CA1102801A - N-phenyl-substituted n-heterocyclic compounds, their preparation and use in agents for regulating plant growth - Google Patents
N-phenyl-substituted n-heterocyclic compounds, their preparation and use in agents for regulating plant growthInfo
- Publication number
- CA1102801A CA1102801A CA301,079A CA301079A CA1102801A CA 1102801 A CA1102801 A CA 1102801A CA 301079 A CA301079 A CA 301079A CA 1102801 A CA1102801 A CA 1102801A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- pyrrolidin
- alkyl
- dimethylphenyl
- compound
- 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
- 230000008635 plant growth Effects 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 230000001105 regulatory effect Effects 0.000 title description 4
- -1 nitrogen heterocyclic compounds Chemical class 0.000 claims abstract description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
- 241000196324 Embryophyta Species 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 230000012010 growth Effects 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 235000013339 cereals Nutrition 0.000 claims description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 241000209504 Poaceae Species 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 244000068988 Glycine max Species 0.000 claims description 5
- 235000010469 Glycine max Nutrition 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 244000061176 Nicotiana tabacum Species 0.000 claims description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 4
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- NQGLSXLJOHWQMF-UHFFFAOYSA-N n-[2,4-dimethyl-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(C)=C1N1C(=O)CCC1 NQGLSXLJOHWQMF-UHFFFAOYSA-N 0.000 claims description 3
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 claims description 3
- KKSZUINUYGAPQZ-UHFFFAOYSA-N 1,1,1-trifluoro-n-[2-methyl-5-(2-oxopyrrolidin-1-yl)phenyl]methanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC=C1N1C(=O)CCC1 KKSZUINUYGAPQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- WTMXWTJMTQHSFC-UHFFFAOYSA-N n-[2,4-dimethyl-5-(2-methyl-5-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound CC1CCC(=O)N1C1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C WTMXWTJMTQHSFC-UHFFFAOYSA-N 0.000 claims description 2
- ASRPAYCRIPRJQF-UHFFFAOYSA-N n-[2,4-dimethyl-5-(2-oxopiperidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(C)=C1N1C(=O)CCCC1 ASRPAYCRIPRJQF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- KXZFSXQYGMQDQA-UHFFFAOYSA-N 1,1,1-trifluoro-n-(2-methyl-5-piperidin-1-ylphenyl)methanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC=C1N1CCCCC1 KXZFSXQYGMQDQA-UHFFFAOYSA-N 0.000 claims 1
- XLVLDOOGKOPUGL-UHFFFAOYSA-N 1,1,1-trifluoro-n-[2-methyl-5-(2-oxopiperidin-1-yl)phenyl]methanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC=C1N1C(=O)CCCC1 XLVLDOOGKOPUGL-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Chemical group 0.000 claims 1
- BQXDFLYMWHHKMJ-UHFFFAOYSA-N n-(2,4-dimethyl-5-piperidin-1-ylphenyl)-1,1,1-trifluoromethanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(C)=C1N1CCCCC1 BQXDFLYMWHHKMJ-UHFFFAOYSA-N 0.000 claims 1
- HAXKZIPFAYRRSP-UHFFFAOYSA-N n-[2,3-dimethyl-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NC1=C(C)C(C)=CC(N2C(CCC2)=O)=C1 HAXKZIPFAYRRSP-UHFFFAOYSA-N 0.000 claims 1
- CEZMVTBHMCIRFC-UHFFFAOYSA-N n-[2,4-dichloro-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C(F)(F)F)=CC(N2C(CCC2)=O)=C1Cl CEZMVTBHMCIRFC-UHFFFAOYSA-N 0.000 claims 1
