Fungicidal mixtures

Details Fungicidal mixtures Fungicidal mixtures

1998-11-05

2001-01-09

Robinson, Allen J. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S383000, C514S407000, C514S622000

Reexamination Certificate

active

06172063

ABSTRACT:

The present invention relates to a fungicidal mixture which contains
a) a carbamate of the formula I,
 where 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, it being possible for the radicals R to be different if n is 2, and
b) a carboxamide II selected from the group consisting of the compounds IIa and IIb
in a synergistically active amount.
The invention additionally relates to methods of controlling harmful fungi using mixtures of the compounds I and II and the use of the compound I and of the compound II for the production of mixtures of this type.
The compounds of the formula I, their preparation and their action against harmful fungi are known from the literature (WO-A 96/01,256 and 96/01,258).
Likewise known are the carboxamides II [IIa: common name: dimethomorph, EP-A 120 321; IIb: proposed common name: flumetover, AGROW No. 243 (1995) 22], their preparation and their action against harmful fungi.
With a view to lowering the application rates and improving the spectrum of action of the known compounds, it is an object of the present invention to provide mixtures which, together with a decreased total amount of active compounds applied, have an improved action against harmful fungi (synergistic mixtures).
We have found that this object is achieved by the mixtures defined at the outset. We have additionally found that on simultaneous joint or separate application of the compounds I and the compounds II or on application of the compounds I and the compounds II in succession harmful fungi can be controlled better than with the individual compounds.
The formula I in particular represents carbamates where the combination of the substituents corresponds to one line of the following table:
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, the compounds I and II 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 having straight-chain or branched alkyl radicals having from 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 having straight-chain or branched alkyl radicals having from 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), it being possible for the alkyl and aryl radicals to 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 the ions of the elements of the second main group, in particular calcium and magnesium, 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. The metal ions of the elements of the subgroups of the fourth period are particularly preferred. The metals can be present here in the various valences befitting them.
Preferably, in the preparation of the mixtures the pure active compounds I and II are employed, with which, if required, further compounds active against harmful fungi or other pests such as insects, arachnids or nematodes, or alternatively herbicidal or growth-regulating active compounds or fertilizers, can be admixed.
The mixtures of the compounds I and II and the simultaneous joint or separate use of the compounds I and II are distinguished by an outstanding action against a wide spectrum of phytopathogenic fungi, in particular of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes classes. In some cases they are systemically active and can therefore also be employed as foliar and soil fungicides.
They are of particular importance for controlling a multiplicity of fungi on various crop plants such as cotton, vegetable plants (e.g. cucumbers, beans and cucurbits), barley, grass, oats, coffee, corn, fruit plants, rice, rye, soybeans, grapes, wheat, decorative plants, sugar cane and a multiplicity of seeds.
They are particularly suitable for controlling 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, Rhynosporium Secalis,
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, Alternaria species on vegetables and fruit, and Fusarium and Verticillium species.
They are additionally utilizable in the protection of materials (e.g. wood preservation), for example against
Paecilomyces variotii.
The compounds I and II can be applied together or separately at the same time or in succession, the sequence in the case of separate application in general having no effect on the control success.
The compounds I and II are customarily applied in a weight ratio of from 20:1 to 0.1:2, preferably 10:1 to 0.2:1, in particular 5:1 to 0.5:1.
Depending on the type of effect desired, the application rates in the mixtures according to the invention for the compounds I are from 0.01 to 0.5 kg/ha, preferably 0.05 to 0.5 kg/ha, in particular 0.05 to 0.3 kg/ha.
The application rates for the compounds II are correspondingly from 0.05 to 1 kg/ha, preferably 0.1 to 1 kg/ha, in particular 0.1 to 0.8 kg/ha.
In the treatment of seed, in general application rates of mixture of from 0.001 to 50 g/kg of seed, preferably 0.01 to 10 g/kg, in particular 0.01 to 5 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 the mixtures of the compounds I and II is carried out by spraying or dusting the seeds, the plants or the soils before or after sowing the plants or before or after the emergence of the plants.
The fungicidal synergistic mixtures or the compounds I and II according to the invention can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-percentage aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusting compositions, broadcasting compositions or granules and applied by

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