CA1160073A - Beta-substituted ethanesulphinic acids and oxygen or sulphur esters thereof as plant growth regulators - Google Patents
Beta-substituted ethanesulphinic acids and oxygen or sulphur esters thereof as plant growth regulatorsInfo
- Publication number
- CA1160073A CA1160073A CA000144471A CA144471A CA1160073A CA 1160073 A CA1160073 A CA 1160073A CA 000144471 A CA000144471 A CA 000144471A CA 144471 A CA144471 A CA 144471A CA 1160073 A CA1160073 A CA 1160073A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- alkyl
- chlorine
- alkoxy
- bromine
- 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
- -1 Beta-substituted ethanesulphinic acids Chemical class 0.000 title claims abstract description 94
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000001301 oxygen Substances 0.000 title claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000005648 plant growth regulator Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 230000008635 plant growth Effects 0.000 claims abstract description 15
- 230000001105 regulatory effect Effects 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 199
- 239000000460 chlorine Substances 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 229910052801 chlorine Inorganic materials 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 34
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 32
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000004414 alkyl thio group Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 12
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 12
- 239000011630 iodine Substances 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- HIGURQRYZKCDQF-UHFFFAOYSA-N ethanesulfinamide Chemical class CCS(N)=O HIGURQRYZKCDQF-UHFFFAOYSA-N 0.000 abstract description 7
- 238000009472 formulation Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 238000011282 treatment Methods 0.000 description 46
- 229910052799 carbon Inorganic materials 0.000 description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 41
- 241000196324 Embryophyta Species 0.000 description 29
- 239000000243 solution Substances 0.000 description 24
- 240000003768 Solanum lycopersicum Species 0.000 description 19
- 241000894007 species Species 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 235000013399 edible fruits Nutrition 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 230000036253 epinasty Effects 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- RRSCOUPNURHZBJ-UHFFFAOYSA-N 2-chloroethanesulfinic acid Chemical compound OS(=O)CCCl RRSCOUPNURHZBJ-UHFFFAOYSA-N 0.000 description 9
- FKUBZQOURSEZDB-UHFFFAOYSA-N 2-chloroethanesulfinyl chloride Chemical compound ClCCS(Cl)=O FKUBZQOURSEZDB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- DXVLGOVMHHQZFV-UHFFFAOYSA-N methyl 2-chloroethanesulfinate Chemical compound COS(=O)CCCl DXVLGOVMHHQZFV-UHFFFAOYSA-N 0.000 description 8
- FDPHMKBPFLSJRA-UHFFFAOYSA-N 2-chloro-n-phenylethanesulfinamide Chemical compound ClCCS(=O)NC1=CC=CC=C1 FDPHMKBPFLSJRA-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- RQIFXTOWUNAUJC-UHFFFAOYSA-N ethanesulfinic acid Chemical class CCS(O)=O RQIFXTOWUNAUJC-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- FZFGFFCOLUTIPC-UHFFFAOYSA-N 2-chloroethanesulfinamide Chemical class NS(=O)CCCl FZFGFFCOLUTIPC-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 241000234295 Musa Species 0.000 description 5
