Fungicidal aza-heterocycloalkenes

Details Fungicidal aza-heterocycloalkenes Fungicidal aza-heterocycloalkenes

2000-10-31

2002-06-18

Kifle, Bruck (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C544S003000

Reexamination Certificate

active

06407098

ABSTRACT:

The invention relates to novel substituted heterocycloalkenes, to a number of processes for their preparation and to their use as fungicides, and to novel intermediates and to a number of processes for their preparation.
It is known that certain substituted heterocyclic compounds possess fungicidal properties (cf. e.g. WO-A 9422844). However, the action of these compounds, especially at low application rates, is not entirely satisfactory in all areas of application.
The novel substituted heterocycloalkenes have now been found of the general formula (I)
in which
A represents optionally substituted alkylene,
Ar represents optionally substituted arylene or heteroarylene,
E represents a 1-alkene-1,1-diyl grouping which in position 2 contains a radical R
1
, or represents a 2-aza-1-alkene-1,1-diyl grouping which in position 2 contains a radical R
2
, or represents an optionally substituted imino grouping (“azamethylene”, N—R
3
), or represents a 3-aza-1-propene-2,3-diyl grouping which contains in position 1 a radical R
1
and in position 3 a radical R
3
, or represents a 3-oxa-1-propene-2,3-diyl grouping which contains in position 1 a radical R
1
, or represents a 3-thia-1-propene-2,3-diyl grouping which contains in position 1 a radical R
1
, or represents a 1-aza-1-propene-2,3-diyl grouping which contains in position 1 a radical R
2
and in position 3 a radical R
3
, or represents a 1-aza-1-propene-2,3-diyl grouping which contains in position 1 a radical R
1
and in position 3 a radical R
3
, or represents a 1,3-diaza-1-propene-2,3-diyl grouping which contains in position 1 a radical R
2
and in position 3 a radical R
3
or represents a 1-aza-3-oxa-1-propene-2,3-diyl grouping which contains in position 1 a radical R
2
, or represents a 1-aza-3-thia-1-propene-2,3-diyl grouping which contains in position 1 a radical R
2
, where
R
1
represents hydrogen, halogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R
2
represents hydrogen, amino, hydroxyl, cyano or in each case optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
R
3
represents hydrogen, cyano, hydroxyl or in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylalkyl,
G represents a single bond, oxygen, sulphur or represents alkanediyl, alkenediyl or alkinediyl each of which is optionally substituted by halogen, hydroxyl, alkyl, halogenoalkyl or cycloalkyl, or represents one of the following groupings —Q—CQ—, —CQ—Q—, —CH
2
—Q—; —Q—CH
2
—, —CQ—Q—CH
2
—, —CH
2
—Q—CQ—, —Q—CQ—CH
2
—, —Q—CQ—Q—CH
2
—, —N═N—, —S(O)
n
—, —CH
2
—S(O)
n
—, —CQ—, —S(O)
n
—CH
2
—, —C(R
4
)═N—O—, —C(R
4
)═N—O—CH
2
—, —N(R
5
)—, —CQ—N(R
5
)—, —N(R
5
)—CQ—, —Q—CQ—N(R
5
)—, —N═C(R
4
)—Q—CH
2
—, —CH
2
—O—N═C(R
4
)—, —N(R
5
)—CQ—, —Q—, —CQ—N(R
5
)—CQ—Q—, —N(R
5
)—CQ—Q—CH
2
—, —Q—C(R
4
)═N—O—CH
2
—, —N(R
5
)—C(R
4
)═N—O—CH
2
—, —O—CH
2
—C(R
4
)═N—O—CH
2
—, —N═N—C(R
4
)═N—O—CH
2
—, —T—Ar
1
— or —T—Ar
1
—Q—, where
Ar
1
represents optionally substituted arylene, heteroarylene, cycloalkylene, or heterocycloalkylene (i.e. a divalent aliphatic ring in which one or more carbon atoms are replaced by heteroatoms, i.e. atoms other than carbons.
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulphur,
R
4
represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R
5
represents hydrogen, hydroxyl, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl, and
T represents a single bond, oxygen, sulphur, —CH
2
—O—, —CH
2
—S— or optionally substituted alkanediyl,
Y
1
represents oxygen, sulphur, or an optionally alkyl-substituted imino grouping (“azamethylene”, NH, N-alkyl),
Y
2
represents oxygen, or an optionally alkyl-substituted imino grouping (“azamethylene”, NH, N-alkyl),
where Y
1
and Y
2
do not simultaneously represent oxygen, and
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, for example phenyl, naphthyl, anthryl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.
Heterocyclyl represents saturated or unsaturated, and aromatic, cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom other than carbon. If the ring comprises two or more heteroatoms, they can be identical or different. Heteroatoms are preferably oxygen, nitrogen or sulphur. The cyclic compounds may form a polycyclic ring system together with further carbocyclic or heterocyclic, fused-on or bridge-connected rings. Preferred systems are mono- or bicyclic ring systems, especially mono- or bicyclic aromatic ring systems.
It has also been found that the novel substituted heterocycloalkenes of the general formula (I) are obtained if
a) hydroxyl compounds of the general formula (II)
 in which
A, Ar, E, G and Z have the meaning given above and where
Y
3
represents oxygen, sulphur or an optionally alkyl-substituted imino grouping (“azamethylene”, NH, N-alkyl), and
Y
4
represents oxygen, or an optionally alkyl-substituted imino grouping (“azamethylene”, NH, N-alkyl),
 are reacted with a sulphurizing reagent and/or a condensing agent, optionally in the presence of a diluent,
 or if
b) nitrogen-containing carboxylic acid derivatives of the general formula (III)
 in which
A, Ar, E, G, Y
1
, Y
2
and Z have the meaning given above, and
X
1
represents halogen, arylsulfonyl or alkylsulfonyl
 are reacted with an acid acceptor, optionally in the presence of a diluent.
Finally it has been found that the novel substituted heterocycloalkenes of the general formula (I) show a very strong fungicidal action.
The compounds according to the invention can if appropriate be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z isomers, if appropriate also of tautomers. The claimed subject-matter comprises both the E isomers and the Z isomers, any desired mixtures of these isomers, and the possible tautomeric forms.
The invention preferably provides compounds of the formula (I) in which
A represents alkylene having 1 to 4 carbon atoms,
Ar represents in each case optionally substituted phenylene or naphthylene, or represents mono- or bicyclic heteroarylene having in each case 5 or 6 ring members, or represents benzo-fused heteroarylene having 5 or 6 ring members of which in each case at least one represents oxygen, sulphur or nitrogen and optionally one or two others represent nitrogen, the possible substituents preferably being selected from the following list:
Halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms, in each case straight-chain or branched alkenyl, alkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxyiminoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, in each case divalent alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being in each case optionally substituted by one or more identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
E

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