WO2012084812A1 - Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions - Google Patents

Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions Download PDF

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Publication number
WO2012084812A1
WO2012084812A1 PCT/EP2011/073225 EP2011073225W WO2012084812A1 WO 2012084812 A1 WO2012084812 A1 WO 2012084812A1 EP 2011073225 W EP2011073225 W EP 2011073225W WO 2012084812 A1 WO2012084812 A1 WO 2012084812A1
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Prior art keywords
group
spp
indanyl
methyl
compounds
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Ceased
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PCT/EP2011/073225
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English (en)
French (fr)
Inventor
Isabella Venturini
Matteo Santino Vazzola
Entela SINANI
Franco Pellacini
Lucio Filippini
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Isagro Ricerca SRL
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Isagro Ricerca SRL
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Priority to PL11802073T priority Critical patent/PL2655333T3/pl
Priority to ES11802073.4T priority patent/ES2544291T3/es
Priority to MA36117A priority patent/MA34831B1/fr
Priority to DK11802073.4T priority patent/DK2655333T3/en
Priority to CN201180066324.XA priority patent/CN103502220B/zh
Priority to CA2821225A priority patent/CA2821225C/en
Priority to HRP20150808TT priority patent/HRP20150808T1/hr
Priority to EA201390859A priority patent/EA022503B1/ru
Priority to US13/995,853 priority patent/US9192160B2/en
Priority to RS20150526A priority patent/RS54168B1/sr
Priority to KR1020137018995A priority patent/KR101861398B1/ko
Priority to JP2013545260A priority patent/JP5844382B2/ja
Priority to PH1/2013/501219A priority patent/PH12013501219A1/en
Priority to SI201130560T priority patent/SI2655333T1/sl
Priority to MX2013007196A priority patent/MX345229B/es
Priority to MYPI2013701037A priority patent/MY190321A/en
Priority to AU2011347585A priority patent/AU2011347585B2/en
Priority to EP20110802073 priority patent/EP2655333B1/en
Application filed by Isagro Ricerca SRL filed Critical Isagro Ricerca SRL
Priority to NZ613430A priority patent/NZ613430A/en
Priority to CR20200294A priority patent/CR20200294A/es
Priority to BR112013015516A priority patent/BR112013015516B8/pt
Priority to UAA201308725A priority patent/UA109924C2/uk
Publication of WO2012084812A1 publication Critical patent/WO2012084812A1/en
Priority to TNP2013000255A priority patent/TN2013000255A1/fr
Priority to IL227035A priority patent/IL227035B/en
Anticipated expiration legal-status Critical
Priority to ZA2013/05238A priority patent/ZA201305238B/en
Priority to US14/927,432 priority patent/US20160113278A1/en
Priority to US15/712,080 priority patent/US10149473B2/en
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • the present invention relates to new amides of 4- aminoindanes having a high fungicidal activity, the relative phytosanitary compositions and their use for the control of phytopathogenic fungi.
  • EP199822 describes 1 , 3 , 5-trimethyl-
  • the object of the present invention therefore relates to aminoindanes amides having the structural formula
  • Ri, R2 and R4 equal to or different from each other, represent a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, the groups Ri and R2 can possibly be joined to form a C3-C6 cycloalkyl group spiro-condensed with indanyl;
  • - R3 represents a hydrogen atom, a C 1 -C3 alkyl group, a C 1 -C3 haloalkyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group;
  • R 5 represents a halogen atom, a C 1 -C4 alkyl group, a C 1 -C4 haloalkyl group, a C 1 -C4 alkoxy group, a C 1 -C4 haloalkoxy group, an SH group, a C 1 -C4 alkylthio group, a C 1 -C4 haloalkylthio group;
  • - n represents an integer ranging from 1 to 3;
  • R-6 is a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, an SH group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group .
  • Preferred compounds having general formula (I) are those wherein A represents Ai, Ri, R2, R4 and R6 are a methyl group, R3 is a hydrogen atom, R 5 represents a halogen .
  • halogen examples include fluorine, chlorine, bromine, iodine.
  • C1-C4 alkyl linear or branched, are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.
  • C1-C4 haloalkyl examples include fluoromethyl, difluoromethyl , trifluoromethyl , chloromethyl , dichloromethyl , 2 , 2 , 2-trifluoroethyl , 1,1,2,2- tetrafluoroethyl , pentafluoroethyl , heptafluoropropyl ,
  • C1-C4 alkoxy linear or branched, are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy.
  • C1-C4 haloalkoxy examples include fluoromethoxy , difluoromethoxy, trifluoromethoxy, chloromethoxy , dichloromethoxy , 2 , 2 , 2-trifluoroethoxy, 1, 1, 2, 2-tetra- fluoroethoxy, 1 , 1 , 2 , 3 , 3 , 3-hexafluoropropoxy, 4,4,4- trichlorobutoxy .
