Oxymethoxy-3-aryl-pyrone derivatives

Details Oxymethoxy-3-aryl-pyrone derivatives Oxymethoxy-3-aryl-pyrone derivatives

2000-03-29

2003-06-10

Morris, Patricia L. (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S292000

Reexamination Certificate

active

06576771

ABSTRACT:

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)
have now been found,
in which
X represents halogen, nitro, cyano, alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenoalkyl, halogenoalkenyl, halogenoalkoxy, halogenoalkenyloxy or in each case unsubstituted or substituted phenyl, phenoxy, phenylthio, benzyloxy or benzylthio,
Y represents hydrogen, halogen, nitro, cyano, alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenoalkyl, halogenoalkenyl, halogenoalkoxy or halogenoalkenyloxy,
Z represents halogen, nitro, cyano, alkyl, alkenyl, alkoxy, alkenyloxy, halogenoalkyl, halogenoalkenyl, halogenoalkoxy or halogenoalkenyloxy,
n represents one of the numbers 0, 1, 2 or 3,
A represents hydrogen, halogen; an unsubstituted or substituted radical selected from the group comprising alkyl, cycloalkyl, alkenyl, alkinyl, arylalkyl, aryl, hetarylalkyl or hetaryl; or one of the groups —COR
3
, —CO
2
R
3
, —CN, —CONR
3
R
4
, —SO
2
R
3
or —P(O)(OR
3
)OR
4
, in which
R
3
and R
4
independently of one another represent hydrogen or in each case unsubstituted or substituted alkyl, alkenyl, arylalkyl, aryl, hetarylalkyl or hetaryl or
R
3
and R
4
together represent an unsubstituted or substituted alkylene group, in which one or more methylene groups is or are optionally replaced by the same number of hetero atoms,
D represents hydrogen or an unsubstituted or substituted radical selected from the group comprising alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl and hetaryl or
A and D together represent in each case an unsubstituted or substituted 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,
R
1
represents hydrogen or alkyl which is optionally substituted by halogen and
R
2
represents alkyl, alkenyl or alkinyl, each of which is optionally 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)
a
and (I)
b
,
which is intended to be expressed by the dashed line in the formula (I).
The compounds of the formulae (I)
a
and (I)
b
can occur both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulae (I)
a
and (I)
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)
in which
A, D, X, Y, Z, R
1
, R
2
and n have the meanings given above, are obtained when compounds of the formula (II)
in which
A, D, X, Y, Z and n have the meanings given above,
are reacted with compounds of the formula (III)
in which
R
1
and R
2
have the meanings given above and
Hal represents halogen (preferably chlorine or bromine),
in the presence or absence of a diluent and in the presence or absence of a 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, preferably as insecticides and acaricides, but also against parasites in animal husbandry. Furthermore, some of the novel compounds of the formula (I) have very good microbicidal, preferably fungicidal, activity. Herbicidal activities were preferentially found at higher application rates.
The compounds according to the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals cited in the formulae mentioned above and below are described below:
X preferably represents fluorine, chlorine, bromine, iodine, nitro, cyano, C
1
-C
8
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl; C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy or C
2
-C
6
-alkenyloxy, each of which is substituted by fluorine, chlorine or bromine; or phenyl, phenoxy, phenylthio, benzyloxy or benzylthio, each of which is optionally substituted by fluorine, chlorine, bromine, iodine, nitro, cyano or by C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy, each of which is optionally substituted by fluorine, chlorine or bromine.
Y preferably represents hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, C
1
-C
8
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl; or C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy or C
2
-C
6
-alkenyloxy, each of which is substituted by fluorine, chlorine or bromine.
Z preferably represents fluorine, chlorine, bromine, iodine, nitro, cyano, C
1
-C
8
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy; or C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy or C
2
-C
6
-alkenyloxy each of which is substituted by fluorine, chlorine or bromine.
n preferably represents one of the numbers 0, 1, 2 or 3.
A preferably represents hydrogen, fluorine, chlorine, bromine or iodine; a radical selected from the group consisting of C
1
-C
10
-alkyl, C
3
-C
10
-cycloalkyl, C
3
-C
10
-alkenyl and C
3
-C
10
-alkinyl, which radical is optionally substituted by fluorine, chlorine, bromine or iodine; a radical selected from the group consisting of phenyl, naphthyl, 5- or 6-membered hetaryl having one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, phenyl-C
1
-C
6
-alkyl and 5- or 6-membered hetaryl-C
1
-C
6
-alkyl having one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, which radical is optionally substituted by fluorine, chlorine, bromine, iodine, nitro, C
1
-C
8
-alkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-alkylthio, C
1
-C
8
-halogenoalkyl, C
1
-C
8
-halogenoalkoxy or cyano, or one of the groups —COR
3
, —CO
2
R
3
, —CN, —CONR
3
R
4
, —SO
2
R
3
or —P(O)(OR
3
)OR
4
, in which
R
3
and R
4
independently of one another represent hydrogen; C
1
-C
10
-alkyl or C
3
-C
10
-alkenyl, each of which is optionally substituted by fluorine, chlorine, bromine or iodine, or a radical selected from the group consisting of phenyl, naphthyl, 5- or 6-membered hetaryl having one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitro

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