( 12 ) United States Patent
`Fabri et al .
`
`US 11,445,727 B2
`( 10 ) Patent No .:
`( 45 ) Date of Patent :
`* Sep . 20 , 2022
`
`US011445727B2
`
`( 54 ) FUNGICIDAL COMBINATIONS
`( 71 ) Applicant : UPL LTD , Haldia ( IN )
`( 72 ) Inventors : Carlos Eduardo Fabri , Sao Paulo - SP
`( BR ) ; Rajju Devidas Shroff ,
`Maharashtra ( IN ) ; Jaidev Rajnikant
`Shroff , Dubai ( AE ) ; Vikram Rajnikant
`Shroff , Dubai ( AE )
`( 73 ) Assignee : UPL LTD , West Bengal ( IN )
`Subject to any disclaimer , the term of this
`( * ) Notice :
`patent is extended or adjusted under 35
`U.S.C. 154 ( b ) by 0 days .
`This patent is subject to a terminal dis
`claimer .
`
`( 21 ) Appl . No .:
`
`16 / 347,283
`Oct. 30 , 2017
`PCT / IB2017 / 056710
`
`( 22 ) PCT Filed :
`( 86 ) PCT No .:
`$ 371 ( c ) ( 1 ) ,
`May 3 , 2019
`( 2 ) Date :
`( 87 ) PCT Pub . No .: WO2018 / 083577
`PCT Pub . Date : May 11 , 2018
`Prior Publication Data
`Sep. 12 , 2019
`US 2019/0274307 A1
`Foreign Application Priority Data
`( 30 )
`Nov. 4 , 2016 ( IN )
`201631037704
`( 51 ) Int . Ci .
`AOIN 47/14
`AOIN 37/36
`AOIN 43/16
`AOIN 43/40
`AOIN 43/54
`AOIN 43/56
`AOIN 43/60
`AOIN 43/653
`AOIN 45/02
`( 52 ) U.S. CI .
`CPC
`
`( 65 )
`
`( 2006.01 )
`( 2006.01 )
`( 2006.01 )
`( 2006.01 )
`( 2006.01 )
`( 2006.01 )
`( 2006.01 )
`( 2006.01 )
`( 2006.01 )
`A01N 47/14 ( 2013.01 ) ; AOIN 37/36
`( 2013.01 ) ; AOIN 43/16 ( 2013.01 ) ; AOIN
`43/40 ( 2013.01 ) ; AOIN 43/54 ( 2013.01 ) ;
`AOIN 43/56 ( 2013.01 ) ; A01N 43760
`( 2013.01 ) ; AOIN 43/653 ( 2013.01 ) ; AOIN
`45/02 ( 2013.01 )
`( 58 ) Field of Classification Search
`A01N 47/14 ; A01N 37/36 ; A01N 43/16 ;
`CPC
`AOIN 43/40 ; A01N 43/54 ; A01N 43/56 ;
`A01N 43/60 ; A01N 43/653 ; AO1N 45/02
`See application file for complete search history .
`
`( 56 )
`
`References Cited
`U.S. PATENT DOCUMENTS
`10,362,782 B2 *
`7/2019 Oliveira
`10,448,636 B2 * 10/2019 Oliveira
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`1/2020 Oliveira
`10,694,744 B2 *
`6/2020 Oliveira
`10,694,745 B2 *
`6/2020 Oliveira
`2008/0113979 Al
`5/2008 Foor
`2009/0131462 Al
`5/2009 Gewehr et al .
`2010/0216640 A1
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`2015/0181870 A1 *
`7/2015 Kemmitt
`
`AOIN 43/653
`A01N 43/40
`AOIN 43/653
`AOIN 25/00
`AOIN 43/653
`
`AOIN 37/42
`514 / 229.2
`AOIN 43/54
`2016/0360751 A1 * 12/2016 Oliveira
`2020/0170251 A1 *
`6/2020 Hermenegildo de Oliveira
`A01N 25/00
`2021/0007355 A1
`1/2021 Gongora et al .
`2021/0022343 Al
`1/2021 Gongora et al .
`2021/0106006 A1
`4/2021 Fabri et al .
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`5/2021 Fabri et al .
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`5/2021 Fabri et al .
`2022/0039388 A1
`2/2022 Fabri et al .
