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
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

• the present invention relates to a method for controlling Septoria tritici (synonym Zymoseptoria tritici ) resistant to C14-demethylase (in sterol biosynthesis) inhibitor fungicides (also called DMI fungicides) on cereal plants, comprising applying to the plants, their seed or the soil a fungicid- ally effective amount of 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4,5- dihydro-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (I) or 4-[[6-[2-(2,4-difluorophenyl)-1,1- difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyri
• resistance refers to an acquired, heritable reduction in sensitivity of a fungus to a specific anti-fungal agent (or fungicide).
• Septoria tritici is a species of filamentous fungus, an ascomycete in the family Myco- sphaerellaceae. It is a plant pathogen causing septoria leaf blotch, which is currently the most dominant cereal disease. Control of Septoria leaf blotch is becoming more and more difficult for farmers.
• Reason is the capability of the fungi to develop resistance to widely used powerful fun gicidal agents. For example, fungicides containing azole and strobilurine mixtures have been widely and suc cessfully used in recent years for Septoria control.
• DM I Demethlyation inhibitor
• DM I fungicides are acting by inhibiting the enzyme lanosterol 14a-demethylase encoded by the CYP51 gene resulting in amino acid alterations.
• the most important mechanisms leading to reduced DMI sensitivity are based on development of new mutations or on the accumulation of mutations in the CYP51 gene.
• the present invention comprises a method for controlling Septoria tritici that is already resistant to DMI fungicides, in particular, Septoria tritici comprising mutations in the CYP51 gene, on cereals, said method comprising applying to the plants, their seed or the soil a fungi- cidally effective amount of 4-[[6-[2-(2,4-difluorophenyl)-1 ,1-difluoro-2-hydroxy-3-(5-thioxo-4,5- dihydro-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (I) or 4-[[6-[2-(2,4-difluorophenyl)-1,1- difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (II).
• compound (II) is applied.
• compound (I) and compound (II) can be used in form of
• compound (I) is used as racemate.
• compound (I) is used as (R)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, pref erably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
• compound (I) is used as a pure (R)-enantiomer.
• compound (I) is used as (S)-enantiomer with an en antiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, prefera bly at least 90%, more preferably at least 95%, yet more preferably at least 98% and most pref erably at least 99%.
• compound (I) is used as a pure (S)- enantiomer.
• compound (II) is used as race- mate.
• compound (II) is used as (R)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
• compound (II) is used as a pure (R)-enantiomer.
• compound (II) is used as (S)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, pref erably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
• compound (II) is used as a pure (S)-enantiomer.
• Septoria tritici resistant to DMI fungicides in particular Septo- ria tritici comprising at least one mutation in the CYP51 gene, is controlled.
• the mutation occurs in the amino acid positions selected from 50, 107, 134, 136,
• the mutations are preferably selected from the alterations listed in Table 1.
• Septoria tritici comprises at least one mutation in the CYP51 gene.
• the mutation is in the amino acid position 50, preferably the mutation is M.1.
• the mutation is in the amino acid position 107, prefera bly the mutation is M.2.
• the mutation is in the amino acid position 134, prefera bly the mutation is M.3.
• the mutation is in the amino acid position 136, prefera bly the mutation is M.4 or M5.
• the mutation is in the amino acid position 137, prefera bly the mutation is M.6.
• the mutation is in the amino acid position 178, prefera bly the mutation is M.7.
• the mutation is in the amino acid position 188, prefera bly the mutation is M.8. According another specific embodiment, the mutation is in the amino acid position 208, prefera bly the mutation is M.9.
• the mutation is in the amino acid position 259, prefera bly the mutation is M.10.
• the mutation is in the amino acid position 284, prefera bly the mutation is M.11.
• the mutation is in the amino acid position 303, prefera bly the mutation is M.12.
• the mutation is in the amino acid position 311 , prefera bly the mutation is M.13.
• the mutation is in the amino acid position 312, prefera bly the mutation is M.14.
• the mutation is in the amino acid position 379, prefera bly the mutation is M.15.
• the mutation is in the amino acid position 381 , prefera bly the mutation is M.16.
• the mutation is in the amino acid position 410, prefera bly the mutation is M.17.
• the mutation is in the amino acid position 412, prefera bly the mutation is M.18.
• the mutation is in the amino acid position 459, prefera bly the mutation is M.19, M.20, M.21 or M.22.
• the mutation is in the amino acid position 460, prefera bly the mutation is M.23 or M.24.
• the mutation is in the amino acid position 461 , prefera bly the mutation is M.25, M.26, M.27, M.28, M.29 or M.30.
• the mutation is in the amino acid position 476, prefera bly the mutation is M.31.
• the mutation is in the amino acid position 490, prefera bly the mutation is M.32.
• the mutation is in the amino acid position 510, prefera bly the mutation is M.33.
• the mutation is in the amino acid position 513, prefera bly the mutation is M.34.
• the mutation is in the amino acid position 524, prefera bly the mutation is M.35.
