WO1993010081A1 - Derives herbicides de 2(oxime substitue)-cyclohexane-1,3-dione - Google Patents
Derives herbicides de 2(oxime substitue)-cyclohexane-1,3-dione Download PDFInfo
- Publication number
- WO1993010081A1 WO1993010081A1 PCT/AU1992/000612 AU9200612W WO9310081A1 WO 1993010081 A1 WO1993010081 A1 WO 1993010081A1 AU 9200612 W AU9200612 W AU 9200612W WO 9310081 A1 WO9310081 A1 WO 9310081A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- group
- compounds
- formula
- optionally substituted
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims description 15
- 150000002923 oximes Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000004009 herbicide Substances 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 12
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 47
- -1 nitro, cyano, amino Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical group 0.000 claims description 24
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 23
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 15
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 14
- 241000196324 Embryophyta Species 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical group [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 230000008635 plant growth Effects 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- NDJUOOUVOLMJLY-UHFFFAOYSA-N 2-[1-[[4-(4-fluorophenyl)phenyl]methoxyamino]butylidene]-5,5-dimethylcyclohexane-1,3-dione Chemical compound O=C1CC(C)(C)CC(=O)C1=C(CCC)NOCC(C=C1)=CC=C1C1=CC=C(F)C=C1 NDJUOOUVOLMJLY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- CAJBMIBYINQAEH-UHFFFAOYSA-N 5,5-dimethyl-2-[1-[(4-phenylphenyl)methoxyamino]butylidene]cyclohexane-1,3-dione Chemical compound O=C1CC(C)(C)CC(=O)C1=C(CCC)NOCC(C=C1)=CC=C1C1=CC=CC=C1 CAJBMIBYINQAEH-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 241000209504 Poaceae Species 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- KJIOBICDOWPOMU-UHFFFAOYSA-N 2-[1-[[4-(4-fluorophenyl)phenyl]methoxyamino]butylidene]-5-propan-2-ylcyclohexane-1,3-dione Chemical compound O=C1CC(C(C)C)CC(=O)C1=C(CCC)NOCC(C=C1)=CC=C1C1=CC=C(F)C=C1 KJIOBICDOWPOMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000001963 growth medium Substances 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 64
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 48
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000003921 oil Substances 0.000 description 27
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 22
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 240000007594 Oryza sativa Species 0.000 description 11
- 235000007164 Oryza sativa Nutrition 0.000 description 11
- 235000009566 rice Nutrition 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241001148683 Zostera marina Species 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- PNCNFDRSHBFIDM-WOJGMQOQSA-N chembl111617 Chemical compound C=CCO\N=C(/CCC)C1=C(O)C(C(=O)OC)C(C)(C)CC1=O PNCNFDRSHBFIDM-WOJGMQOQSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- JSBJQQZPQJIGFJ-UHFFFAOYSA-N 1-fluoro-4-(4-methylphenyl)benzene Chemical compound C1=CC(C)=CC=C1C1=CC=C(F)C=C1 JSBJQQZPQJIGFJ-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- LYCAUXHKTHJGSM-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-phenylmethoxyisoindole-1,3-dione Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=C(OCC=3C=CC=CC=3)C=CC=C2C1=O LYCAUXHKTHJGSM-UHFFFAOYSA-N 0.000 description 2
- JYUSHNFOXUEQIH-UHFFFAOYSA-N 2-[(4-phenylphenyl)methoxy]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OCC(C=C1)=CC=C1C1=CC=CC=C1 JYUSHNFOXUEQIH-UHFFFAOYSA-N 0.000 description 2
- VAPNOYMBLCEKKH-UHFFFAOYSA-N 2-butanoyl-5,5-dimethylcyclohexane-1,3-dione Chemical compound CCCC(=O)C1C(=O)CC(C)(C)CC1=O VAPNOYMBLCEKKH-UHFFFAOYSA-N 0.000 description 2
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 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
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
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- 239000000284 extract Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 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 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- 229910052717 sulfur Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- AXCHZLOJGKSWLV-UHFFFAOYSA-N (4-phenylphenyl)methanol Chemical compound C1=CC(CO)=CC=C1C1=CC=CC=C1 AXCHZLOJGKSWLV-UHFFFAOYSA-N 0.000 description 1
- AZGSFFJSOZLRCY-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-methylcyclohexan-1-ol Chemical compound C1CC(C)CCC1(O)C1=CC=C(F)C=C1 AZGSFFJSOZLRCY-UHFFFAOYSA-N 0.000 description 1
- HLQZCRVEEQKNMS-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylbenzene Chemical compound C1=CC(CCl)=CC=C1C1=CC=CC=C1 HLQZCRVEEQKNMS-UHFFFAOYSA-N 0.000 description 1
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- HNUKTDKISXPDPA-UHFFFAOYSA-N 2-oxopropyl Chemical compound [CH2]C(C)=O HNUKTDKISXPDPA-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005501 Cycloxydim Substances 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001767 cationic compounds Chemical group 0.000 description 1
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical class O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GGWHBJGBERXSLL-UHFFFAOYSA-N cycloxydim Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910001411 inorganic cation Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine 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
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002892 organic cations Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening 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
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- 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
- A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
-
- 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
- A01N35/08—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 at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—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 at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/42—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Definitions
- the present invention relates to organic compounds having herbicidal properties and plant growth regulating properties; to herbicidal compositions and processes utilising such compounds and to plant growth regulating compositions and processes utilising such compositions.
- cyclohexanone oxime ether compounds similar to those of Formula 1 below except that the substituent on the oxyamino group consists of an optionally substituted phenyl connected by a C 4 alkylene or alkenylene bridging chain to the ether oxygen, and that the cyclohexanone ring carries a single substituent in the 4-position. It is claimed that these compounds are herbicides with high selectivity for grasses. In a recently published European Patent Application EP 0 456 069 Al, (13 November 1991) BASF AG claim herbicides differing from those of US 5,022,914 in that the bridging chains are C 3 , C 5 and C 6 alkylene or alkenylene.
- the single substituent claimed on 4-position of the cyclohexanone ring is selected from C 1 -C 4 alkoxy- C 1 -C 4 alkyl, C 1 -C 4 alkythio-C 1 -C 6 -alkyl, optionally substituted C 3 -C 7 cycloalkyl, an optionally substituted five membered saturated heterocycle containing one or two heteroatoms selected from O or S, an optionally substituted saturated or unsaturated 6 to 7 membered heterocycle containing one or two heteroatoms selected from O or S, an optionally substituted five membered heteroaromatic containing one or two nitrogen atoms and one oxygen or sulphur atom, or phenyl or pyridyl which may be substituted with a substituent selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy,
- EP 0 456 069 specifically discloses as pendent substituents at the 4-position of the cyclohexanone ring only ethylthiopropyl, cyclohexyl, cyclohexenyl, or one of a series of heterocyclic rings, e.g. tetrahydrofuranyl, tetrahydrothiophenyl, dioxolanyl, dithiolanyl,
- US 5,022,914 and EP 0 456 069 in which the oxime capping group includes a phenyl or substituted' phenyl group other than those disclosed in US 4,440,566, US 5,022,914 or EP 0 456 069 are highly active pre-emergent and/or post-emergent herbicides or plant growth regulators and are particularly useful for controlling certain grass weeds in dryland and paddy rice.
- this invention provides novel compounds of Formula (1), agriculturally useful compositions of these compounds and methods of using these compounds as pre-emergent and/or post-emergent herbicides, and plant growth regulators: wherein
- A is selected from the group C 1 -C 3 alkylene and C 3 alkenylene each optionally substituted with 1-4 independently selected C 1 -C 3 alkyl substituents;
- X is selected from the group O, and a single bond
- R 1 is selected from the group H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl,
- R 2 is selected from the group C 1 -C 6 alkyl, C 2 -C 8 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkylthio, C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 1 -C 4 alkyl substituted with a substituent selected from the group consisting of phenyl, phenoxy and thiophenoxy wherein the aromatic ring of said substituents is optionally substituted with 1- substituents selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, nitro, cyano, amino, C 1 -C 4 haloalkyl and C 1 -C 4 haloalkoxy, and phen
- R 5 and R 6 are independently selected from the group H, C 1 -C 6 alkyl, C 2 -C 4
- R 5 and R 6 together with the ring carbon to which they are attached form a saturated or an unsaturated 3- to 7-membered carbocyclic ring, or a saturated or an unsaturated 5- to 7-membered heterocyclic ring containing 1-3 heteroatoms selected from the group consisting of 0-3 nitrogen, 0-2 oxygen and 0-2 sulphur atoms; the carbocyclic or heterocyclic ring being optionally substituted with 1-4 substituents independently selected from the group halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkoxycarbonyl, -COOH, C 2 -C 8 alkoxyalkyl, C 2 -C 8 alkylthioalkyl, and
- R 7 , R 8 and R 9 are independently selected from the group H; halogen; C 1 -C 4 alkyl;
- M is selected from the group Li + , Na + , K + , NH 4 + , and N(R 11 ) 4 + where R 11 is C 1 -C 4 alkyl;
- R 12 is selected from the group H, C 1 -C 4 alkyl ,benzyl, CO(C 1 -C 4 alkyl), and CO 2 (C 1 -C 4 alkyl);
- R 13 , R 15 , R 18 , R 22 and R 23 are independently selected from H and C 1 -C 3 alkyl;
- R 14 , R 16 , R 17 , R 19 and R 20 are independently selected from C 1 -C 3 alkyl;
- R 16 and R 17 can be taken together as -(CH 2 ) 2 - or -(CH 2 ) 3 -;
- R 19 and R 20 can be taken together as -(CH 2 ) 2 - or -(CH 2 ) 3 -; provided that:
- alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl”, denotes straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl or the different butyl, pentyl or hexyl isomers.
