Substituted azadioxacycloalkenes and their use as fungicides

Details Substituted azadioxacycloalkenes and their use as fungicides Substituted azadioxacycloalkenes and their use as fungicides

1996-02-05

1997-10-21

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

544 65, 540544, 548124, A61K 31535, C07D27300

Patent

active

056796765

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 or PCT/EP94/02533 filed Jul. 29, 1994.
The invention relates to novel substituted azadioxacycloalkenes, to a process for their preparation, and to their use as fungicides.
It has been disclosed that certain substituted 5,6-di-hydro-1,4,2-dioxazines have fungicidal properties (cf. JP-A 01221371--cited in Chem. Abstracts 112: 98566t; JP 02001484--cited in Chem. Abstracts 113: 6381y).
However, these compounds have not gained particular importance.
The new substituted azadioxacycloalkenes of the general formula (I) ##STR2## have now been found, in which
A represents optionally substituted alkanediyl (alkylene),
Ar represents in each case optionally substituted arylene or heteroarylene,
E represents a 1-alkene-1,1-diyl group with a radical R.sup.1 in the 2-position, or a 2-aza-1-alkene-1,1-diyl group with a radical R.sup.2 in the 2-position, or a 3-oxa- or 3-thia-1-propene-2,3-diyl group with a radical R.sup.1 in the 1-position,
or represents a 3-aza-1-propene-2,3-diyl group with a radical R in the 3-position and a radical R.sup.1 in the 1-position, or represents a 1-aza-1-propene-2,3-diyl group with a radical R.sup.2 in the 1-position, or represents a 3-oxa- or 3-thia-1-aza-propene-2,3-diyl group with a radical R.sup.2 in the 1-position, or represents a 1,3-diaza-1-propene-2,3-diyl group with a radical R in the 3-position and a radical R.sup.2 in the 1-position, or represents an optionally substituted imino group ("azamethylene", N--R.sup.3),
R represents alkyl,
R.sup.1 represents hydrogen, halogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R.sup.2 represents hydrogen, amino, cyano or in each case optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
R.sup.3 represents hydrogen, cyano or in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylalkyl,
G represents a single bond, oxygen, or represents alkanediyl, alkenediyl, oxaalkenediyl, alkinediyl, each of which is optionally substituted by halogen, hydroxyl, alkyl, halogenoalkyl or cycloalkyl, or represents one of the groups below
--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--, --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 --, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, --S(O).sub.n --CH.sub.2 --, --C(R.sup.4).dbd.N--O--, --C(R.sup.4).dbd.N--O--CH.sub.2 --, --N(R.sup.5)--, --CQ--N(R.sup.5)--, --N(R.sup.5)--CQ--, --Q--CQ--N(R.sup.5)--, --N.dbd.C(R.sup.4)--Q--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.4)--, --N(R.sup.5)--CQ--Q--, --CQ--N(R.sup.5)--CQ--Q--, --N(R.sup.5)--CQ--Q--CH.sub.2 --, --CQ--CH.sub.2 -- or --N.dbd.N--C(R.sup.4).dbd.N--O--,
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulphur,
R.sup.4 represents hydrogen, cyano, or represents alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, each of which is optionally substituted, and
R.sup.5 represents hydrogen, hydroxyl, cyano, or represents alkyl, alkoxy or cycloalkyl, each of which is optionally substituted, and
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
Furthermore, it has been found that the new substituted azadioxacycloalkenes of the general formula (I) are obtained when
(a) carboxylic acid derivatives of the general formula (II) ##STR3## in which
Ar, E, G and Z have the abovementioned meaning and
R represents alkyl
are reacted, in a first step, with hydroxylamine or with a hydrohalide thereof, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, and the product of the first step is reacted in situ, i.e. without intermediate isolation, in a second step with disubstituted alkanes of the general formula (III),
A has the abovementioned meaning and
X represents halogen; alkylsulphonyloxy or arylsulphonyloxy,
if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or when,
(b) in the event that, in formula (I), G represents

Affiliated with

Also associated with

Rating

Substituted azadioxacycloalkenes and their use as fungicides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Substituted azadioxacycloalkenes and their use as fungicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted azadioxacycloalkenes and their use as fungicides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1006945