CH618682A5 - - Google Patents
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- Publication number
- CH618682A5 CH618682A5 CH1442775A CH1442775A CH618682A5 CH 618682 A5 CH618682 A5 CH 618682A5 CH 1442775 A CH1442775 A CH 1442775A CH 1442775 A CH1442775 A CH 1442775A CH 618682 A5 CH618682 A5 CH 618682A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- alkyl
- carboxylic acid
- unsubstituted
- formula
- Prior art date
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 241000196324 Embryophyta Species 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 230000012010 growth Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 235000013339 cereals Nutrition 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000008635 plant growth Effects 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- 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 claims description 4
- 241000209504 Poaceae Species 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 244000068988 Glycine max Species 0.000 claims description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 3
- 244000061176 Nicotiana tabacum Species 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000286 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 3
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 229910001414 potassium ion Inorganic materials 0.000 claims 1
- 229910001415 sodium ion Inorganic materials 0.000 claims 1
- -1 aliphatic alcohols Chemical class 0.000 description 51
- 239000004480 active ingredient Substances 0.000 description 29
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000008187 granular material Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000013543 active substance Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000006072 paste Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000005995 Aluminium silicate Substances 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000012141 concentrate 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
- 239000002904 solvent Substances 0.000 description 7
- GZVHQYZRBCSHAI-UHFFFAOYSA-N 5-oxopyrrolidine-3-carboxylic acid Chemical compound OC(=O)C1CNC(=O)C1 GZVHQYZRBCSHAI-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000005690 diesters Chemical class 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
- 150000002148 esters Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 235000021374 legumes Nutrition 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 230000008121 plant development Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- OPPJYODZNFUYTP-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CC1=CC=CC(N2C(CC(C2)C(O)=O)=O)=C1C OPPJYODZNFUYTP-UHFFFAOYSA-N 0.000 description 1
- DCROVTQLKXLIHL-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CC1=CC=C(C)C(N2C(CC(C2)C(O)=O)=O)=C1 DCROVTQLKXLIHL-UHFFFAOYSA-N 0.000 description 1
- KKIVDCGOBHNFQC-UHFFFAOYSA-N 1-(2,6-diethylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CCC1=CC=CC(CC)=C1N1C(=O)CC(C(O)=O)C1 KKIVDCGOBHNFQC-UHFFFAOYSA-N 0.000 description 1
- PMFQUYSCBXNYOR-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CC1=CC=CC(C)=C1N1C(=O)CC(C(O)=O)C1 PMFQUYSCBXNYOR-UHFFFAOYSA-N 0.000 description 1
- GFEHBRAXQVGPQH-UHFFFAOYSA-N 1-(2-ethylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CCC1=CC=CC=C1N1C(=O)CC(C(O)=O)C1 GFEHBRAXQVGPQH-UHFFFAOYSA-N 0.000 description 1
