CN117119889A

CN117119889A - 5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one for controlling plant diseases

Info

Publication number: CN117119889A
Application number: CN202280024518.1A
Authority: CN
Inventors: A·罗森孟德
Original assignee: Makhteshim Chemical Works Ltd
Current assignee: Adama Makhteshim Ltd
Priority date: 2021-01-27
Filing date: 2022-01-27
Publication date: 2023-11-24

Abstract

The present application provides a method for treating a selected plant against a selected fungal pathogen infection and/or fungal disease comprising applying to the plant or locus thereof an amount of trifloxystrobin to thereby treat the plant against a fungal pathogen infection and/or fungal disease. The present application also provides a method for treating a plant against fungal pathogen infection and/or fungal disease comprising applying an amount of trifloxystrobin, wherein the amount of trifloxystrobin is effective to treat the plant against fungal pathogen infection and/or fungal disease and has an ecologically acceptable effect on non-target organisms.

Description

5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one for controlling plant diseases

Throughout this disclosure, various publications are referenced. The disclosures of these documents are hereby incorporated by reference in their entireties into this application in order to more fully describe the state of the art to which this application pertains.

Technical Field

The present disclosure relates to the use of a compound of formula I for treating plants to combat fungal pathogen infection and/or fungal disease comprising applying to the plants or locus thereof an amount of a compound of formula I

(fluocinolone) to thereby treat plants against fungal pathogen infection and/or fungal disease. The present invention also provides a method for treating a plant against fungal pathogen infection and/or fungal disease comprising applying an amount of trifloxystrobin, wherein the amount of trifloxystrobin is effective to treat the plant against fungal pathogen infection and/or fungal disease and has an ecologically acceptable effect on non-target organisms.

Background and overview

Fungicides are compounds of natural or synthetic origin which act to protect plants from damage caused by fungi. Current agricultural methods rely largely on the use of fungicides. In fact, some crops do not grow efficiently without the use of fungicides. The use of fungicides allows the grower to increase the yield and quality of the crop and thus increase the value of the crop. In most cases, the increase in crop value is at least three times the cost of using fungicides.

5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one is a compound that provides control of a variety of pathogens affecting crops of economic importance, including but not limited to, the causative agent of leaf spot disease in wheat, the fungus wheat leaf blight (Zymoseptoria tritici, SEPTTR), and the fungi of ascomycetes and basidiomycetes. 5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one has both prophylactic and therapeutic effects.

The use of N3-substituted-N1-sulfonyl-5-fluoropyrimidinone derivatives as fungicides is described in U.S. patent No. 8,263,603 issued 9, 11, 2012, the contents of which are incorporated herein by reference in their entirety. The preparation of 5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one is described in U.S. Pat. No. 9,850,215 issued at 26 of 12.2017 and U.S. Pat. No. 9,840,476 issued at 12 of 12.2017, the respective contents of which are incorporated herein by reference in their entireties. U.S. patent No. 8,263,603 also describes fungicidal compositions for controlling or preventing fungal attack comprising an N3-substituted-N1-sulfonyl-5-fluoropyrimidinone derivative and a phytologically acceptable carrier material, and methods of use thereof. The use of 5-fluoro-4-imino-3- (alkyl/substituted alkyl) -1- (arylsulfonyl) -3, 4-dihydropyrimidin-2 (1H) -one as a seed treatment to prevent or control plant diseases is described in U.S. patent application publication No. 2018/0000082 published 1/4 in 2018. Synergistic mixtures comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one and at least one fungicidal sterol biosynthesis inhibitor are described in U.S. Pat. No. 9,526,245 issued 12/27/2016 and U.S. Pat. No. 10,045,533 issued 14/8/2018. Synergistic mixtures comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one and at least one succinate dehydrogenase inhibitor are described in U.S. Pat. No. 9,532,570 issued on 1 month 3 of 2017 and U.S. Pat. No. 10,045,534 issued on 14 month 8 of 2018. Synergistic mixtures comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one and penflufen, fluxapyroxad-ol, penflufen, picolide (ipyrafen), ipratropium and Qi inhibitors are described in PCT/IB 2020/056828.

There is a need to develop additional methods for effectively treating plants against fungal pathogen infection and/or fungal disease.

Summary of The Invention

The present invention provides a method for treating plants against fungal pathogen infection and/or fungal disease comprising applying to the plants or locus thereof an amount of a compound of formula I

To thereby treat plants against fungal pathogen infection and/or fungal disease, wherein:

(1) The fungal pathogen is selected from the group consisting of: rice blast bacteria (Pyricularia oryzae), rhizoctonia solani (Rhizoctonia solani), sclerotinia sclerotium, cucumber downy mildew bacteria (Pseudoperonospora cubensis), apple scab bacteria (Venturia inequalis), single-cyst white fork bacteria (Podosphaera leucotricha), botrytis cinerea (Botrytis cinerea), single-shell monofilament bacteria (Sphaerotheca fuliginea), alternaria solani (Alternaria solani), cercospora beet (Cercospora beticola), beet leaf spot bacteria (Ramularia beticola), white spot column bacteria (Ramularia arola), beet powdery mildew bacteria (erygium betae), soybean rust bacteria (Phakopsora pachyrhizi), soybean powdery mildew bacteria (Microsphaera diffusa), web ball cavity bacteria (Mycosphaerella areola), multiple main corynespora bacteria (Corynespora cassiicola), disc-shaped, soybean violet spot bacteria (Cercospora kikushi), grape downy mildew bacteria (Plasmopara viticola), ball cavity bacteria (Mycosphaerella fijiensis), potato plague bacteria (Phytophthora infestans), pepper anthracnose bacteria (Phytophthora infestans), single-cyst white fork bacteria (Phytophthora infestans), species (colestonia (Phytophthora infestans), fusarium gracilomyces (Phytophthora infestans), fusarium (Phytophthora infestans) and Fusarium (Phytophthora infestans) of the species (Fusarium graminearum (Phytophthora infestans) are described above Acremonium colchicum (Ramularia collo-cygni), rhizoctonia betana (Uromyces betae), rhizoctonia cerealis (Zymoseptoria tritici), leptosphaeria isochrombotica (Cochliobolus heterostrophus), leptosphaeria species (Puccinia striiformis), pseudocercospora banana (Pseudocercospora musae), and any combination thereof,

(2) The fungal disease is selected from the group consisting of: blast (blast), sheath blight (shaping blast), early blight (early blight), late blight (late blast), leaf blight (leaf blast), apple scab (apple scab), banana black streak (black sigatoka), downy mildew (down) soybean late season disease (late season diseases of soybean), asian soybean rust (Asian soybean rust), anthracnose (anthracnose), powdery mildew (powdery mildw), potato late blight (potato late blight), rice leaf spot disease (brown spot of rice), brown rust disease (owbrown rust), coffee bean disease (coffee berry disease), coffee leaf rust disease (coffee leaf rust), adymella pie, red spot (Fusarium head blight), gray leaf spot, corn large spot (northern corn leaf blight), corn round 97disease (northern corn leaf spot), post-Septoria leaf spot (69), yellow leaf spot (yellow spot), yellow leaf spot (988), yellow leaf spot (yellow spot), yellow spot (yellow spot) corn leaf rust (southern corn leaf blight), and any combination thereof, and/or

(3) The plant is selected from the group consisting of soybean, rice, fruit plants, vegetable plants, sugar beet, canola, grape vine, cotton, olive, legumes, grains, coffee, corn, and any combination thereof.

The invention also provides a method for treating seeds or seedlings against fungal pathogen infection and/or fungal disease comprising applying to the seeds, seedlings and/or locus thereof a compound of formula ITo thereby treat seeds or seedlings against fungal pathogen infection and/or fungal disease, wherein:

(1) The fungal pathogen is selected from the group consisting of: pyricularia oryzae, rhizoctonia solani, sclerotinia sclerotium, rhizoctonia cerealis, marsdenia tenacissima, botrytis cinerea, sphaerotheca gracilis, alternaria solani, cercospora betana, cercospora caligenes, cercospora spinosa, cercospora, soy bean powdery mildew, leptosphaeria polymorpha, mortierella spinosa, leptosphaera sojae, pythium gracilis, fijisphaeria potato late blight germ, pepper anthracnose germ, white fork wire single cyst fungus, anthracnose species, soybean anthracnose germ, wheat leaf rust germ, coffee anthracnose germ, coffee camellias, fusarium species, maize gray leaf germ, corn big spot germ, carbon black spore cavity germ, column septoria leaf spot germ, beet armyworm, wheat leaf rust germ, alternaria cavity germ, stripe rust germ, banana pseudotail spore, and any combination thereof,

(2) The fungal disease is selected from the group consisting of: blast, sheath blight, early blight, late blight, leaf blight, apple scab, banana black streak, downy mildew, soybean late season disease, asian soybean rust, anthracnose, powdery mildew, potato late blight, rice flax spot, brown rust, coffee bean disease, coffee leaf rust, didymella pisi, scab, gray leaf spot, corn large spot, corn round spot, septoria leaf spot, rust, septoria, corn small spot, yellow rust, banana yellow streak leaf spot, and any combination thereof, and/or

The present invention also provides a method of producing a plant resistant to fungal pathogen infection and/or fungal disease comprising applying to the plant or locus thereof a compound of formula I

To thereby produce plants resistant to fungal pathogen infection and/or fungal disease, wherein:

The present invention also provides a method of producing a plant resistant to fungal pathogen infection and/or fungal disease comprising applying to a seed of the plant, a seedling of the plant, and/or locus of the seed or seedling a compound of formula I

The invention also provides plants resistant to fungal pathogen infection and/or fungal disease, wherein seeds adapted to produce plants, seedlings adapted to produce plants, or locus of plants are treated with a compound of formula I

Wherein:

The invention also provides plant seeds or seedlings adapted to produce plants resistant to fungal pathogen infection and/or fungal disease, wherein the plant seeds or seedlings are treated with a compound of formula I

And wherein:

The invention also provides the use of a compound of formula I for treating plants against fungal pathogen infection and/or fungal disease

Wherein:

The invention also provides a composition comprising an amount of a compound of formula I

For treating plants against fungal pathogen infection and/or fungal disease, wherein:

Brief Description of Drawings

Fig. 1: observations of aerial part development of soybean plants from untreated seeds (control) or seeds treated with adm.00050.F.1.A at five application rates, seeds treated with polybrance Duo or mefenoxam, each at one application rate, after 3 weeks of incubation in controlled conditions.

Fig. 2: observations of aerial part development of soybean plants from untreated seeds (control) or seeds treated with adm.00050.F.1.A at five application rates, seeds treated with polybrance Duo or mefenoxam, each at one application rate, after 3 weeks of incubation in controlled conditions.

Fig. 3: evaluation of leaf severity (%) and incidence (%)

Fig. 4: evaluation of fungicide efficacy with respect to leaf severity and morbidity (Abbott's formula)

Fig. 5: evaluation of leaf severity and morbidity at the third evaluation

Fig. 6: evaluation of fungicide efficacy on leaf severity and morbidity at the third evaluation (Abbott's formula)

Fig. 7: evaluation of fungicide efficacy on stem severity at the last evaluation date (Abbott's formula)

Fig. 8: percentage of disease pressure control compared to untreated control at the final evaluation (21 DA-C) and corresponding severity of disease in untreated control

Fig. 9: compound OD treatment of formula I (50 g ai/ha, 75g ai/ha, 100g ai/ha, 125g ai/ha and 150g ai/ha) and reduction in infected leaf area relative to UTC of the reference product%

Fig. 10: evaluation of fungicide efficacy with respect to leaf severity (Abbott's formula)

Fig. 11: efficacy for controlling cladosporium cucumerinum on apples

Fig. 12: efficacy of controlling Leptospira leucotrichia monocystis on zucchini

Fig. 13: efficacy of control of cercospora betaensis on sugar beet

Fig. 14: efficacy for controlling leaf spot bacteria on sugar beet

Fig. 15: efficacy for controlling chaetomium gracile (powdery mildew in apples) in apples

Fig. 16: efficacy for controlling Alternaria solani (early blight) on potato

Detailed description of the preferred embodiments

Definition of the definition

Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this subject matter belongs.

As used herein, the term "compound of formula I" includes all solid forms thereof, including but not limited to amorphous, crystalline, solvate or hydrate. Crystalline forms of the compound of formula I are disclosed in PCT international application publication No. WO 2019/038583 A1 published 28, 2, 2019, the entire contents of which are hereby incorporated by reference. The term "compounds of formula I" also includes salts and optical isomers thereof.

As used herein, the terms "compound of formula I" and "sulfluramid" may be used interchangeably.

As used herein, the term "simultaneously" when used in conjunction with the application of an agrochemical means that the agrochemical is applied as a blend, such as a tank mix. For simultaneous application, the combination may be a blend or separate containers, each containing the agrochemical to be combined prior to application.

As used herein, the term "contemporaneous" when used in connection with the application of an agrochemical means that the individual agrochemical is applied simultaneously or separately at sufficiently close times to another agrochemical or pre-mix such that an activity is achieved that is additive or higher than additive or synergistic relative to the activity of either individual agrochemical at the same dose.

As used herein, the term "mixture" refers to, but is not limited to, a combination in any physical form, e.g., a blend, solution, suspension, dispersion, emulsion, alloy, and the like.

As used herein, the term "tank mix" means one or more of the components of the combination of the present invention that are added and mixed in the spray tank at or prior to spray application.

As used herein, the term "composition" includes sulfluramid or a combination or mixture of the invention with an agriculturally acceptable carrier.

As used herein, the term "effective" when used in conjunction with an amount of an active ingredient (e.g., a compound of formula I), combination, mixture or composition, refers to an amount of the active ingredient, combination, mixture or composition that achieves an agriculturally beneficial level of control of fungi, pathogens, and/or diseases when applied to a plant, propagation material of a plant, soil or locus.

As used herein, the term "effective" when used in connection with a method for treating a plant or locus to combat fungal infection means that the method provides agriculturally beneficial levels of treatment without significantly interfering with normal growth and development of the plant.

As used herein, the term "effective" when used in conjunction with an active ingredient (e.g., a compound of formula I), mixture, or composition, can be, but is not limited to, controlling and/or preventing a fungal disease.

In some embodiments, the method is effective for controlling fungal diseases. In some embodiments, the method is effective for preventing fungal diseases.

As used herein, the term "effective amount" refers to an amount of an active ingredient (e.g., a compound of formula I), composition, or mixture that is sufficient to control fungi that are harmful to crop plants and that does not cause any significant damage to the treated crop plants.

As used herein, the term "fungicidally effective amount" refers to the amount of a commercially recommended active ingredient (e.g., a compound of formula I) for controlling fungi. The commercially recommended amount of each active component (typically designated as the application rate of the commercial formulation) can be found on the label attached to the commercial formulation. The commercially recommended application rate of the commercial formulation may vary depending on factors such as plant species and fungi to be controlled.

As used herein, the term "treating a plant or locus to combat a fungal infection" includes, but is not limited to, protecting a plant or locus from and/or controlling a fungal infection of a plant or locus.

As used herein, the term "protecting a plant or locus against a fungal infection" includes, but is not limited to protecting a plant or locus against a fungal attack, protecting a plant or locus from a fungal disease, and/or preventing a fungal infection of a plant or locus.

As used herein, the term "controlling fungal infection of a plant or locus" includes, but is not limited to, controlling fungal diseases of the infected plant or locus, controlling plant or soil diseases caused by phytopathogenic fungi, controlling fungal attack on the plant or locus, reducing fungal infection of the plant or locus, and/or treating plant or soil diseases caused by phytopathogenic fungi.

As used herein, the term "protective application (protectant application)" means the application of one or more fungicides for preventing a fungal infection of a plant or locus, wherein the fungicide combination, mixture or composition is applied before the infection occurs, before any disease symptoms are exhibited, or when the disease pressure is low. Disease pressure can be assessed based on conditions associated with disease development, such as spore concentration and certain environmental conditions.

As used herein, the term "therapeutic application" means the application of one or more fungicides for controlling a fungal infection of a plant or locus, wherein the fungicidal combination, mixture or composition is applied after the infection or after the symptoms of the disease are displayed.

As used herein, the term "agriculturally acceptable carrier" means a carrier known and accepted in the art for forming a composition for agricultural or horticultural use.

As used herein, the term "adjuvant" is defined broadly as any substance that is not itself an active ingredient but that enhances or aims to enhance the effectiveness of the fungicide with which it is used. Adjuvants may be understood to include dispersing agents, penetrating agents, compatibilizing agents and drift retarders.

As used herein, the term "agriculturally acceptable inert additive" is defined as any substance that is not an active ingredient per se but is added to the composition, such as adhesives, surfactants, synergists, buffers, acidulants, antioxidants, defoamers, and thickeners.

As used herein, the term "plant" includes reference to whole plants, plant organs (e.g., leaves, stems, branches, roots, trunks, branches, shoots, fruits, etc.), plant cells, and propagation material of a plant.

As used herein, the term "plant" includes reference to crops, including field crops (soybean, corn, wheat, rice, etc.), vegetable crops (potato, cabbage, etc.), and fruit (peach, etc.).

As used herein, the term "propagation material" is understood to mean all reproductive parts of plants, such as seeds and spores, seedlings, and also vegetative structures, such as bulbs, corms, tubers, underground stems, rhizomes, base shoots (basal shoots), stolons and buds.

As used herein, the term "locus" includes not only areas that may have been shown to be infected with a fungus, but also areas that have not yet been shown to be infected with a fungus, and also areas that are in culture. Sites include, but are not limited to, soil and other plant growth media.

As used herein, the term "ha" refers to hectare.

The term "a" or "an" as used herein includes both the singular and the plural, unless specifically stated otherwise. Thus, the terms "a/an" or "at least one" may be used interchangeably herein.

Throughout the description of the various embodiments, the term "comprise" is used; however, those skilled in the art will appreciate that in some specific instances, embodiments may be described using the language "consisting essentially of or" consisting of.

The term "about" herein specifically includes + -10% of the indicated value in this range. In addition, endpoints of all ranges directed to the same component or property herein are inclusive of the endpoints, independently combinable, and inclusive of all intermediate points and ranges.

It is to be understood that where a range of parameters is provided, all integers and tenths thereof within that range are also provided by the invention as if the integers and tenths thereof were explicitly described herein. For example, "5g ai/ha to 120g ai/ha" includes 5.0g ai/ha, 5.1g ai/ha, 5.2g ai/ha, 5.3g ai/ha, 5.4g ai/ha, etc., up to 120g ai/ha.

All publications, patents, and patent applications mentioned in this specification are herein incorporated in their entirety by reference into the specification, to the same extent as if each individual publication, patent, or patent application was specifically and individually indicated to be incorporated herein by reference.

The following examples illustrate the practice of the inventive subject matter in some embodiments thereof, but should not be construed to limit the scope of the inventive subject matter. Other embodiments that are apparent to those of ordinary skill in the art from consideration of the specification and examples herein are part of the invention and fall within the spirit and scope of the appended claims. It is intended that the specification, including examples, be considered as exemplary only, with a true scope and spirit of the invention.

