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Ethyl N-(4-methylphenyl)sulfonylcarbamate, also known as Tosylurethane, is an organic compound that serves as an intermediate in the synthesis of Gliclazide, a sulfonylurea hypoglycemic agent. It is characterized by its chemical structure, which includes an ethyl group, a sulfonyl group, and a carbamate group attached to a 4-methylphenyl group.

5577-13-9

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5577-13-9 Usage

Uses

Used in Pharmaceutical Industry:
Ethyl N-(4-methylphenyl)sulfonylcarbamate is used as an intermediate in the synthesis of Gliclazide for the development of antidiabetic medications. It plays a crucial role in the production of Gliclazide, which is an important drug for managing blood sugar levels in patients with diabetes.
Ethyl N-(4-methylphenyl)sulfonylcarbamate is used as a key component for [application reason] in the pharmaceutical industry, specifically in the synthesis of Gliclazide, an antidiabetic drug. Its presence in the synthesis process is essential for the development of effective treatments for diabetes, helping to regulate blood sugar levels and improve the quality of life for patients with this condition.

Check Digit Verification of cas no

The CAS Registry Mumber 5577-13-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,7 and 7 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5577-13:
(6*5)+(5*5)+(4*7)+(3*7)+(2*1)+(1*3)=109
109 % 10 = 9
So 5577-13-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H13NO4S/c1-3-15-10(12)11-16(13,14)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3,(H,11,12)

5577-13-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl N-(4-methylphenyl)sulfonylcarbamate

1.2 Other means of identification

Product number -
Other names ethyl p-tosylcarbamate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5577-13-9 SDS

5577-13-9Synthetic route

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
With palladium diacetate In acetonitrile at 20℃; under 15 Torr; for 12h; Schlenk technique; Sealed tube;94%
N,N'-carbonyl-bis(4-methylbenzenesulfonamide)
5219-81-8

N,N'-carbonyl-bis(4-methylbenzenesulfonamide)

Diethyl carbonate
105-58-8

Diethyl carbonate

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
With silica gel-supported lanthanum(III) oxide at 150℃; for 10h; Autoclave; Inert atmosphere;90%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Reflux;87%
With sodium hydroxide
ethanol
64-17-5

ethanol

n-butyl tosylcarbamate
31224-37-0

n-butyl tosylcarbamate

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
at 120℃; for 0.333333h; Sealed tube; Microwave irradiation;84%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Hexamethylphosphorous triamide
1608-26-0

Hexamethylphosphorous triamide

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
With diethylazodicarboxylate In tetrahydrofuran for 2h; Ambient temperature;33%
p-Toluol-(-N-carbethoxy)-iminosulfonsaeurechlorid
93506-31-1

p-Toluol-(-N-carbethoxy)-iminosulfonsaeurechlorid

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
With potassium hydroxide
4-methylbenzenesulfinyl chloride
10439-23-3

4-methylbenzenesulfinyl chloride

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzene
2: aq. KOH
View Scheme
Tosyl isocyanate
4083-64-1

Tosyl isocyanate

Tosylurethane
5577-13-9

Tosylurethane

methyl tosylcarbamate
14437-03-7

methyl tosylcarbamate

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation
2: 0.33 h / 120 °C / Sealed tube; Microwave irradiation
View Scheme
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Tosylurethane
5577-13-9

Tosylurethane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 0.17 h / 0 °C
1.2: 2.5 h / 0 - 20 °C
2.1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation
3.1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 0.17 h / 0 °C
1.2: 2.5 h / 0 - 20 °C
2.1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation
3.1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation
View Scheme
Tosylurethane

Tosylurethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium azide / water; acetonitrile / 0.33 h / 20 °C / Schlenk technique
2: palladium diacetate / acetonitrile / 12 h / 20 °C / 15 Torr / Schlenk technique; Sealed tube
View Scheme
Tosylurethane
5577-13-9

Tosylurethane

1-butyn-4-ol
927-74-2

1-butyn-4-ol

O-ehtyl-N-but-3-ynyl-N-(4-methylphenyl)sulfonylcarbamate
349451-03-2

O-ehtyl-N-but-3-ynyl-N-(4-methylphenyl)sulfonylcarbamate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h;96%
Tosylurethane
5577-13-9

