Use of succinate dehydrogenase inhibitors and/or respiratory chain complex iii inhibitors for improving the ratio of harmful to beneficial microorganisms
Abstract
The present invention relates to the use of succinate dehydrogenase inhibitors and/or complex III inhibitors for controlling undesired fungal pathogens and simultaneously improving the ratio of harmful to beneficial microorganisms in crops and to a method for treating crops or parts of crops for controlling undesired fungal pathogens and simultaneously improving the ratio of harmful to beneficial microorganisms by treating the crops or parts of crops with a succinate dehydrogenase inhibitor and/or a complex III inhibitor.

Term
4.8 yearsleft in the term
Expires 22 July 2031.
- Priority and filed
- Granted
- Today
- Expires
1 claim: 1 independent, 0 dependent
- 1CA 02806419 2013-01-23 ¢12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 2 February 2812 (82.02.2812) (18) International Publication Number WO 2012/013590 A3 (51 ) International Patent Classification :A01N 43/40 (2006.01 ) A011V 61/00 ¢2006.01 ) A01N 37/50 (2006.01 ) A01P 3/00 (2006.01 ) (21) Internationa f Applica tio η N umber : PCT/EP2011/062614 (22) International Filing Date: 22 July 20 il (22.07.201!) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 61/367,525 26 July 2010(26.07.2010) US 10172128.0 6 August 2010 (06.08.2010) EP (71) Applicant (for all designated States except US)·. BAYER CROPSCIENCE AG [DE/DE];Alfied-Nobel-Str. 50, 40789 Monheim (DE). (72) Inventors;and (75) In venters/Applicants (for US only);FOUGHT, Lorianne [US/US];P.O. Box 438, Kennan, CA 93630 (US). YOUNG, Herbert [US/US};501 Belmont Circle, Wake Forest, NC 27587 (US). MUSSON, George [US/US], 5205 Calverton Dr., Raleigh, NC 27613 (US). LaBOURDETTE, Gilbert [FR/FR];53, rue Antoine Renard, F7i600 Paray-le-Monial (FR). STEIGER, Dominique [FR/DE];Am Bonneshof 30, 40474 Dusseldorf (DE). RIECK, Helko [DE/DE];Dierath 29 A, 51399 Burseheid (DE). (74) Common Representative: BAYER CROPSCIENCE AG;Business Planning and Administrai ion, Law and Patents, Patents and Licensing, Alfted-Nobel-Str. 50, Building 6100,40789 Monheim (DE). Designated States (unless otherwise indicated, for every kind of national protection available)·. AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, ÏL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, M.X, MY, MZ, NA, NG, NI, NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available)·. ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG. ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FL FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). Published: — with international search report (Art. 21(3)) — before the expiration of the tinte limit for amending the claims and to be republished in the event of receipt of amendments (Rule 48.2(h)) (88) Date of publication of the international search report: 31 May 2012 wo 2012/013590 A3 IIIIIIIIIIIIIIIIIIIIIIIIIIIIIU (54) Title: USE OF SUCCINATE DEHYDROGENASE INHIBITORS AND/OR RESPIRATORY CHAIN COMPLEX III INHIBITORS FOR IMPROVING THE RATIO OF HARMFUL TO BENEFICIAL MICROORGANISMS (57) Abstract: The present invention relates to the use of succinate dehydrogenase inhibitors and/or complex 111 inhibitors for con trolling undesired fungal pathogens and simultaneously improving the ratio of harmful to beneficial microorganisms in crops and to a method for heating crops or pans of crops for controlling undesired fungal pathogens and simultaneously improving the ratio of harmful to beneficial microorganisms by treating the crops or parts of crops with a succinate dehydrogenase inhibitor and/or a com plex III inhibitor.
236 paragraphs in 45 sections, as filed
81590560
-2aetivities of beneficial microorganisms. It would be desirable if such active ingredients even would increase the quantity of beneficial microorganisms.
It has been surprisingly found by the present inventors that succinate dehydrogenase inhibitors and/or respiratory chain complex III inhibitors, in particular fluopyram, effectively control the presence of a large number of harmful or at least undesired fungal pathogens, while the presence of beneficial microorganisms on the treated crop is at least not impaired or more preferably even significantly increased. Consequently, the treatment of the crops according to the invention leads to an improved ratio of harmful to beneficial microorganisms.
Thus, the present invention relates to the use of succinate dehydrogenase inhibitors and/or respiratory chain complex 111 inhibitors for controlling undesired fungal pathogens without impairing the content of beneficial microorganisms in crops and more preferably to a simultaneous improvement of the ratio of harmful to beneficial microorganisms.
The present invention as claimed relates to use of a succinate dehydrogenase inhibitor and a complex Ill inhibitor for controlling undesired fungal pathogens without impairing the content of beneficial microorganisms in crops, wherein the succinate dehydrogenase inhibitor is fluopyram and the complex HI inhibitor is trifloxystrobin, and wherein the undesired fungal pathogens are selected from the group consisting of Botrytis spp, Rhizopus spp, Pénicillium spp., Cladosporimn spp., Aspergillus niger, Aspergillus flavus, Aspergillus spp., Alternaria spp., Fusarium spp., Aerobasidium spp., and Powdery Mildew Diseases, and wherein the beneficial microorganisms are selected from the group consisting of pink yeast, white yeast, yellow yeast, Bacillus spp., Epicoccum spp., white bacteria, yellow bacteria, black bacteria, Paecilomyces spp., and Ulocladium spp.
Figure 1 : demonstrates the percentual change of beneficial and harmful microorganisms in the surface mtcroflora of stone fruits after a preharvest treatment with LUNA Sensation™ (SC 500 formulation of a mixture of fluopyram and trifloxystrobin in a 1:1 ratio).
In conjunction with the present invention “controlling” denotes a significant reduction of pathogens in comparison to the untreated crop, more preferably the infestation is essentially diminished (50-79%), most preferably the infestation is totally suppressed (80-100%).
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- 2aIn conjunction with the present invention not impaired” means that neither the content nor the activity of the beneficial microorganisms after the treatment with the succinate dehydrogenase inhibitor and/or the complex II] inhibitor is decreased.
In conjunction with the present invention increasing the content of beneficial microorganisms” means that after the treatment with the succinate dehydrogenase inhibitor and/or the complex 1Π inhibitor the content of the beneficial microorganism is higher than before treatment. Preferably the content of the bene ficial microorganism is as twice as high as before treatment with the succinate dehydrogenase inhibitor and/or the complex III inhibitor, More preferably the content of the beneficial microorganism is tenfold increased after treatment with the succinate dehydrogenase inhibitor and/or the complex III inhibitor.
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-3The phrase “improved ratio of harmful to beneficial microorganisms” denotes that the content of harmful microorganisms is decreased while the content of beneficial microorganisms remains . constant or preferably is increased.
In the context of the presort invention, succinate dehydrogenase inhibitors arc all active compounds 5 ' having an inhibiting action on the enzyme succinate dehydrogenase in the mitochondrial respiratory chain, hr a preferred embodiment of the present invention, the succinate dehydrogenase inhibitors are selected from the group consisting of fluopyram, isopyrazam, boscalid, penthiopyrod, penfltifen, sedaxane, fluxapyroxad, bixafeti, N-[9-(dichloromethylene)-l<sub>t</sub>2,3,4-tetrahydro-l,4medianonaphthalen-5-yl]'3-(difluoioinclhyl)-l-niethyMH-pyrazole-4-CBrboxamidc and 310 difluoromethyl-l-mcthyHH-pyrazolc-4-carbaxylic acid (2-(2,4-dichlorophenyI)-2-mcthoxy-lmethyl-ethylj-amide and also from mixtures of these compounds. In a particularly preferred embodiment of the present invention, the succinate dehydrogenase inhibitor is fluopyram.
Bixafea of the chemical name N-Q'/t’-dichloro-S-fluoro-l.l’-biphenyJ^-yO-S-idifluoroinethyl}-!mcthyi-1 H-pyrazole-4-c'arboxairlide and processes suitable for its preparation from commercially available starting materials are described in WO 03/070705.
. Penflufen of the chemical name N-[2-(l^-dimethylbutyl)ph«ylJ-5-{hjoro-l,3-diniethyl-!Hpyrazole-4-carboxaniidc and processes suitable for its preparation from commercially available starting materials are described in WO 034)10149.
Fluopyram of the chemical name N-([3-ch1oro-5-(trifluororaethyl)-2-pyridinyl]elhyl}-220 (trifluoromethyljberwamide and processes suitable for its preparation from commercially available starting materials are described in EP-A-1 389 614.
. Sedaxane is a mixture comprising the two cis-isomcrs of 2'-[( 1RS,2RS)-1, l'-bicycloprop-2-yl}-3(difli!oromcthyl)-I-iirethylpyrazDie-4-carboxaiijlidc and the two trans-isomers of 2'-[(lRS/SR)l,r-bicycIoprop-2-yl]-3-(difluoromediyl)-l-mclhylpyrazole-4-cartxjxflnilide. Sedaxanc and processes suitable for its preparation from commercially available starling materials are described in WO 03/074491, WO 2006/015865 and WO 2006/015866.
Isopyrazam is a mixture comprising the two syn-isomers of 3-(difluoromelhyl)-l-methyl-N[(1 RS ,4 5R,9RS)-1 ^,3,4-telrabydro-9-isopropyl-1 <sub>t</sub>4-metbanonaphthale&-5 -ylJpyrazole-4 carboxamide and the two anti-isomers of 3-{difliwromethyl)-l-mcthyl-N-[(lRS,4SR,9SR)-l ,23,4CA 02Θ06419 2013-01-23
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-4tetrahydro-9-isopropyl-l,4-methanonaphthalen-5-yl]pyrazole-4-carboxam ide. 1 sopyrazam and processes suitable for its preparation from commercially available starting materials are described in WO 2004/035589.
PcnthiopyTad of the chemical name (RS)-N-[2-(1,3-dimethylbutyl)-3-thienyl]-1 -methyl-3(trifluoromethyl)pyrazole-4-carboxamide and processes suitable for its preparation from commercially available starting materials are described in EP-A-0 737 682.
Boscalid of the chemical name 2-chloro-N-(4'-chlorobiphenyl-2-yl)nicotinamide and processes suitable for its preparation from commercially available starting materials are described in DE-A 195 31 813.
