Information
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Patent Application
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20020099062
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Publication Number
20020099062
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Date Filed
January 16, 200222 years ago
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Date Published
July 25, 200222 years ago
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Inventors
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Original Assignees
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CPC
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US Classifications
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International Classifications
Abstract
The invention relates to a novel fungicidal composition comprising a fungicidally acceptable carrier and/or surface active agent together with, and synergistically effective amounts of
Description
BACKGROUND OF THE INVENTION
[0001] The present invention relates to a fungicidal composition comprising a fungicidally acceptable carrier and/or surface active agent and synergistically effective amounts of
[0002] (a) at least one benzophenone of formula I
3
[0003] wherein
[0004] R1 represents a halogen atom, an optionally substituted alkyl, alkanoyloxy or alkoxy group; or a hydroxy group,
[0005] R2 represents a halogen atom or an optionally substituted alkyl group, m is 0 or an integer of 1 to 3;
[0006] R3 independently represents a halogen atom, an optionally substituted alkyl or alkoxy group or a nitro group;
[0007] R4 represents a halogen atom, a cyano, carboxy, hydroxy or nitro group or an optionally substituted alkyl, alkoxy, alkenyl, alkylthio, alkylsulphinyl, alkylsulphonyl or amino group;
[0008] R5 represents an optionally substituted alkyl group;
[0009] R6 represents a halogen atom or a nitro group, an optionally substituted alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, cycloalkyl, cycloalkyloxy, aryloxy group;
[0010] n is 1 or 1; and
[0011] R7 independently represents a halogen atom, an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkoxy group;
[0012] (b) at least one fungicidally active ingredient selected from the following groups
[0013] (A), (B), (C), (D) and (E):
[0014] (A) an ergosterol biosynthesis inhibitor;
[0015] (B) a strobilurine derivative,
[0016] (C) a melanin biosynthesis inhibitor,
[0017] (D) a compound selected from the group consisting of acibenzolar, benomyl, captan, carboxin, chlorothalonil, copper, cyprodinil, dinocap, dithianon, dimethomorph, dodine, ethirimol, famoxadone, fenpiclonil, fluazinam, mancozeb, metalaxyl, pyrifenox, sulfur and vinclozolin, and
[0018] (E) an azolopyrimidine of formula II
4
[0019] in which
[0020] R8 and R9 each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group, or
[0021] R8 and R9 together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring,
[0022] R10 represents hydrogen or an alkyl or aryl group,
[0023] R11 represents a hydrogen or halogen atom or an alkyl or alkoxy group,
[0024] L independently represents a halogen atom or an optionally substituted alkyl or alkoxy group,
[0025] A represents N or CR12, wherein R12 has the meaning given for R10, and p is 0 or an integer from 1 to 5.
[0026] The fungicidal compounds of formula I to be used according to the present invention are known for example from U.S. pat. No. 5,773,663.
[0027] The compounds of the classes (A), (B) and (D) are known from The Pesticide Manual 11th edition 1997, Editor Clive Tomlin.
[0028] The class of melanin biosynthesis inhibitors (MBI) (C) are chemical compounds which are capable of diminishing the in-vivo synthesis of melanin by inhibiting any of the reductase and/or dehydratase enzymes which are responsible for converting tetrahydroxynaphthalene into dihydroxynaphthalene. This class of compounds includes the following known compounds: carpropamid, chlobenthiazione, diclocymet, pyroquilon, phthalide, tricyclazole and certain phenoxyamides, which are known for example from EP 0 262 393, in particular AC 382042 and Japanese patent application JP 5-9165-A.
[0029] The fungicidal compounds of formula II to be used according to the present invention are known for example from U.S. pat. No. 5,593,996 and from International patent applications WO 98/46607 and WO 98/46608.
[0030] U.S. pat. No. 5,773,663 suggests to combine fungicidal benzophenone derivatives with other fungicides such as 4,6-dinitro-o-cresol, benalaxyl, benomyl, captafol, captan, carbendazim, chlorothalonil, copper, cymoxanil, dichlofluanid, dichlone, difenoconazole, dimethomorph, diniconzole, dinocap, dithianon, fenpiclonil, fenpropiomorph, hymaxazol, imazalil, iprodione, isoprothiolane, kasugamycin, mancozeb, mepronil, mercuric oxide, oxadixyl, oxolinic acid, penconazole, propineb, pyrifenox, thiabendazole, thiram, toldlofos-methyl, triadimefon, triflumizole, triforine validamycin A, vinclozolin, zineb and ziram.
[0031] However, there is no hint that such mixtures show synergistic effects and can advantageously be used for controlling diseases such as wheat powdery mildew, wheat leaf rust and wheat Septoria leaf blotch, Botrytis diseases and others.
[0032] Surprisingly, a strong synergy between the compounds of formula I and the fungicidally active ingredients selected from the classes (A), (B), (C), (D) and (E) as described above in greenhouse and field trials was found when these two compounds were in-tank mixed and when the activity of these mixtures was compared with that of the solo activity of each active ingredient.
[0033] A mixture of fungicides shows synergistic effect if the fungicidal activity of the mixture is larger than the sum of activities of the separately applied compounds. The expected fungicidal activity for a given mixture of two fungicides can also be calculated as follows (See Colby, S. R., “Calculating synergistic and antagonistic response of herbicide combinations”, Weeds 15, pp 20-22 (1967):
1
[0034] wherein
[0035] x is the efficacy in % compared with an untreated control upon treatment with a fungicidal active ingredient A at a dose rate a;
[0036] y is the efficacy in % compared with an untreated control upon treatment with a fungicidal active ingredient B at a dose rate b;
[0037] EE is the expected efficacy with a combination of fungicidal active ingredients A and B at a dose of a+b, respectively.
[0038] If the actual efficacy (E) exceeds the expected (calculated) one (EE), the mixture displays a synergistic effect.
SUMMARY OF THE INVENTION
[0039] (b) The present invention includes a fungicidal composition comprising an acceptable carrier and/or surface active agent and synergistically effective amounts of at least one compound of formula I and at least one fungicidal active ingredient selected from the following the following groups (A), (B), (C), (D) and (E):
[0040] (A) an ergosterol biosynthesis inhibitor;
[0041] (B) a strobilurine derivative,
[0042] (C) a melanin biosynthesis inhibitor,
[0043] (D) a compound selected from the group consisting of acibenzolar (BION), benomyl, captan, carboxin, chlorothalonil, copper, cyprodinil, dinocap, dithianon, dimethomorph, dodine, ethirimol, famoxadone, fenpiclonil, fluazinam, mancozeb, metalaxyl, pyrifenox, sulfur and vinclozolin, and
[0044] (E) an azolopyrimidine of formula II.
[0045] The present invention also includes a method of controlling the growth of phytopathogenic fungi at a locus which comprises applying synergistically effective amounts of at least one benzophenone of formula I and at least one fungicidally active ingredient selected from the following classes (A), (B), (C), (D) and (E) as defined above to the locus.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0046] Preferred compounds of formula I are benzophenones of formula IA,
5
[0047] wherein
[0048] R1 represents a halogen atom, a methyl, trifluoromethyl, methoxy or hydroxy group, in particular a chlorine atom, a methyl or methoxy group;
[0049] R2 represents a halogen atom, in particular a chlorine atom or a methyl group;
[0050] R3 represents a bromine or chlorine atom, a methyl, trifluoromethyl or nitro group, in particular a bromine atom;
[0051] R4 represents a methyl group;
[0052] R5 represents an alkyl group, in particular a methyl group;
[0053] R6 and R7 each independently represent an alkoxy group which may be substituted by a phenyl, alkylphenyl or halophenyl group, preferably C1-6 alkoxy being optionally substituted by a phenyl, methylphenyl or fluorophenyl group, in particular methoxy, benzyloxy and 2-fluorobenzyloxy; and
[0054] n is 0 or 1.
