Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-05-17
2003-01-07
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...
C424S630000, C424S632000, C424S633000, C424S635000, C424S637000, C424S638000, C514S161000, C514S312000, C514S407000, C514S499000
Reexamination Certificate
active
06503936
ABSTRACT:
This application is a 371 of PCT/EP99/08512, filed Nov. 6, 1999. The present invention relates to a fungicidal mixture which comprises
a.1) a carbamate of the formula I.a,
in which X 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, where the radicals R can be different if n is 2, and
b) a copper-containing fungicidal active compound (II) in a synergistically active amount.
Moreover, the invention relates to processes for controlling harmful fungi using mixtures of the compounds I and II and the use of the compounds I and the compounds II for the production of mixtures of this type.
The compounds of the formula I, their preparation and their action against harmful fungi are disclosed in the literature (WO-A 96/01,256; WO-A 96/01,258).
The use of copper-containing compounds for controlling harmful fungi is likewise known.
With respect to the lowering of the application rates and an improvement in the spectrum of action of the known compounds I and II, the present invention is based on mixtures which have an improved action against harmful fungi together with a decreased total amount of applied active compounds (synergistic mixtures).
Accordingly, the mixture defined at the outset has been found. It has moreover been found that on simultaneous, to be precise, joint or separate application of the compound I and the compound II or on application of the compound I and the compound II in succession, harmful fungi can be controlled better than with the individual compounds on their own.
The formula I.a in particular represents carbamates in which the combination of the substituents corresponds to one line of the following Table:
I.a
No.
X
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
The compounds I.12, I.23, I.32 and I.38 are particularly preferred.
Because of the basic character of the nitrogen atoms contained in them, the compounds I are able to form 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, sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with straight-chain or branched alkyl radical having 1 to 20 carbon atoms), arylsulfonic acids or -disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or -diphosphonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two phosphoric acid radicals), where the alkyl and aryl radicals can carry further substituents, e.g. p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid etc.
Suitable metal ions are in particular ions of the elements of the first to eighth subgroup, especially chromium, manganese, iron, cobalt, nickel, copper, zinc, and in addition of the second main group, especially calcium and magnesium, and of the third and fourth main group, in particular aluminum, tin and lead. The metals can in this case optionally be present in various valences befitting them.
Suitable copper-containing fungicidal active compounds (II) are in general the known commercially available fungicides. Those which are particularly suitable are copper-containing fungicides from the group consisting of copper hydroxide, copper oxide, copper oxychloride sulfate, copper sulfate, oxine-copper, copper bis(3-phenylsalicylate), copper dihydrazinium disulfate, dicopper chloride trihydroxide and tricopper dichloride dimethyldithiocarbamate.
The pure active compounds I and II are preferably employed in the preparation of the mixtures, to which can be admixed further active compounds against harmful fungi or against other pests such as insects, arachnids or nematodes or alternatively herbicidal or growth-regulating active compounds or fertilizers.
The mixtures of the compounds I and II and the compounds I and II applied simultaneously, jointly or separately are distinguished by an outstanding action against a broad spectrum of phytopathogenic fungi, in particular from the Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes classes. In some cases they are systemically active and can therefore be employed as foliar and soil fungicides.
They have particular importance for the control of a multiplicity of fungi on various crop plants such as cotton, vegetable plants (e.g. cucumbers, beans, tomatoes, potatoes and cucurbits), barley, grass, oats, bananas, coffee, corn, fruit plants, rice, rye, soybeans, grapes, wheat, decorative plants, sugar cane and also on a large number of seeds.
In particular, they are suitable for the control of the following phytopathogenic fungi:
Erysiphe graminis
(powdery mildew) on cereals,
Erysiphe cichoracearum
and
Sphaerotheca fuliginea
on
cucurbits, Podosphaera leucotricha
on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawns, Ustilago species on cereals and sugar cane, venturia inaequalis (scab) on apples, Helminthosporium species on cereals,
Septoria nodorum
on wheat,
Botrytis cinerea
(gray mold) on strawberries, vegetables decorative plants and vines,
Cercospora arachidicola
on ground nuts,
Pseudocercosporella herpotrichoides
on wheat and barley,
Pyricularia oryzae
on rice,
Phytophthora infestans
on potatoes and tomatoes,
Plasmopara viticola
on vines, Pseudoperonospora species in hops and cucumbers, Alternaria species on vegetables and fruit, Mycosphaerella species in bananas and also Fusarium and Verticillium species.
They can moreover be used in the protection of materials (e.g. wood preservation), for example against
Paecilomyces variotii.
The compounds I and II can be applied simultaneously, to be precise together or separately, or in succession, the sequence in the case of separate application in general having no effect on the control result.
The compounds I and II are customarily used in a weight ratio of 1:1 to 1:1000, preferably 1:1 to 1:100, in particular 1:3 to 1:10.
The application rates of the mixtures according to the invention are, especially in the case of agricultural cultivation areas, 0.01 to 5 kg/ha, preferably 0.05 to 3.5 kg/ha, in particular 0.1 to 2.0 kg/ha, depending on the type of effect desired.
The application rates here for the compounds I are 0.01 to 2.5 kg/ha, preferably 0.05 to 2.5 kg/ha, in particular 0.1 to 1.0 kg/ha.
The application rates for the compounds II are correspondingly 0.1 to 10 kg/ha, preferably 0.5 to 5 kg/ha, in particular 0.5 to 2.0 kg/ha.
In the treatment of seed, in general application rates of mixture of 0.001 to 250 g/kg of seed, preferably 0.01 to 100 g/kg, in particular 0.01 to 50 g/kg, are used.
If harmful fungi which are pathogenic to plants are to be controlled, the separate or joint application of the compounds I and II or of the mixtures of the compounds I an
Ammermann Eberhard
Birner Erich
Leyendecker Joachim
Lorenz Gisela
Möller Bernd
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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