WO2001017973A2 - Neue herbizide - Google Patents
Neue herbizide Download PDFInfo
- Publication number
- WO2001017973A2 WO2001017973A2 PCT/EP2000/008657 EP0008657W WO0117973A2 WO 2001017973 A2 WO2001017973 A2 WO 2001017973A2 EP 0008657 W EP0008657 W EP 0008657W WO 0117973 A2 WO0117973 A2 WO 0117973A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- halogen
- alkyl
- alkoxy
- formula
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 150000002367 halogens Chemical class 0.000 claims description 114
- 229910052736 halogen Inorganic materials 0.000 claims description 113
- 239000001257 hydrogen Substances 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 89
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- -1 hydroxy, mercapto Chemical class 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 150000002431 hydrogen Chemical class 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 239000001301 oxygen Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 18
- 229910052717 sulfur Chemical group 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 239000011593 sulfur Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 230000002363 herbicidal effect Effects 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 241000251730 Chondrichthyes Species 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 125000004354 sulfur functional group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 3
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims 2
- 239000004327 boric acid Substances 0.000 claims 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000003606 tin compounds Chemical class 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000011734 sodium Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000012074 organic phase Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000012043 crude product Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 0 CCc1c(C(C(NN2*)=O)C2=O)c(CC)cc(*)c1 Chemical compound CCc1c(C(C(NN2*)=O)C2=O)c(CC)cc(*)c1 0.000 description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 5
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 5
- JGBZTJWQMWZVNX-UHFFFAOYSA-N palladium;tricyclohexylphosphane Chemical compound [Pd].C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 JGBZTJWQMWZVNX-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 235000015424 sodium Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000006880 cross-coupling reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000694440 Colpidium aqueous Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 235000009973 maize Nutrition 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- SZOLUXDHHKCYKT-UHFFFAOYSA-N but-1-en-1-amine Chemical compound CCC=CN SZOLUXDHHKCYKT-UHFFFAOYSA-N 0.000 description 1
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 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
- 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 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
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 125000004310 dioxan-2-yl group Chemical group [H]C1([H])OC([H])([H])C([H])(*)OC1([H])[H] 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- VYCUDDORRRFANN-UHFFFAOYSA-N furan-2-yloxyboronic acid Chemical class OB(O)OC1=CC=CO1 VYCUDDORRRFANN-UHFFFAOYSA-N 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 229940028332 halog Drugs 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
- 125000000592 heterocycloalkyl 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
- 150000004678 hydrides Chemical class 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- OBWFJXLKRAFEDI-UHFFFAOYSA-N methyl cyanoformate Chemical compound COC(=O)C#N OBWFJXLKRAFEDI-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DJUWKQYCYKRJNI-UHFFFAOYSA-N n-ethoxyaniline Chemical class CCONC1=CC=CC=C1 DJUWKQYCYKRJNI-UHFFFAOYSA-N 0.000 description 1
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- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- KLJUVCXLKBGKOY-UHFFFAOYSA-N n-hexylheptan-1-amine Chemical compound CCCCCCCNCCCCCC KLJUVCXLKBGKOY-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- SKLXFEQHEBALKG-UHFFFAOYSA-N n-hexyloctan-1-amine Chemical compound CCCCCCCCNCCCCCC SKLXFEQHEBALKG-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical class CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
- OZIXTIPURXIEMB-UHFFFAOYSA-N n-methylnonan-1-amine Chemical compound CCCCCCCCCNC OZIXTIPURXIEMB-UHFFFAOYSA-N 0.000 description 1
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
- CNCBAEHAEKNSPZ-UHFFFAOYSA-N n-methylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNC CNCBAEHAEKNSPZ-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-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
- 150000005002 naphthylamines Chemical class 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 150000004995 p-toluidines Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- ODOPKAJVFRHHGM-UHFFFAOYSA-N phenyltin Chemical compound [Sn]C1=CC=CC=C1 ODOPKAJVFRHHGM-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 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
- 238000004904 shortening Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
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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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/616—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Definitions
- the present invention relates to new, herbicidally active pyrazolinone derivatives, processes for their preparation, compositions which comprise these compounds and their use for controlling weeds, especially in crops of useful plants or for inhibiting plant growth.
- the present invention thus relates to compounds of the formula I.
