Novel insecticidally active heterocyclic compounds of the formula ##STR1## wherein W represents a substituted pyridyl group, or a 5- or 6-membered optionally substituted heterocyclic group containing at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms, R represents a hydrogen atom or an alkyl group, Y represents =N-- or ##STR2## R' represents a hydrogen atom, an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group or a cyano group, Z represents a nitro group or a cyano group, and T represents 3 or 4 optionally substituted ring members of a 5- or 6-membered unsaturated heterocyclic ring which it forms together with the adjoining carbon atom and nitrogen atom, said 5- or 6-membered unsaturated heterocyclic ring containing 1 to 3 hetero atoms which are selected from oxygen, sulfur and nitrogen atoms and at least one of which is a nitrogen atom.
This is a division of application Ser. No. 243,545, filed Sept. 13, 1988, now U.S. Pat. No. 4,882,344 issued 11/21/89 which is a division of Ser. No. 088,932 filed Aug. 24, 1987 now U.S. Pat. No. 4,803,277 issued 2/7/89.
The present application relates to a process for preparing compounds of the formula (I) ##STR1## in which R.sup.1, A, X and Z are each as defined in the description by reacting compounds of the formula (II) ##STR2## in which A and X are each as defined in the description with compounds of the formula (III) ##STR3## in which Z, R.sup.1 and M.sup.1 are each as defined in the description.
The present application relates to novel guanidine derivatives of the formula (I) ##STR1## in which R.sup.1 represents a five- or six-membered heterocyclic group; R.sup.2 represents hydrogen or alkyl, R.sup.3 represents the groupings --OR.sup.4, --OCOR.sup.5, --OCOOR.sup.6, --OCONR.sup.7 R.sup.8 and --OSO.sub.2 R.sup.9, where R.sup.4, R.sup.5 and R.sup.6 independently of one another represent alkyl, alkoxyalkyl, halogenoalkyl, alkenyl, alkinyl, alkylaminoalkyl, dialkylaminoalkyl, optionally substituted cycloalkyl and in each case optionally substituted phenyl or benzyl, R.sup.7 and R.sup.8 independently of one another represent hydrogen, alkyl, alkenyl and in each case optionally substituted phenyl or benzyl and R.sup.9 represents alkyl or optionally substituted phenyl, A represents the groupings --CH.sub.2 CH.sub.2 --, (CH.sub.2).sub.3 and --CH.dbd.CH-- and z represents cyano or nitro, with the proviso that, if Z represents NO.sub.2 and A represents --CH.sub.2 CH.sub.2 --, the radical R.sup.2 represents hydrogen; and the compound of the formula (I) in which R.sup.1 ##STR2## R.sup.2 H, R.sup.3 OCH.sub.3, A --CH.sub.2 CH.sub.2 -- and Z NO.sub.2 is excluded. The compounds serve for controlling insects, arachnids and nematodes.
Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl; Q is a linkage group of the formula --CHR.sup.2 -- or --CHR.sup.3 --CHR.sup.4 --where R.sup.2 is hydrogen or alkyl, R.sup.3 is hydrogen or alkyl, and R.sup.4 is hydrogen or alkyl; X is nitrogen or .dbd.CH--; and Z is halogen, show insecticidal activity. Also disclosed are the processes for producing the compounds and methods of using them as insecticides.
