TW200942173A - Novel herbicides - Google Patents

Info

Publication number

TW200942173A

TW200942173A TW097148351A TW97148351A TW200942173A TW 200942173 A TW200942173 A TW 200942173A TW 097148351 A TW097148351 A TW 097148351A TW 97148351 A TW97148351 A TW 97148351A TW 200942173 A TW200942173 A TW 200942173A

Authority

TW

Taiwan

Prior art keywords

formula

compound

alkyl

group

ch3ch2

Prior art date

2007-12-13

Links

• Espacenet
• Global Dossier
• Discuss

• 239000004009 herbicide Substances 0.000 title claims abstract description 16
• 150000001875 compounds Chemical class 0.000 claims description 898
• -1 cyano, thio Chemical group 0.000 claims description 444
• 125000000217 alkyl group Chemical group 0.000 claims description 295
• 239000000203 mixture Substances 0.000 claims description 227
• 239000007789 gas Substances 0.000 claims description 211
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 149
• 239000000460 chlorine Substances 0.000 claims description 132
• 229910052739 hydrogen Inorganic materials 0.000 claims description 120
• 239000001257 hydrogen Substances 0.000 claims description 120
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 110
• 125000003545 alkoxy group Chemical group 0.000 claims description 81
• 238000002360 preparation method Methods 0.000 claims description 81
• 229910052736 halogen Inorganic materials 0.000 claims description 74
• 150000002367 halogens Chemical class 0.000 claims description 70
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 63
• 125000001188 haloalkyl group Chemical group 0.000 claims description 63
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
• 239000002904 solvent Substances 0.000 claims description 56
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 54
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• 150000002431 hydrogen Chemical group 0.000 claims description 43
• 239000002253 acid Substances 0.000 claims description 40
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 39
• 238000000034 method Methods 0.000 claims description 38
• 238000006243 chemical reaction Methods 0.000 claims description 35
• 125000004414 alkyl thio group Chemical group 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
• 239000007787 solid Substances 0.000 claims description 30
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 29
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 28
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 25
• 229910052760 oxygen Inorganic materials 0.000 claims description 25
• 239000001301 oxygen Substances 0.000 claims description 24
• 241000196324 Embryophyta Species 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 239000003054 catalyst Substances 0.000 claims description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 229920006395 saturated elastomer Polymers 0.000 claims description 14
• 239000003446 ligand Substances 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
• 125000004434 sulfur atom Chemical group 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 229910052763 palladium Inorganic materials 0.000 claims description 12
• 101150010802 CVC2 gene Proteins 0.000 claims description 11
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 230000002363 herbicidal effect Effects 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• 150000003254 radicals Chemical class 0.000 claims description 9
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 150000002148 esters Chemical class 0.000 claims description 8
• 229910052707 ruthenium Inorganic materials 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 238000002156 mixing Methods 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 239000002841 Lewis acid Substances 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 150000001768 cations Chemical class 0.000 claims description 5
• 150000007517 lewis acids Chemical class 0.000 claims description 5
• 125000003566 oxetanyl group Chemical group 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 241000209504 Poaceae Species 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000000463 material Substances 0.000 claims description 4
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
• 125000005418 aryl aryl group Chemical group 0.000 claims description 2
• 239000012267 brine Substances 0.000 claims description 2
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
• 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 claims 1
• KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims 1
• 108091081050 CrcZ Proteins 0.000 claims 1
• 229920000858 Cyclodextrin Polymers 0.000 claims 1
• BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 claims 1
• HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 claims 1
• 150000001345 alkine derivatives Chemical class 0.000 claims 1
• BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 claims 1
• 125000005577 anthracene group Chemical group 0.000 claims 1
• 229910052785 arsenic Inorganic materials 0.000 claims 1
• RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 1
• 125000004997 halocarbonyl group Chemical group 0.000 claims 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
• BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 claims 1
• 238000006467 substitution reaction Methods 0.000 claims 1
• 244000045561 useful plants Species 0.000 claims 1
• SJSBKIXOCNOEFF-UHFFFAOYSA-N 2h-thiopyran 1,1-dioxide Chemical compound O=S1(=O)CC=CC=C1 SJSBKIXOCNOEFF-UHFFFAOYSA-N 0.000 abstract 1