- Ri and R 3 independently of one another hydrogen, halogen, nitro, cyano, -CC 4 alkyl, C 2 -C 4 -
- R 2 is phenyl, naphthyl or a 5- or 6-membered aromatic ring which is 1 or 2
- Heteroatoms selected from the group containing nitrogen, oxygen and sulfur can, wherein the phenyl ring, the naphthyl ring and the 5- or 6-membered aromatic ring by halogen, C 3 -C 8 cycloalkyl, hydroxy, mercapto, amino, amino-CrC 6 -alkyl, carboxyl -C-C 6 -alkyl , Cyano, nitro or formyl may be substituted; and / or the phenyl ring, the naphthyl ring and the 5- or 6-membered aromatic ring by dC 6 - alkyl, -C-C 6 alkoxy, hydroxy-d-Ce-alkyl, Ci-Ce-alkoxy-CrCe-alkyl, dC 6 -alkoxy-C ⁇ -C 6 - alkoxy, dC 6 -alkylcarbonyl, dC 6 -alkylthio, CrC 6 -alkyl
- R5 2 , R 5 3, Rw and R 55 independently of one another hydrogen, dC 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl or by halogen, hydroxy, alkoxy, mercapto, amino, cyano, nitro , Alkylthio, alkylsulfinyl or alkylsulfonyl substituted d-C ⁇ -alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl,
- R and R 5 are independently hydrogen, d-C ⁇ 2 -alkyl, C 2 -Halogenalky
- R 4 and R 5 together with the atoms to which they are attached form a 5- to 8-membered group
- Form ring which may contain 1 or 2 oxygen atoms, sulfur atoms or groups NR 6 , wherein
- R 6 is hydrogen, dC 4 alkyl, dC 6 alkylcarbonyl, C ⁇ -C 6 alkylsulfonyl, C 3 -C 6 alkenyl or
- Haloalkyl, C 3 -C 8 cycloalkyl, phenyl or benzyl may be substituted; or with halogen, dC 6 -alkyl, dC 6 -haloalkyl, C 3 -C 6 -cycloalkyl, hydroxy, -C-C 6 -alkoxy,
- C 1 -C 6 -alkoxy-C 6 -C 6 alkoxy, dC ⁇ -haloalkoxy or nitro substituted phenyl or with Halogen, C ⁇ -C6 alkyl, Ci-Ce-haloalkyl, C 3 -C 6 alkoxy, Ci-Ce-haloalkoxy or nitro substituted benzyl may be substituted 6 -cycloalkyl, hydroxy, C ⁇ -C; or with CH 2 heteroaryl, the aryl part having 5 or 6 members, or with halogen, Ci-Ce alkyl, Ci-Ce haloalkyl, dC 6 cycloalkyl, hydroxy, Ci-Ce alkoxy, dC 6 -Halogenalkoxy or nitro substituted CH 2 heteroaryl, where the aryl part is 5- or 6-membered, may be substituted; or the heteroaryl substituted with heteroaryl, the aryl part being 5- or 6-membered, or with
- G is hydrogen, -C (X ⁇ ) -R 30 , -C (X 2 ) -X 3 -R 3 ⁇ , -C (X 4 ) -N (R 32 ) -R 33 , -SOa-R ⁇ , an alkali -, alkaline earth metal, sulfonium or ammonium cation, -P (X 5 ) (R35) -R36 or -CH 2 X6C (X 7 ) -R 37l -CH 2 X 8 C (X 9 ) -X ⁇ 0 - R 8, -CH 2 X ⁇ C (X ⁇ 2 ) -N (R 3 9) -R o or -CH 2 X ⁇ 3 SO 2 -R 4 ⁇ , wherein X 1 t X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 X 9 , X 1 0, Xu, X 12 and
- R36, R37, R38, R39, R 4 o and R 4 ⁇ independently of one another hydrogen, C1-C12-alkyl or with halogen, formyl, cyano, nitro, tri- CrC 6 -alkylsilyl, hydroxy, C ⁇ -C 6 -alkoxy, d-C 6 -alkoxycarbonyl, amino, -C-C 6 -alkylamino, di-dC 6 -alkylamino, mercapto, dC 6 - alkylthio, dC 6 -alkylcarbonyl, C ⁇ Ce-alkylcarbonylthio, C ⁇ -C 6 -alkylcarbonylamino, dC 6 - alkoxycarbonylamino, C ⁇ -C 6 alkylaminocarbonylamino, Ci-Ce-alkylthiocarbonyloxy, CC 6 - alkylthiocarbonylamino, d-C ⁇ -alk
- R M additionally C 2 -C 20 alkenyl or with halogen, dC 6 -alkylcarbonyl, CrC 6 -alkoxycarbonyl, Ci-Ce-alkylcarbonyloxy, -C-C 6 -alkoxy, C ⁇ -C 6 -thioalkyl, C ⁇ -C 6 -alkylthiocarbonyl , dC 6 - alkylcarbonylthio, -C-C 8 alkylsulfonyl, C ⁇ -C 6 -alkylsulfinyl, Ci-Ce-alkylaminosulfonyl, di-C Ce-alkylaminosulfonyl, dC 6 -alkylsulfonyloxy, C ⁇ -C 6 -alkylsulfonylamino, C ⁇ -C 6 - alkylamino, di- C ⁇ -C 6 -alkylamino, C ⁇ -C 6 alkylcarbonyla
- Ci-Ce-alkylcarbonyl Ci-Ce-alkylcarbonyl, dC 6 -alkoxycarbonyl, Ci-Ce- alkylcarbonyloxy, -C-C 6 -alkoxy, C ⁇ -C 6 -thioalkyl, CrC ⁇ -alkylthiocarbonyl, C ⁇ -C 6 - alkylcarbonylthio, Ci-Ce-alkylsulfonyl, d-Ce-alkylsulfinyl, -C-C 6 -alkylaminosulfonyl, di- d- C 6 -alkylaminosulfonyl, CrC 6 -alkylsulfonyloxy, C ⁇ -C 6 -alkylsulfonylamino, -C ⁇ -C 6 alkylamino , C 1 -C 6 alkylamino, CrC 6 alkylcarbonylamino,
- alkyl groups occurring in the substituent definitions can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl and hexyl and branched Isomers thereof.
- Suitable alkenyl and alkynyl groups as well as alkoxy and allylthio groups and other groups containing an alkyl unit are derived from the alkyl groups mentioned.
- cycloalkyl groups which are suitable according to the invention are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
- Halogen substituents are preferably fluorine, chlorine or bromine.
- 5- and 6-membered aromatic rings with heteroatoms are thiophenyl, furanyl and pyridinyl.
- Examples of 5- to 8-membered heteroaryls and heterocycloalkyls are pyrazolidine, 1, 2,3,6-tetrahydropyridazine, hexahydropyridazine, 1, 4,5-oxadiazepane, 1, 4,5-thiadiazepane and 1, 4,5-oxadiazoxane call.
- the invention also encompasses the salts which the compounds of the formula I can preferably form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
- Suitable salt formers are described, for example, in WO98 / 41089.
- the invention also includes the salts which the compounds of formula I can form with amines, alkali and alkaline earth metal bases or quaternary ammonium bases.
- alkali and alkaline earth metal hydroxides as salt formers, the hydroxides of lithium, sodium, potassium, magnesium or calcium should be emphasized, but especially those of sodium or potassium.
- Examples of amines suitable for the formation of ammonium salt include both ammonia and also primary, secondary and tertiary C 1 -C 8 -alkylamines, C 1 -C 4 -hydroxyalkylamines and C 2 -C -alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, iso -Propylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methyl-iso-propylamine, methylhexylamine, methyl nonylamine, methylpentadecylamine, methyl
- Preferred quaternary ammonium bases which are suitable for salt formation correspond, for example, to the formula [N (R a R b R c Rd)] OH, where R a , R, R c and R d independently of one another are C 1 -C 4 alkyl.
