SU592352A3 - Method of preparing diurethans - Google Patents

Method of preparing diurethans

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Publication number
SU592352A3
SU592352A3 SU752130994A SU2130994A SU592352A3 SU 592352 A3 SU592352 A3 SU 592352A3 SU 752130994 A SU752130994 A SU 752130994A SU 2130994 A SU2130994 A SU 2130994A SU 592352 A3 SU592352 A3 SU 592352A3
Authority
SU
USSR - Soviet Union
Prior art keywords
alkyl
solution
general formula
halogen
substituted
Prior art date
Application number
SU752130994A
Other languages
Russian (ru)
Inventor
Борошевски Герхард
Арндт Фридрих
Original Assignee
Шеринг Аг (Фирма)
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 Шеринг Аг (Фирма) filed Critical Шеринг Аг (Фирма)
Application granted granted Critical
Publication of SU592352A3 publication Critical patent/SU592352A3/en

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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
    • A01N47/12—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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Landscapes

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

Description

(54) СПОСОБ ПОЛУЧЕНИЯ ДИУРЕТАНОВ(54) METHOD FOR OBTAINING DIURETHANES

П р и м е р 1. Эгил- N - з-(Ы,М-дипропилкарбамоилокси-феннл -кар&amp;амаг (соединение № 2 в нижеследующей таблице), PRI me R 1. Egil-N - s- (S, M-dipropylcarbamoyloxy-fenl-kar-amp (compound No. 2 in the table below),

Раствор 16,7 г метилсжого эфира 3-ок сикарбаминовой кислоты и 19,6 гЫ,К-дипро пидкарбамоилхлорида в 50 мл сухого пиридииа нагревают до 90°С на вод ной бане в течение 45 мин. После выпаривани  в вакууме остаток раствор ют в уксусном эфире , промывают при О°С концентрированным раствором едкого натра, разбавленной сол ной кислотой и водой, затем раствор сушат сульфатом магни  и концентрируют в вакууме; Остаток после выпаривани  кристаллизуют при доб авлений пентана, далее перекристаллизовывают из смеси тетрагидрофуран-пентан . Выход 21,0 г (68%), температура воспламенени  82-84 °С.A solution of 16.7 g of methyl 3-oxacarbamic acid ester and 19.6 gy, K-dipropidarbamoyl chloride in 50 ml of dry pyridium is heated to 90 ° C in a water bath for 45 minutes. After evaporation in vacuo, the residue is dissolved in ethyl acetate, washed at 0 ° C with a concentrated solution of caustic soda, dilute hydrochloric acid and water, then the solution is dried with magnesium sulfate and concentrated in vacuo; The residue after evaporation is crystallized with the addition of pentane, then recrystallized from tetrahydrofuran-pentane. Yield 21.0 g (68%), flash point 82-84 ° C.

При м е р 2. Этил -N- 3- (N -метил- N -циклогексилкарбамоилсжси)-фенил чсарбамат (втаблице соединение М 35).Example 2. Ethyl-N-3- (N-methyl-N-cyclohexylcarbamoylszhsi) -phenyl chsarbamate (in the table M 35).

Раствор 18,4 г этилового эфира карбаминовой кислоты и 21,0 г -метилN -циклогексилкарбамоилхлорида в 50 мл сухого пиридина нагревают 15 мин на вод ной бане до 115°С. После выпаривани  в вакууме остаток раствор ют в уксусном эфире , промывают при слабо разбавленным раствором едкого натра, разбавленной сол ной кислотой и водой, затем раствор сушат сульфатом магни  и концентрируют в вакууме . Остаток после выпаривани  кристаллизуют при добавлении пентана, а затем перекристалли .зовывают из смеси тетрагидрофу- рана-пентан. Выход целевого продукта 25,0 ( 72%), т. пл. 77-79°С.A solution of 18.4 g of carbamic acid ethyl ester and 21.0 g of α-methylN-cyclohexylcarbamoyl chloride in 50 ml of dry pyridine is heated for 15 minutes in a water bath to 115 ° C. After evaporation in vacuo, the residue is dissolved in ethyl acetate, washed with slightly dilute sodium hydroxide solution, dilute hydrochloric acid and water, then the solution is dried with magnesium sulfate and concentrated in vacuo. The residue after evaporation crystallized upon the addition of pentane, and then recrystallized from tetrahydrofuran-pentane mixture. The yield of the target product is 25.0 (72%), so pl. 77-79 ° C.