Fluxapyroxad of the chemical name 3·(άίί!υθΓοηιεών!)-Ι·ηΐ6ΐΙινΙ'Ν-(3'.4'.5'·!ηΠυθΓθ-ΚίρΙιεηγ|·2· yl)-iH-pyTazole-4-carboxamide and processes suitable for its preparation from commercially available starting materials are described in WO 2005/J 23690.
N-[9-( dichloromethylene )-1,2,3,4-tetrahydro- l,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1methyl-lH-pyTazole-4-carboxamide and processes suitable for its preparation from commercially available starting materials are described in WO 2007/048556.
-Difluoromethyl-1 -methyl-1 H-pvrazoIe-4-caiboxylie acid [2-(2.4-dichloropheny I)-2-methoxy-1 methyl-ethyl]-amide usually is a mixture of 4 different stereo isomers. Processes suitable for its preparation from commercially available starting materials are described in WO 2008/148570. The different stereo isomers (+)-3-difluoromethvl-1 -methyl- lH-pyrazole-4-carboxylie acid [(lR,2S)-2(2,4-dichloropheny l)-2-methoxy-1 -methyl-ethyl]-amide, (-)-3-difluoromethyl-1 -methyl-1Hpyrazole-4-carboxylic acid [( I S,2R)-2-(2,4-dichloropheny 1)-2-methoxy-1 -methyl-ethvlj-amide; (-)3 -difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxyhc acid[(lR_2R)-2-(2,4-dichlorophenyl)-2methoxy-l-methyl-ethyl]-amide and (+)-3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid ((1 S,2S)-2-(2,4-dichloropheny I )-2 -methoxy-1-methyl-ethvlj-amide can be separated, for example by HPLC, using a chiral stationary phase column, as described in WO 2010/000612.
Inhibitors of the respirator.' chain at complex III. also referred herein to complex III inhibitors”, which can be used in accordance with the present invention are selected from the group consisting of for example (3.1) amisulbrom (348635-87-0), (3.2) azoxystrobin (131860-33-8),(3.3) cyazofamid (120116-88-3), (3.4) dimoxystrobin (141600-52-4), (3.5) enestroburin (238410-11-2)
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-5(known from WO 2004/058723). {3.6) famoxadone (131807-57-3) (known from WO 2004/058723), (3.7) fenamidone (161326-34-7) (known from WO 2004/058723). (3.8) fluoxastrobin (361377-29-9) (known from WO 2004/058723). (3.9) kresoxim-methy! (143390-890) (known from WO 2004/058723), (3.10) metommostrobin (133408-50-1) (known from WO 2004/058723), (3.11) oiysastrobin (189892-69-1) (known from WO 2004/058723), (3.12) picoxystrobin (117428-22-5) (known from WO 2004/058723), (3.13) pyraclostrobin (175013-18-0) (known from WO 2004/Û58723), (3.14) pyrametostrobin (915410-70-7) (known from WO 2004/058723), (3.15), pyraoxystrobin (862588-11-2) (known from WO 2004/058723), (3.16) pyribcncarb (799247-52-2) (known from WO 2004/058723), (3.17) trifloxystrobin (141517-21-7) (known from WO 2004/058723), (3.18) (2E)-2-(2-{ [6-(3-chloro-2-methylphenoxy )-5fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-rnethylethanamide (known from WO 2004/058723), (3.19) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(lE)-l-[3.
(trifluoromethyl)plienyl]ethy lidene}amino}oxy]methy!}plienyl)etlianamide (known from WO 2004/058723) and salts thereof. (3.20) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({l-[3(trifluoroniethvl)phenyl]etlioxy }iiniiio)nietliyl]plienyl Jethanamide ( 158169-73-4), (3.21 ) (2 E)-2-(2[(( [( IE)-1 -(3-( [(E)-1 -lluoro-2-phenyletheny!]oxy }phenyl)ethylidene]amino}oxy)methyl[phenyl] 2-(methoxyimino)-N-methylethanamide ¢326896-28-0), (3.22) (2E)-2-(2-[(([(2E,3E)-4-(2,6dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]plienyl}-2-(methoxy!mino)-Nmetliylethananiide, (3.23) 2-chlofo-N-( 1,1,3-trimethy 1-2,3-dihvdro-1 H-inden-4-yl)py ridine-3carboxamide (119899-14-8). (3.24) 5-methoxy-2-methyl-4-(2-{[(i(lE)-l-[3-(trifluoromethyl)phenyl]ethylideiie}ammo)oxy]melhyl}phe!iyl)-2,4-diiiydro-3H-l,2,4-lriazol-3-one, (3,27) 2-(2[(2.5-dimethylphenoxy)methy! [phenyl} -2-methoxy-N-methylacetamide ( 173662-97-0 ), ( 3.2 8 ) (2R)-2-(2-[(2,5-dimethylphenoxy)methyl]phenyl [-2-methoxy-N-methylacetamide (394657-24-0) and salts thereof.
In a preferred embodiment oftlie invention the complex ill inhibitor is a strobilurine selected from the group consisting of (3.1) amisulbrom (348635-87-0), (3,2) azoxystrobin (131860-33-8).(3.4) dimoxystrobin (141600-524), (3.5) enestroburin (238410-11-2) (known from WO 2004/058723), (3.8) fluoxastrobin (361377-29-9) (known from WO 2004/058723), (3.9) kresoxim-methyl (143390-89-0) (known from WO 2004/058723), (3.10) metommostrobin (133408-50-1) (known from WO 2004/058723), (3.11) oiysastrobin (189892-69-1) (known from WO 2004/058723), (3.12) picoxystrobin (117428-22-5) (known from WO 2004/058723). (3.13) pyraclostrobin (175013-18-0) (known from WO 2004/058723), (3.14) pyrametostrobin (9Î5410-70-7) (known from WO
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-62004/058723), (3.15), pyraoxystrobin (862588-11-2) (known from WO 2004/058723), (3.16) pyribencarb (799247-52-2) (known from WO 2004/058723), (3.17) trifloxvstrobin (141517-21-7) (known from WO 2004/058723), (3.18) (2E)-2-(2-( [6-(3-chloro-2-methvlphenoxy )-5fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide (known from WO 2004/058723), (3.19) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(lE)-i-[3(trifluoromethyl)phenyl]ethylidene}ainino)oxy]methyl}phenyl}ethanamide (known from WO 2004/058723) and sails thereof., (3.20) {2E)-2-(methoxyimmo)-N-methyl-2-{2-[(E)-({l-[3· (trifluoromethyl)phenyl]ethoxy }imino)methy l]phenyi}ethanamide ( 158169-73-4), (3.21 ) (2E)-2-{2[({[( 1 E)-1 -{3-{ [(E)-1 -ftuoro-2-phenylethenyl]oxv }phenyl)ethylidene]amino}oxY)methyl]phenyl} 2-(methoxyimino)-N-methylethanamide (326896-28-0), (3.22) (2E)-2-{2-[({[(2E,3E}4-(2<sub>;</sub>6dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-Nmethylethanamide, (3,23) 2-chloro-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)pyridine-3carboxainide (119899-14-8), ¢3.24) 5-methoxy-2-methyl-4-(2-{[(i(lE)-l-[3-(triiluoromethyi)phenyl]ethylidene}amino)oxylmethyl [phenyl)-2,4-dihydro-3H- l,2,4-triazol-3-one, (3.27) 2-(2[(2,5-dimetbylpheiioxy)metbyl]plienyl}-2-nietlioxy-N-niethylacetamide ( i 73662-97-0), (3.2 8) (2R)-2-[2-[(2,5-dimelhvlphenoxv)methyl]phenyl}-2-methoxy-N-methylacetamide (394657-24-0) and salts thereof.
Most preferably, trifloxystrobine or fluopvram or a combination of both is used.
As a non-exhaustive enumeration, examples of beneficial microorganisms are selected from the group consisting of pink yeast, white yeast, yellow yeast, Bacillus spp.. Epicocctim spp., white bacteria, yellow bacteria, black bacteria, Paecilomyces spp., and Ulocladtum spp., preferably from Paecilomyces spp., Ulodadium spp.. white and yellow yeasts and white and yellow bacteria most preferably<sup>7</sup> of yellow bacteria
As a non-exhaustive enumeration, examples of harmful microorganisms are selected from the group consisting of Botrytis spp, Rhizopus spp, Perici/Hum spp,, Cladospormm spp., Aspergillus niger, Aspergillus flavus, Aspergillus spp., Alfernaria spp., Fusarium spp, Aerobasidium spp. Powdery Mildew Diseases such as Blumeria diseases caused for example by Blumeria grammis.
Podosphaera diseases caused for example by Podosphaera leucotricha
Sphaerotheca diseases caused for example by Sphaerotjieca fiiliginea
Uncinula diseases caused for example by<sup>7</sup> Uncinula necator
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-7Rust Diseases such as
Gymnosporangium diseases caused for example by Gymnosporangium sabinae Hemileia diseases caused for example by Hemileia vastatrix
Phakopsora diseases caused for example by Phakopsora pachyrhizi and Phakopsora meibomiae 5 Puccinis diseases caused for example by Puccinia recondite, and Puccinia Lriticina;
Uromyces diseases caused for example by Uromyces appendiculahis Oomycete Diseases such as
Bremia diseases caused for example by Brcniia lactucac
Peronospora diseases caused for example by Peronospora pisi and Peronospora brassicae
Phstophthora diseases caused for example by Phvtophthora infestans Plasmopara diseases caused for example by Plasmopara vkicola
Pseudoperonospora diseases caused for example by Pseudoperonospora humuli and Pseudoperonospora cubensis
Pythium diseases caused for example by Pythium ultimum
5 Leafspot, Leaf blotch and Leaf Blight Diseases such as
Altemaria diseases caused for example by Altemaria solani Cercospora diseases caused for example by Cercospora beticola Cladiosporium diseases caused for example by Cladiosporium cucumerinum Cochliobolus diseases caused for example by Cochliobolus sativus (Conidiaform: Drechslera, Syn: Helnnnthosporium);
Colletotrichum diseases caused for example by Colletotrichum lindemuthianum Cvcloconium diseases caused for example by Cvcloconium oleaginum Diaporthe diseases caused for example bv Diaporthe ci tri
Elsinoe diseases caused for example by Elsinoe fawcettii
Glocosporium diseases caused for example by Glocosponum lacticolor Glomerella diseases caused for example by Glomerella cingulata
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-8Guignardia diseases caused for example by Guignardia bidwellii
Leptosphaeria diseases caused for example by Leptosphaeria macufans
Magnaporthe diseases caused for example by Magnaporthe grisea
Mycosphaerella diseases caused for example by Mycosphaerella graminicola and Mycosphaerella fijiensis
Phaeosphaeria diseases caused for example by Phaeosphaena nodonim
Pyrenophora diseases caused for example by Pyrenophora teres
Ramularia diseases caused for example by Ramularia collo-cygni
Rhynchosporium diseases caused for example by Rhynchosporium sccalis
Septoria diseases caused for example by Septoria apii;
Typhula diseases caused for example by Thyphula mcamata
Venturia diseases caused for example by Venturia inaequalis
Root- and Stem Diseases such as
Corticium diseases caused for example by Corticiiun graminearum
Fusarium diseases caused for example by Fusarium oxysponim
Gaeumannomyces diseases caused for example by Gaeumannomyces graminis
Rhizoctonia diseases caused for example by Rhizoctonia solani
Oculimacuia (Tapesia) diseases caused for example by Oeulimacula Tapesia acuformis Thielaviopsis diseases caused for example by Thielaviopsis basicola Ear and Panicle Diseases including Maize cob such as Altemaria diseases caused for example by Altemaria spp.
