Use of isoxazoline carboxamides for sprout control.

Abstract

The present invention relates to the field of food preservation, more specifically to the use of methyl(2R)- * ,4R * The present invention relates to the use of 3-(4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I), the use of a combination thereof or a composition comprising same for sprout inhibition in crops, and a method for inhibiting sprouts in crops.

Description

[Technical field]

[0001] The present invention relates to the field of food preservation, more specifically to the use of methyl(2R)- * ,4R * The present invention relates to the use of 3-(4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I), the use of a combination thereof or a composition comprising same for sprout inhibition in crops, and a method for inhibiting sprouts in crops. [Background technology]

[0002] Potatoes harvested in the fall are often expected to be stored throughout the winter, at least until earlier potatoes become available again, and well into the following spring. Even when potatoes are stored at low temperatures, as is customary in the potato processing industry, potatoes begin to sprout after only a few weeks when stored at 6-8°C, with significant sprout development after 3-4 months.

[0003] Other crops such as onion, cassava (Manihot esculenta), sweet potato (Ipomoea batatas), yams (Dioscorea spp.), Jerusalem artichoke (Helianthus tuberosus) and ginger (Zingiber officinale) are similarly affected by the problem.

[0004] The use of sprout inhibitors has been known for a long time. Known sprout inhibitors are certain essential oils, in particular peppermint and also the essential oil of the "munya" plant, which is closely related to peppermint. Peppermint oil and "munya" oil are relatively expensive, so that any industrial application based solely on said essential oils is not viable.

[0005] Chemical agents currently used for sprout control in connection with potatoes include propham:isopropylphenylcarbamate, either alone or in combination with chlorpropham.

[0006] Medium and long chain alcohols, especially C 17 ~C 24 -Alcohols are also known, which are often combined with propham and / or chlorpropham when used as sprout suppressants.

[0007] WO 93 / 00008 discloses aromatic aldehydes or aromatic alcohols or thymol or mixtures thereof that are useful as sprout suppressants.EP 0287946 A2 describes the use of essential oils from the genus Mentha, in particular oil of Mentha piperita L, as well as peppermint oil and oils of various types of mint, to reduce tuber sprouts.

[0008] As mentioned above, the exclusive use of the various essential oils is discouraged for practical reasons by the high costs, given that storage conditions result in only slight losses of these oils, and because the amounts required, even when potatoes are stored in the absence of oxygen, generally amount to 10-20 ml of oil per 50 kg of potatoes for a storage period of 50 days, if the potatoes are stored at +3°C to +8°C, and approximately double said amounts for storage periods of 100 days or more.

[0009] WO 94 / 28716 A2 discloses rapeseed oil methyl ester as a sprout inhibitor, if necessary in admixture with known medium and long chain alcohols and / or essential oils and / or known chemical sprout inhibitors, whereby it is disclosed that a combination of rapeseed oil methyl ester, an alcohol and, if necessary, one of the above-mentioned essential oils (especially peppermint oil) is preferred to achieve the best results.

[0010] Compounds from the structural class of substituted isoxazoline carboxamides are known as herbicides that are useful for weed control against a wide range of weeds from WO 2018 / 228985 and WO 2019 / 145245 in burndown applications. It is also known to combine such herbicidal active ingredients with some other herbicides for weed control (see, for example, WO 2020 / 114932). [Prior art documents] [Patent documents]

[0011] [Patent Document 1] International Publication No. 93 / 00008 [Patent Document 2] European Patent Application Publication No. 0287946(A2) [Patent Document 3] WO 94 / 28716(A2) [Patent Document 4] International Publication No. 2018 / 228985 [Patent Document 5] International Publication No. 2019 / 145245 [Patent Document 6] International Publication No. 2020 / 114932 Summary of the Invention [Means for solving the problem]

[0012] It has now been found that some compounds selected from the above group of substituted isoxazoline carboxamides can surprisingly be used for sprout inhibition without substantial damage to the harvested crop and, on the other hand, with high efficiency in terms of sprout inhibition.

[0013] One object of the present invention is to provide a compound which exists in the form of two stereoisomeric forms: methyl (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (Ia) and methyl (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (Ib) * ,4R * )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I) for the prevention of sprouts: [ka]

[0014] Another object of the present invention is to provide a method for the inhibition of sprouts comprising administering to a subject a compound comprising the steps of: * ,4R * )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

[0015] Another object of the present invention is to provide a method for the inhibition of sprouts comprising administering to the patient a compound comprising the steps of: * ,4R * )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

[0016] Another object of the present invention is to provide a method for the inhibition of sprouts comprising administering to the patient at least one additional active ingredient and at least one additional sprout inhibitor in combination with methyl(2R * ,4R * )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

[0017] Another object of the present invention is to provide a method for the treatment of sprout suppression using methyl(2R * ,4R * )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

[0018] Another object of the present invention is to provide a method for the treatment of methyl(2R * ,4R * )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

[0019] In another embodiment, the additional sprout inhibitor is selected from the group including ethylene, green mint oil, carvone, maleic hydrazide and 1,4-dimethylnaphthalene, isopropyl-(3-chlorophenyl)carbamate (CIPC, chlorpropham), extracts of peppermint oil, rapeseed oil methyl ester, and mixtures of two or more thereof.

[0020] In a preferred embodiment, the other sprout inhibitor is selected from the group comprising isopropyl-(3-chlorophenyl)carbamate (CIPC, chlorpropham), and extracts of peppermint oil, and mixtures of two or more thereof.

[0021] In another embodiment, the active ingredient is selected from the group comprising herbicides, insecticides, acaricides, fungicides, safeners, fertilizers and / or growth regulators, and mixtures of two or more thereof.

[0022] In a preferred embodiment, the active ingredient is one or more additional herbicides.

