# US 2014/0154336 A1 · Active Compound Combinations

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- Number: US 2014/0154336 A1
- Document ID: US20140154336A1
- Status: Published application
- Kind: A1
- Application number: 13/915,831
- Filed: 2013-06-12
- Published: 2014-06-05
- Earliest claimed: 2009-09-14
- Assignees: Bayer Intellectual Property GmbH
- Inventors: Thomas SEITZ; Ulrike WACHENDORFF-NEUMANN; Peter DAHMEN
- Web page: https://patentgrep.com/patent/US20140154336A1

## CPC

- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 25/02: containing liquids as carriers, diluents or solvents
- A01N 39/00: Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group [IMAGE cpc-sch-A01N-0940.gif] or [IMAGE cpc-sch-A01N-0941.gif], e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N 43/16: with oxygen as the ring hetero atom
- A01N 43/40: six-membered rings
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- A01N 47/12: containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N 57/12: containing acyclic or cycloaliphatic radicals
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

The present invention relates to compositions, in particular within a fungicide composition, which comprises (A) a dithiino-tetracarboximide of formula (I) and a further fungicidally active compound (B). Moreover, the invention relates to a method for curatively or preventively controlling the phytopathogenic fungi of plants or crops, to the use of a combination according to the invention for the treatment of seed, to a method for protecting a seed and to the treated seed.

## Claims

### Claim 1

A composition comprising
(A) at least one dithiino-tetracarboximide of formula (I)
in which R1 and R2 are identical and represent methyl, ethyl, n-propyl or isopropyl, and
n represents 0 or 1,
or an agrochemically acceptable salt thereof,
and
(B) at least one further active compound selected from the group consisting of
(1) inhibitors of the ergosterol synthesis,
(2) inhibitors of the respiratory chain at complex I or II,
(4) inhibitors of the mitosis and cell division,
(5) compounds capable of having a multisite action,
(6) compounds capable of inducing a host defense,
(7) inhibitors of the amino acid and/or protein biosynthesis,
(8) inhibitors of the ATP production,
(9) inhibitors of the cell wall synthesis,
(10) inhibitors of the lipid and membrane synthesis,
(11) inhibitors of the melanine biosynthesis,
(12) inhibitors of the nucleic acid synthesis,
(13) inhibitors of the signal transduction,
(14) compounds capable of acting as uncoupler, and
(15) other fungicides.

### Claim 2 (depends on 1)

The composition according to claim 1, herein the compound of formula (I) is 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone.

### Claim 3 (depends on 1)

The composition according to claim 1 wherein the at least one further active compound is selected from the group consisting of aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol, pefurazoate, penconazole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, tradimenol, tridemorph, triflumizole, triforine, triticonazole, uniconazole, viniconazole, 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate, O-{1-[(4-methoxyphenoxy)methyl]-2,2-di-methylpropyl}-1H-imidazole-1-carbothioate, N-ethyl-N-methyl-N′-{2-methyl-5-(difluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}-imidoformamide, N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}-imidoformamide, voriconazole, diflumetorim, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, furametpyr, furmecyclox, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, thifluzamide, 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide, 1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-[4′-(triflouromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(4′-prop-1-yn-1-ylbiphenyl-2-yl)-1H-pyrazole-4-carboxamide, 5-fluoro-1,3-dimethyl-N-(4′-prop-1-yn-1-ylbiphenyl-2-yl)-1H-pyrazole-4-carboxamide, 2-chloro-N-(4′-prop-1-yn-1-ylbiphenyl-2-yl)nicotinamide, 3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, N-[4′-(ethinylbiphenyl-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-(4′-ethinylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, 2-chloro-N-(4′-ethinylbiphenyl-2-yl)-nicotinamide, 2-chloro-N-[4′-(3,3-dimethylbut-1-in-1-yl)biphenyl-2-yl]-nicotinamide, 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide, 5-fluoro-N-[4′-3-hydroxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, 2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-nicotinamide, 3-difluoromethyl-N-[4′-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, 5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1H-pyrazole-4-carboxamide, 2-chloro-N-[4′-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-nicotinamide, benomyl, carbendazim, diethofencarb, ethaboxam, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine, bordeaux mixture, captafol, captan, chorothalonil, dichlofluanid, dithianon, dodine, ferbam, folpet, guazatine, iminoctadine, iminoctadine triacetate iminoctadine tris(albesilate), copper oxide, copper oxychlorid, copper hydroxide, copper sulfate mancopper, mancozeb, maneb, metiram, oxine copper, propineb, sulphur, sulphur preparations, calcium polysulphide, thiram, tolylfluanid, zineb, ziram, copper naphthenate, dodine free base, fluorofolpet, guazatine acetate, metiram zinc, propamidine, acibenzolar-S-methyl, probendazole, tiadinil, andoprim, blasticidin-S, cyprodinyl, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil, fentin acetate, fentin hydroxide, silthiofam, benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins, polyoxorim, porthiocarb, validamycin A, valifenalate, N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide, biphenyl, chlozolinate, edifenfos, etridiazole, iodocarb, iprobenfos, iprodione, isoprothiolane, procymidone, propamocarb, propamocarb-hydrochloride, pyrazophos, tolcofos-methyl, vinclozolin, carpropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole, benalaxyl, benalaxyl-M, bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid, fenpiclonil, fludioxonil, quinoxyfen, dinocap, fluazinam, meptyldinocap, binapacryl, ametoctradin, benthiazole, bethoxazin, carvone, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, dichlorophen, diclomezine, dicloran, difenzoquat, diphenylamine, ferimzone, flumetover, fluopicolide, fluoroimide, flusulfamide, fosetyl-A1, hexachlorobenzene, isotianil, methasulfocarb, methylisothiocyanate, metrafenone, nitrothal-isopropyl, octhilinone, oxyfenthiin, propamocarbfosetylate, proquinazid, pyrrolnitrine, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamide, 8-hydroxyquinoline sulfate, 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide, 2-butoxy-6-iodo-3-propyl-benzopyran-4-one, N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide, N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichlornicotinamide, N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, S-allyl-5-amino-2-isopropyl-4-(2-methylphenyl)-3-oxo-2,3-dihydro-1H-pyrazole-1-carbothioate, 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, 5-amino-1,3,4-thiadiazole-2-thiol, 1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl 1H-imidazole-1-carboxylate, 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, tebufloquin, flutianil, (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone, tolnifanide, N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, phosphorous acid and its salts, 5-chloro-N′-phenyl-N′-prop-2-yn-1-ylthiophene-2-sulfonohydrazide, N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide, N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide, pentyl 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)-methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate, capsimycin, chloroneb, cufraneb, cyprosulfamide, difenzoquat methylsulphate, ecomate, fosetyl-calcium, fosetyl-sodium, irumamycin, mildiomycin, natamycin, nickel dimethyldithiocarbamate, oxamocarb, pentachlorophenol and salts, phenazine-1-carboxylic acid, phenothrin, propanosine-sodium, quinolin-8-ol, 2-phenylphenol and salts, 5-methyl-6-octyl-3,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide, 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, and 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone.