- R a , R, R c and R d independently of one another are C 1 -C 4 alkyl.
- Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.
- R 1 and R 3 are, independently of one another, dC-alkyl, in particular methyl or ethyl, C 2 -C -alkynyl, in particular ethynyl, C 1 -C 6 -alkoxy, in particular methoxy, dd-alkylthio, in particular Methylthio, C 1 -C 6 -haloalkyl, in particular chloromethyl and chloroethyl, formyl, C 1 -C 4 -alkylcarbonyl, in particular acetyl, or CC 4 -alkylamino or di- (C 1 -C 4 ) -alkylamino.
- methyl, ethyl, ethynyl and methoxy are particularly preferred.
- R 2 is phenyl, 2-thiophenyl, 3-thiophenyl, 2-furanyl, 3-furanyl, 2-pyridinyl, 3-pyridinyl or 4-pyridinyl, phenyl being particularly preferred.
- the corresponding substituted ring systems are also preferred, the substituents being halogen, hydroxy, mercapto, amino, cyano, nitro, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 3 -C 8 -cycloalkyl.
- R 4 and R 5 are independently C ⁇ -Ci2-alkyl, d-C ⁇ -C ⁇ 0 alkoxy-C 8 -alkyl or C 3 -C 8 -alkyl which one or can contain two oxygen atoms, or R and R 5 together with the atoms to which they are attached form a saturated, 5- to 8-, in particular 6- or 7- membered ring.
- R 4 and R 5 together form a radical -CH 2 CH 2 -O-CH2CH2- or - (CH 2 ) 4 -, these radicals with C 1 -C 10 -alkyl, dC 10 alkoxy, d-C ⁇ -alkoxy -CrCe alkoxy or hydroxyl can be substituted and a 2 to 6 Carbon atoms can contain alkylene or alkenylene chain, which can be interrupted by oxygen.
- Further preferred compounds of the formula I have, as substituents G, hydrogen or COR 30 , in particular pivaloyl, C (O) X 3 R 3 or in which X 3 is oxygen or sulfur, R 3i -CC 2 -alkyl, d -CC 2 -haloalkyl, C 2 -C 12 -alkenyl, d -CC 2 -alkoxyalkyl, C 3 -C 2 -cycloalkyl or phenyl, and R M -C-C 6 alkyl, Ci-Ce-haloalkyl, phenyl, phenyl substituted with chlorine, cyano or methyl; or heteroaryl or heteroaryl substituted with chlorine, cyano or methyl.
- R 1 and R 3 are, independently of one another, C 1 -C 4 -alkyl, in particular methyl or ethyl, C 2 -C -alkynyl, in particular ethynyl, CrC 6 -alkoxy, in particular methoxy or C 1 - C 4 alkylthio, especially methylthio
- R 2 is phenyl, 2-thiophenyl, 3-thiophenyl, 2-furanyl or 3-furanyl
- R 4 and R 5 are independently C 1 -C 2 alkyl or R and R 5 together with the atoms to which they are attached, a radical -CH 2 CH 2 -O-CH 2 CH 2 - or - (CH 2 ) -, these radicals with -C-C ⁇ o-alkyl or C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkoxy can be substituted and
- G is hydrogen or COR 30 , in particular piva
- the compounds of the formula I can be prepared by processes known per se, for example described in WO97 / 02243 or the references mentioned below, for example by introducing the aromatic ring R 2 through Pd (0) -catalyzed cross-coupling of aromatic tin compounds such as, for example, phenyltin trialkyl compounds , (Stille, JK Angew. Chem. Int. Ed. Engt. 1986, 25, 508. Kwon, HB; McKee, BH; Stille, JKJ Org. Chem. 1990, 55, 3114), or zinc compounds such as phenyl zinc halides (Negishi, E .; Valente, LF; Kobayashi, MJ Am. Chem. Soc. 1980.
- aromatic tin compounds such as, for example, phenyltin trialkyl compounds , (Stille, JK Angew. Chem. Int. Ed. Engt. 1986, 25, 508. Kwon, HB; McKee, BH; Still
- aromatic boric acids such as Furanyl boric acids (Miyaura; N .; Yanagi, T .; Suzuki, A. Synth. Commun. 1981, 11, 513), or aromatic boric acid esters such as phenyl boric acid dialkyl esters (Sato, M .; Miyaura, N .; Suzuki, A. Chem. Lett. 1989, 1405. Watanabe, T .; Miyaura, N .; Suzuki, A.
- R 7 - R 0 can be hydrogen and / or alkyl, in particular Ci-Ce-alkyl, and / or aryl, preferably phenyl and naphthyl.
- the malonic ester IV or the malondiamide V can be prepared, for example, by Pd (0) -catalyzed cross-coupling according to the following scheme:
- R 1t R 2 and R 3 have the meaning given under formula I and Hai represents chlorine, bromine or iodine, in the presence of an inert solvent, a base and a palladium catalyst at temperatures of 30 to 250 ° C.
- the reaction is preferably carried out under an inert gas atmosphere.
- the compounds of the formula XXX are known or by known processes, as described, for example, in J. Chem. Soc. Perkin Trans. 1 (1987), (4), 877-884.
- the compounds of formula VIII can, for example, by known methods such as. Sandmeyer reaction from the corresponding anilines of the formula VI
- R 1 and R 3 have the meanings given under formula I, via which diazonium salts are prepared.
- Such reactions are described, for example, in Vogel's Textbook of Practical Organic Chemistry, 5th Edition, BS Furniss, AJ Hannaford, PWG Smith, AR Tatchell; Longman Scientific & Technical 1989, page 923.
- the Compounds of the formula VI are known, some are commercially available or can be prepared analogously to known ones.
