JPH0672130B2 - 除草剤化合物及びその組成物 - Google Patents
除草剤化合物及びその組成物Info
- Publication number
- JPH0672130B2 JPH0672130B2 JP58011595A JP1159583A JPH0672130B2 JP H0672130 B2 JPH0672130 B2 JP H0672130B2 JP 58011595 A JP58011595 A JP 58011595A JP 1159583 A JP1159583 A JP 1159583A JP H0672130 B2 JPH0672130 B2 JP H0672130B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- formula
- halogen
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 139
- 239000000203 mixture Substances 0.000 title claims description 99
- 230000002363 herbicidal effect Effects 0.000 title claims description 25
- 239000004009 herbicide Substances 0.000 title description 31
- -1 nitro, hydroxy Chemical group 0.000 claims description 123
- 238000000034 method Methods 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 22
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 17
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 17
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 150000002892 organic cations Chemical class 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 150000001767 cationic compounds Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000003935 benzaldehydes Chemical class 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
- 239000001963 growth medium Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 8
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical class [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 239000000047 product Substances 0.000 description 51
- 239000000243 solution Substances 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 230000003595 spectral effect Effects 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 238000001228 spectrum Methods 0.000 description 21
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 19
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 238000004611 spectroscopical analysis Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 239000003480 eluent Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 235000013339 cereals Nutrition 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 230000008635 plant growth Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- JQLUPCVBJIXLEQ-UHFFFAOYSA-N 5-(3-acetyl-2,4,6-trimethylphenyl)-2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound C1C(=O)C(C(CC)=NOCC)=C(O)CC1C1=C(C)C=C(C)C(C(C)=O)=C1C JQLUPCVBJIXLEQ-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 150000002923 oximes Chemical class 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000007900 aqueous suspension Substances 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WMEITEQAFPMBCC-UHFFFAOYSA-N [4-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-3,5-dimethylphenyl] acetate Chemical compound C1C(=O)C(C(CC)=NOCC)=C(O)CC1C1=C(C)C=C(OC(C)=O)C=C1C WMEITEQAFPMBCC-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 6
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 6
- HPNCFHATRQVYJY-UHFFFAOYSA-N 3-[4-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-2,4,6-trimethylbenzonitrile Chemical compound C(C)ON=C(CCC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)C#N)C)=O HPNCFHATRQVYJY-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 241000721671 Ludwigia Species 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 150000002790 naphthalenes Chemical class 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 229940035044 sorbitan monolaurate Drugs 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000000375 suspending agent Substances 0.000 description 5
- AMSDJJBYTGADDE-UHFFFAOYSA-N 2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-(2,4,6-trimethyl-3-methylsulfinylphenyl)cyclohex-2-en-1-one Chemical compound CCON=C(CC)C1=C(O)CC(CC1=O)c1c(C)cc(C)c(c1C)S(C)=O AMSDJJBYTGADDE-UHFFFAOYSA-N 0.000 description 4
- FNJMSKSVAZGQQU-UHFFFAOYSA-N 2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(CC)=NOCC)=C(O)CC1C1=C(C)C=C(C)C([N+]([O-])=O)=C1C FNJMSKSVAZGQQU-UHFFFAOYSA-N 0.000 description 4
