DK169030B1 - Fremgangsmåde til fremstilling af trisubstituerede N-phenylurinstofderivater - Google Patents

Fremgangsmåde til fremstilling af trisubstituerede N-phenylurinstofderivater Download PDF

Info

Publication number: DK169030B1
Authority: DK; Denmark
Prior art keywords: process according; group; reaction; equal; urea
Prior art date: 1985-02-11

Application number

DK063186A

Other languages

Danish (da)

English (en)

Other versions

DK63186D0 (da

DK63186A (da

Inventor

Jean Claude Parron

Original Assignee

Rhone Poulenc Agrochimie

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.)

1985-02-11

Filing date

1986-02-10

Publication date

1994-08-01

1986-02-10 Application filed by Rhone Poulenc Agrochimie filed Critical Rhone Poulenc Agrochimie

1986-02-10 Publication of DK63186D0 publication Critical patent/DK63186D0/da

1986-08-12 Publication of DK63186A publication Critical patent/DK63186A/da

1994-08-01 Application granted granted Critical

1994-08-01 Publication of DK169030B1 publication Critical patent/DK169030B1/da

Links

238000000034 method Methods 0.000 title claims description 21
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 5
238000006243 chemical reaction Methods 0.000 claims description 18
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
239000004202 carbamide Substances 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
150000001448 anilines Chemical class 0.000 description 5
PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 4
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
-1 cyclohexanone Chemical compound 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 2
SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 2
XQVCBOLNTSUFGD-UHFFFAOYSA-N 3-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1Cl XQVCBOLNTSUFGD-UHFFFAOYSA-N 0.000 description 2
RQKFYFNZSHWXAW-UHFFFAOYSA-N 3-chloro-p-toluidine Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 2
239000005510 Diuron Substances 0.000 description 2
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000005265 dialkylamine group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 2
LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
FXFCLNJIQWLFEL-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1,3-dimethylurea Chemical compound CNC(=O)N(C)C1=CC=C(Cl)C(Cl)=C1 FXFCLNJIQWLFEL-UHFFFAOYSA-N 0.000 description 1
CJTOLCKZKYTGNU-UHFFFAOYSA-N 1-(3-chloro-4-methoxyphenyl)-1,3-dimethylurea Chemical compound CNC(=O)N(C)C1=CC=C(OC)C(Cl)=C1 CJTOLCKZKYTGNU-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000005494 Chlorotoluron Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000005533 Fluometuron Substances 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
239000005573 Linuron Substances 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical class CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
238000009434 installation Methods 0.000 description 1
ABBKOIZWGCVCKE-UHFFFAOYSA-N isoproturon-didemethyl Chemical compound CC(C)C1=CC=C(NC(N)=O)C=C1 ABBKOIZWGCVCKE-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
- C07C273/1863—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety from urea

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK063186A 1985-02-11 1986-02-10 Fremgangsmåde til fremstilling af trisubstituerede N-phenylurinstofderivater DK169030B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8502079		1985-02-11
FR8502079A FR2577221B1 (fr)	1985-02-11	1985-02-11	Procede de preparation d'une phenyluree substituee

Publications (3)

Publication Number	Publication Date
DK63186D0 DK63186D0 (da)	1986-02-10
DK63186A DK63186A (da)	1986-08-12
DK169030B1 true DK169030B1 (da)	1994-08-01

Family

ID=9316250

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK063186A DK169030B1 (da)	1985-02-11	1986-02-10	Fremgangsmåde til fremstilling af trisubstituerede N-phenylurinstofderivater

Country Status (27)

Country	Link
US (1)	US4814499A (fr)
JP (1)	JPS61183258A (fr)
KR (1)	KR940003067B1 (fr)
CN (1)	CN1009274B (fr)
AT (1)	AT395848B (fr)
AU (1)	AU577178B2 (fr)
BE (1)	BE904217A (fr)
BR (1)	BR8600539A (fr)
CH (1)	CH666681A5 (fr)
DD (1)	DD242803A5 (fr)
DE (1)	DE3602657A1 (fr)
DK (1)	DK169030B1 (fr)
ES (1)	ES8702347A1 (fr)
FI (1)	FI84597C (fr)
FR (1)	FR2577221B1 (fr)
GB (1)	GB2170808B (fr)
HU (1)	HU199111B (fr)
IE (1)	IE58978B1 (fr)
IN (1)	IN166514B (fr)
IT (1)	IT1190483B (fr)
LU (1)	LU86296A1 (fr)
NL (1)	NL8600189A (fr)
NZ (1)	NZ215067A (fr)
PH (1)	PH20993A (fr)
PL (1)	PL257891A1 (fr)
SE (1)	SE465927B (fr)
ZA (1)	ZA86931B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE59005183D1 (de) *	1989-11-10	1994-05-05	Agrolinz Agrarchemikalien	Verfahren zur Herstellung reiner, unsymmetrisch disubstituierter Harnstoffe.
AT397384B (de) *	1991-08-16	1994-03-25	Chemie Linz Gmbh	Verfahren zur herstellung reiner n,n'-unsymmetrisch substituierter phenylharnstoffe
CN1045002C (zh) *	1995-03-28	1999-09-08	天津大学	２，６－二氯苯胺的制备方法
CN106008276B (zh) *	2016-05-20	2018-07-06	湖北出入境检验检疫局检验检疫技术中心	苯脲类除草剂或氘代标记的苯脲类除草剂的合成方法
CN110938019B (zh) *	2019-12-10	2022-06-24	江苏快达农化股份有限公司	连续化合成异丙隆方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2878284A (en) *	1945-06-09	1959-03-17	Du Pont	Process for preparing symmetrical hexachlorodiphenyl urea
US2673877A (en) *	1951-10-26	1954-03-30	Du Pont	Preparation of chlorphenyldimethyl-ureas
US2729677A (en) *	1954-03-16	1956-01-03	Allied Chem & Dye Corp	Process for the manufacture of substituted ureas
US2768971A (en) *	1954-05-26	1956-10-30	Ici Ltd	Preparation of alkyl-aryl-ureas
DE1064051B (de) *	1958-04-09	1959-08-27	Basf Ag	Verfahren zur Herstellung von substituierten Harnstoffen
NL255093A (fr) *	1959-08-21
CA1201725A (fr) *	1979-12-06	1986-03-11	Terence Gilkerson	Derive de l'uree, sa preparation, herbicide qui le renferme, et methode de repression des mauvaises herbes
DE3133794A1 (de) *	1980-01-25	1982-04-01	Daroczi I	Verfahren zur Herstellung von N'-(mono-oder disubstituierten) N-Aryl-Harnstoff-Derivaten
CH652391A5 (de) *	1982-01-15	1985-11-15	Sandoz Ag	Harnstoff-derivate.
IT1152510B (it) *	1982-08-25	1987-01-07	Anic Spa	Procedimento per la produzione di uree asimmetriche sostituite

