PH26899A - Derivatives of N-phenylpyrazoles compositions and use - Google Patents

Info

Publication number

PH26899A

PH26899A PH38904A PH38904A PH26899A PH 26899 A PH26899 A PH 26899A PH 38904 A PH38904 A PH 38904A PH 38904 A PH38904 A PH 38904A PH 26899 A PH26899 A PH 26899A

Authority

PH

Philippines

Prior art keywords

general formula

cyano

dichloro

group

compound

Prior art date

1988-07-15

Links

• Espacenet
• Global Dossier
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• WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 title claims abstract description 8
• 239000000203 mixture Substances 0.000 title claims description 80
• -1 1,2,3-triazol-2-yl Chemical group 0.000 claims abstract description 48
• 239000002253 acid Substances 0.000 claims abstract description 27
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 26
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 24
• 239000000460 chlorine Substances 0.000 claims abstract description 22
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 15
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 11
• 239000011737 fluorine Substances 0.000 claims abstract description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims abstract description 5
• 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims abstract description 5
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
• 230000000507 anthelmentic effect Effects 0.000 claims abstract description 4
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 4
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims abstract description 3
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims abstract description 3
• 230000001069 nematicidal effect Effects 0.000 claims abstract description 3
• 230000000842 anti-protozoal effect Effects 0.000 claims abstract 2
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract 2
• 150000001875 compounds Chemical class 0.000 claims description 131
• 241000238421 Arthropoda Species 0.000 claims description 40
• 238000006243 chemical reaction Methods 0.000 claims description 35
• 244000000013 helminth Species 0.000 claims description 19
• 238000000034 method Methods 0.000 claims description 19
• 241000607479 Yersinia pestis Species 0.000 claims description 18
• 239000002585 base Substances 0.000 claims description 17
• 241000244206 Nematoda Species 0.000 claims description 16
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
• 229910052783 alkali metal Inorganic materials 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 108010034145 Helminth Proteins Proteins 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• UPSNEEHCIMBEEJ-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-pyrrol-1-yl-4-(trifluoromethylsulfanyl)pyrazole-3-carbonitrile Chemical compound FC(F)(F)SC=1C(C#N)=NN(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)C=1N1C=CC=C1 UPSNEEHCIMBEEJ-UHFFFAOYSA-N 0.000 claims description 5
• 239000003638 chemical reducing agent Substances 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
• 150000001241 acetals Chemical class 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
• GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical class COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims description 3
• 150000001345 alkine derivatives Chemical class 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
• 150000002460 imidazoles Chemical class 0.000 claims description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• OCTIHQYULBGYEW-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(1,2,4-triazol-1-yl)-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(N2N=CN=C2)=C(S(=O)(=O)C(F)(F)F)C(C#N)=N1 OCTIHQYULBGYEW-UHFFFAOYSA-N 0.000 claims description 2
• JFFKPSGMEFUJOG-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-piperidin-1-yl-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(N2CCCCC2)=C(S(=O)(=O)C(F)(F)F)C(C#N)=N1 JFFKPSGMEFUJOG-UHFFFAOYSA-N 0.000 claims description 2
• YNVYAMLMDCPMPK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-pyrrolidin-1-yl-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(N2CCCC2)=C(S(=O)(=O)C(F)(F)F)C(C#N)=N1 YNVYAMLMDCPMPK-UHFFFAOYSA-N 0.000 claims description 2
• 125000005077 diacylhydrazine group Chemical group 0.000 claims description 2
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 150000003852 triazoles Chemical class 0.000 claims description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• CWWJXDRBOBCIHJ-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(2,5-dimethylpyrrol-1-yl)-4-(trifluoromethylsulfanyl)pyrazole-3-carbonitrile Chemical compound CC1=CC=C(C)N1C1=C(SC(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl CWWJXDRBOBCIHJ-UHFFFAOYSA-N 0.000 claims 1
• DKMDWKLLPLGMSM-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-imidazol-1-yl-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(N2C=NC=C2)=C(S(=O)(=O)C(F)(F)F)C(C#N)=N1 DKMDWKLLPLGMSM-UHFFFAOYSA-N 0.000 claims 1
• NGNFWYZZNAKBDX-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-pyrrol-1-yl-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(N2C=CC=C2)=C(S(=O)C(F)(F)F)C(C#N)=N1 NGNFWYZZNAKBDX-UHFFFAOYSA-N 0.000 claims 1
• 208000006968 Helminthiasis Diseases 0.000 claims 1
• 239000003904 antiprotozoal agent Substances 0.000 claims 1
• 239000000969 carrier Substances 0.000 claims 1
• 150000002084 enol ethers Chemical class 0.000 claims 1
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
• 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims 1
• 208000028172 protozoa infectious disease Diseases 0.000 claims 1
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
• 229910052736 halogen Inorganic materials 0.000 abstract description 6
• 150000002367 halogens Chemical class 0.000 abstract description 6
• 239000011630 iodine Substances 0.000 abstract description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 5
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• 239000000543 intermediate Substances 0.000 description 37
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
• 239000000243 solution Substances 0.000 description 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
• 239000007787 solid Substances 0.000 description 30
• 241001465754 Metazoa Species 0.000 description 27
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
• 238000010992 reflux Methods 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000012442 inert solvent Substances 0.000 description 20
• 241000196324 Embryophyta Species 0.000 description 18
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
• 239000002904 solvent Substances 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• 239000000047 product Substances 0.000 description 13
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 12
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• 239000004480 active ingredient Substances 0.000 description 10
• 125000001153 fluoro group Chemical group F* 0.000 description 10
• 241000238876 Acari Species 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 241000254173 Coleoptera Species 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 206010061217 Infestation Diseases 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
• 241000251539 Vertebrata <Metazoa> Species 0.000 description 9
• 239000008187 granular material Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
• 235000019341 magnesium sulphate Nutrition 0.000 description 9
• 238000002156 mixing Methods 0.000 description 9
• 239000000377 silicon dioxide Substances 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 241000255925 Diptera Species 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 239000003960 organic solvent Substances 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 229940067157 phenylhydrazine Drugs 0.000 description 7
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• 239000003995 emulsifying agent Substances 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• 150000004820 halides Chemical class 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 208000015181 infectious disease Diseases 0.000 description 6
• 239000004615 ingredient Substances 0.000 description 6
• 229910052500 inorganic mineral Inorganic materials 0.000 description 6
• 235000010755 mineral Nutrition 0.000 description 6
• 235000010288 sodium nitrite Nutrition 0.000 description 6
• 239000002689 soil Substances 0.000 description 6
• 238000005507 spraying Methods 0.000 description 6
• 239000001117 sulphuric acid Substances 0.000 description 6
• 235000011149 sulphuric acid Nutrition 0.000 description 6
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
• 241000256602 Isoptera Species 0.000 description 5
• 239000012141 concentrate Substances 0.000 description 5
• 239000013078 crystal Substances 0.000 description 5
• 230000008020 evaporation Effects 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 238000000227 grinding Methods 0.000 description 5
• 244000144972 livestock Species 0.000 description 5
• 239000011707 mineral Substances 0.000 description 5
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 4
• CBFIKOBUXGUSNV-UHFFFAOYSA-N 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(S(=O)(=O)C(F)(F)F)C(C#N)=N1 CBFIKOBUXGUSNV-UHFFFAOYSA-N 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
• 241000257303 Hymenoptera 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
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
• 241000238814 Orthoptera Species 0.000 description 4
• 241000500437 Plutella xylostella Species 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 240000008042 Zea mays Species 0.000 description 4
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
• 150000001540 azides Chemical class 0.000 description 4
• 235000013339 cereals Nutrition 0.000 description 4
• 239000002270 dispersing agent Substances 0.000 description 4
• 239000003651 drinking water Substances 0.000 description 4
• 235000020188 drinking water Nutrition 0.000 description 4
• 239000000839 emulsion Substances 0.000 description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• 239000002245 particle Substances 0.000 description 4
• 239000008188 pellet Substances 0.000 description 4
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
• 159000000001 potassium salts Chemical class 0.000 description 4
• 239000004540 pour-on Substances 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 239000007921 spray Substances 0.000 description 4
• 238000009736 wetting Methods 0.000 description 4
• 239000000080 wetting agent Substances 0.000 description 4
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• 241000258937 Hemiptera Species 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
• 150000001340 alkali metals Chemical class 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
• 150000001450 anions Chemical class 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000008280 blood Substances 0.000 description 3
• 210000004369 blood Anatomy 0.000 description 3
• 230000037396 body weight Effects 0.000 description 3
• 229950005228 bromoform Drugs 0.000 description 3
• 150000001733 carboxylic acid esters Chemical class 0.000 description 3
• ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
• 235000021186 dishes Nutrition 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 210000003608 fece Anatomy 0.000 description 3
• 235000013312 flour Nutrition 0.000 description 3
• 230000037406 food intake Effects 0.000 description 3
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 239000003921 oil Substances 0.000 description 3
• 235000019198 oils Nutrition 0.000 description 3
• 239000007800 oxidant agent Substances 0.000 description 3
• 230000003647 oxidation Effects 0.000 description 3
• 238000007254 oxidation reaction Methods 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
• 244000144977 poultry Species 0.000 description 3
• 235000013594 poultry meat Nutrition 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• 239000001632 sodium acetate Substances 0.000 description 3
• 235000017281 sodium acetate Nutrition 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
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