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United States Patent [191 [11] Patent Number: 4,940,721 Nevill Et Al

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United States Patent [191 [11] Patent Number: 4,940,721 Nevill Et Al United States Patent [191 [11] Patent Number: 4,940,721 Nevill et al. [45] Date of Patent: Jul. 10, 1990 [54] MICROBICIDAL COMPOSITIONS [56] References Cited FOREIGN PATENT DOCUMENTS [75] Inventors: David J. Nevill, Riehen; Bernhard 0236272 9/1987 European Pat. Off, . Steck, Muntelier, both of 2024824 l/ 1980 United Kingdom . Switzerland 2098607 11/1982 United Kingdom . [73] Assignee: Ciba-Geigy Corporation, Ardsley, Primary Examiner-Allen J. Robinson N.Y. Attorney, Agent, or Firm-George R. Dohmann; Edward McC. Roberts [21] App1.No.: 388,177 [57] ‘ ABSTRACT The combination of the plant microbicide 3-cyano-4 [22] Filed: 3111.31, 1989 (2,3-dichlorophenyl)-pyrrole (“fenpiclonil”) with the plant microbicide l-{2-[2-chloro-4-(4-chlorophenoxy) [30] Foreign Application Priority Data phenyl]-4-methyl- 1,3-dioxo1an-2-yln1ethyl}- 1H-1,2,4 triazole results in a synergistrically enhanced activity in Aug. 4, 1988 [CH] Switzerland ....................... .. 2960/88 the control of plant diseases. Plant microbicidal compo sitions based on such combinations are especially suit ' [51] Int. (21.5 .................... .. A01N 43/36; AOlN 43/64 able for treating seed. [52] us. c1. ................................... .. 514/383; 514/427 [58] Field of Search .............................. .. 514/383, 427 4 Claims, No Drawings 4,940,72 1 1 2 fourth main groups, such as aluminium, tin or lead, and ‘MICROBICIDAL COMPOSITIONS of the ?rst to eighth sub-groups, such as chromium, manganese, iron, cobalt, nickel, copper, zinc, etc. The The present invention relates to microbicidal mix sub-group elements of the 4th period are preferred. The tures having synergistically enhanced activity against metals may be present in any of the various valencies plant diseases and to methods of using such mixtures, attributed to them. The metal complexes may be mono especially for dressing seed. or poly-nuclear, that is to say they may contain one or The invention relates especially to the control or more organic molecular components as ligands. prevention of diseases in cereal cultivation. It is known to the person skilled in the art that the It has been found that a combination of the active activity of a fungicidal active ingredient can be greatly ingredient component I), 3-cyano-4-(2,3-dichloro enhanced or broadened by the addition of another fun phenyD-pyrrole (“fenpiclonil”) of formula I gicide having a different spectrum of activity. It has surprisingly been found, however, that the Cl Cl (1) combination of the active ingredients I and II results in CN a quite unexpectedly substantial enhancement of activ ity against seed-borne and soil-borne fungi. The enh abncement of activity achieved by the combination according to the invention is distinctly greater than the activity that would be expected from the addition of the N activities of the two individual components, that is to H say, the combination has synergistic activity. with the active ingredient component II), 1-{2-[2 Apart from synergistic fungicidal activity, the mix chloro-4-(4»chlorophenoxy)-phenyl]-4-methyl-1,3-diox tures according to the invention exhibit a pronounced olan-2-ylmethyl}-lH-l,2,4-triazole of formula II plant growth promoting activity which depends on the 25 composition of the mixture according to the invention to approximately the same extent as does the fungicidal (II) activity. Accordingly, the plant growth promoting ac tivity of the mixtures according to the invention can also be regarded as synergistic. The present invention therefore permits the dressing of seeds with lower amounts of biocides than known hitherto and therefore constitutes a very substantial or with a salt thereof results in a synergistically en enrichment of the state of the art. hanced activity in the control and prevention of plant 35 The present invention reltates not only to the applica diseases. tion of mixtures of components I and II to seed but also The compound of formula I is mentioned in DE-OS to the application of the individual pure components in No. 2,927,480 (or in GB Patent Application No. immediate succession. 2,024,824) among other intermediates. Its use as a fungi Favourable ratios of the two active ingredients are cidal active ingredient is described in EP-A No. 236272. 40 I:II=20:1 to 1:20, especially 1211: 10:1 to 1:10 and very It is distinguished especially as a contact fungicide. especially I:II=5:l to 1:5. Other advantageous ratios The compound of formula II is described as a fungi are 1:11:52 to 2:5 or 3:2 to 2:3 or_l:l. cidal active ingredient in GB Patent Application No. An enhanced activity is also observed when the com 2,098,607. The action of that triazole derivative is based pound of formula I is combined with other active ingre on the inhibition of ergosterol biosynthesis. 