CH619704A5 - Process for the preparation of novel optionally ring-substituted cycloalkano[b]thiophene ureas or thioureas and use thereof - Google Patents

Abstract

The novel compounds correspond to the formula: <IMAGE> in which X, Y, Z, R1, R2, R3 and U have the meanings given in Claim 1. They are prepared by reacting 1 mol equivalent of an appropriate compound I or II, in which the -NH-CX-NR2R3 radical is replaced by -NCX, with 1 to 1.5 mol equivalents of HNR2R3 or its acid addition salt. The reaction is carried out in a solvent at 0 to 100 DEG C. Compounds of the formula I, in which X denotes oxygen and Y, Z and R1 denote hydrogen and U denotes the carbonyl radical and R2 and R3 have the meanings given in Claim 4, are prepared from 4-amino-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene hydrochloride. This is reacted with phosgene at reflux temperature. Benzene, toluene, xylene or a mixture of isomeric xylenes is used in this reaction as a solvent, and one mol equivalent of the isocyanates obtained is reacted with 1 to 1.5 mol equivalents of HNR2R3. The reaction is carried out in an alkanol having 1 to 3 carbon atoms at 0 to 100 DEG C. The novel compounds of the formulae I and II are administered orally to warm-blooded animals to improve the extent of the feed effect and to increase the growth rate. A supplementary feed for increasing the growth rate of poultry, fur-bearing animals and agricultural productive animals contains 70 to 99% by weight of an edible carrier and, as the remainder, a novel compound of the formula I or II.

Description

The invention is further illustrated by the following examples.

619704

8th

example 1

Preparation of l-methoxy-3- (4,5,6,7-tetrahydrobenzo- [b] - thien-4-yl) urea

A mixture of 5 g of methoxyamine hydrochloride and 60 ml of methylene chloride is cooled to about 15 ° C. and 6 g of triethylamine in 15 ml of methylene chloride are added. After 20 minutes, 5.38 g of 4,5,6,7-tetrahydrobenzo- [b] -thien-4-yl isocyanate in 20 ml of methylene chloride are added in the course of 20 minutes at 15 to 20 ° C. After stirring for one hour, the mixture is filtered and the filtrate is washed with water and finally with an aqueous sodium bicarbonate solution. The solution is then dried and evaporated to give a white solid, which is recrystallized from an acetone / hexane mixture and 5.1 g of l-methoxy-3- (4,5,6,7-tetrahydrobenzo- [b] - thien-4-yl) urea with a melting point of 138.5 to 141 ° C.

Similarly, if instead of methoxyamine hydrochloride ethoxyamine hydrochloride or n-butoxyamine hydrochloride is used, l-ethoxy-3- (4,5,6,7 - tetrahydrobenzo- [b] -thien-4 -yl) urea or l-butoxy-3 - (4,5,6,7-tetrahydrobenzo- [b] thien-4-yl) urea.

Example 2

Preparation of I- (benzyloxy) -3- (4,5,6,7-tetrahydrobenzo - [b] thien-4-yl) urea

In the manner described in Example 1, O-benzyl hydroxylamine hydrochloride is reacted with 4,5,6,7-tetrahydrobenz - [b 1 -thien-4-yi-isocyanate, l - (benzyloxy) -3 - (4,5,6,7-tetrahydrobenzo- [b] thien-4-yl) urea is obtained, which is recrystallized from a mixture of 95% ethyl alcohol and methyl isobutyl ketone. The product melts at 96.5 to 99 ° C.

Example 3

Preparation of l-hydroxy-l-methyl-3- (4,5,6,7-tetrah.yd.ro-benzo [b] thien-4-yl) urea

In the manner described in Example 1, N-methyl-hydroxylamine hydrochloride is reacted with 4,5,6,7-tetrahydro-benzo [b] thien-4-yl isocyanate, 1-hydroxy- l - methyl-3- (4,5,6,7-tetrahydrobenzo- [b] -thien-4-yl) urea is obtained, which is recrystallized from an acetone / hexane / ether mixture, with crystals having a Receives melting point of 98 to 102 ° C.

Example 4

Preparation of l-methoxy-l-methyl-3- (4,5,6,7-tetrahydro-benzo [b] thien-4-yl) urea

In the manner described in Example 1, N, 0-dimethyl-hydroxylamine hydrochloride is reacted with 4,5,6,7-tetrahy-drobenzo- [b] -thien-4-yl isocyanate, with 1-methoxy - 1-Methyl l-3- (4,5,6,7-tetrahydrobenzo- [b] -thien-4-yl) urea, which is recrystallized from an acetone / hexane / ether mixture and a product with gives a melting point of 60 to 62.5 ° C.

Example 5

Preparation of l-phenethyl-3- (4,5,6,7-tetrahydrobenzo- [b] - thien-4-yl) urea

Under a nitrogen atmosphere, a mixture of 3.82 g of phenethylamine and 100 ml of diethyl ether is reacted with 5.38 g of 4,5,6,7-tetrahydrobenzo- [b] -thien-4-yl isocyanate in 25 ml of diethyl ether, where the isocyanate is added dropwise in the ethyl ether. After stirring for one hour at room temperature, the mixture is filtered and washed with ether, 7.9 g of l-phenethyl-3- (4,5,6,7-tetrahydrobenzo- [b] thien-4-yl) -Urea with a melting point of 163 to 166 ° C.

Similarly, if methylamine, ethylamine, isopropylamine, n-hexylamine or cyclohexylamine are reacted with the isocyanate mentioned above, 1-methyl-, 1-ethylI, 1-isopropyl-, 1-hexyl- or 1-hexyl- or l-Cyclohexyl-3- (4,5,6,7 - tetrahydrobenzo- [b] thien-4-yl) urea.

Example 6

Preparation of 1, l-dimethyl-3- (4, .5,6,7-tetrahydrobenzo- [bJ - thien-4-yl) urea

A solution of 6.27 g of 4,5,6,7-tetra-hydrobenzo [b] thien-4-yl isocyanate in 200 ml of diethyl ether is charged with gaseous dimethylamine, which is fed in through a capillary tube. After a gas introduction time of 0.5 hours, the gas supply is interrupted and the mixture is evaporated to dryness, a solid residue being obtained. This residue is recrystallized from an acetone / hexane / ether mixture and gives l, l-dimethyl-3- (4,5,6,7 - tetrahydrobenzo- [b] -thien-4-yl) urea, which at 117 to 120 ° C melts.