- KTADIBBATRQANR-UHFFFAOYSA-N n-[2,4-dimethyl-5-(2-oxoazepan-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(C)=C1N1C(=O)CCCCC1 KTADIBBATRQANR-UHFFFAOYSA-N 0.000 claims 1
- NIJLQOHADLACOC-UHFFFAOYSA-N n-[2,4-dimethyl-5-(3-methyl-2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound O=C1C(C)CCN1C1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C NIJLQOHADLACOC-UHFFFAOYSA-N 0.000 claims 1
- YGHNLSCTFPKQDI-UHFFFAOYSA-N n-[2-chloro-4-methyl-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound CC1=CC(Cl)=C(NS(=O)(=O)C(F)(F)F)C=C1N1C(=O)CCC1 YGHNLSCTFPKQDI-UHFFFAOYSA-N 0.000 claims 1
- GOLPYJDOLZARBB-UHFFFAOYSA-N n-[5-(3-ethyl-2-oxopyrrolidin-1-yl)-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound O=C1C(CC)CCN1C1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C GOLPYJDOLZARBB-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 22
- 230000002363 herbicidal effect Effects 0.000 abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 36
- 235000013350 formula milk Nutrition 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000008187 granular material Substances 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229960001701 chloroform Drugs 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 229960000443 hydrochloric acid Drugs 0.000 description 8
- 235000011167 hydrochloric acid Nutrition 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 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 8
- 239000005995 Aluminium silicate Substances 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 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 7
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 229940086542 triethylamine Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000006286 aqueous extract Substances 0.000 description 5
- 239000012876 carrier material Substances 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000010410 dusting Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical class O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000003966 growth inhibitor Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LAOUPUPMWFEWQK-UHFFFAOYSA-N 1-(3-amino-4-methylphenyl)-3,4-dimethylpyrrole-2,5-dione Chemical compound O=C1C(C)=C(C)C(=O)N1C1=CC=C(C)C(N)=C1 LAOUPUPMWFEWQK-UHFFFAOYSA-N 0.000 description 2
- JPWYHWFXQQVCID-UHFFFAOYSA-N 1-(3-amino-4-methylphenyl)pyrrolidin-2-one Chemical compound C1=C(N)C(C)=CC=C1N1C(=O)CCC1 JPWYHWFXQQVCID-UHFFFAOYSA-N 0.000 description 2
- SRSWRZAAMYMOMH-UHFFFAOYSA-N 1-(5-amino-2,4-dimethylphenyl)azetidin-2-one Chemical compound C1=C(N)C(C)=CC(C)=C1N1C(=O)CC1 SRSWRZAAMYMOMH-UHFFFAOYSA-N 0.000 description 2
- WXDRSESPRBOCTG-UHFFFAOYSA-N 1-(5-amino-2,4-dimethylphenyl)piperidin-2-one Chemical compound C1=C(N)C(C)=CC(C)=C1N1C(=O)CCCC1 WXDRSESPRBOCTG-UHFFFAOYSA-N 0.000 description 2
- PFUFDQACGFALAE-UHFFFAOYSA-N 1-(5-amino-4-chloro-2-methylphenyl)pyrrolidin-2-one Chemical compound CC1=CC(Cl)=C(N)C=C1N1C(=O)CCC1 PFUFDQACGFALAE-UHFFFAOYSA-N 0.000 description 2
- DCSSXQMBIGEQGN-UHFFFAOYSA-N 4,6-dimethylbenzene-1,3-diamine Chemical compound CC1=CC(C)=C(N)C=C1N DCSSXQMBIGEQGN-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 241000220485 Fabaceae Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000004296 Lolium perenne Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 241000209056 Secale Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 229940022682 acetone Drugs 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- DXEVSEQSWDCEGX-UHFFFAOYSA-N n-[2,4-dimethyl-5-(2-oxoazetidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(C)=C1N1C(=O)CC1 DXEVSEQSWDCEGX-UHFFFAOYSA-N 0.000 description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical class O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- ZPXDNSYFDIHPOJ-UHFFFAOYSA-N 1,5-dichloro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C=C1Cl ZPXDNSYFDIHPOJ-UHFFFAOYSA-N 0.000 description 1
