HUT61534A - 3,5-dioxo-3,4,5,6-tetrahydro-1,2-oxazine derivatives, herbicidal, acaricidal and plant growth regulating composition comprising such compounds as active ingredient, process for applying the composition and for producing the active ingredients, as well as 2-nitro-4-(trifluoromethoxy)-benzoic acid intermediate - Google Patents

3,5-dioxo-3,4,5,6-tetrahydro-1,2-oxazine derivatives, herbicidal, acaricidal and plant growth regulating composition comprising such compounds as active ingredient, process for applying the composition and for producing the active ingredients, as well as 2-nitro-4-(trifluoromethoxy)-benzoic acid intermediate Download PDF

Info

Publication number: HUT61534A
Authority: HU; Hungary
Prior art keywords: hydrogen; formula; alkyl; nitro; compound
Prior art date: 1990-10-25

Application number

HU922107A

Other languages

English (en)

Hungarian (hu)

Other versions

HU9202107D0 (en

Inventor

Shy-Fuh Lee

Original Assignee

Sandoz Ag

Priority date (The priority date 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 date listed.)

1990-10-25

Filing date

1991-10-23

Publication date

1993-01-28

1991-10-23 Application filed by Sandoz Ag filed Critical Sandoz Ag

1992-10-28 Publication of HU9202107D0 publication Critical patent/HU9202107D0/hu

1993-01-28 Publication of HUT61534A publication Critical patent/HUT61534A/hu

Links

239000000203 mixture Substances 0.000 title claims abstract description 22
238000000034 method Methods 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 title claims description 53
230000002363 herbicidal effect Effects 0.000 title claims description 10
JANOFBIDZFXRKA-UHFFFAOYSA-N 2-nitro-4-(trifluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC(F)(F)F)C=C1[N+]([O-])=O JANOFBIDZFXRKA-UHFFFAOYSA-N 0.000 title claims description 5
230000000895 acaricidal effect Effects 0.000 title abstract description 5
KDZFOYZCCXIDJJ-UHFFFAOYSA-N oxazinane-3,5-dione Chemical class O=C1CONC(=O)C1 KDZFOYZCCXIDJJ-UHFFFAOYSA-N 0.000 title abstract description 4
239000004480 active ingredient Substances 0.000 title description 7
230000008635 plant growth Effects 0.000 title description 3
230000001105 regulatory effect Effects 0.000 title description 2
238000002360 preparation method Methods 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 37
239000001257 hydrogen Substances 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 24
150000002431 hydrogen Chemical class 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
-1 enol ester Chemical class 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
241000196324 Embryophyta Species 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
150000001768 cations Chemical class 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
239000004009 herbicide Substances 0.000 abstract description 10
239000000642 acaricide Substances 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 14
239000002585 base Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229940121375 antifungal agent Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
229940043265 methyl isobutyl ketone Drugs 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
RJIQRRVMKNNZPE-UHFFFAOYSA-N 2-nitro-4-(trifluoromethoxy)benzonitrile Chemical compound [O-][N+](=O)C1=CC(OC(F)(F)F)=CC=C1C#N RJIQRRVMKNNZPE-UHFFFAOYSA-N 0.000 description 2
KDWOWCBQAGEUCF-UHFFFAOYSA-N 2-nitro-4-(trifluoromethoxy)benzoyl chloride Chemical compound [O-][N+](=O)C1=CC(OC(F)(F)F)=CC=C1C(Cl)=O KDWOWCBQAGEUCF-UHFFFAOYSA-N 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
229910000318 alkali metal phosphate Inorganic materials 0.000 description 2
230000000843 anti-fungal effect Effects 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
UZLYNDVQAFMVEP-UHFFFAOYSA-N (2,6,6-trimethyl-3-oxooxazin-5-yl) 2-nitro-4-(trifluoromethoxy)benzoate Chemical compound O=C1N(C)OC(C)(C)C(OC(=O)C=2C(=CC(OC(F)(F)F)=CC=2)[N+]([O-])=O)=C1 UZLYNDVQAFMVEP-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
NMNYJDXGMIUETI-UHFFFAOYSA-N 2,6,6-trimethyl-4-[2-nitro-4-(trifluoromethoxy)benzoyl]oxazinane-3,5-dione Chemical compound O=C1N(C)OC(C)(C)C(=O)C1C(=O)C1=CC=C(OC(F)(F)F)C=C1[N+]([O-])=O NMNYJDXGMIUETI-UHFFFAOYSA-N 0.000 description 1
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
YCGFVAPIBALHRT-UHFFFAOYSA-N 2-nitro-4-(trifluoromethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)F)C=C1[N+]([O-])=O YCGFVAPIBALHRT-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
CWVZGJORVTZXFW-UHFFFAOYSA-N [benzyl(dimethyl)silyl]methyl carbamate Chemical compound NC(=O)OC[Si](C)(C)CC1=CC=CC=C1 CWVZGJORVTZXFW-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
230000004075 alteration Effects 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
ACFWNPRMLAECCX-UHFFFAOYSA-N formonitrile propan-2-one Chemical compound N#C.CC(C)=O ACFWNPRMLAECCX-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)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
235000014666 liquid concentrate Nutrition 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
230000000051 modifying effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/02—1,2-Oxazines; Hydrogenated 1,2-oxazines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

