Substituted aminosalicylic acid amides with fungicidal...

Details Substituted aminosalicylic acid amides with fungicidal... Substituted aminosalicylic acid amides with fungicidal...

2000-12-19

2002-04-30

Lambkin, Deborah C. (Department: 1626)

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C544S303000, C548S130000

Reexamination Certificate

active

06380386

ABSTRACT:

This invention relates to novel substituted aminosalicylamides, to a plurality of processes for their preparation and to their use as fungicides, and also to novel intermediates and to a plurality of processes for their preparation.
Certain substituted acylaminosalicylamides, such as, for example, the compounds 3-formamido-salicylanilide and 3-(formylamino)-2-hydroxy-N-(phenylmethyl)-benz-amide, are already known (compare, for example, Biochim. Biophys. Acta (1993), 1142(3), 262-8, J. Med. Chem. (1990), 33(1), 136-42 or J. Biol. Chem. (1971), 246(23), 7125-30). However, a pesticidal activity of these prior-art compounds has hitherto not been described.
The present invention, accordingly, provides the novel substituted aminosalicylamides of the general formula (I),
in which
R
1
represents hydrogen, alkyl or alkoxy,
Y
1
, Y
2
, Y
3
, Y
4
and Y
5
are identical or different and each represents hydrogen, halogen, cyano, alkyl, halogenoalkyl, alkoxy or halogenalkoxy, and either
Y
2
or Y
3
represents —G—Z, in which
G represents one of the groupings below
—Q—CQ—, —CQ—Q—, —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
3
)═N—O—, —C(R
3
)═N—O—CH
2
—, —N(R
4
)—, —CQ—N(R
4
)—, —N(R
4
)—CQ—, —Q—CQ—N(R
4
)—, —N═C(R
3
)—Q—CH
2
—, —CH
2
—O—N═C(R
3
)—, —C(CH
3
)—O—N═C(R
3
)—, —N(R
4
)—CQ—Q—, —CQ—N(R
4
)—CQ—Q—, —N(R
4
)—CQ—Q—CH
2
—, —Q—C(R
3
)═N—O—CH
2
—, —N(R
4
)—C(R
3
)═N—O—CH
2
—, —O—CH
2
—C(R
3
)═N—O—CH
2
—, —N═N—C(R
3
)═N—O—CH
2
—, —C(═N—O—R
5
)—C(R
3
)═N—O—CH
2
—, —C(═N—O—R
5
)—C(R
3
)—O—N═CH—, —C(═N—O—R
5
)—C(R
3
)—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. by atoms different from carbon),
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulphur,
R
3
represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R
4
represents hydrogen, hydroxyl, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl,
R
5
represents hydrogen or alkyl and
T represents a single bond, represents oxygen, sulphur, —CH
2
—O—, —CH
2
—S— or represents optionally substituted alkanediyl,
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
In the definitions, the hydrocarbon chains, such as alkyl, alkylene, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as an alkoxy, alkylthio or alkylamino.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
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 also aromatic, cyclic compounds having up to eight ring members 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 or sulphur. If appropriate, the cyclic compounds form, together with further carbocyclic or heterocyclic, fused-on or bridged rings, a polycyclic ring system. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic cyclic compounds which form, if appropriate, a polycyclic ring system with other carbocyclic fused-on or bridged rings.
Cycloalkenyl represents carbocyclic cyclic compounds which contain at least one double bond and which form, if appropriate, a polycyclic ring system with other carbocyclic fused-on or bridged rings.
Furthermore, it has been found that the novel substituted acylamino-salicylamides of the general formula (I) are obtained when
a) aminosalicylamides of the general formula (II),
 in which
Y
1
, Y
2
, Y
3
, Y
4
and Y
5
are each as defined above,
are reacted with acylating agents of tile general formula (III),
 in which
R
1
is as defined above and
X
1
represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy,
if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor, and if appropriate in the presence of a further reaction auxiliary, or when
b) nitrosalicylamides of the general formula (IV)
 in which
Y
1
, Y
2
, Y
3
, Y
4
and Y
5
are each as defined above
are reacted with formic acid, if appropriate in the presence of a catalyst and if appropriate in the presence of a further reaction auxiliary, or when
c) O-benzyl-nitrosalicylamides of the general formula (V),
 in which
Y
1
, Y
2
, Y
3
, Y
4
and Y
5
are each as defined above,
are reacted with formic acid, if appropriate in the presence of hydrogen or a base metal, if appropriate in the presence of a catalyst and if appropriate in the presence of a further reaction auxiliary.
Finally, it has been found that the novel substituted aminosalicylamides of the general formula (I) have very strong fungicidal activity.
If appropriate, the compounds according to the invention and their precursors are present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers or else tautomers. What is claimed are both the E and the Z isomers, and also the threo and erythro and the optical isomers, and also the possible tautomers, and any mixtures of these isomers.
In the general formula (I),
R
1
preferably represents hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms;
in particular represents hydrogen, methyl, ethyl, n- or i-propyl, methoxy or ethoxy; preferably hydrogen, methyl or methoxy; particularly preferably hydrogen.
In the general formula (I),
Y
1
, Y
4
and Y
5
independently of one another each preferably represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms; in particular represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably hydrogen.
In the general formula (I),
Y
2
and Y
3
independently of one another each preferably represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and one of the radicals Y
2
or Y
3
represents the group —G—Z.
In particular, Y
2
represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably hydrogen.
In particular, Y
3
represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably the group —G—Z.
In the general formula (I), G preferably represents one of the groupings below
—Q—CQ—, —CQ—Q—, —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
3
)═N—O—, —C(R
3
)═N—O—CH
2
—, —N(R
4
)—, —CQ—N(R
4
)—, —N(R
4
)—CQ—, —Q—CQ—N(R
4
)—, —N═C(R
3
)—Q—CH
2
—, —CH
2
—O—N═C(R
3
)—, —C(CH
3
)—O—N═C(R
3
)—, —N(R
4
)—CQ—Q—, —CQ—N(R
4
)—CQ—Q—,—N(R
4
)—CQ—Q—CH
2
—, —Q—C(R
3
)═N—O—CH
2
—, —N(R
4
)—C(R
3
)═N—O—CH
2
—, —O—CH
2
—C(R
3
)═N—O—CH
2
—, —N═N—C(R
3
)═N—O—CH
2
—, —C(═N—O—R
5
)—C(R
3
)═N—O—CH
2
—, —C(═N—O—R
5
)—C(R
3
)—O—N═CH—, —C(═N—O—R
5
)—C(R
3
)—O—N—═C(CH
3
—)—, —T—Ar
1
— or —T—Ar
1
—Q—;
where Q, n, R
3
, R
4
and R
5
are each as defined in the application.
In particular, G represents —C(R
3
)&boxH

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