acarina, for example, Acarus siro, Argas spp., 
Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta 
oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma 
spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., 
Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., 
Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.. 
From the order of the Isopoda, for example, Oniscus asellus, Armadium 
vulgar and Porcellio scaber. From the order of the Diplopoda, for example, 
Blaniulus guttulatus. 
From the order of the Chilopoda, for example, Geophilus carpophagus and 
Scutigera spp. 
From the order of the Symphyla, for example, Scutigerella immaculata. 
From the order of the Thysanura, for example, Lepisma saccharina. 
From the order of the Collembola, for example, Onychiurus armatus. 
From the order of the Orthoptera, for example, Blatta orientalis, 
Periplaneta americana, Leucophaea madeirae, Blattella germanica, Acheta 
domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, 
Melanoplus differentialis and Schistocerca gregaria. 
From the order of the Isoptera, for example, Reticulitermes spp.. 
From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus 
spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.. 
From the order of the Mallophaga, for example, Trichodectes spp. and 
Damalinea spp.. 
From the order of the Thysanoptera, for example, Hercinothrips femoralis 
and Thrips tabaci. 
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus 
intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and 
Triatoma spp.. From the order of the Homoptera, for example, Aleurodes 
brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, 
Bravicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, 
Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., 
Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, 
Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax 
striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, 
Pseudococcus spp. and Psylla spp.. 
From the order of the Lepidoptera, for example, Pectinophora gossypiella, 
Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, 
Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis 
chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis 
citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, 
Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, 
Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, 
Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria 
mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, 
Clysia ambiguella, Homona magnanima and Tortrix viridana. 
From the order of the Coleoptera, for example, Anobium punctatum, 
Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, 
Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon 
cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna 
varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., 
Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, 
Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma 
spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, 
Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., 
Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, 
Amphimallon solstitialis and Costelytra zealandica. 
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa 
spp., Lasius spp., Monomorium pharaonis and Vespa spp.. 
From the order of the Diptera, for example, Aedes spp., Anopheles spp., 
Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora 
erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., 
Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma 
spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia 
spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula 
paludosa. 
From the order of the Siphonaptera, for example, Xenopsylla cheopsis and 
Ceratophyllus spp.. 
From the order of the Arachnida, for example, Scorpio maurus and 
Latrodectus mactans. 
From the class of the helminths, for example, Haemonchus, Trichostrongulus, 
Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, 
Hyostrongulus, Ancylostoma, Ascaris and Heterakis and also Fasciola. 
From the class of the Gastropoda, for example, Deroceras spp., Arion spp., 
Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. 
and Oncomelania spp.. 
From the class of the Bivalva, for example, Dreissena spp.. The 
plant-parasitic nematodes which can be controlled in accordance with the 
invention include, for example, the root-parasitic soil nematodes such as, 
for example, those of the genera Meloidogyne (root knot eelworms, such as 
Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), 
Heterodera and Globodera (cyst nematodes, such as Globodera rostochiensis, 
Globodera pallida, Heterodera trifolii) and of the genera Radopholus, such 
as Radopholus similis, Pratylenchus, such as Pratylenchus neglectus, 
Pratylenchus penetrans and Pratylenchus curvitatus; 
Tylenchulus, such as Tylenchulus semipenetrans, Tylenchorhynchus, such as 
Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus such as 
Rotylenchus robustus, Helicotylenchus, such as Helicotylenchus 
multicinctus, Belonoaimus, such as Belonoaimus longicaudatus, Longidorus, 
such as Longidorus elongatus, Trichodorus, such as Trichodorus primitivus, 
and Xiphinema, such as Xiphinema index. 
The compounds according to the invention can also be used to control the 
nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci 
and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as 
Aphelenchoides ritzemabosi) and Anguina (leaf-gall nematodes, such as 
Anguina tritici). 
The invention also relates to compositions, especially insecticidal and 
acaricidal compositions, which comprise the compounds of the formula I in 
addition to suitable formulation auxiliaries. 
The compositions according to the invention comprise the active substances 
of the formulae I in general in a proportion of from 1 to 95% by weight. 
They can be formulated in various ways depending on the biological and/or 
chemicophysical parameters which prevail. Possible formulations which are 
suitable are therefore: 
wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions 
(SL), emulsions, sprayable solutions, oil- or water-based dispersions 
(SC), suspoemulsions (SE), dusts (DP), seed-dressing products, granules in 
the form of microgranules, spray granules, coated granules and adsorption 
granules, water-dispersible granules (WG), ULV formulations, 
microcapsules, waxes or baits. 
These individual types of formulation are known in principle and are 
described, for example, in: 
Winnacker-Kuchler, "Chemische Technologie" Chemical Technology!, Volume 7, 
C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides 
Formulations", Marcel Dekker N.Y., 2nd ed. 1972-73; K. Martens, "Spray 
Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd. London. 
The formulation auxiliaries required, such as inert materials, surfactants, 
solvents and other additives, are likewise known and are described, for 
example, in: 
Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., 
Darland Books, Caldwell N.J.; H. v. Olphen, "Introduction to Clay Colloid 
Chemistry", 2nd ed., J. Wiley & Sons, N.Y.; Marsden, "Solvents Guide", 2nd 
ed., lnterscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers 
Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of 
Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, 
"Grenzflachenaktive Athylenoxidaddukte" Surface-Active Ethylene oxide 
adducts!, Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Kuchler, 
"Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986. 
Based on these formulations, it is also possible to produce combinations 
with other pesticidally active substances, fertilizers and/or growth 
regulators, for example in the form of a readymix or a tank mix. Wettable 
powders are preparations, uniformly dispersible in water, which contain, 
beside the active substance and in addition to a diluent or inert 
material, wetting agents, for example polyoxethylated alkylphenols, 
polyoxethylated fatty alcohols, alkyl- or alkylphenolsulfonates, and 
dispersing agents, for example sodium ligninsulfonate or sodium 
2,2'-dinaphthylmethane-6,6'-disulfonate. Emulsifiable concentrates are 
prepared by dissolving the active substance in an organic solvent, for 
example butanol, cyclohexanone, dimethylformamide, xylene or 
higher-boiling aromatics or hydrocarbons, with addition of one or more 
emulsifiers. As emulsifiers, the following can be used, for example: 
calcium salts of alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, 
or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl 
polyglycol ethers, fatty alcohol polyglycol ethers, propylene 
oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan 
fatty acid esters, polyoxyethylene sorbitan fatty acid esters or 
polyoxethylene sorbitol esters. 
Dusting agents are obtained by grinding the active substance with finely 
divided solid substances, for example talc, natural clays such as kaolin, 
bentonite, poryphillite or diatomaceous earth. Granules can be prepared 
either by atomizing the active substance onto adsorptive, granulated inert 
material or by applying active substance concentrates onto the surface of 
carrier materials such as sand or kaolinites, or of granulated inert 
material, by means of adhesives, for example polyvinyl alcohol or sodium 
polyacrylate, or alternatively mineral oils. Suitable active substances 
can also be granulated in the fashion conventional for the preparation of 
fertilizer granules, if desired as a mixture with fertilizers. 
In wettable powders, the concentration of active substance is, for example, 
from approximately 10 to 90% by weight, the remainder to 100% by weight 
being composed of customary formulation components. In the case of 
emulsifiable concentrates, the concentration of active substance may be 
from approximately 5 to 80% by weight. Formulations in dust form comprise 
in most cases from 5 to 20% by weight of active substance, sprayable 
solutions from about 2 to 20% by weight. In the case of granules, the 
content of active substance depends partly on whether the active compound 
is in liquid or solid form and on which granulation auxiliaries, fillers, 
etc. are being used. 
In addition, the abovementioned formulations of active substance comprise, 
if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, 
penetrants, solvents, fillers or carriers which are customary in each 
case. 
The concentrates, which are in the commercially customary form, are if 
appropriate diluted in the customary manner for their use, for example 
using water in the case of wettable powders, emulsifiable concentrates, 
dispersions and some microgranules. Dust and granule preparations, and 
also sprayable solutions, are normally not diluted any further with other 
inert substances before being used. 
The application rate required varies with the external conditions, such as 
temperature and humidity among others. It can fluctuate within wide 
limits, for example between 0.0005 and 10.0 kg/ha or more of active 
substance, but is preferably between 0.001 and 5 kg/ha. 
The active substances according to the invention may be present in their 
commercially customary formulations, and in the application forms prepared 
from these formulations, as mixtures with other active substances, such as 
insecticides, attractants, sterilants, acaricides, nematicides, 
fungicides, growth regulators or herbicides. 
The pesticides include, for example, phosphates, carbamates, carboxylates, 
formamidines, tin compounds and substances produced by microorganisms, 
inter alia. 