Aspergillus diseases caused for example by Aspergillus flavus Oadosporium diseases caused for example by Cladiosponum cladosporioides Claviceps diseases caused for example by Claviceps purpurea Fusarium diseases caused for example by Fusanum culmorum Gibberella diseases caused for example by Gibberella zeae
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-9Monographella diseases caused for example by Monographeila nivalis
Smut- and Bunt Diseases such as
Sphacelotheca diseases caused for example by Sphacelotheca reiliana Tilletia diseases caused for example by Tilleda caries
Urocvslis diseases Urocvslis occulta
Ustdago diseases caused for example by Ustdago mida,
Fruit Rot and Mould Diseases such as
Aspergillus diseases caused for example by Aspergillus flavus Botntis diseases caused for example by Botrylis cinerea
Pénicillium diseases caused for example by Pénicillium expansum and Pénicillium purpurogenum Sclerotinia diseases caused for example by Sclerotinia sclerotiorum;
Verticillium diseases caused for example by Verticillium alboatrum Seed- and Soilbome Decay, Mould, Will, Rot and Damping-off diseases Fusarium diseases caused for example by Fiisarium culnionun
Phytophthora diseases caused for example by Phytophthora cactomm Pvthium diseases caused for example by Pythium ultimum Rhizoctonia diseases caused for example by Rhizoctoma solani Scierotium diseases caused for example by Sclerotium rolfsii Canker, Broom and Dieback Diseases such as
Nectria diseases caused for example by Nectria galligena Blight Diseases such as
Monilinia diseases caused for example by Monilinia laxa
Leaf Blister or Leaf Curl Diseases including deformation of blooms and fruits such as Taphrina diseases caused for example by Taphrina deformans
Decline Diseases of Wooden Plants such as
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-10Esca disease caused for example by Phaeomoniella clatnydospora and Pbaeoacremonium aleophilum and Fomitiporia mediterranea
Diseases of Flowers and Seeds such as
Botrytis diseases caused for example by Botrytis cinerea
Diseases of Tubers such as
Rhizoctonia diseases caused for example by Rhizoctonia soiani
Helminthosporiiiui diseases caused for exauiple by Helmifithosporium soiani
Diseases caused by Bacterial Organisms such as Xanthomanas species for example Xanthomonas campestris pv. Orvzac
Pseudomonas species for example Pseudomonas syringac pv. Lachrymans
Erwinia species for example Erwinia amylovora.
Aspergillus flavus. most strains of Aspergillus parasiticus. Aspergillus nomius, Aspergillus bombycis. Aspergillus pseudotamarii, Aspergillus ochraceoroseus, Aspergillus rambefli, Emericella astellata. Emericella venezuelensis, Bipolaris spp,. Chaetomium spp,. Farrowia spp,. and Monocillium spp,. in particular Aspergillus flavus and Aspergillus parasiticus. Fusarium graminearum, Fusarium culmonim. Fusanum cerealis Fusarium acuminatum. Fusarium crookwellense. Fusarium verticiilioides. Fusarium culmorum. Fusarium avenaceum, Fusarium equiseti, Fusarium moniliforme, Fusarium graminearum (Gibberelia zeae), Fusariuin latentium, Fusarium poae, Fusarium sambucinum (G. pulicaris), Fusarium proliferatum. Fusarium subglutinans, Fusarium sporotrichioides and other Fusarium species.
In general, the use/method according to the present invention can be applied to any kind of crops/planls
By plant parts is meant all above ground and below ground parts and organs of plants such as shoot leaf flower, blossom and root, whereby for example leaves, needles, stems, branches, blossoms, fruit ing bodies, fruits and seed as well as roots, corms and rhizomes are listed. Crops and vegetative and generative propagating material, for example cuttings, corms, rhizomes, runners, tubers, grains, and seeds also belong to plant parts.
Among the plants that can he protected by the method according to the invention, mention may be made of major field crops like com, soybean, cotton, Brassica oilseeds such as Brassica napus {e.g. canola), Brassica rapa, B. juncea (e.g. mustard) and Brassica carinata, rice, wlieat, sugarbeet, sugarcane, oats, rye.
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-11 barley, millet, tnticale. flax, vine and various fruits and vegetables of various botanical taxa such as Rosaceae spp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, cherries, almonds and peaches, berry fruits such as strawberries), Ribesioidae spp., Juglandaceae spp.. Betukiceae spp., Anacardiaceae spp., Fagaceae spp.Momcvae spp., Oleaceae spp., Actinidaceae spp., Lauraceae spp., Mi/saceae spp. (for instance banana trees and plantings), Rubiaceae spp. (for instance coffee), Theaceae spp., Sterculiceae spp., Rutaceae spp. (for instance lemons, oranges and grapefruit) ; Sokmaceae spp. (for instance tomatoes, potatoes, peppers, eggplant), Liliaceae spp., Compositiae spp. (for instance lettuce, artichoke and chicory - including root chicory', endive or common chicory), Umbelliferae spp (for instance canot, parsley-, celery and celeriac), Cucurbitaceae spp. (for instance cucumber - including pickling cucumber, squash, watermelon, gourds and melons), Alliaceae spp. (for instance onions and leek), Cruciferae spp. (for instance white cabbage, red cabbage, broccoli, cauliflower, brussel sprouts, pak choi, kohlrabi, radish, horseradish, cress, Chinese cabbage), Legtirmtiosae spp. (for instance peanuts, peas and beans beans - such as climbing beans and broad beans), Chenopodtaceae spp. (for instance mangold, spinach beet, spinach, beetroots), Asteraceae spp. (for instance sunflower), Brassicaceae spp. (for instance white cabbage, red cabbage, brokkoii, cauliflower, brussel sprouts, pak choi. kohlrabi, radish as well as canola, rapeseed, mustard, horseradish, cress). (Cruciferae spp. (for instance colza), Fabctcae spp. (for instance peanuts and beans), Papihonaceae spp. (for instance soybean). Solanaceae spp. (for instance potatoes), Malvaceae (for instance okra), Asparagaceae (for instance asparagus) ; horticultural and forest crops; ornamental plants ; as well as genetically modified homologues of these crops.
According to tire invention all cereal, nut, fruit and spice plants are comprised, in particular cereals like all wheat species, rye, barley, tnticale, rice, sorghum, oats, millets, quinoa, buckwheat, fonio, amaranth, teff and durum; in particular fruits of various botanical taxa such as Rosaceae spp (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, cherries, almonds and peaches, berry fruits such as strawberries). Vit is spp. (for instance Vitis vuiifera: grape vine, raisins), Manihoteae spp. (for instance Manihot escttlenta, manioc), Theobroma spp. (for instance Theobroma cacao: cocoa), Ribesioidae spp., Juglandaceae spp., Belulaceae spp.. Anacardiaceae spp., Fagaceae spp,, Moraceae spp,, Oleaceae spp,, Actinidaceae spp,, Lauraceae spp., Musaceae spp. (for instance banana trees and plantings), Rubiaceae spp. (for instance coffee), Theaceae spp., Stcrculiccec spp., Rutaceae spp. (for instance lemons, oranges and grapefruit) ; Solanaceae spp. (for instance tomatoes, potatoes, peppers, eggplant), Liliaceae spp.; in particular nuts of various botanical taxa such as peanuts, Juglandaceae s/p,(Wainut. Persian Walnut (Juglans regia). Butternut (Jugions), Hickory, Shagbark Hickory. Pecan
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- 12(Caiya), Wingnut (Pterocarya)), Fagaceae spp. (Chestnut (Castanea), Chestnuts, including Chinese Chestnut Malabar chestnut, Sweet Chestnut, Beech (Fagus), Oak (Quercus), Stone-oak, Tanoak (Lithocarpus)); Betulaceae spp. (Alder (Alims). Birch (Betula), Hazel, Filbert (Corvlus), Hornbeam), Legittninosae spp. (for instance peanuts, peas and beans beans - such as climbing beans and broad beans), Asteraceae spp. (for instance sunflower seed), Almond, Beech, Butternut, Brazil nut, Candlenut, Cashew, Colocvnth, Cotton seed, Cucurbita ficifolia. Filbert Indian Beech or Pongam Tree, Kola nut, Lotus seed, Macadamia, Mamoncillo, May a nut, Mongongo, Oak acorns, Ogbono nut Paradise nut. Pili nut Pine nut Pistacchio, Pumpkin seed, water Caltrop; soybeans (Glycine spp., Glycine max); in particular spices like Ajwain (Trachyspemium ammi), Allspice (Pimenta dioica), Alkanet (Anchusa anensis), Amchur - mango powder (Mangifera), Angelica (Angelica archangelica), Anise (Pimpinella anisum), Aniseed myrtle (Syzygium anisatum), Annatto (Bixa orellana L,), Apple mint (Mentha suaveolens). Artemisia vulgaris/Mugworl, Asafoetida (Ferula assafoetida), Berberis. Banana, Basil (Ocimutn basilicum), Bay leaves. Bistort (Persicaria bistorta), Black cardamom. Black cumin, Blackcurrant Black limes. Bladder wrack (Fucus vesiculosus). Blue Cohosh, Blue-leaved Mallee (Eucalyptus polybrnctea), Bog Labrador Tea (Rhododendron groenlandiciiin), Boldo (Peuiuus boldus), Bolivian Coriander (Porophyllum ruderale), Borage (Borago officinalis), Calamus, Calendula, Calumba (Jateorhiza calumba), Chamomile, Candle nut. Cannabis, Caper (Capparis spinosa), Caraway, Cardamom. Carob Pod, Cassia. Casuarma, Catnip, Cat’s Claw, Catsear, Cayenne pepper, Celastrus Paniculate - Herb., Celery salt. Celery seed, Centaury; Chervi! (Anthriscus cerefolium), Chiekweed, Chicory; Chile pepper, Chili powder. Cinchona, Chives (Allium schoenoprasum). Cicely (Myrrhis odorata), Cilantro (see Coriander) (Coriandrum sativum). Cinnamon (arid Cassia), Cinnamon Myrtle (Backhousia myrtifolia). Clary, Cleavers, Clover, Cloves. Coffee, Coltsfoot, Comfrey, Common Rue, Condurango, Coptis, Coriander. Costmary (Tanacetum balsamita), Couehgrass, Cow Parsley·' (Anthnscus sylvesfris), Cowslip, Cramp Bark (Viburnum opulus), Cress, Cuban Oregano (Plectranthus amboinicus), Cudweed, Cumin, Curry leaf (Murraya koenigii), Damiana (Tumera aphrodisiaca. T. diffusa), Dandelion (Taraxacum officinale). Demulcent, Dev il’s claw<sup>1</sup> (Harpagophyhim procumbcns), Dill seed, Dill (Anethum graveolens), Dorrigo Pepper (Tasmannia stipilata), Echinacea -, Eehinopanax Elatum, Edelweiss, Elderberry, Elderflower, Elecampane. Elcuthcrococcus scnticosus. Emmcnagoguc, Epazote (Chenopodium ambrosioides), Ephedra -, Eryngium foetidum. Eucalyptus. Fennel (Foeniculum vulgare), Fenugreek, Feverfew; Figwort, File powder. Five-spice powder (Chinese), Fo-ti-tieng, Fumitory, Galangai. Garam masala, Garden cress, Garlic chives. Garlic, Ginger (Zingiber officinale), Ginkgo biloba. Ginseng, Ginseng, Siberian (Eleutherococcus senticosus), Goat’s Rue (Galega officinalis), Goada masala, Golden Rod, Golden Seal, Goto Kola, Grains of paradise (Aframomum
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- 13 melegueta), Grains of Selim (Xvlopia aethiopica), Grape seed extract Green tea, Ground Ivy, Gtiaco, Gypsy wort. Hawthorn (Crataegus sanguinea), Hawthorne Tree, Hemp, Herbes de Provence, Hibiscus, Holly, Holy Thistle, Hops, Horehound, Horseradish. Horsetail (Equisetum tefmateia), Hyssop (Hyssopus officinalis), Jalap, Jasmine, Jiaogulan (Gynostemma pentaphyllum), Joe Pye weed (Gravelroot), John the Conqueror, Juniper, Kaffir Lime Leaves (Citrus hystrix, C. papedia), Kaala masala, Knotweed, Kokam, Labrador tea. Lady's Bedstraw, Lady's Mantle, Land cress, Lavender (Lavandula spp.}, Ledum, Lemon Balm (Melissa Officinalis), Lemon basil, Lemongrass (Cymbopogon citratus, C. flexuosus, and other species). Lemon Ironbark (Eucalyptus staigeriana), Lemon mint Lemon Myrtle (Backhou5ia citriodora), Lemon Thyme. Lemon verbena (Lippia citriodora), Licorice adaptogen. Lime Flower, Limnophila aromatica, Lingzhi, Linseed, Liquorice, Long pepper, Lovage (Levisticum officinale), Luohanguo, Mace, Mahlab, Malabathrum, Manchurian Thom Tree (Aralia manchurica)]], Mandrake, Maijoram (Origanum majorana), Mamtbium vulgare, Marsh Labrador Tea. Marshmallow. Mastic, Meadowsweet Mei Yen, Melegueta pepper ( Aframomum melegueta), Mint (Mentha spp.), Milk thistle (Silybum), Bergamot (Monarda didyma), Motherwort, Mountain Skullcap. Mullein (Verbascuin ibapsus), Mustard, Mustard seed, Nasbia inaguensis, Neem, Nepeta. Nettle. Nigella sativa. Nigella (Kolanji, Black caraway), Noni, Nutmeg (and Mace) Marijuana, Oenothera (Oenothera biennis et al), Olida (Eucalyptus olida), Oregano (Origanum vulgare, O. heracleoticum, and other species), Orris root Osmorhiza. Olive Leaf (used in tea and as herbal supplement). Panax quinquefolius. Pandan leaf, Paprika, Parsley (Petroselinum crispiun), Passion Flower, Patchouli, Pennyroyal, Pepper (black, white, and green). Peppermint, Peppermint Gum (Eucalyptus dives), Perilla, Plantain. Pomegranate, Ponch phoran, Poppy seed, Pnmrose (Primula) — candied flowers, tea, Psyllium, Purslane, Quassia, Quatre épices. Ramsons, Ras el-honout. Raspberry (leaves), Reishi, Resthanow, Rhodiola rosea, Ribeny (Syzygium luehmannii), Rocket/Arugula, Roman chamomile, Rooibos. Rosehips, Rosemary (Rosmarinus officinalis), Rowan Bernes. Rue, Safflower, Saffron, Sage (Salvia officinalis), Saigon Cinnamon, St John's Wort, Salad Burnet (Sanguisorba minor or Poterium sanguisorba), Salvia, Sichuan Pepper (Sansho), Sassafras, Savory (Saturcja hortensis, S. Montana), Schisandra (Schisandra chinensis), Scutellaria costaricana. Senna (herb), Senna obtusi folia, Sesame seed, Sheep Sorrel, Shepherd's Purse, Sialagoguc, Siberian Chaga, Siberian ginseng (Elcuthcrococcus senticosus), Siraitia grosvenorii (luohanguo), Skullcap, Sloe Berries, Smudge Stick. Sonchus. Sorrel (Rumex spp.), Southernwood, Spearmint, Speedwell, Squill. Star anise, Stevia, Strawberry Leaves, Suma (Pfaffia paniculata), Sumac. Summer savory, Sutherlandia fhirescens. Sweet grass, Sweet cicely (Myrrhis odorala), Sweet woodruff, Szechuan pepper (Xanthoxylum piperitum), Tacamahac. Tamarind, Tandoori masala. Tansy, Tarragon (Artemisia dracunculus), Tea, Teucrium polium, Thai basil, Thistle,
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-14Thyme. Toor Dali, Tomientil, Tnbulus terrestris, Tulsi (Ocimum tenuiflorum), Turmenc (Curcuma tonga). Ova Uisi also known as Beaiberry, Vanilla (Vanilla planifolia), Vasaka, Vervain, Vetiver, Vietnamese Coriander (Persicana odorata), Wasabi (Wasabia japonica), Watercress, Wattleseed, Wild ginger, Wild Lettuce, Wild thyme, Winter savon', Witch Hazel, Woliberry, Wood Avens, Wood Beton\<sup>r</sup>, Woodruff) Wormwood, Yarrow, Yerba Buena, Yohimbe, Za'atar, Zedoary Root.
Examples of fruits which can be treated according to the present invention are selected from the non-exhaustive enumeration of fruits consisting of banana, blackcurrant, redcurrant, gooseberry, tomato, eggplant, guava, lucuma, chili pepper, pomegranate, kiwifruit, grape, table grapes, pumpkin, gourd, cucumber, melon, orange, lemon, lime, grapefruit, banana, cranberry, blueberry, blackberry, raspberry, boysenberry, hedge apple, pineapple, fig, mulberry, apple, pear, apricot, peach, cherry, plum, nectarine, green beau, sunflower seed and strawberry.
Examples of vegetables which can be treated according lo the present invention are selected from the non-exhaustive enumeration of vegetables consisting of flower buds, such as: broccoli, cauliflower, globe artichokes; seeds, such as sweetcorn also known as maize, leaves, such as kale, collard greens, spinach, beet greens, turnip greens, endive; leaf sheaths, such as leeks; buds, such as Brussels sprouts, stems of leaves, such as celery, rhubarb; stem of a plant when it is still a young shoot, such as asparagus, ginger; underground stem of a plant, also known as a tuber, such as potatoes. Jerusalem artichokes, sweet potato, yam; whole immature plants, such as bean sprouts; Roots, such as carrots, parsnips, beets, radishes, turnips; bulbs, such as onions, garlic, shallots.
In a preferred embodiment of the invention the succinate dehydrogenase inhibitors and/or the complex III inhibitor ore applied to stone fruit such as apricots, cherries, almonds and peaches in order to improve the ratio of harmful to beneficial microorganisms. It has been found that the improved ratio leads to a significantly extended shelf life and storcability compared with untreated fruits.
The succinate dehydrogenase inhibitors and/or die complex III inhibitors, preferably fluopyrain, can be employed for controlling fungal pathogens without impairing the content of beneficial microorganisms in crops within a certain period of time after treating the crops bearing the fruits or vegetables or after treating the fruits or vegetables itself. Generally, the succinate dehydrogenase inhibitor is applied to the crop or to its fruits or vegetables prior to the harvest, more preferably poor to the maturation of fruits and vegetables, most preferably during the plant and fruit growth prior to its contamination with the fungal pathogen.
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- 15 Even if the succinate dehydrogenase inhibitor and/or the complex III inhibitor is applied to the crop in a pre-harvest interval the microflora on the surface of the harvested fruits is significantly improved in terms of increased beneficial and reduced harmful microorganisms.
The period of time within which fungal pathogens can be controlled generally extends from 1 hour to 6 months, preferably from 1 iveek to 1 month after the treatment of the crops or its fruits or vegetables with the active compounds.
When employing the succinate dehydrogenase inhibitors and/or the complex III inhibitor, preferably fhiopvram and/or tnfloxystrobin. according to (lie present invention for controlling fungal pathogens without impairing beneficial microorganisms, the application rates can be varied within a broad range, depending on the type of application. For foliar applications the application rates of active compound are generally ranging from 1 to 3000 g/lia, more preferably from 25 to 750 g/lia, most preferably from 30 to 500 g/lia based upon the pure a.s. (active substance).