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`22222
`
`CN
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`WO
`WO
`WO
`WO
`
`FOREIGN PATENT DOCUMENTS
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`6/2016
`2969545 A1
`7/2008
`101222847 A
`3/2010
`101677558 A
`11/2011
`102258039 A
`102835407 A 12/2012
`105744834 A
`7/2016
`* 12/2014
`2783569
`2006037632
`4/2006
`2006037634 A1
`4/2006
`2008095913 A2
`8/2008
`2013127818 Al
`9/2013
`2015079334 Al
`6/2015
`
`OTHER PUBLICATIONS
`Brent K. J. et al . , “ Fungicide Resistance in Crop Pathogens : How
`Can It Be Managed ? ” ; 2nd Revised Edition , Fungicide Resistance
`Action Committee , 2007 , ISBN 90-72398-07-6 ; 60 pages .
`International Search Report and Written Opinion ; International
`Application No. PCT / IB2017 / 056710 ; International Filing Date
`Oct. 30 , 2017 ; dated Jan. 12 , 2018 ; 10 pages .
`Lalancette , Norman , “ New Fungicide for Apple Disease Control ”
`Plant & Pest Advisory , Rutgers Cooperative Extension , Mar. 17 ,
`2016 , 2 pages .
`Rosenberger , David ; “ Apple Scab Models & Suggestions for Scab
`Control in 2015 ” ; 70th North Jersey Commercial Fruit Growers
`Meeting , Flemington , NJ , Mar. 4 , 2015 , 31 pages .
`Rosenberger Presentation “ Fire Blight and NEWA — How to Con
`trol Blight in 2015 ” ; 70th North Jersey Commercial Fruit Growers
`Meeting ; Mar. 4 , 2015 , Flemington , NJ ; 43 pages .
`* cited by examiner
`Primary Examiner — Mina Haghighatian
`( 74 ) Attorney , Agent , or Firm — Cantor Colburn LLP
`( 57 )
`ABSTRACT
`A combination comprising a dithiocarbamate fungicide , a
`succinate dehydrogenase fungicide and at least one of ergos
`terol biosynthesis inhibitor fungicide or a quinone outside
`inhibitor fungicide .
`10 Claims , No Drawings
`
`SYNGENTA EXHIBIT 1001
`Syngenta v. UPL, PGR2023-00017
`
`

`

`US 11,445,727 B2
`
`CROSS REFERENCE TO RELATED
`APPLICATIONS
`
`5
`
`a
`
`1
`FUNGICIDAL COMBINATIONS
`
`2
`imposed and resistance being increasingly observed , there is
`a need for a combination of actives that allows for broader
`disease control spectrum that combines curative and pre
`ventive actives and has a lower dosage .
`Therefore , embodiments of the present invention may
`This application is a National Stage application of PCT /
`ameliorate one or more of the above mentioned problems :
`IB2017 / 056710 , filed on Oct. 30 , 2017 , which claims the
`Therefore , embodiments of the present invention may
`benefit of Indian Application No. 201631037704 , filed on
`provide combinations of fungicides that possess
`an
`Nov. 4 , 2016 , both of which are incorporated by reference in
`enhanced efficacy over the individual fungicides used in
`their entirety herein .
`10 isolation .
`Another object of the present invention is to provide a
`fungicidal combination that causes an enhanced greening of
`TECHNICAL FIELD
`the crops to which it is administered .
`The present invention relates to a combination of fungi-
`Another object of the present invention is to provide a
`cides . More specifically , the present invention relates to 15 fungicidal combination that causes late senescence to the
`fungicidal combinations comprising succinate dehydroge-
`crop to which it is applied thereby resulting into an increas
`nase inhibitor fungicides for controlling a broad spectrum of
`ing yield of the crop .
`fungal diseases .
`Yet another object of the present invention is to provide a
`fungicidal combination that results into reduced fungal
`BACKGROUND OF THE INVENTION
`20 disease incidence in the crops to which it is applied .
`Another object of the present invention is to provide a
`fungicidal combination that achieves increased yield in the
`Fungicides are an integral and important tool yielded by
`farmers to control diseases , as well as to improve yields and
`crops to which it is applied .
`quality of the crops . There are various fungicides that have
`Some or all these and other objects of the invention are
`been developed over the years with many desirable attri- 25 can be achieved by way of the invention described herein
`butes such as specificity , systemicity , curative and eradicant
`after .
