DE1907739A1 - 5- (N-methyl-carbamoyloxy) -1,3-dimethyl-pyrazole, process for its preparation and its use as a fungicide - Google Patents
5- (N-methyl-carbamoyloxy) -1,3-dimethyl-pyrazole, process for its preparation and its use as a fungicideInfo
- Publication number
- DE1907739A1 DE1907739A1 DE19691907739 DE1907739A DE1907739A1 DE 1907739 A1 DE1907739 A1 DE 1907739A1 DE 19691907739 DE19691907739 DE 19691907739 DE 1907739 A DE1907739 A DE 1907739A DE 1907739 A1 DE1907739 A1 DE 1907739A1
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- methyl
- pyrazole
- active ingredient
- soil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen 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
- 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
- A01N47/18—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, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
Description
LEVERKUSEN-Bayerwerk Patent-AbteilungLEVERKUSEN-Bayerwerk patent department
13; FEB. 195913; FEB. 1959
5-(N-Methyl-carbamoyloxy-)-1,3-dimethyl-pyrazol, Verfahren zu seiner Herstellung sowie seine Verwendung als Fungizid5- (N-methyl-carbamoyloxy -) - 1,3-dimethyl-pyrazole, method for its manufacture and its use as a fungicide
Die vorliegende Erfindung betrifft das neue 5-(N-Methylearbamoyloxy-)-1,3-dimethyl-pyrazol, welches fungizide Eigenschaften hat sowie ein Verfahren zu seiner Herstellung,The present invention relates to the new 5- (N-methylearbamoyloxy -) - 1,3-dimethyl-pyrazole, which has fungicidal properties and a process for its production,
Es ist bereits bekannt geworden, daß man 6-(N-Methyl-carbamoyloxy-)-^pyrazole zur Bekämpfung von Pilzen verwenden kann (vgl. Schweizerisches Patent 414 249].It has already become known that 6- (N-methyl-carbamoyloxy -) - ^ pyrazole can be used to control fungi (cf. Swiss Patent 414 249).
Es wurde gefunden, daß das neue 5-(N-Methyl-carbamoyloxy-)-1,3~dimethyl-pyrazol der FormelIt has been found that the new 5- (N-methyl-carbamoyloxy -) - 1,3-dimethyl-pyrazole the formula
HGHG
CDCD
-0-C-NHCH5 -0-C-NHCH 5
starke fungizide Eigenschaften aufweist.has strong fungicidal properties.
Weiterhin wurde gefunden, daß man das 5-(N-Methyl-carbamoyl· oxy-)-1,3-dimethyl-pyrazol erhält, wenn man 1,3-Dimethylpyrazolon der FormelIt has also been found that 5- (N-methyl-carbamoyl oxy -) - 1,3-dimethylpyrazole is obtained when 1,3-dimethylpyrazolone the formula
(II)(II)
Ie A 11 997Ie A 11 997
009835/1923009835/1923
19077301907730
mit Methylisocyanat gegebenenfalls in Gegenwart eines Lösungsmittels umsetzt.with methyl isocyanate, optionally in the presence of a Reacts solvent.
Überraschenderweise zeigt der erfindungsgemäße Wirkstoff eine erhebliche höhere fungitoxische Wirkung als die vorbekannten Carbaminsäureester von Pyrazolonen, welche die' chemisch nächstliegenden vorbekannten Wirkstoffe gleicher. Wirkungsart sind. Der erfindungsgemäße Wirkstoff stellt somit eine Bereicherung der Technik dar. .Surprisingly, the active ingredient according to the invention shows a considerably higher fungitoxic effect than the previously known carbamic acid esters of pyrazolones, which the ' chemically closest known active ingredients the same. Type of action are. The active ingredient according to the invention thus represents an enrichment of the technology..
Die Umsetzung zur Herstellung des Wirkstoffes kann durch folgendes Pcrmelschema wiedergegeben werdenThe implementation for the production of the active ingredient can through the following Pcrmelschema can be reproduced
Z0 CHx-C- CH .-■-..- Z 0 CH x -C- CH .- ■ -..-
2 3 Il I ■ Cm) 2 3 Il I ■ Cm)
=0 + OCNCH, —^ IT ^C-O-C 0-ITHCH3 = 0 + OCNCH, - ^ IT ^ COC 0-ITHCH 3
Das als Ausgangsstoff verwendete 1,3-Dimethyl-pyrazolon ist bereits bekannt. Das gleiche gilt für das Methylisocyanat.The starting material used is 1,3-dimethylpyrazolone already known. The same applies to the methyl isocyanate.
