Heterocyclic imino derivatives

Details Heterocyclic imino derivatives Heterocyclic imino derivatives

1996-11-27

1999-07-13

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548194, 548193, 548195, 548233, 548236, 540544, 540596, 544 63, 504219, 504261, 504266, 504270, 504223, C07D20722, C07D26316, C07D27718, A61K 3140

Patent

active

059228814

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel heterocyclic imino derivatives, several processes for preparing them and their use for controlling pests.
It is known that various substituted alkoximino- and alkoxymethyleneacetamides have fungicidal properties (compare, for example, EP-A 398 692, EP-A 468 775, DE-A 40 30 038 and WO-A 92/13 830).
However, the efficacy of these previously disclosed compounds is not entirely satisfactory in all areas of application, especially at low application rates.
Novel heterocyclic imino derivatives of the general formula (I) ##STR1## in which
A represents oxygen, sulphur or the CH.sub.2 group,
B represents the CH.sub.2 or the CH.sub.2 CH.sub.2 group,
X represents the groups .dbd.CHR.sup.1 or .dbd.NR.sup.2, where which is in each case optionally substituted by halogen, cyano or alkoxy, and dialkylamino, which is in each case optionally substituted by halogen, cyano or alkoxy,
Y represents the groups --CO-alkyl, --COOalkyl, --CO--NHalkyl, --CO--N(alkyl).sub.2, --CONR.sup.3 --OR.sup.4 and ##STR2## where
R.sup.3 represents hydrogen or alkyl,
R.sup.4 represents hydrogen or a group which can easily be eliminated, and
D represents optionally substituted alkanediyl,
Z represents a direct linkage; represents in each case optionally substituted alkylene, alkenylene and alkinylene, and represents the groups --(CHR.sup.5).sub.n --O--, --(CHR.sup.5).sub.n --S--, --(CHR.sup.5).sub.n --NH--, --(CHR.sup.5).sub.n --NR.sup.6 --, --(CHR.sup.5).sub.n --SO--, --(CHR.sup.5).sub.n --SO.sub.2 --, --(CHR.sup.5).sub.n --O--SO--, --(CHR.sup.5).sub.n --SO--O--, --(CHR.sup.5).sub.n --O--SO.sub.2, --(CHR.sup.5).sub.n --SO.sub.2 --O--, --(CHR.sup.5).sub.n --CO--, --(CHR.sup.5).sub.n --CO--O--, --(CHR.sup.5).sub.n --O--CO--, --(CHR.sup.5).sub.n --CR.sup.6 .dbd.N--O--, --(CHR.sup.5).sub.n --CR.sup.6 .dbd.N--N.dbd.CR.sup.7 --, --(CHR.sup.5).sub.n --N.dbd.CR.sup.7 --, --(CHR.sup.5).sub.n --O--N.dbd.CR.sup.7 --, where
n represents the numbers 0, 1, 2, 3 or 4, where the radicals R.sup.5 can be different when n is greater than 1; and hydrogen, cyano and represent in each case optionally substituted alkyl, alkenyl, alkinyl or aryl; and
R represents hydrogen; halogen; represents in each case optionally substituted alkyl, alkenyl or alkinyl; and represents in each case optionally substituted cycloalkyl, cycloalkenyl, cycloalkinyl, heterocyclyl, aryl, heteroaryl, --(CHR.sup.5).sub.m -cycloalkyl, --(CHR.sup.5).sub.m -cycloalkenyl, --(CHR.sup.5).sub.m -cycloalkinyl, --(CHR.sup.5).sub.m -heterocyclyl, --(CHR.sup.5).sub.m -aryl, --(CHR.sup.5).sub.m -heteroaryl, --(CHR.sup.5).sub.m --O-cycloalkyl, --(CHR.sup.5).sub.m --O-cycloalkenyl, --(CHR.sup.5).sub.m --O-cycloalkinyl, --(CHR.sup.5).sub.m --O-heterocyclyl, --(CHR.sup.5).sub.m --O-aryl, --(CHR.sup.5).sub.m --O-heteroaryl, --(CHR.sup.5).sub.m --S-cycloalkyl, --(CHR.sup.5).sub.m --S-cycloalkenyl, --(CHR.sup.5).sub.m --S-cycloalkinyl, --(CHR.sup.5).sub.m --S-heterocyclyl, --(CHR.sup.5).sub.m --S-aryl, --(CHR.sup.5).sub.m --S-heteroaryl, --(CHR.sup.5).sub.m --NH-cycloalkyl, --(CHR.sup.5).sub.m --NH-cycloalkenyl, --(CHR.sup.5).sub.m --NH-cycloalkinyl, --(CHR.sup.5).sub.m --NH-heterocyclyl, --(CHR.sup.5).sub.m --NH-aryl, --(CHR.sup.5).sub.m --NH-heteroaryl, --(CHR.sup.5).sub.m --NR.sup.6 -cycloalkyl, --(CHR.sup.5).sub.m --NR.sup.6 -cycloalkenyl, --(CHR.sup.5).sub.m --NR.sup.6 -cycloalkinyl, --(CHR.sup.5).sub.m --NR.sup.6 -heterocyclyl, --(CHR.sup.5).sub.m --NR.sup.6 -aryl, --(CHR.sup.5).sub.m --NR.sup.6 -heteroaryl, where different when m is greater than 1,
It has furthermore been found that the novel heterocyclic imino derivatives of the formula (I) are obtained when
a) heterocyclic keto derivatives of the general formula (II) ##STR3## in which A, B, X and Y have the abovementioned meaning, aid; or
b) heterocyclic keto derivatives of the general formula (II) ##STR4## in which A, B, X and Y have the abovementioned meaning,
c) heterocyclic imino derivatives of the general formula (V) ##STR5## in which A, B, X and Y have the abovementioned meaning, aid; or
d) heterocyclic imino derivative

REFERENCES:
patent: 5663185 (1997-09-01), Mueller et al.
Farag et al. J. Pharm. Sci. 66, 423 (Mar. 1977).

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