[0023] In another preferred embodiment, the active ingredient is one or more additional fungicides or insecticides. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0024] definition As used in this application, and unless otherwise indicated, the term "herbicide" refers to a compound that is manufactured, sold, or used in the field to kill or otherwise inhibit the growth of unwanted plants (such as, but not limited to, noxious or nuisance weeds, broadleaf plants, grasses, and sedges) and can be used for crop protection, building protection, or turf protection. The term "herbicide" includes end-use herbicide products. The compositions can be pure compounds, solutions of chemical compounds, mixtures of chemical compounds, emulsions, suspensions, solid-liquid mixtures, or liquid-liquid mixtures. The term "herbicide" also refers to the product that passes from the manufacturer through commercial channels to the ultimate end user, who can either apply the herbicide as sold to the infested field or mix the herbicide with other excipients.

[0025] "Herbicides" disclosed in the context of the present invention include, but are not limited to: Acetochlor, acifluorfen, acifluorfen sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor potassium, aminocyclopyrachlor methyl, aminopyralid, amitrole, s Ammonium sulfamate, anilophos, asulam, atrazine, azafenidine, azimsulfuron, beflubutamid, benazolin, benazolin ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron methyl, bensulide, bentazon, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanaphos, bilanaphos sodium, bispyribac, bispyribac sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, bromo xynyl-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamiphos, butenachlor, butralin, butroxydim, butyrate, cafenstrole, carbetamide, carfentrazone, carfentrazone ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac sodium, chlorfenprop, chlorflurenol, chlorflurenol methyl, chloridazon, chlorimuron, chlori Muron-ethyl, chlorophthalim, chlorotoluron, chlorthal dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinosulfuron, clasifos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-Butotyl, -Butyl, -Dimethylammonium, -Diolamine, -Ethyl, -2-Ethylhexyl, -Isobutyl, -Isooctyl, -Isopropylammonium, -Potassium, -Triisopropanolammonium and -Trolamine, 2,4-DB, 2,4-DB-Butyl, -Dimethylammonium, -Isooctyl, -Potassium and -Sodium, Dimron (Dimron), Dalapon, Dazomet, n-Decanol, Desmedif , detosylpyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop P, diclofop, diclofop methyl, diclofop P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, dif Lufenzopyr sodium, dimefuron, dimepiperate, dimethachlor, dimethamethrin, dimethenamid, dimethenamid P, dimetrasulfuron, dinitramine, dinoterb, diphenamide, diquat, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron methyl, ethiozin, ethofumesate, ethoxyphene, ethoxyphenethy F-5231, i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop P, fenoxaprop ethyl, fenoxaprop P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop M-isopropyl, flamprop M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop P, fluazifop butyl, fluazifop P-butyl, flucarbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, flufenacet, flu Fenpyr, Flufenpyr-ethyl, Flumetsulam, Flumicrac, Flumicrac-pentyl, Flumioxazin, Fluometuron, Flurenol, Flurenol-butyl, -dimethylammonium and -methyl, Fluoroglycofen, Fluoroglycofen-ethyl, Flupropanate, Flupyrsulfuron, Flupyrsulfuron-methyl sodium, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurtamone, Fluthiacet, Fluthiacet-methyl, Fomesafen, Fomesafen sodium, Foramsulfuron, Fosamine, Glufosinate, Glufosinate ammonium, Glufosinate P-sodium, Glufosinate P-ammonium, Glufosinate P-sodium, Glufosate, Glufosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201 i.e. O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropyl phosphoramidothioate, Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron-methyl, Haloxyfop, Haloxyfop P, Haloxyfop-ethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop-methyl, Haloxyfop-P-methyl, Hexazinone, HW-02 i.e. 1-(dimethoxyphosphoryl) Ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz methyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropyl ammonium, imazaquin, imazaquin ammonium, imazethapyr, imazethapyr ammonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron methyl sodium, ioxynil, ioxynil-octanoate, potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-Oxazole, Ketospiradox, Lactofen, Lenacil, Linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, Mecoprop, Mecoprop-sodium and -butotyl, Mecoprop P, Mecoprop P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, Mefenacet, Mefluidide, Mesosulfuron, Mesosulfuron-methyl, Mesotrione, Methabenzthiazuro , metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metoslam, methoxuron, metribuzin, metsulfuron, metsulfuron methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., 4-(2,4-Dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, nebulon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petoxamide, petroleum, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, pro Propoxycarbazone, Propoxycarbazone sodium, Propyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolinate (pyrazolate), Pyrazosulfuron, Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenzisopropyl, Pyribambenzpropyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-sodium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinmelac, Quinclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron methyl, Sulfosulfuron, SYN-523, SYP-249 i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP -300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), sodium TCA, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb , terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone methyl, thifensulfuron, thifensulfuron methyl, thiobencarb, thiaphenacyl, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tribenuron methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, as well as the following compounds: [ka]

[0026] Examples of plant growth regulators as possible mixture partners include: Acibenzolar, Acibenzolar-S-methyl, 5-aminolevulinic acid, Ancymidol, 6-benzylaminopurine, Brassinolide, Catechol, Chlormequat chloride, Cloprop, Cyclanilide, 3-(Cycloprop-1-enyl)propionic acid, Daminozide, Dazomet, n-Decanol, Dikegulac, Dikegulac sodium, Endothal, Endothal-dipotassium, -disodium and -mono(N,N-dimethylalkylammonium), Ethephon, Flumetralin, Flurenol, Flurenol butyl, Flurprimidol, Forchlorfenuron, Gibberellic acid, Inabenfide, Indole-3-acetic acid (IAA), 4-Indole 3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenoxide mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, chitodef, uniconazole, uniconazole P.

