Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-11-15
2003-03-04
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...
C514S384000, C514S539000, C514S549000, C514S619000
Reexamination Certificate
active
06528536
ABSTRACT:
The present invention relates to a fungicidal mixture which comprises
a
1
) a phenyl benzyl ether derivative of the formula I.a, I.b or I.c
and/or
a
2
) a carbamate of the formula Id
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, or one of its salts or adducts, and
b) a dinitrophenol derivative of the formula II.a or II.b
where n is 0, 1 or 2 in a synergistically effective amount.
The invention further relates to methods for controlling harmful fungi using mixtures of the compounds I (I.a, I.b or I.c) and II (II.a or II.b) and to the use of the compound I and the compound II for preparing such mixtures.
The compounds of the formula Ia-c, their preparation and their activity against harmful fungi are known from the literature (EP-A 253 213; EP-A 254 426; EP-A 398 692).
The compounds of the formula Id, their preparation and their activity are known from WO-A 93/15046, WO-A 96/01256 and WO-A 96/01258.
Also known is the mixture of the compounds II (II.a and II.b) (common name: Dinocap), their preparation and their activity against harmful fungi and arachnids (U.S. Pat. Nos. 2,526,660; 2,810,767).
It is 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 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. In addition, we have found that, by applying the compound I and the compound II simultaneously, that is to say separately as well as together, or by applying the compound I and the compounds II in succession, better control of harmful fungi is possible than when the individual compounds are used.
The formula Id in particular represents carbamates where the combination of the substituents corresponds to a row of the table below:
(I)
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
Particular preference is given to the compounds I.12, I.23, I.32 and I.38.
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.
The mixtures of the compounds I and II, or the simultaneous joint or separate use of the compounds I and II, have outstanding action 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 also 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 (eg. cucumbers, beans, tomatoes, potatoes and cucurbits), barley, grass, oats, bananas, 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 lawns, 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,
Plasmopara viticola
in grapevines Pseudocercosporella 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 (eg. in the protection of wood), for example against
Paecilomyces variotii.
The compounds I and II can be applied simultaneously, that is 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 in a weight ratio of 10:1 to 0.01:1, preferably 5:1 to 0.05:1, in particular 1:1 to 0.05:1.
Depending on the nature of the desired effect, the application rates of the mixtures according to the invention are, in particular, in agricultural crops, from 0.01 to 8 kg/ha, preferably 0.1 to 5 kg/ha, in particular 0.5 to 3.0 kg/ha.
The application rates are, in the case of the compounds I, from 0.01 to 2.5 kg/ha, preferably 0.05 to 2.5 kg/ha, in particular 0.05 to 1.0 kg/ha.
In the case of the compounds II, the application rates are from 0.01 to 10 kg/ha, preferably 0.05 to 5 kg/ha, in particular 0.1 to 2.0 kg/ha.
For seed treatment, the application rates of the mixture are generally from 0.001 to 250 g/kg of seed, preferably 0.01 to 100 g/kg, in particular 0.01 to 50 g/kg.
If phytopathogenic harmful fungi are to be controlled, the separate or joint application of the compounds I and II or of the mixtures of the compounds I and II is effected by spraying or dusting the seeds, the plants or the soils before or after sowing of the plants, or before or after plant emergence.
The fungicidal synergistic mixtures according to the invention, or the compounds I and II, can be formulated for example in the form of ready-to-spray solutions, powders and suspensions or in the form of highly concentrated aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules, and applied by spraying, atomizing, dusting, spreading or pouring. The use form depends on the intended purpose; in any case, it should guarantee as fine and uniform as possible a distribution of the mixture according to the invention.
The formulations are prepared in a manner known per se, eg. by adding solvents and/or carriers. It is usual to admix inert additives, such as emulsifiers or dispersants, to the formulations.
Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, eg. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, or of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene; or polyoxypropylene alkyl ethers lauryl alcohol polyglycol ether acetate,
Ammermann Eberhard
Birner Erich
Leyendecker Joachim
Lorenz Gisela
Möller Bernd
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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