CA1066294A - 1,2-dialkyl-3,4,5-trisubstituted pyrazolium salts as herbicidal agents - Google Patents
1,2-dialkyl-3,4,5-trisubstituted pyrazolium salts as herbicidal agentsInfo
- Publication number
- CA1066294A CA1066294A CA230,261A CA230261A CA1066294A CA 1066294 A CA1066294 A CA 1066294A CA 230261 A CA230261 A CA 230261A CA 1066294 A CA1066294 A CA 1066294A
- Authority
- CA
- Canada
- Prior art keywords
- dimethyl
- compound according
- diphenyl
- methyl
- methyl sulfate
- 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
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title abstract description 11
- 239000004009 herbicide Substances 0.000 title abstract description 6
- -1 hydrogen halogen Chemical class 0.000 claims abstract description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical group 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 150000001450 anions Chemical group 0.000 claims abstract description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 231100000208 phytotoxic Toxicity 0.000 claims abstract description 3
- 230000000885 phytotoxic effect Effects 0.000 claims abstract description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 18
- 241001148683 Zostera marina Species 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 229940077388 benzenesulfonate Drugs 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 6
- HOICMKJQBOYRNE-UHFFFAOYSA-M 4-methoxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OC)=C1C1=CC=CC=C1 HOICMKJQBOYRNE-UHFFFAOYSA-M 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000006371 dihalo methyl group Chemical group 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 3
- OHRGUJAZEAVCGX-UHFFFAOYSA-M 4-methoxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OC)=C1C1=CC=CC=C1 OHRGUJAZEAVCGX-UHFFFAOYSA-M 0.000 claims description 2
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 claims description 2
- LMTCHGGUTAQCCC-UHFFFAOYSA-M 4-butoxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OCCCC)=C1C1=CC=CC=C1 LMTCHGGUTAQCCC-UHFFFAOYSA-M 0.000 claims 2
- JGTCFXNARFYYEV-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenyl-4-phenylmethoxypyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C=1C=CC=CC=1C1=[N+](C)N(C)C(C=2C=CC=CC=2)=C1OCC1=CC=CC=C1 JGTCFXNARFYYEV-UHFFFAOYSA-M 0.000 claims 1
- SRNJAIRXQTVVHK-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenyl-4-prop-2-ynoxypyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=C(OCC#C)C=1C1=CC=CC=C1 SRNJAIRXQTVVHK-UHFFFAOYSA-M 0.000 claims 1
- LCCFUDRBHKEYMZ-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenyl-4-propoxypyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OCCC)=C1C1=CC=CC=C1 LCCFUDRBHKEYMZ-UHFFFAOYSA-M 0.000 claims 1
- JFIDWFPUAIXAMM-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenyl-4-tridecoxypyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OCCCCCCCCCCCCC)=C1C1=CC=CC=C1 JFIDWFPUAIXAMM-UHFFFAOYSA-M 0.000 claims 1
- VPOHTULWZZBKOI-UHFFFAOYSA-M 1,2-dimethyl-4-pentoxy-3,5-diphenylpyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OCCCCC)=C1C1=CC=CC=C1 VPOHTULWZZBKOI-UHFFFAOYSA-M 0.000 claims 1
- AWAIAJLLABXSLK-UHFFFAOYSA-M 1,2-dimethyl-4-pentoxy-3,5-diphenylpyrazol-2-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OCCCCC)=C1C1=CC=CC=C1 AWAIAJLLABXSLK-UHFFFAOYSA-M 0.000 claims 1
- NXIMVHQAPWRVCG-UHFFFAOYSA-M 4-butan-2-yloxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OC(C)CC)=C1C1=CC=CC=C1 NXIMVHQAPWRVCG-UHFFFAOYSA-M 0.000 claims 1
- XAYZFRAPLHMGKL-UHFFFAOYSA-M 4-butan-2-yloxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OC(C)CC)=C1C1=CC=CC=C1 XAYZFRAPLHMGKL-UHFFFAOYSA-M 0.000 claims 1
- VZMFHPDPIKIYMJ-UHFFFAOYSA-M 4-ethoxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OCC)=C1C1=CC=CC=C1 VZMFHPDPIKIYMJ-UHFFFAOYSA-M 0.000 claims 1
- GJUBJCPCMXVKQZ-UHFFFAOYSA-M 4-hexadecoxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OCCCCCCCCCCCCCCCC)=C1C1=CC=CC=C1 GJUBJCPCMXVKQZ-UHFFFAOYSA-M 0.000 claims 1
- ORJHRDWUOOJHJT-UHFFFAOYSA-M 4-hexoxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(OCCCCCC)=C1C1=CC=CC=C1 ORJHRDWUOOJHJT-UHFFFAOYSA-M 0.000 claims 1
- WDLZGIRJEQKLJD-UHFFFAOYSA-M 4-methoxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;bromide Chemical compound [Br-].CN1[N+](C)=C(C=2C=CC=CC=2)C(OC)=C1C1=CC=CC=C1 WDLZGIRJEQKLJD-UHFFFAOYSA-M 0.000 claims 1
- KUZPFROWGZVUSR-UHFFFAOYSA-M 4-methoxy-1,2-dimethyl-3,5-diphenylpyrazol-2-ium;iodide Chemical compound [I-].CN1[N+](C)=C(C=2C=CC=CC=2)C(OC)=C1C1=CC=CC=C1 KUZPFROWGZVUSR-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 54
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 35
- 239000007787 solid Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 229960001701 chloroform Drugs 0.000 description 26
- 239000010410 layer Substances 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229940083608 sodium hydroxide Drugs 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229940076134 benzene Drugs 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 244000058871 Echinochloa crus-galli Species 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 235000007320 Avena fatua Nutrition 0.000 description 5
- 240000006122 Chenopodium album Species 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 5
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- 239000012044 organic layer Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
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- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000036244 malformation Effects 0.000 description 2
- 125000005527 methyl sulfate group Chemical group 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- VUCUYKQOVICZBP-UHFFFAOYSA-N 1,2-dimethyl-3,5-diphenylpyrazol-2-ium-4-ol;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=C(O)C=1C1=CC=CC=C1 VUCUYKQOVICZBP-UHFFFAOYSA-N 0.000 description 1
- JEBPXHXMTVKEMY-UHFFFAOYSA-N 1-methyl-3,5-diphenyl-4-phenylmethoxypyrazole Chemical class C=1C=CC=CC=1C=1N(C)N=C(C=2C=CC=CC=2)C=1OCC1=CC=CC=C1 JEBPXHXMTVKEMY-UHFFFAOYSA-N 0.000 description 1
- QRXFXIFOJQEYHC-UHFFFAOYSA-N 1-methyl-3,5-diphenyl-4-phenylsulfanylpyrazole Chemical compound C=1C=CC=CC=1C=1N(C)N=C(C=2C=CC=CC=2)C=1SC1=CC=CC=C1 QRXFXIFOJQEYHC-UHFFFAOYSA-N 0.000 description 1
- FAMXMDSBUUBKLN-UHFFFAOYSA-N 1-methyl-4-[(2-methylpropan-2-yl)oxy]-3,5-diphenylpyrazole Chemical compound CN1N=C(C=2C=CC=CC=2)C(OC(C)(C)C)=C1C1=CC=CC=C1 FAMXMDSBUUBKLN-UHFFFAOYSA-N 0.000 description 1
- KAUABWYBFARJAF-UHFFFAOYSA-N 1h-pyrazol-4-ol Chemical compound OC=1C=NNC=1 KAUABWYBFARJAF-UHFFFAOYSA-N 0.000 description 1
- GBNOSMRRYYJCFQ-UHFFFAOYSA-N 1h-pyrazole;hydrate Chemical compound O.C=1C=NNC=1 GBNOSMRRYYJCFQ-UHFFFAOYSA-N 0.000 description 1
- IJEUECPYNRXTQZ-UHFFFAOYSA-N 2-(1-methyl-3,5-diphenylpyrazol-4-yl)oxyethanol Chemical compound CN1N=C(C=2C=CC=CC=2)C(OCCO)=C1C1=CC=CC=C1 IJEUECPYNRXTQZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 description 1
- XUGMIFAZWUJPTP-UHFFFAOYSA-N 3,5-diphenyl-4-phenylmethoxy-1h-pyrazole Chemical compound C=1C=CC=CC=1COC=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 XUGMIFAZWUJPTP-UHFFFAOYSA-N 0.000 description 1
- VNFHSHCUHWJQLL-UHFFFAOYSA-N 3,5-diphenyl-4-propoxy-1h-pyrazole Chemical compound CCCOC=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 VNFHSHCUHWJQLL-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- WTKTVGJZPASPEI-UHFFFAOYSA-N 4-(1-methyl-3,5-diphenylpyrazol-4-yl)oxyaniline Chemical compound C=1C=CC=CC=1C=1N(C)N=C(C=2C=CC=CC=2)C=1OC1=CC=C(N)C=C1 WTKTVGJZPASPEI-UHFFFAOYSA-N 0.000 description 1
- MLDXTFUNOFVJRF-UHFFFAOYSA-N 4-(2-bromoethoxy)-1-methyl-3,5-diphenylpyrazole Chemical compound CN1N=C(C=2C=CC=CC=2)C(OCCBr)=C1C1=CC=CC=C1 MLDXTFUNOFVJRF-UHFFFAOYSA-N 0.000 description 1
- WIFLPRFLIZUDLW-UHFFFAOYSA-N 4-(heptoxymethoxy)-1-methyl-3,5-diphenylpyrazole Chemical compound CCCCCCCOCOC=1C(C=2C=CC=CC=2)=NN(C)C=1C1=CC=CC=C1 WIFLPRFLIZUDLW-UHFFFAOYSA-N 0.000 description 1
- QTQLSKMNUJJFSP-UHFFFAOYSA-N 4-butoxy-1-methyl-3,5-diphenylpyrazole Chemical compound CCCCOC=1C(C=2C=CC=CC=2)=NN(C)C=1C1=CC=CC=C1 QTQLSKMNUJJFSP-UHFFFAOYSA-N 0.000 description 1
- IMJDOPWSZWSKMU-UHFFFAOYSA-N 4-butylsulfanyl-1-methyl-3,5-diphenylpyrazole Chemical compound CCCCSC=1C(C=2C=CC=CC=2)=NN(C)C=1C1=CC=CC=C1 IMJDOPWSZWSKMU-UHFFFAOYSA-N 0.000 description 1
- GUVQHFNSXZGZHF-UHFFFAOYSA-N 4-methoxy-1-methyl-3,5-diphenylpyrazole Chemical compound COC=1C(C=2C=CC=CC=2)=NN(C)C=1C1=CC=CC=C1 GUVQHFNSXZGZHF-UHFFFAOYSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 235000004535 Avena sterilis Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101100456896 Drosophila melanogaster metl gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- PQUGCKBLVKJMNT-UHFFFAOYSA-N SC560 Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 PQUGCKBLVKJMNT-UHFFFAOYSA-N 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- 235000002834 Sida rhombifolia Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SRXOCFMDUSFFAK-UHFFFAOYSA-N dimethyl peroxide Chemical compound COOC SRXOCFMDUSFFAK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 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
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48782674A | 1974-07-12 | 1974-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1066294A true CA1066294A (en) | 1979-11-13 |
Family
ID=23937260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,261A Expired CA1066294A (en) | 1974-07-12 | 1975-06-26 | 1,2-dialkyl-3,4,5-trisubstituted pyrazolium salts as herbicidal agents |
Country Status (12)
-
1975
- 1975-06-17 ZA ZA00753894A patent/ZA753894B/xx unknown
- 1975-06-20 GB GB26396/75A patent/GB1519494A/en not_active Expired
- 1975-06-23 AU AU82363/75A patent/AU498491B2/en not_active Expired
- 1975-06-26 CA CA230,261A patent/CA1066294A/en not_active Expired
- 1975-06-26 AR AR259362A patent/AR216425A1/es active
- 1975-07-04 RO RO7582753A patent/RO68992A/ro unknown
- 1975-07-08 IT IT50419/75A patent/IT1050692B/it active
- 1975-07-09 FI FI752005A patent/FI752005A7/fi not_active Application Discontinuation
- 1975-07-11 BE BE158210A patent/BE831272R/xx not_active IP Right Cessation
- 1975-07-11 FR FR7521950A patent/FR2295027A2/fr active Granted
- 1975-07-11 SE SE7508002A patent/SE7508002L/xx unknown
- 1975-07-11 DK DK317975A patent/DK317975A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2295027A2 (fr) | 1976-07-16 |
| ZA753894B (en) | 1976-05-26 |
| RO68992A (ro) | 1981-07-30 |
| AU498491B2 (en) | 1979-03-15 |
| AU8236375A (en) | 1977-01-06 |
| GB1519494A (en) | 1978-07-26 |
| IT1050692B (it) | 1981-03-20 |
| AR216425A1 (es) | 1979-12-28 |
| DK317975A (da) | 1976-01-13 |
| FI752005A7 (enrdf_load_stackoverflow) | 1976-01-13 |
| BE831272R (fr) | 1976-01-12 |
| FR2295027B2 (enrdf_load_stackoverflow) | 1978-09-22 |
| SE7508002L (sv) | 1976-02-11 |
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