DE1248031B - Process for the preparation of propynyl-N-phenylcarbamates - Google Patents
Process for the preparation of propynyl-N-phenylcarbamatesInfo
- Publication number
- DE1248031B DE1248031B DEF43289A DEF0043289A DE1248031B DE 1248031 B DE1248031 B DE 1248031B DE F43289 A DEF43289 A DE F43289A DE F0043289 A DEF0043289 A DE F0043289A DE 1248031 B DE1248031 B DE 1248031B
- Authority
- DE
- Germany
- Prior art keywords
- propynyl
- phenylcarbamates
- coo
- preparation
- active ingredient
- 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
- 238000000034 method Methods 0.000 title claims description 7
- TZEJISNGHLGRGZ-UHFFFAOYSA-N prop-1-ynyl n-phenylcarbamate Chemical class CC#COC(=O)NC1=CC=CC=C1 TZEJISNGHLGRGZ-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 10
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 241000500437 Plutella xylostella Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- FYWJWWMKCARWQG-UHFFFAOYSA-N 1,2-dichloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1Cl FYWJWWMKCARWQG-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000387321 Aspidiotus nerii Species 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- 235000011303 Brassica alboglabra Nutrition 0.000 description 1
- 235000011302 Brassica oleracea Nutrition 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 241001221118 Cecidophyopsis ribis Species 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- 241001221110 Eriophyidae Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001396980 Phytonemus pallidus Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241001509970 Reticulitermes <genus> Species 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241001065719 Tetranychus ludeni Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- YSZCDDOREQFOHK-UHFFFAOYSA-N prop-2-ynyl n-phenylcarbamate Chemical compound C#CCOC(=O)NC1=CC=CC=C1 YSZCDDOREQFOHK-UHFFFAOYSA-N 0.000 description 1
- -1 propionyl-N-phenylcarbamates Chemical class 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
Int. CL: C 07 cInt. CL: C 07 c
DEUTSCHESGERMAN
PATENTAMT Deutsche Kl.: 12 ο -17/01 PATENT OFFICE German class: 12 ο - 17/01
AUSLEGESCHRIFTEDITORIAL
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
F 43289 IV b/12 ο
27.Juni 1964
24. August 1967F 43289 IV b / 12 ο
June 27, 1964
August 24, 1967
Die Erfindung betrifft ein Verfahren zur Herstellung von Propinyl-N-phenylcarbamaten, die akarizide, insektizide und ovizide Eigenschaften haben.The invention relates to a process for the preparation of propynyl-N-phenylcarbamates, the acaricidal, have insecticidal and ovicidal properties.
Es ist bereits bekannt, daß man Carbamate als Insektizide und Akarizide verwenden kann. Einige dieser Carbamate haben bereits eine große Bedeutung in der Praxis erlangt. Zu den bedeutendsten und wirksamsten Carbamaten gehören das a-Naphthyl-N-methylcarbamat und das l-Isopropyl-3-methylpyrazolyl-(5)-N-dimethyl-carbamat. It is already known that carbamates can be used as insecticides and acaricides. Some these carbamates have already achieved great importance in practice. Among the most significant and Most effective carbamates include the a-naphthyl-N-methylcarbamate and 1-isopropyl-3-methylpyrazolyl- (5) -N-dimethyl-carbamate.
Es wurde gefunden, daß die Propinyl-N-phenylcarbamate der allgemeinen FormelIt has been found that the propynyl-N-phenylcarbamate the general formula
NH — C — OCH2 — C = CHNH - C - OCH 2 - C = CH
IlIl
O (I)O (I)
in welcher χ und y für 0 oder 1 stehen, starke akarizide, insektizide und ovizide Wirkungen aufweisen. Diese Propinyl-N-phenylcarbamate der allgemeinen Formel (I) werden erhalten, wenn man in an sich bekannter Weise Isocyanate der allgemeinen Formelin which χ and y stand for 0 or 1, have strong acaricidal, insecticidal and ovicidal effects. These propynyl-N-phenylcarbamates of the general formula (I) are obtained when isocyanates of the general formula are used in a manner known per se
NCONCO
in welcher χ und y die vorstehend angegebene Bedeutung haben, gegebenenfalls in Gegenwart von inerten organischen Lösungsmitteln mit Propargylalkohol der Formelin which χ and y have the meaning given above, optionally in the presence of inert organic solvents with propargyl alcohol of the formula
HO — CH2 — C = CHHO - CH 2 - C = CH
(III)(III)
umsetzt.implements.
