JPS6228141B2 - - Google Patents
Info
- Publication number
- JPS6228141B2 JPS6228141B2 JP56194354A JP19435481A JPS6228141B2 JP S6228141 B2 JPS6228141 B2 JP S6228141B2 JP 56194354 A JP56194354 A JP 56194354A JP 19435481 A JP19435481 A JP 19435481A JP S6228141 B2 JPS6228141 B2 JP S6228141B2
- Authority
- JP
- Japan
- Prior art keywords
- dithiine
- formula
- dihydro
- hydrogen
- groups
- 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
Links
- 238000000034 method Methods 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical compound C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- RIYVKHUVXPAOPS-UHFFFAOYSA-N dithiine Chemical compound S1SC=CC=C1 RIYVKHUVXPAOPS-UHFFFAOYSA-N 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000009835 boiling Methods 0.000 description 10
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- -1 hydrogen halides Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 4
- 150000004662 dithiols Chemical class 0.000 description 4
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical compound S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 description 3
- OVBZTVYBXDWHAA-UHFFFAOYSA-N 4-hydroxyhexan-3-one Chemical compound CCC(O)C(=O)CC.CCC(O)C(=O)CC OVBZTVYBXDWHAA-UHFFFAOYSA-N 0.000 description 3
- FAYLFGHUYPPDPQ-UHFFFAOYSA-N 5,6-dimethyl-2,3-dihydro-1,4-dithiine Chemical compound CC1=C(C)SCCS1 FAYLFGHUYPPDPQ-UHFFFAOYSA-N 0.000 description 3
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 3
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 2
- FLVUYLNVCUGFGX-UHFFFAOYSA-N 2,3-dihydro-1,4-dithiine Chemical class C1CSC=CS1 FLVUYLNVCUGFGX-UHFFFAOYSA-N 0.000 description 2
- ZERRJEOSIUQKQQ-UHFFFAOYSA-N 2,5-dimethyl-2,3-dihydro-1,4-dithiine Chemical compound CC1CSC(C)=CS1 ZERRJEOSIUQKQQ-UHFFFAOYSA-N 0.000 description 2
- ZSYNOYIEMSXEPO-UHFFFAOYSA-N 2-ethyl-5,6-dipropyl-2,3-dihydro-1,4-dithiine Chemical compound CCCC1=C(CCC)SC(CC)CS1 ZSYNOYIEMSXEPO-UHFFFAOYSA-N 0.000 description 2
- ABBZAFKMTJQVSR-UHFFFAOYSA-N 2-methyl-5,6-dipropyl-2,3-dihydro-1,4-dithiine Chemical compound CCCC1=C(CCC)SC(C)CS1 ABBZAFKMTJQVSR-UHFFFAOYSA-N 0.000 description 2
- BCSWHSJJPYWUHO-UHFFFAOYSA-N 5,6-dibutyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCC1=C(CCCC)SCCS1 BCSWHSJJPYWUHO-UHFFFAOYSA-N 0.000 description 2
- ZZVIQKZCYRVUSW-UHFFFAOYSA-N 5,6-dihexyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCCC1=C(CCCCCC)SCCS1 ZZVIQKZCYRVUSW-UHFFFAOYSA-N 0.000 description 2
- VTFYQACVDBZANX-UHFFFAOYSA-N 5,6-dihexyl-2-methyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCCC1=C(CCCCCC)SC(C)CS1 VTFYQACVDBZANX-UHFFFAOYSA-N 0.000 description 2
- XRCNPRZPSUNYAI-UHFFFAOYSA-N 5-methyl-2,3-dihydro-1,4-dithiine Chemical compound CC1=CSCCS1 XRCNPRZPSUNYAI-UHFFFAOYSA-N 0.000 description 2