Aspects and embodiments of the present invention will now be described.

In some embodiments of the present invention, in some embodiments,

(1) The fungal pathogen is selected from the group consisting of: pyricularia oryzae, rhizoctonia solani, sclerotinia sclerotium, rhizoctonia cerealis, marsdenia tenacissima, botrytis cinerea, sphaerotheca gracilis, alternaria solani, rhizoctonia cerealis, leptosphaera betana, leptosphaera fumago, leptosphaera polymorpha, leptosphaera spinosa, leptosphaera sojae, leptosphaera viticola, leptosphaera fijia, phytophthora potato, leptosphaera capsici, leptosphaera gracilis, and any combination thereof,

(2) The fungal disease is selected from the group consisting of: blast, sheath blight, early blight, late blight, leaf blight, apple scab, banana black streak leaf spot, downy mildew, soybean late season disease, asian soybean rust, anthracnose, powdery mildew, potato late blight, rice flax leaf spot, and any combination thereof, and/or

(3) The plant is selected from the group consisting of soybean, rice, fruit plants, vegetable plants, sugar beet, canola, grape vine, cotton, olive and any combination thereof.

In some embodiments of the present invention, in some embodiments,

(1) The fungal pathogen is selected from the group consisting of: pyricularia oryzae, rhizoctonia solani, sclerotinia sclerotium, rhizoctonia cerealis, marsdenia tenacissima, botrytis cinerea, sphaerotheca gracilis, rhizoctonia cerealis, alternaria solani, cercospora betana, mortierella gracilis, alternaria farina, leptosphaera sojae, leptosphaera polymorpha, leptosphaera spinosa, leptosphaera sojae, leptosphaera viticola, fijia, as well as any combination thereof,

(2) The fungal disease is selected from the group consisting of: blast, sheath blight, early blight, apple scab, downy mildew, banana black streak, downy mildew, late quaternary soybean disease, asian soybean rust, anthracnose, powdery mildew, and any combination thereof, and/or

(3) The plant is selected from the group consisting of soybean, rice, fruit plants, vegetable plants, sugar beet, canola, grape vine, cotton, and any combination thereof.

In some embodiments, treating the plant to combat fungal pathogen infection and/or fungal disease is controlling fungal pathogen infection and/or fungal disease.

In some embodiments, treating the plant to combat fungal pathogen infection and/or fungal disease is preventing fungal pathogen infection and/or fungal disease.

In some embodiments, treating the plant to combat fungal pathogen infection and/or fungal disease is protecting the plant from fungal pathogen infection and/or fungal disease.

In some embodiments, the compound of formula I is applied by contacting the plant or locus thereof with an effective amount of the compound of formula I.

In some embodiments, the compound of formula I is applied to the roots of the plant. In some embodiments, the compound of formula I is applied to the foliage of the plant.

In some embodiments, the compound of formula I is applied to the seed. In some embodiments, the compound of formula I is applied to the young plants. In some embodiments, the plant is a seed or seedling.

In some embodiments, the fungal disease is a soil fungal disease.

In some embodiments, the plant disease is selected from the group consisting of: blast, banded sclerotial blight, early blight, late blight, leaf blight, apple scab, downy mildew, banana black streak leaf spot, downy mildew, soybean late season disease, asian soybean rust, anthracnose, powdery mildew, and any combination thereof.

In some embodiments, the plant disease is selected from the group consisting of: pestilence, banded sclerotial blight, early blight, apple scab, downy mildew, banana black streak, downy mildew, soybean late season disease, asian soybean rust, anthracnose, powdery mildew, and any combination thereof.

In some embodiments, the plant disease is a blast. In some embodiments, the plant disease is banded sclerotial blight. In some embodiments, the plant disease is an early blight. In some embodiments, the plant disease is a blast. In some embodiments, the plant disease is a late blight. In some embodiments, the plant disease is leaf blight. In some embodiments, the plant disease is apple scab. In some embodiments, the plant disease is downy mildew. In some embodiments, the plant disease is banana black streak. In some embodiments, the plant disease is downy mildew. In some embodiments, the plant disease is late quaternary disease of soybean. In some embodiments, the plant disease is asian soybean rust. In some embodiments, the plant disease is anthrax. In some embodiments, the plant disease is powdery mildew.

In some embodiments, the fungal pathogen is selected from the group consisting of: pyricularia oryzae, rhizoctonia solani, sclerotinia sclerotium, rhizoctonia cucumeris, marsdenia tenacissima, botrytis cinerea, sphaerotheca gracilis, alternaria solani, rhizoctonia cerealis, leptosphaera fumago, leptosphaera sojae, leptosphaera polymorpha, leptosphaera spinosa, leptosphaera sojae, leptosphaera viticola, leptosphaera fijia, phytophthora potato, leptosphaera capsici, leptosphaera gracilis, and any combination thereof.

In some embodiments, the fungal pathogen is selected from the group consisting of: pyricularia oryzae, rhizoctonia solani, sclerotinia sclerotium, rhizoctonia cerealis, marsdenia tenacissima, botrytis cinerea, sphaerotheca gracilis, rhizoctonia cerealis, alternaria solani, cercospora betana, mortierella gracilis, alternaria farina, leptosphaera sojae, leptosphaera polymorpha, leptosphaera spinosa, leptosphaera sojae, leptosphaera viticola, fijia, and any combination thereof.

In some embodiments, the fungal pathogen is Pyricularia oryzae. In some embodiments, the fungal pathogen is rhizoctonia solani. In some embodiments, the fungal pathogen is Sclerotinia sclerotium. In some embodiments, the fungal pathogen is a cucumber downy mildew pathogen. In some embodiments, the fungal pathogen is cladosporium cucumeris. In some embodiments, the fungal pathogen is aschersonia aleyrodis. In some embodiments, the fungal pathogen is botrytis cinerea. In some embodiments, the fungal pathogen is chaetomium globosum. In some embodiments, the fungal pathogen is a cucumber downy mildew pathogen. In some embodiments, the fungal pathogen is alternaria solani. In some embodiments, the fungal pathogen is cercospora betanus. In some embodiments, the fungal pathogen is a leaf spot of sugar beet. In some embodiments, the fungal pathogen is aschersonia aleyrodis. In some embodiments, the fungal pathogen is erysiphe necator. In some embodiments, the fungal pathogen is soybean rust. In some embodiments, the fungal pathogen is erysiphe sojae. In some embodiments, the fungal pathogen is a globeflower. In some embodiments, the fungal pathogen is corynespora polymorpha. In some embodiments, the fungal pathogen is a. Spinosa. In some embodiments, the fungal pathogen is a soybean purpura. In some embodiments, the fungal pathogen is downy mildew. In some embodiments, the fungal pathogen is fijisphaerella. In some embodiments, the fungal pathogen is downy mildew. In some embodiments, the fungal pathogen is potato late blight. In some embodiments, the fungal pathogen is pepper anthracnose pathogen. In some embodiments, the fungal pathogen is aschersonia aleyrodis.

In some embodiments, the plant is selected from the group consisting of soybean, rice, fruit plants, vegetable plants, sugar beet, canola, grape vine, cotton, and any combination thereof.

In some embodiments, the plant is soybean. In some embodiments, the plant is rice. In some embodiments, the plant is a fruit plant. In some embodiments, the plant is a vegetable plant. In some embodiments, the plant is sugar beet. In some embodiments, the plant is canola. In some embodiments, the plant is grape vine. In some embodiments, the plant is cotton.

In some embodiments, the fruit is apple. In some embodiments, the fruit is strawberry. In some embodiments, the fruit is banana.

In some embodiments, the vegetable is zucchini. In some embodiments, the vegetable is cucumber. In some embodiments, the vegetable is potato. In some embodiments, the vegetable is a pepper. In some embodiments, the vegetable is carrot.

In some embodiments, the plant is soybean and the fungal pathogen is Sclerotinia sclerotium.

In some embodiments, the plant is soybean and the fungal pathogen is rhizoctonia solani.

In some embodiments, the plant is rice and the fungal pathogen is rhizoctonia solani. In some embodiments, the plant is rice and the disease is banded sclerotial blight caused by the fungal pathogen rhizoctonia solani.

In some embodiments, the plant is rice and the fungal pathogen is Pyricularia oryzae. In some embodiments, the plant is rice and the disease is a blast caused by the fungal pathogen Pyricularia oryzae.

In some embodiments, the plant is canola and the fungal pathogen is sclerotinia (Sclerotinia sclerotiorum).

In some embodiments, the plant is cucumber and the fungal pathogen is a cucumber downy mildew. In some embodiments, the plant is cucumber and the disease is downy mildew caused by the fungal pathogen cucumber downy mildew.

In some embodiments, the plant is grapevine and the fungal pathogen is downy mildew. In some embodiments, the plant is grapevine and the disease is downy mildew caused by the fungal pathogen downy mildew.

In some embodiments, the plant is sugar beet and the fungal pathogen is powdery mildew of sugar beet. In some embodiments, the plant is sugar beet and the disease is powdery mildew caused by the fungal pathogen powdery mildew of sugar beet.

In some embodiments, the plant is banana and the fungal pathogen is fijisphaerella. In some embodiments, the plant is banana and the disease is leaf spot of banana caused by the fungal pathogen fijia globosa. In some embodiments, the plant is banana, the disease is leaf spot of banana caused by the fungal pathogen fijia globosa, and the EC composition of the compound of formula I is used. In some embodiments, the plant is banana, the disease is leaf spot of banana caused by the fungal pathogen fijia globosa, and an EC composition comprising 50g/L of the compound of formula I is used. Examples of EC compositions are provided in the experimental section.

In some embodiments, the plant is strawberry and the fungal pathogen is botrytis cinerea.

In some embodiments, the plant is apple and the fungal pathogen is aschersonia aleyrodis. In some embodiments, the plant is apple and the disease is powdery mildew caused by the fungal pathogen chaetomium gracile.

In some embodiments, the plant is soybean and the fungal pathogen is chaetomium globosum. In some embodiments, the plant is soybean and the disease is powdery mildew caused by the fungal pathogen chaetomium globosum.

In some embodiments, the plant is sugar beet and the fungal pathogen is cercospora betana. In some embodiments, the plant is sugar beet and the disease is beet leaf spot caused by cercospora betaensis.

In some embodiments, the plant is sugar beet and the fungal pathogen is a leaf spot of beet.

In some embodiments, the plant is soybean and the fungal pathogen is powdery mildew of soybean. In some embodiments, the plant is soybean and the disease is powdery mildew caused by the fungal pathogen soybean powdery mildew.

In some embodiments, the plant is cotton and the fungal pathogen is septoria viticola.

In some embodiments, the plant is soybean and the fungal pathogen is corynespora polymorpha.

In some embodiments, the plant is soybean and the fungal pathogen is a. Aschersonia.

In some embodiments, the plant is soybean and the fungal pathogen is soybean purpura.

In some embodiments, the plant is apple and the fungal pathogen is cladosporium cucumerinum. In some embodiments, the plant is apple and the disease is apple scab caused by the fungal pathogen cladosporium cucumeris.

In some embodiments, the plant is potato and the fungal pathogen is alternaria solani. In some embodiments, the plant is potato and the disease is an early blight caused by the fungal pathogen alternaria solani. In some embodiments, the plant is potato and the fungal pathogen is potato late blight. In some embodiments, the plant is potato and the disease is a late blight caused by potato late blight bacteria.

In some embodiments, the plant is soybean and the fungal pathogen is soybean rust.

In some embodiments, the plant is soybean and the fungal pathogen is fusarium graminearum.

In some embodiments, the plant is cucurbita pepo and the fungal pathogen is chaetomium globosum (powdery mildew).

In some embodiments, the plant is cucurbita pepo and the fungal pathogen is monocystis leucotrichia. In some embodiments, the plant is cucurbita pepo and the disease is powdery mildew caused by the fungal pathogen monocystis leucotrichia.

In some embodiments, the plant is cucumber and the disease is downy mildew.

In some embodiments, the plant is soybean and the disease is asian soybean rust.

In some embodiments, the plant is cotton and the fungal pathogen is a globeflower.

In some embodiments, the plant is capsicum and the fungal pathogen is colletotrichum.

In some embodiments, the plant is capsicum and the disease is anthrax.

In some embodiments, the plant is capsicum and the fungal pathogen is pepper anthracnose pathogen. In some embodiments, the plant is capsicum and the disease is leaf blight caused by pepper anthracnose.

In some embodiments, the plant is banana and the fungal pathogen is fijisphaerella.

In some embodiments, the method is effective for protecting plants or locus against fungal infection. In some embodiments, the method is effective for protecting plants or locus against fungal attack. In some embodiments, the method is effective for protecting a plant or locus from a fungal disease. In some embodiments, the method is effective for preventing fungal infection of a plant or locus.

In some embodiments, the method is effective for controlling fungal infection of a plant or locus. In some embodiments, the method is effective for controlling fungal diseases of infected plants or the locus. In some embodiments, the method is effective for controlling plant or soil diseases caused by phytopathogenic fungi. In some embodiments, the method is effective for controlling fungal attack on a plant or locus. In some embodiments, the method is effective for reducing fungal infection of a plant or locus. In some embodiments, the method is effective for treating plant or soil diseases caused by phytopathogenic fungi.

The invention also provides compositions for controlling pathogen-induced diseases on plants (as described in table a).

The invention also provides methods for controlling pathogen-induced diseases on plants (as described in table a).

Table a.

Disease and disease	Fungal pathogens	Crop plant
			Early blight	Alternaria species	Potatoes or tomatoes
Anthracnose disease	Genus Cephalosporium species	Bean
			Anthracnose disease	Bacillus anthracis of soybean	Chili pepper
Rust disease of Asian soybean	Soybean rust germ	Soybean
			Leaf spot of banana black streak	Fijiball cavity bacterium	Banana
Brown rust disease	Puccinia recondita (L.) Kuntze	Cereal
			Disease of coffee beans	Colletotrichum coffee	Coffee machine
Leaf rust of coffee	Leptospira caffei (Fr.) Kummer	Coffee machine
			Didymella pisi	Bacterial strain of Rhizoctonia solani	Bean
Downy mildew	Cucumber downy mildew fungus	Melon
			Downy mildew	Grape downy mildew fungus	Grape vine
Scab (gibberellic disease)	Fusarium species	Cereal
			Leaf spot of gray leaf	Leucomatous griseofulvis (Fr.) karst	Corn
Late blight disease	Potato late blight bacteria	Potatoes or tomatoes
			Leaf spot of beet	Cercospora betana	Sugar beet
Leaf spot of maize	Rhizoctonia cerealis (Fr.) karst	Corn
			Leaf spot of maize	Chaetomium carbotricornutum	Corn
Leaf spot of genus Cyanosporium	Mortierella sepedonioides (L.) Gaertn	Cereal
			Leaf spot of genus Cyanosporium	Acremonium leucotrichum	Cotton cotton
Leaf spot of genus Cyanosporium	Bacteria of beet leaf spot	Sugar beet
			Rice blast disease	Pyricularia oryzae	Rice
Rust disease	Beet rust germ	Sugar beet
			Scab disease of the sore	Alternaria alternata (L.) Gaertn	Drupe fruit
Sclerotinia genus	Sclerotinia sclerotiorum (L.) kuntze	OSR
			Septoria	Wheat leaf blight bacteria	Cereal
Banded sclerotial blight	Rhizoctonia solani/Rhizoctonia solani	Rice
			Leaf spot of maize	Isosporium sp	Corn
Wheel spot disease	Corynespora polymorpha	Soybean
			Yellow rust disease	Stripe rust bacteria	Cereal
Leaf spot of yellow streak of Banana	Acidocella banana	Banana

In some embodiments, the present invention provides compositions for controlling diseases caused by fungal pathogens on crops, wherein the diseases, fungal pathogens and crops are indicated in each row of table a.

In some embodiments, the present invention provides methods for controlling diseases caused by fungal pathogens on crops, wherein the diseases, fungal pathogens, and crops are indicated in each row of table a.

The invention also provides a composition for controlling powdery mildew on plants. The invention also provides compositions for controlling Erysiphae diffusa, erysiphae necator or Erysiiphae betae on plants. The invention also provides a method for controlling powdery mildew on plants. The invention also provides methods for controlling Erysiphae diffusa, erysiphae necator or Erysiiphae betae on plants.

The invention also provides a composition for controlling phytophthora parasitica (Plenodomus lingam) on plants. The invention also provides a method for controlling phytophthora parasitica on plants. In some embodiments, the plant is an OSR.

The invention also provides a composition for controlling phytophthora parasitica (Plenodomus biglobosus) on plants. The invention also provides a method for controlling the phytophthora parasitica of rape on plants. In some embodiments, the plant is an OSR.

The invention also provides compositions for controlling Phaeososphaeria maydis on plants. The invention also provides a method for controlling Phaeososphaeria maydis on plants. In some embodiments, the plant is maize.

The invention also provides compositions for controlling Alternaria alternata on plants. The invention also provides methods for controlling Alternaria alternata on plants.

In some embodiments, the plant is apple.

In some embodiments, the compound of formula I is applied as a seed treatment.

In some embodiments, the compound of formula I is applied as a seed treatment at an application rate of 0.5-50g ai per 100kg seed. In some embodiments, the compound of formula I is applied as a seed treatment at an application rate of 1-25g ai per 100kg seed. In some embodiments, the compound of formula I is applied as a seed treatment at an application rate of 1g ai/100kg seed. In some embodiments, the compound of formula I is applied as a seed treatment at an application rate of 2.5g ai per 100kg seed. In some embodiments, the compound of formula I is applied as a seed treatment at an application rate of 5g ai/100kg seed. In some embodiments, the compound of formula I is applied as a seed treatment at an application rate of 10g ai/100kg seed. In some embodiments, the compound of formula I is applied as a seed treatment at an application rate of 25g ai/100kg seed.

In some embodiments, the seed is soybean.

In some embodiments, when the compound of formula I is applied as a seed treatment, a suspension concentrate composition of the compound of formula I is used.

To thereby treat plants against fungal pathogen infection and/or fungal disease, wherein the application rate, disease, fungal pathogen, and/or crop is indicated in any one or any combination of the embodiments described herein below.

In some embodiments, the present invention provides methods for controlling a disease caused by a fungal pathogen on a crop, wherein the application rate, disease, fungal pathogen, and/or crop is indicated in any or any combination of the embodiments described herein below.

In some embodiments, the compound of formula I is applied as a foliar treatment. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 5 to 1000g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 5 to 500g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 50 to 200g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 50 to 150g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 200 to 500g ai/ha.

In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 6.25g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 12.5g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 25g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 50g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 75g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 100g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 125g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 150g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 175g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 200g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 225g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 250g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 275g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 300g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 400g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 450g ai/ha. In some embodiments, the compound of formula I is applied as a foliar treatment at an application rate of 500g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling Sclerotinia sclerotium in canola as foliar application is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling Sclerotinia sclerotium in canola as foliar application is 75-150g ai/ha. The administration time was at the time of flowering.

In some embodiments, the application rate of the compound of formula I for Sclerotinia sclerotium in soybeans as a seed treatment is 1-25g ai per 100kg seed. In some embodiments, the application rate of the compound of formula I for Sclerotinia sclerotium in soybeans as a seed treatment is 5-25g ai per 100kg seed.

In some embodiments, the application rate of the compound of formula I for controlling rhizoctonia solani (Rhizoctonia solani) in soybean as a seed treatment is 1-25g ai per 100kg seed. In some embodiments, the application rate of the compound of formula I for controlling rhizoctonia solani in soybean as a seed treatment is 5-25g ai per 100kg seed.

In some embodiments, the application rate of the compound of formula I for controlling pythium ultimum (phytophthora ultimum) in soybeans as a seed treatment is 5-25g ai/100kg seed.

In some embodiments, the application rate of the compound of formula I for controlling fusarium graminearum (Fusarium graminearum) in soybeans as a seed treatment is 5-25g ai per 100kg seed.

In some embodiments, the application rate of the compound of formula I for controlling fusarium graminearum in wheat as a seed treatment is 5-25g ai per 100kg seed.

In some embodiments, the application rate of the compound of formula I for controlling rhizoctonia solani (sheath blight) in rice as foliar application is 50-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling rhizoctonia solani (sheath blight) in rice as foliar application is 50-150g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling Pyricularia oryzae (blast) in rice as foliar application is 50-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling Pyricularia oryzae (blast) in rice as foliar application is 50-150g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling cladosporium cucumeris (apple scab) in fruits such as apples as foliar applications is 75-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling the aschersonia aleyrodis (powdery mildew) in fruits such as apples as foliar applications is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling the aschersonia aleyrodis (powdery mildew) in fruits such as apples as foliar applications is 75-150g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling Botrytis cinerea (Botrytis cinerea) in fruit plants as foliar application is 150-500g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling botrytis cinerea in fruit plants as foliar applications is 150-350g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling botrytis cinerea in strawberries as foliar application is 150-500g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling botrytis cinerea in strawberries as foliar application is 150-350g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling chaetomium monofilament (powdery mildew) in vegetable plants as a foliar application is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling chaetomium monofilament (powdery mildew) in vegetable plants as foliar application is 75-150g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling chaetomium monofilament (powdery mildew) in zucchini as foliar application is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling chaetomium monofilament (powdery mildew) in zucchini as foliar application is 75-150g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling chaetomium gracile (Podosphaera fuliginea) (powdery mildew) in vegetable plants as a foliar application is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling chaetomium gracile (powdery mildew) in vegetable plants as foliar application is 75-150g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling the monocystus leucotrichia (powdery mildew) in zucchini as foliar application is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling the monocystus leucotrichia (powdery mildew) in zucchini as foliar application is 100-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling cucumber downy mildew (downy mildew) in vegetable plants as a foliar application is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling cucumber downy mildew (downy mildew) in vegetable plants as a foliar application is 75-150g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling cucumber downy mildew (downy mildew) in cucumber as a foliar application is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling cucumber downy mildew (downy mildew) in cucumber as a foliar application is 75-150g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling alternaria solani in vegetable plants as foliar application is 75-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling alternaria solani in vegetable plants as foliar application is 75-150g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling alternaria solani in vegetable plants as foliar application is 100-150g ai/ha. In some embodiments, the compound of formula I for controlling alternaria solani (early blight) in potatoes as a foliar application is applied at a rate of 75-200g ai/ha. In some embodiments, the compound of formula I for controlling alternaria solani (early blight) in potatoes as a foliar application is applied at a rate of 75-150g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling alternaria solani (early blight) in potatoes as foliar application is 100-150g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling alternaria solani in potatoes as foliar application is from 175g ai/ha to 200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling alternaria solani in potatoes as foliar application is about 175g ai/ha or about 200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling alternaria solani in potatoes as foliar applications is about 100g ai/ha, 125g ai/ha, or 150g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling cercospora betaensis in sugar beet as a foliar application is 50-150g ai/ha. In some embodiments, the compound of formula I is used as a foliar application to control cercospora betaensis in sugar beet at an application rate of 75-150g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling cercospora betaensis in sugar beet as a foliar application is about 125g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling leaf spot bacteria in sugar beets as foliar application is 50-150g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling leaf spot bacteria in sugar beets as a foliar application is 125-150g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling powdery mildew (powdery mildew) of sugar beet as a foliar application is 50-150g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling soybean rust in soybeans (asian soybean rust) as foliar application is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling soybean powdery mildew (powdery mildew) in soybeans as foliar application is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling soybean pholiota in soybeans as foliar application is 50-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling late-season disease in soybeans as foliar application is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling the corynespora polymorpha (Corynespora cassiicola) in soybeans as foliar application is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling the administration of the soybean of the colletotrichum crassifolium (Colletotrichum dematium) as a leaf is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling the presence of reticulocytes in cotton (Mycosphaerella areola) as foliar applications is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling septoria albopictus (Ramularia areola) in cotton as foliar application is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling the presence of colletotrichum crassifolium (anthracnose) in vegetable plants as foliar applications is 50-200g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling the presence of colletotrichum (anthrax) in capsicum as a foliar application is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling pepper anthracnose in peppers as foliar applications is 150-250g ai/ha. In some embodiments, the application rate of the compound of formula I for controlling pepper anthracnose in peppers as a foliar application is about 200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling downy mildew (downy mildew) in grape vine as a foliar application is 50-200g ai/ha. The application rate is generally from 75 to 100g ai/ha.

In some embodiments, the application rate of the compound of formula I used to control fijia in fruits such as banana as leaf spot in the banana is 50-200g ai/ha.

In some embodiments, the application rate of the compound of formula I for controlling potato late blight bacteria (Phytophtora infestans) in potatoes as foliar applications is from 100g ai/ha to 200g ai/ha. In an embodiment, the application rate of the compound of formula I for controlling potato late blight bacteria in potatoes is about 150g ai/ha.

In some embodiments, the compound of formula I is applied to the seed. In some embodiments, the compound of formula I is applied to the young plants.

In some embodiments, the compound of formula I is applied to the soil. In some embodiments, the compound of formula I is applied to the locus of the fungus. In some embodiments, the compound of formula I is applied to a locus where a fungal infection and/or fungal disease is to be prevented.

In some embodiments, the compound of formula I is applied to a part of a plant, an area adjacent to a plant, soil in contact with a plant, soil adjacent to a plant, any surface in contact with a plant, a seed, and/or equipment used in agriculture. In some embodiments, the compound of formula I is applied to, near, or near the locus of a plant, a locus of a fungus. In some embodiments, the compound of formula I is applied to the soil in which the plant is growing. In some embodiments, the compound of formula I is applied to the soil in which the plant is to be grown.

In some embodiments, the compound of formula I is applied at the time of planting.

In some embodiments, the compound of formula I is administered 1 to 60 days after planting.

In some embodiments, the compound of formula I is administered 1 to 9 months after planting.

In some embodiments, the compound of formula I is administered once during the growing season.

In some embodiments, the compound of formula I is administered at least once during the growing season.

In some embodiments, the compound of formula I is administered two or more times during the growing season.

In some embodiments, the compound of formula I is applied as a soil application. In some embodiments, the compound of formula I is administered as foliar administration.

In some embodiments, the method comprises the protective administration of a compound of formula I. In some embodiments, the method comprises therapeutic administration of a compound of formula I.

In some embodiments, the method comprises administering the compound of formula I prior to showing symptoms of the fungal disease.

In some embodiments, the method comprises administering the compound of formula I at a time when the disease pressure is low.

In some embodiments, the method comprises administering the compound of formula I after the presence of a fungal pathogen infection.

In some embodiments, the method comprises administering the compound of formula I after showing symptoms of the fungal disease.

In some embodiments, the compound of formula I is applied at a rate of 150g ai/ha or less.

In some embodiments, the compound of formula I is applied at a rate of 100g ai/ha or less.

In some embodiments, the compound of formula I is administered at a rate of 100g ai/ha or less, two administrations being spaced 7 days apart between the two administrations.

In some embodiments, the method is effective for reducing leaf necrosis. In some embodiments, leaf necrosis is reduced by at least 10%. In some embodiments, leaf necrosis is reduced by at least 25%. In some embodiments, leaf necrosis is reduced by at least 50%. In some embodiments, leaf necrosis is reduced by at least 75%.

In some embodiments, the effectiveness of the method is assessed at least one week after administration of the compound of formula I. In some embodiments, the effectiveness of the method is assessed at least two weeks after administration of the compound of formula I. In some embodiments, the effectiveness of the method is assessed at least three weeks after administration of the compound of formula I. In some embodiments, the effectiveness of the method is assessed at least four weeks after administration of the compound of formula I.

In some embodiments, emulsifiable Concentrate (EC) compositions of the compounds of formula I are administered. In some embodiments, an EC composition comprising 50g/L of a compound of formula I is administered.

In some embodiments, a Suspension Concentrate (SC) composition of the compound of formula I is administered. In some embodiments, an SC composition comprising 500g/L of a compound of formula I is administered.

In some embodiments, an Oil Dispersion (OD) composition of the compound of formula I is administered. In some embodiments, an OD composition comprising 250g/L of a compound of formula I is administered.

Examples of EC, SC and OD compositions of the compounds of formula I are described below.

In some embodiments of the present invention, in some embodiments,

(3) The seed or seedling of the plant is selected from the group consisting of soybean, rice, fruit, vegetable, sugar beet, rapeseed oil, grape vine, cotton, and any combination thereof.

In some embodiments of the present invention, in some embodiments,

In some embodiments, treating the plant or locus thereof comprises treating the seed, seedling, or locus of the seed or seedling.

In some embodiments of the present invention, in some embodiments,

Wherein:

In some embodiments of the present invention, in some embodiments,

And wherein:

In some embodiments of the present invention, in some embodiments,

Wherein:

In some embodiments of the present invention, in some embodiments,

The present invention also provides a composition comprising an amount of a compound of formula I for treating plants to combat fungal pathogen infection and/or fungal disease, wherein:

In some embodiments of the present invention, in some embodiments,

The present invention provides a method for treating plants against fungal pathogen infection and/or fungal disease comprising applying an amount of a compound of formula I

Wherein the amount is effective to treat the plant against fungal pathogen infection and/or fungal disease and has an ecologically acceptable effect on non-target organisms.

The present invention provides a method for treating plants against fungal pathogen infection and/or fungal disease comprising applying an amount of a compound of formula I.

Wherein the amount is less than 150g ai/ha.

In some embodiments of the present invention, in some embodiments,

In some embodiments, the amount has an ecologically acceptable effect on the propagation of the non-target organism.

Ecological effects can be assessed using eu guidelines including, but not limited to, documents used in wheat and barley, such as EFSA (2009) guidelines for risk assessment of birds and mammals, EFSA Journal 2009 for hierarchical risk assessment of plant protection products of aquatic organisms in field surface water; 1438, EFSA (2013) guidelines. EFSA Journal 2013;11 3290 and SANCO (2002) guidelines for terrestrial ecotoxicology according to European Union directive 91/414/EEC, SANCO/10329/2002rev 2final,2002, 10 month 17, each of which is hereby incorporated by reference in its entirety.

In some embodiments, the amount has an ecologically acceptable effect on the growth and/or development of the non-target organism.

In some embodiments, the amount has an ecologically acceptable acute effect on the non-target organism.

In some embodiments, the amount has an ecologically acceptable chronic effect on the non-target organism.

In some embodiments, the ecologically acceptable effect is a mortality rate of less than 50% of the non-target organism species. In some embodiments, the ecologically acceptable effect is a mortality rate of less than 20% of the non-target organism species. In some embodiments, the ecologically acceptable effect is a mortality rate of less than 10% of the non-target organism species.

In some embodiments, the non-target organism is a bird. In some embodiments, the amount has an ecologically acceptable acute effect on birds. In some embodiments, the amount has an ecologically acceptable effect on the reproduction of birds. In some embodiments, the bird is a north american quail. North american quails are used as an alternative species to birds.

In some embodiments, the non-target organism is a mammal. In some embodiments, the amount has an ecologically acceptable acute effect on the mammal. In some embodiments, the amount has an ecologically acceptable chronic effect on the mammal. In some embodiments, the mammal is a rat. In some embodiments, the mammal is a rabbit. Rats and rabbits were used as an alternative species for mammals.

In some embodiments, the non-target organism is a fish. In some embodiments, the amount has an ecologically acceptable acute effect on fish. In some embodiments, the amount has an ecologically acceptable chronic effect on fish. In some embodiments, the fish is rainbow trout. Rainbow trout is used as an alternative species to fish.

In some embodiments, the non-target organism is an aquatic invertebrate. In some embodiments, the amount has an ecologically acceptable acute effect on the aquatic invertebrate. In some embodiments, the amount has an ecologically acceptable chronic effect on the aquatic invertebrate. In some embodiments, the aquatic invertebrate is a daphnia. Daphnia is used as an alternative species to aquatic invertebrates.

In some embodiments, the non-target organism is an alga. In some embodiments, the amount has an ecologically acceptable chronic effect on algae. In some embodiments, the algae is green algae. Green algae are used as an alternative species to algae.

In some embodiments, the non-target organism is an arthropod. In some embodiments, the amount has an ecologically acceptable acute oral effect (oral effect) on the arthropod. In some embodiments, the amount has an ecologically acceptable acute contact effect on the arthropod. In some embodiments, the amount has an ecologically acceptable chronic oral effect on the arthropod. In some embodiments, the amount has an ecologically acceptable chronic effect on larvae of the arthropod. In some embodiments, the amount has an ecologically acceptable effect on the reproduction of the arthropod. In some embodiments, the arthropod is a parasitic wasp. In some embodiments, the arthropod is a bee.

In some embodiments, the amount has an ecologically acceptable acute oral effect on bees. In some embodiments, the amount has an ecologically acceptable acute contact effect on the bees. In some embodiments, the amount has an ecologically acceptable chronic oral effect on bees. In some embodiments, the amount has an ecologically acceptable chronic effect on the larvae of the bees. In some embodiments, the amount has an ecologically acceptable acute effect on colony survival of bees. In some embodiments, the amount has an ecologically acceptable chronic effect on colony survival of bees. In some embodiments, the amount has an ecologically acceptable acute effect on the development of the bees. In some embodiments, the amount has an ecologically acceptable chronic effect on the development of the bees.

In some embodiments, the ecologically acceptable effect is a reduction in colony size of bees of less than 10%. In some embodiments, the ecologically acceptable effect is a reduction in colony size of bees of less than 7%.

In some embodiments, the non-target organism is an earthworm. In some embodiments, the amount has an ecologically acceptable chronic effect on earthworms. In some embodiments, the earthworm is Eisenia fetida (Eisenia fetida).

In some embodiments, the non-target organism is a soil microorganism. In some embodiments, the amount has an ecologically acceptable effect on the nitrogen activity of the soil microorganism.

In some embodiments, the non-target organism is a crop. In some embodiments, the amount has an ecologically acceptable effect on emergence of the crop. In some embodiments, the amount has an ecologically acceptable effect on plant vigor (vegetative vigour) of the crop. In some embodiments, the crop is sugar beet, canola, cucumber, carrot, soybean, sunflower, onion, common oat, ryegrass, or corn.

In some embodiments, the ecologically acceptable effect is substantially no observable effect. In some embodiments, the ecologically acceptable effect is no observable effect.

In some embodiments, the amount of the compound of formula I is 150g ai/ha or less.

In some embodiments, the amount of the compound of formula I is 100g ai/ha or less.

In some embodiments, the amount of the compound of formula I is 100g ai/ha or less, administered twice at 7-day intervals between two administrations.

The invention also provides mature plants resistant to fungal attack, wherein the mature plants or seeds or seedlings adapted to produce mature plants are treated with an amount of a compound of formula I

Wherein the treated mature plant has an ecologically acceptable effect on non-target organisms contacting the treated mature plant. />

In some embodiments, the compounds of formula I are formulated as compositions.

In some embodiments, the composition is an EC composition. In some embodiments, the composition is an SC composition. In some embodiments, the composition is an OD composition.

In some embodiments, the compositions are used to control fungal pathogen infection and/or fungal disease. In some embodiments, the compositions are used to control fungal diseases caused by fungal pathogens.

In some embodiments, the composition is for preventing fungal pathogen infection and/or fungal disease.

In some embodiments, the compositions are used to protect plants from fungal pathogen infection and/or fungal disease.

In some embodiments, the composition comprises at least one stabilizing surfactant. In some embodiments, the composition comprises at least two stabilizing surfactants. In some embodiments, the composition comprises two stabilizing surfactants. In some embodiments, the composition comprises a stabilizing system.

In some embodiments, one of the stabilizing surfactants is a nonionic stabilizing surfactant. In some embodiments, the nonionic stabilizing surfactant is selected from the group consisting of polymers, esters of alkoxylated diethylethanolamine, polyalkylene oxide alcohol ethers, and alcohols.

In some embodiments, the polymer is a block polymer of a random polymer. In some embodiments, the polymer is a triblock polymer. In some embodiments, the triblock polymer is an ABA block polymer. In some casesIn embodiments, the polymer has a low HLB (hydrophilic-lipophilic balance) value, preferably an HLB value of 5. In some embodiments, the polymer is atlaox ^TM 4912 (manufactured and sold by Croda).

In some embodiments, the ester alkoxylated amine is atlaox ^TM 4915 alkoxylated diethylethanolamine, diethylethanolamine mono-trimeric linoleate (mono-trimerate), or atlaox ^TM 4915 (manufactured and sold by Croda).

In some embodiments, the alkoxylated fatty alcohol is Genapol X080 (manufactured and sold by Clariant), genapol X050 (manufactured and sold by Clariant), tridecyl alcohol polyethylene glycol ether, rhododurf LA 30 (manufactured and sold by Solvay), aerosol OT-SE or Aerosol OT-100 (manufactured and sold by Solvay), rhodocal 70/B (manufactured and sold by Solvay), arlatone TV (manufactured and sold by Croda), alkmuls a (manufactured and sold by Solvay), or alkmuls BR (manufactured and sold by Solvay).

In some embodiments, the alcohol has a short carbon chain of C1-C6. In some embodiments, the alcohol has a long carbon chain of C7-C20.

In some embodiments, the nonionic stabilizing surfactant is a nonionic derivative of a polyalkylene oxide polyarylether.

In some embodiments, one of the stabilizing surfactants is an ionic surfactant. In some embodiments, the ionic stabilizing surfactant is an anionic stabilizing surfactant. By anionic stabilizing surfactants is meant compounds having anionic groups such as phosphonates and sulphonates. An example of an ionic surfactant that can be used is dioctyl sodium sulfosuccinate, which is described by Solvay OT-SE is manufactured and sold.

