IL44187A - 5-acetamido-2,4 dimethyltrifluoromethanesulfonanilide and its preparation - Google Patents

5-acetamido-2,4 dimethyltrifluoromethanesulfonanilide and its preparation

Info

Publication number: IL44187A
Authority: IL; Israel
Prior art keywords: acetamido; dimethyltrifluoromethanesulfonanilide; reaction; compound; salts
Prior art date: 1973-02-12

Application number

IL44187A

Other languages

English (en)

Other versions

IL44187A0 (en

Original Assignee

Minnesota Mining & Mfg

Priority date (The priority date 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 date listed.)

1973-02-12

Filing date

1974-02-11

Publication date

1977-04-29

1974-02-11 Application filed by Minnesota Mining & Mfg filed Critical Minnesota Mining & Mfg

1974-05-16 Publication of IL44187A0 publication Critical patent/IL44187A0/xx

1977-04-29 Publication of IL44187A publication Critical patent/IL44187A/en

Links

OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 17
-1 nitro, amino Chemical group 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
150000008064 anhydrides Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 16
238000000034 method Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
244000025254 Cannabis sativa Species 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
241000196324 Embryophyta Species 0.000 description 9
239000002253 acid Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000004009 herbicide Substances 0.000 description 8
230000008635 plant growth Effects 0.000 description 8
230000002363 herbicidal effect Effects 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
230000012010 growth Effects 0.000 description 6
230000000051 modifying effect Effects 0.000 description 6
239000005648 plant growth regulator Substances 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000012535 impurity Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
230000008569 process Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
SLVAEVYIJHDKRO-UHFFFAOYSA-N trifluoromethanesulfonyl fluoride Chemical compound FC(F)(F)S(F)(=O)=O SLVAEVYIJHDKRO-UHFFFAOYSA-N 0.000 description 5
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
150000004982 aromatic amines Chemical class 0.000 description 4
239000008187 granular material Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000003630 growth substance Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
230000017066 negative regulation of growth Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
241000209049 Poa pratensis Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002027 dichloromethane extract Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
238000007429 general method Methods 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000003607 modifier Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000010076 replication Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003892 spreading Methods 0.000 description 2
230000007480 spreading Effects 0.000 description 2
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
KVGOXGQSTGQXDD-UHFFFAOYSA-N 1-decane-sulfonic-acid Chemical class CCCCCCCCCCS(O)(=O)=O KVGOXGQSTGQXDD-UHFFFAOYSA-N 0.000 description 1
DUIOVGPUAJSYCD-UHFFFAOYSA-N 2,4-dimethyl-5-nitroaniline Chemical group CC1=CC(C)=C([N+]([O-])=O)C=C1N DUIOVGPUAJSYCD-UHFFFAOYSA-N 0.000 description 1
XVBLEUZLLURXTF-UHFFFAOYSA-N 2,4-dimethylbenzene-1,3-diamine Chemical compound CC1=CC=C(N)C(C)=C1N XVBLEUZLLURXTF-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
DCSSXQMBIGEQGN-UHFFFAOYSA-N 4,6-dimethylbenzene-1,3-diamine Chemical compound CC1=CC(C)=C(N)C=C1N DCSSXQMBIGEQGN-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
241000234653 Cyperus Species 0.000 description 1
235000005853 Cyperus esculentus Nutrition 0.000 description 1
244000075634 Cyperus rotundus Species 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
240000007049 Juglans regia Species 0.000 description 1
235000009496 Juglans regia Nutrition 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
241000699696 Meriones Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical class [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
241001148683 Zostera marina Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000033228 biological regulation Effects 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
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000035613 defoliation Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
YVIGPQSYEAOLAD-UHFFFAOYSA-L disodium;dodecyl phosphate Chemical class [Na+].[Na+].CCCCCCCCCCCCOP([O-])([O-])=O YVIGPQSYEAOLAD-UHFFFAOYSA-L 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 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
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
230000006870 function Effects 0.000 description 1
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239000007789 gas Substances 0.000 description 1
208000037824 growth disorder Diseases 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002505 iron Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000010687 lubricating oil Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
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238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
RLJSXMVTLMHXJS-UHFFFAOYSA-M sodium;4-decylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 RLJSXMVTLMHXJS-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000012085 test solution Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
238000006478 transmetalation reaction Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IL44187A 1973-02-12 1974-02-11 5-acetamido-2,4 dimethyltrifluoromethanesulfonanilide and its preparation IL44187A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US331676A US3894078A (en)	1973-02-12	1973-02-12	5-Acetamido-2,4-dimethyltrifluoromethanesulfonanilide

Publications (2)