[0055] Particularly preferred are the benzophenones selected from the group consisting of 6′-butoxy-2,6-dichloro-4′,5′-dimethoxy-2′-methylbenzophenone coded BP-1,2,6-dichloro-4′,5′-dimethoxy-6′-(2-fluorobenzyloxy)-2′-methylbenzophenone coded BP-2,6′-benzyloxy-4′,5′-dimethoxy-2,6-dimethyl-2′-methylbenzophenone coded BP-3; 5-bromo-2′,6-dimethyl-2,4′,5′, 6′-tetramethoxybenzophenone coded BP-4 and 2,6-dichloro-2′-methyl-4′,5′, 6′-trimethoxybenzophenone coded BP-5, most preferred is BP-4.
[0056] Preferred ergosterol biosynthesis inhibiotors of group (A) are selected from the group consisting of fenarimol, fenpropimorph, fenpropidine, spiroxamine and triforine.
[0057] Another group of ergosterol biosynthesis inhibiotors are azole derivatives of formulae IIIA and IIIB,
6
[0058] wherein
[0059] E represents a linking group selected from the groups (a), (b), (c), (d) and (e):
7
[0060] in which
[0061] X1 represents an alkyl or an optionally substituted phenyl group;
[0062] X2 and X3 each independently represent a hydrogen atom or an alkyl group;
[0063] X4 represents an alkyl or cyclopropylalkyl group;
[0064] X5 represents a hydroxy or cyano group;
[0065] X6 represents an optionally substituted phenyl group;
[0066] X7 represents a halogen atom;
[0067] q is 1,2 or3; and
[0068] r is 0 or 2;
8
[0069] wherein X7 and q have the meaning given for formula IIIA, and
[0070] E represents a group of formula —N(X8)—(CH2)s—O—, in which X8 represents a hydrogen atom or an alkyl group and s is an integer from 1 to 6.
[0071] Particularly preferred azole derivatives of group (A) are selected from the group consisting of cyproconazole, epoxiconazole, flusilazole, metconazole, myclobutanil, penconazole, prochloraz, propiconazole, tebuconazole, triadimefon and tridimenol. Most preferred are epoxiconazole, metconazole, myclobutanil and prochloraz.
[0072] Preferred strobilurine derivatives of group (B) are the compounds of formula IV,
9
[0073] wherein
[0074] W represents N or CH;
[0075] B represents a —O—, —OCH2—, a —CH2O—, a pyrimid-4,6-dioxydiyl group or a group
10
[0076] of formula
[0077] R12 represents a C1-4 alkyl group;
[0078] R13 represents a C1-6 alkoxy or a C1-6 alkylamino group;
[0079] R14 represents a hydrogen or halogen atom or a cyano, a C1-4 alkyl or a C1-4 haloalkyl group; and
[0080] s is 0, 1 or2;
[0081] in particular azoxystrobin, kresoxim methyl, trifloxystrobin or SSF126, most preferred azoxystrobin and kresoxim methyl.
[0082] Preferred melanin inhibitors of group (C) are selected from the group consisting of capropamid, chlobenthiazone, diclocymet, pyroquilon, phthalide, tricyclazole and a phenoxamide coded AC 382042, most preferred is AC 382042.
[0083] Preferred compounds of group (D) are selected from the group consisting of acibenzolar (BION), cyprodinil, dodine, ethirimol, famoxadone, fenpiclonil, fluazinam, mancozeb and metalaxyl.
[0084] Preferred azolopyrimidines of group (E) are the compounds of formula IIA,
11
[0085] wherein
[0086] R8 represents a C1-8 alkyl, C2-8 alkenyl, C3-8 cycloalkyl or C1-8 haloalkyl group, in particular a straight-chained or branched C3-6 alkyl, C2-6 alkenyl, C5-6 cycloalkyl or C2-6 fluoroalkyl group, most preferred an isopropyl, 2-butyl, cyclopentyl, methallyl, 2,2,2-trifluoroethyl or 1,1,1-trifluoroprop-2-yl group;
[0087] and
[0088] R9 represents a hydrogen atom, or a C1-8 alkyl group; most preferred a hydrogen atom or a methyl or ethyl group; or
[0089] R8 and R9 together form an optionally substituted alkylene group having 3 to 6 carbon atoms in the main chain, in which one CH2 group may be replaced by O, S or NH, in particular a piperid-1-yl group being optionally substituted by a C1-6 alkyl group, most preferred a 4-methylpiperid-1-yl group;
[0090] L1, L2 and L3 each independently represent a hydrogen or halogen atom or a C1-4 alkoxy group, at least one of which represents a halogen atom, in particular wherein L1 represents a fluorine atom, L2 represents a hydrogen or fluorine atom or a methoxy group and L3 represents a fluorine or chlorine atom; and
[0091] Hal denotes a halogen atom, in particular a chlorine atom.
[0092] Particularly preferred are the azolopyrimidines of formula II selected from the group consisting of 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(cyclopropylamino)-[1,2,4]triazolo[1,5-a]pyrimidine coded AP-1, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperid-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine coded AP-2,5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[1,5-a]pyrimidine coded AP-3 and 5-chloro-6-(2,4,6-trifluorophenyl)-7-[2-(1 1,1 -trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine coded AP-4, most preferred is AP-4.
[0093] A particularly preferred embodiment of this invention are compositions of three active ingredients which comprise one compound of formula I and two different compounds selected from the groups (A), (B), (C), (D) and (E), preferably one strobilurine compound selected from group (B) and one ergosterol biosynthesis inhibitor of group (A), in particular kresoxim-methyl and epoxiconazole or kresoxim-methyl and fenpropimorph.
[0094] Another particularly preferred embodiment of the invention are compositions comprising one compound of formula I and two different compounds of group (D), in particular dimethomorph and mancozeb.
[0095] Preferred are co-formulations, comprising the following constituents:
[0096] a carrier;
[0097] at least one benzophenone of formula I,
[0098] at least one compound selected from the classes (A) through (E) as defined above;
[0099] optionally an adjuvant selected from the group consisting of polyalkoxylated alcohols, triglycerides and amines, in particular Synperonic 91-6, which is commercially available from Uniqema, formerly ICI Surfactants;
[0100] optionally a foam breaking agent.
[0101] The compound of formula I and the compound selected from the classes (A) through (E) as defined above are to be applied together, in synergistically effective amounts. These synergistic mixtures exhibit an extraordinary efficacy against a broad range of phytopathogenic fungi, in particular against fungi from the classes ascomycetes, basidiomycetes, oomycetes and deuteromycetes.
[0102] Therefore, they can be applied advantageously against a broad range of diseases in different crops. They may be applied as leaf, stem, root, into-water, seed dressing, nursery box or soil fungicides.
[0103] The mixture according to the invention may be preferably applied for controlling phytopathogenic fungi of the genera: Achlya, Altemaria, Balansia, Bipolaris, Blumeria, Botrytis, Cercospora, Cochliobolus, Curvularia, Cylindrocladium, Drechslera, Entyloma, Erysiphe, Fusarium, Gaeumannomyces, Gerlachia, Gibberella, Guignardia, Leptosphaeria, Magnaporthe, Mucor, Mycosphaerella, Myrothecium, Nigrospora, Peronospora, Phoma, Pseudoperonospora, Pseudocercosporella, Phytophthora, Puccinia, Pyrenophora, Pyricularia, Pythium, Rhizoctonia, Rhizopus, Rhynchosporium, Sarocladium, Sclerophthora, Sclerotium, Septoria, Tilletia, Uncinula, Ustilago, Ustilaginoidea, and Venturia, in particular the species Blumeria graminis f. sp. tritici, Cercospora beticola, Septoria tritici, Erysiphe cichoracearum, Puccinia recondita and Pyrenophora teres.