Preferred mixture components are 
1. from the group of the phosphorus compounds acephate, azamethiphos, 
azinphosethyl, azinphosmethyl, bromophos, bromophos-ethyl, 
chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifosmethyl, demeton, 
demeton-S-methyl, demeton-S-methylsulphone, dialifos, diazinon, 
dichlorvos, dicrotophos, O,O-1,2,2,2-tetrachloroethyl phosphorothioate (SD 
208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, 
famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, 
formothion, heptenophos, isozophos, isothioate, isoxathion, malathion, 
methacrifos, methamidophos, methidathion, salithion, mevinphos, 
monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, 
parathionmethyl, phenthoate phorate, phosalone, phosfolan, phosmet, 
phosphamidon, phoxim, pirimiphos, pirimiphosethyl, pirimiphosmethyl, 
profenofos, propaphos, proetamphos, prothiofos, pyraclofos, 
pyridapenthion, quinalphos, sulprofos, temephos, terbufos, 
tetraclorvinphos, thiometon, triazophos, trichlorphon, vamidothion; 
2. from the group of the carbamates aldicarb, 2-sec-butylphenyl 
methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, 
benfuracarb, ethiefencarb, furathiocarb, isoprocarb, methomyl, 
5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, 
thiodicarb, thiofanox, ethyl 
4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate 
(OK 135), 
1-methylthio(ethylideneamino)-N-methyl-N-(morpholinothio)carbamate (UC 
51717); 
3. from the group comprising the carboxylates allethrin, alphametrin, 
5-benzyl-3-furylmethyl (E)-(1R) 
cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, 
bioallethrin, bioallethrin ((S)cyclopentyl isomer), bioresmethrin, 
biphenate, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl 
(1RS)-trans-3-(4-tert-butyl-phenyl)-2,2-dimethylcyclopropanecarboxylate 
(NCI 85193), cycloprothrin, cyhalothrin, cythithrin, cypermethrin, 
cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, 
fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate 
(D-isomers), permethrin, phenothrin ((R)-isomers), d-prallethrin, 
pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, 
tralomethrin; 
4. from the group of the amidines amitraz, chlordimeform; 
5. from the group of the tin compounds cyhexatin, fenbutatin oxide; 
6. others abamectin, Bacillus thuringiensis, bensultap, binapacryl, 
bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, 
chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), 
clorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), 
cyromazin, 
N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propoxy)phenyl)carbamoyl)-2-ch 
lorobenzocarboximide, DDT, dicofol, 
N-(N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,6- 
difluorobenzamide (XRD 473), diflubenzuron, 
N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)2,4-xylidine, dinobuton, 
dinocap, endosulfan, ethofenprox, 
(4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)-propyl)silane, 
(4-ethoxyphenyl)(3-(4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane, 
fenoxycarb, 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl 
ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenthiocarb, 
flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, 
hydramethyinon (AC 217300), ivermectin, 
2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 
2-nitromethyl-3,4-dihydrothiazole (SD 35651), 
2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), propargite, 
teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron and 
imidacloprid. 
The active substance content of the use forms prepared from the 
commercially customary formulations can be from 0.00000001 to 95% by 
weight of active substance, preferably between 0.00001 and 1% by weight. 
Application is effected in a conventional fashion, matched to the use 
forms. 
The active substances according to the invention are also suitable for 
controlling ecto- and endoparasites in the veterinary sector or in the 
sector of animal husbandry. 
The active substances according to the invention are in this case applied 
in a known fashion, such as by oral application in the form of, for 
example, tablets, capsules, potions or granules, by dermal application in 
the form of, for example, dipping, spraying, pouring-on and spotting-on 
and powdering, and also by parenteral application in the form of, for 
example, injection. 
The novel compounds, according to the invention, of the formula I can 
accordingly also be employed particularly advantageously in livestock 
husbandry (for example cattle, sheep, pigs and poultry such as chickens, 
geese etc.). In a preferred embodiment of the invention, the novel 
compounds, if appropriate in suitable formulations (cf. above) and if 
appropriate with the drinking water or feed, are administered orally to 
the animals. Since excretion in the droppings occurs in an effective 
fashion, the development of insects in the animal droppings can be 
prevented very simply in this fashion. The dosages and formulations 
suitable in each case are particularly dependent on the type and stage of 
development of the productive animals and also on the degree of 
infestation, and can easily be determined and fixed by conventional 
methods. In the case of cattle, the novel compounds can be employed, for 
example, in dosages of 0.01 to 1 mg/kg of body weight. 
The compounds of the formula I according to the invention are also 
distinguished by an outstanding fungicidal action. Fungal pathogens which 
have already penetrated the plant tissue can be successfully subjected to 
curative control. This is particularly important and advantageous in the 
case of those fungal diseases which can no longer be controlled 
effectively with the otherwise customary fungicides when infection has 
taken place already. The spectrum of action of the claimed compounds 
embraces various economically important phytopathogenic fungi, for example 
Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, 
Piricularia oryzae, Pyrenophora teres, Leptosphaeria nodorum, Pellicularia 
sasakii and Puccinia recondite. 
In addition, the compounds according to the invention are also suitable for 
use in technical fields, for example as wood preservatives, as 
preservatives in paints, in cooling lubricants for metalworking, or as 
preservatives in drilling and cutting oils. 
The active substances according to the invention in their commercially 
customary formulations can be employed either alone or in combination with 
other fungicides known from the literature. 
Examples of fungicides which are known from the literature and which can be 
combined, in accordance with the invention, with the compounds of the 
formula I are the following products: aldimorph, andoprim, anilazine, BAS 
480F, BAS 450F, BAS 490F, benalaxyl, benodanil, benomyl, binapacryl, 
bitertanol, bromuconazole, buthiobate, captafol, captan, carbendazim, 
carboxin, CGA 173506, cyprodinil, cyprofuram, dichlofluanid, dichlomezin, 
diclobutrazol, diethofencarb, difenconazol (CGA 169374), difluconazole, 
dimethirimol, dimethomorph, diniconazole, dinocap, dithianon, dodemorph, 
dodine, edifenfos, ethirimol, etridiazole, epoxiconazole, fenbuconazole, 
fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin 
acetate, fentin hydroxide, ferimzone (TF164), fluazinam, fluobenzimine, 
fludioxinil, fluquinconazole, fluorimide, flusilazole, flutolanil, 
flutriafol, folpet, fosetylaluminium, fuberidazole, fulsulfamide (MT-F 
651), furalaxyl, furconazole, furmecyclox, guazatine, hexaconazole, ICI 
A5504, imazalil, imibenconazole, iprobenfos, iprodione, isoprothiolane, 
KNF 317, copper compounds, such as Cu oxychloride, oxine-Cu, Cu oxide, 
mancozeb, maneb, mepanipyrim (KIF 3535), metconazol, mepronil, metalaxyl, 
methasulfocarb, methfuroxam, MON 24000, myclobutanil, nabam, 
nitrothalidopropyl, nuarimol, ofurace, oxadixyl, oxycarboxin, penconazole, 
pencycuron, PP 969, probenazole, propineb, prochloraz, procymidon, 
propamocarb, propiconazole, prothiocarb, pyracarbolid, pyrazophos, 
pyrifenox, pyrimethanil, pyroquilon, rabenzazole, RH7592, sulfur, 
tebuconazole, TF 167, thiabendazole, thicyofen, thiofanatemethyl, thiram, 
tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxid, 
tricyclazole, tridemorph, triflumizol, triforine, trifionazol, 
validamycin, vinchlozolin, XRD 563, zineb, sodium dodecyl-sulfonate, 
sodium dodecyl sulfate, sodium C13/C15 alcohol ether sulfonate, sodium 
cetostearyl phosphate ester, sodium dioctylsulfosuccinate, sodium 
isopropyinaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, 
cetyltrimethylammonium chloride, salts of long-chain primary, secondary or 
tertiary amines, alkylpropyleneamines, laurylpyrimidinium bromide, 
ethoxylated quaternized fatty arnines, alkyldimethylbenzylammonium 
chloride and 1-hydroxyethyl-2-alkylimidazoline. 
The abovementioned components for combinations are known active substances 
of which many are described in Ch. R. Worthing, S. B. Walker, The 
Pesticide Manual, 7th edition (1983), British Crop Protection Council. The 
active substance content of the use forms prepared from commercially 
customary formulations can vary within wide limits, and the concentration 
of active substance in the use forms can be from 0.0001 up to 95% by 
weight of active substance, preferably between 0.0001 and 1% by weight. 
The formulations are applied in a customary manner adapted to suit the use 
forms. 
The examples which follow illustrate the invention without limiting it 
thereto.

A. FORMULATION EXAMPLES 
a) A dusting agent is obtained by mixing 10 parts by weight of active 
substance and 90 parts by weight of talc as inert material and comminuting 
in a hammer mill. 
b) A wettable powder which is easily dispersible in water is obtained by 
mixing 25 parts by weight of active substance, 65 parts by weight of 
kaolin-containing quartz as inert material, 10 parts by weight of 
potassium ligninsulfonate and 1 part by weight of sodium 
oleoylmethyltaurinate as wetting and dispersing agent, and grinding in a 
pinned disk mill. 
c) A dispersion concentrate which is easiiy dispersible in water is 
prepared by mixing 40 parts by weight of active substance with 7 parts by 
weight of a sulfosuccinic monester, 2 parts by weight of a sodium 
ligninsulfonate and 51 parts by weight of water and grinding in a ball 
mill to a fineness of below 5 microns. 
d An emulsifiable concentrate can be prepared from 15 parts by weight of 
active substance, 75 parts by weight of cyclohexane as solvent and 10 
parts by weight of ethoxylated nonylphenol (10 EO) as emulsifier. 
e) Granules can be prepared from 2 to 15 parts by weight of active 
substance and an inert granule carrier material such as attapulgite, 
granulated pumice and/or quartz sand. It is expedient to use a suspension 
of the wettable powder of Example b) with a solids content of 30% which is 
sprayed onto the surface of attapulgite granules which are then dried and 
intimately mixed. The proportion by weight of the wettable powder in this 
case is about 5% and that of the inert carrier material is about 95% of 
the finished granules. 
