EP4384014A1

EP4384014A1 - Fungicidal compositions of metconazole

Info

Publication number: EP4384014A1
Application number: EP22765767.3A
Authority: EP
Inventors: Stefaan Reybrouck; Kerim SCHELLINGEN
Original assignee: Globachem NV
Current assignee: Globachem NV
Priority date: 2021-08-13
Filing date: 2022-08-12
Publication date: 2024-06-19
Also published as: WO2023017167A1

Abstract

Stable fungicidal compositions comprising metconazole are provided herein.

Description

Fungicidal compositions of metconazole

Description

Technical field

The present invention relates to stable compositions comprising metconazole and use of such compositions in methods of the growth of plants, as well as in methods for controlling, preventing and/or treating of phytopathogenic fungi in crop plants.

Background art

Metconazole is a triazole fungicide, ISO common name for (1 RS,5RS; 1 RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1 H-1 ,2,4-triazol-1 - ylmethyl)cyclopentanol.

Metconazole is an effective fungicide and is typically formulated as emulsifiable concentrate at concentrations of 60 g/L and 90 g/L.

There is an interest to introduce formulations to the market that are higher strength due to economic and environmental reasons.

Higher strength (higher load or higher concentration) formulations are desirable for various environmental and economic reasons, such as reduction of packaging and solvents released into environment. However, higher strength formulations are challenging due to chemical and/or physical instability of active ingredient, such as agglomeration, crystallization, phase separation and gelling.

Desirable requirements for higher strength formulations are storage stability and potency retention, stability at various temperatures and homogeneity and no precipitation at lower temperatures.

A major limitation of the emulsifiable concentrate of metconazole is its limited stability at low temperature and high concentration.

The present invention addresses these needs and provides a wide variety of benefits and advantages, such as high strength formulations of metconazole which exhibit chemical and physical stability at broad temperature range.

Disclosure of invention

The following description and examples are shown for exemplary and explanatory purposes and are not intended to limit the scope of the present invention. The features and characteristics illustrated and/or described herein in connection with various examples presented herein may be combined with the features and characteristics of other examples also provided herein and such modifications and variations are intended to be included within the scope of the present invention.

For the purpose of the present disclosure, following terms and abbreviations have the following meaning:

As used herein, term “fungicidally effective amount” means the relative amount that is effective to inhibit or control fungus growth rate, increase mortality, or eradicate the fungus when the fungicidal composition is applied to the target fungus at a given application rate.

As used herein, and unless otherwise indicated, the term “about” when used in connection with numeric values, parameters or numerical ranges such as amounts, volumes, volume ratios, volume percentages, weight ratios, weight percentages, or application rates of ingredients of a composition, means an amount, a volume, a volume ratio, a volume percentage, a weight ratio, a weight percentage, or an application rate that is recognized by those of ordinary skill in the art to provide a desired effect equivalent to that obtained from the specified amount, volume, volume ratios, volume percentages, weight ratio, weight percentage, or application rate, is encompassed herein and should be construed in light of the number of reported significant digits and applying ordinary rounding techniques.

Any numerical range disclosed herein is meant to include all sub-ranges subsumed within the recited one. For instance, range from 1 to 10 includes all sub-ranges between and including the recited minimal value 1 and the recited maximum value 10 and any value in-between, including any and all decimal values.

As used herein, a "composition" comprises at least one active ingredient and at least one auxiliary agent.

In the present invention, an "active ingredient" is a compound which directly exerts a biologically relevant effect, preferably a pesticidal effect as described herein.

The term "auxiliary agent" or “auxiliary” refers to a compound or combination of compounds which do not exert a biologically relevant effect of their own but support the effects of the active ingredient(s). When auxiliary agents are used, their choice will depend on the active ingredients and on the procedures selected for the treatment. One aspect of the present invention is to provide compositions as described above additionally comprising at least one auxiliary component selected from the group comprising of emulsifiers, solvents, surfactants, carriers, dispersants, thickeners, hydrophobizing agents, moisture-retaining agents, extenders, solid carriers, anti-foaming agents and/or other auxiliaries.

The compositions of the present invention can be formulated into any customary type of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.

Composition types examples are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP), pressings (e.g. BR, TB), granules (e.g. WG, SG, GR), etc.

Terms “composition” and “formulation” are used interchangeably throughout the text and are meant as having the same meaning.

The present invention is directed to high-strength fungicidal formulations containing metconazole.

Surprisingly, it has now been found that high strength concentrates of metconazole can be prepared by adding N,N-dimethyl alkylamide as the solvent, preferably N,N-dimethyl (Ce-Ci2)alkylamide, and even more preferably is N,N-dimethyldecanamide. Such concentrates show stability at both low and high temperatures for high strength formulations.

The present invention provides a high-strength fungicidal formulation comprising: a) metconazole, wherein the formulation comprises from about 100 g/L to about 450 g/L of metconazole; b) an emulsifier or mixture of emulsifiers from about 50 g/L to about 300 g/L: c) solvent N,N-dimethyl (Ce-Ci2)alkylamide from about 200 g/L to about 700 g/L.

The emulsifiers according to the present invention can be anionic, cationic or non-ionic in character. Emulsifiers conventionally used in the art of formulation and which may also be used in the present formulations are described, for example, in "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, 1998 and in "Encyclopedia of Surfactants", Vol. 1-111 , Chemical publishing Co., New York, 1980- 81. Typical emulsifiers include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkyl and/or arylalkylphenolalkylene oxide addition products, such as nonylphenolCis ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Cie ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono and dialkyl phosphate esters; and mixtures thereof.