[0104] The mixtures according to the invention are in particular applied for controlling the above phytopathogenic fungi on monocotylydoneous plants, such as barley and wheat, rice and turf grases or fruit crops such as pomefruits, stonefruits and vines as well as all kinds of vegetables and ornamentals.
[0105] The application rate of the compound of formula I according to this invention is usually in the range of 1 to 2000 grams of active ingredient (g a.i.) per hectare, with rates between 20-500 g a.i./ha often achieving satisfactory control. The optimal rate for a specific application will depend on the crop(s) under cultivation and the predominant species of infesting fungi, and readily may be determined by established biological tests known to those skilled in the art.
[0106] In general, the preferred application rate of the compounds of formula I is in the range of 10 to 500 g a.i./ha, preferably 20-300 g a.i./ha.
[0107] The optimal rate for the compound of group (b) including the classes (A) through (E) will, however, depend on the crop(s) under cultivation and the level of infestation by the fungus, and can readily be determined by established biological tests.
[0108] The ratio (by weight) of the compound of formula I to the fungicidal active ingredient of the classes (A) through (E) as defined above is as a rule, from 100:1 to 1:100. The preferred ratio formula I: (A) through (E) may vary, e.g., from about 10:1 to about 1:10, in particular from about 5:1 to about 1:5, most preferred from 2:1 to 1:2.
[0109] In the three-ways-compositions according to the present invention, i.e. the compositions containing one compound of formula I and two different compounds selected from the classes (A) through (E), the preferred relative ratios (by weight) are as follows:
[0110] compound of formula I: 200 to 1, preferably 20 to 1
[0111] 1st compound of (A) to (E): 1 to 100, preferably 1 to 10
[0112] 2nd compound of (A) to (E): 1 to 100, preferably 1 to 10.
[0113] The active compounds can be co-formulated together in a suitable ratio according to the present invention, together with usual carriers or diluents and/or additives known in the art.
[0114] Accordingly the invention further provides a fungicidal composition which comprises a carrier and, as active ingredient, at least one compound of formula I as defined above and at least one fungicidal active ingredient selected from the classes (A) through (E) as defined above.
[0115] A method of making such a composition is also provided which comprises bringing the compound of formula I and the fungicidal active ingredient selected from the classes(A) through (E) as defined above into association with at least one carrier. It is also envisaged that different isomers or mixtures of isomers of formula I and/or the fungicidal active ingredient selected from the classes (A) through (E) may have different levels or spectra of activity and thus compositions may comprise individual isomers or mixtures of isomers.
[0116] A composition according to the invention preferably contains from 0.1% to 99.9%, preferably 0.2 to 80% by weight (w/w) of active ingredients.
[0117] A carrier in a composition according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed, foliage, soil, or into the water where the plant grow, or to the roots or to facilitate storage, transport or handling. A carrier may be a solid or a liquid, including material which is normally a gas but which has been compressed to form a liquid.
[0118] The compositions may be manufactured into e.g. emulsion concentrates, solutions, oil in water emulsions, wettable powders, soluble powders, suspension concentrates, dusts, granules, water dispersible granules, tablets, micro-capsules, gels and other formulation types by well-established procedures. These procedures include intensive mixing and/or milling of the active ingredients with other substances, such as fillers, solvents, solid carriers, surface active compounds (surfactants), and optionally solid and/or liquid auxilaries and/or adjuvants. The form of application such as spraying, atomizing, dispersing or pouring may be chosen like the compositions according to the desired objectives and the given circumstances.
[0119] Solvents may be aromatic hydrocarbons, e.g. Solvesso® 200, substituted naphthalenes, phthalic acid esters, such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons, e.g. cyclohexane or paraffins, alcohols and glycols as well as their ethers and esters, e.g. ethanol, ethyleneglycol mono- and dimethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, or y-butyrolactone, higher N-alkylpyrrolidones, e.g. N-octylpyrrolidone or N-cyclohexylpyrrolidone, epoxidized plant oil esters, e.g. methylated coconut or soybean oil ester and water. Mixtures of different liquids are often suitable.
[0120] Solid carriers, which may be used for dusts, wettable powders, water dispersible granules, or granules, may be mineral fillers, such as calcite, talc, kaolin, montmorillonite or attapulgite or others. The physical properties may be improved by addition of highly dispersed silica gel or polymers. Carriers for granules may be porous material, e.g. pumice, kaolin, sepiolite, bentonite; non-sorptive carriers may be calcite or sand or others. Additionally, a multitude of pre-granulated inorganic or organic materials may be used, such as dolomite or crushed plant residues.
[0121] Pesticidal compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application. The presence of small amounts of a carrier which is a surfactant facilitates this process of dilution. Thus, preferably at least one carrier in a composition according to the invention is a surfactant. For example, the composition may contain at two or more carriers, at least one of which is a surfactant.
[0122] Surfactants may be nonionic, anionic, cationic or zwitterionic substances with good dispersing, emulsifying and wetting properties depending on the nature of the compound according to general formula I to be formulated. Surfactants may also mean mixtures of individual surfactants.
[0123] The compositions of the invention may for example be formulated as wettable powders, water dispersible granules, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Wettable powders usually contain 5 to 90% w/w of active ingredient and usually contain in addition to solid inert carrier, 3 tol 0% w/w of dispersing and wetting agents and, where necessary, 0 to 10% w/w of stabilizer(s) and/or other additives such as penetrants or stickers. Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and may be diluted in the field with further solid carrier to give a composition usually containing 0.5 to 10% w/w of active ingredient. Water dispersible granules and granules are usually prepared to have a size between 0.15 mm and 2.0 mm and may be manufactured by a variety of techniques. Generally, these types of granules will contain 0.5 to 90% w/w active ingredient and 0 to 20% w/w of additives such as stabilizer, surfactants, slow release modifiers and binding agents. The so-called “dry flowables” consist of relatively small granules having a relatively high concentration of active ingredient. Emulsifiable concentrates usually contain, in addition to a solvent or a mixture of solvents, 1 to 80% w/v active ingredient, 2 to 20% w/v emulsifiers and 0 to 20% w/v of other additives such as stabilizers, penetrants and corrosion inhibitors. Suspension concentrates are usually milled so as to obtain a stable, non-sedimenting flowable product and usually contain 5 to 75% w/v active ingredient, 0.5 to 15% w/v of dispersing agents, 0.1 to 10% w/v of suspending agents such as protective colloids and thixotropic agents, 0 to 10% w/v of other additives such as defoamers, corrosion inhibitors, stabilizers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation and crystalization or as antifreeze agents for water.
[0124] Aqueous dispersions and emulsions, for example compositions obtained by diluting the formulated product according to the invention with water, also lie within the scope of the invention.
[0125] Of particular interest in enhancing the duration of the protective activity of the compounds of this invention is the use of a carrier which will provide slow release of the pesticidal compounds into the environment of a plant which is to be protected.
[0126] The biological activity of the active ingredient can also be increased by including an adjuvant in the formulation or the spray dilution. An adjuvant is defined here as a substance which can increase the biological activity of an active ingredient but is not itself significantly biologically active. The adjuvant can either be included in the formulation as a coformulant or carrier, or can be added to the spray tank together with the formulation containing the active ingredient.