  • C3-C6 cycloalkyl examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl.
  • C3-C6 halocycloalkyl examples are 2 , 2-dichloro- cyclopropyl, 2, 2-difluorocyclopropyl, 2,2,3,3- tetrafluorocyclobutyl, 3, 3-difluorocyclopentyl, 2- fluorocyclohexyl .
  • C1-C4 alkylthio linear or branched, are methylthio, ethylthio, n-propylthio , isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert- butylthio .
  • C1-C4 haloalkylthio examples include fluoromethylthio , difluoromethylthio , trifluoromethyl- thio, chloromethylthio , dichloromethylthio , 2,2,2- trifluoroethylthio , 1 , 1 , 2 , 2-tetra-fluoroethylthio,
  • the compounds having formula (I) may occur as mixtures of optical isomers and possibly diastereoisomers.
  • the compounds having formula (I) are prepared by reacting a substituted acid or one of its derivatives having formula (II), with an aniline having formula (III), according to the reaction scheme indicated below :
  • A, Ri , R2 , R3, R4, R5 and n have the meanings defined above ;
  • X represents a hydroxy OH ; a halogen atom; a C1-C4 alkoxy group; a phenoxy group; an acyloxy group RCOO wherein R in turn represents a group A, a C1-C4 alkyl group or a phenyl optionally substituted by C1-C4 alkyl groups, C1-C4 haloalky groups, halogen atoms.
  • reaction is normally carried out in the presence of an inert solvent and in the presence of an organic or inorganic base, at a temperature ranging from -20°C to the boiling point of the reaction mixture.
  • X represents a halogen atom, preferably chlorine
  • the reaction is normally carried out in the presence of an inert solvent and in the presence of an organic or inorganic base, at a temperature ranging from -20°C to the boiling point of the reaction mixture.
  • solvents which can be used for the above reaction include water, aliphatic or cycloaliphatic hydrocarbons (petroleum ether, hexane, cyclohexane etc.), chlorinated hydrocarbons (methylene chloride, chloroform, carbon tetrachloride, dichloroethane , etc.), aromatic hydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), ethers (diethyl ether, diisopropyl ether, dimethoxyethane, dioxane, tetrahydrofuran, etc.), esters (ethyl acetate etc.), ketones (acetone, methylethylketone, methylpropyl- ketone, methylisobutylketone, etc.), nitriles ( acetonitrile, benzonitrile, etc.), aprotic dipolar solvents (dimethylformamide, dimethylacet
  • Inorganic bases which can be used for the purpose are, for example, hydroxides, carbonates and bicarbonates of sodium or potassium.
  • Organic bases which can be used for the purpose are, for example, triethylamine, pyridine, 4-N,N- dimethyl-aminopyridine , N, N-dimethylaniline, N-methyl- piperidine, lutidine, diazabicyclo-octane (DABCO) , diazabicyclononene (DBN) , diazabicycloundecene (DBU) .
  • DABCO diazabicyclo-octane
  • DBN diazabicyclononene
  • DBU diazabicycloundecene
  • the compounds having general formula (I) have a very high fungicidal activity which is exerted with respect to numerous phytopathogenic fungi which attack important agricultural crops.
  • a further object of the present invention therefore relates to the use of the compounds having general formula (I) for the control of phytopathogenic fungi of agricultural crops.
  • phytopathogenic fungi which can be effectively fought with the compounds of general formula (I) according to the present invention, are those belonging to the groups of Basidiomycetes , Ascomycetes, Deuteromycetes or fungi imperfecti, Oomycetes: Puccinia spp . , Ustilago spp . , Tilletia spp .
  • Uromyces spp. Phakopsora spp., Rhizoctonia spp., Erysiphe spp., Sphaerotheca spp., Podosphaera spp., Uncinula spp., Helminthosporium spp., Rhynchosporium spp., Pyrenophora spp., Monilinia spp., Sclerotinia spp., Septoria spp.
  • Mycosphaerella spp. Venturia spp., Botrytis spp., Alternaria spp., Fusarium spp., Cercospora spp., Cercosporella herpotrichoides, Colletotrichum spp., Pyricularia oryzae, Sclerotium spp., Phytophtora spp., Pythium spp., Plasmopara viticola, Peronospora spp., Pseudoperonospora cubensis, Bremia lactucae.
  • the main crops which can be protected with the compounds of the present invention comprise cereals (wheat, barley, rye, oats, rice, corn, sorghum, etc.), fruit trees (apple, pear, plumb, peach, almond, cherry, banana, vines, strawberry, raspberry, blackberry, etc.), citrus trees (orange, lemon, mandarin, grapefruit, etc.), legumes (beans, peas, lentils, soybean, etc.), vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, aubergines, peppers, etc.), cucurbitaceae (pumpkins, zucchini, cucumbers, melons, water-melons, etc.), oilseeds (sunflower, rape, peanut, castor-oil plant, coconut, etc.) tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton.
  • cereals wheat, barley, rye, oats, rice, corn, sorghum, etc.
  • fruit trees
  • the compounds having general formula (I) have proved to be considerably effective in the control of Plasmopara viticola on vines, Phytophtora infestans and Botrytis Cinerea on tomatoes, Puccinia recondita, Erysiphe graminis, Helminthosporium teres, Septoria nodorum and Fusarium spp . on cereals; in the control of Phakopsora pachyrhizi on soya; in the control of Uromyces appendiculatus on beans; in the control of Venturia inaequalis on apples, in the control of Sphaeroteca fuliginea on cucumbers.
  • the compounds having general formula (I) are also effective in the control of phytopathogenic bacteria and viruses, such as for example Xanthomonas spp., Pseudomonas spp., Erwinia amylovora, the mosaic virus of tobacco.
  • the compounds having formula (I) are capable of exerting a fungicidal action of both in curative and preventive applications and have a very low or zero phytotoxicity on the crops treated.
  • fungicidal compositions containing compounds having formula (I) according to the present invention suitably formulated.
  • a further object of the present invention relates to fungicidal compositions comprising one or more compounds having formula (I), a solvent and/or solid or liquid diluent, possibly a surfactant.
  • the above fungicidal compositions can be in the form of dry powders, wettable powders, emulsifiable concentrates, emulsions, micro-emulsions, pastes, granulates, water dispersible granules, solutions, suspensions, etc.: the choice of the type of composition will depend on the specific use.
  • the fungicidal compositions are prepared in the known way, for example by diluting or dissolving the active substance with a solvent medium and/or a solid or liquid diluent, possibly in the presence of surfactants .
  • Solid diluents or supports which can be used for example are: silica, kaolin, bentonite, talc, diatomaceous earth, dolomite, calcium carbonate, magnesia, gypsum, clays, synthetic silicates, attapulgite, sepiolite.
  • Solvents or liquid diluents which can be used are for example, in addition to water, aromatic organic solvents (xylols or blends of alkylbenzols , chlorobenzene , etc.), paraffins (petroleum fractions), alcohols (methanol, propanol, butanol, octanol, glycerine, etc.), esters (ethyl acetate, isobutyl acetate, alkyl carbonates, alkyl esters of adipic acid, alkyl esters of glutaric acid, alkyl esters of succinic acid, alkyl esters of lactic acid, etc.), vegetable oils (rape oil, sunflower oil, soybean oil, castor oil, corn oil, peanut oil, and their alkyl esters), ketones ( cyclohexanone , acetone, acetophenone, isophorone, ethylamylketone , etc.), amides (N, N
  • the fungicidal compositions can also contain special additives for particular purposes, such as for example, antifreeze agents such as propylene glycol, or adhesion agents, such as gum Arabic, polyvinyl alcohol, polyvinyl pyrrolidone, etc.
  • antifreeze agents such as propylene glycol
  • adhesion agents such as gum Arabic, polyvinyl alcohol, polyvinyl pyrrolidone, etc.
  • fungicidal compositions containing the compounds of general formula (I) can be added to the fungicidal compositions containing the compounds of general formula (I), such as, for example, fungicides different from those having general formula
  • fungicides different from those having general formula (I), which can be included in the fungicidal compositions object of the present invention are: acibenzolar, ametoctradin, amisulbrom, ampropylfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benalaxyl-M, benomyl, benthiavalicarb, bitertanol, bixafen, blasticidin-S , boscalid, bromuconazole, bupirimate, buthiobate, captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat , chloroneb, chlorothalonil , chlozolinate, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, debacarb, dichlo
  • concentration of compounds having general formula (I) in the above compositions can vary within a wide range; it generally ranges from 1% to 90%, preferably from 5% to 50%.
  • compositions can be effected on each part of the plant, for example on the leaves, stems, branches and roots, or on the seeds themselves before sowing, or on the ground in which the plant grows .
  • a further object of the present invention therefore relates to a method for the control of phytopathogenic fungi in agricultural crops, which consists in the application of effective dosages of the compounds having formula (I), used as such or formulated in fungicidal compositions as described above.
  • the quantity of compound to be applied for obtaining the desired effect can vary in relation to different factors, such as, for example, the compound used, the crop to be preserved, the type of pathogen, the degree of infection, the climatic conditions, the application method, the formulation adopted.
  • Doses of compound ranging from 10 g to 5 kg per hectare of agricultural crop generally provide a sufficient control.
  • the raw product obtained was subsequently purified on a silica gel column (eluent hexane/ethyl acetate 8/2) to give 0.45 g of the desired product, a white solid with a melting point of 147°C.
  • Leaves of wheat plants of the Salgemma variety grown in pots in a conditioned environment kept at 20°C and 70% of relative humidity (R.H.), were treated by spraying on both sides of the leaves with the compounds under examination, dispersed in hydroacetonic solutions at 20% by volume of acetone.
  • R.H. relative humidity
  • the plants were infected under dry conditions by shaking over them, in order to distribute the inoculum, plants previously infected by Erysiphe graminis .
  • the plants were then maintained in the same cell, in a humidity-saturated environment and at a temperature ranging from 18 to 24°C for 12 days.
  • the external symptoms of the pathogen appeared and it was therefore possible to proceed with the evaluation of the intensity of the infection, on both the parts treated directly with the products (T), and also on the parts which had developed during the test (NT), by means of a visible percentage evaluation scale of the area of affected leafs; the scale comprises, as extremes, the value 100 (healthy plant) and the value 0 (completely infected plant) .
  • the evaluation scale varies from 0 (completely healthy plant) to 100 (completely necrotized plant) .
  • Table 2 shows the results obtained by carrying out the test described with compound N. 1, compared with the following reference products described in prior art :

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
PCT/EP2011/073225 2010-12-20 2011-12-19 Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions Ceased WO2012084812A1 (en)

Priority Applications (27)

Application Number Priority Date Filing Date Title
UAA201308725A UA109924C2 (uk) 2010-12-20 2011-12-19 Аміди аміноінданів, які мають високу фунгіцидну активність та їх фітосанітарна композиція
MX2013007196A MX345229B (es) 2010-12-20 2011-12-19 Amidas de aminoindanos con alta actividad fungicida y sus composiciones fitosanitarias.
MA36117A MA34831B1 (fr) 2010-12-20 2011-12-19 Amides d'aminoindanes presentant une forte activite fongicide et leurs compositions phytosanitaires
DK11802073.4T DK2655333T3 (en) 2010-12-20 2011-12-19 AMINOINDANAMIDER WITH A HIGH antifungal ACTIVITY AND THEIR PLANT FORMATIONS
CN201180066324.XA CN103502220B (zh) 2010-12-20 2011-12-19 具有高杀真菌活性的氨基茚满酰胺及其植物保健组合物
CA2821225A CA2821225C (en) 2010-12-20 2011-12-19 Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
HRP20150808TT HRP20150808T1 (hr) 2010-12-20 2011-12-19 Aminoindanski amidi s visokom antifungalnom aktivnošä†u i njihovi fitosanitarni pripravci
EA201390859A EA022503B1 (ru) 2010-12-20 2011-12-19 Аминоинданамиды, обладающие высокой фунгицидной активностью, и фитосанитарные композиции на их основе
US13/995,853 US9192160B2 (en) 2010-12-20 2011-12-19 Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
RS20150526A RS54168B1 (sr) 2010-12-20 2011-12-19 Aminoindanamidi koji imaju visoku fungicidnu aktivnost i njihove fitosanitarne kompozicije
KR1020137018995A KR101861398B1 (ko) 2010-12-20 2011-12-19 높은 살진균 활성을 가지는 아미노인단 아미드 및 그의 식물 위생 조성물
JP2013545260A JP5844382B2 (ja) 2010-12-20 2011-12-19 高殺菌力を有するアミノインダンアミド及びその植物衛生組成物
PH1/2013/501219A PH12013501219A1 (en) 2010-12-20 2011-12-19 Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
SI201130560T SI2655333T1 (sl) 2010-12-20 2011-12-19 Amidi aminoindanov, ki imajo visoko fungicidno aktivnost, in njihovi fitosanitarni sestavki
MYPI2013701037A MY190321A (en) 2010-12-20 2011-12-19 Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
PL11802073T PL2655333T3 (pl) 2010-12-20 2011-12-19 Amidy aminoidanowe mające wysoką aktywność grzybobójczą i ich kompozycje fitosanitarne
ES11802073.4T ES2544291T3 (es) 2010-12-20 2011-12-19 Amidas de aminoindanos que presentan una actividad fungicida elevada y sus composiciones fitosanitarias
EP20110802073 EP2655333B1 (en) 2010-12-20 2011-12-19 Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
AU2011347585A AU2011347585B2 (en) 2010-12-20 2011-12-19 Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
NZ613430A NZ613430A (en) 2010-12-20 2011-12-19 Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
CR20200294A CR20200294A (es) 2010-12-20 2011-12-19 AMIDA AMINOINADANES CON UNA ALTA ACTIVIDAD FUNGICIDA Y SUS COMPOSICIONES FITOSANITARIAS (Divisional 2013-0337)
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