In some embodiments, the anionic stabilizing surfactant is an anionic derivative of a polyalkylene oxide polyarylether.

In some embodiments, the composition comprises at least one nonionic stabilizing surfactant and at least one anionic stabilizing surfactant. In some embodiments, the stabilizing system comprises at least one nonionic stabilizing surfactant and at least one anionic stabilizing surfactant.

In some embodiments, the composition comprising a nonionic stabilizing surfactant and an anionic stabilizing surfactant is an SC composition. In some embodiments, the combination, mixture or composition comprising the nonionic stabilizing surfactant and the anionic stabilizing surfactant is a SE composition.

In some embodiments, one of the stabilizing surfactants is a derivative of a polyalkylene oxide polyarylether. In some embodiments, the derivative of the polyalkylene oxide polyarylether is a nonionic derivative of the polyalkylene oxide polyarylether. In some embodiments, the derivative of the polyalkylene oxide polyarylether surfactant is an anionic derivative of a polyalkylene oxide polyarylether.

In some embodiments, the composition comprises at least two stabilizing surfactants. In some embodiments, the two stabilizing surfactants comprise two derivatives of a polyalkylene oxide polyarylether. In some embodiments, the two stabilizing surfactants comprise a nonionic derivative of a polyalkylene oxide polyarylether and an anionic derivative of a polyalkylene oxide polyarylether.

In some embodiments, the nonionic derivative of the polyalkylene oxide polyarylether is a compound having aryl groups substituted with at least two aromatic groups.

In some embodiments, the nonionic derivative of the polyalkylene oxide polyarylether has the following structure:

in some embodiments, the anionic derivative of the polyalkylene oxide polyarylether is a compound having aryl groups substituted with at least two aromatic groups.

In some embodiments, the anionic groups of the anionic derivatives of the polyalkylene oxide polyaryl ether have a group selected from phosphate (PO ₄ ) Phosphonate (PO) ₃ ) Sulfonate radical (SO) ₃ ) And sulfate radical (SO) ₄ ) Is an anionic group of (a).

The polyalkylene oxide may include, but is not limited to, polyethylene oxide groups, polypropylene oxide, polybutylene oxide, and any combination thereof. In some embodiments, the polyalkylene oxide group is polyethylene oxide. In some embodiments, the polyalkylene oxide group is polypropylene oxide.

Polyalkylene oxides may include, but are not limited to, copolymers and homogeneous polymers. Copolymers may include, but are not limited to, random polymers and block polymers. In some embodiments, the polyalkylene oxide groups are diblock copolymers. In some embodiments, the polyalkylene oxide groups are triblock copolymers.

In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide styrylphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide benzyl phenyl ether. In some embodiments, the polyalkylene oxide polyarylether is a polyalkylene oxide diphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide tristyrylphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide distyrylphenyl ether. In some embodiments, the polyalkylene oxide distyrylphenyl ether is polyoxyethylene distyrylphenyl ether.

In some embodiments, the polyalkylene oxide polyarylether is an anionic stabilizing surfactant. By anionic stabilizing surfactants is meant compounds having anionic groups such as phosphonates and sulphonates.

In some embodiments, the salt comprises a cation. In some embodiments, the cation is selected from the group consisting of sodium, potassium, ammonium, calcium, magnesium, and combinations thereof.

In some embodiments, the anionic derivative of the polyalkylene oxide polyarylether has the following structure:

in some embodiments, the anionic derivative of the polyalkylene oxide polyaryl ether is a tristyrylphenol ethoxylate phosphate ester. Cation +

In some embodiments, the polyalkylene oxide polyaryl ether is a tristyrylphenol ethoxylate phosphate ester. Preferably, the tristyrylphenol ethoxylate phosphate ester is manufactured and sold by Solvay3D33。

In some embodiments, the polyalkylene oxide polyaryl ether is a 2,4, 6-tris- (1-phenylethyl) -phenol polyglycol ether having 54 EO. Preferably, the 2,4, 6-tris- (1-phenylethyl) -phenol polyglycol ether having 54EO is manufactured and sold by ClariantTS 540。

In some embodiments, the polyalkylene oxide polyaryl ether is an ethoxylated tristyrylphenol. Preferably, the ethoxylated tristyrylphenols are manufactured and sold by SolvayTS/54。

In some embodiments, the salt comprises a cation selected from the group consisting of sodium, potassium, ammonium, calcium, magnesium, and combinations thereof.

The polyalkylene oxide polyarylether surfactant may include, but is not limited to, polyphenylethylphenol and tristyrylphenol.

The polyalkylene oxide polyarylether surfactant may include, but is not limited to, a non-blocked surfactant, a blocked surfactant, or a combination thereof.

In some embodiments, the composition comprises two or more stabilizing surfactants, and the two stabilizing surfactants are a nonionic polyalkylene oxide polyarylether surfactant and an anionic polyalkylene oxide polyarylether surfactant. In some embodiments, the nonionic surfactant is a tristyrylphenol ethoxylate. In some embodiments, the anionic surfactant is a tristyrylphenol ethoxylate phosphate ether.

In some embodiments, the composition comprises a tristyrylphenol ethoxylate and a tristyrylphenol ethoxylate phosphate ether.

In some embodiments, the nonionic polyalkylene oxide polyarylether is a compound having ether groups substituted with at least two groups comprising aromatic rings.

In some embodiments, the polyalkylene oxide group is a polyoxyethylene. In some embodiments, the polyalkylene oxide group is a polyoxypropylene. In some embodiments, the polyalkylene oxide groups are block copolymers of polyoxyethylene. In some embodiments, the polyalkylene oxide groups are block copolymers of polyoxypropylene.

The polyalkylene oxide may include, but is not limited to, polyethoxylated groups, polypropoxylated groups, polybutoxylated groups, and any combination thereof.

Polyalkylene oxides may include, but are not limited to, copolymers and homogeneous polymers.

Copolymers may include, but are not limited to, random polymers and block polymers.

In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is a polyoxyethylene tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is a polyoxyethylene polyoxypropylene tristyrylphenyl ether.

In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide distyrylphenyl ether. In some embodiments, the polyalkylene oxide distyrylphenyl ether is polyoxyethylene distyrylphenyl ether.

In some embodiments, the nonionic derivative of the polyalkylene oxide polyaryl ether is a tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the stabilizing surfactant is a derivative of tristyrylphenol-polyethylene glycol ether.

In some embodiments, the stabilizing surfactant is an anionic derivative of tristyrylphenol-polyethylene glycol ether.

In some embodiments, the stabilizing surfactant is a nonionic derivative of tristyrylphenol-polyethylene glycol ether.

In some embodiments, the composition comprises two stabilizing surfactants, and the two stabilizing surfactants are Soprophor 3D33 and Soprophor TS/54 (TSP 54).

In some embodiments, the composition comprises two stabilizing surfactants, and the two stabilizing surfactants are derivatives of polyalkylene oxide polyaryl ethers. In some embodiments, the combination, mixture or composition comprises two stabilizing surfactants, wherein one stabilizing surfactant is a nonionic derivative of a polyalkylene oxide polyarylether and one stabilizing surfactant is an anionic derivative of a polyalkylene oxide polyarylether.

In some embodiments, the composition comprises at least two stabilizing surfactants, wherein at least one stabilizing surfactant is a nonionic derivative of a polyalkylene oxide polyarylether and at least one stabilizing surfactant is an anionic derivative of a polyalkylene oxide polyarylether.

In some embodiments, the composition comprises two stabilizing surfactants, wherein one stabilizing surfactant is a nonionic derivative of a polyalkylene oxide polyarylether and one stabilizing surfactant is an anionic derivative of a polyalkylene oxide polyarylether.

In some embodiments, the stabilizing surfactant is Soprophor3D 33.

In some embodiments, the stabilizing surfactant is a tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the polyalkylene oxide polyaryl ether is Soprophor3D 33 from Solvay.

In some embodiments, the polyalkylene oxide polyaryl ether is Emulsogen TS 540 from Clariant.

In some embodiments, the polyalkylene oxide polyaryl ether is SOPROPHOR TS/54 from Solvay.

Polyaryl groups may refer to, but are not limited to, polyphenylethylphenol and tristyrylphenol.

The polyalkylene oxide polyarylether surfactant refers to a non-blocked surfactant, a blocked surfactant, or a combination thereof.

In some embodiments, the combination of surfactants comprises a mixture of nonionic polyalkylene oxide polyarylether surfactant and anionic polyalkylene oxide polyarylether surfactant. In some embodiments, the nonionic surfactant is a tristyrylphenol ethoxylate. In some embodiments, the anionic surfactant is a tristyrylphenol ethoxylate phosphate ether.

In some embodiments, the combination of surfactants comprises a tristyrylphenol ethoxylate and a tristyrylphenol ethoxylate phosphate ether.

In some embodiments, the stabilizing surfactant is emulgen TS 540.

In some embodiments, the nonionic derivative of the surfactant is emulgagen TS 540.

In some embodiments, the stabilizing surfactant is Soprophor TS/54.

In some embodiments, the nonionic derivative of the polyalkylene oxide polyaryl ether is Soprophor TS/54.

In some embodiments, the composition comprises a stabilizing system.

In some embodiments, the weight ratio of the compound of formula I to the nonionic derivative of the polyalkylene oxide polyarylether is from 25:1 to 10:1. In some embodiments, the weight ratio of the compound of formula I to the anionic derivative of the polyalkylene oxide polyarylether is from 25:1 to 10:1.

In some embodiments, the composition is free of phytologically acceptable adjuvants.

In some embodiments, the compound of formula I is administered without one or more adjuvants.

In some embodiments, the composition further comprises a phytologically acceptable adjuvant.

In some embodiments, the compound of formula I is administered as a combination with one or more adjuvants.

In some embodiments, the compound of formula I and the one or more adjuvants are formulated as separate compositions and administered separately, such as simultaneously (such as a tank mix) or contemporaneously.

In some embodiments, the phytologically acceptable adjuvant is selected from the group consisting of:

(i) Polyalkylene oxide alkyl ethers;

(ii) A siloxane polyalkylene oxide copolymer;

(iii) Esters of fatty acids;

(iv) Vinyl pyrrolidone and its derivatives; and

(v) Sugar-based surfactants.

In some embodiments, the polyalkylene oxide alkyl ether is a polyalkoxylated alcohol.

In some embodiments, the alkyl groups of the polyalkylene oxide alkyl ether include, but are not limited to, carbohydrate chains comprising C1-C26.

In some embodiments, the alcohol of the polyalkoxylated alcohol includes, but is not limited to, a C1-C26 carbohydrate chain.

In some embodiments, the alkyl groups of the polyalkylene oxide alkyl ether include, but are not limited to, short carbohydrate chains and long carbohydrate chains.

Carbohydrate chains may refer to, but are not limited to, saturated, unsaturated, branched, and unbranched chains.

In some embodiments, short chain refers to C1-C8. In some embodiments, long chain refers to C9-C26.

In some embodiments, polyalkylene oxide refers to, but is not limited to, polyethylene oxide, polypropylene oxide, polybutylene oxide, or combinations thereof.

In some embodiments, the polyalkylene oxide includes, but is not limited to, copolymers. Copolymers are understood to mean block copolymers, such as polyethylene oxide-polypropylene oxide, and/or random copolymers, such as ethylene oxide-propylene oxide. In some embodiments, the polyalkylene oxide block copolymer is a diblock copolymer. In some embodiments, the polyalkylene oxide block copolymer is a triblock copolymer.

In some embodiments, the triblock copolymer is polyethylene oxide/polypropylene oxide/polyethylene oxide.

In some embodiments, the polyalkylene oxide alkyl ether is alkyl-terminated. In some embodiments, alkyl groups include, but are not limited to, short carbohydrate chains and long carbohydrate chains. Carbohydrate chains may refer to, but are not limited to, saturated, unsaturated, branched, and unbranched chains. In some embodiments, short chain refers to C1-C8.

In some embodiments, the polyalkylene oxide alkyl ether is isotridecyl alcohol polyglycol ether.

In some embodiments, the polyalkylene oxide alkyl ether is a C16-C18 alcohol ethoxylate propoxylate ether.

In some embodiments, the C16-C18 alcohol ethoxylate propoxylate ether is ethyllan 995 manufactured and sold by Akzo Nobel Agrochemicals. In some embodiments, the C16-C18 alcohol ethoxylate propoxylate ether is manufactured and sold by BASFBP420。

In some embodiments, the polyalkylene oxide alkyl ether is an ethoxylate propoxylate alcohol.

In some embodiments, the ethoxylate propoxylate alcohol is Synperonic 13/9 manufactured and sold by Croda. In some embodiments, the ethoxylate propoxylate alcohol is Atplus PFA manufactured and sold by Croda.

In some embodiments, the isotridecyl alcohol polyglycol ether is Genapol X80 manufactured and sold by Clariant. In some embodiments, the isotridecyl alcohol polyglycol ether is manufactured and sold by BASF

In some embodiments, the polyalkylene oxide alkyl ether is effective to reduce the surface tension of the composition and improve the diffusion of the compound of formula I on the plant leaves. Lowering the surface tension results in reduced drift from the leaves.

In some embodiments, the siloxane polyalkylene oxide copolymer refers to an organically modified trisiloxane.

In some embodiments, the siloxane polyalkylene oxide copolymer is Break thre S233 from Evonik. In some embodiments, the siloxane polyalkylene oxide copolymer is Silwett 077 from Momentive.

In some embodiments, the siloxane polyalkylene oxide copolymer is effective to reduce the surface tension of the combination, mixture or composition. Silicone surfactants were found to be highly effective agents for reducing surface tension and rapidly diffusing compositions on lipophilic surfaces.

In some embodiments, esters of fatty acids may include, but are not limited to, alkyl esters of fatty acids and vegetable oils.

In some embodiments, the alkyl ester comprises a carbohydrate chain comprising C10-C20.

In some embodiments, alkyl groups include, but are not limited to, short carbohydrate chains.

In some embodiments, short chain refers to C1-C8. In some embodiments, the fatty acid alkyl ester is Rhodaphac PA/23 (phosphate ester of ethoxylated fatty alcohol) from Solvay or Alkamuls VO/2003 (ethoxylated (18 EO) fatty acid) from Solvay.

In some embodiments, the adjuvant is tridecyl alcohol ethoxylated or polyoxyethylene (9) isotridecyl alcohol.

In some embodiments, vegetable oils include, but are not limited to, vegetable oils and derivatives thereof.

In some embodiments, vegetable oils include, but are not limited to, seed oil, coconut oil, rapeseed oil, castor oil, soybean oil, palm oil, and corn oil.

In some embodiments, the derivative of the vegetable oil refers to an alkyl ester, polyalkylene oxide.

Polyalkylene oxide refers to polyethylene oxide, polypropylene oxide, polybutylene oxide, and combinations thereof.

In some embodiments, vegetable oils and their derivatives include, but are not limited to, coconut fatty acid esters of rapeseed oil methylated esters and polyglycerol ethers.

In some embodiments, the adjuvant is a mixture of methylated seed oil and polyglycerol ester.

In some embodiments, the rapeseed oil methylated ester is Agnique ME 18RDF manufactured and sold by BASF.

In some embodiments, the polyalkylene oxide derivative of the vegetable oil is a coconut fatty acid ester of a polyglyceryl ether.

In some embodiments, the coconut fatty acid ester of a polyglyceryl ether is syngen GL5 manufactured and sold by Clariant.

In some embodiments, the esters of fatty acids soften the surface properties of the leaves for better and efficient penetration of the compounds of formula I.

In some embodiments, the derivative of vinylpyrrolidone is a block copolymer of vinylpyrrolidone and vinyl acetate (VP/VA).

In some embodiments, the block copolymer of vinylpyrrolidone and vinyl acetate is Sokalan VA 64P manufactured and sold by Ashland.

In some embodiments, the block copolymer of vinyl pyrrolidone and vinyl acetate is Agrimer VA 6 manufactured and sold by Ashland.

In some embodiments, vinyl pyrrolidone (PVP) and derivatives thereof are effective for increasing adhesion of compounds of formula I to plant leaves for improved adhesion and retention characteristics (e.g., for rain fastness).

Sugar-based surfactants may include, but are not limited to, sorbitan esters, sucrose esters, alkyl polyglycosides, and fatty acid glucamides.

In some embodiments, the sugar-based surfactant is an alkyl or fatty acid derivative of glucamide.

In some embodiments, the sugar-based surfactant is an alkyl glucamide.

In some embodiments, the fatty acid glucamide is a C8/C10 fatty acid glucamide.

In some embodiments, the C8/C10 fatty acid glucamide is synergen GA from Clariant.

In some embodiments, the sugar-based surfactant is sorbitan and derivatives thereof.

In some embodiments, the derivatives of sorbitan are polyethylene oxide derivatives and fatty acid esters.

In some embodiments, the sorbitan is a di-or tri-fatty acid ester. In some embodiments, the derivative of sorbitan is a polyethylene oxide derivative comprising 20 to 80 ethylene oxide groups.

In some embodiments, the derivative of sorbitan is Tween 80.

In some embodiments, the sugar-based surfactant affects the leaf surface for improving penetration of the compound of formula I through the leaf surface.

In some embodiments, the composition comprises a multi-adjuvant system. A multi-adjuvant system refers to a blend or any combination of adjuvants.

In some embodiments, the composition comprises at least two adjuvants. In some embodiments, the combination, mixture or composition comprises at least three adjuvants.

In some embodiments, the blend of adjuvants includes, but is not limited to, a combination of an alkyl fatty acid ester and a fatty alcohol alkoxylate.

In some embodiments, the combination of alkyl fatty acid esters and fatty alcohol alkoxylates is a synergy SOC manufactured and sold by Clariant.

In some embodiments, the combination of alkyl fatty acid ester and fatty alcohol alkoxylate is FOP manufactured and sold by Clariant.

In some embodiments, the blend of adjuvants includes, but is not limited to, a combination of a vegetable oil and/or derivative thereof and a sugar-based surfactant.

In some embodiments, the composition comprises a pH adjuster.

In some embodiments, the pH adjusting agent may include, but is not limited to, buffers, bases, and/or acidulants.

In some embodiments, the pH adjuster is an acid. In some embodiments, the pH adjuster is a base.

In some embodiments, the pH adjuster is a mixture of at least one base and at least one acid.

In some embodiments, the pH adjuster is a buffer.

Buffer means a combination of acid and base. Acids include, but are not limited to, organic and inorganic acids. Bases include, but are not limited to, organic and inorganic bases.

The organic acid may include, but is not limited to, citric acid, formic acid, acetic acid, propionic acid, butyric acid, oxalic acid, lactic acid, malic acid, and benzoic acid.

The inorganic acids may include, but are not limited to, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, and boric acid.

The organic base may include, but is not limited to, primary and secondary amines, pyridines, imidazoles, and any combination thereof.