[0127] As a commodity the compositions may preferably be in a concentrated form whereas the end user generally employs diluted compositions. The compositions may be diluted to a concentration down to 0.001% of active ingredient. The doses usually are in the range from 0.01 to 10 kg a.i./ha.
[0128] Examples of formulations which can be used according to the invention are:
1|
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SC-I 1
active ingredientBP-1100.0 g
Dispersing agentMotwet D4251) 25.0 g
Dispersing agentPluronic ® PE105002) 5.0 g
Antifoaming agentRhodorsil ® 426R3) 1.5 g
Dispersing agentRhodopol ® 233) 2.0 g
Antifreezing agentPropylene glycol 80.0 g
Biocidal agentProxel ® GXL4) 1.0 g
Waterto 1000 ml
SC-I 2
active ingredientBP-4100.0 g
Dispersing agentSoprophor ® FL3) 30.0 g
Antifoaming agentRhodorsil ® 426R3) 1.5 g
Dispersing agentRhodopol ® 233) 2.0 g
Antifreezing agentPropylene glycol 80.0 g
Biocidal agentProxel ® GXL4) 1.0 g
Waterto 1000 ml
SC-A-E
active ingredientfungicide selected from classes200.0 g
(A) through (E)
Dispersing agentSoprophor ® FL3) 25.0 g
Antifoaming agentRhodorsil ® 426R3) 1.5 g
Dispersing agentRhodopol ® 233) 2.0 g
Antifreezing agentPropylene glycol 80.0 g
Biocidal agentProxel ® GXL4) 1.0 g
Waterto 1000 ml
SC-I + A-E
active ingredientBP-4 60.0 g
active ingredientfungicide selected from classes120.0 g
(A) through (E)
Dispersing agentSoprophor ® FL3) 25.0 g
Antifoaming agentRhodorsil ® 426R3) 1.5 g
Dispersing agentRhodopol ® 233) 2.0 g
Antifreezing agentPropylene glycol 80.0 g
Biocidal agentProxel ® GXL4) 1.0 g
Waterto 1000 ml
DC-I 1
active ingredientBP-4100.0 g
Wetting agentPluronic ® PE64002) 50.0 g
Dispersing agentLutensol ® TO 122) 50.0 g
Solventbenzyl alcoholto 1000 ml
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1)Product commercially available from Witco
2)Product commercially available from BASF AG, Germany
3)Product commercially available from Rhône-Poulenc
4)Product commercially available from Zeneca
[0129] The formulation SC-A-E comprising a compound selected from the classes (A) through (E) is in-tank mixed with any of the other formulations SC-I 1, SC-I 2, SC-I 3, or DC-I which comprise the compound of formula I.
[0130] In a preferred embodiment the active ingredients are added to the tank mix together each as solo formulation.
[0131] Therefore, the present invention relates to a kit for the preparation of a spray mixture consisting of two separate containments:
[0132] (i) a containment which comprises at least one benzophenone of formula I, in particular one or more compounds selected from BP-1 through BP-4, conventional carriers and optionally adjuvants;
[0133] (ii) a containment which comprises at least one active ingredient selected from the classes (A) through (E).
[0134] In a preferred embodiment the said kit will consist of two bottles with dispensing means which allow the easy and correct addition of the active ingredients (a) and (b) to the tank mix.
[0135] The formulation SC-I+A-E comprising BP-4 and a fungicidal active ingredient selected from the classes (A) through (E) as defined above can be used directly for preparing the tank mix according to the present invention.
[0136] A composition according to the invention preferably contains from 0.5% to 95% by weight of active ingredients.
[0137] As commodity the compositions may preferably be in a concentrated form whereas the end-user generally employs diluted compositions. The compositions may be diluted down to a concentration of 0.0001% of active ingredients.
[0138] The compositions of this invention can be applied to the plants or their environment simultaneous with or in succession with other active substances. These other active substances can be either fertilizers, agents which donate trace elements or other preparations which influence plant growth. However, they can also be other fungicides, selective herbicides, insecticides, bactericides, nematicides, algicides, molluscidides, rodenticides, virucides, compounds inducing resistance into plants, biological control agents such as viruses, bacteria, nematodes, fungi and other microorganisms, repellents of birds and animals, and plant growth regulators, or mixtures of several of these preparations, if appropriate together with other carrier substances conventionally used in the art of formulation, surfactants or other additives which promote application.
[0139] Examples of insecticidal compounds are alpha-cypermethrin, benfuracarb, BPMC, buprofezine, carbosulfan, cartap, chlorfenvinphos, chlorpyrifos-methyl, cycloprothrin, cypermethrin, esfenvalerate, ethofenprox, fenpropathrin, flucythrinate, flufenoxuron, hydramethylnon, imidacloprid, isoxathion, MEP, MPP, nitenpyram, PAP, permethrin, propaphos, pymetrozine, silafluofen, tebufenozide, teflubenzuron, temephos, terbufos, tetrachlorvinphos and triazamate.
[0140] Examples of biological control agents are: Bacillus thuringiensis, Verticillium lecanii, Autographica califomica NPV, Beauvaria bassiana, Ampelomyces quisqualis, Bacilis subtilis, Pseudomonas cholororaphis, Pseudomonas fluorescens, Steptomyces griseoviridis and Trichoderma harzianum.
[0141] Examples of chemical agents that induce systemic acquired resistance in plants such are: isonicotinic acid or derivatives thereof, 2,2-dichloro-3,3-dimethylcyclopropylcarboxylic acid.
[0142] The present invention is of wide applicability in the protection of crops, trees, residential and ornamental plants against fungal attack. Preferred crops are cereals, such as wheat and barley, rice as well as vines and apples. The duration of the protection is normally dependent on the individual compound selected, and also a variety of external factors, such as climate, whose impact is normally mitigated by the use of a suitable formulation.
[0143] The following examples further illustrate the present invention. It should be understood, however, that the invention is not limited solely to the particular examples given below.
EXAMPLES
[0144] General Methods
[0145] The trials are carried out under greenhouse (Examples 1 to 18) or field conditions (Example 19) in residual or curative applications. The fungicides are applied in single treatments, or in a combination comprising a benzophenone of formula I and a compound selected from the classes (A) through (E) as defined above. The compounds are applied in form of an aqueous spray mix obtained from concentrated formulation or the technical material.
[0146] I. Cereals and Dicots—Greenhouse
[0147] 1. Seed is planted in 6 cm diameter plastic pots and maintained in the greenhouse.
[0148] 2. When the primary leaf is fully expanded in the case of cereals or several leaves are present in the case of dicots, formulated test compounds are sprayed with a three nozzle overhead fungicide sprayer to near run-off. Alternatively, a single nozzle overhead track sprayer is used for application of the compounds to cereals at a rate of 200 I/ha. Plants are then allowed to air-dry.
[0149] 3. Inoculation precedes treatment in the case of curative evaluations and follows treatment in case of residual evaluations. For inoculation of powdery mildew disease, plants are set up on greenhouse benches with bottom watering mats and inoculated by dusting them with conidia from infected plants. Between inoculation and treatment for curative evaluations and between treatment and inoculation for residual evaluations, plants are maintained in the greenhouse with bottom watering. For inoculation of non-powdery mildew diseases, an aqueous spore suspension of the pathogen is applied to the plant and the plants are kept 1-2 days in a moist infection chamber before being returned to the greenhouse where they are maintained by bottom watering.
[0150] 4. Disease on the foliage as percent leaf area with disease symptoms/signs is evaluated about 7 days after inoculation. In the case of wheat, the tips and bases of the leaves are excluded from the evaluation.
