NZ208702A - Cyclohexenone oxime derivatives and herbicidal compositions - Google Patents
Cyclohexenone oxime derivatives and herbicidal compositionsInfo
- Publication number
- NZ208702A NZ208702A NZ208702A NZ20870284A NZ208702A NZ 208702 A NZ208702 A NZ 208702A NZ 208702 A NZ208702 A NZ 208702A NZ 20870284 A NZ20870284 A NZ 20870284A NZ 208702 A NZ208702 A NZ 208702A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- alkyl
- substituted
- alkoxy
- halogen
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 26
- WNPVAXLJVUXYFU-UHFFFAOYSA-N n-cyclohex-2-en-1-ylidenehydroxylamine Chemical class ON=C1CCCC=C1 WNPVAXLJVUXYFU-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 154
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 104
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 77
- -1 hydroxy, mercapto Chemical group 0.000 claims abstract description 75
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 67
- 150000002367 halogens Chemical class 0.000 claims abstract description 67
- 239000001257 hydrogen Substances 0.000 claims abstract description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 40
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 33
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 32
- 125000002252 acyl group Chemical group 0.000 claims abstract description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 24
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 21
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 17
- 239000004480 active ingredient Substances 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 14
- 150000002923 oximes Chemical class 0.000 claims abstract description 14
- 150000001767 cationic compounds Chemical class 0.000 claims abstract description 12
- 150000002892 organic cations Chemical group 0.000 claims abstract description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 10
- 239000002262 Schiff base Chemical class 0.000 claims abstract description 9
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 9
- 150000002466 imines Chemical class 0.000 claims abstract description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910001411 inorganic cation Inorganic materials 0.000 claims abstract description 7
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract description 6
- 150000002373 hemiacetals Chemical class 0.000 claims abstract description 6
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 4
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 241000196324 Embryophyta Species 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 51
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000001188 haloalkyl group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 238000012360 testing method Methods 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- 239000001963 growth medium Substances 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 230000002147 killing effect Effects 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 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 claims 2
- MDOAYCRGBFVYAL-UHFFFAOYSA-N 3-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-N,N,2,4,6-pentamethylbenzamide Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)C(N(C)C)=O)C)=O MDOAYCRGBFVYAL-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- SYAXRRBWFBYNDY-UHFFFAOYSA-N ethyl 3-[3-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-2,4,6-trimethylphenyl]-3-oxopropanoate Chemical compound C(C)OC(=O)CC(=O)C=1C(=C(C(=CC1C)C)C1CC(=C(C(C1)=O)C(CC)=NOCC)O)C SYAXRRBWFBYNDY-UHFFFAOYSA-N 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 13
- 230000008635 plant growth Effects 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 11
- 230000001105 regulatory effect Effects 0.000 abstract description 9
- 230000007363 regulatory process Effects 0.000 abstract description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 1
- 125000004426 substituted alkynyl group Chemical group 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000004009 herbicide Substances 0.000 description 30
- 239000007787 solid Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-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