Die Reaktion kann in inerten Lösungsmitteln vorgenommen werden. Hierfür eignen sich z.B. Kohlenwasserstoffe,wie Benzin und Benzol,1 chlorierte Kohlenwasserstoffe, wie Methylenchlorid und Chlorbenzol, aber auch Äther, wie Dioxan sowie -Mischungen aus solchen lösungsmitteln. Es ist jedoch auch möglich, die Umsetzung in Abwesenheit von lösungsmitteln durchzuführen.The reaction can be carried out in inert solvents. Suitable for this are, for example, hydrocarbons such as gasoline and benzene, 1 chlorinated hydrocarbons such as methylene chloride and chlorobenzene, but also ethers such as dioxane and mixtures of such solvents. However, it is also possible to carry out the reaction in the absence of solvents.
Zur Beschleunigung der Umsetzung gibt man zweckmäßigerweise ein tertiäres Amin zu, z.B. Triäthylamin oder Diazabieyclo-oktan,It is expedient to give to accelerate the implementation a tertiary amine to, e.g. triethylamine or diazabieyclo-octane,
Die Reaktionstemperatur kann in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man zwischen 0 und TOO0C, vorzugsweise zwischen 10 und 800C. The reaction temperature can be varied over a wide range. In general, one works between 0 and TOO 0 C, preferably between 10 and 80 0 C.
Le A 11 997 - 2 - Le A 11 997 - 2 -
0 0 98 35/19.2 30 0 98 35 / 19.2 3
19077331907733
Bei der Durchführung der Umsetzung setzt man auf 1 Mol Pyrazolon etwa 1 - 2 MbI Methylisocyanat ein. Die erhaltene Reaktionsmischung wird in üblicher V/eise aufgearbeitet.When carrying out the reaction, 1 mole is used Pyrazolone contains about 1 - 2 MbI of methyl isocyanate. The received The reaction mixture is worked up in the usual way.
Der erfindungsgemäße Wirkstoff weist eine starke fungitoxische Wirkung auf, besitzt eine relativ geringe Warmblütertoxizität und übt auf die Haut und Schleimhäute in den fungitoxisch wirksamen'Konzentrationen bzw. Aufwandmengen keine Reizwirkungen aus.The active ingredient according to the invention has a strong fungitoxic effect Effect on, has a relatively low toxicity to warm blooded animals and exerts on the skin and mucous membranes in the fungitoxic effective 'concentrations or application rates no irritating effects the end.
Da der Wirkstoff auch eine gute Verträglichkeit mit höheren Pflanzen und mit Samen höherer Pflan sen zeigt, kann er zur Bekämpfung von phytopathogenen Pilzen im Pflanzenschutz eingesetzt werden.Because the active ingredient is also well tolerated with higher Plants and with seeds of higher plants he can show Control of phytopathogenic fungi can be used in crop protection.
So zeigt er eine gute Wirkung gegen !samenübertragbare Pilze, wie Tilletia tritici, Ustilago avenae, Fusarium nivale, Helminthosporium und gegen bodenbewohnende Pilze, wie Rhlzoctonia-Arten, Pusarium-Arten, Pythium-Arten, PhytophthOra-Arten,Verticillium alboatrum, Thielaviopsis basicola und Corticium rolfsii.It shows a good action against seed-borne fungi, such as Tilletia tritici, Ustilago avenae, Fusarium nivale, and Helminthosporium and against soil-dwelling fungi, such as Rhlzoctonia species, Pusarium species, Pythium species, PhytophthOra species, Verticillium alboatrum, Thielaviopsis basicola and Corticium rolfsii.
Der Wirkstoff ist also besonders gut zur Bodenbehandlung und Saatgutbeizung geeignet.The active ingredient is therefore particularly good for soil treatment and Suitable for seed dressing.
Der erfindungegemäße Wirkstoff kann in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate. Diese werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln. Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als*Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen imThe active ingredient according to the invention can be used in the customary formulations such as solutions, emulsions, suspensions, powders, pastes and granulates. These are known in Manufactured in a manner, e.g. by mixing the active ingredients with extenders, i.e. liquid solvents and / or solids Carriers, optionally with the use of surface-active agents, that is to say emulsifiers and / or dispersants. If water is used as an extender, organic solvents, for example, can also be used as auxiliary solvents be used. The liquid solvents are im
Le A 11 997 - 3 - Le A 11 997 - 3 -
0 09835/1923 ORIGINAL INSPECTED0 09835/1923 ORIGINAL INSPECTED
19077301907730
wesentlichen infrage: Aromaten, wie Xylol und Benzol, chlo*- rierte Aromaten, wie Chlorbenzole, Paraffine, wie Erdölfraktionen, Alkohole, wie Methanol und Butanol, stark polare LbV sungsmittel, wie Dimethylformamid und Dimethylsulfoxyd, sowie Wasser; als feste Trägerstoffe: natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum und Kreide, und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure und Silikate j als Emulgiermittel: nichtionogene und anionische Emulgatoren, wie PqIy- oxyäthylen-Fettsäure-Ester, Polyoxyäthyien-Fettalkohol-A'ther, z.B. Alkylaryl-polyglykol-äther, Alkylsulfonate und Arylsulfonate; als Dispergiermittel: z.B. lignin, Sulfitablaugen und Methylcellulose. _ V;essential question: aromatics, such as xylene and benzene, chlo * - rated aromatics such as chlorobenzenes, paraffins such as petroleum fractions, alcohols such as methanol and butanol, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water; as solid carrier materials: natural rock flour, such as Kaolins, clays, talc and chalk, and synthetic minerals, such as highly dispersed silica and silicates j as emulsifiers: nonionic and anionic emulsifiers, such as PqIy- oxyethylene fatty acid ester, polyoxyethylene fatty alcohol ether, e.g., alkylaryl polyglycol ethers, alkyl sulfonates and aryl sulfonates; as dispersants: e.g. lignin, sulphite waste liquors and Methyl cellulose. _ V;
• ■ ■ " " ".■■""■■ ■-'.■.■.·.■.■'.■■"='";-'"■■ ι ;;■■;• ■ ■ "" ". ■■" "■■ ■ - '. ■. ■. ·. ■. ■'. ■■" = '"; -'" ■■ ι ;; ■■;
w Der erfindungsgemäße Wirkstoff kann in den Tormulierungen in Mischungen mit anderen bekannten Wirkstoffen vorliegen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden,Herbizideiiy Schutzstoff en gegen Vogelfraß, Viuchsst of fen, Pflanzennährstoffen und Bodenstrukturyerbesserungsmitteln. Die Formülie- rungen enthalten im allgemeinen zwischen 1 und 95 $ Wirkstoff, vorzugsweise zwischen 5 und 90. ■ . w The active ingredient of the invention can be present in the Tormulierungen in mixtures with other known active compounds, such as fungicides, fen insecticides, acaricides, nematicides, Herbizideiiy protectant s bird repellents, Viuchsst of, plant nutrients and Bodenstrukturyerbesserungsmitteln. The formulations generally contain between 1 and 95% active ingredient, preferably between 5 and 90%.
Der Wirkstoff kann als solcher, in Form seiner Formulierurigen oder der daraus durch weiteres Verdünnen bereiteten Anwendungsformen wie gebrauchsfertige Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate angewendet werden. Die Anwendung φ geschieht in der üblichen Weise, z.B. durch Gießen, Spritzen, Sprühen, Stäuben, Streuen, Trockenbeizen, Naßbeizen oder Inkrustieren. ' ',.-,■""The active ingredient can be used as such, in the form of its formulation or the application forms prepared therefrom by further dilution such as ready-to-use solutions, emulsions, suspensions, Powders, pastes and granules can be used. The application φ happens in the usual way, e.g. by watering, spraying, spraying, dusting, scattering, dry pickling, wet pickling or Encrusting. '', .-, ■ ""
Bei der Saatgutbehandlung werden im allgemeinen WirkstoffΪ-mengen von 0,1 g bis 10 g je kg Saatgut, vorzugsweise 0,5 bis 5 g benötigt. Zur Bodenbehandlung sind Wirkstoffmengen von 1 bis 500 g je Kubikmeter Boden, vorzugsweise 10 bis 200 g erforderlich.In the treatment of seeds, amounts of active ingredient are generally used from 0.1 g to 10 g per kg of seed, preferably 0.5 to 5 g required. For soil treatment, amounts of active ingredient are 1 to 500 g per cubic meter of soil, preferably 10 to 200 g, is required.
