DE1768296B2 - AETHYL-N-CYCLOHEXYL-N-PROPARGYLTHIOLCARBAMATE - Google Patents

AETHYL-N-CYCLOHEXYL-N-PROPARGYLTHIOLCARBAMATE

Info

Publication number
DE1768296B2
DE1768296B2 DE19681768296 DE1768296A DE1768296B2 DE 1768296 B2 DE1768296 B2 DE 1768296B2 DE 19681768296 DE19681768296 DE 19681768296 DE 1768296 A DE1768296 A DE 1768296A DE 1768296 B2 DE1768296 B2 DE 1768296B2
Authority
DE
Germany
Prior art keywords
ethyl
cyclohexyl
propargyl
carbamate
millet
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.)
Granted
Application number
DE19681768296
Other languages
German (de)
Other versions
DE1768296A1 (en
DE1768296C3 (en
Inventor
Karl Dr. 6840 Lampertheim; König Karl-Heinz Dr. 6710 Frankenthal; Fischer Adolf Dr. 6704 Mutterstadt Kiehs
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE1768296A priority Critical patent/DE1768296C3/en
Priority to AT322669A priority patent/AT290197B/en
Priority to BG012085A priority patent/BG16167A3/en
Priority to FR6913019A priority patent/FR2007003A1/fr
Priority to NL6906354.A priority patent/NL162900C/en
Priority to CS2919A priority patent/CS171678B2/cs
Priority to BE732023D priority patent/BE732023A/xx
Priority to GB1253112D priority patent/GB1253112A/en
Priority to PL1969133195A priority patent/PL69675B1/pl
Publication of DE1768296A1 publication Critical patent/DE1768296A1/en
Publication of DE1768296B2 publication Critical patent/DE1768296B2/en
Application granted granted Critical
Publication of DE1768296C3 publication Critical patent/DE1768296C3/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/14Dithiocarbamic acids; Derivatives thereof
    • C07C333/16Salts of dithiocarbamic acids

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Beispiel 1
Äthyl-N-cyclohexyl-N-propargyl-thiolcarbamat
example 1
Ethyl N-cyclohexyl-N-propargyl-thiol carbamate

Zu einem Gemisch von 14 Gewichtsteilen Triäthyl- »5 amin, 20 Gewichtsteilen N-Cyclohexyl-N-propargylamin und 120 Gewichtsteilen Benzol werden bei 70 bis 8O0C 18 Gewichtsteile Chlorameisensäurethioäthylester zugetropft. Man hält 2 Stunden bei Rückflußbedingungen, zersetzt das Gemisch mit Wasser, 30 wäscht mit verdünnter Schwefelsäure, trocknet, destilliert und erhält so das Endprodukt; Kp.o Oi mm = 117 bis 119aC (Ausbeute: 85% der Theorie). "Amine To a mixture of 14 parts by weight of triethyl "5, 20 parts by weight of N-cyclohexyl-N-propargylamine and 120 weight parts of benzene are added dropwise 18 parts by weight Chlorameisensäurethioäthylester at 70 to 8O 0 C. The mixture is kept under reflux conditions for 2 hours, the mixture is decomposed with water, washed with dilute sulfuric acid, dried and distilled, and the end product is thus obtained; Bp. O O i mm = 117 to 119 a C (yield: 85% of theory). "

Der Wirkstoff kann als Lösung, Emulsion, Suspension oder Stäubemittel angewendet werden. Die 35 Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollen in jedem Fall eine feine Verteilung der wirksamen Substanz gewährleisten.The active ingredient can be used as a solution, emulsion, suspension or dust. The 35 Forms of application depend entirely on the intended use; they should be a fine one in any case Ensure distribution of the active substance.

Zur Herstellung von direkt versprühbaren Lösungen können Kohlenwasserstoffe, wie Tetrahydronaphtha- 40 lin, und olkylierte Naphthaline als Spritzflüssigkeiten verwendet werden.Hydrocarbons such as tetrahydronaphtha- 40 can be used to produce solutions that can be sprayed directly lin, and alkylated naphthalenes as spray liquids be used.

Wäßrige Anwendungsformen können aus Emul- _ . . , .Aqueous use forms can be made from emulsions. . ,.

sionskonzentraten, Pasten oder netzbaren Pulvern e' ^sion concentrates, pastes or wettable powders e '^

(Spritzpulvern) durch Zusatz von Wasser bereitet 45 Eine 2 m2 große Parzelle mit einem Bestand an Kohl werden. Zur Herstellung von Emulsionen können die (Brassica oleracea var. vulgaris), Rüben (Beta vulgaris), Substanzen als solche oder in einem Lösungsmittel einjährigem Rispengras (Poa annua), Flughafer (Avena gelöst, mittels Netz- oder Dispergiermitteln in Wasser fatua), Hühnerhirse (Echinochloa crus-galli) wurde oder organischen Lösungsmitteln homogenisiert wer- mit 3 kg je ha Äthyl-N-propargyl-N-cyclohexyl-thiolden. Es können abei auch aus wirksamer Substanz, 50 carbamat (I) dispergiert in 500 Liter Wasser je ha Emulgier- oder Dispergiermittel und eventuell Lö- behandelt. Nach 3 bis 4 Wochen wurde ferstgestellt, sungsmittel bestehende Konzentrate hergestellt werden, daß die Ungräser fast vollkommen abgestorben waren, die zur Verdünnung mit Wasser geeignet sind. während Kohl und Rüben nur eine geringe Wachs-(Wettable powders) can be prepared by adding water 45 A 2 m 2 large parcel with a stock of cabbage. To produce emulsions, beets (Brassica oleracea var. Vulgaris), beets (Beta vulgaris), substances as such or in a solvent annual bluegrass (Poa annua), wild oats (Avena dissolved, fatua by means of wetting agents or dispersants in water), chicken millet (Echinochloa crus-galli) or organic solvents are homogenized with 3 kg per hectare of ethyl-N-propargyl-N-cyclohexyl-thioldene. It is also possible to use an active substance, 50 carbamate (I) dispersed in 500 liters of water per hectare of emulsifying or dispersing agent, and possibly soldering. After 3 to 4 weeks it was established that concentrates consisting of solvents were produced so that the grass weeds had almost completely died and were suitable for dilution with water. while cabbage and beets have only a slight

Gtäubemittel können durch Mischen oder gemein- tumshemmung zeigten, die sich später wieder auswuchs.Pigeons can be shown by mixing, or by community inhibition, which later grew out again.

WirkstoffActive ingredient IIII II. NutzpflanzenCrops 20 bis 3020 to 30 MaisCorn 1010 1010 RübenBeets 0 bis 100 to 10 20 bis 3020 to 30 KohlCabbage 1010 Unerwünschte PflanzenUnwanted plants 9090 EinjährigesAnnual 9090 RispengrasBluegrass 100100 FlughaferWild oats 90 bis 10090 to 100 9090 HühnerhirseChicken millet 90 bis 10090 to 100 90 bis 10090 to 100 Grüne BorstenhirseGreen millet 90 bis 10090 to 100 70 bis 8070 to 80 BluthirseBlood millet 8080 0 = keine Schädigung0 = no damage 100 = totale Schädigung100 = total damage

Claims (2)

