CS219905B2 - Fungicide means and method of making the active agents - Google Patents
Fungicide means and method of making the active agents Download PDFInfo
- Publication number
- CS219905B2 CS219905B2 CS795676A CS567679A CS219905B2 CS 219905 B2 CS219905 B2 CS 219905B2 CS 795676 A CS795676 A CS 795676A CS 567679 A CS567679 A CS 567679A CS 219905 B2 CS219905 B2 CS 219905B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- anilide
- furyl
- acid
- oxoperhydro
- methyl
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 11
- 239000013543 active substance Substances 0.000 title description 15
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000417 fungicide Substances 0.000 title 1
- -1 C3-C6-alkynyl Chemical group 0.000 claims abstract description 59
- 239000002253 acid Substances 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical class CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
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- 239000011593 sulfur Chemical group 0.000 claims description 3
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- 239000011230 binding agent Substances 0.000 claims description 2
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- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof 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
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof 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
- A01N47/14—Di-thio analogues thereof
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
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- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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- Plural Heterocyclic Compounds (AREA)
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Abstract
Description
(54) Fungicidní prostředek a způsob výroby účinných látek . . ' . 1(54) Fungicidal composition and process for the manufacture of active substances. . '. 1
Nové fungicidní prostředky obsahující jako účinné látky anihdy kyseliny oct:ové obecného vzorce I Y new fungicidal compositions comprising as active ingredients gamma anihd acid -acetic b s of the formula I
ve kterém R, je vodík nebo methyl, R2 je fenyl nebo fenyl substituovaný methylem, chlorem, fluorem, kyanem, methoxyskupino^ dvakrát methylem nebo cMorem a methylem, R3 je Ct—C4-alkyl, fenyl nebo methylkarbonyl, а X je kyslík, síra nebo sulfonyl. Tyto fungicidní prostředky nemají fytotoxický účinek, přičemž vykazují jak kurativní, tak systemický účinek při ošetřování rostlinných kultur; lze jich používat mnoha způsoby na rostliny, do· půdy nebo/a na osivo.wherein R is hydrogen or methyl, R2 is phenyl or phenyl substituted by methyl, chloro, fluoro, cyano, methoxy-methyl twice no b of chloro and methyl, R3 is C t -C 4 -alkyl, phenyl or methylcarbonyl, а X is oxygen, sulfur or sulfonyl. These fungicidal compositions have no phytotoxic effect and show both curative and systemic action in the treatment of plant crops; they can be used in many ways for plants, soil and / or seed.
Je popsán také způsob výroby sloučenin obecného vzorce Ί.Also described is a process for the preparation of compounds of the general formula Ί.
Vynález se 'týká způsobu výroby nových anílidů kyseliny octové, které jsou účinnými ' -složeninami pro nové fungtóidní prostředky, jakož i těclito fungicidní prostředků k hubení fytopatogenní hub obsahujících alespoň jednu ze zmíněných sloučenin.The invention pertains to novel anilide acetic acid, which are effective '-složeninami for newly fungtóidní midst alkyl, and j and k oz těclito fun gi CIDNA Dec. tředků kh b in learning fy topato g Ennio hu b containing at least one of said compounds .
Prostředky k hubení fytopatogenní hub jsou již známy. Prostředky tohoto druhu, známými z praxe, _ jsou například -tetramethylthiuramdisulfid (DE-PS 642 532) a maganethylen-bisdithiokarbamát (US-PS Thanks to prostrata kh b u fy learning that p g ato Ennio hu b are already known. Compositions of this kind, known from practice _ are the example, -tetramethylthiuramdisulfid (DE-PS 642 532) and Leu-maganeth y b isdithiokarbamát (U.S.
504 404).504,404).
Olíolem tohoto vynálezu je vývoj nových fungicidů . s d-ožým žinžm na listové a půdní houby.Olíolem characterized in that n and l is the development of new cut un f gi cidů. D-Ozyme BTI for foliar and soil nus Hou would.
Tento úkol je vyřešen podle vynálezu fungicidním prostředkem, jehož podstata spočívá v tom, že jako účinnou látku obsahuje alespoň jeden anilid kyseliny octové obecného vzorce I ·This task is solved according to the invention a fungicidal composition, which is characterized in that it comprises as active ingredient at least one of acetic acid anilide, in general formula I above ·
ve kterém znamenáer in kt m = s
Rt vodík nebo methyl,Rt is hydrogen or methyl,
R2 fenyl nebo fenyl substituovaný methylem, chlorem, fluorem, kyanem, metžxy-skupincž dvakrát methylem než chlorem a methylem,R2 phenyl or phenyl substituted by methyl, CH l Orem, fluorine, alkyl anus, metžxy-skupincž than twice by methyl, chlorine and methyl,
R3 C až C4-alkyl, fenyl nebo methylkarbonyl aR3 is C1-C4-alkyl, phenyl or methylcarbonyl;
X tyshk síru než sulfonylovou skupinu.X tyshk sulfur than sul f onyl SKU P inu.
Složeniny podle. vynálezu překvapivě předčí známé prostředky výše uvedeného druhu žžkem proti fytopatogenní houbám, jsou kromě tož rostlinami dobře snášeny a mají dostatečně dlouž trvání žínku. V používaných množstvích, která přicházejí prakticky v úvahu, nejsou fytotoxické, takže při její používání jsou vyloučeny negativní vlivy na růst rostlin. Díky těmto výhodným vlastnostem lze proto tyto sloučeniny používat v zemědělství nebo zahradnictví k' ošetřování půdy a prsti nebo k aplikaci na listy. With loženin yp of dl e. Y is N, climb straight EKVA p Iva BC e DCI known e p rost salaries above kind žžkem against phytopathogenic hou b AM are ave Whence plants to Sn women y and have a sufficiently long duration of washcloth. In the amounts employed, which are virtually not phytotoxic when Z t e when the p ou f IV and it excludes negative effects on plant growth. Due to these advantageous properties, the compounds can therefore be used in agriculture or horticulture for the treatment of soil and toes or foliar application.
