Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-09-05
2002-09-24
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...
Reexamination Certificate
active
06455563
ABSTRACT:
The present invention relates to novel microbicidal active ingredient mixtures having synergistically enhanced action, comprising at least two active ingredient components, and to methods of using such mixtures in plant protection.
Component I is a compound selected from the group:
(IA) 1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole (“epoxiconazol”; reference: EP-A-196 038);
(IB) 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)-butyronitrile (“fenbuconazol”; reference: EP-A-251 775);
(IC) 5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-cyclopentanol (“metconazol”; reference: EP-A-267 778);
(ID) 2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl-1,1,2,2-tetrafluoroethyl ether (“tetraconazol”; reference: EP-A-234 242);
(IE) &agr;-[2-(4-chlorophenyl)ethyl]-&agr;-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol (“tebuconazol”; reference: EP-A-40 345);
(IF) 1-[4-bromo-2-(2,4-dichlorophenyl)tetrahydrofurfuryl]-1-1,2,4-triazole (“bromuconazol”; reference EP-A-246 982),
or in each case one of the salts or metal complexes thereof; and
component II is the compound:
(IIA) 1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (“propiconazol”; reference: GB-1 522 657) and/or
(IIB) 4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidineamine (“cyprodinil”; reference: EP-A-310 550)
or in each case one of the salts or metal complexes thereof.
Of the acids that can be used for the preparation of salts of compounds of formulae I and II, the following may be mentioned: hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid; sulfuric acid, phosphoric acid, nitric acid, and organic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid and 1,2-naphthalene-disulfonic acid.
The term salts also includes metal complexes of basic components I and II. Those complexes may as desired involve only one component or both components independently. It is also possible to produce metal complexes in which the two active ingredients I and II are linked to one another to form a mixed complex.
Metal complexes consist of the underlying organic molecule and an inorganic or organic metal salt, for example a halide, nitrate, sulfate, phosphate, acetate, trifluoroacetate, trichloroacetate, propionate, tartrate, sulfonate, salicylate, benzoate, etc., of an element of main group II, such as calcium and magnesium, and of main groups III and IV, such as aluminium, tin or lead, and of subgroups I to VIII, such as chromium, manganese, iron, cobalt, nickel, copper, zinc, etc.. Preference is given to the subgroup elements of the 4th period. The metals may have any of the different valencies in which they occur. The metal complexes can be mono- or poly-nuclear, i.e. they can contain one or more organic molecule components as ligands.
Further agrochemical active ingredients, such as insecticides, acaricides, nematicides, herbicides, growth regulators and fertilisers, but especially additional microbicides, may also be added to the active ingredient mixture according to the invention.
Synergistic mixtures are known wherein
a) component I is compound IA (“epoxiconazol”) and component II is compound IIB (“cyprodinil”);
b) component I is compound IB (“fenbuconazol”) and component II is compound IIB (“cyprodinil”);
c) component I is compound IE (“tebuconazol”) and component II is compound IIB (“cyprodinil”) (reference for a), b) and c): EP-A-548 025); and
d) component I is compound IE (“tebuconazol”) and component II is compound IIA (“propiconazol”) (reference: EP-A-393 746).
The present invention does not relate to those mixtures.
It has now been found, surprisingly, that the fungicidal action of mixtures according to the invention of components I and II is not merely additive but is clearly synergistically enhanced.
Preference is given to two-component mixtures wherein
(1) component I is a compound selected from the group IA (“epoxiconazol”), IB (“fenbuconazol”), IC (“metconazol”), ID (“tetraconazol”) and IE (“tebuconazol”); and component II is compound IIA (“propiconazol”) and/or IIB (“cyprodinil”);
(2) component I is a compound selected from the group IA (“epoxiconazol”), IB (“fenbuconazol”), IC (“metconazol”), ID (“tetraconazol”) and IF (“bromuconazol”); and component II is compound IIA (“propiconazol”);
(3) component I is a compound selected from the group IC (“metconazol”), ID (“tetraconazol”) and IF (“bromuconazol”); and component II is compound IIB (“cyprodinil”).
(4) A further preferred group is formed by three-component mixtures wherein component I is a compound selected from the group IA (“epoxiconazol”), IB (“fenbuconazol”), IC (“metconazol”), ID (“tetraconazol”), IE (“tebuconazol”) and IF (“bromuconazol”); and component II is a mixture of IIA (“propiconazol”) and IIB (“cyprodinil”) and the ratio by weight of IIA:IIB=1:6 to 6:1.
(5) Of the above, preference is given especially to three-component mixtures wherein component I is compound IE (“tebuconazol”) and component II is a mixture of IIA (“propiconazol”) and IIB (“cyprodinil”).
The present invention relates also to a method of controlling fungi which comprises treating a site infested by or threatened with infestation by fungi with, in any desired sequence or simultaneously, a) a compound of formula I or one of the salts thereof and b) the compound of formula II or one of the salts thereof, it being possible also for the salts to be so selected that the two compounds are bonded to an acid radical or, in the case of a metal complex, to a central metal cation.
Advantageous mixing ratios of the two compounds are I:II=1:10 to 10:1, preferably I:II=1:6 to 6:1 and especially I:II=1:3 to 3:1.
Other advantageous mixing ratios I:II are, for example, 1:1, 1:2, 1:4, 2:1, 2:3.
In the three-component mixtures, preferred mixing ratios IIA:IIB for component II=1:6 to 6:1 and especially 1:5 to 1:1.
The compound mixtures I+II according to the invention have very advantageous curative, preventive and systemic fungicidal properties for protecting plants. The compound mixtures of the invention can be used to inhibit or to destroy the microorganisms occurring on plants or on parts of plants (the fruit, blossom, leaves, stems, tubers or roots) of different crops of useful plants, while at the same time parts of plants that grow later are also protected against such microorganisms. They can also be used as dressings in the treatment of plant propagation material, especially seed (fruit, tubers, grains) and plant cuttings (for example rice), to provide protection against fungal infections and against phytopathogenic fungi occurring in the soil. The compound mixtures according to the invention are distinguished by the fact that they are especially well tolerated by plants and are environmentally friendly.
The compound mixtures are effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Uncinula); Basidiomycetes (e.g. the genera Hemileia, Rhizoctonia, Puccinia); Fungi imperfecti (e.g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Altemaria, Pyricularia and
Pseudocercosporella herpotrichoides
); and Oomycetes (e.g. Phytophthora, Peronospora, Bremia, Pythium and Plasmopara).
Target crops to be protected within the scope of the present invention comprise, for example, the following species of plants: cereals: (wheat, barley, rye, oats, rice, sorghum and related species); beets: (sugar beet and fodder beet); pomes, stone fruit and soft fruit: (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and black-berries); leguminous plants: (beans, lentils, peas and soybean
Knauf-Beiter Gertrude
Zeun Ronald
Allen Rose M.
Robinson Allen J.
Syngenta Investment Corporation
Teoli, Jr. William A.
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