45 dients, provided the latter are inhibitors of demethyla The mentioned salts of the compound of formula II tion by the ergosterol synthesis route of fungi. Such can be prepared by reacting the base with acids. demethylation inhibitors are bitertanol, diniconazole, Of the acids that may be used for the preparation of ethyltrianol, ?utriafol, flusilazole, furconazole, imazalil, salts of formula II there may be mentioned: hydrohalic myclobutanil, cyproconazole, triadimefon, triadimenol acid, such as hydro?uoric acid, hydrochloric acid, hy and others, whose structure and fungicidal activity are drobromic acid or hydriodic acid and sulfuric acid, know to the person skilled in the art. ' phosphoric acid, nitric acid and organic acids, such as The combinations of active components I and II ac acetic acid, tri?uoroacetic acid, trichloroacetic acid, cording to the present invention have useful contact propionic acid, glycolic acid, thiocyanic acid, lactic action and systemic and long-lasting action in the con acid, succinic acid, citric acid, benzoic acid, cinnamic 55 trol of seed-borne and soil-borne plant diseases. Micro acid, oxalic acid, formic acid, benzenesulfonic acid, organisms in the seed are destroyed and plants in the p-toluenesulfonic acid, methanesulfonic acid, salicylic process of developing are protected from attack by acid, p-aminosalicylic acid, Z-phenoxybenzoic acid, soil-borne microorganisms by the combinations accord 2-acetoxybenzoic acid or l,2-naphthalenedisulfonic ing to the invention. acid. The mixtures according to the invention are effective The term “salts” also includes metal complexes of the against phytopathogenic fungi belonging to the follow basic component II. Those complexes consist of the ing classes: Ascomycetes (e.g. the genera Mycospha fundamental organic molecule and an inorganic or or erella, Pyrenophora); Basidiomycetes (e.g. the genera ganic metal salt, for example the halides, nitrates, sul Tilletia, Rhizoctonia); Fungi imperfecti (e. g. the genera fates, phosphates, acetates, trifluoroacetates, trichlor 65 Fusarium, Septoria, Phoma, Alternaria). The combina oacetates, propionates, tartrates, sulfonates, salicylates, tions according to the invention are especially effective _ benzoates, etc. of elements of the second main group, in seed treatment (fruit, tubers, grains), activity against such as calcium and magnesium, and of the third and Fusarium nivale on wheat ‘being especially pronounced. 4,940,72 1 3 4 They are, however, also suitable for direct treatment of impregnating the locus of the plant with a liquid formu the soil or other plant parts. They are well tolerated by lation, or by applying the compounds in solid form to plants and are ecologically non-harmful. the soid, e.g. in granular form (soil application). The In practice, the mixture according to the invention is mixture of the compounds of formulae I and II can, normally used together with the adjuvants customarily according to an especially preferred method, be applied employed in the art of formulation. The active compo to seed grains, tubers, fruit or other plant material to be nents of formulae I and II are formulated in known protected (coating) either by impregnating the material manner, e.g. to emulsi?able concentrates, coatable with a liquid formulation of the active ingredients or by pastes, directly sprayable or dilutable solutions, dilute coating it with a solid formulation. In special cases, emulsions, wettable powders, soluble powders, dusts, further types of application are also possible, for exam granulates, and also encapsulations in, e.g., polymer ple selective treatment of the plant stems or buds. substances. The methods of application, such as spray ing, atomising, dusting, scattering, coating or pouring, The compounds of formulae I and II are used in un and the form of the composition are in accordance with modi?ed form or, preferably, together with the adju the intended objectives and the prevailing circum~ vants conventionally employed in the art of formula stances. Advantageous rates of application are generally tion, and are therefore formulated in known manner e.g. from 0.0005 to a maximum of 0.5 kg, especially from into emulsifrable concentrates, coatable pastes, directly 0.001 to 0.01 kg of each of active ingredients I and II per sprayable or dilutable solutions, dilute emulsions, wetta 100 kg of material to be protected. The application ble powders, soluble powders, dusts, granulates, and conditions depend to a very considerable extent, how 20 also encapsulations in e.g. polymer substances. As with ever, on the nature (size of the surface, consistency, the nature of the compositions, the methods of applica moisture content) of the material and on environmental tion, such as spraying,
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