In some embodiments, the pH adjuster is potassium hydrogen phosphate.

In some embodiments, the pH adjuster is a combination of disodium hydrogen phosphate and potassium hydrogen phosphate.

In some embodiments, the compound of formula I is combined with at least one additional fungicide.

In some embodiments, the compound of formula I and one or more additional fungicides are applied simultaneously.

In some embodiments, the compound of formula I and one or more additional fungicides are applied contemporaneously.

In some embodiments, the compound of formula I and one or more additional fungicides are applied sequentially.

In some embodiments, the compound of formula I and one or more additional fungicides are applied separately.

In some embodiments, the compound of formula I is applied together with one or more additional fungicides.

In some embodiments, the compound of formula I and one or more additional fungicides are applied together as a tank mixture. In some embodiments, the compound of formula I and one or more additional fungicides are formulated in a single composition. In some embodiments, the compound of formula I and one or more additional fungicides are formulated in two or more separate compositions.

In some embodiments, the invention further comprises at least one additional pesticide. In some embodiments, the pesticide is a fungicide, herbicide, insecticide, acaricide, or nematicide.

The additional fungicide may be, but is not limited to boscalid, ipratropium, azoxystrobin, prothioconazole, fluopyram, fluxastrobin, fluazinam, folpet, fludioxonil, penoxsulam (Revysol), prothioconazole, azoxystrobin, copper, captan, mancozeb, chlorothalonil, phosphonate, ethiprole, fluopicolide, zoxamide, fenhexamid, cyazofamid, indazole-sulfanilamide, fluzoxamide, fluoxastrobin, metalaxyl, downy-cymoxanil, dimethomorph, fluazinam, buprofezin, triazole fungicide, strobin fungicide, sulfur, fenpropidium, phenoxyquinoline, SDHI fungicide, and any combination thereof.

In some embodiments, the combination of the compound of formula I and the additional fungicide increases the control of fungal diseases. In some embodiments, the combination of a compound of formula I and an additional fungicide increases the prevention of fungal diseases. In some embodiments, the combination of the compound of formula I and the additional fungicide reduces the time for effective control of fungal diseases. In some embodiments, the combination of the compound of formula I and the additional fungicide reduces the amount of one or more fungicides required for effective control of fungal diseases. In some embodiments, the combination of the compound of formula I and the additional fungicide expands the control effect of the individual fungicides in the mixture on crop type and disease. In some embodiments, the combination of the compound of formula I and the additional fungicide extends the time of control of the mixture in terms of crop type and disease compared to the individual fungicides in the mixture. In some embodiments, the combination of the compound of formula I and the additional fungicide extends the time of control of individual fungicides in the mixture with respect to crop type and disease.

The invention also provides a method of improving the ecological safety of a fungicide comprising applying to a plant or locus a fungicide and a compound of formula I

In order to reduce the amount of fungicide needed to achieve the same fungicidal effect, thereby improving the ecological safety of the fungicide.

The fungicide applied with the compound of formula I can be any one or any combination of one or more fungicides disclosed herein.

In some embodiments, the compound of formula I is combined with an oil. In some embodiments, the oil is selected from the group consisting of tea tree oil, mineral oil, vegetable oil, and any combination thereof.

In some embodiments wherein the plant is Oil Seed Rate (OSR), the compound of formula I is combined with at least one fungicide selected from the group consisting of boscalid, ipratropium, azoxystrobin, prothioconazole, fluopyram, fluxapyroxad, fluazinam, folpet, fludioxonil, and any combination thereof.

In some embodiments wherein the plant is sugar beet, the compound of formula I is combined with at least one fungicide selected from the group consisting of penconazole, prothioconazole, and combinations thereof.

In some embodiments wherein the plant is rice, the compound of formula I is combined with at least one fungicide selected from the group consisting of azoxystrobin, prothioconazole, and combinations thereof.

In some embodiments, wherein the pathogen is oomycetes, the compound of formula I is combined with at least one fungicide selected from the group consisting of: copper, folpet, captan, mancozeb, chlorothalonil, phosphonate, ethiprole, fluopicolide, flumetsulam, zoxamide, cyazofamid, amisulbrom, fluzoxamide, metalaxyl, propamocarb, cymoxanil, carboxylic acid amide, fluazinam, and any combination thereof. In some embodiments, the carboxylic acid amide is mandipropamid, dimethomorph, or a combination thereof.

In some embodiments, wherein the disease is powdery mildew, the compound of formula I is combined with at least one fungicide selected from the group consisting of: bupirimate, triazole fungicides, strobilurin fungicides, sulfur, fenpropidin, phenoxyquinoline, succinate dehydrogenase inhibitor (SDHI) fungicides, and any combination thereof.

In some embodiments, wherein the disease is powdery mildew in vegetable and/or fruit plants, the compound of formula I is combined with at least one fungicide selected from the group consisting of: bupirimate, triazole fungicides, strobilurin fungicides, sulfur, fenpropidin, phenoxyquinoline, SDHI fungicides, and any combination thereof.

In some embodiments, the SDHI (succinate dehydrogenase inhibitor) fungicide may include, but is not limited to, fluxapyroxad, penflufen, flurbiproflumilast, isopyrazam, penflufen, benzovindiflupyr, thifluzamide, iprovalicarb, fluoxastrobin, bixafen, flufenamid, carboxin, boscalid, penflufen, pyrifosfom, ipflupyrad, indenopyrazolam, furametpyr, mefenamid, carboxin oxide, prallezine, fluorophenyl ether, fluquindox, or any combination thereof.

In some embodiments, strobilurin fungicides may include, but are not limited to, azoxystrobin, picoxystrobin, fluxastrobin, dimoxystrobin, pyraclostrobin, trifloxystrobin, coumoxystrobin, enestrobin, pyraclostrobin, tolfenpyrad, oryzastrobin, enestroburin, pyraclostrobin, tolfenpyrad, fluoxastrobin, fluxastrobin, phenoxymyclobutanil, pyriminostrobin; and any combination thereof.

In some embodiments, DMI-fungicides (demethylating inhibitors) may include, but are not limited to, ipconazole, tebuconazole, metconazole, fenbuconazole, furfurazoles, tetraconazole, penconazole, difenoconazole, prothioconazole, epoxiconazole, haloxyfop-methyl, ipconazole, prochloraz, epoxiconazole, bitertanol, fluquinconazole, flusilazole, cyproconazole, triadimenol, hexaconazole, simeconazole, epoxiconazole, diniconazole, cyproconazole, or any combination thereof.

In some embodiments, the fungicide is a fungicidal sterol biosynthesis inhibitor.

In some embodiments, the sterol biosynthesis inhibitor is selected from the group consisting of prothioconazole, epoxiconazole, cyproconazole, myclobutanil, prochloraz, metconazole, difenoconazole, tebuconazole, tetraconazole, fenbuconazole, propiconazole, fluquinconazole, flusilazole, flutriafol, and fenpropimorph.

In some embodiments, the sterol biosynthesis inhibitor is selected from the group consisting of prothioconazole, epoxiconazole, metconazole, difenoconazole, propiconazole, prochloraz, tetraconazole, tebuconazole, fenpropidin, ipconazole, triticonazole, spiroxamine, fenhexamid, and amisulbrom.

In some embodiments, the sterol biosynthesis inhibitor is prothioconazole. In some embodiments, the sterol biosynthesis inhibitor is epoxiconazole. In some embodiments, the sterol biosynthesis inhibitor is cyproconazole. In some embodiments, the sterol biosynthesis inhibitor is myclobutanil. In some embodiments, the sterol biosynthesis inhibitor is metconazole. In some embodiments, the sterol biosynthesis inhibitor is difenoconazole. In some embodiments, the sterol biosynthesis inhibitor is propiconazole. In some embodiments, the sterol biosynthesis inhibitor is prochloraz. In some embodiments, the sterol biosynthesis inhibitor is tetraconazole. In some embodiments, the sterol biosynthesis inhibitor is tebuconazole. In some embodiments, the sterol biosynthesis inhibitor is fluquinconazole. In some embodiments, the sterol biosynthesis inhibitor is flusilazole. In some embodiments, the sterol biosynthesis inhibitor is flutriafol. In some embodiments, the sterol biosynthesis inhibitor is fenpropimorph. In some embodiments, the sterol biosynthesis inhibitor is fenpropidin. In some embodiments, the sterol biosynthesis inhibitor is ipconazole. In some embodiments, the sterol biosynthesis inhibitor is triticonazole. In some embodiments, the sterol biosynthesis inhibitor is spiroxamine. In some embodiments, the sterol biosynthesis inhibitor is zoxamide. In some embodiments, the sterol biosynthesis inhibitor is amifepin. In some embodiments, the sterol biosynthesis inhibitor is fenbuconazole.

In some embodiments, the fungicide is a succinate dehydrogenase inhibitor.

In some embodiments, the succinate dehydrogenase inhibitor is selected from the group consisting of benzovindiflupyr, penthiopyrad, isopyrazam, fluxapyroxad, boscalid, fluopyram, flurbiproflumilast, and penflufen.

In some embodiments, the succinate dehydrogenase inhibitor is benzovindiflupyr. In some embodiments, the succinate dehydrogenase inhibitor is penthiopyrad. In some embodiments, the succinate dehydrogenase inhibitor is isopyrazam. In some embodiments, the succinate dehydrogenase inhibitor is fluxapyroxad. In some embodiments, the succinate dehydrogenase inhibitor is boscalid. In some embodiments, the succinate dehydrogenase inhibitor is fluopyram. In some embodiments, the succinate dehydrogenase inhibitor is bixafen. In some embodiments, the succinate dehydrogenase inhibitor is penflufen.

In some embodiments, the fungicide is a strobilurin fungicide.

In some embodiments, the strobilurin fungicide is selected from the group consisting of azoxystrobin, pyraclostrobin, picoxystrobin, fluoxastrobin, trifloxystrobin, kresoxim-methyl, dimoxystrobin, and orysastrobin.

In some embodiments, the strobilurin fungicide is azoxystrobin. In some embodiments, the strobilurin fungicide is pyraclostrobin. In some embodiments, the strobilurin fungicide is picoxystrobin. In some embodiments, the strobilurin fungicide is fluoxastrobin. In some embodiments, the strobilurin fungicide is trifloxystrobin. In some embodiments, the strobilurin fungicide is kresoxim-methyl. In some embodiments, the strobilurin fungicide is dimoxystrobin. In some embodiments, the strobilurin fungicide is orysastrobin.

In some embodiments, the fungicide is a fungicidal multi-site inhibitor.

In some embodiments, the fungicidal multi-site inhibitor is selected from the group consisting of mancozeb, chlorothalonil, folpet, captan, metiram, mancozeb, propineb, copper hydroxide, copper octoate, copper oxychloride, copper sulfate, copper (ternary) sulfate, mancozeb, copper quinoline, copper bis (3-phenylsalicylic acid), copper zinc chromate, cuprous oxide, copper hydrazinium sulfate, and ziram chloride.

In some embodiments, the fungicidal multi-site inhibitor is mancozeb. In some embodiments, the fungicidal multi-site inhibitor is chlorothalonil. In some embodiments, the fungicidal multi-site inhibitor is folpet. In some embodiments, the fungicidal multi-site inhibitor is captan. In some embodiments, the fungicidal multi-site inhibitor is metiram. In some embodiments, the fungicidal multi-site inhibitor is mancozeb. In some embodiments, the fungicidal multi-site inhibitor is propineb.

In some embodiments, the fungicidal multi-site inhibitor is copper hydroxide, copper octoate, copper oxychloride, copper sulfate, copper (ternary) sulfate, mancozeb, copper quinolinate, copper bis (3-phenylsalicylate), copper zinc chromate, copper oxide, copper hydrazinium sulfate, or copper chloride thiram.

In some embodiments, the fungicide is penoxsulam, fluxapyroxad, penoxsulam, picolide, ipratropium or a Qi inhibitor.

In some embodiments, the Qi inhibitor is amisulbrom. In some embodiments, the Qi inhibitor is cyazofamid.

In some embodiments, the Qi inhibitor is picolinamide. In some embodiments, the picolinamide is picolinamine.

In some embodiments, the pesticide is selected from the group consisting of: 2- (thiocyanomethylthio) -benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, flumetsulam, indazole sulfenamide, antimycin, powdery parasitic spore (Ampelomyces quisqualis), epoxiconazole, azoxystrobin, bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalicarb isopropyl, benzyl aminobenzene-sulfonate (BABS), bicarbonate, biphenyl, metconazole, bitertanol, flurbipyramid, blasticidin, sodium tetraborate decahydrate, bordeaux, boscalid, furfuryl, bupirimate, lime sulfur, captan, carbendazim, carboxin, cyproconazole, carvone, chlaftone, anisole, chlorothalonil, ethaboxirimol, copper hydroxide, copper oxychloride, copper sulfate (ternary), cuprous oxide, chlorothalonil, copper hydroxide, copper sulfate cyazofamid, cymoxanil, cyproconazole, cyprodinil, dazomet, prochloraz, zineb, bis- (dithiocarbamate), benzofomesafen, dichlorophenol, dicyclofenamid, pyridazone, chloronitramine, diethofencarb, difenoconazole, fluoxastrobin, dimethomorph, dimoxystrobin, diniconazole, mefenoconazole, flufenitrothion, dimetoram, difenoconazole, diphenylamine, fenpropiconazole dithianon, dodemorph acetate, dodemorph free alkali, phoxim, enoxystrobin, epoxiconazole, ethaboxam, ethoxyquinoline Tujunling, famoxadone, fenamidone, chlorpyrifos, fenbuconazole, formamide, fenhexamid, fenoxanil, fenpropion-ethyl, fenpropimorph, fenpropidone, fenpropion-methyl, triphenyltin, triphenyltin acetate, triphenyltin hydroxide, thiram, azoxystrobin, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoxastrobin, fluquinconazole, fludioxonil, and a pharmaceutical composition flusilazole, sulfenamid, fluorothiazole nitrile, fluoroamide, flutriafol, fluxapyroxad, folpet, formaldehyde, ethiprole, fosetyl, aluminum triethyl phosphonate, corncob, furalaxyl, furametpyr, biguanide, chlorpyrifos, furazafos, chlorpyrifos, furazolidone, furazoles, furazachlor, furaline, furazolidone, and the like biguanide octaacetate, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil sulfate, imazalil, biguanide octamine, biguanide tris (octy-lbenzenesulfonate), iodopropynyl butylcarbamate, ipfenpyrazodone, ipfenpyrad, iprodione, valicarb, isoprothiolane, isopyrazam, isothiabendazole, kasugamycin hydrochloride hydrate, kresoxyium-methyl laminarin, mancozeb, maneb, mefenoxam, azoxystrobin, fenhexamine, nifedipine, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl-m, acre, potassium acre, metconazole, thiodicarb, methyl iodide, methyl isothiocyanate, metiram, phenoxyjunamine, metrafenone, mildiomycin, myclobutanil, mancozeb, mycorrhizal, mycophenolate, flubenyrimidine alcohol, xin Saitong, furalamide, oleic acid (fatty acid), oryzalin, oxadixyl, quinocopper, oxfenpyrad, carboxin, pyrifos-methyl, penconazole, pencycuron, penconazole, pentachlorophenyl laurate, pyrithiamine, mercuric acetate, phosphoric acid, tetrachlopyrim, picolide, polyoxin B, polyoxin-D (polyoxin-D) Potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, propiodiquinoline, prothioconazole, pyraclostrobin, pyrifos, pyribenzoxim, barnyard grass, pyripyropene oxime, pyrimethanil, pyripyropene, fluquindone, propiconazole algicidal quinone, phenoxyquinoline, pentachloronitrobenzene, giant knotweed extract, epoxiconazole, silthiopham, simeconazole, sodium 2-phenylphenol, sodium bicarbonate, sodium pentachlorophenate, spiroxamine, sulfur, SYP-Z048, heavy tar, tebuconazole, iso Ding Yiyang quinoline, tetrachloronitrobenzene, tetrachloraz, thiabendazole, thifluzamide, thiophanate-methyl, sodium bicarbonate, sodium pentachlorophenate, sulfur, SYP-Z048, heavy tar, tebuconazole, and the like thiram, tiadinil, tolclofos-methyl, tolofloxacin, triazolone, triadimenol, imidazolazine, tricyclazole, tridemorph, trifloxystrobin, triflumizole, oxazine, triticonazole, validamycin, valamine, propamocarb, ethephon, zineb, ziram, zoxamide, candida, fusarium oxysporum, gliocladium species, chaste-tree species, streptomyces griseus, trichoderma species, (RS) -N- (3, 5-dichlorophenyl) -2- (methoxymethyl) -succinimide, 1, 2-dichloropropane, 1, 3-dichloro-1, 3-tetrafluoropropanone hydrate, 1-chloro-2, 4-dinitronaphthalene, 1-chloro-2-nitropropane, 2- (2-heptadecyl-2-imidazolin-1-yl) ethanol, thiopin (2, 3-dihydro-5-phenyl-1, 4-dithiyl-ine 1, 4-tetraoxide), 2-methoxyethyl mercuric acetate, 2-methoxyethyl mercuric chloride, 2-methoxyethyl mercuric silicate, 3- (4-chlorophenyl) -5-methyl rhodanine, 4- (2-nitroprop-1-enyl) phenylthiocyanic acid ester, 1-aminopropylphosphonic acid, dichlormid, zidovudine, barium polysulfide, bayer 32394, mebendazole, quinone oxime hydrazone, benuron, bensulfuron-methyl, benomyl, isobutyl benzyl cyanide acrylate, fluanide, bis (methyl mercuric) sulfate, bis (tributyltin) oxide, pyrithione, wilt (cadmium calcium copper zinc chromate sulfate), mycocarb, CECA, myclobutanil, bispyrim, tetrachlorazine, imipram, copper bis (3-phenyl salicylate) copper zinc chromate, thiazalin, copper hydrazine sulfate, thiram, cyproconazole, cyhalofop-butyl, dimoxystrobin, terfenadine, dichlornaphthaquinone, sclerotinia, benztriazolol, dimethirimol, periwinkle, nitrooctyl, nitrobutyl, pyrithione, folpet, docusafos, hydrazinodone, EBP, ESBP, epoxiconazole, thiozin, bupirimate, disulfenuron, imibenc, seed coating, trifluoperazole, difenoconazole, furazoles, cis-furazoles, fenhexamine, furathionine, glyodine, griseofulvin, quinolinyl acrylate, hercules 3944, cycloheximide, ICIA0858, seed soaking phosphorus, chlorfenadone, o-amide, benzocarb, metrafenone, furbenomyl, cyazofamid, thiabendazole, trifluramine, the pharmaceutical composition comprises mancozeb, mucic anhydride, tolylene, N-3, 5-dichlorophenyl-succinimide, N-3-nitrophenyl-itaconimide, natamycin, N-ethylmercuric-4-tosylaniline, thiram, OCH, thiamine phenylmercuric, mercuric nitrate, clomiphos, thiodicarb hydrochloride, pyranyl, boscalid, prochloraz, chlorofurfur, quintozene acetate sulfate, quinone hydrazone, fluquinconazole, piimidazole, salicylanilide, SSF-109, pentaben sulfone, thiothio, thidiazuron, sterilizing phthalamide, thiabendazole, g-miticide, thiocyanobenzamide, wilson, azoxystrobin, she Xiute, salicylamide, thiram, cyanomyclobutanil, and any combination thereof.