- BQQBMILQUDEPIK-UHFFFAOYSA-N 1-(2-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound COC1=CC=CC=C1N1C(=O)CC(C(O)=O)C1 BQQBMILQUDEPIK-UHFFFAOYSA-N 0.000 description 1
- GWCVJEVNUIDHPH-UHFFFAOYSA-N 1-(2-methylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CC1=CC=CC=C1N1C(=O)CC(C(O)=O)C1 GWCVJEVNUIDHPH-UHFFFAOYSA-N 0.000 description 1
- FVLRNFDPKXYNTR-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1N1C(=O)CC(C(O)=O)C1 FVLRNFDPKXYNTR-UHFFFAOYSA-N 0.000 description 1
- ZVYUEYJQRCOJDI-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CC1=CC(C)=CC(N2C(CC(C2)C(O)=O)=O)=C1 ZVYUEYJQRCOJDI-UHFFFAOYSA-N 0.000 description 1
- ZCPWASRXJNDMDW-UHFFFAOYSA-N 1-(3-chloro-4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC=C1N1C(=O)CC(C(O)=O)C1 ZCPWASRXJNDMDW-UHFFFAOYSA-N 0.000 description 1
- MYNNLWVFRWATKE-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC=C1N1C(=O)CC(C(O)=O)C1 MYNNLWVFRWATKE-UHFFFAOYSA-N 0.000 description 1
- DEFUAHXVPYNTKQ-UHFFFAOYSA-N 1-(3-fluoro-4-methylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=C(F)C(C)=CC=C1N1C(=O)CC(C(O)=O)C1 DEFUAHXVPYNTKQ-UHFFFAOYSA-N 0.000 description 1
- UFHSYKGLJVRMNV-UHFFFAOYSA-N 1-(3-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound COC1=CC=CC(N2C(CC(C2)C(O)=O)=O)=C1 UFHSYKGLJVRMNV-UHFFFAOYSA-N 0.000 description 1
- FEIYFABONGDZKQ-UHFFFAOYSA-N 1-(3-methylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CC1=CC=CC(N2C(CC(C2)C(O)=O)=O)=C1 FEIYFABONGDZKQ-UHFFFAOYSA-N 0.000 description 1
- NHDHIMKQGYJLII-UHFFFAOYSA-N 1-(3-methylsulfanylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CSC1=CC=CC(N2C(CC(C2)C(O)=O)=O)=C1 NHDHIMKQGYJLII-UHFFFAOYSA-N 0.000 description 1
- QQDZRLNEBVHNOB-UHFFFAOYSA-N 1-(4-butan-2-ylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)CC(C(O)=O)C1 QQDZRLNEBVHNOB-UHFFFAOYSA-N 0.000 description 1
- NNRCIICGPROCOR-UHFFFAOYSA-N 1-(4-butoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1N1C(=O)CC(C(O)=O)C1 NNRCIICGPROCOR-UHFFFAOYSA-N 0.000 description 1
- LMCVFDCBQBJVTN-UHFFFAOYSA-N 1-(4-butylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=CC(CCCC)=CC=C1N1C(=O)CC(C(O)=O)C1 LMCVFDCBQBJVTN-UHFFFAOYSA-N 0.000 description 1
- ZKFRIZLJBPRXKI-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1N1C(=O)CC(C(O)=O)C1 ZKFRIZLJBPRXKI-UHFFFAOYSA-N 0.000 description 1
- JIKAEHOGWAHVIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C(=O)CC(C(O)=O)C1 JIKAEHOGWAHVIJ-UHFFFAOYSA-N 0.000 description 1
- QLLPDFKYJGBZCA-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound COC1=CC=C(Cl)C=C1N1C(=O)CC(C(O)=O)C1 QLLPDFKYJGBZCA-UHFFFAOYSA-N 0.000 description 1
- HFMQBZLBNDOOFS-UHFFFAOYSA-N 1-(5-chloro-2-methylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CC1=CC=C(Cl)C=C1N1C(=O)CC(C(O)=O)C1 HFMQBZLBNDOOFS-UHFFFAOYSA-N 0.000 description 1
- WBWKJDPXSLQGKZ-UHFFFAOYSA-N 1-(5-fluoro-2-methylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound CC1=CC=C(F)C=C1N1C(=O)CC(C(O)=O)C1 WBWKJDPXSLQGKZ-UHFFFAOYSA-N 0.000 description 1
- JMVIVASFFKKFQK-UHFFFAOYSA-N 1-phenylpyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=CC=C1 JMVIVASFFKKFQK-UHFFFAOYSA-N 0.000 description 1
- LRERZFUFCDUJEX-UHFFFAOYSA-N 2,3-dimethylaniline;2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1.CC1=CC=CC(N)=C1C LRERZFUFCDUJEX-UHFFFAOYSA-N 0.000 description 1
- BMIPMKQAAJKBKP-UHFFFAOYSA-N 2,4,5-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C=C1C BMIPMKQAAJKBKP-UHFFFAOYSA-N 0.000 description 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
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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
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1442775A CH618682A5 (pt) | 1975-11-07 | 1975-11-07 | |
| US05/736,656 US4129573A (en) | 1975-11-07 | 1976-10-28 | Compositions for and method of influencing plant growth and novel 1-phenyl-2-oxo-pyrrolidine-4-carboxylic acid derivatives |
| NL7612152A NL7612152A (nl) | 1975-11-07 | 1976-11-02 | Middelen en werkwijzen ter beinvloeding van de plantengroei en nieuwe 1-fenyl-2-oxo-pyrrolidine- -4-carbonzuurderivaten. |
| FR7633248A FR2330318A1 (fr) | 1975-11-07 | 1976-11-04 | Agent et procede pour influencer la croissance des plantes, et nouveaux derives d'acide 1-phenyl 2-oxo-pyrrolidine-4-carboxylique |
| DE19762650604 DE2650604A1 (de) | 1975-11-07 | 1976-11-04 | Mittel und verfahren zur beeinflussung des pflanzenwachstums und neue 1-phenyl-2-oxo-pyrrolidin-4- carbonsaeurederivate |
| AT824576A AT344755B (de) | 1975-11-07 | 1976-11-05 | Mittel zur beeinflussung des pflanzenwachstums und verwendung der wirksubstanzen des mittels zur hemmung des wachstums |
| SE7612365A SE7612365L (sv) | 1975-11-07 | 1976-11-05 | L-fenyl-2-oxo-pyrrolidin-4-karbonsyraderivat |
| TR19368A TR19368A (tr) | 1975-11-07 | 1976-11-05 | Bitkilerin bueyuemesini etkilemeye mahsus maddeler |
| ZA766643A ZA766643B (en) | 1975-11-07 | 1976-11-05 | Compositions for and method of influencing plant growth and novel 1-phenyl-2-oxopyrrolidine-4-carboxylic acid derivatives |
| IL50855A IL50855A0 (en) | 1975-11-07 | 1976-11-05 | Method and compositions containing 1-phenyl-2-oxo-pyrrolidine-4-carboxylic acid derivatives for influencing plant growth,certain such novel derivatives and their manufacture |
| BR7607425A BR7607425A (pt) | 1975-11-07 | 1976-11-05 | Composicoes e processo para influenciar o crescimento das plantas,novos derivados do acido 1-fenil-2oxo-pirrolidino-4-carboxilico e processo para sua preparacao |
| DD7600195636A DD128633A5 (de) | 1975-11-07 | 1976-11-05 | Mittel und verfahren zur beeinflussung des pflanzenwachstums |
| GB46177/76A GB1563835A (en) | 1975-11-07 | 1976-11-05 | Compositions for and method of influencing plant growth using 1-phenyl-2-oxo pyrrolidine-4-carboxylic acid dervatives |
| DK501276A DK501276A (da) | 1975-11-07 | 1976-11-05 | Middel og fremgangsmade til pavirkning pa plantevekst og nye 1-phenyl-2-oxo-pyrrolidin-4-carboxylsyrederivater |
| GR52108A GR61133B (en) | 1975-11-07 | 1976-11-05 | Medium and method to influence plants growth and novel 1-phenyl-2-oxo-pyrrolidin-4-hydrocarbon derivatives |
| BE172093A BE848015A (fr) | 1975-11-07 | 1976-11-05 | Agent et procede pour influencer la croissance des plantes, et nouveaux derives d'acide 1-phenyl-2-oxo-pyrrolidine-4-carboxylique |
| CA264,979A CA1079289A (en) | 1975-11-07 | 1976-11-05 | Composition for and method of influencing plant growth and novel 1-phenyl-2-oxopyrrolidine-4-carboxylic acid derivatives |
| AU19350/76A AU511853B2 (en) | 1975-11-07 | 1976-11-05 | l-Phenyl-2-Oxo-Pyrroliaine-4-carboxylic acid derivatives |
| ES453087A ES453087A1 (es) | 1975-11-07 | 1976-11-06 | Procedimiento para la preparacion de nuevos derivados de acido 1-fenil-2-oxo-pirrolidin-4-carboxilico. |
| ES453089A ES453089A1 (es) | 1975-11-07 | 1976-11-06 | Procedimiento para la preparacion de agentes para regular elcrecimiento y desarrollo de las plantas. |
| JP51133684A JPS5261226A (en) | 1975-11-07 | 1976-11-06 | Composition to control plant growth containing new 11phenyll22oxoopyrrolidinee44carbon acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1442775A CH618682A5 (pt) | 1975-11-07 | 1975-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618682A5 true CH618682A5 (pt) | 1980-08-15 |
Family
ID=4400741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1442775A CH618682A5 (pt) | 1975-11-07 | 1975-11-07 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4129573A (pt) |
| JP (1) | JPS5261226A (pt) |
| AT (1) | AT344755B (pt) |
| AU (1) | AU511853B2 (pt) |
| BE (1) | BE848015A (pt) |
| BR (1) | BR7607425A (pt) |
| CA (1) | CA1079289A (pt) |
| CH (1) | CH618682A5 (pt) |
| DD (1) | DD128633A5 (pt) |
| DE (1) | DE2650604A1 (pt) |
| DK (1) | DK501276A (pt) |
| ES (2) | ES453087A1 (pt) |
| FR (1) | FR2330318A1 (pt) |
| GB (1) | GB1563835A (pt) |
| GR (1) | GR61133B (pt) |
| IL (1) | IL50855A0 (pt) |
| NL (1) | NL7612152A (pt) |
| SE (1) | SE7612365L (pt) |
| TR (1) | TR19368A (pt) |
| ZA (1) | ZA766643B (pt) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007500A1 (en) * | 1988-12-27 | 1990-07-12 | Ici Americas Inc. | 1-phenyl-3-carboxyamidopyrrolidones and their use as herbicides |
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| FR2428032A1 (fr) * | 1978-06-09 | 1980-01-04 | Delalande Sa | Nouvelles oxazolidimones, oxazolidinethiones et pyrrolidinones, leur procede de preparation et leur application en therapeutique |
| EP0011693A1 (de) * | 1978-10-03 | 1980-06-11 | Ciba-Geigy Ag | Neue N-(trifluormethansulfonylaminophenyl)-substituierte N-Heterocyclen, ihre Herstellung, sie enthaltende Mittel und ihre Verwendung zur Beeinflussung des Pflanzenwachstums |
| 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 |
| US4476311A (en) * | 1980-03-12 | 1984-10-09 | The Purdue Frederick Company | Analgesic 4-carboxy-pyrrolidin-2-one compound |
| US4946967A (en) * | 1988-11-03 | 1990-08-07 | Gaf Chemicals Corporation | Polymerizable derivatives of 5-oxo-pyrrolidinecarboxylic acid |
| EP0496884B1 (en) * | 1989-10-17 | 1997-01-08 | Nippon Soda Co., Ltd. | Pyrrole monomer, process for preparing the same, and functional polymer film |
| US5278034A (en) * | 1990-04-27 | 1994-01-11 | Fuji Photo Film Co., Ltd. | Process for forming color image |
| US6849639B2 (en) * | 1999-12-14 | 2005-02-01 | Amgen Inc. | Integrin inhibitors and their methods of use |
| CN102827056B (zh) * | 2012-09-03 | 2014-07-23 | 华东理工大学 | N-芳基取代吡咯烷酮衍生物及其用途 |
| JP2016526538A (ja) | 2013-06-20 | 2016-09-05 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺ダニ剤及び殺虫剤としてのアリールスルフィド誘導体及びアリールスルホキシド誘導体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2757125A (en) * | 1952-05-16 | 1956-07-31 | Colgate Palmolive Co | N-higher alkyl-4-carboxy-2-pyrrolidones and compositions therewith |
| US2811496A (en) * | 1955-06-21 | 1957-10-29 | Pfizer & Co C | Vinyl halide resins plasticized with 1-substituted-4-carboalkoxy-2-pyrrolidinone |
| FR1233278A (fr) * | 1959-05-11 | 1960-10-12 | Mead Johnson & Co | Perfectionnements apportés aux procédés de préparation d'alcools 3-pyrrolidylméthyliques substitués en position 1 |
| AT218016B (de) * | 1959-05-11 | 1961-11-10 | Mead Johnson & Co | Verfahren zur Herstellung eines 1-substituierten 3-Pyrrolidylmethylalkohols |
| GB1053635A (pt) * | 1961-12-18 | |||
| BE626904A (pt) * | 1962-01-09 | |||
| US3149954A (en) * | 1962-02-16 | 1964-09-22 | Du Pont | Method of retarding the growth of vegetation |
| US3306909A (en) * | 1964-05-05 | 1967-02-28 | Mead Johnson & Co | 3-carbamoyl-1,5-diphenyl-2,4-pyrrolidinediones |
| US3637746A (en) * | 1968-06-10 | 1972-01-25 | American Home Prod | Process for preparing n-aryl-alpha-oxocyclopolymethylene amines an related compounds |
| GB1323061A (en) * | 1969-06-16 | 1973-07-11 | Castrol Ltd | Functional fluids and additives therefor |
| GB1361388A (en) * | 1970-08-05 | 1974-07-24 | Geistlich Soehne Ag | Ny--sulphamoylaryl--pyrrolidines |
| TR18917A (tr) * | 1974-10-31 | 1977-12-09 | Ciba Geigy Ag | 1-(bis-triflormetilfenil)-2-oksopirolidin-4-karbonik asitleri ve bunlarin tuerevleri |
| US4064264A (en) * | 1976-01-07 | 1977-12-20 | Pfizer Inc. | Pyrrolidonecarboxylic acid derivatives as anti-ulcer agents |
-
1975
- 1975-11-07 CH CH1442775A patent/CH618682A5/de not_active IP Right Cessation
-
1976
- 1976-10-28 US US05/736,656 patent/US4129573A/en not_active Expired - Lifetime
- 1976-11-02 NL NL7612152A patent/NL7612152A/xx not_active Application Discontinuation
- 1976-11-04 FR FR7633248A patent/FR2330318A1/fr active Granted
- 1976-11-04 DE DE19762650604 patent/DE2650604A1/de not_active Withdrawn
- 1976-11-05 ZA ZA766643A patent/ZA766643B/xx unknown
- 1976-11-05 IL IL50855A patent/IL50855A0/xx unknown
- 1976-11-05 AU AU19350/76A patent/AU511853B2/en not_active Expired
- 1976-11-05 GR GR52108A patent/GR61133B/el unknown
- 1976-11-05 AT AT824576A patent/AT344755B/de not_active IP Right Cessation
- 1976-11-05 DK DK501276A patent/DK501276A/da unknown
- 1976-11-05 BE BE172093A patent/BE848015A/xx unknown
- 1976-11-05 BR BR7607425A patent/BR7607425A/pt unknown
- 1976-11-05 CA CA264,979A patent/CA1079289A/en not_active Expired
- 1976-11-05 TR TR19368A patent/TR19368A/xx unknown
- 1976-11-05 SE SE7612365A patent/SE7612365L/xx unknown
- 1976-11-05 GB GB46177/76A patent/GB1563835A/en not_active Expired
- 1976-11-05 DD DD7600195636A patent/DD128633A5/xx unknown
- 1976-11-06 ES ES453087A patent/ES453087A1/es not_active Expired
- 1976-11-06 JP JP51133684A patent/JPS5261226A/ja active Pending
- 1976-11-06 ES ES453089A patent/ES453089A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007500A1 (en) * | 1988-12-27 | 1990-07-12 | Ici Americas Inc. | 1-phenyl-3-carboxyamidopyrrolidones and their use as herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| AU511853B2 (en) | 1980-09-11 |
| ES453089A1 (es) | 1977-11-01 |
| ZA766643B (en) | 1977-10-26 |
| ATA824576A (de) | 1977-12-15 |
| BE848015A (fr) | 1977-05-05 |
| DE2650604A1 (de) | 1977-05-12 |
| AU1935076A (en) | 1978-05-11 |
| FR2330318A1 (fr) | 1977-06-03 |
| BR7607425A (pt) | 1977-09-20 |
| GR61133B (en) | 1978-09-15 |
| DD128633A5 (de) | 1977-11-30 |
| FR2330318B1 (pt) | 1980-03-14 |
| GB1563835A (en) | 1980-04-02 |
| AT344755B (de) | 1978-08-10 |
| CA1079289A (en) | 1980-06-10 |
| SE7612365L (sv) | 1977-05-08 |
| TR19368A (tr) | 1979-01-22 |
| JPS5261226A (en) | 1977-05-20 |
| ES453087A1 (es) | 1977-11-01 |
| US4129573A (en) | 1978-12-12 |
| IL50855A0 (en) | 1977-01-31 |
| NL7612152A (nl) | 1977-05-10 |
| DK501276A (da) | 1977-05-08 |
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Legal Events
| Date | Code | Title | Description |
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| PL | Patent ceased |