Ie A 11 997 - 4 - Ie A 11 997 - 4 -
0 098 3 5/192 30 098 3 5/192 3
19077301907730
. ' . -■£ ■■■■.■ ' :. '. - ■ £ ■■■■. ■ ':
Bödenbehandlungsmittel-Test / bodenbürtige MykosenSoil treatment agent test / soil-borne mycoses
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung verstreckt man den Wirkstoff mit Talkum auf 5 % und anschließend mit*Quarzsand auf 0,5 $> Wirkst off gehalt.To produce an appropriate preparation of the active ingredient, the active ingredient is stretched to 5 % with talc and then to 0.5 % with quartz sand> active ingredient content.
Die Wirkstoffzubereitung vermengt man gleichmäßig mit 3Pruhstorfer Einheitserde, die zunächst sterilisiert und dann mitThe active ingredient preparation is mixed evenly with 3Pruhstorfer Standard earth, which is first sterilized and then with
Reinkulturen der Testpilze beimpft worden ist. Die ErdePure cultures of the test mushrooms has been inoculated. The earth
wird in Töpfe gefüllt und mit 5 χ TC. Samen der Wirtspflanze besät. Die Töpfe werden bei den angegebenen Temperaturen ™is filled in pots and with 5 χ TC. Host plant seeds sown. The pots are heated at the specified temperatures ™
im.Gewächshaus aufgestellt und normal feucht gehalten.placed in the greenhouse and kept normally moist.
3 Wochen nach der Aussaat bestimmt n.an die Anzahl der gesunden Pflanzen in Prozent der ausgelegten Samen. 0 # bedeutet, daß keine gesunde Pflanze aufgewachsen ist, 100 io bedeutet, daß aus allen Samen gesunde· Pflanzen entstanden sind.3 weeks after sowing, n.an determines the number of healthy plants as a percentage of the seeds laid out. 0 # means that no healthy plant has grown up, 100 io means that healthy plants have arisen from all seeds.
Wirkstoffe, Wirkstoffkonzentrationen in der Erde, Testpilze, ' Wirtspflanzen, Gewächshaustemperaturen sowie Ergebnisse gehen hervor aus der nachfolgenden Tabelle.Active ingredients, active ingredient concentrations in the earth, test mushrooms, ' Host plants, greenhouse temperatures and results are shown in the table below.
Ie A 11 997 '' - 4a - Ie A 11 997 '' - 4a -
009835/1923009835/1923
Testpilze»Test mushrooms »
Wirtepflanzes Teaiperaturber.:Host plant Teaiperaturber .:
Fusarium Verticill. Corticiu» Thielaviopsie culmorum alboatrua rolfsii basicolaFusarium Verticill. Corticiu »Thielaviopsia culmorum alboatrua rolfsii basicola
Erbse 22-25Pea 22-25
Erbse 22-25° Pea 22-25 °
Erbse 22-25*Pea 22-25 *
Bauewolle 22-25° Cotton 22-25 °
in
mg/Liter ErdeActive ingredient conc.
in
mg / liter of soil
beimpftsterilized u.
inoculates
8888
8888
76
60 86
76
60
4068
40
88
■ ν'· .74■..■■..■■,■..■,.. ' :'
. , ' ■' ■■ * ■ .' ■■ ■ ■. . · ';. "■■ 94 ( ' ν- ■." ■■ - ■
88
■ ν '· .74 ■ .. ■■ .. ■■, ■ .. ■, ..' : '
. , '■' ■■ * ■. ' ■■ ■ ■. .