Example 7

Preparation of I-benzyl-3- (4,5,6,7-tetrahydrobenzo- [b] - thien-4-yl) urea

In the manner described in Example 1, but with the difference that diethyl ether is used instead of methylene chloride, reaction of benzylamine with 4,5,6,7-tetrahydrobenzo- [b] -thien-4-yl- isocyanate l-benzyl-3- (4,5,6,7-tetrahydrobenzo- [b] thien-4-yl) urea. The product melts at 211 to 214 ° C.

Example 8

Preparation of l-hydroxy-3- (4,5,6,7-tetrahydrobenzo- [b] thien-4-yl) urea

The above compound is prepared in the manner given in Example 1 by reacting 4,5,6,7-tetrahydrobenzo [b] thien-4-y! Isocyanate with hydroxylamine hydrochloride in the presence of triethylamine. The product melts at 158.5 to 160.5 ° C.

Example 9

Preparation of N- (4,5,6,7-tetrahydrobenzo- [b] -thien-4-yl) -4-morpholine carboxamide

If one proceeds in the manner given in Example 1, but uses diethyl ether instead of methylene chloride and 4,5,6,7-tetrahydrobenzo- [b] -thien-4-yI-isocyanate is reacted with morpholine, N- (4 , 5,6,7-tetrahydro-benzo- [b] -thien-4-yl) -4-morpholine carboxamide, which melts at 152 to 154 ° C.

Preparation of 4,5,6,7-tetrahydrobenzo [b] thien-4-yl isocyanate

47.6 g of 4,5,6,7-tetrahydrobenzo- [b] -thiophene-4-amine hydrochloride are stirred in 150 ml of water and 350 ml of a 10% sodium hydroxide solution are added. The mixture is shaken and extracted twice with benzene. The extract is dried and evaporated to dryness to give the amine which is kept under nitrogen. Then the amine is added dropwise under a nitrogen atmosphere at 20 ° C. to 866 ml of a 12.5% solution of phosgene in benzene. After stirring for one hour

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

9

619704

At room temperature, the mixture is gradually heated to 60 ° C. and left at this temperature for 7 hours. The mixture is then cooled to room temperature, evaporated to dryness and a residue is obtained which, after distillation, contains 22.4 g of 4,5,6,7-tetrahydrobenzo- [b] thien-4-yl isocyanate with a boiling point from 98 to 101 ° C / 0.6 Torr.

Preparation of 4,5,6,7-tetrahydrobenzo [b] thien-4-yl isothiocyanate

47.5 g of 4,5,6,7-tetrahydrobenzo- [b] -thiophene-4-amine hydrochloride are stirred in a methyl chloride / water mixture and little by little a 5% sodium hydroxide solution is added until a pH of about 10 is reached. The methylene chloride layer is then separated off and the aqueous layer is extracted with methylene chloride. The organic layers are combined, dried over magnesium sulfate and evaporated to dryness to give the oily amine. The amine is stirred under a nitrogen atmosphere in 500 ml of ethyl acetate and 25.4 g of triethylamine are added. After about 15 minutes, 20.9 g of carbon disulfide are added, giving a voluminous precipitate. A further 200 ml of ethyl acetate are added and the solid is pulverized with a spatula. After stirring for 1 hour, 51.5 g of dicyclohexylcarbodiimide are added and the mixture is stirred overnight. The mixture is then heated to about 50 ° C. for 2 hours and then cooled. The solid is filtered off and washed with ethyl acetate. The filtrate is evaporated to give a mixture of a solid and a predominant amount of oil. The solid is filtered off after the addition of ether. The ether filtrate is evaporated to dryness and gives the crude isothiocyanate, which is purified by chromatography on a dry column filled with silica gel.

ether / methylene chloride mixture (65/35, volume / volume) used.

Example 10

5 Preparation of N- (4,5,6,7-tetrahydrobenzo- [b] -thien-4-yl) -4-piperidine thiocarboxamide

50 ml of tetrahydrofuran and 5.85 g of 4,5,6,7-tetrahydrobenzo- [bj-thien-4-yl isothiocyanate are stirred in and 2.81 g of io piperidine are added. An exothermic reaction is observed, causing the temperature to rise to about 40 to 50 ° C. After 2% hours, the mixture is refluxed for 3% hours. After stirring overnight, the mixture is evaporated to dryness and a sticky yellow-brown solid is obtained. This material is mixed with ether and an almost white, insoluble product is obtained. The crude product obtained in an amount of 5.25 g melts at 102 to 104 ° C.

20 Example 11

The compounds listed in Table I below are obtained using the procedures outlined in Examples 1-10.

25th

30th

ivj «x! II - c-

N

y

* 2

* 3

619704

10th

table i

Ri '

R,

Reaction solvent

Melting point ° C

-ch3

h h

s

-ch3

h h

O

-ch3

h h

O

-ch3

h h

o h

-ch3

h s

H

-ch3

h o

H

-ch3

h o

h h

h o

h h

h o

h h

h o

h h

h o

h h

h s

h h

h o

h h

h o

h h

h o

h h

h o

h h

h s

h h

h o

h h

h s

h h

h s

h h

h s

h h

h s

h h

h s

h h

h s

h h

h o

h h

H

0

h h

H

0

h h h h h h h h h h

h h

h h

h h h h h

h h h

ethyl

Ethyl sec-butyl n-hexyl

Ethyl sec-butyl n-hexyl

-chj, CH = ch2

-ch2co2c2h5

-ch

- (ch,), - (ch2) 6-

-n-qhç,

-ch2-ch2- {o)

-ch2ch2-oh - (CH2) b-

-n-CsH,

D> -

-ch2ch = ch2

-ch2- <g) -ç

Vch2

-ch.

r (ôy ~ -

Cl

-ch2-c = ch

~ <Q> -och,

ch., - ch = ch, -ch2ch = ch "

thf thf thf thf thf thf thf thf thf

ether

ether

ether

ether

Ether ether ether thf

Ether thf thf thf thf thf thf ether ch2c12 ether

118-121

209-211

182.5-185

118-120

120.5-123.5

197-198

148-150

175-176

147-149

219-221

109-111

122-125 279-283

137-139 128-130 94-96

oil

140-154

103-106 66-69

125-129

101-103

123-127

137-144 188-189 223-226 69-72

11

TABLE I (continued)