- Alkoxy denotes straight chain or branched alkoxy, e.g. methoxy, ethoxy, n-propoxy, isopropyloxy, and the different butyloxy isomers.
- Alkenyl denotes groups formed from straight chain or branched alkenes, e.g. vinyl, 1-propenyl, 2-propenyl, 3-propenyl, etc.
- Alkynyl denotes groups formed from straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl, and the different butynyl isomers.
- Alkylsulphonyl denotes methylsulphonyl, ethylsulphonyl, propylsulphonyl, and the different butylsulphonyl isomers.
- Alkylthio alkylsulphinyl
- alkylamino alkylamino
- Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.
- halogen either alone or in compound words such as “haloalkyl”, denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl” said alkyl may be partially halogenated or fully substituted with halogen atoms which may be the same or different. Examples of haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl. "Alkylcarbonyl” denotes acetyl, propionyl, and the different butyryl isomers.
- Alkoxycarbonyl denotes methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, and the different butoxycarbonyl isomers.
- C i -C j prefix where i and j are numbers from 1 to 10.
- C 2 -C 3 alkylthioalkyl would designate -CH 2 SCH 3 , -CH 2 SC 2 -CH 2 CH 2 SCH 3 or -CH(CH 3 )SCH 3
- C 2 -C 5 alkoxyalkyl would represent -CH 2 OCH 3 through to -(CH 2 ) 4 OCH 3 or
- Groups of compounds of general formula (1) which are preferred for reasons including ease of synthesis and greater herbicidal efficacy include the following:
- R 1 is H, alkylsulphonyl, arylsulphonyl or M; and R 2 is C 1 -C 4 alkyl,
- C 1 -C 4 haloalkyl C 1 -C 4 alkenyl or C 2 -C 4 alkynyl .
- A is C 1 -C 2 alkylene or C3 -C 4 alkenylene optionally substituted with CH 3 or C 2 H 5 ;
- R 7 , R 8 and R 9 are independently H, Cl, Br, F, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, nitro, cyano or
- R 1 is H, Li+, Na +, or K+;
- R 2 is CH 3 , C 2 H 5 , n-C 3 H 7 or n-C 4 H 9 ;
- R 3 and R 4 are independently H, CH 3 or C 2 H 5 ;
- R 7 R 8 and R 9 are independently H, Cl, Br, F, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 , CF 3 , CHF 2 , CF 2 CF 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 , NO 2 , CN CO 2 CH 3 Ph, SO 2 Ph, COPh, CH 2 Ph, OCH 2 Ph, OPh, SPh, NHPh or N(Me)Ph.
- R 5 and R 6 are independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkylthio or C 2 -C 6 alkylthioalkyl.
- R 1 is H, Li+, Na+ or K +;
- R 2 is CH 3 , C 2 H 5 , n-C 3 H 7 or n-C 4 H 9 ;
- R 3 and R 4 are independently H or CH 3 ;
- R 7 , R 8 and R 9 are independently H, Cl, Br, F, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 , CF 3 , CHF 2 CF 2 CF 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 , NO 2 , CN, CO 2 CH 3 , Ph, SO 2 Ph, COPh, CH 2 Ph, OCH 2 Ph, OPh, SPh, NHPh or N(Me)Ph.
- R 5 and R 6 together with the carbon to which they are attached form a saturated or unsaturated 5-, 6- or 7-membered heterocyclic ring containing 1-2 heteroatoms selected from the group consisting of 0-2 nitrogen, 0-1 oxygen and 0-2 sulphur atoms; said ring is optionally substituted with 1-4 CH 3 groups.
- R 1 is H, Li +, Na+ or K+;
- R 2 is CH 3 C 2 H 5 , n-C 3 H 7 or n-C 4 H 9 ;
- R 3 and R 4 are independently H, CH 3 or C 2 H 5 ;
- R 7 , R 8 and R 9 are independently H, Cl, Br, F, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 , CF 3 , CHF 2 , CF 2 CF 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 , NO 2 , CN, CO 2 CH 3 , Ph, SO 2 Ph, COPh, CH 2 Ph, OCH 2 Ph, OPh, SPh, NHPh or N(Me)Ph. Examples of compounds within the scope of this invention are given in the Table 1 which follows.
- the compounds of the invention may be prepared by standard synthetic procedures including the process outlined in US 4,440,566.
- Appropriate cyclohexanediones may be acylated on oxygen and the enol esters isomerised (Fries rearrangement) to give th C-substituted products .
- the C-acylated derivatives may be reacted with O-substituted hydroxylamines which may in turn be generated in situ from appropriate precursors, to afford derivatives of the general Formula (1) wherein R 1 is hydrogen.
- R 1 is not hydrogen
- compounds of the inventio of Formula (1) wherein R 1 is an organic or inorganic cation may be prepared from compounds of the invention of Formula (1) wherein R 1 is hydrogen by reacting thes latter compounds with an appropriate inorganic or organic base.
- the compounds of the invention are highly active pre- emergent and/or post-emergent herbicides or plant growth regulants. These compounds are useful for controlling certain grass weeds in small grain cereals such as wheat (Triticum aestivum) and barley (Hordeum vulgare), examples of which include, but are not limited to, Centurk wheat, Era wheat, Igri barley and Klages barley.
- Many of the compounds of this invention are especially useful for the control of selected grass weeds, such as wild oats (Avena fatua), black grain (Alopecurus myosoides), crabgrass (Digitaria sanguinalis), foxtails (Setaria spp.) and Italian ryegrass (Lolium multiflonim). These compounds are also particularly useful for controlling certain grass weeds in dryland and paddy rice (Orysa sativa), examples of which include, but are not limited to, Indica and Japonica varieties of the crop. Many of the compounds of this invention are especially useful for the control of selected grass weeds, such as barnyardgrass (Echinochloa crusgalli), in paddy rice.
- selected grass weeds such as barnyardgrass (Echinochloa crusgalli), in paddy rice.
- these compounds also have utility for broad-spectrum pre- and/or post-emergence weed control in areas where control of all vegetation is required. Alternatively, these compounds are useful to regulate plant growth. Rates of application for compounds of this invention are determined by a number of factors. These factors include formulation selection, method of application, amount of vegetation present, growing conditions, etc. In general, the subject compounds should be applied at rates of 0.005 to 5 kg/ha with a preferred rate range of 0.01 to 1 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.
- the invention provides a herbicidal composition comprising a mixture of at least one herbicidal compound of formula (1) as hereinbefore defined with at least one other herbicide.
- the invention provides a method for regulating the growth of a plant comprising applying to the plant, to the seed of the plant, or to the growth medium of the plant an effective amount of a compound of Formula (1) as hereinbefore defined.
- Rates of application of these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Weed grasses in graminaceous crops can normally be killed when treated at a rate of from less than 0.1 to about 1 kg active ingredient/ha.
- the compounds of this invention can be mixed with fungicides, bactericides, acaricides, nematicides, insecticides, or other biologically active compounds in order to achieve desired results with a minimum expenditure of time, effort and material.
- Amounts of these biologically active materials added for each part by weight of the composition of this invention may vary from 0.05 to 25 parts by weight. Suitable agents of this type are well known to those skilled in the art.
- Useful formulations of the compounds within the scope of this invention can be prepared in conventional ways. They include dusts, granules, pellets, solutions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from one litre to several hundred litres per hectare. High strength compositions are primarily used as intermediates for further
- the formulations broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the approximate proportions given in the table below:
- compositions may be in the form of dusting powders or granules comprising the active ingredient and a solid diluent or carrier therefor, for example, kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, Hewill's earth, diatomaceous earth, and China clay.
- the compositions may also be in the form of dispersible powders or grains comprising a wetting agent to facilitate the dispersion in liquids of the powder or grains which may contain also solid diluents, fillers and suspending agents.
- Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for the wettable powders and the denser ones for dusts. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
- compositions for dressing seed may contain an agent (for example a mineral oil) for assisting the adhesion of the composition to the seed.
- agent for example a mineral oil
- the aqueous dispersions or emulsions may be prepared by dissolving the active ingredient(s) in an organic solvent optionally containing wetting, dispersing or emulsifying agent(s) and then adding the mixture to water which may also contain wetting, dispersing or emulsifying agent(s).
- Suitable solvents are acetone, ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, the xylenes and trichloroethylene amongst others.
- Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C.
- McCutcheon's Detergents and Emulsif ⁇ ers Annual MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses.
- compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, US Pat. No. 3.060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. The synthesis and biological activity of the compounds of formula 1 is illustrated by the following non-limiting examples.
- N,N-diisopropylethylamine (15.4g) in DMF (30 ml). After 48 hours at 20°C and 48 hours at 45°C the mixture was diluted with water (1000 ml) and filtered. The residue was washed thoroughly with water to give the product as a white solid (13.8g ), m.p.
- Tri-N-propylamine (31.5g) was added dropwise to a mixture of 5,5-dimethylcyclohexane-1,3-dione(14g), butyric anhydride(17.4g) and
- N,N-(4-dimethyIamino)pyridine (1g) and the mixture stirred at room temperature for 16 hours.
- the solution was cooled in ice, acidified to pH 3 with 2N hydrochloric acid and extracted with ether (x3).
- the combined ether extracts were washed with water, dried and the solvent removed under reduced pressure.
- the product was freed from residual butyric acid and butyric anhydride by heating at 50°C and 1mm pressure until no further material was removed and the residue was used in the next step without further purification.
- N-(4-phenylbenzyloxy)phthalimide (2.2g) in ethanol (24 ml). After a clear solution had formed the butyroyl compound (1.3g) was added and the solution was buffered t pH 4 by the addition of glacial acetic acid. After 16 hours at 20° the solvent was removed under reduced pressure, the residue was acidified to pH 2-3 with dilute hydrochloric acid and then extracted with ether (3x). The combined ether extracts were washed with water, the ether removed by evaporation and the residue was purified by chromatography over silica to give the product as a colourless solid (1.3g m.p.
- N,N-Diethylethylenediamine (0.5g) was added to a stirred suspension of N-(4-fluorophenyl)benzyloxyphthalimide (1g) in ethanol (12ml). After a clear solution had formed the crude triketone (1c, 0.6g) was added and the reaction mixture was buffered to pH4 by the addition of glacial acetic acid. After 24hrs volatile materials were removed under reduced pressure, the residue was stirred into water (50ml) and the mixture was extracted with ether. The ether extract was washed with brine, dried and the ether removed by evaporation.
- Example 6 To demonstrate the effectiveness of compounds of Formula (1) of the present invention as herbicidal agents, the compounds of Formula (1) listed in Table 2 were applied to bamyardgrass and rice postemergent at 0.1 and 0.4 kg/hectare. The herbicidal data are shown in Table 2 In the table 0 signifies no effect and 10 signifies plant dead. As can be seen the compounds of Formula (1) selectively control bamyardgrass in rice, although a few of the compounds, notably 1.48 and 1.118 are sufficiently active to kill rice at the test concentrations. In secondary screening tests at lower application rates (30 and 60 g/ha) these compounds show good selectivity.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Nouveaux composés selon la formule (1) et leurs formes isomère et/ou tautomère, dans lesquels A représente un alcylène C1-C3 ou un alkénylène C3, chacun substitué optionnellement avec 1 à 4 substituants alkyle C1-C3; X représente l'oxygène ou une liaison simple; et R1 à R9 sont différents substituants. Les combinaisons de ces composés et leurs procédés d'utilisation sont utiles en agriculture en tant qu'herbicides pré ou post-émergents, et régulateurs de croissance des plantes.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5508826A JPH07500841A (ja) | 1991-11-15 | 1992-11-13 | 除草性の2(置換オキシム)‐シクロヘキサン‐1,3‐ジオン誘導体 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPK9513 | 1991-11-15 | ||
AUPK951391 | 1991-11-15 | ||
AUPL169692 | 1992-04-03 | ||
AUPL1696 | 1992-04-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993010081A1 true WO1993010081A1 (fr) | 1993-05-27 |
Family
ID=25644157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/AU1992/000612 WO1993010081A1 (fr) | 1991-11-15 | 1992-11-13 | Derives herbicides de 2(oxime substitue)-cyclohexane-1,3-dione |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPH07500841A (fr) |
CN (1) | CN1073675A (fr) |
PT (1) | PT101060A (fr) |
TW (1) | TW221367B (fr) |
WO (1) | WO1993010081A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994026696A1 (fr) * | 1993-05-11 | 1994-11-24 | Dunlena Pty. Limited | Herbicides a base de cyclohexanes |
US5618775A (en) * | 1992-02-13 | 1997-04-08 | Basf Aktiengesellschaft | Mixtures of optically active cyclohexenone oxime ethers, their preparation, intermediates for this purpose and their use as herbicides |
US5674812A (en) * | 1994-03-31 | 1997-10-07 | Basf Aktiengesellschaft | 5(sulfo-/carbamoylmethyl)cyclohexenone oxime ethers |
US5739085A (en) * | 1994-05-05 | 1998-04-14 | Basf Aktiengesellschaft | O-(oximino)ethylcyclohexenone oxime ethers and their use as herbicides |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU7748481A (en) * | 1980-11-25 | 1982-06-03 | Tomen Corporation | Substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3- diones |
EP0456069A1 (fr) * | 1990-05-09 | 1991-11-13 | BASF Aktiengesellschaft | Ethers de cyclohexenonoxim, procédé et intermédiaires pour leur production et leur application comme herbicides |
EP0456090A2 (fr) * | 1990-05-09 | 1991-11-13 | BASF Aktiengesellschaft | Agents herbicides contenant des dérivés de la cyclohexénone comme matières actives et des dérivés du naphtalène comme antidotes |
AU8956591A (en) * | 1990-11-20 | 1992-06-11 | Dunlena Pty. Limited | Herbicides |
-
1992
- 1992-11-03 TW TW081108711A patent/TW221367B/zh active
- 1992-11-13 PT PT101060A patent/PT101060A/pt not_active Application Discontinuation
- 1992-11-13 JP JP5508826A patent/JPH07500841A/ja active Pending
- 1992-11-13 WO PCT/AU1992/000612 patent/WO1993010081A1/fr active Application Filing
- 1992-11-14 CN CN92114386A patent/CN1073675A/zh active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU7748481A (en) * | 1980-11-25 | 1982-06-03 | Tomen Corporation | Substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3- diones |
EP0456069A1 (fr) * | 1990-05-09 | 1991-11-13 | BASF Aktiengesellschaft | Ethers de cyclohexenonoxim, procédé et intermédiaires pour leur production et leur application comme herbicides |
EP0456090A2 (fr) * | 1990-05-09 | 1991-11-13 | BASF Aktiengesellschaft | Agents herbicides contenant des dérivés de la cyclohexénone comme matières actives et des dérivés du naphtalène comme antidotes |
AU8956591A (en) * | 1990-11-20 | 1992-06-11 | Dunlena Pty. Limited | Herbicides |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5618775A (en) * | 1992-02-13 | 1997-04-08 | Basf Aktiengesellschaft | Mixtures of optically active cyclohexenone oxime ethers, their preparation, intermediates for this purpose and their use as herbicides |
WO1994026696A1 (fr) * | 1993-05-11 | 1994-11-24 | Dunlena Pty. Limited | Herbicides a base de cyclohexanes |
US5674812A (en) * | 1994-03-31 | 1997-10-07 | Basf Aktiengesellschaft | 5(sulfo-/carbamoylmethyl)cyclohexenone oxime ethers |
US5739085A (en) * | 1994-05-05 | 1998-04-14 | Basf Aktiengesellschaft | O-(oximino)ethylcyclohexenone oxime ethers and their use as herbicides |
Also Published As
Publication number | Publication date |
---|---|
PT101060A (pt) | 1994-03-31 |
CN1073675A (zh) | 1993-06-30 |
JPH07500841A (ja) | 1995-01-26 |
TW221367B (fr) | 1994-03-01 |
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