Die nach dem Verfahren der Erfindung erhältlichen Propinyl-N-phenylcarbamate haben eine höhere insektizide und akarizide Wirkung als die für den gleichen Zweck bereits bekannten Carbamate. Besonders überraschend ist, daß die neuen Propionyl-N-phenylcarbamate eine gute Pflanzenverträglichkeit aufweisen, da bekannt ist, daß ähnliche Propinyl-N-phenylcarbamate als Unkrautbekämpfungsmittel verwendet werden können, also sehr stark phytotoxisch sind (vgl. die deutsche Auslegeschrift 1 017 407).The propynyl-N-phenylcarbamates obtainable by the process of the invention have a higher level of insecticidal properties and acaricidal action than the carbamates already known for the same purpose. Particularly It is surprising that the new propionyl-N-phenylcarbamates are well tolerated by plants since it is known that similar propynyl-N-phenylcarbamates are used as weed control agents can be used, i.e. are very strongly phytotoxic (see the German Auslegeschrift 1 017 407).
Der Reaktionsverlauf kann durch das folgende Formelschema wiedergegeben werden, wenn man
Verfahren zur Herstellung von
Propinyl-N-phenylcarbamatenThe course of the reaction can be represented by the following equation if one processes for the preparation of
Propynyl-N-phenylcarbamates
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,
LeverkusenLeverkusen
Als Erfinder benannt:Named as inventor:
Dr. Rudolf Heiß, Altenfurt;Dr. Rudolf Heiss, Altenfurt;
Dr. Ingeborg Hammann, Köln;Dr. Ingeborg Hammann, Cologne;
Dr. Engelbert Kühle, Bergisch-GladbachDr. Engelbert Kühle, Bergisch-Gladbach
2,3-Dichlorphenylisocyanat als Ausgangsmaterial verwendet :2,3-dichlorophenyl isocyanate used as the starting material :
Cl ClCl Cl
NCO + HOCH2-C =NCO + HIGH 2 -C =
Cl ClCl Cl
(H) NH — C — OCH, — C = CH (H) NH - C - OCH, - C = CH
Als weitere Beispiele für zu verwendende Isocyanate seien genannt: 2,4-Dichlor-, 2,6-Dichlor-, 2,5-Dichlor-, 2-Chlor-4-methyl-, 2-Chlor-5-methyl- und I^-Dichlor-S-methyl-phenyl-isocyanat.Further examples of isocyanates to be used include: 2,4-dichloro, 2,6-dichloro, 2,5-dichloro, 2-chloro-4-methyl-, 2-chloro-5-methyl- and 1-4 -dichloro-S-methyl-phenyl-isocyanate.
Als Verdünnungsmittel für die Umsetzung kommen alle inerten organischen Lösungsmittel in Frage, z. B. Benzol, Chlorbenzol und Dioxan. Man kann die Umsetzung auch in überschüssigem Propargylalkohol durchführen. Zur Beschleunigung des Reaktionsablaufs setzt man zweckmäßigerweise geringe Mengen eines stark basischen Amins, ζ. B. Trimethylamin, zu.All inert organic solvents are suitable as diluents for the reaction, z. B. benzene, chlorobenzene and dioxane. The reaction can also be carried out in excess propargyl alcohol carry out. To accelerate the course of the reaction, it is expedient to use small amounts Amounts of a strongly basic amine, ζ. B. trimethylamine, too.
Die Reaktionstemperaturen können in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man zwischen 10 und 8O0C, vorzugsweise zwischen 20 und 500C.The reaction temperatures can be varied over a wide range. In general, the reaction is preferably carried out at between 10 and 8O 0 C, between 20 and 50 0 C.
Die Umsetzung und Aufarbeitung werden in üblicher Weise durchgeführt.The reaction and work-up are carried out in the customary manner.
Die nach dem Verfahren der Erfindung herstellbaren Verbindungen weisen starke insektizide und akarizide Wirkungen auf. Die Wirkungen setzenThe compounds which can be prepared by the process of the invention are potent insecticidal and acaricidal effects on. Set the effects
709 638/567709 638/567
schnell ein und halten lange an. Sie können deshalb mit gutem Erfolg zur Bekämpfung von schädlichen saugenden und beißenden Insekten, Dipteren sowie Milben verwendet werden.quickly and last a long time. You can therefore with good success to combat harmful ones sucking and biting insects, dipteras and mites can be used.