Tosylurethane

1,1-Diphenylhydrazine
530-50-7

1,1-Diphenylhydrazine

1,1-Diphenyl-4-(4-tosyl)semicarbazid

1,1-Diphenyl-4-(4-tosyl)semicarbazid

Conditions
ConditionsYield
at 130℃; for 2h;88%
Tosylurethane
5577-13-9

Tosylurethane

7-amino-1,3,5-triazaadamantane
14707-75-6

7-amino-1,3,5-triazaadamantane

N-(p-toluenesulfonyl)-N'-[7-(1,3,5-triazaadamantyl)]urea

N-(p-toluenesulfonyl)-N'-[7-(1,3,5-triazaadamantyl)]urea

Conditions
ConditionsYield
In toluene for 10h; Substitution; Heating;79.9%
Tosylurethane
5577-13-9

Tosylurethane

tert-butyl (1-(4-chlorophenyl)-2-methylene-3-oxobutyl) carbonate
1308286-01-2

tert-butyl (1-(4-chlorophenyl)-2-methylene-3-oxobutyl) carbonate

ethyl 1-(4-chlorophenyl)-2-methylene-3-oxobutyl(tosyl)carbamate
1330174-11-2

ethyl 1-(4-chlorophenyl)-2-methylene-3-oxobutyl(tosyl)carbamate

Conditions
ConditionsYield
With 6'-N-phenylformamide-β-ICD In tetrahydrofuran at 20℃; for 72h; optical yield given as %ee;78%
Tosylurethane
5577-13-9

Tosylurethane

glycyclamide
664-95-9

glycyclamide

Conditions
ConditionsYield
In toluene for 6h; Reflux;75%
Tosylurethane
5577-13-9

Tosylurethane

tert-butyl (2-methylene-3-oxo-1-(p-tolyl)butyl) carbonate
1304688-64-9

tert-butyl (2-methylene-3-oxo-1-(p-tolyl)butyl) carbonate

ethyl 2-methylene-3-oxo-1-p-tolylbutyl(tosyl)carbamate
1330174-12-3

ethyl 2-methylene-3-oxo-1-p-tolylbutyl(tosyl)carbamate

Conditions
ConditionsYield
With 6'-N-phenylformamide-β-ICD In tetrahydrofuran at 20℃; for 72h; optical yield given as %ee;72%
Tosylurethane
5577-13-9

Tosylurethane

4-p-Tolylsulfonylsemicarbazid
18258-96-3

4-p-Tolylsulfonylsemicarbazid

Conditions
ConditionsYield
With hydrazine hydrate In ethanol Heating;71%
With hydrazine hydrate In ethanol for 8h; Heating;
Tosylurethane
5577-13-9

Tosylurethane

2-(6-aminopyridin-3-yl)-4-(morpholin-4-yl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine 6,6-dioxide

2-(6-aminopyridin-3-yl)-4-(morpholin-4-yl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine 6,6-dioxide

4-methyl-N-((5-(4-(morpholin-4-yl)-6,6-dioxido-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-yl)pyridin-2-yl)carbamoyl)benzenesulfonamide

4-methyl-N-((5-(4-(morpholin-4-yl)-6,6-dioxido-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-yl)pyridin-2-yl)carbamoyl)benzenesulfonamide

Conditions
ConditionsYield
In toluene65.3%
Tosylurethane
5577-13-9

Tosylurethane

4-(4-amino-2-fluorophenoxy)-N-methylpicolinamide
757251-42-6

4-(4-amino-2-fluorophenoxy)-N-methylpicolinamide

4-(4-(3-(4-methylbenzenesulfonyl)ureido)-2-fluorophenoxy)-N-methylpyridine-2-carboxamide

4-(4-(3-(4-methylbenzenesulfonyl)ureido)-2-fluorophenoxy)-N-methylpyridine-2-carboxamide

Conditions
ConditionsYield
In toluene for 6h; Reflux;45.3%
Tosylurethane
5577-13-9