619704

Y

Z

ri '

X

r »

r2

Reaction solvent

Melting point ° C

h h

H

S

-ch3

-och3

ch2c12

74-77

h h

H

0

H

-oc2h5

ch2ci2

90-94

h h

h o

H

-och2-ch = ch2

ch2ci2

70-73

h h

H

0

Cyclohexyl

-oh ch2ci2

180-181

H

H

H

O

H

-O-n-C0H1B

ether

54-57

H

H

H

O

-ch (ch3) 2

-oh ch2c12

113-116

H

H

H

0

-ch2-ch =

ch2 -CHz-ch = ch2

ether

69-72

-ch3

H

H

o h

-c, h5

thf

209-211

-ch3

H

H

O

H

-2-c4h9

thf

181-184

-ch3

H

H

s

H

-c2h5

thf

116-118.5

-ch3

H

H

O

H

H

h2o

234.5-236.5

-cha h

H

O

H

-n-C6Hj3

thf

111-121

H

-ch3

H

o <

H

H

h2o

225-227

H

-ch3

h s

H

-c2h0

thf

121-125

H

-ch3

H

O

H

-2-c4H <i thf

197-198

H

-ch3

H

0

H

-n-CßHM

thf

148-150

-ch3

-ch3

H

s

H

-C2H5

thf

153-157

-ch3

-ch3

H

O

H

-2-c4h0

thf

181-183.5

-ch3

-ch3

H

O

H

-®-Cl thf

203-209

-ch3

-cha

H

O

H

H

h2o

233-237

H

H

H

O

- (ch2) 2-n- (ch2) 2-

1

ether

110-113

1

co2c2h5

H

H

H

O

H

-n-QH ;,

ch2c12

159-161

H

H

H

O

H

-chocn thf

179-181

H

H

H

0

H

-ch2-ch2-och3

ether

142-144

H

H

H

O

H

-ch2ch2-s-ch3

ether

128-130

H

H

H

s

- (cH2) 2 ^ ^ (ch2} 2 "

.c

ether

235-238

> -c6H5

HN '

H

H

H

O

H

ri

ether

183-185

H

H

H

O

-ch8

-ch2-c = ch

ether

105-108

H

H

H

0

H

-NH-c02chs

ether

183-186

H

H

H

0

H

ch, ci2

171-172

619704

12

TABLE I (continued)

Y Z

ri "

x r3

r2

Reaction solvent

Melting point ° c h

h h

0

H

- <Ô) -C1

ch2c12

234-237

h h

h o

H

-CH2-Ç1

ether

195-197

h h

H

0

-ch2-c = ch

-ch2-c = ch

ether

118-120

h h

H

0

H

"CH2" {2) Î

ch2cl2

201-204

h h

H

0

H

-ch0- / 0S

ch2ci2

192-195

H

H

H

H

H

H

H

h h

h h

h h

H

H

H

H

H

H

H

H

n-

O

H

-ch.

r®-

0CH-

CH2CL

O

- (ch2) 2-n- (ch2) 2-

CHoCL

"O

O

o o

o o

H

H

H

H

H

îci-i3

(oy $ o

- <o> -c

CH "

3rd

-Cl

• Cl-

. - ^) - 0CH3: och3

~ <ô> oc2h5

CHoCL

CH2C12

CH2Cl2

CH, Clo

CH, CL

188-191

h h

h o

H

-ch ^ -cf3

ch2ci2

208-211

h h

h o

-ch3

-CH2cbh5

ch2ci2

68-70

h h

h o

H

-t-butyl ch2ci2

187-192

h h

h o

H

-C32- (Ô) -C1 "

ch2cl

216-217

h h

h o

H

-ch2ch (och3) 2

ch2cl

125-128

h h

h o

H

<1

CH2Ck

175-178

h h

h o

-CH2cch5

-ch2c = ch ch2c12

112-115

129-133

231-234

241-242.5

242-245

200-204

221-225

13

619704

TABLE I (continued)

r, '

R,

r,

Reaction melting point solvent ° C

h h h h

h h h h h h h h

O

O O

O

h o

H

-CH, CRH5

h h

h o -0

-0-oc4h3

-OH

- <2> (

-o / cà

-oh chocl chocl ch, cl

183-186

CH2C12 121-123

CH2C12 143-146

223-226

CH2C12 159-161

131-133

Example 12

Preparation of 4,5,6,7-tetrahydro-7-oxobenzo [bJ-thien - 4-yl isocyanate and urea

The 4,5,6,7-tetrahydro-7-oxobenzo- [b] -thiophene-4-amine hydrochloride is converted into 4,5,6,7-tetrahydro-7-oxobenzo- [b ] -thien-4-yl isocyanate by heating a mixture of toluene and the hydrochloride to reflux and introducing phosgene. After the mixture has become less cloudy, it is cooled and filtered. Evaporation of the filtrate gives the crude 4,5,6,7-tetrahydro-7-oxobenzo [b] thien-4-yl isocyanate, the IR spectrum of which shows a maximum at 2250 cm-1.

Adding a solution of ammonia in methanol to this isocyanate gives 4,5,6,7-tetrahydro-oxo-benzo [b] thien-4-yl urea.

Example 13

The compounds indicated below are obtained by reacting 4,5,6,7-tetrahydro-7-oxobenzo [b] thien-4-yl isocyanate with the corresponding amines in inert solvents by the method given in Example 11 .

S / r3

nh-c-n

NR->

30th

35

45

50

Amines

R3

Product R2

Mp (° c)

nh2-och, 3

H

-och3

185-188.5

nh2-oh h

-Oh

-

ch, nh-oh

-ch3

-Oh

163-165.5

chanh-ocha

-CHj

-och3

126-129

ch2 = ch-ch2-nh2

H

-ch, -ch = ch ;,

171-174

CH = c-cho-nh2

H

-ch2-c = ch

197-199

(ch3) 2nh

-cha

-cha.

195-197

c0h5ch2nh2

H

-CHo-cuh5

-

c2h5nh2

H

-c2h5

188-190

n-C4HnNH2

H

-n-C4H9

-

O

II

O

II

II

ch3c-nh2

H

II

-c-ch3

-

60

(ö) -ch2-nh2 h -ch2

t [o! Lcn2-NH2 H ~

ch2 -ö

65

ch ,,

-CH-NH ..