2
[0151] FORMULATION, REFERENCE COMPOUNDS AND CONTROLS:
[0152] 1. Technical compounds are formulated in a solvent/surfactant system consisting of 5% acetone and 0.05% Tween 20 in deionized water. Compounds are dissolved in acetone prior to addition of the water; the Tween 20 can be added through either the acetone or the water. Dilutions are made using the solvent/surfactant system.
[0153] Formulated compounds are prepared using deionized water.
[0154] 2. Two kinds of controls are included:
[0155] Plants treated with the solvent/surfactant solution and inoculated (Solvent Blank).
[0156] Untreated plants which are inoculated (Inoculated Control). For the field study formulated benzophenones BP-1 through BP-4 and formulated compounds from the classes (A) through (E) were used.
[0157] Evaluation of the Disease
[0158] Assessments of the diseases took place at the indicated day after the application of the compounds. Per cent infected leaf area infected was evaluated. The efficacy of the compounds/compounds mixtures to control the diseases was calculated by using the formula given above under item 4:
[0159] II. Apple Fruit Botrytis
[0160] 1. Apples (Malus X domestica Borkh.) variety “Golden Delicious” are disinfected by washing them briefly in 70% ethanol. After drying the apples are marked with four short equal-distant lines indicating the positions to be wounded.
[0161] 2. Corresponding with the marks, four holes are poked around the apple equator with a pipette tip. 10 μl of the treatment solution are pipetted into each hole.
[0162] 3. Three hours after application, 10 μl of a conidial suspension of Botrytis cinerea are pipetted into each hole. For incubation, the treated/inoculated apples are stored for five days.
[0163] 4. Disease occurs as rotten apple tissue surrounding the inoculated wounds.
[0164] The diameter of the rotten zone around each wound is measured.
[0165] Formulation, Reference Compounds and Controls:1.
[0166] Technical compounds are formulated in a solvent system consisting of 5% acetone and 0.05% Tween 20 in deionized water.
[0167] Compounds are dissolved in acetone prior to dilution with water.
[0168] Formulated compounds are prepared using deionized water.
[0169] 2. Three kinds of controls are included:
[0170] Apples treated with the solvent solution and inoculated (Solvent Blank).
[0171] Untreated apples which are inoculated (Inoculated Control).
[0172] Untreated apples which are not inoculated (Uninoculated Control).
[0173] Evaluation of the Disease
[0174] Assessments of the diseases took place at the indicated day after the application of the compounds. Per cent infected leaf area infected was evaluated. The efficacy of the compounds/compounds mixtures to control the diseases was calculated by using the formula:
3
[0175] Determination of Synerciy
[0176] Synergy was calculated using the % disease control values of specific treatments for the two COLBY formula given hereinabove
[0177] III. Field Tests
[0178] The compounds are applied according to good agricultural practice in form of an aqueous spray mix obtained from concentrated formulation or the technical material at a rate of 400 I/ha. The disease control is evaluated according to the formula given for the greenhouse tests.
[0179] A Greenhouse Tests
Example 1
[0180] Fungicidal efficacy of the mixture of BP-1 +AP-1 (4 day curative) against Erysiphe graminis on wheat
[0181] The tank mix was obtained from technical materials of BP-1 and AP-1. The observed and expected efficacies with different rates are given in Table l:
2TABLE I
|
|
dose rate (ppm)
BP-1AP-1Observed EfficacyExpected Efficacy
|
125042—
2501—
01250—
0250—
1251255642
125255442
25125211
252541
|
Example 2
[0182] Fungicidal efficacy of the mixture of BP-1 +AP-2 (4 day curative) against Erysiphe graminis on wheat
[0183] The tank mix was obtained from technical materials of BP-1 and AP-2. The observed and expected efficacies with different rates are given in Table II:
3TABLE II
|
|
dose rate (ppm)
BP-1AP-2Observed EfficacyExpected Efficacy
|
125042—
125042—
2501—
01258—
0250—
1251256747
125257342
25125209
252591
|
Example 3
[0184] Fungicidal efficacy of the mixture of BP-1 +triadimefon (4 day curative) against Erysiphe gramiminis on wheat
[0185] The tank mix was obtained from technical material of BP-1 and a wettable powder formulation containing 250 g/kg triadimefon. The observed and expected efficacies with different rates are given in Table III:
4TABLE III
|
|
dose rate (ppm)
BP-1triadimefonObserved EfficacyExpected Efficacy
|
125042—
2501—
012530—
02512—
1251258559
125255649
251254131
2525613
|
Example 4
[0186] Fungicidal efficacy of the mixture of BP-5 +triforine (3 day protective) against Erysiphe graminis on wheat The tank mix was obtained from technical material of BP-5 and an EC formulation containing 190 g/l triforine. The observed and expected efficacies rates are given in Table IV:
5TABLE IV
|
|
dose rate (ppm)
BP-5triforineObserved EfficacyExpected Efficacy
|
25031—
5012—
012512—
251255941
5252624
|
Example 5
[0187] Fungicidal efficacy of the mixture of BP-1 +triadimefon (3 day curative) against Erysiphe gramiminis on wheat
[0188] The tank mix was obtained from technical material of BP-1 and a wettable powder formulation containing 250 g/kg triadimefon. The observed and expected efficacies with different rates are given in Table V:
6TABLE V
|
|
dose rate (ppm)
BP-1triadimefonObserved EfficacyExpected Efficacy
|
5078—
1044
02524—
5259083
1257857
|
Example 6
[0189] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) against Erysiphe cichoracearum on cucumbers The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table VI:
7TABLE VI
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
BP-4TC 100%64100
1651
46
11
DithianonWG 700 g/kg2560
640
160
40
CyprodinilTC 100 %25615
640
160
40
TriforineEC 190 g/l25696
6479
1644
41
FenpropidinEC 750 g/l25669
6421
166
40
MancozebWP 800 g/kg25633
641
160
40
QuinoxyfenTC 100%256100
64100
16100
490
ChlorothalonilSC 500 g/l2561
640
160
40
EthirimolSC 280 g/l256100
6494
1683
450
DimethomorphTC 100%25618
640
160
40
BIONWG 500 g/kg2560
640
160
40
AzoxystrobinTC 100%256100
64100
1696
478
BP-4 +Tankmix64 + 256100100
Dithianon16 + 647351
4 + 16316
1 + 4291
BP-4 +Tankmix64 + 25692100
Cyprodinil16 + 645951
4 + 16516
1 + 4321
BP-4 +Tankmix64 + 256100100
Triforine16 + 649990
4 + 166547
1 + 4313
BP-4 +Tankmix64 + 256100100
Fenpropidin16 + 649661
4 + 166012
1 + 4561
BP-4 +Tankmix64 + 256100100
Mancozeb16 + 649952
4 + 16546
1 + 4381
BP-4 +Tankmix64 + 256100100
Quinoxyfen16 + 64100100
4 + 16100100
1 + 410091
BP-4 +Tankmix64 + 256100100
Chlorothalonil16 + 649951
4 + 16226
1 + 4141
BP-4 +Tankmix64 + 256100100
Ethirimol16 + 6410097
4 + 168584
1 + 45351
BP-4 +Tankmix64 + 256100100
Dimethomorph16 + 649951
4 + 16376
1 + 4101
BP-4 +Tankmix64 + 256100100
BION16 + 645351
4 + 16126
1 + 411
BP-4 +Tankmix64 + 256100100
Azoxystrobin16 + 64100100
4 + 169996
1 + 49278
|
[0190] Fungicidal efficacy of the mixture of BP-4 +triadimefon (4 day curative) against against Puccinia recondita on wheat
[0191] The tank mix was obtained from technical material of BP-4 and a wettable powder formulation containing 250 g/kg triadimefon. The observed and expected efficacies with different rates are given in Table VII:
8TABLE VII
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
BP-4TC 100%25613
640
160
40
DithianonWG 700 g/kg25695
6484
1616
44
CyprodinilTC 100%2560
640
160
40
TriforineEC 190 g/l256100
6490
167
40
FenpropidinEC 750 g/l25697
648
160
40
MancozebWP 800 g/kg25691
6428
160
40
QuinoxyfenTC 100%2560
640
160
40
ChlorothalonilSC 500 g/l25631
640
160
40
EthirimolSC 280 g/l2560
640
160
DimethomorphTC 100%2560
640
160
BIONWG 500 g/kg2560
640
160
40
BP-4 +Tankmix256 + 25610095
Dithianon64 + 6410084
16 + 1610016
4 + 41004
BP-4 +Tankmix256 + 25610013
Cyprodinil64 + 641000
16 + 161000
4 + 41000
BP-4 +Tankmix256 + 256100100
Triforine64 + 6410090
16 + 161007
4 + 41000
BP-4 +Tankmix256 + 25610097
Fenpropidin64 + 64968
16 + 16930
4 + 4910
BP-4 +Tankmix256 + 25610092
Mancozeb64 + 649728
16 + 16940
4 + 4920
BP-4 +Tankmix256 + 2568913
Quinoxyfen64 + 64960
16 + 16950
4 + 4930
BP-4 +Tankmix256 + 25610040
Chlorothalonil64 + 64360
16 + 16400
4 + 490
BP-4 +Tankmix256 + 2569613
Ethirimol64 + 64960
16 + 16640
BP-4 +Tankmix256 + 2565413
Dimethomorph64 + 64280
16 + 1660
BP-4 +Tankmix256 + 2567513
BION64 + 64780
16 + 16640
4 + 4590
|
Example 8
[0192] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) against Leptosphaeria nodorum on wheat The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table VIII:
9TABLE VIII
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
BP-4TC 100%25634
6414
160
40
DithianonWG 700 g/kg25674
6437
161
40
CyprodinilTC 100%25693
6488
1675
40
TriforineEC 190 g/l25685
6451
1631
44
10
FenpropidinEC 750 g/l25621
640
MancozebWP 800 g/kg25669
6447
1621
40
QuinoxyfenTC 100%25618
640
161
DimethomorphTC 100%25614
6411
166
41
AzoxystrobinTC 100%256100
64100
1697
484
BP-4 +Tankmix256 + 2569083
Dithianon64 + 646546
16 + 16271
4 + 440
BP-4 +Tankmix256 + 2569796
Cyprodinil64 + 649290
16 + 168075
4 + 4570
BP-4 +Tankmix256 + 2569790
Triforine64 + 648458
16 + 164731
4 + 4324
BP-4 +Tankmix256 + 2564248
Fenpropidin64 + 642114
BP-4 +Tankmix256 + 2568779
Mancozeb64 + 646555
16 + 163221
4 + 480
BP-4 +Tankmix256 + 2566246
Quinoxyfen64 + 643414
16 + 1681
BP-4 +Tankmix256 + 2568443
CL336 37064 + 646524
Dimethomorph16 + 16316
4 + 4141
BP-4 +Tankmix256 + 256100100
Azoxystrobin64 + 64100100
16 + 169897
4 + 49584
|
Example 9
[0193] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) against Puccinia recondita on wheat The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table IX:
10TABLE IX
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
BP-4TC 100%25638
6416
164
46
CaptanWP 500 g/kg25689
6455
1611
44
FluazinamSC 500 g/l25680
6422
166
40
MetalaxylTC 100%25612
640
FenpiclonilTC 100%25658
6418
160
41
FamoxadoneTC 100%6492
1680
445
BP-4 +Tankmix256 + 2569593
Captan64 + 646562
16 + 163015
BP-4 +Tankmix256 + 2569788
Fluazinam64 + 645335
16 + 162010
BP-4 +Tankmix256 + 2566146
Metalaxyl64 + 641916
BP-4 +Tankmix256 + 2568174
Fenpiclonil64 + 645431
16 + 16124
4 + 477
BP-4 +Tankmix64 + 649393
Famoxadone16 + 168381
4 + 46048
|
Example 10
[0194] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) against Leptosphaeria nodorum on wheat The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table X:
11TABLE X
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
|
BP-4TC 100%25644
6418
1610
40
DodineWP 650 g/kg25659
6424
166
40
CaptanWP 500 g/kg25690
6484
FluazinamSC 500 g/l25691
6481
FamoxadoneTC 100%25697
6480
1669
466
BP-4 +Tankmix256 + 2567577
Dodine64 + 645738
16 + 162915
4 + 4100
BP-4 +Tankmix256 + 2569694
Captan64 + 649387
BP-4 +Tankmix256 + 2569595
Fluazinam64 + 649184
BP-4 +Tankmix256 + 2569498
Famoxadone64 + 648984
16 + 168672
4 + 46766
|
Example 11
[0195] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) against Erysiphe cichoracearum on wheat The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table XI:
12TABLE XI
|
|
dose rateExpected
CompoundFormulation(ppm)Observed EfficacyEfficacy
|
|
BP-4TC 100%5096
1055
22
0.40
Sulfur inorganicTC 100%500
107
20
0.40
PropiconazoleEC 250 g/l5096
1076
219
0.40
EpoxiconazoleSC 125 g/l5077
1068
246
0.40
TebuconazoleEC 250 g/l5095
1079
245
0.410
MetconazoleSL 60 g/l5099
1075
0.42
MyclobutanilWP 60 g/kg5096
1073
252
0.436
Kresoxim-WG 500 g/kg50100
methyl1088
214
0.42
AC 382042TC 100%5025
1014
23
0.47
BRIOSE 450 g/l5096
Epoxiconazole/Fenpropimorph1048
(150 g/l) /(300 g/l)
ACROBAT MZWP 690 g/kg5057
Dimethomorph/ Mancozeb1030
(90 g/kg)/ (600 g/kg)20
0.40
JUWELSC 250 g/l50100
Kresoxim-methyl/Epoxiconazole.1098
(125 g/l)/ (125 g/l)271
0.437
BP-4Tankmix50 + 509296
Sulfur inorganic10 + 107058
2 + 2102
0.4 + 0.490
BP-4Tankmix50 + 50100100
Propiconazole10 + 1010089
2 + 26121
0.4 + 0.4280
BP-4Tankmix50 + 5010099
Epoxiconazole10 + 109886
2 + 27147
0.4 + 0.4410
BP-4Tankmix50 + 50100100
Tebuconazole10 + 109891
2 + 24845
0.4 + 0.42810
BP-4Tankmix50 + 50100100
Metconazole10 + 109789
0.4 + 0.452
BP-4Tankmix50 + 50100100
Myclobutanil10 + 109988
2 + 27552
0.4 + 0.45536
BP-4Tankmix50 + 50100100
Kresoxim10 + 1010095
-methyl2 + 23715
0.4 + 0.422
BP-4Tankmix50 + 5010097
AC 38204210 + 108762
2 + 2285
0.4 + 0.4257
BP-4Tankmix50 + 50100100
BRIO10 + 108577
BP-4Tankmix50 + 5010098
ACROBAT MZ10 + 108969
2 + 2452
0.4 + 0.470
BP-4Tankmix50 + 50100100
JUWEL10 + 109899
2 + 28472
0.4 + 0.45037
|
Example 12
