US3146232A - 5-(5-nitro-2-furyl-mono- and di-vinylene)-1, 3, 4-oxadiazoline-2-one and process - Google Patents
5-(5-nitro-2-furyl-mono- and di-vinylene)-1, 3, 4-oxadiazoline-2-one and process Download PDFInfo
- Publication number
- US3146232A US3146232A US224200A US22420062A US3146232A US 3146232 A US3146232 A US 3146232A US 224200 A US224200 A US 224200A US 22420062 A US22420062 A US 22420062A US 3146232 A US3146232 A US 3146232A
- Authority
- US
- United States
- Prior art keywords
- nitro
- oxadiazoline
- furyl
- compounds
- vinylene
- 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
- 238000000034 method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- -1 5-nitro-2- furyl Chemical group 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- KHZWNDSKYGHLJD-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)prop-2-enoyl chloride Chemical compound [N+](=O)([O-])C1=CC=C(O1)C(C(=O)Cl)=C KHZWNDSKYGHLJD-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XLUWNAXYGUQQJL-UHFFFAOYSA-N 2h-1,3,4-oxadiazol-5-one Chemical group O=C1OCN=N1 XLUWNAXYGUQQJL-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241000223932 Eimeria tenella Species 0.000 description 1
- 241000272496 Galliformes Species 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
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical group NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Definitions
- n is an integer from 1 to 2.
- the new compounds specified above are crystalline solids somewhat soluble in an organic solvent such as methanol, ethanol, acetone and dioxane and of low watersolubility. They have been found to be very active as inhibitory agents against the growth of microorganisms.
- the culture base used I consists of 0.5% of peptone, 0.5% of glucose and 0.3% of extracted yeast, and is adjusted to pH 7.0 and sterilized under 1.46 kglcm. steam pressure for 20 it r l rhinistered orally to rabbits in amount of 100 mgJkg. and measured after 4 hours.
- the compounds of this invention exhibit a pronounced activity in effectively combating Eimeria tenella and Trichomonas vaginalis organisms when administered orally. But the compounds show no toxicity on the animals. This fact is presumably due to a slight difference between the in vitro and the in vivo activity.
- Cornpound I produces a complete cure on domestic fowls infected with coccidium when incorporated in their feed at the level of 0.01% by Weight.
- the LD in mice of Compound I and Compound II is respectively 300 mg./ kg. and 1.0 g./kg., and Compound I produces no chronic toxicity on rats when administered in amount of 30 mg./ kg. for 6 months.
- the compounds of this invention can be employed as very effective antiseptic and antimicrobial agents and parasiticides without any danger of adverse effect.
- the compounds of this invention can be effectively employed with other agents which are apt to lose in vivo activity.
- the dosage can accordingly be confined to a minimum amount, and the compounds can be profitably employed by mixing in foodand feedstufis.
- Compounds I and I produce a satisfactory antiseptic effect within the range of 10 to 2-0 p.p.m.
- the compounds of this invention may be administered with an inert powder as a dust or as a tablet. They may also be dispersed in water with an appropriate dispersant or emulsifying agent, or dissolved in an organic solvent such as propylene glycol. The dispersion or solution thus prepared is sprayed or coated onto a harvested or finished article, or the article to be protected is dipped in said dispersion or solution. Said compounds can further be mixed in foodand feedstuff materials.
- n is an integer from 1 to 2
- n is an integer from 1 to 2
- the precipitating crystalline product 5-nitro-2-furyl acrylic acid hydrazide or 5-nitro-2-furyl divinylene carboxylic acid hydrazide is separated by filtration, dissolved in an aqueous solution of hydrogen chloride, and then phosgene gas is introduced beneath the surface of the resultant solution at a temperature ranging from 0 to C.
- the precipitating yellow crystalline product is separated by filtration and recrystallized according to the ordinary method.
- the resultant solution is cooled to C. and phosgene gas is introduced portionwise beneath the surface of the liquid reaction mixture during 2 hours at a temperature not higher than 80 C.
- the crystalline precipitate which forms during the reaction is separated by filtration.
- n is an integer selected from the group consisting of 1 and 2.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
United States Patent 3,146,232 S-(S-NITRO-Z-FURYlL-MONO- AND DI-VINYLENE)- 1,3,4-XADIAZOLINE-2-0NE AND PROCESS Haruo Saiiraehi, 432 Ryutozaki oaza Kanehira, Fukuoka,
Japan; Akin ()yama, 55 Shimogamo-shibamoto-cho, Sakyo-ku, Kyoto, Japan; Ryuzo Ueno, 65 Nango-cho, Nishinomiya, Japan; and Hiroshige Inoue, 2-136 Nishimikuni-cho, Higashiyodogawa-hu, Osaka, Japan No Drawing. Filed Sept. 17, 1962, Ser. No. 224,200 3 Claims. (Cl. 260240) This invention relates to a series of novel compounds having the formula:
N NH
wherein n is an integer from 1 to 2. (In the following, the compound of n=1 will be described as Compound I and that of n=2 as Compound II.)
The new compounds specified above are crystalline solids somewhat soluble in an organic solvent such as methanol, ethanol, acetone and dioxane and of low watersolubility. They have been found to be very active as inhibitory agents against the growth of microorganisms.
5 (S-nitro-2-furyl)-1,3,4-oxadiazoline-2-one disclosed in the United States Patent 2,918,473 is a similar compound. But the present invention is based upon the discovery that a vinyl group binding the 1,3,4-oxadiazoline- 2-one groups which are bonded to the nitrofuran nucleus at position 2 plays a very pronounced part in increasing antimicrobial efficacy, in lowering toxicity on animals and in maintaining in vivo activity.
The properties of the compounds of this invention are as follows:
Cultivated at 37 C. [or 48 hours. The culture base used Iconsists of 0.5% of peptone, 0.5% of glucose and 0.3% of extracted yeast, and is adjusted to pH 7.0 and sterilized under 1.46 kglcm. steam pressure for 20 it r l rhinistered orally to rabbits in amount of 100 mgJkg. and measured after 4 hours.
The compounds of this invention exhibit a pronounced activity in effectively combating Eimeria tenella and Trichomonas vaginalis organisms when administered orally. But the compounds show no toxicity on the animals. This fact is presumably due to a slight difference between the in vitro and the in vivo activity. For instance, Cornpound I produces a complete cure on domestic fowls infected with coccidium when incorporated in their feed at the level of 0.01% by Weight. The LD in mice of Compound I and Compound II is respectively 300 mg./ kg. and 1.0 g./kg., and Compound I produces no chronic toxicity on rats when administered in amount of 30 mg./ kg. for 6 months.
In view of these findings, the compounds of this invention can be employed as very effective antiseptic and antimicrobial agents and parasiticides without any danger of adverse effect.
The loss of in vivo activity, furthermore, being very slight, the compounds of this invention can be effectively employed with other agents which are apt to lose in vivo activity. The dosage can accordingly be confined to a minimum amount, and the compounds can be profitably employed by mixing in foodand feedstufis. As preservatives, Compounds I and I produce a satisfactory antiseptic effect within the range of 10 to 2-0 p.p.m.
The compounds of this invention may be administered with an inert powder as a dust or as a tablet. They may also be dispersed in water with an appropriate dispersant or emulsifying agent, or dissolved in an organic solvent such as propylene glycol. The dispersion or solution thus prepared is sprayed or coated onto a harvested or finished article, or the article to be protected is dipped in said dispersion or solution. Said compounds can further be mixed in foodand feedstuff materials.
The method of preparing the compounds of this invention comprises reacting hydrazine hydrate with 5-nitro-2- furyl monoor divinylene carboxylic acid chloride having -CH CH- or CH=CHCH=CH- group, and then treating the resultant acid hydrazide with phosgene.
In carrying out the reaction, S-nitro-Z-furyl monoor divinylene carboxylic acid chloride having the formula:
wherein n is an integer from 1 to 2, is dissolved in an organic solvent, and the resultant solution is mixed dropwise in a cooled aqueous solution of hydrazine hydrate. The precipitating crystalline product 5-nitro-2-furyl acrylic acid hydrazide or 5-nitro-2-furyl divinylene carboxylic acid hydrazide is separated by filtration, dissolved in an aqueous solution of hydrogen chloride, and then phosgene gas is introduced beneath the surface of the resultant solution at a temperature ranging from 0 to C. Upon completion of the reaction, the precipitating yellow crystalline product is separated by filtration and recrystallized according to the ordinary method.
Preferred examples are as follows, but they are not construed as limiting the scope and extent of the invention:
EXAMPLE 1 5-(5-Nitro-2-Furylvinylene)-J,3,4-Oxadiaz0line-2-One O N NH and iion=oni=0 A solution of 201.5 g. of 5-nitro-2-furylacrylic acid chloride in 1,000 cc. of benzene is cooled and added dropwise with stirring to an aqueous solution of 313 g. of 80% hydrazine hydrate in 2 liters of water during 2 hours. Stirring is further continued for 30 minutes. The resulting precipitate is separated by filtration and dissolved with stirring in an aqueous solution of 500 cc. of concentrated hydrochloric acid in 2,500 cc. of water at room temperature. The resultant solution is cooled to 10 C. and phosgene gas is introduced portionwise beneath the surface of the liquid reaction mixture with stirring during 2 hours at a temperature not higher than 80 C. The crystalline product which forms during the reaction is separated by filtration. Upon recrystallization from an acetone-water mixture, there are obtained 126 g. of 5-(5-nitro-2-furylvinylene)-1,3,4-oxadiazoline-2-one as yellow crystalline solids which melt at 213 C. with decomposition. Yield is 55%.
Analysis.Calcd. for C H N O C=43.05%; H=2.26%; N=18.83%. Found: C=43.35%; H=2.01%; N=18.80%
EXAL EPLE 2 5- (5-Nitr0-2-Furyldivinylene)-1,3,4-0xadiaz0Iine-2-One GHQH NNH GEN- -CH=CHCH=CH- A solution of 45.5 g. of -nitro-2-furylpentadienic acid chloride in 500 cc. of benzene is cooled and added drop- Wise with stirring to an aqueous solution of 200 g. of 80% hydrazine hydrate in 1,600 cc. of water during 1 hour. Stirring is continued for 30 minutes. The precipitate which forms is separated by filtration and dissolved with stirring in an aqueous solution of 250 cc. of concentrated hydrochloric acid in 2,500 cc. of water at room temperature. The resultant solution is cooled to C. and phosgene gas is introduced portionwise beneath the surface of the liquid reaction mixture during 2 hours at a temperature not higher than 80 C. The crystalline precipitate which forms during the reaction is separated by filtration. Upon recrystallization from a dioxane-water mixture, there are obtained 17.4 g. of a yellow crystalline product which melts at a temperature above 250 C. with decomposition. Yield is 35%.
Analysis.Calcd. for C H N 0 C=48.20%; H=2.83%; N=17.27%. Found: C=48.46%;
4 What is claimed is: 1. A compound of the formula:
|3HCH O2N-C wherein n is an integer selected from the group consisting of 1 and 2.
2. 5-(5-nitro-2-furylvinylene) 1,3,4 oxadiazoline-Z- one.
3. 5-(S-nitro-2-furyldivinylene) 1,3,4 oxadiazoline- 2-or1e.
References Cited in the file of this patent German Patentanmeldung F 12,656 IVb/lZp, April 19, 1956.
Darnow et al.: Chem. Ber., vol. 82, pages 121 to 123 (1949).
Chemical Abstracts, vol. 54, cols. 17359 to 17360 (1960), QDl A51. (Abstract of Saikachi et al., Chem. Pharm. Bull. (Tokyo), vol. 7, pages 584-8 (1959).)
Chemical Abstracts, vol. 55, col. 7380 (1961), Q1) 1A51. (Abstracts of Saikachi et al., Yakugaku Zasshi, vol. 80, pages 1584-8 (1960).)
Claims (1)
1. A COMPOUND OF THE FORUMLA:
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US224200A US3146232A (en) | 1962-09-17 | 1962-09-17 | 5-(5-nitro-2-furyl-mono- and di-vinylene)-1, 3, 4-oxadiazoline-2-one and process |
| GB3575162A GB949288A (en) | 1962-09-17 | 1962-09-19 | Novel 1,3,4-oxadiazoline derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US224200A US3146232A (en) | 1962-09-17 | 1962-09-17 | 5-(5-nitro-2-furyl-mono- and di-vinylene)-1, 3, 4-oxadiazoline-2-one and process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3146232A true US3146232A (en) | 1964-08-25 |
Family
ID=22839670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US224200A Expired - Lifetime US3146232A (en) | 1962-09-17 | 1962-09-17 | 5-(5-nitro-2-furyl-mono- and di-vinylene)-1, 3, 4-oxadiazoline-2-one and process |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3146232A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3260716A (en) * | 1962-09-11 | 1966-07-12 | Toyama Kagaku Kogyo Kabushiki | Process for the preparation of new 5-nitrofuryl compounds |
| US3303188A (en) * | 1962-09-11 | 1967-02-07 | Toyama Kagaku Kogyo Kabushiki | Process for preparing new 5-nitrofuryl compounds |
| US3336304A (en) * | 1964-01-28 | 1967-08-15 | Fujisawa Pharmaceutical Co | 1, 3, 4-oxadiazolin-5-one derivatives and process for the preparation thereof |
| US3474462A (en) * | 1966-03-14 | 1969-10-21 | Squibb & Sons Inc | Nitrofuryl oxadiazolones |
| US3491091A (en) * | 1962-03-28 | 1970-01-20 | Boehringer & Soehne Gmbh | 5-nitrofuran derivatives |
-
1962
- 1962-09-17 US US224200A patent/US3146232A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3491091A (en) * | 1962-03-28 | 1970-01-20 | Boehringer & Soehne Gmbh | 5-nitrofuran derivatives |
| US3260716A (en) * | 1962-09-11 | 1966-07-12 | Toyama Kagaku Kogyo Kabushiki | Process for the preparation of new 5-nitrofuryl compounds |
| US3303188A (en) * | 1962-09-11 | 1967-02-07 | Toyama Kagaku Kogyo Kabushiki | Process for preparing new 5-nitrofuryl compounds |
| US3336304A (en) * | 1964-01-28 | 1967-08-15 | Fujisawa Pharmaceutical Co | 1, 3, 4-oxadiazolin-5-one derivatives and process for the preparation thereof |
| US3474462A (en) * | 1966-03-14 | 1969-10-21 | Squibb & Sons Inc | Nitrofuryl oxadiazolones |
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