Bactericide / fungicide mixture

Abstract

Compositions comprising cyclothiazomycin C and streptimidon, pesticide compositions comprising this mixture, and methods and uses of the compositions in controlling or preventing fungal infestation of plants or other substrates.

Description

[Technical field]

[0001] The present invention relates to a mixture comprising two known compounds cyclothiazomycin C and streptimidon and its use, in particular for controlling fungi in agriculture or horticulture. The present invention also relates to a fungicidal composition, in particular an agrochemical fungicidal composition, comprising this mixture, and to a process for the preparation of this composition. [Background technology]

[0002] Cyclothiazomicin C is a known compound of formula I; [ka] It is.

[0003] The structure of cyclothiazomycin C is disclosed on page 3 of WO2015191789. The disclosure also provides examples of antibacterial activity of cyclothiazomycin C in Table 6 on page 31. In WO2015191789, after Table 6 on page 31, it is clearly stated that "the greatest inhibitory activity was observed against Bacillus. The inventors also decided to evaluate whether cyclothiazomycin C exhibited a growth inhibitory effect against various fungal strains, but no such effect was observed."

[0004] Streptimidone is a known compound of formula (II) [ka] Formula (II) It is. Summary of the Invention [Means for solving the problem]

[0005] Surprisingly, it has been found that cyclothiazomycin C exhibits useful fungicidal activity against a number of fungal pathogens that commonly infect plants in agriculture and horticulture and can be used as an antifungal agent or as a fungicide for a variety of substrates and in a variety of applications.

[0006] It has also been found that not only does cyclothiazomycin C unexpectedly exhibit fungicidal activity, but that mixtures containing cyclothiazomycin C and streptimidon are capable of exhibiting an unexpected synergistic fungicidal effect.

[0007] According to a first aspect of the present invention there is provided a mixture comprising cyclothiazomycin C and streptimidon.

[0008] According to a second aspect of the present invention there is provided an agrochemical composition comprising a mixture comprising a fungicidally effective amount of cyclothiazomycin C and streptimidon, which may further comprise an agrochemically acceptable diluent or carrier.

[0009] According to a third aspect of the present invention there is provided a method for controlling or preventing fungal infestation of a plant comprising administering to the plant, or parts thereof or the plant habitat a fungicidally effective amount of a pesticide composition comprising a mixture comprising cyclothiazomycin C and streptimidon.

[0010] According to a fourth aspect of the present invention there is provided the use of a mixture comprising cyclothiazomycin C and streptimidon as a bactericide / fungicide. According to this particular aspect of the present invention, the use may exclude methods involving the treatment of the human or animal body by surgery or therapy. [Brief description of the drawings]

[0011] [Figure 1A]Photograph of the zones of inhibition caused by whole broth samples of NRRL strain WC-3908 in Botrytis cinerea bioassay plates. [Figure 1B] Photograph of the zone of inhibition caused by whole broth samples of NRRL strain WC-3908 in a Zymoseptoria tritici bioassay plate. [Figure 1C] Photograph of the zones of inhibition caused by whole broth samples of NRRL strain WC-3908 in Fusarium culmorum bioassay plates. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Cyclothiazomicin C is available as disclosed in WO 2015191789. In particular, cyclothiazomycin C is produced by NRRL strain WC-3908 and can be isolated as described in paragraph

[0178] of WO 2015191789. Strain WC-3908 is publicly available from the ARS Culture Collection (NRRL), 1815 N University Street, Peoria, IL, 61604.

[0013] Streptomydon has been described in Kondo, H., Oritani, T., and Kiyota, H. Synthesis and antifungal activity of the four stereoisomers of streptimidone, a glutarimide antibiotic from Streptomyces rimosus forma paromomycinus. Eur. J. Org. Chem. (20), 3459-3462 (2000). Many Streptomyces strains express streptimidon. Streptimidon is also commercially available.

[0014] Mixtures containing cyclothiazomycin C and streptimidon can be used as active ingredients in agricultural and related fields of use, for example, in non-biological materials to control fungal plant pests or to control decay fungi or fungi potentially harmful to humans. Mixtures containing cyclothiazomycin C and streptimidon have surprising effectiveness at low application rates and are well tolerated by plants. They have very useful curative and preventive properties and can be used to protect a wide variety of cultivated plants. Mixtures containing cyclothiazomycin C and streptimidon also have surprising synergistic effects and can be used to inhibit or eliminate fungi occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while these parts of the plants that grow thereafter are also protected at the same time.

[0015] The invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and / or harvested food crops susceptible to fungal attack by treating the plants or plant propagation material and / or harvested food crops, in which a mixture comprising a fungicidally effective amount of cyclothiazomycin C and streptimidon is applied to the plant, its parts or its habitat.

[0016] It is also possible to use a mixture containing cyclothiazomycin C and streptimidon more broadly as a fungicide. As used herein, the term "fungicide" refers to a compound that controls, modifies, or prevents fungal growth. The term "fungicidally effective amount," when used, refers to the amount of such a compound or combination of such compounds that is capable of producing an effect on fungal growth. A controlling or modifying effect includes any deviation from natural occurrence, such as killing, retarding, etc., and prevention includes the formation of a barrier or other defense in the plant to prevent fungal infection.

[0017] For protection against fungal infections and phytopathogenic fungi occurring in the soil, it may also be possible to use a mixture comprising cyclothiazomycin C and streptimidon as a dressing agent for the treatment of plant propagation material, for example seeds, such as fruits, tubers or grains, or plant cuttings. The propagation material can be treated with a composition comprising cyclothiazomycin C and streptimidon before planting: for example, seeds can be dressed before sowing. Cyclothiazomycin C and streptimidon can also be applied to the grains (coating) by impregnating the seeds in a liquid formulation or by coating the seeds with a solid formulation. This composition can also be applied to the planting site, for example in the sowing furrow during sowing, when the propagation material is planted. The present invention also relates to a method for treating such plant propagation material, and to the plant propagation material thus treated.

[0018] Furthermore, mixtures comprising cyclothiazomycin C and streptimidon can be used for controlling fungi, for example in the protection of technical materials including wood and wood-related technical products, food preservation, pharmaceutical applications, veterinary applications and hygiene control, among other related fields.

[0019] In addition, the present invention may be used to protect non-living materials such as timber, wallboard, wallpaper and paint from fungal attack.

[0020] Examples of important fungi which need to be controlled in agriculture and other sectors are: Albugo Candida, Alternaria spp.; Alternaria alternate, Alternaria brassicae, Alternaria brassicicola, Alternaria solani, Alternaria tomatophila, Aphanomyces spp.; Aphanomyces cochlioides, Aphanomyces euteiches, Ascochyta spp.; Ascochyta pisi, Aspergillus spp.; Aspergillus carbonarius carbonarius; Aspergillus flavus, Aspergillus niger, Blumeria spp.; Blumeria graminis f.sp. herdei, Blumeria graminis f.sp. tritici, Blumeriella jaapii, Botryosphaeria spp.; Botryosphaeria dothidea, Botryosphaeria obtusa, Botrytis spp.; Botrytis cinerea, Bremia lactucae lactucae, Cadophora gregata, Ceratocystis spp.; Ceratocystis fimbriata, Cercospora spp.;Cercospora beticola, Cercospora kikuchii, Cercospora sojina, Cercospora zeae-maydis, Cladosporium spp;Cladosporium cucumerinum,Clarireedia homoeocarpa,Claviceps purpurea,Cochliobolus spp;Cochliobolus carbonum,Cochliobolus heterostrophus,Cochliobolus lunatus lunatus, Cochliobolusmiyabeanus, Cochliobolussatibus, Colletotrichum spp; Colletotrichum capsici, Colletotrichum coccodes, Colletotrichum dematium, Colletotrichum gloeosporioides, Colletotrichum graminicola, Colletotrichum lindemuthianum, Colletotrichum musae, Colletotrichum orbiculare, Colletotrichum truncatum truncatum), Corynespora cassiicola,. Diaporthe spp.; Diaporthe helianthi, Diaporthe longicolla, Diaporthe neoviticola, Diaporthe sojae, Didymella spp.; Drechslera spp.; Drechslera gigantea, Elsinoe spp.; Elsinoe glycines, Eremothecium gossypii, Erysiphe spp.; Erysiphe cruciferarum, Erysiphe jifusa diffusa, Erysiphe Necator, Eutypa lata, Fusarium spp; Fusarium culmorum, Fusarium langsethiae, Fusarium oxysporum f.sp. glycines, Fusarium oxysporum f.sp. vasinfectum, Fusarium oxysporum f.sp. betae, Fusarium oxysporum f.sp. cubense f.sp.cubense), Fusarium oxysporum f.sp.lycopersici (Fusarium oxysporum f.sp.lycopersici, Fusarium poae, Fusarium proliferatum, Fusarium sacchari, Fusarium sporotrichioides, Fusarium tricinctum, Fusarium virguliforme, Gaeumannomyces graminis, Gibberella spp; Gibberella avenacea, Gibberella fujikuroi, Gibberella fujikuroi var.subglutinans, Gibberella intricans, Gibberella moniliformis, Gibberella zeae, Golovinomyces cichoracearum, (Gymnosporangium juniperi-virginianae), Helminthosporium spp; Helminthosporium solani, Hemileia spp; Hemileia vastatrix, Hyaloperonospora parasitica, Kabatiella zeae, Laetisaria fuciformis, Leptographium lundbergii, Leveillula taurica, Lophodermium seditiosum,. Microdochium majus, Monilinia spp., Monilinia fructicola, Monographella spp., Monographella albescens, Monographella nivalis, Mycosphaerella spp., Mycosphaerella arachidis, Mycosphaerella areola, Mycosphaerella berkeleyi, Mycosphaerella pomi, Nakataea oryzae, Neopseudocercosporella spp. spp; Neopseudocercosporella brassicae, Neopseudocercosporella capsellae, Oculimacula yallundae, Ophiostoma spp; Ophiostoma piceae, Ophiostoma ulmi, Parastagonospora nodorum, Penicillium spp; Penicillium digitatum, Penicillium expansum, Penicillium italicum italicum), Peronosclerospora spp;Peronosclerospora maydis, Peronosclerospora philippinensis, Peronosclerospora sorghi, Peronosclerospora spp; Peronospora destructor, Peronospora manshurica, Phakopsora pachyrhizi, Phellinus igniarius, Phialophora spp; Phlyctema vagabunda, Phoma spp; Phyllachora spp. Phyllachora pomigena, Phyllosticta spp., Phyllosticta ampelicida, Phyllosticta citricarpa, Phyllosticta sphaeropsoidea, Physoderma maydis, Phytophthora spp., Phytophthora capsici, Phytophthora cinnamomi, Phytophthora infestans, Phytophthora sojae, Plasmodiophora brassicae brassicae, Plasmopara spp; Plasmopara halstedii, Plasmopara viticola, Plenodomus spp;Plenodomus biglobosus, Plenodomus lingam, Pleospora spp., Pleospora herbarum, Podosphaera spp., Podosphaera fusca, Podosphaera leucotricha, Podosphaera macularis, Pseudocercospora fijiensis, Pseudoperonospora spp., Pseudoperonospora cubensis, Pseudoperonospora humuli, Pseudopeziza tracheiphila, Pseudopyrenochaeta lycopersici; Puccinia spp.; Puccinia allii, Puccinia graminis, Puccinia helianthi, Puccinia hordei, Puccinia kuehnii, Puccinia melanocephala, Puccinia polysora, Puccinia sorghi, Puccinia striiformis, Puccinia triticina, Pyrenopeziza spp.; Pyrenopeziza brassicae, Pyrenophora spp. spp; Pyrenophora graminea, Pyrenophora teres, Pyrenophora tritici-repentis, Pyricularia spp; Pyricularia graminis-tritici, Pyricularia oryzae, Pythium spp; Pythium aphanidermatum, Pythium sylvaticum, Pythium ultimum, Ramularia spp; Ramularia colosigni collo-cygni), Remotididymella destructiva, Rhizoctonia spp;Rhizoctonia cerealis, Rhizoctonia oryzae, Rhizoctonia oryzae-sativae, Rhizoctonia theobromae, Rhizopus arrhizus, Rhynchosporium spp; Rhynchosporium secalis, Sarocladium oryzae, Schizothyrium pomi, Sclerophthora macrospora, Sclerotinia spp; Sclerotinia sclerotiorum sclerotiorum, Sclerotium spp., Septoria spp., Septoria glycines, Septoria lycopersici, Setosphaeria turcica, Sphaerotheca fuliginea, Stagonosporopsis cucurbitacearum, Stemphylium spp., Stemphylium solani, Stenocarpella macrospora, Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp;Tilletia laevis, Tilletia tritici, Tranzschelia discolour, Trichoderma spp; Trichoderma viride, Typhula spp; Typhula incarnata, Urocystis spp; Urocystis agropyri, Urocystis colchici, Uromyces spp; Uromyces appendiculatus, Uromyces viciae-fabae, Ustilago spp. spp); Ustilago maydis, Ustilago segetum var. hordei, Ustilago segetum var. nuda, Ustilago segetum var. tritici, Venturia spp; Venturia inaequalis, Venturia pyrina, Verticillium spp; Verticillium dahliae, Wilsonomyces carpophilus, and Zymoseptoria tritici.;

