CA1140569A - N.sup.4-phenoxyalkanoylsulfanilamides and herbicidal composition containing the same - Google Patents
N.sup.4-phenoxyalkanoylsulfanilamides and herbicidal composition containing the sameInfo
- Publication number
- CA1140569A CA1140569A CA000359541A CA359541A CA1140569A CA 1140569 A CA1140569 A CA 1140569A CA 000359541 A CA000359541 A CA 000359541A CA 359541 A CA359541 A CA 359541A CA 1140569 A CA1140569 A CA 1140569A
- Authority
- CA
- Canada
- Prior art keywords
- accordance
- acetyl
- methoxycarbonyl
- sulfanilamide
- compounds
- 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
- 230000002363 herbicidal effect Effects 0.000 title abstract description 35
- 239000000203 mixture Substances 0.000 title abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- -1 alkaline earth metal salt Chemical class 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 136
- 239000002253 acid Substances 0.000 claims description 7
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 7
- 229940124530 sulfonamide Drugs 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- LPTAMPXEWJNOPD-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-n-(4-sulfamoylphenyl)acetamide Chemical compound CC1=CC(Cl)=CC=C1OCC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 LPTAMPXEWJNOPD-UHFFFAOYSA-N 0.000 claims 1
- YBRARIQOTUUATQ-UHFFFAOYSA-N N-[4-(carbamoylsulfamoyl)phenyl]-2-(4-chloro-2-methylphenoxy)acetamide Chemical compound C(N)(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=C(C=C(C=C1)Cl)C)=O)=O YBRARIQOTUUATQ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- CARVZBNUCMFAPA-UHFFFAOYSA-N methyl N-[4-[[2-(2,4-dichlorophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=C(C=C(C=C1)Cl)Cl)=O)=O CARVZBNUCMFAPA-UHFFFAOYSA-N 0.000 claims 1
- UXMAGKILYFLLLD-UHFFFAOYSA-N methyl N-[4-[[2-(2,4-dinitrophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])=O)=O UXMAGKILYFLLLD-UHFFFAOYSA-N 0.000 claims 1
- HINTZHDCNUBZRT-UHFFFAOYSA-N methyl N-[4-[[2-(2-chlorophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=C(C=CC=C1)Cl)=O)=O HINTZHDCNUBZRT-UHFFFAOYSA-N 0.000 claims 1
- WJRAYTKXWFCTSO-UHFFFAOYSA-N methyl N-[4-[[2-(2-methylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=C(C=CC=C1)C)=O)=O WJRAYTKXWFCTSO-UHFFFAOYSA-N 0.000 claims 1
- FRMTUIONKNSFFU-UHFFFAOYSA-N methyl N-[4-[[2-(2-nitrophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=C(C=CC=C1)[N+](=O)[O-])=O)=O FRMTUIONKNSFFU-UHFFFAOYSA-N 0.000 claims 1
- IZAJBHQZQNCLOX-UHFFFAOYSA-N methyl N-[4-[[2-(3,5-dichlorophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC(=CC(=C1)Cl)Cl)=O)=O IZAJBHQZQNCLOX-UHFFFAOYSA-N 0.000 claims 1
- UIUFVYXXKCVRHB-UHFFFAOYSA-N methyl N-[4-[[2-(3,5-dimethylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC(=CC(=C1)C)C)=O)=O UIUFVYXXKCVRHB-UHFFFAOYSA-N 0.000 claims 1
- BRFZMVAVUNPQBS-UHFFFAOYSA-N methyl N-[4-[[2-(3-chlorophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC(=CC=C1)Cl)=O)=O BRFZMVAVUNPQBS-UHFFFAOYSA-N 0.000 claims 1
- GTATVJZDCSMIOO-UHFFFAOYSA-N methyl N-[4-[[2-(3-methylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC(=CC=C1)C)=O)=O GTATVJZDCSMIOO-UHFFFAOYSA-N 0.000 claims 1
- WUDZMGQBDQGBMS-UHFFFAOYSA-N methyl N-[4-[[2-(3-nitrophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC(=CC=C1)[N+](=O)[O-])=O)=O WUDZMGQBDQGBMS-UHFFFAOYSA-N 0.000 claims 1
- JQQPGKDUXPFCLN-UHFFFAOYSA-N methyl N-[4-[[2-(4-bromophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC=C(C=C1)Br)=O)=O JQQPGKDUXPFCLN-UHFFFAOYSA-N 0.000 claims 1
- WGNZAVMBLCJIMZ-UHFFFAOYSA-N methyl N-[4-[[2-(4-fluorophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC=C(C=C1)F)=O)=O WGNZAVMBLCJIMZ-UHFFFAOYSA-N 0.000 claims 1
- GPDNDIMYTVQTDV-UHFFFAOYSA-N methyl N-[4-[[2-(4-methylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(C1=CC=C(C=C1)NC(COC1=CC=C(C=C1)C)=O)=O GPDNDIMYTVQTDV-UHFFFAOYSA-N 0.000 claims 1
- FCRJXWLPZVNEFU-UHFFFAOYSA-N methyl n-[4-[2-(4-chloro-2-methylphenoxy)propanoylamino]phenyl]sulfonylcarbamate Chemical compound C1=CC(S(=O)(=O)NC(=O)OC)=CC=C1NC(=O)C(C)OC1=CC=C(Cl)C=C1C FCRJXWLPZVNEFU-UHFFFAOYSA-N 0.000 claims 1
- QSRAONKHPYBRBR-UHFFFAOYSA-N methyl n-[4-[[2-(3,4-dichlorophenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound C1=CC(S(=O)(=O)NC(=O)OC)=CC=C1NC(=O)COC1=CC=C(Cl)C(Cl)=C1 QSRAONKHPYBRBR-UHFFFAOYSA-N 0.000 claims 1
- LFDDUUFFHPNIPZ-UHFFFAOYSA-N methyl n-[4-[[2-(4-chloro-2-methylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound C1=CC(S(=O)(=O)NC(=O)OC)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C LFDDUUFFHPNIPZ-UHFFFAOYSA-N 0.000 claims 1
- FMIANFJAAYQFAH-UHFFFAOYSA-N n-[4-(acetylsulfamoyl)phenyl]-2-(4-chloro-2-methylphenoxy)acetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C FMIANFJAAYQFAH-UHFFFAOYSA-N 0.000 claims 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 abstract description 5
- 241000196324 Embryophyta Species 0.000 description 67
- 240000007594 Oryza sativa Species 0.000 description 22
- 230000000694 effects Effects 0.000 description 20
- 235000007164 Oryza sativa Nutrition 0.000 description 19
- 235000009566 rice Nutrition 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 230000012010 growth Effects 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 241000894007 species Species 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 244000058871 Echinochloa crus-galli Species 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
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- 239000005574 MCPA Substances 0.000 description 5
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- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000010899 nucleation Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
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- 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 4
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- ABYSGRXBGLVRGO-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetyl chloride Chemical compound CC1=CC(Cl)=CC=C1OCC(Cl)=O ABYSGRXBGLVRGO-UHFFFAOYSA-N 0.000 description 2
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- VZECTCSEONQIPP-UHFFFAOYSA-N 2-(3-methylphenoxy)acetic acid Chemical compound CC1=CC=CC(OCC(O)=O)=C1 VZECTCSEONQIPP-UHFFFAOYSA-N 0.000 description 1
- SZEBGAQWWSUOHT-UHFFFAOYSA-N 2-(4-bromophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1 SZEBGAQWWSUOHT-UHFFFAOYSA-N 0.000 description 1
- ZBIULCVFFJJYTN-UHFFFAOYSA-N 2-(4-fluorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(F)C=C1 ZBIULCVFFJJYTN-UHFFFAOYSA-N 0.000 description 1
- SFTDDFBJWUWKMN-UHFFFAOYSA-N 2-(4-methylphenoxy)acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C=C1 SFTDDFBJWUWKMN-UHFFFAOYSA-N 0.000 description 1
- SNYRXHULAWEECU-UHFFFAOYSA-N 3,4-dichlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C(Cl)=C1 SNYRXHULAWEECU-UHFFFAOYSA-N 0.000 description 1
- QATKOZUHTGAWMG-UHFFFAOYSA-N 4-fluoro-3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(O)=C1 QATKOZUHTGAWMG-UHFFFAOYSA-N 0.000 description 1
- AVDLFIONKHGQAP-UHFFFAOYSA-N 4-nitrophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1 AVDLFIONKHGQAP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000055702 Amaranthus viridis Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 244000108484 Cyperus difformis Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 241000634867 Eleocharis uniglumis Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
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- RRCYYLHJWRYWEI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOO RRCYYLHJWRYWEI-UHFFFAOYSA-N 0.000 description 1
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- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 241000287531 Psittacidae Species 0.000 description 1
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- 235000005010 Scirpus paludosus Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 240000003829 Sorghum propinquum Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- JMLFOZVZGFQYOT-UHFFFAOYSA-N butanedioic acid;sulfuric acid Chemical compound OS(O)(=O)=O.OC(=O)CCC(O)=O JMLFOZVZGFQYOT-UHFFFAOYSA-N 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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 238000010908 decantation Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- AQXRGTADPFHASO-UHFFFAOYSA-N methyl n-acetyl-n-(4-aminophenyl)sulfonylcarbamate Chemical compound COC(=O)N(C(C)=O)S(=O)(=O)C1=CC=C(N)C=C1 AQXRGTADPFHASO-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 108010080511 serum sodium transport inhibitor Proteins 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000009367 silviculture Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WVAKABMNNSMCDK-UHFFFAOYSA-N sulfacarbamide Chemical compound NC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 WVAKABMNNSMCDK-UHFFFAOYSA-N 0.000 description 1
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 1
- 229960002673 sulfacetamide Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 244000259727 waterwort Species 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B6/00—Heating by electric, magnetic or electromagnetic fields
- H05B6/64—Heating using microwaves
- H05B6/6435—Aspects relating to the user interface of the microwave heating apparatus
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B6/00—Heating by electric, magnetic or electromagnetic fields
- H05B6/64—Heating using microwaves
- H05B6/6435—Aspects relating to the user interface of the microwave heating apparatus
- H05B6/6438—Aspects relating to the user interface of the microwave heating apparatus allowing the recording of a program of operation of the microwave heating apparatus
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B6/00—Heating by electric, magnetic or electromagnetic fields
- H05B6/64—Heating using microwaves
- H05B6/647—Aspects related to microwave heating combined with other heating techniques
- H05B6/6482—Aspects related to microwave heating combined with other heating techniques combined with radiant heating, e.g. infrared heating
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Electromagnetism (AREA)
- Physics & Mathematics (AREA)
- Human Computer Interaction (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54122423A JPS6055062B2 (ja) | 1979-09-21 | 1979-09-21 | Ｎ↑４−フエノキシアセチルスルフアニルアミド類および除草剤 |
| JP122423/1979 | 1979-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140569A true CA1140569A (en) | 1983-02-01 |
Family
ID=14835458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000359541A Expired CA1140569A (en) | 1979-09-21 | 1980-09-04 | N.sup.4-phenoxyalkanoylsulfanilamides and herbicidal composition containing the same |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4314845A (OSRAM) |
| JP (1) | JPS6055062B2 (OSRAM) |
| AR (1) | AR228577A1 (OSRAM) |
| AU (1) | AU534963B2 (OSRAM) |
| BR (1) | BR8006038A (OSRAM) |
| CA (1) | CA1140569A (OSRAM) |
| CH (1) | CH644843A5 (OSRAM) |
| DE (1) | DE3034063A1 (OSRAM) |
| ES (1) | ES8107176A1 (OSRAM) |
| FR (1) | FR2465719A1 (OSRAM) |
| GB (1) | GB2061923B (OSRAM) |
| IT (1) | IT1129266B (OSRAM) |
| MX (1) | MX6240E (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8193194B2 (en) * | 2007-05-25 | 2012-06-05 | Vertex Pharmaceuticals Incorporated | Ion channel modulators and methods of use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR4316E (fr) | 1905-07-07 | Francois Roux | Voiture hygiénique pour l'enlèvement des immondices dans les villes | |
| NL283003A (OSRAM) * | 1961-09-08 | |||
| US3849110A (en) * | 1963-01-07 | 1974-11-19 | Lilly Co Eli | Herbicidal method employing aryl-sulfonylureas or salts thereof |
| GB1051011A (OSRAM) * | 1963-02-28 | |||
| CA1072359A (en) * | 1974-10-08 | 1980-02-26 | Hiroyuki Konishi | Method for controlling the growth of plants |
| JPS5233614A (en) * | 1975-09-11 | 1977-03-14 | Daicel Chem Ind Ltd | Process for preparation of acetic acid |
-
1979
- 1979-09-21 JP JP54122423A patent/JPS6055062B2/ja not_active Expired
-
1980
- 1980-09-01 AU AU61937/80A patent/AU534963B2/en not_active Ceased
- 1980-09-04 CA CA000359541A patent/CA1140569A/en not_active Expired
- 1980-09-09 US US06/185,965 patent/US4314845A/en not_active Expired - Lifetime
- 1980-09-10 DE DE19803034063 patent/DE3034063A1/de not_active Ceased
- 1980-09-10 GB GB8029181A patent/GB2061923B/en not_active Expired
- 1980-09-12 FR FR8019764A patent/FR2465719A1/fr active Granted
- 1980-09-15 ES ES495058A patent/ES8107176A1/es not_active Expired
- 1980-09-18 CH CH700280A patent/CH644843A5/de not_active IP Right Cessation
- 1980-09-19 AR AR282591A patent/AR228577A1/es active
- 1980-09-19 IT IT68461/80A patent/IT1129266B/it active
- 1980-09-19 MX MX809038U patent/MX6240E/es unknown
- 1980-09-19 BR BR8006038A patent/BR8006038A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4314845A (en) | 1982-02-09 |
| IT8068461A0 (it) | 1980-09-19 |
| JPS5649347A (en) | 1981-05-02 |
| IT1129266B (it) | 1986-06-04 |
| AU534963B2 (en) | 1984-02-23 |
| MX6240E (es) | 1985-01-25 |
| FR2465719B1 (OSRAM) | 1983-11-25 |
| BR8006038A (pt) | 1981-04-07 |
| ES495058A0 (es) | 1981-10-01 |
| AR228577A1 (es) | 1983-03-30 |
| GB2061923A (en) | 1981-05-20 |
| CH644843A5 (de) | 1984-08-31 |
| DE3034063A1 (de) | 1981-04-09 |
| GB2061923B (en) | 1984-02-29 |
| FR2465719A1 (fr) | 1981-03-27 |
| AU6193780A (en) | 1981-09-24 |
| JPS6055062B2 (ja) | 1985-12-03 |
| ES8107176A1 (es) | 1981-10-01 |
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