DE2513202A1 - Substituierte 2,3-dihydro-1,4- oxathiine als pflanzenwachstumsregler - Google Patents
Substituierte 2,3-dihydro-1,4- oxathiine als pflanzenwachstumsreglerInfo
- Publication number
- DE2513202A1 DE2513202A1 DE19752513202 DE2513202A DE2513202A1 DE 2513202 A1 DE2513202 A1 DE 2513202A1 DE 19752513202 DE19752513202 DE 19752513202 DE 2513202 A DE2513202 A DE 2513202A DE 2513202 A1 DE2513202 A1 DE 2513202A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- phenyl
- oxathiine
- oxide
- oxathiin
- 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.)
- Ceased
Links
- 239000005648 plant growth regulator Substances 0.000 title claims description 7
- 239000000126 substance Substances 0.000 claims description 75
- 241000196324 Embryophyta Species 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 31
- 230000012010 growth Effects 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- -1 2,3-dihydro-5- (4-methylphenyl) -1,4-oxathiine Chemical compound 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 230000008635 plant growth Effects 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000002689 soil Substances 0.000 claims description 11
- 230000001629 suppression Effects 0.000 claims description 11
- CPRVXMQHLPTWLY-UHFFFAOYSA-N 1,4-oxathiine Chemical compound O1C=CSC=C1 CPRVXMQHLPTWLY-UHFFFAOYSA-N 0.000 claims description 10
- GZVBPNSXCWYLJU-UHFFFAOYSA-N 5,6-diphenyl-2,3-dihydro-1,4-oxathiine Chemical compound O1CCSC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GZVBPNSXCWYLJU-UHFFFAOYSA-N 0.000 claims description 10
- 239000004009 herbicide Substances 0.000 claims description 10
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- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- JCAIBTLLMPPCQU-UHFFFAOYSA-N 2,3-dihydro-1,4-oxathiine Chemical class C1CSC=CO1 JCAIBTLLMPPCQU-UHFFFAOYSA-N 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000004883 flower formation Effects 0.000 claims description 6
- NLFKQWFQBZQJAK-UHFFFAOYSA-N 5,6-diphenyl-2,3-dihydro-1,4-oxathiine 4-oxide Chemical compound O=S1CCOC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NLFKQWFQBZQJAK-UHFFFAOYSA-N 0.000 claims description 5
- 230000033228 biological regulation Effects 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- TXHLKPCLEIZMNN-UHFFFAOYSA-N 3-phenyl-1,4-oxathiine Chemical compound O1C=CSC(C=2C=CC=CC=2)=C1 TXHLKPCLEIZMNN-UHFFFAOYSA-N 0.000 claims description 4
- 206010053759 Growth retardation Diseases 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
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- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 231100000001 growth retardation Toxicity 0.000 claims description 3
- YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical compound O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 claims description 3
- 230000001850 reproductive effect Effects 0.000 claims description 3
- NACMIEMEMDLXMA-UHFFFAOYSA-N 2-methyl-5,6-diphenyl-2,3-dihydro-1,4-oxathiine Chemical compound O1C(C)CSC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NACMIEMEMDLXMA-UHFFFAOYSA-N 0.000 claims description 2
- IFIWKFYLFNIQQK-UHFFFAOYSA-N 5-(4-fluorophenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine 4-oxide Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC=CC=2)OCCS1=O IFIWKFYLFNIQQK-UHFFFAOYSA-N 0.000 claims description 2
- RQYCWNNCJQMIIJ-UHFFFAOYSA-N 5-(4-methylphenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine 4-oxide Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC=CC=2)OCCS1=O RQYCWNNCJQMIIJ-UHFFFAOYSA-N 0.000 claims description 2