[0196] Fungicidal efficacy of the mixture of BP-4 +Myclobutanil (4 day residual) against Puccinia recondita on wheat The tank mixes were obtained from technical material of BP-4 and Myclobutanil. The type of formulation, the observed and expected efficacies with different rates are given in Table XII:
13TABLE XII
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
|
BP-4TC 100%5031
1010
27
0.42
MyclobutanilWP 60 g/kg5099
1072
252
0.413
BP-4Tankmix50 + 509999
Myclobutanil10 + 108675
2 + 26555
0.4 + 0.44814
|
Example 13
[0197] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) against Pyrenophora teres on wheat The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table XIII:
14TABLE XIII
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
|
BP-4TC 100%5058
1034
20
0.40
Sulfur inorganicTC 100%100
20
CopperWP 450 g/kg5014
oxychloride1014
20
0.40
PropiconazoleEC 250 g/l5074
1038
20
0.40
MetconazoleSL 60 g/l1047
0.40
MyclobutanilWP 60 g/kg5082
1040
221
0.40
Kresoxim-WG 500221
methylg/kg0.40
ACROBAT MZWP 690 g/kg5047
Dimethomorph/1023
Mancozeb212
0.40
JUWELSC 250 g/l5089
Kresoxim-1062
methyl/245
Epoxiconazole0.45
BP-4Tankmix10 + 104934
Sulfur inorganic2 + 200
BP-4Tankmix50 + 507864
Copper10 + 105443
oxychloride2 + 2380
0.4 + 0.400
BP-4Tankmix50 + 508989
Propiconazole10 + 107859
2 + 2320
0.4 + 0.400
BP-4Tankmix50 + 508986
Tebuconazole2 + 2145
0.4 + 0.400
BP-4Tankmix10 + 106965
Metconazole2 + 22532
0.4 + 0.4180
BP-4Tankmix50 + 509193
Myclobutanil10 + 106761
2 + 24021
0.4 + 0.470
BP-4Tankmix2 + 26721
Kresoxim-methyl0.4 + 0.4360
BP-4Tankmix50 + 508578
ACROBAT MZ10 + 106049
2 + 22912
0.4 + 0.400
BP-4Tankmix50 + 5010095
JUWEL10 + 107875
2 + 24945
0.4 + 0.4405
|
Example 14
[0198] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) against Erysiphe cichoracearum on cucumbers The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table XIV:
15TABLE XIV
|
|
dose rate
CompoundFormulation(ppm)Observed EfficacyExpected Efficacy
|
|
BP-4TC 100%5097
1013
20
0.40
CyproconazoleSL 100 g/l1068
0.419
DinocapWP 190 g/kg100
20
0.40
FenarimolSC 125 g/l5067
1042
234
0.45
FenpropimorphEC 750 g/l107
20
0.40
FlusilazoleWP 200 g/kg5038
1019
20
0.40
PenconazoleEC 100 g/l5067
1037
235
0.46
ProchlorazEC 400 g/l5018
101
20
0.40
PyrifenoxWP 500 g/kg5020
101
20
0.40
TriadimefonWP 250 g/kg5047
1023
26
0.40
TriadimenolEC 250 g/l5068
1045
221
0.41
SpiroxamineEC 500 g/l102
20
0.40
BP-4Tankmix10 + 108472
Cyproconazole0.4 + 0.42319
BP-4Tankmix50 + 509698
Dinocap10 + 103013
2 + 220
0.4 + 0.420
BP-4Tankmix50 + 5010099
Fenarimol10 + 109249
2 + 24934
0.4 + 0.4195
BP-4Tankmix10 + 104319
Fenpropimorph2 + 260
0.4 + 0.420
BP-4Tankmix50 + 5010098
Flusilazole10 +105729
2 + 2140
0.4 + 0.410
BP-4Tankmix50 + 5010099
Penconazole10 + 109645
2 + 26635
0.4 + 0.4236
BP-4Tankmix50 + 5010098
Prochloraz10 + 107113
2 + 2110
0.4 + 0.470
BP-4Tankmix50 + 5010098
Pyrifenox10 + 105613
2 + 270
0.4 + 0.440
BP-4Tankmix50 + 509999
Triadimefon10 + 103932
2 + 2156
0.4 + 0.420
BP-4Tankmix50 + 5010099
Triadimenol10 + 107852
2 + 23021
0.4 + 0.491
BP-4Tankmix10 + 103715
Spiroxamine2 + 2100
0.4 + 0.420
|
Example 15
[0199] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) against Puccinia recondita on wheat The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table XV:
16TABLE XV
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
|
BP-4TC 100%5012
106
20
0.40
CyproconazoleSL 100 g/l299
0.488
DinocapWP 190 g/kg5054
1023
213
0.44
FenarimolSC 125 g/l5090
1023
29
0.40
FenpropimorphEC 750 g/l5060
215
0.42
FlusilazoleWP 200 g/kg50100
228
0.45
PenconazoleEC 100 g/l5026
1010
23
0.40
ProchlorazEC 400 g/l5014
101
20
0.40
PyrifenoxWP 500 g/kg506
101
20
0.40
TriadimenolEC 250 g/l5098
1069
221
0.41
SpiroxamineEC 500 g/l5017
104
BP-4Tankmix2 + 210099
Cyproconazole0.4 + 0.49288
BP-4Tankmix50 + 506160
Dinocap10 + 103828
2 + 22613
0.4 + 0.4104
BP-4Tankmix50 + 509991
Fenarimol10 + 105228
2 + 2159
0.4 + 0.4120
BP-4Tankmix50 + 508465
Fenpropimorph2 + 21915
0.4 + 0.4132
BP-4Tankmix50 + 50100100
Flusilazole2 + 25528
0.4 + 0.4145
BP-4Tankmix50 + 507835
Penconazole10 + 101916
2 + 273
0.4 + 0.440
BP-4Tankmix50 + 503425
Prochloraz10 + 10127
2 + 240
0.4 + 0.400
BP-4Tankmix50 + 503118
Pyrifenox10 + 10157
2 + 250
0.4 + 0.440
BP-4Tankmix50 + 509898
Triadimenol10 + 108971
2 + 23921
0.4 + 0.4101
BP-4Tankmix50 + 504027
Spiroxamine10 + 101110
2 + 230
|
Example 16
[0200] Fungicidal efficacy of the mixture of BP-4 +other fungicides (4 day residual) againstPyrenophora teres on barley The tank mixes were obtained from technical material of BP-4 and different formulations of different active ingredients. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table XVI:
17TABLE XVI
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
|
BP-4TC 100%5011
100
20
0.40
CyproconazoleSL 100 g/l101
24
DinocapWP 190 g/kg5022
105
20
0.40
FenarimolSC 125 g/l104
20
FenpropimorphEC 750 g/l103
20
0.40
FlusilazoleWP 200 g/kg5048
1026
28
ProchlorazEC 400 g/l1048
219
0.48
PyrifenoxWP 500 g/kg5015
108
101
20
0.40
SpiroxamineEC 500 g/l5016
105
23
0.40
BP-4Tankmix10 + 1091
Cyproconazole2 + 2104
BP-4Tankmix50 + 502931
Dinocap10 + 10155
2 + 250
0.4 + 0.490
BP-4Tankmix10 + 1064
Fenarimol2 + 210
BP-4Tankmix10 + 1043
Fenpropimorph2 + 250
0.4 + 0.450
BP-4Tankmix50 + 507054
Flusilazole10 + 104926
2 + 2268
BP-4Tankmix10 + 104948
Prochloraz2 + 23019
0.4 + 0.4198
BP-4Tankmix50 + 502625
Pyrifenox10 + 10108
BP-4Tankmix50 + 502920
Triadimefon10 + 10105
BP-4Tankmix50 + 504621
Triadimenol10 + 10191
2 + 230
0.4 + 0.410
BP-4Tankmix50 + 504326
Spiroxamine10 + 10245
2 + 263
0.4 + 0.430
|
Example 17
[0201] Fungicidal efficacy of the mixture of different benzophenones +metconazole (2 day curative) against Blumeria graminis f. sp. tritici on wheat The tank mixes were obtained from technical material of the-benzophenones BP-2 and BP-4 and metconazole. The benzophenones, the type of formulations, the observed and expected efficacies with different rates are given in Table XVII:
18TABLE XVII
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
|
BP-2EC 100 g/l5467
1825
618
213
0.674
BP-4TC 100%5492
1878
642
227
0.679
MetconazoleEC 100 g/L2740
914
37
12
0.330
BP-2Tankmix27 + 549080
Metconazole9 + 186735
3 + 64623
1 + 22212
0.33 + 0.6794
BP-4Tankmix27 + 549895
Metconazole9 + 189381
3 + 64945
|
Example 18