Пример 3. Метил- N - 3-( N -эгилН№ -6утилкарбамоилокси)-фенил -карбамат (в таблице № 29). Example 3. Methyl-N - 3- (N -egilN№ -6utilcarbamoyloxy) -phenyl-carbamate (in table No. 29).

Раствор 16,7 г метилового эфира 3-оксикарбаминовой кислОты и 19,6 г Ti -этил- N -бутилкарб;амоилхлорида нагревают приблизительно в 50 мл сухого пиридина на вод ной бане в течение 12О мин до 50 С, После выпаривани  в вакууме остаток раствор ют в уксусном эфире, промывают при ОС слабо разбавленным раствором едкого натра, разбавленной сол нсЛ кислотой и водсй, затем раствор высушивают сульфатом магни  и концентрируют в вакууме. Остаток после вьшаривани  криста; пизуют при добавлении пентана, а затем нере cpиcтaллизofeывaюr из смеси тетрагидрофу-paHii eHraH .A solution of 16.7 g of methyl 3-hydroxycarbamic acid ester and 19.6 g of Ti-ethyl-N-butylcarb, amoyl chloride is heated in approximately 50 ml of dry pyridine in a water bath for 12O min to 50 ° C. After evaporation in vacuo, the remaining solution in acetic ether, washed with OC with slightly dilute sodium hydroxide solution, dilute hydrochloric acid and water, then the solution is dried with magnesium sulfate and concentrated in vacuo. The remainder of the cristae; Pizan is added when pentane is added, and then non-proliferative from a mixture of tetrahydro-paHii eHraH.

Аналогично получают другие диуретаны обшей формулы (I ), :псж;азатели которых приведены в таблице.Other diurethanes of the general formula (I) are obtained in a similar manner:

фf

гюgyu

смcm

со соwith so

1 S1 s

« S"S

5  five

Г|R |

0) 00) 0

§§

аbut

.м.m

II

тt

1 313

5 м5 m

7f7f

;;

:г : g

Т T

вat

|.|.

21. р21. р

Sg.Sg.

0) «0) "

«Л,$5"L, $ 5

s: иs: and

МM

0000

ЙФYF

соwith

ЮYU

соwith

шsh

0000

«О"ABOUT

0303

о about

оabout

11eleven

Claims (1)

12 Формула изобретени  Способ получени  диуретанов обшей фор - JO-KC JtH-CO-X-R, I где Uj- аллил, Сц-алкил, замещенный галогеном С -алкил; RJ- замещенный галогеном Сцкил , диклргекснл, бензил или . фенилатил;т К -С|-С J-алкил; Х- кислород ИЛИ сера, отличающийс  тем, что карбамоилхлорид общей формулы 3f-(Jo-Ci л nf где Tl-i и Я, имеют вышеуказанные рначеподвергают взаимодействию с соединением .общей формулы 1 и-Со-х-Нз и где R.J и X имеют вышеуказанные значени , органическом растворителе при 50 115°С в присутствии третичных органических осиований . Источники И11формации, прин тые во внимание при экспертизе: 1. Каррер П. Курс органической химии, Л., Госхимиздат, I960, с. 256-284.12 The claims The method for producing diurethanes of the general form is JO-KC JtH-CO-X-R, I where Uj is allyl, Sc-alkyl, substituted with halogen C-alkyl; RJ-substituted by halogen Skyl, diclgexnl, benzyl or. phenythyl; t K —C | —C J-alkyl; X is oxygen OR sulfur, characterized in that the carbamoyl chloride of the general formula 3f- (Jo-Ci and nf where Tl-i and I have the above-mentioned naccharum reacting with the compound of general formula 1 and-Co-x-Hz and where RJ and X have the above values, an organic solvent at 50–115 ° C in the presence of tertiary organic scattering Sources of information taken into account in the examination: 1. Carrer P. Course in Organic Chemistry, L., Goskhimizdat, I960, pp. 256-284.
SU752130994A 1973-03-01 1975-05-06 Method of preparing diurethans SU592352A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2310648A DE2310648C3 (en) 1973-03-01 1973-03-01 Diurethanes, processes for the preparation of these compounds and selective herbicidal agents containing them

Publications (1)

Publication Number Publication Date
SU592352A3 true SU592352A3 (en) 1978-02-05

Family

ID=5873703

Family Applications (3)

Application Number Title Priority Date Filing Date
SU2005475A SU528019A3 (en) 1973-03-01 1974-02-28 Herbicide
SU7402005371A SU578867A3 (en) 1973-03-01 1974-02-28 Method of preparing diuretan derivatives
SU752130994A SU592352A3 (en) 1973-03-01 1975-05-06 Method of preparing diurethans

Family Applications Before (2)

Application Number Title Priority Date Filing Date
SU2005475A SU528019A3 (en) 1973-03-01 1974-02-28 Herbicide
SU7402005371A SU578867A3 (en) 1973-03-01 1974-02-28 Method of preparing diuretan derivatives

Country Status (25)

Country Link
JP (1) JPS572681B2 (en)
AT (1) AT332163B (en)
BE (1) BE811783A (en)
BG (2) BG27894A4 (en)
BR (1) BR7401460D0 (en)
CH (1) CH586506A5 (en)
CS (1) CS172276B2 (en)
DD (1) DD112071A5 (en)
DE (1) DE2310648C3 (en)
EG (1) EG11202A (en)
ES (1) ES423651A1 (en)
FR (1) FR2219935B1 (en)
GB (1) GB1467513A (en)
HK (1) HK1978A (en)
HU (1) HU168694B (en)
IL (1) IL44276A (en)
IT (1) IT1049220B (en)
MY (1) MY7800110A (en)
NL (1) NL7402851A (en)
PH (1) PH12899A (en)
PL (1) PL89818B1 (en)
RO (2) RO69331A (en)
SU (3) SU528019A3 (en)
YU (1) YU39651B (en)
ZA (1) ZA741366B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2557552C2 (en) * 1975-12-18 1984-12-20 Schering AG, 1000 Berlin und 4709 Bergkamen Diurethanes and herbicidal agents containing these compounds as active ingredients
JPS5833970B2 (en) * 1978-09-08 1983-07-23 富士通株式会社 Inter-processor communication method

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3404975A (en) * 1964-12-18 1968-10-08 Fmc Corp m-(carbamoyloxy)-carbanilates as herbicides
DE1593523A1 (en) * 1966-10-15 1970-07-16 Schering Ag Process for the preparation of N-carbamoyloxyphenyl carbamates
DE2109798C3 (en) * 1971-02-23 1979-12-20 Schering Ag, 1000 Berlin Und 4619 Bergkamen N-3-Carbamoyloxyphenyl-Thiolcarbamate and herbicidal agent containing them

Also Published As

Publication number Publication date
AT332163B (en) 1976-09-10
YU39651B (en) 1985-03-20
DE2310648C3 (en) 1982-05-06
RO69716A (en) 1981-05-30
IT1049220B (en) 1981-01-20
BR7401460D0 (en) 1974-10-29
ZA741366B (en) 1975-01-29
AU6606774A (en) 1975-08-28
DD112071A5 (en) 1975-03-20
ATA165674A (en) 1975-12-15
DE2310648B2 (en) 1981-07-30
BG27871A3 (en) 1980-01-15
RO69331A (en) 1981-05-15
GB1467513A (en) 1977-03-16
ES423651A1 (en) 1976-04-16
JPS5040732A (en) 1975-04-14
YU40474A (en) 1982-05-31
PH12899A (en) 1979-10-04
JPS572681B2 (en) 1982-01-18
SU578867A3 (en) 1977-10-30
DE2310648A1 (en) 1974-09-19
HK1978A (en) 1978-01-20
BG27894A4 (en) 1980-01-15
FR2219935A1 (en) 1974-09-27
MY7800110A (en) 1978-12-31
CH586506A5 (en) 1977-04-15
HU168694B (en) 1976-06-28
NL7402851A (en) 1974-09-03
EG11202A (en) 1977-09-30
IL44276A (en) 1977-10-31
IL44276A0 (en) 1974-05-16
PL89818B1 (en) 1976-12-31
BE811783A (en) 1974-09-02
CS172276B2 (en) 1976-12-29
FR2219935B1 (en) 1977-09-16
SU528019A3 (en) 1976-09-05

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