- DRACQADDOLTVEQ-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine 4-oxide Chemical compound ClC1=CC=CC(C=2S(CCOC=2C=2C=CC=CC=2)=O)=C1 DRACQADDOLTVEQ-UHFFFAOYSA-N 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- AJEYLLNQCMLGEP-UHFFFAOYSA-N 5-(3-methylphenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine 4-oxide Chemical compound CC1=CC=CC(C=2S(CCOC=2C=2C=CC=CC=2)=O)=C1 AJEYLLNQCMLGEP-UHFFFAOYSA-N 0.000 claims 2
- CJZYDBMPQDLCSC-UHFFFAOYSA-N 5-(4-methylphenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC=CC=2)OCCS1 CJZYDBMPQDLCSC-UHFFFAOYSA-N 0.000 claims 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- RXAGXTLXYIZAEI-UHFFFAOYSA-N 5-(3,5-dimethylphenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine 4-oxide Chemical compound CC1=CC(C)=CC(C=2S(CCOC=2C=2C=CC=CC=2)=O)=C1 RXAGXTLXYIZAEI-UHFFFAOYSA-N 0.000 claims 1
- PYFFSPWASRYLDD-UHFFFAOYSA-N 5-(3-methylphenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine Chemical compound CC1=CC=CC(C=2SCCOC=2C=2C=CC=CC=2)=C1 PYFFSPWASRYLDD-UHFFFAOYSA-N 0.000 claims 1
- POBRAMNWUUHJBP-UHFFFAOYSA-N 5-(4-bromophenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine Chemical compound C1=CC(Br)=CC=C1C1=C(C=2C=CC=CC=2)OCCS1 POBRAMNWUUHJBP-UHFFFAOYSA-N 0.000 claims 1
- MXOAKOCDEVLJLO-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-phenyl-2,3-dihydro-1,4-oxathiine Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC=CC=2)OCCS1 MXOAKOCDEVLJLO-UHFFFAOYSA-N 0.000 claims 1
- NFQAVQRNYJBEBM-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-phenyl-2,3-dihydro-1,4-oxathiine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC=CC=2)SCCO1 NFQAVQRNYJBEBM-UHFFFAOYSA-N 0.000 claims 1
- 125000004799 bromophenyl group Chemical group 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
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- YJLWDVDWXUKTFG-UHFFFAOYSA-N 2-phenyl-1,4-oxathiine 4-oxide Chemical compound O=S1C=COC(C=2C=CC=CC=2)=C1 YJLWDVDWXUKTFG-UHFFFAOYSA-N 0.000 description 6
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- 239000006185 dispersion Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000007954 growth retardant Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/459,442 US3947264A (en) | 1974-04-09 | 1974-04-09 | Substituted 2,3-dihydro-,4-oxathiin plant growth stunting agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2513202A1 true DE2513202A1 (de) | 1975-10-23 |
Family
ID=23824789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752513202 Ceased DE2513202A1 (de) | 1974-04-09 | 1975-03-25 | Substituierte 2,3-dihydro-1,4- oxathiine als pflanzenwachstumsregler |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3947264A (en, 2012) |
| JP (1) | JPS50140630A (en, 2012) |
| AR (2) | AR214965A1 (en, 2012) |
| AT (1) | AT339929B (en, 2012) |
| CA (1) | CA1033187A (en, 2012) |
| CH (1) | CH614708A5 (en, 2012) |
| DD (1) | DD116737A5 (en, 2012) |
| DE (1) | DE2513202A1 (en, 2012) |
| DK (1) | DK148975A (en, 2012) |
| FR (1) | FR2267038B1 (en, 2012) |
| GB (1) | GB1499418A (en, 2012) |
| IL (1) | IL47024A (en, 2012) |
| IT (1) | IT1036206B (en, 2012) |
| NL (1) | NL7504007A (en, 2012) |
| SU (1) | SU591118A3 (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4340747A (en) * | 1975-08-15 | 1982-07-20 | Ciba-Geigy Corporation | Esters of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic-acid |
| US4229207A (en) * | 1975-08-15 | 1980-10-21 | Ciba-Geigy Corporation | Esters of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic acid |
| US4340415A (en) * | 1975-08-15 | 1982-07-20 | Ciba-Geigy Corporation | Esters of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic-acid |
| US4127402A (en) * | 1975-10-30 | 1978-11-28 | Uniroyal, Inc. | Substituted 2,3-dihydro-1,4-oxathiin plant growth regulants |
| US4319031A (en) * | 1976-02-06 | 1982-03-09 | Stauffer Chemical Company | Substituted thiazolidines |
| FR2347273A1 (fr) * | 1976-04-06 | 1977-11-04 | Oreal | Opercule muni d'un dispositif d'inviolabilite pour le bouchage d'un recipient |
| CA1130297A (en) * | 1980-05-02 | 1982-08-24 | Michael A. Puttock | Method of making 2,3-dihydro-5,6-diphenyl- 1,4-oxathiin |
| CA1150284A (en) * | 1980-12-02 | 1983-07-19 | Allan K.S. Tsai | Method of making certain 2,3-dihydro-1,4-dithiins |
| US5578498A (en) * | 1991-05-22 | 1996-11-26 | Behringwerke Ag | Metal chelate containing compositions for use in chemiluminescent assays |
| CN107439565A (zh) * | 2017-08-24 | 2017-12-08 | 长沙理工大学 | 一种肾蕨矮控剂及其使用方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3066149A (en) * | 1958-07-30 | 1962-11-27 | Diamond Alkali Co | 1, 3, 5-trithiane compounds |
| US3082214A (en) * | 1958-09-04 | 1963-03-19 | Diamond Alkali Co | Chemical compositions and process |
| US3454391A (en) * | 1966-05-04 | 1969-07-08 | Uniroyal Inc | Stimulation of plant growth |
| DE1957859A1 (de) * | 1969-11-18 | 1971-05-27 | Degussa | Verfahren zur Herstellung von 2,3-Dihydro-p-oxathiinen und deren Sulfoxiden und Sulfonen |
| US3806332A (en) * | 1970-03-09 | 1974-04-23 | Uniroyal Ltd | Plant air pollution protectants |
-
1974
- 1974-04-09 US US05/459,442 patent/US3947264A/en not_active Expired - Lifetime
- 1974-09-04 CA CA208,416A patent/CA1033187A/en not_active Expired
-
1975
- 1975-03-24 GB GB12099/75A patent/GB1499418A/en not_active Expired
- 1975-03-25 DE DE19752513202 patent/DE2513202A1/de not_active Ceased
- 1975-04-01 AR AR258212A patent/AR214965A1/es active
- 1975-04-03 AT AT253375A patent/AT339929B/de not_active IP Right Cessation
- 1975-04-04 NL NL7504007A patent/NL7504007A/xx not_active Application Discontinuation
- 1975-04-06 IL IL47024A patent/IL47024A/xx unknown
- 1975-04-08 JP JP50042709A patent/JPS50140630A/ja active Pending
- 1975-04-08 FR FR7510932A patent/FR2267038B1/fr not_active Expired
- 1975-04-08 IT IT67904/75A patent/IT1036206B/it active
- 1975-04-08 DK DK148975A patent/DK148975A/da not_active IP Right Cessation
- 1975-04-09 CH CH452775A patent/CH614708A5/xx not_active IP Right Cessation
- 1975-04-09 SU SU752121786A patent/SU591118A3/ru active
- 1975-04-09 DD DD185340A patent/DD116737A5/xx unknown
-
1977
- 1977-07-19 AR AR268485A patent/AR223135A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AT339929B (de) | 1977-11-10 |
| IT1036206B (it) | 1979-10-30 |
| DD116737A5 (de) | 1975-12-12 |
| DK148975A (en, 2012) | 1975-10-10 |
| JPS50140630A (en, 2012) | 1975-11-11 |
| CH614708A5 (en, 2012) | 1979-12-14 |
| FR2267038B1 (en, 2012) | 1977-04-15 |
| GB1499418A (en) | 1978-02-01 |
| AR214965A1 (es) | 1979-08-31 |
| ATA253375A (de) | 1977-03-15 |
| FR2267038A1 (en, 2012) | 1975-11-07 |
| AR223135A1 (es) | 1981-07-31 |
| SU591118A3 (ru) | 1978-01-30 |
| AU7924975A (en) | 1976-09-23 |
| US3947264A (en) | 1976-03-30 |
| IL47024A (en) | 1979-05-31 |
| NL7504007A (nl) | 1975-10-13 |
| CA1033187A (en) | 1978-06-20 |
| IL47024A0 (en) | 1975-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |