Substituted heterocyclic compounds and their use as fungicides

Details Substituted heterocyclic compounds and their use as fungicides Substituted heterocyclic compounds and their use as fungicides

1997-08-04

2001-01-23

Morris, Patricia L. (Department: 1612)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C549S491000

Reexamination Certificate

active

06177459

ABSTRACT:

The invention relates to novel substituted heterocyclic compounds, to a plurality of processes for their preparation and to their use as fungicides, and to novel intermediates, to a plurality of processes for their preparation and to their use as fungicides.
Certain substituted heterocyclic compounds are known to have fungicidal properties (cf. EP-A 633252 and WO-A 9422844). However, the activity of these compounds, in particular at low application rates, is not entirely satisfactory in all areas of application.
This invention, accordingly, provides the novel substituted heterocyclic compounds of the general formula (I)
in which
Ar represents optionally substituted arylene or heteroarylene,
E represents a 1-alkene-1,1-diyl grouping which contains a radical R
1
in position 2, or represents a 2-aza-1-alkene-1,1-diyl grouping which contains a radical R
2
in position 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 a radical R
1
in position 1 and a radical R
3
in position 3, or represents a 3-oza-1-propene-2,3-diyl grouping which contains a radical R
1
in position 1, or represents a 3-thia-1-propene-2,3-diyl grouping which contains a radical R
1
in position 1, or represents a 1-aza-1-propene-2,3-diyl grouping which contains a radical R
2
in position 1 and a radical R
3
in position 3, or represents a 1-aza-1-propene-2,3-diyl grouping which contains a radical R′ in position 1 and a radical R
3
in position 3, or represents a 1,3-diaza-1-propene-2,3-diyl grouping which contains a radical R
2
in position 1 and a radical R
3
in position 3, or represents a 1-aza-3-oxa-1-propene-2,3-diyl grouping which contains a radical R
2
in position 1, or represents a 1-aza-3-thia-1-propene-2,3-diyl grouping which contains a radical R
2
in position 1, where
R
1
represents hydrogen, halogen, cyano or represents respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R
2
represents hydrogen, amino, hydroxyl, cyano or represents respectively optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
R
3
represents hydrogen, cyano, hydroxyl or represents respectively optionally substituted alkyl, alkoxy, alkoxyalkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylalkyl,
G represents a single bond, represents oxygen or sulphur or represents respectively optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl, alkenediyl, alkinediyl or one of the groupings below —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. an aliphatic ring which is attached twice and where one or more carbon atoms are replaced by hetero atoms, i.e. atoms that differ from carbon),
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulphur,
R
4
represents hydrogen, cyano or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R
5
represents hydrogen, hydroxyl, cyano or respectively optionally substituted alkyl, alkoxy or cycloalkyl and
T represents a single bond, represents oxygen, sulphur, —CH
2
—O—, —CH
2
—S— or represents optionally substituted alkanediyl and
R represents pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl or tetrazolyl, each of which is attached via a carbon atom and each of which is optionally alkyl-substituted at a nitrogen atom,
represents 1,2,5-oxadiazolyl, furyl, thienyl, 1,2-thiazolyl, 1,3-thiazolyl, 4-oxo-1,3-thiazol-2-yl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, 1,2,3-triazyl, 1,2,4-triazyl, 1,3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl, each of which is attached via a carbon atom and each of which is optionally substituted,
represents respectively optionally substituted saturated heterocyclyl having at least one oxygen and/or at least one sulphur atom,
or represents optionally substituted 1,3-diazacycloalk-1-en-2-yl,
Z represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
Aryl represents aromatic mono- or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Unless otherwise defined, heterocyclyl represents saturated or unsaturated, and aromatic, compounds in the form of a ring in which at least one ring member is a hetero atom, i.e. an atom different from carbon. If the ring contains more than one hetero atom, these may be identical or different. Preferred hetero atoms are oxygen, nitrogen and sulphur. Optionally, the compounds in the form of a ring may form a polycyclic ring system together with other carbocyclic or heterocyclic fused or bridged rings. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Furthermore, it has been found that the novel substituted heterocyclic compounds of the general formula (I) are obtained when
a) ketones of the general formula (II)
in which
Ar, G, R and Z are each as defined above are reacted with an amine of the formula (III)
R
2
—NH2  (III)
in which
R
2
is as defined above, or an acid addition complex thereof, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary,
or
b) nitriles of the general formula (IV)
in which
Ar, E, G and Z are each as defined above are reacted with a bifunctional alkylene compound of the general formula (V)
R
6
—A—R
7
  (V)
in which
A represents optionally substituted alkylene,
R
6
represents amino or —SH,
R
7
represents amino, —COOR
8
or —CH(OR
9
)
2
where
R
8
represents alkyl or hydrogen and
R
9
represents alkyl,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary,
or
c) ketones of the general formula (II)
in which
Ar, G, R and Z are each as defined above
are reacted with phosphorus compounds of the general formula (VI)
{circle around (p)}—R
1
  (VI)
in which
R
1
is as defined above and
{circle around (p)} represents —P(R
10
)
3
+
X
−
or represents —PO(OR
11
)
2
where
R
10
represents aryl or alkyl,
R
11
represents alkyl and
X represents halogen,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary,
or
d) thioamides of the general formula (VII)
in which
Ar, G, E and Z are each as defined above
are reacted with halogenoalkyl compounds of the general formula (VIII)
in which
R
12
represents hydrogen or alkyl,
X
1
represents halogen,
Y
1
represents cyano, alkylcarbonyl, arylcarbonyl, formyl, dialkoxyalkyl or alkoxycarbonyl,
or with acetylene compounds of the formula (IX)
in which
Y
2
represents alkoxycarbonyl and
Y
3
represents hydrogen, alkyl, aryl, alkylcarbonyl, arylcarbonyl or alkoxycarbonyl,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.
If R
2
represents alkoxy, it is advantageous in some cases to prepare initially the corresponding hydroxy compounds (R
2
=OH) by the method of process a) and to alkylate these compounds subsequently by conventional methods.
Finally, it has been found that the novel substituted heterocyclic compounds of the general formula (I) have a very strong fungicidal activity.
The compounds according to the invention may be present as mixtures of various possible isomeric fo

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