GB2106499A - Method for making benzoylphenylureas - Google Patents
Method for making benzoylphenylureas Download PDFInfo
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- GB2106499A GB2106499A GB08128333A GB8128333A GB2106499A GB 2106499 A GB2106499 A GB 2106499A GB 08128333 A GB08128333 A GB 08128333A GB 8128333 A GB8128333 A GB 8128333A GB 2106499 A GB2106499 A GB 2106499A
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- compound
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- alkyl
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- 238000000034 method Methods 0.000 title claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- -1 aniline compound Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 238000010992 reflux Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical group ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims 1
- XYFMGGWVGACNEC-UHFFFAOYSA-N n-carbamoyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C(=O)N)C(=O)C1=CC=CC=C1 XYFMGGWVGACNEC-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QHTKVCGDWAOTGS-UHFFFAOYSA-N 1-(2,2-dichloro-1,1-difluoroethoxy)-4-isocyanatobenzene Chemical compound ClC(Cl)C(F)(F)OC1=CC=C(N=C=O)C=C1 QHTKVCGDWAOTGS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MQJBOCAFCBRKTK-UHFFFAOYSA-N 4-(2,2-dichloro-1,1-difluoroethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)C(Cl)Cl)C=C1 MQJBOCAFCBRKTK-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- DYKCDKICHOCWGU-UHFFFAOYSA-N 4-isocyanatophenol Chemical compound OC1=CC=C(N=C=O)C=C1 DYKCDKICHOCWGU-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- YPSCQJTUAKNUNF-UHFFFAOYSA-N 2-chloro-n-[(4-chlorophenyl)carbamoyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl YPSCQJTUAKNUNF-UHFFFAOYSA-N 0.000 description 1
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WSKXXIMERYQVGJ-UHFFFAOYSA-N ethyl n-(4-chlorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C=C1 WSKXXIMERYQVGJ-UHFFFAOYSA-N 0.000 description 1
- BECNKUVYBNETOM-UHFFFAOYSA-N ethyl n-(4-hydroxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(O)C=C1 BECNKUVYBNETOM-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012948 isocyanate 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing a compound having the general formula: <IMAGE> wherein X and Y are individually H, F, Cl, alkyl or haloalkyl; R and R' are individually H, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro or cyano; wherein T is halogen, halogenated alkyl or the group ZR'' wherein R'' is H, alkyl, aryl, alkyl, halogenated alkyl, halogenated alkylene, pyridyl, substituted pyridyl, phenyl or substituted phenyl and Z is O or S, comprises reacting an aniline compound having the formula: <IMAGE> wherein R, R', R'' and R are as above defined with an active carbonyl compound of the formula: <IMAGE> wherein W is individually Cl, alkoxy or haloalkoxy, optionally in the presence of a tertiary base, and thereafter reacting the resulting compound of the formula: <IMAGE> wherein R, R', R'' and T are as above defined and V is NCO or <IMAGE> wherein W is as above defined with a compound having the formula: <IMAGE> wherein X and Y are as above defined, at a temperature in the range of from 80 DEG C to 180 DEG C.
Description
SPECIFICATION
Method for making benzoylphenylureas
This invention relates to a method for making benzoylphenylureas and, more particularly, relates to a process comprising a novel sequence of steps for preparing penzoylphenylureas.
We have now found that benzoylphenylureas can be conveniently and economically prepared by a process which comprises reacting an aniline compound with an active carbonyl compound and thereafter reacting the resulting product with a benzamide.
More specifically, the present invention comprises a process for making a compound having the formula
wherein X and Y are individually H,F,CI, alkyl or haloalkyl; R and R' are individually H, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro or cyano; wherein T is halogen, halogenated alkyl or the group ZR" wherein R" is H. alkyl aryl, alkyl, halogenated alkyl, halogenated alkylene, pyridyl, substituted pyridyl, phenyl or substituted phenyl and Z is O or S,- which comprises reacting an aniline compound having the formula:-
wherein R, R', R" and T are as above defined with an active carbonyl compound of the formula::-
wherein W is individually Cl, alkoxy or haloalkoxy, optionally in the presence of a tertiary base, and thereafter reacting the resulting compound of the formula:-
wherein R, R', R" and Tare as above defined and
V is NCO or
wherein W is as above defined with a compound having the formula:-
wherein X and Y are as above defined, at a temperature in the range of from 800 to 1 800C.
When carrying out the reactions wherein the active carbonyl compound contains an alkoxy or haloalkoxy group, novel compounds are obtained.
The reactions of the active carbonyl compound with the aniline compound may be carried out at a temperature in the range of from 200 to 1 200C and are preferably carried out at ambient to reflux temperatures in the presence of an inert solvent, preferably ethyl acetate or tetrahydrofuran and an acid acceptor such as a tertiary amine or an excess of the aniline compound.
The reactions of the isocyanate compound with the benzamide compound are preferably carried out at reflux temperatures in the presence of inert solvents such as, for example, o- dichlorobenzene or xylene.
The invention is further illustrated by the following examples.
Example 1 4-(2,2-Dichloro-1 ,1 -difluoroethoxy)phenyl isocyanate
A solution of 4-(2,2-dichloro-1,1 -difluoroethoxy) benzeneamine (72.6 g) in ethyl acetate (200 ml) was added to a solution of phosgene (large excess) in ethyl acetate (800 ml) with stirring. The reaction mixture was allowed to stand at 220C for 20 hours. The ethyl acetate and excess phosgene were removed by distillation at atmospheric pressure. The black residue was then distilled under high vacuum to give a clear distillate (56.0 g, 70 percent), b.p.1mm 1100 to 1 120C.
Structural confirmation was given by NMR and
IR.
Example 2 N-(((4(2,2-Dichlorn-1 1 -difluoroethoxy)- phenyl)amino)carbonyl)-2-chlorobenzamide 4-(2,2-Dichloro- 1 , 1 -difluoroethoxy)phenylisocyanate (2.54 g) was added to a slurry of 2chlorobenzamide (1.56 g) in dry xylene (50 ml) and the mixture heated under reflux for 24 hours.
The hot, clear solution was cooled, producing a dense mass of colorless needles. The suspension was filtered and the solid washed with coid xylene, 40-60 petrol and dried to give the desired compound (3.22 g, 79 percent), m.p.
1550 to 1560C.
Example 3 Ethyl-4-(2,2-dichloro-1,1 -difluoroethoxy)- phenylcarbamate
Ethyl chloroformate (2.23 g) in tetrahydrofuran
(15 ml) was added dropwise over 5 minutes to a
stirred solution of 4-(2,2-dichloro-1,1 - difluoroethoxy)-aniline (10 g) in tetrahydrofuran (35 ml) at OOC. After stirring for 30 minutes, the resulting suspension was filtered and the clear filtrate was partitioned between ethyl acetate and 2N-HCl (70 ml of each). The organic layer was separated, washed with water, dried and the solvent removed to give a brown oil. After standing for 3 hours at -OOC, the partially solidified oil was triturated with 30-40 petrol (50 ml).The resulting suspension was filtered and the solid product dried to give ethyl 4-(2,2 dichloro- 1 1 -difloroethoxy-phenyl-carbamate (5.6 g, 86 percent), m.p. 900 to 930C.
Elemental analysis percent expected/found: C,
42.04/42.05; H 3.55/3.53; N, 4.45/4.46; Cl,
22.27/22.57; F. 12.21/12.09.
Alternatively, this product was also prepared by adding dropwise a solution of 1,1-dichloro2,2-difluoroethylene (10.2 g) in acetonitrile (10 ml) to a stirred slurry of ethyl 4-hydroxyphenylcarbamate (11.6 g) and potassium hydroxide (2.12 g) in acetonitrile (30 ml) at 50C. The rate of addition was such as to maintain a reaction temperature of less than 80C. The mixture was stirred until the reaction was complete (HPLC).
The reaction mixture was concentrated and partitioned between dichloroemethane (30 ml) and water (50 ml) and the organic layer separated and dried. The solution was made up to a known volume with methanol and assayed by high pressure liquid chromatography (HPLC) against an external standard. The yield was 7.0 g, 35 percent.
A further novel process for the preparation of ethyl 4-(2,2-dichloro-1,1 -difluoroethoxy)phenyl carbamate comprises the addition of 4 (2,2-dichloro-1,1 -difluoroethoxy)phenyl isocyanate (2.68 g) to absolute ethanol (30 ml) at 220C. After standing for 10 minutes, the excess ethanol was removed from the clear reaction mixture under reduced pressure to give a colourless solid (3.0 g, 95 percent).
Example 4 N (((4-(2,2-Dichloro-1 1 -difluoroethoxy- phenyl)amino)carbonyl-2-chlorobenzamide
2-Chlorobenzamide (0.8 g) was added to a solution of ethyl 4-(2,2-dichloro-1,1 - difluoroethoxy)phenyl-carbamate (1.6 g) in odichlorobenzene (25 ml). The resulting slurry was heated under a reflux for five hours. The cooled suspension was dissolved in methanol and made up to a known volume and assayed by HPLC against an external standard. The yield was 22 percent.
Example 5
Ethyl-4-chlorophenylcarbamate
Ethyl chloroformate (108.3 g) in tetrahydrofuran (250 ml) was added dropwise over 10 minutes to a stirred solution of 4chlorophenylaniline (128.0 g) and triethylamine (139 ml) at OOC. The resulting suspension was stirred for a further four hours at 0 to 220C. The solids were removed by filtration and the clear filtrate was concentrated to a brown oil which solidified after standing for several hours at OOC.
