CA1092109A - 1,2,4-oxadiazin-5-one derivatives - Google Patents
1,2,4-oxadiazin-5-one derivativesInfo
- Publication number
- CA1092109A CA1092109A CA260,696A CA260696A CA1092109A CA 1092109 A CA1092109 A CA 1092109A CA 260696 A CA260696 A CA 260696A CA 1092109 A CA1092109 A CA 1092109A
- Authority
- CA
- Canada
- Prior art keywords
- oxadiazin
- dihydro
- radical
- carbon atoms
- general formula
- 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
- AXVRAYSRZWEUFX-UHFFFAOYSA-N 2h-1,2,4-oxadiazin-5-one Chemical class O=C1CONC=N1 AXVRAYSRZWEUFX-UHFFFAOYSA-N 0.000 title claims abstract description 21
- -1 trifluoromethylthio, nitro Chemical group 0.000 claims abstract description 58
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 241000196324 Embryophyta Species 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical class C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- GLNKKXSAXSCJFW-UHFFFAOYSA-N 3-(5-methylthiophen-2-yl)-2h-1,2,4-oxadiazin-5-one Chemical compound S1C(C)=CC=C1C1=NC(=O)CON1 GLNKKXSAXSCJFW-UHFFFAOYSA-N 0.000 claims description 3
- VAWRBVUJKDVBIV-UHFFFAOYSA-N 6-phenyl-3-thiophen-2-yl-2h-1,2,4-oxadiazin-5-one Chemical compound O=C1N=C(C=2SC=CC=2)NOC1C1=CC=CC=C1 VAWRBVUJKDVBIV-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 244000045561 useful plants Species 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- OXLMUXAGSAHHNJ-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-2h-1,2,4-oxadiazin-5-one Chemical compound S1C(Cl)=CC=C1C1=NC(=O)CON1 OXLMUXAGSAHHNJ-UHFFFAOYSA-N 0.000 claims 1
- RORUZVBIRGZTOL-UHFFFAOYSA-N 3-thiophen-2-yl-2h-1,2,4-oxadiazin-5-one Chemical compound O=C1CONC(C=2SC=CC=2)=N1 RORUZVBIRGZTOL-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 244000038559 crop plants Species 0.000 claims 1
- QQSGDKKFXBGYON-UHFFFAOYSA-N ethoxy-methylperoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical class CCOP(=S)(OOC)OC1=CC(C)=NC(C(C)C)=N1 QQSGDKKFXBGYON-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 235000013399 edible fruits Nutrition 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 241000227653 Lycopersicon Species 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000149 penetrating effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YOUDLOUFERNGRO-UHFFFAOYSA-N 5-(chloromethyl)-3-thiophen-2-yl-1,2,4-oxadiazole Chemical compound O1C(CCl)=NC(C=2SC=CC=2)=N1 YOUDLOUFERNGRO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 2
- 244000043158 Lens esculenta Species 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- LMVAXOJOCSZBFJ-UHFFFAOYSA-N ethyl 4-chlorobenzenecarboximidate;hydrochloride Chemical compound Cl.CCOC(=N)C1=CC=C(Cl)C=C1 LMVAXOJOCSZBFJ-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- NKMNPRXPUZINOM-UHFFFAOYSA-N n'-hydroxythiophene-2-carboximidamide Chemical compound ON=C(N)C1=CC=CS1 NKMNPRXPUZINOM-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- YTSJWBUJZLIWNE-UHFFFAOYSA-M (2-ethoxy-2-oxoethoxy)azanium;chloride Chemical compound [Cl-].CCOC(=O)CO[NH3+] YTSJWBUJZLIWNE-UHFFFAOYSA-M 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical class O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 description 1
- WKDSDGGFDDJOGO-UHFFFAOYSA-N 2h-oxadiazin-5-one Chemical compound O=C1CONN=C1 WKDSDGGFDDJOGO-UHFFFAOYSA-N 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- ZNKNRQTYMDVOQD-UHFFFAOYSA-N 3-(4-chlorophenyl)-2h-1,2,4-oxadiazin-5-one Chemical compound C1=CC(Cl)=CC=C1C1=NC(=O)CON1 ZNKNRQTYMDVOQD-UHFFFAOYSA-N 0.000 description 1
- AEBTWBSEZVNFFF-UHFFFAOYSA-N 6-ethyl-3-thiophen-2-yl-2h-1,2,4-oxadiazin-5-one Chemical compound O=C1C(CC)ONC(C=2SC=CC=2)=N1 AEBTWBSEZVNFFF-UHFFFAOYSA-N 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 101100238358 Dictyostelium discoideum mpl3 gene Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 240000004322 Lens culinaris Species 0.000 description 1
- 235000010666 Lens esculenta Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003226 decolorizating effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- IKCYQNSSQXAQHC-UHFFFAOYSA-N ethyl 2-aminooxyacetate;hydrochloride Chemical compound Cl.CCOC(=O)CON IKCYQNSSQXAQHC-UHFFFAOYSA-N 0.000 description 1
- BKTKLDMYHTUESO-UHFFFAOYSA-N ethyl 2-bromo-2-phenylacetate Chemical compound CCOC(=O)C(Br)C1=CC=CC=C1 BKTKLDMYHTUESO-UHFFFAOYSA-N 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- RPJVSOWOSUPJJE-UHFFFAOYSA-N ethyl 2-chlorobenzenecarboximidate;hydrochloride Chemical compound Cl.CCOC(=N)C1=CC=CC=C1Cl RPJVSOWOSUPJJE-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR75,27885 | 1975-09-11 | ||
| FR7527885A FR2323692A1 (fr) | 1975-09-11 | 1975-09-11 | Nouveaux derives de la dihydro-5,6 4h-oxadiazine-1,2,4 one-5, leur preparation et les compositions a proprietes herbicides qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1092109A true CA1092109A (en) | 1980-12-23 |
Family
ID=9159863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA260,696A Expired CA1092109A (en) | 1975-09-11 | 1976-09-08 | 1,2,4-oxadiazin-5-one derivatives |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5236679A (enExample) |
| AR (1) | AR222625A1 (enExample) |
| AT (1) | AT346852B (enExample) |
| BE (1) | BE846083A (enExample) |
| BR (1) | BR7606002A (enExample) |
| CA (1) | CA1092109A (enExample) |
| CH (1) | CH600766A5 (enExample) |
| DD (1) | DD129024A5 (enExample) |
| DE (1) | DE2640464A1 (enExample) |
| DK (1) | DK410776A (enExample) |
| ES (1) | ES451145A1 (enExample) |
| FR (1) | FR2323692A1 (enExample) |
| GB (1) | GB1501589A (enExample) |
| HU (1) | HU176418B (enExample) |
| IE (1) | IE43946B1 (enExample) |
| IL (1) | IL50464A (enExample) |
| LU (1) | LU75767A1 (enExample) |
| NL (1) | NL7610067A (enExample) |
| PL (1) | PL101303B1 (enExample) |
| PT (1) | PT65574B (enExample) |
| RO (1) | RO69406A (enExample) |
| SE (1) | SE7610051L (enExample) |
| SU (1) | SU625608A3 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU181588B (en) * | 1980-12-31 | 1983-10-28 | Richter Gedeon Vegyeszet | Process for preparing n4-substituted tetrahydro-1,2,4-oxadiazin-5-one derivatives with anticonvulsive effect |