Sloučeniny podle vynálezu se vyznačují vyrnžjžm úmem proti velkému množství škodlivých hub, jako například Pythium, Phy.tophtora, Plasmopara, Piricularia, Bottytis a datébCompounds of the invention are characterized in vyrnžjžm craft against him LKE LeVeLs Community harmful fungi, such as Pythium, Phy.tophtora, Plasmopara, Piricularia, Botrytis species and datéb
Na rozdíl od prosetredků působících pouze preventivně, jako' je napnklad manganethylen-bisdithiokarbamát, mají sloučeniny podle vynálezu mimořádnou výhodu kurativního a systémového žínku a umožňují tim rovněž 'hužrn tiub které již vnikly do rostlin.Unlike prosetredků p reventivně acting only as 'a n g napnklad anethylen bisdithiocarbamate, the compounds have an outstanding advantage and curative system E mov eh of cloth and thus allow also Ez' hužrn tiub already penetrated into the plants.
Ze sloučenin podle vynálezu se vyznačují velmi- ' dobrým účinkem zejména ty, u kterých ve výše uvedeném vzorci I Rj znam atom vodí než methylovou skupinu, R 2 - znad -fenylovou, methylfenylovou, dL· methylfenylovou, -met-hoxyfenylovou, fluorfenylovou, chlorfenylovou, díchlorfeny11ovou, trifluormethYlfenjdovou nebo kyanfenylovou skupinu, R;j značí methylovou, e^tovo^ propylovou, isopropylovou, terc.butylovou, fenylovou, methylkarbonylovou aOf the compounds of the invention are characterized velmi- 'good effect particularly those where in the above formula I, R represents hydrogen significance than verifies meth yl group, R 2 - znad nominal phen y, y en meth YLF nominal DL meth · y butylphenyl y salicylic, Met-hoxyfenylovou, fluoro f verifies en-yl, chloro, f y en salicylic, dichlorophen yl 11ovou, trifluormethYlfenjdovou or cyanophenyl, R j whose brand methylcarbazole verifies e ^ Tovo ^ p ro py nominal, isopropyl, tert-butyl, phenyl, methylcarbonyl and
X -- značí atom tyslftu, síry nebo sulfonyloivou -skupinu.X - represents considerable tyslftu d SiR y or y su lf he loivou -group.
Sloufenin podle vynálezu lze používat bud jednotlivě, nebo ve směsi nebo s dalšími účinnými WkamL Je--i to žádoucí lze přidávat i jrné fungicidy, nematocid^ insekticidy než jmé prostředky k - hužní škůdců, a -to -podle požadovaného želu. Omnných látek se používá , želž ve formě přípravků, jako například prášků zásypů granulátů roztoků, emulzí nebo suspenzí, za přidání težtých a/než pevných - nosičů popř’ípadě zřeďovadel a v případě potřeby smáčedel, ádhezív, pomocných emulgaíních a/než žspergžní činidel.Sloufenin dl p o ev y n and l l Cutting of t used either singly or in admixture with other active or WkamL Je- - also desirable that Z s can be added jrné f un g ICID y ^ nematicide insecticides than JME midst of the alkyl - hužní pests, and - -p compliance C o and f eh d crosslinked with about želu. Omnných acrylate e k p ou running in á želž in f Orme p at pH rav ku, j and k of P of manufacture kl and d powders backfilling g ranulátů solutions, emulsions or suspensions, with the addition težtých and / than p evných - carriers p o p r beta. Ada diluents and, if necessary, wetting, adhering, p omocných emulgaíních and / žspergžní than agents.
Vhodnými tekutými nosiči jsou voda, minerální oleje ' nebo ostatní organická rozpožtžž jako napNMad xylem chloržnzen, cyklohexanol, dioxan, a^t^et^i^i^ril, ethylacetát, dimethylformamid, isoforon a -dime.thylsulfoxid.Suitable liquid carriers are water, mineral oils or other organic solvents such as xylene, chlorosilane, cyclohexanol, dioxane, ethyl ether, ethyl acetate, dimethylformamide, isophorone and dimethylsulfoxide.
Jako pevné nosiče jsou vhodné vápenec, kaolin, křídy, -talek, attaclay a jiné hlinky, jakož i přirozená - nebo- syntetická kyselina křemičitá.Suitable solid carriers are limestone, kaolin, chalk, talc, attaclay and other clays, as well as natural - or synthetic silicic acid.
Z povrchově aktivních látek ke napnklad uvést: soli kyselin ligniIl,suifonových, soli alkýlóvaných žnzensutionovýž kyselí sžfonované amidy kyselin a jejich so!1, polyethoxylované aminy a alkoholy. The surfaces of the laths to active napnklad include: salts ligniIl, suifonových salts and LK PEGylated žnzensutionovýž acidified sžfonované amides and alkyl Selin so! 1, polyethoxylated amines and alcohols.
Pokud se mají účinné látky - používat k moření osiva, lze přidávat i - barvíva, aby mořené osivo mělo zřetelně viditelné -zbarvení.If the active substances are to be used for seed dressing, dyes can also be added so that the pickled seed has a clearly visible coloring.
Podíl účinné látky (resp. - látek) v prostředku lze měnit v širokých mezích, přičemž přesná koncentrace - žrnž látky použité v prostředku závisí hlavně na množsM, ve kterém mají - být prostřely použity. Prostředky obsahují příkladně 1 až 80 hmotnostní %, s výžžu mezi 20 až 50 hmotnostní % účžž látky a asi 99 až - 20 hmotnostní % tekutých než pevných nosičů jažž i popřípadě až 20 hmotnostní % povrchově aktivních tótekThe proportion of active ingredient (resp. - s) in the composition can vary within wide limits, taking p Comms and concentrations - žrnž alkyl methacrylate p oužité in the composition depends primarily upon solubilizing amount in kt m maj er s i - b YT used also furnished. The compositions comprise, for example, 1 to 80% by weight, výžžu between 20 to 50% by weight účžž agent and about 99 to - 20% by weight of liquid carrier evných than p c u i p o jazz or Ada to 20 weight% P externally to active Totek
Aplikaci prostředků ke prováfót -obvyklým způsobem, například postřikem, rozprašováním, m^en^ poprášení zplynování, zadýmování posypávání zatévání nebo mořením.A p l p ACI also rostrata dk of the prováfót -obvyklým manner, for example by spraying, atomizing s m m ^ en ^ dusting gasification zadýmování posy transmission of p zatévání or pickling.
