WO2020078942A1 - Procédé de lutte contre la septoria tritici résistant aux fongicides inhibiteurs de la c14-déméthylase - Google Patents

Procédé de lutte contre la septoria tritici résistant aux fongicides inhibiteurs de la c14-déméthylase Download PDF

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Publication number
WO2020078942A1
WO2020078942A1 PCT/EP2019/077852 EP2019077852W WO2020078942A1 WO 2020078942 A1 WO2020078942 A1 WO 2020078942A1 EP 2019077852 W EP2019077852 W EP 2019077852W WO 2020078942 A1 WO2020078942 A1 WO 2020078942A1
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WIPO (PCT)
Prior art keywords
mutation
compound
trifluoromethyl
triazol
septoria tritici
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PCT/EP2019/077852
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English (en)
Inventor
Dieter Strobel
Christian Winter
Andreas Koch
Markus Gewehr
Gerd Stammler
Martin Semar
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BASF Agro B.V.
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Application filed by BASF Agro B.V. filed Critical BASF Agro B.V.
Priority to EP19789647.5A priority Critical patent/EP3866602A1/fr
Publication of WO2020078942A1 publication Critical patent/WO2020078942A1/fr

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    • 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 treating the plants, their seed or the soil with a fungi- cidally effective amount of a compound of formula (I)
  • A is CH or N
  • R 1 is selected from hydrogen, (Ci-C 6 )-alkyl, C(0)CH 3 ;
  • R 2 is selected from hydrogen, (Ci-C 6 )-alkyl or (C3-C6)-cycloalkyl;
  • R 3 is selected from hydrogen, halogen, (Ci-C 6 )-alkyl or (Ci-C 6 )-haloalkyl;
  • R 4 is selected from halogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (Ci-C 6 )-alkoxy or (Ci-Ce)- haloalkoxy;
  • n 0, 1 , 2, 3.
  • 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.
  • fungicides containing azole and strobilurine mixtures have been widely and suc- cessfully used in recent years for Septoria control. Strobilurins lost their activity due to the development of the G143A resistance which is mean- while widespread in most cereal growing regions in Europe (Fraaije B. A., Brunett F. J., Clark W. S., Motteram J., Lucas J. A. (2005). Resistance development to Qol inhibitors in populations of Mycosphaerella graminicola in the UK. Modern fungicides and antifungal compounds II, eds Lyr H., Russell P. E., Dehne H-W. Gisi U. Kuck K-H, 14th International Reinhardsbrunn Sympo- sium, BCPC, Alton, UK, pp 63-71 ).
  • DMI Demethlyation inhibitor
  • DMI 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 treating the plants, their seed or the soil with a fungi- cidally effective amount of a compound of formula (I)
  • A is CH or N
  • R 1 is selected from hydrogen, (Ci-C 6 )-alkyl or C(0)CH 3 ;
  • R 2 is selected from hydrogen, (Ci-C 6 )-alkyl or (C3-C6)-cycloalkyl;
  • R 3 is selected from hydrogen, halogen, (Ci-C 6 )-alkyl or (Ci-C 6 )-haloalkyl;
  • R 4 is selected from halogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (Ci-Ce)-alkoxy or (O I -O Q )- haloalkoxy;
  • n 0, 1 , 2, 3.
  • halogen refers to fluorine, chlorine, bromine and iodine.
  • Ci-C 6 -alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2- methylpropyl, 1 ,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,
  • C2-C4-alkyl refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl, 1-methylpropyl (sec. -butyl), 2-methylpropyl (iso-butyl), 1 ,1-dimethylethyl (tert-butyl).
  • Ci-C 6 -haloalkyl refers to an alkyl group having 1 or 6 carbon atoms, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1- chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.
  • C3-C6-cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Ci-C 6 -alkoxy refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen at any position in the alkyl group.
  • Examples are “C1-C4- alkoxy” groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1- methyhpropoxy, 2-methylpropoxy or 1 ,1-dimethylethoxy.
  • Ci-C 6 -haloalkoxy refers to a Ci-C 6 -alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • a preferred embodiment of a Ci-C 6 -haloalkoxy is a Ci-C4-haloalkoxy.
  • C1- C4-haloalkoxy groups include substituents, such as OCH2F, OCHF2, OCF 3 , OCH2CI, OCHC , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2- chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro- 2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichlorcnethoxy, OC2F 5 , OCF2CHF2, OCHF-CF 3 , 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,
  • resistance refers to an acquired, heritable reduction in sensitivity of a fungus to a specific anti-fungal agent (or fungicide).
  • A is CH or N. According to one embodiment, A is CH. Ac- cording to another embodiment, A is N.
  • R 1 is selected from hydrogen, (Ci-C 6 )-alkyl or C(0)CH 3 ; preferably from hydrogen or (Ci-C 6 )-alkyl, more preferably from hydrogen, CH 3 , C2H 5 or CH(CH 3 ) 2 .
  • R 1 is hydrogen
  • R 1 is (Ci-C 6 )-alkyl, preferably CH 3 , C2H 5 or
  • R 1 is C(0)CH 3 .
  • R 2 is selected from hydrogen, (Ci-C 6 )-alkyl or (C 3 -C 6 )- cycloalkyl, preferably from hydrogen, CH 3 , C 2 H 5 or cyclopropyl, more preferably from hydrogen, CH 3 or cyclopropyl.
  • R 2 is hydrogen
  • R 2 is (Ci-C 6 )-alkyl, preferably CH 3 or C 2 H 5 .
  • R 2 is (C3-C6)-cycloalkyl, preferably cyclopropyl.
  • R 3 is selected from hydrogen, halogen, (Ci-C 6 )-alkyl or (C1- C 6 )-haloalkyl; preferably from halogen or (Ci-C 6 )-haloalkyl, more preferably from (O I -O Q )- haloalkyl.
  • R 3 is hydrogen
  • R 3 is halogen, preferably F or Cl.
  • R 3 is (Ci-C 6 )-alkyl, preferably CH 3 or C 2 H 5 .
  • R 3 is (Ci-C 6 )-haloalkyl, preferably CF 3 .
  • R 4 is selected from halogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (Ci-Ce)-alkoxy or (Ci-C 6 )-haloalkoxy; preferably from preferably from halogen, (Ci-C 6 )-alkyl, (C1- C 6 )-haloalkyl or (Ci-C 6 )-haloalkoxy, more preferably from halogen;
  • R 4 is selected from halogen, (Ci-C 6 )-haloalkyl or (O-I-OQ)- haloalkoxy; preferably from hydrogen, F, Cl, Br, CH3, CF3 or OCF3.
  • R 4 is halogen, preferably from Cl or Br.
  • R 4 is (Ci-C 6 )-alkyl, preferably CH 3 .
  • R 4 is (Ci-C 6 )-haloalkyl, preferably CF 3 .
  • R 4 is (Ci-C 6 )-alkoxy, preferably OCH 3 .
  • R 4 is (Ci-C 6 )-haloalkoxy, preferably OCF 3 .
  • n is 0, 1 , 2 or 3, preferably 0, 1 or 2, more preferably 1. According to one specific embodiment, n is 0.
  • n is 1. According to another specific embodiment, n is 2.
  • n 3.
  • R 1 is selected from hydrogen or (Ci-C 6 )-alkyl
  • R 2 is selected from hydrogen, (Ci-C 6 )-alkyl or (C3-C6)-cycloalkyl;
  • R 3 is selected from halogen or (Ci-C 6 )-haloalkyl
  • R 4 is selected from halogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl or (Ci-C 6 )-haloalkoxy; n is 0, 1 or 2.
  • R 1 is selected from hydrogen, CH3, C2H5 or CH(CH3)2;
  • R 2 is selected from hydrogen, CH 3 , C2H 5 or cyclopropyl
  • R 3 is selected from F, Cl or CF 3 ;
  • R 4 is selected from F, Cl, Br, CH 3 , CF 3 or OCF 3 ;
  • n 0, 1 or 2.
  • R 1 is hydrogen
  • R 2 is selected from hydrogen, (Ci-Ce)-alkyl or (C3-C6)-cycloalkyl;
  • R 3 is (Ci-C 6 )-haloalkyl
  • R 4 is selected from halogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl or (Ci-C 6 )-haloalkoxy; n is 1.
  • R 2 is selected from hydrogen, CH 3 , C2H 5 or cyclopropyl
  • R 3 is CF 3 ;
  • R 4 is selected from F, Cl, Br, CH 3 , CF 3 or OCF 3 ;
  • n 1.
  • R 1 is hydrogen
  • R 2 is selected from hydrogen, (Ci-Ce)-alkyl or (C3-C6)-cycloalkyl;
  • R 3 is (Ci-C 6 )-haloalkyl
  • R 4 is halogen
  • n 1.
  • R 1 is hydrogen
  • R 2 is selected from hydrogen, CH 3 or cyclopropyl
  • R 3 is CF 3 ;
  • R 4 is Cl or Br
  • n 1
  • the compounds of formula (I) are selected from
  • the compounds of formula I are selected from
  • Compounds of formula (I) comprise chiral centers and are generally obtained in the form of racemates.
  • the R- and S-enantiomers of compounds of formula (I) can be separated and iso- lated in pure form with methods known by the skilled person, e.g. by using chiral HPLC.
  • compounds of formula (I) especial- ly compounds of formula 1.01 , 1.02, 1.03, 1.04 or 1.05, can be used in form of
  • compound 1.01 is used.
  • Compound 1.01 may be present as racemic composition of the (R)-enantiomer and (S)-enantiomer, but the (R)-enantiomer and the (S)-enantiomer may also be present in any other proportion, for exam- pie the pure enantiomer (R) or the pure enantiomer (S) of 1.01.
  • the compound 1.01 is provided and 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%.
  • an enantiomeric excess e.e.
  • the compound 1.01 is provided and used as (S)- 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 (R)-l.01 (R)-2-(6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl)-1 -(1 H-1 ,2,4- triazol-1 -yl)propan-2-ol;
  • compound 1.02 is used.
  • Compound 1.02 may be present as racemic composition of the (R)-enantiomer and (S)-enantiomer, but the (R)-enantiomer and the (S)-enantiomer may also be present in any other proportion, for exam- pie the pure enantiomer (R) or the pure enantiomer (S) of 1.02.
  • the compound 1.02 is provided and 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%.
  • an enantiomeric excess e.e.
  • the compound 1.02 is provided and used as (S)- 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%.
  • an enantiomeric excess e.e.
  • compound 1.03 is used.
  • Compound 1.03 may be present as racemic composition of the (R)-enantiomer and (S)-enantiomer, but the (R)-enantiomer and the (S)-enantiomer may also be present in any other proportion, for exam- pie the pure enantiomer (R) or the pure enantiomer (S) of 1.03.
  • the compound 1.03 is provided and 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%.
  • an enantiomeric excess e.e.
  • the compound 1.03 is provided and used as (S)- 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%.
  • an enantiomeric excess e.e.
  • compound 1.04 is used.
  • Compound 1.04 may be present as racemic composition of the (R)-enantiomer and (S)-enantiomer, but the (R)-enantiomer and the (S)-enantiomer may also be present in any other proportion, for exam- pie the pure enantiomer (R) or the pure enantiomer (S) of 1.04.
  • the compound 1.04 is provided and 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%.
  • the compound 1.04 is provided and used as (S)- 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%.
  • an enantiomeric excess e.e.
  • compound 1.05 is used.
  • Compound 1.05 may be present as racemic composition of the (R)-enantiomer and (S)-enantiomer, but the (R)-enantiomer and the (S)-enantiomer may also be present in any other proportion, for exam- pie the pure enantiomer (R) or the pure enantiomer (S) of 1.05.
  • the compound 1.05 is provided and 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%.
  • an enantiomeric excess e.e.
  • the compound 1.05 is provided and used as (S)- 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%.
  • an enantiomeric excess e.e.
  • 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.
  • 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.1 1.
  • 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. According another specific embodiment, 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
  • the sign“+” is to be read as“and”, so that, for example, the mutations occuring in the positions 50+107 means that one mutation occurs in the position 50 and the second one in the position 107.
  • 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 treating the cereal plants with a fungicidally effective amount of a compound of formula (I). In a further embodiment, the method comprises treating cereal seeds with a fungicidally effec- tive amount of a compound of formula (I).
  • cereal plants as used herein comprises wheat and triticale.
  • the present invention relates to a method for controlling Sep- toria tritici that is resistant to DMI fungicides on wheat or triticale, comprising treating the plants, their seed or the soil with a fungicidally effective amount of a compound of formula (I).
  • the method comprises treating the wheat or triticale plants with a fungicidally effective amount of a compound of formula (I).
  • the method comprises treating wheat and triticale seeds with a fungicidally effective amount of a compound of formula (I).
  • the present invention relates to a method for controlling Sep- toria tritici that is resistant to DMI fungicides on wheat, comprising treating the plants, their seed or the soil with a fungicidally effective amount of a compound of formula (I).
  • the method comprises treating the wheat plants with a fungicidally effective amount of a compound of formula (I).
  • the method comprises treating wheat seeds with a fungicidally effective amount of a compound of formula (I).
  • Treating the plants, their seed or the soil in the method according to present invention may be carried out in spray application, in seed treatment, 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 a compound of formula (I) include all genetically modified plants or transgenic plants, e.g. crops which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods, or plants which have modified char- acteristics in comparison with existing plants, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures.
  • compounds I in a method according to the present invention can be applied (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 ag- ricultural biotech products on the market or in development (cf.
  • 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. Typically, 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.
  • a compound of formula (I) can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, 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.
  • the formulations are prepared in a known manner (cf. US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning: “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill, New York, 1963, S. 8-57 und ff.
  • 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.
  • 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- iy-
  • 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 of formula (I).
  • Compound of formula (I) may be used together with other pesticides, such as herbicides, fungi- cides, insecticides or bactericides. These agents can be admixed with compound of formula (I) in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1 , if appropriate immediately prior to use (tank mix).
  • Compound of formula (I) may also be used together with fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators and safeners. These may be used sequentially or in combination with the above-described compositions, 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 ferti- lizers.
  • fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators and safeners.
  • Compounds of the formula (I) 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 of formula (I).
  • the application can be carried out both be- fore and after the infection of the materials, plants or plant propagation materials (preferably seeds) by the pests.
  • pesticidally effective amount means the amount of compound of formula (I) or of compositions comprising compound of formula (I) needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruc- tion, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidal ly effective amount can vary.
  • a pesticidally effective amount will also vary according to the pre- vailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the application rates of compound of formula (I) 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 of formula (I) is used for the pro- tection of the seed and the seedlings' roots and shoots, preferably the seeds as set forth above.
  • compositions comprising compound of formula (I) can be applied to plant propagation ma- terials, 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, re- spectively, on to plant propagation material, especially seeds are known in the art, and include dressing, coating, pelleting, dusting and soaking application methods of the propagation materi- al (and also in furrow treatment).
  • the compounds or the composi- tions 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 from10 to 750 g/l of the active(s)) .
  • the active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
  • the spores of Zymoseptoria tritici (formerly known as Septoria tritici) were harvested with a cot- ton swab from an MYA agar plate (1 Og/I malt, 4 g/l yeast extract, 4 g/l glucose, 20 g/l agar) and this is dipped in 3 ml of double concentrated YBG-medium, double concentrated (20 g/l yeast extract, 20 g/l pacto pepton, 40 g/l glycerol) and the suspension is adjusted to a spore density of 1.6x10 4 /ml. Compounds were diluted from stock solution in (dimethylsulfoxide) DMSO in 7 steps.
  • the compound solutions were diluted 1/5 with sterile deionized water before use. 50 pi of the corn- pound solutions were transferred into empty microplates. The plates were then filled with 50 mI of a spore suspension (spore density adjusted to 1 ,6x10 4 spores/ml) of each strain.
  • the antifungal activity was determined by measuring the turbidity of a culture in 96-well micro- plates in the presence of test compounds. Fungal growth was measured by recording the optical density at 405 nm after 7 days. A blank value for each concentration (growth media + compound, but without spores) was substracted from the spore suspension. The relative antifungal activity was calculated by comparison of the effect of the test compounds with the effect of a DMSO control and a standard fungicide.
  • ICso-values concentration of test compound resulting in 50% inhibition of fungal growth

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

Abstract

La présente invention concerne un procédé de lutte contre la Septoria tritici comprenant au moins une mutation dans le gène CYP51 et étant résistante aux fongicides inhibiteurs de la C14-déméthylase (dans la biosynthèse des stérols) (fongicides DMI) sur les céréales, comprenant le traitement des plantes, de leurs graines ou du sol avec une quantité efficace du point de vue fongicide d'un composé selon la formule (I).
PCT/EP2019/077852 2018-10-18 2019-10-15 Procédé de lutte contre la septoria tritici résistant aux fongicides inhibiteurs de la c14-déméthylase WO2020078942A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022034892A1 (fr) * 2020-08-11 2022-02-17 株式会社クレハ Agent de lutte contre les maladies et procédé de lutte contre les maladies pour une utilisation agricole et horticole
WO2023209045A1 (fr) 2022-04-26 2023-11-02 Syngenta Crop Protection Ag Fongicides énantiomériquement enrichis pour la lutte contre des champignons phytopathogènes résistants

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022034892A1 (fr) * 2020-08-11 2022-02-17 株式会社クレハ Agent de lutte contre les maladies et procédé de lutte contre les maladies pour une utilisation agricole et horticole
WO2023209045A1 (fr) 2022-04-26 2023-11-02 Syngenta Crop Protection Ag Fongicides énantiomériquement enrichis pour la lutte contre des champignons phytopathogènes résistants

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