CH624273A5 - Herbicide - Google Patents
Herbicide Download PDFInfo
- Publication number
- CH624273A5 CH624273A5 CH851576A CH851576A CH624273A5 CH 624273 A5 CH624273 A5 CH 624273A5 CH 851576 A CH851576 A CH 851576A CH 851576 A CH851576 A CH 851576A CH 624273 A5 CH624273 A5 CH 624273A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- phenyl
- dihydro
- pyridinone
- subparagraphs
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 13
- 230000002363 herbicidal effect Effects 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims description 146
- 239000000203 mixture Substances 0.000 claims description 34
- -1 phenoxy, phenylthio Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000004480 active ingredient Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- VRWBDTPZJOEALB-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)-5-phenyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C)C=CC=2)C(=O)C=1C1=CC=CC=C1 VRWBDTPZJOEALB-UHFFFAOYSA-N 0.000 claims description 3
- PVJXUIUFKMURFD-UHFFFAOYSA-N 1-methyl-5-(3-methylphenyl)-3-phenyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC=CC=2)C(=O)C=1C1=CC=CC(C)=C1 PVJXUIUFKMURFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- PWNAVYNBODYLMS-UHFFFAOYSA-N 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC=CC=2)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 PWNAVYNBODYLMS-UHFFFAOYSA-N 0.000 claims description 2
- GHJOIYGCNIDYAC-UHFFFAOYSA-N 1-methyl-5-phenyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=CC=C1 GHJOIYGCNIDYAC-UHFFFAOYSA-N 0.000 claims description 2
- OVVCXAPQRAUKRK-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC(Cl)=CC=2)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 OVVCXAPQRAUKRK-UHFFFAOYSA-N 0.000 claims description 2
- DHVKGOFDTAPPAB-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC(F)=CC=2)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 DHVKGOFDTAPPAB-UHFFFAOYSA-N 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 67
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 24
- 239000002689 soil Substances 0.000 description 20
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 238000009472 formulation Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- 238000009739 binding Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 235000019713 millet Nutrition 0.000 description 5
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- FQMOMNJVFAKQQC-UHFFFAOYSA-N 1-ethenylpyridin-4-one Chemical compound C=CN1C=CC(=O)C=C1 FQMOMNJVFAKQQC-UHFFFAOYSA-N 0.000 description 2
- QKBXHIYTGWLVOB-UHFFFAOYSA-N 1-prop-2-ynylpyridin-4-one Chemical compound O=C1C=CN(CC#C)C=C1 QKBXHIYTGWLVOB-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 241001113556 Elodea Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 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 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- KOVIIGLZLUFATR-UHFFFAOYSA-N 1-ethenyl-3-(2-ethylphenyl)-5-(3-propoxyphenyl)piperidin-4-one Chemical compound CCCOC1=CC=CC(C2C(C(CN(C2)C=C)C=2C(=CC=CC=2)CC)=O)=C1 KOVIIGLZLUFATR-UHFFFAOYSA-N 0.000 description 1