Způsob výroby účinných - a-nilidů kyseliny octové fungicidního prostředku podle vynálezu se -provádí tak, že se uvádějí- do reakce stóženiny -ožcnéž vzorce I1 A method for producing active - and-ethyloxanilide acetic fungicidal composition according to the invention -provádí so that uvádějí- reacting stóženiny -ožcnéž formula I 1
ΗΗ
С—CH-N-H I I ! C^C=O Rz (li ve kterémС — CH-NH II! C ^ C = OR z (li in which
Rs а X mají význam udaný v bodě 1 a halogemdy kyselin obecného vzorce IIIR 5 and X are as defined in (1) above and the acid halides of the formula (III)
Hal—СО—CH2—X—R3 (III), ve kterém СО-Hal-CH2 -X-R 3 (III) in which
R3 а X mají význam udaný v bodě 1 aR3 and X have the meanings given in 1 a
Hal znamená halogen, s výhodou chlor, při teplotě —15 až -|-12э °C, popřípadě v přítomnosti látky, která váže kyselinu, rozpuštěné v organickém rozpouštědle, a výsledné produkty se izolují o sobě známým způsobem.Hal represents halogen, preferably chlorine, at a temperature of -15 to -12 ° C, optionally in the presence of an acid-binding agent dissolved in an organic solvent, and the resulting products are isolated in a manner known per se.
Jako látky schopné vázat kyseliny lze popřípadě používat například organické báze, jako pyridin, triethylamm nebo N,N-dimethyanilin nebo anorganické báze, jako hydroxidy, oxidy, a uhličitany alkalických kovů a kovů alkalických zemin.For example, organic bases such as pyridine, triethylamine or N, N-dimethyaniline or inorganic bases such as hydroxides, oxides, and carbonates of alkali metals and alkaline earth metals can optionally be used as acid-binding substances.
Jako rozpouštědel lze používat organických rozpouštědel, jako například ether, tetrahydrofuran, benzen, toluen, xylen, ethylacetát, acetonitril, dimethylformamid nebo dimethylsulfoxid. Reakce se provádějí účelně při teplotách mezi —15 a 150 °C.Organic solvents such as ether, tetrahydrofuran, benzene, toluene, xylene, ethyl acetate, acetonitrile, dimethylformamide or dimethylsulfoxide can be used as solvents. The reactions are conveniently carried out at temperatures between -15 and 150 ° C.
V případě, že X značí sulfinylovou nebo sulfonylovou skupinu, sloučeniny podle vynálezu obecného vzorce I, kde X značí atom • síry, reagují s oxidačními činidly, jako organickými perkyselinami, například kyselinou 3-chlorperbenzoovou, v netečném orga> nickém rozpouštědle, například methylenchloridu nebo chloroformu, nebo s anorganickými činidly, jako například s peroxidem vodíku nebo manganistanem draselným, při teplotách mezi 0 a 100 °V v kyselině octové. Pro přípravu sulfinylderivátů je zapotřebí dvou oxidačních ekvivalentů a v případě sulfonylderivátů asi čtyř oxidačních ekvivalentů.When X is a sulfinyl or sulfonyl group, the compounds of formula I wherein X is a sulfur atom react with oxidizing agents such as organic peracids such as 3-chloroperbenzoic acid in an inert organic solvent such as methylene chloride; chloroform, or with inorganic agents such as hydrogen peroxide or potassium permanganate, at temperatures between 0 and 100 ° V in acetic acid. Two oxidation equivalents are required for the preparation of sulfinyl derivatives and about four oxidation equivalents in the case of sulfonyl derivatives.
Následující příklady osvětlují přípravu sloučenin podle vynálezu.The following examples illustrate the preparation of the compounds of the invention.
Příklady provedeníExamples
Příklad 1 [ 2,6-dimethyl-N - (2-ketoperhydro-3-furyl) anilid] kyseliny methoxyoctovéExample 1 Methoxyacetic acid [2,6-dimethyl-N- (2-ketoperhydro-3-furyl) anilide]
Směs 9,75 g (0,047 mol) 3-(2,6-dimethylanilino)perhydrofuran-2-onu, 6,50 g (0,06 mol) methoxyacetylchloridu, 250 ml toluenu a 2 ml dimethylformamidu se míchá po dobu tří hodin při teplotě 25 °C a potom 1 hodinu při teplotě varu. Reakční směs se odpaří ve vakuu к suchu a pevný zbytek se digeruje diisopropyletherem. Po odsátí krystlů se suší ve vakuu při teplotě 25 °C. Výtěžek: 11,5 g = 88 % teorie.A mixture of 9.75 g (0.047 mol) of 3- (2,6-dimethylanilino) perhydrofuran-2-one, 6.50 g (0.06 mol) of methoxyacetyl chloride, 250 ml of toluene and 2 ml of dimethylformamide is stirred for three hours at 25 ° C and then 1 hour at boiling point. The reaction mixture was evaporated in vacuo to dryness and the solid residue digested with diisopropyl ether. After aspirating the crystals, they are dried under vacuum at 25 ° C. Yield: 11.5 g = 88% of theory.
Teplota tání: 130 až 131 °C.Melting point: 130-131 ° C.
Příklad 2 [ 2,6-dimethyl-N-( 2-oxoperhydro-3-furyl) anilid] kyseliny acetoxyoctovéExample 2 Acetoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]
10,26 g (0,05 mol) 3-(2,6-dimethylamlino) perhydrofuran-2-onu, rozpuštěných ve 200 ml toluenu, se smísí s 6,85 g (0,05 mol) chloridu kyseliny acetoxyoctové a zahřívá se po dobu jedné hodiny к varu. Reakční směs se potom odpaří ve vakuu к suchu. Získaný olej zkrystaluje rozetřením s etherem. Krystaly se odsají, promyjí několikrát malým množstvím etheru a látka se suší asi při 25 °C ve vakuu.10.26 g (0.05 mol) of 3- (2,6-dimethylamino) perhydrofuran-2-one, dissolved in 200 ml of toluene, were mixed with 6.85 g (0.05 mol) of acetoxyacetic acid chloride and heated for one hour to boil. The reaction mixture was then evaporated in vacuo to dryness. The oil obtained is crystallized by trituration with ether. The crystals are sucked off, washed several times with a small amount of ether and dried at about 25 ° C under vacuum.
Výtěžek: 12,64 g = 82.8 % teorie.Yield: 12.64 g = 82.8% of theory.