H

CH,

-CH (CHB) 2

198-200

619704

14

Trial 1

The following studies serve to evaluate the growth promoting properties of 4,5,6,7-tetrahydro-benzo- [b] -thien-4-yl-ureas against chicks.

In these studies, chicks 1 day old are used, which are placed in heated cages and supplied with food and water ad libitum. In each examination, 5 male and 5 female chicks are used per cage and 3 cages per treatment. The treatment consists of a basic feed, which is mixed with 1, 3 or 9 ppm of the compound to be examined. The chicks are weighed at the beginning and at the end of the examination. Feed consumption is determined during the study period, which is 13 days from the start of the day the chicks are 1 day old. The composition of the basic feed used and the results obtained are given below.

Vitamin premix for 1 ton

Basic kitchen food ground yellow corn Soy flour (49%) Menhaden fish meal (60%) Corn gluten meal (60%) Dehydrated alfalfa meal (17%) Stabilized fat Dicalcium phosphate ground limestone Sodium chloride Tra-Min No. 3 * Vitamin premix * *

53.45% 28.0 5.0 5.0 2.0 4.0 1.2 0.5 0.3 0.05 0.5

100.00

10th

15

20th

25th

30th

35

40

D, L-methionine

453.6 g

BHT

113.6

Vitamin A (30,000 units / g)

100.0

Vitamin D; i (200000 units / g)

5.0

Vitamin E (44093 units / kg)

45.5.

Riboflavin

4.0

Niacinamide

25.0

Calcium pantothenate

8.0

Vitamin K (menadione)

1.0

Folic acid (parvo [10%])

13.0

Choline chloride (50%)

908.0

Vitamin B12 (Proferm, 44 mg / kg)

227.0

Corn oil

50.0

finely ground corn

2582.4 4536.0

* Tra-Min No. 3

Result in 0.454 kg / t

Manganese 12.50%

62.5 ppm

Iron 6.00%

30.0

Zinc 5.00%

25.0

Copper 0.65%

3.25

Iodine 0.35%

1.75

Cobalt 0.25%

1.25

Calcium 15.30% min.

18.35% max.

Chick test mean chick weight gain after 13 days (g)

treatment

Dose (ppm)

1928

1929

Experiment 1900 1 931

Average percentage improvement

1.

control

-

189

175

180

188

183

-

2nd

4,5,6,7-tetrahydro-

1

181

193

182

200

189

3.3

'

3rd

benzo- [b] thien-4-

3rd

199

186

197

198

195

6.6

4th

-yl urea

9

190

198

191

191

193

5.5

mean weight gain in kg / kg of feed during the 13 days

1.

control

-

1.54

1.52

1.46

1.48

1.50

-

2nd

4,5,6,7-tetrahydro-

1

1.48

1.45

1.49

1.44

1.46

2.7

3rd

benzo- [b] thien-4-

3rd

1.47

1.40

1.44

1.40

1.43

4.7

4th

. -yl urea

9

1.45

1.45

1.46

1.40

1.44

4.0

15

619704

Trial 2

Growth promotion and feed efficiency ratings in sheep that have received an implant containing the compound to be investigated

In order to investigate the effect of a 4,5,6,7-tetrahydrobenzo- [b] -thien-4-yI-urea compound on sheep, Wether lambs are statistically divided into groups of 6 in enclosures. The sheep are weighed and provided with food and water ad libitum. The feed is weighed daily and the unused feed from the previous day is collected and weighed. The test lambs are provided with the same non-drug-containing feed as the control animals, but are given one or more subcutaneous implants in the base of the ears, which contain the compound to be examined. The formulation of the implant used is given below. After the six-week treatment period, the lambs are weighed again and the total feed consumed is calculated.

In these studies, six groups of six lambs are used per treatment, of which approximately 11 to .105 mg of the investigating compound is administered to each animal.

Table II shows the mean weight gains over the six weeks, while Table III shows the weight gains in kg / kg of feed. From these values it can be seen that the lambs who have been implanted with 11 mg or 99 mg of the compound to be examined show a weight gain of about 10% compared to the untreated control animals 6 weeks after the implantation. The feed utilization during this period compared to the untreated control animals is also improved by about 5%.

Lamb feed

«/»

ground corn cobs

15.0

ground yellow corn

48.0

Soy flour (49%)

10.0

dehydrated alfalfa flour

15.0

molasses

10.0

iodized salt

0.5

Dicalcium phosphate

1.0

Premix

0.5

100.0

Premix for 1 ton g

Tra-Min No. 3 «1 '

454

Vitamin A (30,000 units / g)

133

Vitamin D3 (200,000 units / g)

5

Corn oil

100

ground corn

3848

4540

(1) Tra-Min No. 3 =

V #

calcium

21.00

manganese

12.50

iron

6.00

zinc

5.00

copper

0.65

iodine

0.35

cobalt

0.25

Pellet implant

4,5,6,7-tetrahydrobenzo- [b] thien-4-yl urea

11.0 mg

Glyceryl 12-hydroxystearate

10.50 mg

Magnesium stearate

0.50 mg

22.00 mg

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

619704

16

TABLE II

mean weight gain over 6 weeks, kg / lamb

treatment

Number of drug implants (a)

1

Repetitions 3 4 5

medium

control

0

8.50

8.70

9.93

6.50

7.03

6.75

7.90

4,5,6,7-tetrahydrobenzo

1

11.25

9.32

9.20

8.63

8.05

6.68

8.86

- [b] -thien-4-yl urea

9

10.83

9.60

8.75

7.20

8.53

7.20

8.69

(a) Average weight: 22 mg each

Composition: 50% active ingredient 4- 50% carrier material

TABLE III

average weight gain in kg / kg feed per enclosure

treatment

Number of drug implants (a)

1

2nd

Repetitions 3 4 5

6

medium

control

0

7.88

6.77

7.41

8.82

9.18

8.16

8.04

4,5,6,7-tetrahydro-

1

6.63

6.58

7.41

8.21

8.05

8.49

7.57

- [b] -thien-4-yl urea

9

6.51

6.75

7.80

8.38

7.56

7.97

7.49

(a) Average weight: 22 mg each

Composition: 50% active ingredient + 50% carrier material

Trial 3

Investigation of the growth regulating effect on mice

The female mice (CFI) are obtained from the car worth farm at 6 weeks of age. They are caged in groups of 10 animals that are in air-conditioned rooms [22.2 to 24.4 ° C (72 to 76 ° F)] that are automatically lit for 14 hours and kept dark for 10 hours. The basic diet used in these studies is a Purina Laboratory Chow (Purina Laboratory Chow), the composition given below, which is given ad libitum, as well as water, which is also added ad libitum.