- HFFNVNATEJOMFQ-UHFFFAOYSA-N 2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-5-(2,3,4,5-tetramethyl-6-methylsulfonylphenyl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1C1=C(C)C(C)=C(C)C(C)=C1S(C)(=O)=O HFFNVNATEJOMFQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- DWNDQISEVFLIEU-UHFFFAOYSA-N 5-(3-amino-2,4,6-trimethylphenyl)-2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound C(C)ON=C(CCC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)N)C)=O DWNDQISEVFLIEU-UHFFFAOYSA-N 0.000 description 4
- LSGNPDBCSWUBMO-UHFFFAOYSA-N 5-(3-butanoyl-2,4,6-trimethylphenyl)-2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(C(CCC)=NOCC)=C(O)C2)=C1C LSGNPDBCSWUBMO-UHFFFAOYSA-N 0.000 description 4
- LOONCYLEHBCOBL-UHFFFAOYSA-N 5-[3-(ethoxymethyl)-2,4,6-trimethylphenyl]-2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1C1=C(C)C=C(C)C(COCC)=C1C LOONCYLEHBCOBL-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- WBGDDVMYKAROIK-UHFFFAOYSA-N N-[3-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-2,4,6-trimethylphenyl]acetamide Chemical compound C(C)ON=C(CC)C=1C(CC(CC=1O)C1=C(C(=C(C=C1C)C)NC(C)=O)C)=O WBGDDVMYKAROIK-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002262 Schiff base Chemical class 0.000 description 4
- 150000004753 Schiff bases Chemical class 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 229910001413 alkali metal ion Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- PVSCWHPFPYZBTD-UHFFFAOYSA-N 2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-(2,4,6-trimethyl-3-methylsulfonylphenyl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(CC)=NOCC)=C(O)CC1C1=C(C)C=C(C)C(S(C)(=O)=O)=C1C PVSCWHPFPYZBTD-UHFFFAOYSA-N 0.000 description 3
- RGUZFNYDWVOFPV-UHFFFAOYSA-N 2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-(4-hydroxy-2,6-dimethylphenyl)cyclohex-2-en-1-one Chemical compound CC1=C(C(=CC(=C1)O)C)C1CC(=C(C(C1)=O)C(CC)=NOCC)O RGUZFNYDWVOFPV-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- FQQVKPKMWKIMHK-UHFFFAOYSA-N 3-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-N,N,2,4-tetramethylbenzenesulfonamide Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=CC=C1C)S(N(C)C)(=O)=O)C)=O FQQVKPKMWKIMHK-UHFFFAOYSA-N 0.000 description 3
- XYKWCNJMBWQMDQ-UHFFFAOYSA-N 5-(5-ethoxyimino-2,3,4,6-tetramethylcyclohexa-1,3-dien-1-yl)-2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound C(C)ON=C(CCC)C=1C(CC(CC=1O)C=1C(C(C(=C(C=1C)C)C)=NOCC)C)=O XYKWCNJMBWQMDQ-UHFFFAOYSA-N 0.000 description 3
- HKBVENWRYJKYNO-UHFFFAOYSA-N 5-[3-chloro-6-(difluoromethoxy)-2,4-dimethylphenyl]-2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=C(C=C1OC(F)F)C)Cl)C)=O HKBVENWRYJKYNO-UHFFFAOYSA-N 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- RTJPUWXNDYMZRN-UHFFFAOYSA-N C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(O)C=C1C Chemical compound C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(O)C=C1C RTJPUWXNDYMZRN-UHFFFAOYSA-N 0.000 description 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- 241000209510 Liliopsida Species 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
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- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 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 1
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- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
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- 238000006266 etherification reaction Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
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- 239000003621 irrigation water Substances 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical class C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
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- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- GNUUMFGJGKCCGJ-UHFFFAOYSA-N n-[3-(3-hydroxy-5-oxocyclohex-3-en-1-yl)-2,4,6-trimethylphenyl]acetamide Chemical compound CC(=O)NC1=C(C)C=C(C)C(C2CC(=O)C=C(O)C2)=C1C GNUUMFGJGKCCGJ-UHFFFAOYSA-N 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000276 sauconite Inorganic materials 0.000 description 1
- 230000035040 seed growth Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
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- 239000000344 soap Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- SZXAJDQTPWYNBN-NWBUNABESA-M sodium;4-methoxycarbonyl-5,5-dimethyl-3-oxo-2-[(e)-n-prop-2-enoxy-c-propylcarbonimidoyl]cyclohexen-1-olate Chemical compound [Na+].C=CCO\N=C(/CCC)C1=C([O-])CC(C)(C)C(C(=O)OC)C1=O SZXAJDQTPWYNBN-NWBUNABESA-M 0.000 description 1
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- 230000004936 stimulating effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—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
-
- 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
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; 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
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; 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
- 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
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
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- C—CHEMISTRY; METALLURGY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/542—Alkylated benzaldehydes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPF248982 | 1982-01-29 | ||
AUPF486582 | 1982-07-14 | ||
AU4865 | 1982-07-14 | ||
AU2489 | 1994-03-08 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4236172A Division JPH0672120B2 (ja) | 1982-01-29 | 1992-09-03 | シクロヘキサン誘導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58150537A JPS58150537A (ja) | 1983-09-07 |
JPH0672130B2 true JPH0672130B2 (ja) | 1994-09-14 |
Family
ID=25642524
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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JP58011595A Expired - Lifetime JPH0672130B2 (ja) | 1982-01-29 | 1983-01-28 | 除草剤化合物及びその組成物 |
JP4236172A Expired - Lifetime JPH0672120B2 (ja) | 1982-01-29 | 1992-09-03 | シクロヘキサン誘導体 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4236172A Expired - Lifetime JPH0672120B2 (ja) | 1982-01-29 | 1992-09-03 | シクロヘキサン誘導体 |
Country Status (16)
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU566671B2 (en) * | 1983-07-18 | 1987-10-29 | Ici Australia Limited | Cyclohexene-1,3-dione derivatives |
DE3329017A1 (de) * | 1983-08-11 | 1985-02-28 | Basf Ag, 6700 Ludwigshafen | Cyclohexan-1,3-dionderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
DE3336354A1 (de) * | 1983-10-06 | 1985-04-25 | Basf Ag, 6700 Ludwigshafen | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
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 |
EP0209283B1 (en) * | 1985-07-12 | 1991-10-16 | Ici Australia Limited | Herbicidal cyclohexane-1,3-dione derivatives |
US4795487A (en) * | 1985-08-08 | 1989-01-03 | Ici Australia Limited | Herbicidal cyclohexane-1,3-dione derivatives |
EP0211605B1 (en) | 1985-08-08 | 1991-05-15 | Ici Australia Limited | Herbicidal cyclohexane-1,3-dione derivatives |
DE3543447A1 (de) * | 1985-12-09 | 1987-06-11 | Basf Ag | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide und das pflanzenwachstum regulierende mittel |
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 |
GB8624644D0 (en) * | 1986-10-14 | 1986-11-19 | Ici Plc | Herbicidal compositions |
JPS63156702A (ja) * | 1986-12-19 | 1988-06-29 | Sumitomo Chem Co Ltd | イネ科作物用除草剤 |
GB8702613D0 (en) * | 1987-02-05 | 1987-03-11 | Ici Plc | Compositions |
GB8722838D0 (en) * | 1987-09-29 | 1987-11-04 | Shell Int Research | Oximino ether compounds |
US5102442A (en) * | 1987-10-05 | 1992-04-07 | Basf Corporation | Antagonism defeating crop oil concentrates |
DE3741823A1 (de) * | 1987-12-10 | 1989-06-22 | Basf Ag | Cyclohexenonverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwachstums |
DE3819347A1 (de) * | 1988-06-07 | 1989-12-14 | Basf Ag | Herbizide tetrahydropyran-2,4-dione |
US4966728A (en) * | 1988-08-26 | 1990-10-30 | Basf Corporation | Adjuvants for use with postemergent herbicides |
US4994106A (en) * | 1989-03-09 | 1991-02-19 | Basf Aktiengesellschaft | Cyclohexenone compounds, their preparation and their use for controlling undesirable plant growth |
GB9003553D0 (en) * | 1990-02-16 | 1990-04-11 | Ici Plc | Herbicidal compositions |
US5006159A (en) * | 1990-03-30 | 1991-04-09 | Dowelanco | Substituted cyclohexanediones and their herbicidal uses |
ES2088435T3 (es) * | 1990-10-17 | 1996-08-16 | Tomen Corp | Procedimiento y composicion para mejorar la absorcion y transporte de agentes bioactivos en plantas. |
NZ240662A (en) * | 1990-11-27 | 1993-04-28 | Ici Australia Operations | Preparation of the anhydrous crystalline form of fenoxydim |
GB9111975D0 (en) * | 1991-06-04 | 1991-07-24 | Ici Plc | Chemical process |
SK322292A3 (en) * | 1991-11-15 | 1995-12-06 | Ciba Geigy Ag | Synergic agent and method of selective weed suppression |
US5842033A (en) * | 1992-06-30 | 1998-11-24 | Discovision Associates | Padding apparatus for passing an arbitrary number of bits through a buffer in a pipeline system |
KR100428280B1 (ko) * | 1995-09-20 | 2005-01-15 | 바스프 악티엔게젤샤프트 | 시클로헥세논 옥심에테르를 포함하는 상승작용 제초제 혼합물 |
GB9615091D0 (en) * | 1996-07-18 | 1996-09-04 | Zeneca Ltd | Herbicidal composition |
AUPO132296A0 (en) * | 1996-07-30 | 1996-08-22 | Ici Australia Operations Proprietary Limited | Chemical process |
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 (8)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5521001B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-08-15 | 1980-06-06 | ||
US3950420A (en) * | 1973-08-15 | 1976-04-13 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
JPS577122B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-12-24 | 1982-02-09 | ||
JPS5176245A (en) * | 1974-12-26 | 1976-07-01 | Nippon Soda Co | 22 shikurohekisen 11 onjudotai oyobi josozai |
JPS5390248A (en) * | 1977-08-02 | 1978-08-08 | Nippon Soda Co Ltd | Process for preparation cyclohexanedione derivs. |
US4436666A (en) * | 1978-09-22 | 1984-03-13 | Union Carbide Corporation | Biocidal enol derivatives of 2-aryl-1,3-cycloalkanedione compounds |
US4350705A (en) * | 1979-03-31 | 1982-09-21 | Eisai Co., Ltd. | Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives |
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 |
-
1983
- 1983-01-13 PH PH28382A patent/PH20618A/en unknown
- 1983-01-14 IL IL67683A patent/IL67683A/xx not_active IP Right Cessation
- 1983-01-21 DK DK023983A patent/DK172146B1/da not_active IP Right Cessation
- 1983-01-21 GR GR70309A patent/GR77855B/el unknown
- 1983-01-24 IE IE135/83A patent/IE54546B1/en not_active IP Right Cessation
- 1983-01-25 EP EP83300368A patent/EP0085529B1/en not_active Expired
- 1983-01-25 US US06/460,854 patent/US4666510A/en not_active Expired - Lifetime
- 1983-01-25 DE DE8383300368T patent/DE3365501D1/de not_active Expired
- 1983-01-26 HU HU83247A patent/HU189638B/hu unknown
- 1983-01-27 BR BR8300403A patent/BR8300403A/pt not_active IP Right Cessation
- 1983-01-28 PT PT76160A patent/PT76160B/pt unknown
- 1983-01-28 TR TR21430A patent/TR21430A/xx unknown
- 1983-01-28 JP JP58011595A patent/JPH0672130B2/ja not_active Expired - Lifetime
- 1983-01-28 CA CA000420413A patent/CA1203544A/en not_active Expired
- 1983-01-28 ES ES519367A patent/ES8404672A1/es not_active Expired
- 1983-01-29 EG EG55/83A patent/EG17110A/xx active
-
1986
- 1986-12-17 US US06/942,827 patent/US4767879A/en not_active Expired - Lifetime
-
1992
- 1992-09-03 JP JP4236172A patent/JPH0672120B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
BR8300403A (pt) | 1983-11-01 |
DK172146B1 (da) | 1997-11-24 |
IL67683A (en) | 1986-10-31 |
US4666510A (en) | 1987-05-19 |
JPH061745A (ja) | 1994-01-11 |
EG17110A (en) | 1991-08-30 |
EP0085529A2 (en) | 1983-08-10 |
HU189638B (en) | 1986-07-28 |
EP0085529B1 (en) | 1986-08-27 |
IE54546B1 (en) | 1989-11-08 |
GR77855B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-09-25 |
ES519367A0 (es) | 1984-05-01 |
JPH0672120B2 (ja) | 1994-09-14 |
JPS58150537A (ja) | 1983-09-07 |
DK23983D0 (da) | 1983-01-21 |
PT76160B (en) | 1986-04-30 |
IE830135L (en) | 1983-07-29 |
DE3365501D1 (en) | 1986-10-02 |
ES8404672A1 (es) | 1984-05-01 |
US4767879A (en) | 1988-08-30 |
PT76160A (en) | 1983-02-01 |
CA1203544A (en) | 1986-04-22 |
EP0085529A3 (en) | 1983-11-16 |
TR21430A (tr) | 1984-06-01 |
DK23983A (da) | 1983-07-30 |
PH20618A (en) | 1987-03-06 |
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