Teplota tání: 106 až 108 °C.Melting point: 106-108 ° C.
Příklad 3 [ 2,6-dimethyl-N-(2-oxoperhydr o-3-f uryl)anilid] kyseliny methylthiooctovéExample 3 Methylthioacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]
28,17 g (0,1 mol) [ 2,6-dimethyl-N-(2-oxoperhydro-3-furyl)anilidu] kyseliny chloroctové se rozpustí ve 120 ml acetonitrilu a nechá reagovat s 6,5 g (0,15 mol) methylátu sodného. Směs se ochladí asi na —15 °C a nechá reagovat s 22,4 g (0,47 mol) methylmerkaptanu. Po malém zahřátí na teplotu 20 až 25 °C se směs dále míchá po dobu asi 20 hodin při této teplotě. Potom se rozdělí do směsi ethylacetát/voda a alkalická vodná fáze se oddělí. Organická fáze se vytřepe jednou roztokem hydroxidu sodného a potom promyje do neutrální reakce. Ethylacetátová fáze se suší nad síranem horečnatým, odfiltruje a zahustí ve vakuu. Olejovitý zbytek se vysuší ve vakuu olejové vývěvy.Dissolve 28,17 g (0,1 mol) of chloro-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] in 120 ml of acetonitrile and react with 6,5 g (0,15 g) mol) of sodium methylate. The mixture was cooled to about -15 ° C and treated with 22.4 g (0.47 mol) of methyl mercaptan. After little heating to 20-25 ° C, the mixture was further stirred for about 20 hours at this temperature. It was then partitioned into ethyl acetate / water and the alkaline aqueous phase separated. The organic phase is shaken once with sodium hydroxide solution and then washed until neutral. The ethyl acetate phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The oily residue is dried in an oil pump vacuum.
Výtěžek: 18 g = 61,3 % teorie.Yield: 18 g = 61.3% of theory.
Tqplota tání: 71 až 73 °C.Melting point: 71-73 ° C.
Příklad 4 [ 2,6-dimethyl-N- (2-oxoperhydr o-3-furyl) anilid kyseliny isopropylsulfonyloctovéExample 4 Isopropylsulfonylacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide
9,64 g (0,03 mol) [2,6-dimethyl-N-(2-oxoperhydro-3-furyl]anilidu] kyseliny isopropylthiooctoivé se rozpustí ve 260 ml chloroformu a nechá reagovat s 12,08 g (0,07 mol) kyseliny 3-chlorperbenzoové. Po čtyřhodinovém míchání při teplotě místnosti se přidá dalších 6 g (0,035 mol) kyseliny 3-chlor2199059.64 g (0.03 mol) of isopropylthio-octoic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] is dissolved in 260 ml of chloroform and treated with 12.08 g (0.07) After stirring at room temperature for 4 hours, an additional 6 g (0.035 mol) of 3-chloro acid is added.
per benzoové. Reakční směs se míchá po dobu dalších 14 hodin a organická fáze se vytřepává vícekrát 1 N hydroxidem sodným, vysuší nad síranem hořečnatým a odpaří ve vakuu. Získané krystaly se digerují isoatherem a odsají.per benzoové. The reaction mixture is stirred for a further 14 hours and the organic phase is shaken several times with 1 N sodium hydroxide, dried over magnesium sulphate and evaporated in vacuo. The obtained crystals are digested with isoatherem and aspirated.
Výtěžek: 9 g — 84,9 °/o teorie.Yield: 9 g - 84.9% of theory.
Teplota tání: 177 až 185 °C.Melting point: 177-185 ° C.
Příklad 5 [ 2,6-dimethy 1-N- (2-oxoper hydr o-3-f ury 1) anilinokarbonylmethyl] ester kyseliny dimethyldithiokarbamovéExample 5 Dimethyldithiocarbamic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilinocarbonylmethyl] ester
8,45 g (0,03 mol) [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)anilidu] kyseliny chlor octové se rozpustí ve 100 ml acetonitrilu a po přidání 5,3 g (0,037 mol) dimethyldithiokarbamátu sodného se zahřívá к varu po dobu 6 hodin za uvádění dusíku. Po ochlazení asi na 20 až 25 °C se reakční směs vlije do 400 ml vody a extrahuje se třikrát chloroformem. Spojené chloroformové fáze se vysuší nad síranem hořečnatým a odpaří ve vakuu. Krystalický zbytek se odsaje, promyje methanolem a vysuší ve vakuu při teplotě místnosti.8.45 g (0.03 mol) of [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] chloroacetic acid are dissolved in 100 ml of acetonitrile and after addition of 5.3 g (0.037 mol) of sodium dimethyldithiocarbamate is heated to boiling for 6 hours under nitrogen. After cooling to about 20-25 ° C, the reaction mixture is poured into 400 ml of water and extracted three times with chloroform. The combined chloroform phases were dried over magnesium sulfate and evaporated in vacuo. The crystalline residue is filtered off with suction, washed with methanol and dried under vacuum at room temperature.
Výtěžek: 7,7 g = 70 % teorie.Yield: 7.7 g = 70% of theory.
Teplota tání: 153 až 156 °C.Melting point: 153-156 ° C.
Analogicky lze připravit následující sloučeniny podle vynálezu.The following compounds of the invention can be prepared analogously.
Název sloučeninyName of the compound
Fyzikální konstantaPhysical constant
Fyzikální konstantaPhysical constant
Název sloučeniny [5-chlor-2-methyl-N-(2-oxoperhydro-3-f uryl) anilid] kyseliny ethoxyoctové [2-chlor-N- (2-oxoperhydro-3-furylpanilid] kyseliny ethoxyoctové [ 2,6-dimethyl-N- (5-butyl-2-oxoperhydro-3-furyl) anilid ] kyseliny methoxyoctové [ 4-chlor-N- (2-oxoperhydro-3-f uryl) anilid ] kyseliny methoxyoctové teplota táníName of ethoxyacetic acid [5-chloro-2-methyl-N- (2-oxoperhydro-3-furyl) anilide] [2-chloro-N- (2-oxoperhydro-3-furylpanilide)] ethoxyacetic acid [2,6- Methoxyacetic acid dimethyl N- (5-butyl-2-oxoperhydro-3-furyl) anilide [4-chloro-N- (2-oxoperhydro-3-furyl) anilide] methoxyacetic acid melting point
101 až 103 °C nD 20 1,5387 teplota tání až 81 °C tqplota táníMp 101-103 ° C n D 20 1.5387 melting point up to 81 ° C melting point
105 až 106 °C105-106 ° C
Sloučeniny podle vynálezu jsou zpravidla téměř bezbarvé krystalické látky, bez zápachu, nebo nažloutlé kapaliny, které jsou velmi špatně rozpustné ve vodě a benzinu, naproti tomu jsou velmi dobře rozpustné v polárních rozpouštědlech, jako například v acetonu, dimethylformamidu a dimethylsulfoxidu.The compounds according to the invention are generally almost colorless crystalline substances, odorless or yellowish liquids, which are very poorly soluble in water and gasoline, on the other hand, they are very soluble in polar solvents such as acetone, dimethylformamide and dimethylsulfoxide.