• Septoria tritici comprises at least two mutations in the CYP51 gene.
• the said two mutations occur in the positions selected from 50+107, 50+134, 50+136, 50+137, 50+178, 50+188, 50+208, 50+259, 50+284, 50+303, 50+311 , 50+312, 50+379, 50+381 , 50+410, 50+412, 50+459, 50+460, 50+461, 50+476, 50+490, 50+510, 50+513, 50+524, 107+134, 107+136, 107+137, 107+178, 107+188, 107+208, 107+259, 107+284, 107+303, 107+311, 107+312, 107+379, 107+381, 107+410, 107+412, 107+459, 107+460, 107+461, 107+476, 107+490, 107+510, 107+513, 107+524, 134+136, 134+137, 134+178, 134+178,
• the combination A15 is particularly preferred.
• Septoria tritici comprises at least three mutations in the CYP51 gene.
• the said three mutations occur in the positions selected from
• Septoria tritici comprises at least four mutations in the CYP51 gene.
• the said four mutations occur in the positions selected from
• Septoria tritici comprises at least five mutations in the CYP51 gene.
• Septoria tritici comprises at least six mutations in the CYP51 gene.
• Septoria tritici comprises at least seven mutations in the CYP51 gene.
• Septoria tritici comprises at least eight mutations in the CYP51 gene.
• Septoria tritici comprises at least the following mutation combinations:
• the method comprises applying a fungicidally effective amount of com pound (I) or compound (II) to the cereal plants.
• the method comprises applying a fungicidally effective amount of compound (I) or compound (II) to the cereal seeds.
• cereal as used herein comprises wheat and triticale.
• the present invention relates to a method for controlling Sep- toria tritici that is resistant to DM I fungicides on wheat or triticale, comprising applying to the plants, their seed or the soil a fungicidally effective amount of compound (I) or compound (II).
• the method comprises applying to the wheat or triticale plants a fungicidally effective amount of compound (I) or compound (II).
• the method comprises applying to the wheat or triticale seeds a fungicidally effective amount of compound (I) or compound (II).
• the present invention relates to a method for controlling Sep- toria tritici that is resistant to DM I fungicides on wheat, comprising applying to the plants, their seed or the soil a fungicidally effective amount of compound (I) or compound (II).
• the method comprises applying to the wheat plants a fungicidally effective amount of compound (I) or compound (II).
• the method comprises applying to the wheat seeds a fungicidally effective amount of compound (I) or compound (II).
• Application of the compound (I) or compound (II) to the plants, their seed or the soil in the method according to present invention may be carried out in spray application, in seed treat- merit, in drip and drench applications, in-furrow applications, on-seed application and overall soil incorporation, chemigation, i.e. by addition of the active ingredients to the irrigation water, and in hydroponic/mineral systems.
• fungicidal action against Septoria tritici means a signifi cant reduction in primary infection by Septoria tritici, compared with the untreated plant, prefer ably a significant reduction (by a value of between 40-79% compared to an untreated control plant), compared with the untreated plant (100%); more preferably, the primary infection by Septoria tritici is entirely suppressed (by a value of between 80-100% compared to an untreated control plant).
• the control is for protection of plants which have not yet been infected.
• the above reduction in primary infection by Septoria tritici, compared with the untreated plant is of at least 40%, more preferably at least 60%, even more preferably at least 70%.
• the above reduction of at least 40%, more preferably at least 60%, even more preferably at least 70% is achieved by using at most 200 g a.i. / 100kg seed, such as at most 150 g a.i. / 100kg seed or such as at most 140 g a.i. / 100kg seed.
• plant propagation material is to be understood to denote all the generative parts of the plant in particular seeds
• Plants and as well as the propagation material of said plants, which can be treated with fungi- cidally effective amount of compound (I) or compound (II) include all genetically modified plants or transgenic plants, e.g. crops which tolerate the action of herbicides or fungicides or insecti cides owing to breeding, including genetic engineering methods, or plants which have modified characteristics in comparison with existing plants, which can be generated for example by tradi tional breeding methods and/or the generation of mutants, or by recombinant procedures.
• compounds (I) or (II) in a method according to the present invention can be ap plied (as seed treatment, spray treatment, in furrow or by any other means) also to plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://www.bio.org/speeches/pubs/er/agri_products.asp).
• Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
• one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
• Such genetic modi fications also include but are not limited to targeted post-transitional modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
• compound (I) or compound (II) can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, pow- ders, pastes granules, pressings, capsules, and mixtures thereof.
• the use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound I or compound (II).
• the formulations are prepared in a known manner (cf. US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning: ’’Agglomeration”, Chemical Engi neering, Dec.
• composition types see also “Catalogue of pesticide formulation types and interna tional coding system”, Technical Monograph No. 2, 6 th Ed. May 2008, CropLife International) are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g.
• suspensions e. g. SC, OD, FS
• emulsifiable concentrates e. g. EC
• emulsions e. g. EW, EO, ES, ME
• capsules e. g. CS, ZC
• pastes
• WG WG
• SG GR
• FG GG
• MG MG
• insecti cidal articles e. g. LN
• gel formulations for the treatment of plant propagation mate rials such as seeds (e. g. GF).
• the formulations may comprise auxiliaries which are customary in agrochemical formulations.
• auxiliaries which are customary in agrochemical formulations.
• the auxiliaries used depend on the particular application form and active substance, respective ly.
• auxiliaries are solvents, solid carriers, dispersants or emulsifiers (such as further solubilizers, protective colloids, surfactants and adhesion agents), organic and anorganic thickeners, bactericides, anti-freezing agents, anti-foaming agents, if appropriate colorants and tackifiers or binders (e. g. for seed treatment formulations).
• the formulations generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, most preferably between 0.5 and 90%, by weight of active substances.
• the active substance concentrations in the ready-to-use preparations can be varied within rela tively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.001 to 1% by weight of compound (I) or compound (II).
• Compound (I) or compound (II) may be used together with other pesticides, such as herbicides, fungicides, insecticides or bactericides. These agents can be admixed with compound (I) or compound (II) in a weight ratio of 1:100 to 100:1, preferably 1 :10 to 10:1, if appropriate immedi ately prior to use (tank mix).
• Compound (I) or compound (II) may also be used together with fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators and saf- eners. These may be used sequentially or in combination with the above-described composi tions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with the fertilizers.
• fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators and saf- eners.
• Compound (I) or compound (II) are applied by treating the fungi or the plants, plant propagation materials (preferably seeds), materials or soil to be protected from fungal attack with a pesti- cidally effective amount of compound (I) or compound (II).
• the application can be carried out both before and after the infection of the materials, plants or plant propagation materials (pref erably seeds) by the pests.
• pesticidally effective amount means the amount of compound (I) or compound (II) or of compositions comprising compound (I) or or compound (II) needed to achieve an observa ble effect on growth, including the effects of necrosis, death, retardation, prevention, and re moval, destruction, or otherwise diminishing the occurrence and activity of the target organism.
• the pesticidally effective amount can vary.
• a pesticidally effective amount will also vary accord ing to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
• the application rates of compound (I) or compound (II) are from 0,1 g/ha to 10000 g/ha, preferably 2 g/ha to 2500 g/ha, more preferably from 5 to 1000 g/ha, most preferably from 10 to 750 g/ha, in particular from 20 to 700 g/ha.
• the compound (I) or compound (II) are used for the protection of the seed and the seedlings' roots and shoots, preferably the seeds as set forth above.
• compositions comprising compound (I) or compound (II) can be applied to plant propaga tion materials, particularly seeds, diluted or undiluted.
• the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, prefer ably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
• Methods for applying agrochemical compounds and compositions thereof, respectively, on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting, dusting and soaking application methods of the propa gation material (and also in furrow treatment).
• the compounds or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
• the application rates of the in ventive mixture are generally for the formulated product (which usually comprises from 10 to 750 g/l of the active(s)) .
• the compounds were dissolved in a mixture of acetone and/or dimethylsulfoxide and the wet ting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a ratio (volume) solvent-emulsifier of 99 to 1 to give a total volume of 5 ml. Subsequently, water was added to total volume of 100 ml. This stock solution was then diluted with the described solvent- emulsifier-water mixture to the final concentration given in the table below.
• Wettol which is based on ethoxylated alkylphenoles
• Leaves of potted wheat seedlings were inoculated with an aqueous spore suspension of Zy moseptoria tritici. Then the plants were immediately transferred to a humid chamber at 18-22°C and a saturated relative humidity. After 4 days, the plants were sprayed to run-off with the pre viously described spray solution. The plants were allowed to air-dry and then transferred to a greenhouse chamber at 18-22°C and a relative humidity of about 70 %. After 4 weeks the se verity of fungal attack on leaves was visually assessed as % diseased leaf area.
• Leaves of potted wheat seedlings were sprayed to run-off with the previously described spray solution.
• the plants were allowed to air-dry and then placed in a greenhouse chamber at 19°C and a relative humidity of about 55 %.
• Seven days later the plants were inoculated with an aqueous spore suspension of Zymoseptoria tritici. Thereafter the plants were immediately trans ferred to a humid chamber at 18-22°C and a saturated relative humidity. After 4 days the plants were placed in chamber at 18-22°C and a relative humidity of about 70 %.
• the severity of fungal attack on leaves was visually assessed as % diseased leaf area.
• Isolate (A) carries the following mutations in CYP 51: L50S, V136A and Y461S.
• Isolate (B) carries the following mutations in CYP 51: L50S, V136C, S188N, A379G, 1381V, Del Y459, DelG460, S524T

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• Life Sciences & Earth Sciences (AREA)
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• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
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• Engineering & Computer Science (AREA)
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• 2020
  • 2020-11-16 EP EP20804553.4A patent/EP4064840A1/de active Pending
  • 2020-11-16 WO PCT/EP2020/082205 patent/WO2021104910A1/en unknown

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