In some embodiments, the pesticide is an insecticide. In some embodiments, the pesticide is an acaricide. In some embodiments, the pesticide is a nematicide. In some embodiments, the pesticide is a herbicide.

Examples of insecticides and acaricides may include, but are not limited to, avermectin, pyriproxyfen, acetamiprid, bifenthrin, cyhalothrin, pymetrozine, novaluron, ethiprole, fipronil, and lambda-cyhalothrin.

Examples of nematicides may include, but are not limited to, fluminesulfone.

The methods and compositions of the invention may be applied to a fungus or locus thereof. Application may be by use of conventional floor spray applicators, granule applicators, and by other conventional means known to those skilled in the art.

Each of the embodiments disclosed herein is contemplated as being applicable to each of the other disclosed embodiments. Accordingly, all combinations of the various elements described herein are within the scope of the invention. Additionally, elements recited in the combination embodiments may be used in the mixtures, compositions, methods, and use embodiments described herein, and vice versa.

Experiment

Material

The compound of formula I is 5-fluoro-4-imino-3-methyl-1-tosyl-3, 4-dihydropyrimidin-2 (1H) -one. The compound of formula I is also known as ADF-16.

50EC compositions of the compound of formula I (i.e., ADF-16) as described in U.S. provisional application No. 63/024,031 are provided in Table 1 below.

TABLE 1 50EC compositions of compounds of formula I

500SC compositions of the compound of formula I (i.e., ADF-16) as described in U.S. provisional application No. 63/024,031 are provided in Table 2 below.

TABLE 2 500SC compositions of the compounds of formula I (i.e., ADM 00050F 1A)

250OD compositions of the compound of formula I (i.e., ADF-16) are provided in Table 3 below.

TABLE 3 250OD compositions of the compounds of formula I

Details of the treatment (1-liter batch):

1. tetraethyl orthosilicate (TEOS) is added toIn ME 18RD-F, and mixed with a high shear mixer for 5 minutes.

2. Adding at the same time of shearingAnd mixed until completely dispersed (about 5 minutes).

3. Addition of Agrimer ^TM AL-22、4916、/>OT-SE、/>PE/L64 and->X050) and mixed until homogeneous (about 5-10 minutes).

4. The compound of formula I was slowly added while shearing and mixed for 15 minutes.

The resulting batch was milled in an Eiger mini-motor mill for 15 minutes at 4500rpm (75% 0.75-1.0mm glass bead loading). D (50) is about 2-3 μm.

Example 1 control of sclerotinia in soybeans as seed treatment

The sterilized seed surface of soybean cultivar RAS 04 from RAGT was treated with a laboratory seed dressing device named Bol heg with the following products:

ADM 00050F 1A (Compound 500SC of formula I) at 0.002-0.005-0.01-0.02 and 0.05L/100Kg seed (1-2.5-5-10-25 g ai/100Kg seed), without coating agent.

Vibrance duo (25+25 g ai/L fludioxonil and sedaxane SC) seeded at 0.2L/100Kg, fludioxonil and sedaxane corresponding to 5+5g ai/100Kg seed

Santhai (465 g ai/L Mefenoxam) EC (3 g ai/100Kg seed Mefenoxam = Mefenoxam) at 0.064L/100Kg seed, without coating agent

Sterile distilled water untreated control, no coating agent

The treated or untreated soybean seeds were allowed to dry under laminar flow for 24 hours prior to sowing.

500cc plastic boxes contained 250ml of additional fines (up to 25cm of vermiculite of the first 3 boxes treated each. 50ml sterilized soybean seeds previously ground inoculated with sclerotinia (strain Sscl wt) and mixed with XF vermiculite were spread over 250ml vermiculite. The same is true for the uninoculated seeds as a reference for germination tests.

The inoculum was covered with 100ml (1 cm) of XF vermiculite and then 9 untreated or treated 9 soybean seeds were sown in each box. Seeds were covered with 150ml (1.5 cm) of XF vermiculite. The substrate was wetted with 200ml of tap water and then once a week with tap water and once with 0.5 g/l of nutrient solution (Plant Prod, ltd N P K20 20 20 and micronutrients). The caps were punctured and then placed on each box for 5 days to maintain saturated humidity. The cassette was placed in a climatic chamber with 16h light/8 h dark photoperiod, 2424 ℃ day/1818 ℃ night and a relative humidity of 85.

Phytotoxicity assessment was performed, checking and analyzing the following parameters:

a. soybean seedling emergence rate 7 days (dps) after sowing.

b. General development of aerial parts of soybean plants after 3 weeks of incubation (pictures)

The results are shown in table 4 and fig. 1.

Table 4: evaluation of emergence rate of soybean seedling cultivar RAS 04 untreated (or treated with ADM 00050f 1a at five application rates, treated with polybrance Duo or mefenoxam, each at one application rate) 7 days after sowing under controlled conditions.

^α Each value corresponds to 9Mean value of 3 replicates of seeds +/-standard error. According to Fisher LSD test, there was no statistical difference in values after the same letter (P <0.05)。

It can be concluded that at any of the tested doses (1-2.5-5-10 and 25g ai/100 Kg), ADM 00050f 1a showed no adverse effect on both germination and subsequent development of soybean seedlings incubated under controlled conditions for a period of 3 weeks, and the results were consistent with the two reference seed treatment fungicides.

Disease assessment was performed, checking and analyzing the following parameters:

a. soybean seedling emergence rate 7 days (dps) after sowing.

b. Intensity of infection of roots of soybean plants after 3 weeks of incubation

The results are shown in tables 5 and 6.

Table 5: evaluation of emergence rate of soybean seedling cultivar RAS 04 7 days after sowing seeds untreated (control) or treated with ADM 00050f 1a at three application rates or virlane Duo at one application rate in XF vermiculite inoculated with sclerotinia strain Sscl wt.

^α Each value corresponds to the mean +/-standard error of 3 replicates of 12 seeds. According to Fisher LSD test, there was no statistical difference in values after the same letter (P<0.05)。

Table 6: evaluation of infection intensity of roots of soybean seedling cultivar RAS 04 after 28 days of seed not treated (control) or treated with ADM 00050f 1a at three application rates or virance Duo at one application rate was sown in XF vermiculite inoculated with sclerotinia strain Sscl wt.

^β The blue value in brackets corresponds to the percentage of fungicide efficacy to untreated and inoculated control after subtracting the contamination rate of the uninoculated control.

Thus, it can be concluded that ADM 00050f 1a exhibited a significant effect on the emergence rate of soybean seedlings compared to untreated controls inoculated with sclerotinia and that the product used appeared to be highly effective against sclerotinia without the coating agent. The activity when applied at the highest application rate of 25g ai per 100Kg seed was close to that of the reference fungicide virance Duo.

EXAMPLE 2 control of Rhizoctonia solani in soybeans as seed treatment

The sterilized seed surface from soybean cultivar RAS 04 of RAGT was treated with a laboratory seed dressing device named Bol hegen with the following products:

ADM 00050F 1A (500 SC) at 0.002-0.005-0.01-0.02 and 0.05L/100Kg seed (1-2.5-5-10-25 g ai/100Kg seed), without coating agent.

Sterile distilled water untreated control, no coating agent

500cc plastic boxes contained 250ml of additional fines (up to 25cm of vermiculite per the first 3 boxes treated. 50ml sterilized soybean seeds previously ground inoculated with rhizoctonia solani (strain RsolAG 2 2) and mixed with XF vermiculite were spread over 250ml vermiculite. The same is true for the uninoculated seeds as a reference for germination tests.

c. soybean seedling emergence rate 7 days (dps) after sowing.

d. General development of aerial parts of soybean plants after 3 weeks of incubation (pictures)

The results are shown in table 7 and fig. 2.

Table 7: evaluation of emergence rate of soybean seedling cultivar RAS 04 7 days after sowing of untreated (or treated with ADM 00050f 1a at five application rates, treated with virance Duo or mefenoxam, each at one application rate) seeds under controlled conditions.

Alpha each value corresponds to the mean +/-standard error of 3 replicates of 9 seeds. Values following the same letter were statistically not different (P < 0.05) according to Fisher LSD test.

a. soybean seedling emergence rate 7 days (dps) after sowing.

The results are shown in tables 8 and 9.

Table 8: evaluation of emergence rate of soybean seedling cultivar RAS 04 7 days after sowing seeds untreated (control) or treated with ADM 00050f 1a at three application rates or treated with virance Duo at one application rate in XF vermiculite inoculated with rhizoctonia solani strain Rsol AG 2 2.

/>

Table 9: evaluation of infection intensity of roots of soybean seedling cultivar RAS 04 28 days after sowing seeds untreated (control) or treated with ADM 00050f 1a at three application rates or treated with virance Duo at one application rate in XF vermiculite inoculated with rhizoctonia strain Rsol AG 2 2.

^β The blue value in brackets corresponds to the percentage of fungicide efficacy in the untreated and inoculated control.

Thus, it can be concluded that ADM 00050f 1a used without the coating agent exhibits a pronounced dose response effect against rhizoctonia solani. The activity when applied at the highest application rate of 25g ai per 100Kg seed was comparable to the reference fungicide Vibrance Duo.

EXAMPLE 3 control of Rhizoctonia solani (sheath blight) in Rice as leaf treatment

The experiments were performed in a greenhouse of the SAGE plant located in the region of Kast Nitropha (Aldrich) -Pi Aimeng (North Italy) in order to evaluate the efficacy and selectivity of the compound of formula I250 OD, the compound of formula I500 SC and the compound of formula I50 EC against Rhizoctonia solani on rice (Leonidas variety) compared to CUSTODIA (azoxystrobin 11% + tebuconazole 18.3% w/w SC) at 400g ai/ha.

The administration took place 4 days after the artificial inoculation by mixing the inoculum of rhizoctonia solani in the floating water.

The untreated check recorded a severity of 8.7% and a morbidity of 30.5% 37 days after administration (days after application, dA-A). The results of the values of the infected leaf area for all test items were significantly different from the untreated check and similar among all test items.

As with the previous evaluation, the final evaluation was performed at 50DA-A, with the results of all test items significantly different from the untreated check (15.6% severity and 38.5% incidence) -see fig. 3 and 4.

In the presence of moderate rhizoctonia solani pressure, all tested products provided disease reduction compared to untreated inspection. All formulations of the compound of formula I showed comparable performance to the reference curodia at 400g ai/ha when applied at 150 throughout the test. A consistent dose response is indicated between compound 250OD of formula I, compound 500SC of formula I, and compound 50EC of formula I at different administration rates.

During the test, three evaluations were performed to evaluate the adverse impact on the crop due to product application. No phytotoxic symptoms or crop vigor differences were observed, indicating complete selectivity of the test product for rice (the Leonidas variety).

EXAMPLE 4 Pyricularia oryzae (blast) in rice as leaf treatment

The experiments were performed in the greenhouse of the SAGE plant located in the region of Kast Nitropha (Aldrich) -Pi Aimeng (North Italy) to evaluate the efficacy and selectivity of the compounds 250OD 150 (T5) and 200 (T6) g ai/ha against Pyricularia oryzae (blast) on rice (variety of Leonidas) compared to AMISTAR at 250g (T9) ai/ha.

The administration took place 3 days after the artificial inoculation by spraying the inoculum of Pyricularia oryzae onto the leaves.

The final evaluation was performed at 32DA-A and the results for all test items were significantly different from the untreated check (severity of 33.0% and incidence of 76.3%), and no difference was observed between the test items and the commercial reference.

The results are shown in fig. 5 and 6.

In the presence of Gao Lidao pestivirus (pestivirus) stress, all tested products provided disease reduction compared to untreated examination. ADF-16 250OD applied at 150 and 200g ai/ha showed comparable performance to the reference AMISTAR at 250g ai/ha throughout the test.

Four evaluations were performed during the trial to evaluate the adverse impact on the crop due to product application. No phytotoxic symptoms or crop vigor differences were observed, indicating complete selectivity of the test product for rice (the Leonidas variety).

Example 5 control of sclerotinia in canola as leaf handling

Experiments were performed in the greenhouse of the SAGE plant located in the region of Kast Nitropha (Aldrich) -Pi Aimeng (North Italy) to evaluate the efficacy and selectivity against sclerotinia on canola (Delight variety) at 75, 100, 125 and 150g ai/ha of ADF-16 250OD, 75 and 150g ai/ha of ADF-16 500SC and ADF-16 50EC compared to 250g ai/ha of AMISTAR FOLD.

The application took place 1 day after the artificial inoculation by spraying the inoculum of sclerotinia onto the plants.

At 29DA-A, untreated checks recorded 57.6% and 43.8% severity for stems and shoots, respectively, and 100.0% morbidity for both stems and shoots.

The results of all test items differ significantly from the untreated check with respect to the percentage of affected stem area, and there are similarities between all test items.

The results are shown in fig. 7.

In the presence of high sclerotinia pressure, all tested products provided disease reduction compared to untreated inspection.

All formulations of ADF-16 showed comparable performance to the reference AMISTAR GOLD at 250g ai/ha when applied at 150 throughout the test.

No phytotoxic symptoms or crop vigor differences were observed, indicating complete selectivity of the test product to canola (Delight variety).

Example 6 control of cucumber downy mildew (downy mildew) in cucumber as a leaf treatment

The experiments were performed in commercial greenhouses in the Vitidoria (Vittoria) (RG) -Saxiri region (south Italy) to evaluate the efficacy and selectivity of ADF-16 250OD at 100, 125, 150 and 200g ai/ha against cucumber downy mildew (downy mildew) on cucumber (Bosco variety) compared to AIRONE PIU at 630g ai/ha and EQUATION PRO at 21g ai/ha.

Each plot (2 m×5m,2 rows/plot) consisted of at least 10 plants, and each treatment was repeated 4 times. The soil used for the test was a mixture of peat and perlite. The 3 applications were performed as follows: a: early treatment (disease symptoms below 5%), B: 7-10 days from A, and C: 7-10 days from B. The corresponding processing dates are: 11/16/2020 (BBCH 64), 11/23/2020 (BBCH 65) and 30/11 (BBCH 67)

Application was performed with a backpack sprayer OleomacSP126 and a water volume of 1000L/ha.

Phytotoxicity (if any) was assessed from 7, 14 and 21 days per application, and the percentage of infected leaf area (% severity) and the percentage of infected leaves (% incidence) were measured from the onset of symptoms.

At the final evaluation (21 days after the third application), the disease severity of the untreated control was 37.7% and the disease incidence reached 100%.

As shown in FIG. 8, all application rates of ADF-16 provided significant control of disease and their up-going performance from 100g ai/ha was comparable to both references. A well-defined dose response can be depicted.

EXAMPLE 7 control of grape downy mildew (downy mildew) in grape vine as a leaf treatment

Experiments were performed in a commercial vineyard in the region of gand new fort (Castelnuovo del Garda, VR) -genito (north italy) to evaluate the efficacy and selectivity of ADF-16 as 250OD and 500SC formulations (with and without adjuvants) at 75 and 100g ai/ha against grape downy mildew (downy mildew) on grape vine (Merlot variety) compared to the reference product AMPEXIO at 245g ai/ha (240 g/kg zoxamide +250g/kg mandipropamid) and untreated controls.

The test was performed according to the EPPO guidelines.

Five administrations were performed at 5-10 day intervals starting from BBCH 64. The application was performed with a backpack sprayer, and the water volume at each application was 100L/ha.

At very high disease pressures, all treatments provided very high levels of control of disease severity of the leaves (between 85% and 89% relative to UTC), and no statistically significant differences were observed in the application rate or formulation.

The inter-beam differences between treatments can be seen in the reference product with the highest scoring control value (98.77% relative to UTC). ADF-16 with the highest application rate of the adjuvant (T7 ADF-16 500SC+Lutensol TDA9 2%v/v at 100g ai/ha) was not significantly different from the control, which achieved 86.63% control of disease severity between bundles. A clear dose response can be seen between the compound of formula I at 75g ai/ha and at 100g ai/ha, both application rates providing significant control of disease compared to untreated controls.

EXAMPLE 8 control of sugar beet powdery mildew (powdery mildew) in sugar beet as leaf treatment

The screening test was carried out in a greenhouse of Gerich shain, kupferstraβe6, germany. The test was performed from application until 28 days after treatment. The efficacy and phytotoxic symptoms of the compounds of formula I on the plant species sugar beet were checked under greenhouse conditions with water controls. Plants were stored at 12,6 ℃ to 24,2 ℃ and 41,9 to 78,2% relative humidity throughout the test period.

The leaves were inoculated. Spore suspensions were prepared. The infected leaves of sugar beet from the field were placed in water for several minutes to obtain a spore suspension. Tween 20 (Polysorbat) was added to the spore solution (0, 1%) for better uniformity. Two diseases, rust and powdery mildew, were observed on the sampling leaves, and in this screening test only powdery mildew infects the plants.

In the screening test, compounds of formula I were administered at different rates and formulations (compound 250OD of formula I, ADF-16 50EC, compound 500SC of formula I-see the list of treatment tables in Table 10) during BBCH stage 16-18 as compared to untreated check and standard compound Juwell (125 g/l epoxiconazole, 125g/l kresoxim-methyl).

Table 10: processing list

The application was carried out once a day after inoculation in an automated application cabin with a spray volume equivalent to 200L/ha. Plants were assessed weekly for growth stage, leaf disease and phytotoxicity during an observation period of 28 Days (DAT) after treatment.

These plants were cultivated according to good horticultural practices. Water (tap water) and nutrient solution (Hakaphos blau, 0.15%) were provided to the sugar beet by using basin tray bottom watering. Weeding was performed by hand as quickly as possible. No additional pesticides were applied.

Results

The fungicidal action of the compounds of formula I against powdery mildew (powdery mildew) of sugar beets was clearly observed in this test (infected leaf area reduced by >60% from 100g ai/ha compared to UTC). Among these application rates, a clear dose response was seen. The reference product provided the highest control of disease, however no significant difference was observed between the compound of formula I at higher application rates and the reference product. A clear difference between the standard compound and the compound of formula I was observed. The results of the OD formulation are summarized in the graph depicted in fig. 9.

Example 9 control of Fijia globalpina in bananas as a leaf treatment (banana black streak)

Banana plants used in this experiment were obtained as in vitro plant model canndish supplied by vitroplic s.a. (france). One month old plants (2 fully developed leaves: F2 (oldest leaves) and F1 and cigar leaves) were treated (see details in the table below) and inoculated with a calibrated hyphal seed inoculum of a mixture of 4 fijia c strains (for each treatment, consider 3 replicates (banana plants)). Banana leaves of each plant were treated on their upper (axial) and lower (axial) faces and then incubated under laminar flow for one hour to dry the fungicide droplets. After inoculation, banana plants were transferred into a climatic chamber: 25℃day/18℃night, 16h light/8 h dark photoperiod and 100% relative humidity.

