Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-11-17
2001-11-13
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S407000, C514S422000, C514S427000
Reexamination Certificate
active
06316480
ABSTRACT:
The present invention relates to fungicidal mixtures, comprising
a) a carbamate of the formula I,
where T is CH or N, n is 0, 1 or 2 and R is halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, it being possible for the radicals R to be different if n is 2, and
b) at least one active ingredient of the formula II or III,
in a synergistically effective amount.
Moreover, the invention relates to methods for controlling harmful fungi using mixtures of the compounds I and II or III and to the use of the compounds I and II or III for the preparation of such mixtures.
The compounds of the formula I, their preparation and their activity against harmful fungi are disclosed in the literature (WO-A 96/01,256 and 96/01,258).
The compound II is disclosed in K. Gehmann, R. Nyfeler, A. J. Leadbeater, D. Nevill and D. Sozzi, Proceedings of the Brighton Crop Protection Conference, Pests and Diseases 1990, Vol. 2, page 399 (common name: fludioxinil) and obtainable commercially from Novartis.
The compound III is disclosed in D. Nevill, R. Nyfeler, D. Sozzi, Proceedings of the Brighton Crop Protection Conference, Pests and Diseases 1988, Vol. 1, page 65 (common name: fenpiclonil).
It was an object of the present invention to provide mixtures which have an improved activity against harmful fungi combined with a reduced total amount of active ingredients applied (synergistic mixtures), with a view to reducing the rates of application and to improving the spectrum of action of the known compounds.
Accordingly, we have found that this object is achieved by the mixtures defined at the outset. Moreover, we have found that better control of the harmful fungi is possible by applying the compounds I and II and/or III simultaneously together or separately, or by applying the compounds I and II and/or III in succession, than when the individual compounds are used.
The formula I represents in particular carbamates in which the combination of the substituents corresponds to one row of the table below:
TABLE 1
No.
T
R
n
I.1
N
2-F
I.2
N
3-F
I.3
N
4-F
I.4
N
2-Cl
I.5
N
3-Cl
I.6
N
4-Cl
I.7
N
2-Br
I.8
N
3-Br
I.9
N
4-Br
I.10
N
2-CH
3
I.11
N
3-CH
3
I.12
N
4-CH
3
I.13
N
2-CH
2
CH
3
I.14
N
3-CH
2
CH
3
I.15
N
4-CH
2
CH
3
I.16
N
2-CH(CH
3
)
2
I.17
N
3-CH(CH
3
)
2
I.18
N
4-CH(CH
3
)
2
I.19
N
2-CF
3
I.20
N
3-CF
3
I.21
N
4-CF
3
I.22
N
2,4-F
2
I.23
N
2,4-Cl
2
I.24
N
3,4-Cl
2
I.25
N
2-Cl, 4-CH
3
I.26
N
3-Cl, 4-CH
3
I.27
CH
2-F
I.28
CH
3-F
I.29
CH
4-F
I.30
CH
2-Cl
I.31
CH
3-Cl
I.32
CH
4-Cl
I.33
CH
2-Br
I.34
CH
3-Br
I.35
CH
4-Br
I.36
CH
2-CH
3
I.37
CH
3-CH
3
I.38
CH
4-CH
3
I.39
CH
2-CH
2
CH
3
I.40
CH
3-CH
2
CH
3
I.41
CH
4-CH
2
CH
3
I.42
CH
2-CH(CH
3
)
2
I.43
CH
3-CH(CH
3
)
2
I.44
CH
4-CH(CH
3
)
2
I.45
CH
2-CF
3
I.46
CH
3-CF
3
I.47
CH
4-CF
3
I.48
CH
2,4-F
2
I.49
CH
2,4-Cl
2
I.50
CH
3,4-Cl
2
I.51
CH
2-Cl, 4-CH
3
I.52
CH
3-Cl, 4-CH
3
Particular preference is given to the compounds I.12, I.23, I.32 and I.38.
In relation to the C═Y or C═CH or C═N double bonds, the compounds of the formula I can be present in the E or the Z configuration (in relation to the carboxylic acid function). Accordingly, they can be used in the mixture according to the invention in each case either in the form of the pure E or Z isomers or in the form of an E/Z isomer mixture. The E/Z isomer mixture or the Z isomer is preferably used, the Z isomer being especially preferred.
The C═N double bonds of the oxime ether groups in the side chain of the compounds I can exist in each case in the form of pure E or Z isomers or as E/Z isomer mixtures. The compounds I can be used in the mixtures according to the invention both as isomer mixtures and as pure isomers. With a view to their use, compounds I which are particularly preferred are those where the terminal oxime ether group in the side chain is in the cis configuration (OCH
3
to ZR′).
Owing to their basic character, the compounds I are capable of forming salts or adducts with inorganic or organic acids or with metal ions.
Examples of inorganic acids are hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two sulfo groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphonic acid radicals), it being possible for the alkyl or aryl radicals to carry further substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
Suitable metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, and of the first to eighth subgroup, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Especially preferred are the metal ions of the elements of the subgroups of the fourth period. The metals can exist in the various valences which they can assume.
When preparing the mixtures, it is preferred to employ the pure active ingredients I and II and/or III, to which further ingredients active against harmful fungi or other pests, such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active ingredients or fertilizers can be admixed, if so required.
The mixtures of the compounds I and II and/or III, or the simultaneous joint or separate use of the compounds I and II and/or III, have outstanding action against a wide spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can therefore be employed as folia- and soil-acting fungicides.
They are especially important for controlling the large number of fungi in a variety of crop plants, such as cotton, vegetable species (e.g. cucumbers, beans and cucurbits), barley, grass, oats, coffee, maize, fruit species, rice, rye, soya, grapevine, wheat, ornamentals, sugar cane, and a variety of seeds.
They are particularly suitable for controlling the following phytopathogenic fungi:
Erysiphe graminis
(powdery mildew) in cereals,
Erysiphe cichoracearum
and
Sphaerotheca fuliginea
in cucurbits,
Podosphaera leucotricha
in apples,
Uncinula necator
in grapevines, Puccinia species in cereals, Rhizoctonia species in cotton, rice and lawn, Ustilago species in cereals and sugar cane,
Venturia inaequalis
(scab) in apples, Helminthosporium species in cereals,
Septoria nodorum
in wheat,
Botrytis cinerea
(gray mold) in strawberries, vegetables, ornamentals and grapevines,
Cercospora arachidicola
in groundnuts,
Pseudocercosporella herpotrichoides
in wheat and barley,
Pyricularia oryzae
in rice,
Phytophthora infestans
in potatoes and tomatoes, Pseudoperonospora species in cucurbits and hops,
Plasmopara viticola
in grapevines, Alternaria species in vegetables and fruit and Fusarium and Verticillium species.
Furthermore, they can be used in the protection of materials (e.g. in the protection of wood), for example against
Paecilomyces variotii.
The compounds I and II and/or III can be applied simultaneously together or separately or in succession, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
The compounds I and II and/or III are usually used in a weight ratio of from 0.05:1 to 20:1,
Ammermann Eberhard
Birner Erich
Leyendecker Joachim
Lorenz Gisela
Muller Bernd
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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