[0027] The herbicides referred to in this specification are known, for example, from “The Pesticide Manual” (16th Edition, 2012). The term "safener" means: Examples of useful safeners include the following classes of compounds:

[0028] S1) Compounds from the group of heterocyclic carboxylic acid derivatives: S1 a ) Dichlorophenylpyrazoline-3-carboxylic acid type compounds (S1 a ), preferably, for example, the following compounds: Such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) ("mefenpyr diethyl") and related compounds as described in WO 91 / 07874; S1 b ) Derivatives of dichlorophenylpyrazole carboxylic acid (S1 b ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds, as described, for example, in EP-A-333131 and EP-A-269806; S1 c ) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as, for example, ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds, as described, for example, in EP-A-268554; S1 d ) Triazole carboxylic acid type compounds (S1 d ), preferably compounds such as fenchlorazole (ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (S1-7), and related compounds, as described, for example, in EP-A-174562 and EP-A-346620; S1 e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1 e ), preferably compounds such as, for example, ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds as described in WO 91 / 08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13) as described in WO 95 / 07897.

[0029] S2) Compounds (S2) from the group of 8-quinolinoxy derivatives: S2 a ) 8-quinolinoxyacetic acid type compounds (S2 a), preferably 1-methylhexyl (5-chloro-8-quinolinoxy) acetate ("cloquintocet mexyl") (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy) acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy) acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy) acetate (S2-4), ethyl (5-chloro-8-quinolinoxy) acetate (S2-5), methyl (5-chloro-8 -quinolinoxy)acetate (S2-6), allyl(5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-propylideneiminoxy)-1-ethyl(5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-1-yl(5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds, as well as (5-chloro-8-quinolinoxy)acetic acid (S2-10), as described in WO 2002 / 34048, its hydrates and salts, for example its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts; S2 b )(5-chloro-8-quinolinoxy)malonic acid type compounds (S2 b ), preferably compounds such as diethyl(5-chloro-8-quinolinoxy)malonate, diallyl(5-chloro-8-quinolinoxy)malonate, methylethyl(5-chloro-8-quinolinoxy)malonate and related compounds as described, for example, in EP 0 582 198 A1.

[0030] S3) Active compounds of the dichloroacetamide type (S3), which are frequently used as pre-emergence safeners (soil-acting safeners), such as, for example, “Dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (S3-1), “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (obtained from Stauffer) (S3-2), “R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (obtained from Stauffer) (S3-3), “Benoxacor” (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), “PPG-1292” (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (PPG (obtained from BASF), “Furilazol” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (obtained from Nitrokemia or Monsanto) (S3-7), “TI-35” (1-dichloroacetylazepane) (obtained from TRI-Chemical RT) (S3-8), “Dichloronone” (Dicyclonone) or “BAS145138” or “LAB145138” (S3-9) ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) (obtained from BASF), “Furilazol” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (obtained from Sagro-Chem) (S3-10), “Furilazol” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (obtained from Nitrokemia or Monsanto) (S3-11), “Furilazol” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (obtained from Nitrokemia or Monsanto) (S3-12), “Furilazol” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (obtained from Nitrokemia or Monsanto) (S3-13), “Furilazol” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (obtained from Nitrokemia or Monsanto) (S3-14), “F 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and its (R) isomer (S3-11).

[0031] S4) Compounds from the class of acylsulfonamides (S4): S4 a ) as described in WO 97 / 45016, a ) N-acylsulfonamides and salts thereof, [ka] During the ceremony, R A 1 represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl, with the latter two radicals being selected from the group halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio. A substituted by substituents, and in the case of cyclic groups also by (C1-C4)-alkyl and (C1-C4)-haloalkyl; R A 2 represents halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m A represents 1 or 2; v A represents 0, 1, 2 or 3. S4 b ) as described in WO 99 / 16744, the following formula (S4 b ) 4-(benzoylsulfamoyl)benzamide type compounds and their salts, [ka] During the ceremony, R B 1 , R B 2 are each independently hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, R B 3 represents halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl or (C1-C4)-alkoxy, and m B represents 1 or 2; For example, a compound defined as follows: R B 1 = cyclopropyl, R B 2 = hydrogen, and (R B3 ) = 2-OMe ("cyprosulfamide", S4-1), R B 1 = cyclopropyl, R B 2 = hydrogen, and (R B 3 ) = 5-Cl-2-OMe (S4-2), R B 1 = ethyl, R B 2 = hydrogen, and (R B 3 )=2-OMe(S4-3), R B 1 = isopropyl, R B 2 = hydrogen, and (R B 3 ) = 5-Cl-2-OMe (S4-4), and R B 1 = isopropyl, R B 2 = hydrogen, and (R B 3 )=2-OMe(S4-5); S4 c ) as described in European Patent Application Publication No. 365484, c ) compounds from the class of benzoylsulfamoylphenylureas, [ka] During the ceremony, R C 1 , R C 2 are independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, R C 3 represents halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3, and m C represents 1 or 2; for example, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; S4 d For example, the following formula (S4 d ) N-phenylsulfonyl terephthalamide type compounds and their salts, [ka] During the ceremony, R D 4 represents halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m D represents 1 or 2; R D 5 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl.

[0032] S5) Active compounds (S5) from the class of the hydroxyaromatic and aromatic-aliphatic carboxylic acid derivatives, for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO 2004 / 084631, WO 2005 / 015994, WO 2005 / 016001.

[0033] S6) Active compounds (S6) from the class of 1,2-dihydroquinoxalin-2-ones, for example 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO 2005 / 112630.

[0034] S7) Compounds (S7) from the class of diphenylmethoxyacetic acid derivatives, such as methyl diphenylmethoxyacetate (CAS registration number 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid as described in WO 98 / 38856.

[0035] S8) Compounds of formula (S8) as described in WO 98 / 27049: [ka] During the ceremony, The symbols and subscripts are defined as follows: R D 1 represents halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy, R D 2 represents hydrogen or (C1-C4)-alkyl, R D 3 represents hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, with the proviso that each of the aforementioned carbon-containing groups is unsubstituted or substituted by one or more, preferably up to three, identical or different groups from the group consisting of halogen and alkoxy, or a salt thereof, n Drepresents an integer from 0 to 2.

[0036] S9) active compounds (S9) from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones, for example 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS registration number 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS registration number 95855-00-8), as described in WO 1999 / 000020;

[0037] S10) The following formula (S10 a ) or formula (S10 b ) Compound (Compounds as described in WO 2007 / 023719 and WO 2007 / 023764) [ka] During the ceremony, R E 1 represents halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, or OCF3; Y E , Z E represent, independently of one another, O or S, n E represents an integer from 0 to 4, R E 2 is (C1~C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl; benzyl, halobenzyl; R E 3 represents hydrogen or (C1-C6)-alkyl.

[0038] S11) active compounds of the oxyimino compound type (S11), known as seed dressing compositions, such as "oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), known as a seed dressing safener for millet / sorghum against metolachlor injury; "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed dressing safener for millet / sorghum against metolachlor injury, and "Siometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet / sorghum against metolachlor injury.

[0039] S12) Active compounds (S12) from the class of isothiochromanones, such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS registration number 205121-04-6) (S12-1) and related compounds from WO 1998 / 13361.

[0040] S13) One or more compounds from the following group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against thiocarbamate herbicide injury; "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice; "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet / sorghum against alachlor and metolachlor injury; "CL 304415" (CAS Registry Number 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) (obtained from American Cyanamid), which is known as a safener for corn against injury by imidazolinones; "MG 191" (CAS Registry Number 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) (obtained from Nitrokemia), which is known as a safener for corn; "MG 838" (CAS Registry Number 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) (obtained from Nitrokemia); "Disulfotone" (O,O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), "Diethylate" (O,O-diethyl O-phenylphosphorothioate) (S13-8), “Mephenate” (4-chlorophenylmethylcarbamate) (S13-9).

[0041] S14) Active compounds which, in addition to their herbicidal action against harmful plants, also have a safener action against crop plants such as rice, e.g. "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against injury by the herbicide molinate; "Dymron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against imazosulfuron herbicide injury; "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea (see JP 60087254 A) (which is known as a safener for rice against injury by some herbicides); "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against injury by some herbicides; "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (obtained from Kumiai) (CAS Registry Number 54091-06-4), which is known as a safener for injury by several herbicides in rice.

[0042] S15) As described in WO 2008 / 131861 and WO 2008 / 131860, A compound of the following formula (S15) or a tautomer thereof: [ka] During the ceremony, R H 1 represents a (C1-C6)-haloalkyl group; R H 2 represents hydrogen or halogen, R H 3 , R H 4 are each independently hydrogen, (C1-C 16 )-Alkyl, (C2-C 16 )-alkenyl or (C2-C 16 )-Alkynyl with the proviso that each of the latter three radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclyl, or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl fused on one side to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl fused on one side to a 4- to 6-membered saturated or unsaturated carbocyclic ring; with the proviso that each of the latter four radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclyl. represents or R H 3 represents (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy, and R H 4 represents hydrogen or (C1-C4)-alkyl, or R H 3 and R H 4 represents, together with the directly bonded nitrogen atom, a 4-8 membered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group N, O and S, and which is unsubstituted or substituted by one or more groups from the group halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio.

[0043] S16) Active compounds which are primarily used as herbicides but also have a safener action on crop plants, e.g. (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidiclorethyl).

[0044] The term "crop" is intended to mean a plant or plant product that can be grown extensively and harvested for profit or survival.

[0045] The term "sprout inhibitor" or "sprout inhibitor" refers to a compound that inhibits or reduces sprout formation in a crop for a period of time. Examples of sprout inhibitors include ethylene, green mint oil, carvone, maleic hydrazide and 1,4-dimethylnaphthalene, isopropyl-(3-chlorophenyl)carbamate (CIPC, chlorpropham), extracts of peppermint oil, and rapeseed oil methyl ester. Often, a mixture of two or more sprout inhibitors is used to provide sufficient sprout inhibition.

[0046] The term "combination" is intended to mean any mixture of a compound of formula (I) with one or more additional herbicides.

[0047] The term "composition" is intended to mean any mixture of a compound of formula (I) with other active ingredients and / or compounding agents and / or calcium and / or potash.

[0048] The compounds of formula (I) according to the invention exhibit excellent and desirable effects in terms of sprout inhibition in crops, more preferably in harvested crops, without substantial damage to the crop and its quality.

[0049] "Quality" in this particular case means that the potatoes remain free from external or internal damage, disease and deterioration and remain healthy. It also means that the potatoes retain their typical taste and aroma, as well as their typical firmness. Furthermore, the conversion of starch into sugars due to the development of shoots must be prevented.

[0050] Treatments can be applied as a cover over the top of the plants up to three weeks before actual harvest, when the crop has recovered from any blemishes or damage that occurred during harvest and transportation, and in storage when the crop begins to break natural dormancy after a storage period until shipment to its final destination in the market and processing plant.

[0051] Preferably, the crop is processed after it is harvested until it is released from storage.

[0052] More preferably, the crop is treated in storage after harvest and recovery in storage, generally from 7 days after arrival to about 3 months after harvest up to 12 months after harvest until release from storage. The treatment can be applied once or repeatedly.