Tosylurethane

4"-epi-amino-4"-deoxyavermectin B1a

4"-epi-amino-4"-deoxyavermectin B1a

C56H80N2O16S

C56H80N2O16S

Conditions
ConditionsYield
Reflux;40%
Tosylurethane
5577-13-9

Tosylurethane

2-methoxyethylamine
109-85-3

2-methoxyethylamine

Conditions
ConditionsYield
With 2-methoxy-ethanol
Tosylurethane
5577-13-9

Tosylurethane

3,3-dimethylallylamine
13822-06-5, 108963-90-2

3,3-dimethylallylamine

4-methyl-N-{[(3-methyl-2-butenyl)amino]carbonyl}-benzenesulfonamide
25799-83-1

4-methyl-N-{[(3-methyl-2-butenyl)amino]carbonyl}-benzenesulfonamide

Tosylurethane
5577-13-9

Tosylurethane

3-Methyl-but-2-enoic acid (toluene-4-sulfonylaminocarbonyl)-amide
28490-61-1

3-Methyl-but-2-enoic acid (toluene-4-sulfonylaminocarbonyl)-amide

Tosylurethane
5577-13-9

Tosylurethane

4-Methyl-3-pentenamide
70265-05-3

4-Methyl-3-pentenamide

4-Methyl-pent-3-enoic acid (toluene-4-sulfonylaminocarbonyl)-amide
28490-28-0

4-Methyl-pent-3-enoic acid (toluene-4-sulfonylaminocarbonyl)-amide

Tosylurethane
5577-13-9

Tosylurethane

5-methyl-hex-4-enoic acid amide

5-methyl-hex-4-enoic acid amide

1-(5-methyl-4-hexenoyl)-3-(p-tolylsulfonyl)-urea
28490-29-1

1-(5-methyl-4-hexenoyl)-3-(p-tolylsulfonyl)-urea

Tosylurethane
5577-13-9

Tosylurethane

memantine*
19982-08-2

memantine*

N'--N-<3,5-dimethyl-adamantyl-(1)>-harnstoff
100063-87-4

N'--N-<3,5-dimethyl-adamantyl-(1)>-harnstoff

Tosylurethane
5577-13-9

Tosylurethane

1-Adamantanamine
768-94-5

1-Adamantanamine

N'-p-Toluolsulfonyl-N-adamantyl-(1)-harnstoff
17822-61-6

N'-p-Toluolsulfonyl-N-adamantyl-(1)-harnstoff

Tosylurethane
5577-13-9

Tosylurethane

N-(2-adamantyl)amine
13074-39-0

N-(2-adamantyl)amine

N'--N-<3,5-dimethyl-adamantyl-(2)>-harnstoff
98654-36-5

N'--N-<3,5-dimethyl-adamantyl-(2)>-harnstoff

Tosylurethane
5577-13-9

Tosylurethane

3-methyl-1-aminoadamantane
78056-28-7

3-methyl-1-aminoadamantane

N'--N-<3-methyl-adamantyl>-harnstoff
99998-84-2

N'--N-<3-methyl-adamantyl>-harnstoff

Tosylurethane
5577-13-9

Tosylurethane

1-amino-4-methyl-3-pentene
13296-28-1

1-amino-4-methyl-3-pentene

1-(4-methyl-3-pentenyl)-3-(p-tolylsulfonyl)-urea
28490-23-5

1-(4-methyl-3-pentenyl)-3-(p-tolylsulfonyl)-urea

Tosylurethane
5577-13-9

Tosylurethane

Cinnamyl bromide
4392-24-9

Cinnamyl bromide

ethyl cinnamyl(tosyl)carbamate
32120-97-1

ethyl cinnamyl(tosyl)carbamate

Conditions
ConditionsYield
With sodium 1.) EtOH, RT; 0.5 h, 2.) EtOH, 1 h; Multistep reaction;
Tosylurethane
5577-13-9

Tosylurethane

prenyl bromide
870-63-3

prenyl bromide

C15H21NO4S

C15H21NO4S

Conditions
ConditionsYield
With sodium 1.) EtOH, RT; 0.5 h, 2.) EtOH, 1 h; Multistep reaction;
trans-geranyl bromide
6138-90-5

trans-geranyl bromide

Tosylurethane
5577-13-9

Tosylurethane

ethyl N-geranyl-N-tosylcarbamate
124658-92-0

ethyl N-geranyl-N-tosylcarbamate

Conditions
ConditionsYield
With sodium 1.) EtOH, RT; 0.5 h, 2.) EtOH, 1 h; Yield given. Multistep reaction;

5577-13-9Relevant academic research and scientific papers

Synthesis, characterization and DNA-binding studies of 1-cyclohexyl-3-tosylurea and its Ni(II), and Cd(II) complexes

Xi, Pin-xian,Xu, Zhi-hong,Liu, Xiao-hui,Cheng, Feng-juan,Zeng, Zheng-zhi

, p. 523 - 528 (2008)

1-Cyclohexyl-3-tosylurea (HL) and its two complexes, ML2·2H2O [M{double bond, long}Ni(1), and Cd(2)], have been synthesized and characterized on the basis of elemental analyses, molar conductivities, IR spectra and thermal analyses. In addition, the DNA-binding properties of the ligand and the two complexes have been investigated by electronic absorption, fluorescence, CD spectroscopy and viscosity measurements. The experiment results suggest that the ligand and its two complexes bind to DNA via a groove binding mode, and the binding affinity of the complex 2 is higher than that of the complex 1 and the ligand.

Synthesis, characterization, antioxidant activity, and DNA-binding studies of 1-cyclohexyl-3-tosylurea and its Nd(III), Eu(III) complexes

Xi, Pin-Xian,Xu, Zhi-Hong,Liu, Xiao-Hui,Chen, Feng-Juan,Huang, Liang,Zeng, Zheng-Zhi

, p. 541 - 546 (2008)

A new ligand, 1-cyclohexyl-3-tosylurea (H2L), was prepared by condensation ethyl N-(3-tossulfonyl) carbamate and cyclohexanamine. Its two lanthanide(III) complexes, Ln(H2L)3·3NO3 [Ln=Nd (1), and Eu (2)], have been synthesized and characterized on the base of element analyses, ESI-MS, molar conductivities, IR spectra and thermogravimetry/differential thermal analysis (TG-DTA). In addition, the DNA-binding properties of the ligand and its complexes have been investigated by electronic absorption spectroscopy, fluorescence spectroscopy, circular dichroic (CD) spectroscopy and viscosity measurements. The experiment results suggest that the ligand and its two complexes bind to DNA via a groove binding mode, and the binding affinity of the complex 2 is higher than that of the complex 1 and the ligand. Furthermore, the antioxidant activity (superoxide and hydroxyl radical) of the ligand and its metal complexes was determined by using spectrophotometer methods in vitro. These complexes were found to possess potent antioxidant activity and be better than standard antioxidants like vitamin C and mannitol. In particular, complex 2 displayed excellent activity on the superoxide and hydroxyl radical.

PROCESS FOR PREPARATION OF GRAPIPRANT

-

Paragraph 0134-0135, (2021/03/19)

The invention relates to process for the preparation of grapiprant and its intermediates thereof. The invention also relates to grapiprant having a purity 98% or more and compounds of Formula (A), (B), (C) and (D) in an amount of 0.5 or less, relative to grapiprant, by area percentage of HPLC. The invention also relates to an amorphous form of grapiprant and process for preparation thereof.

A sulfonyl urea, sulfonamide ethyl ester preparation method of compound (by machine translation)

-

Paragraph 0094; 0100-0104; 0110-0115, (2017/08/02)

The description relates to a compound of formula (I) compound of the preparation method, wherein formula (II) with a compound represented by formula (III) as shown in the catalysis of palladium catalyst, under a carbon monoxide atmosphere, reacts in a solvent to obtain the compound. The invention related to the method of the reaction do not require strict-free conditions, does not need a high pressure carbon monoxide atmosphere, convenient and simple to operate, to a functional group and has very high power density and universality, the catalyst consumption is very small, the cost of reaction is very low, and can be widely used for preparing sulfonyl urea compound. R1 - SO2 - NH - CO - X (R3 )n - R2 (I) R1 - SO2 - R4 (II) HX (R3 )n - R2 (III) wherein X is O or N; n is 0 or 1; when X is when O, n=0; when X is when N, n=1; R1 Selected from aryl, heteroaryl, alkyl, alkenyl or alkynyl; R2 Selected from aryl, heteroaryl, alkyl, alkenyl or alkynyl; R3 Is selected from H, R2 , Or R3 And R2 A ring of connection; R4 For N3 Or a halogen atom; when R4 For nails halogen original, system also comprises a sodium azide. (by machine translation)

Product-Derived Bimetallic Palladium Complex Catalyzes Direct Carbonylation of Sulfonylazides

Zhao, Jin,Li, Zongyang,Song, Shaole,Wang, Ming-An,Fu, Bin,Zhang, Zhenhua

, p. 5545 - 5549 (2016/05/09)

A novel product-derived bimetallic palladium complex catalyzes a sulfonylazide-transfer reaction with the σ-donor/π-acceptor ligand CO, and is advantageous given its broad substrate scope, high efficiency, and mild reaction conditions (atmospheric pressure of CO at room temperature). This methodology provides a new approach to sulfonylureas, which are present in both pharmaceuticals and agrochemicals. The synthesis of Glibenclamide on a gram scale further revealed the practical utility of this procedure. Mechanistically, the generation of a bridged bimetallic palladium species derived from the product sulfonylurea is disclosed as the crucial step for this catalytic cycle.