[0021] Examples of other important fungi are: Absidia corymbifera, Aspergillus fumigatus, Emericella nidulans, Aspergillus terreus, Aureobasidium pullulans, Blastomyces dermatitidis, Candida albicans, Candida glabrata, Candida krusei, Candida lusitaniae, Candida parapsilosis, Candida tropicalis, Coccidioides immitis. immitis, Filobasidiella neoformans, Epidermophyton floccosum, Ajellomyces capsulatus, Microsporum spp, Mucor spp, Paracoccidioides spp, Petriellidium spp, Rhizomucor pusillus, Rhizopus arrhizus, Scedosporium spp, Pseudallescheria boydii, Scedosporium prolificans prolificans, Sporothorix spp, Trichophyton spp, Cephaloascus fragrans.

[0022] Other plant pathogens include protists such as Polymyxa graminis and Polymyxa betae.

[0023] Preferred examples are: Albugo Candida, Alternaria alternata, Alternaria brassicae, Alternaria brassicicola, Alternaria tomatophila, Aphanomyces spp.; Aphanomyces cochlioides, Aphanomyces euteiches, Ascochyta spp.; Ascochyta pisi, Aspergillus carbonarius; Aspergillus flavus, Blumeria graminis f.sp. herdei. f.sp.herdei, Blumeriella jaapii, Botryosphaeria spp.; Botryosphaeria dothidea, Botryosphaeria obtusa, Botrytis spp.; Botrytis cinerea, Bremia lactucae, Cadophora gregata, Ceratocystis spp.; Ceratocystis fimbriata, Cercospora spp.;Cercospora beticola, Cercospora kikuchii, Cercospora sojina, Cercospora zeae-maydis, Cladosporium spp;Cladosporium cucumerinum,Clarireedia homoeocarpa,Claviceps purpurea,Cochliobolus spp;Cochliobolus carbonum,Cochliobolus heterostrophus,Cochliobolus lunatus lunatus, Cochliobolusmiyabeanus, Cochliobolussatibus, Colletotrichum spp; Colletotrichum capsica, Colletotrichum coccodes, Colletotrichum dematium, Colletotrichum gloeosporioides, Colletotrichum graminicola, Colletotrichum lindemuthianum, Colletotrichum musae, Colletotrichum orbiculare, Colletotrichum truncatum truncatum), Corynespora cassiicola,. Diaporthe spp.; Diaporthe helianthi, Diaporthe longicolla, Diaporthe neoviticola, Diaporthe sojae, Didymella spp.; Drechslera spp.; Drechslera gigantea, Elsinoe spp.; Elsinoe glycines, Eremothecium gossypii, Erysiphe spp.; Erysiphe cruciferarum, Erysiphe jifusa diffusa, Erysiphe Necator, Eutypa lata, Fusarium langsethiae, Fusarium oxysporum f.sp. glycines, Fusarium oxysporum f.sp. vasinfectum, Fusarium oxysporum f.sp. betae, Fusarium oxysporum f.sp. cubense, Fusarium oxysporum f.sp. lycopersicilycopersici, Fusarium poae, Fusarium proliferatum, Fusarium sacchari, Fusarium sporotrichioides, Fusarium tricinctum, Fusarium virguliforme, Gaeumannomyces graminis, Gibberella spp; Gibberella avenacea, Gibberella fujikuroi, Gibberella fujikuroi var. subglutinans.subglutinans, Gibberella intricans, Gibberella moniliformis, Gibberella zeae, Golovinomyces cichoracearum, (Gymnosporangium juniperi-virginianae), Helminthosporium spp; Helminthosporium solani, Hemileia spp; Hemileia vastatrix, Hyaloperonospora parasitica, Kabatiella zeae, Laetisaria fuciformis, Leptographium lundbergii, Leveillula taurica, Lophodermium seditiosum, Microdochium majus, Monilinia spp.; Monilinia fructicola, Monographella spp.; Monographella albescens, Monographella nivalis, Mycosphaerella spp.; Mycosphaerella arachidis, Mycosphaerella areola, Mycosphaerella verkelleii berkeleyi), Mycosphaerella pomi,. Nakataea oryzae, Neopseudocercosporella spp; Neopseudocercosporella brassicae, Neopseudocercosporella capsellae, Oculimacula yallundae, Ophiostoma piceae, Ophiostoma ulmi, Penicillium spp; Penicillium digitatum, Penicillium expansum, Penicillium italicum italicum, Peronosclerospora spp; Peronosclerospora maydis, Peronosclerospora philippinensis, Peronosclerospora sorghi, Peronosclerospora spp; Peronosclerospora destructor, Peronospora manshurica, Phakopsora pachyrhizi, Phellinus igniarius, Phialophora spp; Phlyctema vagabunda, Phoma spp; Phyllachora spp; Phyllachora pomigena, Phyllosticta spp;Phyllosticta ampelicida, Phyllosticta citricarpa, Phyllosticta sphaeropsoidea, Physoderma maydis, Phytophthora spp., Phytophthora capsici, Phytophthora cinnamomi, Phytophthora infestans, Phytophthora sojae, Plasmodiophora brassicae, Plasmopara spp.; Plasmopara harstezii halstedii, Plasmopara viticola, Plenodomus spp., Plenodomus biglobosus, Plenodomus lingam, Pleospora spp., Pleospora herbarum, Podosphaera spp., Podosphaera fusca, Podosphaera leucotricha, Podosphaera macularis, Pseudocercospora fijiensis, Pseudoperonospora spp. spp; Pseudoperonospora cubensis, Pseudoperonospora humuli, Pseudopeziza tracheiphila, Pseudopyrenochaeta lycopersici;Puccinia spp.; Puccinia allii, Puccinia graminis, Puccinia helianthi, Puccinia hordei, Puccinia kuehnii, Puccinia melanocephala, Puccinia polysora, Puccinia sorghi, Puccinia striiformis, Puccinia triticina, Pyrenopeziza spp.; Pyrenopeziza brassicae, Pyrenophora graminea graminea, Pyrenophora tritici-repentis, Pyricularia graminis-tritici, Pythium spp.; Pythium aphanidermatum, Pythium sylvaticum, Pythium ultimum, Ramularia spp.; Ramularia collo-cygni, Remotididymella destructive, Rhizoctonia spp.; Rhizoctonia cerealis, Rhizoctonia oryzae oryzae, Rhizoctonia oryzae-sativae, Rhizoctonia theobromae, Rhizopus arrhizus, Rhynchosporium spp;Rhynchosporium secalis, Sarocladium oryzae, Schizothyrium pomi, Sclerophthora macrospora, Sclerotium spp; Septoria spp; Septoria glycines; Septoria lycopersici; Setosphaeria turcica; Sphaerotheca fuliginea, Stagonosporopsis cucurbitacearum, Stemphylium spp; Stemphylium solani solani, Stenocarpella macrospora, Stereum hirsutum, Thielaviopsis basicola, Tilletia spp., Tilletia laevis, Tilletia tritici, Tranzschelia discolour, Trichoderma spp., Trichoderma viride, Typhula spp., Typhula incarnata, Urocystis spp., Urocystis agropyri, Urocystis colchici, Uromyces spp;Uromyces appendiculatus, Uromyces viciae-fabae, Ustilago spp;Ustilago maydis, Ustilago segetum var. hordei, Ustilago segetum var. nuda, Ustilago segetum var. tritici; Venturia spp.; Venturia inaequalis, Venturia pyrina, Verticillium spp.; Verticillium dahliae, Wilsonomyces carpophilus, Zymoseptoria tritici, Absidia corymbifera, Aspergillus fumigatus, Emericella nidulans, Aspergillus terreus, Aureobasidium pullulans, Blastomyces dermatitidis dermatitidis, Candida albicans, Candida glabrata, Candida krusei, Candida lusitaniae, Candida parapsilosis, Candida tropicalis, Coccidioides immitis, Filobasidiella neoformans, Epidermophyton floccosum, Ajellomyces capsulatus, Microsporum spp, Mucor spp, Paracoccidioides spp. spp, Petriellidium spp, Rhizomucor pusillus, Rhizopus arrhizus, Scedosporium spp.spp), Pseudallescheria boydii, Scedosporium prolificans, Sporothorix spp, Trichophyton spp, Cephaloascus fragrans, Polymyxa graminis, Polymyxa betae.

[0024] More preferred examples of fungi are: Botrytis cinerea, Cercospora kikuchii, Cercospora sojina, Cochliobolus sativus, Colletotrichum lindemuthianum, Colletotrichum orbiculare, Corynespora cassiicola, Fusarium avenaceum, Fusarium culmorum, Fusarium langsethiae, Fusarium poae, Fusarium sporotrichioides, Fusarium sporot ... sporotrichioides, Fusarium tricinctum, Fusarium virguliforme, Gibberella avenacea, Gibberella fujikuroi, Gibberella zeae, Microdochium majus, Monographella nivalis, Mycosphaerella arachidis, Phakopsora pachyrhizi, Puccinia triticina, Pyrenophora tritici-repentis, Ramularia colosigni collo-cygni, Rhynchosporium secalis, Septoria glycines, Tilletia tritici, Ustilago segetum var. triticiTritici, Venturia inaequalis, and Zymoseptoria tritici.

[0025] Most preferred examples of fungi are Gibberella spp., including Gibberella zeae (also known as Fusarium graminearum), Fusarium spp., including Fusarium virguliforme (also known as Fusarium solani f.sp. glycines, or soybean sudden death syndrome), Microdochium spp., such as Monographella nivalis (also known as Microdichium nivale or cereal head blight), and Zymoseptoria tritici (Septoria tritici, Mycosphaerella Zymoseptoria or Mycosphaerella species such as Zymoseptoria graminicola or Septoria leaf blight, in particular Zymoseptoria tritici, Microdichium nivale (=Monographella nivalis) and Gibberella zeae (=Fusarium graminearum).

[0026] Target crops and / or useful plants to be protected are typically berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fibre plants, such as cotton, flax, hemp, jute and sisal; agricultural crops, such as sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses, such as bermuda grass, strawberry bush, bentgrass, centipede grass, fescue, ryegrass, lawn grass and wild grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olive and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as vines, for example grapes.

[0027] The term "useful plants" should also be understood to include useful plants in which resistance to herbicides such as bromoxynil or to a class of herbicides (e.g. HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors, etc.) has been imparted by conventional breeding or genetic engineering methods. An example of a crop in which resistance to imidazolinones, e.g. imazamox, has been imparted by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (canola). Examples of crops that have been rendered resistant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0028] The term "useful plants" should also be understood to include useful plants which have been transformed by recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as the known ones derived from toxin-producing bacteria, especially those belonging to the genus Bacillus.

[0029] Examples of such plants are YieldGard® (a corn variety expressing a CryIA(b) toxin); YieldGard Rootworm® (a corn variety expressing a CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing CryIA(b) and CryIIIB(b1) toxins); Starlink® (a corn variety expressing a Cry9(c) toxin); Herculex I® (a corn variety expressing a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing a CryIA(c) toxin); Bollgard I® (a cotton variety expressing a CryIA(c) toxin); Bollgard II® (a cotton variety expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (a cotton variety expressing VIP toxin); NewLeaf® (a potato variety expressing CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn root-feeding nematode trait) and Protecta®.

[0030] The term "crop plant" should also be understood to include crop plants which have been transformed using recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly those belonging to the genus Bacillus.

[0031] Toxins which can be expressed by such transformed plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as the δ-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins from Photorhabdus spp. or Xenorhabdus spp., e.g. Photorhabdus luminescens, Xenorhabdus nematophilus, insecticidal proteins of nematode symbiotic bacteria such as Azotoxins, ... ribosome-inactivating proteins (RIPs) such as rufin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0032] Furthermore, in the context of the present invention, delta-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or trophic insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, are also to be understood as being especially hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by new combinations of different domains of these proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0033] Examples of such toxins or transformed plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0034] The processes for the preparation of such transformed plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0035] The toxins contained in the transformed plants confer resistance to harmful insects on the plants, which can be from any taxonomic group of insects, but are particularly commonly found among beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0036] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some are commercially available. Examples of such plants include: YieldGard® (a corn variety expressing Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing Cry9C toxin); Herculex I® (a corn variety expressing Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing Cry1Ac toxin); Bollgard I® (a cotton variety expressing Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0037] Further examples of such genetically modified crops are Bt11 Maize by Syngenta, Bt176 Maize by Syngenta, MIR604 Maize by Syngenta, MON863 Maize by Monsanto, IPC531 Cotton by Monsanto, 1507 Maize by Pioneer, NK603xMON810 Maize by Monsanto.

[0038] Mixtures containing cyclothiazomycin C and streptimidon may also be used, for example, on lawns, ornamental plants such as flowers, shrubs, broadleaf trees, or evergreen trees, for example conifers, as well as for trunk injections, pest control, and the like.

[0039] Preferred crops in which mixtures comprising cyclothiazomycin C and streptimidon can be used include cereals and pulses such as peanuts or soybeans, and grains such as wheat or corn.

[0040] As used herein, the term "locus" means the field in which a plant is growing or in which the seeds of a cultivated plant have been sown or in which the seeds will be sown in the soil. It includes the soil, the seeds and seedlings, as well as the established vegetation.

[0041] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, seedlings, roots, tubers, stems, stalks, foliage and fruits.

[0042] The term "plant propagation material" is understood to refer to reproductive parts of plants, such as seeds, which can be used for their propagation, and vegetative bodies, such as cuttings or tubers, for example potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and plant parts may be mentioned. Also mentioned are sprouted plants and shoots that are to be transplanted after germination or emergence from the soil. These shoots may be protected by a complete or partial treatment by immersion before transplantation. Preferably, "plant propagation material" is understood to refer to seeds.

[0043] The mixtures containing cyclothiazomycin C and streptimidon can be used in their pure form or, preferably, together with the auxiliaries conveniently employed in the field of formulation. For this purpose, they can be conveniently formulated in a known manner into emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and capsules, for example, in polymeric materials. The application method, such as spraying, misting, dusting, scattering, coating, or pouring, as well as the type of composition, are selected according to the intended purpose and the current situation. The composition may also contain further auxiliaries, such as stabilizers, defoamers, viscosity regulators, binders or adhesives, as well as fertilizers, sources of trace elements, or other compounds for obtaining special effects.

[0044] Furthermore, when cyclothiazomycin C is obtained from a microorganism, it may be isolated from the microorganism as described in WO2015191789. Alternatively, significant amounts of cyclothiazomycin C may be present in the medium in which the microorganism is grown, in which case the medium or liquid medium may be used together with streptimidon to formulate the bactericidal and fungicidal composition. As a further alternative, the microorganism may produce both cyclothiazomycin C and streptimidon, in which case the microorganism itself may be used to formulate the composition. Thus, disclosed is a process for producing cyclothiazomycin C and streptimidon, comprising fermenting the microorganism in a suitable fermentation medium under conditions to produce cyclothiazomycin C and streptimidon. In such cases, the microorganism may be formulated as a living cell that actively produces cyclothiazomycin C and streptimidon, or may be inactivated, for example, by heat treatment. The microorganism may be concentrated as needed by centrifugation or other conventional techniques.

[0045] Suitable carriers and adjuvants, for example for use in agriculture, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0046] Suspension concentrates are formulations in which fine solid particles of the active compound are suspended in a liquid. Such formulations contain anti-settling and dispersing agents and may further contain wetting agents to enhance activity, as well as anti-foaming agents and crystal growth inhibitors. In use, these concentrates are diluted in water and usually applied by spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0047] Wettable powders are in the form of fine particles that disperse easily in water or other liquid carriers. These particles contain the active ingredient held in a solid matrix. Typical solid matrices include Fuller's earth, kaolin clay, silica and other easily wet organic or inorganic solids. Wettable powders usually contain 5% to 95% of the active ingredient and small amounts of wetting agents, dispersing agents or emulsifying agents.

[0048] Emulsifiable concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist solely of the active compound and a liquid or solid emulsifier, or may contain a liquid carrier such as xylene, high boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and usually applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0049] Granular formulations include both extrudates and relatively coarse particles, and are usually applied undiluted to the area where treatment is required. Typical carriers for granular formulations include sand, Fuller's earth, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, ground corn cobs, ground peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations usually contain 5% to 25% active ingredient, which may include surfactants such as high-boiling aromatic naphtha, kerosene and other petroleum fractions, or vegetable oils; and / or spreading agents such as dextrin, glue or synthetic resins.

[0050] Dusts are free-flowing admixtures of the active ingredient and finely divided solids such as talc, clays, powders and other organic and inorganic solids which act as dispersants and carriers.

[0051] Microcapsules are typically droplets or granules of active ingredient enclosed in an inert porous shell that allows the encapsulated material to be released into the environment at a controlled rate. The encapsulated droplets are typically 1-50 microns in diameter. The encapsulated liquid typically constitutes 50-95% of the capsule's weight and may contain a solvent in addition to the active compound. Encapsulated granules are generally porous granules with a porous membrane that seals the pore openings of the granule and retains the active species in liquid form within the pores of the granule. The granules are typically in the range of 1 millimeter to 1 centimeter in diameter, preferably 1-2 millimeters. Granules are formed by extrusion, agglomeration or prilling, or are natural. Examples of such materials are vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0052] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which complete dissolution at the desired concentration is achieved, such as water, acetone, alkylated naphthalenes, xylenes and other organic solvents. Pressurized sprayers may also be used in which the active ingredient is dispersed in finely divided form as the low boiling dispersant solvent carrier evaporates.

[0053] Suitable agricultural adjuvants and carriers useful in formulating the compositions of the present invention in the formulation types described above are well known to those skilled in the art.

[0054] Liquid carriers that may be utilized include, for example, water, vegetable oil, toluene, xylene, petroleum naphtha oil, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, kutadeca Examples of suitable solvents include ethyl acetate, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin, and N-methyl-2-pyrrolidinone. For dilution of concentrates, water is the typical carrier of choice.

[0055] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, Kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut hulls, and lignin.

[0056] A wide range of surfactants may be advantageously utilized in both the liquid and solid compositions, particularly those designed to be diluted with a carrier prior to application. These surfactants, when used, typically comprise from 0.01% to 15% by weight of the formulation. They may be anionic, cationic, nonionic or polymeric in nature and may be utilized as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as Tween 20, diethanolammonium lauryl sulfate; alkylaryl sulfonate salts such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide adducts such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide adducts such as tridecyl alcohol-C.sub.16 ethoxylate; soaps such as sodium stearate; alkylnaphthalene sulfonates such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryl trimethyl ammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters.

[0057] Other adjuvants commonly utilized in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray size regulators, pigments, antioxidants, foaming agents, defoamers, light blocking agents, compatibilizers, antifoaming agents, sequestering agents, neutralizing and buffering agents, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, trace elements, emollients, lubricants and adhesives.

[0058] Additionally, other agrochemically active ingredients or compositions may be combined with the compositions of the present invention, used in the methods of the present invention, and applied simultaneously or sequentially with the compositions of the present invention. When applied sequentially, the compositions of the present invention may be applied to the plant during a different growth phase than the other agrochemically active ingredients. When applied simultaneously, these additional active ingredients may be formulated together with the compositions of the present invention or mixed, for example, in a spray tank. These additional agrochemically active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, growth stimulants and / or plant growth regulators.

[0059] Pesticides are referred to herein using their common names and are known, for example from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0060] The mixture of the present invention, or each of its components, cyclothiazomycin C or streptimidon, can be mixed with one or more insecticides known in the art.