[0053] "Harvested crop" in this particular case refers to the crop, or more specifically the tubers and bulbs, after it has been collected from the field and allowed to recover from any damage and bruising that occurred during the harvesting process. The harvesting process includes the actual collection of the bulbs and tubers from the field, their transportation to storage facilities and storage locations, which may include several loading and unloading processes.

[0054] "Tubers" refers to bulbs, corms, stem tubers (potatoes), hypocotyl bulbs, tuberous roots, or bulbs, depending on the crop from which the "tubers" are harvested. Very often, the storage organ of a plant is used for human consumption.

[0055] Preferred crops are onion, cassava (Manihot esculenta), potato (Solanum tuberosum L.), and sweet potato (Ipomoea batatas). * , yams (Dioscorea spp.), Jerusalem artichoke (Helianthus tuberosus), and ginger (Zingiber officinale).

[0056] A particularly preferred crop is the potato.

[0057] The compounds (I) according to the invention are particularly suitable for use with commodity and industrial potatoes.

[0058] The compounds (I) according to the invention can also be used to temporarily inhibit the germination of seed potatoes.

[0059] However, the use of the active compounds and active compound combinations or active compound compositions according to the invention is in no way limited to these genera, but also extends in the same manner to other plants or crops or harvested crops. According to the invention, crop plants are all plants and plant cultivars, including transgenic plants and plant cultivars, for which a shoot inhibitor is also required.

[0060] The application rates for the herbicidal compounds of formula (I) or salts thereof may vary widely and generally depend on weather and storage conditions, as well as on the time of harvest and post-harvest, or whether the compounds are combined with other active ingredients that inhibit germination. Suitable application rates for the compounds of formula (I) are generally within the range of 0.001-2000 g of active ingredient (= compound (I)) / tonne of treatment / tuber (ai / to), preferably within the range of 0.01-500 g ai / to, more preferably within the range of 0.1-100 g ai / to.

[0061] The present invention therefore also relates to a method for controlling harvested plants, comprising the step of applying to the crop a compound of formula (I) or a combination thereof or a composition comprising them, either together or one active ingredient after the other, optionally before or after treatment with one or more other sprout inhibitors.

[0062] Various sprout inhibitors are expected to have an effect on respiration rate, if not during the dormancy period, then at least after the end of the superficial dormancy period. Single and combined applications of sprout inhibitors reduce physiological losses, which is a major advantage.

[0063] In many cases, the combination / composition is surprisingly more efficient / effective than the compounds alone.

[0064] Surprisingly, there is also a superadditive (=synergistic) effect in the combined application of the compound of formula (I) with further active ingredients.The activity of the combination / composition is then stronger than the expected sum of the activities of the individual compounds used for sprout suppression.The synergistic effect allows the application rate to be further reduced.

[0065] Applicable The composition can be used in dry form as a powder or granules that are applied to the potatoes while the storage space is filled with potatoes (this is the so-called basic treatment).

[0066] Instead of being used in powder or granular form, the composition can also be misted or sprayed as a liquid or emulsion, either neat or mixed with a small amount of water, over the potatoes while they are stored in the storage area.

[0067] Additionally, the composition may also be contacted with the potatoes at a later stage during the storage period by misting the composition in the storage space with the assistance of a fan within the storage space.

[0068] In that case, depending on the desired application form, the composition can also contain suitable conventional carriers, suitable solvents, fillers or other substances.

[0069] Suitable powdered or granular carriers and fillers are starch and starch derivatives, clays, talc and other silicas, sand, diatomaceous earth, calcium carbonate and calcium sulfate (gypsum), as well as various (co)polymers which can be used as carriers.

[0070] To prepare granules, an inert carrier can be mixed with each of the compositions or the inert carrier can be impregnated with each of the compositions.

[0071] Suitable for applying the composition in liquid form are solvents of mineral origin, including aliphatic or aromatic solvents, which may or may not be chlorinated, or their mixtures.Examples of these solvents include xylene, dichloromethane, ketones, aldehydes, alcohols, such as glycerol (e.g. polyethylene glycol), or their derivatives or mixtures.It is also possible to use solvents of animal or vegetable origin, such as linseed oil, soybean oil, or their derivatives.It is also possible to use mixtures of such solvents of animal, vegetable and mineral origin.

[0072] Suitable auxiliaries for spray or mist application are cationic, anionic and nonionic surface-active substances of animal, vegetable and mineral origin, such as rapeseed oil methyl ester or nonylphenol polyglycol ethers, ethoxylated fatty acid alcohols or ethoxylated fatty acid amines or derivatives or combinations thereof.

[0073] An extension of the active period can be achieved by repeated applications of the compositions according to the invention as sprout inhibitors during storage.

[0074] Bulk potatoes are first dried and stored at about 15°C for several days, then cooled to the desired storage temperature over a period of about two weeks to ensure good wound healing of the damaged potatoes. This wound healing period is necessary to limit microbial attack and weight loss during storage.

[0075] The damage repair period for one lot is approximately 14 days.

[0076] After the wound repair period, the potatoes are stored at the desired storage temperature, where the temperature is controlled by fresh air cooling or mechanical cooling.

[0077] The desired storage temperatures are 2-4°C for seed potatoes, 4-6°C for commodity potatoes, 5-8°C for the French fry and drying industry, and 7-10°C for potato chips.

[0078] After several months of dormancy after harvest, potatoes begin to show a tendency to sprout (depending on the variety, history and storage method), which becomes more and more pronounced over time.

[0079] If the cooling is carried out in a mechanical manner (so that the desired storage temperature can be reached quickly), the possibility of early germination is now limited. In order to inhibit germination in an optimal manner, the composition according to the invention is then used.

[0080] The use of the compositions according to the invention as sprout inhibitors is now furthermore disclosed.

[0081] The so-called basic treatment consists, for example, of applying the composition (for example in the form of a powder or granules) onto a conveyor which transports the potatoes to a storage space or onto a roller table over which the potatoes pass to reach the storage location. It is also possible to spray or mist the composition over the potatoes (above the conveyor).