Výchozí sloučeniny pro výrobu sloučenin podle vynálezu jsou o sobě známé nebo je lze připravovat známými způsoby.The starting compounds for the preparation of the compounds according to the invention are known per se or can be prepared by known methods.
Následující příklady slouží к objasnění možností použití а к ozřejmění nadřazeného fungicidního účinku sloučenin podle vynálezu.The following examples serve to illustrate the possibilities of use and to elucidate the superior fungicidal activity of the compounds of the invention.
Příklad 6Example 6
Test mezní koncentrace při hubení Pythium ultimum.Pythium ultimum killing test.
20% práškovité přípravky účinných látek byly smíchány rovnoměrně se zeminou, která byla zamořena silně Pythium ultimum. Ošetřená půda byla plněna do 0,5 litrových hliněných misek a každá miska byla oseta bez karenční doby 20 zrny hrachu „Wunder von Kelvedon“. Po kultivaci po dobu tří týdnů při teplotě 20 až 24 °C ve skleníku byl stanoven počet zdravých hrachů a kvalita kořenění (1 až 4).The 20% powder formulations of the active ingredients were mixed evenly with the soil, which was heavily infested with Pythium ultimum. The treated soil was filled into 0.5 liter clay bowls and each dish was sown without a shelf life of 20 grain pea "Wunder von Kelvedon". After cultivation for three weeks at 20-24 ° C in a greenhouse, the number of healthy peas and the spice quality (1-4) were determined.
Účinné látky, použitá množství a výsledky jsou uvedeny v následující tabulce.The active substances, the amounts used and the results are shown in the following table.
Kvalita kořenění:Spice quality:
= bílé kořeny bez nekróz houbami 3 = bílé kořeny, mírné nekrózy houbami 2 = hnědé kořeny, již silnější nekrózy houbami = silné nekrózy houbami, kořeny ztrouchnivělé= white roots without fungi necrosis 3 = white roots, mild fungi necrosis 2 = brown roots, already strong fungi necrosis = strong fungi necroses, rotten roots
Sloučeniny podle vynálezu [ 3-kyan-N- (2-oxoperhydro-3-f uryl) ani.lid ] kyseliny methoxyoctové [ 3-chlor-2-methyl-N- [ 2-oxoperhydro-3-furyl)anilid] kyseliny methoxyoctové [ 2,6-dimethyl-N-(5-rnethyl-2-oxoperhydro-3-fury! Janilid] kyseliny acetoxyoctové [ 2,6-dim ethyl-N- (2 - ох o p e rhy dr o-3--fi ryl ] anilid] kyseliny acetoxyoctové [ 2,6-dimethyl-N - (2-oxoperhydrOf3-f uryl) anihd] k^elm1 frnylth-ooctové [ 2,6--ИтеН] yl-N-( 2-οχορθγ1^ι.1γ·ο-3--ιι^1 )anilid] kyseliny ethylthlooctové [ 2,6-dimethyl-N- (2-oxoperhydro-3-f uryl) anilid] kyseliny isopropylthíooctové [ 2,6^1111611^1-1^ (2-oxoperhydro-3-f uryl ]anilid] kyseliny isopropylsulfonyloctovéCompounds of the invention Methoxyacetic acid [3-cyano-N- (2-oxoperhydro-3-furyl) anilide] [3-chloro-2-methyl-N- [2-oxoperhydro-3-furyl) anilide] Acetoxyacetic acid [2,6-dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl-Janilide)] [2,6-dimethyl-N- (2-hydroxyphenyl) -3-phenyl] ] anilide] acetoxyacetic acid [2,6-dimethyl-N - (2-oxo-beta erhydrOf3 furyl) anihd] k ^ f 1 Elm lt reverse to h - ooctov e [2,6 - ИтеН] yl-N- ( Isopropylthioacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] isopropylthioacetic acid [2,6-dimethyl-N- (2-oxo-3-yl) anilide] [2,6 ^ 1111611 4- (1- (2-Oxoperhydro-3-furyl) anilide) isopropylsulfonylacetic acid
Srovnávací prostředek ManganethylenbisdithiokarbamátComparative Manganethylene bisdithiocarbamate
Kontrola I. (3 opakování) Zamořená neošetřená půdaControl I. (3 reps) Infested untreated soil
Kontrola II. (3 opakování] Vypařená půdaControl II. (3 repetitions] The YP and R da en PU
Příklad 7Example 7
Hubení Phytophtora nica-tanae var. nicotianae v kořenáčové kultuře Sinningia speciosaControl of Phytophtora nica-tanae var. nicotianae in the pot culture of Sinningia speciosa
Mladé rostliny Sinningia druhu „Berliner Rot“ byly nasá.zeny do- Míněných kořenáčů o průměru 11 cm. Substrát ^eďstavoval směs 1 dílu rašelinového substrátu a 1 dílu kompostu.Young plants sinningias species "Berliner Rot" were nasá.zen y co-intentioned DO- of ENaC s o p r mers of 11 cm. The substrate represented a mixture of 1 part peat substrate and 1 part compost.
Po- zasázení hyly rostlrny z^lity jednou WO mililitry udané koncentrace preparátu. 3 dny potom byly kořenáče očkovány myceliem kultury Phytophtora, staré 3 týdny. Následovala doba kultivace po dobu sedmi týdnů při teplotě 22 až 24 ’°C ve skleníku.PO- again and marries hyly rostlrn ^ y z y d lit Nou WO milliliters indicated concentrations preparation. Three days later, the pots were inoculated with a 3 week old Phytophtora mycelium. This was followed by a cultivation period of seven weeks at 22-24 ° C in a greenhouse.