`action and high activity at low use rates .
`Succinate dehydrogenase inhibitor ( SDHI ) fungicides are
`SUMMARY OF THE INVENTION
`known in the art to be broad spectrum and have a high
`Thus , an aspect of the present invention can provide a
`potency . Pyrazolecarboxamides are a group of active com- 30
`fungicidal combination comprising at least one succinate
`pounds within the SDHI family of fungicides that are known
`dehydrogenase inhibitor fungicide , at least one dithiocar
`to be more potent than most other SDHI fungicides . These
`bamate fungicide , and at least another fungicide .
`molecules specifically bind to the ubiquinone - binding site
`Another aspect of the present invention can provide a
`( Q - site ) of the mitochondrial complex II , thereby inhibiting
`fungal respiration . These fungicides are known to control a 35 fungicidal combination comprising at least one succinate
`broad spectrum of fungal diseases .
`dehydrogenase inhibitor fungicide , at least one dithiocar
`Various other classes of fungicides are also known in the
`bamate fungicide and at least two other fungicides .
`art , such as Quinone outside inhibitors ( Qols ) , ergosterol-
`Another aspect of the present invention can provide
`biosynthesis inhibitors , fungicides that act on multiple sites ,
`synergistic compositions comprising at least one succinate
`fungicides that affect mitosis etc. These fungicides have 40 dehydrogenase inhibitor fungicide , at least one dithiocar
`been mixed with SDHI fungicides to achieve a broad
`bamate fungicide , and at least one other fungicide .
`spectrum of disease control .
`Another aspect of the present invention can provide
`WO2006037632 teaches combinations of SDHI fungi-
`synergistic compositions comprising at least one succinate
`cides with a second active compound . WO2013127818
`dehydrogenase inhibitor fungicide , at least one dithiocar
`teaches combinations of SDHI fungicides with various her- 45 bamate fungicide and at least two other fungicides .
`bicides . WO2006037634 teaches methods of controlling
`fungi using a combination of SDHI fungicide with various
`DETAILED DESCRIPTION
`fungicides . However , the prior art does not teach the use of
`ternary or higher combinations of SDHI fungicides .
`The term ' disease control ' as used herein denotes control
`Dithiocarbamate are known in the art as multi - site fun- 50 and prevention of a disease . Controlling effects include all
`a
`gicides . These fungicides are used for broad - spectrum dis-
`deviation from natural development , for example : killing ,
`ease control in more than 70 crops . Mancozeb is especially
`retardation , decrease of the fugal disease . The term “ plants '
`important for controlling devastating and fast spreading
`refers to all physical parts of a plant , including seeds ,
`diseases such as Phytophthora infestans , Venturia inaequalis
`seedlings , saplings , roots , tubers , stems , stalks , foliage and
`etc. Dithiocarbamate fungicides , especially mancozeb , are 55 fruits . The term locus : of a plant as used herein is intended
`particularly useful for disease control because of their broad
`to embrace the place on which the plants are growing , where
`spectrum of activity , high tolerance by crop plants , and
`the plant propagation materials of the plants are sown or
`general usefulness for controlling fungal plant diseases not
`where the plant propagation materials of the plants will be
`controlled by active compounds that act on only a single
`placed into the soil . The term plant propagation material : is
`60 understood to denote generative parts of a plant , such as
`target site in the fungus .
`Mancozeb has been combined with various SDHI fungi-
`seeds , vegetative material such as cuttings or tubers , roots ,
`cides for disease control . There is a need in the art to
`fruits , tubers , bulbs , rhizomes and parts of plants , germi
`improve on the disease spectrum provided by these combi-
`nated plants and young plants which are to be transplanted
`after germination or after emergence from the soil . These
`nations .
`There is therefore a need in the art for combinations of 65 young plants may be protected before transplantation by a
`total or partial treatment by immersion . The term agricul
`SDHIs with a specific fungicide that helps improve spec-
`trum . With crop tolerances decreasing , lower use rates being
`turally acceptable amount of active : refers to an amount of
`
`

`

`3
`an active that kills or inhibits the plant disease for which
`control is desired , in an amount not significantly toxic to the
`plant being treated .