According to the present invention, the succinate dehydrogenase inhibitor, preferably fluopyram, can be applied to all parts of the crops such as shoot, leaf, flower, root, leaves, needles, stalks, stems, flowers, vegetative buds and flower buds fruiting bodies and fruits.
Plants are understood as meaning, in the present context, all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants or crops may be plants which can be obtained by conventional breeding and optimization methods or else by biotechnological and genetic engineering methods or by combinations of these methods, including the transgenic plants and including the plant varieties capable or not capahle of being protected by plant breeders’ rights.
According to the invention the treatment of the plants with the succinate dehydrogenase inhibitors and/or the complex III inhibitor, preferably fluopyram and/or tnfloxystrobin is carried out directly by the customary' treatment methods, for example by immersion, spraying, vaporizing, fogging, injecting, dripping, drenching, broadcasting or painting. In a preferred embodiment of the invention fluopyram is applied by injecting, dripping, drenching or spraying.
The succinate dehydrogenase inhibitors and/or complex IH inhibitor, preferably fluopyram and/or tnfloxystrobin. can be converted to the customary' formulations, such as solutions, emulsions.
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-16suspensions. powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seed, and also ULV cold- and warm-fogging formulations.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents, pressurized liquefied gases and/or solid carriers, optionally with the use of surface-active agents, that is emulsifiers and/or dispersants and/or foam formers. If the extender used is water, it is also possible to employ for example organic solvents as cosolvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorocthylcncs or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water. Liquefied gaseous extenders or carriers are those liquids which are gaseous at ambient temperature and at atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons and also butane, propane, nitrogen and carbon dioxide. As solid carriers there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. As solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, pumice, marble, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. As emulsifiers and/or foam formers there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethy lene fatty alcohol ethers, for example alkylaryl polyglvcol ethers, alkylsulplionates, alkyl sulphates, arylsulphonates and protein hydrolysates. As dispersants, for example, hgnosulphite waste liquors and methy lcellulose are suitable
Tackifiers such as carboxvmethylcellulose and natural and synthetic polymers in the form of powders, granules or ladces, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal
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-17phthalocyanine dyestuffs. and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0,1 and 95 percent by weight of the succinate dehydrogenase inhibitor, preferably between 0.5 and 90 percent by weight, based upon the total formulation.
According to the present invention, tlie succinate dehydrogenase inhibitors and/or complex Ill inhibitors, preferably fluopyram and/or trifloxystrobin, as such or their formulations, can also be used as a mixture wilh known fungicides, bactericides, acaricides, nematicides, or insecticides, for example, to broaden the activity spectrum or prevent the development of resistance. In many instances, synergistic effects are obtained, i.e. the activity of the mixture exceeds the activity of the individual components.
A further embodiment of the invention relates to tlie use of a composition comprising a succinate dehydrogenase inhibitor, preferably fluopyram, and a second fungicide for controlling fungal pathogens without impairing tlie content of beneficial microorganisms
Suitable fungicides which can be used in combination with the succinate dehydrogenase inhibitor, preferably with fiuopjTam are selected from tlie group consisting of (1) inhibitors of the ergosterol biosynthesis, for example (1.1) aldimorph (1704-28-5),(1.2) azaconazole (60207-31-0). (1,3) bitertanol (55179-31-2), (1.4) bromuconazole (116255-48-2), (1,5) cy proconazole (113096-994), (1.6) diclobutrazole (75736-33-3). (1.7) difenoconazoie (119446-683), (1.8) diniconazole (83657-24-3), (1.9) dimconazole-M (83657-18-5), (1.10) dodemorph (159377-7), (1.11) dodemorph acetate (31717-87-0), (1.12) epoxiconazoie (106325-08-0),(1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (11436943-6), (1.16) fenhexamid (126833-17-8), (1.17) fenpropidin (67306-00-7), (1.18) fenpropimorph (6730603-0), (1.19) fluquinconazole (136426-54-5), (1.20) flurprimidol (56425-91-3), (1.21) flusilazoie (85509-19-9), (1.22) flutriafol (76674-2143), (1.23) fluconazole (112839-33-5). (1.24) furconazolecis (112839-324), (1.25) hexaconazole (79983-71-4), (1.26) imazalil (60534-80-7), (1.27) imazalil sulfate (58594-72-2), (1.28) imibenconazole (86598-92-7), (1.29) ipconazole ( 125225-28-7), (1.30) metconazole (125116-23-6), (1.31) myclobutanil (88671-89-0), (1.32) naflifme (65472-88-0), (1.33) nuanntol (63284-71-9), (l,34)oxpoconazole (174212-12-5), (i,35)paclobutrazol (76738-620), (1.36) pefurazoate (101903-304), (1.37) penconazole (66246-88-6), (1.38) piperalin (3478-94CA 02Θ06419 2013-01-23
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- 182), (1.39) prochloraz (67747-09-5), (1.40) propiconazole (60207-90-1), (1.41) prothioconazole (178928-70-6), (1.42) pynbulicarb (88678-67-5), (1.43) pyrifenox (88283414), ( 1.44) qumconazole (103970-75-8), (1.45) simeconazole (149508-90-7). (1.46) gpiroxamine (118134-308), (1.47) tebuconazole (107534-96-3), (1.48) terbinafine (91161-71-6), (1.49) tetraconazole (112281-77-3), (1.50) triadimefon (4312143-3), (1.51) triadimenol ¢89482-17-7),(1.52) tridemorph (81412-43-3), (1.53) triflumizole (68694-11-1), (1.54) triforine (2664446-2),(1.55) triticonazole (131983-72-7), (1.56) uniconazole (83657-22-1), (1.57) uniconazo!e-p (83657-174), (1.58) viniconazole (77174-66-4), (1.59) voriconazole (137234-62-9), (1.60) l-(4-chlorophenyl)-2(lH-l,2,4-triazol-l-yl)cycloheptanol (129586-32-9), (1.61) methyl l-(2,2-dimethyl-2,3-dihvdro-lHinden-l-yl)-lH-imidazole-5-carboxylate (111323-95-0), (1.62) N’-(5-(difluoromethyl)-2-methyl-4[3-(trimethylgilyl)propoxy]phenyl}-N-ethyl-N-methylimidofonnamide, (1.63) N-ethyl-N-methylN'-{2-methyI-5-(trifluoromethy 1)4-(3-(trimethylsilyl)propoxv]phenyl}imidoformamide and (1.64) 0-[l-(4-methoxyphenoxy)-3,3-dmiethylbutaii-2-yl] IH-imidazoIe-l-carbothioate (111226-71-2).
(2) inhibitors of the respiratory chain at complex I or II, for example (2.1) bixafen (58180946-03), (2.2) boscahd (188425-85-6), (2.3) carboxin (5234-684), (2.4) difiumetorim (130339-07-0), (2.5) fcnfuram (24691-80-3), (2.6) fiuopyram (658066-35-4), (2.7) flutolaml (66332-96-5),(2.8) fnrametpyr (123572-88-3). (2.9) furmecvclox (60568-05-0), (2.10) isopyrazam (mixture of synepimeric racemate 1RS.4SR.9RS and anti-epimeric racemate 1RS,4SR,9SR) (881685-58-1), (2.11) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.12) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.13) isopyrazam (anti-cpimcric enantiomer 1S,4R,9R), (2.14) isopyrazam (syn epimeric racemate 1RS,4SR.9RS), (2.15) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.16) isopyrazam (syn-epimeric enantiomer 1 S,4R,9S), (2.17) mepronil (55814-41-0), (2.18) oxycarboxin (5259-88-1), (2.19) penflufen (494793-67-8), (2.20) penlhiopyrad (183675-82-3), (2.21) sedaxane (874967-67-6), (2.22) thifluzamide (130000-40-7), ¢223) l-melhyl-N-[2-(l,L2,2tetrailuoroethoxy)phenyll-3-(triiluoromethyl)-lH-pyrazole4-carboxamide, (2.24) fluxapvroxad (907204-31 -3), (2.25) 3-(di fluoromethyl)-1 -methyl-14-(2-( 1,1,2,2-tetrafluoroethoxy)phenyl]-l Hpyrazole4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-( 1.1,2,3,3,3-hexafluoropropoxy)phenyl]-l-inethy!-lH-pyrazo]e-4-carboxamide and salts thereof.
(3) inhibitors of the respirators' chain at complex III, for example (3.1) amisulbrom (348635-87-0), (3.2) azoxystrobin (131860-33-8), (3 3) cyazofamid (120116-88-3), (3 4) dimoxyslrobin (141600CA 02Θ06419 2013-01-23
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-1952-4). (3.5) enesiroburin (238410-11-2) (known from WO 2004/058723), (3.6) famoxadone (131807-57-3) (known from WO 2004/058723), (3.7) fenamidone (161326-34-7) (known from WO 2004/058723), (3.8) fiuoxastrobin (361377-29-9) {known from WO 2004/058723), (3.9) kresoximmethyl (143390-89-0) (known from WO 2004/058723), (3.10) metominostrobin (133408-50-1) (known from WO 2004/058723), (3.11) orysastrobin (189892-69-1) (known from WO 2004/058723), (3.12) picoxystrobin (117428-22-5) (known from WO 2004/058723),(3.13) pyraclostrobin (175013-18-0) (know from WO 2004/058723), (3.14)pyrametostrobin (915410-707) (known from WO 2004/058723), (3.15) pyraoxystrobin (862588-11-2) (known from WO 2004/058723), (3 16) pyribcncarb (799247-52-2) (known from WO 2004/058723),(3.17) trifloxystrobin (141517-21-7) (known from WO 2004/058723), (3.18) (2E)-2-(2-{[6-(3-chloro-2methylphenoxy)-5-fluoropyrimidin-4-yl]oxy)phenyl)-2 -(methoxyimino )-N-methyletli an amide (known from WO 2004/058723). (3.19) (2E)-2-(methoxyimino)-N-methyl-2-(2-([(((lE)-i-[3(frifluoromethyl)plienyl]ethy lidene} amino)oxy]inethy! }phenyl)e til an aniide (known from WO 2004/058723) and salts thereof.. (3.20) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({l-[3(trifliioromethyl)phenyl]ethoxy }imino)iiietliyl]plienyl}ethaiiamide ( 158169-73-4), (3.21 ) (2 E)-2-(2[(( [( IE)-1 -(3-( [(E)-1 -iluoro-2-phenyletheny!]oxy }phenyl)ethylidene]amino}oxy)methy]|pheny]} 2-(metlioxyimino)-N-methylethanamide ¢326896-28-0), (3.22) (2E)-2-(2-[(([(2E,3E)-4-(2.6dichlorophenyl)buf-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxy!inino)-Ninetliyiethananiide, (3.23) 2-chloro-N-( 1,1,3-triinethy1-2,3-dihydro-1 H-inden-4-yl)pyridine-3carboxamide (119899-14-8). (3.24) 5-methoxy-2-methyl-4-(2-{[(((lE)-l-[3-(trifluoromethyl)phenyl]ethyhdene}ainino)oxy]inelhyl}phenyl)-2,4-diliydro-3H-l,2,4-triazol-3-one, (3.25) methyl (2E)-2-( 2-[((cyelopropyl[(4-methoxyphenyl)imino}methyi} sulfanybmethyi]phenyl J -3methoxyprop-2-enoate (149601-03-6), (3.26) N-(3-ethyl-3.5,5-trimethylcyclohexyl)-3(fonnylamino)-2 -hydroxy benzamide (226551-21-9), (3 27) 2-(2-((2,5dimethylphenoxy)methy!]pheny!}-2-methoxy-N-methylacetamide (173662-97-0). (3.28) (2R)-2-{2[(2,5-dimcthylphenoxy)mcthylJphcnyl}-2-mcthoxy-N-mcthylacctamidc (394657-24-0) and salts thereof.