Thirteen days after arrival, the mice are weighed in groups of 10 animals and statistically selected for various treatments. The concentration of the various compounds in the feed is given in the following tables. The mice are weighed again 12 days later and the experiment is ended. At least 3 cages with untreated control mice (30 mice) are used in each examination. The test results are given in the following Table IV, which shows the values for the percentage weight gain compared to the control animals.

The following is a description of the feed in which the growth promoting compounds are added.

Lining

Guaranteed analytical values:

Raw protein, not less than 23.0%

raw fat, not less than 4.5%

raw fibers, not more than 6.0%

Components:

Meat and bone meal, dried skimmed milk, wheat germ meal, fish meal, animal liver meal, dried leached beet pulp, ground extruded maize, 35 oatmeal meal, soybean meal, dehydrated alfalfa meal, cane sugar molasses, animal fat then preserved with butylated hydroxyanisole, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium choline additive, potassium chinoid additive, potassium choline additive, potassium choline, additive, animal fat, calcium chloride, folium chloride, added to cholesterol; , Riboflavin additive, dried brewer's yeast, thiamine, niacin, vitamin A additive, D-acti-40 fourth plant sterol, vitamin E additive, calcium carbonate, dicalcium phosphate, iodized salt, iron (III) ammonium citrate, iron oxide, manganese (II) -oxide, cobalt carbonate, copper oxide and zinc oxide.

Ash, no more than

9.0%

17th

619704

TABLE III

Effect of 4,5,6,7-tetrahydrobenzo [b] thien-4-yl ureas as animal growth promoting agents. The values determined in mice are given as a percentage weight gain compared to the control animals.

W / r2

n-c-n

^ 3

Dose in ppm in the feed

X

Y

Z

Ri '

ro

R *

Weight gain compared to control animals in%

50

0

h h

h h

H

50.1

400

o h

h h

h h

119.6

50

0

h h

h h

-ch3,

61.8

200

o h

h h

h h

134.2

50

o h

h h

H

-CÄ

40.3

200

o h

h h

H

-c2h5

87.6

400

0

h h

H

-Oh

-ch3,

49.6

400

o h

h h

-ocha h

68.6

400

0

h h

H

■ ch »

-ch8

55.1

400

0

h h

H

-oh h

102.0

400

0

h h

H

-Oh

-ch,

106.8

400

O

H

H

H

H

-ch (ch3) 2

88.0

400

o h

h h

-CH, CHHg>

H

72.3

400

o h

H

H

-ch2- <Ô>

H

32.4

400

s

H

H

h h

-c2h5

54.6

400

O

Br

H

H

H

H

76.3

400

O

Cl h

h h

H

4.8

400

o h

h h

-n-C0h13

H

14.5

400

0

-cha h

h h

H

7.6

400

s h

h h

-ch3,

H

88.5

400

o h

h h

H

(left-turning isomer)

H

122.5

400

o h

h h

-ch2ch = ch2

H

48.4

400

o h

H

H

H

-ch3

134

400

O

H

H

H

H

-c2h5

87.6

400

o h

H

H

H

-CH (ch3) ü

88

400

O

H

H

h n-hexyl h

14.5

400

O

H

H

H

H

-CH2cuh5

32.4

400

O

H

H

H

H

-ch2CH, cch5

72.3

619704

18th

TABLE III (continued)

Dose in ppm in the feed

X

Y

Z

Ri '

R2

Weight gain compared to control animals in%

400

S

h h

h h

-c2h5

54.6

400

0

h h

H

-ch,

-ch3

55.1

400

0

h h

H

-ch2-ch2-o-ch2-ch2-

9.9

400

0

h h

h h

-ch2-ch = ch ..

48.4

400

s h

h h

H

1

-ch3

88

400

0

h h

h itju h

43

400

0

h h

H

-ch2-ch2-

ch2-ch2-

18th

400

0

h h

H

-n-butyl

-n-butyl

6

400

s h

h h

h h

11

400

s h

h h

H

15

400

s

H

H

H

H

-n-butyl

75

400

0

H

H

H

-ch2-ch2-oh

H

3rd

400

s

H

H

H

-n-c8H17

H

16

400

s

H

H

H

- ^

H

32

400

s

H

H

H

H

-ch, -ch = ch

60

400

0

H

H

H

H

-ch2-c = ch

82

Dose in ppm v v 7 w 'w p

in feed i s 2 over control animals in%

200

o h

h h

-n-butyl h

25th

400

o h

h h

H

-ch2cn

12

400

0

h h

H

-CH2CH2 ^ yCH

2 "CH2-

14

0 - • = f v

C6K5

HN '

cv- \

400

0

h h

h h

Kp) -01

18th

400

0

h h

H

-ch3,

\ /

-ch2c = ch

29

400

0

h h

h h

-nh-co2ch3

18th

400

0

h h

h h

- ^ 5) - "och3

78

400

0

h h

H

-ch2-ch = ch2

-ch2-ch = ch.

4.0

400

0

h h

h h

-ch2-Ç

39

400

0

h h

H

-ch2-c = ch

-cha-c = ch

27th

in the ]

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

19th

619704

TABLE III (continued)

X

Y

Z

Ri o

H

H

H

0

H

H

H

O

H

H

H

O

H

H

H

O

H

H

H

O

H

H

H

O

H

H

H

O

H

H

H

O

H

H

H

O

H

H

H

O

H

H

H

O

II

H

H

0

H

H

H

O

H

H

H

n> p -d weight gain against

13 2 over control animals in%

h "ch2- ^ j 48

H "TV-V 21

16

-r @ -Cl

-CH2 - @ - OCH3

-CHff) -. -CH £ <£> - •

clth,

-ch2- <o) -ci -tCH2) 3- (o)

0-

o h h h o h h h h o h h h h

- <ö) -oc2h5

O

H

H

H

H

- \ 2 / ~ 0-n

O

H

H

H

H

-OH

O

H

H

H

H

-OCH,

41

46

- (ch2) 2-n- (ch2) 2-3

-ch2cf3 19th

1

-chx0h5 14

-ch2-ch (och3) 2 22

31

-ch2-c = ch 30

- CCH2) 2 - N— (ch2> 2 "" 24 l <0v0ch3

- @ - U02 9

o h h h h

9

102.9 68.5

in the. I.