- PQESRTWBQJRGON-UHFFFAOYSA-N 8-hydroxytetradecan-7-one Chemical compound CCCCCCC(O)C(=O)CCCCCC PQESRTWBQJRGON-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 125000005283 haloketone group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LFTMJBWNOFFSRW-UHFFFAOYSA-N 1,2-Butanedithiol Chemical compound CCC(S)CS LFTMJBWNOFFSRW-UHFFFAOYSA-N 0.000 description 1
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 1
- NFFXJWRVMWTWHQ-UHFFFAOYSA-N 2,3,5,6,7,8-hexahydro-1,4-benzodithiine Chemical compound S1CCSC2=C1CCCC2 NFFXJWRVMWTWHQ-UHFFFAOYSA-N 0.000 description 1
- ADZQLQDJYZRJEX-UHFFFAOYSA-N 2,3,5,6-tetramethyl-2,3-dihydro-1,4-dithiine Chemical compound CC1SC(C)=C(C)SC1C ADZQLQDJYZRJEX-UHFFFAOYSA-N 0.000 description 1
- HWCZPDGKRZWWID-UHFFFAOYSA-N 2,5,6-triethyl-2,3-dihydro-1,4-dithiine Chemical compound CCC1CSC(CC)=C(CC)S1 HWCZPDGKRZWWID-UHFFFAOYSA-N 0.000 description 1
- XYRKQRCWPGBCMJ-UHFFFAOYSA-N 2,5,6-trimethyl-2,3-dihydro-1,4-dithiine Chemical compound CC1CSC(C)=C(C)S1 XYRKQRCWPGBCMJ-UHFFFAOYSA-N 0.000 description 1
- QPSJWMYYAPGJPU-UHFFFAOYSA-N 2-decyl-5,6-diethyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCCCCCCC1CSC(CC)=C(CC)S1 QPSJWMYYAPGJPU-UHFFFAOYSA-N 0.000 description 1
- ZGQANGOCMGMOMB-UHFFFAOYSA-N 2-ethyl-5,6-bis(2-methylpropyl)-2,3-dihydro-1,4-dithiine Chemical compound CCC1CSC(CC(C)C)=C(CC(C)C)S1 ZGQANGOCMGMOMB-UHFFFAOYSA-N 0.000 description 1
- APGUDOQSOOOBAF-UHFFFAOYSA-N 2-ethyl-5,6-dihexyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCCC1=C(CCCCCC)SC(CC)CS1 APGUDOQSOOOBAF-UHFFFAOYSA-N 0.000 description 1
- LZJAHSXUAKZOOZ-UHFFFAOYSA-N 2-ethyl-5,6-dimethyl-2,3-dihydro-1,4-dithiine Chemical compound CCC1CSC(C)=C(C)S1 LZJAHSXUAKZOOZ-UHFFFAOYSA-N 0.000 description 1
- HMWOHVYKAJFCJB-UHFFFAOYSA-N 2-ethyl-5,6-dipentyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCC1=C(CCCCC)SC(CC)CS1 HMWOHVYKAJFCJB-UHFFFAOYSA-N 0.000 description 1
- DRRIATOSWAYRHW-UHFFFAOYSA-N 2-ethyl-5-methyl-2,3-dihydro-1,4-dithiine Chemical compound CCC1CSC(C)=CS1 DRRIATOSWAYRHW-UHFFFAOYSA-N 0.000 description 1
- HOJFGMXIBCFAMC-UHFFFAOYSA-N 2-ethyl-6-methyl-2,3-dihydro-1,4-dithiine Chemical compound CCC1CSC=C(C)S1 HOJFGMXIBCFAMC-UHFFFAOYSA-N 0.000 description 1
- ODZTXUXIYGJLMC-UHFFFAOYSA-N 2-hydroxycyclohexan-1-one Chemical compound OC1CCCCC1=O ODZTXUXIYGJLMC-UHFFFAOYSA-N 0.000 description 1
- UODHHUNGAMZQRG-UHFFFAOYSA-N 2-methyl-5,6-bis(2-methylpropyl)-2,3-dihydro-1,4-dithiine Chemical compound CC(C)CC1=C(CC(C)C)SC(C)CS1 UODHHUNGAMZQRG-UHFFFAOYSA-N 0.000 description 1
- GTWXMPKUKITHGH-UHFFFAOYSA-N 2-methyl-5,6-dipentyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCC1=C(CCCCC)SC(C)CS1 GTWXMPKUKITHGH-UHFFFAOYSA-N 0.000 description 1
- MXCYSRJCTSJLSA-UHFFFAOYSA-N 3-ethyl-2,3,5,6,7,8-hexahydro-1,4-benzodithiine Chemical compound S1C(CC)CSC2=C1CCCC2 MXCYSRJCTSJLSA-UHFFFAOYSA-N 0.000 description 1
- NCGPDLCBVPEFJB-UHFFFAOYSA-N 5,6-bis(2-methylpropyl)-2,3-dihydro-1,4-dithiine Chemical compound CC(C)CC1=C(CC(C)C)SCCS1 NCGPDLCBVPEFJB-UHFFFAOYSA-N 0.000 description 1