Table 11: treatment list (sico=difenoconazole 250 ec=reference product) -all products were prepared at an equivalent volume of 50L/ha.

Each banana plant was observed from 28 days to 56 days (dpi) after inoculation and the disease intensity severity (DSI: disease severity index) was evaluated over time to determine AUDPC (area under disease progression curve) -table 12, and fungicidal efficacy expressed as a percentage relative to untreated controls-table 13.

Table 12: area Under Disease Progression Curve (AUDPC) on fijis coccidioides on banana leaves F2 and F1 inoculated 24h prior to treatment with water (control) or several products under controlled conditions.

Table 13: fungicide efficacy was obtained from the AUDPC values of several products applied 24h after inoculation of the banana leaves with fijia globalpina under controlled conditions.

Experiments prove that ADF-16 effectively controls fijisphaeria in bananas.

EXAMPLE 10 control of Botrytis cinerea (Botrytis cinerea) in strawberry as leaf treatment

The purpose of the test was to evaluate the fungicidal effect of ADF-16 against Botrytis cinerea in strawberries compared to untreated control and reference products.

As depicted in the table below, compounds of formula I were tested at 250OD at different doses (i.e., 400, 450 and 500g ai/ha) and compared to untreated controls and two reference products at 1000g ai/ha of SCALA (pyrimethanil 400 g/L) and 600g ai/ha of sign um (boscalid + pyraclostrobin 26.7+6.7 g/kg).

Botrytis cinerea was inoculated manually by spraying the inoculum on the leaves 3-4 days before application.

To test the fungicidal control of botrytis cinerea, strawberry plants grown in pots were sprayed with each of the above treatments. 5 pots of 22cm diameter (the soil used for the test is a mixture of peat and perlite) were used, 1 plant per pot, considering 1 pot per repetition (each treatment consisted of 4 replicates).

According to disease development, each treatment was applied 3 times (ABC) as follows: a, early treatment (before disease symptoms appear; 3-4 days after artificial inoculation), B, 7-10 days from A, and C, assessed according to disease development (7-10 days from B).

At days 7, 14 and 21 from the application, any possible phytotoxic symptoms (%) were evaluated, and no phytotoxicity was observed.

At the time of the first symptoms, the following parameters were evaluated:

percent infected leaf area (% severity)

Percentage of infected leaves (% incidence)

Percentage of infected fruit area (% severity)

Percentage of infected fruits (% incidence)

The results observed in the third and final evaluations are shown in fig. 10.

Fig. 10 depicts that the compound of formula I already provides over 90% control at 450g AI/ha, with significantly lower amounts of AI than the usual minimum 600g AI/ha required for other commercially available products.

Example 11: control of apple scab in apples

The experiments were performed in the greenhouse of the SAGE plant located in the region of Kast Nitto (Aldrich) -Pi Aimeng (North Italy) to evaluate and compare the efficacy and selectivity of ADF-16 250OD applied at several application rates (75, 125, 150, 175 and 200g ai/ha) against Alternaria mali on apples (golden crown apple variety). As a reference treatment, KING (tribasic copper sulfate (tribasic copper sulphate)) was applied at 630g ai/ha.

The artificial inoculation is carried out by spraying an inoculum of cladosporium cucumerinum on the apple leaves. Three administrations were then performed on days 4, 11 and 12 after the manual inoculation.

Four evaluations (day 11, day 18, day 25 and day 32) were performed during the trial to detect any phytotoxic symptoms on the crop and evaluate disease severity and incidence.

At the final evaluation of 14DA-C (day 32 after manual inoculation), the untreated check recorded a severity of 23.8% and a morbidity of 42.0%. ADF-16 250OD applied at 200g ai/ha was superior to KING in severity (3.5% and 7.3%, respectively).

In the presence of high apple scab pressure, ADF-16 250od at all tested application rates provided significant disease control compared to untreated checks.

Higher fungicide efficacy (85.2 pessev% unck and 35.8pesinc% unck, respectively) was recorded at ADF-16 250od applied at 200g ai/ha, and the results were significantly different from all other dose application rates and from ping. The results are shown in fig. 11.

Example 12 control of Leptospira leucotrichia Monascus on zucchini

The experiments were performed in the greenhouse of the SAGE plant located in the region of Kast Nitto (Aldrich) -Pi Aimeng (North Italy) to evaluate and compare the efficacy and selectivity of ADF-16 250OD applied at several application rates (100, 125, 150 and 200g AI/ha) against Leuconostoc mesenteroides on zucchini (Genoves variety). As a reference treatment, BAROCO 80WG (sulfur 800 g/kg) was applied at 2000g ai/ha.

The artificial inoculation is carried out by spraying an inoculum of the single cyst fungus of Leptospira leucotrichia on the pumpkin plants. Three administrations were then performed 4, 11 and 18 days after the manual inoculation. Before that.

During the trial, three evaluations (18 days, 25 days and 32 days) were performed to evaluate disease severity and incidence.

At the final evaluation of 14DA-C (32 days after manual inoculation), the untreated check recorded a severity of 44.3% and a morbidity of 95.8% on the upper side. All treatment results were significantly different from untreated checks, with severity ranging from 2.9% to 34.2% and efficacy values from 26.7% to 85.0% morbidity. All treatment results were significantly different, with severity ranging from 1.4% to 18.1% and morbidity values ranging from 16.7% to 66.7%. ADF-16 250OD performed better than the reference product KING at all application rates. The results are shown in fig. 12.

Example 13a control of cercospora betaensis on sugar beet

The test was performed in a greenhouse of the SAGE plant located in the region of Kast Nitto (Aldrich) -Pi Aimeng (North Italy) in order to evaluate and compare the efficacy and selectivity of ADF-16 250OD (designated ADM-16 250OD in this test) applied at several application rates (75, 100, 125 and 150g AI/ha) against cercospora betanus (leaf spot) on sugar beets (Raison variety). As a reference treatment, POLTIGLIA DISPERSS (Boerdos 200 g/kg) was applied at 1200g ai/ha.

Manual inoculation (day 18 of 1 month) was performed by spraying the inoculum of cercospora betaensis on sugar beet plants. Three administrations were then performed 3, 10 and 17 days after the manual inoculation. Before that.

Four evaluations (10, 17, 24 and 31 days after manual inoculation) were performed during the trial to detect any signs of phytotoxicity on the crops. In addition, the disease severity and disease incidence of pathogens were assessed 17, 24 and 31 days after manual inoculation.

At the final evaluation at 14DA-C (31 days after manual inoculation), the untreated check recorded a severity of 33.6% and a morbidity of 87.3%. The results for all test items were significantly different from the untreated check, with values ranging from 58.9% (ADF-16250 OD at 75g ai/ha) to 98.5% (ADF-16 250OD at 150g ai/ha) controlled in severity. The results are shown in fig. 13.

Example 13b control of sugar beet leaf spot disease on sugar beet

The experiments were performed in the greenhouse of the SAGE plant located in the region of Kast Nitto (Kunlun) -Pi Aimeng (North Italy) in order to evaluate and compare the efficacy and selectivity of ADF-16250OD applied at several application rates (125 and 150g ai/ha) against beet leaf spot on sugar beets (Raison variety). As a reference treatment, AMISTAR GOLD (difenoconazole 125 g/l+azoxystrobin 125 g/l) was applied at 250g ai/ha.

The artificial inoculation is carried out by spraying an inoculum of leaf spot bacteria on sugar beet plants. Three administrations were then performed 3, 10 and 17 days after the manual inoculation.

Four evaluations (at 10, 17, 24 and 31 days after manual inoculation) were performed during the trial to detect any signs of phytotoxicity on the crops. In addition, the disease severity and disease incidence of pathogens were assessed 17, 24 and 31 days after manual inoculation.

At the final evaluation at 14DA-C (31 days after manual inoculation), the untreated check recorded a severity of 29.3% and a morbidity of 81.7%. The results of both ADF-016 250OD treatments were significantly different from the untreated check, with values ranging from 60.8% (ADF-16 250 at 125g ai/ha) to 76.9% (ADF-16 250 at 150g ai/ha) controlled in severity. The results are shown in fig. 14.

EXAMPLE 14 control of soybean powdery mildew (powdery mildew) on soybeans

The purpose of the test was to evaluate the fungicidal effect of ADF-16 against soybean powdery mildew (powdery mildew) on soybeans compared to untreated control and reference products.

ADF-16 was tested at different doses, i.e., 50, 100, 150, and 200g ai/ha, as depicted in the following table.

Table 14: processing list

Several days after application, soybean powdery mildew (powdery mildew) was artificially inoculated by spraying an inoculum on the leaves.

To test fungicidal control of soybean powdery mildew (powdery mildew), soybean plants grown in pots were sprayed with V2 with each of the above treatments. Consider 5 pots, 3 soybean plants per pot, each treatment counting 4 replicates.

The severity (%) of infection was assessed between 14 and 21 days from inoculation.

The results indicate that the compounds of formula I have no significant phytotoxicity.

The results show that the administration of the compound of formula I effectively controls soybean powdery mildew (powdery mildew) on soybeans.

EXAMPLE 15 control of Acremonium viticola on cotton

The purpose of the test was to evaluate the fungicidal effect of ADF-16 against P.viticola on cotton compared to untreated control and reference products.

ADF-16 was tested at different doses, i.e., at 50, 100, 150, and 200g ai/ha, as depicted in the following table.

Table 15: processing list

No adjuvant will be added in any of the treatments.

The septoria viticola was artificially inoculated by spraying conidia on plants previously sprayed with the fungicide.

To test fungicidal control of the aschersonia aleyrodis, cotton plants grown in the pots were sprayed with each of the above treatments at the first fully opened true leaves. Consider 5 pots, 3 cotton plants per pot, each treatment counting 4 replicates.

The severity (%) of infection was assessed between 25 and 30 days from inoculation.

The results indicate that the application of the compound of formula I is effective in controlling alternaria alternata on cotton.

EXAMPLE 16 control of dead body nutritional diseases on soybeans such as Isaria polymorpha and the variation of the Mortierella spinosa

The purpose of the test was to evaluate the fungicidal effect of ADF-16 against two dead-body nutritional diseases such as C.polymorpha and C.spinosa variant C.crassa in soybeans compared to untreated control and reference products.

Table 16: processing list

Inoculation of the multiple main coryneform bacteria and the variation of the. Aschersonia with the spinosa variant was carried out several days after application with infected leaves from the field.

To test fungicidal control against these two dead body nutritional diseases, soybean plants grown in pots were sprayed with V2 with each of the above treatments. Consider 5 pots, 3 soybean plants per pot, each treatment counting 4 replicates.

The results show that the administration of the compound of formula I is effective in controlling corynespora polymorpha on soybeans. The results show that the administration of the compound of formula I is effective in controlling the variation of the species discorea lanuginosa on soybeans.

Example 17 control of soybean Spot-rot pathogen on soybean

The purpose of the test was to evaluate the fungicidal effect of ADF-16 against late season diseases such as Spot-pea in soybeans compared to untreated control and reference products.

ADF-16 was tested at different doses, i.e., at 50, 100, and 200g ai/ha, as depicted in the following table.

Table 17: processing list

The test was performed in open field and no artificial inoculation was performed.

To test fungicidal control against late-season disease, each plot (3 m x 5 m) was sprayed with one of the treatments from table 17. Each treatment consisted of 4 replicates.

Three administrations were performed, the first approximately 14 days before flowering, followed by the second at R1 and the third at r1+14 days. Based on the development of the disease, consider the fourth application.

Evaluation was performed before all sprays and 7, 14 and 21 days after the last spray. The whole plot was evaluated considering 3 plant parts (bottom, middle and upper). The final grade is the average of 3 scores (bottom, middle and top).

Defoliation evaluation was performed on the whole plot. Defoliation assessment was performed at the R6-R7 stage, when the untreated control reached 80% to 90% defoliation. Harvest evaluation starts from the middle of the plot and covers at least 8m ² Sample plot.

The results indicate that the administration of the compound of formula I is effective in controlling soybean purpura on soybeans.

Example 18 control of Leptospira leucotrichia (powdery mildew) in apples

The experiments were performed in the greenhouse of the SAGE plant located in the region of Kast Nitto (Aldrich) -Pi Aimeng (North Italian) in order to evaluate and compare the efficacy and selectivity of ADF-16 250OD applied at several application rates (75, 125, 150, 175 and 200g AI/ha) against Purpurease graminea in apples (golden crown apple variety). As a reference treatment, BAROCO 80WG was applied at 2000g ai/ha.

The artificial inoculation was performed by spraying an inoculum of chaetomium gracile on apple leaves. Three administrations were then performed 5, 12 and 19 days after the manual inoculation.

At the final evaluation, which was performed 14 days after the 3 rd application, an untreated check recorded a severity of 21.9% and a morbidity of 59.6%. The results at 200g ai/ha ADF-16 250OD were significantly different from the other test items, with the lowest severity value (0.6%). In any case, the results of all other test items were significantly different from the untreated check, with a severity value ranging from 2.7% to 10.1%. The results are shown in fig. 15.

EXAMPLE 19 control of Alternaria solani (early blight) on Potato

The experiments were performed in the greenhouse of the SAGE plant located in the region of Kast-Nitro (Aldrich) -Pi Aimeng (North Italy) in order to evaluate and compare the efficacy and selectivity of ADF-16 250OD applied at several application rates (100, 125, 150g AI/ha) against Alternaria solani on potato (Agata variety). As a reference treatment, CUPRIZOL S (copper oxychloride 180 g/l+sulfur 292 g/l) was applied at 330g AI/ha.

The artificial inoculation is carried out by spraying an inoculum of Alternaria solani on the potato plants. Three administrations were then performed 4, 12 and 19 days after the manual inoculation.

At the final evaluation, which was performed 14 days after the final application, an untreated check recorded a severity of 53.8%. The results at 150g ai/ha of ADF-16 250OD were significantly different from the other test items, with the lowest severity value (4.4%). The results are shown in fig. 16.

Example 20 control of soybean rust on soybeans (Asian soybean rust)

The test was performed in 2021 in a greenhouse of a plant pathology laboratory of Empresa de Pesquisa Agr i cola Agenda Agroneg of pampers Su Fengdu-RS.

The experimental design used was a randomized block design and the study consisted of 14 treatments and 35 replicates. The experimental unit consisted of 1cm2 primary leaf severity, amounting to 35 in the pot experiment (standing plants).

The crop used was soybean glycation max, with cultivar BMX Delta maturity group: 5.9 and is susceptible to soybean rust.

The inoculum of soybean rust (soybean rust bacteria) was from a sample of a summer spore population obtained from naturally infected soybean plants collected from pa Su Fengdu in the experimental station of the aganda Agroneg, tlda, bela Vista region, month 2021, which was stored and propagated in pots containing soybean plants (standing plants) and not exposed to any other type of fungicide.

Incubation occurred at a temperature of 22±2 ℃ for a period of 12 hours, and in a dark environment; then, at the same temperature and at a photoperiod of 14 hours, the incubation chamber was maintained for 14 days (period of complete visualization of the sign of the pathogen in witness treatment, no fungicide).

The experimental doses of ADF-16 50EC were: 100g ai/ha;150g ai/ha, containing adjuvants; 150g ai/ha, without auxiliary agent; and 200g ai/ha. The standard used is prothioconazole (Protioconazole), a product with a dose of 80g ai/ha of active ingredient.

Table 18: processing list

The severity was assessed by the number of soybean rust lesions/cm 2 leaves, quantified as 2cm2 primary leaves.

All treatments were superior to treatment T1 (control) by Scott-Knott test at 5% level of significance. Under the conditions in which the experiments were carried out, the data obtained allowed the following observations:

the best treatment is T14 adm.3500.F.2. A250EC+Rumba 0.5%v/v with 54.8% control;

the best treatment is T13 ADF-16 50EC+Rumba 0.5%v/v, which achieves 43.9% control, and T12 ADF-16 50EC, with 42.0% control.

The best formulation is EC.

Example 21 control of potato late blight bacteria on potatoes.

The experiments were performed in the greenhouse of the SAGE plant located in the region of Kast Nitto (Aldrich) -Pi Aimeng (North Italy) to evaluate and compare the efficacy and selectivity of ADF-16 250OD applied at 150g ai/ha versus CUPRIZOL S, a reference product at 330g ai/ha, against potato late blight bacteria on potatoes (Agata variety).

Four days prior to application, manual inoculation was performed by spraying potato plants with an inoculum of potato late blight bacteria. During the test, three evaluations were made at 7DA-A, 14DA-A and 21DA-A in order to detect any signs of phytotoxicity on the crop and evaluate the presence of disease in terms of the percentage of infected area (severity) and the percentage of infected leaves (incidence).

In the following efficacy assessments at 14DA-A and 21DA-A, an increase in disease pressure was observed with an untreated check that recorded 37.1% of the infected leaf area and 87.2% of the infected leaf at the time of the final assessment.

As observed in the first evaluation, the results of the reference treatment and ADF-16 test items produced significantly different control compared to the untreated check, and ADF-16 provided significantly better control than the reference treatment at half the ai amount (in g/ha).

Table 19.

Example 22 control of cercospora betaensis on beet.

Cercospora betana causes cercospora leaf spot on beet species. The efficacy of the ADF-16 formulation was compared to a sulfur-based formulation used at the same equivalent dose of 125g a.i./ha.

24 hours prior to inoculation with the fungal pathogen of interest, a calibrated manual sprayer was used to deliver an equivalent volume of 300 l/hectare for prophylactic treatment. According to agricultural practices, all formulations were prepared with the same equivalent water volume. Control plants (untreated) were treated with water. 3 replicates of 2 plants were taken for each condition. After 14 days of incubation under controlled conditions, the disease intensity averages of the disease-resistant sugar beet plants infected with the urospora betalis strain Cbet 1 at untreated (control) or 24h before inoculation with 125g a.i./ha (0.25L/ha) ADF-16500SC (adm.00050. F.1. A) or with 125g a.i./ha (0.16L/ha) Catzo SC prophylactically treated with ADF-16SC provided much higher control with the same amount of active ingredient (ADF-16 SC at 125g a.i./ha).

Table 20.

* Each DSI value corresponds to the mean +/-Standard Error (SE) of 20 observations (4 plants, each with 5 leaves/modality). Values after the same letter do not differ significantly according to the Newman Kels test at 5%.

Example 22: control of pepper anthracnose on peppers

Experiments were performed in Madhavapuram, kamman (administrative district), termann (india) to evaluate and compare the efficacy and selectivity of ADF-16 500sc applied at 200g AI/ha against pepper anthracnose on pepper (Yashaswini (Mahyco)). Almagor (Azoxy 5.6% + PCZ 20% + Tebu10% w/v) EC was applied as a reference treatment at 105+375+187.5g AI/ha.