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052716 thallium Inorganic materials 0.000 description 5
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 5
- KBINHYOGLICIMS-UHFFFAOYSA-N 2-hydroxyethanesulfinic acid Chemical compound OCCS(O)=O KBINHYOGLICIMS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- 241001506766 Xanthium Species 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000021015 bananas Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 4
- NNYBQONXHNTVIJ-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229940063718 lodine Drugs 0.000 description 4
- VFLYOLOQOBMHLI-UHFFFAOYSA-N octyl 2-chloroethanesulfinate Chemical compound CCCCCCCCOS(=O)CCCl VFLYOLOQOBMHLI-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 230000005070 ripening Effects 0.000 description 4
- 230000007226 seed germination Effects 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 230000006578 abscission Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229940076134 benzene Drugs 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 3
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 2
- PXHZCZFXMOGGAJ-UHFFFAOYSA-N 2-chloro-n-hexylethanesulfinamide Chemical compound CCCCCCNS(=O)CCCl PXHZCZFXMOGGAJ-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000005976 Citrus sinensis Nutrition 0.000 description 2
- 240000002319 Citrus sinensis Species 0.000 description 2
- 235000005853 Cyperus esculentus Nutrition 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241001024304 Mino Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000003953 Solanum lycopersicum var cerasiforme Nutrition 0.000 description 2
- 240000003040 Solanum lycopersicum var. cerasiforme Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- YYHLBTHZFWSZLD-UHFFFAOYSA-N butyl 2-chloroethanesulfinate Chemical compound CCCCOS(=O)CCCl YYHLBTHZFWSZLD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- QNGCMDVCEXVOMM-UHFFFAOYSA-N dodecyl 2-chloroethanesulfinate Chemical compound CCCCCCCCCCCCOS(=O)CCCl QNGCMDVCEXVOMM-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- CXAVWUXAKZJEBR-UHFFFAOYSA-N ethanesulfinyl chloride Chemical class CCS(Cl)=O CXAVWUXAKZJEBR-UHFFFAOYSA-N 0.000 description 2
- AAFAGAHZFPLKOI-UHFFFAOYSA-N ethyl 2-chloroethanesulfinate Chemical compound CCOS(=O)CCCl AAFAGAHZFPLKOI-UHFFFAOYSA-N 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- UHMZHYUCMREDRI-UHFFFAOYSA-N ethyl thiohypochlorite Chemical class CCSCl UHMZHYUCMREDRI-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- HZINEDNLYLGGLR-UHFFFAOYSA-N hexadecyl 2-chloroethanesulfinate Chemical compound CCCCCCCCCCCCCCCCOS(=O)CCCl HZINEDNLYLGGLR-UHFFFAOYSA-N 0.000 description 2
- VTGAFTYVPGUPPM-UHFFFAOYSA-N hexyl 2-chloroethanesulfinate Chemical compound CCCCCCOS(=O)CCCl VTGAFTYVPGUPPM-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003054 hormonal effect Effects 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- UKHWJBVVWVYFEY-UHFFFAOYSA-M silver;hydroxide Chemical compound [OH-].[Ag+] UKHWJBVVWVYFEY-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- XLEYMOKKKIAULW-UHFFFAOYSA-N 1-bromoethanesulfinic acid Chemical compound CC(Br)S(O)=O XLEYMOKKKIAULW-UHFFFAOYSA-N 0.000 description 1
- XDFZUXHZXUFQOS-UHFFFAOYSA-N 1-chloro-2-(2-chloroethyldisulfanyl)ethane Chemical compound ClCCSSCCCl XDFZUXHZXUFQOS-UHFFFAOYSA-N 0.000 description 1
- WJJNHWIPKZQTAF-UHFFFAOYSA-N 1-chloroethanesulfinamide Chemical compound ClC(C)S(=O)N WJJNHWIPKZQTAF-UHFFFAOYSA-N 0.000 description 1
- ZUQKROYNVKICEM-UHFFFAOYSA-N 1-chloroethanesulfinic acid Chemical compound CC(Cl)S(O)=O ZUQKROYNVKICEM-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- HAOXTAJLDMZCQJ-UHFFFAOYSA-N 1-ethoxydodecane Chemical compound CCCCCCCCCCCCOCC HAOXTAJLDMZCQJ-UHFFFAOYSA-N 0.000 description 1
- OIFNLBREENAINB-UHFFFAOYSA-N 2-(2-chloroethylsulfinyloxy)ethyl 2-chloroethanesulfinate Chemical compound ClCCS(=O)OCCOS(=O)CCCl OIFNLBREENAINB-UHFFFAOYSA-N 0.000 description 1
- DPPGKOHSYIXANJ-UHFFFAOYSA-N 2-(2-methoxyethylsulfinylsulfanyl)butane Chemical compound COCCS(SC(C)CC)=O DPPGKOHSYIXANJ-UHFFFAOYSA-N 0.000 description 1
- ADYQPDKQSLFDDQ-UHFFFAOYSA-N 2-bromoethanesulfinamide Chemical compound NS(=O)CCBr ADYQPDKQSLFDDQ-UHFFFAOYSA-N 0.000 description 1
- JXJMYPUDIPBWSB-UHFFFAOYSA-N 2-bromoethanesulfinic acid Chemical compound OS(=O)CCBr JXJMYPUDIPBWSB-UHFFFAOYSA-N 0.000 description 1
- PKQHNCPRJGIMLH-UHFFFAOYSA-N 2-butanoyloxyethanesulfinic acid Chemical compound CCCC(=O)OCCS(O)=O PKQHNCPRJGIMLH-UHFFFAOYSA-N 0.000 description 1
- CQBWBQLOBJHXJL-UHFFFAOYSA-N 2-butoxypropyl 2-chloroethanesulfinate Chemical compound CCCCOC(C)COS(=O)CCCl CQBWBQLOBJHXJL-UHFFFAOYSA-N 0.000 description 1
- FNTROZHABZLBJM-UHFFFAOYSA-N 2-chloro-n-cyclohexylethanesulfinamide Chemical compound ClCCS(=O)NC1CCCCC1 FNTROZHABZLBJM-UHFFFAOYSA-N 0.000 description 1
- QRWHCHWIJSFRMT-UHFFFAOYSA-N 2-chloro-n-heptylethanesulfinamide Chemical compound CCCCCCCNS(=O)CCCl QRWHCHWIJSFRMT-UHFFFAOYSA-N 0.000 description 1
- FGYGQQXIMRWFNR-UHFFFAOYSA-N 2-chloro-n-propan-2-ylethanesulfinamide Chemical compound CC(C)NS(=O)CCCl FGYGQQXIMRWFNR-UHFFFAOYSA-N 0.000 description 1
- BHRUWIQZTUKVLN-UHFFFAOYSA-N 2-chloroethylsulfinylsulfanylmethylbenzene Chemical compound ClCCS(SCC1=CC=CC=C1)=O BHRUWIQZTUKVLN-UHFFFAOYSA-N 0.000 description 1
- FLSRPCREYIPVFZ-UHFFFAOYSA-N 2-chlorosulfinylethyl methanesulfonate Chemical compound CS(=O)(=O)OCCS(=O)Cl FLSRPCREYIPVFZ-UHFFFAOYSA-N 0.000 description 1
- CGPZBNYUHKAQKB-UHFFFAOYSA-N 2-ethoxyethanesulfinic acid Chemical compound CCOCCS(O)=O CGPZBNYUHKAQKB-UHFFFAOYSA-N 0.000 description 1
- WMMYFRDJZMITRO-UHFFFAOYSA-N 2-ethylsulfanylethyl 2-chloroethanesulfinate Chemical compound CCSCCOS(=O)CCCl WMMYFRDJZMITRO-UHFFFAOYSA-N 0.000 description 1
- PDEKLCLCBUZCBD-UHFFFAOYSA-N 2-methoxyethanesulfinic acid Chemical compound COCCS(O)=O PDEKLCLCBUZCBD-UHFFFAOYSA-N 0.000 description 1
- DCFSBQRLLJCFOH-UHFFFAOYSA-N 2-methoxyethyl 2-chloroethanesulfinate Chemical compound COCCOS(=O)CCCl DCFSBQRLLJCFOH-UHFFFAOYSA-N 0.000 description 1
- SLMPXVDEYLTLDL-UHFFFAOYSA-N 2-methoxypropyl 2-bromoethanesulfinate Chemical compound COC(C)COS(=O)CCBr SLMPXVDEYLTLDL-UHFFFAOYSA-N 0.000 description 1
- IJUVRAWYTGZULW-UHFFFAOYSA-N 2-phenoxyethanesulfinic acid Chemical compound OS(=O)CCOC1=CC=CC=C1 IJUVRAWYTGZULW-UHFFFAOYSA-N 0.000 description 1
- AZWVGKTZEBTBIK-UHFFFAOYSA-N 2-phenylethyl 2-chloroethanesulfinate Chemical compound ClCCS(=O)OCCC1=CC=CC=C1 AZWVGKTZEBTBIK-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 240000001505 Cyperus odoratus Species 0.000 description 1
- 244000075634 Cyperus rotundus Species 0.000 description 1
- 241001547070 Eriodes Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- XUGJXJRKPPEIAX-UHFFFAOYSA-N N-butan-2-yl-2-chloroethanesulfinamide Chemical compound C(C)(CC)NS(=O)CCCl XUGJXJRKPPEIAX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101710172602 Sproutin Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 229910001422 barium ion Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- HPTMZNZYFRTOKS-UHFFFAOYSA-N ethenesulfinic acid Chemical compound OS(=O)C=C HPTMZNZYFRTOKS-UHFFFAOYSA-N 0.000 description 1
- AKMPVPNYVNVBOB-UHFFFAOYSA-N ethyl-hydroxy-sulfanylidene-$l^{4}-sulfane Chemical class CCS(O)=S AKMPVPNYVNVBOB-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000004345 fruit ripening Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- KJBLMTNFRDSZOY-UHFFFAOYSA-N heptyl 2-chloroethanesulfinate Chemical compound CCCCCCCOS(=O)CCCl KJBLMTNFRDSZOY-UHFFFAOYSA-N 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 101150085091 lat-2 gene Proteins 0.000 description 1
- 230000028514 leaf abscission Effects 0.000 description 1
- 230000002015 leaf growth Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- OVTJMPMILNESKM-UHFFFAOYSA-N methyl 2-bromoethanesulfinate Chemical compound COS(=O)CCBr OVTJMPMILNESKM-UHFFFAOYSA-N 0.000 description 1
- OYPSOTBALOTWRN-UHFFFAOYSA-N methyl 2-nitroethanesulfinate Chemical compound [N+](=O)([O-])CCS(=O)OC OYPSOTBALOTWRN-UHFFFAOYSA-N 0.000 description 1
- HNWUSDMNZOAUQR-UHFFFAOYSA-N methyl 3-methylhept-2-enoate Chemical compound CCCCC(C)=CC(=O)OC HNWUSDMNZOAUQR-UHFFFAOYSA-N 0.000 description 1
- WXEHBUMAEPOYKP-UHFFFAOYSA-N methylsulfanylethane Chemical compound CCSC WXEHBUMAEPOYKP-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SMWPFZHDKHWHCD-UHFFFAOYSA-N n-benzyl-2-chloroethanesulfinamide Chemical compound ClCCS(=O)NCC1=CC=CC=C1 SMWPFZHDKHWHCD-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- UKYFXXFYJYHTDO-UHFFFAOYSA-N octyl 2-bromoethanesulfinate Chemical compound BrCCS(=O)OCCCCCCCC UKYFXXFYJYHTDO-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- VODVYCRWWNQRFU-UHFFFAOYSA-N phenyl 2-bromoethanesulfinate Chemical compound BrCCS(=O)OC1=CC=CC=C1 VODVYCRWWNQRFU-UHFFFAOYSA-N 0.000 description 1
- YXKVWSQDJUJDEW-UHFFFAOYSA-N phenyl 2-chloroethanesulfinate Chemical compound ClCCS(=O)OC1=CC=CC=C1 YXKVWSQDJUJDEW-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- MYMMBQGZFVELKS-UHFFFAOYSA-N prop-1-ynyl 2-bromoethanesulfinate Chemical compound CC#COS(=O)CCBr MYMMBQGZFVELKS-UHFFFAOYSA-N 0.000 description 1
- SQPYNGUNZZYGKA-UHFFFAOYSA-N prop-2-ynyl 2-chloroethanesulfinate Chemical compound ClCCS(=O)OCC#C SQPYNGUNZZYGKA-UHFFFAOYSA-N 0.000 description 1
- KBRIJYGGGXRJDH-UHFFFAOYSA-N propan-2-yl 2-chloroethanesulfinate Chemical compound CC(C)OS(=O)CCCl KBRIJYGGGXRJDH-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- GBECUEIQVRDUKB-UHFFFAOYSA-M thallium monochloride Chemical compound [Tl]Cl GBECUEIQVRDUKB-UHFFFAOYSA-M 0.000 description 1
- ZLUSCZLCHQSJRU-UHFFFAOYSA-N thallium(1+) Chemical compound [Tl+] ZLUSCZLCHQSJRU-UHFFFAOYSA-N 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/06—Sulfinamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/10—Sulfenic acids; Esters thereof
- C07C313/12—Sulfenic acids; Esters thereof having sulfur atoms of sulfenic groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- 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
- C07C323/46—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 having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/49—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 having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16271071A | 1971-07-14 | 1971-07-14 | |
| US16270971A | 1971-07-14 | 1971-07-14 | |
| US162-710 | 1971-07-14 | ||
| US162,709 | 1971-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1160073A true CA1160073A (en) | 1984-01-10 |
Family
ID=26858998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000144471A Expired CA1160073A (en) | 1971-07-14 | 1972-06-12 | Beta-substituted ethanesulphinic acids and oxygen or sulphur esters thereof as plant growth regulators |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU470362B2 (enExample) |
| CA (1) | CA1160073A (enExample) |
| CH (1) | CH582468A5 (enExample) |
| DE (1) | DE2231463A1 (enExample) |
| FR (1) | FR2145674B1 (enExample) |
| GB (1) | GB1397450A (enExample) |
| HU (1) | HU170068B (enExample) |
| IT (1) | IT956691B (enExample) |
| NL (1) | NL7208619A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833856A1 (de) * | 1978-08-02 | 1980-02-21 | Bayer Ag | Mittel zur regulierung des pflanzenwachstums |
| US5765062A (en) * | 1994-04-19 | 1998-06-09 | Keepsake, Inc. | Reusable fun photography double exposure camera |
| US5546146A (en) * | 1994-04-19 | 1996-08-13 | Keepsake, Inc. | Single use camera film pre-exposure method |
| IL311938A (en) * | 2021-10-08 | 2024-06-01 | Crop Health Vision B V | Organosulfur compounds as plant biostimulants |
-
1972
- 1972-06-12 CA CA000144471A patent/CA1160073A/en not_active Expired
- 1972-06-15 AU AU43470/72A patent/AU470362B2/en not_active Expired
- 1972-06-16 GB GB2830472A patent/GB1397450A/en not_active Expired
- 1972-06-19 IT IT2589572A patent/IT956691B/it active
- 1972-06-23 NL NL7208619A patent/NL7208619A/xx not_active Application Discontinuation
- 1972-06-27 DE DE19722231463 patent/DE2231463A1/de active Pending
- 1972-07-05 HU HUSE001633 patent/HU170068B/hu unknown
- 1972-07-11 CH CH1038372A patent/CH582468A5/xx not_active IP Right Cessation
- 1972-07-13 FR FR7225443A patent/FR2145674B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT956691B (it) | 1973-10-10 |
| HU170068B (enExample) | 1977-03-28 |
| DE2231463A1 (de) | 1973-01-18 |
| CH582468A5 (enExample) | 1976-12-15 |
| FR2145674B1 (enExample) | 1974-07-26 |
| AU470362B2 (en) | 1973-12-20 |
| NL7208619A (enExample) | 1973-01-16 |
| FR2145674A1 (enExample) | 1973-02-23 |
| GB1397450A (en) | 1975-06-11 |
| AU4347072A (en) | 1973-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |