Methoximinophenylacetic acid amides

Details Methoximinophenylacetic acid amides Methoximinophenylacetic acid amides

2001-04-05

2002-06-11

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C546S102000, C544S319000, C514S608000

Reexamination Certificate

active

06403600

ABSTRACT:

The invention relates to novel methoximinophenylacetamides, to a process for their preparation and to their use as fungicides.
It is already known that certain compounds which are constitutionally similar to those described below have fungicidal properties (compare, for example, EP-A-398 692, EP-A-528 681, WO 97/00 856). However, the fungicidal activity of these compounds is unsatisfactory, in particular at low application rates.
This invention, accordingly, provides the novel methoximinophenylacetamides of the general formula (I)
in which
A represents hydrogen, alkoxycarbonyl, methyl, ethyl or cyclopropyl, or has the same meaning as R,
R represents alkylthio, halogenoalkylthio, optionally substituted arylthio, alkoxycarbonylthio, alkylthiocarbonyl, —S—Y, —S—N(R
1
R
2
), —CO—N(R
3
R
4
), —CN, —CH
2
—O—R
5
, —PO(OR
6
)R
7
, —PS(OR
6
)R
7
, in which
R
1
represents alkyl,
R
2
represents alkyl, alkoxycarbonyl, or together with R
1
and the nitrogen atom to which they are attached represents an optionally substituted heterocyclic ring,
R
3
represents alkyl or optionally substituted aryl,
R
4
represents alkylthio, alkylsulphonyl or halogenoalkylthio, or together with R
3
and the nitrogen atom to which they are attached represents an optionally substituted heterocyclic ring,
R
5
represents alkyl,
R
6
represents alkyl,
R
7
represents alkyl, alkoxy or alkylamino,
Y represents the same grouping which is already linked to the S atom,
or, if A represents methyl,
R also represents alkylcarbonyl, alkoxycarbonyl, halogenoalkoxycarbonyl, alkoxycarbonylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulphonyl or optionally substituted arylsulphonyl,
G represents a single bond, represents oxygen, sulphur or represents in each case optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl, alkenediyl, alkinediyl or one of the groupings below, in which in each case the left side is attached to Z: —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
8
)═N—O—, —C(R
8
)═N—O—CH
2
—, —N(R
9
)—, —CQ—N(R
9
)—, —N(R
9
)—CQ—, —Q—CQ—N(R
9
)—, —N═C(R
8
)—Q—CH
2
—, —CH(R
8
)—O—N═CH—, —C(R
8
)═N—N═CH—, —N(R
9
)—CQ—Q—, —CQ—N(R
9
)—CQ—Q—, —N(R
9
)—CQ—Q—CH
2
—, —Q—C(R
8
)═N—O—CH
2
—, —N(R
9
)—C(R
8
)═N—O—CH
2
—, —O—CH
2
—C(R
8
)═N—O—CH
2
—, —N═N—C(R
8
)═N—O—CH
2
—, —C(═N—O—R
10
)—C(R
8
)═N—O—CH
2
—, —C(═N—O—R
10
)—C(R
8
)—O—N═CH—, —C(═N—O—R
10
)—C(R
8
)═N—N═CH—, —C(═N—O—R
10
)—C(R
8
)—O—N═C(CH
3
)—, —T—Ar
1
—or—T—Ar
1
—Q—, where
Ar
1
represents optionally substituted arylene, heteroarylene, cycloalkylene or heterocycloalkylene (i.e. a doubly attached aliphatic ring in which one or more carbon atoms are replaced by heteroatoms, i.e. atoms different from carbon),
n represents the number 0, 1 or 2,
Q represents oxygen or sulphur,
R
8
represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl,
R
9
represents hydrogen, hydroxyl, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl,
R
10
represents hydrogen, alkyl or optionally substituted benzyl and
T represents a single bond, represents oxygen, sulphur, —CH
2
—O—, —CH
2
—S— or represents optionally substituted alkanediyl,
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represent hydrogen, halogen or alkyl,
W represents hydrogen, fluorine, cyano or thiocyanato and
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as in alkoxy or alkylthio.
Halogenoalkyl represents partially or fully halogenated alkyl. In the case of polyhalogenated halogenoalkyl, the halogen atoms can be identical or different. Preferred halogen atoms are fluorine and chlorine and in particular fluorine. If the halogenoalkyl carries further substituents, the maximum possible number of the halogen atoms is reduced to the remaining free valencies.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen and sulphur. If the ring contains a plurality of oxygen atoms, these are not directly adjacent. If appropriate, the cyclic compounds form, together with other carbocyclic or heterocyclic, fused-on or bridged rings, a polycyclic ring system. A polycyclic ring system can be attached via the heterocyclic ring or a fused-on carbocyclic ring. 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 methoximinophenylacetamides of the general formula (I) are obtained when amides of the formula (II)
in which
A, G, L
1
, L
2
, L
3
, L
4
, W and Z are each as defined above,
are reacted with an electrophilic reagent of the formula (III)
R—X  (III)
 in which
R is as defined above and
X represents a leaving group,
if appropriate in the presence of a diluent and if appropriate in the presence of a base.
Finally, it has been found that the novel methoximinophenylacetamides of the general formula (I) have very strong fungicidal activity.
If appropriate, the compounds according to the invention can be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z or optical isomers. What is claimed are both the E and the Z isomers, the individual enantiomers, the racemates, and any mixtures of these isomers.
The present invention preferably provides methoximinophenylacetamides of the formula (I)
in which
A represents hydrogen, methyl, ethoxycarbonyl, ethyl or cyclopropyl, or has the same meaning as R,
R represents alkylthio, halogenoalkylthio, alkoxycarbonylthio, alkylthiocarbonyl, having in each case 1 to 4 carbon atoms in the alkyl chains, represents phenylthio which is optionally substituted by halogen, cyano, alkyl, alkoxy or alkoxycarbonyl having in each case 1 to 4 carbon atoms, halogenoalkyl or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, —S—Y, —S—N(R
1
R
2
), —CO—N(R
3
R
4
), —CN, —CH
2
—O—R
5
, —PO(OR
6
)R
7
, —PS(OR
6
)R
7
where
R
1
represents alkyl having 1 to 4 carbon atoms,
R
2
represents alkyl having 1 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl moiety, or together with R
1
and the nitrogen atom to which they are attached represents an optionally methyl- or ethyl-substituted heterocyclic ring having 5 or 6 ring members,
R
3
represents alkyl having 1 to 4 carbon atoms or phenyl which is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 6 carbon atoms, halogenoalkyl or halogenoalkoxy having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
R
4
represents alkylthio or alkylsulphonyl having in each case 1 to 4 carbon atoms or halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms or together with R
3
and the nitrogen atom to which they are attached represents an optionally methyl- or ethyl-substituted heterocyclic ring having 5 or 6 ring members,
R
5
represents alkyl having 1 to 4 carbon atoms,
R
6
represents alkyl having 1 to 4 carbon atoms,
R
7
represents alkyl, alkoxy or alkylamino having in each case 1 to 4 carbon atoms in the alkyl chains,
Y represents the same grouping which is already linked to the sulphur atom,
or, if A represents

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