0činné látk1, použitá množství a výsledky jsou uvedeny v následující tabulce.0činn E of a substance 1, p ouži those quantities, and sends d are indicated in the following table.
Příklad 8Example 8
Hubení Phylophtora parasitica var. nicotianae v kultuře tabákuPhylophtora parasitica var. nicotianae in tobacco culture
Mladé rostliny tabáku druhu „Havana“ byly nasázeny do kořenáčů o průměru 14 centimerů. Substrát představoval směs 1 dílu rašelinového substrátu a 1 dílu písčitéYoung 'Havana' tobacco plants were planted in pots with a diameter of 14 centimeters. The substrate represented a mixture of 1 part peat substrate and 1 part sandy
Sloučeniny podle vynálezu [ 2,6-dime thyl-N- (5-methyl-2-oxoperhydro-3-furyl) anilid] kyseliny methoxyoctové [ 2,6-dime thyl-N- [ 2-oxoperhydro-3-furyl) anilid] kyseliny methoxyoctové[2,6-Dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) anilide] Methoxyacetic acid [2,6-dimethyl-N- [2-oxoperhydro-3-furyl) anilide] ] Methoxyacetic acid
Kontrola 1. očkovánoControl 1. vaccinated
Kontrola II. neočkovánoControl II. neočkováno
Příklad 9Example 9
Hubení Phytophtora capsiei v kultuře papriky (Capsicum annuum)Control of Phytophtora capsiei in paprika culture (Capsicum annuum)
Mladé rostliny papriky byly nasázeny do kořenáčů o průměru 14 cm. Substrát představoval směs 1 dílu rašelinového substrátu a 1 dílu písčité kompostované zeminy.The young pepper plants were planted in pots of 14 cm diameter. The substrate represented a mixture of 1 part peat substrate and 1 part sandy composted soil.
Sloučenina podle vynálezu [ 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilid] kyseliny methoxyoctové [3-chlor-N-(2-oxoperhydro-3-furyl] anilid] kyseliny methoxyoctovéMethoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] methoxyacetate [3-chloro-N- (2-oxoperhydro-3-furyl) anilide]
Kontrola I. očkovánoControl I. vaccinated
Kontrola II. neočkovánoControl II. neočkováno
Příklad 10Example 10
Hubení Phytophtora cryptogaea v kořenáčové kultuře Senecio cruentusControl of Phytophtora cryptogaea in pot culture Senecio cruentus
Mladé rostliny Cineraria druhu „Erfurter Zwerg“ byly sázeny do kořenáčů o průměru 11 cm. Substrát kořenáčů představoval kompostované zeminy. Po nasázení byly rostliny zality jednou 100 ml udané končen trace preparátu. Tři dny potom byly koře náče rovnoměrně očkovány kulturou Phy tophitory starou 4 týdny. Následovala kul tivace po dobu 4 týdnů při teplotě 24 až 26 °C ve skleníku.Young Cineraria plants of Erfurter Zwerg were planted in pots with a diameter of 11 cm. The pots substrate was composted soil. After planting, the plants were watered once with 100 ml of the indicated trace preparation. Three days later, the roots were uniformly inoculated with a 4-week-old Phy tophitory culture. This was cultured for 4 weeks at 24-26 ° C in a greenhouse.
Po třech dnech po nasázení byly rostliny zality jednou 100 ml preparátu udané koncentrace. Tři dny potom byly kořenáče rovnoměrně očkovány myceliem kultury Phytophtora, staré 4 týdny. Následovala kultivace po dobu 4 týdnů při teplotě 24 až 26 stupňů Celsia ve skleníku.Three days after seeding, the plants were watered once with 100 ml of the indicated concentration. Three days later, the pots were evenly inoculated with a 4 week old Phytophtor culture mycelium. This was followed by cultivation for 4 weeks at 24 to 26 degrees Celsius in a greenhouse.
Účinné látky, použitá množství a výsledky jsou uvedeny v následující tabulce.The active substances, the amounts used and the results are shown in the following table.
— 0 směs 1 dílu rašelinového substrátu s 1 dílem písčité kompostované zeminy. Tri dny po nasázení byly rostliny rovnoměrně očkovány kulturou Phytophtora starou 3 týdny. Následovala kultivace po dobu 7 týdnů při teplotě 20 až 22 °C ve skleníku.- 0 mixture of 1 part peat substrate with 1 part sandy composted soil. Three days after seeding, the plants were evenly inoculated with a 3 week old Phytophtora culture. Cultivation was carried out for 7 weeks at 20-22 ° C in a greenhouse.
Účinné látky, použitá množství a výsledky jsou uvedeny v následující tabulce.The active substances, the amounts used and the results are shown in the following table.
Sloučeniny podle vynálezuCompounds of the invention
Koncentrace účinné Ztráta rostlin po 7 látky [%i] týdnech [%']Concentration effective Plant loss after 7 substances [% i] weeks [% ']
215303215303
Příklad 11Example 11
Moření fazolové setbyPickling bean seedlings
Fazolová setba (Phaseolus vulgaris var. nanus) druhu „Wachs Beste von Allen“ byla mořena 20% práškovitými přípravky účinné látky. Dvoulitrové hliněné miskyBean seedlings (Phaseolus vulgaris var. Nanus) of the species 'Wachs Beste von Allen' were stained with 20% powder formulations of the active substance. Two liter clay bowls
Sloučeniny podle vynálezu [ 2,6-dimethyl-N- (2-oxoperhydro-3-furyl)anilid] kyseliny methoxyoctové [ 3-chlor-N- (2-oxoperhydro-3-f uryl) anilid] kyseliny methoxyoctové [ 2,6-dimethyl-N- [ 5-methy 1-2-oxoperhydro-3-furyl)anilid] kyseliny methoxyoctové [Ν'(2-oxoperhydro-3-furyl)anilid] kyseliny methoxyoctové [ 3-methyl-N- (2- oxoperhydro-3-f uryl) anilid] kyseliny methoxyoctovéMethoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] methoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] Dimethyl-N- [5-methyl-2-oxoperhydro-3-furyl) anilide] methoxyacetic acid [Ν '(2-oxoperhydro-3-furyl) anilide] methoxyacetic acid [3-methyl-N- (2-oxoperhydro) Methoxy-acetic acid -3-furyl) anilide
Srovnávací látka tetramethylthiuramdisulfidReference substance tetramethylthiuram disulfide
Kontrola I. zamořená půdaControl I. Contaminated soil
Kontrola II. propařená půda (20 x 20 x 5 cm) byly plněny normální kompostovanou půdou (vypařenou) a každá miska byla oseta 25 fazolemi. Po kultivaci po dobu 15 dní při teplotě 19 až 21 °C ve skleníku byly stanoveny zdravé semenáčky.Control II. the steamed soil (20 x 20 x 5 cm) was filled with normal composted soil (evaporated) and each dish was sown with 25 beans. Healthy seedlings were determined after cultivation for 15 days at 19 to 21 ° C in a greenhouse.
Účinné látky, použitá množství a výsledky jsou uvedeny v následující tabulce.The active substances, the amounts used and the results are shown in the following table.
Příklad 12Example 12
Působení profylaktického ošetření listů proti Plasmopara viticola na rostlinách vinné révy ve skleníkuEffect of prophylactic treatment of leaves against Plasmopara viticola on vine plants in greenhouse
Mladé rostliny vinné révy asi s 5 až 8 listy byly postříkány do mokra 0,025% koncentrací účinné látky, po oschnutí postřiku byly postříkány vodnou suspenzí spor-angií houby (asi 20 000 na 1 ml) na spodní stranu listů a okamžitě inkubovány ve skleníku při teplotě 22 až 24 °C a pokud možno v atmosféře nasycené vodní parou.Young vine plants with about 5 to 8 leaves were sprayed in the wet with 0.025% active compound concentrations, after spraying dried they were sprayed with an aqueous spore-sponge fungi suspension (about 20,000 per 1 ml) on the underside of the leaves and immediately incubated in a greenhouse 22 to 24 ° C and preferably in a steam saturated atmosphere.
Od druhého dne byla vzdušná vlhkost snížena po dobu 3 až 4 dní na normální hodnotu (30 až 70% nasycení) a potom udržována jeden den na stavu nasycení vodní parou. Potom byl hodnocen u každého listu procentuální podíl plochy napadené houbou a vypočten následujícím způsobem průměr každého ošetření ke stanovení fungicidního účinku:From the next day, the humidity was reduced to a normal value (30 to 70% saturation) for 3 to 4 days and then maintained for one day at the steam saturation state. Then, the percentage of fungal infested area was evaluated for each leaf and the average of each treatment was calculated as follows to determine the fungicidal effect:
10. napadeni ošetřených л/ 10. attacked treated л /
100 — ----------—x 7 -— — % účinnosti napadeni neosetrených100 - ------------ x 7- - -% Effectiveness of untreated attack
Sloučeniny podle vynálezu [ 2,6-dimethyl-N-(2-oxoperhydro-3-f uryl) anilid] .kyseliny methoxyoctové [ 3-chlor-N- (2-oxoperhydro-3-f uryl) anilid ] kyseliny methoxyoctové [ 2,6-dimethyl-N- [ 5-methyl-2-oxoperhydr o-3-furyl)anilid] kyseliny methoxyoctové [N-(2-oxoperhydro-3-furyl)anilid] kyseliny methoxyoctové [ 3-methyl-N- (2-oxoperhydro-3-furyl ] anilid] kyseliny methoxyoctové [2,3-dimethyl-N-(2-oxoperhydro-3-furyl]anilid] kyseliny methoxyoctové [ 3-f luor-N- (5-methyl-2-oxoperhydro-3-furyl]anilid] kyseliny methoxyoctové [ 3-chlor-N- (5-methyl-2-oxoperhydro-3-furyl]anilid] kyseliny methoxyoctové [ 2,6-dimethyl-N-(5-methyl-2-oxoperhydro-3-furyl]anilid] kyseliny acetoxyoctové [ 2,6-dimethyl-N-(2-oxoperhydro-3-f uryl)anilid] kyseliny fenylthiooctové [ 2-methyl-N- [ 2-oxo per hydro-3-f uryl ]anilid] kyseliny acetoxyootové [ 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilid] kyseliny acetoxyoctové [ 2-methyl-N- (2-oxoperhydro-3-f uryl ] anilid] kyseliny methoxyoctové [ 2-methoxy-N- (2-oxoperhydro-3-furyl ] anilid] kyseliny methoxyoctové [ 3-chlor-2-methyl-N- (2-oxoperhydro-3-furyl]anilid] kyseliny methoxyoctové [ 3-chlor-N- (2-oxoperhydro-3-f uryl) anilid] kyseliny acetoxyoctové [ 3-k у an-N- (2-oxoperhydro-3-f uryl ] anilid ] kyseliny methoxyoctové [ 3-kyan-N- (2-owoperhydro-3-furyl)anilid] kyseliny methoxyoctové [ 2,6-dimethyl-N- (2-oxoiperhydr o-3-furyl ] anilid] kyseliny ethylthiooctové [ 2,6-dimethyl-N- (2-oxojperhydro-3-furyl ] anilid] kyseliny isopropylthiooctové [ 2,6-dimethyl-N-] 2-oxoperhydro-3-furyl ] anilid] kyseliny terc.butylthiooctové [ 2,6-dimethyl-N- (2-oxoperhydro-3-furyl )anilid] kyseliny isopropylsulfonyloctové % účinnostiCompounds of the invention [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] methoxyacetic acid [3-chloro-N- (2-oxoperhydro-3-furyl) anilide] methoxyacetic acid [2 6-Dimethyl-N- [5-methyl-2-oxoperhydro-3-furyl) anilide] methoxyacetic acid [N- (2-oxoperhydro-3-furyl) anilide] methoxyacetic acid [3-methyl-N- (2 Methoxyacetic acid-oxoperhydro-3-furyl] anilide] Methoxyacetic acid [2,3-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] [3-fluoro-N- (5-methyl-2-oxoperhydro- Methoxyacetic acid 3-furyl] anilide [3-chloro-N- (5-methyl-2-oxoperhydro-3-furyl) anilide] [2,6-dimethyl-N- (5-methyl-2-oxoperhydro- Acetoxyacetic acid 3-furyl] anilide [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] phenylthioacetic acid [2-methyl-N- [2-oxo-perhydro-3-furyl]] Acetoxyootic acid anilide [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] Acetoxyacetic acid [2-methyl-N- (2-oxoperhydro-3-furyl) anilide] Methoxyacetic acid [2- methoxy Methoxyacetic acid N- (2-oxoperhydro-3-furyl] anilide] [3-chloro-2-methyl-N- (2-oxoperhydro-3-furyl] anilide] [3-chloro-N- (2- Acetoxyacetic acid oxoperhydro-3-furyl) anilide [3-cyano-N- (2-oxoperhydro-3-furyl) anilide] Methoxyacetic acid [3-cyano-N- (2-owoperhydro-3-furyl)] Methoxyacetic acid anilide [2,6-dimethyl-N- (2-oxoiperhydro-3-furyl) anilide] Ethylthioacetic acid [2,6-dimethyl-N- (2-oxo -perhydro-3-furyl) anilide] Isopropylthioacetic acid [ Tert-butylthioacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] isopropylsulfonylacetic acid 2,6-dimethyl-N-] 2-oxoperhydro-3-furyl] anilide