[0082] It is also possible to send the composition to the storage space via a ventilation system. For this mode of application, the agent can be, for example, misted or sprayed into the air. For this purpose, the mixture can be combined with a gaseous carrier to facilitate their introduction into the air stream. These two treatments can be combined or one can be carried out after the other. The herbicidal composition according to the invention is applied later in the conventional manner of dilution with water, but can also be present as a mixed formulation of components i) and ii), and, if appropriate, with further agrochemically active compounds, additives and / or conventional formulation auxiliaries, or can be prepared as a so-called tank mix by diluting the separately formulated or partially separately formulated components together with water. In certain cases, the mixed formulation can be applied diluted with other liquids or solids or otherwise in undiluted form. These treatments can also be combined or one can be carried out after the other.

[0083] The mixtures / compositions of the present invention can be formulated in various ways according to the required biological and / or physicochemical parameters. Examples of common formulation options include wettable powders (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous liquids (SL), emulsifiable concentrates (EW) (such as oil-in-water emulsions and water-in-oil emulsions), sprayable liquids or emulsions, suspension concentrates (SC), dispersions, oil dispersions (OD), suspoemulsions (SE), dusts (DP), seed dressing formulations, granules (GR) for soil application or soil spreading or water-dispersible granules (WG), ultra-low-volume formulations, microcapsule dispersions or wax dispersions.

[0084] These individual types of formulations are known in principle and are described, for example, in "Manual on Development and Use of FAO and WHO Specifications for Pesticides" (FAO and WHO, Rome, Italy, 2002); Winnacker-Kuchler, "Chemische Technologie" [Chemical Engineering] (Volume 7, C. Hanser Verlag, Munich, 4th Edition, 1986); van Valkenburg, "Pesticide Formulations" (Marcel Dekker, NY, 1973); K. Martens, "Spray Drying Handbook" (3rd Edition, 1979, G. Goodwin Ltd., London).

[0085] The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers" (2nd ed., Darland Books, Caldwell, NJ); HvOlphen, "Introduction to Clay Colloid Chemistry" (2nd ed., J. Wiley & Sons, NY); Marsden, "Solvents Guide" (2nd ed., Interscience, NY, 1950); McCutcheon's "Detergents and Emulsifiers Annual" (MC Publ. Corp., Ridgewood, NJ); Sisley and Wood, "Encyclopedia of Surface Active Agents" (Chem. Publ. Co. Inc., NY, 1964); Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Interface-active ethylene oxide adducts] (Wiss. Verlagsgesellschaft, Stuttgart, 1976); Winnacker-Kuchler, "Chemische Technologie [Chemical Engineering]" (Vol. 7, C. Hanser Verlag, Munich, 4th edition, 1986).

[0086] On the basis of these formulations it is also possible to prepare combinations with other agriculturally active compounds, such as, for example, fungicides, insecticides and also safeners, fertilizers and / or growth regulators, for example in the form of ready mixes or as tank mixes.

[0087] Wettable powders (sprayable powders) are products which are homogeneously dispersible in water and which, besides the active compound, also contain, in addition to one or more diluents or inert substances, ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols or polyoxyethylated fatty amines, polypropylene oxide / ethylene oxide copolymers, alkanesulfonates or alkylbenzenesulfonates or alkylnaphthalenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoyl methyl taurate.

[0088] Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent or mixture of organic solvents, such as butanol, cyclohexanone, dimethylformamide, acetophenone, xylene, or other high-boiling aromatics or hydrocarbons, together with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).Examples of emulsifiers that may be used include calcium alkylarylsulfonates, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide copolymers, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

[0089] Dustable preparations are obtained by grinding the active compounds with finely divided solids, for example with talc, natural clays (such as kaolin, bentonite and pyrophyllite) or diatomaceous earth.

[0090] Suspension thickener is the suspension of active compound based on water.Suspension thickener can be prepared by, for example, wet grinding with commercially available bead mill, and adding additional surfactants as required, for example, as already listed above for other formulation types.In addition to the suspended active compound(s), other active compounds can also be present in the formulation in dissolved form.

[0091] Oil dispersions are suspensions of active compounds based on oil, where oil should be understood to mean any organic liquid, for example vegetable oil, aromatic or aliphatic solvent, or fatty acid alkyl ester.Oil dispersions can be prepared, for example, by wet grinding in a commercial bead mill, and, if appropriate, by adding further surfactants (wetting agents, dispersants), for example, as already mentioned above in the case of other formulation types.In addition to the suspended active compound(s), other active compounds may also be present in the formulation in dissolved form.

[0092] Emulsions, for example oil-in-water emulsions (EW), can be prepared, for example, from a mixture of water and water-immiscible organic solvents and, if appropriate, further surfactants, for example as already mentioned above in the case of the other formulation types, by means of stirrers, colloid mills and / or static mixers, in which the active compound is present in dissolved form.

[0093] Granules can be prepared by spraying the active compound onto an adsorbent granulated inert material, or by applying a concentrate of the active compound onto the surface of a carrier (such as sand, kaolinite, chalk, or granulated inert material) with the aid of a binder (such as polyvinyl alcohol, sodium polyacrylate, or otherwise mineral oil). Suitable active compounds can also be granulated in a conventional manner for the manufacture of fertilizer granules, if desired as a mixture with fertilizer. Water-dispersible granules are generally produced by conventional processes, such as spray drying, fluidized bed granulation, pan granulation, mixing with a high-speed mixer, and extrusion without solid inert materials. For the production of granules by pan, fluid bed, extruder and spray, see, for example, the processes in "Spray Drying Handbook" (3rd ed., 1979, G. Goodwin Ltd., London), JE Browning, "Agglomeration" (Chemical and Engineering, 1967, p. 147 ff.), and "Perry's Chemical Engineer's Handbook" (5th ed., McGraw Hill, New York 1973, p. 8-57).