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

400

20th

TABLE III (continued)

Weight gain compared to control animals in%

o h

h h

-ch3

-Oh

49.6

o h

h h

-ch3

-0ch3

106.8

s h

h h

-ch3

-OCH3.

66

0

h h

h h

-oc2h3

61

o h

h h

H

-o-ch, -ch = ch2

5

0

h h

h rO

-Oh

19th

o h

h h

H

-o-n-qjhjg,

29

o h

h h

-CH (ch3) o

-Oh

32

o h

h h

-ctlca

-Oh

12

O

Br h

h h

H

76.3

O

Cl h

h h

H

4.8

O

-ch »

h h

h h

7.6

O

-cha h

H

-2-butyl h

2nd

o h

-ch3

H

H

H

26

0

H

-ch3

H

H

-n-hexyl

21st

O

-chs

-ch3

H

-2-butyl

H

3rd

O

-ch3

-ch3

H

H

H

0

21st

619704

TABLE IV

Efficacy of cycloalkano- [b] thienylurea compounds as animal growth promoters. The test results determined on mice are given as a percentage weight gain compared to the control animals.

Dose in ppm

in the lining compound

Weight gain compared to the control animals in%

400

nh-co-nh-r.

ch3 ch3

-CH.,

15

400

h-co-nh-r.

400 400

400

400 50 * 100 * 200 * 400 *

nh-conh-r.

1jih-c0-nh-r o nh-co-nh-r2

-ch3.

39

H

110

H

99

-ch3

41

-c2h5

40

H

54

-ch2-o-chs

10th

H

134

H

112

H

108

H

117

H

105

'5 cages of 10 mice were examined per dose.

v

Claims (9)

619704 2nd 1. A process for the production of new, optionally ring-substituted cycloalkano - [b] -thiophene-ureas or -thioureas of the formula or in which X is oxygen or sulfur, Y is hydrogen, C,. ., - means alkyl or halogen, Z means hydrogen or Cji_4-alkyl, Rj means hydrogen or C ^ -alkyl, R2 means hydrogen, C ^^ - alkyl, jCj ^ -cycloalky !, allyl, 2-propynyl, hydroxyl, C, _ "- Alkoxy, allyloxy, methallyloxy, 2-butenyloxy, methoxymethyl, phenoxy, -CH2-CH2-OH, -CH2-CH20 - CH3, -CH2-CH2-S-CH3, -CH2-CH (OR1) "-CH2-CF3, -CH2-CN, -CH2-C02Rj, -NH-CO2R1; 20th 25th o o II II -C-Rj, -C-CC13, c ch2-3 0 0 ii c-nh-3 ch2-, h-g-nh-ch2- o ~ ch2-3 ch2-ch2- or cch2) n- means and R3 is hydrogen, C, _4-alkyl, C3.0-cycloalkyl, allyl, 2-propynyl or azino, 4- (4-methoxyphenyl) piperazino, 1,2,3,4-tetrahydroquinolino or isoquinolino or a radical of the formula where n is 0, 1 or 2 and Q if n is 0 stands, hydrogen, 3,4-methylenedioxy, 2-, 3- or 4-methoxy, 4-ethoxy, 4-chloro, 4-butoxy, 4-methylthio, 2,4-dimethyl, 2,4-dimethoxy, 2, 4-dichloro, 4-nitro or 2-methyl-4-bromo, if n is 1, is hydrogen, 4-chloro, 4-methoxy or 3,4-methylenedioxy and, if n is 2, is hydrogen , or R2 and R3 together with the nitrogen atom to which they are attached, morpholino, piperidino, pyrrolidino, 4-phenylpiperazino, 4-carbäthoxypiper- 55 60 or R2 is hydrogen and R3 is benzyloxy, 65 and U is a divalent radical of the formula H R4 ^ C = 0, or OH Rr, 3rd 619704 means, wherein R4 and R5, which are the same or different, represent hydrogen or Cj_4-alkyl, characterized in that one has a molar equivalent of a compound of the formula CX respectively (Iii) (IV) in a solvent at a temperature of 0 to 100 ° C rature of 0 to 100 ° C with 1 to 1.5 molar equivalents of one with 1 to 1.5 molar equivalents of a compound of the formula compound of the formula H-N; R2 r, 20th H-N; R2 ' R * or an acid addition salt thereof. 2. The method according to claim 1, characterized in that the amine is used in the form of an acid addition salt and the reaction is carried out in the presence of an acid acceptor. 3. The method according to claim 1 or 2 for the preparation of the cis or trans isomers, if U is -CHOH-, or the optical isomers of the compounds of the formula I or II. 4. Process for the preparation of new 7-oxo-4,5,6,7-tetrahydrobenzo- [b] -thien-4-yl-ureas of the formula 25 implemented and the product isolated. 5. A method for improving the feed efficiency and increasing the growth rate of warm-blooded animals, characterized in that the animals an effective amount of a new compound of 30 formula I or II administered orally. 6. The method according to claim 5, characterized in that the compound in the feed is administered in an amount of 0.0001 to 0.08% by weight, based on the feed. 7. The method according to claim 5 or 6, characterized in 35 shows that an isomeric or trans isomer if U is -CHOH, or an optical isomer of the new compound of formula I or II used. 8. Supplementary feed to increase the growth rate of poultry, fur animals and agricultural 40 farm animals, characterized in that it contains 70 to 99% by weight of an edible carrier material and 1 to 30% by weight of a new compound of the formula I or II. 9. co-feed according to claim 8, characterized in that it is an ice or trans isomer, if U for 45 -CHOH, or contains an optical isomer of the new compound of formula I or II. wherein R2 'is hydrogen, C 1-6 alkyl, allyl, C1_4 alkoxy, 50 2-propynyl, methoxymethyl or hydroxyl and R: t 'What- From US Pat. No. 3,776,924 are compounds with serstoff or C1.d-alkyl means, characterized, known herbicidal activity, which has the formula that the Compound of the formula where W is ^; CH2, ^ CH-Q, -S-, ^ S (0) n in benzene, toluene, xylene or a mixture of isomers (where n is from zero to 2) or ^; NR stands, Z for O Xylenes as aromatic solvent with phosgene at or S, x is from zero to 6 and R, R1 and Q are water Reflux temperature, the 4,5,6,7-tetra-65 formed or different substituents mean. hydro-7-oxobenzo- [b] -thien-4-yl isocyanate wins, 1 mol- The invention relates to a process for the preparation of equivalent of the isocyanate obtained in an alkanol with 1 new optionally ring-substituted cycloalkano- [b] - up to 3 carbon atoms as a solvent in a Tempe-thiophene urea or thiourea of the formula 619704 4th wherein X is oxygen or sulfur, Y is hydrogen, C 1-4 alkyl or halogen, Z is hydrogen or C 1-4 alkyl, Rt is hydrogen or C1.4 alkyl, R; Hydrogen, CV ^ -alkyl, Ca_B-cycloalkyI, allyl, 2-propynyl, hydroxyl, Qu-alkoxy, allyloxy, methallyloxy, 2-butenyloxy, methoxymethyl, phenoxy, CH2-CH2-OH, -CH2-CH ,, 0-CH3, -CH2-CH2-S-CH3, -CH2-CH (ORx) 2, -CH2-CF3, -CH ..- CN, -CH2-C02R „-NH-COaRj, 20th o o -C-Ri, -C-CC13, \, ch2-, e o 0 c-nh-, c ■ CHjj-, L k-c-nh-ch -, - ch2-, SN ^ • CH2-CH2- or is and R3 is hydrogen, Ci ralkyl, C3_G-cycloalkyl, allyl, 2-propynyl or, where n is 0, 1 or 2 and Q, if n is 0, is hydrogen, 3,4-methylenedioxy, 2-, 3- or 4-methoxy, 4-ethoxy, 4-chloro, 4-butoxy, 4-methylthio, 2,4-dimethyl, 2,4-dimethoxy, 2,4-dichloro, 4-nitro or 2-methyl-4 -bromine, if n is the number 1, represents hydrogen, 4-chloro, 4-methoxy or 3,4-methylenedioxy and, if n is 2, is hydrogen, or R2 and R3 together with the nitrogen atom that they are bound, morpholino, piperidino, pyrrolidino, 4-phenylipiperazino, 4-cai bäthoxy-piperazino, 4- (4-methoxyphenyl) -piperazino, 1,2,3,4-tetra-hydroquinolino or isoquinolino or a residue of the formula 60 is or R2 is hydrogen and R3 is benzyloxy and U is a divalent radical of the formula H R4 ^ C = 0, or os OH Ra, where R4 and R5, which are the same or different, represent hydrogen or Cj_4-alkyl. You can also get one 5 619704 ice or trans isomer if U is -CHOH- or produce an optical isomer of the compound of formula I or II. The process according to the invention is characterized in that one molar equivalent of a compound of the formula 5 (III) in a solvent at a temperature of 0 to 100 ° C with 1 to 1.5 molar equivalents of a compound of the formula R2 H-Nd ' r3 or an acid addition salt thereof. Preferred compounds obtainable according to the invention correspond to the formulas I and II, in which Y, Z and R denote hydrogen, U represents -CH2- and R2 and R: l together with the nitrogen atom to which they are attached for morpholino, pyrrolidino, 4-phenylpiperazino, 4- (4-methoxyphenyl) piperazino, 1,2,3,4-tetrahydroquinolino or a radical of the formula (IV) where Q, if n is 0, 4-chloro, 3,4-methylenedioxy, 2-, 30 3- or 4-methoxy, 4-ethoxy, 4-butoxy, 4-methylthio, 2,4-dimethyl, 2, 4-dichloro, 4-nitro or 2-methyl-4-bromo means. if n is 1, represents hydrogen or 4-methoxy and, if n stands for 2, is only hydrogen, and the symbol R :, hydrogen, Cl t-alkyl, C3 _ ,, - cycloalkyl, 35 allyl, 2-propynyl or <2> 40 0 means. The compounds of the formulas I and II obtainable according to the invention can be in the form of the cis and trans isomers and in the form of racemic mixtures or the optically active isomers. According to the definition of U, the compounds obtainable according to the invention are further divided into three separate subclasses, i.e. Compounds in which U is or are optically active isomers of these compounds. In the case of further preferred compounds obtainable according to the invention, the symbol R2 represents hydrogen, Qg-Al-ky], C3_c-cycloalkyl, allyl, 2-propynyl, hydroxyl, C 1 -, -alk-oxy, allyloxy, methallyloxy, 2-butenyloxy, Methoxymethyl, phenoxy, -CH2-CH2-OH, -CH2CH (OR,) 2, -CH2-CF3, -CH2-CN, -NH-COoRJ, O O II II -C-Rl -C-CCI3, u- ■ ch0-, c ch2-, 50 H Ri ^; C = 0, ^ Cd or OH R5 stands. Preference is given to the compounds of the formulas I and 55 II, in which U is -CH2-, where in formula I Y is hydrogen or bromine and Z is hydrogen and in formula II Y and Z are both hydrogen. In particularly preferred compounds of this type, R2 represents hydrogen, C 1-4 alkyl, C 3 -C 6 -cycloalkyl, 60 allyl, 