HRP960292A2 - Herbicides - Google Patents
Herbicides Download PDFInfo
- Publication number
- HRP960292A2 HRP960292A2 HR9512819.5A HRP960292A HRP960292A2 HR P960292 A2 HRP960292 A2 HR P960292A2 HR P960292 A HRP960292 A HR P960292A HR P960292 A2 HRP960292 A2 HR P960292A2
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- oxazin
- oxo
- dihydro
- methylpropanamide
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 249
- 239000000203 mixture Substances 0.000 claims description 105
- 241000196324 Embryophyta Species 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- -1 methoxy, ethoxy Chemical group 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 230000002363 herbicidal effect Effects 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 20
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- TZBHPYXJOJGKDT-UHFFFAOYSA-N 1,3-oxazin-4-one Chemical class O=C1C=COC=N1 TZBHPYXJOJGKDT-UHFFFAOYSA-N 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 239000012042 active reagent Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- KSIUCNSOWKVODE-UHFFFAOYSA-N 2-methyl-2-[6-(methylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1OC(CSC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 KSIUCNSOWKVODE-UHFFFAOYSA-N 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- HEEMJBYVERWPHT-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-(6-formyl-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(C=O)=C1C1=CC=CC=C1 HEEMJBYVERWPHT-UHFFFAOYSA-N 0.000 claims description 6
- UGFYHUFYEIYFIM-UHFFFAOYSA-N n-(3-chlorophenyl)-2-[6-(iodomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CI)=C1C1=CC=CC=C1 UGFYHUFYEIYFIM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 5
- PCCWCBPDOBKBSK-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-(6-hydroxyimino-2-methylidene-4-oxo-5-phenyl-1,3-oxazinan-3-yl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)C(=C)OC(=NO)C1C1=CC=CC=C1 PCCWCBPDOBKBSK-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 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 claims description 4
- WQWUHAZMDZVKJC-UHFFFAOYSA-N 2-[6-(bromomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CBr)=C1C1=CC=CC=C1 WQWUHAZMDZVKJC-UHFFFAOYSA-N 0.000 claims description 4
- PIFDMVNLNIREAS-UHFFFAOYSA-N 2-[6-(bromomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(3-chlorophenyl)-2-methylpropanamide Chemical compound C=1C=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CBr)=C1C1=CC=CC=C1 PIFDMVNLNIREAS-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- YKXRVTJQOPGEQR-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-methyl-2-[6-(methylhydrazinylidene)-2-methylidene-4-oxo-5-phenyl-1,3-oxazinan-3-yl]propanamide Chemical compound CNN=C1OC(=C)N(C(C)(C)C(=O)NC=2C=C(Cl)C=C(Cl)C=2)C(=O)C1C1=CC=CC=C1 YKXRVTJQOPGEQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000466 oxiranyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- XQDBPQIFMCYJGF-UHFFFAOYSA-N 2-(6-cyano-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl)-n-(3,5-dichlorophenyl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(C#N)=C1C1=CC=CC=C1 XQDBPQIFMCYJGF-UHFFFAOYSA-N 0.000 claims description 3
- XJXMXXABXUXBSK-UHFFFAOYSA-N 2-[6-(bromomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(2,5-difluorophenyl)-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CBr)=C1C1=CC=CC=C1 XJXMXXABXUXBSK-UHFFFAOYSA-N 0.000 claims description 3
- TUHHWKLRILIFOJ-UHFFFAOYSA-N 2-[6-(bromomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(3,5-dichlorophenyl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CBr)=C1C1=CC=CC=C1 TUHHWKLRILIFOJ-UHFFFAOYSA-N 0.000 claims description 3
- OJOMNJTZEGQQDZ-UHFFFAOYSA-N 2-[6-(chloromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(2,5-difluorophenyl)-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CCl)=C1C1=CC=CC=C1 OJOMNJTZEGQQDZ-UHFFFAOYSA-N 0.000 claims description 3
- YKUPREWGXSSXGF-UHFFFAOYSA-N 2-[6-(chloromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(3,5-dichlorophenyl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CCl)=C1C1=CC=CC=C1 YKUPREWGXSSXGF-UHFFFAOYSA-N 0.000 claims description 3
- IHQYQXFZSNTMMO-UHFFFAOYSA-N 2-[6-(ethoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1OC(COCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 IHQYQXFZSNTMMO-UHFFFAOYSA-N 0.000 claims description 3
- PSNSUMBKWVSHJX-UHFFFAOYSA-N 2-[6-(ethylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1OC(CSCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 PSNSUMBKWVSHJX-UHFFFAOYSA-N 0.000 claims description 3
- XEEMKXWKCHIXFY-UHFFFAOYSA-N 2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-(3,4,5-trifluorophenyl)propanamide Chemical compound C=1C(F)=C(F)C(F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 XEEMKXWKCHIXFY-UHFFFAOYSA-N 0.000 claims description 3
- NPFYNMHBCPTCHX-UHFFFAOYSA-N 2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 NPFYNMHBCPTCHX-UHFFFAOYSA-N 0.000 claims description 3
- JWBJENNNRLDCAO-UHFFFAOYSA-N 2-[6-(hydroxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CO)=C1C1=CC=CC=C1 JWBJENNNRLDCAO-UHFFFAOYSA-N 0.000 claims description 3
- VQSBPXZSMPVTIJ-UHFFFAOYSA-N 2-methyl-2-[6-(methylaminomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1OC(CNC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 VQSBPXZSMPVTIJ-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- YQTPBSBKVPFTBY-UHFFFAOYSA-N CON=C1OC(=C)N(C(C)(C)C(=O)NC=2C(=CC=C(F)C=2)F)C(=O)C1C1=CC=CC=C1 Chemical compound CON=C1OC(=C)N(C(C)(C)C(=O)NC=2C(=CC=C(F)C=2)F)C(=O)C1C1=CC=CC=C1 YQTPBSBKVPFTBY-UHFFFAOYSA-N 0.000 claims description 3
- DJSKNICCEPLERY-UHFFFAOYSA-N CON=C1OC(=C)N(C(C)(C)C(=O)NC=2C=C(Cl)C=C(Cl)C=2)C(=O)C1C1=CC=CC=C1 Chemical compound CON=C1OC(=C)N(C(C)(C)C(=O)NC=2C=C(Cl)C=C(Cl)C=2)C(=O)C1C1=CC=CC=C1 DJSKNICCEPLERY-UHFFFAOYSA-N 0.000 claims description 3
- ZSJDGADHIYIFIQ-UHFFFAOYSA-N ClC=1C=C(C=C(C1)Cl)NC(C(C)(C)N1COC(=C(C1=O)C1=CC=CC=C1)CSC)=O Chemical compound ClC=1C=C(C=C(C1)Cl)NC(C(C)(C)N1COC(=C(C1=O)C1=CC=CC=C1)CSC)=O ZSJDGADHIYIFIQ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- QRQZROXHSAPXAZ-UHFFFAOYSA-N [3-[1-(2,5-difluoroanilino)-2-methyl-1-oxopropan-2-yl]-4-oxo-5-phenyl-2h-1,3-oxazin-6-yl]methyl acetate Chemical compound C1OC(COC(=O)C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F QRQZROXHSAPXAZ-UHFFFAOYSA-N 0.000 claims description 3
- DNFYJFRQQUXIGS-UHFFFAOYSA-N [[3-[1-(3,5-dichloroanilino)-2-methyl-1-oxopropan-2-yl]-2-methylidene-4-oxo-5-phenyl-1,3-oxazinan-6-ylidene]amino] acetate Chemical compound CC(=O)ON=C1OC(=C)N(C(C)(C)C(=O)NC=2C=C(Cl)C=C(Cl)C=2)C(=O)C1C1=CC=CC=C1 DNFYJFRQQUXIGS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- ONDPUBOZVQKGTD-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-(6-formyl-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl)-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(C=O)=C1C1=CC=CC=C1 ONDPUBOZVQKGTD-UHFFFAOYSA-N 0.000 claims description 3
- DWBJLEPRQXCCEL-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-[6-(ethoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(COCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F DWBJLEPRQXCCEL-UHFFFAOYSA-N 0.000 claims description 3
- IUQITTWRHOZERH-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 IUQITTWRHOZERH-UHFFFAOYSA-N 0.000 claims description 3
- VRACOVDIVNRFIO-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-[6-(hydroxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CO)=C1C1=CC=CC=C1 VRACOVDIVNRFIO-UHFFFAOYSA-N 0.000 claims description 3
- UUJOYHYWOYUDCG-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-[6-(methoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(COC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F UUJOYHYWOYUDCG-UHFFFAOYSA-N 0.000 claims description 3
- YGUKMKLDQDYULW-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-methyl-2-[6-(methylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]propanamide Chemical compound C1OC(CSC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F YGUKMKLDQDYULW-UHFFFAOYSA-N 0.000 claims description 3
- MYRRPZUXVDLKSJ-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-methyl-2-[6-(methylsulfonylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]propanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CS(C)(=O)=O)=C1C1=CC=CC=C1 MYRRPZUXVDLKSJ-UHFFFAOYSA-N 0.000 claims description 3
- VCUXVHZZUHODAF-UHFFFAOYSA-N n-(2-chloro-3,5-difluorophenyl)-2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(F)=CC(F)=C(Cl)C=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 VCUXVHZZUHODAF-UHFFFAOYSA-N 0.000 claims description 3
- DXZRXAYVEISCHD-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(ethoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(COCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 DXZRXAYVEISCHD-UHFFFAOYSA-N 0.000 claims description 3
- XQLMLOYTBSHFIP-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(ethylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(CSCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 XQLMLOYTBSHFIP-UHFFFAOYSA-N 0.000 claims description 3
- DMLYNNBAELXOAI-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 DMLYNNBAELXOAI-UHFFFAOYSA-N 0.000 claims description 3
- BXIUMGYZZUMBKF-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(hydroxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CO)=C1C1=CC=CC=C1 BXIUMGYZZUMBKF-UHFFFAOYSA-N 0.000 claims description 3
- BJVBZMHLEXQBJC-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(methoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(COC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 BJVBZMHLEXQBJC-UHFFFAOYSA-N 0.000 claims description 3
- CONBQCNTXNVXRL-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-[(dimethylamino)methyl]-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(CN(C)C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 CONBQCNTXNVXRL-UHFFFAOYSA-N 0.000 claims description 3
- NUFLKLBNNMZVIW-UHFFFAOYSA-N n-(3,5-difluorophenyl)-2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(F)=CC(F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 NUFLKLBNNMZVIW-UHFFFAOYSA-N 0.000 claims description 3
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- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- NXRYUCYUXQCUPD-UHFFFAOYSA-N ethyl 2-(6-cyclopropyl-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl)-2-methylpropanoate Chemical compound C=1C=CC=CC=1C=1C(=O)N(C(C)(C)C(=O)OCC)COC=1C1CC1 NXRYUCYUXQCUPD-UHFFFAOYSA-N 0.000 description 1
- YREPHXXOTHNLEV-UHFFFAOYSA-N ethyl 2-amino-2-methylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(C)(C)N YREPHXXOTHNLEV-UHFFFAOYSA-N 0.000 description 1
- KFSKMRRJYCRSSC-UHFFFAOYSA-N ethyl 2-methyl-2-(6-methyl-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl)propanoate Chemical compound O=C1N(C(C)(C)C(=O)OCC)COC(C)=C1C1=CC=CC=C1 KFSKMRRJYCRSSC-UHFFFAOYSA-N 0.000 description 1
- ZZDVCYRTIWVOGM-UHFFFAOYSA-N ethyl 2-methyl-2-[6-(methylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]propanoate Chemical compound O=C1N(C(C)(C)C(=O)OCC)COC(CSC)=C1C1=CC=CC=C1 ZZDVCYRTIWVOGM-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012493 hydrazine sulfate Substances 0.000 description 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 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
- 239000010410 layer Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- IKEPNVAJOHDSLU-UHFFFAOYSA-N methyl 3-cyclopropyl-3-oxo-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C(=O)C1CC1 IKEPNVAJOHDSLU-UHFFFAOYSA-N 0.000 description 1
- BAZZERBWEWNHPP-UHFFFAOYSA-N methyl n-(1-butyl-4-carbamoylbenzimidazol-2-yl)carbamate Chemical compound C1=CC=C2N(CCCC)C(NC(=O)OC)=NC2=C1C(N)=O BAZZERBWEWNHPP-UHFFFAOYSA-N 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SMBBZHGTZJNSRQ-UHFFFAOYSA-N n'-(6,6-dichlorohexyl)methanediimine Chemical compound ClC(Cl)CCCCCN=C=N SMBBZHGTZJNSRQ-UHFFFAOYSA-N 0.000 description 1
- OTUFWCOPVDVASG-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-methyl-2-[6-(methylsulfinylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]propanamide Chemical compound C1OC(CS(=O)C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F OTUFWCOPVDVASG-UHFFFAOYSA-N 0.000 description 1
- NTPMSMBPOKDKEW-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-methyl-2-[6-(methylaminomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]propanamide Chemical compound C1OC(CNC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 NTPMSMBPOKDKEW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SLVXVMRPJIFKCE-UHFFFAOYSA-N tert-butyl 2-[6-(hydroxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanoate Chemical compound O=C1N(C(C)(C)C(=O)OC(C)(C)C)COC(CO)=C1C1=CC=CC=C1 SLVXVMRPJIFKCE-UHFFFAOYSA-N 0.000 description 1
- SQVOSXZZUXIFBY-UHFFFAOYSA-N tert-butyl 2-methyl-2-(methylideneamino)propanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)N=C SQVOSXZZUXIFBY-UHFFFAOYSA-N 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
-
- 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
- A01N43/86—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9512819.5A GB9512819D0 (en) | 1995-06-23 | 1995-06-23 | Herbicides |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP960292A2 true HRP960292A2 (en) | 1998-02-28 |
Family
ID=10776564
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR9512819.5A HRP960292A2 (en) | 1995-06-23 | 1996-06-19 | Herbicides |
Country Status (23)
Country | Link |
---|---|
US (1) | US6028032A (xx) |
EP (1) | EP0833821A1 (xx) |
JP (1) | JPH11507932A (xx) |
KR (1) | KR19990028369A (xx) |
CN (1) | CN1066443C (xx) |
AR (1) | AR002550A1 (xx) |
AU (1) | AU708121B2 (xx) |
BG (1) | BG102147A (xx) |
BR (1) | BR9609675A (xx) |
CA (1) | CA2225603A1 (xx) |
CZ (1) | CZ418097A3 (xx) |
EA (1) | EA001145B1 (xx) |
GB (1) | GB9512819D0 (xx) |
HR (1) | HRP960292A2 (xx) |
HU (1) | HUP9901329A3 (xx) |
IL (1) | IL122721A0 (xx) |
MX (1) | MX9800122A (xx) |
NZ (1) | NZ312112A (xx) |
PL (1) | PL324400A1 (xx) |
SK (1) | SK177497A3 (xx) |
TR (1) | TR199701680T1 (xx) |
WO (1) | WO1997000865A1 (xx) |
ZA (1) | ZA965192B (xx) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9608399D0 (en) * | 1996-04-23 | 1996-06-26 | Mitsubishi Chemical Company | New Herbicides |
NZ334028A (en) * | 1996-08-05 | 2000-11-24 | Bayer Ag | 1-heterocyclic substituted 2- and 2,5-substituted phenylketoenol derivatives |
PT102162B (pt) * | 1997-06-10 | 2001-05-31 | Rhone Poulenc Agriculture | Herbicidas |
GB9818666D0 (en) * | 1998-08-27 | 1998-10-21 | Rhone Poulenc Agriculture | New herbicidal method |
UA119648C2 (uk) | 2013-09-11 | 2019-07-25 | Сінгента Партісіпейшнс Аг | Гетероциклічна амідна сполука й гербіцид |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2144455T3 (es) * | 1992-01-30 | 2000-06-16 | Mitsubishi Chem Corp | Derivado de 1,3-oxazin-4-ona, herbicida que lo contiene, e intermedio nuevo para producirlo. |
JPH07112976A (ja) * | 1993-10-14 | 1995-05-02 | Mitsubishi Chem Corp | 1,3−オキサジン−4−オン誘導体及びそれを有効成分とする除草剤、並びにその製造中間体 |
IL112014A (en) * | 1993-12-24 | 1999-10-28 | Rhone Poulenc Agrochimie | 1,3-Oxazin-4-one derivatives and herbicides containing the same |
JPH08151364A (ja) * | 1994-02-18 | 1996-06-11 | Nissan Chem Ind Ltd | 含窒素環状化合物および除草剤 |
-
1995
- 1995-06-23 GB GBGB9512819.5A patent/GB9512819D0/en active Pending
-
1996
- 1996-06-18 WO PCT/EP1996/002616 patent/WO1997000865A1/en not_active Application Discontinuation
- 1996-06-18 AU AU63565/96A patent/AU708121B2/en not_active Ceased
- 1996-06-18 CA CA002225603A patent/CA2225603A1/en not_active Abandoned
- 1996-06-18 KR KR1019970709685A patent/KR19990028369A/ko not_active Application Discontinuation
- 1996-06-18 BR BR9609675A patent/BR9609675A/pt unknown
- 1996-06-18 TR TR97/01680T patent/TR199701680T1/xx unknown
- 1996-06-18 SK SK1774-97A patent/SK177497A3/sk unknown
- 1996-06-18 CN CN96196424A patent/CN1066443C/zh not_active Expired - Fee Related
- 1996-06-18 NZ NZ312112A patent/NZ312112A/en unknown
- 1996-06-18 PL PL96324400A patent/PL324400A1/xx unknown
- 1996-06-18 IL IL12272196A patent/IL122721A0/xx unknown
- 1996-06-18 EP EP96922822A patent/EP0833821A1/en not_active Ceased
- 1996-06-18 US US08/981,569 patent/US6028032A/en not_active Expired - Fee Related
- 1996-06-18 HU HU9901329A patent/HUP9901329A3/hu unknown
- 1996-06-18 EA EA199800083A patent/EA001145B1/ru not_active IP Right Cessation
- 1996-06-18 CZ CZ974180A patent/CZ418097A3/cs unknown
- 1996-06-18 MX MX9800122A patent/MX9800122A/es not_active IP Right Cessation
- 1996-06-18 JP JP9503564A patent/JPH11507932A/ja active Pending
- 1996-06-19 ZA ZA9605192A patent/ZA965192B/xx unknown
- 1996-06-19 HR HR9512819.5A patent/HRP960292A2/hr not_active Application Discontinuation
- 1996-06-21 AR ARP960103255A patent/AR002550A1/es unknown
-
1997
- 1997-12-23 BG BG102147A patent/BG102147A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
AR002550A1 (es) | 1998-03-25 |
EA001145B1 (ru) | 2000-10-30 |
US6028032A (en) | 2000-02-22 |
KR19990028369A (ko) | 1999-04-15 |
EA199800083A1 (ru) | 1998-08-27 |
IL122721A0 (en) | 1998-08-16 |
AU708121B2 (en) | 1999-07-29 |
NZ312112A (en) | 1999-09-29 |
CZ418097A3 (cs) | 1998-07-15 |
EP0833821A1 (en) | 1998-04-08 |
PL324400A1 (en) | 1998-05-25 |
TR199701680T1 (xx) | 1998-05-21 |
CA2225603A1 (en) | 1997-01-09 |
HUP9901329A3 (en) | 2000-12-28 |
MX9800122A (es) | 1998-04-30 |
BR9609675A (pt) | 1999-07-06 |
CN1066443C (zh) | 2001-05-30 |
HUP9901329A2 (hu) | 1999-08-30 |
SK177497A3 (en) | 1998-08-05 |
CN1193970A (zh) | 1998-09-23 |
GB9512819D0 (en) | 1995-08-23 |
BG102147A (en) | 1998-08-31 |
ZA965192B (en) | 1997-02-03 |
JPH11507932A (ja) | 1999-07-13 |
AU6356596A (en) | 1997-01-22 |
WO1997000865A1 (en) | 1997-01-09 |
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