The product was crystallized from ethanol/water (1:1, 1 liter) to give an off-white solid (145 g, 73 percent), m.p. 690C.
Elemental analysis percent expected/found: C, 54.14/54.17 H, 5.05/5.07; N. 7.02/6.93; Cl, 17.76/17.51.
Example 6
N-( (4-Chlorophenyl )am ino)carbonyl-2chlorobenzamide
2-Chlorobenzamide (0.8 g) was added to a solution of ethyl 4-chlorophenylcarbamate (1.0 g) in o-dichlorobenzene (25 ml). The resulting slurry was heated under reflux for 24 hours. The cooled suspension was dissolved in methanol and made up to a known volume and assayed by HPLC against an external standard of N-((4chlorophenyl)amino)carbonyl-2-chlorobenzamide previously prepared. The yield of the desired compound was 83 percent.
Example 7 N-((4-Chlorophenyl)amino)carbonyl-2- chlorobenzamide
2-Chlorobenzamide (15.5 g) and 4chlorophenyl-isocyanate (16.89 g) in dry xylene (200 ml) were heated to gentle reflux and the ensuing orange solution heated further under reflux for 24 hours. The solution was cooled and a solid formed, 26 g, 84 percent, m.p. 195.50 to 1 960C, filtered and crystallized successively from acetic acid and ethyl acetate, m.p. 1 96.50C to 1 970C.
Found: C, 55.38; H, 3.58; N, 9.49. Required: C,
54.37; H, 3.24; N. 9.06.
Example 8 4-Hydroxyphenylisocyanate
To a solution of phosgene (39.6 g) in ethyl acetate (125 ml) at 50 was added a slurry of 4aminophenol (21.89) in ethyl acetate (200 ml).
The reaction was allowed to stand for an hour at 50--200. The resulting clear solution was heated to reflux and phosgene slowly passed into the solution through a gas sparge tube. After 30 minutes the passage of gas was stopped, and the reaction allowed to cool. The ethyl acetate and excess phosgene were removed by atmospheric distillation. The residue was vacuum distilled to give a colourless oil (17.8 g 66%).
Example 9
N-((4-Hydroxyphenyl)amino)carbonyl-2chlorobenza mide
A suspension of 2-chlorobenzamide (1.4 g) in dry xylene (35 ml) was treated with 4hydroxyphenylisocyanate (0.6 g) in dry xylene (5 ml) and the resulting mixture heated under reflux for 1 hour. The reaction mixture was cooled and then diluted to known volume with methanol and assayed by HPLC against an external standard.
Yield of desired compound 84%.
Claims (9)
1. A process for preparing a compound having the general formula:-
wherein X and Y are individually H,F,CI, alkyl or haloalkyl; R and R' are individually H, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro or cyano; wherein T is halogen, halogenated alkyl or the group ZR" wherein R" is H, alkyl aryl, alkyl, halogenated alkyl, halogenated alkylene, pyridyl, substituted pyridyl, phenyl or substituted phenyl and Z is O or S, which comprises reacting an aniline compound having the formula:-
wherein R, R', R" and Tare as above defined with an active carbonyl compound of the formula:-
wherein W is individually Cl, alkoxy or haloalkoxy, optionally in the presence of a tertiary base, and thereafter reacting the resulting compound of the formula::
wherein R, R', R" and Tare as above defined and
V is NCO or
wherein W is as above defined with a compound of the formula:-
wherein X and Y are as above defined, at a temperature in the range of from 800 to 1800 C.
2. A process as claimed in claim 1 wherein the compound of the formula:-
wherein V is NHCOW, is prepared by reacting a compound wherein V is NCO with an alkanol of the formula WH.
3. A process as claimed in claim 1 or claim 2, wherein R" is pyridyl substituted with Cl, CF3,
NO2, or CN, or phenyl substituted with F, Cl, CF3, NO2 or CN.
4. A process as claimed in any one of the preceding claims which is carried out in an inert aromatic solvent.
5. A process as claimed in claim 4 wherein the solvent is o-dichlorobenzene.
6. A process as claimed in claim 4 wherein the solvent is xylene.
7. A process as claimed in any one of claims 4 to 6 wherein the reaction is carried out at reflux temperature.
8. A process as claimed in claim 1 substantially as hereinbefore described with reference to any one of the Examples.
9. A benzoylphenylurea as defined in claim 1 whenever prepared by a process as claimed in any one of the preceding claims.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08128333A GB2106499B (en) | 1981-09-18 | 1981-09-18 | Method for making benzoylphenylureas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08128333A GB2106499B (en) | 1981-09-18 | 1981-09-18 | Method for making benzoylphenylureas |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2106499A true GB2106499A (en) | 1983-04-13 |
| GB2106499B GB2106499B (en) | 1986-01-02 |
Family
ID=10524606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08128333A Expired GB2106499B (en) | 1981-09-18 | 1981-09-18 | Method for making benzoylphenylureas |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2106499B (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4550202A (en) * | 1983-01-24 | 1985-10-29 | Duphar International Research B.V. | Benzoylurea compounds, and pesticidal and pharmaceutical compositions comprising same |
| EP0143302A3 (en) * | 1983-10-27 | 1985-12-18 | Nihon Tokushu Noyaku Seizo K.K. | Benzoylurea derivatives and intermediates |
| US4567295A (en) * | 1983-01-24 | 1986-01-28 | Duphar International Research B.V. | Composition active against mites, whitefly and thrips, pharmaceutical composition, and new benzoylurea compounds |
| EP0176868A1 (en) * | 1984-09-29 | 1986-04-09 | Shell Internationale Researchmaatschappij B.V. | Benzoyl ureas having an insecticidal activity |
| US4594451A (en) * | 1983-04-22 | 1986-06-10 | Montedison S.P.A. | Benzoyl-ureas exerting an insecticide activity |
| EP0205049A1 (en) * | 1985-05-31 | 1986-12-17 | BASF Aktiengesellschaft | N-benzoyl-N'-(1,1-difluoro-phenylmethyl)-phenyl ureas, processes for their production and their use in pest control |
| US4632938A (en) * | 1984-02-27 | 1986-12-30 | Takeda Chemical Industries, Ltd. | Thiophenylureas, their production and use |
| US4665235A (en) * | 1983-01-24 | 1987-05-12 | Duphar International Research B.V. | Benzoylurea compounds, and pesticidal and pharmaceutical compositions comprising same |
| EP0268952A1 (en) * | 1986-11-25 | 1988-06-01 | Bayer Ag | Benzoyl(thio) ureas |
| WO1993004044A1 (en) * | 1991-08-20 | 1993-03-04 | Korea Research Institute Of Chemical Technology | Pyrazole containing benzoyl urea derivatives, composition and use |
| US5210100A (en) * | 1984-08-31 | 1993-05-11 | Ciba-Geigy Corporation | Phenylbenzoylureas |
-
1981
- 1981-09-18 GB GB08128333A patent/GB2106499B/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4710516A (en) * | 1983-01-24 | 1987-12-01 | Duphar International Research B.V. | Insecticidal and acaricidal composition comprising a benzoylurea compound |
| US4567295A (en) * | 1983-01-24 | 1986-01-28 | Duphar International Research B.V. | Composition active against mites, whitefly and thrips, pharmaceutical composition, and new benzoylurea compounds |
| US4550202A (en) * | 1983-01-24 | 1985-10-29 | Duphar International Research B.V. | Benzoylurea compounds, and pesticidal and pharmaceutical compositions comprising same |
| US4609676A (en) * | 1983-01-24 | 1986-09-02 | Duphar International Research B.V. | Benzoylurea compounds, and pesticidal and pharmaceutical compositions comprising same |
| US4665235A (en) * | 1983-01-24 | 1987-05-12 | Duphar International Research B.V. | Benzoylurea compounds, and pesticidal and pharmaceutical compositions comprising same |
| US4594451A (en) * | 1983-04-22 | 1986-06-10 | Montedison S.P.A. | Benzoyl-ureas exerting an insecticide activity |
| EP0143302A3 (en) * | 1983-10-27 | 1985-12-18 | Nihon Tokushu Noyaku Seizo K.K. | Benzoylurea derivatives and intermediates |
| US4632938A (en) * | 1984-02-27 | 1986-12-30 | Takeda Chemical Industries, Ltd. | Thiophenylureas, their production and use |
| US5210100A (en) * | 1984-08-31 | 1993-05-11 | Ciba-Geigy Corporation | Phenylbenzoylureas |
| EP0176868A1 (en) * | 1984-09-29 | 1986-04-09 | Shell Internationale Researchmaatschappij B.V. | Benzoyl ureas having an insecticidal activity |
| US5607977A (en) * | 1984-09-29 | 1997-03-04 | Shell Agrar Gmbh & Co. Kg | Benzoylureas |
| EP0205049A1 (en) * | 1985-05-31 | 1986-12-17 | BASF Aktiengesellschaft | N-benzoyl-N'-(1,1-difluoro-phenylmethyl)-phenyl ureas, processes for their production and their use in pest control |
| EP0268952A1 (en) * | 1986-11-25 | 1988-06-01 | Bayer Ag | Benzoyl(thio) ureas |
| WO1993004044A1 (en) * | 1991-08-20 | 1993-03-04 | Korea Research Institute Of Chemical Technology | Pyrazole containing benzoyl urea derivatives, composition and use |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2106499B (en) | 1986-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19970918 |