B. PREATION EXAMPLES 
Example 1 
4-(cis-4-tert-Butylcyclohexylamino)-6-ethyl-5-iodopyrimidine 
7.25 g (30 mmol) of 4-chloro-5-iodo-5-ethylpyrimidine (EP 470 600), 5.6 g 
(36 mmol) of cis-4-tert-butylcyclohexylamine and 6.1 g of triethylamine 
were heated at from 80.degree. to 90.degree. C. for 4 hours without 
solvent. After cooling, the mixture was taken up in water/toluene and the 
organic phase was dried and concentrated. The crude product was purified 
by chromatography on silica gel using petroleum ether/ethyl acetate (7:3), 
to give 7.4 g (56.7% of theory) of a yellow oil. 
Example 2 
4-(cis-4-tert-Butylcyclohexylamino)-5-cyano-6-ethylpyrimidine 
1.8 g (5 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1) 
and 1.0 g of copper(I) cyanide were stirred at 200.degree. C. for 30 
minutes without solvent. After cooling, the mixture was taken up in 
water/dichloromethane, the organic phase was again extracted by stirring 
with aqueous ammonia solution, and the extract was dried and concentrated. 
The crude product was purified by chromatography on silica gel using 
petroleum ether/ethyl acetate (7:3), to give 750 mg (52.4% of theory) of a 
colorless oil which crystallized on standing. 
m.p.: 66.degree. to 67.degree. C. 
Example 2a 
5-Cyano-6-ethyl-4-cis-4-(1,1,2-trimethylpropyl)cyclohexylamino!pyrimidine 
Prepared as in Example 2 from 
6-ethyl-5-iodo-4-cis-4-(1,1,2-trimethylpropyl)cyclohexylamino!pyrimidine 
and copper(I) cyanide. 
m.p.: 51.degree. to 53.degree. C. 
Example 3 
5-Ethoxycarbonyl-6-ethyl-4-(cis-4-trimethylsilylcyclohexylamino)pyrimidine 
1.00 g (4.66 mmol) of 4-chloro-5-ethoxycarbonyl-6-ethylpyrimidine (EP 606 
011), 0.84 g (4.89 mmol) of cis-4-trimethylsilylcyclohexylamine and 0.94 g 
(9.29 mmol) of triethylamine were heated at 70.degree. C. for 5 hours 
without solvent. After cooling, the mixture was taken up in water/methyl 
chloride and the organic phase was dried and concentrated. The residue was 
purified by chromatography on silica gel using petroleum ether/ethyl 
acetate (4:1), to give 1.1 g (67% of theory) of a colorless oil. 
Preparation of the starting material cis-4-trimethylsilylcyclohexylamine 
A solution of 18.0 g (106 mmol) of 4-trimethylsilylcyclohexanone (prepared 
according to R. J. Fessenden, K. Seeler, M. Dagani, J. Org. Chem. 1966, 
31, 2483) in 120 ml of ammoniacal isopropanol (90 g/l) was hydrogenated at 
50.degree. C. and 50 bar for 20 hours over 2 g of 5% Pd/Rh (4:1) on active 
charcoal (Degussa). For working up, the catalyst was filtered off and the 
solvent was removed, to give 15.9 g (93 mmol, 88%) of a colorless oil 
which was used subsequently without further purification. 
Example 4 
4-(cis-4-tert-Butylcyclohexylamino)-5-ethoxycarbonyl-6-ethylpyrimidine 
In analogy to Example 2, 1.00 g (4.66 mmol) of 
4-chloro-5-ethoxycarbonyl-6-ethylpyrimidine, 0.76 g (4.85 mmol) of 
cis-4-tert-butylcyclohexylamine and 0.94 g (9.29 mmol) of triethylamine 
gave 1.1 g (70% of theory) of the product as a colorless solid. 
m.p.: 69.degree. to 70.degree. C. 
Example 5 
4-(cis-4-tert-Butylcyclohexylamino)-6-ethyl-5-methoxycarbonylpyrimidine 
5.8 g (15 mmol) of 
4-(cis-tert-butylcyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1) 
were reacted with 80 bar of carbon monoxide in an autoclave at 50.degree. 
C. in the presence of 2.5 g of triethylamine and 0.1 g of 
bis(triphenylphosphine)palladium dichloride in 100 ml of methanol. The 
catalyst was removed by filtration and the filtrate was concentrated. 
Chromatography on silica gel (petroleum ether/ethyl acetate 7:3) gave 2.1 
g (30.3% of theory) of colorless oil. 
Example 6 
6-Ethyl-5-methoxycarbonyl-4- 
(cis-4-trimethylsilylcyclohexylamino)pyrimidine 
12.4 g (62.0 mmol) of 4-chloro-6-ethyl-5-methoxycarbonylpyrimidine, 11.1 g 
(62.0 mmol) of cis-4-trimethylsilylcyclohexylamine and 12.55 g (124 mmol) 
of triethylamine were heated in 30 ml of toluene at 90.degree. C. for 3 
hours. After complete reaction, the mixture was partitioned between 
dichloromethane and water to give, after further extraction with 
dichloromethane and column chromatography on silica gel, 17.76 g (85.4% of 
theory) of the cyclohexylaminopyrimidine as a pale brown oil, 
n.sub.D.sup.21 =1.5230. 
Preparation of the precursor 4-chloro-6-ethyl-5-methoxycarbonylpyrimidine 
20 g (74.5 mmol) of 4-chloro-6-ethyl-5-iodopyrimidine, 12.6 g (125 mmol) of 
triethylamine and 0.86 g (0.7 mmol) of 
tetrakistriphenylphosphinepalladium(0) were reacted for 24 hours at 
70.degree. C. and 100 bar carbon monoxide pressure. The solvent was 
removed and the solid residue was partitioned between water and ethyl 
acetate. Further extraction and column chromatography gave 12 g (80% of 
theory) of the methoxycarbonylpyrimidine as a colorless oil, 
n.sub.D.sup.21 =1.5063. 
Example 7 
4-(cis-4-tert-Butylcyclohexylamino)-6-ethyl-5-(trimethylsilylethynyl)pyrimi 
dine 
6.5 g (17 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1), 
3.24 g (33 mmol) of bis(triphenyl)palladium(II) chloride and 0.035 g (0.2 
mmol) of copper(I) iodide were stirred in 20 ml of triethylamine at 
50.degree. C. for 6 hours. The mixture was worked up by concentrating it, 
taking up the residue in toluene, filtering off the insoluble material and 
concentrating the filtrate. Chromatography on silica gel left 4.1 g (61.6% 
of theory) of colorless oil. 
Example 7a 
4-(cis-4-tert-Butylcyclohexylamino)-5-ethynyl-6-ethylpyrimidine 
2.8 g (7.7 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-6-ethyl-5-(trimethylsilylethynyl)pyrim 
idine (Example 7) were stirred in 25 ml of a 0.4 molar solution of 
potassium hydroxide in methanol at room temperature for 4 hours. The 
mixture was concentrated, the residue was taken up in toluene/water and 
the organic phase was dried and concentrated to leave 1.85 g (84.2% of 
theory) of a colorless solid. 
m.p.: 96.degree. to 97.degree. C. 
Example 8 
6-Ethyl-5-iodo-4-(cis-4-phenylcyclohexylamino)pyrimidine 
Prepared as in Example 1 from 4-chloro-5-iodo-6-ethylpyrimidine and 
cis-4-phenylcyclohexylamine. 
m.p.: 90.degree. to 91.degree. C. 
Example 9 
6-Ethyl-4-(cis-4-phenylcyclohexylamino)-5-trimethylsilylethynylpyrimidine 
Prepared as in Example 7 from 
6-ethyl-5-iodo-4-(cis-4-phenylcyclohexylamino)pyrimidine (Example 8) and 
trimethylsilylacetylene (colorless solid). 
Example 10 
5-Ethynyl-6-ethyl-4-(cis-4-phenylcyclohexylamino)pyrimidine 
Prepared as in Example 6 from 
6-ethyl-4-(cis-4-phenylcyclohexylamino)-5-trimethylsilylethynylpyrimidine 
(Example 9) by eliminating the silyl group in methanolic potassium 
hydroxide solution. 
m.p.: 92.degree. to 93.degree. C. 