`Succinate dehydrogenase inhibitor ( SDHI ) fungicides
`play an important role in plant protection against many
`phytopathogenic fungi . These molecules specifically bind to
`the ubiquinone - binding site ( Q - site ) of the mitochondrial
`complex II , thereby inhibiting fungal respiration . Dithiocar
`bamate are multi - site contact fungicides . These molecules
`attack multiple sites within the fugal cells .
`It has surprisingly been found that the addition of a
`dithiocarbamate fungicide to the combinations of succinate
`dehydrogenase inhibitors with at least another fungicide
`selected from an ergosterol biosynthesis inhibitors or Qui
`none outside inhibitors or a combination thereof , resulted in 15
`surprising and unexpected advantages . It was surprising that
`the addition of a dithiocarbamate fungicide to the combina
`tion of a succinate dehydrogenase inhibitor with at least
`another fungicide selected from an ergosterol biosynthesis
`inhibitors and / or Quinone outside inhibitors or a combina
`tion thereof resulted in an enhancement of the efficacy , and
`a surprising reduction in fungal disease incidence , seen only
`with the combination of succinate dehydrogenase inhibitors
`with at least another fungicide selected from an ergosterol
`biosynthesis inhibitors or Quinone outside inhibitors or a
`combination thereof . It has further been found that the 25
`addition of a dithiocarbamate fungicide to these combina
`tions and application of these combinations during the
`flowering stage of the crop delayed the senescence in the
`crop to which they were applied , which led to better green
`ing in the crop thereby increasing the level of photosynthesis 30
`occurring within the plant , thereby leading to a greater yield
`from the crop to which they were applied .
`These surprising advantages of the combinations of the
`invention were not observed when the dithiocarbamate
`fungicide was not present in the combination . Therefore ,
`these unexpected advantages of the combination of the
`present invention could be attributed to the inclusion of a
`dithiocarbamate fungicide to the combination of a succinate
`dehydrogenase inhibitor with at least another fungicide
`selected from an ergosterol biosynthesis inhibitors and / or
`Quinone outside inhibitors or a combination thereof .
`Thus , in an aspect , the present invention provides a
`fungicidal combination comprising :
`( a ) at least one dithiocarbamate fungicide ;
`( b ) at least one succinate dehydrogenase inhibitor fungi
`cide ; and
`( c ) at least another fungicide selected from an ergosterol
`biosynthesis inhibitors and / or Quinone outside inhibi
`tors .
`In an embodiment , the dithiocarbamate fungicide is
`selected from the group consisting of amobam , asomate ,
`azithiram , carbamorph , cufraneb , cuprobam , disulfiram , fer- 50
`bam , metam , nabam , tecoram , thiram , urbacide , ziram ,
`dazomet , etem , milneb , mancopper , mancozeb , maneb ,
`metiram , polycarbamate , propineb and zineb .
`In an embodiment , the preferred dithiocarbamate fungi
`cide is mancozeb .
`In an embodiment , the succinate dehydrogenase inhibitor
`is selected from pyrazole carboxamide class of succinate
`dehydrogenase inhibitor fungicides . However , it should be
`understood that the choice of succinate dehydrogenase
`inhibitors is not understood to be limited to these pyrazole
`carboxamide fungicides alone .
`In an embodiment , the pyrazole carboxamide class of
`succinate dehydrogenase inhibitor fungicide may be
`selected from benzovindiflupyr , bixafen , fluxapyroxad ,
`furametpyr , isopyrazam , penflufen , penthiopyrad , and
`sedaxane .
`Benzovindiflupyr has the chemical name N - [ ( 1RS , 4SR )
`9- ( dichloromethylene ) -1,2,3,4 - tetrahydro - 1,4 - methanon
`
`4
`aphthalen - 5 - yl ] -3- ( difluoromethyl ) -1 - methylpyrazole - 4
`carboxamide and has the structure :
`
`Ci
`
`H
`
`CH3
`
`HC- -F
`/
`F
`
`Bixafen has the chemical name N- ( 35,4 ' - dichloro - 5 - fluo
`robiphenyl - 2 - yl ) -3- ( difluoromethyl ) -1 - methylpyrazole - 4
`carboxamide and the structure :
`
`CI
`
`H
`
`CH3
`
`HC - F
`/
`F.
`
`F
`
`Fluxapyroxad has the chemical name 3- ( difluoromethyl )
`1 - methyl - N- ( 3,4,5 - trifluorobiphenyl - 2 - yl ) pyrazole - 4 - car
`boxamide and has the structure :
`
`F
`
`CH3
`
`F
`
`H
`
`HC - F
`
`F
`
`Furametpyr has the chemical name ( RS ) -5 - chloro - N- ( 1 ,
`3 - dihydro - 1,1,3 - trimethylisobenzofuran - 4 - yl ) -1,3 - dimeth
`ylpyrazole - 4 - carboxamide and has the structure :
`
`CI
`
`CH3
`
`H
`
`N
`
`CH3
`
`CH3
`
`H3C
`
`CH3
`
`US 11,445,727 B2
`
`5
`
`10
`
`20
`
`35
`
`40
`
`45
`
`55
`
`60
`
`65
`
`

`

`US 11,445,727 B2
`
`a
`
`5
`Isopyrazam is a mixture of 2 isomers 3- ( difluoromethyl )
`1 - methyl - N - [ ( 1RS , 4SR , 9RS ) -1,2,3,4 - tetrahydro - 9 - isopro
`pyl - 1,4 - methanonaphthalen - 5 - yl ] pyrazole - 4 - carboxamide
`and 2 aisomers 3- ( difluoromethyl ) -1 - methyl - N - [ ( IRS , 4SR ,
`9SR ) -1,2,3,4 - tetrahydro - 9 - isopropyl - 1,4 - methanonaphtha
`len - 5 - yllpyrazole - 4 - carboxamide and its tautomer's have
`the structure :
`
`5
`
`10
`
`6
`
`H
`
`H
`
`CH3
`
`sing
`
`In an embodiment , the succinate dehydrogenase inhibitor
`15 fungicide may be selected from the group consisting of
`benodanil , flutolanil , mepronil ,
`isofetamid , fluopyram ,
`fenfuram , carboxin , oxycarboxin , thifluzamide , boscalid and
`IR9792 .
`In an embodiment , the third and / or fourth fungicides in
`20 the combinations of the present invention may be selected
`from ergosterol biosynthesis inhibitors , and / or Quinone out
`side ( Qo ) inhibitors or mixtures thereof .
`Thus in an embodiment , the ergosterol biosynthesis
`inhibitors may be selected from the group consisting of
`azaconazole , bitertanol , bromuconazole , cyproconazole ,
`difenoconazole , diniconazole , epoxiconazole , etaconazole ,
`fenbuconazole , fluquinconazole , flusilazole , flutriafol , hexa
`conazole ,
`imibenconazole ,
`Ipconazole ,
`metconazole ,
`myclobutanil , penconazole , Propiconazole , simeconazole ,
`tebuconazole , tetraconazole , triadimefon , triadimenol , triti
`conazole , prothioconazole , imazalil , oxpoconazole , pefura
`zoate ,
`prochloraz ,
`triflumizole ,
`fenarimol , nuarimol ,
`pyrifenox , pyrisoxazole , triforine and mixtures thereof .
`In another embodiment , the ergosterol biosynthesis
`inhibitors may be selected from prothioconazole , tebucona
`zole , hexaconazole , cyroconazole or epoxiconazole .
`In an embodiment , the third fungicide may be a Quinone
`outside ( Qo ) inhibitor fungicide selected from azoxystrobin ,
`40 coumoxystrobin , enoxastrobin , flufenoxystrobin , picox
`ystrobin , pyraoxystrobin , mandestrobin , pyraclostrobin ,
`pyrametostrobin , triclopyricarb , kresoxim - methyl , dimox
`ystrobin , fenaminostrobin , metominostrobin , trifloxystrobin ,
`famoxadone , fluoxastrobin , fenamidone , pyribencarb and
`mixtures thereof .
`In an embodiment , the Quinone outside ( Qo ) inhibitor
`fungicide may be selected from azoxystrobin , picoxystrobin ,
`kresoxim - methyl , pyraclostrobin and trifloxystrobin .
`In an embodiment of the combinations of the present
`50 invention , the preferred succinate dehydrogenase inhibitor
`fungicide is isopyrazam .