Wirtspflanze: Tenperaturber.sHost plant: Temperature range s
Fusarium culmoruaFusarium culmorua
Verticill. Corticiue alboatruB rolfeiiVerticill. Corticiue AlboatruB rolfeii
Erbse 22-25( Pea 22-25 (
Erbsepea
Erbse 22-25*Pea 22-25 *
Thielariopsie basicolaThielariopsy basicola
Baiunrolle 22»25°Baiunroll 22 »25 °
inin
mg/Liter Erdemg / liter of soil
5252
22
00
" z ■ ■ '■■" z ■ ■ '■■
2020th
00
00
5050
2525th
, 50, 50
2525th
[ ([(
3-0-GO-NH-CH3 3-0-GO-NH-CH 3
S-O-OO-HH-OH,S-O-OO-HH-OH,
le A 11 997le A 11 997
T a be lieT a be lie
Wirtspflanze: Temperaturber.:Host plant: Temperature range:
Fusarium Verticill. Corticiua Thielaviopeia culmorum alboatrua rolfsii basicolaFusarium Verticill. Corticiua Thielaviopeia culmorum alboatrua rolfsii basicola
Erbse 22-25*Pea 22-25 *
Erbse 22-25c Pea 22-25 c
Erbse 22-25*Pea 22-25 *
Bauawolle 22-25°Construction wool 22-25 °
inin
mg/Liter Erdemg / liter of soil
2020th
8.8th.
44th
2020th
5050
2525th
:■'■■■■■■·■■■■.■ , ■ .■■■■ ■' '■ ■■■■■'■■ ', Λ$ :'.■■ ·.■: ■ '■■■■■■ · ■■■■. ■, ■. ■■■■ ■''■■■■■■' ■■ ', Λ $:'. ■■ ·. ■
2424
4040
CH,CH,
jj
■...■■-■ 50 ,■.-.: ■■'■ ... ■■ - ■ 50, ■ .- .: ■■ '
1 - : , ■·■■■■ . .,·■ · . ■ ; '■.■■■ ":' ::·, ..'■ ■■ ■ ■' 1 -:, ■ · ■■■■. ., · ■ ·. ■; '■. ■■■ ":' :: ·, .. '■ ■■ ■ ■'
, ■ , . 1: ■.■■.■ \ ';■■■, ■ ' ' ' ,;■:■.; ; ;■■, ■,. 1: ■. ■■. ■ \ '; ■■■, ■''',; ■: ■ .; ; ; ■■
.■ ·: . : ΓΙ "■ .■"■ ' ". '■ '■ ■■:'■ .' "■ ' ■::■" ■ ".-.■■-■ "". ■ · :. : ΓΙ "■. ■" ■ '".' ■ '■ ■■:' ■ . '"■'■ :: ■" ■ ".-. ■■ - ■""
Ansah! gesunder Pflanzen in ψ Pusarium Verticill. CorticiunLooked! healthy plants in ψ Pusarium Verticill. Corticiun
Wirtepflanzes Temparaturber.Host plant temperature regulator.
in mg/Liter Erdein mg / liter of soil
CH,-CCH, -C
GH,GH,
Ie A 11 997Ie A 11 997
100 50100 50
-0-CO-NH-CH2-CH=CH2 25-0-CO-NH-CH 2 -CH = CH 2 25
100 50 25100 50 25
culmorum .Erbse 22-25°culmorum .Pea 22-25 °
alboatrunalboatrun
Erbsepea 22-25°22-25 °
rolfBiirolfBii
Erbsepea
22-25°22-25 °
Thielariopeis basicplaThielariopeis basicpla
Bauanrolle ,22-25°Bauanroll, 22-25 °
2222nd
1414th
1212th
22
4848
2626th
Beispiel . Example .
Bodenbehandlungsmittel-Test /lithium ultimumSoil treatment agent test / lithium ultimum
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung verstreckt man den Wirkstoff mit Talkum auf 5 1» und anschließend mit Quarzsand auf 0,5 # Wirkstoffgehalt. νTo produce a suitable preparation of active ingredient with talc stretched to 5 to 1 "and then with quartz sand to 0.5 # active substance content. ν
Die Wirkstoffzubereitung vermengt man gleichmäßig mit natürlich infizierter Komposterde, die bei Einsaat von Markerbsen erfahrungsgemäß 2",u hohen Ausfällen unter den Keimpflanzen durch Pythium ultimum führt. Die Erde wird in Töpfe gefüllt und mit 5 χ 10 Samen der Markerbse besät. Die Töpfe werden bei 15 — 18 im Gewächshaus aufgestellt und"normal feucht gehalten.The active ingredient preparation is mixed evenly with natural infected compost soil, which experience has shown when sowing marrow peas 2 ", and high losses among the seedlings Pythium ultimum leads. The earth is filled in pots and with Sown 5 χ 10 seeds of the marrow pea. The pots are placed in the greenhouse at 15-18 and kept "normally moist."