Example 11 
6-Ethyl-5-iodo-6-(cis-4-trimethylsilylcyclohexylamino)pyrimidine 
Prepared as in Example 1 from 4-chloro-5-iodo-6-ethylpyrimidine and 
cis-4-trimethylsilylcyclohexylamine (yellow oil). The following compounds 
were further prepared analogously: 
Example 11a 
6-Ethyl-5-iodo-4-cis-4-dimethyl- 
(2-ethoxyethyl)silyl!-cyclohexylamino!pyrimidine, colorless oil 
Example 11b 
6-Ethyl-5-iodo-4-cis-4-(dimethylmethoxymethylsilyl)-cyclohexylamino!pyrimi 
dine, colorless oil 
Examples 12 to 18 (Table 1) 
##STR16## 
Prepared as in Example 7 from in each case 5 mmol of one of the 
silylcyclohexylamino derivatives of Examples 11 to 11b, 15 mmol of 
acetylene component, 150 mg of tetrakis-(triphenylphosphine)palladium(0) 
and 100 mg of copper(I) iodide. 
TABLE 1 
______________________________________ 
Ex. No. 
R.sup.1 R.sup.2 m.p. .degree.C.! 
Yield %! 
______________________________________ 
12 Si(CH.sub.3).sub.3 
CH.sub.3 Resin 78.5 
13 Si(CH.sub.3).sub.3 
CH.sub.2 OCH.sub.3 
Resin 63.4 
14 Si(CH.sub.3).sub.3 
(CH.sub.2).sub.2 OC.sub.2 H.sub.5 
Resin 72.3 
15 Si(C.sub.2 H.sub.5).sub.3 
CH.sub.3 Resin 71.7 
16 Si(i-C.sub.3 H.sub.7) 
CH.sub.3 Resin 70.7 
17 Si(C.sub.6 H.sub.5).sub.3 
CH.sub.3 95 to 97 
69.7 
18 CH.sub.3 CH.sub.3 Resin 44.0 
______________________________________ 
Examples 19 to 20a 
##STR17## 
2.7 mmol of a trimethylsilyl compound from Table 1 (R.sup.1 
.dbd.Si(CH.sub.3).sub.3) were stirred at room temperature under inert gas 
in 0.4N methanolic KOH until the protecting group had been eliminated 
completely. The solvent was removed in vacuo, the solid residue was taken 
up in water and neutralized and the mixture was extracted with 
dichloromethane. Chromatography on silica gel gave the alkines as 
colorless oils. 
TABLE 2 
______________________________________ 
Ex. No. R Yield %! 
______________________________________ 
19 Si(CH.sub.3).sub.3 
82.3 
20 Si(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 
72.4 
20a Sl(CH.sub.3).sub.2 (CH.sub.2).sub.2 OC.sub.2 H.sub.5 
82.9 
______________________________________ 
Example 21 
5-(tert-Butyidimethylsilylethynyl)-6-ethyl-4-(cis-4-trimethylsilylcyclohexy 
lamino)pyrimidine 
1.0 g (3.3 mmol) of 
5-ethynyl-6-ethyl-4-(cis-4-trimethylsilylcyclohexylamino)pyrimidine 
(Example 19) dissolved in 5 ml of absolute THF was added to 1.8 ml of a 
3.0M solution of methylmagnesium chloride. After 1 hour, 1.25 g (8.3 mmol) 
of tert-butyidimethylsilyl chloride in 10 ml of absolute THF were added 
dropwise and the mixture was stirred at room temperature. Hydrolysis, 
extraction with ether and column chromatography gave 0.26 g (19% of 
theory) of the silylated acetylene (colorless oil) and 0.33 g (0.11 
mmol)=33% of the starting material. 
Example 22 
4-(cis-4-tert-Butylcyclohexylamino)-6-ethyl-5-vinylpyrimidine 
3.9 g (10 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1) 
were treated with 10 bar of ethylene in an autoclave at 120.degree. C. in 
the presence of 1.5 g (15 mmol) of potassium acetate and 50 mg of 
palladium black in 100 ml of methanol. After 24 hours, the catalyst was 
removed by filtration and the mixture was concentrated. Chromatography on 
silica gel gave 1.70 g (61.8% of theory) of colorless oil. 
Example 23 
5-Cyanoethyl-6-(cis-4-phenylcyclohexylamino)pyrimidine 
Prepared as in Example 2 from 
6-ethyl-5-iodo-4-(cis-4-phenylcyclohexylamino)pyrimidine (Example 8) and 
copper(I) cyanide, colorless solid, m.p. 58.degree.-59.degree. C. 
Example 24 
6-Ethyl-4-(cis-4-phenylcyclohexylamino)-5-vinylpyrimidine 
Starting from 4.07 g (10 mmol) of 
6-ethyl-5-iodo-6-(4-phenylcyclohexylamino)pyrimidine (Example 8) and in 
analogy to Example 22, 1.94 g (63.2% of theory) of yellow solid were 
obtained. 
m.p.: 53.degree. to 54.degree. C. 
Example 25 
4-(cis-4-tert-Butylcyclohexylamino)-5-chloro-6-vinylpyrimidine 
A solution of 7.6 g (21 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-(1-methylsulfinylethyl)pyri 
midine (Example 26) in 100 ml of diethylene glycol dimethyl ether to which 
a little hydroquinone had been added was heated at 150.degree. C. for 30 
minutes. After cooling to room temperature the mixture was poured into 
water and extracted by stirring with dichloromethane. This left a brown 
oil which was extracted twice by stirring with petroleum ether. The 
petroleum ether phase was concentrated and the residue was purified with 
chromatography on silica gel, to give 1.1 g (17.8% of theory) of colorless 
solid. 
m.p.: 51.degree.-52.degree. C. 
Example 26 
##STR18## 
4-(cis-4-tert-Butylcyclohexylamino)-5-chloro-6-( 
1-methylsulfinylethyl)pyrimidine 
10.25 g (30 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-(1-methylthioethyl)pyrimidi 
ne were placed in 120 ml of dichloroethane, and a solution of 7.40 g (30 
mmol) of 70% 3-chloroperbenzoic acid in 50 ml of dichloromethane was added 
dropwise at 0.degree. C. The mixture was stirred at room temperature for 8 
hours and extracted by stirring with sodium bicarbonate solution and 
water. The organic phase was dried and concentrated, to give 10.5 g (98% 
of theory) of a colorless resin (diastereomer mixture). 
Preparation of the precursor 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-(1-methylthioethyl)pyrimidi 
ne 
19.8 g (60 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-(1-chloroethyl)pyrimidine 
and 4.2 g (60 mmol) of sodium methanethiolate were heated at reflux in 100 
ml of methanol for 6 hours. The mixture was concentrated and the residue 
was taken up in water/toluene. The organic phase was dried and 
concentrated, to give 17.7 g (85% of theory) of a colorless resin which 
was subsequently reacted without further purification. 
Preparation of the precursor 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-(1-chloroethyl)pyrimidine 
32.3 g (0.15 mol) of 4,5-dichloro-6-(1-chloroethyl)pyrimidine(EP 543 402) 
were stirred in 200 ml of toluene with 23.3 g (0.15 mol) of 
cis-4-tert-butylcyclohexylamine and 20.2 g (0.20 mol) of triethylamine at 
from 80.degree. to 90.degree. C. for 6 hours. The mixture was extracted by 
stirring with water and the organic phase was dried and concentrated. The 
residue was purified by chromatography on silica gel, to give 36.3 g 
(73.2% of theory) of a colorless oil. 
Example 27 
4-(cis-4-tert-Butylcyclohexylamino)-5-chloro-6-(trimethylsilylethynyl)pyrim 
idine 
In analogy to Example 7, 1.6 g (4 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-iodopyrimidine, 2.0 g of 
trimethylsilylacetylene, 100 mg of bis-triphenylphosphine palladium 
dichloride and 20 mg of copper(I) iodide in 20 ml of triethylamine gave, 
after chromatography on silica gel (petroleum ether/ethyl acetate 9:1), 
0.7 g (47.3% of theory) of a colorless oil which gradually crystallized. 
m.p.: 92.degree. to 93.degree. C. 
Preparation of the precursor 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-iodopyrimidine 
3.6 g (10 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-6-iodopyrimidine and 
2.0 g of N-chlorosuccinimide were heated at reflux for 8 hours in 15 ml of 
chloroform. After cooling to room temperature, the mixture was extracted 
by stirring with dilute sodium hydroxide solution and water and the 
organic phase was dried and concentrated. The residue was purified by 
chromatography on silica gel (petroleum ether/ethyl acetate 4:1) to give 
first of all 2.3 g (58.4% of theory) of product (a colorless oil which 
gradually crystallized, m.p. 89.degree. to 90.degree. C.) and, finally, 
1.0 g of unreacted starting material. 
Preparation of the precursor 
4-(cis-4-tert-butylcyclohexylamino)-6-iodopyrimidine 
2.0 g (7.5 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-6-chloropyrimidine 
were heated at reflux for 5 hours in 20 ml of aqueous hydroiodic acid (57% 
strength). After cooling the mixture was filtered with suction, the solid 
was suspended in water and the suspension was rendered basic using ammonia 
solution. It was extracted with dichloromethane and the organic phase was 
dried and concentrated, to leave 1.2 g (44.5% of theory) of colorless 
resin which gradually crystallized. 
m.p.: 99.degree. to 100.degree. C. 