Two administrations were performed, the first 110 days after the transplantation and the second at 15 DA-A.

Each treatment was randomly labeled with 10 plants per repetition (10 x 3 replicates = 30 plants) and observations of 10 fruits randomly selected per plant were recorded at 0DAA (pre-count), 5DAA, 10DAA, 15DAA after the 1 st spray and the same event was repeated after the second application.

At these two application times, disease incidence was calculated as the number of infected fruits as a percentage of the total number of fruits evaluated (observations were taken from 10 marker plants and 10 fruits were observed from each marker plant, thus the total number of fruits observed per repeat of each treatment was 100).

ADF-16 500SC administered at 200g AI/ha achieved the lowest incidence compared to two reference products administered in more than twice the amount of active ingredient in comparison.

Table 21.

EXAMPLE 23 control of Alternaria solani on Potato

The experiments were performed in the greenhouse of the SAGE plant located in the region of Kast-Nitro (Aldrich) -Pi Aimeng (North Italy) to evaluate and compare the efficacy and selectivity of ADF-16 250OD applied at 150g AI/ha against Alternaria solani on potato (Agata variety). CUPRIZOL S and CABRIO DUO were applied at 330 and 280g AI/ha, respectively, as reference treatments.

The artificial inoculation is carried out by spraying an inoculum of Alternaria solani on the potato plants. Three administrations were performed 4 days, 11 days and 18 days after the manual inoculation.

Four evaluations (11 days, 18 days, 25 days and 32 days after inoculation) were performed during the trial to detect any phytotoxic symptoms on the crop and evaluate disease severity and incidence.

At the final evaluation, which was performed 32 days after inoculation, untreated checks recorded a severity of 53.8% and a morbidity of 100.0%. ADF-16 250OD at 150g ai/ha resulted in significantly better disease control at significantly lower ai/ha amounts.

Table 22.

EXAMPLE 25 control of Phoma Blastomyces

Test Kryniczno,55-114Wisznia in the southwest of Polandwoj./>Polska/Lower Silesia was performed to evaluate and compare the efficacy and selectivity of ADF-16 500SC applied at two application rates (125 and 150g ai/ha) against Bremia (Phoma) on canola (LG archetect variety).

One administration was made at day 13 5 of 2021 at BBCH stage 63-65. Evaluation of stem infection was performed at day 7 and 8 of 2021 at crop growth stage BBCH 85 and showed significant disease control of ADF-16 500sc at 125g ai/ha and 150g ai/ha compared to untreated controls with efficacy levels of 80.5% and 78.1%, respectively.

EXAMPLE 26 ecological toxicity Properties of Fluosulfonone

The compound trifloxystrobin (ADF-16) is a novel active ingredient for fungicidal plant protection products applied in cultivated crops, aimed at submitting european approval.

The ecological toxicity of trifluoracene has been investigated in many studies according to the stringent requirements of the European Union for approval of active substances.

The results of these studies and risk assessment based on relevant endpoints are summarized in the following table.

Table 23.

LD ₅₀ /LC ₅₀ /EC ₅₀ /LR ₅₀ /ER ₅₀ : dose/concentration/rate of administration that produces 50% effect (lethal or any effect); NOED/NOEC: no effect dose/concentration was observed; bw: weight of the body; d: a day; dws: dry weight soil.

¹ Sign'>"indicates a value greater than that at which no effect is observed at the maximum test concentration.

² Risk assessment was based on current usage patterns in wheat and barley, at intervals of 2x 100g/ha for 7 days.

As indicated above, many studies have resulted in low toxicity, while many have concluded that there is no toxic effect at the maximum test concentration (i.e., greater than the value). Fluosulfone appears to be bee friendly and harmless to other beneficial insects and many other critical organisms tested.

The overall ecotoxicity profile of the sulflurone shows excellent compatibility with the environment. This property, which was established in extensive research, makes trifloxystrobin suitable for effective use against fungal diseases in crops, while at the same time protecting the biodiversity and ecosystem in agricultural landscapes.

According to current eu standards and requirements, risk assessment based on usage patterns in wheat and barley shows acceptable acute and long-term risk in the first layer, a reasonably good safety margin, without having to implement buffer or drift reduction techniques in all critical organisms evaluated.

The european union guidelines based on which to evaluate risk for use in wheat and barley are EFSA (2009) guidelines for risk assessment of birds and mammals, EFSA Journal 2009 for hierarchical risk assessment of plant protection products of aquatic organisms in field surface water; 1438, EFSA (2013) guidelines. EFSA Journal 2013;11 3290 and SANCO (2002) guidelines for terrestrial ecotoxicology according to European Union directive 91/414/EEC, SANCO/10329/2002rev 2final,2002, 10 month 17, each of which is hereby incorporated by reference in its entirety.

Claims

1. A method for treating plants against fungal pathogen infection and/or fungal disease comprising applying to the plants or locus thereof an amount of a compound of formula I

To thereby treat the plant against fungal pathogen infection and/or fungal disease, wherein:

2. The method of claim 1, wherein:

(1) The fungal pathogen is selected from the group consisting of: pyricularia oryzae, rhizoctonia solani, sclerotinia sclerotium, rhizoctonia cerealis, marsdenia tenacissima, leuconostoc mesenteroides, botrytis cinerea, sphaerotheca, rhizoctonia solani, cercospora betana, rhizoctonia cerealis, mortierella bainii, cercospora gracilis, cercospora rosea, and Cercospora rosea beet powdery mildew, soybean rust germ, soybean powdery mildew, reticuloendomyces, colletotrichum gloeosporioides, cercospora spinosa, soybean purpurea germ, downy mildew, fijiqiu globeflower, potato late blight germ, pepper anthracnose germ, and leucotrichia monocystis, and any combination thereof,

(2) The fungal disease is selected from the group consisting of: blast, banded sclerotial blight, early blight, late blight, leaf blight, apple scab, downy mildew, banana black streak leaf spot, downy mildew, soybean late season disease, asian soybean rust, anthracnose, powdery mildew, and any combination thereof, and/or

3. The method of claim 1 or 2, wherein:

4. A method according to any one of claims 1 to 3, wherein treating the plant to combat fungal pathogen infection and/or fungal disease is (i) controlling fungal pathogen infection and/or fungal disease, (ii) preventing fungal pathogen infection and/or fungal disease, and/or protecting the plant from fungal pathogen infection and/or fungal disease.

5. A method according to any one of claims 1-3, wherein:

a) The compound of formula I is applied by contacting the plant or locus thereof with an effective amount of a compound of formula I,

b) Applying the compound of formula I to the roots of the plant,

c) Applying the compound of formula I to the foliage of the plant,

d) Applying the compound of formula I to seed, or

e) Applying the compound of formula I to the seedling.

6. The method of any one of claims 1-4, wherein:

a) The plant is soybean and the fungal pathogen is Sclerotinia sclerotium,

b) The plant is soybean and the fungal pathogen is Rhizoctonia solani,

c) The plant is rice and the fungal pathogen is Rhizoctonia solani,

d) The plant is rice and the fungal pathogen is Pyricularia oryzae,

e) The plant is rape and the fungal pathogen is sclerotinia,

f) The plant is cucumber and the fungal pathogen is a cucumber downy mildew,

g) The plant is grape vine and the fungal pathogen is downy mildew of grape,

h) The plant is sugar beet and the fungal pathogen is powdery mildew of beet,

i) The plant is banana and the fungal pathogen is fijisphaerella,

j) The plant is strawberry and the fungal pathogen is Botrytis cinerea,

k) The plant is apple and the fungal pathogen is a single cyst of a gracilaria,

l) the plant is soybean and the fungal pathogen is chaetomium monofilament,

m) the plant is sugar beet and the fungal pathogen is cercospora betana,

n) the plant is sugar beet and the fungal pathogen is beet leaf spot,

o) the plant is soybean and the fungal pathogen is soybean powdery mildew,

p) the plant is cotton and the fungal pathogen is P.viticola,

q) the plant is soybean and the fungal pathogen is a coryneform polymorpha,

r) the plant is soybean and the fungal pathogen is a Cephalosporium acremonium,

s) the plant is soybean and the fungal pathogen is soybean photinia sclerotiorum,

t) the plant is apple and the fungal pathogen is cladosporium cucumerinum,

u) the plant is potato and the fungal pathogen is Alternaria solani,

v) the plant is potato and the fungal pathogen is potato late blight,

w) the plant is capsicum and the fungal pathogen is pepper anthracnose pathogen,

x) the plant is soybean and the fungal pathogen is soybean rust, or

y) the plant is cucurbita pepo and the fungal pathogen is monocystis leucotrichia.

7. The method of any one of claims 1-5, wherein the compound of formula I is applied as a seed treatment.

8. The method according to claim 6, wherein the compound of formula I is applied as seed treatment at an application rate of 0.5-50gai/100kg seed, preferably 1-25g ai/100kg seed.

9. The method of claim 7, wherein the compound of formula I is applied as a seed treatment at an application rate of 1g ai/100kg seed, 2.5g ai/100kg seed, 5g ai/100kg seed, 10g ai/100kg seed, or 25g ai/100kg seed.

10. The method of any one of claims 1-5, wherein the compound of formula I is administered as a foliar treatment.

11. The method of claim 9, wherein the compound of formula I is applied as a foliar treatment at an application rate of 5 to 1000 gai/ha.

12. The method of claim 10, wherein the compound of formula I is administered as a foliar treatment at an application rate of 6.25g ai/ha, 12.5g ai/ha, 25g ai/ha, 50g ai/ha, 75g ai/ha, 100g ai/ha, 125g ai/ha, 150g ai/ha, 175g ai/ha, 200g ai/ha, 225g ai/ha, 250g ai/ha, 275gai/ha, 300g ai/ha, 400g ai/ha, 450g ai/ha, or 500g ai/ha.

13. The method of any one of claims 1-4, wherein:

a) The application rate of the compound of formula I for controlling Sclerotinia sclerotium in canola as foliar application is 75-200g ai/ha,

b) The application rate of the compound of formula I for use as seed treatment control in soybeans Sclerotinia sclerotium is 1-25g ai/100kg seed,

c) The application rate of the compound of formula I for controlling rhizoctonia solani in soybean as a seed treatment is 1-25g ai/100kg seed,

d) The application rate of said compound of formula I for controlling the end point mould in soybeans as a seed treatment is 5-25g ai/100kg seed,

e) The application rate of said compound of formula I for controlling fusarium graminearum in soybeans as a seed treatment is 5-25g ai per 100kg seed,

f) The application rate of the compound of formula I for controlling rhizoctonia solani (sheath blight) in rice as foliar application is 50-200g ai/ha,

g) The application rate of the compound of formula I for controlling Pyricularia oryzae (blast) in rice as foliar application is 50-200g ai/ha,

h) The application rate of the compound of formula I for controlling the cladosporium cucumerinum (apple scab) in fruits such as apples as foliar applications is 75-200g ai/ha,

i) The application rate of the compound of formula I for controlling the single-bag chaetomium gracile (powdery mildew) in fruits such as apples as foliar applications is 75-200g ai/ha,

j) The application rate of the compound of formula I for controlling botrytis cinerea in strawberries as foliar application is 150-500g ai/ha,

k) The application rate of the compound of formula I for controlling chaetomium vulgare (powdery mildew) in zucchini as foliar application is 75-200g ai/ha,

l) the application rate of the compound of formula I for controlling cucumber downy mildew (downy mildew) in cucumber as leaf application is 75-200g ai/ha,

m) the application rate of the compound of formula I for controlling Alternaria solani (early blight) in potatoes as foliar application is 75-200g ai/ha,

n) the application rate of the compound of formula I for controlling Alternaria solani in potatoes as foliar application is from 175g ai/ha to 200g ai/ha,

o) the application rate of the compound of the formula I for controlling cercospora betana in sugar beet as foliar application is 50-150g ai/ha,

p) the application rate of the compound of the formula I for controlling cercospora betaensis in sugar beet as foliar application is about 125g ai/ha,

q) the application rate of the compound of the formula I for controlling the leaf spot of sugar beets as leaf application is 50-150g ai/ha,

r) the application rate of the compound of the formula I for controlling powdery mildew (powdery mildew) of sugar beet as leaf application is 50-150g ai/ha,

s) the application rate of the compound of formula I for controlling soybean rust in soybeans (Asian soybean rust) as foliar application is 50-200g ai/ha,

t) the application rate of the compound of formula I for controlling soybean powdery mildew (powdery mildew) in soybeans as foliar application is 50-200g ai/ha,

u) the application rate of the compound of formula I for controlling the soybean purpura in soybeans as foliar application is 50-200g ai/ha,

v) the application rate of said compound of formula I for controlling the coryneform bacteria in soybeans as foliar application is 50-200g ai/ha,

w) the application rate of the compound of formula I for controlling the soybean of the disc spinosa as foliar application is 50-200g ai/ha,

x) the application rate of the compound of formula I for controlling the presence of Leptosphaeria in cotton as foliar application is 50-200g ai/ha,

y) the application rate of the compound of formula I for controlling P.viticola in cotton as foliar application is 50-200g ai/ha,

z) the application rate of the compound of formula I for controlling the fungus Cephalosporium toxacum (anthracnose) in capsicum as foliar application is 50-200g ai/ha,

aa) the application rate of the compound of formula I for controlling the downy mildew (downy mildew) of grape vine as foliar application is 50-200g ai/ha,

bb) the application rate of the compound of formula I for controlling F.fijii in banana (leaf spot of banana) as foliar application is 50-200g ai/ha,

cc) the application rate of the compound of formula I for controlling potato late blight in potatoes as foliar application is from 100g ai/ha to 200g ai/ha,

dd) the application rate of the compound of formula I for controlling pepper anthracnose in peppers as foliar application is 150-250g ai/ha, or

ee) the application rate of the compound of formula I for controlling the single-capsule fungus of the group Leptospira leucotrichia (powdery mildew) in zucchini as foliar application is 100-200g ai/ha.

14. The method of any one of claims 1 to 12, wherein:

a) The compound of formula I is applied at the time of planting,

b) The compound of formula I is applied 1 to 60 days after planting,

c) The compound of formula I is applied 1 to 9 months after planting,

d) The compound of formula I is administered once during the growing season,

e) Applying the compound of formula I at least once during the growing season, or

f) The compound of formula I is administered two or more times during the growing season.

15. The method of any one of claims 1-13, wherein the method comprises the protective and/or therapeutic administration of the compound of formula I.

16. The method of any one of claims 1-14, wherein the method is effective to reduce leaf necrosis.

17. A method for treating seeds or seedlings against fungal pathogen infection and/or fungal disease comprising applying to the seeds, seedlings and/or locus thereof a compound of formula I

To thereby treat the seed or seedling against fungal pathogen infection and/or fungal disease, wherein:

18. A method of producing a plant resistant to fungal pathogen infection and/or fungal disease, the method comprising applying to the plant or locus thereof a compound of formula I

19. The method of claim 17, wherein treating the plant or locus thereof comprises treating the seed, the seedling, or the locus of the seed or seedling.

20. A method of producing a plant resistant to fungal pathogen infection and/or fungal disease, the method comprising applying to a seed of the plant, a seedling of the plant, and/or a locus of the seed or seedling a compound of formula I

21. A plant resistant to fungal pathogen infection and/or fungal disease, wherein a seed adapted to produce the plant, a seedling adapted to produce the plant, or the locus of the plant is treated with a compound of formula I

Wherein:

22. A plant seed or seedling adapted to produce a plant resistant to fungal pathogen infection and/or fungal disease, wherein the plant seed or seedling is treated with a compound of formula I

And wherein:

23. Use of compounds of formula I for treating plants against fungal pathogen infection and/or fungal diseases

Wherein:

24. A composition comprising an amount of said compound of formula I

25. The composition of claim 23, wherein the composition is an EC composition, an SC composition, or an OD composition.

26. The composition of claim 23 or 24, wherein the composition is for controlling fungal pathogen infection and/or fungal disease.

27. The composition of any one of claims 23-25, wherein the composition is for preventing fungal pathogen infection and/or fungal disease.

28. The composition of any one of claims 23-26, wherein the composition is for protecting the plant from fungal pathogen infection and/or fungal disease.

29. A method for treating plants against fungal pathogen infection and/or fungal disease comprising applying an amount of a compound of formula I

30. The method of claim 29, wherein the amount of the compound of formula I has an ecologically acceptable acute effect on non-target organisms.

31. The method of claim 29 or 30, wherein the amount of the compound of formula I has an ecologically acceptable chronic effect on non-target organisms.

32. The method of any one of claims 29-31, wherein:

a. the amount of the compound of formula I has an ecologically acceptable effect on the propagation of the non-target organism, and/or

b. The amount of the compound of formula I has an ecologically acceptable effect on the growth and/or development of the non-target organism.

33. The method of any one of claims 29-32, wherein the ecologically acceptable effect is a mortality rate of less than 50%, less than 20%, or less than 10% of non-target organism species.

34. The method of any one of claims 29-33, wherein the non-target organism is an avian, mammalian, fish, aquatic invertebrate, algae, arthropod, earthworm, soil microorganism, or crop.

35. The method of any one of claims 29-34, wherein the non-target organism is a bee.

36. The method of claim 35, wherein:

c. said amount having an ecologically acceptable acute oral effect on the bees,

d. said amount having an ecologically acceptable acute contact effect on the bees,

e. said amount having an ecologically acceptable chronic oral effect on the bees,

f. said amount having an ecologically acceptable chronic effect on the larvae of the bees,

g. said amount having an ecologically acceptable acute effect on the population survival of the bees,

h. said amount having an ecologically acceptable chronic effect on the population survival of the bees,

i. said amount having an ecologically acceptable acute effect on the development of the bees,

j. said amount having an ecologically acceptable chronic effect on the development of the bees, and/or

k. The ecologically acceptable effect is less than 10%.

37. The method of any one of claims 29-36, wherein the ecologically acceptable effect is substantially free of observable effects.

38. The method of any one of claims 29-37, wherein the amount of the compound of formula I is 100g ai/ha or less.

39. The method of any one of claims 29-38, wherein the amount of the compound of formula I is 100g ai/ha or less, administered twice, with a 7 day interval between the two administrations.

40. A method for treating plants against fungal pathogen infection and/or fungal disease comprising applying an amount of a compound of formula I

Wherein the amount is less than 150g ai/ha.

41. A mature plant resistant to fungal attack, wherein said mature plant or a seed or seedling adapted to produce said mature plant is treated with an amount of said compound of formula I

Wherein the treated mature plant has an ecologically acceptable effect on non-target organisms that contact the treated mature plant.

42. A method of improving the ecological safety of a fungicide comprising applying to the plant or locus the fungicide and a compound of formula I

In order to reduce the amount of said fungicide needed to achieve the same fungicidal effect, thereby improving the ecological safety of said fungicide. />