Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
1999-11-17
2001-07-03
Spivack, Phyllis G. (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
active
06255352
ABSTRACT:
The present invention relates to a method of controlling harmful fungi, which comprises treating the fungi, or the materials, plants, the soil or seeds to be protected against fungal infection, with an effective amount of a bisoxime of the formula I
or a salt or adduct thereof, the index and the substituents having the following meanings:
R
1
is halogen, C
1
-C
6
-alkyl or C
1
-C
4
-haloalkyl;
R
2
is cyano, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylamino, di-C
1
-C
4
-alkylamino, C
1
-C
4
-alkylaminocarbonyl,
phenyl, phenoxy or phenylthio, it being possible for these radicals to be partially or fully halogenated in the phenyl moiety and/or to have attached to them one to three of the following groups: cyano, formyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, phenyl or naphthyl;
n is 0, 1, 2 or 3, it being possible for the radicals R
2
to be different if n is 2 or 3;
R
3
is C
1
-C
10
-alkyl, C
1
-C
6
-haloalkyl, C
3-C
6
-alkenyl, C
3-C
6
-haloalkenyl, C
3-C
6
-alkynyl, C
3-C
6
-haloalkynyl or phenyl-C
1
-C
4
-alkyl.
In addition, the invention relates to the use of the compounds I for the preparation of a composition which is suitable for controlling harmful fungi.
Bisoximes of the formula I defined at the outset have been disclosed in the literature (cf. WO-A 95/18,789; WO-A 95/21,153; WO-A 95/21,154; WO-A 95/21,156; WO-A 96/06,072; WO-A 96/16,026; WO-A 96/16,030; WO-A 97/01,530; WO-A 97/02,255; DE Appl. No. 19 540 989; DE Appl. No. 19 545 878; DE Appl. No. 19 548 370) as intermediates for the preparation of fungicidally active ingredients of the type of the formula A:
However, apart from the usefulness of these compounds as intermediates, these documents do not suggest any additional possible applications of the bisoximes.
In addition, PCT/EP 96/01,306 describes processes for the preparation of essentially isomerically pure bisoximes of the type of the compounds I. As regards the use of such compounds, this document refers to the suitability as intermediate for the preparation of the compounds of type (A).
It is an object of the present invention to provide compounds with fungicidal properties.
We have found that this object is achieved by the prior-art bisoximes, which are suitable for controlling harmful fungi in an efficient manner.
The meaning of the collective terms used in the definition of the compounds I can be seen, for example, from the relevant information in WO-A 95/21,156.
As regards their intended use for controlling harmful fungi, particularly suitable compounds I are those where R
1
is fluorine, chlorine or bromine (in particular chlorine) or methyl, ethyl, propyl or iso-propyl (in particular methyl or ethyl).
Other preferred compounds I are those where n is 1, 2 or 3 (especially 1 or 2).
In the event that n is 1, preferred compounds I are those where the radical R
2
is bonded in the 4-position of the phenyl ring.
In the event that n is 2, preferred compounds I are those where the radicals R
2
are bonded in the relative position 2,4 or 3,4 (especially 2,4).
In the event that n is 3, preferred compounds I are those where the radicals R
2
are bonded in the relative position 2,4,5 or 2,4,6 (especially 2,4,5).
Especially suitable as radicals R
2
are halogen (in particular fluorine, chlorine and bromine), C
1
-C
4
-alkyl (in particular methyl), C
1
-C
4
-haloalkyl (in particular trifluoromethyl), C
1
-C
4
-alkoxy (in particular methoxy), C
1
-C
4
-haloalkoxy (in particular trifluoromethoxy) and C
1
-C
4
-alkylthio (in particular methylthio), nitro and dimethylamino.
Additional preferred compounds I are those where R
2
(preferably one of the radicals R
2
) is phenyl, phenoxy or phenylthio (in particular phenyl), it being possible for these radicals to have attached to them in the phenyl moiety preferably one to three of the following groups: halogen (in particular chlorine and bromine), C
1
-C
4
-alkyl (in particular methyl), C
1
-C
4
-haloalkyl (in particular trifluoromethyl), C
1
-C
4
-alkoxy (in particular methoxy), and C
1
-C
4
-haloalkoxy (in particular trifluoromethoxy).
Other particularly preferred compounds I are those where at least one of the radicals R
2
is halogen.
With regard to the radical R
3
, preferred compounds I are those which have attached to them, in this position,
C
1
-C
10
-alkyl (especially C
1
-C
4
-alkyl),
C
3
-C
6
-alkenyl or C
3
-C
6
-haloalkenyl [especially C
3
-C
4
-alkenyl which may have attached to it one to three (in particular one or two) halogen atoms (in particular chlorine or bromine)],
C
3
-C
6
-alkynyl or C
3
-C
6
-haloalkynyl [especially C
3
-C
4
-alkynyl which may have attached to it one to three (in particular one or two) halogen atoms (in particular chlorine or bromine), or
phenyl-C
1
-C
4
-alkyl (in particular benzyl).
The compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them are systemically active, and they can be employed in crop protection as foliar- and soil-acting fungicides.
They are especially important for controlling a large number of fungi on a variety of crop plants, such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soya, coffee, sugarcane, grapevines, fruit species, ornamentals and vegetables such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.
Specifically, they are suitable for controlling the following plant diseases:
Alternaria species on vegetables and fruit,
Botrytis cinerea
(gray mold) on strawberries, vegetables, ornamentals and grapevines,
Cercospora arachidicola
on peanuts,
Erysiphe cichoracearum
and
Sphaerotheca fuliginea
on cucurbits,
Erysiphe graminis
(powdery mildew) on cereals,
Fusarium and Verticillium species on a variety of plants,
Helminthosporium species on cereals,
Mycosphaerella species on bananas,
Phytophthora infestans
on potatoes and tomatoes,
Plasmopara viticola
on grapevines,
Podosphaera leucotricha
on apples,
Pseudocercosporella herpotrichoides
on wheat and barley,
Pseudoperonospora species on hops and cucumbers,
Puccinia species on cereals,
Pyricularia oryzae
on rice,
Rhizoctonia species on cotton, rice and turf,
Septoria nodorum
on wheat,
Uncinula necator
on grapevines,
Ustilago species on cereals and sugarcane, and
Venturia inaequalis
(scab) on apples.
The compounds I are particularly suitable for controlling Erysiphe species and
Plasmopara viticola.
In addition, the compounds I are suitable for controlling harmful fungi such as
Paecilomyces variotii
in the protection of materials (eg. wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
The compounds I are applied by treating the fungi, or the plants, seeds, materials or the soil to be protected against fungal infection, with a fungicidally active amount of the active ingredients. Application may be effected before or after infection of the materials, plants, or seeds by the fungi.
When applied in crop protection, the rates of application are from 0.001 to 5.0 kg, preferably 0.01 to 2 kg, in particular 0.05 to 1 kg, of active ingredient per ha, depending on the nature of the desired effect.
In the treatment of seed, amounts of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, of active ingredient are generally required per kilogram of seed.
When used in the protection of materials or stored products, the rate of application of active ingredient depends on the nature of the field of application and of the desired effect. Normal rates of application in the protection of materials are, for example, from 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of material treated.
Due to the basic character of the nitrogen atoms, the compounds I may form salts or adducts with acids and metal ions and may be applied in the for
Ammermann Eberhard
Bayer Herbert
Grammenos Wassilios
Grote Thomas
Gypser Andreas
BASF - Aktiengesellschaft
Keil & Weinkauf
Spivack Phyllis G.
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