[0061] The mixture according to the invention or each of its components, cyclothiazomycin C or streptimidon, can be mixed with one or more of the following known bactericides and fungicides: A compound selected from the group of substances consisting of petroleum, 1,1-bis(4-chloro-phenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-cinnamaldehyde, 4-chlorophenyl phenylsulfone, acetoprole, aldoxicarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramite, arsenic trioxide, azobenzene, azotoate, benomyl, benoxaphos, benzyl benzoate, bixafen, bromocyclohexane ... Clen, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium polysulfate, camphechlor, carbanolate, carbophenothione, cymiazole, thio-methionate, chlorbeneside, chlordimeform, chlordimeform hydrochloride, chlorphenetole, chlorfenson, chlorophenesulfide, chlorobenzilate, chloromebuform, chloromethiuron, chloropropylate, chlorthiophos, cinerin I, cinerin II, cinerin, closantel, coumaphos, Crotamiton, Crotoxyphos, Kufraeb, Cyanthoate, DCPM, DDT, Demefion, Demefion-O, Demefion-S, Demeton-Methyl, Demeton-O, Demeton-O-Methyl, Demeton-S, Demeton-S-Methyl, Demeton-S-Methyl Sulfone, Dichlofluanid, Dichlorvos, Dicrifos, Dienochlor, Dimefox, Zinex, Zinex-Diclexin, Dinocap-4, Dinocap-6, Dinocton, Dino-Penton, Dinosulfone, Dinotervone, Dioxathion, Diphenylsulfone, Disulfiram, DNOC, Doxathione ... Fenapine, doramectin, endothion, epirimectin, etheoate methyl, etrimphos, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fen-pyroximate, fenpyrazamine, fenson, fentrifanil, flubenzimine, flucycloxuron, fluenethyl, fluorbenside, FMC1137, formetanate, formetanate hydrochloride, formoparanate, gamma-HCH, gliodin, halfenprox, hexadecylcyclopropanecarboxylate, isocarbophos, jasmolin I,Jasmolin II, Jodofenphos, Lindane, Malonoben, Mecarbam, Mefosfolan, Mesulfen, Methacrifos, Methyl Bromide, Metolcarb, Mexacarbate, Milbemycin Oxime, Mipafox, Monocrotophos, Morphothion, Moxidectin, Naled, 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, Nifluridide, Nikkomycin, Nitrilacarb, Nitri Lacarb 1:1 zinc chloride complex, omethoate, oxydeprophos, oxydisulfoton, pp'-DDT, parathion, permethrin, fencapton, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactin, proclonol, promacyl, propoxur, protidathion, protoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pyrimitate, quinalphos, quinthiophos, R-1492, phosglycine, rotenone, Schradan, cebufos, selamectin, sofamid, SSI-121, sulfiram, sulfuramide, sulfotep, sulfur, diflovidazin, tau-fluvalinate, TEPP, terbam, tetradifon, tetrasul, thiafenox, thiocarboxim, thiofanox, thiometon, thioquinox, thuringiensin, triamiphos, triaratene, triazophos, triazuron, tripenophos, trinactin, vamidothion, vaniliprole, bethoxazin, copper dioctanoate, copper sulfate, sibutrin, diclofen, dichlorophen, endothal, fentin, hydrated lime, nerbam, quinoclamine, quinoneamide, simazine, triphenyltin acetate, triphenyltin hydroxide, crufomate, piperazine, thiophanate, Chloralose, Fenthion, Pyridin-4-amine, Strychnine, 1-Hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-Hydroxyquinoline sulfate, Bronopol, Copper hydroxide, Cresol, Dipyrithione, Doditin, Fenaminosulf, Formaldehyde, Hydralagafen, Kasugamycin, Kasugamycin hydrochloride hydrate, Nickel bis(dimethyldithiocarbamate), Nitrapyrin, Octilinone, Oxolinic acid, Oxytetracycline, Hydroxyquinoline potassium sulfate, Probenazole, Streptomycin, Streptomycin sesquisulfate, Tecloftalam, Thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp.), Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae var. anisopliae, Neodiprion sertifer NPV and N. lecontei NPV, Orius spp.), Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis occidentalis), Verticillium lecanii,. Apholate, Visadil, Busulfan, Dimatif, Hemel, Hempa, Metepa, Methiotepa, Methyl Apholate, Molzide, Penfluron, Tepa, Thiohempa, Thiotepa, Tretamine, Uredep, (E)-Deca-5-en-1-yl acetate + (E)-Deca-5-en-1-ol, (E)-Trideca-4-en-1-yl acetate, (E)-6-Methylhept-2-en-4-ol, (E,Z)-Tetradeca-4,10-dien-1-yl acetate, (Z)-Dodec-7-en-1-yl acetate, (Z)-Hexadec-11-enal, (Z)-Hexadec-11-en-1-yl acetate, (Z)-Hexadec-13-en-11-yn-1-yl acetate, (Z)-Icos-13-en-10-one, (Z)-Tetradec-7-en-1-al, (Z)-Tetradec-9-en-1-ol, (Z)-Tetradec-9-en-1-yl acetate, (7E,9Z)-Dodeca-7,9-diene-1 -yl acetate, (9Z,11E)-tetradec-9,11-dien-1-yl acetate, (9Z,12E)-tetradec-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnonan-5-ol + 4-methylnonan-5-one, α-multistriatin, brevicomin, codrel, codremon, querle, disparlure, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate, dodecyl Ca-8,10-dien-1-yl acetate, dominicalure, ethyl 4-methyloctanoate, eugenol, frontalin, grandolure, grandolure I, grandolure II, grandolure III, grandolure IV, hexalure, ipsdienol, ipsenol, japonirure, lineatin, litalure, loopurure, medulure, megatomoic acid, methyleugenol, muscalure, octadeca-2,13-dien-1-yl acetate, octadeca-3,13-Dien-1-yl acetate, Olfrular, Orictalure, Ostramon, Siglua, Soldigin, Sulcatol, Tetradec-11-en-1-yl acetate, Trimedulure, Trimedulure A, Trimedulure B1, Trimedulure B2, Trimedulure C, Trunc-call, 2-(octylthio)-ethanol, Butapyronoxyl, Butoxy(polypropylene glycol), Dibutyl adipate, Dibutyl phthalate ethyl, dibutyl succinate, diethyl toluamide, dimethylcarbate, dimethyl phthalate, ethyl hexanediol, hexamide, methoquin-butyl, methyl neodecaneamide, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)-ethane, 1,2-dichloropropane + 1,3-dichloropropene, 1-bromo-2-chloroethane, 2,2,2-trichloro-1-(3,4- Dichloro-phenyl)ethyl acetate, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidone , 2-Isovalerylindan-1,3-dione, 2-Methyl(prop-2-ynyl)aminophenyl methyl carbamate, 2-Thiocyanatoethyl laurate, 3-Bromo-1-chloroprop-1-ene, 3-Methyl-1-phenylpyrazol-5-yl dimethyl carbamate, 4-Methyl(prop-2-ynyl)amino-3,5-xylyl methyl carbamate, 5,5-Dimethyl-3-oxocyclohex-1-enyl dimethyl carbamate,, Acetione, acrylonitrile, aldrin, allosamidin, alixicarb, α-ecdysone, aluminum phosphide, aminocarb, anabasine, atidathion, azamethiphos, Bacillus thuringiensis thuringiensis) delta endotoxin, barium hexafluorosilicate, barium polysulfide, bartholin, Bayer 22 / 190, Bayer 22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl)ether, sodium borate, bromfenvinphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sebazine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlor Prazophos, cis-resmethrin, cismethrin, clocithrin, copper acetoarsenite, copper arsenate, copper oleate, cumitoate, cryolite, CS708, cyanofenphos, cyanophos, ciclethrin, cithioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dicapton, dichlorophenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilol, dimefluthrin, dimethane, dimethrin, dimethylvinphos, dimethylan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ecdysterone, EI 1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, dichloroethane, ethylene oxide, EXD, fenchlorphos, fenetacarb, fenitrothion, fenoxacrim, fenpyritrin, fensulfothion, fenthion-ethyl, flucofuron, fosmetiran, fospirate, fostietan, furathiocarb, fretrin, guazatine, guazatine acetate, sodium tetrathiocarboxylate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hikincarb, IPSP, isazofos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I,Juvenile hormone II, juvenile hormone III, kereban, kinoprene, lead arsenate, leptophos, lilimphos, ritidathion, m-cumenylmethylcarbamate, magnesium phosphide, magidox, mecarfone, menazone, mercurous chloride, mesulfenphos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, methoclotophos, methoprene, methotrin, methoxychlor, methyl isothiocyanate, methyl chloroform, methylene chloride, methoxa Diazon, Mirex, Naphthalophos, Naphthalene, NC-170, Nicotine, Nicotine sulfate, Nithiazine, Nornicotine, O-5-Dichloro-4-iodophenyl O-Ethyl Ethyl Phosphorothioate, O,O-Diethyl O-4-Methyl-2-Oxo-2H-Chromen-7-yl Phosphorothioate, O,O-Diethyl O-6-Methyl-2-Propyl Pyrimidin-4-yl Phosphorothioate, O,O,O',O'-Tetrapropyl Dithiopyrophosphate , oleic acid, para-dichlorobenzene, parathion-methyl, pentachlorophenol, pentachlorophenyl laurate, PH60-38, fenkapton, phosnichlor, phosphine, phoxim-methyl, pyrimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, pyrimidophos, profluthrin, promecarb, prothiophos, pyrazophos, pyresmethrin, Cassia, Quinalphos-methyl, Quinothione, Lafoxanide, Resmethrin, Rotenone, Cadethrin, Lyania, Ryanodine, Sabadila, Shradan, Cebufos, SI-0009, Tiapronil, Sodium arsenite, Sodium cyanide, Sodium fluoride, Sodium hexafluorosilicate, Sodium pentachlorophenoxide salt, Sodium selenate, Sodium thiocyanate, Sulcofuron, Sulcofuron-sodium, Sulfuryl fluoride, Sulprofos, Tall oil, thionazine, TDE, tebupirimphos, temephos, telallethrin, tetrachloroethane, cyclofos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormethaphos-3, trichloronath, trimethacarb, tolprocarb, triclopyricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprophos, meperfluthrin, tetramethylfluthrin, bis(tributyltin)oxide, bromoa Cetamide, Ferric phosphate, Niclosamide-olamine, Tributyltin oxide, Pyrimorph, Trifenmorph, 1,2-Dibromo-3-chloropropane, 1,3-Dichloropropene, 3,4-Dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, Anicifluprine, Benclothiaz, Cytokinin, DCIP, Lufural, Isamidophos, Kinetin, Myrothecium verrucaria verrucaria composition, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis extract, alpha-chlorohydrin, anth, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropazine, flupropazine hydrochloride, norbormide, fosacetim, phosphorus, pindone, pyrinuron, sciriloside, sodium fluoride acetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)-ethyl piperonylate, 5-(1,3-Benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol + nerolidol, berubutin, MGK 264, piperonyl butoxide, piperotal, propyl isomer, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chloroinconazide, mercury oxide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole , Cyproconazole, Difenoconazole, Diniconazole, Epoxycon-azole, Fenbuconazole, Fluquinconazole, Flusilazole, Flutriafol, Furametpyr, Hexaconazole, Imazalil, Imiben-con-azole, Ipconazole, Metconazole, Myclobutanil, Paclobutrazol, Pefurazoate, Penconazole, Prothioconazole, Pyrifenox, Prochlorazol, Pro Piconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpicloride nil, fludioxonil, benalaxyl, furalaxyl, meta-lacyl, R-metalaxyl, ofrace, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, diclozolin, myclozolin, procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine,, Iminoctadine, azoxystrobin, dimoxystrobin, enestrobulin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, methominostrobin n, trifloxystrobin, oryzastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, Bordeaux mixture, copper oxide, mancopper, oxine copper , nitrothal-isopropyl, edifenphos, iprobenphos, phosdifen, turkphos-methyl, anilazine, benthiavalicarb, blasticidin-S, chloroneb, chlorotalonil, cyflufenamid, cymoxanil, cyclobutrifluram, diclocymet, diclomedine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, flumethylsulpholim forim), fluopicolide, fluoxythioconazole, flusulfamide, fluxapyroxad, fenhexamid, phos-ethyl-aluminum, hymexazole, iprovalicarb, cyazofamid, methasulfo-carb, metrafenone, pencycuron, phthalide, polyoxin, propamocarb, pyribencarb, proquinazid, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamid, fulve tetraam, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucipram, isotianil, dipimethitrone, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, methoxystrobin (jiaxiangjunzhi), lvbenmixianan, diclobenthiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiproline, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumide, impirfluxam, tulorprocarb, mefentrifluconazole, ipfentrifluconazole , 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazole-4- yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonic acid, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridaclomethyl, 3-( Difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, amethoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamide, fenpicoxamide, methallylpicoxamide, tebufloquine, ipurfenoquine, quinofumelin, isofetamide, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1 -Methyl-pyrazole-4-carboxamide, benzothiostrobin, phenamacryl, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenoxadiazam, flutianil, fluopimomide, pyrapropoin, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, 4-[[ 6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiproline, enoxastrobin, 4-[ [6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, Trinexapac, cumoxystrobin, zhongshengmycin, copper thiodiazole, zinc thiazole, amethotropin, iprodione, seboctylamin, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo -2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared according to the method described in WO 2015 / 155075); N'-[5- Bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared according to the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl N-ethyl-N-methyl-formamidine (these compounds may be prepared according to the methods described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds may be prepared according to the methods described in WO 2019 / 110427);N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide; N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared according to the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro- 3,3-Dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-di Fluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds may be prepared according to the method described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1, 2,4-Oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds may be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared from the method described in WO 2016 / 156290). 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared from the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1 -(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound may be prepared from the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound may be prepared from the method described in WO 2016 / 202742);2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared according to the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds may be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (these compounds may be prepared from the methods described in WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]pyrazole-4-carboxylate (this compound can be prepared from the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2 ,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared from the method described in WO 2018 / 202428).