Rapid and straightforward transesterification of sulfonyl carbamates

Isaksson, Rebecka,Kumpi?a, Ilze,Larhed, Mats,Wannberg, Johan

, p. 1476 - 1478 (2016/03/12)

A fast and convenient method for the alkoxy exchange of sulfonyl carbamates by simply heating in a chosen alkyl alcohol is described. No catalysts or additives are required. Microwave heating at 100-120 °C for 20-60 min resulted in good to excellent yields (53-93%) of alkyl (arylsulfonyl)carbamates where the alkyl part originates from the alcohol solvent. The developed protocol was applied to the synthesis of an angiotensin II type 2 receptor (AT2R) ligand.

Green and practical synthesis of carbamates from ureas and organic carbonates

Guo, Xiaoguang,Shang, Jianpeng,Li, Jian,Wang, Liguo,Ma, Yubo,Shi, Feng,Deng, Youquan

experimental part, p. 1102 - 1111 (2011/05/02)

A practical method for the synthesis of carbamates from ureas and organic carbonates was developed with 100% atom economy using La2O 3/SiO2 as catalyst without any additional solvent. The scope of the protocol is demonstrated in the synthesis of 14 carbamates with various functional groups in excellent yields (76-95%).

Use of an arylsulphonylurethane as film forming resin in nitrocellulose nail varnishes, new arylsulphonylurethanes and new nitrocellulose nail varnishes

-

, (2008/06/13)

The present invention lies in the field of nitrocellulose nail varnishes and its subject is the use of an arylsulphonylurethane as film forming resin in these varnishes, which makes it possible in particular to avoid the release of formaldehyde, a carcinogenic compound which is formed when an arylsulphonamide-formaldehyde resin is employed. Another subject of the invention is new poly(arylsulphonylurethanes) containing from 2 to 5 arylsulphonylurethane groups and possessing a molecular mass of between 450 and 1500.

Synthesis of N-Acyl-, N-Sulfonyl-, and N-Phosphinylphospha-λ5-azenes by a Redox-Condensation Reaction Using Amides, Triphenylphosphine, and Diethyl Azodicarboxylate

Bittner, Shmuel,Assaf, Yonit,Krief, Penina,Pomerantz, Martin,Ziemnicka, Barbara T.,Smith, Christina G.

, p. 1712 - 1718 (2007/10/02)

The reaction of phosphines and amides with diethyl azodicarboxylate (DAD) produced phospha-λ5-azenes.Thus aromatic amides and those aliphathic amides with electron-withdrawing substituents gave N-acyl-P,P,P-triphenylphospha-λ5-azenes (5) when triphenylphosphine (TPP) was employed.Both aryl- and alkylsulfonamides reacted with TPP and DAD to produce the N-sulfonylphospha-λ5-azenes (9).Diphenylphosphinamide (10) and ethyl carbamate (12) also produced the respective phosphazenes (11 and 13) with TPP and DAD.Secondary carboxamides and sulfonamides did not react with TPP and DAD.The reaction of triethyl phosphite with sulfonamides in the presence of DAD produced the phosphorimidates (20) in an analogous reaction, along with the corresponding N,N-diethylsulfonamides and the deethylated adduct of triethyl phosphite and DAD (23).Triethyl phosphite-DAD failed, however, to give a phosphorimidate with carboxamides but gave, instead, the rearranged adduct of DAD and triethyl phosphite (19).Tris(dimethylamino)phosphine reacted with sulfonamides and DAD but the products were the corresponding ethyl N-sulfonylcarbamates (26) rather than the phosphazenes.Tris(dimethylamino)phosphine reacted with azodicarbonamide (a molecule which contains both the azo and carboxamide groups) with the production of N,N-dimethylurea, again without formation of the phosphazene.Finally, the reaction of triphenylarsine with benzenesulfonamide and DAD produced N-(phenylsulfonyl)triphenylarsa-λ5-azene (30) but triphenylstibene with DAD and benzenesulfonamide only gave triphenylstibene oxide.Mechanistic possibilities for these reactions are also discussed.

N-arylsulfonyl carbamates

-

, (2008/06/13)

The present invention relates to amine, alkali metal and alkaline earth metal salts of N-benzene sulfonyl carbamic acid esters and to lower alkenyl N-benzene sulfonyl carbamates. These compounds are useful as herbicides.

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