### Claim 4 (depends on 1)

The composition according to claim 1 further comprising auxiliaries, solvents, carriers, surfactants or extenders.

### Claim 5 (depends on 1)

A method for controlling phytopathogenic fungi in crop protection comprising applying, the composition according to claim 1 to seed, to a plant, to a fruit of the plant, or to soil on which the plant grows or soil from which the seed, the plant, or the fruit of the plant grows.

### Claim 6 (depends on 5)

The method according to claim 5, wherein the composition is applied to the soil on which the seed, the plant, or the fruit of the plant grows or from which the seed, the plant or the fruit of the plant grows.

### Claim 7 (depends on 5)

The method according to claim 5, wherein the composition is applied as a foliar treatment.

### Claim 8 (depends on 7)

The method according to claim 7 wherein the composition is applied at a rate from 0.1 to 10 000 g/ha.

### Claim 9 (depends on 5)

The method according to claim 5 wherein the composition is applied to the seed.

### Claim 10 (depends on 9)

The method according to claim 9 wherein the composition is applied at rate of from 2 g to 200 g per 100 kg of seed.

### Claim 11 (depends on 5)

The method according to claim 5 wherein the plant is a transgenic plant.

### Claim 12 (depends on 5)

The method according to claim 5 wherein the seed is seed of a transgenic plant

### Claim 13 (depends on 5)

The method according to claim 5 wherein the phytopathogenic fungi is selected from the group consisting of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

### Claim 14

(canceled)

### Claim 15 (depends on 5)

The method according to claim 5 wherein the phytopathogenic fungi are controlled preventatively.

### Claim 16 (depends on 5)

The method according to claim 5 wherein the plant is selected from the group consisting of cereals, maize, cotton, soya bean, rice, potatoes, sunflowers, beans, coffee, beets peanuts, oilseed rape, poppies, olives, coconuts, cacao, sugar cane, tobacco, vegetables, lawn and ornamental plants.

### Claim 17 (depends on 5)

The method according to claim 5 wherein the plant is selected from the group consisting of cereals, maize and rice.

### Claim 18 (depends on 1)

The composition according to claim 1 wherein the at least one dithiino-tetracarboximide and the least one further active compound are present in a synergistically effective weight ratio.

### Claim 19 (depends on 18)

The composition according to claim 18 wherein the at least one dithiino-tetracarboximide and the least one further active compound are present in a weight ratio of 100:1 to 1:100.

### Claim 20 (depends on 18)

The composition according to claim 18 wherein the at least one dithiino-tetracarboximide and the at least one further active compound are present in a weight ratio of 50:1 to 1:50.

### Claim 21 (depends on 18)

The composition according to claim 18 wherein the at least one dithiino-tetracarboximide and the at least one further active compound are present weight ratio of 20:1 to 1:20.