Acylaminosalicylic acid amides and their uses as pesticides

Details Acylaminosalicylic acid amides and their uses as pesticides Acylaminosalicylic acid amides and their uses as pesticides

1998-02-18

1999-12-14

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

564158, C07C23714, A01N 3718

Patent

active

060018798

DESCRIPTION:

BRIEF SUMMARY
The invention relates to known and to new acylaminosalicylamides, to a plurality of processes for their preparation and to their use as pesticides. The present application furthermore relates to novel intermediates, to a plurality of processes for their preparation and to their use as pesticides.
Certain acylaminosalicylamides, such as, for example, the compounds 3-formamido-salicylanilide and 3-(formylamino)-2-hydroxy-N-(phenylmethyl )-benzamide, have already been disclosed (compare, for example, B. Biochim. Biophys. Acta (1993), 1143(3), 262-8, J. Med. Chem. (1990), 33(1), 136-42 or J. Biol. Chem. (1971), 246(23), 7125-30).
However, an activity against pests has not been described to date of these prior-art compounds.
It has now been found that the acylaminosalicylamides of the general formula (I) ##STR1## in which A represents a single linkage or an alkylene chain, cycloalkenyl, aryl or heterocyclyl in plants and industrial materials.
In the definitions, the hydrocarbon chains such as alkyl, alkene, alkenyl or alkinyl, also in conjunction with hetero atoms such as in alkoxy, alkylthio or alkylamino, are in each case straight-chain or branched.
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 hetero atom, that is to say an atom other than carbon. If the ring contains more than one hetero atom, they can be identical or different. Hetero atoms are preferably oxygen, nitrogen or sulphur. If appropriate, the cyclic compounds together with other carbocyclic or heterocyclic, fused or bridged rings form a polycyclic ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic cyclic compounds which, if appropriate, together with other carbocyclic, fused or bridged rings form a polycyclic ring system.
Cycloalkenyl represents carboxycyclic cyclic compounds which contain at least one double bond and, if appropriate, together with other carbocyclic, fused or bridged rings form a polycyclic ring system.
The present application also relates to new acylaminosalicylamides of the general formula (I) ##STR2## in which A represents a single linkage or optionally substituted alkylene, cycloalkenyl, aryl or heterocyclyl, with the exception of the nitro group as substituent, 3-(formylamino)-2-hydroxy-N-{4-[2,4,6-tris(1-methylpropyl)-phenoxy]phenyl }-benzamide, N-{4-[3,5-bis-(1,1-dimethylethyl)-phenoxy]-phenyl}-3-(formylamino)-2-hydro xy-benzamide, N-{4-[2,4-bis-(1,1-dimethylethyl)-phenoxy]-phenyl}-3-(formylamino)-2-hydro xy-benzamide, N-{4-[2,6-bis-(1-methylpropyl)-phenoxy]-phenyl}-3-(formylamino)-2-hydroxy- benzamide, 3-(formylamino)-2-hydroxy-N-{4-[3-(trifluoromethyl)-phenoxy]-phenyl}-benza mide, N-{4-[4-(1,1-dimethylethyl)-phenoxy]-phenyl}-3-(formylamino)-2-hydroxy-ben zamide, 3-(formylamino)-2-hydroxy-N-(4-phenoxyphenyl)-benzamide, N-(4-butylphenyl)-3-(formylamino)-2-hydroxy-benzamide and N-{3-chloro-4-(4-chlorophenoxy)phenyl}-3-(formylamino)-2-hydroxy-benzamide , 3-(formylamino)-2-hydroxy-N-(phenylmethyl)-benzamide, 3-formamido-salicylanilide and 3-(formylamino)-2-hydroxy-N-(2-phenylethyl)-benzamide are excepted.
Furthermore, it has been found that the new acylaminosalicylamides of the general formula (I) are obtained when ##STR3## in which A and R.sup.2 have the abovementioned meanings ##STR4## in which R.sup.1 has the abovementioned meaning, and presence of an acid acceptor and if appropriate in the presence of a further reaction auxiliary, or when ##STR5## in which A and R.sup.2 have the abovementioned meanings and if appropriate in the presence of further reaction auxiliary, or when ##STR6## in

REFERENCES:
patent: 3148995 (1964-09-01), Hemwall
patent: 3929879 (1975-12-01), Taborsky

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