1 2 Patentansprüche· sames Vermählen der wirksamen Substanzen mit einsrn festen Trägerstoff hergestellt werden.1 2 patent claims · grinding the active substances with a solid carrier material can be produced. 1. Äthyl-N-q'dohexyl-K-propargyl-thiolcarb- Die biologische Wirkung der neuen Verbindung amat, ergibt sich aus den nachfolgenden Beispielen.1. Ethyl-N-q'dohexyl-K-propargyl-thiolcarb- The biological effect of the new compound amat, results from the following examples. 2. Herbizid, enthaltend einen festen oder flüssi- 5 .2. Herbicide containing a solid or liquid 5. gen Trägerstoff und Äthyl-N-cyclohexyl-N-pro- B e ι s ρ ι e 1 2gene carrier and ethyl-N-cyclohexyl-N-pro- B e ι s ρ ι e 1 2 pargyl-thiolcarbamat. In Versuchstöpfe wurde lehmiger Sandboden einpargyl thiol carbamate. Loamy sandy soil was placed in the test pots gefüllt und die Samen von Mais (Zea mays), Rübenfilled and the seeds of maize (Zea mays), beets (Beta vulgaris), Kohl (Brassica oleracea var. vulgaris),(Beta vulgaris), cabbage (Brassica oleracea var. Vulgaris), ίο einjährigem Rispengras (Poa annua), Flughafer (Avena fatua), Hühnerhirse (Echinochloa crus-galli), grüneίο annual bluegrass (Poa annua), flying oats (Avena fatua), chicken millet (Echinochloa crus-galli), green Die vorliegende Erfindung betrifft die neue Verbin- Borstenhirse (Seraria viridis), Bluthirse (Digitaria dung Äthyl-N-cyclohexyl-N-propargyl-thiolcarbamat sanguinalis) eingesät und der so vorbereitete Boden und dieses enthaltende Herbizide. mit Äthyl-N-propargyl-N-cyclohexylthiolcarbamat (I)The present invention relates to the new connecting millet (Seraria viridis), blood millet (Digitaria Ethyl-N-cyclohexyl-N-propargyl-thiolcarbamate sanguinalis) sown and the soil prepared in this way and herbicides containing them. with ethyl N-propargyl-N-cyclohexylthiol carbamate (I) Es ist bekannt, Äthyl-N-äthyl-N-cyclohexyl-thiol- 15 und im Vergleich mit Äthyl-N-äthyl-N-cyclohexylthiolcarbamat als Herbizid zu verwenden (US-Patent- carbamat(II) behandelt. Die Aufwandmengen beschrift 31 85 720; GB-Patentschrift 9 95 316). trugen jeweils 3 kg Wirkstoff je ha und wurden disper-It is known, ethyl-N-ethyl-N-cyclohexyl-thiol- 15 and in comparison with ethyl-N-ethyl-N-cyclohexylthiol carbamate to be used as a herbicide (US patent carbamate (II) treated. The application rates are labeled 31 85 720; GB Patent Specification 9 95 316). each carried 3 kg of active ingredient per hectare and were dispersed _ Es wurde nun gefunden, daß die neue Verbindung giert in 500 Liter Wasser je ha. Nach 4 bis 5 Wochen Äthyl-N-cyclohexyl-N-propargyl-thiolcarbamat sehr wurde festgestellt, daß I eine bessere Pflanzenverträggute herbizide Eigenschaften besitzt. ao lichkeit an Mais und Kohl zeigte als II.It has now been found that the new compound yaws in 500 liters of water per hectare. After 4 to 5 weeks Ethyl-N-cyclohexyl-N-propargyl-thiolcarbamate was found to be a better plant tolerant possesses herbicidal properties. Ao possibility on maize and cabbage showed as II.
DE1768296A 1968-04-26 1968-04-26 Ethyl N-cyclohexyl-N-propargylthiol carbamate Expired DE1768296C3 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
DE1768296A DE1768296C3 (en) 1968-04-26 1968-04-26 Ethyl N-cyclohexyl-N-propargylthiol carbamate
AT322669A AT290197B (en) 1968-04-26 1969-04-02 herbicide
BG012085A BG16167A3 (en) 1968-04-26 1969-04-18 HERBICIDE
NL6906354.A NL162900C (en) 1968-04-26 1969-04-24 PROCESS FOR PREPARING SUBSTITUTED ALKYLTHIOL CARBAMATES
FR6913019A FR2007003A1 (en) 1968-04-26 1969-04-24
CS2919A CS171678B2 (en) 1968-04-26 1969-04-24
BE732023D BE732023A (en) 1968-04-26 1969-04-24
GB1253112D GB1253112A (en) 1968-04-26 1969-04-25
PL1969133195A PL69675B1 (en) 1968-04-26 1969-04-25

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1768296A DE1768296C3 (en) 1968-04-26 1968-04-26 Ethyl N-cyclohexyl-N-propargylthiol carbamate

Publications (3)

Publication Number Publication Date
DE1768296A1 DE1768296A1 (en) 1971-10-28
DE1768296B2 true DE1768296B2 (en) 1976-02-19
DE1768296C3 DE1768296C3 (en) 1978-12-21

Family

ID=5699683

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1768296A Expired DE1768296C3 (en) 1968-04-26 1968-04-26 Ethyl N-cyclohexyl-N-propargylthiol carbamate

Country Status (9)

Country Link
AT (1) AT290197B (en)
BE (1) BE732023A (en)
BG (1) BG16167A3 (en)
CS (1) CS171678B2 (en)
DE (1) DE1768296C3 (en)
FR (1) FR2007003A1 (en)
GB (1) GB1253112A (en)
NL (1) NL162900C (en)
PL (1) PL69675B1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5811842B2 (en) * 1975-08-15 1983-03-04 クミアイカガクコウギヨウ カブシキガイシヤ Satsudanizai

Also Published As

Publication number Publication date
BG16167A3 (en) 1972-07-20
DE1768296A1 (en) 1971-10-28
NL162900C (en) 1980-07-15
CS171678B2 (en) 1976-10-29
NL162900B (en) 1980-02-15
GB1253112A (en) 1971-11-10
PL69675B1 (en) 1973-08-31
AT290197B (en) 1971-05-25
BE732023A (en) 1969-10-24
FR2007003A1 (en) 1970-01-02
NL6906354A (en) 1969-10-28
DE1768296C3 (en) 1978-12-21

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Legal Events

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C3 Grant after two publication steps (3rd publication)
8330 Complete renunciation