NZ540462A - Pesticidal 5-(acylamino) pyrazole derivatives - Google Patents

Info

Publication number

NZ540462A

NZ540462A NZ540462A NZ54046203A NZ540462A NZ 540462 A NZ540462 A NZ 540462A NZ 540462 A NZ540462 A NZ 540462A NZ 54046203 A NZ54046203 A NZ 54046203A NZ 540462 A NZ540462 A NZ 540462A

Authority

NZ

New Zealand

Prior art keywords

alkyl

compound

haloalkyl

group

formula

Prior art date

2002-12-03

Links

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• 230000000361 pesticidal effect Effects 0.000 title claims abstract description 12
• 150000003217 pyrazoles Chemical class 0.000 title 1
• 239000000203 mixture Substances 0.000 claims abstract description 94
• 238000000034 method Methods 0.000 claims abstract description 47
• 150000003839 salts Chemical class 0.000 claims abstract description 42
• 241000607479 Yersinia pestis Species 0.000 claims abstract description 37
• 238000002360 preparation method Methods 0.000 claims abstract description 10
• 150000001875 compounds Chemical class 0.000 claims description 173
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 150000002367 halogens Chemical class 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 238000012360 testing method Methods 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
• 241000258924 Ctenocephalides felis Species 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 239000004094 surface-active agent Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 238000011282 treatment Methods 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 230000000694 effects Effects 0.000 claims description 7
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 241001481696 Rhipicephalus sanguineus Species 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 5
• 230000010933 acylation Effects 0.000 claims description 5
• 238000005917 acylation reaction Methods 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
• 238000012216 screening Methods 0.000 claims description 5
• 229910052721 tungsten Inorganic materials 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 230000007717 exclusion Effects 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
• 229910006069 SO3H Inorganic materials 0.000 claims description 2
• 230000029936 alkylation Effects 0.000 claims description 2
• 238000005804 alkylation reaction Methods 0.000 claims description 2
• 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
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• -1 (C2-C6)-haIoalkynyl Chemical group 0.000 description 55
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• 150000003254 radicals Chemical class 0.000 description 28
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 23
• 239000000047 product Substances 0.000 description 20
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• 238000005481 NMR spectroscopy Methods 0.000 description 17
• 239000000843 powder Substances 0.000 description 17
• 241000238876 Acari Species 0.000 description 16
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
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• 239000007788 liquid Substances 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 12
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 12
• 239000004615 ingredient Substances 0.000 description 11
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
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• 125000000217 alkyl group Chemical group 0.000 description 9
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 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
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 241000255925 Diptera Species 0.000 description 6
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 235000013339 cereals Nutrition 0.000 description 6
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• 239000000839 emulsion Substances 0.000 description 6
• DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 6
• 244000144972 livestock Species 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 230000009261 transgenic effect Effects 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
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• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
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