2-propynyl, hydroxyl, C 1-4 alkoxy, methoxymethyl, phenoxy, 4-methoxyphenyl or 65 c 0 ' -gh, and the symbol Ra means hydrogen, Ci_4-alkyl, C3 "g-cycloalkyl, allyl, 2-propynyl or 619704 6 Further particularly preferred compounds correspond to the formula in which R2 is hydrogen, C1-4-alkyl, allyl, Cx_4-alkoxy, 2-propynyl, methoxymethyl or hydroxyl and R3 is hydrogen or C1_4-alkyl. Very particularly preferred compounds correspond to the formula x .rp I! £ " nh-c-n l \ r 'S there) uQ wherein R2 is hydrogen, C ^ alkyl, allyl, Cj. ^ - alkoxy, 2-propynyl, methoxymethyl or hydroxyl and R3 is hydrogen or C ^ alkyl. The preferred, particularly preferred and very particularly preferred compounds defined above can be in the form of the ice and trans isomers and in the form of racemic mixtures or in the form of the optically active isomers. The preparation of the compounds of the formulas (I) and (II) according to the invention is usually carried out in practice using a slight excess (ie up to an excess of 20%) of the isocyanate or of the isothioeyanate of the formula III or IV in the presence of a solvent . Although the reaction occurs at elevated pressure and at temperatures from 0 to 100 ° C, it is generally preferred to carry out the reaction at atmospheric pressure and at a temperature between 0 and 80 ° C. When an acid salt of a compound of formula R2R3NH is used, it is most convenient to work in the presence of an acid acceptor. Suitable organic solvents are aprotic aromatic solvents, such as benzene, toluene or xylene; Chlorinated hydrocarbons, such as methylene chloride, chloroform or dichloroethane; Ether, such as tetrahydrofuran, diethyl ether, dimethoxyethane, dimethylene glycol, dimethyl ether or dioxane; Ketones with alkyl groups with 1 to 4 carbon atoms, such as acetone, methyl ethyl ketone, methyl butyl ketone or methyl isobutyl ketone; or mixtures of these solvents. Suitable acid acceptors are trialkylamines, such as triethylamine, trimethylamine or pyridine; Alkali carbonates such as sodium and potassium carbonate; Alkaline earth carbonates, such as calcium carbonate, as well as strongly basic ion exchange resins and an aqueous alkali in a two-phase system, which contains an immiscible hydrocarbon solvent, such as benzene or toluene, or a chlorinated hydrocarbon, such as chloroform or dichloroethane. 5 If a solution of the compound of the formula R2R3NH in water or an alcohol having 1 to 3 carbon atoms is used in the above reaction sequence, compounds of the formula (I) or (II) are obtained in which R2 and R3 have the meanings given above . The isocyanates of the formula (III) or (IV) required as starting products in the process according to the invention can be readily prepared by reacting the corresponding amines or their acid addition salts with 15 phosgene, preferably under anhydrous conditions, e.g. works under an inert gas such as nitrogen. The reaction can initially be carried out at a temperature between about 0 and 40 ° C, preferably at a temperature of 10 to 20 ° C, after which the reaction mixture is brought to a temperature between about 50 and 100 ° C, preferably at a temperature of 60 to 80 ° C, can heat. The reaction can be carried out in the usual way in the presence of an organic solvent, such as benzene, toluene or xylene. 25 For the preparation of the new compounds of the formula I in which X is oxygen, R1; Y and Z are hydrogen and U is -CO-, R2 is hydrogen, C1_s-alkyl, allyl, C ^ -alkoxy, 2-propynyl, methoxymethyl or hydroxyl and R3 is hydrogen or C ^ -alkyl, 30 this is how it is done before that the compound of formula nh ^ 'hcl 0 in benzene, toluene, xylene or a mixture of isomeric xylenes as aromatic solvent with phosgene at reflux temperature, the 4,5,6,7-tetra-45 hydro-7-oxobenzo- [b] -thien-4-yl- formed Isocyanate wins, 1 molar equivalent of the isocyanate obtained in an alkanol with 1 to 3 carbon atoms as a solvent at a temperature of 0 to 100 ° C with 1 to 1.5 molar equivalents of a corresponding compound of the formula 50 R2 h-nc; r3 55 and the product is isolated. The isothiocyanates of the formula III or IV required as starting materials in the process according to the invention can be prepared by reacting the corresponding amines with equimolar amounts of carbon disulphide, tri-60 ethylamine and a carbodiimide of the formula G-N = C = N-G, in which G e.g. represents cyclohexyl, cycloheptyl or C.I. (rAlkyl. This reaction is generally carried out in the presence of a solvent, such as tetrahydrofuran, or an ether, such as diethyl ether, at a temperature between 65 and about -10 and + 25 ° C. The product can be isolated by distillation or by dry column chromatography and the reaction can be represented by the following equations: 7 619 -m or, + cs2 + (c2h5) 3n + g-n = c = n-g ir ma M v Optionally, the above isothiocyanates can also be prepared by reacting the amines of the formulas V and VI in the presence of chloroform at room temperature with 1,1'-thiocarbonyldiimidazole. The reaction can be expressed as follows: v vi N = v n- s II J • n \ = chc1. v purple v. IVa The new compounds obtainable according to the invention are suitable as growth-promoting agents for animals, such as poultry, fur animals or agricultural livestock, the use of these compounds for this purpose giving the additional advantage that better conversion of feed is achieved in the animals. The term "feed conversion" as used herein means the ratio of the weight unit of feed to the increase in weight by one unit of weight, where an improvement in feed conversion means an increased weight gain for a given amount of feed consumed. The method according to the invention for improving the feed efficiency and increasing the growth rate of warm-blooded animals is characterized in that the animals are orally administered an effective amount of a new compound of the formula I or II. The supplementary feed according to the invention for increasing the The growth rate of poultry, fur animals and farm animals is characterized in that it contains 70 to 99% by weight of an edible carrier material and 1 30 to 30% by weight of a new compound of the formula (I) or (II). In practice, animals can be given a growth promoting amount of a new compound of formula (I) or (II) or an optically active isomer thereof in or with the feed. However, the compound can also be implanted under the animal's skin or administered by parenteral injection. When the compounds obtainable according to the invention are introduced into the feed of chickens, turkeys, sheep, cattle, goats and the like, it is normally about 0.0001 to 0.08% by weight, preferably 0.001 to 0.04% by weight. %, the compound of formula (I) or (II) sufficient to increase the rate of growth and to improve feed conversion. When the products are injected parenterally or implanted subcutaneously, the desired improvement in weight gain and increased feed conversion are achieved if the active compound is used in an amount of about 0.001 to 0.2 mg per day, preferably in an amount of 0.005 to 0 mg, 10 mg, administered per kg of the body weight of the animal, so. Tests carried out on 1-day-old chickens had shown that adding 1 to 9 ppm of 4,5,6,7-tetrahydro-benzo- [ bJ-thien-4-yl - urea in the chicken feed compared to the untreated control animals can achieve an improvement in weight gain by 55 3.3 to 6.6% and an increase in feed conversion by 2.7 to 4.7%. The new compounds obtainable according to the invention are also suitable as herbicidal compositions. Thus, they are suitable for controlling the undesired broad-leaved weeds 6o and the grass weeds, if they are applied to the soil containing the seeds of the unwanted weeds or to the foliage of these plants. It is usually sufficient to control the undesirable plants if the active compound is applied in an amount of from about 5.60 to 16.8 kg / ha, preferably in an amount of about 11.2 kg / ha.