`In an embodiment , the combinations of the present inven
`tion include the following preferred combinations :
`
`25
`
`30
`
`35
`
`45
`
`55
`
`S No. I
`
`1
`2
`3
`4
`5
`6
`7
`8
`9
`10
`11
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`60
`
`65
`
`II
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`
`III
`Cyproconazole
`Difenoconazole
`Epoxiconazole
`Hexaconazole
`Tebuconazole
`Tetraconazole
`Prothioconazole
`
`IV
`
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`
`HF2C
`
`Me
`
`Penflufen has the chemical name N- [ 2- ( 1,3 - dimethyl-
`butyl ) phenyl ] -5 - fluoro - 1,3 - dimethyl - 1H - pyrazole - 4 - car-
`boxamide , and has the following structure :
`
`F.
`
`CH3
`
`N
`
`CH3
`
`NH
`
`CH3
`-CH - CH2 - HC
`CH3
`CH3
`
`Penthiopyrad has the chemical name ( RS ) —N- [ 2- ( 1,3-
`dimethylbutyl ) -3 - thienyl ] -1 - methyl - 3- ( trifluoromethyl )
`pyrazole - 4 - carboxamide , and has the following structure :
`
`CH3
`
`H3C
`
`CH3
`CH
`CH3
`CH
`
`H3C
`
`F
`
`S
`
`H See F
`
`Sedaxane is a mixture of 2 cis - isomers 2 ' - [ ( 1RS , 2RS ) -1 ,
`1 ' - bicycloprop - 2 - yl ) -3- ( difluoromethyl ) -1 - methylpyrazole
`4 - carboxanilide and 2 trans - isomers 2 - [ ( 1RS , 2SR ) -1,1 ' - bi
`cycloprop - 2 - yl ) -3- ( difluoromethyl ) -1 - methylpyrazole - 4
`carboxanilide , and its tautomer's have the structure :
`
`

`

`US 11,445,727 B2
`
`8
`-continued
`
`7
`-continued
`
`II
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`Isopyrazam
`
`III
`
`Cyproconazole
`Cyproconazole
`Cyproconazole
`Cyproconazole
`Cyproconazole
`Difenoconazole
`Difenoconazole
`Difenoconazole
`Difenoconazole
`
`Difenoconazole
`Epoxiconazole
`Epoxiconazole
`Epoxiconazole
`Epoxiconazole
`Epoxiconazole
`Hexaconazole
`Hexaconazole
`Hexaconazole
`Hexaconazole
`
`Hexaconazole
`Tebuconazole
`Tebuconazole
`Tebuconazole
`Tebuconazole
`
`Tebuconazole
`Tetraconazole
`Tetraconazole
`Tetraconazole
`Tetraconazole
`
`Tetraconazole
`Prothioconazole
`Prothioconazole
`Prothioconazole
`Prothioconazole
`
`Prothioconazole
`
`IV
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`
`5
`
`10
`
`15
`
`20
`
`25
`
`30
`
`35
`
`S No. 1
`
`23456 12
`
`13
`14
`15
`16
`
`17
`18
`19
`20
`21
`
`22
`23
`24
`25
`26
`
`27
`28
`29
`30
`31
`
`32
`33
`34
`35
`36
`
`37
`38
`39
`40
`41
`
`42
`43
`44
`45
`46
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`47
`
`Mancozeb
`
`
`
`75
`76
`77
`78
`
`S No. I
`III
`II
`68 Mancozeb Benzovindiflupyr Difenoconazole
`69 Mancozeb Benzovindiflupyr Difenoconazole
`70 Mancozeb Benzovindiflupyr Epoxiconazole
`71 Mancozeb Benzovindiflupyr Epoxiconazole
`72 Mancozeb Benzovindiflupyr Epoxiconazole
`73 Mancozeb Benzovindiflupyr Epoxiconazole
`Mancozeb Benzovindiflupyr Epoxiconazole
`gSnus HSB ? ? 74
`Mancozeb Benzovindiflupyr Hexaconazole
`Mancozeb Benzovindiflupyr Hexaconazole
`Mancozeb Benzovindiflupyr Hexaconazole
`Mancozeb Benzovindiflupyr Hexaconazole
`Mancozeb Benzovindiflupyr Hexaconazole
`Mancozeb Benzovindiflupyr Tebuconazole
`Mancozeb Benzovindiflupyr Tebuconazole
`Mancozeb Benzovindiflupyr Tebuconazole
`Mancozeb Benzovindiflupyr Tebuconazole
`Mancozeb Benzovindiflupyr Tebuconazole
`Mancozeb Benzovindiflupyr Tetraconazole
`Mancozeb Benzovindiflupyr Tetraconazole
`Mancozeb Benzovindiflupyr Tetraconazole
`Mancozeb Benzovindiflupyr Tetraconazole
`Mancozeb Benzovindiflupyr Tetraconazole
`Mancozeb Benzovindiflupyr Prothioconazole
`Mancozeb Benzovindiflupyr Prothioconazole
`Mancozeb Benzovindiflupyr Prothioconazole
`Mancozeb Benzovindiflupyr Prothioconazole
`94 Mancozeb Benzovindiflupyr Prothioconazole
`
`79
`80
`81
`82
`83
`
`84
`85
`86
`87
`88
`
`89
`90
`91
`92
`93
`
`IV
`
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`
`In an embodiment of the combinations of the present
`invention , the preferred succinate dehydrogenase inhibitor
`fungicide is Penthiopyrad .