According to the present invention, emulsifier or mixture of emulsifiers is usually present at a concentration of from about 50 g/L to about 300 g/L.

The solvent, which typically makes up the remainder of the high-strength fungicidal formulation, is N,N-dimethyl (C6-Ci2)alkylamide present at concentration from about 200 g/L to about 700 g/l, more preferably from about 400 g/L to about 600 g/L.

According to the present invention, high-strength fungicidal formulation comprises: a) metconazole in concentration from about 200 to about 400 g/L b) an emulsifier or mixture of emulsifiers from about 50 g/L to about 200 g/L; c) solvent N,N-dimethyl (C6-Ci2)alkylamide from about 400 g/L to about 600 g/L.

The high-strength, fungicidal formulation does not exhibit separation or precipitation (or crystallization) of any of the components at low or high temperatures.

The high-strength formulation remains a clear solution at temperatures below about 10°C, more preferably at temperatures about 0°C.

The herein disclosed compositions can further comprise one or more agriculturally acceptable adjuvant or auxiliary.

An adjuvant or an auxiliary in the context of the present invention is a component which enhances the performance effect of the formulation.

Examples of adjuvants and auxiliaries are agents which promote one or more of the following effects: retention, spreading, attachment to the leaf/crop surface, penetration, physical, chemical, technical and/or biological effect, etc. One aspect of the present invention is to provide compositions as described above additionally comprising at least one auxiliary component selected from the group comprising of fungicides, emulsifiers, solvents, surfactants, carriers, dispersants, thickeners, anti-foaming agents and/or other auxiliaries.

The compositions of the present invention are diluted with water prior to being applied.

Provided herein is also a method of the growth of plants as well as controlling, preventing and/or treating of phytopathogenic fungi causing fungal infections in plants, wherein the method comprises treating the crops or plants with a fungicidally effective amount of a compositions according to the present invention, wherein phytopathogenic fungi are selected from Septoria, Mildew, fungi causing brown rust or yellow rust, Fusarium, Rhynchosporium, Botrytis, Phoma, Alternaria, Sclerotinia and Pyrenopeziza.

According to the present invention crops or plants are selected from sunflower, maize, sorghum, soybeans, oilseed rape, cereals, sugar beets, peas and other leguminosae, winter and spring wheat, durum wheat, winter and spring barley, triticale, rye, peas, field beans, sugar beet, lupins, grassland, ornamentals, golf courses and lawns.

Example 1 :

A high-strength formulation was prepared containing 270 g/L of metconazole by dissolving 270 g/L metconazole into 600 g/L N,N-dimethyldecanamide under gentle heating to 40°C and stirring until metconazole is completely dissolved. Followed by addition of 106 g/L of emulsifier EO-PO block copolymer blend under stirring and slow cooling down of the formulation.

The prepared formulation remained stable with appearance unchanged after post-accelerated storage for two weeks at 54°C ± 2°C.

Formulation according to Example 1 was also tested in the field trial in wheat against Puccinia to confirm the efficacy as well as the absence of negative effects.

0,0% - disease progressed to maximum

100,0% - no disease symptoms observed

A - first treatment

B - second treatment DA-A - days after first treatment (application)

DA-B - days after second treatment (application)

FL-1 , FL-2, FL-n, etc. - means flag leaf minus 1 , flag leaf minus 2, flag leaf minus n, wherein leaf-n is the oldest leaf on the plant (first emerged) FLAGLE - means flag leaf

Formulation applied in the treatment was prepared by dilution with water of formulation according to Example 1 to predetermined concentration according to the table below.

Obtained results show pest severity as percentage (%) of leaf that has disease for the row in the table marked as UNTREATED, wherein control of the disease is shown as percentage (%) of control in rows wherein treatments were applied.

Application timing: A = +/- BBCH32 (wheat)

B = BBCH 39-51 (wheat) (21 DA-A)

*Caramba is a market available product containing metconazole

The results, show that the efficacy of the new formulations according to the present invention is sufficiently similar or better to that of the market standard.

Claims

7 Claims

1. Agricultural fungicidal formulation comprising: a) metconazole, wherein the formulation comprises from about 100 g/L to about 450 g/L of metconazole; b) an emulsifier or mixture of emulsifiers from about 50 g/L to about 300 g/L; c) solvent N,N-dimethyl (C6-Ci2)alkylamide from about 200 g/L to about 700 g/L.

2. Agricultural formulation according to claim 1 comprising: a) metconazole in concentration from about 200 to about 400 g/L; b) an emulsifier or mixture of emulsifiers from about 50 g/L to about 200 g/L; c) solvent N,N-dimethyl (C6-Ci2)alkylamide from about 400 g/L to about 600 g/L.

3. Agricultural formulation according to claim 1 or 2 wherein N,N-dimethyl (Ce- Ci2)alkylamide is N,N-dimethyldecanamide.

4. Method for controlling the growth of plants as well as, preventing and/or treating of phytopathogenic fungi causing fungal infections in plants, wherein the method comprises treating the crops or plants with a formulation according to any of the claims 1-3, wherein phytopathogenic fungi are selected from Septoria, Mildew, fungi causing brown rust or yellow rust, Fusarium, Rhynchosporium, Botrytis, Phoma, Alternaria, Sclerotinia and Pyrenopeziza.

5. Method according to claim 4, wherein crops or plants are selected from sunflower, maize, sorghum, soybeans, oilseed rape, cereals, sugar beets, peas and other leguminosae, winter and spring wheat, durum wheat, winter and spring barley, triticale, rye, peas, field beans, sugar beet, lupins, grassland, ornamentals, golf courses and lawns.