Preparation of the precursor 
4-(cis-4-tert-butylcyclohexylamino)-6-chloropyrimidine 
58.6 g (0.39 mol) of 4,6-dichloropyrimidine were placed in 400 ml of 
toluene, and a mixture of 61.0 g (0.39 mol) of 
cis-4-tert-butylcyclohexylamine and 50.0 g (0.50 mol) of triethylamine in 
100 ml of toluene was added dropwise at from 70.degree. to 80.degree. C. 
The mixture was subsequently stirred at reflux for 4 hours. After cooling, 
it was extracted by stirring with water, the organic phase was dried and 
concentrated, to give a colorless oil which crystallized after trituration 
with petroleum ether. Filtration with suction left 70.5 g (67.0% of 
theory) of colorless crystals. 
m.p.: 112.degree. to 113.degree. C. 
Example 28 
##STR19## 
4-(cis-4-tert-Butylcyclohexylamino)-5-chloro-6-(1-cyanoethyl)pyrimidine 
3.3 g (10 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-(1-chloroethyl)pyrimidine 
(precursor to Example 26) and 1.3 g (20 mmol) of potassium cyanide were 
heated at reflux in 20 ml of ethanol in the presence of 250 mg of 
potassium iodide. After stripping off the solvent, the residue was taken 
up in water/toluene and the organic phase was dried and concentrated. 
Chromatography on silica gel (petroleum ether/ethyl acetate 7:3) gave, 
after 1.0 g of starting material, 1.1 g (34.3% of theory) of product as 
colorless oil. 
Example 29 
##STR20## 
6-(1-Acetoxyethyl)-4-(cis-tert-butylcyclohexylamino)-5-chloropyrimidine 
10.0 g (42.5 mmol) of 6-(1-acetoxyethyl)-4,5-dichloropyrimidine (EP 543 
402), 6,6 g (42.5 mmol) of cis-4-tert-butylcyclohexylamine and 4.7 g (46.9 
mmol) of triethylamine were stirred in 100 ml of toluene at from 
80.degree. to 90.degree. C. for 6 hours. The mixture was extracted by 
stirring with water and the organic phase was dried and concentrated, to 
leave 15.0 g (100% of theory) of a colorless oil. 
Example 30 
##STR21## 
4-(cis-4-tert-Butylcyclohexylamino)-5-chloro-6-(1-hydroxyethyl)pyrimidine 
1.5 g (40 mmol) of lithium aluminum hydride were placed in 100 ml of dry 
tetrahydrofuran, and a solution of 14 g (40 mmol) of 
6-(1-acetoxyethyl)-4-(cis-4-tert-butylcyclohexylamino)-5-chloropyrimidine 
(Example 30) in 50 ml of dry tetrahydrofuran was added dropwise at a 
temperature of 20.degree. to 30.degree. C. The mixture was then heated at 
reflux for 2 hours. After cooling, 5 ml of water were added carefully 
dropwise and, after standing overnight, the mixture was filtered with 
suction to remove the inorganic material. The filtrate was concentrated 
and the residue was chromatographed on silica gel (ethyl acetate/methanol 
9:1) to give 6.0 g (48.1% of theory) of a colorless oil. 
Example 31 
Ethyl 4-(cis-4-tert-butylcyclohexylamino)-6-methylpyrimidin-5-yl!acetate 
15.2 g (71 mmol) of methyl (4-chloro-6-methylpyrimidin-5-yl)acetate, 11.0 g 
(71 mmol) of cis-4-tert-butylcyclohexylamine and 20.2 g (0.2 mol) of 
triethylamine were heated at 80.degree. to 90.degree. C. for 6 hours 
without solvent. After cooling, the mixture was taken up in water/toluene 
and the organic phase was dried and concentrated. In the chromatography on 
silica gel (petroleum ether/ethyl acetate 1:1, then ethyl acetate/methanol 
9:1), 5.3 g of chloropyrimidine starting material were first of all 
retained and then 10.0 g (27.7% of theory) of product were obtained as a 
yellow solid. 
m.p.: 68.degree. to 69.degree. C. 
Preparation of the precursor ethyl (4-chloro-6-methylpyrimidin-5-yl)acetate 
30.6 g (0.16 mol) of ethyl (4-hydroxy-6-methylpyrimidin-5-yl)acetate, 17.8 
g (0.18 mol) of triethylamine and 263.2 g (1.72 mol) of phosphorus 
oxychloride were heated at reflux for 4 hours. The excess phosphorus 
oxychloride was stripped off, the residue was taken up in dichloromethane, 
and the mixture was added dropwise to 500 ml of sodium bicarbonate 
solution and neutralized by addition of solid sodium bicarbonate. The 
organic phase was separated off, dried and concentrated to give 30.4 g 
(88.5% of theory) of a dark oil which was reacted further without 
purification. 
Preparation of the precursor ethyl 
(4-hydroxy-6-methylpyrimidin-5-yl)acetate 
216.24 g (1.0 mol) of ethyl acetylsuccinate and 104.11 g (1.0 mol) of 
formamidine acetate were placed in 500 ml of ethanol, and 360.13 g (2.0 
mol) of 30% methanolic sodium methylate solution were added dropwise at 
0.degree. C. The mixture was stirred at room temperature for 6 hours and 
concentrated and the residue was taken up in toluene/water. The aqueous 
phase was brought to a pH of 3-4 with conc. hydrochloric acid and 
extracted by stirring a number of times with dichloromethane. Drying and 
concentration of the combined dichloromethane phases left a resinous 
solid. This solid was stirred with a mixture of diisopropyl ether and 
ethyl acetate (2:1) which was then filtered with suction to leave 55.6 g 
(28.3% of theory) of colorless crystals of m.p. 148.degree. to 149.degree. 
C. 
Example 32 
Ethyl 6-Methyl-4-(cis-4-phenylcyclohexylamino)pyrimidin-5-yl!acetate 
In analogy to Example 31, 15.2 g (0.071 mol) of ethyl 
4-chloro-6-methylpyrimidin-5-yl!acetate (precursor to Example 31), 12.4 g 
(0.071 mol) of cis-4-phenylcyclohexylamine and 20.2 g (0.02 mol) of 
triethylamine gave, in addition to 7.5 g of recovered chloropyrimidine, 
5.0 g (19.9% of theory) of product as a dark resin. 
Example 33 
4-(cis-4-tert-Butylcyclohexylamine)-5-(2-hydroxyethyl)-6-methyl-pyrimidine 
A solution of 8.26 g (25 mmol) of ethyl 
4-(cis-4-tert-butyl-cyclohexylamino)-6-methylpyrimidin-5-yl!acetate 
(Example 31) in 50 ml of dry tetrahydrofuran was added dropwise to a 
suspension of 1.14 g (30 mmol) of lithium aluminum hydride in 100 ml of 
dry tetrahydrofuran. The mixture was stirred at 50.degree. C. for 2 hours, 
cooled and decomposed by the dropwise addition of 20 ml of ethyl acetate 
and 10 ml of water. After standing overnight it was filtered with suction 
and the filtrate was dried and concentrated. Chromatography of the crude 
product on silica gel (ethyl acetate/methanol 4:1) left 4.31 g of a yellow 
solid. 
m.p.: 150.degree. to 152.degree. C. 
Example 34 
5-(2-Hydroxyethyl)-6-methyl-4-(cis-4-phenylcyclohexylamino)pyrimidine 
In analogy to Example 33, 4.0 g (11 mol) of ethyl 
6-methyl-4-(cis-4-phenylcyclohexylamino)pyrimidin-5-yl!acetate (Example 
32) and 0.46 g (12 mmol) of lithium aluminum hydride gave 1.83 g (53.4% of 
theory) of product. 
m.p. 134.degree. to 136.degree. C. 
Example 35 
4-(cis-4-tert-Butylcyclohexylamino)-6-methyl-5-(2-fluoroethyl)pyrimidine 
2.0 g (6.5 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-6-methyl-5-(2-hydroxyethyl)pyrimidine 
(Example 33) were dissolved in 30 ml of dichloromethane, and 1.16 g (7.2 
mmol) of diethylaminosulfur trifluoride (DAST) were added at -50.degree. 
C. The mixture was allowed to rise to room temperature, and was 
subsequently stirred for 4 hours. It was poured into water, the 
dichloromethane phase was extracted by stirring with sodium hydrogen 
carbonate solution and the organic extracts were dried and concentrated. 
Chromatography on silica gel gave 1.55 g (77.6% of theory) of product as 
colorless oil. 
Example 36 
5-(2-Fluoroethyl)-6-methyl-4-(cis-4-phenylcyclohexylamino)pyrimidine 
In analogy to Example 35, 1.13 g (3.6 mmol) of 
5-(2-hydroxyethyl)-6-methyl-4-(cis-4-phenylcyclohexylamino)pyrimidine 
(Example 34) and 0.66 g (41 mmol) of DAST gave, after chromatography on 
silica gel, 0.76 g (67.4% of theory) of product as a colorless oil. 