(4) Inhibitors of the mitosis and cell division, for example (4.1) benomyl (17804-35-2),(4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96-7). (4.4) diethofencarb (87130-20-9), (4.5) ethaboxam (162650-77-3), (4.6) fluopicohde (239110-15-7), (4.7) fuberidazole (3878-19-1), (4.8) pencycuron (66063-05-6), (4 9) thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.11) thiophanatc (23564-06-9). (4.12) zoxarmdc ¢156052-68-5), (4.13) 5-chloro-7-(4CA 02Θ06419 2013-01-23
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-20methylpipendin-l-yl)-6-{2,4,6-tnfluorophenyl)[l,2,4]triazolo[l,5-a]pyninidine (214706-53-3) and (4.14) 3-chtoro-5-(6-chloropyridin-3-yl)-6-methyl4-(2.4,6-trifluorophenyl)pyridazine (100275687-7) and salts thereof.
(5) Compounds capable to have a multisite action, like for example (5.1 ) bordeaux mixture ¢80115 63-0), (5.2) captafol (2425-06-1), (5.3) captan (133-06-2) (known from WO 02/12172), (5.4) chlorothalonil (1897-45-6), (5.5) copper hydroxide ¢20427-59-2), (5.6) copper naphthenate (133802-9), (5,7) copper oxide (1317-39-1), (5.8) copper oxychionde (1332-40-7), (5.9) copper(2+) sulfate (7758-98-7), (5.10) dichlofluanid (1085-98-9). (5.11) dithianon (3347-22-6), (5.12) dodine (2439-10-3), (5.13) dodine free base, (5.14) ferbam (14484-64-1), (5.15) lluorofolpct (719-96-0), (5.16) folpet (133-07-3), (5.17) guazatine (108173-90-6), (5,18) guazatine acetate, (5.19) lmtnoctadinc (13516-27-3), (5.20) uninoctadinc albcsilatc (169202-06-6), (5.21) lmmoctadinc triacetate (57520-17-9), (5.22) mancopper (53988-93-5), (5.23) mancozeb (2234562), (5.24) maneb (12427-38-2), (5.25) metiram (9006-42-2), (5.26) metiram zinc (900642-2), (5.27) oxine-copper (10380-28-6), (5.28) propamidine (104-32-5), (5.29) propineb (12071-83-9), (5.30) sulphur and sulphur preparations including calcium polysulphidc (7704-34-9). (5.31) thiram (137-26-8), (5.32) tolylfluanid (731-27-1), ¢5.33) zineb (12122-67-7), (5.34) ziram (137-304) and salts thereof.
(6) Compounds capable to induce a host defence, like for example (6.1) acibcnzolar-S -methyl (135158-54-2), (6.2) isotianil ¢224049-04-1), (6.3) probenazole (27605-76-1) and (6.4) tiadinil (223580-51-6).
(7) Inhibitors of the amino acid and/or protein biosynthesis, for example (7.1 ) andoprim (23951 -851), (7.2) blasticidin-S (2079-00-7), (7.3) cyprodiml (121552-61-2), (7.4) kasugamvein (6980-18-3).
(7.5) kasugamvein hydrochloride hydrate (1940846-9), (7 6) mepanipyrim (11023547-7) and (7,7) pyrimetham! (53112-28-0).
(8) Inhibitors of the ATP producüon, for example (8.1) fenlin acetate (900-95-8), (8,2) lenlin chloride (639-58-7), (8.3) fentin hydroxide (76-87-9) and (8.4) silthiofam (175217-20-6).
(9) Inhibitors of the cell wall synthesis, for example (9.1) benthiavalicarb (177406-68-7),(9.2) dimethomorph (110488-70-5), (9.3) flumorph (21186747-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polvoxins (11113-80-7), (9.7) polyoxorim (22976-86-9), (9.8) validamycin A (37248-47-8) and (9.9) valifenalate (283159-944; 283159-90-0),
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-21(10) inhibitors of the lipid and membrane synthesis, for example ( 10. i) biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (1710949-8), (10.5) etndiazole (2593-15-9), (10.6) iodocaib (55406-53-6), (10.7) iprobenfos (26087-47-8), (10,8) isoprothiolane (50512-35-1), (10.9) propamocarb (25606-41-1), (10.10) propamocarb hydrochloride (2560641 -1 ). (10.11) prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18-6), (10.13) quintozene (82-68-8), (10,14) tecnazene (117-18-0) and (10.15) tolclofos-methyl (57018-04-9).
(11) Inhibitors of tbe melamne biosynthesis, for example (11.1) carpropamid (104030-54-8), (11,2) dicloevmet (139920-32-4). (11.3) fenoxaml (115852-48-7), (11.4) phthalide (27355-22-2), (11.5) pyroquilon (57369-32-1) and (11.6) tricyclazolc (41814-78-2).
(12) Inhibitors of (he nucleic acid synthesis, for example (12.1) benalaxyl (71626-114), ( 12.2) benalaxyi-M (kiralaxyl) (98243-83-5), (12.3) bupirimate (4148343-6), (12.4) elozylacon (6793285-8), (12.5)dimelhiriinol (5221-534), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-307), (12.8) hymexazol (10004 44-1). (12.9) metalaxyl (57837-19-1). (12.10) metalaxyl-M (mefenoxam) (70630-17-0), (12.11) ofurace (5881048-3), (12.12) oxadixyl (77732-09-3) and (12.13) oxolinic acid (14698-29-4).
(13) inhibitors of the signal transduction, for example (13.1) chlozolinate (84332-86-5),(13.2) fenpicioml (74738-17-3). (13.3) fludioxonil (131341-86-1). (13.4) iprodione (36734-19-7),(13.5) procyrnidone (32809-16-8).(13.6) quinoxyfen( 124495-18-7) and (13.7) vinclozolin (5047144-8).
(14) Compounds capable to act as an uncoupler, like for example (14.1) binapacryl (485-314).
(14,2) dinocap (131-72-6), (14,3) fenmzone (89269-64-7), (14.4) fluazinam (79622-59-6) and ( 14,5) meptyldinocap ( 131-72-6).
