CS270206B2 - Herbicide - Google Patents
Herbicide Download PDFInfo
- Publication number
- CS270206B2 CS270206B2 CS859551A CS955185A CS270206B2 CS 270206 B2 CS270206 B2 CS 270206B2 CS 859551 A CS859551 A CS 859551A CS 955185 A CS955185 A CS 955185A CS 270206 B2 CS270206 B2 CS 270206B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- align
- alkyl
- formula
- methyl
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 21
- 230000002363 herbicidal effect Effects 0.000 title claims description 59
- 239000001257 hydrogen Substances 0.000 claims abstract description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 128
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 62
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 11
- 239000000203 mixture Substances 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- -1 chloro, fluoro, bromo, methyl Chemical group 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 24
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 48
- 235000019198 oils Nutrition 0.000 description 48
- 239000008188 pellet Substances 0.000 description 34
- 241000196324 Embryophyta Species 0.000 description 26
- 238000012360 testing method Methods 0.000 description 21
- 239000002585 base Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 231100000208 phytotoxic Toxicity 0.000 description 6
- 230000000885 phytotoxic effect Effects 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003440 toxic substance Substances 0.000 description 5
- 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 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 231100000167 toxic agent Toxicity 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZZJZBPYZTKGWTD-UHFFFAOYSA-N 2-(2-nitrobenzoyl)cyclohexane-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C1C(=O)CCCC1=O ZZJZBPYZTKGWTD-UHFFFAOYSA-N 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical group CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-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
- QLLNXSNPTUSROU-UHFFFAOYSA-N 2-chloro-4-n-ethyl-6-n-propan-2-yl-1h-triazine-4,6-diamine Chemical compound CCNC1=NN(Cl)NC(NC(C)C)=C1 QLLNXSNPTUSROU-UHFFFAOYSA-N 0.000 description 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
- FBMDQVBGIYSDTI-UHFFFAOYSA-N 2-n,4-n-bis(3-methoxypropyl)-6-methylsulfanyl-1,3,5-triazine-2,4-diamine Chemical compound COCCCNC1=NC(NCCCOC)=NC(SC)=N1 FBMDQVBGIYSDTI-UHFFFAOYSA-N 0.000 description 1
- NAOCHJCREOAPOF-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 NAOCHJCREOAPOF-UHFFFAOYSA-N 0.000 description 1
- VMWMKRZFRQQQGV-UHFFFAOYSA-N 3-butoxy-n-phenylpropanamide Chemical compound CCCCOCCC(=O)NC1=CC=CC=C1 VMWMKRZFRQQQGV-UHFFFAOYSA-N 0.000 description 1
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
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- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
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- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
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- 150000003983 crown ethers Chemical group 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000011088 parchment paper Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LCHWKMAWSZDQRD-UHFFFAOYSA-N silylformonitrile Chemical class [SiH3]C#N LCHWKMAWSZDQRD-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 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
- 229960000278 theophylline Drugs 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 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
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68390084A | 1984-12-20 | 1984-12-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS955185A2 CS955185A2 (en) | 1989-10-13 |
| CS270206B2 true CS270206B2 (en) | 1990-06-13 |
Family
ID=24745917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS859551A CS270206B2 (en) | 1984-12-20 | 1985-12-19 | Herbicide |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP0186118B1 (OSRAM) |
| JP (1) | JPH0723347B2 (OSRAM) |
| KR (1) | KR900006759B1 (OSRAM) |
| CN (2) | CN1015044B (OSRAM) |
| AR (1) | AR240794A1 (OSRAM) |
| AT (1) | ATE52495T1 (OSRAM) |
| AU (1) | AU585917B2 (OSRAM) |
| BG (2) | BG46454A3 (OSRAM) |
| BR (1) | BR8506425A (OSRAM) |
| CA (1) | CA1314558C (OSRAM) |
| CS (1) | CS270206B2 (OSRAM) |
| DD (1) | DD247210A5 (OSRAM) |
| DE (1) | DE3577547D1 (OSRAM) |
| DK (1) | DK174478B1 (OSRAM) |
| ES (1) | ES8704444A1 (OSRAM) |
| FI (1) | FI84815C (OSRAM) |
| GR (1) | GR853113B (OSRAM) |
| HU (1) | HU197170B (OSRAM) |
| IE (1) | IE58400B1 (OSRAM) |
| IL (1) | IL77349A (OSRAM) |
| MY (1) | MY102051A (OSRAM) |
| NL (1) | NL350003I2 (OSRAM) |
| NO (1) | NO162663C (OSRAM) |
| NZ (1) | NZ214631A (OSRAM) |
| PH (1) | PH21518A (OSRAM) |
| PL (2) | PL256983A1 (OSRAM) |
| PT (1) | PT81733B (OSRAM) |
| RO (2) | RO92905A (OSRAM) |
| SU (1) | SU1715190A3 (OSRAM) |
| TR (1) | TR22573A (OSRAM) |
| YU (1) | YU44906B (OSRAM) |
| ZA (1) | ZA859736B (OSRAM) |
| ZW (1) | ZW23685A1 (OSRAM) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR22585A (tr) * | 1984-12-20 | 1987-12-07 | Stauffer Chemical Co | Bazi 2-(2'-alkilbenzoil)-1,3-sikloheksandion'lar |
| IL77348A (en) * | 1984-12-20 | 1991-05-12 | Stauffer Chemical Co | 2-(2'-substituted benzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
| IL77350A (en) * | 1984-12-20 | 1991-01-31 | Stauffer Chemical Co | Production of acylated diketonic compounds |
| DE3604871A1 (de) * | 1986-02-15 | 1987-08-20 | Basf Ag | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung als mittel zur regulierung des pflanzenwachstums |
| US4775411A (en) * | 1986-06-09 | 1988-10-04 | Stauffer Chemica Company | Certain substituted 3-amino-2-benzoylcyclohex-2-enones |
| US4783213A (en) * | 1986-10-16 | 1988-11-08 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones |
| KR890003680A (ko) * | 1986-10-16 | 1989-04-17 | 죤 알.페넬 | 2-(2-치환 벤조일)-4-(치환)-1,3-시클로헥산디온 및 그 제조방법과 이를 이용한 조성물 및 식물체의 억제방법 |
| US4838932A (en) * | 1987-08-20 | 1989-06-13 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted imino, oximino or carbonyl)-1,3-cyclohexanediones |
| EP0274634A1 (en) * | 1986-12-04 | 1988-07-20 | Stauffer Chemical Company | Synergistic herbicide compositions and method of application |
| US4774360A (en) * | 1987-06-29 | 1988-09-27 | Stauffer Chemical Company | Converting enol ester precursor of a benzoyl-1,3-cycloalkyldione to a benzoyl-1,3-cycloalkyldione |
| US4938796A (en) * | 1987-07-06 | 1990-07-03 | Ici Americas Inc. | Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor |
| US4859234A (en) * | 1987-09-14 | 1989-08-22 | Ici Americas Inc. | Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and phenoxyalkanoic acids, salts, amides and esters therof as antidotes |
| HUT50312A (en) * | 1988-02-01 | 1990-01-29 | Sandoz Ag | Herbicide composition containing new dion-compounds and process for producing these compounds |
| HU202851B (en) * | 1988-04-04 | 1991-04-29 | Sandoz Ag | Herbicidal or acaricidal compositions and process for producing the active ingredient aryldione derivatives |
| US5089046A (en) * | 1988-04-04 | 1992-02-18 | Sandoz Ltd. | Aryl and heteroaryl diones |
| DK184489A (da) * | 1988-04-18 | 1989-10-19 | Sandoz Ag | Bicyclodioner |
| JPH0219355A (ja) * | 1988-07-07 | 1990-01-23 | Nippon Soda Co Ltd | ４，４，５−トリメチル−２−（２−ニトロ−４−メチルスルホニルベンゾイル）シクロヘキサン−１，３−ジオン、その製造方法及び除草剤 |
| ZA904951B (en) | 1989-07-04 | 1991-05-29 | Nippon Soda Co Limited | Substituted bicycloheptandione derivatives |
| WO1991005469A2 (de) * | 1989-10-18 | 1991-05-02 | Hoechst Aktiengesellschaft | Herbizide wirkstoffkombinationen |
| JPH0774126B2 (ja) * | 1989-10-18 | 1995-08-09 | ヘキスト・アクチェンゲゼルシャフト | イネにおける有害植物の防除方法 |
| US5306695A (en) * | 1991-03-06 | 1994-04-26 | Hoechst Aktiengesellschaft | Haloalkoxy-substituted benzoylcyclohexanediones as herbicides and plant growth regulators |
| GB9108199D0 (en) * | 1991-04-17 | 1991-06-05 | Rhone Poulenc Agriculture | New compositions of matter |
| DE122005000032I2 (de) * | 1991-06-24 | 2006-06-08 | Syngenta Ltd | Verwendung von 2-(2-Nitro-4-Trifluormethylbenzoyl)-1,3-Cyclohexandion zur Behandlung von Tyrosin{miesowie Pharmazeutische Zusammensetzungen |
| EP0563817A3 (en) * | 1992-03-31 | 1993-11-03 | Hoechst Ag | Salts of 2-benzoyl-cyclohexane diones, selective herbicidal agents, process for their preparation and their use for combatting weeds |
| US5716901A (en) * | 1993-02-18 | 1998-02-10 | Sandoz Ltd. | Synergistic herbicidal compositions of dimethenamid, sulcotrione, and atrazine |
| PT2272342E (pt) | 1993-02-18 | 2012-07-24 | Basf Se | Composições herbicidas |
| US5895773A (en) * | 1993-02-18 | 1999-04-20 | Fenderson; John M. | Herbicidal compositions comprising dimethenamid and a pyridazinone herbicide |
| IL113138A (en) * | 1994-04-22 | 1999-05-09 | Zeneca Ltd | Herbicidal composition comprising a substituted 1, 3-cyclohexanedione compound and a 2-chloro-4- ethylamino-6- isopropylamino-s- triazine and a method of use thereof |
| DE4427995A1 (de) * | 1994-08-08 | 1996-02-15 | Basf Ag | Saccharinderivate |
| US5506195A (en) * | 1994-11-01 | 1996-04-09 | Zeneca Limited | Selective 1,3-cyclohexanedione corn herbicide |
| GB9501434D0 (en) * | 1995-01-25 | 1995-03-15 | Zeneca Ltd | Chemical process |
| EA001321B1 (ru) * | 1995-02-24 | 2001-02-26 | Басф Акциенгезельшафт | Производные бензоила, обладающие гербицидным действием |
| DE19532311A1 (de) * | 1995-09-01 | 1997-03-06 | Basf Ag | Benzoylderivate |
| CA2247167C (en) * | 1996-02-24 | 2005-07-12 | Basf Aktiengesellschaft | 2-hetaroylcyclohexane-1,3-diones |
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| CN100447718C (zh) * | 2005-12-23 | 2008-12-31 | 联想(北京)有限公司 | 一种数字设备的输入键盘 |
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| EP2545774A1 (en) | 2011-07-12 | 2013-01-16 | Cheminova A/S | Aqueous HPPD inhibitor suspension concentrate compositions comprising smectite clay |
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| CN102948423A (zh) * | 2012-11-12 | 2013-03-06 | 辽宁海佳农化有限公司 | 一种含甲基磺草酮、特丁津的除草剂组合物及制法 |
| WO2015054887A1 (zh) * | 2013-10-18 | 2015-04-23 | 浙江省诸暨合力化学对外贸易有限公司 | 三酮类铵盐化合物及其制备方法及应用 |
| CN106912487A (zh) * | 2017-04-27 | 2017-07-04 | 江苏辉丰农化股份有限公司 | 具有增效作用的除草组合物 |
| CN108947985A (zh) * | 2017-05-22 | 2018-12-07 | 苏州偶领生物医药有限公司 | 用作自噬调节剂的化合物及其制备方法和用途 |
| CN110078647B (zh) * | 2019-05-15 | 2021-04-13 | 北京颖泰嘉和生物科技股份有限公司 | 一种硝磺草酮反应产物的后处理方法 |
| WO2024023035A1 (en) | 2022-07-25 | 2024-02-01 | Syngenta Crop Protection Ag | Herbicidal compositions |
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| WO2025016884A1 (en) | 2023-07-20 | 2025-01-23 | Syngenta Crop Protection Ag | Herbicidal compositions |
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| US4175135A (en) * | 1978-07-18 | 1979-11-20 | Union Carbide Corporation | Method of controlling acarina ectoparasites on warmblooded animals by orally administering to the animal an ectoparasitically effective amount of a 2-aryl-1,3-cyclohexanedione compound, and alkali metal salts, ammonium salts and enol esters thereof |
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| EP0137963B1 (en) * | 1983-09-16 | 1988-09-28 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
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| IL77348A (en) * | 1984-12-20 | 1991-05-12 | Stauffer Chemical Co | 2-(2'-substituted benzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
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1985
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- 1985-12-17 AU AU51336/85A patent/AU585917B2/en not_active Expired
- 1985-12-18 DE DE8585116162T patent/DE3577547D1/de not_active Expired - Lifetime
- 1985-12-18 AT AT85116162T patent/ATE52495T1/de active
- 1985-12-18 PH PH33208A patent/PH21518A/en unknown
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- 1985-12-18 AR AR302635A patent/AR240794A1/es active
- 1985-12-18 EP EP85116162A patent/EP0186118B1/en not_active Expired - Lifetime
- 1985-12-18 KR KR1019850009557A patent/KR900006759B1/ko not_active Expired
- 1985-12-19 CS CS859551A patent/CS270206B2/cs not_active IP Right Cessation
- 1985-12-19 CN CN85109771A patent/CN1015044B/zh not_active Expired
- 1985-12-19 DK DK198505948A patent/DK174478B1/da active IP Right Maintenance
- 1985-12-19 SU SU853995880A patent/SU1715190A3/ru active
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- 1985-12-19 ZW ZW236/85A patent/ZW23685A1/xx unknown
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- 1985-12-19 IE IE325585A patent/IE58400B1/en not_active IP Right Cessation
- 1985-12-19 HU HU854875A patent/HU197170B/hu active Protection Beyond IP Right Term
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- 1985-12-20 JP JP60287589A patent/JPH0723347B2/ja not_active Expired - Lifetime
- 1985-12-20 PL PL1985262569A patent/PL148140B1/pl unknown
- 1985-12-20 TR TR51031A patent/TR22573A/xx unknown
- 1985-12-20 RO RO85128089A patent/RO96552A7/ro unknown
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- 1985-12-20 GR GR853113A patent/GR853113B/el not_active IP Right Cessation
- 1985-12-20 YU YU2012/85A patent/YU44906B/xx unknown
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1986
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| Date | Code | Title | Description |
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| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20001219 |