3 Wochen nach der Aussaat bestimmt man die Anzahl der gesunden Pflanzen in Prozent der ausgelegten Samen. 0 $ bedeutet, daß keine gesunde Pflanze aufgewachsen ist, 10-0 fo bedeutet, daß aus allen Samen gesunde Pflanzen entstanden sind.3 weeks after sowing, the number of healthy plants is determined as a percentage of the seeds laid out. 0 $ means that no healthy plant has grown up, 10-0 fo means that healthy plants have arisen from all seeds.
Wirkstoffe, Wirkstoffkonzentrationen in der Erde und Ergebnisse gehen hervor aus der nachfolgenden Tabelle.Active ingredients, active ingredient concentrations in the earth and The results are shown in the table below.
Le A 11 997 - 8a - Le A 11 997 - 8a -
009835/1923009835/1923
T a b βT a b β
ii Λ" 1907730 ii Λ " 1907730
BodenbehandlungBmittel-Teet / Pythium ultimumSoil treatmentBmittel-Teet / Pythium ultimum
WirketoffkönB. Wirkstoffe . inWirketoffkönB. Active ingredients. in
mg/liter Erdemg / liter of soil
Ansah! gesunder Fflausen in % Looked! healthy Ff lausen in%
unbehandeltuntreated
erfindungegemäß:according to the invention:
-O-CO-NH--GH,-O-CO-NH - GH,
GH,GH,
bekannt:known:
^-0-CO-NH-CH3 ^ -0-CO-NH-CH 3
0-0-CO-NH-CH3 0-0-CO-NH-CH 3
CO-NH-CH,CO-NH-CH,
100100
too 100too 100
9494
-0-CO-NH-C2H5 100 -0-CO-NH-C 2 H 5 100
Le A 11 997Le A 11 997
- 9—- 9-
0 09835/ T9230 09835 / T923
Tabelle Bodenbehandluneemittel-Teet / Pythium ultimum Table of soil treatment agents-Teet / Pythium ultimum
19077331907733
mg/liter Erdemg / liter of soil
H -Ο-ΟΟ-ΝΗ-/~ΛH -Ο-ΟΟ-ΝΗ- / ~ Λ
100100
CH,CH,
CH,CH,
H -0-CO -H -0-CO -
100100 100100
1010
Ie All 997Ie All 997
- 10 -- 10 -
009835/192009835/192
r.' . " 43 . r. ' . "43.
Beispiel" 1 ' "·' ; >'■ f :-> -i> Example "1 '"·' ; >'■ f : -> -i>
-1907730-1907730
-O-C-HHOH,-O-C-HHOH,
97 g (0,865 Mol) 1^-Dimethylpyrazolon-S (v. Auwerns und Niemeyer, J. pr. CIu (2), VK), 182) werden in 300 ecm Methylenchlorid suspendiert. Nach Zugabe von 3 ecm Triäthylamin tropft man 59 g (1,035 Mol)i;Methylisocyanat zu. Die Reaktion^V' ist exotherm. Die Temperatur.wird während.des?iSintropfens des Methylisocyanates durch Kühlen bei '25-3O0 gehalten. Nach halbstündigem Nachrühren bei Zimmertemperatur destilliert ma:i das Lösungsmittel im Vakuum bei nur wenig erhöhter Temperatur ab, weil das Reaktionsprodukt.in lösung bleibt. Nach Abdestillieren des Lösungsmittels hinterbleiben 146 g (86,5 i° d.Th.) eines gelben Pulvers, das auch Benzol (1 g/4 ecm) umkristaliisier% .; Λ werden kann. Man erhält dabei das S-iN-Me-thylioarb^amoyloxy)-^ 1,3-dimethyl-pyrazol in Form derber, etwas rosafarbener >; Kristalle vom Fp. 99-100°. Das Carbamat ist wasserlöslich.:·97 g (0.865 mol) 1 ^ -dimethylpyrazolone-S (v. Auwerns and Niemeyer, J. pr. CIu (2), VK), 182) are suspended in 300 ecm of methylene chloride. After adding 3 ecm of triethylamine, 59 g (1.035 mol) of i; Methyl isocyanate too. The reaction ^ V 'is exothermic. The temperature is kept at 25-3O 0 by cooling while the methyl isocyanate is dripping. After stirring for half an hour at room temperature, the solvent is distilled off in vacuo at a slightly elevated temperature because the reaction product remains in solution. After the solvent has been distilled off, 146 g (86.5 i ° of theory) of a yellow powder remain, which also recrystallizes benzene (1 g / 4 ecm). Λ can be. The S-iN-methylioarb ^ amoyloxy) - ^ 1,3-dimethylpyrazole is obtained in the form of a coarse, somewhat pinkish color>; Crystals of m.p. 99-100 °. The carbamate is soluble in water.: ·