• CZVTYGFISHLVHK-UHFFFAOYSA-N 4h-pyran-2,3-dione Chemical compound O=C1CC=COC1=O CZVTYGFISHLVHK-UHFFFAOYSA-N 0.000 abstract 1
• SUEVWEWAIVZWCQ-UHFFFAOYSA-N cyclohexane-1,2,3-trione Chemical class O=C1CCCC(=O)C1=O SUEVWEWAIVZWCQ-UHFFFAOYSA-N 0.000 abstract 1
• 239000002585 base Substances 0.000 description 211
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 136
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 136
• 239000011541 reaction mixture Substances 0.000 description 116
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
• 239000000243 solution Substances 0.000 description 68
• 235000019439 ethyl acetate Nutrition 0.000 description 58
• 230000002829 reductive effect Effects 0.000 description 53
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 49
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
• 229920002554 vinyl polymer Polymers 0.000 description 38
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 239000003921 oil Substances 0.000 description 34
• 235000019198 oils Nutrition 0.000 description 34
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• 239000000706 filtrate Substances 0.000 description 30
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
• 238000004440 column chromatography Methods 0.000 description 28
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
• 239000004480 active ingredient Substances 0.000 description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 239000012074 organic phase Substances 0.000 description 24
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
• 238000000746 purification Methods 0.000 description 22
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 21
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
• 241000237858 Gastropoda Species 0.000 description 20
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 20
• ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 19
• 239000012299 nitrogen atmosphere Substances 0.000 description 19
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
• 239000000284 extract Substances 0.000 description 18
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
• 150000001412 amines Chemical class 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
• 239000000654 additive Substances 0.000 description 16
• 101150041968 CDC13 gene Proteins 0.000 description 15
• 239000000741 silica gel Substances 0.000 description 15
• 229910002027 silica gel Inorganic materials 0.000 description 15
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
• 125000000304 alkynyl group Chemical group 0.000 description 14
• 239000008346 aqueous phase Substances 0.000 description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
• 150000002576 ketones Chemical class 0.000 description 14
• 125000003342 alkenyl group Chemical group 0.000 description 13
• 238000009472 formulation Methods 0.000 description 13
• 229910052708 sodium Inorganic materials 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
• 230000015572 biosynthetic process Effects 0.000 description 12
• BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 12
• 235000019441 ethanol Nutrition 0.000 description 11
• 239000007788 liquid Substances 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• 239000004094 surface-active agent Substances 0.000 description 11
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
• 239000003153 chemical reaction reagent Substances 0.000 description 10
• GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
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• 239000007983 Tris buffer Substances 0.000 description 9
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
• 125000000262 haloalkenyl group Chemical group 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
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• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 240000008042 Zea mays Species 0.000 description 8
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
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• 230000000996 additive effect Effects 0.000 description 8
• 125000003277 amino group Chemical group 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• 235000005822 corn Nutrition 0.000 description 8
• 238000005859 coupling reaction Methods 0.000 description 8
• 238000006460 hydrolysis reaction Methods 0.000 description 8
• 229910052744 lithium Inorganic materials 0.000 description 8
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
• 239000002689 soil Substances 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• 244000025254 Cannabis sativa Species 0.000 description 7
• 239000012298 atmosphere Substances 0.000 description 7
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
• 238000010828 elution Methods 0.000 description 7
• 230000007062 hydrolysis Effects 0.000 description 7
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical class NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 7
• 229940067157 phenylhydrazine Drugs 0.000 description 7
• XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
• 239000005977 Ethylene Substances 0.000 description 6
• 239000005574 MCPA Substances 0.000 description 6
• WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 6
• 125000003282 alkyl amino group Chemical group 0.000 description 6
• 239000012230 colorless oil Substances 0.000 description 6
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