[0202] Fungicidal efficacy of the mixture of BP-4 +AP-4 (1 day residual) against Uncinula necator on vines The tank mixes were obtained from technical material of BP-4 and AP-4. The active ingredients, the type of formulations, the observed and expected efficacies with different rates are given in Table XVIII:
19TABLE XVIII
|
|
dose rateObservedExpected
CompoundFormulation(ppm)EfficacyEfficacy
|
|
BP-4TC 100%842
443
29
128
0.521
0.250
AP-4TC 100%176
0.576
0.2550
0.1232
0.067
0.0313
BP-4Tank mix8 + 18886
AP-44 + 0.59187
2 + 0.258579
1 + 0.128983
0.5 + 0.068881
0.25 + 0.037976
|
[0203] B Field Tests
Example 19
[0204] Fungicidal efficacy of the mixture of BP-1 +metconazole in the field against the sugar beet disease Cercospora beticola The tank mix was obtained from a SC formulation containing 100 g of BP-1 per liter and a SL formulation containing 60 g of metconazole per liter. The observed and expected efficacies are given in Table XIX
20TABLE XIX
|
|
dose rate g/ha
BP-1metconazoleObserved EfficacyExpected Efficacy
|
250042.5—
09058—
2509085.475.9
|
Claims
- 1. A fungicidal composition comprising a fungicidally acceptable carrier and/or surface active agent together with, and synergistically effective amounts of
(a) at least one benzophenone of formula I 12wherein R1 represents a halogen atom, an optionally substituted alkyl, alkanoyloxy or alkoxy group; or a hydroxy group, R2 represents a halogen atom or an optionally substituted alkyl group, m is 0 or an integer of 1 to 3; R3 independently represents a halogen atom, an optionally substituted alkyl or alkoxy group or a nitro group; R4 represents a halogen atom, a cyano, carboxy, hydroxy or nitro group or an optionally substituted alkyl, alkoxy, alkenyl, alkylthio, alkylsulphinyl, alkylsulphonyl or amino group; R5 represents an optionally substituted alkyl group; R6 represents a halogen atom or a nitro group, an optionally substituted alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, cycloalkyl, cycloalkyloxy, aryloxy group; n is 0 or 1; and R7 independently represents a halogen atom, an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkoxy group; (b) at least one fungicidally active ingredient selected from the following groups (A), (B), (C), (D) and (E): (A) an ergosterol biosynthesis inhibitor; (B) a strobilurine derivative, (C) a melanin biosynthesis inhibitor, (D) a compound selected from the group consisting of acibenzolar, benomyl, captan, carboxin, chlorothalonil, copper, cyprodinil, dinocap, dithianon, dimethomorph, dodine, ethirimol, famoxadone, fenpiclonil, fluazinam, mancozeb, metalaxyl, pyrifenox, sulfur, vinclozolin and (E) an azolopyrimidine of formula II 13in which R8 and R9 each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group, or R8 and R9 together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring, R10 represents hydrogen or an alkyl or aryl group, R11represents a hydrogen or halogen atom or an alkyl or alkoxy group, L independently represents a halogen atom or an optionally substituted alkyl or alkoxy group, A represents N or CR12, wherein R12 has the meaning given for R10, and p is 0 or an integer from 1 to 5.
- 2. A composition as claimed in claim 1, wherein the benzophenone is a compound of formula IA,
- 3. A composition according to claim 1, wherein the benzophenone of formula I is selected from the group consisting of 6′-butoxy-2,6-dichloro-4′,5′-dimethoxy-2′-methylbenzophenone; 2,6-dichloro-4′,5′-dimethoxy-6′-(2-fluorobenzyloxy)-2′-methylbenzophenone; 6′-benzyloxy-4′,5′-dimethoxy-2,6-dimethyl-2′-methylbenzophenone; 5-bromo-2′,6-dimethyl-2,4′,5′,6′-tetramethoxybenzophenone; and 2,6-dichloro-2′-methyl-4′,5′,6′-trimethoxybenzophenone.
- 4. A composition as claimed in claim 1, wherein the ergosterol biosynthesis inhibitor of group (A) is selected from fenarimol, fenpropimorph, fenpropidine, spiroxamine, triforine, cyproconazole, epoxiconazole, flusilazole, metconazole, myclobutanil, penconazole, prochloraz, propiconazole, tebuconazole, triadimefon and tridimenol.
- 5. A composition as claimed in claim 4, wherein the ergosterol biosynthesis inhibitor of group (A) is metconazole.
- 6. A composition as claimed in claim 1, wherein the strobilurine derivative group (B) is selected from azoxystrobin, kresoxim-methyl and trifloxystrobin.
- 7. A composition as claimed in claim 1, which comprises one compound of formula I, one strobilurine compound selected from group (B) and one ergosterol biosynthesis inhibitor of group (A), or one compound of formula I and two different compounds of group (D).
- 8. A composition as claimed in claim 1, wherein the melanin biosynthesis inhibitor of group (C) is selected from capropamid, chlobenthiazone, diclocymet, pyroquilon, phthalide, tricyclazole and AC 382042.
- 9. A composition as claimed in claim 1, wherein the azolopyrimidine of group (E) is a compound of formula IIA,
- 10. A composition as claimed in claim 9, wherein Hal represents a chlorine atom, L1 represents a fluorine atom; L2 represents a hydrogen or fluorine atom or a methoxy group and L3 represents a fluorine or chlorine atom.
- 11. A composition as claimed in claim 9, wherein the azolopyrimidine of formula II is selected from the group consisting of
5-chloro-6-(2-chloro-6-fluorophenyl)-7-(cyclopropylamino)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperid-1 -yl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[1,5-a]pyrimidine; and 5-chloro-6-(2,4,6-trifluorophenyl)-7-[2-(1,1,1 -trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine.
- 12. A composition as claimed in claim 1, wherein the ratio (by weight) of the benzophenone of formula I to the fungicidal compound selected from the groups (A), (B), (C), (D) and (E) is from 10:1 to 1:10.
- 13. A composition as claimed in claim 12, wherein the ratio (by weight) of the benzophenone of formula I to the fungicidal selected from the groups (A), (B), (C), (D) and (E) is from 5:1 to 1:5.
- 14. Method of controlling the growth of fungi at a locus which comprises applying a composition as claimed in claim 1 to the locus.
- 15. Method of controlling the growth of powdery mildew at a locus which comprises applying a composition as claimed in claim 1 to the locus.
Continuations (1)
|
Number |
Date |
Country |
Parent |
09240412 |
Jan 1999 |
US |
Child |
10046190 |
Jan 2002 |
US |