[0062] The mixture according to the invention or each of its components, cyclothiazomycin C or streptimidon, may be mixed with one or more of the following known biological fungicides: Biological bactericides and fungicides selected from the following group: (2.1) bacteria, such as Bacillus subtilis, in particular the strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, having the NRRL accession number B21661 and described in US Pat. No. 6,060,051); Bacillus pumilus, in particular the strain QST2808 (available from Bayer CropScience LP, US as SONATA®, having the accession number NRRL B-30087 and described in US Pat. No. 6,245,551); Bacillus pumilus, in particular the strain GB34 (available from Bayer AG, DE as Yield Shield®); Bacillus pumilus, in particular the strain BU F-33, having NRRL accession number 50185 (available as part of the CARTISSA products from BASF, EPA Reg. No. 71840-19); Bacillus amyloliquefaciens, specifically strain D747 (available as Double Nickel™ from Kumiai Chemical Industry Co., Ltd., having accession number FERM BP-8234, U.S. Pat. No. 7,094,592); Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered in Taiwan as a biological fungicide under registration numbers 4764, 5454, 5096 and 5277); Bacillus subtilis strain MBI600 (available as SUBTILEX from BASF SE), having accession number NRRL No. 5,061,495, having B-50595; Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, DE);Bacillus subtilis var. amyloliquefaciens, strain FZB24, having accession number DSM10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5)); Bacillus mycoides, isolate J, having accession number B-30890 (available from Certis USA LLC, a subsidiary of Mitsui & Co., Ltd., as BMJ TGAI® or WG and LifeGard®); Bacillus licheniformis, in particular strain SB3086, having accession number ATCC 55406, as disclosed in WO 2003 / 000051 (available from Novozymes as ECOGUARD® Biofungicide and GREEN Biofungicide); RELEAF®); Paenibacillus sp. strains having accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297; Bacillus subtilis strain BU1814, (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA); Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.); Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768; WO 2014 / 028521) (Marrone Bio Innovations' STARGUS®); Bacillus amyloliquefaciens strain FZB42, accession number DSM23117 (available as RHIZOVITAL® from ABiTEP, DE);Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation); Bacillus mojavensis strain R3B (Accession number NCAIM(P)B001389) from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.) (WO 2013 / 034938); Paenibacillus polymyxa ssp. plantarum from BASF SE (WO 2016 / 020371); Paenibacillus epiphyticus from BASF SE (WO 2016 / 020371); Accession number NRRL Pseudomonas chlororaphis strain AFS009 carrying B-50897, WO 2017 / 019448 (e.g. HOWLER™ and ZIO® from AgBiome Innovations, US); Pseudomonas chlororaphis, in particular strain MA342 (e.g. CEDOMON®, CERALL® and CEDRESS® from Bioagri and Koppert); Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (ACTINO-IRON® and ACTINOVATE® from Novozymes); Agrobacterium radiobacter Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA); Agrobacterium radiobacter strain K1026 (e.g., NOGALL™ from BASF SE);Bacillus subtilis strain KTSB (FOLIACTIVE® from Donaghys); Bacillus subtilis IAB / BS03 (AVIV® from STK Bio-Ag Technologies); Bacillus subtilis strain Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered in Taiwan as a biological fungicide under registration numbers 4764, 5454, 5096 and 5277); Bacillus amyloliquefaciens isolate B246 (e.g. AVOGREEN® from University of Pretoria); Bacillus methylotrophicus strain BAC-9912 (available from Chinese Academy of Sciences' Institute of Applied Sciences); Pseudomonas proradix (e.g. PRORADIX® from Sourcon Padena); Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (Accession Number DSM 7206) (MYCOSTOP® from Verdera; PREFENCE® from BioWorks; see Crop Protection 2006, 25, 468-475); Pseudomonas fluorescens strain A506 (e.g. BLIGHTBAN® A506 by NuFarm); and (2.2) Fungi, for example: Coniothyrium minitans, in particular the strain CON / M / 91-8 (accession number DSM 9660; e.g. Contans® from Bayer CropScience Biologics GmbH); Metschnikowia fructicola, in particular the strain NRRL Y-30752; (B2.2.3) Microsphaeropsis ochracea; Trichoderma atroviride, in particular the strain SC1 (with accession number CBS122089, WO 2009 / 116106 and US Pat. No. 8,431,120 (Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (for example from Agrimm Technologies Sentinel from Biocontrol Limited; Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa SimbT5 (from Simbiose Agro); Gliocladium roseum (also known as Clonostachys rosea f rosea), in particular strain 321U from Adjuvants Plus, strain ACM941 as disclosed in ue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3):519-524), or strain IK726 (Jensen DF, et al.Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain ’IK726’;Australas Plant Pathol.2007;36:95-101);タラロマイセスフラバス(Talaromyces flavus)、. strain V117b; Trichoderma viride, in particular the strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137); Trichoderma asperellum, in particular the strain SKT-1, having the accession number FERM P-16510 (e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd.), the strain T34 (e.g. T34 Biocontrol from Biocontrol Technologies SL, ES) or the strain ICC 012 from Isagro; Trichoderma atroviride, strain CNCM1-1237 (e.g. Esquive® WP from Agrauxine, FR); Trichoderma atroviride, in particular the strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137); Trichoderma asperellum, in particular the strain SKT-1, having the accession number FERM P-16510 (e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd.), the strain T34 (e.g. T34 Biocontrol from Biocontrol Technologies SL, ES) or the strain ICC 012 from Isagro; Trichoderma atroviride, strain CNCM1-1237 (e.g. Esquive® WP from Agrauxine, FR); atroviride, strain number V08 / 002387; Trichoderma atroviride, strain NMI number V08 / 002388; Trichoderma atroviride, strain NMI number V08 / 002389; Trichoderma atroviride, strain NMI number V08 / 002390; Trichoderma atroviride, strain LC52 (e.g., Tenet by Agrimm Technologies Limited); Trichoderma atroviride, strain ATCC20476 (IMI206040); Trichoderma atroviride atroviride, strain T11 (IMI352941 / CECT20498); Trichoderma harmatum; Trichoderma harzianum; Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US);Trichoderma asperellum, in particular the strain kd (e.g. T-Gro from Andermatt Biocontrol); Trichoderma harzianum, strain ITEM908 (e.g. Trianum-P from Koppert); Trichoderma harzianum, strain TH35 (e.g. Root-Pro from Mycontrol); Trichoderma virens (also known as Gliocladium virens), in particular the strain GL-21 (e.g. SoilGard by Certis, US); Trichoderma viride, strain TV1 (e.g. Trianum-P from Koppert); Ampelomyces quisqualis, in particular the strain AQ10 (e.g. AQ from IntrachemBio Italia). 10 (registered trademark); blastospores of Aureobasidium pullulans, in particular of the strain DSM 14940; blastospores of Aureobasidium pullulans, in particular of the strain DSM 14941; a mixture of blastospores of Aureobasidium pullulans, in particular of the strains DSM 14940 and DSM 14941 (e.g. Botector (registered trademark) by bio-ferm, CH); Cladosporium cladosporioides, strain H39, having the accession number CBS 122244, US Patent Application Publication No. 2010 / 0291039 (Stichting Dienst Landbouwkundig Onderzoek); Gliocladium catenulatum catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g. Prestop® by Lallemand);Conidia of Lecanicillium lecanii (formerly known as Verticillium lecanii) strain KV01 (e.g. Vertalec® by Koppert / Arysta); Penicillium vermiculatum; Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Pat. No. 7,579,183; Trichoderma atroviride, strain SKT-1 (FERM P-16510), JP-A-11-253151; Trichoderma atroviride, strain SKT-2 (FERM P-16511), JP-A-11-253151; Trichoderma atroviride, strain SKT-3 (FERM P-17021), JP-A-11-253151; Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC392151CABI, e.g. BioDerma by AGROBIOSOL DE MEXICO, SADE CV); Trichoderma harzianum, strain DB103 (available as T-GRO® 7456 by Dagutat Biolab); Trichoderma polysporum, strain IMI206039 (e.g. Binab TF WP by BINAB Bio-Innovation AB, Sweden); Trichoderma stromaticum, with accession number Ts3550 (e.g. Tricovab by CEPLAC, Brazil); Ulocladium audemansi oudemansii strain U3, having accession number NM99 / 06216 (e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® by BioWorks, Inc.);Verticillium albo-atrum (formerly V. dahliae), strain WCS850 with accession number WCS850, deposited at the Central Bureau for Fungi Cultures (e.g. DUTCH TRIG® from Tree Care Innovations); Verticillium chlamydosporium; Trichoderma asperellum strain ICC012 (also known as Trichoderma harzianum ICC012), with accession number CABI CC IMI392716; and Trichoderma gamsii (formerly T. viride), strain ICC080 with accession number IMI392151 (e.g. Isagro BIO-TAM™ from USA, Inc. and BIODERMA™ from Agrobiosol de Mexico, SA de CV); Trichoderma asperelloides JM41R (accession number NRRL B-50759) (TRICHO PLUS™ from BASF SE); Aspergillus flavus strain NRRL21882 (product known as AFLA-GUARD™ from Syngenta / ChemChina); Chaetomium cupreum (accession number CABI353812) (e.g. BIOKUPRUM™ from AgriLife); Saccharomyces cerevisiae, in particular the strain LASO2 (Agro-Levures et al. Derives), strain LAS117 cell wall (CEREVISANE® from Lesaffre; ROMEO® from BASF SE), strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790);Trichoderma virens strain G-41, formerly known as Gliocladium virens (accession number ATCC 20906) (e.g. ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US); Trichoderma hamatum, having accession number ATCC 28012; Ampelomyces quisqualis strain AQ10, having accession number CNCM1-807 (e.g. AQ10® from IntrachemBio Italia); Phlebiopsis gigantea strain VRA1992 (ROTSTOP® C from Danstar Ferment); Penicillium stickii from BASF SE steckii (DSM27859; WO 2015 / 067800); Chaetomium globosum (available as RIVADIOM® from Rivale); Cryptococcus flavescens, strain 3C (NRRL Y-50378); (B2.2.99) Dactylaria Candida; Dilophosphora alopecuri (available as TWIST FUNGUS®); Fusarium oxysporum, strain Fo47 (available as FUSACLEAN® from Natural Plant Protection); Pseudozyma flocculosa, strain PF-A22 UL (available as SPORODEX® L from Plant Products Co., CA);(2.2.103) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC392151CABI) (available under the trademark BIODERMA® by AGROBIOSOL DE MEXICO, SADE CV); Trichoderma fertile (for example the product TrichoPlus from BASF); Muscodor roseus, in particular the strain A3-5 (accession number NRRL30548); Simplicillium lanosoniveum; (3) Biological stimulants having the effect of improving plant growth and / or plant health that can be combined with the combination of compounds of the present invention, including: (3.1) Bacteria selected from the group consisting of Bacillus pumilus, in particular the strain QST2808 (having the accession number NRRL No. B-30087); Bacillus subtilis, in particular the strain QST713 / AQ713 (having the NRRL accession number B-21661 and described in U.S. Pat. No. 6,060,051; available as SERENADE® OPTI or SERENADE® ASO from Bayer CropScience LP, US); Bacillus subtilis, in particular the strain AQ30002 (having the accession number NRRL B-50421 and described in U.S. Patent Application Publication No. 13 / 330,576); Bacillus subtilis, in particular the strain AQ30004 (as well as NRRL B-50455, and described in U.S. Patent Application Publication No. 13 / 330,576; Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience); Bacillus subtilis strain BU1814 (available as TEQUALIS® from BASF SE); Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection); Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection);Bacillus mycoides BT155 (NRRL No. B-50921), Bacillus mycoides EE118 (NRRL No. B-50918), Bacillus mycoides EE141 (NRRL No. B-50916), Bacillus mycoides BT46-3 (NRRL No. B-50922), Bacillus cereus family member EE128 (NRRL No. B-50917), Bacillus thuringiensis BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7), Bacillus Bacillus cereus family member EE349 (NRRL No. B-50928), Bacillus amyloliquefaciens SB3281 (ATCC No. PTA-7542; WO 2017 / 205258), Bacillus amyloliquefaciens TJ1000 (available as QUIKROOTS® from Novozymes); Bacillus firmus, particularly strain CNMC1-1582 (e.g., VOTIVO® from BASF SE); Bacillus pumilus, particularly strain GB34 (e.g., YIELD SHIELD® from Bayer Crop Science, DE); Bacillus amyloliquefaciens, in particular the strain IN937a; Bacillus amyloliquefaciens, in particular the strain FZB42 (e.g. RHIZOVITAL® from ABiTEP, DE); Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015);Mixtures of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as QUARTZO® (WG), PRESENCE® (WP)); Bacillus cereus, particularly strain BP01 (ATCC 55675; e.g. MEPICHLOR® from Arysta Lifescience, US); Bacillus subtilis, particularly strain MBI600 (e.g. SUBTILEX® from BASF SE); Bradyrhizobium japonicum (e.g. OPTIMIZE® from Novozymes); Mesorhizobium cicer (e.g. NODULATOR from BASF SE); Rhizobium hairy vetch leguminosarium biovar viciae (e.g., NODULATOR from BASF SE); Delftia acidovorans, particularly strain RAY209 (e.g., BIOBOOST® from Brett Young Seeds); Lactobacillus sp. (e.g., LACTOPLANT® from LactoPAFI); Paenibacillus polymyxa, particularly strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.); Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena); Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.); Azospirillum lipoferum lipoferum) (e.g., VERTEX-IF™ from TerraMax, Inc.);A mixture of Azotobacter vinelandii and Clostridium pasteurianum (available as INVIGORATE® from Agrinos); Pseudomonas aeruginosa, in particular the strain PN1; Rhizobium leguminosarum, in particular the bv.viceae strain Z25 (accession number CECT4585); Azorhizobium caulinodans, in particular the strain ZB-SK-5; Azotobacter chroococcum, in particular the strain H23; Azotobacter vinelandii, in particular the strain ATCC12837; Bacillus siamensis siamensis, in particular strain KCTC13613T; Bacillus tequilensis, in particular strain NII-0943; Serratia marcescens, in particular strain SRM (accession number MTCC8708); Thiobacillus sp. (e.g. CROPAID® from Cropaid Ltd UK); and; (3.2) Fungi selected from the group consisting of: Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus), strain 251 (AGAL 89 / 030550; e.g. BioAct from Bayer CropScience Biologics GmbH), Penicillium bilaii, strain ATCC 22348 (e.g. JumpStart® from Acceleron BioAg), Talaromyces flavus, strain V117b; Trichoderma atroviride, strain CNCM1-1237 (e.g. Esquive® WP from Agrauxine, FR), Trichoderma viride, for example strain B35 (Pietr et al. al., 1993, Zesz. Nauk.AR w Szczecinie 161:125-137; Trichoderma atroviride strain LC52 (Trichoderma atroviride strain LU132; also known as Sentinel, for example, from Agrimm Technologies Limited; described in WO 2008 / 000196) Trichoderma atroviride strain SC1; Trichoderma asperellum strain kd (for example, T-Gro, from Andermatt Biocontrol); Trichoderma asperellum strain Eco-T (Plant Health Products, ZA); Trichoderma harzianum strain T-22 (for example, from Andermatt Trianum-P from Biocontrol or Koppert; Myrothecium verrucaria strain AARC-0255 (e.g. DiTera™ from Valent Biosciences); Penicillium bilaii strain ATCC ATCC20851; Pythium oligandrum strain M1 (ATCC38472; e.g. Polyversum from Bioprepraty, CZ); Trichoderma virens strain GL-21 (e.g. SoilGard™ from Certis, USA); Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS276.92; e.g. Dutch Trig from Tree Care Innovations; Trichoderma atroviride, in particular strain number V08 / 002387, strain number NMI number V08 / 002388, strain number NMI number V08 / 002389, strain number NMI number V08 / 002390; Trichoderma harzianum strain ITEM908; Trichoderma harzianum, strain TSTh20; Trichoderma harzianum strain 1295-22; Pythium oligandrum strain DV74; Rhizopogon amylopogon (e.g. Helena Chemical Company, in Myco-Sol; Rhizopogon fulvigleba (e.g., as contained in Myco-Sol from Helena Chemical Company); or Trichoderma virens strain GI-3.

[0063] The mixture according to the invention or each of its components (cyclothiazomycin C or streptimidon) can be mixed with or further contain malonomycin, which can be prepared according to the method disclosed in EP 1 860 939, Examples I A. and B.

[0064] In addition, the compositions of the present invention may also be applied with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and are described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0065] The mixtures containing cyclothiazomycin C and streptimidon can be used in the form of agrochemical compositions and can be applied to crop areas or treated plants simultaneously or sequentially with further compounds. These further compounds can be, for example, fertilizers or sources of trace elements or other preparations that affect plant growth. They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, together with further carriers, surfactants or application-promoting adjuvants, if desired, which are customarily employed in the field of formulations.

[0066] The mixture containing cyclothiazomycin C and streptimidon can be used in the form of a (fungicidal) composition for the control or protection against phytopathogenic microorganisms, which contains as active ingredients cyclothiazomycin C and streptimidon and at least one of the above-mentioned adjuvants.

[0067] The present invention therefore provides a composition, preferably a fungicidal composition, comprising cyclothiazomycin C, streptimidon, an agriculturally acceptable carrier, and optionally an adjuvant. An agriculturally acceptable carrier is, for example, a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may comprise, in addition to cyclothiazomycin C and streptimidon, at least one more pesticidally active compound, for example an additional fungicidal active ingredient.

[0068] The compositions according to the invention may also comprise further solid or liquid auxiliaries, such as stabilizers, e.g. unepoxidized or epoxidized vegetable oils (e.g. epoxidized coconut oil, rapeseed oil or soybean oil), antifoaming agents, e.g. silicone oils, preservatives, viscosity regulators, binders and / or adhesives, fertilizers or other active ingredients to achieve a particular effect, e.g. fungicides, bactericides / fungicides, nematicides, plant activators, molluscicides or herbicides.

[0069] The compositions according to the invention are prepared in a manner known per se in the absence of auxiliaries, for example by pulverizing, screening and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example by intimately mixing and / or pulverizing the active ingredient with one or more auxiliary agents. These preparation processes of the compositions and the use of compound (I) for preparing these compositions are also the subject of the present invention.

[0070] Another aspect of the invention relates to the use of a composition comprising cyclothiazomycin C and streptimidon, or a fungicidal or insecticidal mixture comprising cyclothiazomycin C and streptimidon, in admixture with other fungicides or insecticides as mentioned above, for the control or prevention of infestation by insects or by phytopathogenic microorganisms, preferably fungal organisms, on plants, such as useful plants, e.g. crop plants, their propagation material, e.g. seeds, harvested crops, e.g. harvested food crops, or on non-living material.

[0071] A further aspect of the invention relates to a method for controlling or preventing infestation of plants, e.g. useful plants such as crop plants, their propagation material, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material, by insects or by phytopathogenic or spoilage microorganisms or by organisms potentially harmful to humans, in particular fungal organisms, which comprises the step of applying a mixture comprising cyclothiazomycin C and streptimidon as active ingredients to the plant, to parts of the plant or its habitat, to its propagation material, or to any part of the non-living material.

[0072] Control or prevention means the reduction of infestation by phytopathogenic or spoilage microorganisms, or by organisms potentially harmful to humans, especially fungal organisms, to the extent that an improvement can be demonstrated.

[0073] Preferred methods for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects include those in which the application of the compound of formula (I) and the compound of formula (II) or the agrochemical composition containing at least one of said compounds is a foliar treatment. The frequency and amount of application will depend on the risk of infestation by the corresponding pathogen. However, the compositions of the invention can also be introduced into the plant through the roots via the soil, by irrigating the plant habitat with a liquid formulation, or by applying the compound in solid form, for example in granular form, to the soil (soil application). In rice crops, such granules can be applied to flooded rice fields. The mixtures of the invention can also be applied to seeds by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation (coating).

[0074] Formulations, e.g. compositions, containing the mixtures of the invention and, if desired, solid or liquid auxiliary agents or monomers encapsulating the mixtures of the invention, can typically be prepared in a known manner by intimately mixing and / or grinding the compounds together with extenders, e.g. solvents, solid carriers and, optionally, surface-active compounds (surfactants).

[0075] The weight / molar ratio of cyclothiazamicin C to streptimidon is preferably from 10:1 to 1:500, more preferably from 1:1 to 1:300.

[0076] Advantageous application rates are usually from 0.1 g to 6 kg of active ingredient (ai; the combined weight of cyclothiazamicin C and streptimidon) per hectare (ha), preferably from 0.1 g to 1 kg ai / ha, most preferably from 10 g to 800 g ai / ha.

[0077] When the combinations according to the invention are used for the treatment of seeds, a rate of from 0.001 to 100 g of active ingredient per kg of seed, preferably from 0.01 to 10 g per kg of seed, is generally sufficient.

[0078] Advantageously, the compositions comprising cyclothiazomycin C and streptimidon according to the invention are applied either prophylactically, meaning before the onset of disease, or curatively, meaning after the onset of disease.

[0079] Certain mixtures of CtmC and streptimidon may show synergistic effects. This occurs whenever the action of the combination of active ingredients is greater than the sum of the actions of the individual components. The expected action E for a given combination of active ingredients can be calculated according to the so-called Colby formula as follows (COLBY, SR “Calculating synergistic and antagonistic responses of herbicide combination”. Weeds, Vol. 15, pages 20-22; 1967): ppm = milligrams of active ingredient per litre of spray mixture (=ai) X = % effect of active ingredient A) using p ppm of active ingredient Y=% effect of active ingredient B) using q ppm of active ingredient.

[0080] According to COLBY, the expected (additive) effect of active ingredients A) + B) using p+q ppm of active ingredients is as follows:

number

[0081] If the actual observed effect (O) is greater than the expected effect (E), the effect of the combination is superadditive, i.e., a synergistic effect is present. In mathematical terms, synergy corresponds to a positive value for the difference (OE). In the case of a purely complementary addition of activity (expected activity), the difference (OE) is zero. A negative value for the difference (OE) indicates a loss of activity compared to the expected activity.

[0082] However, besides the actual synergistic action with regard to the fungicidal and fungicidal activity, the compositions according to the invention may also have further unexpected advantageous properties. Examples of such advantageous properties that may be mentioned are: more favorable degradability; improved toxicological and / or ecotoxicological behavior; or improved useful plant characteristics, including emergence, crop yield, more developed root system, increased tillers, increased plant height, larger leaf blades, less dead basal leaves, stronger tillers, darker green leaf color, reduced fertilizer requirements, reduced seed number required, more productive tillers, earlier flowering, earlier grain maturation, less plant verse (lodging), increased shoot growth, plants with improved vigor, and earlier germination.

[0083] The compositions of the present invention may be in any conventional form, such as, for example, two-part systems, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (WG), sorbent granules (RM ... The present invention may be employed in the form of an emulsion, such as an EG, an emulsion, a water-in-oil (EO), an emulsion, an oil-in-water (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL), a soluble concentrate (SL), a very low volume suspension (SU), a very low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), or any technically desirable formulation in combination with an agriculturally acceptable adjuvant.

[0084] Such compositions can be produced in a conventional manner, for example by mixing the active ingredient with suitable inert compounding agents (diluents, solvents, fillers, and any other compounding agents such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds that provide adjuvant activity effects). Conventional slow-release formulations can also be employed when long-lasting efficacy is intended. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvant effects, such as, for example, condensates of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0085] The seed dressing formulation is applied to the seed in a manner known per se, utilizing the combination and diluent of the present invention in a suitable seed dressing formulation form, such as an aqueous suspension or a dry powder form with good adhesion to the seed. Such seed dressing formulations are known in the art. The seed dressing formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example as a slow release capsule or microcapsule.

[0086] Generally, the formulations contain 0.01-90% by weight of active agent, 0-20% of an agriculturally acceptable surfactant and 10-99.99% of a solid or liquid inert compounding agent, and adjuvants, cyclothiazomycin C, streptimidon, optionally with other active agents, such as microbicides, preservatives, etc. Concentrated forms of the composition generally contain about 2-80%, preferably about 5-70% by weight of active agent. Application forms of the formulations may contain, for example, 0.01-20%, preferably 0.01-5% by weight of active agent. Commercial products will preferably be formulated as concentrates, but end users will usually utilize diluted formulations.

