Hydroxamic-acid derivatives, method of preparing them and...

Details Hydroxamic-acid derivatives, method of preparing them and... Hydroxamic-acid derivatives, method of preparing them and...

1999-07-20

2001-05-22

Richter, Johann (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C544S182000, C544S216000, C544S219000, C546S316000, C546S323000, C549S069000, C562S623000, C564S235000, C564S256000

Reexamination Certificate

active

06235790

ABSTRACT:

The invention relates to novel hydroxamic acid derivatives, to a process for preparing them and to their use as fungicides. Certain hydroxamic acid derivatives, such as, for example, the compound N-hydroxy-&agr;-hydroxyimino-farazan-ethanimidic acid, are already known (cf. Liebigs Ann. Chem. 1975, 1029-1050—cited in Chem. Abstracts 88:50732c). However, nothing has been disclosed with regard to the biological properties of such compounds.
The novel hydroxamic acid derivatives of the general formula (I) have now been found,
in which
A represents hydrogen or a grouping which can readily be eliminated,
A
1
represents hydrogen or alkyl,
Ar represents in each case optionally substituted arylene or heteroarylene,
E represents a 1-alkene-1,1-diyl grouping which contains a radical R
1
in the 2 position, or represents a 2-aza-1-alkene-1,1-diyl grouping which contains a radical R
2
in the 2 position, or represents an optionally substituted imino grouping (“azarethylene”, N—R
3
),
 where
R
1
represents hydrogen, halogen or cyano, or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R
2
represents hydrogen, amino or cyano, or in each case optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
R
3
represents hydrogen or cyano, or in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylalkyl,
G represents oxygen, or alkanediyl, alkenediyl or alkinediyl which are in each case optionally substituted by halogen, hydroxyl, alkyl, halogenoalkyl or cycloalkyl, or 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—, or —N(R
5
)—CQ—Q—CH
2
—,
 where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulphur,
R
4
represents hydrogen or cyano, or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, or cycloalkyl, and
R
5
represents hydrogen, hydroxyl or cyano, or in each case optionally substituted alkyl, alkoxy or cycloalkyl, and
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
In addition, it has been found that the novel hydroxamic acid derivatives of the general formula (I) are obtained if carboxylic acid derivatives of the general formula (II)
in which
Ar, B, G and Z have the abovementioned meaning, and
R represents hydrogen or alkyl,
are reacted with a hydroxylamine of the general formnula (III)
A
1
—NH—O—A  (III)
 in which
A and A
1
have the abovementioned meaning,
—or with a hydrogen halide thereof—
optionally in the presence of an acid acceptor and optionally in the presence of a diluent.
Finally, it has been found that the novel hydroxamic acid derivatives of the general formula (I) exhibit a very powerful fungicidal activity.
The compounds according to the invention may optionally be present as mixtures of different possible isomeric forms, in particular of E and Z isomers, optionally, however, also of tautomers. Both the E and the Z isomers, and also arbitrary mixtures of these isomers, as well as the possible tautomeric forms, are claimed.
The invention preferably relates to compounds of the formula (I) in which
A represents hydrogen, alkyl having 1 to 8 carbon atoms which is optionally substituted by halogen, cyano, hydroxyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxy, N,N-di-(C
1
-C
4
-alkyl)-amino, N-(C
1
-C
4
-alkyl-carbonyl)-amino, N-(C
1
-C
4
-alkyl)-N-(C
1
-C
4
-alkyl-carbonyl)-amino, N-(C
1
-C
4
-alkoxy-carbonyl)-amino or N-(C
1
-C
4
-alkyl)-N-(C
1
-C
4
-alkoxy-carbonyl)-amino, C
1
-C
4
-alkoxy-carbonyl, C
1
-C
4
-alkylamino-carbonyl or di-(C
1
-C
4
-alkyl)-amino-carbonyl,
A
1
represents hydrogen or alkyl having 1 to 6 carbon atoms,
Ar represents in each case optionally substituted phenylene or naphthylene. or heteroarylene having 5 or 6 ring members, of which at least one represents oxygen, sulphur or nitrogen and optionally one or two additional members represent nitrogen, where the possible substituents are preferably selected from the following list:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl 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, halogenoalkylsulphinyl or halogenoalkylsulphonyl 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 13 identical or different halogen atoms, in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or in each case doubly linked alkylene or dioxyalkylene which have in each case 1 to 6 carbon atoms and which are in each case optionally substituted, once or more than once, identically or differently, by 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 represents one of the following groupings
 in which
R represents hydrogen or alkyl having 1 to 6 carbon atoms,
R
1
represents hydrogen, halogen or cyano, or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino which have in each case 1 to 6 carbon atoms in the alkyl radicals and which are in each case optionally substituted by halogen, cyano or C
1
-C
4
-alkoxy,
R
2
represents hydrogen, amino or cyano, or alkyl, alkoxy, alkylamino or dialkylamino which have in each case 1 to 6 carbon atoms in the alkyl radicals and which are in each case optionally substituted by halogen, cyano or C
1
-C
4
-alkoxy, and
R
3
represents hydrogen or cyano, or alkyl, alkenyl or alkinyl which have in each case up to 6 carbon atoms and which are in each case optionally substituted by halogen, cyano or C
1
-C
4
-alkoxy, or cycloalkyl or cycloalkylalkyl which have 3 to 6 carbon atoms in the cycloalkyl moieties and optionally 1 to 4 carbon atoms in the alkyl moiety and which are in each case optionally substituted by halogen, cyano, carboxyl, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy-carbonyl,
G represents oxygen, alkanediyl, alkenediyl or alkinediyl which have in each case up to 4 carbon atoms and which are in each case optionally substituted by halogen, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl or C
3
-C
6
-cycloalkyl, or 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—, or —N(R
5
)—CQ—Q—CH
2
—,
 where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulphur,
R
4
represents hydrogen or cyano, or alkyl, alkoxy, alkylthio, alkylamino, or dialkylamino which have in each case 1 to 6 carbon atoms in the alkyl groups and which are optionally substituted by halogen, cyano or C
1
-C
4
-alkoxy, or cycloalkyl which has from 3 to 6 carbon atoms and which is in each case optionally substituted by halogen, cyano, carboxyl, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy-carbonyl, and
R
5
represents hydrogen, hydroxyl or cyano, or alkyl which has 1 to 6 carbon atoms and which is optionally substituted by halogen, cyano or

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