- HBPGEXVIQNVUJY-UHFFFAOYSA-N 1-ethenyl-3-(3-ethylphenyl)piperidin-4-one Chemical compound CCC1=CC=CC(C2C(CCN(C2)C=C)=O)=C1 HBPGEXVIQNVUJY-UHFFFAOYSA-N 0.000 description 1
- FXDJSJMBCILBKS-UHFFFAOYSA-N 1-ethenyl-3-(3-methoxyphenyl)piperidin-4-one Chemical compound COC1=CC=CC(C2C(CCN(C2)C=C)=O)=C1 FXDJSJMBCILBKS-UHFFFAOYSA-N 0.000 description 1
- GACQIFBWFLBELU-UHFFFAOYSA-N 1-ethenyl-5-(3-fluorophenyl)-2,3-dihydropyridin-4-one Chemical compound FC1=CC=CC(C=2C(CCN(C=2)C=C)=O)=C1 GACQIFBWFLBELU-UHFFFAOYSA-N 0.000 description 1
- ACZCJXJAFHZMKO-UHFFFAOYSA-N 1-ethyl-3,5-bis(3-methylphenyl)-2,3-dihydropyridin-4-one Chemical compound C=1N(CC)CC(C=2C=C(C)C=CC=2)C(=O)C=1C1=CC=CC(C)=C1 ACZCJXJAFHZMKO-UHFFFAOYSA-N 0.000 description 1
- HKZQJJJDTDRXNR-UHFFFAOYSA-N 1-ethyl-3-(3-ethylphenyl)-2,3-dihydropyridin-4-one Chemical compound O=C1C=CN(CC)CC1C1=CC=CC(CC)=C1 HKZQJJJDTDRXNR-UHFFFAOYSA-N 0.000 description 1
- ZKGGLAMFWHOHPU-UHFFFAOYSA-N 1-ethyl-3-ethylsulfanyl-5-(3-propoxyphenyl)piperidin-4-one Chemical compound CCCOC1=CC=CC(C2C(C(SCC)CN(CC)C2)=O)=C1 ZKGGLAMFWHOHPU-UHFFFAOYSA-N 0.000 description 1
- PDXQVSLSVHXFES-UHFFFAOYSA-N 1-ethyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(CC)CC(C=2C=CC=CC=2)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 PDXQVSLSVHXFES-UHFFFAOYSA-N 0.000 description 1
- NLPSIXIIAZMRLH-UHFFFAOYSA-N 1-ethyl-5-phenyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(CC)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=CC=C1 NLPSIXIIAZMRLH-UHFFFAOYSA-N 0.000 description 1
- PVMGDJVUYFHZES-UHFFFAOYSA-N 1-methyl-3,5-diphenylpiperidin-4-one Chemical class C1N(C)CC(C=2C=CC=CC=2)C(=O)C1C1=CC=CC=C1 PVMGDJVUYFHZES-UHFFFAOYSA-N 0.000 description 1
- AEVBNVKTPKVEJR-UHFFFAOYSA-N 1-methyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound O=C1C=CN(C)CC1C1=CC=CC(C(F)(F)F)=C1 AEVBNVKTPKVEJR-UHFFFAOYSA-N 0.000 description 1
- PTDRULRSQWMKJB-UHFFFAOYSA-N 1-methyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound CN1CCC(=O)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 PTDRULRSQWMKJB-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MIUVWJJNPDWVMH-UHFFFAOYSA-N 1-propylpyridin-4-one Chemical compound CCCN1C=CC(=O)C=C1 MIUVWJJNPDWVMH-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SIEABVOJVIRNRJ-UHFFFAOYSA-N 3,5-bis(3-chlorophenyl)-1-methyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(Cl)C=CC=2)C(=O)C=1C1=CC=CC(Cl)=C1 SIEABVOJVIRNRJ-UHFFFAOYSA-N 0.000 description 1
- AZNGUIUOJDPDOI-UHFFFAOYSA-N 3,5-bis(3-chlorophenyl)-1-methylpiperidin-4-one Chemical compound C1N(C)CC(C=2C=C(Cl)C=CC=2)C(=O)C1C1=CC=CC(Cl)=C1 AZNGUIUOJDPDOI-UHFFFAOYSA-N 0.000 description 1
- LMGGTKVFSIJNDZ-UHFFFAOYSA-N 3,5-bis(3-fluorophenyl)-1-methylpiperidin-4-one Chemical compound C1N(C)CC(C=2C=C(F)C=CC=2)C(=O)C1C1=CC=CC(F)=C1 LMGGTKVFSIJNDZ-UHFFFAOYSA-N 0.000 description 1
- ZZBXHJIJTJTDQZ-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical compound C1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1Cl ZZBXHJIJTJTDQZ-UHFFFAOYSA-N 0.000 description 1
- ZCNAAOTUCFEJKD-UHFFFAOYSA-N 3-(3-bromophenyl)-1,5-diethylpiperidin-4-one Chemical compound O=C1C(CC)CN(CC)CC1C1=CC=CC(Br)=C1 ZCNAAOTUCFEJKD-UHFFFAOYSA-N 0.000 description 1
- HTZZAUNQHDRLCB-UHFFFAOYSA-N 3-(3-bromophenyl)-1-ethyl-5-phenylsulfanylpiperidin-4-one Chemical compound O=C1C(C=2C=C(Br)C=CC=2)CN(CC)CC1SC1=CC=CC=C1 HTZZAUNQHDRLCB-UHFFFAOYSA-N 0.000 description 1
- AHKRINXVBJZUJM-UHFFFAOYSA-N 3-(3-bromophenyl)-1-ethyl-5-propan-2-ylpiperidin-4-one Chemical compound C1N(CC)CC(C(C)C)C(=O)C1C1=CC=CC(Br)=C1 AHKRINXVBJZUJM-UHFFFAOYSA-N 0.000 description 1
- FUIZPYCPINPZTH-UHFFFAOYSA-N 3-(3-bromophenyl)-1-ethyl-5-propylpiperidin-4-one Chemical compound O=C1C(CCC)CN(CC)CC1C1=CC=CC(Br)=C1 FUIZPYCPINPZTH-UHFFFAOYSA-N 0.000 description 1
- KPZCKGCMLNHNDZ-UHFFFAOYSA-N 3-(3-bromophenyl)-1-methyl-5-phenyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(Br)C=CC=2)C(=O)C=1C1=CC=CC=C1 KPZCKGCMLNHNDZ-UHFFFAOYSA-N 0.000 description 1
- VTXHPGFBNYABPK-UHFFFAOYSA-N 3-(3-bromophenyl)-1-methyl-5-phenylpiperidin-4-one Chemical compound C1N(C)CC(C=2C=CC=CC=2)C(=O)C1C1=CC=CC(Br)=C1 VTXHPGFBNYABPK-UHFFFAOYSA-N 0.000 description 1
- MMIFJRVTORYNIG-UHFFFAOYSA-N 3-(3-bromophenyl)-1-methyl-5-propylsulfanylpiperidin-4-one Chemical compound O=C1C(SCCC)CN(C)CC1C1=CC=CC(Br)=C1 MMIFJRVTORYNIG-UHFFFAOYSA-N 0.000 description 1
- QHKJSOUDTAIPQO-UHFFFAOYSA-N 3-(3-bromophenyl)-1-methylpiperidin-4-one Chemical compound C1N(C)CCC(=O)C1C1=CC=CC(Br)=C1 QHKJSOUDTAIPQO-UHFFFAOYSA-N 0.000 description 1
- OXWHHUGKZGMOCE-UHFFFAOYSA-N 3-(3-bromophenyl)-5-(2-methylpropyl)-1-propylpiperidin-4-one Chemical compound C1N(CCC)CC(CC(C)C)C(=O)C1C1=CC=CC(Br)=C1 OXWHHUGKZGMOCE-UHFFFAOYSA-N 0.000 description 1
- WLJPHFUIBIPBOQ-UHFFFAOYSA-N 3-(3-bromophenyl)-5-ethoxy-1-methylpiperidin-4-one Chemical compound O=C1C(OCC)CN(C)CC1C1=CC=CC(Br)=C1 WLJPHFUIBIPBOQ-UHFFFAOYSA-N 0.000 description 1
- URRJYHATQMAOTR-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-(3-fluorophenyl)-1-methylpiperidin-4-one Chemical compound C1N(C)CC(C=2C=C(F)C=CC=2)C(=O)C1C1=CC=CC(Cl)=C1 URRJYHATQMAOTR-UHFFFAOYSA-N 0.000 description 1
- PFHSFFSNPSUPIO-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-(4-chlorophenyl)-1-methyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(Cl)C=CC=2)C(=O)C=1C1=CC=C(Cl)C=C1 PFHSFFSNPSUPIO-UHFFFAOYSA-N 0.000 description 1
- POXOWTWAYFMUDK-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-(4-chlorophenyl)-1-methylpiperidin-4-one Chemical compound C1N(C)CC(C=2C=CC(Cl)=CC=2)C(=O)C1C1=CC=CC(Cl)=C1 POXOWTWAYFMUDK-UHFFFAOYSA-N 0.000 description 1
- SASVVXMAIYXRON-UHFFFAOYSA-N 3-(3-ethoxyphenyl)-5-(4-ethoxyphenyl)-1-prop-1-en-2-ylpiperidin-4-one Chemical compound C1=CC(OCC)=CC=C1C1C(=O)C(C=2C=C(OCC)C=CC=2)CN(C(C)=C)C1 SASVVXMAIYXRON-UHFFFAOYSA-N 0.000 description 1
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- KDPPLBDZTUSFCW-UHFFFAOYSA-N 3-(3-fluorophenyl)-1-methyl-5-phenoxypiperidin-4-one Chemical compound O=C1C(C=2C=C(F)C=CC=2)CN(C)CC1OC1=CC=CC=C1 KDPPLBDZTUSFCW-UHFFFAOYSA-N 0.000 description 1
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- SSJIIVXIYSZMCX-UHFFFAOYSA-N 3-(3-fluorophenyl)-1-methyl-5-propoxypiperidin-4-one Chemical compound O=C1C(OCCC)CN(C)CC1C1=CC=CC(F)=C1 SSJIIVXIYSZMCX-UHFFFAOYSA-N 0.000 description 1
- NHHKJUWLMVJWOV-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-methyl-5-phenyl-2,3-dihydropyridin-4-one Chemical compound COC1=CC=CC(C2C(C(=CN(C)C2)C=2C=CC=CC=2)=O)=C1 NHHKJUWLMVJWOV-UHFFFAOYSA-N 0.000 description 1
- VZEODMLXOOKCGA-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-methyl-5-phenylpiperidin-4-one Chemical compound COC1=CC=CC(C2C(C(CN(C)C2)C=2C=CC=CC=2)=O)=C1 VZEODMLXOOKCGA-UHFFFAOYSA-N 0.000 description 1
- IBWOOLSKQOIRRM-UHFFFAOYSA-N 3-(3-propan-2-yloxyphenyl)-1-prop-1-enylpiperidin-4-one Chemical compound C1N(C=CC)CCC(=O)C1C1=CC=CC(OC(C)C)=C1 IBWOOLSKQOIRRM-UHFFFAOYSA-N 0.000 description 1
- TZCAGFKVIQCAIC-UHFFFAOYSA-N 3-(3-propan-2-yloxyphenyl)-5-(3-propylphenyl)-1-prop-2-ynylpiperidin-4-one Chemical compound CCCC1=CC=CC(C2C(C(CN(CC#C)C2)C=2C=C(OC(C)C)C=CC=2)=O)=C1 TZCAGFKVIQCAIC-UHFFFAOYSA-N 0.000 description 1
- WEAPXEUEJNJKJT-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical compound C1N(C)CC(C=2C=CC(Cl)=CC=2)C(=O)C1C1=CC=CC(C(F)(F)F)=C1 WEAPXEUEJNJKJT-UHFFFAOYSA-N 0.000 description 1
- FRLGICOECSXHFB-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical compound C1N(C)CC(C=2C=CC(F)=CC=2)C(=O)C1C1=CC=CC(C(F)(F)F)=C1 FRLGICOECSXHFB-UHFFFAOYSA-N 0.000 description 1
- LPKLSMUPSHGTPA-UHFFFAOYSA-N 3-butoxy-5-(3-chlorophenyl)-1-prop-2-ynyl-2,3-dihydropyridin-4-one Chemical compound O=C1C(OCCCC)CN(CC#C)C=C1C1=CC=CC(Cl)=C1 LPKLSMUPSHGTPA-UHFFFAOYSA-N 0.000 description 1
- IQJPWIUOXXLFTH-UHFFFAOYSA-N 3-butyl-1-ethyl-5-(3-propan-2-ylphenyl)piperidin-4-one Chemical compound O=C1C(CCCC)CN(CC)CC1C1=CC=CC(C(C)C)=C1 IQJPWIUOXXLFTH-UHFFFAOYSA-N 0.000 description 1
- MJZQAJKFEPQIAS-UHFFFAOYSA-N 3-butylsulfanyl-1-ethyl-5-(3-fluorophenyl)piperidin-4-one Chemical compound O=C1C(SCCCC)CN(CC)CC1C1=CC=CC(F)=C1 MJZQAJKFEPQIAS-UHFFFAOYSA-N 0.000 description 1
- HSVGPWIPGSNALY-UHFFFAOYSA-N 3-ethoxy-5-(3-methylphenyl)-1-prop-2-ynylpiperidin-4-one Chemical compound O=C1C(OCC)CN(CC#C)CC1C1=CC=CC(C)=C1 HSVGPWIPGSNALY-UHFFFAOYSA-N 0.000 description 1
- QFZOFZFIZGHMRN-UHFFFAOYSA-N 3-ethyl-1-methyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound O=C1C(CC)CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 QFZOFZFIZGHMRN-UHFFFAOYSA-N 0.000 description 1
- UBFIMJNRWYPSEV-UHFFFAOYSA-N 3-ethyl-1-methyl-5-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical compound O=C1C(CC)CN(C)CC1C1=CC=CC(C(F)(F)F)=C1 UBFIMJNRWYPSEV-UHFFFAOYSA-N 0.000 description 1
- AZLJERYFXPBDTN-UHFFFAOYSA-N 3-ethyl-5-(3-methylphenyl)-1-prop-1-enylpiperidin-4-one Chemical compound O=C1C(CC)CN(C=CC)CC1C1=CC=CC(C)=C1 AZLJERYFXPBDTN-UHFFFAOYSA-N 0.000 description 1
- QGBFUZJUARPDLM-UHFFFAOYSA-N 3-methoxy-1-methyl-5-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical compound O=C1C(OC)CN(C)CC1C1=CC=CC(C(F)(F)F)=C1 QGBFUZJUARPDLM-UHFFFAOYSA-N 0.000 description 1
- XCTZABOCOCICEZ-UHFFFAOYSA-N 3-phenoxy-5-(3-propan-2-yloxyphenyl)-1-propylpiperidin-4-one Chemical compound O=C1C(C=2C=C(OC(C)C)C=CC=2)CN(CCC)CC1OC1=CC=CC=C1 XCTZABOCOCICEZ-UHFFFAOYSA-N 0.000 description 1
- JVNOICQSAUDZDP-UHFFFAOYSA-N 3-phenoxy-5-phenyl-1-prop-1-enyl-2,3-dihydropyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(C=CC)CC1OC1=CC=CC=C1 JVNOICQSAUDZDP-UHFFFAOYSA-N 0.000 description 1
- GCSFYHTYULPVGT-UHFFFAOYSA-N 3-phenylpiperidin-4-one Chemical compound O=C1CCNCC1C1=CC=CC=C1 GCSFYHTYULPVGT-UHFFFAOYSA-N 0.000 description 1
- DQXLHRDVPCQLNC-UHFFFAOYSA-N 3-tert-butyl-1-ethyl-5-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical compound O=C1C(C(C)(C)C)CN(CC)CC1C1=CC=CC(C(F)(F)F)=C1 DQXLHRDVPCQLNC-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MMJYDQSZBHUUAB-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-methyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=CC=C1Cl MMJYDQSZBHUUAB-UHFFFAOYSA-N 0.000 description 1
- HKKVGDHYQYPCOP-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-(4-chlorophenyl)-1-methyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC(Cl)=CC=2)C(=O)C=1C1=CC=CC(Cl)=C1 HKKVGDHYQYPCOP-UHFFFAOYSA-N 0.000 description 1
- ANRMIUJOFHKXDD-UHFFFAOYSA-N 5-(3-methoxyphenyl)-1-methyl-3-phenyl-2,3-dihydropyridin-4-one Chemical compound COC1=CC=CC(C=2C(C(CN(C)C=2)C=2C=CC=CC=2)=O)=C1 ANRMIUJOFHKXDD-UHFFFAOYSA-N 0.000 description 1
- ATCKRZPSIMWFTF-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-methyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=C(Cl)C=C1 ATCKRZPSIMWFTF-UHFFFAOYSA-N 0.000 description 1
- AVSUIEDSKCPYKV-UHFFFAOYSA-N 5-(4-fluorophenyl)-1-methyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=C(F)C=C1 AVSUIEDSKCPYKV-UHFFFAOYSA-N 0.000 description 1
- OFMGQZDONDFFOQ-UHFFFAOYSA-N 5-ethyl-1-methyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound O=C1C(CC)=CN(C)CC1C1=CC=CC(C(F)(F)F)=C1 OFMGQZDONDFFOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241001674345 Callitropsis nootkatensis Species 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- 235000005853 Cyperus esculentus Nutrition 0.000 description 1
- 244000075634 Cyperus rotundus Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000052355 Hydrilla verticillata Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 244000207740 Lemna minor Species 0.000 description 1
- 235000006439 Lemna minor Nutrition 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 240000000982 Malva neglecta Species 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000000851 Vaccinium corymbosum Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 240000003307 Zinnia violacea Species 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical group O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
-
- 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
- C07D213/68—One oxygen atom attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59309575A | 1975-07-03 | 1975-07-03 | |
| US05/685,409 US4065290A (en) | 1975-07-03 | 1976-05-20 | Herbicidal β-phenyl-4-piperidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624273A5 true CH624273A5 (en) | 1981-07-31 |
Family
ID=27081623
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH851576A CH624273A5 (en) | 1975-07-03 | 1976-07-02 | Herbicide |
| CH322980A CH624392A5 (en) | 1975-07-03 | 1980-04-25 | Process for the preparation of novel beta-phenyl-4-piperidinones and -dihydropyridinones |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH322980A CH624392A5 (en) | 1975-07-03 | 1980-04-25 | Process for the preparation of novel beta-phenyl-4-piperidinones and -dihydropyridinones |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS527970A (enExample) |
| AU (1) | AU497882B2 (enExample) |
| BR (1) | BR7604362A (enExample) |
| CA (1) | CA1088543A (enExample) |
| CH (2) | CH624273A5 (enExample) |
| DE (1) | DE2628992A1 (enExample) |
| ES (1) | ES449530A1 (enExample) |
| FR (1) | FR2315851A1 (enExample) |
| GB (1) | GB1555966A (enExample) |
| GR (1) | GR62256B (enExample) |
| IE (1) | IE43851B1 (enExample) |
| IL (1) | IL49858A (enExample) |
| IT (1) | IT1065058B (enExample) |
| NL (1) | NL7607421A (enExample) |
| OA (1) | OA05373A (enExample) |
| PT (1) | PT65313B (enExample) |
| SU (2) | SU691060A3 (enExample) |
| TR (1) | TR18922A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2720612C2 (de) * | 1977-05-07 | 1987-02-19 | Basf Ag, 6700 Ludwigshafen | 3,5-Dimethyl-piperidin-4-one |
| US4808720A (en) * | 1986-06-09 | 1989-02-28 | Stauffer Chemical Company | Certain 3-benzoyl-4-oxolactams |
-
1976
- 1976-06-14 CA CA254,796A patent/CA1088543A/en not_active Expired
- 1976-06-15 GR GR51000A patent/GR62256B/el unknown
- 1976-06-15 IE IE1295/76A patent/IE43851B1/en unknown
- 1976-06-22 IL IL49858A patent/IL49858A/xx unknown
- 1976-06-28 GB GB26770/76A patent/GB1555966A/en not_active Expired
- 1976-06-28 DE DE19762628992 patent/DE2628992A1/de not_active Withdrawn
- 1976-07-01 OA OA55871A patent/OA05373A/xx unknown
- 1976-07-02 IT IT25001/76A patent/IT1065058B/it active
- 1976-07-02 SU SU762377702A patent/SU691060A3/ru active
- 1976-07-02 ES ES449530A patent/ES449530A1/es not_active Expired
- 1976-07-02 BR BR7604362A patent/BR7604362A/pt unknown
- 1976-07-02 CH CH851576A patent/CH624273A5/de not_active IP Right Cessation
- 1976-07-02 PT PT65313A patent/PT65313B/pt unknown
- 1976-07-02 AU AU15538/76A patent/AU497882B2/en not_active Expired
- 1976-07-02 TR TR18922A patent/TR18922A/xx unknown
- 1976-07-02 FR FR7620260A patent/FR2315851A1/fr active Granted
- 1976-07-03 JP JP51079407A patent/JPS527970A/ja active Pending
- 1976-07-05 NL NL7607421A patent/NL7607421A/xx not_active Application Discontinuation
-
1977
- 1977-02-17 SU SU772453148A patent/SU688126A3/ru active
-
1980
- 1980-04-25 CH CH322980A patent/CH624392A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE43851B1 (en) | 1981-06-17 |
| OA05373A (fr) | 1981-02-28 |
| ES449530A1 (es) | 1977-12-01 |
| JPS527970A (en) | 1977-01-21 |
| DE2628992A1 (de) | 1977-01-20 |
| BR7604362A (pt) | 1977-07-26 |
| AU497882B2 (en) | 1979-01-18 |
| CA1088543A (en) | 1980-10-28 |
| SU688126A3 (ru) | 1979-09-25 |
| IL49858A (en) | 1980-06-30 |
| GB1555966A (en) | 1979-11-14 |
| FR2315851A1 (fr) | 1977-01-28 |
| SU691060A3 (ru) | 1979-10-05 |
| NL7607421A (nl) | 1977-01-05 |
| AU1553876A (en) | 1978-01-05 |
| IT1065058B (it) | 1985-02-25 |
| PT65313B (en) | 1978-01-05 |
| IL49858A0 (en) | 1976-08-31 |
| PT65313A (en) | 1976-08-01 |
| IE43851L (en) | 1977-01-03 |
| FR2315851B1 (enExample) | 1978-05-05 |
| GR62256B (en) | 1979-03-19 |
| TR18922A (tr) | 1977-12-20 |
| CH624392A5 (en) | 1981-07-31 |
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