SU1709909A3 - Method for synthesis of (2-thienylmethyl)-thiourea derivatives - Google Patents

Method for synthesis of (2-thienylmethyl)-thiourea derivatives Download PDF

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SU1709909A3
SU1709909A3 SU894613916A SU4613916A SU1709909A3 SU 1709909 A3 SU1709909 A3 SU 1709909A3 SU 894613916 A SU894613916 A SU 894613916A SU 4613916 A SU4613916 A SU 4613916A SU 1709909 A3 SU1709909 A3 SU 1709909A3
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USSR - Soviet Union
Prior art keywords
feed
compounds
weight
experiment
animals
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SU894613916A
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Russian (ru)
Inventor
Ратц Илдико
Береньи Эдит
Бенко Пал
Божинг Даниел
Мадьяр Карой
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Эгиш Дьедьсердьяр (Инопредприятие)
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/116Heterocyclic compounds
    • A23K20/121Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

Abstract

Изобретение относитс  к гетероциклическим соединени м, в частности к получению производных The invention relates to heterocyclic compounds, in particular to the preparation of derivatives

Description

Изобретение относитс  к способу получени  новых производных (2-тиенилметил )-тиомочевииы, которые могут быть использованы в качестве кормовых добавок дл  различных животных.This invention relates to a process for the preparation of (2-thienylmethyl) thiourea derivatives, which can be used as feed additives for various animals.

Целью изобретени   вл етс  раара .ботка способа получени  новых производных тиомочевины, которые были бы более эффективными добавками к кормам животных, чем структурные аналоги . Например фурфурилтиомочевина, известный препарат цинк-бацитрацин. The aim of the invention is a method for producing new thiourea derivatives, which would be more effective additives to animal feed than structural analogues. For example, furfurylthiourea, a well-known drug zinc bacitracin.

Приме р 1. Ы-5ензил-Ы -(2-тиенилметил )-тиомочевина.Example 1. P-5Zen-5- (2-thienylmethyl) -thiourea.

К эмульсии 73,56 г .(0,65 моль) тениламина и 500 мл бензина по капл м добавл ют при перемешивании 97,0 (0,65 моль) бензилизотиоцианата. Реакционную смесь перемешивают приTo the emulsion of 73.56 g (0.65 mol) of tenylamine and 500 ml of gasoline, 97.0 (0.65 mol) of benzyl isothiocyanate are added dropwise with stirring. The reaction mixture is stirred at

Комнатной температуре в течение ч, затем фильтруют и промывают бензином Получают 153,75 г целевого соединени . Выход 89,6%, т.пл. 108-109С (из метанола).Room temperature for an hour, then filtered and washed with gasoline. 153.75 g of the expected compound are obtained. Yield 89.6%, mp. 108-109С (from methanol).

9 .9 .

П р и м е р 2. Ы-Циклогекс,ил-Ы - (2-тиенилметил)-тиомочевина.PRI mme R 2. Y-Cyclohex, IL-S - (2-thienylmethyl) -thiourea.

82,6 г (0,7 моль) тениламина и 98,86 г (0,7 моль) циклогексил-изотиоцианата подвергают взаимодействию по аналогии с примером 1. Получают 171,6 г целевого соединени . Выход 96,4, т.пл. 112-ПЗ°С (из метанола).82.6 g (0.7 mol) of tenylamine and 98.86 g (0.7 mol) of cyclohexyl isothiocyanate are reacted by analogy with example 1. 171.6 g of target compound are obtained. Exit 96.4, m.p. 112-ПЗ ° С (from methanol).

Примерз. N-(1-Нафтил)-N- (2-тиенилметил)-тиомочевина.Froze N- (1-Naphthyl) -N- (2-thienylmethyl) -thiourea.

Claims (2)

2,2б г (0,02 моль) тениламина и 3,7 г (0,02 моль) 1-на()тилизотиоцианата подвергают взаимодействию по Получают 5,8 аналогии с примером 1 целевого соединени , выход 38 т.пл. (из этанола). Соединени  общей формулы I вызывают увеличение веса животных особе но свиней, овец, цыпл т, что св зан с улучшенной усваиваемостькз кормов. Действие предлагаемых соединений изучали в тестовых опытах. , Опыт на  гн тах. Этот опыт проводили на  гн тах дл  жаркого с временем откорма 0 дней. Животные получали корм следую щего состава, мас.: Измельченна  кукуруза70,0 Мука из люцерны II класса24,0 Мочевина3,0 Кормова  известь0,5 Монокальцийфосфат1 ,0 Кристаллический сульфат натри  , .0,5 Кормова  соль 0,5 ( корм дл   гн т) Ламмпремикс XIX ( филакси )0,5 Испытуемые соединени  добавл ли в виде стандартных гранул в концентрации 50 млн . Животные контрольной группы получали корм указанного выше состава, однако без активного вещества. . Дл  опыта были вз ты исключитель но венгерские мериносы. Кажда  груп состо ла из 12  гн т, дл  каждой об работки использовали 3 группы живот ных. Во врем  О-дневного опыта каж дого  гненка взвешивали п ть раз, а именно в начале опыта и каждые 10 д ( последний раз на 40-й день), всегд в одно и то же врем . Указывали вес без округлений. Количество съеденно корма определ ли а каждой декаде и дл  каждой группы. 9 Результаты приведены в табл. 1 причем увеличение веса и количество съеденного корма -указано как среднее значение дл  трех опытов. Как видно из указанных результатов соединени  общей формулы I существенно улучшают усваиваемость корма, т.е. увеличение веса на 1 кг может быть достигнуто с меньшим количеством корма . Соединени  общей формулы I не оказывают антибиоцидного действи , поэтому при их применении не про вл ютс  недостатки антибиотиков. Кроме того, существенное преимущество соединений общей формулы I заключаетс  в том, что они не обладают мутагенным действием. Опыт с цыпл тами. Опыт проводили с бройлерными цыпл тами . Полученные результаты приведены в табл. 2.2b g (0.02 mol) of tenylamine and 3.7 g (0.02 mol) of 1-per () thylisothiocyanate are reacted as follows. 5.8 analogies are obtained with Example 1 of the title compound, yield 38 mp. (from ethanol). The compounds of general formula I cause an increase in the weight of animals, especially pigs, sheep, chickens, which is associated with improved digestibility of feed. The effect of the proposed compounds was studied in test experiments. , Experience on the slopes. This experiment was carried out on hot rods with a fattening time of 0 days. The animals received feed of the following composition, wt .: Grinded corn70.0 Flour from alfalfa Class II 24.0 Urea 3.0 Feed lime 0.50 Monocalcium phosphate 1, 0 Crystalline sodium sulfate, .0.5 Feed salt 0.5 (feed for bed) Lampmpreix XIX (phylaxi) 0.5 Test compounds were added in the form of standard granules at a concentration of 50 ppm. Animals of the control group received feed of the above composition, but without the active substance. . For the experience, only Hungarian merino were taken. Each group consisted of 12 rats, for each treatment 3 groups of animals were used. During the O-day experiment, each head was weighed five times, namely at the beginning of the experiment and every 10 days (the last time on the 40th day), always at the same time. Indicated weight without rounding. The amount of food eaten was determined in each decade and for each group. 9 The results are shown in Table. 1 and the increase in weight and the amount of food eaten is indicated as an average of three experiments. As can be seen from the above results, the compounds of general formula I significantly improve the digestibility of the feed, i.e. weight gain per 1 kg can be achieved with less feed. The compounds of general formula I do not have an antibiocidal effect, therefore, their use does not show the disadvantages of antibiotics. In addition, a significant advantage of the compounds of the general formula I is that they do not have a mutagenic effect. Experience with chick tami. The experiment was carried out with broiler chickens. The results are shown in Table. 2. В группе цыпл т в возрасте 9 дней можно сэкономить 2,3% корма, счита  на контрольную группу (рассчитано на 1 кг живого веса). Формула изобретени  Способ получени  производных (2-тиенилметил )-тиомочевины формулы O-%-NH-C-KH-A 8 II ) где А - фенил- С -С -алкил, С -Сд-циклоалкил или нафтил, отличаюс   тем, что изотиоцианат форА - NCS имеет указанные значени . подвергают взаимодействию тениламином формулы iL CHj-NH2. In the group of chickens at the age of 9 days, 2.3% of feed can be saved, based on the control group (calculated for 1 kg of live weight). Claims for the preparation of (2-thienylmethyl) -thiourea derivatives of the formula O -% - NH-C-KH-A 8 II) where A is phenyl-C-C-alkyl, C-Cd-cycloalkyl or naphthyl, characterized in that phorA-NCS isothiocyanate has the indicated values. interact with tenylamine formula iL CHj-NH Таблица 1Table 1 Средний ежедневный прирост веса, гAverage daily weight gain, g То же, Also, Удельное потреблени корма, кг/кгSpecific feed consumption, kg / kg То же, Also, 266,7 105,2266.7 105.2 3,79 95,93.79 95.9 Таблица 2table 2
SU894613916A 1987-10-02 1989-04-18 Method for synthesis of (2-thienylmethyl)-thiourea derivatives SU1709909A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU874437A HU202516B (en) 1987-10-02 1987-10-02 Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds

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JP (1) JPH01156975A (en)
KR (1) KR890006612A (en)
AU (1) AU607811B2 (en)
BE (1) BE1003234A4 (en)
CH (1) CH676849A5 (en)
DD (1) DD282914A5 (en)
DE (1) DE3833603A1 (en)
DK (1) DK549788A (en)
ES (1) ES2012122A6 (en)
FR (1) FR2621315A1 (en)
GB (1) GB2210616B (en)
HU (1) HU202516B (en)
IL (1) IL87874A0 (en)
IT (1) IT1226862B (en)
NL (1) NL8802406A (en)
PL (3) PL151836B1 (en)
RU (1) RU1792415C (en)
SU (2) SU1739847A3 (en)
YU (3) YU182188A (en)

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NO20093460A1 (en) * 2009-12-02 2011-06-03 Ewos Innovation As Feed composition for fish containing a semiochemical masking compound and use of the compound.

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NL125059C (en) * 1963-05-31
US4267191A (en) * 1980-05-21 1981-05-12 American Cyanamid Company Process for enhancing growth promotion in animals
US4313885A (en) * 1980-05-21 1982-02-02 American Cyanamid Company Furfuryl thiourea compounds
JP2581556B2 (en) * 1986-05-06 1997-02-12 メレルダウファーマスーティカルズ インコーポレーテッド Novel dopamine beta-hydroxylase inhibitor
DE3703963A1 (en) * 1987-02-10 1988-08-18 Hoechst Ag PYRIDINE-2,4- AND 2,, 5-DICARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, USE THEREOF, AND MEDICINAL PRODUCTS BASED ON THESE COMPOUNDS

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Title
Вейнганд-Хильгетаг. Методы эксперимента в органический химии. М.: Хими , 1968, с. 377. *

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BE1003234A4 (en) 1992-02-04
AU607811B2 (en) 1991-03-14
DE3833603A1 (en) 1989-04-13
HU202516B (en) 1991-03-28
IL87874A0 (en) 1989-03-31
PL151572B1 (en) 1990-09-28
RU1792415C (en) 1993-01-30
KR890006612A (en) 1989-06-14
PL274988A1 (en) 1989-06-12
FR2621315A1 (en) 1989-04-07
PL151837B1 (en) 1990-10-31
PL277628A1 (en) 1989-08-21
IT1226862B (en) 1991-02-19
YU20490A (en) 1990-06-30
NL8802406A (en) 1989-05-01
DK549788A (en) 1989-04-03
YU182188A (en) 1990-06-30
HUT48879A (en) 1989-07-28
DK549788D0 (en) 1988-09-30
GB8823012D0 (en) 1988-11-09
YU20590A (en) 1990-06-30
ES2012122A6 (en) 1990-03-01
GB2210616A (en) 1989-06-14
GB2210616B (en) 1991-03-27
CH676849A5 (en) 1991-03-15
PL277629A1 (en) 1989-08-21
DD282914A5 (en) 1990-09-26
JPH01156975A (en) 1989-06-20
IT8822147A0 (en) 1988-09-30
AU2332988A (en) 1989-04-06
SU1739847A3 (en) 1992-06-07
PL151836B1 (en) 1990-10-31

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