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
2001-06-12
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...
C514S383000, C514S619000
Reexamination Certificate
active
06245798
ABSTRACT:
The present invention relates to a fungicidal mixture which comprises
a) a carbamate of the formula I,
in which X is CH or N, n is 0, 1 or 2 and Y is halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, it being possible for the radicals Y to be different if n is 2, or a salt or adduct thereof,
and
b) an oxime ether carboxamide of the formula II
in which R represents hydrogen or halogen
in a synergistically effective amount.
Moreover, the invention relates to methods for controlling harmful fungi using mixtures of the compounds I and II and to the use of the compounds I and the compounds II for preparing such mixtures.
The compounds of the formula I, their preparation and their activity against harmful fungi are disclosed in the literature (WO-A 93/15,046; WO-A 96/01,256 and WO-A 96/01,258).
Also disclosed are the compounds of the formula II, their preparation and their activity against harmful fungi (WO-A 95/18,789).
It is an object of the present invention to provide mixtures which have improved activity against harmful fungi combined with a reduced total amount of active ingredients applied (synergistic mixtures), with a view to reducing the application rates and to improving the activity spectrum of the known compounds I and II.
We have found that this object is achieved by the mixture defined at the outset. Moreover, we have found that better control of harmful fungi is possible by applying the compounds I and the compounds II simultaneously, that is either together or separately, or by applying the compounds I and the compounds II in succession than when the individual compounds are used.
The formula I in particular represents carbamates in which the combination of the substituents corresponds to a row of the following table:
No.
X
Y
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 the formula II, R is hydrogen or a halogen atom such as fluorine, chlorine, bromine and iodine, especially hydrogen, fluorine and chlorine, in particular hydrogen or fluorine.
In relation to the C═N double bonds, the compounds of the formula II 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 a pure E or Z isomer or else in the form of an E/Z isomer mixture. The E/Z isomer mixture or the E isomer is preferably used, the E isomer being especially preferred.
The C═N double bonds of the oxime ether groups in the side chain of the compounds II can exist in each case in the form of pure E or Z isomers or in the form of E/Z isomer mixtures. The compounds II can be used in the mixtures according to the invention as isomer mixtures or else as the pure isomers. With a view to their use, compounds II which are particularly preferred are those where both oxime ether groups in the side chain are in the E configuration (E/E).
Owing to the basic character of their nitrogen atoms, the compounds I and II 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 hydriodic acid, and furthermore, sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid, carboxylic 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 aryl disulfonic acids (aromatic radicals, such as phenyl and naphtbyl 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 aryl diphosphonic 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-amino salicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
Suitable metal ions are, in particular, the ions of the elements of the first to eighth sub-groups, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc, and furthermore of the second main group, in particular calcium and magnesium, and of the third and fourth main groups, in particular aluminum, tin and lead. The metals can exist in the various valencies which they can assume.
When preparing the mixtures, it is preferred to employ the pure active ingredients I and II, to which further active ingredients 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, or the simultaneous joint and separate use of the compounds I and II, exhibit outstanding activity against a wide range of phytopathogenic fungi, in particular from the classes of the ascomycetes, basidiomycetes, phycomycetes and deuteromycetes. Some of them act systemically and can therefore be employed as foliar and soil-acting fungicides.
They are especially important for controlling a large number of fungi in a variety of crop plants, such as cotton, vegetable species (e.g. cucumbers, beans, tomatoes, potatoes and cucurbits) barley, grass, oats, bananas, coffee, maize, fruit species, rice, rye, soya, grapevine, wheat, ornamentals, sugarcane 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 lawns, Ustilago species in cereals and sugarcane,
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,
Plasmopara viticola
in grapevines, Pseudoperonospora species in hops and cucumbers, Alternaria species in vegetables and fruit, Mycosphaerella species in bananas 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 can be applied simultaneously, either 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 are usually used in a weight ratio of 10:1 to 0.1:1, preferably 5:1 to 0.2:1, in particular 3:1 to 0.3:1.
Depending on the kind of effect desired, the application rates of the mixtures according to the inventi
Ammermann Eberhard
Birner Erich
Leyendecker Joachim
Lorenz Gisela
Muller Bernd
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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