[0087] Another aspect of the invention relates to the use of a mixture comprising cyclothiazomycin C and streptimidon as an antifungal agent in a food, feed, beverage or cosmetic product. Preferably, the food product is fruit and fruit-derived products, vegetables and vegetable-derived products, grains and grain-derived products, dairy products, meat, poultry and seafood, and mixtures thereof. Preferably, the food product is selected from dairy products or baked products. Preferably, the dairy product is a fermented dairy product such as yoghurt or cheese. More preferably, the dairy product is selected from the group consisting of yoghurt, low-fat yoghurt, non-fat yoghurt, kefir, dahi, ymer, buttermilk, butter, sour cream, sour whipped cream, fresh cheese, unripened or curdled cheese and ripened cheese. Preferably, the present invention relates to the use of a mixture comprising cyclothiazomycin C and streptimidon as an antifungal agent, wherein the fungus is selected from the group consisting of Aspergillus (Aspergillus), Penicillium (Penicillium), Cladosporium (Cladosporium), Rhizopus (Rhizopus), eurotium (Eurotium), Paecilomyces (Paecilomyces), Saccharomyces (Saccharomyces), and the like. saccharomyces (Saccharomyces), zygosaccharomyces (Zygosaccharomyces), debaryomyces (Debaryomyces), Candida (Candida), rhizopus (Rhizopus), Fusarium (Fusarium), altemaria (Altemaria) and Mucor (Mucor).More preferably, the present invention relates to the use of a mixture comprising cyclothiazomycin C and streptimidon as an antifungal agent in a baked product, wherein the fungus is selected from the group consisting of Aspergillus niger, Aspergillus fumigatus, Aspergillus flavus, Eurotium rubrum, Paecilomyces variotii, Penicillium roquefori.

[0088] More preferably, the present invention relates to the use of a mixture comprising cyclothiazomycin C and streptimidon as an antifungal agent in a beverage, wherein the fungus is selected from the group consisting of Aspergillus niger, Saccharomyces cerevisiae and Zygosaccharomyces bailii.

[0089] More preferably, the present invention relates to the use of a mixture comprising cyclothiazomycin C and streptimidon as an antifungal agent in a dairy product as defined above, wherein the fungus is selected from the group consisting of Kluyveromyces marxianus, Yarrowia lipolytica, Penicillium nalgiovense, Cladiosporium ssp., Penicillium commune, Mucor ssp., Penicillium brevicompactum, Aspergillus versicolor, Penicillium crustosum, Kluyveromyces lactis, Kluyveromyces cerevisiae ... lactis, more preferably the fungus is Penicillium roquefori or Debaryomyces hansenii.

[0090] The mixture containing cyclothiazomycin C and streptimidon can be used in several ways to produce an antifungal effect. Preferably, the mixture containing cyclothiazomycin C and streptimidon is administered in an effective amount. The mixture containing cyclothiazomycin C and streptimidon can be added at the final stage or intermediate stage in the production of food, feed, beverage or cosmetic products. Preferably, the surface of the food, feed, beverage or cosmetic product is treated with the mixture containing cyclothiazomycin C and streptimidon. For example, the mixture containing cyclothiazomycin C and streptimidon is sprayed or coated on the surface of the food, feed, beverage or cosmetic product. For example, the mixture containing cyclothiazomycin C and streptimidon is sprayed or coated on a dairy product, such as yogurt or cheese. Alternatively, the mixture containing cyclothiazomycin C and streptimidon is mixed with the food, feed, beverage or cosmetic product. For example, the mixture containing cyclothiazomycin C and streptimidon is mixed with milk or a dairy product, such as yogurt. Alternatively, a mixture containing cyclothiazomycin C and streptimidon is mixed into dough for the preparation of baked products.

[0091] The mixture containing cyclothiazomycin C and streptimidon may be used in native form or, preferably, formulated as defined above. Preferably, the composition containing the mixture containing cyclothiazomycin C and streptimidon comprises an adjuvant, a surfactant, a solid carrier and / or a liquid carrier, all as defined above. As a further alternative, the microorganism itself may be used to formulate the composition. In such a case, the microorganism may be formulated as a living cell that actively produces cyclothiazomycin C and streptimidon, or may be inactivated, for example, by heat treatment. The microorganism may be concentrated as necessary by centrifugation or other conventional techniques.

[0092] According to a further aspect, the present invention relates to a mixture comprising cyclothiazomycin C and streptimidon for use as a medicament. Furthermore, the present invention relates to a mixture comprising cyclothiazomycin C and streptimidon for use as a pharmaceutical product for treating infections caused by pathogenic fungi, preferably pathogenic yeasts. In a preferred embodiment, the pharmaceutical product is a product useful for the administration of a mixture comprising cyclothiazomycin C and streptimidon to humans or animals to inhibit pathogenic microorganisms and to alleviate symptoms associated with pathogenic microorganisms. Examples of such symptoms include symptoms associated with yeast infections. In such an embodiment, the pharmaceutical product may be a unit dosage form comprising cyclothiazomycin C and streptimidon. Preferably, the unit dosage form is a capsule or tablet. However, the unit dosage form may also be suitable for application to mucous membranes or skin and may therefore be in the form of a paste, cream, ointment, etc. EXAMPLES

[0093] The following examples are intended to illustrate the invention.

[0094] Throughout this specification, temperatures are given in degrees Celsius (° C.), "mp." means melting point, rh means relative humidity, CtmC means cyclothiazomycin C, and ppm means parts per million by weight.

[0095] Streptimidone was synthesized according to the method disclosed in Kondo, H., Oritani, T., and Kiyota, H. Synthesis and antifungal activity of the four stereoisomers of streptimidone, a glutarimide antibiotic from Streptomyces rimosus forma paromomycinus. Eur. J. Org. Chem. (20), 3459-3462 (2000).

[0096] Example 1: Isolation of cyclothiazomycin C from NRRL WC-9803. NRRL strain WC-3908 was obtained from the NRRL Culture Collection and was grown in 100 mL baffled shaker flasks at 225 rpm in an Innova 44 shaker incubator (1 inch stroke). Flasks contained 25 mL of medium containing 10 g / L Merck casein hydrolysate, 8 g / L Difco Bacto tryptone, 2 g / L Difco Bacto soytone, 1.25 g / L K2HPO4, and 0.3 g / L Basildon antifoam. Flasks were closed with foam plugs. The pH was adjusted to 6.8 with 4N H2SO4 prior to autoclaving. 15 g / L glucose.H2O was added from a separately autoclaved 500 g / L glucose.H2O stock. Inoculation was performed with biomass or spores and incubation at 28°C was continued until glucose reached 1-5 g / L, which required approximately 2-3 days. CtmC was purified according to WO2015191789.

[0097] Example 2: Efficacy of a mixture of streptimidon and cyclothiazamicin C (CtmC) 2.1 General method Mixtures of streptimidon and CtmC were tested at various concentrations on various fungal species and isolates. The active components were first dissolved separately in dimethyl sulfoxide (DMSO) to form two stock solutions: 1000 ppm CtmC and 10000 ppm streptimidon. These stock solutions were used to form test solutions by dispersing an appropriate amount of each stock solution in water with 0.025% by weight of the test solution of Tween 20, a commercially available dispersant. The amount of each component used in each test is shown in the results table below.

[0098] Samples of seven fungal pathogens were obtained by dispersing them in potato dextrose broth (PDB) at the following spore concentrations per milliliter of water: Zymoseptoria tritici K6105 80,000Sp / ml Zymoseptoria tritici K6420 80,000Sp / ml Zymoseptoria tritici K6318 80,000Sp / ml Gibberella zeae K6934 15,000Sp / ml Fusarium virguliforme K6285 15,000Sp / ml Fusarium virguliforme K6286 15,000Sp / ml Wheat head blight fungus (Microdochium nivale) K7484 30,000~50,000Sp / ml

[0099] For each test, 10 μl of test solution was mixed with 90 μl of a dispersion of fungal pathogen in PDP in a single well of an assay plate. The assay plate was incubated at 24° C. and 80% RH for 3 days. The results were evaluated using an optical density reader at a wavelength of 620 nm.

[0100] 2.2 Results Synergistic efficacy occurs whenever the effect of a combination of active ingredients is greater than the sum of the effects of the individual components. The expected effect E for a given combination of active ingredients can be calculated according to the so-called Colby formula as follows (COLBY, SR “Calculating synergistic and antagonistic responses of herbicide combination”. Weeds, Vol. 15, pages 20-22; 1967): ppm = milligrams of active ingredient per liter of spray mixture (= streptimidon or CtmC) X = % effect of active ingredient A) using p ppm of active ingredient Y=% effect of active ingredient B) using q ppm of active ingredient.

[0101] According to COLBY, the expected (additive) effect of active ingredients A) + B) using p+q ppm of active ingredients is as follows:

number

[0102] If the actual observed effect (O) is greater than the expected effect (E), the effect of the combination is superadditive, i.e., a synergistic effect is present. In mathematical terms, synergy corresponds to a positive value for the difference (OE). In the case of a purely complementary addition of activity (expected activity), the difference (OE) is zero. A negative value for the difference (OE) indicates a loss of activity compared to the expected activity.

[0103] The synergistic fungicidal efficacy calculated according to Colby's formula was observed in the following Experiments 2.2.1 to 2.2.4, where the difference (OE) is shown in parentheses after the efficacy percentage.

[0104] [Table 1]

[0105] [Table 2]

[0106] [Table 3]

[0107] [Table 4]

[0108] The efficacy of the mixture was also demonstrated against additional fungal species.

[0109] [Table 5]

[0110] [Table 6]

[0111] [Table 7]

[0112] Example 3: Efficacy of CtmC alone against certain fungi; plate bioassays against Botrytis cinerea and Zymoseptoria tritici Preparation of bioassay plates. Media for bioassay plates was prepared by mixing equal volumes of Difeo Plate Count Agar and Difeo Potato Dextrose Agar. 40 mL was used in Nunc™ OmniTray™ single well plates. After solidification and cooling to 20° C., a 10 mL top layer containing equal volumes of sterile water and Difeo Potato Dextrose Agar was applied at 42° C. Just before pouring the top layer, spores of Fusarium culmorum, Botrytis cinerea or Zymoseptoria tritici were added. Spore concentrations used were 1000 cfu / mL for B. cinerea and 20,000 cfu / mL for Z. tritici. After pouring the top layer, the bioassay plates were dried in a laminar flow cabinet for 1 hour and used immediately. After sample application, the plates were incubated at 22°C until visual assessment of the zone of fungal inhibition was possible.

[0113] The liquid medium from Example 1 was added to the bioassay plates as 7 μl droplets.

[0114] An example of the zones of inhibition seen is shown in FIG. 1A, which shows the zones of inhibition caused by whole broth samples of NRRL strain WC-3908 in Botrytis cinerea bioassay plates.

[0115] An example of the zones of inhibition seen is shown in FIG. 1B, which shows the zones of inhibition caused by whole broth samples of NRRL strain WC-3908 in Zymoseptoria tritici bioassay plates.

[0116] An example of the zones of inhibition seen is shown in FIG. 1C, which shows the zones of inhibition caused by whole broth samples of NRRL strain WC-3908 in Fusarium culmorum bioassay plates.

[0117] Example 4: Efficacy of purified CtmC against Fusarium virguliforme A Fusarium virguliforme spore suspension was prepared at 25,000 spores / ml in PDB (Potato Dextrose Broth) medium supplemented with 0.3% agar. This isolate was from the Syngenta internal collection (CH). A stock solution was prepared by dissolving CtmC in DMSO (Dimethyl Sulfoxide) to a final concentration of 1000 ppm. Different dilutions of CtmC were prepared in DMSO: 1000 ppm, 330 ppm, 110 ppm, 37 ppm, 12 ppm and 4.1 ppm. 10 μl of DMSO or CtmC solution was transferred to a 96-well-dilution plate and diluted 10-fold with 90 μl of 0.025% Tween20 / H2O solution. From the dilution plate, 10 μl was transferred to a 96-well assay plate and 90 μl of spore suspension was added to each well.

