CA2532718A1 - 2-substituted pyrimidines - Google Patents

Info

Publication number

CA2532718A1

CA2532718A1 CA002532718A CA2532718A CA2532718A1 CA 2532718 A1 CA2532718 A1 CA 2532718A1 CA 002532718 A CA002532718 A CA 002532718A CA 2532718 A CA2532718 A CA 2532718A CA 2532718 A1 CA2532718 A1 CA 2532718A1

Authority

CA

Canada

Prior art keywords

compounds

alkyl

formulae

row

case

Prior art date

2003-07-24

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

• -1 2-substituted pyrimidines Chemical class 0.000 title claims abstract description 201
• 238000000034 method Methods 0.000 claims abstract description 12
• 239000000575 pesticide Substances 0.000 claims abstract description 5
• 238000004519 manufacturing process Methods 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 516
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 168
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 76
• 239000001257 hydrogen Substances 0.000 claims description 67
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 60
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 55
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 47
• 125000001424 substituent group Chemical group 0.000 claims description 25
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
• 239000000460 chlorine Substances 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 241000233866 Fungi Species 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000001931 aliphatic 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
• 239000000463 material Substances 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• 239000007787 solid Substances 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
• 150000001298 alcohols Chemical class 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 150000002825 nitriles Chemical class 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 230000003032 phytopathogenic effect Effects 0.000 claims description 4
• 239000002689 soil Substances 0.000 claims description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 230000002538 fungal effect Effects 0.000 claims description 3
• 230000007062 hydrolysis Effects 0.000 claims description 3
• 238000006460 hydrolysis reaction Methods 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 239000011630 iodine Substances 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 2
• 125000002723 alicyclic group Chemical group 0.000 claims description 2
• 125000003118 aryl group Chemical group 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 239000003795 chemical substances by application Substances 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
• 125000004962 sulfoxyl group Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
• 239000007788 liquid Substances 0.000 claims 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 125000006823 (C1-C6) acyl group Chemical group 0.000 claims 1
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• 150000002463 imidates Chemical class 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• 239000000203 mixture Substances 0.000 description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
• 241000196324 Embryophyta Species 0.000 description 18
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• 239000006185 dispersion Substances 0.000 description 10
• 239000000417 fungicide Substances 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• 238000010790 dilution Methods 0.000 description 9
• 239000012895 dilution Substances 0.000 description 9
• 239000008187 granular material Substances 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 150000003230 pyrimidines Chemical class 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 239000002270 dispersing agent Substances 0.000 description 8
• 239000000839 emulsion Substances 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 239000000969 carrier Substances 0.000 description 6
• 235000013339 cereals Nutrition 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 125000001153 fluoro group Chemical group F* 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 230000000855 fungicidal effect Effects 0.000 description 6
• 208000015181 infectious disease Diseases 0.000 description 6
• IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 6
• UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 5
• 101150041968 CDC13 gene Proteins 0.000 description 5
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 239000006072 paste Substances 0.000 description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 239000008096 xylene Substances 0.000 description 5
• 239000004215 Carbon black (E152) Substances 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 240000007594 Oryza sativa Species 0.000 description 4
• 235000007164 Oryza sativa Nutrition 0.000 description 4
• 240000003768 Solanum lycopersicum Species 0.000 description 4
• 229910052783 alkali metal Inorganic materials 0.000 description 4
• 235000014113 dietary fatty acids Nutrition 0.000 description 4
• 239000000194 fatty acid Substances 0.000 description 4
• 229930195729 fatty acid Natural products 0.000 description 4
• 229930195733 hydrocarbon Natural products 0.000 description 4
• 235000012054 meals Nutrition 0.000 description 4
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 4
• 229920000151 polyglycol Polymers 0.000 description 4
• 239000010695 polyglycol Substances 0.000 description 4
• 235000009566 rice Nutrition 0.000 description 4
• CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 235000013311 vegetables Nutrition 0.000 description 4
• 239000000080 wetting agent Substances 0.000 description 4
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
• FDCRZTKUSHPCSS-YFKPBYRVSA-N 4-chloro-5-(2,4,6-trifluorophenyl)-6-[[(2s)-1,1,1-trifluoropropan-2-yl]amino]pyrimidine-2-carbonitrile Chemical compound FC(F)(F)[C@H](C)NC1=NC(C#N)=NC(Cl)=C1C1=C(F)C=C(F)C=C1F FDCRZTKUSHPCSS-YFKPBYRVSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 235000021307 Triticum Nutrition 0.000 description 3
• 244000098338 Triticum aestivum Species 0.000 description 3
• 240000006365 Vitis vinifera Species 0.000 description 3
• 235000014787 Vitis vinifera Nutrition 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• 235000012211 aluminium silicate Nutrition 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 239000004359 castor oil Substances 0.000 description 3
• 235000019438 castor oil Nutrition 0.000 description 3
• 239000004495 emulsifiable concentrate Substances 0.000 description 3
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
• 229910052500 inorganic mineral Inorganic materials 0.000 description 3
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
• 239000011707 mineral Substances 0.000 description 3
• 235000010755 mineral Nutrition 0.000 description 3
• 150000002790 naphthalenes Chemical class 0.000 description 3
• 125000004430 oxygen atom Chemical group O* 0.000 description 3
• 230000001681 protective effect Effects 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
• LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 2
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
• CXOZCAUZFGYNAO-BYPYZUCNSA-N 4-chloro-5-(2,4,6-trifluorophenyl)-6-[[(2s)-1,1,1-trifluoropropan-2-yl]amino]pyrimidine-2-carboxamide Chemical compound FC(F)(F)[C@H](C)NC1=NC(C(N)=O)=NC(Cl)=C1C1=C(F)C=C(F)C=C1F CXOZCAUZFGYNAO-BYPYZUCNSA-N 0.000 description 2
• GFYUGVRWUJDHRQ-BYPYZUCNSA-N 4-chloro-5-(2,4,6-trifluorophenyl)-6-[[(2s)-1,1,1-trifluoropropan-2-yl]amino]pyrimidine-2-carboxylic acid Chemical compound FC(F)(F)[C@H](C)NC1=NC(C(O)=O)=NC(Cl)=C1C1=C(F)C=C(F)C=C1F GFYUGVRWUJDHRQ-BYPYZUCNSA-N 0.000 description 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• 239000005995 Aluminium silicate Substances 0.000 description 2
• 241000123650 Botrytis cinerea Species 0.000 description 2
• 240000004160 Capsicum annuum Species 0.000 description 2
• 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 2
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• 240000005979 Hordeum vulgare Species 0.000 description 2
• 235000007340 Hordeum vulgare Nutrition 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 244000070406 Malus silvestris Species 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• 240000005561 Musa balbisiana Species 0.000 description 2
• AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
• 240000000111 Saccharum officinarum Species 0.000 description 2
• 235000007201 Saccharum officinarum Nutrition 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 244000061456 Solanum tuberosum Species 0.000 description 2
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• 230000009471 action Effects 0.000 description 2
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• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
• 150000008052 alkyl sulfonates Chemical class 0.000 description 2
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• FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
• 150000001450 anions Chemical class 0.000 description 2
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• OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
• 238000006555 catalytic reaction Methods 0.000 description 2
• 229910052802 copper Inorganic materials 0.000 description 2
• 239000010949 copper Substances 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 125000000753 cycloalkyl group Chemical group 0.000 description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
• QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 2
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• 238000001125 extrusion Methods 0.000 description 2
• 150000004665 fatty acids Chemical class 0.000 description 2
• 239000003337 fertilizer Substances 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 125000001188 haloalkyl group Chemical group 0.000 description 2
• 125000005843 halogen group Chemical group 0.000 description 2
• 239000004009 herbicide Substances 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 2
• HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
• 235000019341 magnesium sulphate Nutrition 0.000 description 2
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