JP2005531549A - 置換ピラゾロ−ピリミジン−４−オン - Google Patents

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Publication number

JP2005531549A

JP2005531549A JP2004501408A JP2004501408A JP2005531549A JP 2005531549 A JP2005531549 A JP 2005531549A JP 2004501408 A JP2004501408 A JP 2004501408A JP 2004501408 A JP2004501408 A JP 2004501408A JP 2005531549 A JP2005531549 A JP 2005531549A

Authority

JP

Japan

Prior art keywords

chlorine

fluorine

substituted

optionally

methyl

Prior art date

2002-05-02

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• 150000001875 compounds Chemical class 0.000 claims abstract description 128
• -1 optionally Chemical group 0.000 claims description 305
• 229910052801 chlorine Inorganic materials 0.000 claims description 82
• 239000000460 chlorine Substances 0.000 claims description 79
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 78
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 56
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 49
• 229910052794 bromium Inorganic materials 0.000 claims description 49
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 47
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 45
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 41
• 239000011737 fluorine Substances 0.000 claims description 40
• 229910052731 fluorine Inorganic materials 0.000 claims description 40
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 40
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 39
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 39
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 39
• 238000000034 method Methods 0.000 claims description 39
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 38
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 34
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 34
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 239000000203 mixture Substances 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
• 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 21
• 238000006243 chemical reaction Methods 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 19
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 18
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000001153 fluoro group Chemical group F* 0.000 claims description 18
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 18
• 125000005981 pentynyl group Chemical group 0.000 claims description 18
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 18
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 18
• 230000008569 process Effects 0.000 claims description 17
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 11
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 11
• 125000001544 thienyl group Chemical group 0.000 claims description 11
• 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 10
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000006003 dichloroethyl group Chemical group 0.000 claims description 9
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 9
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 9
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 9
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 9
• 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 9
• 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 9
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 9
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 9
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 7
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 241000244206 Nematoda Species 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
• 239000004606 Fillers/Extenders Substances 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• XUBDVXOHGQSAHX-UHFFFAOYSA-N chembl188441 Chemical compound C12=NC(C)=NC(O)=C2C=NN1C1=C(Cl)C=C(Cl)C=C1Cl XUBDVXOHGQSAHX-UHFFFAOYSA-N 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• 239000002168 alkylating agent Substances 0.000 claims description 2
• 229940100198 alkylating agent Drugs 0.000 claims description 2
• 125000005998 bromoethyl group Chemical group 0.000 claims description 2
• 125000005997 bromomethyl group Chemical group 0.000 claims description 2
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
• 239000004094 surface-active agent Substances 0.000 claims description 2
• 125000006000 trichloroethyl group Chemical group 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
• 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 claims 1
• 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 1
• 239000004009 herbicide Substances 0.000 abstract description 9
• 230000002363 herbicidal effect Effects 0.000 abstract description 8
• 238000004519 manufacturing process Methods 0.000 abstract description 8
• 239000005645 nematicide Substances 0.000 abstract description 4
• 241000196324 Embryophyta Species 0.000 description 76
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
• 239000007858 starting material Substances 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 240000008042 Zea mays Species 0.000 description 12
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
• 235000005822 corn Nutrition 0.000 description 12
• 239000011734 sodium Substances 0.000 description 12
• 229910052708 sodium Inorganic materials 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
• 229920000742 Cotton Polymers 0.000 description 10
• 241000219146 Gossypium Species 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 238000002844 melting Methods 0.000 description 10
• 230000008018 melting Effects 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 239000002689 soil Substances 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• 239000008187 granular material Substances 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 235000010469 Glycine max Nutrition 0.000 description 7
• 244000068988 Glycine max Species 0.000 description 7
• 238000005507 spraying Methods 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 239000003995 emulsifying agent Substances 0.000 description 6
• 238000003306 harvesting Methods 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 108090000623 proteins and genes Proteins 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 238000000967 suction filtration Methods 0.000 description 6
• 230000009261 transgenic effect Effects 0.000 description 6
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 241001465754 Metazoa Species 0.000 description 5
• 235000002595 Solanum tuberosum Nutrition 0.000 description 5
• 244000061456 Solanum tuberosum Species 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• 241000607479 Yersinia pestis Species 0.000 description 5
• 239000012141 concentrate Substances 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 238000005259 measurement Methods 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• 0 *C(N1*)=Nc([n](*)nc2)c2C1=O Chemical compound *C(N1*)=Nc([n](*)nc2)c2C1=O 0.000 description 4
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 241000238631 Hexapoda Species 0.000 description 4
• 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 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• 244000062793 Sorghum vulgare Species 0.000 description 4
• 235000021307 Triticum Nutrition 0.000 description 4
• 241000209140 Triticum Species 0.000 description 4
• 125000002877 alkyl aryl group Chemical group 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 239000000839 emulsion Substances 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 229910052500 inorganic mineral Inorganic materials 0.000 description 4
• 239000000463 material 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
• 239000011591 potassium Substances 0.000 description 4
• 229910052700 potassium Inorganic materials 0.000 description 4
• 239000007921 spray Substances 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
• SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 3
• QCCPRTLVGONCQE-UHFFFAOYSA-N 5-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=NC=C(C(F)(F)F)C=C1Cl QCCPRTLVGONCQE-UHFFFAOYSA-N 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
• 240000002791 Brassica napus Species 0.000 description 3
• 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
• 244000301850 Cupressus sempervirens Species 0.000 description 3
• 239000005562 Glyphosate Substances 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• 235000006484 Paeonia officinalis Nutrition 0.000 description 3
• 244000170916 Paeonia officinalis Species 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 238000009395 breeding Methods 0.000 description 3
• 235000013399 edible fruits Nutrition 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 239000000499 gel Substances 0.000 description 3
• XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 3
• 239000002917 insecticide Substances 0.000 description 3
• 239000002480 mineral oil Substances 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 230000001069 nematicidal effect Effects 0.000 description 3
• 150000002894 organic compounds Chemical class 0.000 description 3
• 239000006072 paste Substances 0.000 description 3
• 239000012071 phase Substances 0.000 description 3
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
• 102000004169 proteins and genes Human genes 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 229910000104 sodium hydride 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
• 238000003860 storage Methods 0.000 description 3
• 239000010902 straw Substances 0.000 description 3
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