- YSVXRYLPTVXKKC-UHFFFAOYSA-N 1-(2,4-dimethyl-5-nitrophenyl)azetidin-2-one Chemical compound CC1=CC(C)=C([N+]([O-])=O)C=C1N1C(=O)CC1 YSVXRYLPTVXKKC-UHFFFAOYSA-N 0.000 description 1
- JXMKEUOFVUVRRX-UHFFFAOYSA-N 1-(2-amino-4,5-dimethylphenyl)pyrrolidin-2-one Chemical compound C1=C(C)C(C)=CC(N)=C1N1C(=O)CCC1 JXMKEUOFVUVRRX-UHFFFAOYSA-N 0.000 description 1
- IHNQMLSTCVEMCR-UHFFFAOYSA-N 1-(2-amino-4-methylphenyl)pyrrolidin-2-one Chemical compound NC1=CC(C)=CC=C1N1C(=O)CCC1 IHNQMLSTCVEMCR-UHFFFAOYSA-N 0.000 description 1
- OFWIPSFSNBNOQC-UHFFFAOYSA-N 1-(2-aminophenyl)pyrrolidin-2-one Chemical compound NC1=CC=CC=C1N1C(=O)CCC1 OFWIPSFSNBNOQC-UHFFFAOYSA-N 0.000 description 1
- LVFOAYJQHDACLT-UHFFFAOYSA-N 1-(3-amino-2,4,6-trimethylphenyl)piperidin-2-one Chemical compound CC1=C(N)C(C)=CC(C)=C1N1C(=O)CCCC1 LVFOAYJQHDACLT-UHFFFAOYSA-N 0.000 description 1
- WTFVXXJGMSQGJJ-UHFFFAOYSA-N 1-(3-amino-2,4-dimethylphenyl)pyrrolidin-2-one Chemical compound CC1=C(N)C(C)=CC=C1N1C(=O)CCC1 WTFVXXJGMSQGJJ-UHFFFAOYSA-N 0.000 description 1
- SGFUUFQFNKKLAZ-UHFFFAOYSA-N 1-(3-amino-2,6-diethylphenyl)piperidin-2-one Chemical compound CCC1=CC=C(N)C(CC)=C1N1C(=O)CCCC1 SGFUUFQFNKKLAZ-UHFFFAOYSA-N 0.000 description 1
- UUYGXIWQQLGNAD-UHFFFAOYSA-N 1-(3-amino-2,6-diethylphenyl)pyrrolidin-2-one Chemical compound CCC1=CC=C(N)C(CC)=C1N1C(=O)CCC1 UUYGXIWQQLGNAD-UHFFFAOYSA-N 0.000 description 1
- GAIIEUXSQGXFLO-UHFFFAOYSA-N 1-(3-amino-2,6-dimethylphenyl)pyrrolidin-2-one Chemical compound CC1=CC=C(N)C(C)=C1N1C(=O)CCC1 GAIIEUXSQGXFLO-UHFFFAOYSA-N 0.000 description 1
- NCOQADGJQJOWML-UHFFFAOYSA-N 1-(3-amino-4,5-dimethylphenyl)-3-methylpiperidin-2-one Chemical compound O=C1C(C)CCCN1C1=CC(C)=C(C)C(N)=C1 NCOQADGJQJOWML-UHFFFAOYSA-N 0.000 description 1
- CRQOQBIIZGVVHZ-UHFFFAOYSA-N 1-(3-amino-4,5-dimethylphenyl)-3-methylpyrrolidin-2-one Chemical compound O=C1C(C)CCN1C1=CC(C)=C(C)C(N)=C1 CRQOQBIIZGVVHZ-UHFFFAOYSA-N 0.000 description 1
- BLKUXFKJQGSMRD-UHFFFAOYSA-N 1-(3-amino-4,5-dimethylphenyl)-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C1=CC(C)=C(C)C(N)=C1 BLKUXFKJQGSMRD-UHFFFAOYSA-N 0.000 description 1
- HAPYJSNASVQWPV-UHFFFAOYSA-N 1-(3-amino-4,5-dimethylphenyl)piperidin-2-one Chemical compound NC=1C=C(C=C(C1C)C)N1C(CCCC1)=O HAPYJSNASVQWPV-UHFFFAOYSA-N 0.000 description 1
- UTQYBJIGOGAKLA-UHFFFAOYSA-N 1-(3-amino-4-chlorophenyl)piperidin-2-one Chemical compound C1=C(Cl)C(N)=CC(N2C(CCCC2)=O)=C1 UTQYBJIGOGAKLA-UHFFFAOYSA-N 0.000 description 1
- FKKHUKSEZMOSDB-UHFFFAOYSA-N 1-(3-amino-4-fluorophenyl)pyrrolidin-2-one Chemical compound C1=C(F)C(N)=CC(N2C(CCC2)=O)=C1 FKKHUKSEZMOSDB-UHFFFAOYSA-N 0.000 description 1
- GNNNRVCHXXOQQH-UHFFFAOYSA-N 1-(3-amino-4-methoxyphenyl)piperidin-2-one Chemical compound C1=C(N)C(OC)=CC=C1N1C(=O)CCCC1 GNNNRVCHXXOQQH-UHFFFAOYSA-N 0.000 description 1
- DRKHUQSUGLBYNX-UHFFFAOYSA-N 1-(3-amino-4-methylphenyl)azetidin-2-one Chemical compound C1=C(N)C(C)=CC=C1N1C(=O)CC1 DRKHUQSUGLBYNX-UHFFFAOYSA-N 0.000 description 1
- WRFVXNWWICHDEG-UHFFFAOYSA-N 1-(3-amino-5-methylphenyl)-3-methylpyrrolidin-2-one Chemical compound O=C1C(C)CCN1C1=CC(C)=CC(N)=C1 WRFVXNWWICHDEG-UHFFFAOYSA-N 0.000 description 1
- NHIOOHNRMMBILP-UHFFFAOYSA-N 1-(3-amino-5-methylphenyl)pyrrolidin-2-one Chemical compound CC1=CC(N)=CC(N2C(CCC2)=O)=C1 NHIOOHNRMMBILP-UHFFFAOYSA-N 0.000 description 1
- UARRSOFEBFWVDN-UHFFFAOYSA-N 1-(3-aminophenyl)-3-ethylpiperidin-2-one Chemical compound O=C1C(CC)CCCN1C1=CC=CC(N)=C1 UARRSOFEBFWVDN-UHFFFAOYSA-N 0.000 description 1
- IMPFXUIACTVYNW-UHFFFAOYSA-N 1-(3-aminophenyl)-3-methylpyrrolidin-2-one Chemical compound O=C1C(C)CCN1C1=CC=CC(N)=C1 IMPFXUIACTVYNW-UHFFFAOYSA-N 0.000 description 1
- IKAXDWLBXTZJNN-UHFFFAOYSA-N 1-(3-aminophenyl)piperidin-2-one Chemical compound NC1=CC=CC(N2C(CCCC2)=O)=C1 IKAXDWLBXTZJNN-UHFFFAOYSA-N 0.000 description 1
- ZQGGRBIDRBYUJS-UHFFFAOYSA-N 1-(3-aminophenyl)pyrrolidin-2-one Chemical compound NC1=CC=CC(N2C(CCC2)=O)=C1 ZQGGRBIDRBYUJS-UHFFFAOYSA-N 0.000 description 1
- DYVRGGYVRXOILD-UHFFFAOYSA-N 1-(4-amino-2-methoxy-5-methylsulfonylphenyl)piperidin-2-one Chemical compound COC1=CC(N)=C(S(C)(=O)=O)C=C1N1C(=O)CCCC1 DYVRGGYVRXOILD-UHFFFAOYSA-N 0.000 description 1
- UYVSSZOWTACRLF-UHFFFAOYSA-N 1-(4-amino-2-methoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC(N)=CC=C1N1C(=O)CCC1 UYVSSZOWTACRLF-UHFFFAOYSA-N 0.000 description 1
- OEBJMFHDKOSECF-UHFFFAOYSA-N 1-(4-amino-5-chloro-2-methylphenyl)pyrrolidin-2-one Chemical compound CC1=CC(N)=C(Cl)C=C1N1C(=O)CCC1 OEBJMFHDKOSECF-UHFFFAOYSA-N 0.000 description 1
- XWDUBOSLSYWJTR-UHFFFAOYSA-N 1-(4-aminophenyl)piperidin-2-one Chemical compound C1=CC(N)=CC=C1N1C(=O)CCCC1 XWDUBOSLSYWJTR-UHFFFAOYSA-N 0.000 description 1
- VBSPSDGSNVEMHI-UHFFFAOYSA-N 1-(5-amino-2,3-dimethylphenyl)pyrrolidin-2-one Chemical compound CC1=CC(N)=CC(N2C(CCC2)=O)=C1C VBSPSDGSNVEMHI-UHFFFAOYSA-N 0.000 description 1
- SYYJSRYNTHFUOW-UHFFFAOYSA-N 1-(5-amino-2,4-dichlorophenyl)piperidin-2-one Chemical compound C1=C(Cl)C(N)=CC(N2C(CCCC2)=O)=C1Cl SYYJSRYNTHFUOW-UHFFFAOYSA-N 0.000 description 1
- NAVOYYVLTMJUGW-UHFFFAOYSA-N 1-(5-amino-2,4-dichlorophenyl)pyrrolidin-2-one Chemical compound C1=C(Cl)C(N)=CC(N2C(CCC2)=O)=C1Cl NAVOYYVLTMJUGW-UHFFFAOYSA-N 0.000 description 1
- AIXQBXYSBRIVPG-UHFFFAOYSA-N 1-(5-amino-2,4-dimethylphenyl)-4-propan-2-ylpiperidin-2-one Chemical compound O=C1CC(C(C)C)CCN1C1=CC(N)=C(C)C=C1C AIXQBXYSBRIVPG-UHFFFAOYSA-N 0.000 description 1
- QHLHPWBDTLVWTQ-UHFFFAOYSA-N 1-(5-amino-2,4-dimethylphenyl)pyrrolidin-2-one Chemical compound C1=C(N)C(C)=CC(C)=C1N1C(=O)CCC1 QHLHPWBDTLVWTQ-UHFFFAOYSA-N 0.000 description 1
- HSDUIRGOSMIAAD-UHFFFAOYSA-N 1-(5-amino-2-methylphenyl)pyrrolidin-2-one Chemical compound CC1=CC=C(N)C=C1N1C(=O)CCC1 HSDUIRGOSMIAAD-UHFFFAOYSA-N 0.000 description 1
- FJEJVDQFOSHWIC-UHFFFAOYSA-N 1-(5-amino-4-chloro-2-methylphenyl)-3-butylpyrrolidin-2-one Chemical compound O=C1C(CCCC)CCN1C1=CC(N)=C(Cl)C=C1C FJEJVDQFOSHWIC-UHFFFAOYSA-N 0.000 description 1
- ZSNVSWQNQOTGOK-UHFFFAOYSA-N 1-(6-amino-2,3-dimethylphenyl)pyrrolidin-2-one Chemical compound CC1=CC=C(N)C(N2C(CCC2)=O)=C1C ZSNVSWQNQOTGOK-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- DNGLCPBASGKOBI-UHFFFAOYSA-N 1-[3-amino-4-[4-(trifluoromethyl)phenoxy]phenyl]pyrrolidin-2-one Chemical compound NC1=CC(N2C(CCC2)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 DNGLCPBASGKOBI-UHFFFAOYSA-N 0.000 description 1
- XBHVXORLBUPCQJ-UHFFFAOYSA-N 1-butyl-2-(trifluoromethyl)benzimidazole Chemical compound C1=CC=C2N(CCCC)C(C(F)(F)F)=NC2=C1 XBHVXORLBUPCQJ-UHFFFAOYSA-N 0.000 description 1
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 1
- JCRNSBKSAQHNIN-UHFFFAOYSA-N 2,4-dibutylnaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC(CCCC)=C21 JCRNSBKSAQHNIN-UHFFFAOYSA-N 0.000 description 1
- ZQMDUXIAMFHSLQ-UHFFFAOYSA-N 2,4-dimethyl-5-piperidin-1-ylaniline Chemical compound C1=C(N)C(C)=CC(C)=C1N1CCCCC1 ZQMDUXIAMFHSLQ-UHFFFAOYSA-N 0.000 description 1
- BQNOUQUCOMSVIU-UHFFFAOYSA-N 2,4-dimethyl-5-pyrrolidin-1-ylaniline Chemical compound C1=C(N)C(C)=CC(C)=C1N1CCCC1 BQNOUQUCOMSVIU-UHFFFAOYSA-N 0.000 description 1
- FJKVVIALTHZRGM-UHFFFAOYSA-N 2-methyl-5-piperidin-1-ylaniline Chemical compound C1=C(N)C(C)=CC=C1N1CCCCC1 FJKVVIALTHZRGM-UHFFFAOYSA-N 0.000 description 1
- NTNQDORDXJEARH-UHFFFAOYSA-N 2-methyl-5-pyrrolidin-1-ylaniline Chemical compound C1=C(N)C(C)=CC=C1N1CCCC1 NTNQDORDXJEARH-UHFFFAOYSA-N 0.000 description 1
- XKDPBYCPNJRCSM-UHFFFAOYSA-N 3,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(C)C(=O)N1 XKDPBYCPNJRCSM-UHFFFAOYSA-N 0.000 description 1
- MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical class O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 description 1
- SSXPQLXWKPOYLJ-UHFFFAOYSA-N 4,6-dichlorobenzene-1,3-diamine Chemical compound NC1=CC(N)=C(Cl)C=C1Cl SSXPQLXWKPOYLJ-UHFFFAOYSA-N 0.000 description 1
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical compound CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 description 1
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 1
- CDPMBLDIDQIKBJ-UHFFFAOYSA-N 5-(azepan-1-yl)-2-methylaniline Chemical compound C1=C(N)C(C)=CC=C1N1CCCCCC1 CDPMBLDIDQIKBJ-UHFFFAOYSA-N 0.000 description 1
- NPOQWQKUDROJNP-UHFFFAOYSA-N 5-methylpyrrolidin-2-one Chemical compound CC1CCC(N1)=O.C1(CCC(C)N1)=O NPOQWQKUDROJNP-UHFFFAOYSA-N 0.000 description 1
- MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000006463 Brassica alba Nutrition 0.000 description 1
- 244000140786 Brassica hirta Species 0.000 description 1
- 241001148727 Bromus tectorum Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 240000004585 Dactylis glomerata Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 101100001675 Emericella variicolor andJ gene Proteins 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241000410074 Festuca ovina Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XAJIKHWMKUDENG-UHFFFAOYSA-N NC=1C=C(C(=CC1C)C)N1C(C(CC1)C)=O.NC=1C=C(C(=CC1C)C)N1C(CCCC1C)=O Chemical compound NC=1C=C(C(=CC1C)C)N1C(C(CC1)C)=O.NC=1C=C(C(=CC1C)C)N1C(CCCC1C)=O XAJIKHWMKUDENG-UHFFFAOYSA-N 0.000 description 1
- 229910000503 Na-aluminosilicate Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 240000004370 Pastinaca sativa Species 0.000 description 1
- 235000002769 Pastinaca sativa Nutrition 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000219053 Rumex Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000007226 Setaria italica Nutrition 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 241000358324 Viverricula indica Species 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 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
- 150000001408 amides Chemical class 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical compound O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 229940092782 bentonite Drugs 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000019993 champagne Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229910052914 metal silicate Inorganic materials 0.000 description 1
- NLAHIHCKROMQEI-UHFFFAOYSA-N methyl 1-(3-aminophenyl)-5-chloro-2-methyl-4-oxopyridine-3-carboxylate Chemical compound C1=C(Cl)C(=O)C(C(=O)OC)=C(C)N1C1=CC=CC(N)=C1 NLAHIHCKROMQEI-UHFFFAOYSA-N 0.000 description 1
- XIBKKNPVTLJFKG-UHFFFAOYSA-N methyl 1-(5-amino-2,4-dimethylphenyl)-5-chloro-2-methyl-4-oxopyridine-3-carboxylate Chemical compound C1=C(Cl)C(=O)C(C(=O)OC)=C(C)N1C1=CC(N)=C(C)C=C1C XIBKKNPVTLJFKG-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BLRZHBWEWXGYIN-UHFFFAOYSA-N n-[2,4-dimethyl-5-(2-methyl-6-oxopiperidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound CC1CCCC(=O)N1C1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C BLRZHBWEWXGYIN-UHFFFAOYSA-N 0.000 description 1
- AELLFKPPLQHPRV-UHFFFAOYSA-N n-propan-2-yl-7-propan-2-yliminocyclohepta-1,3,5-trien-1-amine Chemical compound CC(C)NC1=CC=CC=CC1=NC(C)C AELLFKPPLQHPRV-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 239000000419 plant extract Chemical group 0.000 description 1
- 239000002373 plant growth inhibitor Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH470277A CH629076A5 (en) | 1977-04-15 | 1977-04-15 | Herbicidal and plant-growth-inhibiting compositions containing, as active substances, novel N-phenyl-substituted N-heterocycles, and their preparation and use |
| CH4702/77 | 1977-04-15 | ||
| CH13661/77 | 1977-11-09 | ||
| CH1366177A CH632131A5 (en) | 1977-11-09 | 1977-11-09 | Plant growth regulator, and process for the preparation of the novel N-phenyl-substituted N-heterocycles, which they contain as active substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1102801A true CA1102801A (en) | 1981-06-09 |
Family
ID=25696101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA301,079A Expired CA1102801A (en) | 1977-04-15 | 1978-04-13 | N-phenyl-substituted n-heterocyclic compounds, their preparation and use in agents for regulating plant growth |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US4208202A (en:Method) |
| JP (1) | JPS53130652A (en:Method) |
| AR (1) | AR231634A1 (en:Method) |
| AT (1) | AT370280B (en:Method) |
| AU (1) | AU520407B2 (en:Method) |
| BR (1) | BR7802330A (en:Method) |
| CA (1) | CA1102801A (en:Method) |
| CS (1) | CS274252B2 (en:Method) |
| DD (1) | DD137655A5 (en:Method) |
| DE (1) | DE2815820A1 (en:Method) |
| DK (1) | DK164678A (en:Method) |
| ES (1) | ES468807A1 (en:Method) |
| FR (1) | FR2387219B1 (en:Method) |
| GB (1) | GB1593809A (en:Method) |
| GR (1) | GR73529B (en:Method) |
| HU (1) | HU185923B (en:Method) |
| IL (1) | IL54501A (en:Method) |
| IT (1) | IT1094916B (en:Method) |
| NL (1) | NL7803885A (en:Method) |
| PL (1) | PL111168B2 (en:Method) |
| SE (1) | SE7804244L (en:Method) |
| TR (1) | TR20413A (en:Method) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7803885A (nl) * | 1977-04-15 | 1978-10-17 | Ciba Geigy | Nieuwe aan n door een fenylgroep gesubstitueerde n-heterocyclische verbindingen, hun bereiding en toe- passing in preparaten voor het beinvloeden van de plantengroei. |
| US4312663A (en) * | 1980-09-18 | 1982-01-26 | Minnesota Mining And Manufacturing Company | Cyclicacylaminoperfluoroalkanesulfonanilides and derivatives thereof |
| US4534786A (en) * | 1982-06-23 | 1985-08-13 | Chevron Research Company | 1-Alkyl derivatives of 3-aryloxy-4-(2-carbalkoxy)-phenyl-azet-2-ones as plant growth regulators |
| JPS6289651A (ja) * | 1985-06-11 | 1987-04-24 | Kumiai Chem Ind Co Ltd | トリフルオロメタンスルホンアニリド誘導体及びこれを含有する除草剤 |
| EP0338986B1 (de) * | 1988-04-19 | 1993-01-07 | Ciba-Geigy Ag | Pflanzenwuchshemmendes Mittel |
| US4956006A (en) * | 1988-12-27 | 1990-09-11 | Ici Americas Inc. | Substituted 1-phenyl pyrrolidones and their use as herbicides |
| US5223018A (en) * | 1989-04-04 | 1993-06-29 | Ciba-Geigy Corporation | 1-phenyl-piperdine-2,6-diones with herbicidal activity |
| EP0391847A1 (de) * | 1989-04-04 | 1990-10-10 | Ciba-Geigy Ag | 1-Phenyl-piperidin-2,4-dione mit herbizider Wirkung |
| US5278034A (en) * | 1990-04-27 | 1994-01-11 | Fuji Photo Film Co., Ltd. | Process for forming color image |
| DE10043790A1 (de) * | 2000-09-06 | 2002-03-14 | Bayer Ag | Substituierte 1-Aryl-pyridin-2-(thi)one |
| DE10139060A1 (de) | 2001-08-08 | 2003-02-20 | Merck Patent Gmbh | Phenylderivate |
| WO2004011429A1 (ja) * | 2002-07-26 | 2004-02-05 | Nihon Nohyaku Co., Ltd. | 新規なハロアルキルスルホンアニリド誘導体及び除草剤並びにその使用方法 |
| JP2004107323A (ja) * | 2002-07-26 | 2004-04-08 | Nippon Nohyaku Co Ltd | 新規なハロアルキルスルホンアニリド誘導体及び除草剤並びにその使用方法 |
| US6818593B2 (en) * | 2003-03-24 | 2004-11-16 | E. I. Du Pont De Nemours And Company | Production of 5-Methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid with nitro compounds |
| US6855731B2 (en) * | 2003-03-24 | 2005-02-15 | E. I. Du Pont De Nemours And Company | Production of 5-methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with nitro compounds |
| WO2010026989A1 (ja) * | 2008-09-02 | 2010-03-11 | 日産化学工業株式会社 | オルト置換ハロアルキルスルホンアニリド誘導体及び除草剤 |
| CN115279735A (zh) * | 2020-04-14 | 2022-11-01 | 巴斯夫欧洲公司 | β-内酰胺类及其作为除草剂的用途 |
| JP2024506366A (ja) * | 2021-02-16 | 2024-02-13 | エフ エム シー コーポレーション | ハロアルキルスルホニルアニリド基でｎ－置換された除草性の環状アミド |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1349517A (fr) * | 1962-01-09 | 1964-04-15 | Rohm & Haas | Composés herbicides à base de lactames |
| NL7803885A (nl) * | 1977-04-15 | 1978-10-17 | Ciba Geigy | Nieuwe aan n door een fenylgroep gesubstitueerde n-heterocyclische verbindingen, hun bereiding en toe- passing in preparaten voor het beinvloeden van de plantengroei. |
| JPS5471550A (en) * | 1977-11-18 | 1979-06-08 | Hitachi Ltd | Base metal material for direct heating oxide cathode |
-
1978
- 1978-04-12 NL NL7803885A patent/NL7803885A/xx not_active Application Discontinuation
- 1978-04-12 DE DE19782815820 patent/DE2815820A1/de active Granted
- 1978-04-12 US US05/896,970 patent/US4208202A/en not_active Expired - Lifetime
- 1978-04-12 FR FR7810761A patent/FR2387219B1/fr not_active Expired
- 1978-04-13 DD DD78204774A patent/DD137655A5/xx unknown
- 1978-04-13 IL IL54501A patent/IL54501A/xx unknown
- 1978-04-13 AU AU35084/78A patent/AU520407B2/en not_active Expired
- 1978-04-13 AR AR271769D patent/AR231634A1/es active
- 1978-04-13 CA CA301,079A patent/CA1102801A/en not_active Expired
- 1978-04-14 AT AT0264078A patent/AT370280B/de active
- 1978-04-14 BR BR787802330A patent/BR7802330A/pt unknown
- 1978-04-14 IT IT22345/78A patent/IT1094916B/it active
- 1978-04-14 HU HU78CI1825A patent/HU185923B/hu unknown
- 1978-04-14 TR TR20413A patent/TR20413A/xx unknown
- 1978-04-14 DK DK164678A patent/DK164678A/da not_active IP Right Cessation
- 1978-04-14 CS CS244578A patent/CS274252B2/cs unknown
- 1978-04-14 SE SE7804244A patent/SE7804244L/xx unknown
- 1978-04-14 GB GB14762/78A patent/GB1593809A/en not_active Expired
- 1978-04-14 ES ES468807A patent/ES468807A1/es not_active Expired
- 1978-04-15 GR GR55990A patent/GR73529B/el unknown
- 1978-04-15 PL PL1978206125A patent/PL111168B2/xx unknown
- 1978-04-15 JP JP4473978A patent/JPS53130652A/ja active Granted
-
1980
- 1980-01-14 US US06/111,552 patent/US4294606A/en not_active Expired - Lifetime
-
1981
- 1981-10-26 US US06/314,620 patent/US4394156A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1593809A (en) | 1981-07-22 |
| DE2815820A1 (de) | 1978-10-26 |
| CS244578A2 (en) | 1990-09-12 |
| AU3508478A (en) | 1979-10-18 |