(15) Further compounds like for example (15.1) i-(4-{4-[(5R.)-5-(2,6-difiuorophenyl)4,5-dihydrol^-oxazol-3-yll-l,3-thiazol-2-yl}piperidin-l-yl)-2-f5-methyl-3-(tri fluoromethvl)-IH-pyrazoI-lyljethanone, (15,2) 1 -(4-methoxyphenoxy)-3,3-diinethyîhutan-2-yl IH-i in id azole-1 -carhoxyiate (111227-17-9), (15.3) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyTidine (13108-52-6). (15.4) 2,3dibutyl-6-clilorothieno[2,3-d]pyriniidiri-4(3H)-one (221451-58-7), ( 15.5) 2-[5-metliyl-3(trifluoromethyl)-lH-pyrazol-l-yl]-l-(4-{4-[(5R)-5-phenyl-4.5-dihydro-1.2-oxazol-3-yl]-l,3lhiazoI-2-yl}piperidin-l-yl)ethanone, (15,6) 2-butoxy-6-iodo-3-propyl-4H-ehromen-4-one, (15.7)2phenylphenol and salts (9043-7), (15.8) 3,4.5-tnchloropyTidine-2,6-dicarbonitnle (17824-85-0), (15,9) 3-[5-(4-ch!orophenyl)-2,3-dimethyl-l,2-oxazolidin-3-yi]pyridiue, (15.10) 3-chloro-5-(4CA 02Θ06419 2013-01-23
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-22chloropheny l)-4-(2,6-difluorophenvl)-6-melhylpyridazine. ( 15.11 ) 4-(4-chlorophenyl )-5 -(2.6difluorophenyl)-3,6-dimeihylpyridazine, (15.12) 5-amino-l,3.4-thiadiazole-2-thiol, (15.13) 5chloro-N<sup>,</sup>-phenyl-N<sup>,</sup>-(prop-2-yn-l-yl)lhiophene-2-sulfonohydrazide (134-31-6), (15.14) 5-methyl-6octyl[l,2,4]triazoIo[l,5-a]pyrimidin-7-amine, (15.15) ametoctradin (865318-974), (15.16) benthiazole (21564-17-0), (15.17) bethoxazin (163269-30-5), (15.18) capsimycin (70694-08-5), (15,19) carvone (99-49-0), (15,20) chinomethionat (2439-01-2). (15,21) chlazafenone (688046-61 9), (15.22) cufraneb (11096-18-7), (15.23) cyflufenamid (180409-60-3), (15.24) cymoxani! (5796695-7), (15.25) cyprosulfamide (221667-31-8), (15.26) dazomet (533-74-4), (15.27) debacarb (62732-91-6), (15.28) dichlorophen (97-234), ¢15.29) diclomezine (62865-36-5),(15.30) difenzoquat (43222-48-6), (15.31) difenzoquat methylsulphate (4322248-6), (15.32) diphenylamine (122-39-4), (15.33) ecomate, (15,34) ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2enoate, (15.35) flumetover (154025-044), (15.36) fluoroimide (41205-214).(15,37) flusulfamide (106917-52-6), ¢15.38) flutianil (304900-25-2), (15.39) fosetyl-aluminium (39148-24-8),(1540) fosetyl-calcium. (15.41) fosetyl-sodium (39148-16-8), (15.42) hexachlorobenzene (118-74-1), (15.43) inimamvcin (81604-73-1), (15.44) metliasulfocarb (6695249-6), ( 15.45) methyl isothiocyanate (556-61-6), (15,46) metrafenone (220899-03-6), (15.47) mildioinycin (67527-71-3), ( 15.48) N-(4-chlorobenzyl)-3-(3-methoxy4-(prop-2-yii-l -y ioxv)pheny Ijpropanamide, ( 15.49) N[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy4-(prop-2-yn- l-vloxy)phenyl)propanamide, ( 15,50) N-[(5-bromo-3 -chloropy rid in-2-y l)methyl]-2,4-dichloropyridine-3 -carboxamide, ( 15.51 ) N-[ 1 -(5 bromo-3-chloropyrid in-2-yl)ethyl]-2,4-dichloropvTidine-3-carboxamide. ( 15.52) N-[ l-(5-bromo-3chloropyridin-2-yl)elhyl]-2-fli!oro-4-iodopyridine-3-carboxamide. (15.53) N-{(E)[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, ( 15.54) N- {(Z)-[(cyclopropylmetho.xy)immo][6-(difluoroinethoxy)-2,3-difluorophenyl]methy 1} -2 phenylacetamide (221201-92-9), (15.55) natamycm (7681-93-8), ( 15.56) nickel dimethyldithiocarbamate (15521-65-0), (15.57) nilrothal-isopropvl (10552-74-6), (15.58) N-methyi2-( 1-( [5-mcthyl-3-(trifluoroincthyl)· 1 H-pyrazol-1 -yl]acetyl}pipcndin-4-y 1)-14-(1,2.3,4tetrahydronaphthalen-1 -yl)-l ,3-thiazole-4-carboxamide, (15.59) N-methyl-2-(l-{[5-methyl-3(trifluoromcthyl)-l H-pyrazol- 1-yl J acetyl }pipcridin4-yl)-N-((lR)-l, 2,3,4-tctrahydronaphthalcn-lyl]-l,3-thiazole-4-carboxamide, (15.60) octhilinone (26530-20-1), (15,61) oxantocarb (917242-127), (15,62) oxyfenthiin (34407-87-9), (15.63) pentachlorophenol and salts (87-86-5), (15,64) pentyl (6-[({[(l-methyl-lH-tetrazol-5-yl)(phenyi)methylidene]ainino}oxy)methyl]pyridin-2-yl}carbamate, (15.65) phenazine-1-carboxylic acid, (15.66) phenothrin, (15.67) phosphorous acid and its salts (13598-36-2), (15.68) propamocaib-fosetylate, (15.69) propanosine-sodium (88498-02-6),(15.70)
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-23 proquinazid (189278-124), (15.71) pxTrolnitrine (1018-71-9) (known from EP-A 1 559 320), (15.72) qumotin-8-ol (134-31-6), (15.73) quinolin-8-ol sulfate (2:1) (134-31-6), (15.74) fenpyrazamine (473798-59-3), (15.75) tebufloquin (376645-78-2), (15.76) tecloflalam (76280-916), (15.77) tolnifanide (304911-98-6), (15.78) triazoxide (72459-58-6), (15.79) trichlamide (701935 21-4),(15.80) zanlamid (84527-51-5) and salts thereof.
(16) Further compounds like for example (2.27) l-methyl-3-(trifluoromethyl)-N-[2’(tnfluoromethyl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (2.28) N-(4'-chlorobiphenyl-2-yl)-3(difluoromethyl)-1 -methyl-lH-pyrazole-4-carboxamide, (2.29) N-(2',4'-dichlorobiphenyl-2-yl)-3(difluoromcthy 1)-1 -methyl· lH-pyrazolc-4-carboxamidc, (2.30) 3-(dilluoromcthyl)- l-mcthyl-N«l4’· (frifluoromethy])biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (2,31) N-(2\5’-difluorobxphetiy!-2-y!)1 -methyl-3-(trifluoromethy 1)-1 H-pyrazolc-4-carboxamidc, (2.32) 3-{difluoromethyl)- l-mcthyl-Nfd’-tprQp-l-yn-l-yObiphenyl^-ylJ-lH-pvrazole^-carboxamide (known from WO 2004/058723), (2.33) 5-fluoro-L3-dimethyl-N-[4<sup>,</sup>-(prop-l-yn-l-yl)biphenyl-2-yl)-tH-p>Tazole-4-carboxamide (known from WO 2004/058723), (2.34) 2-chloro-N-[4'-(prop-l-yn-l-yl)b)phenyl-2-y(]pyndine-315 carboxamide (known from WO 2004/058723). (2,35) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbut-l· yn-l-yl)biphenyl-2-yl]-l-methyl-lH-pyrazole-4-carboxamide (known from WO 2004/058723), (2.36) Ν-ί4'-(3,34ΐπκΰιν1όώ-1-νη-1-ν1)&ρ1κην1-2-ν1]-5-ί]ιΐ0Γ0-1,3-όΐπκώνΙ-1Η-ρνΓ3ζο1ε-4carboxamide (known from WO 2004/058723), (2.37) 3-(difluoromethyl)-N-(4'-ethynylbipheny!-2yl)-l-methyl-lH-pyrazoie-4-caiboxantide (known from WO 2004/058723), (2.38) N-(4'20 ethynylbiphenyl-2 yl)-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide (known from WO 2ΟΟ4/Ο58723), (2.39) 2-chloro-N-(4'-etbynylbipbenyl-2-yl)pyridiiie-3-carboxaniide (known from WO 2004/05 8 723), (2.40) 2-chloro-N-[4’-(3,3 -dimethylbut-1 -yn-1 -yl)biphenyl-2-yl]pyridine-3 carboxamide (known from WO 2004/058723), (2.41) 4-(4ί(1ϋοΐΌΐικΐ1ιν1)-2-πιοΐ1ΐ}Ι-Ν-[4'-(ίπίΙιιθΓθmethy!)biphenyl-2-yl]-1.3-thiazole-5-caiboxamide (known from WO 2004/058723), (2.42) 52 5 fhioro-N-[4'-(3 -hvdroxy-3-niethy lbut-1 -yn-1 -yl )b iphenyl-2-yl]-1.3 -dimethyl-1 H-pyrazole-4carboxamide (known from WO 2004/058723), (243)2-chloro-N-)4’-(3-hydroxy-3-meihv!but-l-ynl-yl)bipheny!-2-y!]pyridine-3-carboxamide (known from WO 2004/058723), (2.44) 3(difiuoromethyl)-N-[4'-(3-methoxy -3-methylbut-l-\n-f-yl)biphenyl-2-yl]-l-methyl- lH-pyrazole-4carboxamide (known from WO 2004/058723), (2.45)5-fluoro-N-[4<sup>,</sup>-(3-methoxy-3-methylbut-l-yn30 l-yl)biphenyl-2-yl]-l,3-dimethyl-lH-pyrazole-4-carboxamide (known from WO 2004/058723), (2.46) 2-chloro-N-[4'-(3-metho.xy-3-methylbut-1 -yn-1 -yl)biphenyl-2-yl]pyridine-3-carboxamide (known from WO 2004/058723) and salts thereof., (15.81) (5-bromo-2-mctho.xy-4-mcthylpyridinCA 02Θ06419 2013-01-23
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-243-ylX23,4-trimethoxy-6-methylphenyl)methanone (known from EP-A 1 559 320) and (9.10) N-[2(4-{[3-(4-chlorophenyl)prop-2-yn-l-yl]oxy}-3-methoxyphenvi)ethyl]-N2-(methylsulfonyl)valinamide (220706-934).
In a preferred embodiment the second fongicide is tnfloxvstrobm in a more preferred embodiment of the invention a composition comprising fluopyram and tnfloxvstrobm is used for controlling fungal pathogens, for instance Botryris spp. and Pénicillium spp. in stone fruits, such as cherries, nectarines, apricots and peaches.
In a further embodiment of the invention, it has been found that the pre-harvest or in season treatment of a succinate dehydrogenase inhibitor, preferably of fluopvTam. increases the storabilitv and/or the shelf life of Ihe harvested fruits or vegetables.
Investigations earned out on harvested stone fruits which were obtain from crops treated with succinate dehydrogenase inhibitors and/or strobilunnes prior to the harvest of the fruits have shown that the number of pathogen colonies was significantly reduced. In particular the presence of pathogens like Botryris spp. and Pénicillium spp. which both are the main pathogens causing post harvest problems, like of fruit rot, decreases. Likewise, the number of colonies of beneficial microorganisms, like pink yeast, while yeast, yellow yeast. Bacillus spp., Epicoccum spp., white bacteria, yellow bacteria, black bacteria, Paecilomycesspp. and Ulocloclium spp. was significantly increased.
Thus, in a preferred embodiment the invention relates to the increase of Paecilomyces spp.. Uiocladium spp.. white and yellow yeasts and white and yellow bacteria in the surface microflora of fruits, preferably of stone fruits, such as peaches, nectarines and apricots, by in-season and/or preharvest application of compositions comprising fluopyram and trifloxystrobin.
In a most preferred embodiment the invention relates to the increase of yellow bacteria in the surface microflora of fruits, preferably of stone fruits, such as peaches, nectarines and apricots, by in-season and/or preharvest application of compositions comprising fluopyram and trifloxystrobin.
The present invention is exemplified by the following example.
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-25Ex am pi es
Example I: Stone Fruit Surface Microflora Reduction
The present example demonstrates the perceptual change of beneficial and harmful microorganisms in the surface microflora of stone fruits after a preharvest treatment with LUNA Sensation (SC 500 formulation of a mixture of 21.4 vvl.-% fluopwam and 21.4 wt-% triftoxvsfcrobin in a 1:1 ratio). Multiple applications were made from March-July in 935 liters per hectare with an air-blast sprayer: harvested fruit were washed, the wash was plated on selective media; and resulting colonies were enumerated.
Table 1 and Figure 1
<td colspan="2"> Harmful/ Undesired Microorganisms</td>
<td> Botrytis</td><td> -100%</td>
<td> Pénicillium</td><td> -55%</td>
<td> Cladosporium</td><td> -91%</td>
<td> Aspergillus niger</td><td> -79%</td>
<td> Aspergillus flams</td><td></td>
<td> Aspergillus spp.</td><td> 166%</td>
<td> Altemaria</td><td> -30%</td>
<td> Fusarium spp.</td><td> -100%</td>
<td> Aercbasidium</td><td> -56%</td>
<td colspan="2"> Beneficial Microorganisms</td>
<td> Paecilomyces</td><td> 680%</td>
<td> Ulocladinm</td><td> 680%</td>
<td> Yeast Pink</td><td> -10%</td>
<td> Yeast, White</td><td> 198%</td>
<td> Yeast, Yellow</td><td> 1460%</td>
<td> Bacillus</td><td> 164%</td>
<td> Bacteria, White</td><td> 322%</td>
<td> Bacteria, Yellow'</td><td> 41620%</td>
<td> Bacteria, Black</td><td> -100%</td>
81590560
-26Κι ample 2: Stone Fruit SnrCue Mkro flora Redaction
He present example demonstrates the percentual change of bénéficia] and turmfol microorganisms in the eurfbce microflora of stone fruits following b treatment program with LUNA Sensation (SC 500 formulation of a mixture of 214 wt-% flunpyram and 21.4 wt % trifloxyarobin in a 1:1 ratio).
Multiple appUcatious were made on a two-week interval from March-July in 935 liters per hectare with an air-blast sprqyer; harvested fruit were wished, the wash was diluted ini range 1:1 to 1:1000 and plated on selective media; incubated, and resulting colonies were identified and enumerated as colony forming units pa apricot 6 days later. The samples can be described aa follow:
Pristine^ WG:
Pristine containing 280 g ai/Ha (185 g/Ha boscatid sod 94 g/Ha pyraciostrobin) was applied on dales: 6/3ΛΟ, 12/3/10,2/4/10,23M/1Q, 14/5/10,12/6/10,3/7/10, 20/7Λ0,13/8/10,4/9/10,25/W10.
LS eariy:
Lota Sensation 500 SC containing 183 g al/Ha (91 g/Ha fluopyram and 91 g/Ha trifloxystrobin) wft applied ondatra: 6Û/10,12/3/10,2M/10,23/4/10,14/5/10,12/6/10,
LSIate:
Luna Sensation 500 containing 183 g ai/Ha (91 g/Ha fluopyram and 91 g/Ha trifiootystrobm) was applied ou dates 3/7Λ0, 20/7/10,13/8/10,4/9/10,25ÆV10
LSIulfc
Luna Sensation 500 SC containing 183 g ai/Ha ¢91 g/Ha fluopyram and 91 g/Ha trifloxystrobin) was applied on dates «3/10,12/3/10,2/4/10,23/4/10, 14/5/10,12Λ5/10,3/7/10,20/7/10,13/8/10, 4/9/10,25/9/10.
CA 2806419 2017-11-02
CA 02Θ06419 2013-01-23
WO 21)12/013590
PCT/EP2011/062614
-27Table2
<td></td><td> Untre a ted</td><td> Untre ated</td><td> LS early</td><td> LS early</td><td> LS full</td><td> LS full</td><td> Pristi ne</td><td> Pristi ne</td><td> LS late</td><td> LS late</td>
<td> Dilution</td><td> 1:1</td><td> 1:1</td><td> 1:1</td><td> 1:1</td><td> 1:1</td><td> 1:1</td><td> 1:1</td><td> 1:1</td><td> 1:1</td><td> 1:1</td>
<td> Aureo- basidium</td><td> 212,5</td><td> 335</td><td> 530</td><td> 242,5</td><td> 542,5</td><td> 607,5</td><td> 767,5</td><td> 105</td><td> 315</td><td> 272,5</td>
<td> Rodtorula</td><td> 30.75</td><td> 24.5</td><td> 41,25</td><td> 7,5</td><td> 51,75</td><td> 61,25</td><td> 61.5</td><td> 32,25</td><td> 50,75</td><td> 44.5</td>
<td> Clado- sporium</td><td> 28.75</td><td> 28.5</td><td> 30,25</td><td> 1.25</td><td> 14,75</td><td> 34.5</td><td> 35,25</td><td> 10,75</td><td> 33,5</td><td> 11.75</td>
<td> Altemana</td><td> 0.5</td><td> 1.75</td><td> 1,75</td><td> 0</td><td> 1</td><td> 0,75</td><td> 1,25</td><td> 1</td><td> 0</td><td> 1,25</td>
<td> Botrytis</td><td> 0,75</td><td> 0</td><td> 0,25</td><td> 0</td><td> 0</td><td> 0</td><td> 0,25</td><td> 0</td><td> 0</td><td> 0</td>
<td> Como- Ühiium</td><td> 0</td><td> 1</td><td> 0.25</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0.25</td><td> 0.5</td><td> 0</td>
<td> Pénicillium</td><td> 0.5</td><td> 1</td><td> 2</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0.25</td><td> 0,5</td><td> 0</td>
<td> Monilinia</td><td> 0,25</td><td> 0</td><td> 0</td><td> 0,25</td><td> 0</td><td> 0</td><td> 0,25</td><td> 0</td><td> 0</td><td> 0</td>
<td> Fusarium</td><td> 0,75</td><td> 1,25</td><td> 0</td><td> 0</td><td> I</td><td> 0,25</td><td> 0</td><td> 0,5</td><td> 1,25</td><td> 0,5</td>
<td> Rhizopus</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0,25</td><td> 0</td>
<td> A. flavus</td><td> 0</td><td> 0,5</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td>
<td> A. nigcr</td><td> 0</td><td> 0</td><td> 0,75</td><td> 0</td><td> 0</td><td> 0</td><td> 0,25</td><td> 0.25</td><td> 0</td><td> 0</td>
<td> Epicoccum</td><td> 0,25</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0.25</td><td> 0</td><td> 0</td>
<td> Other Yeasts</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0,25</td><td> 0,25</td><td> 0</td><td> 0</td><td> 0</td><td> 0-5</td>
<td> Other & Unknown</td><td> 0,25</td><td> 0,25</td><td> 1.33</td><td> 0,25</td><td> 0.25</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0.25</td>
81590560
-28CLA1MS:
1. Use of a succinate dehydrogenase inhibitor and a complex til inhibitor for controlling undesired fungal pathogens without impairing the content of bénéficiai microorganisms in crops, wherein the succinate dehydrogenase inhibitor is fluopyram and the complex 111 inhibitor is trifioxystrobin, and wherein the undesired fungal pathogens are selected from the group consisting of Botrytis spp, Rhlzopus spp, Pénicillium spp., Cladosporium spp., Aspergillus niger, Aspergillusflavus, Aspergillus spp., Alternaria spp., Fusarium spp., Aerobasidium spp., and Powdery Mildew Diseases, and wherein the beneficial microorganisms are selected from the group consisting of pink, yeast, white yeast, yellow yeast, Bacillus spp., Epicoccum spp., white bacteria, yellow bacteria, black bacteria,
Paecilomyces spp., and Ulocladmm spp.
2. Use according to claim 1, wherein the ratio of the undesired fungal pathogens to beneficial microorganisms is improved.
3. Use according to claim 1 or 2, wherein the content of beneficial microorganisms on the surface of the treated crops and/or on the surface of fruits obtained from the treated crops is increased.
4. Use according to any one of claims 1 to 3, wherein the crops are stone fruit crops.
5. Use according to claim 4, wherein the crops are apricots, cherries, almonds, peaches, or combinations thereof,
6. Use according to any one of claims 1 to 5, wherein the succinate dehydrogenase inhibitor and the complex HI inhibitor are applied at an application rate of from 0.01 to 3 kg/ha based on the pure active ingredient.
7. Use according to any one of claims 1 to 6, wherein the succinate dehydrogenase inhibitor and the complex ill inhibitor are applied to the crops prior to the harvest of fruits.
8. Use according to any one of claims 1 to 7, wherein the succinate dehydrogenase inhibitor and the complex 111 inhibitor are applied in combination with a further fungicidally active compound.
9. Use according to claim 6 for controlling Botrytis spp, and Pénicillium spp. in cherries, nectarines, apricots, peaches, or combinations thereof.
CA 2Θ06419 2017-11-02
Contents45
1 sheet
Sheet 1
30 members in 16 offices
Members30
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| CA2806419A1 | Canada | A1 | |
| WO2012013590A2 | World Intellectual Property Organization (WIPO) | A2 | |
| US2012046323A1 | United States of America | A1 | |
| WO2012013590A3 | World Intellectual Property Organization (WIPO) | A3 | |
| MX2013000998A | Mexico | A | |
| KR20130041233A | Republic of Korea | A | |
| EP2597951A2 | European Patent Office (EPO) | A2 | |
| CN103237449A | China | A | |
| JP2013532672A | Japan | A | |
| CL2013000238A1 | Chile | A1 | |
| ZA201301430B | South Africa | B | |
| RU2013108173A | Russian Federation | A | |
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| RU2572759C2 | Russian Federation | C2 | |
| BR112013001959A2 | Brazil | A2 | |
| JP5974000B2 | Japan | B2 | |
| EP2597951B1 | European Patent Office (EPO) | B1 | |
| JP2016193924A | Japan | A | |
| PT2597951T | Portugal | T | |
| ES2610657T3 | Spain | T3 | |
| PL2597951T3 | Poland | T3 | |
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| KR20180004333A | Republic of Korea | A | |
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| KR101869524B1 | Republic of Korea | B1 | |
| CA2806419CThis record | Canada | C | |
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Numbers
- Publication
- 2806419
- Application
- 2806419
Titles2
- English
- USE OF SUCCINATE DEHYDROGENASE INHIBITORS AND/OR RESPIRATORY CHAIN COMPLEX III INHIBITORS FOR IMPROVING THE RATIO OF HARMFUL TO BENEFICIAL MICROORGANISMS
- French
- UTILISATION D'INHIBITEURS DE LA SUCCINATE DESHYDROGENASE ET/OU D'INHIBITEURS DU COMPLEXE III DE LA CHAINE RESPIRATOIRE POUR L'AMELIORATION DU RAPPORT DES MICROORGANISMES DANGEREUXA BENEFIQUES
Classification
- CPC, 7
- A01N37/50
- A01N43/40
- A01N61/00
- A01N43/32
- A01N43/56
- A01N43/653
- A01N57/20
- IPC, 3
- A01N37 50
- A01N61 00
- A01P3 00