[0118] The wells of the 96 well plate contain:

[0119] [Table 8]

[0120] The 96-well plates were then incubated at 24° C., 90% relative humidity, and in the dark for 72 hours. The plates were evaluated by reading the OD at 620 nm.

[0121] Assays were performed with two independent isolates of these species. Each isolate was tested twice (Assay 1 and Assay 2), and each isolate x fungicide dose combination was replicated on the test plates.

[0122] The OD620 was averaged between two wells and used to calculate IC50 values ​​(the fungicide concentration that causes 50% inhibition of growth) using the GraphPad prism program, and four independent IC50 values ​​were obtained. No significant differences were found between both tested isolates.

[0123] [Table 9]

[0124] As shown in Table 2 above, both isolates tested have similar IC50s of approximately 1 ppm.

[0125] Example 5: Efficacy of purified CtmC against fungal species in vitro A stock solution was made by dissolving CtmC in DMSO (dimethylsulfoxide) to a final concentration of 1000 ppm. A second 1:10 dilution was made in water + 0.025% Tween 20. From this second dilution, 10 μl was aliquoted into a 96-well plate. To each well, 90 μl of medium containing fungal spores was added and mixed, resulting in a final CtmC concentration of 10 ppm. All wells containing CtmC also contained DMSO (1%) and Tween 20 (0.0025%).

[0126] Botrytis cinerea (gray mold): Fungal conidia stored at low temperature were mixed directly into nutrient broth (PDB potato dextrose broth). A solution of the test compound was placed in a microtiter plate (96-well format) followed by the addition of nutrient broth containing fungal spores. The test plates were incubated at 24°C and growth inhibition was measured photometrically after 72 hours.

[0127] Monographella nivalis (snow rot, root rot of cereals): Fungal conidia stored at low temperature were mixed directly into nutrient broth (PDB potato dextrose broth). A solution of the test compound was placed in a microtiter plate (96-well format) followed by the addition of nutrient broth containing fungal spores. The test plates were incubated at 24°C and growth inhibition was measured photometrically at 620 nm after 72 hours.

[0128] Mycosphaerella arachidis (peanut brown spot disease): Fungal conidia stored at low temperature were mixed directly into nutrient broth (PDB potato dextrose broth). A solution of the test compound was placed in a microtiter plate (96-well format) followed by the addition of nutrient broth containing fungal spores. The test plates were incubated at 24°C and after approximately 5-6 days, growth inhibition was measured photometrically at 620 nm.

[0129] Zymoseptoria tritici (Septoria leaf blight): Fungal conidia stored at low temperature were mixed directly into nutrient broth (PDB potato dextrose broth). A solution of the test compound was placed in a microtiter plate (96-well format) followed by the addition of nutrient broth containing fungal spores. The test plates were incubated at 24°C and growth inhibition was measured photometrically after 72 hours.

[0130] [Table 10]

[0131] Conidiospores of the four species tested were inhibited in the presence of 10 ppm cyclothiazomycin C (90-100% reduction).

[0132] Example 6: Potency of purified CtmC against fungal species in a leaf disc assay. CtmC stock was made up in DMSO at 1000 ppm and then diluted 1:50 in water + Tween 20 (0.025%) to give a 20 ppm solution.

[0133] Puccinia triticina (also known as Puccinia recondite, leaf rust, wheat): Wheat leaf segments are placed on agar in multiwell plates (24-well format) and sprayed with the test solution. After drying, the leaf segments are inoculated with a fungal spore suspension. After appropriate incubation, the activity of the compounds is evaluated 8 dpi (days post inoculation) as preventive fungicidal / fungicidal activity.

[0134] Phakopsora pachyrhizi (Asian soybean rust): Soybean leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with the test solution. After drying, the leaf disks are inoculated with a fungal spore suspension. After appropriate incubation, the activity of the compounds is evaluated approximately 12 dpi (days post inoculation) as preventive fungicidal / fungicidal activity.

[0135] [Table 11]

[0136] At 20 ppm, CtmC was able to reduce the occurrence of the two rust species tested by 50-90%.

[0137] Example 7: Efficacy of purified CtmC against fungal species in the greenhouse Purified cyclothiazomycin C (CtmC) was formulated as an EC50 formulation. The formulation was diluted with water to give 100 ppm and 50 ppm CtmC. Plants were treated with 400 L / ha of the diluted product, supplemented with adjuvants to improve adhesion and spreadability, resulting in treatments with 40 g / ha and 20 g / ha of CtmC, respectively.

[0138] Zymoseptoria tritici Wheat / Preventative (Septoria tritici Wheat Spot). Two-week-old wheat plants (cv. Riband) are sprayed with the formulated test compounds diluted in water in a spray chamber. One day after application, the test plants are inoculated by spraying with a spore suspension. After a one-day incubation period at 22°C / 21°C (day / night) and 95% rh, the inoculated test plants are maintained in a greenhouse at 22°C / 21°C (day / night) and 70% rh. Efficacy is assessed directly after an appropriate level of disease appears on untreated check plants (16-19 days after application).

[0139] Puccinia triticina (also known as Puccinia recondata, wheat leaf rust). Two-week-old wheat plants (cv. Arina) are sprayed with the formulated test compounds diluted in water in a spray chamber. One day after application, the test plants are inoculated by spraying with a spore suspension. After a one-day incubation period at 20° C. and 95% rh, the inoculated test plants are maintained in a greenhouse at 20° C. / 18° C. (day / night) and 60% rh. The percentage leaf area covered by disease is assessed once an appropriate level of disease appears on untreated check plants (12-14 days after application).

[0140] Botrytis cinerea Tomato / Preventative (Botrytis in Tomato) Four-week-old tomato plants (cv. Roter Gnom) are treated with the formulated test compound diluted in water in a spray chamber. Two days after application, the test plants are inoculated by spraying with a spore suspension. The inoculated test plants are incubated in a greenhouse at 20°C and 95% rh and the percentage leaf area covered by disease is assessed once an appropriate level of disease appears on untreated check plants (5-6 days after application).

[0141] Mycosphaerella arachidis Peanut / Preventative (Brown Spot Disease in Peanut) Three-week-old peanut plants (cv. Georgia Green) are sprayed with the formulated test compound diluted in water in a spray chamber. One day after application, the test plants are inoculated by spraying a spore suspension on the underside of the leaves. After a four-day incubation period at 23°C and 100% rh under a plastic hood, the inoculated test plants are maintained in a greenhouse at 23°C / 20°C (day / night) and 70% rh. The percentage leaf area covered by disease is assessed once an appropriate level of disease appears on untreated check plants (12-14 days after application).

[0142] [Table 12]

[0143] The results show that CtmC is active as a bactericide and reduces disease severity in plants in the greenhouse.

[0144] Example 8: Effect of Tween 20 on the efficacy of purified CtmC against Fusarium virguliforme. Prior art WO2015191789 clearly states that the inventors found no fungal inhibitory effect for cyclothiazomycin C. This is contrary to the results of the present inventors. To exclude the possibility that the bactericidal and fungicidal effects observed by the present inventors were due to the presence of Tween 20, the present inventors performed several experiments such as those in Example 3 at various levels, including without Tween 20.

[0145] The experiment outlined in Example 3 was repeated to evaluate EC50 values ​​for the CtmC control against Fusarium virguliforme in the presence of four different Tween 20 rates: 0% (no Tween 20), 0.0025%, 0.0050% (same as Example 3) and 0.0100%. The plate layout was the same as in Example 7, except that the plates were replicated four times to accommodate the different Tween 20 concentrations in the assay plates. All other experimental conditions were kept comparable. Fusarium isolates were tested at 25,000 sp / ml.

[0146] [Table 13]

[0147] The results are consistent with Example 3, showing that Tween 20 has no significant effect on the EC50 values ​​for control of Fusarium virguliforme in vitro.

[0148] Example 9: Efficacy of purified CtmC alone against a wider range of fungal species in vitro A stock solution was made by dissolving CtmC in DMSO (dimethylsulfoxide) to a final concentration of 1000 ppm. A second 1:10 dilution was made in water + 0.025% Tween 20. From this second dilution, 10 μl was aliquoted into a 96-well plate. To each well, 90 μl of medium (PDB-Potato Dextrose Broth + 0.3% Agar) containing fungal spores was added and mixed, resulting in a final CtmC concentration of 10 ppm. All wells containing CtmC also contained DMSO (1%) and Tween 20 (0.0025%). In Table 4 below, some of these species were tested with a number of different isolates (internal strain numbers shown) to understand the variability associated with different isolates of the same species, taken from different locations, producing different mycotoxins (Fusarium) or expressing different tolerances to fungicides of the SDHI (succinate dehydrogenase inhibitors), SBI (sterol biosynthesis inhibitors) and / or QoI (quinone external inhibitor) classes (e.g. Zymoseptoria tritici). As shown, the inoculum density and number of biological replicates were different for the different isolates.

[0149] [Table 14] TIFF2024531932000020.tif142168

[0150] The results indicate that a wide variety of fungal species can be at least partially controlled, and that numerous isolates of the same species have similar susceptibility to CtmC.

Claims

1. A composition comprising cyclothiazomycin C and streptimidon.

2. 2. The composition of claim 1, wherein the ratio of cyclothiazomycin C to streptimidon is from 10:1 to 1:500 by weight.

3. 3. The composition of claim 2, wherein the ratio of cyclothiazomycin C to streptimidon is from 1:1 to 1:300 by weight.

4. A pesticide composition comprising a fungicidally effective amount of a mixture comprising cyclothiazomycin C and streptimidon.

5. 5. The pesticide composition of claim 4, further comprising an agrochemically acceptable diluent or carrier.

6. 10. A pesticide composition comprising the composition of claim 1.

7. 10. A method for controlling or preventing fungal infestation of plants, comprising applying a fungicidally effective amount of the composition of any one of claims 1 to 6 to the plant, its parts or its habitat.

8. 8. The method of claim 7, wherein the composition is applied to plants at a rate of 0.1 g to 6 kg of combined weight of cyclothiazomycin C and streptimidon per hectare.

9. 8. The method of claim 7, wherein the composition is applied to seeds at a rate of 0.001 to 100 g of the combined weight of cyclothiazomycin C and streptimidon per kg of seeds.

10. 8. The method of claim 7, wherein the plant is selected from the group consisting of cereals and legumes.

11. The fungi include Botrytis cinerea, Cercospora kikuchii, Cercospora sojina, Cochliobolus sativus, Colletotrichum lindemuthianum, Colletotrichum orbiculare, Corynespora cassiicola, Fusarium avenaceum, Fusarium culmorum, and the like. culmorum, Fusarium langsethiae, Fusarium poae, Fusarium sporotrichioides, Fusarium tricinctum, Fusarium virguliforme, Gibberella avenacea, Gibberella fujikuroi, Gibberella zeae, Microdochium majas majus, Monographella nivalis, Mycosphaerella arachidis, Phakopsora pachyrhizi, Puccinia triticina, Pyrenophora tritici-repentis, Ramularia collocygni, Rhynchosporium secalis, Septoria glycines, Tilletia tritici tritici), Ustilago segetum var. Tritici, Venturia8. The method of claim 7, wherein the pathogen is selected from the group consisting of Zymoseptoria tritici, Zymoseptoria inaequalis, and Zymoseptoria tritici.

12. 8. The method of claim 7, wherein the fungus is selected from the group consisting of Fusarium virguliforme, Monographella nivalis, Gibberella zeae, or Zymoseptoria tritici.

13. Use of a composition comprising cyclothiazomycin C and streptimidon according to any one of claims 1 to 3 as an antifungal agent or a bactericide / fungicide.

14. Use of a composition comprising cyclothiazomycin C and streptimidon according to any one of claims 1 to 3 as an antifungal agent in food, feed, beverage or cosmetic products.

15. 15. The use according to claim 14, wherein the food product is selected from dairy products or baked products.

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