Example 37 
6-Ethyl-5-hydroxymethyl-4-(cis-4-trimethylsilylcyclohexylamino)pyrimidine 
A solution of 7.0 g (20.9 mmol) of 
5-methoxycarbonyl-6-ethyl-4-(cis-4-(trimethylsilyl)cyclohexylamino)pyrimid 
ine (Example 6) in 30 ml of absolute tetrahydrofuran was added dropwise to 
a suspension, cooled to -30.degree. C., of 1.03 g (27.1 mmol) of lithium 
aluminum hydride in 10 ml of absolute tetrahydrofuran, and the mixture was 
stirred at room temperature until the end of reaction. Following the 
hydrolysis, the mixture was subjected to extraction with diethyl ether to 
give, after drying and removal of the solvent, 6.13 g (19.9 mmol)=95% of 
the hydroxymethyl compound in the form of white crystals. 
m.p.=136.degree. to 138.degree. C. 
Example 38 
Ethyl 4-(cis-4-tert-butylcyclohexylamino)pyrimidin-6-yl!acetate 
1.80 g (9 mmol) of ethyl (4-chloropyrimidin-6-yl)acetate, 1.40 g (9 mmol) 
of cis-4-tert-butylcyclohexylamine and 1.82 g (18 mmol) of triethylamine 
were heated at 80.degree. to 90.degree. C. for 8 hours. After cooling, the 
mixture was taken up in water/toluene and the organic phase was dried and 
concentrated. Purification was carried out by chromatography on silica gel 
(ethyl acetate) to give 1.85 g (64.4% of theory) of a colorless resin. 
Preparation of the precursor ethyl (4-chloropyrimidin-6-yl)acetate 
2.7 g (50 mmol) of sodium hydride (80% dispersion in oil) were placed in 
100 ml of dry dioxane, and 11.7 g (90 mmol) of ethyl acetoacetate were 
added dropwise. The mixture was then stirred at 50.degree. C. for 1 hour. 
After cooling to room temperature, a solution of 4.5 g (30 mmol) of 
4,6-dichloropyrimidine in 50 ml of dioxane was added dropwise. After 
heating at reflux for 6 hours the mixture was cooled to room temperature, 
10 ml of methanol were added dropwise in order to destroy superfluous 
sodium hydride, and the mixture was concentrated. The residue was taken up 
in water and brought to a pH of 3 to 4 with conc. hydrochloric acid. After 
extractive stirring with toluene, the organic phase was dried and 
concentrated. Chromatography on silica gel left 1.8 g (30% of theory) of a 
colorless oil. 
Example 39 
4-(cis-4-tert-Butylcyclohexylamino)-5-chloro-6-ethynylpyrimidine 
0.64 g (1.76 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-trimethylsilylethynylpyrimi 
dine (Example 27) was dissolved in 20 ml of tetrahydrofuran, and 2 ml of a 
1.0M solution of tetrabutylammonium fluoride in tetrahyrofuran were added 
at 0.degree. C. The mixture was stirred at room temperature for 2 hours, 
diluted with toluene and exracted by stirring with sodium hydrogen 
carbonate solution and water. The organic phase was dried and 
concentrated. Chromatography on silica gel left 0.44 g (86.0% of theory) 
of a colorless oil which gradually solidified. 
m.p.: 124.degree. to 125.degree. C. 
Example 40 
4-(cis-4-tert-Butylcyclohexylamino)-6-carbomethoxy-5-chloropyrimidine 
This compound was obtained in analogy to Example 5, from 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-iodopyrimidine (precursor 
for Example 27), in 55% yield as a colorless oil. 
Example 41 
4-(cis-4-tert-Butylcyclohexylamino)-5-chloro-6-cyanopyrimidine 
In analogy to Example 2, 3.9 g (10 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-iodopyrimidine and 1.8 g 
(20 mmol) of copper(I) cyanide gave, after chromatography on silica gel 
(petroleum ether/ethyl acetate 9:1), 0.9 g (30.8% of theory) of product as 
a colorless oil which gradually solidified. 
m.p.: 107.degree. to 108.degree. C. 
Example 42 
4-(cis-4-tert-Butylcyclohexylamino)-6-ethyl-5-fluoromethylpyrimidine 
This compound can be prepared starting from 
5-carbomethoxy-4-(cis-4-tert-butylcyclohexylamino)-6-ethylpyrimidine 
(Example 5) by reduction to the 5-hydroxymethyl compound (in analogy to 
Example 37) and fluorination with diethylaminosulfur trifluoride (DAST). 
EXAMPLES FOR PREATION PROCESS 2 
Example 43 
4-(cis-4-tert-Butylcyclohexylamino )-6-ethyl-5-trifluoromethylpyrimidine 
8.4 g of trifluoromethyl iodide and 5 g of copper powder were stirred with 
20 ml of hexamethylphosphoric triamide in a stainless steel laboratory 
autoclave (Hastelloy) at 120.degree. C. for 2.5 hours. The mixture was 
filtered with suction over Celite, under nitrogen, to remove the excess 
copper powder. 1.92 g (5 mmol) of 
4-(cis-4-tert-butyl-cyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1) 
were added in order to dissolve the trifluoromethyl-copper complex, and 
the mixture was stirred under nitrogen at 100.degree. C. for 2 hours. 
After cooling, 200 ml of diethyl ether were added, the precipitated copper 
salts were filtered off and the filtrate was extracted by stirring with 
water. The organic phase was dried and concentrated. The product was 
purified by filtration over a silica gel column (petroleum ether/ethyl 
acetate 7:3) to give 0.52 g (32% of theory) of product as a colorless oil. 
Example 43a 
4-(cis-4-tert-Butylcyclohexylamino)-6-ethyl-5-pentafluoroethylpyrimidine 
Prepared as in Example 43 from pentafluoroethyl iodide and 
4-(cis-4-tert-butylcyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1), 
colorless oil. 
Example 44 
4-(cis-4-tert-Butylcyclohexylamino)-6-ethyl-5-trifluoromethylthiopyrimidine 
1.93 g (5 mmol) of 
4-(cis-4-tert-butylcyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1) 
and 1.64 g (10 mmol) of trifluoromethylthio copper (Synthesis 1975, 721) 
were stirred in 20 ml of dimethylformamide, under nitrogen, at 150.degree. 
C. for 7 hours. After cooling, the mixture was diluted with 200 ml of 
water and subjected to extraction by stirring with ether. The organic 
phase was again washed with water, dried and concentrated. The crude 
product was purified by filtration over a silica gel column (petroleum 
ether/ethyl acetate 7:3), to give 0.59 g (33% of theory) of product as a 
colorless oil. 
Example 45 
6-Ethyl-5-methoxy-4-(cis-4-phenylcyclohexylamino)pyrimidine 
7.20 g (20 mmol) of 
5-bromo-6-ethyl-4-(cis-4-phenylcyclohexylamino)pyrimidine (DE-A-42 08 254) 
and 0.44 g (3 mmol) of copper(I) bromide were heated under reflux for 12 
hours in 10 ml of 30% methanolic sodium methylate solution, to which 0.70 
g of ethyl acetate have been added. For working up, the solvent is 
stripped off, the residue is taken up in ethyl acetate, this mixture is 
subjected to extraction by stirring with water, and the organic phase is 
dried and concentrated. For purification, the crude product is 
chromatographed on silica gel using ethyl acetate/petroleum ether (8:2). 
3.7 g (60% of theory) of a colorless oil were obtained which gradually 
solidified. 
m.p.: 79.degree. to 80.degree. C. 
Example 46 
4-(cis-4-tert-Butylcyclohexylamino)-6-ethyl-5-methoxypyrimidine 
In analogy to Example 7, 6.8 g (20 mmol) of 
5-bromo-4-(cis-4-tert-butylcyclohexylamino)-6-ethylpyrimidine and 10 ml of 
30% methanolic sodium methylate solution gave, with addition of 0.44 g of 
copper(I) bromide and 0.70 g of ethyl acetate, 1.9 g (33% of theory) of 
product as a colorless oil. 
The following compounds were also obtained in analogy to Example 44: 
Example 47 
4- (cis-4-tert-Butylcyclohexylamino)-5-ethoxy-6-ethylpyrimidine, colorless 
oil. 
Example 48 
6-Ethyl-5-methoxy-4-cis-4-(1,1,3,3-tetramethylbutyl)-cyclohexylamino!pyrim 
idine, colorless oil. 
Example 49 
6-Ethyl-5-methoxy-4-(cis-4-trimethylsilylcyclohexylamino)pyrimidine, 
colorless oil. 
Example 50 
6-Ethyl-4-(2-decylamino)-5-methoxypyrimidine, colorless oil. 
Example 51 
6-Ethyl-4-2-(2,4-dimethylphenoxy)ethylamino!-5-methoxypyrimidine 
Example 52 
6-Ethyl-5-isopropoxy-4-(cis-4-tert-butylcyclohexylamino)pyrimidine, 
colorless oil. 
