CA2484997A1 - Substituted pyrazolo-pyrimidine-4-ones - Google Patents

Info

Publication number

CA2484997A1

CA2484997A1 CA002484997A CA2484997A CA2484997A1 CA 2484997 A1 CA2484997 A1 CA 2484997A1 CA 002484997 A CA002484997 A CA 002484997A CA 2484997 A CA2484997 A CA 2484997A CA 2484997 A1 CA2484997 A1 CA 2484997A1

Authority

CA

Canada

Prior art keywords

substituted

chlorine

fluorine

methyl

cyano

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 claims abstract description 125
• 238000000034 method Methods 0.000 claims abstract description 41
• 238000004519 manufacturing process Methods 0.000 claims abstract 2
• -1 cyano- Chemical class 0.000 claims description 751
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 108
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 60
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 56
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 43
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 42
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 41
• 239000000203 mixture Substances 0.000 claims description 40
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 35
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 35
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
• 125000006005 fluoroethoxy group Chemical group 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 238000006243 chemical reaction Methods 0.000 claims description 20
• 125000004369 butenyl group Chemical class C(=CCC)* 0.000 claims description 18
• 125000000480 butynyl group Chemical class [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 18
• 125000002255 pentenyl group Chemical class C(=CCCC)* 0.000 claims description 18
• 125000005981 pentynyl group Chemical class 0.000 claims description 18
• 125000004368 propenyl group Chemical class C(=CC)* 0.000 claims description 18
• 125000002568 propynyl group Chemical class [*]C#CC([H])([H])[H] 0.000 claims description 18
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 17
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 17
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 17
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 17
• 239000000460 chlorine Substances 0.000 claims description 16
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
• 229910052794 bromium Inorganic materials 0.000 claims description 15
• 229910052801 chlorine Inorganic materials 0.000 claims description 15
• 239000003085 diluting agent Substances 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 12
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical class C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
• 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 11
• 125000002541 furyl group Chemical group 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000001544 thienyl group Chemical group 0.000 claims description 11
• 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
• 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 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
• 125000006003 dichloroethyl group Chemical group 0.000 claims description 9
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 9
• 125000003754 ethoxycarbonyl group Chemical class C(=O)(OCC)* 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
• 125000003718 tetrahydrofuranyl 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
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 8
• 125000001160 methoxycarbonyl group Chemical class [H]C([H])([H])OC(*)=O 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 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
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical class 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical class 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical class 0.000 claims description 4
• 241000244206 Nematoda Species 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 125000000623 heterocyclic group Chemical class 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
• 239000004606 Fillers/Extenders Substances 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
• 125000004191 (C1-C6) alkoxy group Chemical class 0.000 claims description 2
• 230000002152 alkylating effect Effects 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
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
• 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 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
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 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
• 125000006527 (C1-C5) alkyl group Chemical class 0.000 claims 2
• 125000006729 (C2-C5) alkenyl group Chemical class 0.000 claims 2
• 125000006730 (C2-C5) alkynyl group Chemical class 0.000 claims 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical class 0.000 claims 1
• 125000006700 (C1-C6) alkylthio group Chemical class 0.000 claims 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 239000004009 herbicide Substances 0.000 abstract description 8
• 239000005645 nematicide Substances 0.000 abstract description 4
• 241000196324 Embryophyta Species 0.000 description 78
• 230000008569 process Effects 0.000 description 33
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• 239000007858 starting material Substances 0.000 description 22
• 238000002360 preparation method Methods 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
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 239000000047 product Substances 0.000 description 14
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 240000008042 Zea mays Species 0.000 description 12
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 12
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
• 235000009973 maize Nutrition 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 238000009472 formulation Methods 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• 244000038559 crop plants Species 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
• 239000002904 solvent Substances 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 241000219146 Gossypium Species 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 239000003995 emulsifying agent Substances 0.000 description 9
• 239000002689 soil Substances 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
• 229920000742 Cotton Polymers 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• 229910052799 carbon Inorganic materials 0.000 description 8
• 239000008187 granular material Substances 0.000 description 8
• 108090000623 proteins and genes Proteins 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 6
• 235000010469 Glycine max Nutrition 0.000 description 6
• 241001465754 Metazoa Species 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-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
• 230000006378 damage Effects 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 230000002363 herbicidal effect Effects 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 150000003254 radicals Chemical class 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 239000011734 sodium Substances 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
• 241000607479 Yersinia pestis Species 0.000 description 5
• 239000003086 colorant Substances 0.000 description 5
• 235000013399 edible fruits Nutrition 0.000 description 5
• 229910052500 inorganic mineral Inorganic materials 0.000 description 5
• 235000010755 mineral Nutrition 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
• 239000000243 solution Substances 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• 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
• SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
• 241000238631 Hexapoda Species 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
• 235000002595 Solanum tuberosum Nutrition 0.000 description 4
• 244000061456 Solanum tuberosum Species 0.000 description 4
• 241000209140 Triticum Species 0.000 description 4
• 235000021307 Triticum Nutrition 0.000 description 4
• 125000002877 alkyl aryl group Chemical group 0.000 description 4
• 239000012141 concentrate Substances 0.000 description 4
• 238000011161 development Methods 0.000 description 4
• 230000018109 developmental process Effects 0.000 description 4
• 239000000839 emulsion Substances 0.000 description 4
• 235000019441 ethanol Nutrition 0.000 description 4
• HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 238000003306 harvesting Methods 0.000 description 4
• 229920000151 polyglycol Polymers 0.000 description 4
• 239000010695 polyglycol Substances 0.000 description 4
• 239000007921 spray Substances 0.000 description 4
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
• 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
• XABUNAPAHLOXCT-UHFFFAOYSA-N 5-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]pyrazole-4-carboxamide Chemical compound NC1=C(C(=O)N)C=NN1C1=NC=C(C(F)(F)F)C=C1Cl XABUNAPAHLOXCT-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
• 235000006008 Brassica napus var napus Nutrition 0.000 description 3
• 239000005562 Glyphosate Substances 0.000 description 3
• 241000207783 Ipomoea Species 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
• 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
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• 239000006260 foam Substances 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
• 239000007788 liquid Substances 0.000 description 3
• 239000011707 mineral 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
• 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
• 150000003839 salts Chemical class 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
• 238000005507 spraying Methods 0.000 description 3
• 238000003860 storage Methods 0.000 description 3
• 239000001117 sulphuric acid Substances 0.000 description 3
• 235000011149 sulphuric acid Nutrition 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 239000008096 xylene Substances 0.000 description 3
• ZLULYWOWSRIQOI-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-6-methyl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC(C)=NC=2N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZLULYWOWSRIQOI-UHFFFAOYSA-N 0.000 description 2
• XZJIUOSBYRIKJP-UHFFFAOYSA-N 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-5-[(1-fluorocyclopropanecarbonyl)amino]pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NN(C=2C(=CC(=CN=2)C(F)(F)F)Cl)C=1NC(=O)C1(F)CC1 XZJIUOSBYRIKJP-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
• KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-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
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