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Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841824 DE2841824A1 (en) | 1978-09-22 | 1978-09-22 | ACETIC ACID ANILIDE, METHOD FOR PRODUCING THESE COMPOUNDS, AND THIS FUNGICIDAL CONTAINER |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS219905B2 true CS219905B2 (en) | 1983-03-25 |
Family
ID=6050476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS795676A CS219905B2 (en) | 1978-09-22 | 1979-08-20 | Fungicide means and method of making the active agents |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5545682A (en) |
| AT (1) | AT365890B (en) |
| AU (1) | AU5107679A (en) |
| BE (1) | BE878924A (en) |
| BG (1) | BG30624A3 (en) |
| BR (1) | BR7905455A (en) |
| CS (1) | CS219905B2 (en) |
| DD (1) | DD145989A5 (en) |
| DE (1) | DE2841824A1 (en) |
| DK (1) | DK346179A (en) |
| ES (1) | ES483787A1 (en) |
| FR (1) | FR2436782A1 (en) |
| GB (1) | GB2033379B (en) |
| HU (1) | HU182612B (en) |
| IL (1) | IL58273A0 (en) |
| IT (1) | IT1165288B (en) |
| LU (1) | LU81703A1 (en) |
| NL (1) | NL7905267A (en) |
| PL (1) | PL119374B1 (en) |
| RO (1) | RO78587A (en) |
| SU (1) | SU988191A3 (en) |
| YU (1) | YU204879A (en) |
| ZA (1) | ZA795021B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2845454A1 (en) * | 1977-11-01 | 1979-05-10 | Chevron Res | 3- (N-ACYL-N-ARYLAMINO) - GAMMA -BUTYROLACTONE AND - GAMMA -BUTYROTHIOLACTONE AND FUNGICIDE AGENTS |
| JPH02124375U (en) * | 1989-03-27 | 1990-10-12 |
-
1978
- 1978-09-22 DE DE19782841824 patent/DE2841824A1/en not_active Withdrawn
-
1979
- 1979-07-05 NL NL7905267A patent/NL7905267A/en not_active Application Discontinuation
- 1979-08-17 DK DK346179A patent/DK346179A/en not_active Application Discontinuation
- 1979-08-20 CS CS795676A patent/CS219905B2/en unknown
- 1979-08-21 YU YU02048/79A patent/YU204879A/en unknown
- 1979-08-21 IT IT25202/79A patent/IT1165288B/en active
- 1979-08-24 BR BR7905455A patent/BR7905455A/en unknown
- 1979-08-31 ES ES483787A patent/ES483787A1/en not_active Expired
- 1979-09-12 DD DD79215492A patent/DD145989A5/en unknown
- 1979-09-17 GB GB7932156A patent/GB2033379B/en not_active Expired
- 1979-09-19 IL IL58273A patent/IL58273A0/en unknown
- 1979-09-20 PL PL1979218428A patent/PL119374B1/en unknown
- 1979-09-20 LU LU81703A patent/LU81703A1/en unknown
- 1979-09-21 RO RO7998732A patent/RO78587A/en unknown
- 1979-09-21 SU SU792817359A patent/SU988191A3/en active
- 1979-09-21 BE BE0/197256A patent/BE878924A/en not_active IP Right Cessation
- 1979-09-21 ZA ZA00795121A patent/ZA795021B/en unknown
- 1979-09-21 BG BG044915A patent/BG30624A3/en unknown
- 1979-09-21 AT AT0622679A patent/AT365890B/en not_active IP Right Cessation
- 1979-09-21 AU AU51076/79A patent/AU5107679A/en not_active Abandoned
- 1979-09-21 JP JP12092979A patent/JPS5545682A/en active Pending
- 1979-09-22 HU HU79SCHE692A patent/HU182612B/en unknown
- 1979-09-24 FR FR7923680A patent/FR2436782A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL58273A0 (en) | 1979-12-30 |
| BR7905455A (en) | 1980-05-20 |
| ES483787A1 (en) | 1980-05-16 |
| ZA795021B (en) | 1980-09-24 |
| DE2841824A1 (en) | 1980-04-03 |
| IT1165288B (en) | 1987-04-22 |
| AU5107679A (en) | 1980-04-17 |
| BE878924A (en) | 1980-03-21 |
| JPS5545682A (en) | 1980-03-31 |
| AT365890B (en) | 1982-02-25 |
| FR2436782B1 (en) | 1983-07-22 |
| ATA622679A (en) | 1981-07-15 |
| FR2436782A1 (en) | 1980-04-18 |
| BG30624A3 (en) | 1981-07-15 |
| GB2033379B (en) | 1982-12-22 |
| GB2033379A (en) | 1980-05-21 |
| DK346179A (en) | 1980-03-23 |
| HU182612B (en) | 1984-02-28 |
| PL218428A1 (en) | 1980-07-14 |
| SU988191A3 (en) | 1983-01-07 |
| RO78587A (en) | 1982-03-24 |
| IT7925202A0 (en) | 1979-08-21 |
| DD145989A5 (en) | 1981-01-21 |
| NL7905267A (en) | 1980-03-25 |
| LU81703A1 (en) | 1980-01-24 |
| PL119374B1 (en) | 1981-12-31 |
| YU204879A (en) | 1983-02-28 |
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