- Bases such as tri-alkali metal phosphates, alkali and alkaline earth metal hydrides, alkali and alkaline earth metal amides or alkali metal alcoholates, for example tri-potassium phosphate, sodium hydride, lithium diisopropylamide (LDA), sodium tert-butoxide or K-tert-butoxide are suitable for this reaction.
- tri-potassium phosphate sodium hydride, lithium diisopropylamide (LDA), sodium tert-butoxide or K-tert-butoxide
- Na-tert-butoxide, K-tert-butoxide and tripotassium phosphate are particularly preferred.
- Suitable solvents include aromatic hydrocarbons such as e.g. Xylene or toluene, ethers such as tetrahydrofuran, dioxane or ethylene glycol dimethyl ether, dimethyl sulfoxide or tertiary amides such as dimethylformamide, N-methylpyrrolidinone or dimethylacetamide or acyclic ureas such as N, N'-dimethylpropylene urea.
- aromatic hydrocarbons such as e.g. Xylene or toluene
- ethers such as tetrahydrofuran, dioxane or ethylene glycol dimethyl ether
- dimethyl sulfoxide or tertiary amides such as dimethylformamide, N-methylpyrrolidinone or dimethylacetamide or acyclic ureas such as N, N'-dimethylpropylene urea.
- the palladium catalysts which are suitable for the CC linkage reaction of a compound of the formula XXX with a compound of the formula VIII are generally palladium (II) or palladium (0) complexes such as, for example, palladium (II) dihalides, palladium (II) acetate , Palladium (ll) sulfate, bis (triphenylphosphine) palladium (ll) dichloride, bis (tricyclopentylphosphine) palladium (ll) dichloride, bis (tricyclohexylphosphine) palladium (ll) dichloride, bis ( dibenzylidene acetone) palladium (0) or tetrakis (triphenylphosphine) - palladium (O).
- palladium (II) dihalides palladium (II) acetate , Palladium (ll) sulfate
- the palladium catalyst can also be prepared from palladium (II) or palladium (O) compounds by complexation with the desired ligands 'in situ', for example by the palladium (II) salt to be complexed, for example palladium (II) dichloride (PdCI 2 ) or palladium (II) acetate (Pd (OAc) 2 ) together with the desired ligand, for example triphenylphosphine (PPh 3 ), tricyclopentylphosphine or tricyclohexylphosphine together with the selected solvent, a compound of formula VIII, a compound of formula XXX and base is presented.
- the palladium (II) salt for example palladium (II) dichloride (PdCI 2 ) or palladium (II) acetate (Pd (OAc) 2
- PdCI 2 palladium (II) acetate
- Pd (OAc) 2 palladium (OAc) 2
- Bidendate ligands are also possible, such as, for example, 1,1 'bis (diphenylphosphino) ferrocene or 1,2-bis (diphenylphosphino) ethane.
- the palladium (II) or palladium (O) complex desired for the CC coupling reaction is formed 'in situ', which then starts the CC coupling reaction.
- the palladium catalysts are used in an amount of 0.001-50 mol%, preferably in an amount of 0.1-15 mol%, based on the compound of the formula VIII.
- the reaction temperatures are chosen depending on the solvent used and, if appropriate, the pressure.
- the reaction is preferably carried out at atmospheric pressure.
- type compounds can be cyclized by aminal formation with aldehydes (here with formaldehyde). Ic is like by reaction of hydrazinal carbons
- R 0 is COOR 7 , COOR 8 , CONR 7 R, CONR 8 R ⁇ o or Cyano and R ⁇ is hydrogen, COOR 7 , COOR 8 , CONR 7 R 9 , CONR 8 R ⁇ 0 or Cyano, and R 7 ⁇ R 8 , R 9 and Rio and R 1f R 2 and R 3 have the meaning given above, where Ri and R 3 are not simultaneously hydrogen.
- Preferred intermediates correspond to the formulas
- R 1f R 2 and R 3 have the meanings given above, and shark is chlorine, bromine or iodine, where shark is different from iodine if Ri and R 3 are methyl and R 2 is phenyl.
- Hydrazine components required for the compounds according to the invention can be prepared by a new process. This is therefore also the subject of the present invention.
- This process is characterized in that the last stage in anhydrous alcohol is carried out directly with anhydrous hydrohalic acid or with in situ generated hydrohalic acid, for example from the action of methanol on acetyl chloride.
- the hydrohalic acid can be generated by reacting anhydrous alcohol such as methanol with an acyl halide such as acetyl halide.
- anhydrous alcohol such as methanol
- an acyl halide such as acetyl halide.
- Preferred hydrohalic acid is hydrochloric acid.
- aprotic, inert organic solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, carbon tetrachloride or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile, aminopropyl amine, nitrile such as acetonitrile or amine propylene nitrate such as acetonitrile or form Diethylformamide or N-methylpyrrolidinone.
- hydrocarbons such as benzene, toluene, xylene or cyclohexane
- chlorinated hydrocarbons such as dichloromethane, trichloromethane, carbon tetrachloride
- the reaction temperatures are preferably between -20 ° C and + 120 ° C.
- the reactions are generally slightly exothermic and can usually be carried out at room temperature.
- To the Shortening the reaction time or also to initiate the reaction can optionally be warmed up to the boiling point of the reaction mixture for a short time.
- the reaction times can also be shortened by adding a few drops of base as the reaction catalyst.
- Bases include, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo [2.2.2] octane, 1,5-diazabicyclo [4.3.0] non-5-ene or 1,5-diazabicyclo [5.4. 0] undec-7-en suitable.
- inorganic bases such as hydrides such as sodium or calcium hydride, hydroxides such as sodium or potassium hydroxide, carbonates such as sodium and potassium carbonate or hydrogen carbonates such as potassium and sodium hydrogen carbonate can also be used as bases.
- the compounds of the formula I can be isolated in a conventional manner by concentrating and / or evaporating the solvent and purified by recrystallizing or triturating the solid residue in solvents in which they do not dissolve well, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
- the active ingredient is drawn up in solution onto mineral granulate carriers or polymerized granules (urea / formaldehyde) and dried. If necessary, a coating can also be applied (coating granules), which allows the active ingredient to be dispensed in doses over a certain period of time.
- the compounds of formula I can be used in unchanged form, i.e. as they arise in the synthesis, are used as herbicides. However, they are preferably processed in the customary manner with the auxiliaries customary in formulation technology, e.g. to emulsifiable concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described for example in WO 97/34485 on pages 9 to 13.
- the application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, are chosen in the same way as the type of agent, the intended goals and the given conditions.
- the formulations ie the agents, preparations or compositions comprising the active ingredient of the formula I or at least one active ingredient of the formula I and generally one or more solid or liquid formulation auxiliaries are produced in a known manner, for example by intimately mixing and / or grinding the active ingredients with the formulation auxiliaries, such as, for example, solvents or solid carriers.
- formulation auxiliaries such as, for example, solvents or solid carriers.
- surface-active compounds surfactants
- solvents and solid carriers are given, for example, in WO 97/34485 on page 6.
- suitable surface-active compounds are nonionic, cationic and / or anionic surfactants and surfactant mixtures with good emulsifying, dispersing and wetting properties.
- suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8.
- the surfactants commonly used in formulation technology which include in "Mc Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981, Stumbleen, H., “Tensid-Taschenbuch", Carl Hanser Verlag, Kunststoff / Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants ", Vol III, Chemical Publishing Co., New York, 1980-81, are suitable for the preparation of the herbicidal compositions according to the invention.
- the herbicidal formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant. While concentrated products are preferred as a commodity, the end user generally uses diluted products.
- the agents can also contain other additives such as stabilizers e.g. optionally epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, e.g. Contain silicone oil, preservatives, viscosity regulators, binders, adhesives as well as fertilizers or other active ingredients.
- the active compounds of the formula I are generally applied to the plant or its habitat at a rate of from 0.001 to 4 kg / ha, in particular from 0.005 to 2 kg / ha.
- the dosage required for the desired effect can be determined by experiment. It depends on the type of action, the stage of development of the crop and the weed, and on the application (place, time, method) and, depending on these parameters, can vary within wide ranges.
- the compounds of the formula I are distinguished by herbicidal and growth-inhibiting properties which they have for use in crops of useful plants, in particular in Enable cereals, cotton, soybeans, sugar beets, sugar cane, plantations, rapeseed, maize and rice as well as for non-selective weed control. Cultures are also to be understood as meaning those which have been made tolerant to herbicides or herbicide classes by conventional breeding or genetic engineering methods, such as, for example, IMI Maize, Poast Protected Maize, Liberty Link Maize, Bt / Liberty Link Maize, IMI / Liberty Link Maize, IMI / Liberty Link / Bt Maize, Roundup Ready Maize and Roundup Ready / Bt Maize.
- the weeds to be controlled can be both monocotyledonous and dicotyledonous weeds, such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
- Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon,
- the compound of formula I can be used advantageously with a number of other known herbicides, preferably selected from the groups of the sulfonylureas, ureas, chloroacetanilides, chloroacetamides, diphenyl ethers, nitroanilines, oxadiazolones, pyrazoles, triazines, (hetero) aryloxypropionic acids, carbamates, thiocarbamates Mix, thiatriazines, cyclohexanediones, imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyloxypyridinecarboxylic acids, pyrimidinyloxybenzoic acids.
- other known herbicides preferably selected from the groups of the sulfonylureas, ureas, chloroacetanilides, chloroacetamides, diphenyl ethers, nitroanilines, oxadiazolones,
- the mixing partners of the compound of formula I can optionally also be in the form of esters or salts, such as z. B. in The Pesticide Manual, Eleventh Edition, 1997, BCPC.
- the compound of formula I and mixtures thereof with the other herbicides mentioned above can also be used in combination with safeners.
- safeners are preferably suitable: a compound of the formula S-1
- RSi hydrogen or chlorine and Rs 2 is hydrogen, dC 8 -alkyl or Ci-C ⁇ -alkyl substituted by Ci-Ce-alkoxy or C 3 -C 6 -alkenyloxy; or a compound of the formula S-Il
- egg is nitrogen or methine
- Rs ⁇ 8 , Rs ⁇ 9 , Rs 20 and Rs 2 ⁇ independently of one another are hydrogen or CC 4 alkyl, or Rs 18 and Rs ⁇ 9 or Rs 2 o and Rs 2 ⁇ together form a C 4 -C 6 alkylene bridge through oxygen , NH or -N (-CC-alkyl) - can be interrupted;