1985
- 1985-02-11 FR FR8502079A patent/FR2577221B1/fr not_active Expired
1986
- 1986-01-28 IN IN79/DEL/86A patent/IN166514B/en unknown
- 1986-01-28 NL NL8600189A patent/NL8600189A/nl not_active Application Discontinuation
- 1986-01-29 DE DE19863602657 patent/DE3602657A1/de not_active Ceased
- 1986-01-30 PH PH33351A patent/PH20993A/en unknown
- 1986-02-06 CN CN86101095A patent/CN1009274B/zh not_active Expired
- 1986-02-06 LU LU86296A patent/LU86296A1/fr unknown
- 1986-02-07 ZA ZA86931A patent/ZA86931B/xx unknown
- 1986-02-07 BR BR8600539A patent/BR8600539A/pt not_active IP Right Cessation
- 1986-02-07 NZ NZ215067A patent/NZ215067A/xx unknown
- 1986-02-07 JP JP61025684A patent/JPS61183258A/ja active Pending
- 1986-02-07 AU AU53299/86A patent/AU577178B2/en not_active Ceased
- 1986-02-07 US US06/827,782 patent/US4814499A/en not_active Expired - Fee Related
- 1986-02-07 IE IE35286A patent/IE58978B1/en not_active IP Right Cessation
- 1986-02-07 DD DD86286892A patent/DD242803A5/de unknown
- 1986-02-07 IT IT47634/86A patent/IT1190483B/it active
- 1986-02-10 DK DK063186A patent/DK169030B1/da not_active IP Right Cessation
- 1986-02-10 PL PL25789186A patent/PL257891A1/xx unknown
- 1986-02-10 GB GB08603223A patent/GB2170808B/en not_active Expired
- 1986-02-10 ES ES551790A patent/ES8702347A1/es not_active Expired
- 1986-02-10 AT AT0032586A patent/AT395848B/de not_active IP Right Cessation
- 1986-02-10 KR KR1019860000901A patent/KR940003067B1/ko not_active Expired - Fee Related
- 1986-02-10 FI FI860597A patent/FI84597C/fi not_active IP Right Cessation
- 1986-02-10 HU HU86542A patent/HU199111B/hu not_active IP Right Cessation
- 1986-02-11 CH CH545/86A patent/CH666681A5/fr not_active IP Right Cessation
- 1986-02-11 SE SE8600596A patent/SE465927B/sv not_active IP Right Cessation
- 1986-02-11 BE BE0/216258A patent/BE904217A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1190483B (it)	1988-02-16
CN1009274B (zh)	1990-08-22
IE860352L (en)	1986-08-11
JPS61183258A (ja)	1986-08-15
IN166514B (fr)	1990-05-19
SE8600596L (sv)	1986-08-12
AU5329986A (en)	1986-08-14
NZ215067A (en)	1989-04-26
IE58978B1 (en)	1993-12-15
DK63186D0 (da)	1986-02-10
PH20993A (en)	1987-06-18
KR940003067B1 (ko)	1994-04-13
FI860597A0 (fi)	1986-02-10
FR2577221B1 (fr)	1987-02-20
FI84597C (fi)	1991-12-27
AU577178B2 (en)	1988-09-15
US4814499A (en)	1989-03-21
PL257891A1 (en)	1987-03-09
ES8702347A1 (es)	1986-12-16
HU199111B (en)	1990-01-29
SE465927B (sv)	1991-11-18
GB2170808B (en)	1988-08-17
SE8600596D0 (sv)	1986-02-11
LU86296A1 (fr)	1987-09-10
BR8600539A (pt)	1986-10-21
DE3602657A1 (de)	1986-08-14
KR860006436A (ko)	1986-09-11
FR2577221A1 (fr)	1986-08-14
AT395848B (de)	1993-03-25
CN86101095A (zh)	1986-08-06
DK63186A (da)	1986-08-12
DD242803A5 (de)	1987-02-11
ES551790A0 (es)	1986-12-16
GB8603223D0 (en)	1986-03-19
BE904217A (fr)	1986-08-11
GB2170808A (en)	1986-08-13
CH666681A5 (fr)	1988-08-15
FI84597B (fi)	1991-09-13
NL8600189A (nl)	1986-09-01
ATA32586A (de)	1992-08-15
IT8647634A0 (it)	1986-02-07
HUT42432A (en)	1987-07-28
ZA86931B (en)	1986-09-24
FI860597L (fi)	1986-08-12

Legal Events

Date	Code	Title	Description
1994-08-01	B1	Patent granted (law 1993)
1995-10-23	PBP	Patent lapsed

Publication	Publication Date	Title
US2093265A (en)	1937-09-14	Process for the manufacture of diaryl ureas
US3764624A (en)	1973-10-09	N-substituted-2,6-dinitro-3-(alkoxy or alkylthio)-4-substituted-aniline compounds
US2326501A (en)	1943-08-10	Isocyanates
US2655534A (en)	1953-10-13	Preparation of n-aromatic-n'-aliphatic hydrocarbon ureas
SK279982B6 (sk)	1999-06-11	Spôsob výroby čistej, nesymetricky disubstituovane
FI84597B (fi)	1991-09-13	Foerfarande foer framstaellning av en trisubstituerad fenylurea.
US3852317A (en)	1974-12-03	Production of isocyanates
KR880002297B1 (ko)	1988-10-22	방향족 아미노설폰산의 제조방법
CN110105251A (zh)	2019-08-09	一种邻硝基苯磺酰氯的工业化生产方法
Semenuk et al.	1969	Icosahedral carboranes. X. Carborane bis (sulfenyl chlorides) as polymer intermediates
US4968835A (en)	1990-11-06	Process for the preparation of aminoaryl-sulphonic acids
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