Example 53 
5-Ethoxy-6-ethyl-4-(cis-4-phenylcyclohexylaminopyrimidine, colorless oil. 
Example 54 to 61 
##STR22## 
TABLE 3 
______________________________________ 
Ex. No. R.sup.1 R.sup.2 
______________________________________ 
54 --(CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.2 H.sub.5 
CH.sub.3 
55 --(CH.sub.2).sub.3 (OCH.sub.2 CH.sub.2)O.sub.2 C.sub.2 
H.sub.5 CH.sub.3 
56 --(CH.sub.2).sub.2 OC.sub.2 H.sub.5 
CH.sub.3 
57 --(CH.sub.2).sub.2 OC.sub.2 H.sub.5 
C.sub.2 H.sub.5 
58 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2 
CH.sub.3 
59 (CH.sub.2).sub.2 Si(CH.sub.3).sub.3 
CH.sub.3 
60 (CH.sub.2).sub.3 Si(CH.sub.3).sub.3 
CH.sub.3 
61 (CH.sub.2).sub.2 CH(CH.sub.3).sub.3 
CH.sub.3 
______________________________________ 
All of the examples from Table 3 were isolated as colorless oils. 
In analogy to the examples given above, it is also possible to prepare 
derivatives with different side chains X-E-Q from formula 1, for example 
with the radicals: 
cis-4-n-propylcyclohexylamino, 
cis-4-isopropylcyclohexylamino, 
cis-4-n-butylcyclohexylamino, 
cis-4-sec-butylcyclohexylamino, 
cis-4-isobutylcyclohexylamino, 
cis-4-(tert-amylcyclohexylamino, 
cis-4-n-hexylcyclohexylamino, 
cis-4-n-octylcyclohexylamino, 
cis-4-(1,1,3,3-tetramethylbutyl)cyclohexylamino, 
cis-4-(1,1,3,3-tetramethylbutyl)cyclohexyloxy, 
cis-4-cyclopentylcyclohexylamino, 
cis-4-(1-methylcyclopentyl)cyclohexylamino, 
cis-4-cyclohexylcyclohexylamino, 
cis-4-(1-methylcyclohexyl)cyclohexylamino, 
cis-4-trimethylsilylcyclohexylamino, 
cis-4-trifluoromethylcyclohexylamino, 
cis-4-phenylcyclohexylamino, 
cis-4-(4-methylphenyl)cyclohexylamino, 
cis-4-(4-ethylphenyl)cyclohexylamino, 
cis-4-(4-tert-butylphenyl)cyclohexylamino, 
cis-4-(4-trifluoromethylphenyl)cyclohexylamino, 
cis-4-(4-trimethylsilylphenyl)cyclohexylamino, 
cis-4-(4-ethynylphenyl)cyclohexylamino, 
cis-4-(4-chlorophenyl)cyclohexylamino, 
cis-4-(4-fluorophenyl)cyclohexylamino, 
cis-4-(4-methoxyphenyl)cyclohexylamino, 
cis-4-(4-ethoxyphenyl)cyclohexylamino, 
cis-4-(4-isopropoxyphenyl)cyclohexylamino, 
cis-4-(4-trifluoromethoxyphenyl)cyclohexylamino, 
cis-4-vinylcyclohexylamino, 
cis-4-phenylcyclohexyloxy, 
cis-4-benzylcyclohexylamino, 
cis-4-ethoxycyclohexylamino, 
cis-4-n-propoxycyclohexylamino, 
cis-4-isopropoxycyclohexylamino, 
cis-4-n-butoxycyclohexylamino, 
cis-4-cyclohexyloxycyclohexylamino, 
cis-4-phenoxycyclohexylamino, 
cis-4-(4-methylphenoxy)cyclohexylamino, 
4-tert-butylcycloheptylamino, 
4-phenylcycloheptylamino, 
3-ethylcyclopentylamino, 
3-tert-butylcyclopentylamino, 
3-tert-amylcyclopentylamino, 
3-phenylcyclopentylamino, 
3-tert-butylcyclobutylamino, 
3-phenylcyclobutylamino, 
(4-tert-butylcyclohex-1-yl)methylamino, 
(4-phenylcyclohex-1-yl)methylamino, 
4-tert-butoximinocyclohexylamino. 
C. BIOLOGICAL EXAMPLES 
Insecticidal Action 
Example 1: Action on the Rice Brown Planthopper 
Young rice plants (Oryza sativa) were dipped into aqueous dilutions of a 
wettable powder concentrate having a concentration of 250 ppm (based on 
active substance) and, after the drops had run off, these plants were 
populated with L4 larvae of the rice brown planthopper Nilaparvata lugens. 
After placing the treated plants in an experimental cage, they were 
observed for 3 days at 28.degree. C. and high atmospheric humidity, and 
the mortality of the test organisms was determined. 
At 250 ppm, the compounds according to Example 2, 2a, 5, 7, 7a, 8, 10, 11, 
11a, 12, 14, 18, 19, 20a, 22, 25, 29, 30, 43, 43a, 44, 45, 46, 49, 50, 51, 
55, 56, 59, 60 and 61 produced 100% mortality in the test organisms. 
Example 2: Action on Diabrotica Undecimpunctata 
Larvae (L2) of the southern corn rootworm (Diabrotica undecimpunctata) were 
placed on filter paper disks which had each been soaked with 1 ml of an 
acetone-diluted formulation of a wettable powder in a concentration of 250 
ppm based on active substance. After the acetone had evaporated, the 
dishes were sealed and stored at 28.degree. C. for 3 days, after which the 
mortality of the larvae was determined. 
100% mortality was found with the compounds according to Example 1, 2, 2a, 
7, 7a, 8, 10, 11, 11a, 12, 13, 14, 18, 19, 20a, 22, 24, 25, 29, 30, 43, 
43a, 44, 45, 46, 47, 49, 50, 53, 54, 55, 56, 57, 58, 59, 60 and 61. 
Example 3: Action on the Black Bean Aphid 
Field bean plants (Vicia faba) which were severely infested with black bean 
aphids (Aphis fabae, full population) were sprayed to the beginning of 
runoff with an aqueous preparation comprising 250 ppm of the active 
substance in question. After the plants had been grown in the greenhouse 
for 3 days, the mortality of the aphids (full population) was checked. 
100% mortality was found in the case of Examples 1, 2, 2a, 3, 5, 7, 7a, 8, 
10, 11, 11a, 11b, 12, 13, 14, 18, 19, 20a, 22, 24, 25, 43, 45, 49, 50, 51, 
53, 54, 55, 56, 57, 58, 59, 60 and 61. 
Example 4: Action on the Common Citrus Mealy Bug 
Bean plants (Phaseolus vulgaris ssp. vulgaris var. nanus) which were 
severely infested with common citrus mealy bugs (Planococcus citri, 2nd 
instar larvae) were sprayed to the beginning of runoff with an aqueous 
preparation comprising 250 ppm of the active substance in question. After 
the plants had been grown in the greenhouse for 7 days, the mortality of 
the common citrus mealy bug (full population) was checked. 100% mortality 
was found in the case of Example 2. 
Example 5: Action on the Common Housefly 
The bottom and lid of a Petri dish were coated on the inside with in each 
case 3 ml of an aqueous dilution of a wettable powder concentrate 
comprising 250 ppm of the active substance in question. After the coating 
had dried on, 24-hour-old common houseflies (Musca domestica) were placed 
in the Petri dishes, which were sealed with the treated lid. After 3 hours 
at 20.degree. C., the mortality of the flies was checked. 100% mortality 
was obtained with the compounds 1, 2, 2a, 7a, 8, 11, 11a, 11b, 12, 18, 19, 
20a, 22, 28, 43, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 56 and 61. 
Example 6: Larvae (L4) of the Cockroach, Blaberus Craniifer, were injected 
with Active Substances dissolved in Methanol 
Following application of the compounds according to Example 1, 2, 5, 7, 7a, 
8, 9, 22, 44, 45, 46, 48, 50, 51 and 53 (2.times.10.sup.-4 g a.i./animal), 
100% mortality was found after 48 hours. 
Example 7 
Larvae (L4) of the tobacco hornworm, Manduca sexta, were injected with 
active substances dissolved in acetone. 
Following application of the compound according to Example 1, 2, 5, 7, 7a, 
8, 9, 22, 44, 45, 46, 48, 50, 51 and 53 (2.times.10.sup.-4 g a.i./animal), 
100% mortality was found after 48 hours. 
Ovicidal action 
Example 8: Manduca Sexta 
Japan filter paper was used to line the inside of the bottom of Petri 
dishes, and in each case 20 1-day-old eggs of Manduca sexta were placed on 
the paper. Approximately 1 ml of an artificial insect feed diet was then 
placed in the center of the Petri dish, and the inside of the base, 
together with eggs and feed diet, was sprayed with an aqueous wettable 
powder suspension of the test products, corresponding to 600 I/ha. After 
the Petri dishes had been sealed and stored at room temperature for 5 
days, the mortality of the eggs was determined. 100% action was provided 
by the compounds of Examples 11, 11b, 12, 19, 22, 45, 46, 49, 50, 51 and 
54. 
