US2870205A - Substituted ureas - Google Patents
Substituted ureas Download PDFInfo
- Publication number
- US2870205A US2870205A US616592A US61659256A US2870205A US 2870205 A US2870205 A US 2870205A US 616592 A US616592 A US 616592A US 61659256 A US61659256 A US 61659256A US 2870205 A US2870205 A US 2870205A
- Authority
- US
- United States
- Prior art keywords
- urea
- hydroxypropyl
- weight
- substituted ureas
- compounds
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 235000013877 carbamide Nutrition 0.000 title description 10
- 150000003672 ureas Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- -1 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea Chemical compound 0.000 description 5
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- YDCBQSVFPRBGKG-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-(3-hydroxypropyl)urea Chemical compound ClC=1C=C(C=C(C1)Cl)NC(=O)NCCCO YDCBQSVFPRBGKG-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XFKZYUOOMFMGLG-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)urea Chemical compound OCCCNC(=O)NC1=CC=C(Cl)C(Cl)=C1 XFKZYUOOMFMGLG-UHFFFAOYSA-N 0.000 description 2
- VHEYHMGSWDZXEN-UHFFFAOYSA-N 2-hydroxypropylurea Chemical compound CC(O)CNC(N)=O VHEYHMGSWDZXEN-UHFFFAOYSA-N 0.000 description 2
- DNPHEDNKXRMPAX-UHFFFAOYSA-N 3-hydroxypropylurea Chemical compound NC(=O)NCCCO DNPHEDNKXRMPAX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GLCIMEOOSALMQT-UHFFFAOYSA-N 1,2,3-trichloro-5-isocyanatobenzene Chemical compound ClC1=CC(N=C=O)=CC(Cl)=C1Cl GLCIMEOOSALMQT-UHFFFAOYSA-N 0.000 description 1
- DSEXYRJTIPASEZ-UHFFFAOYSA-N 1,2-dibromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1Br DSEXYRJTIPASEZ-UHFFFAOYSA-N 0.000 description 1
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 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
- C07C275/30—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 being further substituted by halogen atoms, or by nitro or nitroso groups
Definitions
- This invention relates to new and useful substituted ureas and to processes for making same.
- the substituted ureas of this invention may be represented by the structure .1-(3,4dichlorophenyl) 3-(3-hydroxypropyl) urea 1-(3,4-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea l-(3,4,5-tribromophenyl) 3-(3-hydroxypropyl) 'urea
- the preparation of the compounds of this invention is the following:
- Example I To a suitable reaction vessel equipped with an agitator is added and mixed approximately 18.8 parts by weight of 3,4-dichlorophenylisocyanate, approximately 7.5 parts by weight of 3-amino-1-propanol and approximately 54 parts by weight of diethyl ether. The reaction is exothermic and upon its completion, as evidenced by a temperature drop, the mass is cooled and permitted to stand for one hour at room temperature. The mass is filtered and the filter cake is washed with two successive 18 parts by weight portions of diethyl ether. Upon air drying the filter cake, approximately 26 parts by weight of l- (3,4-dichlorophenyl) 3-(3-hydroxypropyl) urea is obtained as white granules, M. P. 126.5- 128 C.
- Example II Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with an equal weight of 3,5-dichlorophenylisocyanate, there is obtained 1-(3,5- dichlorophenyl) 3-(3-hydroxypropyl) urea.
- Example Ill Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a' chemically equivalent weight of 3,4,5-trichlorophenylisocyanate, there is obtained 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea.
- Example IV Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a chemically equivalent weight of 3,4-dibromophenylisocyanate, there is obtained 1-(3,4-dibromophenyl) 3'(3-hydroxyproPYl) urea.
- the compounds of this invention are particularly useful in controlling bacterial growth, especially M icrococcus pyogenes var. aureus.
- a detergent soap i. e. an alkali metal salt of a fatty acid of animal or vegetableorigin such as stearic acid, lauric acid, palmitic acid, ole'ic cid, ricinoleic acid, myristic acid, and the like,
- Example II prepared from 3,4-dichlorophenylisocyanate and 2-hydroxy-n-propylamine in accordance with the process of Example I).
- the respective compounds were incorporated in the said alkali metal fatty acid soap in a weight ratio of 1 part to 50 parts soap.
- Aliquots of each were added to a Sabourards dextrose agar medium so as to give concentrations of 1, 10 and parts per 100,000 of the respective urea derivatives in the agar.
- the agar in each case was then poured into a petri dish, allowed to harden, and then inoculated with a standard culture of Micrococcus pyogenes var. aureus of standard resistance.
- the incubation in each instance was made at 37 C. for 48 hours. The extent of growth is noted below:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Description
2,870,205 7 SUBSTITUTED UREAS David J. Beaver, Richmond Heights, and Paul I. Stotfel,
St. Louis, Mo., assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware Application October 18, 1956 Serial No. 616,592
6 Claims. (Cl. 260-553) No Drawing.
This invention relates to new and useful substituted ureas and to processes for making same.
The substituted ureas of this invention may be represented by the structure .1-(3,4dichlorophenyl) 3-(3-hydroxypropyl) urea 1-(3,4-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea l-(3,4,5-tribromophenyl) 3-(3-hydroxypropyl) 'urea As illustrative of the preparation of the compounds of this invention is the following:
Example I To a suitable reaction vessel equipped with an agitator is added and mixed approximately 18.8 parts by weight of 3,4-dichlorophenylisocyanate, approximately 7.5 parts by weight of 3-amino-1-propanol and approximately 54 parts by weight of diethyl ether. The reaction is exothermic and upon its completion, as evidenced by a temperature drop, the mass is cooled and permitted to stand for one hour at room temperature. The mass is filtered and the filter cake is washed with two successive 18 parts by weight portions of diethyl ether. Upon air drying the filter cake, approximately 26 parts by weight of l- (3,4-dichlorophenyl) 3-(3-hydroxypropyl) urea is obtained as white granules, M. P. 126.5- 128 C.
Example II Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with an equal weight of 3,5-dichlorophenylisocyanate, there is obtained 1-(3,5- dichlorophenyl) 3-(3-hydroxypropyl) urea.
Example Ill Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a' chemically equivalent weight of 3,4,5-trichlorophenylisocyanate, there is obtained 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea.
Example IV Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a chemically equivalent weight of 3,4-dibromophenylisocyanate, there is obtained 1-(3,4-dibromophenyl) 3'(3-hydroxyproPYl) urea.
In the preparation of the new compounds of this invention other inert solvents than diethyl ether may be employed, e. g. di-isopropyl ether, methyl butyl ether,
United States Patent Patented Jan. 2 1959 ICE ' 2 the liquid alkanes, and the like. The reaction tempera ture employed in making the new compounds may vary widely but ingcneral will be .between room temperature and the reflux temperature of the system.
The compounds of this invention are particularly useful in controlling bacterial growth, especially M icrococcus pyogenes var. aureus. In this regard the substituted ureas of this invention when compounded with a detergent soap (i. e. an alkali metal salt of a fatty acid of animal or vegetableorigin such as stearic acid, lauric acid, palmitic acid, ole'ic cid, ricinoleic acid, myristic acid, and the like,
or mixtures thereof obtained from tallow, lard, coconut Percent Oleic and linoleic acid About 46 Stearic About 14 Palmitic acid -l. About 30 Lower fatty acids, e. g. myristic, lauric, etc About 10) and compared to l-(3,4-dichlorophenyl) 3-(2-hydroxypropyl) urea (a white solid melting at 152.0152.8 C.
prepared from 3,4-dichlorophenylisocyanate and 2-hydroxy-n-propylamine in accordance with the process of Example I). The respective compounds were incorporated in the said alkali metal fatty acid soap in a weight ratio of 1 part to 50 parts soap. Aliquots of each were added to a Sabourards dextrose agar medium so as to give concentrations of 1, 10 and parts per 100,000 of the respective urea derivatives in the agar. The agar in each case was then poured into a petri dish, allowed to harden, and then inoculated with a standard culture of Micrococcus pyogenes var. aureus of standard resistance. The incubation in each instance was made at 37 C. for 48 hours. The extent of growth is noted below:
Compound/Concentration in parts per 100,00(
1-(3,4-dich1oropheny1) 3-(2-hydroxypropyl) urea. 1-(3.4-rlichl0rophenyl) 3-(3-hydroxypropyl) urea.
none. heavy. heavy.
droxypropyl) urea with an equal weight of 1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea or 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea. Similar control is obtained employing the corresponding bromine substituted analogues thereof.
Relatively small amounts of these new substituted ureas in a detergent soap composition have been found to yield efiective antiseptic detergent soap compositions. Amounts as low as 0.5% by weight based on the weight of the detergent soap have proved satisfactory. However, it is preferred to employ amounts in the order of l to 5% by weight. Larger amounts, e. g. up to 10% by weight, may be employed, however, such upper limit will be determined by practical considerations.
While this invention has been described with respect to certain embodiments, it is not so limited and it is to be understood that variations and modifications thereof What is claimed is: l 6. The process of making the compounds of claim 1, 1. Compounds of the structure which comprises reacting in substantially equimolecular proportions 3-amino-l-propanol and an isocyanate of the 5 ing the same significance as in claim 1, in the presence of an inert solvent at a temperature in the range of room where X C is a halo en substituted: hen l: radical n 6H5 g p y temperature to the reflux temperature of the system.
free of substituents ortho to the nitrogen atom,- where X gf ii ig fg and where n 18 a whole number r References Cited in the file of this patent 2. Compounds of claim 1 where X is selected from 10 UNITED STATES PATENTS the g p consisting of bromine n chlorine 3,663,729 m et a1 D6012, 1953 wgrgrclarrrlugggnds of claim 1 wherein X 18 chlorine and OTHER REFERENCES 4. 1-(3,4-dichlorophenyl) 3-(3-hydroxypropyl) urea. Thompson et al.: Botanical Gazette, vol. 107: pages 5. 1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea. 15 494 to 498 (1946).
Claims (1)
1. COMPOUNDS OF THE STRUCTURE
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US616592A US2870205A (en) | 1956-10-18 | 1956-10-18 | Substituted ureas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US616592A US2870205A (en) | 1956-10-18 | 1956-10-18 | Substituted ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2870205A true US2870205A (en) | 1959-01-20 |
Family
ID=24470158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US616592A Expired - Lifetime US2870205A (en) | 1956-10-18 | 1956-10-18 | Substituted ureas |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2870205A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3006955A (en) * | 1957-12-05 | 1961-10-31 | Basf Ag | N'-cyclohexyl or octyl, n'-beta-hydroxyethyl or propyl, n2,n2-dimethyl or diethyl-urea |
| US3072719A (en) * | 1959-04-23 | 1963-01-08 | Monsanto Chemicals | 3, 4-dichlorophenyl substituted alkyl ureas |
| US3112342A (en) * | 1960-10-03 | 1963-11-26 | Du Pont | 1-methoxy-1-methyl-3-(3-chloro-4-cumenyl) urea |
| US3125601A (en) * | 1964-03-17 | I-phenyl | ||
| US3133079A (en) * | 1960-10-13 | 1964-05-12 | Du Pont | Herbicidal aryl alkyl imidazolinones |
| US3254984A (en) * | 1963-01-09 | 1966-06-07 | Du Pont | Herbicidal composition and method |
| US3321415A (en) * | 1963-08-28 | 1967-05-23 | Bayer Ag | Polyurethanes prepared from polyhydroxyurea polyamines |
| US4109081A (en) * | 1975-05-15 | 1978-08-22 | Mallinckrodt, Inc. | 1-(3,5-disubstituted-2,4,6-triiodophenyl)-3-(polyhydroxy-alkyl)urea compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2663729A (en) * | 1952-11-04 | 1953-12-22 | Du Pont | Haloarylhydroxyalkyl-ureas |
-
1956
- 1956-10-18 US US616592A patent/US2870205A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2663729A (en) * | 1952-11-04 | 1953-12-22 | Du Pont | Haloarylhydroxyalkyl-ureas |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125601A (en) * | 1964-03-17 | I-phenyl | ||
| US3006955A (en) * | 1957-12-05 | 1961-10-31 | Basf Ag | N'-cyclohexyl or octyl, n'-beta-hydroxyethyl or propyl, n2,n2-dimethyl or diethyl-urea |
| US3072719A (en) * | 1959-04-23 | 1963-01-08 | Monsanto Chemicals | 3, 4-dichlorophenyl substituted alkyl ureas |
| US3112342A (en) * | 1960-10-03 | 1963-11-26 | Du Pont | 1-methoxy-1-methyl-3-(3-chloro-4-cumenyl) urea |
| US3133079A (en) * | 1960-10-13 | 1964-05-12 | Du Pont | Herbicidal aryl alkyl imidazolinones |
| US3254984A (en) * | 1963-01-09 | 1966-06-07 | Du Pont | Herbicidal composition and method |
| US3321415A (en) * | 1963-08-28 | 1967-05-23 | Bayer Ag | Polyurethanes prepared from polyhydroxyurea polyamines |
| US4109081A (en) * | 1975-05-15 | 1978-08-22 | Mallinckrodt, Inc. | 1-(3,5-disubstituted-2,4,6-triiodophenyl)-3-(polyhydroxy-alkyl)urea compounds |
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