Ratte peros t. g/kgRat peros t. g / kg
Le A 11 997 - 10a -; ; , Le A 11 997-10a - ; ; ,
0 0 983^/19»0 0 983 ^ / 19 »
Claims (6)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691907739 DE1907739A1 (en) | 1969-02-15 | 1969-02-15 | 5- (N-methyl-carbamoyloxy) -1,3-dimethyl-pyrazole, process for its preparation and its use as a fungicide |
IL33784A IL33784A0 (en) | 1969-02-15 | 1970-01-27 | 5-(n-methylcarbamoyloxy)-1,3-dimethylpyrazole,its preparation and its use as a fungicide |
CH112370A CH528512A (en) | 1969-02-15 | 1970-01-27 | Process for the preparation of 5- (N-methyl-carbamoyloxy -) - 1,3-dimethyl-pyrazole |
NL7001588A NL7001588A (en) | 1969-02-15 | 1970-02-04 | |
GB7108/70A GB1242810A (en) | 1969-02-15 | 1970-02-13 | 5-(n-methylcarbamoyloxy)-1,3-dimethylpyrazole |
BE745961D BE745961A (en) | 1969-02-15 | 1970-02-13 | NEW 5- (N-METHYL-CARBAMOYLOXY) -1,3-DIMETHYLPYRAZOLE, ITS PREPARATION PROCESS AND ITS APPLICATION TO THE FIGHT AGAINST PHYTOPATHOGENOUS FUNGI |
ES376575A ES376575A1 (en) | 1969-02-15 | 1970-02-14 | 5-(n-methylcarbamoyloxy)-1,3-dimethylpyrazole |
FR7005483A FR2035495A5 (en) | 1969-02-15 | 1970-02-16 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691907739 DE1907739A1 (en) | 1969-02-15 | 1969-02-15 | 5- (N-methyl-carbamoyloxy) -1,3-dimethyl-pyrazole, process for its preparation and its use as a fungicide |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1907739A1 true DE1907739A1 (en) | 1970-08-27 |
Family
ID=5725412
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19691907739 Pending DE1907739A1 (en) | 1969-02-15 | 1969-02-15 | 5- (N-methyl-carbamoyloxy) -1,3-dimethyl-pyrazole, process for its preparation and its use as a fungicide |
Country Status (8)
Country | Link |
---|---|
BE (1) | BE745961A (en) |
CH (1) | CH528512A (en) |
DE (1) | DE1907739A1 (en) |
ES (1) | ES376575A1 (en) |
FR (1) | FR2035495A5 (en) |
GB (1) | GB1242810A (en) |
IL (1) | IL33784A0 (en) |
NL (1) | NL7001588A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5436648B2 (en) * | 1974-03-28 | 1979-11-10 | ||
US4230481A (en) * | 1977-08-12 | 1980-10-28 | Ishihara Sangyo Kaisha Limited | Pyrazole derivatives useful as a herbicidal component |
-
1969
- 1969-02-15 DE DE19691907739 patent/DE1907739A1/en active Pending
-
1970
- 1970-01-27 CH CH112370A patent/CH528512A/en not_active IP Right Cessation
- 1970-01-27 IL IL33784A patent/IL33784A0/en unknown
- 1970-02-04 NL NL7001588A patent/NL7001588A/xx unknown
- 1970-02-13 BE BE745961D patent/BE745961A/en unknown
- 1970-02-13 GB GB7108/70A patent/GB1242810A/en not_active Expired
- 1970-02-14 ES ES376575A patent/ES376575A1/en not_active Expired
- 1970-02-16 FR FR7005483A patent/FR2035495A5/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
IL33784A0 (en) | 1970-03-22 |
FR2035495A5 (en) | 1970-12-18 |
BE745961A (en) | 1970-08-13 |
ES376575A1 (en) | 1972-05-01 |
NL7001588A (en) | 1970-08-18 |
GB1242810A (en) | 1971-08-11 |
CH528512A (en) | 1972-09-30 |
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