- 239000002585 base Substances 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000007900 aqueous suspension Substances 0.000 description 7
- 235000013339 cereals Nutrition 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 238000004611 spectroscopical analysis Methods 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- HBXUKEYLLIXGAE-UHFFFAOYSA-N C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C=C1C Chemical compound C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C=C1C HBXUKEYLLIXGAE-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 240000001931 Ludwigia octovalvis Species 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 241000209504 Poaceae Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 150000002790 naphthalenes Chemical class 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
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- 239000008187 granular material Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 2
- UKRQMDIFLKHCRO-UHFFFAOYSA-N 2,4,6-trimethylbenzoyl chloride Chemical compound CC1=CC(C)=C(C(Cl)=O)C(C)=C1 UKRQMDIFLKHCRO-UHFFFAOYSA-N 0.000 description 2
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
- 239000002794 2,4-DB Substances 0.000 description 2
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 2
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
- PYGBICXCVJEFME-UHFFFAOYSA-N 3-formyl-2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1C=O PYGBICXCVJEFME-UHFFFAOYSA-N 0.000 description 2
- POEUTNSTNQDWQV-UHFFFAOYSA-N 3-formyl-n,n,2,4,6-pentamethylbenzamide Chemical compound CN(C)C(=O)C1=C(C)C=C(C)C(C=O)=C1C POEUTNSTNQDWQV-UHFFFAOYSA-N 0.000 description 2
- PJOPLUVTUPVUAO-UHFFFAOYSA-N 3-hydroxy-5-(2,4,6-trimethylphenyl)cyclohex-2-en-1-one Chemical compound CC1=CC(C)=CC(C)=C1C1CC(=O)C=C(O)C1 PJOPLUVTUPVUAO-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 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
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 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
-
- 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
-
- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- 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
-
- 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
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPG034183 | 1983-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ208702A true NZ208702A (en) | 1987-11-27 |
Family
ID=3770237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ208702A NZ208702A (en) | 1983-07-18 | 1984-06-28 | Cyclohexenone oxime derivatives and herbicidal compositions |
Country Status (17)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3433767A1 (de) * | 1984-07-27 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| EP0202042B1 (en) * | 1985-05-06 | 1990-05-09 | Ici Australia Limited | Cyclohexane-1,3-dione derivatives, compositions containing them, processes for preparing them, and their use as herbicides and plant growth regulators |
| US4888043A (en) * | 1985-07-12 | 1989-12-19 | Ici Australia Limited | Herbicidal amino-mesityl cyclohexane-1,3-dione compounds |
| US4795487A (en) * | 1985-08-08 | 1989-01-03 | Ici Australia Limited | Herbicidal cyclohexane-1,3-dione derivatives |
| DE3611418A1 (de) * | 1986-04-05 | 1987-10-08 | Basf Ag | 2,5-substituierte dihydroresorcinenoletherderivate |
| AU595040B2 (en) * | 1986-07-01 | 1990-03-22 | Ici Australia Operations Proprietary Limited | Cyclohexane-1, 3-dione herbicides |
| GB8711525D0 (en) * | 1987-05-15 | 1987-06-17 | Shell Int Research | Oximino ether compounds |
| JP2618639B2 (ja) * | 1987-07-03 | 1997-06-11 | 住友化学工業株式会社 | シクロヘキセノン誘導体およびそれを有効成分とする除草剤 |
| GB8722838D0 (en) * | 1987-09-29 | 1987-11-04 | Shell Int Research | Oximino ether compounds |
| DE3741823A1 (de) * | 1987-12-10 | 1989-06-22 | Basf Ag | Cyclohexenonverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwachstums |
| DE3838309A1 (de) * | 1988-11-11 | 1990-05-31 | Basf Ag | Cyclohexenonoximether, verfahren zu ihrer herstellung und ihre verwendung als herbizid |
| US5364833A (en) * | 1990-05-09 | 1994-11-15 | Basf Aktiengesellschaft | Cyclohexenone oxime ethers, their preparation and their use as herbicides |
| DE4014988A1 (de) * | 1990-05-09 | 1991-11-14 | Basf Ag | Cyclohexenonoximether, verfahren zu ihrer herstellung und ihre verwendung als herbizid |
| NZ240662A (en) * | 1990-11-27 | 1993-04-28 | Ici Australia Operations | Preparation of the anhydrous crystalline form of fenoxydim |
| AU650495B2 (en) * | 1990-11-27 | 1994-06-23 | Crop Care Australasia Pty Ltd | Crystallisation process |
| KR950003497B1 (ko) * | 1992-08-07 | 1995-04-13 | 재단법인 한국화학연구소 | 제초성 시클로헥산-1,3-디온 유도체와 그 제조방법 |
| DE4305696A1 (de) * | 1993-02-25 | 1994-09-01 | Hoechst Ag | Nachweisverfahren zur Identifizierung von Inhibitoren |
| CA2289114A1 (en) | 1997-05-07 | 1998-11-12 | Basf Aktiengesellschaft | Substituted 2-(3-alkenyl-benzoyl)-cyclohexane-1,3-diones |
| DE19724502C1 (de) * | 1997-06-11 | 1998-10-08 | Webasto Thermosysteme Gmbh | Heizgerät |
| JP2001294581A (ja) * | 2000-04-12 | 2001-10-23 | Nippon Bayer Agrochem Co Ltd | イソチアゾール誘導体 |
| US8916723B2 (en) | 2010-03-22 | 2014-12-23 | Council Of Scientific & Industrial Research | Substituted cyclohexane-1, 3-dione compounds, process for preparation thereof and its applications |
| CN106831488B (zh) * | 2015-12-04 | 2018-09-28 | 沈阳中化农药化工研发有限公司 | 一种5-(3,4-二取代苯基)-1,3-环己二酮类化合物及其应用 |
| CN116041156B (zh) * | 2023-01-29 | 2024-04-05 | 南京合创药业有限公司 | 5-(2,4,6-三甲苯基)-2-丙酰基-3-羟基-2-环己烯-1-酮的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ202284A (en) * | 1981-11-20 | 1986-06-11 | Ici Australia Ltd | 2-(1-(alkoxyimino)alkyl)-3-hydroxy-5-poly(methyl)phenyl-cyclohex-2-en-1-ones and herbicidal compositions |
| FR2518990B1 (fr) * | 1981-12-29 | 1986-04-18 | Nippon Soda Co | Derives de cyclohexenone, compositions herbicides les contenant et procede pour leur preparation |
| JPS58206549A (ja) * | 1982-05-26 | 1983-12-01 | Nippon Soda Co Ltd | ５−フエニルシクロヘキセノン誘導体、その製造方法及び選択的除草剤 |
| GB2116544B (en) * | 1981-12-29 | 1985-06-19 | Nippon Soda Co | Cyclohexanone derivatives |
| PH20618A (en) * | 1982-01-29 | 1987-03-06 | Ici Australia Ltd | Herbicidal 5-(substituted phenyl)-cyclohexan-1,3-dione derivatives |
| JPS59163361A (ja) * | 1983-03-07 | 1984-09-14 | Nippon Soda Co Ltd | シクロヘキセノン誘導体その製造方法及び除草剤 |
-
1983
- 1983-07-18 AU AU30330/84A patent/AU566671B2/en not_active Ceased
-
1984
- 1984-06-28 NZ NZ208702A patent/NZ208702A/en unknown
- 1984-07-02 US US06/627,297 patent/US4652303A/en not_active Expired - Fee Related
- 1984-07-04 ZA ZA845144A patent/ZA845144B/xx unknown
- 1984-07-09 PH PH30942A patent/PH23621A/en unknown
- 1984-07-10 GR GR75257A patent/GR81554B/el unknown
- 1984-07-11 DE DE8484304748T patent/DE3474139D1/de not_active Expired
- 1984-07-11 AT AT84304748T patent/ATE37357T1/de not_active IP Right Cessation
- 1984-07-11 EP EP84304748A patent/EP0133349B1/en not_active Expired
- 1984-07-11 IL IL72386A patent/IL72386A/xx unknown
- 1984-07-16 HU HU842760A patent/HU191424B/hu not_active IP Right Cessation
- 1984-07-17 BR BR8403562A patent/BR8403562A/pt not_active IP Right Cessation
- 1984-07-17 JP JP59147039A patent/JPS6038354A/ja active Pending
- 1984-07-18 EG EG45484A patent/EG17123A/xx active
- 1984-07-18 ES ES84534421A patent/ES8602647A1/es not_active Expired
- 1984-07-18 DK DK352284A patent/DK352284A/da not_active Application Discontinuation
- 1984-07-18 CA CA000459208A patent/CA1233466A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3474139D1 (en) | 1988-10-27 |
| US4652303A (en) | 1987-03-24 |
| ES534421A0 (es) | 1985-12-01 |
| HU191424B (en) | 1987-02-27 |
| IL72386A0 (en) | 1984-11-30 |
| IL72386A (en) | 1989-09-28 |
| AU3033084A (en) | 1985-01-24 |
| EP0133349B1 (en) | 1988-09-21 |
| EP0133349A1 (en) | 1985-02-20 |
| HUT34425A (en) | 1985-03-28 |
| DK352284D0 (da) | 1984-07-18 |
| ES8602647A1 (es) | 1985-12-01 |
| BR8403562A (pt) | 1985-06-25 |
| AU566671B2 (en) | 1987-10-29 |
| JPS6038354A (ja) | 1985-02-27 |
| CA1233466A (en) | 1988-03-01 |
| EG17123A (en) | 1993-12-30 |
| DK352284A (da) | 1985-01-19 |
| ATE37357T1 (de) | 1988-10-15 |
| GR81554B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-11 |
| PH23621A (en) | 1989-09-11 |
| ZA845144B (en) | 1985-03-27 |
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