Zu den saugenden Insekten gehören im wesentlichen Blattläuse, wie die Pfirsichblattlaus (Myzus persicae), die schwarze Bohnenblattlaus (Doralis fabae); Schildläuse, wie Aspidiotus hederae; Thysanopterenrwie Hercinothrips femoralis, und Wanzen, wie die Rübenwanze (Piesma quadrata).The sucking insects mainly include aphids, such as the peach aphid (Myzus persicae), the black bean aphid (Doralis fabae); Scale insects such as Aspidiotus hederae; Thysanoptera r such as Hercinothrips femoralis, and bed bugs such as the beet bug (Piesma quadrata).
Zu den beißenden Insekten zählen im wesentlichen Schmetterlingsraupen, wie Plutella maculipennis; Käfer, wie Kronkäfer (Calandra granaria), aber auch im Boden lebende Arten, wie die Drahtwürmer (Agriotes sp.); Schaben, wie die Deutsche Schabe (Blattella germanica); Orthopteren, wie das Heimchen (Gryllus domesticus); Termiten, wie Reticulitermes; Hymenopteren, wie Ameisen.The biting insects essentially include caterpillars such as Plutella maculipennis; Beetles, such as the crown beetle (Calandra granaria), but also species that live in the ground, such as wireworms (Agriotes sp.); Cockroaches, such as the German cockroach (Blattella germanica); Orthoptera, like the cricket (Gryllus domesticus); Termites such as Reticulitermes; Hymenoptera, like ants.
Die Dipteren umfassen insbesondere die Fliegen, wie die Taufliege (Drosophila melanogaster), die Stubenfliege (Musca domestica) und Mücken, wie die Stechmücke (Aedes aegypti).The Diptera include in particular the flies, such as the fruit fly (Drosophila melanogaster), the House fly (Musca domestica) and mosquitoes such as the mosquito (Aedes aegypti).
Bei den Milben sind besonders wichtig die Spinnmilben (Tetranychidae), wie die gemeine Spinnmilbe (Tetranychus telarius); Gallmilben, wie die Johannisbeergallmilbe (Eriophyes ribis), und Tarsonemiden, wie Tarsonemus pallidus, und Zecken.Among the mites, the spider mites (Tetranychidae), like the common spider mite, are particularly important (Tetranychus telarius); Gall mites, such as the currant gall mite (Eriophyes ribis), and tarsonemids, like Tarsonemus pallidus, and ticks.
Besonders hervorzuheben ist die Wirkung der herstellbaren Verbindungen gegen die Eier von Insekten und Milben.Particularly noteworthy is the effect of the compounds that can be produced against the eggs of insects and mites.
Die herstellbaren Verbindungen können in die üblichen Zubereitungen, wie Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate, übergeführt werden und darin auch in Mischung mit anderen bekannten Wirkstoffen vorliegen.The compounds that can be prepared can be incorporated into the usual preparations, such as solutions, emulsions, Suspensions, powders, pastes and granulates, are transferred and also mixed with them other known active ingredients are present.
Die Zubereitungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 Gewichtsprozent.The preparations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90 percent by weight.
Die herstellbaren Verbindungen können als solche in Form ihrer Zubereitungen oder der daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate, angewendet werden. Die Anwendung geschieht in üblicher Weise.The compounds which can be prepared can be prepared as such in the form of their preparations or those prepared therefrom Application forms such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. It is used in the usual way.
Vergleichsversuch A
Plutella-TestComparative experiment A
Plutella test
Lösungsmittel:Solvent:
3 Gewichtsteile Aceton,3 parts by weight of acetone,
Emulgator:Emulsifier:
1 Gewichtsteil Alkylarylpolyglykoläther.1 part by weight of alkylaryl polyglycol ether.
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, das die angegebene Menge Emulgator enthält, und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the specified amount of solvent, which contains the specified amount of emulsifier, and diluted the concentrate with water to the desired concentration.
Mit der Wirkstoffzubereitung besprüht man Kohlblätter (Brassica oleracea) taufeucht und besetzt sie mit Raupen der Kohlschabe (Plutella maculipennis). Nach den angegebenen Zeiten wird der Abtötungsgrad in Prozent bestimmt. Dabei bedeutet 1000/o, daß alle Raupen getötet wurden, während 0% angibt, daß keine Raupen getötet wurden.Cabbage leaves (Brassica oleracea) are sprayed with the preparation of active compound and they are populated with caterpillars of the cabbage moth (Plutella maculipennis). After the specified times, the degree of destruction is determined in percent. Here, 100 0 / o that all the caterpillars were killed, whereas 0% indicates that no caterpillars have been killed.
Wirkstoffe, Wirkstoffkonzentrationen, Auswertungszeiten und Ergebnisse gehen aus der nachfolgenden Tabelle I hervor.Active ingredients, active ingredient concentrations, evaluation times and results are based on the following Table I.
