US 5,691,321 A · Heterocyclylamino-and heterocyclyloxy-cycloalkyl derivatives, their preparation, and their use as pesticides and fungicides

Abstract

Heterocyclylamino- and heterocyclyloxy-cycloalkyl derivatives, their preparation, and their use as pesticides and fungicides ##STR1## in which Ar is optionally substituted 4-pyridyl or 4-pyrimidinyl; X is NH, O or S; E is a bond or alkanediyl; n is 2-7; R.sup.4 is H or alkyl, Y is O or a bond; and Ac is acyl, and salts thereof. The invention furthermore relates to processes for their preparation, to compositions comprising them, and to their use as pesticides and fungicides.

A compound of the formula I ##STR39## 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 in each case 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.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)-hydroxyalkayl, (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,1 thiocyano, (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)-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)-haloalkaylsulfinyl, (C.sub.1 -C.sub.4)-alkylsulfonyl or (C.sub.1 -C.sub.4)-haloalkylsulfony;
X is NH, oxygen or sulfur;
E is a direct bond or a straight-chain or branched (C.sub.1 -C.sub.4)-alkanediyl group;
n is an integer from 2 to 7;
R.sup.4 is hydrogen or (C.sub.1 -C.sub.4)-alkyl;
Y is oxygen or a direct bond;
W is oxygen or sulfur;
Z is a radical DR.sup.5 or NR.sup.5 R.sup.6 ;
D is oxygen, sulfur or a direct bond;
R.sup.5 and R.sup.6 are identical or different and are hydrogen, hydroxyl, cyano, thiocyano, nito, halogen alkyl, alkenyl, alkynyl, aryl or heterocyclyl, it being possible for the aryl or heterocyclyl radicals mentioned to be unsubstituted or to have attached to them up to three, in the case of fluorine also up to the maximum number of, identical or different radicals and it being possible for one or more nonadjacent saturated carbon units in the abovementioned alkyl, alkenyl or alkynyl radicals to be replaced by a carbonyl group or by hetero atom units, S(O).sub.x, where x=0, 1 or 2, NR.sup.9 or SiR.sup.7 R.sup.8, R.sup.9 being 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 being (C.sub.1 -C.sub.4)-alkyl;
and in which moreover 3 to 12 atoms of these hydrocarbon radicals which are optionally modified as above can form a cycle and it is possible for these hydrocarbon radicals, with or without the abovementioned variations, to be optionally substituted by one or more in the case of fluorine up to the maximum number of, identical or different radicals selected from the series consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclythio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoqloxy, aroyloxy, arylakanoyloxy, heterocyclylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, it being possible for the cycloaliphatic, aromatic or heterocyclic ring systems amongst the substituents which have just been mentioned to be unsubstituted or to have attached to them up to three, in the case of fluorine also up to the maximum number of, identical or different substituents,
R.sup.5 and R.sup.6 form a ring system of the formula II or III ##STR40## in which the six-membered ring Q' is saturated or aromatic;
m is an integer from 2 to 7;
q and r are zero or integers whose total is a number from 2 to 4 and in which one CH.sub.2 unit is optionally replaced by oxygen, sulfur or a group NR.sup.8, and
R.sup.7 and R.sup.8 are identical or different and are in each case hydrogen, alkyl, haloalkyl, alkoxy, alkylthio, phenylalkyl or phenyl and the phenyl groups can be unsubstituted or have attached to them up to three, in the case of fluorine also up to the maximum number of, identical or different substituents,
wherein a heterocyclyl is a heteroaromatic or heteroaliphatic ring system, a heteroaromatic ring system is a (C.sub.6 -C.sub.14)-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, a heteroaliphatic ring system is (C.sub.3 -C.sub.8)-cycloalkyl in which at least one carbon unit is replaced by O, S or NR.sup.11, and
R.sup.11 is (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.6 -C.sub.14)-aryl,
or salts thereof.

15 more elements

Heterocyclylamino-and heterocyclyloxy-cycloalkyl derivatives, their preparation, and their use as pesticides and fungicides

Life of this patent

Heterocyclylamino-and heterocyclyloxy-cycloalkyl derivatives, their preparation, and their use as pesticides and fungicides

Life of this patent

Abstract

Claims16