HU922107A 1990-10-25 1991-10-23 3,5-dioxo-3,4,5,6-tetrahydro-1,2-oxazine derivatives, herbicidal, acaricidal and plant growth regulating composition comprising such compounds as active ingredient, process for applying the composition and for producing the active ingredients, as well as 2-nitro-4-(trifluoromethoxy)-benzoic acid intermediate HUT61534A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US60470890A	1990-10-25	1990-10-25

Publications (2)

Publication Number	Publication Date
HU9202107D0 HU9202107D0 (en)	1992-10-28
HUT61534A true HUT61534A (en)	1993-01-28

Family

ID=24420699

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU922107A HUT61534A (en)	1990-10-25	1991-10-23	3,5-dioxo-3,4,5,6-tetrahydro-1,2-oxazine derivatives, herbicidal, acaricidal and plant growth regulating composition comprising such compounds as active ingredient, process for applying the composition and for producing the active ingredients, as well as 2-nitro-4-(trifluoromethoxy)-benzoic acid intermediate

Country Status (12)

Country	Link
EP (1)	EP0506907A1 (cs)
JP (1)	JPH05503106A (cs)
KR (1)	KR927003554A (cs)
AU (1)	AU642052B2 (cs)
BR (1)	BR9106194A (cs)
CA (1)	CA2072134A1 (cs)
CS (1)	CS193492A3 (cs)
HU (1)	HUT61534A (cs)
IL (1)	IL99834A0 (cs)
PL (1)	PL295411A1 (cs)
WO (1)	WO1992007837A1 (cs)
ZA (1)	ZA918535B (cs)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5716901A (en) *	1993-02-18	1998-02-10	Sandoz Ltd.	Synergistic herbicidal compositions of dimethenamid, sulcotrione, and atrazine
US5888935A (en) *	1993-02-18	1999-03-30	Sandoz Ltd.	Synergistic herbicidal compositions of dimethenamid and glyphosate
EP2272341A3 (en)	1993-02-18	2011-02-16	Basf Se	Herbizide Zusammensetzungen
AU2001242451A1 (en) *	2000-03-09	2001-09-17	Syngenta Participations Ag	Acylated phenyl or pyridine herbicides
GT200100103A (es)	2000-06-09	2002-02-21		Nuevos herbicidas
DE10117503A1 (de)	2001-04-07	2002-10-17	Bayer Cropscience Gmbh	Derivate von Benzoylcyclohexandionen und ihre Verwendung als Herbizide
WO2003011298A1 (en) *	2001-08-03	2003-02-13	Chirologix Pharmaceuticals Inc.	Antibacterial oxazinones and methods for their use and synthesis
DE10144529A1 (de) *	2001-09-11	2003-03-27	Bayer Cropscience Gmbh	3-Aminocarbonyl substituierte Benzoylcyclohexandione
DE10160007A1 (de)	2001-12-06	2003-06-18	Bayer Cropscience Ag	[1.2]-Oxazin-3,5-dione
DE10215723A1 (de)	2002-04-10	2003-10-30	Bayer Cropscience Gmbh	3-Keto oder 3-Oximether substituierte Benzoylcyclohexandione
ES2632567T3 (es)	2009-03-11	2017-09-14	Bayer Intellectual Property Gmbh	Cetoenoles sustituidos con haloalquilmetilenoxi-fenilo
DE102010008644A1 (de)	2010-02-15	2011-08-18	Bayer Schering Pharma Aktiengesellschaft, 13353	Zyklische Ketoenole zur Therapie
DK2806741T3 (da)	2012-01-26	2020-05-18	Bayer Ip Gmbh	Phenylsubstituerede ketoenoler til bekæmpelse af fiskeparasitter

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0090262B1 (en) *	1982-03-25	1992-08-05	Stauffer Chemical Company	Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones
IL77350A (en) *	1984-12-20	1991-01-31	Stauffer Chemical Co	Production of acylated diketonic compounds
TR24452A (tr) *	1989-04-25	1991-11-01	Sandoz Ltd	Pestisidler ve bitki bueyueme duezenleyicileri olarak heterosiklik dionlar

1991
- 1991-10-23 BR BR919106194A patent/BR9106194A/pt unknown
- 1991-10-23 AU AU87442/91A patent/AU642052B2/en not_active Ceased
- 1991-10-23 PL PL29541191A patent/PL295411A1/xx unknown
- 1991-10-23 EP EP91918021A patent/EP0506907A1/en not_active Withdrawn
- 1991-10-23 WO PCT/EP1991/002014 patent/WO1992007837A1/en not_active Ceased
- 1991-10-23 JP JP3517054A patent/JPH05503106A/ja active Pending
- 1991-10-23 IL IL99834A patent/IL99834A0/xx unknown
- 1991-10-23 KR KR1019920701501A patent/KR927003554A/ko not_active Withdrawn
- 1991-10-23 CA CA002072134A patent/CA2072134A1/en not_active Abandoned
- 1991-10-23 HU HU922107A patent/HUT61534A/hu unknown
- 1991-10-25 ZA ZA918535A patent/ZA918535B/xx unknown
1992
- 1992-06-23 CS CS921934A patent/CS193492A3/cs unknown

Also Published As

Publication number	Publication date
CS193492A3 (en)	1992-10-14
ZA918535B (en)	1993-04-26
CA2072134A1 (en)	1992-04-26
EP0506907A1 (en)	1992-10-07
KR927003554A (ko)	1992-12-18
AU642052B2 (en)	1993-10-07
PL295411A1 (en)	1993-06-28
HU9202107D0 (en)	1992-10-28
BR9106194A (pt)	1993-03-23
WO1992007837A1 (en)	1992-05-14
IL99834A0 (en)	1992-08-18
AU8744291A (en)	1992-05-26
JPH05503106A (ja)	1993-05-27

Legal Events

Date	Code	Title	Description
1995-04-28	DFC4	Cancellation of temporary protection due to refusal

Publication	Publication Date	Title
KR960012178B1 (ko)	1996-09-16	피리미딘 유도체, 그의 제조방법, 제초방법 및 제초조성물
HU206242B (en)	1992-10-28	Herbicidal compositions comprising substituted benzoyl bicyclodione derivatives as active ingredient
CS197236B2 (en)	1980-04-30	Herbicide means and method of preparation of active component
EP0394889B1 (en)	1994-08-03	Heterocyclic diones as pesticides and plant growth regulators
US5801120A (en)	1998-09-01	Substituted benzoyl (hetero) cyclic diones
HUT61534A (en)	1993-01-28	3,5-dioxo-3,4,5,6-tetrahydro-1,2-oxazine derivatives, herbicidal, acaricidal and plant growth regulating composition comprising such compounds as active ingredient, process for applying the composition and for producing the active ingredients, as well as 2-nitro-4-(trifluoromethoxy)-benzoic acid intermediate
US5178663A (en)	1993-01-12	3-alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same
US5728831A (en)	1998-03-17	Process for preparing oxazines
EP0046467B1 (en)	1985-03-27	Quinoxaline derivatives and herbicidal composition
RO110333B1 (ro)	1995-12-29	Derivati 2(-benzoil-2`,3`,4`-trisubstituit)-1,3-ciclohexandione, compozitie erbicida, continindu-i si metoda pentru controlul vegetatiei nedorite
US4921526A (en)	1990-05-01	Substituted bicycloakly-1,3-diones
GB2205316A (en)	1988-12-07	Herbicidal benzoyl pyran, thiopyran or piperidine compounds
JPS60109578A (ja)	1985-06-15	３−（置換フエニル）−５−置換−１，３，４−オキサゾリン−２−オン類およびこれを有効成分とする除草剤
EP0427445B1 (en)	1994-06-08	Benzylideneaminoxyalkanoic acid (thio) amide derivative, process for preparing the same and herbicide
JPH05246998A (ja)	1993-09-24	アリールインダゾール誘導体およびそれを有効成分とする除草剤
JPH0678339B2 (ja)	1994-10-05	縮合ヘテロ環誘導体
JP2809481B2 (ja)	1998-10-08	２―アルコキシカルボニル―３―ピリジンカルボン酸誘導体、その製造法及び除草剤
KR100745205B1 (ko)	2007-08-02	6-(1-플루오로에틸)-5-요오도-4-아미노피리미딘 화합물, 그 제조 방법 및 농원예용 방제제
US4528145A (en)	1985-07-09	Herbicidal N-substituted-5(substituted-phenoxy)-2-substituted benzoic acid sulfamidoyl fluoride
JPH03200772A (ja)	1991-09-02	アルカン酸アミド誘導体及び除草剤
JPS62106084A (ja)	1987-05-16	農園芸用殺菌剤
JPH02270867A (ja)	1990-11-05	２，３‐ジヒドロベンゾフラン誘導体及びこれらを有効成分とする除草剤
JPH04235178A (ja)	1992-08-24	２，３−ジヒドロベンゾフラン誘導体およびこれらを有効成分とする除草剤