[0094] For further details regarding the formulation of crop protection compositions, see, for example, G.C. Klingman, "Weed Control as a Science" (John Wiley and Sons, Inc., New York, 1961, pp. 81-96), and J.D. Freyer, S.A. Evans, "Weed Control Handbook" (5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103).

[0095] Agrochemical formulations generally contain 0.1-99% by weight, in particular 2-95% by weight, of the active compound of the herbicidal component, the following concentrations being customary depending on the type of formulation: in wettable powders the active compound concentration is, for example, about 10-95% by weight, the remainder up to 100% by weight being made up of customary formulation components. In the case of emulsifiable concentrates the active compound concentration can be, for example, 5-80% by weight. In most cases, formulations in the form of dusts contain 5-20% by weight of active compound, sprayable liquids contain about 0.2-25% by weight of active compound. In the case of granules (such as, for example, dispersible granules), the active compound content depends in part on whether the active compound is present in liquid or solid form and on which granulation aids and fillers are used. In water-dispersible granules the content is generally between 10-90% by weight.

[0096] In addition, the active compound formulations mentioned may contain, where appropriate, the respective customary adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, antifoaming agents, evaporation inhibitors, and pH or viscosity modifiers.

[0097] The herbicidal action of the combinations / compositions according to the invention can be improved, for example, by surfactants, for example by wetting agents from the group of the fatty alcohol polyglycol ethers. The fatty alcohol polyglycol ethers preferably contain 10 to 18 carbon atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether moiety. The fatty alcohol polyglycol ethers can be present in non-ionic form or in ionic form, for example in the form of fatty alcohol polyglycol ether sulfates or fatty alcohol polyglycol ether phosphates, which are used, for example, as alkali metal salts (for example sodium and potassium salts) or ammonium salts or even as alkaline earth metal salts (for example magnesium salts, etc.); for example C 12 / C 14- sodium fatty alcohol diglycol ether sulfate (Genapol® LRO, Clariant GmbH), etc.; see, for example, EP-A-0 476 555, EP-A-0 048 436, EP-A-0 336 151 or US-A-4 400 196, and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988). Non-ionic fatty alcohol polyglycol ethers contain, for example, 2 to 20, preferably 3 to 15, ethylene oxide units (C 10 ~C 18 )-, preferably (C 10 ~C 14 )-Fatty alcohol polyglycol ethers (e.g. isotridecyl alcohol polyglycol ethers), for example from the Genapol® X series: such as, for example, Genapol® X-030, Genapol® X-060, Genapol® X-080 or Genapol® X-150 (all available from Clariant GmbH).

[0098] The present invention further comprises a mixture of the combination / composition according to the invention with the above-mentioned wetting agent from the group of fatty alcohol polyglycol ethers, which preferably contain 10 to 18 carbon atoms in the fatty alcohol group and 2 to 20 ethylene oxide units in the polyglycol ether moiety, and which may be present in non-ionic form or in ionic form (for example as fatty alcohol polyglycol ether sulfates). 12 / C 14- sodium fatty alcohol diglycol ether sulfate (Genapol® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ethers having 3 to 15 ethylene oxide units, such as those from the Genapol® X series, such as Genapol® X-030, Genapol® X-060, Genapol® X-080 and Genapol® X-150 (all available from Clariant GmbH), are preferred. Fatty alcohol polyglycol ethers, such as non-ionic or ionic fatty alcohol polyglycol ethers (e.g. fatty alcohol polyglycol ether sulfates), are also known to be suitable as penetrants and activity enhancers for a large number of other herbicides, including those from the group of imidazolinone herbicides (see, for example, EP 0502014 A1).

[0099] The herbicidal action of the combination / composition according to the present invention can also be enhanced by using vegetable oil.The term vegetable oil should be understood as meaning the oil of oleaginous plant species, such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil or castor oil, in particular rapeseed oil, and also their transesterification products, such as alkyl esters (such as rapeseed oil methyl ester or rapeseed oil ethyl ester).

[0100] The vegetable oil is preferably C 10 ~C 22 - of fatty acids, preferably C 12 ~C 20 -Esters of fatty acids. 10 ~C 22 Fatty acid esters are, for example, unsaturated or saturated C 10 ~C 22 - esters of fatty acids, such as erucic acid, lauric acid, palmitic acid and especially C 18- They are esters of fatty acids, such as, for example, stearic acid, oleic acid, linoleic acid or linolenic acid.

[0101] C 10 ~C 22 Examples of fatty acid esters are those which combine glycerol or glycol, e.g., with the C 10 ~C 22 - esters obtained by reacting with fatty acids or, for example, with glycerol or glycol, as described above C 10 ~C 22 -Fatty acid esters, C1-C 20 - C, which can be obtained by transesterification with alcohols (e.g., methanol, ethanol, propanol or butanol) 10 ~C 22 -Fatty acid C1~C 20 -alkyl esters. This transesterification can be carried out by known methods, for example as described in Rompp Chemie Lexikon (9th edition, volume 2, page 1343, Thieme Verlag, Stuttgart).

[0102] Preferred C 10 ~C 22 -Fatty acid C1~C 20 -Alkyl esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters. Preferred C of glycol and glycerol 10 ~C 22 -Fatty acid ester is C 10 ~C 22 - fatty acids, in particular fatty acids having an even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid and in particular C 18 - homogeneous or mixed glycol and glycerol esters of fatty acids, such as, for example, stearic acid, oleic acid, linoleic acid or linolenic acid.

[0103] In the herbicidal combinations / compositions according to the invention, the vegetable oils can be present, for example, in the form of commercially available oil-containing formulation additives, in particular formulation additives based on rapeseed oil, such as Hasten® (Victorian Chemical Company (Australia); hereinafter referred to as Hasten; main component: rapeseed oil ethyl ester), Actirob® B (Novance (France); hereinafter referred to as Actirob B; main component: rapeseed oil methyl ester), Rako-Binol® (Bayer AG (Germany); hereinafter referred to as Rako-Binol; main component: rapeseed oil), Renol® (Stefes (Germany); hereinafter referred to as Renol; vegetable oil component: rapeseed oil methyl ester) or Stefes Mero® (Stefes (Germany); hereinafter referred to as Mero; main component: rapeseed oil methyl ester).

[0104] In a further embodiment, the present invention encompasses a combination of components i) and ii) with a vegetable oil as described above (such as, for example, rapeseed oil), preferably in the form of a commercially available oil-containing formulation additive, in particular a formulation additive based on rapeseed oil (such as, for example, Hasten®, Actirob® B, Rako-Binol®, Renol®, or Stefes Mero®).

[0105] For application, the commercial formulations are diluted, if appropriate, in the customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Dust-type preparations, granules for soil application or for scattering, and sprayable formulations are usually not further diluted with other inert substances prior to application.

[0106] The active compounds can be applied to the plants, plant parts, plant seeds or the area under cultivation (soil), preferably to immature plants and plant parts and optionally also to the soil.

[0107] One possible use is the joint application of the active compounds in the form of a tank mix, in which optimally formulated concentrated formulations of the individual active compounds are mixed together with water in a tank and the resulting spray is applied.

[0108] A co-weedicidal formulation of the herbicidal composition according to the invention comprising component i) and component ii) has the advantage that it can be applied more easily, since the amounts of the components are already adjusted to the correct ratio with respect to one another. Moreover, the auxiliaries in the formulation can be optimized with respect to one another.

[0109] A. Typical Mixing Examples a) Dusts are obtained by mixing 10 parts by weight of active compound / active compound mixture with 90 parts by weight of talc, as inert substance, and comminuted the mixture in a hammer mill.

[0110] b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound / active compound mixture with 64 parts by weight of kaolin-containing clay as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoyl methyl taurate as wetting and dispersing agent and grinding the mixture in a pinned-disc mill.

[0111] c) A suspension concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of active compound / active compound mixture with 5 parts by weight of tristyrylphenol polyglycol ether (Soprophor BSU), 1 part by weight of sodium lignosulfonate (Vanisperse CB) and 74 parts by weight of water and grinding the mixture in an attrition ball mill to a fineness of less than 5 microns.

[0112] d) A readily water-dispersible oil dispersion is obtained by mixing 20 parts by weight of active compound / active compound mixture with 6 parts by weight of alkylphenol polyglycol ether (Triton® X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling point range, for example, approximately 255-277° C.) and grinding the mixture in an antifriction ball mill to a fineness of less than 5 microns.

[0113] e) An emulsifiable concentrate is obtained from 15 parts by weight of active compound / active compound mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.

[0114] f) The water-dispersible granule comprises 75 parts by weight of active compound / active compound mixture, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol, and 7 parts by weight of kaolin Mix the The mixture is milled in a pin disc mill and the powder is obtained by granulating in a fluidized bed by spray application of water as the granulating fluid.

[0115] g) The water-dispersible granules are also milled in a colloid mill. 25 parts by weight of active compound / active compound mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoyl methyl taurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate, and 50 parts by weight of water is homogenized and pre-milled, The mixture is then milled in a bead mill and the resulting suspension is atomized in a spray tower by means of a single-phase nozzle and dried.

[0116] B. Biological Examples Show me how The application was carried out on a roller table. The application was carried out by spray application, covering the outside of the tubers evenly with a spray solution containing the compound of formula (I) at the respective dose and, depending on the treatment, additional MSO (methylated seed oil), as shown in the table below. The spray solution was prepared to correspond to the equivalent of 10 L of water per ton of potatoes.

[0117] [Table 1]

[0118] [Table 2]

Claims

1. Methyl (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (Ia) and methyl (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (Ib) ＊ , 4R ＊ Use of (5S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I) for sprout inhibition: 【Chemistry 1】 。

2. The methyl(2R) compound according to claim 1 in combination with at least one additional sprout inhibitor for sprout inhibition. ＊ , 4R ＊ )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

3. The methyl (2R) compound according to claim 1 in combination with chlorpropham. ＊ , 4R ＊ )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

4. The methyl (2R) ester of claim 1 in combination with an extract of peppermint oil. ＊ , 4R ＊ )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

5. 5. The methyl(2R) compound according to any one of claims 1 to 4 in combination with at least one additional active ingredient from the group comprising herbicides, insecticides, acaricides, fungicides, safeners, fertilizers, growth regulators. ＊ , 4R ＊ )-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I).

6. 6. Use according to any one of claims 1 to 5, characterized in that the compound of formula (I) or a salt or combination or composition thereof is applied to harvested crops before or after shoot emergence.

7. Use according to any one of claims 1 to 6, characterized in that 0.01 to 2000 g of a compound of formula (I) or a salt or combination or composition thereof per tonne is applied to the crops.

8. 13. A method for suppressing sprouts in crops which comprises applying to said crops a compound of formula (I) or a salt or combination or composition thereof.

9. 9. Use / method according to any one of claims 1 to 8, characterized in that the crops are onion, cassava (Manihot esculenta), sweet potato (Ipomoea batatas), yam (Dioscorea spp.), Jerusalem artichoke (Helianthus tuberosus), ginger (Zingiber officinale).

10. 10. The use / method according to claim 9, characterized in that the crop is potato.

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