OA20722A - Methods of controlling or preventing infestation of peanut plants by phytopathogenic microorganisms. - Google Patents

Methods of controlling or preventing infestation of peanut plants by phytopathogenic microorganisms. Download PDF

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Publication number
OA20722A
OA20722A OA1202200225 OA20722A OA 20722 A OA20722 A OA 20722A OA 1202200225 OA1202200225 OA 1202200225 OA 20722 A OA20722 A OA 20722A
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OAPI
Prior art keywords
substituted
phenyl
compound
haloalkyl
halogen
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OA1202200225
Inventor
Katherine BUXTON
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Syngenta Crop Protection Ag
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Publication of OA20722A publication Critical patent/OA20722A/en

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Abstract

The present invention relates to methods for controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, a compound according to formula (I)

Description

METHODS OF CONTROLLING OR PREVENTING INFESTATION OF PEANUT PLANTS BY PHYTOPATHOGENIC MfCROORGANISMS
Technical Field
The présent invention relates to methods for controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Ceroospora.
Background
Cercospora is a fungal pathogen in peanut that attacks any above-ground part of the plant, but leaf spots are the most conspicuous symptom. Depending upon weather conditions and cropping history, leaf symptoms usually appear between 30 to 50 days after planting. Yield loss occurs from the shedding or défoliation of diseased leaflets. Défoliation reduces healthy leaf area and weakens the stems and pegs causing pods to fall off the vine during digging and harvest. Yield losses of 50 percent or more are possible when leaf spot is not controlled and nearly complété défoliation occurs. Thus, there is a need for providing improved methods to control or prevent infestation of peanut plants by the phytopathogenic microorganism Cercospora.
The current invention provides further methods for controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora, in partîcular Cercospora arachidicola.
Description of the embodiments
Cyclobutylcarboxamide compounds and processes fortheir préparation hâve been disclosed in WO2013/143811 and WO2015/003Ô51. It has now been surprisingly found that partîcular cyclobutylcarboxamide compounds disclosed in WO2013/143811 and/or WO2015/003951 are highly effective at controlling or preventing the infestation of peanut plants by the phytopathogenic microorganism Cercospora. These highly effective compounds thus represent an important new solution for farmers to control or prevent infestation of peanut plants by the fungal pathogen Cercospora.
Hence, as embodiment 1, there is provided a method of controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora comprising applying to a crop of plants, the locus thereof, or propagation material thereof, a compound according to formula (I)
(î)
wherein
Yis O, 0=0, orCR12R13;
A is a 5- or 6-membered heteroaromatic ring containing 1 to 3 heteroatoms, each independently selected from oxygen, nitrogen and sulphur, or a phenyl ring; the heteroaromatic ring orthe phenyl 5 being optionally substituted by one or more R6;
R6 is, independently of each other, hafogen, cyano, C1-C4-alkyl, C1-C4-haioalkyl, C1-C4-alkoxy, C1-C4-ha!oalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxy-C1-4-alkyl or C1-C4-haloalkoxy-C1-C4-alkyl; R1, R2, R3, R4, R12 and R13, independently of each other, are hydrogen, halogen, cyano, C1-C4alkyl, C1-C4-alkoxy or C1-C4-haloalkyl,
R5 is hydrogen, methoxy or hydroxyl,
B is phenyl substituted by one or more R8,
R8 is, independently of each other, halogen, cyano or a group -L-R9, where each L is independently of each other a bond, -O-, -00(0)-, -NR7-, -NR7CO-, -NR7S(O)n-, -S(O)n-, -S(O)nNR7-, -COO- or CONR7-, n îs 0, 1 or 2,
R7 is hydrogen, C1-C4-alkyl, C1-C4-haioalkyl, benzyl or phenyl, where benzyl and phenyl is unsubstituted or substituted with halogen, cyano, C1-C4-alky! or C1-C4-haloalkyl,
R9 is, independently ofeach other, C1-C6-alkyl, which is unsubstituted or substituted by one or more R10, C3-C6-cycloalkyl, which is unsubstituted or substituted by one or more R10, 06-01420 bicycfoalkyl, which is unsubstituted or substituted by one or more RIO, C2-C6-alkenyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkynyl, which is unsubstituted or substituted by one or more RIO, phenyl, which is unsubstituted or substituted by R10, or heteroaryl, which is unsubstituted or substituted by one or more R10, R10 is, independently ofeach other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy,
01-04-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-alkenyloxy, or C3-C6-alkynyloxy;
or a sait or N-oxide thereof;
wherein B and A-CO-NR5 are cis to each other on the four-membered ring, or a tautomer or stereoisomer of these compounds,
More preferred methods according to embodiment 1 are given in the embodiments below.
As embodiment 2, there is provided a method according to embodiment 1 wherein YisOorCH2;
A is a 6-membered heteroaromatic ring containing 1 to 2 nitrogen atoms, or a phenyl ring; the heteroaromatic ring or the phenyl being optionally substituted by one or more R6;
R6 is, independently ofeach other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4haloalkoxy;
R1, R2, R3, R4, and R5 are each hydrogen;
B is phenyl substituted by one or more R8;
I 3
R8 is, independently of each other, selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyi, C1C4-haloalkoxy and C3-C6-cycloalkyl.
As embodiment 3, there is provided a method according to either embodiment 1 or embodiment 2 5 wherein A is a 6-membered tieteroaromatic ring containing 1 to 2 nitrogen atoms and having 1 to 3 substituents selected from R6, or a phenyl ring having 1 or 3 substitutents selected from R6.
As embodiment 4, there is provided a method according to any one of embodiments 1 to 3 wherein B is a phenyl substituted by 1 to 3 substitutents R8.
As embodiment 5, there is provided a method according to any one of embodiments 1 to 4 wherein B is a phenyl substituted by 1 to 3 substituents, independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, difluoromethoxy and trifluoromethoxy;
A is a phenyl, pyridyl or pyrazinyl, which rings, independently of each other, are unsubstituted or 15 substituted by 1 to 3 substituents, independently selected from chloro, bromo, fluoro, methyl, cyano, and trifluoromethyl, Y is O orCH2, and R1, R2, R3, R4 and R5 are each hydrogen.
As embodiment 6, there is provided a method according to any one of embodiments 1 to 5 wherein Yis CH2;
B is a mono ordi-halogen substituted phenyl;
A is selected from phenyl, pyrazinyl and pyridyl, each of which is mono or di-substîtuted by substituents independently selected from halogen and C1-C4-haloalkyl;
R1, R2, R3, R4 and R5 are each hydrogen.
Compounds of fomula (I) as disclosed in any one of embodiments 1 to 6 represent the cis racemate: the phenyl ring on the left hand side and the A-C(=O)-NH group on the right hand side are cis to each other on the cyclobutyl ring:
Thus, the racemic compound of formula (I) is a 1:1 mixture ofthe compounds of formula (la) and (Ib). The wedged bonds shown in the compounds of formula (la) and (Ib) represent absolute stereochemistry, whereas the thick straight bonds such as those shown for the compounds of formula (I) represent relative stereochemistry in racemic compounds.
Il has also surprisingly been found that one enantiomer of the compounds of formula (I) is particularly useful in controlling or preventing the infestation of peanut plants by the phytopathogenic microorganism Cercospora.
Th us, as embodiment 7, there is provided the method according to any one of embodiments 1 to 6 wherein the compound is of formula (la) R2 R5
A skilled person is aware that according to the method of embodiment 2, the compound of formula (la) is generaliy applied as part of a pesticidal composition. Hence, as embodiment 8, there is provided a method of controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora, comprising applying to a crop of plants, the locus thereof, or propagation material thereof a pesticidal composition comprising a compound according to anyone of embodiments 1-7 and one or more formulation adjuvants. As embodiment 9, there is provided a method of controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora, comprising applying to a crop of plants, the locus thereof, or propagation material thereof a pesticidal composition comprising a compound of formula (la) and one or more formulation adjuvants. In a method according to embodiment 9, for pesticidal compositions comprising both a compound of formula (la) and a compound of formula (ib), the ratio ofthe compound of formula (la) to its enantiomer (the compound offormula (Ib)) must be greaterthan 1:1. Preferably, the ratio ofthe compound of formula (1a) to the compound of formula (Ib) is greater than 1.5:1, more preferably greater than 2.5:1, especially greaterthan 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.