| JPH0321545B2 (en:Method) | 1991-03-22 |
| HU185923B (en) | 1985-03-28 |
| NL7803885A (nl) | 1978-10-17 |
| FR2387219A1 (en:Method) | 1978-11-10 |
| PL111168B2 (en) | 1980-08-30 |
| GR73529B (en:Method) | 1984-03-12 |
| US4394156A (en) | 1983-07-19 |
| IT7822345A0 (it) | 1978-04-14 |
| US4208202A (en) | 1980-06-17 |
| SE7804244L (sv) | 1978-10-16 |
| AR231634A1 (es) | 1985-01-31 |
| BR7802330A (pt) | 1979-02-13 |
| ES468807A1 (es) | 1979-12-16 |
| FR2387219B1 (en:Method) | 1982-11-19 |
| IL54501A0 (en) | 1978-07-31 |
| US4294606A (en) | 1981-10-13 |
| ATA264078A (de) | 1982-08-15 |
| DD137655A5 (de) | 1979-09-19 |
| AU520407B2 (en) | 1982-01-28 |
| DK164678A (da) | 1978-10-16 |
| CS274252B2 (en) | 1991-04-11 |
| IL54501A (en) | 1982-09-30 |
| JPS53130652A (en) | 1978-11-14 |
| PL206125A1 (pl) | 1979-06-04 |
| DE2815820C2 (en:Method) | 1989-12-28 |
| AT370280B (de) | 1983-03-10 |
| IT1094916B (it) | 1985-08-10 |
| TR20413A (tr) | 1981-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1102801A (en) | N-phenyl-substituted n-heterocyclic compounds, their preparation and use in agents for regulating plant growth | |
| US4129573A (en) | Compositions for and method of influencing plant growth and novel 1-phenyl-2-oxo-pyrrolidine-4-carboxylic acid derivatives | |
| RU2028294C1 (ru) | Пиримидиновые производные | |
| US4138243A (en) | Novel heterocyclic compounds | |
| US5840654A (en) | Herbicidal heterocyclic-substituted pyridines | |
| CA1083574A (en) | 1-(bis-trifluoromethylphenyl)-2-oxo-pyrrolidine-4- carboxylic acid derivatives, their production and their use as plant-growth regulators and herbicides | |
| US4749403A (en) | Herbicidal derivatives of imidazolidinone and imidazolidine thione | |
| IE50011B1 (en) | A method of combating fungus and/or combating or regulating plant growth using heterocyclic compounds | |
| EP0372586B1 (en) | Cyclic amide compounds and herbicides | |
| DK163703B (da) | Fremgangsmaade til regulering af svampe under anvendelse af pyridylethenderivater | |
| US4082535A (en) | Pyrimidine derivatives | |
| US4743296A (en) | Heterocyclically fused pyridine compounds as herbicides | |
| US4205977A (en) | Agent and method for influencing plant growth | |
| GB2056974A (en) | Heterocyclic acylamino compounds having fungicidal, herbicidal and plant-growth regulating properties | |
| IE49460B1 (en) | Oxime derivatives for protecting plant crops | |
| AU679731B2 (en) | Nicotinic acid derivative and herbicide | |
| IE47202B1 (en) | 3-phenyl-5-substituted-4(1h)-pyridones(thiones) | |
| DK157832B (da) | Anvendelse af phenyliminomethylpyridinderivater som fungicider og eventuelt plantevaekstregulerende midler, saadanne midler og phenyliminomethylpyridinderivater til anvendelse heri | |
| SK281197B6 (sk) | Pyrazolyloxypikolínamidové deriváty, spôsob ich výroby, použité medziprodukty, herbicídna kompozícia obsahujúca pyrazolyloxypikolínamidové deriváty a jej herbicídne použitie | |
| KR970010173B1 (ko) | 함헤테로 시클로헥산디온 유도체, 그의 제조방법 및 제초제 | |
| US4595408A (en) | N-m-phenyl succinimide and glutarimide derivatives and their use as herbicides | |
| GB2124615A (en) | Heterocyclic compounds having fungicidal, herbicidal and plant- growth regulating properties | |
| US4767446A (en) | Trifluoromethanesulfonanilides, and their production and use | |
| EP0046445A1 (de) | 3-Phenoxy-methylenaniline als Herbizide, ihre Herstellung und Verwendung | |
| US4564386A (en) | Trifluoromethanesulfonanilides, and their production and use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |