DE2640464A1 - Derivate des 1.2.4-oxadiazin-5-ons, ihre herstellung und verwendung - Google Patents
Derivate des 1.2.4-oxadiazin-5-ons, ihre herstellung und verwendungInfo
- Publication number
- DE2640464A1 DE2640464A1 DE19762640464 DE2640464A DE2640464A1 DE 2640464 A1 DE2640464 A1 DE 2640464A1 DE 19762640464 DE19762640464 DE 19762640464 DE 2640464 A DE2640464 A DE 2640464A DE 2640464 A1 DE2640464 A1 DE 2640464A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- alkyl part
- general formula
- alkyl
- group
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- -1 trifluoromethylthio, carboxy Chemical group 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound 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 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- AXVRAYSRZWEUFX-UHFFFAOYSA-N 2h-1,2,4-oxadiazin-5-one Chemical class O=C1CONC=N1 AXVRAYSRZWEUFX-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 244000025254 Cannabis sativa Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241000219739 Lens Species 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 241000227653 Lycopersicon Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 241000220259 Raphanus Species 0.000 description 4
- 235000006140 Raphanus sativus var sativus Nutrition 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
- 235000013399 edible fruits Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 235000011293 Brassica napus Nutrition 0.000 description 3
- 240000008100 Brassica rapa Species 0.000 description 3
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- 238000000889 atomisation Methods 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
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- NKMNPRXPUZINOM-UHFFFAOYSA-N n'-hydroxythiophene-2-carboximidamide Chemical compound ON=C(N)C1=CC=CS1 NKMNPRXPUZINOM-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 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
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000005094 fruit set Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- ZLOMCSQFNVLEJV-UHFFFAOYSA-N 2-(ethylaminooxy)acetic acid Chemical compound CCNOCC(O)=O ZLOMCSQFNVLEJV-UHFFFAOYSA-N 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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 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 description 1
- 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 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 1
- 244000043158 Lens esculenta Species 0.000 description 1
- 235000010666 Lens esculenta Nutrition 0.000 description 1
- 235000019057 Raphanus caudatus Nutrition 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000011380 Raphanus sativus Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides 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
- 239000012914 anti-clumping agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004042 decolorization Methods 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
- 239000000428 dust Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- YDXVOCXVQXQYPX-UHFFFAOYSA-N ethyl 2-chlorobenzenecarboximidate Chemical compound CCOC(=N)C1=CC=CC=C1Cl YDXVOCXVQXQYPX-UHFFFAOYSA-N 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
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000005286 illumination Methods 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
- 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
- 229920005610 lignin Polymers 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000000873 masking effect Effects 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
- 210000001672 ovary Anatomy 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 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
- 230000000630 rising effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000004062 sedimentation Methods 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
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000003643 water by type Substances 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| DE2640464A1 true DE2640464A1 (de) | 1977-04-14 |
Family
ID=9159863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762640464 Withdrawn DE2640464A1 (de) | 1975-09-11 | 1976-09-08 | Derivate des 1.2.4-oxadiazin-5-ons, ihre herstellung und verwendung |
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) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0055484A1 (de) * | 1980-12-31 | 1982-07-07 | Richter Gedeon Vegyeszeti Gyar R.T. | Tetrahydro-1,2,4-oxadiazin-5-onderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| EP0055490A1 (de) * | 1980-12-31 | 1982-07-07 | Richter Gedeon Vegyeszeti Gyar R.T. | Tetrahydro-1,2,4-oxadiazin-5-onderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| EP0200051A3 (en) * | 1985-04-22 | 1987-09-30 | Hoechst Aktiengesellschaft | Process for the preparation of imidates, and phenyl-substituted imidates |
| CN107629020A (zh) * | 2017-09-28 | 2018-01-26 | 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63173419A (ja) * | 1987-01-12 | 1988-07-18 | Fujitsu Ltd | 原子発振器 |
-
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
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0055484A1 (de) * | 1980-12-31 | 1982-07-07 | Richter Gedeon Vegyeszeti Gyar R.T. | Tetrahydro-1,2,4-oxadiazin-5-onderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| EP0055490A1 (de) * | 1980-12-31 | 1982-07-07 | Richter Gedeon Vegyeszeti Gyar R.T. | Tetrahydro-1,2,4-oxadiazin-5-onderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| EP0200051A3 (en) * | 1985-04-22 | 1987-09-30 | Hoechst Aktiengesellschaft | Process for the preparation of imidates, and phenyl-substituted imidates |
| CN107629020A (zh) * | 2017-09-28 | 2018-01-26 | 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 |
| 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 |
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 |
| CA1092109A (en) | 1980-12-23 |
| 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 |
| SE7610051L (sv) | 1977-03-12 |
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