CA1083574A - 1-(bis-trifluoromethylphenyl)-2-oxo-pyrrolidine-4- carboxylic acid derivatives, their production and their use as plant-growth regulators and herbicides - Google Patents
1-(bis-trifluoromethylphenyl)-2-oxo-pyrrolidine-4- carboxylic acid derivatives, their production and their use as plant-growth regulators and herbicidesInfo
- Publication number
- CA1083574A CA1083574A CA238,543A CA238543A CA1083574A CA 1083574 A CA1083574 A CA 1083574A CA 238543 A CA238543 A CA 238543A CA 1083574 A CA1083574 A CA 1083574A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- bis
- carboxylic acid
- oxo
- pyrrolidine
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- ZDGFPURRXYZUHZ-UHFFFAOYSA-N 1-[2,3-bis(trifluoromethyl)phenyl]-5-oxopyrrolidine-3-carboxylic acid Chemical class O=C1CC(C(=O)O)CN1C1=CC=CC(C(F)(F)F)=C1C(F)(F)F ZDGFPURRXYZUHZ-UHFFFAOYSA-N 0.000 title claims abstract 4
- 239000004009 herbicide Substances 0.000 title abstract description 3
- 239000005648 plant growth regulator Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 7
- 230000008635 plant growth Effects 0.000 claims abstract description 6
- 230000033228 biological regulation Effects 0.000 claims abstract description 5
- 241000196324 Embryophyta Species 0.000 claims description 56
- -1 triethanolamine cation Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- IVNOUUBBVOWAST-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-5-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 IVNOUUBBVOWAST-UHFFFAOYSA-N 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- CDIDGWDGQGVCIB-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDIDGWDGQGVCIB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004069 aziridinyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 55
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 26
- 230000012010 growth Effects 0.000 description 24
- 238000012360 testing method Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 241000209504 Poaceae Species 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000005995 Aluminium silicate Substances 0.000 description 7
- 244000025254 Cannabis sativa Species 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 235000013339 cereals Nutrition 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
- 239000003921 oil Substances 0.000 description 7
- 239000006072 paste Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 244000061176 Nicotiana tabacum Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000002222 fluorine compounds Chemical class 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 241000209764 Avena fatua Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 244000285774 Cyperus esculentus Species 0.000 description 3
- 235000005853 Cyperus esculentus Nutrition 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 240000004658 Medicago sativa Species 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 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 3
- 230000017066 negative regulation of growth Effects 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
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- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- 241000743985 Alopecurus Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
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- LYNFVELAUJGXHI-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-n,n-dimethyl-5-oxopyrrolidine-3-carboxamide Chemical compound O=C1CC(C(=O)N(C)C)CN1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LYNFVELAUJGXHI-UHFFFAOYSA-N 0.000 description 1
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- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical class C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
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- GHTSPNBSVDWGED-UHFFFAOYSA-N 5-oxo-1-phenylpyrrolidine-3-carboxylic acid Chemical class O=C1CC(C(=O)O)CN1C1=CC=CC=C1 GHTSPNBSVDWGED-UHFFFAOYSA-N 0.000 description 1
- GZVHQYZRBCSHAI-UHFFFAOYSA-N 5-oxopyrrolidine-3-carboxylic acid Chemical compound OC(=O)C1CNC(=O)C1 GZVHQYZRBCSHAI-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 101100372602 Arabidopsis thaliana VDAC3 gene Proteins 0.000 description 1
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- 230000003115 biocidal effect Effects 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
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- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 239000002917 insecticide Substances 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 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 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
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- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000012219 potassium aluminium silicate Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000026267 regulation of growth Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
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- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-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
- 241000894007 species Species 0.000 description 1
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- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
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- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1459574A CH611773A5 (en, 2012) | 1974-10-31 | 1974-10-31 | |
| CH14595/74 | 1974-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1083574A true CA1083574A (en) | 1980-08-12 |
Family
ID=4402184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA238,543A Expired CA1083574A (en) | 1974-10-31 | 1975-10-29 | 1-(bis-trifluoromethylphenyl)-2-oxo-pyrrolidine-4- carboxylic acid derivatives, their production and their use as plant-growth regulators and herbicides |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4013445A (en, 2012) |
| JP (1) | JPS51125745A (en, 2012) |
| AR (1) | AR217232A1 (en, 2012) |
| AT (1) | AT345317B (en, 2012) |
| AU (1) | AU507492B2 (en, 2012) |
| BE (1) | BE835040A (en, 2012) |
| BR (1) | BR7507116A (en, 2012) |
| CA (1) | CA1083574A (en, 2012) |
| CH (1) | CH611773A5 (en, 2012) |
| CS (1) | CS193531B2 (en, 2012) |
| DD (1) | DD124728A5 (en, 2012) |
| DE (1) | DE2548231A1 (en, 2012) |
| DK (1) | DK430975A (en, 2012) |
| ES (1) | ES442215A1 (en, 2012) |
| FR (1) | FR2289498A1 (en, 2012) |
| GB (1) | GB1522686A (en, 2012) |
| GR (1) | GR58590B (en, 2012) |
| IL (1) | IL48381A (en, 2012) |
| IT (1) | IT1044089B (en, 2012) |
| NL (1) | NL7512672A (en, 2012) |
| PL (1) | PL102551B1 (en, 2012) |
| SE (1) | SE405852B (en, 2012) |
| SU (1) | SU584739A3 (en, 2012) |
| TR (1) | TR18917A (en, 2012) |
| ZA (1) | ZA756836B (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5187185A (en) * | 1988-12-09 | 1993-02-16 | Rhone-Poulenc Ag Company | Pesticidal 1-arylpyrroles |
| CH618682A5 (en, 2012) * | 1975-11-07 | 1980-08-15 | Ciba Geigy Ag | |
| US4097260A (en) * | 1975-11-28 | 1978-06-27 | Monsanto Company | 2-Substituted-1,3(2H,4H)-isoquinolinediones as plant growth regulants |
| DE2928305A1 (de) * | 1979-07-13 | 1981-02-05 | Hoechst Ag | 2-dihalogenmethylen-3-halogen-3- carboalkoxy-5-oxopyrrolidine, verfahren zu ihrer herstellung und ihre verwendung als fungizide, bakterizide und algizide schaedlingsbekaempfungsmittel |
| US4344788A (en) * | 1980-07-15 | 1982-08-17 | Gaf Corporation | Method of plant growth regulation |
| US4643762A (en) * | 1984-08-27 | 1987-02-17 | Chevron Research Company | Herbicidal 5-amino-3-oxo-4-(3-substituted-phenyl)-4-pyrroline and derivatives thereof |
| US4874422A (en) * | 1988-12-27 | 1989-10-17 | Ici Americas Inc. | 1-Phenyl-3-carboxyamidopyrrolidones and their use as herbicides |
| EP0397602A1 (de) * | 1989-05-12 | 1990-11-14 | Ciba-Geigy Ag | Neue N-Phenylpyrrolidine |
| CA2371618A1 (en) * | 1999-04-28 | 2000-11-09 | Yuji Ishihara | Cyclic amide compounds, their production and use |
| RU2195447C1 (ru) * | 2001-07-31 | 2002-12-27 | Кубанский государственный технологический университет | 1-(4-нитрофенил)-4-n-x-аминопирролидоны-2, проявляющие рострегулирующую и антистрессовую активность, и способ их получения |
| US7064211B2 (en) * | 2002-03-22 | 2006-06-20 | Eisai Co., Ltd. | Hemiasterlin derivatives and uses thereof |
| TWI350168B (en) * | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| BRPI0512410A (pt) * | 2004-06-24 | 2008-03-04 | Incyte Corp | compostos de amido e seu uso como produtos farmacêuticos |
| EP1773773A4 (en) * | 2004-06-24 | 2009-07-29 | Incyte Corp | AMID COMPOUNDS AND THEIR USE AS MEDICAMENTS |
| JP2008504280A (ja) * | 2004-06-24 | 2008-02-14 | インサイト・コーポレイション | ２−メチルプロパンアミドおよびその医薬としての使用 |
| NZ551603A (en) | 2004-06-24 | 2010-11-26 | Incyte Corp | N-substituted piperidines and their use as pharmaceuticals |
| WO2006020598A2 (en) * | 2004-08-10 | 2006-02-23 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| US20070213311A1 (en) * | 2006-03-02 | 2007-09-13 | Yun-Long Li | Modulators of 11-beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| US20070208001A1 (en) * | 2006-03-03 | 2007-09-06 | Jincong Zhuo | Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| EP2013163A1 (en) * | 2006-05-01 | 2009-01-14 | Incyte Corporation | Tetrasubstituted ureas as modulators of 11-beta hydroxyl steroid dehydrogenase type 1 |
| JP2009537564A (ja) * | 2006-05-17 | 2009-10-29 | インサイト・コーポレイション | １１−βヒドロキシルステロイドデヒドロゲナーゼタイプＩの複素環阻害剤およびそれを用いる方法 |
| KR102070057B1 (ko) * | 2012-03-19 | 2020-01-29 | 제이에스알 가부시끼가이샤 | 포토레지스트 조성물, 화합물 및 그의 제조 방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1053635A (en, 2012) * | 1961-12-18 | |||
| US3149954A (en) * | 1962-02-16 | 1964-09-22 | Du Pont | Method of retarding the growth of vegetation |
-
1973
- 1973-10-28 TR TR18917A patent/TR18917A/xx unknown
-
1974
- 1974-10-31 CH CH1459574A patent/CH611773A5/xx not_active IP Right Cessation
-
1975
- 1975-09-25 DK DK430975A patent/DK430975A/da not_active Application Discontinuation
- 1975-10-07 SE SE7511210A patent/SE405852B/xx unknown
- 1975-10-23 US US05/625,234 patent/US4013445A/en not_active Expired - Lifetime
- 1975-10-23 SU SU7502183002A patent/SU584739A3/ru active
- 1975-10-28 FR FR7532902A patent/FR2289498A1/fr active Granted
- 1975-10-28 DE DE19752548231 patent/DE2548231A1/de not_active Ceased
- 1975-10-29 PL PL1975184337A patent/PL102551B1/pl unknown
- 1975-10-29 IL IL48381A patent/IL48381A/xx unknown
- 1975-10-29 CA CA238,543A patent/CA1083574A/en not_active Expired
- 1975-10-29 DD DD189104A patent/DD124728A5/xx unknown
- 1975-10-29 NL NL7512672A patent/NL7512672A/xx not_active Application Discontinuation
- 1975-10-29 AR AR260985A patent/AR217232A1/es active
- 1975-10-30 CS CS757331A patent/CS193531B2/cs unknown
- 1975-10-30 GR GR49243A patent/GR58590B/el unknown
- 1975-10-30 GB GB45066/75A patent/GB1522686A/en not_active Expired
- 1975-10-30 IT IT28845/75A patent/IT1044089B/it active
- 1975-10-30 ZA ZA00756836A patent/ZA756836B/xx unknown
- 1975-10-30 AT AT826575A patent/AT345317B/de not_active IP Right Cessation
- 1975-10-30 ES ES442215A patent/ES442215A1/es not_active Expired
- 1975-10-30 BR BR7507116*A patent/BR7507116A/pt unknown
- 1975-10-30 AU AU86194/75A patent/AU507492B2/en not_active Expired
- 1975-10-30 BE BE161395A patent/BE835040A/xx not_active IP Right Cessation
- 1975-10-31 JP JP50132080A patent/JPS51125745A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU507492B2 (en) | 1980-02-14 |
| DD124728A5 (en, 2012) | 1977-03-09 |
| NL7512672A (nl) | 1976-05-04 |
| IL48381A0 (en) | 1975-12-31 |
| GB1522686A (en) | 1978-08-23 |
| DK430975A (da) | 1976-05-01 |
| IT1044089B (it) | 1980-03-20 |
| SU584739A3 (ru) | 1977-12-15 |
| SE7511210L (sv) | 1976-05-03 |
| IL48381A (en) | 1979-07-25 |
| ZA756836B (en) | 1976-10-27 |
| GR58590B (en) | 1977-11-10 |
| BR7507116A (pt) | 1976-08-03 |
| FR2289498B1 (en, 2012) | 1978-09-22 |
| JPS51125745A (en) | 1976-11-02 |
| CH611773A5 (en, 2012) | 1979-06-29 |
| BE835040A (fr) | 1976-04-30 |
| ES442215A1 (es) | 1977-04-16 |
| TR18917A (tr) | 1977-12-09 |
| AU8619475A (en) | 1977-05-05 |
| US4013445A (en) | 1977-03-22 |
| AR217232A1 (es) | 1980-03-14 |
| AT345317B (de) | 1978-09-11 |
| PL102551B1 (pl) | 1979-04-30 |
| DE2548231A1 (de) | 1976-05-06 |
| SE405852B (sv) | 1979-01-08 |
| ATA826575A (de) | 1978-01-15 |
| CS193531B2 (en) | 1979-10-31 |
| FR2289498A1 (fr) | 1976-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |