Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-01-22
2003-03-11
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S005000, C548S123000
Reexamination Certificate
active
06531496
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to new O-aryldithiazole dioxides, to two processes for their preparation, and to their use as pesticides in crop protection and in the protection of materials.
BACKGROUND OF THE INVENTION
Certain aryldithiazole dioxides with a similar substitution pattern and their action against organisms which are harmful to plants and materials have already been disclosed (cf. DE-19545635 and WO98-29400). However, the action of these state-of-the-art compounds is not entirely satisfactory in all fields of application, in particular when low application rates and concentrations are used.
DETAILED DESCRIPTION
There have now been found the new compounds of the general formula (I)
in which
Ar represents substituted or unsubstituted aryl and
Y represents substituted or unsubstituted, straight-chain or branched alkanediyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, are in each case straight-chain or branched, also when linked to hetero atoms, such as in alkoxy or alkylthio.
Aryl represents aromatic, mono or polycyclic hydrocarbon rings such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Substituents of the present application are to be understood as meaning in particular those where individual preferred ranges are mentioned.
The following are substituents for aryl or for alkanediyl, in particular for aryl: halogen, cyano, thiocyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl, hydrogen, hydroxyl; in each case straight-chain or branched alkyl, cyanoalkyl, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 8 carbon atoms; in each case straight-chain or branched alkenyl, alkenyloxy or alkenylcarbonyl, each of which has 2 to 6 carbon atoms in the alkenyl moiety and each of which is optionally monosubstituted or disubstituted by cyano, nitro, phenyl, nitrophenyl, dinitrophenyl, alkoxycarbonylamino, phthalimidyl, bis-(alkoxycarbonylamino) or dioxobenzimidazolyl; in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy, each of which has 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, thiocyanoalkylcarbonyl, halogenoalkylcarbonyl (having 1 to 3 halogen atoms), alkoxycarbonyl, alkoxycarbonylazoalkyl, alkylaminocarbonyl, dialkyl-aminocarbonyl or arylalkylaminocarbonyl having 1 to 6 carbon atoms in the respective hydrocarbon chains, or cycloalkylcarbonylamino or cycloalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl moiety and each of which is optionally monosubstituted to tetrasubstituted by halogen or alkyl having 1 to 4 carbon atoms; cycloalkyl or cycloalkyloxy, each of which has 3 to 6 carbon atoms; phenyl, phenoxy, phenylazo, phenylthio, phenylsulphonyl, phenylcarbonyl, phenylalkylcarbonyl, or phenylalkoxy having 1 to 4 carbon atoms in the alkyl moiety, optionally substituted in each case by halogen, alkyl, phenyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, heterocyclyl, heterocyclylalkyl having 1 to 4 carbon atoms in the alkyl moiety, heterocyclyloxy, heterocyclylthio, heterocyclylsulphinyl, heterocyclylsulphonyl, heterocyclylcarbonyl, heterocyclylthiocarbonyl, benzoheterocyclyl, benzoheterocyclylalkyl having 1 to 4 carbon atoms in the alkyl moiety, benzoheterocyclyloxy, benzoheterocyclylthio, benzoheterocyclylsulphinyl, benzoheterocyclylsulphonyl, benzoheterocyclylcarbonyl or benzoheterocyclylthiocarbonyl, each of which has 5 or 6 ring members in the heterocyclyl moiety, in each case optionally substituted by halogen, oxo, alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms or phenyl, or a group
where
T represents CH or nitrogen,
A
1
represents hydrogen or alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, phenyl, heterocyclyl having 5 or 6 ring members, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl moiety, benzylaminocarbonyl, benzyloxyaminocarbonyl or aminocarbonyl, and
A
2
represents hydroxyl, amino, alkyl, phenyl, benzyl, alkoxy, cyanoalkoxy, benzyloxy, alkylamino, dialkylamino, alkoxycarbonylamino, alkoxycarbonylphenyl, in each case having 1 to 4 carbon atoms in the respective alkyl chains, or alkenyloxy having 2 to 4 carbon atoms.
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 has additionally attached to it further substituents, the maximum number of halogen atoms which is possible is reduced to the free valencies which remain.
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 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. If the ring contains more than one oxygen atom, these are not adjacent to each other. If appropriate, the cyclic compounds together with further carbocyclic or heterocyclic, fused or bridged rings form a polycyclic ring system. A polycyclic ring system can be linked via the heterocyclic ring or a fused carbocyclic ring. Preferred are mono- or bicyclic ring systems, in particular mono- or bicyclic aromatic ring systems.
Furthermore, it has been found that the new compounds of the general formula (I) are obtained (process a) when dithiazole dioxides of the general formula (II)
in which
Y is as stated above and
X represents halogen, alkyl- or arylsulphonyl
are reacted with phenols of the general formula (III)
Ar—OH (III)
in which
Ar is as stated above and
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 catalyst.
Finally, it has been found that the new compounds of the general formula (I) have a very potent fungicidal and insecticidal action.
If appropriate, the compounds according to the invention can exist as mixtures of various isomeric forms which are possible, in particular in the form of stereoisomers, such as, for example, E- and Z-isomers, or optical isomers. All of the E- and Z-isomers, the individual enantiomers, the racemates, and any mixtures of these isomers are claimed.
Subject-matter of the invention are preferably compounds of the formula (I-a)
in which
R
1
, R
2
, R
3
, R
4
and R
5
are identical or different and independently of one another represent the following substituents:
halogen, cyano, thiocyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl, hydrogen, hydroxyl;
in each case straight-chain or branched alkyl, cyanoalkyl, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl, alkenyloxy or alkenylcarbonyl, each of which has 2 to 6 carbon atoms in the alkenyl moiety and each of which is optionally monosubstituted or disubstituted by cyano, nitro, phenyl, nitrophenyl, dinitrophenyl, alkoxyc
Boie Christiane
Heinemann Ulrich
Krüger Bernd-Wieland
Kuck Karl-Heinz
Kugler Martin
Bayer Aktiengesellschaft
Gerstl Robert
Gil Joseph C.
Henderson Richard E.L.
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