DK2461687T3 - Pesticidal compositions - Google Patents

Info

Publication number

DK2461687T3

DK2461687T3 DK10807147.3T DK10807147T DK2461687T3 DK 2461687 T3 DK2461687 T3 DK 2461687T3 DK 10807147 T DK10807147 T DK 10807147T DK 2461687 T3 DK2461687 T3 DK 2461687T3

Authority

DK

Denmark

Prior art keywords

alkyl

spp

mmol

haloalkyl

het

Prior art date

2009-08-07

Links

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• 239000000203 mixture Substances 0.000 title claims description 63
• 230000000361 pesticidal effect Effects 0.000 title description 3
• -1 C 1 -C 6 alkylphenyl Chemical group 0.000 claims description 60
• 150000001875 compounds Chemical class 0.000 claims description 51
• 239000002917 insecticide Substances 0.000 claims description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
• 238000000034 method Methods 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 241000196324 Embryophyta Species 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 10
• 241000721621 Myzus persicae Species 0.000 claims description 8
• 241000256247 Spodoptera exigua Species 0.000 claims description 8
• 239000004009 herbicide Substances 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 230000002363 herbicidal effect Effects 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 230000000694 effects Effects 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 4
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 239000001301 oxygen Chemical group 0.000 claims description 3
• 229910052760 oxygen Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 239000012453 solvate Substances 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 239000011593 sulfur Chemical group 0.000 claims description 3
• 244000299507 Gossypium hirsutum Species 0.000 claims description 2
• 230000000895 acaricidal effect Effects 0.000 claims description 2
• 239000000642 acaricide Substances 0.000 claims description 2
• 244000078703 ectoparasite Species 0.000 claims description 2
• 244000079386 endoparasite Species 0.000 claims description 2
• 239000000417 fungicide Substances 0.000 claims description 2
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
• 238000007911 parenteral administration Methods 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 14
• XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
• 235000009432 Gossypium hirsutum Nutrition 0.000 claims 1
• 230000002500 effect on skin Effects 0.000 claims 1
• 150000002148 esters Chemical class 0.000 claims 1
• 230000000855 fungicidal effect Effects 0.000 claims 1
• 239000000243 solution Substances 0.000 description 60
• 239000000575 pesticide Substances 0.000 description 58
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
• 241000607479 Yersinia pestis Species 0.000 description 52
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
• 229910001868 water Inorganic materials 0.000 description 49
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
• 238000002360 preparation method Methods 0.000 description 40
• 239000000543 intermediate Substances 0.000 description 39
• 239000007787 solid Substances 0.000 description 32
• 239000000047 product Substances 0.000 description 29
• 235000019439 ethyl acetate Nutrition 0.000 description 28
• 238000005160 1H NMR spectroscopy Methods 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
• 238000009472 formulation Methods 0.000 description 23
• 239000002904 solvent Substances 0.000 description 21
• 238000006243 chemical reaction Methods 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• 150000001299 aldehydes Chemical class 0.000 description 17
• 239000004094 surface-active agent Substances 0.000 description 17
• 241000254171 Curculionidae Species 0.000 description 15
• 238000006254 arylation reaction Methods 0.000 description 15
• 125000001188 haloalkyl group Chemical group 0.000 description 15
• 238000010992 reflux Methods 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 14
• 230000000052 comparative effect Effects 0.000 description 14
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
• 239000000463 material Substances 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 13
• 238000004587 chromatography analysis Methods 0.000 description 13
• 238000000746 purification Methods 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000011541 reaction mixture Substances 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 11
• 238000002451 electron ionisation mass spectrometry Methods 0.000 description 11
• 230000000749 insecticidal effect Effects 0.000 description 11
• 239000002245 particle Substances 0.000 description 11
• 230000009467 reduction Effects 0.000 description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• 239000007788 liquid Substances 0.000 description 10
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 241001124076 Aphididae Species 0.000 description 9
• 241000258937 Hemiptera Species 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• HUOFUOCSQCYFPW-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(OC(F)(F)F)C=C1 HUOFUOCSQCYFPW-UHFFFAOYSA-N 0.000 description 9
• 235000019441 ethanol Nutrition 0.000 description 9
• 235000011181 potassium carbonates Nutrition 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 239000004546 suspension concentrate Substances 0.000 description 9
• 238000003828 vacuum filtration Methods 0.000 description 9
• 241000254173 Coleoptera Species 0.000 description 8
• 241000257303 Hymenoptera Species 0.000 description 8
• 150000002825 nitriles Chemical class 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 241000255925 Diptera Species 0.000 description 7
• 241000255967 Helicoverpa zea Species 0.000 description 7
• 241000256259 Noctuidae Species 0.000 description 7
• 239000002270 dispersing agent Substances 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 239000000126 substance Substances 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• 239000004562 water dispersible granule Substances 0.000 description 7
• 241000238876 Acari Species 0.000 description 6
• 241001147381 Helicoverpa armigera Species 0.000 description 6
• 241000238631 Hexapoda Species 0.000 description 6
• 241000256602 Isoptera Species 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• 241000244206 Nematoda Species 0.000 description 6
• 241001509970 Reticulitermes <genus> Species 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 239000003995 emulsifying agent Substances 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 235000013305 food Nutrition 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• 235000019198 oils Nutrition 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• 239000005725 8-Hydroxyquinoline Substances 0.000 description 5
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
• 230000009471 action Effects 0.000 description 5
• 239000003905 agrochemical Substances 0.000 description 5
• 239000002518 antifoaming agent Substances 0.000 description 5
• 239000012267 brine Substances 0.000 description 5
• 239000004495 emulsifiable concentrate Substances 0.000 description 5
• 239000002316 fumigant Substances 0.000 description 5
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
• 150000007857 hydrazones Chemical class 0.000 description 5
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
• CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• 229960003540 oxyquinoline Drugs 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 5
• 238000010898 silica gel chromatography Methods 0.000 description 5
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
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• 241001414720 Cicadellidae Species 0.000 description 4
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
• 241000353522 Earias insulana Species 0.000 description 4
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• 241001477931 Mythimna unipuncta Species 0.000 description 4
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• 241001674048 Phthiraptera Species 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 241001414989 Thysanoptera Species 0.000 description 4
• 125000005037 alkyl phenyl group Chemical group 0.000 description 4
• 238000004166 bioassay Methods 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 230000008878 coupling Effects 0.000 description 4
• 238000010168 coupling process Methods 0.000 description 4
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• BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• 239000002949 juvenile hormone Substances 0.000 description 4
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• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
• 239000002689 soil Substances 0.000 description 4
• 239000003053 toxin Substances 0.000 description 4
• 231100000765 toxin Toxicity 0.000 description 4
• 108700012359 toxins Proteins 0.000 description 4
• OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 3
• RTUDBROGOZBBIC-UHFFFAOYSA-N 1-iodo-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(I)C=C1 RTUDBROGOZBBIC-UHFFFAOYSA-N 0.000 description 3
• KBVIWLGAVURNLR-UHFFFAOYSA-N 4-(1h-pyrazol-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=NN1 KBVIWLGAVURNLR-UHFFFAOYSA-N 0.000 description 3
• LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 description 3
• RBTXNWWNDUZLDU-UHFFFAOYSA-N 4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]benzaldehyde Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1N=C(C=2C=CC(C=O)=CC=2)N=C1 RBTXNWWNDUZLDU-UHFFFAOYSA-N 0.000 description 3
• JDDSQGPWIJFHKD-UHFFFAOYSA-N 4-bromo-1-[4-(trifluoromethoxy)phenyl]imidazole Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C=C(Br)N=C1 JDDSQGPWIJFHKD-UHFFFAOYSA-N 0.000 description 3
• ZASQHVAGPKBSHH-UHFFFAOYSA-N 5-(4-methylphenyl)-1h-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1C1=NNC=N1 ZASQHVAGPKBSHH-UHFFFAOYSA-N 0.000 description 3
• 241001600407 Aphis <genus> Species 0.000 description 3
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• 229920005682 EO-PO block copolymer Polymers 0.000 description 3
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
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• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
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• ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 3
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• SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
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• 230000002378 acidificating effect Effects 0.000 description 3
• 125000002015 acyclic group Chemical group 0.000 description 3
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• 125000000129 anionic group Chemical group 0.000 description 3
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• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
• 230000001276 controlling effect Effects 0.000 description 3
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 239000011737 fluorine Substances 0.000 description 3
• JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 3
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
• 125000005843 halogen group Chemical group 0.000 description 3
• 230000002209 hydrophobic effect Effects 0.000 description 3
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• 239000007791 liquid phase Substances 0.000 description 3
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
• 235000019341 magnesium sulphate Nutrition 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
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• 239000003208 petroleum Substances 0.000 description 3
• ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
• 108090000623 proteins and genes Proteins 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
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• 238000001308 synthesis method Methods 0.000 description 3
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• 150000003852 triazoles Chemical class 0.000 description 3
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