Tabelle I
(Pflanzenschädigende Insekten)Table I.
(Plant damaging insects)
I Cl
I.
nach 4 TagenDegree of destruction in%
after 4 days
ö- Cl Cl
ö-
ICl
I.
Fortsetzungcontinuation
WirkstoffeActive ingredients
Wirkstoffkonzentration in %Active ingredient concentration in%
Abtötungsgrad in %
nach 4 TagenDegree of destruction in%
after 4 days
ClCl
CH3 CH 3
NH — COO — CH2 — C = CHNH - COO - CH 2 - C = CH
NH — COO — CH2 — C = CHNH - COO - CH 2 - C = CH
L- O — CO — N(CH3)'L - O - CO - N (CH 3 ) '
N7 N 7
CH(CH3)oCH (CH 3 ) o
(Vergleichsverbindung,
schweizerische Patentschrift 282 655)(Comparison connection,
Swiss patent 282 655)
0,020.02
0,020.02
8080
8080
0,20.2
9090
Vergleichsversuch BComparative experiment B
Tetranychus-TestTetranychus test
Lösungsmittel:Solvent:
3 Gewichtsteile Aceton,3 parts by weight of acetone,
Emulgator:Emulsifier:
1 Gewichtsteil Alkylarylpolyglykoläther.1 part by weight of alkylaryl polyglycol ether.
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, das die angegebene Menge Emulgator enthält, und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the specified amount of solvent, which contains the specified amount of emulsifier, and diluted the concentrate with water to the desired concentration.
Mit der Wirkstoffzubereitung werden Bohnenpflanzen (Phaseolus vulgaris), die ungefähr eine Höhe von 10 bis 30 cm haben, tropfnaß besprüht. Diese Bohnenpflanzen sind stark mit allen Entwicklungsstadien der Bohnenspinnmilbe (Tetranychus telarius) befallen.Bean plants (Phaseolus vulgaris) which are approximately one height from 10 to 30 cm, sprayed until dripping wet. These bean plants are strong with all stages of development of the bean spider mite (Tetranychus telarius) infested.
Nach den angegebenen Zeiten wird die Wirksamkeit der Wirkstoffzubereitung bestimmt, indem man die toten Tiere auszählt. Der so erhaltene Abtötungsgrad wird in Prozent angegeben. 100% bedeutet, daß alle Spinnmilben abgetötet wurden, 0% bedeutet, daß keine Spinnmilben abgetötet wurden. Wirkstoffe, Wirkstoffkonzentrationen, Auswertungszeiten und Ergebnisse gehen aus der nachfolgenden Tabelle II hervor.After the times indicated, the effectiveness of the active compound preparation is determined by counts the dead animals. The degree of destruction obtained in this way is given in percent. 100% means that all spider mites have been killed, 0% means that none of the spider mites have been killed. Active ingredients, active ingredient concentrations, evaluation times and results are based on the following Table II.
Tabelle II (Pflanzenschädigende Milben)Table II (Mites that are harmful to plants)
nach 2 TagenDegree of destruction in "/ 0
after 2 days
I I Cl Cl
II
1 248 03!1 248 03!
Fortsetzungcontinuation
Wirkstoffe Wirkstoffkonzentration in %Active ingredients Active ingredient concentration in%
Abtötungsgrad in °/o nach 2 TagenDegree of destruction in% after 2 days
NH — COO — CH2 -C =NH - COO - CH 2 -C =
NH — COO — CH2 -C =NH - COO - CH 2 -C =
NH — COO — CH2 -C =NH - COO - CH 2 -C =
CH3
O — CO — NH — CH3 CH 3
O - CO - NH - CH 3
(Vergleichsverbindung, USA.-Patentschrift 2 903 478) 0,02(Comparative compound, U.S. Patent 2,903,478) 0.02
0,020.02
0,20.2
0,20.2
9090
8080
100100
Beispiel Cl ClExample Cl Cl
<^ y— NH — COOCH2 — C = CH<^ y - NH - COOCH 2 - C = CH
18,8 g 2,3-Dichlorphenyl-isocyanat werden in 50 ml Aceton gelöst und bei Raumtemperatur in 100 ml Propargylalkohol unter Zusatz von 1 g Triäthylamin eingetropft. Hierbei steigt die Temperatur bis etwa 300C an. Man rührt eine Zeit bei 500C und engt die Reaktionslösung unter vermindertem Druck ein. Hierbei erhält man 23 g Propinyl-N-(2,3-dichlorphenyl)-carbamat vom F. = 69°C.18.8 g of 2,3-dichlorophenyl isocyanate are dissolved in 50 ml of acetone and added dropwise to 100 ml of propargyl alcohol at room temperature with the addition of 1 g of triethylamine. The temperature rises to about 30 ° C. during this process. The mixture is stirred for a time at 50 ° C. and the reaction solution is concentrated under reduced pressure. This gives 23 g of propynyl N- (2,3-dichlorophenyl) carbamate with a melting point of 69 ° C.