| FR2497202A1 (fr) * | 1980-12-31 | 1982-07-02 | Richter Gedeon Vegyeszet | Nouveaux derives de tetrahydro-1,2,4-oxadiazin-5-one, leur preparation et compositions pharmaceutiques les contenant |
| DE3514450A1 (de) * | 1985-04-22 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von imidaten sowie neue arylsubstituierte imidate |
| JPS63173419A (ja) * | 1987-01-12 | 1988-07-18 | Fujitsu Ltd | 原子発振器 |
| CN107629020B (zh) * | 2017-09-28 | 2020-09-04 | 湖北科技学院 | 一种4h-1,2,4-噁二嗪-5(6h)-酮类化合物及其合成方法 |
-
1975
- 1975-09-11 FR FR7527885A patent/FR2323692A1/fr active Granted
-
1976
- 1976-09-01 ES ES451145A patent/ES451145A1/es not_active Expired
- 1976-09-08 IE IE2009/76A patent/IE43946B1/en unknown
- 1976-09-08 DD DD7600194682A patent/DD129024A5/xx unknown
- 1976-09-08 DE DE19762640464 patent/DE2640464A1/de not_active Withdrawn
- 1976-09-08 CA CA260,696A patent/CA1092109A/en not_active Expired
- 1976-09-08 GB GB37226/76A patent/GB1501589A/en not_active Expired
- 1976-09-09 SU SU762395116A patent/SU625608A3/ru active
- 1976-09-10 LU LU75767A patent/LU75767A1/xx unknown
- 1976-09-10 BR BR7606002A patent/BR7606002A/pt unknown
- 1976-09-10 PL PL1976192320A patent/PL101303B1/pl unknown
- 1976-09-10 AT AT669876A patent/AT346852B/de not_active IP Right Cessation
- 1976-09-10 RO RO7687500A patent/RO69406A/ro unknown
- 1976-09-10 DK DK410776A patent/DK410776A/da unknown
- 1976-09-10 CH CH1155976A patent/CH600766A5/xx not_active IP Right Cessation
- 1976-09-10 IL IL50464A patent/IL50464A/xx unknown
- 1976-09-10 SE SE7610051A patent/SE7610051L/xx not_active Application Discontinuation
- 1976-09-10 JP JP51109353A patent/JPS5236679A/ja active Pending
- 1976-09-10 PT PT65574A patent/PT65574B/pt unknown
- 1976-09-10 BE BE170534A patent/BE846083A/xx unknown
- 1976-09-10 NL NL7610067A patent/NL7610067A/xx not_active Application Discontinuation
- 1976-09-10 HU HU76PI538A patent/HU176418B/hu unknown
- 1976-09-10 AR AR264651A patent/AR222625A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1501589A (en) | 1978-02-15 |
| CH600766A5 (enExample) | 1978-06-30 |
| ES451145A1 (es) | 1977-11-16 |
| IL50464A (en) | 1979-03-12 |
| IL50464A0 (en) | 1976-11-30 |
| IE43946L (en) | 1977-03-11 |
| RO69406A (ro) | 1982-09-09 |
| PT65574A (fr) | 1976-10-01 |
| BE846083A (fr) | 1977-03-10 |
| BR7606002A (pt) | 1977-08-23 |
| JPS5236679A (en) | 1977-03-22 |
| DD129024A5 (de) | 1977-12-21 |
| NL7610067A (nl) | 1977-03-15 |
| DK410776A (da) | 1977-03-12 |
| IE43946B1 (en) | 1981-07-01 |
| AR222625A1 (es) | 1981-06-15 |
| PT65574B (fr) | 1978-07-04 |
| PL101303B1 (pl) | 1978-12-30 |
| SU625608A3 (ru) | 1978-09-25 |
| AT346852B (de) | 1978-11-27 |
| FR2323692A1 (fr) | 1977-04-08 |
| ATA669876A (de) | 1978-04-15 |
| FR2323692B1 (enExample) | 1978-10-27 |
| LU75767A1 (enExample) | 1978-05-12 |
| HU176418B (en) | 1981-02-28 |
| DE2640464A1 (de) | 1977-04-14 |
| SE7610051L (sv) | 1977-03-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |