Oxymethoxy-3-aryl-pyrone derivatives

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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5462821, A01N 4340, C07D40704

Patent

active

060719370

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel oxymethoxy-3-aryl-pyrone derivatives, a process for their preparation and their use as pesticides, fungicides and herbicides.
Certain phenyl-pyrone derivatives which are unsubstituted in the phenyl ring have already been disclosed (cf. A. M. Chirazi, T. Kappe and E. Ziegler, Arch. Pharm. 309, 558 (1976) and K.-H. Boltze and K. Heidenbluth, Chem. Ber. 91, 2849 (1958)), no possible use as pesticides being specified for these compounds. Phenyl-ring-substituted phenyl-pyrone derivatives having herbicidal, acaricidal and insecticidal properties are described in EP-A-588 137.
However, the activity and spectrum of activity of these compounds is not always completely satisfactory, in particular at low application rates and concentrations. In addition, the tolerance by plants is frequently inadequate.
Novel compounds of the formula (I) ##STR2## have now been found, in which alkylthio, alkylsulfinyl, alkylsulfonyl, halogenoalkyl, halogenoalkenyl, halogenoalkoxy, halogenoalkenyloxy or in each case unsubstituted or substituted phenyl, phenoxy, phenylthio, benzyloxy or benzylthio, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenoalkyl, halogenoalkenyl, halogenoalkoxy or halogenoalkenyloxy, halogenoalkyl, halogenoalkenyl, halogenoalkoxy or halogenoalkenyloxy, selected from the group comprising alkyl, cycloalkyl, alkenyl, alkinyl, arylalkyl, aryl, hetarylalkyl or hetaryl; or one of the groups --COR.sup.3, --CO.sub.2 R.sup.3, --CN, --CONR.sup.3 R.sup.4, --SO.sub.2 R.sup.3 or --P(O)(OR.sup.3)OR.sup.4, in which each case unsubstituted or substituted alkyl, alkenyl, arylalkyl, aryl, hetarylalkyl or hetaryl or alkylene group, in which one or more methylene groups is or are optionally replaced by the same number of hetero atoms, from the group comprising alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl and hetaryl or alkylene or alkenylene group, in each of which one or more methylene groups is or are optionally replaced by the same number of hetero atoms or hetero groups, halogen and substituted by halogen.
The compounds of the formula (I) can also be present, depending on the nature of the substituents, as geometric and/or optical isomers or isomer mixtures, in differing composition, which can optionally be separated in a conventional manner. Both the pure isomers and the isomer mixtures, and their preparation and use and compositions containing these are subject-matter of the present invention.
However, for the sake of simplicity, compounds of the formula (I) will always be referred to below, although both the pure compounds and, optionally, also mixtures having differing proportions of isomeric compounds are intended.
The compounds of the formula (I) can, depending on the position of the keto group, occur in the two isomeric forms of the formulae (I).sub.a and (I).sub.b, ##STR3## which is intended to be expressed by the dashed line in the formula (I).
The compounds of the formulae (I).sub.a and (I).sub.b can occur both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulae (I).sub.a and (I).sub.b may optionally be separated by physical methods in a manner known per se, for example by chromatographic methods.
For reasons of increased clarity, only one of the possible isomers in each case will be cited below. This includes the possibility of the compounds, if appropriate, occurring in the form of the isomeric mixtures or in the other respective isomeric form.
It has further been found that the novel compounds of the formula (I) ##STR4## in which A, D, X, Y, Z, R.sup.1, R.sup.2 and n have the meanings given above, ##STR5## in which A, D, X, Y, Z and n have the meanings given above, ##STR6## in which R.sup.1 and R.sup.2 have the meanings given above and reaction auxiliary.
It has further been found that the novel compounds of the formula (I), together with good tolerance by plants, have a very good activity as pesticides,

REFERENCES:
patent: 5393729 (1995-02-01), Fischer et al.

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