TW297024B

TW297024B -

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Publication number: TW297024B
Authority: TW; Taiwan
Prior art keywords: group; carbon atoms; formula; ministry; branched
Prior art date: 1993-03-26

Application number

TW083101605A

Other languages

English (en)

Chinese (zh)

Inventor

Santel Hans-Joachim

Dollinger Markus

Original Assignee

Bayer Ag

Priority date

1993-03-26

Filing date

1994-02-25

Publication date

1997-02-01

1994-02-25 Application filed by Bayer Ag filed Critical Bayer Ag

1997-02-01 Application granted granted Critical

1997-02-01 Publication of TW297024B publication Critical patent/TW297024B/zh

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125000004432 carbon atom Chemical group C* 0.000 claims description 132
125000000217 alkyl group Chemical group 0.000 claims description 100
125000001424 substituent group Chemical group 0.000 claims description 78
150000001875 compounds Chemical class 0.000 claims description 77
238000000034 method Methods 0.000 claims description 60
-1 Alkyloxyalkoxy Chemical group 0.000 claims description 54
239000011737 fluorine Substances 0.000 claims description 51
229910052731 fluorine Inorganic materials 0.000 claims description 51
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 46
229910052794 bromium Inorganic materials 0.000 claims description 46
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 45
239000007789 gas Substances 0.000 claims description 44
239000001257 hydrogen Substances 0.000 claims description 44
229910052739 hydrogen Inorganic materials 0.000 claims description 44
238000011049 filling Methods 0.000 claims description 43
125000003545 alkoxy group Chemical group 0.000 claims description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
125000004093 cyano group Chemical group *C#N 0.000 claims description 31
238000006243 chemical reaction Methods 0.000 claims description 28
125000000753 cycloalkyl group Chemical group 0.000 claims description 27
229910052760 oxygen Inorganic materials 0.000 claims description 26
239000001301 oxygen Substances 0.000 claims description 26
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
125000005843 halogen group Chemical group 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
125000004414 alkyl thio group Chemical group 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
239000003085 diluting agent Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
150000002431 hydrogen Chemical group 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 11
239000004009 herbicide Substances 0.000 claims description 10
229960005437 etoperidone Drugs 0.000 claims description 9
230000002363 herbicidal effect Effects 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 8
239000003638 chemical reducing agent Substances 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
230000021736 acetylation Effects 0.000 claims description 3
238000006640 acetylation reaction Methods 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
238000006277 sulfonation reaction Methods 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 10
125000004076 pyridyl group Chemical group 0.000 claims 3
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
125000002541 furyl group Chemical group 0.000 claims 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
125000001725 pyrenyl group Chemical group 0.000 claims 2
IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical class O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 claims 1
239000008267 milk Substances 0.000 claims 1
210000004080 milk Anatomy 0.000 claims 1
235000013336 milk Nutrition 0.000 claims 1
239000012434 nucleophilic reagent Substances 0.000 claims 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 41
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 40
125000000623 heterocyclic group Chemical group 0.000 description 38
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 35
239000000460 chlorine Substances 0.000 description 34
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 25
229910052801 chlorine Inorganic materials 0.000 description 25
239000000203 mixture Substances 0.000 description 25
125000003118 aryl group Chemical group 0.000 description 23
229910052757 nitrogen Inorganic materials 0.000 description 21
229910052717 sulfur Inorganic materials 0.000 description 21
239000011593 sulfur Substances 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
241000196324 Embryophyta Species 0.000 description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 19
238000012360 testing method Methods 0.000 description 19
239000002585 base Substances 0.000 description 18
125000004429 atom Chemical group 0.000 description 17
230000000704 physical effect Effects 0.000 description 16
229920006395 saturated elastomer Polymers 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000004390 alkyl sulfonyl group Chemical group 0.000 description 12
125000000304 alkynyl group Chemical group 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
125000001188 haloalkyl group Chemical group 0.000 description 11
125000005842 heteroatom Chemical group 0.000 description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
239000007858 starting material Substances 0.000 description 11
241000282376 Panthera tigris Species 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
244000025254 Cannabis sativa Species 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000004644 alkyl sulfinyl group Chemical group 0.000 description 8
238000009472 formulation Methods 0.000 description 8
150000002576 ketones Chemical class 0.000 description 8
239000007787 solid Substances 0.000 description 8
240000005979 Hordeum vulgare Species 0.000 description 7
235000007340 Hordeum vulgare Nutrition 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
238000007639 printing Methods 0.000 description 7
125000000547 substituted alkyl group Chemical group 0.000 description 7
WNWOTMKHOLCHRJ-UHFFFAOYSA-N 1,4-dihydrotriazol-5-one Chemical class O=C1CN=NN1 WNWOTMKHOLCHRJ-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000004666 alkoxyiminoalkyl group Chemical group 0.000 description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
239000002689 soil Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000013589 supplement Substances 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 5
241001290610 Abildgaardia Species 0.000 description 5
244000017020 Ipomoea batatas Species 0.000 description 5
235000002678 Ipomoea batatas Nutrition 0.000 description 5
241000209140 Triticum Species 0.000 description 5
235000021307 Triticum Nutrition 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
125000005415 substituted alkoxy group Chemical group 0.000 description 5
235000021419 vinegar Nutrition 0.000 description 5
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
DLKNOGQOOZFICZ-UHFFFAOYSA-N 2,4,5-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C=C1F DLKNOGQOOZFICZ-UHFFFAOYSA-N 0.000 description 4
241000219318 Amaranthus Species 0.000 description 4
244000075850 Avena orientalis Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000004606 Fillers/Extenders Substances 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
241000207763 Solanum Species 0.000 description 4
235000002634 Solanum Nutrition 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
230000002079 cooperative effect Effects 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000012973 diazabicyclooctane Substances 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
150000002825 nitriles Chemical group 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
125000004149 thio group Chemical group *S* 0.000 description 4
IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
239000005695 Ammonium acetate Substances 0.000 description 3
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
239000005944 Chlorpyrifos Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000005561 Glufosinate Substances 0.000 description 3
235000007232 Matricaria chamomilla Nutrition 0.000 description 3
244000042664 Matricaria chamomilla Species 0.000 description 3
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
241000218989 Trichosanthes Species 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
239000000654 additive Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
235000019257 ammonium acetate Nutrition 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
239000001099 ammonium carbonate Substances 0.000 description 3
235000012501 ammonium carbonate Nutrition 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000003958 fumigation Methods 0.000 description 3
238000002309 gasification Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
229910052750 molybdenum Inorganic materials 0.000 description 3
239000011733 molybdenum Substances 0.000 description 3
ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
125000003884 phenylalkyl group Chemical group 0.000 description 3
235000011056 potassium acetate Nutrition 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000004659 sterilization and disinfection Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
238000009333 weeding Methods 0.000 description 3
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
235000009328 Amaranthus caudatus Nutrition 0.000 description 2
240000001592 Amaranthus caudatus Species 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
241001666377 Apera Species 0.000 description 2
235000016068 Berberis vulgaris Nutrition 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
241001674044 Blattodea Species 0.000 description 2
235000006463 Brassica alba Nutrition 0.000 description 2
235000011371 Brassica hirta Nutrition 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
235000007516 Chrysanthemum Nutrition 0.000 description 2
240000005250 Chrysanthemum indicum Species 0.000 description 2
241000207199 Citrus Species 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
241000208296 Datura Species 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
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