Example 9: Action on the Eggs of the Large Milkweed Bug 
Filter paper disks supporting eggs (egg age: 2 days) of the large milkweed 
bug (Oncopeltus fasciatus) were treated with in each case 1 ml of an 
aqueous preparation comprising 250 ppm of the active substance in 
question. After the coating had dried on, the filterpaper disks were 
stored in Petri dishes at room temperature and maximum atmospheric 
humidity. After 7 days the ovicidal action was determined. 100% ovicidal 
action (egg mortality) was found in the case of Examples 8, 11, 11b, 12, 
19, 22, 45, 46, 49, 50, 51 and 53. 
Acaricidal action 
Example 10: Action on the Greenhouse Red Spider Mite 
Bean plants (Phaseolus vulgaris ssp. vulgaris var. nanus) which were 
severely infected with greenhouse red spider mites (Tetranychus urticae, 
full population) were sprayed to the beginning of runoff with an aqueous 
preparation comprising 250 ppm of the active substance in question. After 
the plants had been grown in the greenhouse for 7 days, the mortality of 
the spider mites (full population) was checked. 100% mortality was found 
in the case of Example 1, 2, 2a, 3, 7a, 8, 10, 11, 11a, 11b, 12, 13, 14, 
19, 20a, 22, 24, 29, 45, 46, 47, 48, 49, 50, 51, 54, 55, 56, 57, 58, 59, 
60 and 61. 
Example 11: Action on the Fruit Tree Red Spider Mite 
Apple plants (Malus domestics) which were severely infested with fruit tree 
red spider mites (Panonychus ulmi, full population) were sprayed to the 
beginning of runoff with an aqueous preparation comprising 250 ppm of the 
active substance in question. After the plants had been grown in the 
greenhouse for 9 days, the mortality of the fruit tree red spider mites 
(full population) was checked. 100% mortality was found in the case of 
Examples 1, 2, 11, 11a, 19, 20a, 45, 46, 48, 49, 54, 55, 56, 57, 58, 59 
and 60. 
Nematicidal action 
Example 12: Control of Root-knot Nematodes 
An aqueous preparation comprising 30 ppm of active substance is prepared in 
a glass vessel (final volume 30 ml). To this mixture are added about 5000 
freshly hatched, active (mobile) larvae (2nd instar) of root-knot 
nematodes (Meloidogyne incognita). After 48-hour exposure of the nematode 
larvae to the active substance, the percentage of individuals which have 
become motionless (immobile) by the action of said substance is determined 
in comparison with the untreated controls. 
The compounds of Examples 2, 7, 7a, 9, 10, 12, 13, 19, 22, 25, 45, 49 and 
53 showed an action of from 90 to 100% relative to the root-knot nematodes 
Meloidogyne incognita. 
Use as an antiparasitic agent 
Example 13 
In Vitro Test on Tropical Cattle Ticks (Boophilus microplus) 
The following experimental setup was used to demonstrate the activity of 
the compounds according to the invention against ticks: To prepare an 
appropriate preparation of active substance, the active substances were 
dissolved in a mixture consisting of dimethylformamide (85 g), nonylphenol 
polyglycol ether (3 g) and ethoxylated castor oil (7 g) to give a 10% 
(w/v) mixture, and the resulting emulsion concentrates were diluted with 
water to a test concentration of 500 ppm. 
Batches of ten females of the tropical tick Boophilus microplus which had 
sucked themselves full were immersed for five minutes in these active 
substance dilutions. The ticks were subsequently dried on filter paper and 
then attached by their backs to an adhesive film in order to lay eggs. The 
ticks were kept in an incubator at 28.degree. C. and an atmospheric 
humidity of 90%. 
For control purposes, female ticks were immersed in plain water. The 
activity was assessed two weeks after the treatment, on the basis of 
inhibition of oviposition. 
In this test, oviposition was inhibited to an extent of 100% by the 
compounds according to Examples 1, 2, 5, 7, 7a, 8, 11, 11a, 11b, 12, 13, 
18, 19, 20a, 22, 45, 46, 47, 49, 51, 53, 54, 55 and 56 at an active 
substance concentration of 500 ppm. 
Use as fungicide 
The activity of the preparations according to the invention was assessed in 
accordance with a scale of 0-4, where 
0=0-24% disease suppression 
1=25-49% disease suppression 
2=50-74% disease suppression 
3=75-97% disease suppression 
4=97-100% disease suppression. 
Example 14 
Barley plants of the variety "Maris Otter" at the 2-leaf stage were sprayed 
until dripping wet with a solution of the compounds according to the 
invention in a mixture of 40% acetone and 60% water. 24 hours later, the 
plants were inoculated with conidia of barley mildew (Erysiphe graminis f. 
sp. hordei) and stored in a controlled-environment cabinet at 20.degree. 
C. and a relative atmospheric humidity of 75-80%. 7 days after the 
treatment, the plants were investigated for infestation with barley 
mildew. 
The following compounds were given a rating of 3 or 4 at 500 mg of active 
substance/l of spray liquor: Compounds according to Example Nos. 20a, 45, 
48 and 60. 
Example 15 
Tomato plants of the variety "First in the Field" at the 3-4-leaf stage 
were sprayed until dripping wet with a solution of the compounds according 
to the invention in a mixture of 40% acetone and 60% water. 24 hours 
later, the plants were inoculated with a spore suspension of Phytophthora 
infestans (20,000 spores/ml) and were stored in a controlled-environment 
cabinet at 15.degree. C. first for 2 days at 99% relative atmospheric 
humidity and then for 4 days at 75-80% relative atmospheric humidity. 6 
days after the treatment, the plants were investigated for infestation 
with Phytophthora infestans. The following compounds were given a rating 
of 3 or 4 at 500 mg of active substance/I of spray liquor: Compounds 
according to Example Nos. 43a, 46, and 47. 
Example 16 
Seedlings of the vine variety "Gruner Veltliner" aged about 6 weeks were 
sprayed until dripping wet with a solution of the compounds according to 
the invention in a mixture of 40% acetone and 60% water. 24 hours later 
the plants were inoculated by spraying with a zoospore suspension 
(100,000/ml) of Plasmopara viticola and stored in a controlled-environment 
cabinet at 70.degree. C. and a relative atmospheric humidity of about 99%. 
14 days after treatment the plants were investigated for their infestation 
with Plasmopara viticola. The following compounds were given a rating of 3 
or 4 at 500 mg of active substance/l of spray liquor: Compounds according 
to Example Nos. 2, 44, 45, 47, 48, 52 and 53. 
Example 17 
Wheat plants of the variety "Hornet" at the 2-leaf stage were sprayed until 
dripping wet with a solution of the compounds according to the invention 
in a mixture of 40% acetone and 60% water. 24 hours later, the plants were 
inoculated by spraying with a pycnospore suspension (500,000/ml) of 
Leptosphaeria nodorum and stored in a controlled-environment cabinet at 
18.degree.-20.degree. C. and a relative atmospheric humidity of about 99%. 
14 days after inoculation the plants were investigated for their 
infestation with Leptosphaeria nodorum. The following compounds were given 
a rating of 3 or 4 at 500 mg of active substance/l of spray liquor: 
Compounds according to Example Nos. 3 and 49. 
Example 18 
Rice plants of the variety "Nihonbare" at the 1.5-leaf stage were sprayed 
until dripping wet with a solution of the compounds according to the 
invention in a mixture of 40% acetone and 60% water. At the same time, the 
plants were watered with a solution of the substances in a mixture of 5% 
acetone and 95% water. 24 hours later, the plants were inoculated by 
spraying with a pycnospore suspension (10.sup.6 /ml) of Pyricularia 
oryzae. The plants were stored for 2 days in a darkened 
controlled-environment cabinet at 26.degree. C. and a relative atmospheric 
humidity of 99% and then transferred to an illuminated 
controlled-environment cabinet at about 18.degree. C. and a relative 
atmospheric humidity of 75-80%. 7-9 days after inoculation the plants were 
investigated for their infestation with Pyricularia oryzae. The following 
substances were given a rating of 3 or 4 at 500 mg of active substance/l 
of spray liquor: Compounds according to Example Nos. 47 and 53. 
Example 19 
Apple seedlings (Malus sp.) aged about 3 weeks were sprayed until dripping 
wet with a solution of the compounds according to the invention in a 
mixture of 40% acetone and 60% water. After 24 hours the plants were 
inoculated by spraying with a spore suspension (300,000/ml) of Venturia 
inaequalis. The plants were stored for 2 days in the dark at 
18.degree.-20.degree. C. and a relative atmospheric humidity of 99% and 
then in the light for 5 days at the same atmospheric humidity, and finally 
for 7 days at 75-80% atmospheric humidity. 14 days after treatment the 
plants were investigated for their infestation with Venturia inaequalis. 
The following substances were given a rating of 3 or 4 at 500 mg of active 
substance/l of spray liquor: Compounds according to Example Nos. 46 and 
48.