- QIRJITPNJWLUKY-UHFFFAOYSA-N 5,6-dibutyl-2-ethyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCC1=C(CCCC)SC(CC)CS1 QIRJITPNJWLUKY-UHFFFAOYSA-N 0.000 description 1
- LLWKMERHOXDRAP-UHFFFAOYSA-N 5,6-dibutyl-2-methyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCC1=C(CCCC)SC(C)CS1 LLWKMERHOXDRAP-UHFFFAOYSA-N 0.000 description 1
- HYMVECPCAGTRFN-UHFFFAOYSA-N 5,6-diethyl-2,3-dihydro-1,4-dithiine Chemical compound CCC1=C(CC)SCCS1 HYMVECPCAGTRFN-UHFFFAOYSA-N 0.000 description 1
- BOQCUORNRHAOKP-UHFFFAOYSA-N 5,6-diethyl-2-(propoxymethyl)-2,3-dihydro-1,4-dithiine Chemical compound CCCOCC1CSC(CC)=C(CC)S1 BOQCUORNRHAOKP-UHFFFAOYSA-N 0.000 description 1
- CGXJFIOSVNQTAS-UHFFFAOYSA-N 5,6-diethyl-2-methyl-2,3-dihydro-1,4-dithiine Chemical compound CCC1=C(CC)SC(C)CS1 CGXJFIOSVNQTAS-UHFFFAOYSA-N 0.000 description 1
- IRYIPXQAIOAFHN-UHFFFAOYSA-N 5,6-dimethyl-2-(propoxymethyl)-2,3-dihydro-1,4-dithiine Chemical compound CCCOCC1CSC(C)=C(C)S1 IRYIPXQAIOAFHN-UHFFFAOYSA-N 0.000 description 1
- AXADKKSSMXXTSH-UHFFFAOYSA-N 5,6-dipentyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCC1=C(CCCCC)SCCS1 AXADKKSSMXXTSH-UHFFFAOYSA-N 0.000 description 1
- ODMMTPOMHVDNHF-UHFFFAOYSA-N 5,6-dipropyl-2,3-dihydro-1,4-dithiine Chemical compound CCCC1=C(CCC)SCCS1 ODMMTPOMHVDNHF-UHFFFAOYSA-N 0.000 description 1
- ORLDHCIQVZTBQQ-UHFFFAOYSA-N 6-hydroxydecan-5-one Chemical compound CCCCC(O)C(=O)CCCC ORLDHCIQVZTBQQ-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004429 atom Chemical group 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
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000004863 dithiolanes Chemical class 0.000 description 1
- GWNVJSUBDMCUDB-UHFFFAOYSA-N dodecane-1,2-dithiol Chemical compound CCCCCCCCCCC(S)CS GWNVJSUBDMCUDB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000365995A CA1150284A (en) | 1980-12-02 | 1980-12-02 | Method of making certain 2,3-dihydro-1,4-dithiins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57140782A JPS57140782A (en) | 1982-08-31 |
| JPS6228141B2 true JPS6228141B2 (en:Method) | 1987-06-18 |
Family
ID=4118618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56194354A Granted JPS57140782A (en) | 1980-12-02 | 1981-12-02 | Manufacture of 2,3-dihydro-1,4-dithiin |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4319033A (en:Method) |
| EP (1) | EP0053494B1 (en:Method) |
| JP (1) | JPS57140782A (en:Method) |
| KR (1) | KR870000285B1 (en:Method) |
| AU (1) | AU548047B2 (en:Method) |
| BR (1) | BR8107821A (en:Method) |
| CA (1) | CA1150284A (en:Method) |
| DE (1) | DE3175599D1 (en:Method) |
| HU (1) | HU187479B (en:Method) |
| IL (1) | IL64412A (en:Method) |
| IN (1) | IN163673B (en:Method) |
| SU (1) | SU1085508A3 (en:Method) |
| YU (1) | YU280581A (en:Method) |
| ZA (1) | ZA818232B (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1186321A (en) * | 1982-05-06 | 1985-04-30 | Uniroyal, Ltd. | Method of synthesizing dihydro-1, 4-dithiins |
| US5580544A (en) * | 1995-03-29 | 1996-12-03 | Uniroyal Chemical Company, Inc. | Paste formulation useful for seed treatment and foliar treatment of plants |
| US5719103A (en) * | 1996-05-02 | 1998-02-17 | Uniroyal Chemical Company, Inc. | Powder formulation useful for seed treatment and foliar treatment of plants |
| US7081436B2 (en) | 2001-01-26 | 2006-07-25 | General Electric Company | Paste formulation for seed treatment of plants |
| JP4811573B2 (ja) * | 2003-10-31 | 2011-11-09 | 日産化学工業株式会社 | １，４−ジチイン環を有する化合物を含む電荷輸送性有機材料 |
| RU2574393C9 (ru) * | 2010-05-21 | 2016-10-10 | Байер Кропсайенс Аг | Способ синтеза дитиин-тетракарбокси-диимидов |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920438A (en) * | 1973-05-07 | 1975-11-18 | Uniroyal Inc | Substituted dithin tetroxide plant growth regulants |
| US3947264A (en) * | 1974-04-09 | 1976-03-30 | Uniroyal, Inc. | Substituted 2,3-dihydro-,4-oxathiin plant growth stunting agents |
| US4004018A (en) * | 1974-06-20 | 1977-01-18 | Uniroyal Inc. | 2,3-Dihydro-1,4-dithiin 1,1,4,4-tetroxide antimicrobials |
| US4026906A (en) * | 1975-01-10 | 1977-05-31 | Uniroyal Inc. | Substituted dithiin tetroxide plant growth regulants |
-
1980
- 1980-12-02 CA CA000365995A patent/CA1150284A/en not_active Expired
-
1981
- 1981-03-26 US US06/247,670 patent/US4319033A/en not_active Expired - Lifetime
- 1981-11-26 IN IN745/DEL/81A patent/IN163673B/en unknown
- 1981-11-26 ZA ZA818232A patent/ZA818232B/xx unknown
- 1981-11-27 DE DE8181305614T patent/DE3175599D1/de not_active Expired
- 1981-11-27 EP EP81305614A patent/EP0053494B1/en not_active Expired
- 1981-11-30 AU AU78107/81A patent/AU548047B2/en not_active Expired
- 1981-12-01 SU SU813364684A patent/SU1085508A3/ru active
- 1981-12-01 BR BR8107821A patent/BR8107821A/pt unknown
- 1981-12-01 IL IL64412A patent/IL64412A/xx not_active IP Right Cessation
- 1981-12-01 KR KR1019810004667A patent/KR870000285B1/ko not_active Expired
- 1981-12-02 YU YU02805/81A patent/YU280581A/xx unknown
- 1981-12-02 HU HU813624A patent/HU187479B/hu unknown
- 1981-12-02 JP JP56194354A patent/JPS57140782A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| KR830007621A (ko) | 1983-11-04 |
| IL64412A0 (en) | 1982-03-31 |
| EP0053494B1 (en) | 1986-11-12 |
| SU1085508A3 (ru) | 1984-04-07 |
| BR8107821A (pt) | 1982-09-08 |
| DE3175599D1 (en) | 1987-01-02 |
| US4319033A (en) | 1982-03-09 |
| AU7810781A (en) | 1982-06-10 |
| IN163673B (en:Method) | 1988-10-29 |
| IL64412A (en) | 1985-02-28 |
| YU280581A (en) | 1984-02-29 |
| CA1150284A (en) | 1983-07-19 |
| KR870000285B1 (ko) | 1987-02-25 |
| JPS57140782A (en) | 1982-08-31 |
| ZA818232B (en) | 1983-04-27 |
| AU548047B2 (en) | 1985-11-21 |
| HU187479B (en) | 1986-01-28 |
| EP0053494A1 (en) | 1982-06-09 |
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