CN1305466A

CN1305466A - 取代的苯基哒嗪酮类化合物

取代的苯基哒嗪酮类化合物 Download PDF

Info

Publication number: CN1305466A
Authority: CN; China
Prior art keywords: group; alkyl; bases; fluoro; amino
Prior art date: 1998-04-09
Legal status : Pending

Application number

CN99807143A

Other languages

English (en)

Chinese (zh)

Inventor

K·H·林克尔

A·胡珀茨

M·W·德鲁斯

M·多林格

I·维特肖洛夫斯基

C·埃尔德伦

Current Assignee

Bayer AG

Original Assignee

Bayer AG

Priority date

1998-04-09

Filing date

1999-03-26

Publication date

2001-07-25

1999-03-26 Application filed by Bayer AG filed Critical Bayer AG

2001-07-25 Publication of CN1305466A publication Critical patent/CN1305466A/zh

Status Pending legal-status Critical Current

Links

TVKFDBOFBKXOQT-UHFFFAOYSA-N 5-phenyl-1h-pyridazin-6-one Chemical class O=C1NN=CC=C1C1=CC=CC=C1 TVKFDBOFBKXOQT-UHFFFAOYSA-N 0.000 title claims abstract description 24
-1 formamyl Chemical group 0.000 claims description 454
239000002585 base Substances 0.000 claims description 238
150000001875 compounds Chemical class 0.000 claims description 78
239000000460 chlorine Substances 0.000 claims description 76
239000001301 oxygen Substances 0.000 claims description 61
229910052760 oxygen Inorganic materials 0.000 claims description 61
125000004093 cyano group Chemical group *C#N 0.000 claims description 53
239000001257 hydrogen Substances 0.000 claims description 51
229910052739 hydrogen Inorganic materials 0.000 claims description 51
150000002431 hydrogen Chemical class 0.000 claims description 50
229910052801 chlorine Inorganic materials 0.000 claims description 49
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 48
239000000203 mixture Substances 0.000 claims description 48
125000000217 alkyl group Chemical group 0.000 claims description 45
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 42
229910052794 bromium Inorganic materials 0.000 claims description 42
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 41
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
229910052731 fluorine Inorganic materials 0.000 claims description 38
238000000034 method Methods 0.000 claims description 38
239000011737 fluorine Substances 0.000 claims description 37
229910052799 carbon Inorganic materials 0.000 claims description 36
150000001721 carbon Chemical group 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
241000196324 Embryophyta Species 0.000 claims description 28
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
150000001345 alkine derivatives Chemical class 0.000 claims description 21
239000003795 chemical substances by application Substances 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000004414 alkyl thio group Chemical group 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
239000005864 Sulphur Substances 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
125000002541 furyl group Chemical group 0.000 claims description 16
125000004076 pyridyl group Chemical group 0.000 claims description 16
125000003282 alkyl amino group Chemical group 0.000 claims description 14
125000003368 amide group Chemical group 0.000 claims description 14
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 14
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 13
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 12
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 12
239000004215 Carbon black (E152) Substances 0.000 claims description 11
229930195733 hydrocarbon Natural products 0.000 claims description 11
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 11
MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 claims description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
150000002430 hydrocarbons Chemical class 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 8
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
125000003226 pyrazolyl group Chemical group 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
125000004306 triazinyl group Chemical group 0.000 claims description 8
125000001425 triazolyl group Chemical group 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 7
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims description 6
QOAMWZMAXNNNDC-UHFFFAOYSA-N 4-(1,2-thiazol-3-yl)oxadiazole Chemical compound S1C=CC(C=2N=NOC=2)=N1 QOAMWZMAXNNNDC-UHFFFAOYSA-N 0.000 claims description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
125000005879 dioxolanyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
230000000802 nitrating effect Effects 0.000 claims description 5
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
TWBIDQDUOXHFSN-UHFFFAOYSA-N C[CH]C=O Chemical compound C[CH]C=O TWBIDQDUOXHFSN-UHFFFAOYSA-N 0.000 claims description 4
NRAINUFKKPBZQY-UHFFFAOYSA-N [O]C1CC1 Chemical compound [O]C1CC1 NRAINUFKKPBZQY-UHFFFAOYSA-N 0.000 claims description 4
GYAPJISEIGCPQO-UHFFFAOYSA-N [O]C1CCC1 Chemical compound [O]C1CCC1 GYAPJISEIGCPQO-UHFFFAOYSA-N 0.000 claims description 4
DWDAZFJBSZTCCM-UHFFFAOYSA-N [O]C1CCCCC1 Chemical compound [O]C1CCCCC1 DWDAZFJBSZTCCM-UHFFFAOYSA-N 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 4
125000006323 alkenyl amino group Chemical group 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000001118 alkylidene group Chemical group 0.000 claims description 4
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
VCZIFQMEDXLHEA-UHFFFAOYSA-N cyclopentylperoxycyclohexane Chemical compound C1(CCCC1)OOC1CCCCC1 VCZIFQMEDXLHEA-UHFFFAOYSA-N 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 4
125000003566 oxetanyl group Chemical group 0.000 claims description 4
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 4
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 4
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 4
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 3
ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical class OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 2
WWAUPJGLSKKLCL-UHFFFAOYSA-N C(CCC)=CC=CON Chemical compound C(CCC)=CC=CON WWAUPJGLSKKLCL-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 14
241000607479 Yersinia pestis Species 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
241000405414 Rehmannia Species 0.000 claims 1
239000004009 herbicide Substances 0.000 abstract description 4
239000013067 intermediate product Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
239000003999 initiator Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
238000003756 stirring Methods 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
150000004702 methyl esters Chemical class 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
238000001035 drying Methods 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
244000025254 Cannabis sativa Species 0.000 description 10
239000012141 concentrate Substances 0.000 description 10
230000000694 effects Effects 0.000 description 10
235000011167 hydrochloric acid Nutrition 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
125000004494 ethyl ester group Chemical group 0.000 description 9
239000002904 solvent Substances 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
239000002689 soil Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000001632 sodium acetate Substances 0.000 description 7
235000017281 sodium acetate Nutrition 0.000 description 7
239000003643 water by type Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
241000209140 Triticum Species 0.000 description 6
235000021307 Triticum Nutrition 0.000 description 6
239000000975 dye Substances 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
239000000463 material Substances 0.000 description 6
229940067157 phenylhydrazine Drugs 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 5
239000007789 gas Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
238000005507 spraying Methods 0.000 description 5
235000005781 Avena Nutrition 0.000 description 4
244000075850 Avena orientalis Species 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
241000209117 Panicum Species 0.000 description 4
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 4
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
241000207763 Solanum Species 0.000 description 4
235000002634 Solanum Nutrition 0.000 description 4
241000209072 Sorghum Species 0.000 description 4
235000011684 Sorghum saccharatum Nutrition 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 4
230000008029 eradication Effects 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000002363 herbicidal effect Effects 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229940043265 methyl isobutyl ketone Drugs 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000010902 straw Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000219198 Brassica Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
241000801118 Lepidium Species 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000004176 ammonification Methods 0.000 description 3
230000006378 damage Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
KZENFXVDPUMQOE-UHFFFAOYSA-N ethyl 2-(triphenyl-$l^{5}-phosphanylidene)propanoate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C(C)C(=O)OCC)C1=CC=CC=C1 KZENFXVDPUMQOE-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 3
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