"In gleicher Weise erhält man die folgenden Verbindungen :"The following compounds are obtained in the same way :
ClCl
5°5 °
NH — COOCH2 — C = CHNH - COOCH 2 - C = CH
F. = 730CF. = 73 0 C
— NH — COOCH2 — C = CH- NH - COOCH 2 - C = CH
6o6o
F. = 75°CF. = 75 ° C
NH — COOCH2 — C ξ= CHNH - COOCH 2 - C ξ = CH
F. = 82°CM.p. = 82 ° C
CH3 CH 3
NH — COOCH2 -C = NH - COOCH 2 -C =
F. = 102°CM.p. = 102 ° C
NH — COO — CH2 NH - COO - CH 2
-C = CH -C = CH
F. = 60°CF. = 60 ° C
CH3 CH 3
Claims (1)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF43289A DE1248031B (en) | 1964-06-27 | 1964-06-27 | Process for the preparation of propynyl-N-phenylcarbamates |
| GB2275065A GB1034499A (en) | 1964-06-27 | 1965-05-28 | Propynyl-n-phenyl carbamates |
| CH742665A CH465585A (en) | 1964-06-27 | 1965-05-28 | Process for the preparation of propynyl-N-phenylcarbamates |
| IL2363865A IL23638A (en) | 1964-06-27 | 1965-05-31 | Propynyl-n-phenyl carbamates and a process for their preparation |
| DK321865A DK109916C (en) | 1964-06-27 | 1965-06-24 | Agent for controlling mites and insects as well as methods for preparing propinyl N-phenylcarbamates for use in the agent. |
| NL6508202A NL6508202A (en) | 1964-06-27 | 1965-06-25 | |
| BE665930D BE665930A (en) | 1964-06-27 | 1965-06-25 | |
| FR22439A FR1438812A (en) | 1964-06-27 | 1965-06-25 | Manufacturing process of propinyl-nu-phenylcarbamates |
| BR17076065A BR6570760D0 (en) | 1964-06-27 | 1965-06-25 | PROCESS OF PRODUCING PROPINYL-N-PHENYLIC CARBAMATES AND COMPOSITES PRAGUICIDES BASED ON THESE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF43289A DE1248031B (en) | 1964-06-27 | 1964-06-27 | Process for the preparation of propynyl-N-phenylcarbamates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1248031B true DE1248031B (en) | 1967-08-24 |
Family
ID=7099486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF43289A Pending DE1248031B (en) | 1964-06-27 | 1964-06-27 | Process for the preparation of propynyl-N-phenylcarbamates |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE665930A (en) |
| BR (1) | BR6570760D0 (en) |
| CH (1) | CH465585A (en) |
| DE (1) | DE1248031B (en) |
| DK (1) | DK109916C (en) |
| GB (1) | GB1034499A (en) |
| IL (1) | IL23638A (en) |
| NL (1) | NL6508202A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1148409B (en) * | 1960-10-29 | 1963-05-09 | Basf Ag | Fungicides |
-
1964
- 1964-06-27 DE DEF43289A patent/DE1248031B/en active Pending
-
1965
- 1965-05-28 GB GB2275065A patent/GB1034499A/en not_active Expired
- 1965-05-28 CH CH742665A patent/CH465585A/en unknown
- 1965-05-31 IL IL2363865A patent/IL23638A/en unknown
- 1965-06-24 DK DK321865A patent/DK109916C/en active
- 1965-06-25 BR BR17076065A patent/BR6570760D0/en unknown
- 1965-06-25 NL NL6508202A patent/NL6508202A/xx unknown
- 1965-06-25 BE BE665930D patent/BE665930A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1148409B (en) * | 1960-10-29 | 1963-05-09 | Basf Ag | Fungicides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6508202A (en) | 1965-12-28 |
| GB1034499A (en) | 1966-06-29 |
| IL23638A (en) | 1968-12-26 |
| BR6570760D0 (en) | 1973-09-20 |
| BE665930A (en) | 1965-12-27 |
| CH465585A (en) | 1968-11-30 |
| DK109916C (en) | 1968-07-29 |
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