IL130537A - 1 - Arylpirazoles, pesticide preparations containing them, process for their preparation and methods for pest control - Google Patents

Info

Publication number

IL130537A

IL130537A IL13053797A IL13053797A IL130537A IL 130537 A IL130537 A IL 130537A IL 13053797 A IL13053797 A IL 13053797A IL 13053797 A IL13053797 A IL 13053797A IL 130537 A IL130537 A IL 130537A

Authority

IL

Israel

Prior art keywords

alkyl

formula

compound

amino

halogen

Prior art date

1996-12-24

Links

• Espacenet
• Global Dossier
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• 239000000203 mixture Substances 0.000 title claims description 87
• 241000607479 Yersinia pestis Species 0.000 title claims description 38
• 238000000034 method Methods 0.000 title claims description 36
• 230000000361 pesticidal effect Effects 0.000 title claims description 7
• 125000004961 1-arylpyrazolyl group Chemical group 0.000 title claims description 4
• 230000008569 process Effects 0.000 title description 5
• 238000002360 preparation method Methods 0.000 title description 3
• -1 1H-pyrazol-1-yl Chemical group 0.000 claims abstract description 105
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 68
• 150000003839 salts Chemical class 0.000 claims abstract description 42
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 28
• 150000002367 halogens Chemical class 0.000 claims abstract description 28
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 25
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 18
• 150000003254 radicals Chemical class 0.000 claims abstract description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 10
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 8
• 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims abstract description 8
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 7
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims abstract description 6
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims abstract description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
• 125000006519 CCH3 Chemical group 0.000 claims abstract description 4
• 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
• 239000001257 hydrogen Substances 0.000 claims abstract description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
• 125000004429 atom Chemical group 0.000 claims abstract description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
• 125000001475 halogen functional 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
• 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 3
• 102220315634 rs1196125127 Human genes 0.000 claims abstract 3
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• 238000006243 chemical reaction Methods 0.000 claims description 24
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
• 230000003647 oxidation Effects 0.000 claims description 6
• 238000007254 oxidation reaction Methods 0.000 claims description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 230000037396 body weight Effects 0.000 claims description 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
• 239000003513 alkali Substances 0.000 claims description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
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• ZTOXNAIRALLYRB-UHFFFAOYSA-N 5-amino-1-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Br ZTOXNAIRALLYRB-UHFFFAOYSA-N 0.000 claims description 2
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• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
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• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 230000029936 alkylation Effects 0.000 claims 2
• 238000005804 alkylation reaction Methods 0.000 claims 2
• 230000032050 esterification Effects 0.000 claims 2
• 238000005886 esterification reaction Methods 0.000 claims 2
• XPEOQIUFBJRCKE-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(SC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XPEOQIUFBJRCKE-UHFFFAOYSA-N 0.000 claims 1
• CICWDLGVJKMEIX-UHFFFAOYSA-N 5-amino-1-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazole-3-carbothioamide Chemical compound N1=C(C(N)=S)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Br CICWDLGVJKMEIX-UHFFFAOYSA-N 0.000 claims 1
• 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 1
• 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
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• 239000002689 soil Substances 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• 238000011282 treatment Methods 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 239000004615 ingredient Substances 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
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