Publication Number	Publication Date
IL44187A0 IL44187A0 (en)	1974-05-16
IL44187A true IL44187A (en)	1977-04-29

Family

ID=23294892

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL44187A IL44187A (en)	1973-02-12	1974-02-11	5-acetamido-2,4 dimethyltrifluoromethanesulfonanilide and its preparation

Country Status (9)

Country	Link
US (1)	US3894078A (fr)
JP (2)	JPS5745217B2 (fr)
CA (1)	CA1023385A (fr)
DE (1)	DE2406475C2 (fr)
FR (1)	FR2217322B1 (fr)
GB (1)	GB1459870A (fr)
IL (1)	IL44187A (fr)
IT (1)	IT1049267B (fr)
PH (1)	PH10755A (fr)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2900685A1 (de) *	1979-01-10	1980-07-24	Basf Ag	Substituierte sulfonsaeureanilide, ihre herstellung und verwendung
US4405359A (en) *	1980-09-18	1983-09-20	Minnesota Mining And Manufacturing Company	Acyclicacylaminoperfluoroalkanesulfonanilides and derivatives thereof
US4380464A (en) *	1980-09-18	1983-04-19	Minnesota Mining And Manufacturing Company	N,N-Diacylaminoperfluoroalkanesulfonanilides and derivatives thereof
US4312663A (en) *	1980-09-18	1982-01-26	Minnesota Mining And Manufacturing Company	Cyclicacylaminoperfluoroalkanesulfonanilides and derivatives thereof
EP0049042B1 (fr) *	1980-09-18	1984-03-21	Minnesota Mining And Manufacturing Company	Acycloacylaminoperfluoroalcanesulfonanilides et leurs dérivés
US4556410A (en) *	1981-03-10	1985-12-03	Minnesota Mining And Manufacturing Company	Compositions for tobacco sucker growth control
US4341902A (en) *	1981-06-26	1982-07-27	Mobay Chemical Corporation	Process for the production of 5-nitro-acet-2,4-xylidine
US4552981A (en) *	1981-11-27	1985-11-12	Mobay Chemical Corporation	Process for the production of 5-nitro-acet-2,4-xylidine
US5116403A (en) *	1985-02-04	1992-05-26	American Cyanamid Company	Turfgrass management composition using a 2-imidazole-2-yl nicotinic acid derivative composition
US4603214A (en) *	1985-02-14	1986-07-29	Bayer Aktiengesellschaft	Agents for combating pests
US4965254A (en) *	1985-02-14	1990-10-23	Bayer Aktiengesellschaft	Agents for combating pests
US4656163A (en) *	1985-02-14	1987-04-07	Bayer Aktiengesellschaft	Compositions and methods of combating pests employing sulphenic acid amides in combination with known nematicides or insecticides
FR2785283B1 (fr) *	1998-11-04	2000-12-15	Maubrac Soc D Expl Ets	Procede et reactif utile pour la synthese de sulfanilide perhalogene sur le carbone porte par l'atome de soufre de la fonction sulfanilide
FR2799459B1 (fr) *	1999-10-06	2001-12-14	Rhodia Chimie Sa	Procede et reactif utile pour la synthese de sulfanilide perhalogene sur le carbone porte par l'atome de soufre de la fonction sulfanilide
WO2000026161A1 (fr) *	1998-11-04	2000-05-11	Rhodia Chimie	Procede et reactif de sulfonylation utiles pour la synthese de sulfanilide perhalogene
US6451741B1 (en) *	2000-08-29	2002-09-17	Thomas L. Watschke	Inhibition of vegetative growth
US6642179B2 (en) *	2000-08-29	2003-11-04	Thomas L. Watschke	Inhibition of vegetative growth
EP2052606A1 (fr)	2007-10-24	2009-04-29	Bayer CropScience AG	Combinaison d'herbicide
DE102008037620A1 (de)	2008-08-14	2010-02-18	Bayer Crop Science Ag	Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
PL2627183T5 (pl)	2010-10-15	2024-02-05	Bayer Cropscience Aktiengesellschaft	Zastosowanie herbicydów inhibitorów ALS do kontroli niechcianej roślinności w roślinach Beta vulgaris z tolerancją herbicydów inhibitorów ALS
UA117447C2 (uk)	2011-05-04	2018-08-10	Байєр Інтеллектуал Проперті Гмбх	Застосування гербіцидів інгібіторів als для боротьби з небажаною рослинністю на площі вирощування brassica
RS57806B2 (sr)	2012-12-13	2022-07-29	Bayer Cropscience Ag	Upotreba als inhibitora herbicida za kontrolu neželjene vegetacije kod beta vulgaris biljaka tolerantnih na als inhibitore herbicida

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3639474A (en) *	1969-06-12	1972-02-01	Minnesota Mining & Mfg	N-substituted perfluoroalkane-sulfonamides
US3793372A (en) *	1971-07-28	1974-02-19	Minnesota Mining & Mfg	N-cyanohaloalkanesulfonanilides

1973
- 1973-02-12 US US331676A patent/US3894078A/en not_active Expired - Lifetime
1974
- 1974-01-18 CA CA190,447A patent/CA1023385A/fr not_active Expired
- 1974-02-09 JP JP49015900A patent/JPS5745217B2/ja not_active Expired
- 1974-02-11 PH PH15494A patent/PH10755A/en unknown
- 1974-02-11 IL IL44187A patent/IL44187A/en unknown
- 1974-02-11 FR FR7404471A patent/FR2217322B1/fr not_active Expired
- 1974-02-11 GB GB604874A patent/GB1459870A/en not_active Expired
- 1974-02-11 DE DE2406475A patent/DE2406475C2/de not_active Expired
- 1974-02-11 IT IT48263/74A patent/IT1049267B/it active
1981
- 1981-11-17 JP JP56183162A patent/JPS57112365A/ja active Granted

Also Published As

Publication number	Publication date
JPS5757471B2 (fr)	1982-12-04
FR2217322A1 (fr)	1974-09-06
PH10755A (en)	1977-09-02
CA1023385A (fr)	1977-12-27
FR2217322B1 (fr)	1976-11-26
GB1459870A (en)	1976-12-31
DE2406475C2 (de)	1983-04-28
US3894078A (en)	1975-07-08
IL44187A0 (en)	1974-05-16
IT1049267B (it)	1981-01-20
JPS49102642A (fr)	1974-09-27
JPS5745217B2 (fr)	1982-09-27
DE2406475A1 (de)	1974-08-29
JPS57112365A (en)	1982-07-13

Publication	Publication Date	Title
IL44187A (en)	1977-04-29	5-acetamido-2,4 dimethyltrifluoromethanesulfonanilide and its preparation
US4270948A (en)	1981-06-02	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
US4046553A (en)	1977-09-06	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US3639474A (en)	1972-02-01	N-substituted perfluoroalkane-sulfonamides
KR910002946B1 (ko)	1991-05-11	제초성 플루오로페녹시페녹시알카노산 및 이의 유도체
US4979982A (en)	1990-12-25	Herbicidal cinnamic ester uracils
JPH0339482B2 (fr)	1991-06-14
US4148918A (en)	1979-04-10	Substituted 2-higher alkyl-3-hydroxy-1,4-naphthoquinone carboxylic acid esters and their use as miticides
US4013444A (en)	1977-03-22	Inhibiting grass growth with 5-acetamido-2,4-dimethyltrifluoromethanesulfonanilide
US4191554A (en)	1980-03-04	Herbicidal benzamides
US4945113A (en)	1990-07-31	herbicidal sulfonamide derivatives
US4092151A (en)	1978-05-30	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US6642179B2 (en)	2003-11-04	Inhibition of vegetative growth
US3793372A (en)	1974-02-19	N-cyanohaloalkanesulfonanilides
EP0205821A1 (fr)	1986-12-30	Dérivés halogéno-alkoxy-anilidés d'acides (hétérocyclyloxy-4 phénoxy)-2 alcanoiques et leur application comme herbicides
US3985539A (en)	1976-10-12	4,5-Dihalopyrrole-2-carbonitrile-containing terrestrial and aquatic hebicidal composition
EP0048550B1 (fr)	1984-03-28	Sulfonanilides cycliques acylaminoperfluoroalcane et leurs dérivés
US4076519A (en)	1978-02-28	N-substituted perfluoroalkanesulfonamides as herbicides
US4163659A (en)	1979-08-07	Stunting plant growth with N-substituted perfluoroalkanesulfonamides
US3766193A (en)	1973-10-16	N heterocyclicalkyl fluoroalkane sulfonamides
US3512955A (en)	1970-05-19	Method of protecting plant growth
US5032168A (en)	1991-07-16	4-((aryloxy)phenoxy)fluoroalkanoic acid derivatives and their herbicidal uses
US6451741B1 (en)	2002-09-17	Inhibition of vegetative growth
EP0249858B1 (fr)	1990-12-05	Dérivés de la quinoléine fluoroalkyl-substitués, leur synthèse et leur utilisation contre les plantes non-désirées
US4380464A (en)	1983-04-19	N,N-Diacylaminoperfluoroalkanesulfonanilides and derivatives thereof