[go: up one dir, main page]

WO2025031989A1 - Procédés de lutte contre l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola ou de prévention de celle-ci - Google Patents

Procédés de lutte contre l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola ou de prévention de celle-ci Download PDF

Info

Publication number
WO2025031989A1
WO2025031989A1 PCT/EP2024/072023 EP2024072023W WO2025031989A1 WO 2025031989 A1 WO2025031989 A1 WO 2025031989A1 EP 2024072023 W EP2024072023 W EP 2024072023W WO 2025031989 A1 WO2025031989 A1 WO 2025031989A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
plants
compound
formula
phytopathogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2024/072023
Other languages
English (en)
Inventor
David Beattie
Caio PRATES
Douglas MARQUES
Ricardo DESJARDINS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Syngenta Crop Protection AG Switzerland
Original Assignee
Syngenta Crop Protection AG Switzerland
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Crop Protection AG Switzerland filed Critical Syngenta Crop Protection AG Switzerland
Publication of WO2025031989A1 publication Critical patent/WO2025031989A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • the present invention relates to methods for controlling or preventing infestation of plants by the phytopathogenic microorganism Corynespora cassiicola.
  • Corynespora cassiicola infects over 530 species of plants in 53 families (Dixon, L. J., et al., Phytopathology 2009, 99(9), 1015-27). It is most common in the tropics and subtropics. It has also been isolated from nematodes and from human skin. Corynespora cassiicola is known as a pathogen of many agricultural crop plants, for example soybeans, corn, wheat, cotton, beans, potatoes, sweet potato, and tobacco. The disease caused by Corynespora cassiicola is called target leaf spot or target spot on several plants, for example target leaf spot of soybeans and target leaf spot on cotton.
  • pesticidal compositions comprising particular 5-(trifluoro- methyl)-1 ,2,4-oxadiazole compounds and one or more formulation adjuvants, are highly effective at controlling or preventing the infestation of plants, in particular field-grown plants, by the phytopathogenic microorganisms of the family Corynesporascaceae, in particular Corynespora cassiicola.
  • These highly effective pesticidal compositions thus represent an important new solution for farmers to control or prevent infestation of plants, in particular field-grown plants, by the phytopathogenic microorganism Corynespora cassiicola.
  • Agrochemical compositions comprising said 5-(trifluoro-methyl)-1 ,2,4-oxadiazole compounds have been disclosed in WO 2021/209360, WO2018/202428, WO 2019/233826, and methods for preparation have been disclosed in WO 2015/185485, WO 2017/211649, WO 2013/008162 and WO 2023/280630.
  • a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Corynespora cassiicola comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidally effective amount of a compound according to formula (I) wherein
  • X is O, or S
  • R 1 is selected from methyl, 2-fluorophenyl, or 2,4-difluorophenyl; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.
  • a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Corynespora cassiicola comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a pesticidal composition comprising a compound of formula (I), and one or more formulation adjuvants.
  • the compound according to formula (I), or the pesticidal composition comprising a compound of formula (I) and one or more formulation adjuvants is applied in the field.
  • a method of controlling or preventing infestation of field-grown plants by the phytopathogenic microorganism Corynespora cassiicola comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a compound of formula (I), or a pesticidal composition comprising a compound of formula (I) and one or more formulation adjuvants, formulation auxiliaries, diluents, and/or carriers.
  • the method according to any one of embodiments above comprising the steps of providing a composition comprising a compound of formula (I); and applying the composition to a propagation material; and planting the propagation material, preferably in the field.
  • the method comprising the steps of providing a composition comprising a compound of formula (I); applying the composition to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen.
  • the pesticidal composition comprises at least and one or more formulation adjuvants, as well as and one or more formulation auxiliaries, diluents, and/or carriers.
  • a compound of formula (I) for controlling or preventing infestation of plants by the phytopathogenic microorganism Corynespora cassiicola.
  • the plant is selected from soybeans, corn, wheat, cotton, beans, potatoes, sweet potato, and tobacco.
  • the plants are genetically modified plants, preferably Bt plants.
  • the present invention preferably also relates to a pesticidal composition suitable for control of diseases caused by phytopathogens comprising a component (A) and at least one or more compound(s) (B), wherein said component A is a compound of formula (I) wherein
  • X is O, or S
  • R 1 is selected from methyl, 2-fluorophenyl, or 2,4-difluorophenyl; and wherein said at least one or more compound(s) (B) is selected from other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides, one or more adjuvants), and a diluent or carrier or formulation auxiliary, or a combination thereof.
  • said at least one or more compound(s) (B) is selected from other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides, one or more adjuvants), and a diluent or carrier or formulation auxiliary, or a combination thereof.
  • the present invention preferably also relates to a pesticidal composition suitable for control of diseases caused by phytopathogens comprising a component (A) and at least one or more compound(s) (B), wherein said component A is a compound of formula (I) wherein
  • X is O, or S
  • R 1 is selected from methyl, 2-fluorophenyl, or 2,4-difluorophenyl; and wherein said at least one or more compound(s) (B) is selected from pesticides.
  • Compounds of formula (I) which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as Ci- C4alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as Ci- 04 alkane- or arylsulfonic acids which are unsubstituted or substituted, for example
  • Compounds of formula (I) which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- ortrihydroxy-lower-alkylamine, for example mono-, di- ortriethanolamine.
  • bases for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts
  • salts with ammonia or an organic amine such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, die
  • the compounds of formula (I) according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g., an agronomically usable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991 .
  • the compounds of formula (I) according to the invention also include hydrates which may be formed during the salt formation.
  • controlling refers to reducing the number of pests, eliminating pests and/or preventing further pest damage such that damage to a plant or to a plant derived product is reduced.
  • pest refers to insects, and molluscs that are found in agriculture, horticulture, forestry, the storage of products of vegetable origin (such as fruit, grain, and timber); and those pests associated with the damage of man-made structures.
  • the term pest encompasses all stages in the life cycle of the pest.
  • the term "effective amount” refers to the amount of the compound, or a salt thereof, which, upon single or multiple applications provides the desired effect.
  • an effective amount is readily determined by the skilled person in the art, using known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered including, but not limited to the type of plant or derived product to be applied; the pest to be controlled and its lifecycle; the particular compound applied; the type of application; and other relevant circumstances.
  • room temperature or “RT” or “rt” or “ambient temperature” refer to a temperature of about 15° C to about 35° C.
  • rt can refer to a temperature of about 20° C to about 30° C.
  • Embodiments according to the invention are provided as set out below.
  • compounds of formula (I) are selected from N-(2-fluorophenyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide according to structure l-A
  • compound of formula (I) is N-(2-fluorophenyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide according to structure l-A.
  • compound of formula (I) is N-methyl-4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]benzenecarbothioamide according to structure l-B.
  • the compound or compounds are generally applied as part of a pesticidal composition.
  • composition comprising a compound of formula (I) for controlling or preventing infestation of plants by the phytopathogenic microorganism Corynespora cassiicola.
  • Such pesticidal compositions typically comprise one or more adjuvants, formulation auxiliaries, diluents, and/or carriers as described in detail below, preferably at least one or more adjuvants.
  • compositions comprising a compound of formula (I) and preferably one or more adjuvants, formulation auxiliaries, diluents, and/or carriers for controlling or preventing infestation of plants by the phytopathogenic microorganism Corynespora cassiicola comprising the steps of providing a composition comprising said compound of formula (I); and applying said composition to the phytopathogen, to the locus ofthe phytopathogen, orto a plant susceptible to attack by the phytopathogen.
  • a fungicidal composition comprising a mixture of component (A) and a component (B) as active ingredients, wherein component (A) is selected from a compound of formula (I), (l-A), or (l-B), and component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxytioconazole, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4- triazol-1-y
  • component (A) is N-(2-fluorophenyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide (compound l-A), or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxytioconazole, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]
  • component (A) is N-(2-fluorophenyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide (compound l-B), or a salt, enantiomer, tautomer or N-oxide thereof, and component (B) is selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole
  • the weight ratio of component (A) to component (B) may be from 1000: 1 to 1 :1000, may be from 100:1 to 1 :100, preferably from 50:1 to 1 :50, more preferably from 20:1 to 1 :40, even more preferably from 15:1 to 1 :30, still more preferably from 12:1 to 1 :25, or from 10:1 to 1 :20, or from 10:1 to 1 :10, or from 5:1 and 1 :15, or from 5:1 to 1 :5, or from 4:1 to 1 :4, or from 3:1 to 1 :10, or from 3:1 to 1 :3, or from 2:1 to 1 :5, or 1 :1.
  • the composition may comprise an additional active ingredient component (C), which is different to component (B), and is selected from the group consisting of metyltetrapole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, epoxiconazole, hexaconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pydiflumetofen, fluxapyroxad, sedaxane, bixafen, isopyrazam, fluopyram, fluindapyr, isoflucypram, inpyrfluxam, quinofumelin, ipflufenoquin, aminopyrifen, fluazinam, fludioxonil, fen
  • C additional active ingredient component
  • the component (C) compounds are referred to herein and above by a so-called "ISO common name” or another "common name” being used in individual cases or a trademark name.
  • the component (C) compounds are known and are commercially available and/or can be prepared using procedures known in the art.
  • a fungicidal composition comprising a mixture of component (A) and a component (B) and a component (C) as active ingredients, wherein component (A) is selected from a compound of formula (I), (l-A), or (l-B), and component (B) and (C) are a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxytioconazole, 2-[2-chloro-4- (4-chlorophenoxy)phenyl]-2-hydroxy-3-(1
  • component (A) is N-(2-fluorophenyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide (compound l-A), or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) and (C) are a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxytioconazole, 2-[2-chloro-4-(4-chloroph)
  • the plants are selected from cotton, corn, or soybean.
  • said plants are genetically modified plants, preferably Bt plants, more preferably Bt soybean plant, Bt cotton or Bt corn.
  • component (A) is N-(2-fluorophenyl)- 4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide (compound l-B), or a salt, enantiomer, tautomer or N- oxide thereof
  • component (B) and (C) are a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxytioconazole, 2-[2-chloro-4-(4-chlorophenoxy)
  • Components (B) and (C) in combination with component (A) may enhance the effectiveness of the latter against fungi, and vice versa. Additionally, the fungicidal compositions may be effective against a wider spectrum of fungal pathogens that can be combated with the individual active ingredients when used solely.
  • the weight ratio of component (A) to the mixture of components (B) and (C) may be from 100:1 to 1 :100, or 50:1 to 1 :50, or 20:1 to 1 :20, or 10:1 to 1 :10, or 5:1 and 1 :5.
  • the weight ratio of component (A) to the mixture of components (B) and (C) may be from 2:1 to 1 :2, or 4:1 to 2:1 , or 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 WOO, or 1 WOO, or 1 :1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750.
  • Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand
  • the weight ratio of component (A) to the sum of component (B) and component (C) may be from 100:1 to 1 :100, preferably from 50:1 to 1 :50, more preferably from 20:1 to 1 :40, even more preferably from 15:1 to 1 :30, still more preferably from 12:1 to 1 :25, or from 10:1 to 1 :20, or from 10:1 to 1 :10, or from 5:1 and 1 :15, or from 5:1 to 1 :5, or from 4:1 to 1 :4, or from 3:1 to 1 :10, or from 3:1 to 1 :3, or from 2:1 to 1 :5, or 1 :1 .
  • the component (B) compounds are referred to herein and above by a so-called "ISO common name” or another "common name” being used in individual cases or a trademark name.
  • the component (B) compounds are known and are commercially available and/or can be prepared using procedures known in the art and/or procedures reported in the literature such as, for instance, WO 2015/155075 and WO 2016/202742, WO 2017/005710, WO 2018/108977, WO 2018/153707, WO 2018/098216, WO 2019/093522, WO 2018/145921 , WO 2015/185485, WO 2017/076742, WO 2017/081311 , WO 2017/085100, WO 2017/093019, WO 2017/178245, and WO 2017/211649.
  • the weight ratio of component (A) to the sum of first component (B) and second component (B) may be from 100:1 to 1 : 100, preferably from 50:1 to 1 :50, more preferably from 20:1 to 1 :40, even more preferably from 15:1 to 1 :30, still more preferably from 12:1 to 1 :25, or from 10:1 to 1 :20, or from 10:1 to 1 :10, or from 5:1 and 1 :15, or from 5:1 to 1 :5, or from 4:1 to 1 :4, or from 3:1 to 1 :10, or from 3:1 to 1 :3, or from 2:1 to 1 :5, or 1 :1.
  • composition stands for the various mixtures or combinations of component A, wherein said component A is selected from a compound of formula (I), (l-A), or (l-B), and components (B) (including the above-defined embodiments), for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the component A, wherein said component A is selected from a compound of formula (I), (l-A), or (I- B), and component (B) is not essential for working the present invention.
  • a method for controlling harmful fungi wherein the pest, their habitat, breeding grounds, their locus or the plants to be protected against pest attack, the soil or plant propagation material (preferably seed) are treated with a pesticidally effective amount of a compound of formula (I) according to the present invention.
  • a method for controlling harmful fungi wherein the pest, their habitat, breeding grounds, their locus or the plants to be protected against pest attack, the soil or plant propagation material (preferably seed) are treated with a composition comprising a pesticidally effective amount of a compound of formula (I) according to the present invention.
  • the compounds of the present invention and compositions comprising said compound of formula (I) are suitable for controlling fungal plant diseases.
  • the compounds of the present invention are also important for controlling a multitude of fungi on various cultivated plants, such as bananas, cotton, vegetable species, for example cucumbers, beans, and cucurbits; cereals such as maize, wheat, rye, barley, rice, oats; grass coffee, potatoes, sweet potatoes, corn, fruit species, soybean, tobacco, tomatoes, grapevines, ornamental plants, sugar cane and also on a large number of seeds.
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention are used in soybean, cotton, and corn.
  • compounds of formula (I), (l-A), or (l-B) according to the present invention are used on genetically modified plants selected from soybean, cotton, and corn.
  • said genetically modified plants selected from soybean, cotton, and corn are Bt plants, like Bt soybeans, Bt cotton and Bt corn.
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention are particularly suitable for controlling cotton diseases caused by Alternaria spp. (Alternaria leaf spot), Cercospora spp. (Cercospora leaf spots), Corynespora cassiicola (leaf spots); Ascochyta gossypii (ascochyta blight of cotton); Fusarium wilt in cotton (Gossypium hirsutum L.) caused by Fusarium oxysporum f. sp..
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention are particularly suitable for controlling cotton diseases caused by Corynespora cassiicola (leaf spots).
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention are suitable for controlling the following fungal diseases on soybeans: Alternaria spp. (Alternaria leaf spot); Cercospora spp. (Cercospora leaf spots), e.g., C. sojina or C. kikuchii Colletotrichum (teleomorph: Glomerella) spp. (anthracnose), e.g., C. truncatum or C.
  • gloeosporioides Corynespora cassiicola (leaf spots); Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot); Diaporthe spp., e.g., D. phaseolorum (damping off); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot), e.g. F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans; Macrophomina phaseolina (syn. phaseoli) (root and stem rot); Microsphaera diffusa (powdery mildew); Peronospora spp.
  • Phialophora spp. e.g., P. gregata. stem rot
  • Phomopsis spp. e.g., stem rot: P. phaseoli (teleomorph: Diaporthe phaseolorum); Pythium spp. (damping-off); Phytophthora spp. (wilt, root, leaf, fruit and stem root), e.g., P. megasperma, syn. P. sojae); Rhizoctonia spp., e.g., R.
  • solani root and stem rot
  • Sclerotinia spp. stem rot or white mold
  • Septoria spp. e.g., S. glycines (brown spot);
  • S. rolfsii syn. Athelia rolfsii
  • Thielaviopsis spp. black root rot.
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention are suitable for controlling the soybean diseases caused by Corynespora cassiicola (leaf spots).
  • the compounds of the invention or fungicidal compositions according to the present invention comprising said compounds may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Corynespora cassiicola) on soybean plants.
  • phytopathogenic fungi such as Corynespora cassiicola
  • said genetically modified plants are selected from soybean, cotton and maize.
  • said genetically modified plants are BT plants, selected from Bt soybean, Bt cotton and Bt maize.
  • said genetically modified plants are BT plants, selected from Bt soybean, and Bt cotton.
  • Examples of commercially available genetically modified soybean plants which can preferably be treated according to the invention, include, but not limited to, commercially available products such as plant seeds Intacta®, lntacta®2, Intacta® Roundup ReadyTM 2 Pro (lntacta®RR2 PRO), lntacta®2 XtendTM, Cultivance, Conkesta Soybean, Conkesta Enlist E3TM Soybean, EnlistTM Soybean, Enlist E3TM Soybean, Roundup ReadyTM Soybean, Roundup ReadyTM 2 XtendTM, Genuity® Roundup ReadyTM 2 XtendTM, Genuity® Roundup Ready 2 YieldTM, Herbicide-tolerant Soybean line, Optimum GATTM, Liberty LinkTM Soybean, Vistive GoldTM, Verdeca HB4 Soybean, TreusTM, PlenishTM.
  • commercially available products such as plant seeds Intacta®, lntacta®
  • said Bt soybean plants are selected from Intacta RR2 PRO®, or Conkesta Enlist E3®.
  • a method for controlling Corynespora cassiicola on soybean plants wherein said soybean plants are genetically modified soybean plants, preferably Bt soybean plants, characterized by comprising the step of contacting the plant, parts thereof, propagation material thereof, the pests, their food source, habitat, or breeding ground with a compound selected from N- (2-fluorophenyl)-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide according to structure l-A
  • soybean plants are genetically modified soybean plants, preferably Bt soybean plants, characterized by comprising the step of contacting the plant, parts thereof, propagation material thereof, the pests, their food source, habitat, or breeding ground with a compound of formula (l-A).
  • soybean plants are genetically modified soybean plants, preferably Bt soybean plants, characterized by comprising the step of contacting the plant, parts thereof, propagation material thereof, the pests, their food source, habitat, or breeding ground with a compound of formula (l-B).
  • the compounds of the invention or fungicidal compositions according to the present invention comprising said compounds may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Corynespora cassiicola) on cotton plants.
  • phytopathogenic fungi such as Corynespora cassiicola
  • Examples of commercially available genetically modified cotton plants which can preferably be treated according to the invention, include, but not limited to, commercially available products such as plant seeds Bollgard®, Bollgard II TM Cotton, LibertyLink®, Roundup ReadyTM, WideStrikeTM Cotton, Bollgard® III x Roundup ReadyTM FlexTM, GlyTolTM, GlyTolTM Liberty LinkTM, GlytolTM x TwinlinkTM, GlyTol LibertyLink TwinLink® Plus, FibermaxTM Liberty LinkTM, BollgardTM Cotton, IngardTM, Roundup ReadyTM BollgardTM Cotton, Roundup ReadyTM FlexTM Cotton, Roundup ReadyTM FlexTM Bollgard IITM Cotton, TwinLinkTM Cotton, BXNTM Cotton.
  • commercially available products such as plant seeds Bollgard®, Bollgard II TM Cotton, LibertyLink®, Roundup ReadyTM, WideStrikeTM Cotton, Bollgard® III x Roundup ReadyTM FlexTM, GlyTolTM, GlyTolTM Liberty LinkTM, GlytolTM x TwinlinkTM, Gly
  • said Bt cotton plants are selected from WideStrikeTM Cotton, Bollgard® III x Roundup ReadyTM FlexTM, GlyTolTM Liberty LinkTM, GlyTol LibertyLink TwinLink® Plus, Bollgard II TM Cotton, BollgardTM Cotton IngardTM, Roundup ReadyTM BollgardTM Cotton, Roundup ReadyTM FlexTM Cotton, and TwinLinkTM Cotton.
  • a method for controlling Corynespora cassiicola on cotton plants wherein said cotton plants are genetically modified cotton plants, preferably Bt cotton plants, characterized by comprising the step of contacting the plant, parts thereof, propagation material thereof, the pests, their food source, habitat, or breeding ground with a compound from N-(2-fluorophenyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide according to structure l-A
  • a method for controlling Corynespora cassiicola on cotton plants wherein said cotton plants are genetically modified cotton plants, preferably Bt cotton plants, characterized by comprising the step of contacting the plant, parts thereof, propagation material thereof, the pests, their food source, habitat, or breeding ground with a compound of formula (l-A).
  • a method for controlling Corynespora cassiicola on cotton plants wherein said cotton plants are genetically modified cotton plants, preferably Bt cotton plants, characterized by comprising the step of contacting the plant, parts thereof, propagation material thereof, the pests, their food source, habitat, or breeding ground with a compound of formula (l-B).
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention, or fungicidal compositions comprising said compounds according to the present invention may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Corynespora cassiicola) on soybean plants.
  • phytopathogenic diseases especially phytopathogenic fungi (such as Corynespora cassiicola) on soybean plants.
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention, or fungicidal compositions comprising said compounds according to the present invention may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Corynespora cassiicola) on genetically modified soybean plants, preferably Bt soybean plants.
  • phytopathogenic diseases especially phytopathogenic fungi (such as Corynespora cassiicola) on genetically modified soybean plants, preferably Bt soybean plants.
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention, or fungicidal compositions comprising said compounds according to the present invention may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Corynespora cassiicola) on cotton plants.
  • phytopathogenic fungi such as Corynespora cassiicola
  • the compounds of formula (I), (l-A), or (l-B) according to the present invention, or fungicidal compositions comprising said compounds according to the present invention may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Corynespora cassiicola) on genetically modified cotton plants, preferably Bt cotton plants.
  • phytopathogenic diseases especially phytopathogenic fungi (such as Corynespora cassiicola) on genetically modified cotton plants, preferably Bt cotton plants.
  • fungicidal compositions according to the present invention comprising a compound of formula (I), (l-A), or (l-B) when used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Corynespora cassiicola) on plants selected from soybean and cotton (in particular any of the transgenic plants as described above), may display a synergistic interaction between the active ingredients.
  • phytopathogenic fungi such as Corynespora cassiicola
  • Transgenic soybean plants expressing toxins for example insecticidal proteins such as delta-endotoxins, e.g., CrylAc (CrylAc Bt protein). Accordingly, this may include transgenic soybean plants comprising event MON87701 (disclosed in W02009/064652), event MON87701 x MON89788 (disclosed in WO2014/170327, e.g.
  • event MON87751 (disclosed in WO2014/201235)
  • event DAS-44406-6 e.g., commercially available as Enlist E3TM, DAS-44406-6, disclosed in WO2012/075426
  • event DAS-81419-2 (described in WO2013/016527, e.g., commercially available as ConkestaTM soybean); event DAS-81419-2 x DAS-44406-6 (e.g., commercially available as ConkestaTM Enlist E3TM Soybean).
  • transgenic events in transgenic soybean plants include event DAS-44406-6/pDAB8264.44.06.1 (soybean, herbicide-tolerance, disclosed in WO2012/075426); event DAS-81419-2 (described in WO2013/016527 (e.g., commercially available as aka ConkestaTM soybean, ConkestaTM Enlist E3TM soybean, DAS-81419-2 x DAS-44406-6); event DAS-14536-7/pDAB8291 .45.36.2 (soybean, herbicide-tolerance, disclosed in WO2012/075429); DAS-68416-4 (soybean, herbicide-tolerance, ATCC Accession No.
  • PTA-10442 disclosed in WO2011/066384, WO2011/066360
  • event DP-305423-1 (soybean, quality mark, disclosed in W02008/054747, e.g. commercially available as TreusTM, PlenishTM, Plenish® High Oleic Soybeans)
  • event DP-356043-5 (soybean, herbicide-tolerance, deposited as ATCC PTA- 8287, disclosed in W02008/002872, e.g.
  • event FG72 (soybean, herbicide-tolerance, disclosed in WO2011/063413); event LL27 (soybean, herbicide-tolerance, disclosed in W02006/108674); event LL55 (soybean, herbicide-tolerance, disclosed in WO 2006/108675); event EE- GM3/FG72 (soybean, herbicide-tolerance) optionally stacked with event EE-GM1/LL27 or event EE-GM2/LL55 (disclosed in WO2011/063413); event MON87701 (soybean, insect control, disclosed in W02009/064652, WO2014/170327); event MON87701 x MON89788 (disclosed in WO2014/170327, e.g.
  • event MON87705 (soybean, improved fatty acid profile, herbicide-tolerance, disclosed in W02010/037016 or US20100080887A, e.g. commercially available as Vistive GoldTM); event MON87751 (lepidopteran-resistant, ATCC accession no. PTA-120166. disclosed in WO2014/201235); event MON87751xMON87701xMON89788xMON87708 (commercially available as Intacta2 Xtend®); event MON87708 (soybean, herbicide-tolerance, disclosed in WO2011/034704, e.g.
  • event MON- 04032-6 event code: GTS 40-3-2, http://www.agbios.com/static/cropdb/LONG-GTS-40-3-2-printer.html, e.g. commercially available as Roundup Ready® soybean
  • event HB4 event code IND-00410-5, US2022/009011 , e.g., commercially available as Verdeca HB4 Soybean.
  • transgenic events in transgenic soybean plants which can preferably be treated according to the invention, include event A2704-12 (glufosinate tolerance, disclosed in W02006/108647, e.g., commercially available as Liberty LinkTM soybean), event A5547-127 (phosphinothricin tolerant, disclosed in W02006/108675, US8952142B2, e.g., commercially available as Liberty LinkTM soybean); A5547-35 (event code: ACS-GM008-6, gene: pat, e.g., commercially available as Liberty LinkTM soybean), event MON89788 (soybean, herbicide-tolerance, disclosed in W02006/130436, e.g.
  • Genuity® Roundup Ready 2 YieldTM DP-305423-1 (soybean, quality mark, disclosed in W02008/054747, e.g., commercially available as TreusTM, PlenishTM, Plenish® High Oleic Soybeans); event MON87701 (soybean, insect resistant, disclosed in W02009/064652); event MON87701 x MON89788 (disclosed in WO2014/170327, e.g., commercially available as Intacta RR2 PRO® soybean); event MON87705 (soybean, improved fatty acid profile, herbicide-tolerance, disclosed in WO2010/037016 or US20100080887A, e.g.
  • event FG72 (soybean, herbicide-tolerance, disclosed in WO2011/063413); evet FG72xA5547-127 (e.g. commercially available as LibertyLink® GT27TM); event SYHT0H2/SYN-000H2-5 (soybean, herbicide-tolerance, disclosed in WO2012/082548); event DAS-81419-2 (described in WO2013/016527, e.g., commercially available as ConkestaTM soybean); event DAS-44406-6 (disclosed in WO2012/075426, e.g., commercially available as Enlist E3TM), or event DAS-81419-2 (described in WO2013/016527, e.g., commercially available as ConkestaTM soybean); DAS81419-2xDAS4406 (e.g., commercially available as ConkestaTM Enlist E3TM soybean); event DP305423x GT
  • event DP-356043-5 sibean, herbicide-tolerance, deposited as ATCC PTA-8287, disclosed in W02008/002872, e.g. commercially available as Optimum GATTM
  • event MON-04032-6 event code: GTS 40-3-2, http://www.aqbios.com/static/cropdb/LONG-GTS-4Q-3-2-printer.html, e.g. commercially available as Roundup Ready® soybean).
  • transgenic events are provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the World Wide Web at aphis.usda.gov.
  • USDA United States Department of Agriculture's
  • APIS Animal and Plant Health Inspection Service
  • Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547- 127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • a compound of formula (I) (l-A), or (l-B) for controlling phytopathogenic fungi in genetically modified soybean plants, wherein said transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • said transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS6841
  • Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19- 51 a, 31707, 42317, 81910, 281 -24-236, 3006-210-23, BXN1021 1 , BXN 10215, BXN10222, BXN 10224, MON1445, MON1698, MON88701 , MON88913, GHB1 19, GHB614, LLCotton25, T303-3 and T304-40.
  • Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281 -24-236, 3006-210-23, GHB1 19 and SGK321. Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
  • Transgenic cotton events comprising glufosinate tolerance genes are for example, but not excluding others, 3006-210-23 x 281-24-236 x MON 1445 (event code: DAS-21023-5 x DAS- 24236-5 x MON-01445-2, gene: bar, e.g., commercially available as WideStrikeTM Roundup ReadyTM Cotton), 3006-210-23 x 281-24-236 x MON88913 (event code: DAS-21023-5 x DAS-24236-5 x MON-88913-8, gene: bar, e.g., commercially available as WidestrikeTM Roundup Ready FlexTM Cotton), 3006-210-23 x 281-24-236 x MON88913 x COT102 (event code: DAS- 21023-5 x DAS-24236-5 x MON-88913-8 x SYN-IR102-7, gene: pat, e.g., commercially available as WidestrikeTM x Roundup Ready FlexTM x
  • a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Corynespora cassiicola comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a compound according to formula (I) (l-A), or (l-B) according to the invention, wherein the compound according to formula (I) (l-A), or (l-B) is applied in the field.
  • the terms “applied in the field”, “field-applied”, “field-grown” and “field cultivation” refer broadly to the application of the pesticidal compounds or compositions directly onto plants growing in an open field or traditional agricultural setting, as opposed to “liquid culture application” which typically involves the use of pesticidal compounds and compositions in a controlled, hydroponic, or soilless environment where plants are grown in nutrient-rich aqueous solutions, such as for the purpose of scientific research.
  • the compounds and composition as defined herein have surprisingly proven to be particularly effective for field application as compared to liquid culture applications.
  • the compound according to formula (I) (l-A), or (l-B) according to the invention is applied to a field-grown plant susceptible to attack by the phytopathogen by means of foliar application, soil application, in furrow application or drench application.
  • the compound according to formula (I) (l-A), or (l-B) according to the invention is applied to the plant propagation material for the purpose of field cultivation of a plant susceptible to attack by the phytopathogen.
  • the compound of formula (I), (l-A), or (l-B) according to the invention may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g., in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating, or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • adjuvants conventionally
  • Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g., natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders, or fertilizers.
  • Such carriers are for example described in WO 1997/33890.
  • Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally 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.
  • Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers.
  • the particles contain the active ingredient retained in a solid matrix.
  • Typical solid matrices include fuller’s earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
  • Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally 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.
  • Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required.
  • Typical carriers for granular formulations include sand, fuller’s earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound.
  • Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils
  • Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours, and other organic and inorganic solids which act as dispersants and carriers.
  • the active ingredients can also be contained in microcapsules.
  • Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g., slow-release).
  • Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight.
  • the active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution.
  • the encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane, or chemically modified polymers, and starch xanthates, or other polymers that are known to the person skilled in the art.
  • very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
  • Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates.
  • Encapsulated droplets are typically 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound.
  • Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
  • Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring.
  • Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • compositions for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents.
  • Pressurised sprayers wherein the active ingredient is dispersed in finely divided form because of vaporisation of a low boiling dispersant solvent carrier, may also be used.
  • Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2- butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 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-dimethyl formamide, dimethyl sulfoxide
  • Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller’s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.
  • a broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application.
  • These agents when used, normally comprise from 0.1 % to 15% by weight of the formulation. They can be anionic, cationic, nonionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes.
  • Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.
  • alcohol-alkylene oxide addition products such as tridecyl alcohol-C.sub. 16 ethoxylate
  • soaps such as sodium stearate
  • alkylnaphthalenesulfonate salts such as sodium dibutylnaphthalenesulfonate
  • dialkyl esters of sulfosuccinate salts such as sodium di(2- ethylhexyl) sulfosuccinate
  • sorbitol esters such as sorbitol oleate
  • quaternary amines such as lauryl trimethylammonium chloride
  • polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
  • salts of mono and dialkyl phosphate esters such as mono and dialkyl phosphate esters.
  • adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.
  • the compounds of formula (I), (l-A), or (l-B) according to the invention may be used in the form of a pesticidal composition further comprising one or more adjuvants selected from stabilizers, viscosity regulators, binders, tackifiers, fertilizers, crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilising agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants, and sticking agents.
  • adjuvants selected from stabilizers, viscosity regulators, binders, tackifiers, fertilizers, crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents,
  • the pesticidal composition may also comprise one or more agents that act as a carrier or as a diluent of the active ingredients, or both.
  • the agent acting as a carrier or diluent, or both, hereinafter called “carrier or diluent”, may be liquid or solid.
  • the compounds of formula (I), (l-A), or (l-B) according to the invention may be used in the form of a pesticidal composition further comprising one or more liquid carriers or diluents selected from xylene, heavy aromatic naphthas, isophorone, water, toluene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1 ,2-dichloropropane, diethanolamine, p diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether,
  • the compounds of formula (I), (l-A), or (l-B) according to the invention may be used in the form of a pesticidal composition further comprising one or more solid diluents or carriers selected from talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.
  • solid diluents or carriers selected from talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.
  • the compounds of formula (I), (l-A), or (l-B) according to the invention may be used in the form of a pesticidal composition further comprising one or more formulation auxiliaries selected from unepoxidized or epoxidized vegetable oils, preservatives, inorganic compounds.
  • biocidal active ingredients or compositions may be combined with the compounds or compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compounds or compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compounds or compositions of the invention or mixed in, for example, the spray tank. These further biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.
  • Pesticidal agents are referred to herein using their common name are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.
  • compositions of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer).
  • SAR inducers are known and described in, for example, United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar- S-methyl.
  • the compounds of formula (I), (l-A), or (l-B) according to the invention are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds.
  • further compounds can be e.g., fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non- selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • the compounds of formula (I), (l-A), or (l-B) according to the invention may be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient a compound as defined herein, in free form or in agrochemical usable salt form, and at least one of the above-mentioned adjuvants, and preferably at least one formulation auxiliary, diluent and/or carrier.
  • the invention therefore provides a composition, preferably a fungicidal composition, comprising a compound of formula (I), (l-A), or (l-B) according to the invention, an agriculturally acceptable carrier and optionally an adjuvant, or an adjuvant and one or more auxiliaries, diluents and/or carriers.
  • An agricultural acceptable carrier is for example a carrier that is suitable for agricultural use.
  • Agricultural carriers are well known in the art.
  • said composition may comprise at least one or more pesticidal-active compounds, for example an additional fungicidal active ingredient in addition to a compound of formula (I), (l-A), or (l-B).
  • the compound of formula (I), (l-A), or (l-B) according to the invention may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, including fungicides, herbicide, insecticide, synergist, or plant growth regulator where appropriate.
  • additional active ingredient may, in some cases, result in unexpected synergistic activities.
  • Suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fung
  • a further aspect of the present invention is a method of controlling diseases on useful plants or on propagation material thereof caused by phytopathogens, which comprises applying to the useful plants, the locus thereof or propagation material thereof a composition according to the invention.
  • a method which comprises applying to the useful plants or to the locus thereof a composition according to the invention, more preferably to the useful plants.
  • a method which comprises applying to the propagation material of the useful plants a composition according to the invention.
  • composition refers to the various mixtures or combinations of components (A) and (B), for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the components (A) and (B) is not essential for working the present invention.
  • compositions according to the invention are effective against harmful microorganisms, such as microorganisms, that cause phytopathogenic diseases, in particular against phytopathogenic fungi and bacteria.
  • the formulation comprising a composition according to the invention may comprise of from 0.01 to 90% by weight of the composition comprising components (A) and (B), and of from 0 to 20% of an agriculturally acceptable surfactant.
  • the formulation further comprises other active agents, in particular microbiocides and pesticides, more generally.
  • the formulation further comprises of from 10 to 99.99% solid or liquid formulation inerts, conservatives and/or adjuvants.
  • the present invention preferably also relates to a concentrated composition for dilution by the user, comprising a composition according or a formulation according to the invention, comprising of from 2 to 80% by weight, preferably between 5 and 70% by weight, of active agents comprising at least a composition comprising (A) and (B), and optionally, other active agents.
  • the present invention preferably also relates to a seed dressing formulation for application to plant propagation materials, comprising a composition according to the invention, and further comprising a diluent.
  • the seed dressing formulation is in the form of an aqueous suspension or in a dry powder form having good adherence to the plant propagation materials.
  • the seed dressing formulation may comprise the active agents in an encapsulated form, preferably a slow-release capsules and/or microcapsules.
  • the present invention preferably also relates to a method of combating and controlling phytopathogens, comprising applying a fungicidally effective amount of a composition according to the invention to a pest, a locus of pest, or to a plant susceptible to attack by a pest, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.
  • the methods, compositions and uses according to any one of embodiments according to the invention are preferably for controlling or preventing infestation of the crop by the phytopathogenic microorganisms Corynespora cassiicola, that are resistant to other fungicides.
  • Corynespora cassiicola that are "resistant" to a particular fungicide refer e.g., to strains of Corynespora cassiicola fungi that are less sensitive to that fungicide compared to the expected sensitivity of the same species of Corynespora cassiicola fungi.
  • the expected sensitivity can be measured using e.g., a strain that has not previously been exposed to the fungicide.
  • an “effective” amount herein refers to an amount of the active ingredient that shows sufficient biocidal activity, e.g., at least 10 %, more preferably at least 20%, yet more preferably at least 50%, and again more preferably at least 70 % effectiveness, compared to the blind test.
  • the composition according to the invention preferably comprise at least 0.01 ppm, more preferably at last 0.025 ppm of active ingredient, more preferably at least for example 6 ppm, 3 ppm, 2.2 ppm, 1.5 ppm, 0.8 ppm, 0.74 ppm, 0.25 ppm, 0.2 ppm, or 0.082 ppm as applied.
  • Application according to the methods or uses according to any one of embodiments according to the invention is preferably to a crop of plants, the locus thereof or propagation material thereof.
  • Preferably application is to the phytopathogen, to the locus ofthe phytopathogen, orto a plant susceptible to attack by the phytopathogen, or to a propagation material thereof.
  • Application of the compounds as defined in any one of embodiments 1 to 13 can be performed according to any of the usual modes of application, e.g., foliar, drench, soil, in furrow etc.
  • the compounds or pesticidal compositions as defined herein are applied in the field to the foliage of the plant (foliar application), thus allowing to select frequency and rate of application to match the danger of infestation with the pest in question.
  • the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants in the field with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants in the field, for example into the soil or furrow, such as in the form of granules. In the case of paddy rice crops, such granules can be metered into the flooded paddy-field.
  • the compounds as defined in any one of embodiments according to the invention are suitable for use on any plant, including those that have been genetically modified to be resistant to active ingredients such as herbicides, or to produce biologically active compounds that control infestation by plant pests.
  • a compound as defined in any one of embodiments according to the invention is used in the form of a composition (e.g., formulation) containing a carrier.
  • a compound as defined in any one of embodiments according to the invention and compositions thereof can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra-low volume (ulv) liquid, ultra-low volume (ulv) suspension, water dispersible granules or tablets, water dispers
  • compositions of this invention can be mixed with one or more further pesticides including further fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • further pesticides including further fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • a formulation typically comprises a liquid or solid carrier and optionally one or more customary formulation auxiliaries, which may be solid or liquid auxiliaries, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers.
  • auxiliaries for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers.
  • composition may also further comprise a fertilizer, a micronutrient donor or other preparations which influence the growth of plants as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.
  • a fertilizer such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.
  • compositions are prepared in a manner known perse, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention
  • at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries).
  • the grinding/milling of the compounds is to ensure specific particle size.
  • compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound of formula (I) as defined herein and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.
  • the compositions comprise 0.1 to 99 %, especially 0.1 to 95 %, of a compound (A), and optionally compound (B), as defined in any one of embodiments according to the invention and 1 to 99.9 %, especially 5 to 99.9 %, of at least one solid or liquid carrier, it being possible as a rule for 0 to 25 %, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight).
  • surfactants % in each case meaning percent by weight.
  • the weight ratio of component (A) to component (B) is from 2000 : 1 to 1 : 1000.
  • the weight ratio of component (A) to component (B) is preferably from 100 : 1 to 1 : 100; more preferably from 20 : 1 to 1 : 50, yet more preferably from 12 : 1 to 1 : 25; yet more preferably from 10 : 1 to 1 : 10, again more preferably from 5 : 1 to 1 : 15; and most preferably from 2 :1 to 1 : 5.
  • compositions according to the invention can also have further surprising advantageous properties.
  • advantageous properties are: more advantageous degradability; improved toxicological and/or ecotoxicological behaviour; or improved characteristics of the useful plants including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigour, and early germination.
  • Additional beneficial effects can be the suppression or reduction of development of resistance against a certain active ingredient, by combinations that may have one or more different modes of action may in particular be beneficial.
  • compositions according to the invention have a systemic action and can be used as foliar, soil and seed treatment fungicides.
  • compositions according to the invention it is possible to inhibit or destroy the phytopathogenic microorganisms which occur in plants or in parts of plants (fruit, blossoms, leaves, stems, tubers, roots) in different useful plants, while at the same time the parts of plants which grow later are also protected from attack by phytopathogenic microorganisms.
  • compositions according to the invention can be applied to the phytopathogenic microorganisms, the useful plants, the locus thereof, the propagation material thereof, storage goods or technical materials threatened by microorganism attack.
  • compositions according to the invention may be applied before or after infection of the useful plants, the propagation material thereof, storage goods or technical materials by the microorganisms.
  • the amount of a composition according to the invention to be applied will depend on various factors, such as the compounds employed; the subject of the treatment, such as, for example plants, soil or seeds; the type of treatment, such as, for example spraying, dusting or seed dressing; the purpose of the treatment, such as, for example prophylactic or therapeutic; the type of fungi to be controlled or the application time.
  • component (A) When applied to the useful plants component (A) is typically applied at a rate of 5 to 2000 g a.i./ha, particularly 10 to 1000 g a.i./ha, e.g., 50, 75, 100 or 200 g a.i./ha, preferably in association with 1 to 5000 g a.i./ha, particularly 2 to 2000 g a.i./ha, e.g., 100, 250, 500, 800, 1000, 1500 g a.i./ha of component (B).
  • the compounds of formula (I) as defined in any one of embodiments according to the invention are used for pest control at rates of 1 to 500 g/ha, preferably 15 to 400 g/ha, more preferably 20-300 g/ha, most preferably 30-200 g/ha, such as 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, or 65 g a.i /ha.
  • the compounds of formula (I) and pesticidal compositions comprising these compounds as defined in any one of embodiments according to the invention are applied at rates of 70 to 150 g a.i./ha, preferably 70-120 g a.i./ha, more preferably at rates of 70 to 90 g a.i./ha, such as 70, 80, 90, 100, 110, or 120 g a.i /ha.
  • the compound according to formula (I) is applied at a rate of at least 10 g/ha, preferably at least 5, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70 g/ha.
  • the compound according to formula (I) is applied at a rate of at most 150 g/ha, preferably at most 120, 115, 110, 105, 100, 95, 90, 85, or 80 g/ha.
  • g a.i./ha refers to the application rate given in gram [g] of active ingredient [a.i.] per unit of surface [ha].
  • the unit hectare symbol ha is the metric unit of area that equals a square with 100 m side (1 hm 2 ) or 10,000 square meters. Hectare is a commonly used unit of area in the metric system.
  • compositions according to the invention depend on the type of effect desired, and typically range from 20 to 4000 g of total composition per hectare.
  • compositions according to the invention are used for treating seed, rates of 0.001 to 50 g of a compound of component (A) per kg of seed, preferably from 0.01 to 10g per kg of seed, and preferably 0.001 to 50 g of a compound of component (B), per kg of seed, preferably from 0.01 to 10g per kg of seed, are generally sufficient.
  • foliar formulation types for pre-mix compositions are:
  • WP wettable powders
  • WG water dispersible granules (powders)
  • DC dispersible concentrate
  • EW emulsions, oil in water
  • SE aqueous suspo-emulsion.
  • seed treatment formulation types for pre-mix compositions are:
  • WS wettable powders for seed treatment slurry
  • WG water dispersible granules
  • CS aqueous capsule suspension.
  • formulation types suitable fortank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.
  • the methods of application such as foliar, drench, spraying, atomizing, dusting, scattering, coating, or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.
  • a solvent for example, water
  • Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g., natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders, or fertilizers.
  • a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, of the desired ingredients, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for example, a diluent or solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation.
  • auxiliaries including, for example, a diluent or solvent such as water
  • a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.9 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, of the desired ingredients, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.
  • auxiliaries including, for example, a solvent such as water
  • a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • Preferred seed treatment pre-mix formulations are aqueous suspension concentrates.
  • the formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful.
  • the seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
  • the compounds of the present invention are particularly suited for use in soil and seed treatment applications.
  • the pre-mix compositions of the invention contain 0.5 to 99.9 especially 1 to 95, advantageously 1 to 50 % by mass of the desired ingredients, and 99.5 to 0.1 , especially 99 to 5 % by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries (or adjuvant) can be a surfactant in an amount of 0 to 50, especially 0.5 to 40 % by mass based on the mass of the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • biocidally active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.
  • compositions of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer).
  • SAR inducers are known and described in, for example, United States Patent No. US6, 919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar- S-methyl.
  • the compounds as defined in any one of embodiments according to the invention are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds.
  • further compounds can be e.g., fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • the compounds of formula (I) may be used in the form of (fungicidal) compositions for controlling or protecting against the phytopathogen(s) Corynespora cassiicola, comprising as active ingredient at least one compound as defined in any one of embodiments according to the invention, in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.
  • the plants and / or target crops in accordance with the invention include conventional as well as genetically enhanced or engineered varieties such as, for example, insect resistant (e.g., Bt. and VIP varieties) as well as disease resistant, herbicide tolerant (e.g., glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®) and nematode tolerant varieties.
  • suitable genetically enhanced or engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.
  • plants and/or “target crops” is to be understood as including also plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3- phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS (5-enol-pyrovyl-shikimate-3- phosphate-synthase) inhibitors
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • An example of a crop that has been rendered tolerant to imidazolinones, e.g., imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinateresistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.
  • plants and/or “target crops” is to be understood as including those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include 8- endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonizing nematodes, and toxins produced by scorpions, arachnids, wasps, and fungi.
  • Vip vegetative insecticidal proteins
  • insecticidal proteins of bacteria colonizing nematodes and toxins produced by scorpions, arachnids, wasps, and fungi.
  • An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds).
  • An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds).
  • Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification).
  • a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).
  • plants and/or “target crops” is to be understood as also including plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g., EP0392225A).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP0392225A, WO95/33818, and EP0353191A.
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 8-endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp.
  • insecticidal proteins from Bacillus cereus or Bacillus popilliae such as 8-endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid- UDP-glycosyl-transferase, cholesterol oxidases, ecd
  • 8-endotoxins for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins.
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701).
  • Truncated toxins for example a truncated CrylAb, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • amino acid replacements preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WG03/018810).
  • Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard ® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1 Ac toxin); Bollgard I® (cotton variety that expresses
  • transgenic crops are:
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810.
  • NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to denote seeds.
  • Pesticidal agents referred to herein using their common name are known, for example, from “The Pesticide Manual”, 15 th Ed., British Crop Protection Council 2009.
  • the compounds as defined in any one of embodiments according to the invention for use in the inventive methods may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • An additional active ingredient may, in some cases, result in unexpected synergistic activities.
  • compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.
  • auxiliaries such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematicides, plant
  • the compounds, and compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • Another aspect of the invention is related to the use of a compound as defined in any one of embodiments according to the invention, of a composition comprising at least one compound as defined in, or of a fungicidal or insecticidal mixture comprising at least one compound as defined in any one of embodiments according to the invention, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • plants e.g. plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • a further aspect of invention is related to a method of controlling or preventing an infestation of plants, e.g. plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or of non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound as defined in any one of embodiments according to the invention as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.
  • plants e.g. plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or of non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms
  • a compound as defined in any one of embodiments according to the invention as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation
  • Controlling or preventing means reducing infestation by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.
  • a preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound as defined in any one of embodiments according to the invention, or an agrochemical composition which contains at least one of said compounds, is foliar application.
  • the frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect.
  • the compounds of formula (I), preferably in association with a compound (B), can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g., in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • compositions comprising compounds of formula (I) their application methods to cereals and their use rates are as described for compositions comprising compounds of formula (I) and additionally preferably at least one component (B) as described above.
  • a compound of formula (I) can be used on its own, the application rates in the method according to the invention are as described above, e.g., typical are rates of 5 to 2000 g a.i./ha, particularly 10 to 1000 g a.i./ha, e.g., 50, 75, 100 or 200 g a.i./ha.
  • Compounds of formula (I) can be applied to the plants once or more than once during a growing season.
  • the compounds of formula (I) can be converted into the customary formulations described above, e.g., solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the use form will depend on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound of formula (I).
  • plant as used herein includes seedlings, bushes and crops of fruits and vegetables.
  • compositions comprising only a compound of formula (I) as the active ingredient.
  • the compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by a person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates, if necessary, for example 60 ppm, 20 ppm or 2 ppm.
  • Compounds of formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).
  • Wettable powders a) b) c) active ingredients 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % sodium lauryl sulfate 3 % 5 % sodium diisobutylnaphthalenesulfonate 6 % 10 % phenol polyethylene glycol ether (7-8 mol of ethylene oxide) 2 % highly dispersed silicic acid 5 % 10 % 10 %
  • the combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • Powders for dry seed treatment a) b) c) active ingredients 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % Kaolin 65 % 40 % - Talcum 20 %
  • the combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsifiable concentrate active ingredients 10 % octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) 3 % calcium dodecylbenzene sulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 %
  • Emulsions of any required dilution which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • the combination is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • the finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol.
  • Non-dusty coated granules are obtained in this manner.
  • Flowable concentrate for seed treatment active ingredients 40 % propylene glycol 5 % copolymer butanol PO/EO 2 %
  • Silicone oil (in the form of a 75 % emulsion in water) 0.2 %
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1).
  • This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved.
  • a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added.
  • the mixture is agitated until the polymerization reaction is completed.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • Formulation types include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.
  • EC emulsion concentrate
  • SC suspension concentrate
  • SE suspo-emulsion
  • CS capsule suspension
  • WG water dispersible granule
  • EG
  • the activity of the compounds against Corynespora cassiicola in the field providing overall control similar to that of the commercial triple mix - is surprising and unexpected given the lack of activity against the same fungus in liquid culture, especially when compared to the relative activity of the active ingredients from the commercial product in liquid culture.
  • the compounds of formula (I), (l-A), or (l-B) may for example be distinguished from other compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the above biological test, using lower application rates, if necessary, for example 6 ppm, 3 ppm, 2.2 ppm, 1 .5 ppm, 0.8 ppm or 0.74 ppm.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Mycology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des procédés de lutte contre l'infestation d'une plante par le micro-organisme phytopathogène Corynespora cassiicola ou de prévention d'une telle infestation, comprenant l'application sur le phytopathogène, le locus du phytopathogène, ou une plante susceptible d'être attaquée par le phytopathogène, ou un matériel de propagation de celle-ci, d'une quantité efficace du point de vue fongicide d'un composé, d'un N-oxyde de celui-ci ou de sels de celui-ci acceptables sur le plan agricole tels que définis dans la revendication 1.
PCT/EP2024/072023 2023-08-04 2024-08-02 Procédés de lutte contre l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola ou de prévention de celle-ci Pending WO2025031989A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23189867.7 2023-08-04
EP23189867 2023-08-04

Publications (1)

Publication Number Publication Date
WO2025031989A1 true WO2025031989A1 (fr) 2025-02-13

Family

ID=87557578

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/072023 Pending WO2025031989A1 (fr) 2023-08-04 2024-08-02 Procédés de lutte contre l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola ou de prévention de celle-ci

Country Status (1)

Country Link
WO (1) WO2025031989A1 (fr)

Citations (79)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353191A2 (fr) 1988-07-29 1990-01-31 Ciba-Geigy Ag Séquences d'ADN codant des polypeptides avec activité béta-1,3-glucanase
EP0367474A1 (fr) 1988-11-01 1990-05-09 Mycogen Corporation Souche de bacillus thuringiensis appelée b.t. ps81gg, active contre les lépidoptères nuisibles et gène codant une toxine active contre les lépidoptères.
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
WO1990013651A1 (fr) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Genes bacteriens
EP0401979A2 (fr) 1989-05-18 1990-12-12 Mycogen Corporation Souches de bacillus thuringiensis actives contre les lépidoptères nuisibles, et gènes codant pour des toxines actives contre les lépidoptères
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1995033818A2 (fr) 1994-06-08 1995-12-14 Ciba-Geigy Ag Genes pour la synthese des substances antipathogenes
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
WO1997033890A1 (fr) 1996-03-11 1997-09-18 Novartis Ag Derives de pyrimidine-4-one utilises comme pesticide
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
US6919298B2 (en) 2002-04-04 2005-07-19 Valent Biosciences Corporation Enhanced herbicide composition
WO2006108675A2 (fr) 2005-04-11 2006-10-19 Bayer Bioscience N.V. Evenement elite a5547-127 et procedes et trousses pour l'identification d'un tel evenement dans des echantillons biologiques
WO2006108647A1 (fr) 2005-04-12 2006-10-19 Vekoerrer Franz Procede de production de pieces moulees dentaires
WO2006108674A2 (fr) 2005-04-08 2006-10-19 Bayer Bioscience N.V. Evenement elite a2704-12 et procedes et trousses permettant d'identifier cet evenement dans des prelevements biologiques
WO2006130436A2 (fr) 2005-05-27 2006-12-07 Monsanto Technology Llc Evenement de soja mon89788 et procedes de detection de celui-ci
WO2008002872A2 (fr) 2006-06-28 2008-01-03 Pioneer Hi-Bred International, Inc. Événement de soja 3560.4.3.5 et compositions et procedes d'identification et/ou de détection de celui-ci
WO2008054747A2 (fr) 2006-10-31 2008-05-08 E. I. Du Pont De Nemours And Company Événement de soja dp-305423-1, leurs compositions et leurs procédés d'identification et/ou de détection
WO2009064652A1 (fr) 2007-11-15 2009-05-22 Monsanto Technology Llc Plante et graine de soja correspondant à l'événement transgénique mon87701 et procédés pour les détecter
WO2009102873A1 (fr) 2008-02-15 2009-08-20 Monsanto Technology Llc Plante de soja et graine correspondant à l’évènement transgénique mon87769 et leurs procédés de détection
WO2010024976A1 (fr) 2008-08-29 2010-03-04 Monsanto Technology Llc Plante et semences de soja correspondant à l’événement transgénique mon87754 et procédés pour détection de celui-ci
US20100080887A1 (en) 2008-09-29 2010-04-01 Monsanto Technology Llc Soybean Transgenic Event MON87705 and Methods for Detection Thereof
WO2010080829A1 (fr) 2009-01-07 2010-07-15 Basf Agrochemical Products B.V. Évènement de soja 127 et procédés apparentés
WO2011034704A1 (fr) 2009-09-17 2011-03-24 Monsanto Technology Llc Variété transgénique mon 87708 du soja et ses méthodes d'utilisation
WO2011063413A2 (fr) 2009-11-23 2011-05-26 Bayer Bioscience N.V. Plantes de soja tolérant un herbicide et leurs procédés d'identification
WO2011066360A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Détection de l'événement 416 du soja aad-12
WO2011066384A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Événement 416 de la transformation aad-12, lignées de soja transgéniques associées, et leur identification spécifique à l'événement
WO2012033794A2 (fr) 2010-09-08 2012-03-15 Dow Agrosciences Llc Événement 1606 d'aad-12 et lignées de soja transgénique associées
WO2012051199A2 (fr) 2010-10-12 2012-04-19 Monsanto Technology Llc Plante et semence de soja correspondant à l'événement transgénique mon87712 et procédé pour les détecter
WO2012075426A1 (fr) 2010-12-03 2012-06-07 Dow Agrosciences Llc Événement 8264.44.06.1 de tolérance aux herbicides empilé, lignées de soja transgéniques apparentées, et sa détection
WO2012075429A1 (fr) 2010-12-03 2012-06-07 Dow Agrosciences Llc Événement 8291.45.36.2 de tolérance aux herbicides empilé, lignées de soja transgéniques apparentées, et sa détection
WO2012082548A2 (fr) 2010-12-15 2012-06-21 Syngenta Participations Ag Soja comprenant le mécanisme de transformation syht04r, et compositions et procédés de détection de ce mécanisme
WO2013010094A1 (fr) 2011-07-13 2013-01-17 Dow Agrosciences Llc Événement 8264.42.32.1 « empilé » de tolérance aux herbicides, lignées de soja transgénique associées et détection dudit événément
WO2013008162A1 (fr) 2011-07-08 2013-01-17 Novartis Ag Nouveaux dérivés de trifluorométhyl-oxadiazole et leur utilisation pour le traitement de maladies
WO2013016527A1 (fr) 2011-07-26 2013-01-31 Dow Agrosciences Llc Evénement de soja 9582.814.19.1 résistant aux insectes et tolérant aux herbicides
WO2014170327A1 (fr) 2013-04-19 2014-10-23 Bayer Cropscience Ag Procédé de lutte contre les organismes nuisibles
WO2014201235A2 (fr) 2013-06-14 2014-12-18 Monsanto Technology Llc Événement transgénique de soja mon87751 et procédés de détection et d'utilisation de celui-ci
WO2015155075A1 (fr) 2014-04-11 2015-10-15 Syngenta Participations Ag Dérivés fongicide de n'- [2-méthyl -6- [2-alcoxy-éthoxy]-3-pyridyl]-n-alkyl-formamidine destinés à être utilisés dans l'agriculture
WO2015185485A1 (fr) 2014-06-06 2015-12-10 Basf Se Utilisation d'oxadiazoles substitués pour lutter contre des fongus phytopathogènes
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2017005710A1 (fr) 2015-07-08 2017-01-12 Bayer Cropscience Aktiengesellschaft Phénoxyhalogénophénylamidines et leur utilisation comme fongicides
WO2017055473A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017076742A1 (fr) 2015-11-05 2017-05-11 Basf Se Utilisation d'oxadiazoles substitués pour lutter contre les champignons phytopathogènes
WO2017081311A1 (fr) 2015-11-13 2017-05-18 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017085100A1 (fr) 2015-11-19 2017-05-26 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017093019A1 (fr) 2015-12-03 2017-06-08 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017153380A1 (fr) 2016-03-10 2017-09-14 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2017178245A1 (fr) 2016-04-11 2017-10-19 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
US9823801B2 (en) 2010-10-04 2017-11-21 Au Optronics Corporation Touch panel and repairing method thereof
WO2017207362A1 (fr) 2016-05-30 2017-12-07 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2017211649A1 (fr) 2016-06-09 2017-12-14 Basf Se Oxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes
WO2018098216A1 (fr) 2016-11-22 2018-05-31 Vps-3, Inc. Utilisation d'un composé difluoro-(2-hydroxypropyl)pyridine en tant que fongicide pour lutter contre les champignons phytopathogènes de l'orge
WO2018108977A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
WO2018145921A1 (fr) 2017-02-10 2018-08-16 Bayer Aktiengesellschaft Composition pour lutter contre des micro-organismes nuisibles comprenant des dérivés de 1-(phénoxy-pyridinyl)-2-(1,2,4-triazol-1-yl)-éthanol
WO2018153707A1 (fr) 2017-02-22 2018-08-30 Basf Se Formes cristallines d'un composé de type strobilurine pour lutter contre des champignons phytopathogènes
WO2018202428A1 (fr) 2017-05-02 2018-11-08 Basf Se Mélange fongicide comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2019093522A1 (fr) 2017-11-13 2019-05-16 株式会社クレハ Dérivé d'azole, composé intermédiaire, procédé de production d'un dérivé d'azole, agent à usage agricole et horticole, et agent de protection de matériau à usage industriel
WO2019105933A1 (fr) 2017-11-29 2019-06-06 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2019233826A1 (fr) 2018-06-05 2019-12-12 Basf Se Mélanges fongicides comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2020109511A1 (fr) 2018-11-30 2020-06-04 Syngenta Crop Protection Ag Dérivés de 2-acylamino-thiazole-4-carboxamide microbiocides
WO2020109509A1 (fr) 2018-11-30 2020-06-04 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2020127780A1 (fr) 2018-12-20 2020-06-25 Bayer Aktiengesellschaft Hétérocyclyl-pyridazine utilisée en tant que composés fongicides
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2021176057A1 (fr) * 2020-03-05 2021-09-10 Syngenta Crop Protection Ag Compositions fongicides
WO2021180975A1 (fr) * 2020-03-13 2021-09-16 Syngenta Crop Protection Ag Procédés de lutte contre ou de prévention de l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola
WO2021180976A1 (fr) * 2020-03-13 2021-09-16 Syngenta Crop Protection Ag Procédés de lutte contre ou de prévention de l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola, cercospora sojina et/ou cercospora kikuchii
WO2021180974A1 (fr) * 2020-03-13 2021-09-16 Syngenta Crop Protection Ag Procédés de lutte contre ou de prévention de l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola
WO2021209360A1 (fr) 2020-04-14 2021-10-21 Basf Se Mélanges fongicides comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2021224268A1 (fr) * 2020-05-04 2021-11-11 Syngenta Crop Protection Ag Compositions fongicides
WO2021244952A1 (fr) 2020-06-03 2021-12-09 Syngenta Crop Protection Ag Dérivés microbiocides
WO2021255070A1 (fr) 2020-06-18 2021-12-23 Bayer Aktiengesellschaft Combinaisons de composés actifs
US20220009011A1 (en) 2020-07-09 2022-01-13 Nanjing Chervon Industry Co., Ltd. Reciprocating saw
WO2022017836A1 (fr) * 2020-07-20 2022-01-27 BASF Agro B.V. Compositions fongicides comprenant du (r)-2-[4-(4-chlorophénoxy)-2-(trifluorométhyl)phényl]-1-(1,2,4-triazol-1-yl)propan-2-ol
WO2023280630A1 (fr) 2021-07-08 2023-01-12 Basf Se Préparation d'amidoximes substituées
JP2023078251A (ja) 2023-03-10 2023-06-06 住友化学株式会社 アクリル酸誘導体の製造方法

Patent Citations (81)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
EP0353191A2 (fr) 1988-07-29 1990-01-31 Ciba-Geigy Ag Séquences d'ADN codant des polypeptides avec activité béta-1,3-glucanase
EP0367474A1 (fr) 1988-11-01 1990-05-09 Mycogen Corporation Souche de bacillus thuringiensis appelée b.t. ps81gg, active contre les lépidoptères nuisibles et gène codant une toxine active contre les lépidoptères.
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
WO1990013651A1 (fr) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Genes bacteriens
EP0401979A2 (fr) 1989-05-18 1990-12-12 Mycogen Corporation Souches de bacillus thuringiensis actives contre les lépidoptères nuisibles, et gènes codant pour des toxines actives contre les lépidoptères
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1995033818A2 (fr) 1994-06-08 1995-12-14 Ciba-Geigy Ag Genes pour la synthese des substances antipathogenes
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
WO1997033890A1 (fr) 1996-03-11 1997-09-18 Novartis Ag Derives de pyrimidine-4-one utilises comme pesticide
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
US6919298B2 (en) 2002-04-04 2005-07-19 Valent Biosciences Corporation Enhanced herbicide composition
WO2006108674A2 (fr) 2005-04-08 2006-10-19 Bayer Bioscience N.V. Evenement elite a2704-12 et procedes et trousses permettant d'identifier cet evenement dans des prelevements biologiques
WO2006108675A2 (fr) 2005-04-11 2006-10-19 Bayer Bioscience N.V. Evenement elite a5547-127 et procedes et trousses pour l'identification d'un tel evenement dans des echantillons biologiques
US8952142B2 (en) 2005-04-11 2015-02-10 Bayer Cropscience N.V. Elite event A5547-127 and methods and kits for identifying such event in biological samples
WO2006108647A1 (fr) 2005-04-12 2006-10-19 Vekoerrer Franz Procede de production de pieces moulees dentaires
WO2006130436A2 (fr) 2005-05-27 2006-12-07 Monsanto Technology Llc Evenement de soja mon89788 et procedes de detection de celui-ci
WO2008002872A2 (fr) 2006-06-28 2008-01-03 Pioneer Hi-Bred International, Inc. Événement de soja 3560.4.3.5 et compositions et procedes d'identification et/ou de détection de celui-ci
WO2008054747A2 (fr) 2006-10-31 2008-05-08 E. I. Du Pont De Nemours And Company Événement de soja dp-305423-1, leurs compositions et leurs procédés d'identification et/ou de détection
WO2009064652A1 (fr) 2007-11-15 2009-05-22 Monsanto Technology Llc Plante et graine de soja correspondant à l'événement transgénique mon87701 et procédés pour les détecter
WO2009102873A1 (fr) 2008-02-15 2009-08-20 Monsanto Technology Llc Plante de soja et graine correspondant à l’évènement transgénique mon87769 et leurs procédés de détection
WO2010024976A1 (fr) 2008-08-29 2010-03-04 Monsanto Technology Llc Plante et semences de soja correspondant à l’événement transgénique mon87754 et procédés pour détection de celui-ci
US20100080887A1 (en) 2008-09-29 2010-04-01 Monsanto Technology Llc Soybean Transgenic Event MON87705 and Methods for Detection Thereof
WO2010037016A1 (fr) 2008-09-29 2010-04-01 Monsanto Technology Llc Événement transgénique de soja t mon87705 et procédés pour la détection de celui-ci
WO2010080829A1 (fr) 2009-01-07 2010-07-15 Basf Agrochemical Products B.V. Évènement de soja 127 et procédés apparentés
WO2011034704A1 (fr) 2009-09-17 2011-03-24 Monsanto Technology Llc Variété transgénique mon 87708 du soja et ses méthodes d'utilisation
WO2011063413A2 (fr) 2009-11-23 2011-05-26 Bayer Bioscience N.V. Plantes de soja tolérant un herbicide et leurs procédés d'identification
WO2011066360A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Détection de l'événement 416 du soja aad-12
WO2011066384A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Événement 416 de la transformation aad-12, lignées de soja transgéniques associées, et leur identification spécifique à l'événement
WO2012033794A2 (fr) 2010-09-08 2012-03-15 Dow Agrosciences Llc Événement 1606 d'aad-12 et lignées de soja transgénique associées
US9823801B2 (en) 2010-10-04 2017-11-21 Au Optronics Corporation Touch panel and repairing method thereof
WO2012051199A2 (fr) 2010-10-12 2012-04-19 Monsanto Technology Llc Plante et semence de soja correspondant à l'événement transgénique mon87712 et procédé pour les détecter
WO2012075426A1 (fr) 2010-12-03 2012-06-07 Dow Agrosciences Llc Événement 8264.44.06.1 de tolérance aux herbicides empilé, lignées de soja transgéniques apparentées, et sa détection
WO2012075429A1 (fr) 2010-12-03 2012-06-07 Dow Agrosciences Llc Événement 8291.45.36.2 de tolérance aux herbicides empilé, lignées de soja transgéniques apparentées, et sa détection
WO2012082548A2 (fr) 2010-12-15 2012-06-21 Syngenta Participations Ag Soja comprenant le mécanisme de transformation syht04r, et compositions et procédés de détection de ce mécanisme
WO2013008162A1 (fr) 2011-07-08 2013-01-17 Novartis Ag Nouveaux dérivés de trifluorométhyl-oxadiazole et leur utilisation pour le traitement de maladies
WO2013010094A1 (fr) 2011-07-13 2013-01-17 Dow Agrosciences Llc Événement 8264.42.32.1 « empilé » de tolérance aux herbicides, lignées de soja transgénique associées et détection dudit événément
WO2013016527A1 (fr) 2011-07-26 2013-01-31 Dow Agrosciences Llc Evénement de soja 9582.814.19.1 résistant aux insectes et tolérant aux herbicides
WO2014170327A1 (fr) 2013-04-19 2014-10-23 Bayer Cropscience Ag Procédé de lutte contre les organismes nuisibles
WO2014201235A2 (fr) 2013-06-14 2014-12-18 Monsanto Technology Llc Événement transgénique de soja mon87751 et procédés de détection et d'utilisation de celui-ci
WO2015155075A1 (fr) 2014-04-11 2015-10-15 Syngenta Participations Ag Dérivés fongicide de n'- [2-méthyl -6- [2-alcoxy-éthoxy]-3-pyridyl]-n-alkyl-formamidine destinés à être utilisés dans l'agriculture
WO2015185485A1 (fr) 2014-06-06 2015-12-10 Basf Se Utilisation d'oxadiazoles substitués pour lutter contre des fongus phytopathogènes
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2017005710A1 (fr) 2015-07-08 2017-01-12 Bayer Cropscience Aktiengesellschaft Phénoxyhalogénophénylamidines et leur utilisation comme fongicides
WO2017055473A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017076742A1 (fr) 2015-11-05 2017-05-11 Basf Se Utilisation d'oxadiazoles substitués pour lutter contre les champignons phytopathogènes
WO2017081311A1 (fr) 2015-11-13 2017-05-18 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017085100A1 (fr) 2015-11-19 2017-05-26 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017093019A1 (fr) 2015-12-03 2017-06-08 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017153380A1 (fr) 2016-03-10 2017-09-14 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2017178245A1 (fr) 2016-04-11 2017-10-19 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017207362A1 (fr) 2016-05-30 2017-12-07 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2017211649A1 (fr) 2016-06-09 2017-12-14 Basf Se Oxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes
WO2018098216A1 (fr) 2016-11-22 2018-05-31 Vps-3, Inc. Utilisation d'un composé difluoro-(2-hydroxypropyl)pyridine en tant que fongicide pour lutter contre les champignons phytopathogènes de l'orge
WO2018108977A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
WO2018145921A1 (fr) 2017-02-10 2018-08-16 Bayer Aktiengesellschaft Composition pour lutter contre des micro-organismes nuisibles comprenant des dérivés de 1-(phénoxy-pyridinyl)-2-(1,2,4-triazol-1-yl)-éthanol
WO2018153707A1 (fr) 2017-02-22 2018-08-30 Basf Se Formes cristallines d'un composé de type strobilurine pour lutter contre des champignons phytopathogènes
WO2018202428A1 (fr) 2017-05-02 2018-11-08 Basf Se Mélange fongicide comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2019093522A1 (fr) 2017-11-13 2019-05-16 株式会社クレハ Dérivé d'azole, composé intermédiaire, procédé de production d'un dérivé d'azole, agent à usage agricole et horticole, et agent de protection de matériau à usage industriel
WO2019105933A1 (fr) 2017-11-29 2019-06-06 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2019233826A1 (fr) 2018-06-05 2019-12-12 Basf Se Mélanges fongicides comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2020109511A1 (fr) 2018-11-30 2020-06-04 Syngenta Crop Protection Ag Dérivés de 2-acylamino-thiazole-4-carboxamide microbiocides
WO2020109509A1 (fr) 2018-11-30 2020-06-04 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2020127780A1 (fr) 2018-12-20 2020-06-25 Bayer Aktiengesellschaft Hétérocyclyl-pyridazine utilisée en tant que composés fongicides
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2021176057A1 (fr) * 2020-03-05 2021-09-10 Syngenta Crop Protection Ag Compositions fongicides
WO2021180975A1 (fr) * 2020-03-13 2021-09-16 Syngenta Crop Protection Ag Procédés de lutte contre ou de prévention de l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola
WO2021180976A1 (fr) * 2020-03-13 2021-09-16 Syngenta Crop Protection Ag Procédés de lutte contre ou de prévention de l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola, cercospora sojina et/ou cercospora kikuchii
WO2021180974A1 (fr) * 2020-03-13 2021-09-16 Syngenta Crop Protection Ag Procédés de lutte contre ou de prévention de l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola
WO2021209360A1 (fr) 2020-04-14 2021-10-21 Basf Se Mélanges fongicides comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2021224268A1 (fr) * 2020-05-04 2021-11-11 Syngenta Crop Protection Ag Compositions fongicides
WO2021244952A1 (fr) 2020-06-03 2021-12-09 Syngenta Crop Protection Ag Dérivés microbiocides
WO2021255070A1 (fr) 2020-06-18 2021-12-23 Bayer Aktiengesellschaft Combinaisons de composés actifs
US20220009011A1 (en) 2020-07-09 2022-01-13 Nanjing Chervon Industry Co., Ltd. Reciprocating saw
WO2022017836A1 (fr) * 2020-07-20 2022-01-27 BASF Agro B.V. Compositions fongicides comprenant du (r)-2-[4-(4-chlorophénoxy)-2-(trifluorométhyl)phényl]-1-(1,2,4-triazol-1-yl)propan-2-ol
WO2023280630A1 (fr) 2021-07-08 2023-01-12 Basf Se Préparation d'amidoximes substituées
JP2023078251A (ja) 2023-03-10 2023-06-06 住友化学株式会社 アクリル酸誘導体の製造方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"The Pesticide Manual", 2009, BRITISH CROP PROTECTION COUNCIL
DIXON, L. J. ET AL., PHYTOPATHOLOGY, vol. 99, no. 9, 2009, pages 1015 - 27

Similar Documents

Publication Publication Date Title
CN106614620B (zh) 杀真菌组合物
AU2005270320B2 (en) Method for protecting useful plants or plant propagation material
US10111433B2 (en) Fungicidal compositions
CN109430279B (zh) 杀真菌组合物
CN115209735A (zh) 杀真菌组合物
CN115334885B (zh) 控制或预防植物被植物病原性微生物多主棒孢菌、大豆灰斑病菌和/或大豆紫斑病菌侵染的方法
CN115297727B (zh) 控制或预防植物被植物病原性微生物多主棒孢菌侵染的方法
WO2025031989A1 (fr) Procédés de lutte contre l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola ou de prévention de celle-ci
WO2025031990A1 (fr) Procédés de lutte contre l'infestation de plantes de soja par le micro-organisme phytopathogène corynespora cassiicola ou de prévention de celle-ci
EP4117433A1 (fr) Procédés de lutte contre ou de prévention de l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola
WO2025031913A1 (fr) Procédés de lutte contre l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola ou de prévention de celle-ci
WO2025125639A1 (fr) Procédé de lutte contre les agents pathogènes chez le soja
WO2024223858A1 (fr) Procédés de lutte contre l'infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola ou de prévention de celle-ci
AU2023379602A1 (en) Mixtures of succinate dehydrogenase inhibitors and picolinamides
CN117241668A (zh) 杀微生物的喹啉/喹喔啉苯并噻嗪衍生物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24752049

Country of ref document: EP

Kind code of ref document: A1