- C alkyl may be substituted, or Rs i3 and Rs M together form a C 3 -C -
- Alkenylene bridge which can be substituted by halogen or dC 4 alkyl, or Rs ⁇ 3 and
- RS 22 , Rs 23 , Rs 24 and Rs 25 independently of one another represent hydrogen, halogen, dC 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, -COORs 26 , trifluoromethyl, nitro or cyano, where Rs 6 are each hydrogen, d-C ⁇ 0 alkyl, dC 4 -alkoxy-C ⁇ -C 4 alkyl, dd-dd-alkylthio-alkyl, di-Ci-d-alkylamino-d-d alkyl, halo-dC 8 alkyl, C 2 -C 8 alkenyl, halo-C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 7 cycloalkyl, halo-C 3 -C 7 cycloalkyl, -C-C 8 alkylcarbonyl , Allylcarbony
- Rs ⁇ 7 represents hydrogen or -CC 4 alkyl
- Rs 27 is hydrogen, halogen, nitro, -CC alkyl or methoxy
- Rs 28 is hydrogen, halogen, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, - COOH or -COO-C 1 -C 4 -alkyl;
- Rs 29 is hydrogen, halogen, cyano, nitro, CrC 4 -alkyl, -C-C 4 -haloalkyl, CC 4 -alkylthio, C ⁇ -C 4 -alkylsulfinyl, C, -C 4 -alkylsulfonyl, -COOH, -COO-C ⁇ - C 4 alkyl, -CONRs 30 Rs 3 ⁇ , C (O) - phenyl, or phenyl substituted by halogen, C ⁇ -C alkyl, methoxy, nitro or trifluoromethyl, or -SO 2 NRS 32 RS 3S , -OSO 2 -dC 4 -alkyl, Ci-C ⁇ -alkoxy, or dC 6 -alkoxy substituted by -CC 4 -alkoxy or halogen, or C 3 -C 6 -alkenyloxy or C 3 -C 6 -alkenyloxy substitute
- Rs 38 is hydrogen, halogen or -CC alkyl
- Rs 39 is hydrogen, halogen, -CC 4 -alkyl, -COOH, -COO-C C 4 -alkyl, trifluoromethyl or
- Rs 40 is hydrogen, halogen, nitro, dC 4 alkyl, CC 4 alkoxy, C 1 -C 4 alkylthio, CC 4 -
- Alkylsulfinyl, CC -Alkylsulfonyl, -COOH, -COO-C ⁇ -C 4 alkyl or CONRs 42 Rs 43 means;
- Rs 4 is hydrogen, halogen or dC 4 alkyl; or Rs 0 and Rs 4i together form a C 3 -C alkylene bridge;
- Rs 42 and Rs "independently of one another are hydrogen or dd-alkyl, or Rs 42 and Rs" together form a C 4 -C 6 alkylene bridge which can be replaced by oxygen, NH or -N (d-
- C 4 alkyl) - can be interrupted
- RS J is hydrogen, halogen, -CC 4 -alkyl, -COOH, -COO-dC 4 -alkyl, trifluoromethyl or
- Rs 45 is hydrogen, halogen, nitro, C 1 -C 4 -alkyl, dC 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 -
- Alkylsulfinyl, CC 4 -alkylsulfonyl, -COOH, -COO-C ⁇ -C 4 alkyl or CONRs 46 Rs 47 means;
- Rs 46 and Rs 47 independently of one another are hydrogen or dC 4 -alkyl, or Rs ⁇ and Rs 47 together form a C 4 -C 6 -alkylene bridge which can be replaced by oxygen, NH or -N (C
- C-alkyl) - can be interrupted
- Alkylsulfinyl, dC 4 -alkylsulfonyl, -COOH, -COO-C ⁇ -C 4 alkyl or CONRs 50 Rs 5 ⁇ means;
- Rs 51 and Rs 52 independently of one another are hydrogen or C -C 4 alkyl, or Rs 5 ⁇ and Rs 52 together form a C 4 -C 6 alkylene bridge which is replaced by oxygen, NH or -N (d-d-alkyl) - can be interrupted; or a compound of formula SV
- RS53 and RS 5 4 are independently dC 6 alkyl or C 2 -C 6 alkenyl; or Rs 53 and Rs 55 and Rs 56 independently
- r represents 0 or 1
- Rs is hydrogen or C 4 -alkyl, which by C ⁇ -C 4 -alkoxy, C 4 alkylthio, CC 4 - alkylsulfinyl, C ⁇ -C 4 alkylsulfonyl, C ⁇ -C 4 haloalkyl, dC 4 haloalkoxy dd- Haloalkylthio, dC -haloalkylsulfinyl, dC 4 -haloalkylsulfonyl, nitro, cyano, - COOH, COO-dC 4 -alkyl, -NRs 80 Rs 8 ⁇ , -SO 2 NRs 82 Rs 83 or -CONRs ⁇ -tRs ⁇ s;
- Rs 78 is hydrogen, halogen, dC 4 alkyl, trifluoromethyl, dC 4 alkoxy or dd haloalkoxy;
- Rs 79 is hydrogen, halogen or -CC 4 alkyl
- Rs 80 is hydrogen, -CC alkyl or -CC 4 alkylcarbonyl
- Rs 8 is hydrogen or C 1 -C 4 alkyl
- Rs 80 and Rs 8 ⁇ together form a C 4 or C 5 alkylene group
- Rs 82 , Rs ⁇ , Rs ⁇ A and Rs ⁇ independently of one another are hydrogen or C 1 -C 4 -alkyl; or Rs 82 together with Rs ⁇ or Rs ⁇ together with Rs 85 independently of one another are C 4 - or C -alkylene, where one carbon atom is oxygen or sulfur, or one or two carbon atoms is -NH- or -N (dC 4 -alkyl ) - can be replaced;
- Rs 86 and Rs 87 are independently hydrogen or Ci-C ⁇ -alkyl; or Rs 86 and Rs 87 together are C 2 -C 6 alkylene;
- Rs 88 and Rs 89 independently of one another are hydrogen or -CC 8 alkyl; or Rs 88 and Rs 89 together form a C 2 -C 6 alkylene group;
- RS 90 stands for Rs 9 ⁇ -O-, Rs 92 -S- or -NRs 93 Rs 94 ;
- Rs 9 ⁇ and Rs 92 independently of one another hydrogen, C ⁇ -C 8 alkyl, Ci-Ce-haloalkyl, d- C 4 alkoxy-C 1 -C 8 alkyl, C 3 -C 6 alkenyloxy-dC 8 alkyl or phenyl-C C 8 -alkyl, where the phenyl ring can be substituted by halogen, dd-alkyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl or methylsulfonyl, or C 3 -C 6 -alkenyl, C 3 -C 6 -halogenalkenyl, phenyl Are -C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, phenyl-C 3 -C 6 alkynyl, oxetanyl, furyl or tetrahydrofuryl;
- Rs 95 and Rs 96 independently of one another are hydrogen or -CC 8 alkyl; or Rs 95 and Rs 96 together form a C 2 -C 6 alkylene group; and Rs 97 is C 2 -C 4 alkenyl or C 2 -C 4 alkynyl; with the provisos that a) at least one of the ring members E 2 , E 3 , E 4 or E 5 is carbonyl, and a ring member adjacent to this or these ring members is the group
