DE10154075A1

DE10154075A1 - Substituierte Pyrimidine

Substituierte Pyrimidine

Info

Publication number: DE10154075A1
Authority: DE; Germany
Prior art keywords: phenyl; optionally substituted; alkyl; methyl; halogen
Prior art date: 2001-11-02
Legal status : Withdrawn

Application number

DE10154075A

Other languages

German (de)

English (en)

Inventor

Ernst R F Gesing

Mark Wilhelm Drewes

Peter Dahmen

Dieter Feucht

Rolf Pontzen

Current Assignee

Bayer CropScience AG

Original Assignee

Bayer CropScience AG

Priority date

2001-11-02

Filing date

2001-11-02

Publication date

2003-05-15

2001-11-02 Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG

2001-11-02 Priority to DE10154075A priority Critical patent/DE10154075A1/de

2002-10-21 Priority to EP02777320A priority patent/EP1444208A1/de

2002-10-21 Priority to US10/493,781 priority patent/US20050065166A1/en

2002-10-21 Priority to PCT/EP2002/011744 priority patent/WO2003037878A1/de

2002-10-21 Priority to JP2003540160A priority patent/JP2005512985A/ja

2002-10-29 Priority to ARP020104107A priority patent/AR037130A1/es

2003-05-15 Publication of DE10154075A1 publication Critical patent/DE10154075A1/de

Status Withdrawn legal-status Critical Current

Links

150000003230 pyrimidines Chemical class 0.000 title claims abstract description 11
238000000034 method Methods 0.000 claims abstract description 27
239000004009 herbicide Substances 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 3
-1 Nitro, cyano, carboxy, carbamoyl Chemical group 0.000 claims description 236
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 57
239000000460 chlorine Substances 0.000 claims description 57
229910052801 chlorine Inorganic materials 0.000 claims description 57
229910052736 halogen Inorganic materials 0.000 claims description 55
229910052731 fluorine Inorganic materials 0.000 claims description 54
239000011737 fluorine Substances 0.000 claims description 54
150000002367 halogens Chemical class 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 51
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 42
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 42
229910052794 bromium Inorganic materials 0.000 claims description 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
125000001153 fluoro group Chemical group F* 0.000 claims description 29
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 26
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 25
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 21
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 18
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 11
125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
125000000335 thiazolyl group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
125000002541 furyl group Chemical group 0.000 claims description 9
125000002971 oxazolyl group Chemical group 0.000 claims description 9
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
125000005605 benzo group Chemical class 0.000 claims description 8
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 8
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000003806 alkyl carbonyl amino 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
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000005530 alkylenedioxy group Chemical class 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
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical class SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims description 4
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 3
239000004606 Fillers/Extenders Substances 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
GIDIIKXHRDVQDI-UHFFFAOYSA-N 2-(thiophen-2-ylmethylsulfanyl)-5-(trifluoromethyl)pyrimidine Chemical compound N1=CC(C(F)(F)F)=CN=C1SCC1=CC=CS1 GIDIIKXHRDVQDI-UHFFFAOYSA-N 0.000 claims description 2
FHFIXRRHKSMREA-UHFFFAOYSA-N 2-(thiophen-2-ylmethylsulfinyl)-5-(trifluoromethyl)pyrimidine Chemical compound N1=CC(C(F)(F)F)=CN=C1S(=O)CC1=CC=CS1 FHFIXRRHKSMREA-UHFFFAOYSA-N 0.000 claims description 2
DACORWPQRQVHBR-UHFFFAOYSA-N 2-(thiophen-2-ylmethylsulfonyl)-5-(trifluoromethyl)pyrimidine Chemical compound N1=CC(C(F)(F)F)=CN=C1S(=O)(=O)CC1=CC=CS1 DACORWPQRQVHBR-UHFFFAOYSA-N 0.000 claims description 2
IVTRMSHONMYNDK-UHFFFAOYSA-N 2-benzylsulfanyl-4-chloro-5-methylpyrimidine Chemical compound N1=C(Cl)C(C)=CN=C1SCC1=CC=CC=C1 IVTRMSHONMYNDK-UHFFFAOYSA-N 0.000 claims description 2
CLTWHBOOBMCRCH-UHFFFAOYSA-N 2-benzylsulfanyl-5-(trifluoromethyl)pyrimidine Chemical compound N1=CC(C(F)(F)F)=CN=C1SCC1=CC=CC=C1 CLTWHBOOBMCRCH-UHFFFAOYSA-N 0.000 claims description 2
BDOPQKITZWRPQM-UHFFFAOYSA-N 2-benzylsulfonyl-5-(trifluoromethyl)pyrimidine Chemical compound N1=CC(C(F)(F)F)=CN=C1S(=O)(=O)CC1=CC=CC=C1 BDOPQKITZWRPQM-UHFFFAOYSA-N 0.000 claims description 2
WOOGFIPTSBYUFR-UHFFFAOYSA-N 4,6-dichloro-5-methyl-2-(naphthalen-2-ylmethylsulfanyl)pyrimidine Chemical compound N1=C(Cl)C(C)=C(Cl)N=C1SCC1=CC=C(C=CC=C2)C2=C1 WOOGFIPTSBYUFR-UHFFFAOYSA-N 0.000 claims description 2
NWKNAOQJLIJBGN-UHFFFAOYSA-N 4-chloro-2-[(2,4-dichlorophenyl)methylsulfanyl]-5-methylpyrimidine Chemical compound N1=C(Cl)C(C)=CN=C1SCC1=CC=C(Cl)C=C1Cl NWKNAOQJLIJBGN-UHFFFAOYSA-N 0.000 claims description 2
DHHHQULBJQNTGM-UHFFFAOYSA-N 4-chloro-2-[(4-chlorophenyl)methylsulfanyl]-5-methylpyrimidine Chemical compound N1=C(Cl)C(C)=CN=C1SCC1=CC=C(Cl)C=C1 DHHHQULBJQNTGM-UHFFFAOYSA-N 0.000 claims description 2
XVYALGAWXBETTK-UHFFFAOYSA-N 5-methyl-2-[(1-methyl-5-nitroimidazol-2-yl)methylsulfanyl]pyrimidine Chemical compound N1=CC(C)=CN=C1SCC1=NC=C([N+]([O-])=O)N1C XVYALGAWXBETTK-UHFFFAOYSA-N 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
DWWFADHDYAGCQG-UHFFFAOYSA-N 4-chloro-2-[chloro(phenyl)methyl]sulfanyl-5-methylpyrimidine Chemical compound N1=C(Cl)C(C)=CN=C1SC(Cl)C1=CC=CC=C1 DWWFADHDYAGCQG-UHFFFAOYSA-N 0.000 claims 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
241000196324 Embryophyta Species 0.000 description 76
239000004480 active ingredient Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
230000008569 process Effects 0.000 description 18
239000000203 mixture Substances 0.000 description 17
238000002360 preparation method Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 10
241000219146 Gossypium Species 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229920000742 Cotton Polymers 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000002689 soil Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
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 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
240000008042 Zea mays Species 0.000 description 7
235000002017 Zea mays subsp mays Nutrition 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
108090000623 proteins and genes Proteins 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
235000010469 Glycine max Nutrition 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
240000006394 Sorghum bicolor Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
235000013399 edible fruits Nutrition 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
239000008187 granular material Substances 0.000 description 5
230000002363 herbicidal effect Effects 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
244000068988 Glycine max Species 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
244000061456 Solanum tuberosum Species 0.000 description 4
235000002595 Solanum tuberosum Nutrition 0.000 description 4
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
241001233957 eudicotyledons Species 0.000 description 4
235000009973 maize Nutrition 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000243 solution Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
UWIAZCHVMPFABJ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylsulfanyl]-4-methyl-5,6,7,8-tetrahydroquinazoline Chemical compound N=1C=2CCCCC=2C(C)=NC=1SCC1=CC=C(Cl)C=C1 UWIAZCHVMPFABJ-UHFFFAOYSA-N 0.000 description 3
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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
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241000207783 Ipomoea Species 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000209510 Liliopsida Species 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
230000009471 action Effects 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 3
238000009395 breeding Methods 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
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150000002170 ethers Chemical class 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
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
235000016709 nutrition Nutrition 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
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229920006395 saturated elastomer Polymers 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000009261 transgenic effect Effects 0.000 description 3
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 2
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 2
HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
240000002791 Brassica napus Species 0.000 description 2
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