`In an embodiment , the combinations of the present inven
`tion include the following preferred combinations :
`
`In an embodiment of the combinations of the present
`invention , the preferred succinate dehydrogenase inhibitor
`fungicide is Benzovindiflupyr .
`In an embodiment , the combinations of the present inven
`tion include the following preferred combinations :
`
`S No. I
`II
`III
`48 Mancozeb Benzovindiflupyr Cyproconazole
`49 Mancozeb Benzovindiflupyr Difenoconazole
`50 Mancozeb Benzovindiflupyr Epoxiconazole
`51 Mancozeb Benzovindiflupyr Hexaconazole
`52 Mancozeb Benzovindiflupyr Tebuconazole
`53 Mancozeb Benzovindiflupyr Tetraconazole
`54 Mancozeb Benzovindiflupyr Prothioconazole
`55 Mancozeb Benzovindiflupyr
`56 Mancozeb Benzovindiflupyr
`57 Mancozeb Benzovindiflupyr
`58 Mancozeb Benzovindiflupyr
`59 Mancozeb Benzovindiflupyr
`60 Mancozeb Benzovindiflupyr Cyproconazole
`61 Mancozeb Benzovindiflupyr Cyproconazole
`62 Mancozeb Benzovindiflupyr Cyproconazole
`Mancozeb Benzovindiflupyr Cyproconazole
`63
`64 Mancozeb Benzovindiflupyr Cyproconazole
`65 Mancozeb Benzovindiflupyr Difenoconazole
`66 Mancozeb Benzovindiflupyr Difenoconazole
`67 Mancozeb Benzovindiflupyr Difenoconazole
`
`IV
`
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`
`40
`
`S No. I
`
`95
`96
`97
`98
`99
`100
`101
`102
`103
`104
`105
`
`106
`107
`108
`109
`110
`
`111
`112
`113
`114
`115
`
`116
`117
`118
`119
`120
`
`121
`122
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`
`45
`
`50
`
`55
`
`60
`
`65
`
`II
`III
`Penthiopyrad Cyproconazole
`Penthiopyrad Difenoconazole
`Penthiopyrad Epoxiconazole
`Penthiopyrad Hexaconazole
`Penthiopyrad Tebuconazole
`Penthiopyrad Tetraconazole
`Penthiopyrad Prothioconazole
`Penthiopyrad
`Penthiopyrad
`Penthiopyrad
`Penthiopyrad
`Penthiopyrad
`Penthiopyrad Cyproconazole
`Penthiopyrad Cyproconazole
`Penthiopyrad Cyproconazole
`Penthiopyrad Cyproconazole
`Penthiopyrad Cyproconazole
`Penthiopyrad Difenoconazole
`Penthiopyrad Difenoconazole
`Penthiopyrad Difenoconazole
`Penthiopyrad Difenoconazole
`Penthiopyrad Difenoconazole
`Penthiopyrad Epoxiconazole
`Penthiopyrad Epoxiconazole
`Penthiopyrad Epoxiconazole
`Penthiopyrad Epoxiconazole
`Penthiopyrad Epoxiconazole
`Penthiopyrad Hexaconazole
`
`IV
`
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`
`

`

`US 11,445,727 B2
`
`9
`-continued
`
`10
`-continued
`
`S No. 1
`
`123
`124
`125
`
`126
`127
`128
`129
`130
`
`131
`132
`133
`134
`135
`
`136
`137
`138
`139
`140
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`141 Mancozeb
`
`III
`II
`Penthiopyrad Hexaconazole
`Penthiopyrad Hexaconazole
`Penthiopyrad Hexaconazole
`Penthiopyrad Hexaconazole
`Penthiopyrad Tebuconazole
`Penthiopyrad Tebuconazole
`Penthiopyrad Tebuconazole
`Penthiopyrad Tebuconazole
`Penthiopyrad Tebuconazole
`Penthiopyrad Tetraconazole
`Penthiopyrad Tetraconazole
`Penthiopyrad Tetraconazole
`Penthiopyrad Tetraconazole
`Penthiopyrad Tetraconazole
`Penthiopyrad Prothioconazole
`Penthiopyrad Prothioconazole
`Penthiopyrad Prothioconazole
`Penthiopyrad Prothioconazole
`Penthiopyrad Prothioconazole
`
`IV
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`
`5
`
`10
`
`15
`
`20
`
`S No. I
`
`II
`
`III
`
`178
`179
`180
`181
`182
`
`183
`184
`185
`186
`187
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`
`188 Mancozeb
`
`Boscalid
`
`Tebuconazole
`Tetraconazole
`Tetraconazole
`Tetraconazole
`Tetraconazole
`
`Tetraconazole
`Prothioconazole
`Prothioconazole
`Prothioconazole
`Prothioconazole
`Prothioconazole
`
`IV
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`
`In an embodiment of the combinations of the present
`invention , the preferred succinate dehydrogenase inhibitor
`fungicide is IR9792 . IR9792 is a SDHI fungicide , developed
`by Isagro , with the proposed common name fluindapyr .
`In an embodiment , the combinations of the present inven
`tion include the following preferred combinations :
`
`a
`
`In an embodiment of the combinations of the present
`invention , the preferred succinate dehydrogenase inhibitor
`fungicide is boscalid .
`In an embodiment , the combinations of the present inven
`tion include the following preferred combinations :
`
`S No. I
`
`II
`
`IV
`
`III
`Cyproconazole
`Difenoconazole
`Epoxiconazole
`Hexaconazole
`Tebuconazole
`Tetraconazole
`Prothioconazole
`
`IV
`
`III
`Cyproconazole
`Difenoconazole
`Epoxiconazole
`Hexaconazole
`Tebuconazole
`Tetraconazole
`Prothioconazole
`
`S No. I
`
`25
`
`30
`
`35
`
`189
`190
`191
`192
`193
`194
`195
`196
`197
`198
`199
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`II
`
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`
`142
`143
`144
`145
`146
`147
`148
`149
`150
`151
`152
`
`153
`154
`155
`156
`157
`
`158
`159
`160
`161
`162
`
`163
`164
`165
`166
`167
`
`168
`169
`170
`171
`172
`
`173
`174
`175
`176
`177
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`Boscalid
`
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`
`40
`
`45
`
`50
`
`55
`
`60
`
`65
`
`Cyproconazole
`Cyproconazole
`Cyproconazole
`Cyproconazole
`Cyproconazole
`Difenoconazole
`Difenoconazole
`Difenoconazole
`Difenoconazole
`
`Difenoconazole
`Epoxiconazole
`Epoxiconazole
`Epoxiconazole
`Epoxiconazole
`Epoxiconazole
`Hexaconazole
`Hexaconazole
`Hexaconazole
`Hexaconazole
`
`Hexaconazole
`Tebuconazole
`Tebuconazole
`Tebuconazole
`Tebuconazole
`
`200
`201
`202
`203
`204
`
`205
`206
`207
`208
`209
`
`210
`211
`212
`213
`214
`
`215
`216
`217
`218
`219
`
`220
`221
`222
`223
`224
`
`225
`226
`227
`228
`229
`
`230
`231
`232
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`Mancozeb
`
`Mancozeb
`Mancozeb
`Mancozeb
`
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`
`IR9792
`IR9792
`IR9792
`IR9792
`IR9792
`
`IR9792
`IR9792
`IR9792
`
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`Azoxystrobin
`Picoxystrobin
`Pyraclostrobin
`Kresoxim
`methyl
`Trifloxystrobin
`A