- Rs 98 is hydrogen, -CC 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; and Rs 99 , Rsioo and RS 101 independently of one another denote hydrogen, d-C ⁇ -alkyl, C 3 -C 6 cycloalkyl or CC 6 alkoxy, with the proviso that one of the substituents Rs 99 , Rsioo and RS 101 is different from hydrogen is; or a compound of formula SX
- E 6 is nitrogen or methine
- n for the case that E 6 is nitrogen, 0, 1, 2 or 3 and for the case that E 6 is methine, 0, 1, 2, 3 or 4,
- RS 102 halogen , C ⁇ -C 4 -alkyl, C haloalkyl, C ⁇ -C 4 -alkoxy, C 4 haloalkoxy, nitro, -C 4 alkylthio, dd- alkylsulfonyl, C ⁇ -C 4 alkoxycarbonyl, phenyl or phenoxy, or C ⁇ -C 3 -alkyl, C 3 - haloalkyl, C ⁇ -C 3 -alkoxy, represents C 3 haloalkoxy, halogen, cyano or nitro-substituted phenyl or phenoxy;
- Rs ⁇ 03 hydrogen or -CC 4 alkyl;
- E 7 is oxygen or N-Rsios and Rs i05 a group of the formula
- E 8 is oxygen, sulfur, sulfinyl, sulfonyl or methine, Rsio ⁇ and Rs ⁇ 09 independently of one another CH 2 COORsn 2 or COORsn 3 or together a group of the formula - (CH 2 ) C (O) -OC (O) - (CH 2 ) - mean, and Rsn 2 and Rsn 3 independently of one another hydrogen, dd-alkyl, C 2 -C 4 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 - cycloalkyl, C ⁇ -C haloalkyl Mean metal or an ammonium cation; and Rsno and Rsm independently of one another are hydrogen, halogen or -CC 4 alkyl; or a compound of the formula S-Xlll
- Rs and Rsn 5 independently of one another are hydrogen, halogen or dd-haloalkyl
- Rsne is hydrogen, C, -C -alkyl, C 3 -C -alkenyl, C 3 -C -alkynyl, dC 4 - haloalkyl, C 3 -C 6 Cycloalkyl, a metal cation or an ammonium cation
- Rs 118 , Rsn 9 , Rs 121 and Rs 122 independently represent hydrogen or dd-alkyl;
- Rs 117 and Rs ⁇ 20 independently of one another hydrogen, dd-alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CrC 4 haloalkyl, C 3 -C 6 cycloalkyl, a metal cation or an ammonium cation mean; or a compound of formula S-XIV
- Rs ⁇ 23 is hydrogen, cyano, halogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C alkoxy, d-
- RS 125 and RS 126 independently of one another dC-alkyl, CC 4 -haloalkyl, C 3 -C 4 -alkenyl,
- Heteroaryl or by -CC 3 alkyl, CC 3 haloalkyl, CC 3 alkoxy, C -C 3 haloalkoxy,
- Rs ⁇ 27 and Rs ⁇ 28 independently of one another hydrogen, C ⁇ -C 4 alkyl, C ⁇ -C - haloalkyl, CC 4 -alkoxy, mono-C ⁇ -C 8 - or di-C1-C8-alkylamino, C 3 -C 6 - Mean cycloalkyl, d-C -thioalkyl, phenyl or heteroaryl;
- Rs 129 are hydrogen, C 4 -alkyl, C 4 haloalkyl, C r C 4 alkoxy, mono-C C 8 - or di-C1-C8-alkylamino, C 3 -C 6 cycloalkyl, dC 4 -Thioalkyl, phenyl, heteroaryl, OH, NH 2 , halogen, di -CC-C 4 -aminoalkyl, -C-C 4 -alkylthio, dC 4 -alkylsulfonyl or dC -alkoxycarbonyl;
- Rs 130 is hydrogen, dd-alkyl, C ⁇ -C 4 haloalkyl, C r C alkoxy, C ⁇ -C 8 mono - or di-C1-C8-alkylamino, C 3 -C 6 cycloalkyl, C ⁇ -C 4 - Thioalkyl, phenyl, heteroaryl, cyan
- Rs ⁇ 32 is hydrogen, C -alkyl, CC 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or d- C 4 -alkoxy-C r C 4 -alkyl;
- Rs ⁇ is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy and Rs ⁇ hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or CC 4 alkoxy; with the proviso that Rsi ⁇ and Rs ⁇ do not simultaneously represent hydrogen.
- Safeners which are particularly preferred for the agent according to the invention are selected from the group of compounds of the formula S1.1
- the compounds of the formulas S1.1 to S1.13 are known and are described, for example, in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997 under entry numbers 61 (formula S1.1, Benoxacor), 304 (formula S1.2 , Fenclorim), 154 (Formula S1.3, Cloquintocet), 462 (Formula S1.4, Mefenpyr-diethyl), 377 (Formula S1.5, Furilazole), 363 (Formula S1.8, Fluxofenim), 213 (Formula S1 .9, dichlormid) and 350 (formula S1.10, flurazole).
- the compound of formula S1.11 is known under the name MON 4660 (Monsanto) and e.g. in EP-A-0 436 483.
- the compound of formula S1.6 (AC 304415) is described for example in EP-A-0 613 618, the compound of formula S1.7 in DE-A-2948535.
- the compound of the formula S1.12 is described in DE-A-4331448, the compound of the formula S1.13 in DE-A-3525205.
- reaction mixture was degassed by introducing Agron for 0.33 h. Then was
- Tetrakistriphenylphosphine-Pd (0) (1.46g, 1.28 mmol) was added.
- reaction mixture was heated to 100 ° C. for 16 h, cooled and washed with NaOH solution (1N,
- TMEDA (17.1g, 0.147 mol) was dissolved in THF (distilled over Na, 500 ml), cooled to -78 ° C. and mixed with s-BuLi (113 ml of a 1.3M solution in cyclohexane, 0.147 mol). The reaction mixture was stirred at -78 ° C for 0.25 h, a solution of 13 (33.9 g, 0.134 mol) in THF (100 ml) was added dropwise and the mixture was stirred at -78 ° C for a further 0.25 h. The reaction mixture was treated dropwise with iodoethane (45.2g, 0.29 mol) and warmed to 0 ° C.
- TMEDA (8.9g, 0.077 mol) was dissolved in THF (distilled over Na, 400 ml), the reaction mixture was cooled to -78 ° C. and with s-BuLi (59 ml of a 1.3M solution in cyclohexane, 0.077 mol) and then a solution of 23 (24.8g, 0.07 mol) in THF (75 ml) was added dropwise. After 0.5 h at -78 ° C, the reaction mixture was mixed with iodomethane (13.3g, 0.085 mol) and warmed to 0 ° C. Aqueous, saturated NHCl solution (200 ml) was added to the reaction mixture and the organic phase was separated off.
- TMEDA (15.1g, 0.13 mol) was dissolved in THF (500 ml), cooled to -78 ° C. and s-BuLi (100 ml of a 1.3 M solution in cyclohexane, 0.13 mol) was added dropwise. 13 (30 g, 0.12 mol) was dissolved in THF (100 ml) and added dropwise to the reaction mixture within 0.5 h. After a further 0.5 h at -78 ° C, the reaction mixture was mixed with trimethyl borate. The reaction mixture was stirred at -78 ° C for 0.5 h, warmed to -40 ° C and mixed with an aqueous NH 4 CI solution (250 ml). The organic phase was washed with brine, dried over Na 2 SO4 and concentrated. 32 (36.7 g) was obtained as a crude product.
- TMEDA (1.49 g, 12.8 mmol) was dissolved in THF (50 ml) and cooled to -78 ° C.
- the reaction mixture was mixed with s-BuLi (9.8 ml of a 1.3 M solution in cyclohexane, 12.8 mmol), stirred for 0.25 h at -78 ° C., with a solution of 34 (3.3 g, 11.6 mmol) in THF (15 ml) dropwise added and stirred at -78 ° C for 0.3h.
- Ethyl iodide (2.0g, 13 mmol) was added to the reaction mixture.
- the reaction mixture was warmed to 0 ° C.
- N, N'-diacethylhydrazine 14 (768 g, 6.62 mol), 2,2'-dichlorodiethyl ether (1141 g, 7.9 mol) and potassium carbonate (1827 g, 13.3 mol) were initially charged in DMF (8.5 L) at room temperature.
- the resulting suspension was heated to 130 ° C for 3.5 h, cooled, filtered and concentrated.
- the residue was taken up in toluene (1000 ml) and stirred at 0 ° C for 16 h. After filtration, the product 15 was obtained as white crystals (574 g).
- the mother liquor was evaporated and recrystallized from a little methanol.
- Product 15 (108 g) was again obtained as white crystals.
- LC / MS: M + means the molecular weight determined from the coupled HPLC (High Performance Liquid Chromatography) and MS (Mass Spectrometry) analysis; the numerical values given after "UV” mean the frequency of the absorption maxima of the UV spectrum in nanometers, measured in water / acetonitrile.
- Ph phenyl
- Ph phenyl
- Ph phenyl
- Ph phenyl
- Ph phenyl
- Ph phenyl
- Ph phenyl
- test plants Monocot and dicot test plants are sown in pots in standard soil.
- the test substances are used as an aqueous suspension (made from a wettable powder (example F3, b) according to WO 97/34485) or as an emulsion (made from an emulsion concentrate (example F1, c) according to WO 97 / 34485) sprayed on in optimal dosage (500 l water / ha).
- the test plants are then cultivated further in the greenhouse under optimal conditions.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU75146/00A AU7514600A (en) | 1999-09-07 | 2000-09-05 | Novel herbicides |
PL00356456A PL356456A1 (en) | 1999-09-07 | 2000-09-05 | Novel herbicides |
EP00964108A EP1230245A2 (de) | 1999-09-07 | 2000-09-05 | Neue herbizide |
HU0202844A HUP0202844A3 (en) | 1999-09-07 | 2000-09-05 | Herbicidal 4-phenyl substituted pirazolinone derivatives, intermediates and preparation thereof |
CA002382432A CA2382432A1 (en) | 1999-09-07 | 2000-09-05 | Novel herbicides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH164499 | 1999-09-07 | ||
CH1644/99 | 1999-09-07 |
Publications (2)
Publication Number | Publication Date |
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WO2001017973A2 true WO2001017973A2 (de) | 2001-03-15 |
WO2001017973A3 WO2001017973A3 (de) | 2001-05-10 |
Family
ID=4215283
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2000/008657 WO2001017973A2 (de) | 1999-09-07 | 2000-09-05 | Neue herbizide |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1230245A2 (de) |
CN (1) | CN1377358A (de) |
AU (1) | AU7514600A (de) |
CA (1) | CA2382432A1 (de) |
HU (1) | HUP0202844A3 (de) |
PL (1) | PL356456A1 (de) |
WO (1) | WO2001017973A2 (de) |
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DE10311300A1 (de) | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
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2000
- 2000-09-05 AU AU75146/00A patent/AU7514600A/en not_active Abandoned
- 2000-09-05 PL PL00356456A patent/PL356456A1/xx not_active Application Discontinuation
- 2000-09-05 CN CN00813584A patent/CN1377358A/zh active Pending
- 2000-09-05 HU HU0202844A patent/HUP0202844A3/hu unknown
- 2000-09-05 EP EP00964108A patent/EP1230245A2/de not_active Withdrawn
- 2000-09-05 WO PCT/EP2000/008657 patent/WO2001017973A2/de not_active Application Discontinuation
- 2000-09-05 CA CA002382432A patent/CA2382432A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
CN1377358A (zh) | 2002-10-30 |
HUP0202844A2 (hu) | 2002-12-28 |
CA2382432A1 (en) | 2001-03-15 |
WO2001017973A3 (de) | 2001-05-10 |
HUP0202844A3 (en) | 2003-01-28 |
EP1230245A2 (de) | 2002-08-14 |
PL356456A1 (en) | 2004-06-28 |
AU7514600A (en) | 2001-04-10 |
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