Substituted cycloalkenes and their use as microbices,...

Details Substituted cycloalkenes and their use as microbices,... Substituted cycloalkenes and their use as microbices,...

2000-01-14

2002-08-20

Raymond, Richard L. (Department: 1624)

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

active

06437127

ABSTRACT:

The invention relates to novel substituted cycloalkenes, to a plurality of processes for their preparation, and to novel intermediates and a plurality of processes for their preparation.
Certain substituted cycloalkenes are known to have fungicidal properties [cf. for example EP-A 421102].
However, in many cases the activity of these compounds is unsatisfactory.
This invention, accordingly, provides the novel substituted cycloalkenes of the general formula (I)
in which
E represents methylidene or nitrogen,
G represents a single bond, represents oxygen, sulphur, or represents respectively optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl or alkynediyl 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
1
)═N—O—, —C(R
1
)═N—O—CH
2
—, —N(R
2
)—, —CQ—N(R
2
)—, —N(R
2
)—CQ—, —Q—CQ—N(R
2
)—, —N═C(R
1
)—Q—CH
2
—, —N(R
2
)—CQ—Q—, —CQ—N(R
2
)—CQ—Q—, —N(R
2
)—CQ—Q—CH
2
—, —Q—C(R
1
)═N—O—CH
2
—, —N(R
2
)—C(R
1
)═N—O—CH
2
—, —O—CH
2
—C(R
1
)═N—O—CH
2
—, —N═N—C(R
1
)═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 doubly attached and in which one or more carbon atoms are replaced by hetero atoms, i.e. atoms other than carbon),
n represents the number 0, 1 or 2,
Q represents oxygen or sulphur,
R
1
represents hydrogen, cyano or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R
2
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,
m represents 0, 1 or 2,
R represents alkyl, alkoxy, amino, hydroxylamino, alkoxyamino, alkylamino or dialkylamino.
Y represents methylene, oxygen, sulphur, or an optionally alkyl-substituted imino grouping (“azamethylene”, NH, N-alkyl) and
Z represents respectively optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl, where, if
E represents nitrogen, G may also represent optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkenediyl or —CH
2
—O—N═C(R
1
)—.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
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 other than carbon. If the ring contains more than one hetero atom, these may be identical or different. Preferred hetero atoms are oxygen, nitrogen or sulphur. 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 was found that the novel substituted cycloalkenes of the general formula (I) are obtained when
a) keto compounds of the general formula (II)
in which
m, G, R, Y and Z are each as defined above are reacted with methoxyamine (O-methylhydroxylamine) or acid adducts thereof, or with a methoxymethyltriphenylphosphonium halide,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
where, if E represents nitrogen, it may in some cases be advantageous first to react the keto compounds of the general formula (II) with hydroxylamine or acid adducts thereof to give the corresponding oximes by the method of process a), and then to methylate these by conventional methods, or
b) halogen compounds of the general formula (III)
in which
m, E, R and Y are each as defined above and
X
1
represents halogen, preferably chlorine or bromine
are reacted with a hydroxyl or mercapto compound of the general formula (IV), (V) or (VI)
in which
R
2
and Z are each as defined above and
Q
1
represents oxygen or sulphur,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or
c) phosphorus compounds of the general formula (VII)
in which
m, R and Y are each as defined above,
E represents nitrogen,
{circle around (P)}
represents —P(R
3
)
3
+
X
−
or represents —PO(OR
4
)
2
,
R
3
represents aryl or alkyl,
R
4
represents alkyl and
X represents halogen
are reacted with a keto compound of the general formula (VIII)
in which
Z is as defined above and
R
5
represents hydrogen, alkyl or cycloalkyl,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, or
d) keto compounds of the general formula (IX)
in which
E, m, Y and R are each as defined above
are reacted with halogen compounds of the general formula (X)
Z—A
1
—X
2
  (X)
in which
A
1
represents a single bond, —T—Ar
1
— or —CH
2
— and
T, Ar
1
and Z are each as defined above and
X
2
represents halogen or alkylsulphonyl,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or
e) halogen compounds of the general formula (XI)
in which
m, Ar
1
, E, R and Y are each as defined above and
X
3
represents halogen or alkylsulphonyl
are reacted with hydroxyl or mercapto compounds of the general formula (IV)
Z—Q
1
—H  (IV)
in which
Q
1
and Z are each as defined above,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or
f) esters of the general formula (XII)
in which
m, G, Y and Z are each as defined above and
R
6
represents alkyl
are reacted with an amine of the general formula (XIII)
in which
R
7
represents hydrogen, hydroxyl or represents respectively optionally substituted alkyl or alkoxy and
R
8
represents hydrogen or represents optionally substituted alkyl,
or an acid addition complex thereof,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent or
g) amides of the general formula (XIV)
in which
E, G, m, Y and Z are each as defined above,
are reacted with an alkylating agent of the general formula (XIII)
R
9
—X
4
  (XIII)
in which
R
9
represents alkyl,
X
4
represents halogen or —O—SO
2
—R
10
and
R
10
represents —O—R
9
, alkyl or optionally substituted aryl,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
Finally, it was found that the novel substituted cycloalkenes of the general formula (I) have very strong fungicidal action.
The compounds according to the invention, like the intermediates according to the invention, may be present as mixtures of different possible isomer forms, in particular of stereoisomers such as, for example, E- and Z-isomers, but also, if appropriate, of tautomers. The E- and the Z-isomers, any mixtures of these isomers, and the possible tautomeric forms are claimed.
The invention preferably provides compounds of the formula (I) in which
E represents methylidene or nitrogen,
G represents a single bond, represents oxygen, sulphur, or represents respectively optionally halogen-, hydroxyl-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl- or C
3
-C
6
-cycloalkyl-substituted alkanediyl or alkynediyl having in each case up to 4 carbon atoms, 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
1
)═N—O—, —C(R
1
)═N—O—CH
2
—, —N(R
2
)—, —CQ—N(R
2
)—, —N(R
2
)—CQ—, —Q—CQ—N(R
2
)—, —N═C(R
1
)—Q—CH
2
—, —N(R
2
)—CQ—Q—, —CQ—N(R
2
)—CQ—Q—, —N(R
2
)—CQ—Q—CH
2
—, —Q—C(R
1
)═N—O—CH
2
—, —N(R
2
)—C(R
1
)═N—O—CH
2
—, —O—CH
2
—C(R
1
)═N—O—CH
2
—, —N═N—C(R
1
)═N—O—CH
2
—, —T—Ar
1
or —T—Ar
1
—Q—, where
n represents the numbers 0

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