Mixtures containing up to 50%, preferably up to 40%, more preferably up to 30%, especially up to 20%, advantageously up to 10%, desirably up to 5%, in particular up to 3 %, ofthe trans stereoisomers ofthe compounds offormula (I) (i.e. wherein the B and the A-C(=O)-NH groups are trans to each other) are also understood to be part ofthis invention. Preferably, the ratio ofthe compound of formula (I) to its trans isomer is greater than 1.5:1, more preferably greater than 2.5:1, especially greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.
Preferably, in a composition comprising the compound of formula (la), its trans isomer (i.e. wherein the B and the A-CO-NR2 groups are trans to each other) and the compound of formula (Ib), the composition comprises the compound of formula (la) in a concentration of at least 50%, more preferably 70%, even more preferably 85%, in particular over 90%, and particularly preferably over 95%, each based on the total amount of compound of formula (la), its dans isomer and the compound of formula (Ib).
Further, as embodiment 10, there is provided a method of controlling or preventing infestation of peanut plants by the phytopathogenic micrûorganism Cercospora, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, a compound according to formula (le) wherein
R11 and R12 are independently selected from halogen;
A is pyridyl which is substituted by one or two substituents independently selected from halogen and Ci-C4-haloalkyl.
As embodiment 11, there is provided a method according to embodiment 10, wherein
R11 andR12are independently selected from chloro and fluoro;
A is pyrid-2-yl or pyrid-3-yI, which is substituted by one or two Ci-C4-haloalkyl substituents.
As embodiment 12, there is provided a method according to embodiments 10 or 11, wherein
A is selected from
R13
R13 is Ci-C4-haloalkyl, preferably trifluoromethyl.
As embodiment 13, there is provided a method according to any one of embodiments 10 to 12 wherein the compound is selected from any one of compounds 1 to 12 of formula (le)
(le) wherein R11, RI2 and A are as defined in the following table:
Compound A R11 R12
1 2-trifiuoromethyl-pyrid-3-yl Cl Cl
2 3-trifluoromethyl-pyrid-2-yi Cl Cl
3 3-trifluoromethyl-pyrid-2-yl F F
4 3-trifluoromethyl-pyrid-2-yl Cl F
5 3-chloro-pyrid-2-yl Cl Cl
6 2-methyl-pyrid-3-yl Cl Cl
7 2-trifl u oro methyl- py rid-3-y I Cl F
As embodiment 14, there is provided the method according to any one of embodiments 1 to 13 comprising the steps providing a composition comprising a compound as defined in any one of embodiments 1 to 13;
applying the composition to a propagation material;
plantingthe propagation material.
As embodiment 15, there is provided the method according to any one of embodiments 1 to 13 comprising the steps providing a composition comprising a compound as defined in any one of embodiments 1 to 13;
- applying the composition to a crop of plants or the locus thereof.
As embodiment 16, there is provided the use of a compound as defined in any one of embodiments 1 to 13 for controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora.
As embodiment 17, there is provided the use of a compound as defined in any one of embodiments 1 to 13 for controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora arachidicola.
As embodiment 18, there is provided a method forgrowing peanut plants comprising applying ortreating peanut or a propagation material thereof with a compound as defined in any one of daims 1 to 13.
The préparation ofthe compounds as defined in the methods of any one ofembodiments 1 to 13 has 5 been disclosed in WO2013/143811 and WO2015/003951 which are incorporated herein by reference.
Définitions:
The term halogen represents fluoro, chloro, bromo or iodo, particularly fluoro, chloro or bromo.
The term “alkyl or “alk as used herein either alone or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl and alkylcarbonyl) is a straight or branched Chain and is, for exampîe, methyl, ethyl, π-propyl, n-butyl, isopropyl, sec-butyl, isobutyl, fert-butyl, pentyl, /so-pentyl or n-hexyl. The alkyl groups are suitably Ci-C^alkyl groups.
“Haloalkyl” as used herein are alkyl groups as defined above which are substituted with one or more ofthe same or different halogen atoms and are, for example, CFa, CFiCi, CF2H, CCI2H, FCH2, CICH2, BrCH2, CH3CHF, (CHîkCF, CF3CH2 orCHFaCHï.
The methods and uses according to any one of embodiments 1 to 18 are preferably for controtling or 20 preventing infestation of the crop by the phytopathogenic microorganism Cercospora that are résistant to other fungicides. Cercospora that are résistant to a particular fungicide refer e.g. to strains of Cercospora fungi that are less sensitive to that fungicide compared to the expected sensitivity of the same species of Cercospora fungi. The expected sensitivity can be measured using e.g. a strain that has not previously been exposed to the fungicide.
Application according to the methods or uses according to any one of embodiments 1 to 18 is preferably to a crop of plants, the locus thereof or propagation material thereof. Preferably application is to a crop of plants or propagation material thereof, more preferably to propagation material.
Application ofthe compounds ofthe invention can be performed according to any ofthe usual modes 30 of application, e,g. foliar, drench, soil, in furrow etc.
The compounds as defined in any one of embodiments 1 to 13 are preferably used for pest control at 1 to 500 g active ingrédient (Al) per hectare (ha), preferably 100-200 g active ingrédient (Ai) per hectare (ha).
The compounds as defined in any one of embodiments 1 to 13 are suitable for use on any peanut plant, including those that hâve been genetically modified to be résistant to active ingrédients such as herbicides, orto produce biologically active compounds that control infestation by plant pests.
Generally, a compound as defined in any one of embodiments 1 to 13 is used in the form of a composition (e.g. formulation) containing a carrier. A compound as defined in any one of embodiments 1 to 13 and compositions thereof can be used in various forms such as aérosol dispenser, capsule suspension, coid fogging concentrate, dustable powder, emulsifiable concentrate, 5 émulsion oil in water, émulsion water in oil, encapsulated granule, fine granule, flowable concentrate forseed 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 forseed treatment, suspension concentrate (flowable 10 concentrate), ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, water dispersible granules or ta blets, water dispersible powder for slurry treatment, water soluble granules or ta blets, water soluble powder for seed treatment and wettable powder.
A formulation typically comprises a liquid or solid carrier and optionally one or more customary 15 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. The composition may also further comprise a fertilizer, a micronutrient donor or other préparations 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 bactéricides, fungicides, nematicides, plant activators, acaricides, and insecticides.
The compositions are prepared in a manner knewn per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid compound of the présent invention and in the 25 presence of at least one auxilîary for example by intimately mixing and/or grinding the compound of the présent invention with the auxilîary (auxiliaries). In the case of solid compounds of the invention, the grinding/milling of the compounds is to ensure spécifie particle size.
Examples of compositions for use in agriculture are emulsifiable concentrâtes, suspension 30 concentrâtes, microemulsions, oil dispersibles, directly sprayable or dilatable solutions, spreadable pastes, dilute émulsions, soluble powdecs, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound as defined in any one embodiments 1 to 13 and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.
As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of compound as defined in any one of embodiments 1 to 13 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). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a ru le uses d ilote compositions which hâve substantially lower concentrations of active ingrédient.
Examples offoliar formulation types for pre-mix compositions are:
GR: Granules
WP: wettable powders
WG: water dispersable granules (powders)
SG: water soluble granules
SL: soluble concentrâtes
EC: emulsifiable concentrate
EW: émulsions, oil in water
ME: micro-emulsion
SC: aqueous suspension concentrate
CS: aqueous capsule suspension
OD: oil-based suspension concentrate, and
SE: aqueous sus po-emulsion.
Whereas, examples of seed treatment formulation types for pre-mix compositions are:
WS: wettable powders for seed treatment slurry
LS: solution for seed treatment
ES: émulsions for seed treatment
FS: suspension concentrate for seed treatment
WG: water dispersible granules, and
CS: aqueous capsule suspension.
Exampies of formulation types suitable fortank-mix compositions are solutions, dilute émulsions, suspensions, or a mixture thereof, and dusts.
As with the nature ofthe formulations, 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-mixcompositions 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.
Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated minerai substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilîzers.
Generally, a tank-mix formulation for fohar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, of the desired ingrédients, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for exampie, a 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.
Typîcally, a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, of the desired ingrédients, 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.
Normally, a tank-mix formulation forseed ireatment application comprises 0.25 to 80%, especially 1 to 75 %, of the desired ingrédients, 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.
Typîcally, a pre-mix formulation forseed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, of the desired ingrédients, 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.
Whereas commercial products will preferably be formulated as concentrâtes (e.g., pre-mix composition (formulation)), the end user will normally employ dilute formulations (e.g., tank mix composition).
Preferred seed treatment pre-mix formulations are aqueous suspension concentrâtes. 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 daim coaters. Other methods, such as spouted beds may also be useful. The seeds may be presized before coating. After coating, the seeds are typîcally 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.
In general, 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 ingrédients, 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.
The invention will now be illustrated by the following non-limiting Examples. AU citations are incorporated by reference.
I 11
Biological examples
Effect of different fungicide treatments against Cercospora sp.
A peanut field trial was carried out in Telflair, Georgia, USA, to evaîuate the efficacy of different compounds against the leafspot disease Cercospora arachidicola. Plot borders (peanuts) were planted in early May and left untreated until there was significant leafspot infection on the borders. The peanuts were then planted in July and treatments applied in-furraw at the same day. The disease occurred mid of September and an assessment on disease severity (% infected area) was done 63 days after planting.
Trial location:
Trial Sown Crop Varîety Résistance Status
Location
Quient Field, Telfair, GA, 31549 14th July 2017 Peanut Ga 09b Susceptible
Treatment List - Field Trials:
T reatment Active Ingrédient (Al) Rate (g Al/ha) Application method
1 Untreated —
2 COMPOUND 1 SC450 200 IN FURROW; AT PLANTING ; SOIL
3 Commercial standard: Succinate dehydrogenase inhibitor SC500 (Fluopyram) 250 IN FURROW; AT PLANTING ; SOIL
Crops and targets occurred in the triai:
Latin name Common name
Target CERCOSPORA ARACHIDICOLA Leaf spot
Crop ARACHIS HYPOGAEA Peanut
15
Crop Description:
Test Crop PEANUT
Variety Ga 09b
Sowing or Planting Date 14/07/2017
Trial Layout:
Trial Environment (Test Method) Field trial
Experimental Design RANDOMIZED COMPLETE BLOCK
Plot size 19 m2
# réplications
Application Details:
Application Date 14/07/2017
Appl. Equipment Type In furrow soil application
Spray Volume 100 Uha
Nozzle spacing and type 90cm, Solid stream
Treatments applied 2, 3
Assessments:
Pest severity, 63 days after planting
Pest severity (%), significantly different (Treatments with no letter in common are significantly different at the 5% probability levet) % efficacy based on pest severity
Untreated 31.67,A 0.00
COMPOUND 1 SC450 6.5,B 79.48
Commercial standard: Succinate dehydrogenase inhibitor SC500 (Fluopyram) 15,A 52.64
Conclusion:
Both compounds significantly improved leafspot control. Compound 1 showed very good activity (79%) agaînst Cercospora arachidicola in peanut over a duration of63 days after application. The efficacy of 10 commercial standard compound 2 was moderate (53%).

Claims (13)

  1. Claims
    1. A method of controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, a compound according to formula (I)
    (O wherein
    Yis O, C=O, orCR12R13;
    A is a 5- or 6-membered heteroaromatic ring containing 1 to 3 heteroatoms, each independently selected from oxygen, nitrogen and sulphur, or a phenyl ring; the heteroaromatic ring or the phenyl being optionally substituted by one or more R6;
    R6 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloaikylthio, C1-C4-alkoxy-C1-4-alkyl or C1-C4-haloalkoxy-C1-C4-alkyl; R1, R2, R3, R4, R12 and R13, independently of each other, are hydrogen, halogen, cyano, C1-C4alkyl, C1-C4-alkoxy or C1-C4-haloalkyl,
    R5 is hydrogen, methoxy or hydroxyi,
    B is phenyl substituted by one or more R8,
    R8 is, independently of each other, halogen, cyano or a group -L-R9, where each L is independently of each other a bond, -O-, -OC(O)-, -NR7-, -NR7CO-, -NR7S(O)n-, -S(O)n-, -S(O)nNR7-, -COO- or CONR7-, n is 0, 1 or 2,
    R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, where benzyl and phenyl is unsubstituted or substituted with halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl,
    R9 is, independently of each other, C1-C6-alkyl, which is unsubstituted or substituted by one or more R10, C3-C6-cycloalkyl, which is unsubstituted or substituted by one or more R10, C6-C14bicycloalkyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkenyl, which is unsubstituted or substituted by one or more R10, C2-C6-a!kynyl, which is unsubstituted or substituted by one or more R10, phenyl, which is unsubstituted orsubstituted by RIO, or heteroaryl, which is unsubstituted or substituted by one or more RIO,
    R10 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkytthio, C1-C4-haloalkylthio, C3-C6-alkenyloxy, or C3-C6-alkynyloxy; or a sait or N-oxide thereof;
    wherein B and A-CO-NR5 are cis to each other on the four-membered ring, or a tautomer or stereoisomer of these compounds.
  2. 2. The method according to claim 1 wherein
    YisOorCH2;
    A is a 6-membered heteroaromatic ring containing 1 to 2 nitrogen atoms, or a phenyl ring; the heteroaromatic ring or the phenyl being optionally substituted by one or more R6;
    R6 is, îndependently of each other, hafogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4haloalkoxy;
    R1, R2, R3, R4, and R5 are each hydrogen;
    B is phenyl substituted by one or more R8;
    R8 is, îndependently of each other, selected from halogen, cyano, C1-C4-alkyi, C1-C4-haloalkyl, C1C4'haloalkoxy and C3-C6-cycloaikyl.
  3. 3. A method according to either claim 1 or claim 2 wherein A is a 6-membered heteroaromatic ring containing 1 to 2 nitrogen atoms and having 1 to 3 substituents selected from R6, or a phenyl ring having 1 or 3 substitutents selected from R6.
  4. 4. The method according to any one of cîaims 1 to 3 wherein wherein B is a phenyl substituted by 1 to 3 substitutents R8.
  5. 5. The method according to any one of daims 1 to 4 wherein B is a phenyl substituted by 1 to 3 substituents, îndependently selected from fluoro, chloro, trifluoromethyl, cyctopropyl, difluoromethoxy and trifluoromethoxy;
    A is a phenyl, pyridyl or pyrazinyl, which rings, îndependently of each other, are unsubstituted or substituted by 1 to 3 substituents, îndependently selected, from chloro, bromo, fluoro, methyl, cyano, and trifluoromethyl, Y is O or CH2, and R1, R2, R3, R4 and R5 are each hydrogen.
  6. 6. The method according to any one of daims 1 to 5 wherein
    Y is CH2;
    B is a mono or di-halogen substituted phenyl;
    A is selected from phenyl, pyrazinyl and pyridyl, each of which îs mono ordi-substituted by substituents îndependently selected from halogen and C1-C4-haloalkyl;
    R1, R2, R3, R4 and R5 are each hydrogen.
  7. 7. The method according to any one of daims 1 to 6, wherein the compound is a compound of formula (le)
    wherein
    R11 and R12 are independently selected from halogen;
    A is pyridyl which is substituted by one or two substituents independently selected from halogen and Ci-C4-haloalkyl.
  8. 8. The method according to claim 7 wherein
    R11 andR12are independently selected from chloro and fluoro;
    A is pyrid-2-yl or pyrid-3-yl, which is substituted by one or two Ci-C4-haloalkyl substituents.
  9. 9. The method according to any one of daims 1 to 3 wherein
    A is selected from
    R13 is Ci-C4-haloalkyl.
  10. 10. The method according to claim 1 wherein the compound is selected from any one of compounds 1 to 7 of formula (le)
    (le) wherein R11, R12 and A are as defined in the following table:
    Compound A R11 R12
    1 2-trifluoromethyl-pyrid-3-yl Cl Cl
    2 3-trifiu oromethyl-pyrid-2-yl Cl Cl
    3 3-triflu oro methyl- pyrid-2-yl F F
    4 3-trifiu oro methyl-py rid-2-y I Cf F
    5 3-chloro-pyrid-2-yl Cl Cl
    6 2-methyl-pyrid-3-yl Cl Cl
    7 2-trifluoromethykpyrid-3“yl Cl F
  11. 11. The method according to any one of daims 1 to 10 wherein the phytopathogenic microorganism is Cercospora arachidicola.
    5 12 Use of a compound as defined in any one of daims 1 to 10 for controiling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora.
  12. 13. Use of a compound according to daim 12 wherein the phytopathogenic microorganism is Cercospora arachidicola.
  13. 14. A method forgrowing peanut plants comprising applying ortreating peanut or a propagation material thereof with a compound as defined in any one of daims 1 to 10.
    Abstract
    The présent invention relates to methods for controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, a compound according to formula (I)
    wherein R1, R2, R3, R4, R5, Y, A, B are as defined herein.
OA1202200225 2019-12-10 2020-12-03 Methods of controlling or preventing infestation of peanut plants by phytopathogenic microorganisms. OA20722A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP19214687.6 2019-12-10

Publications (1)

Publication Number Publication Date
OA20722A true OA20722A (en) 2022-12-30

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