BG61076B1 - 1-арил-5-/субституирани алкилиденимино/пиразоли с пестицидна активност - Google Patents

Info

Publication number

BG61076B1

BG61076B1 BG96285A BG9628592A BG61076B1 BG 61076 B1 BG61076 B1 BG 61076B1 BG 96285 A BG96285 A BG 96285A BG 9628592 A BG9628592 A BG 9628592A BG 61076 B1 BG61076 B1 BG 61076B1

Authority

BG

Bulgaria

Prior art keywords

alkyl

formula

cyano

compound

phenyl

Prior art date

1991-04-30

Links

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• 230000000361 pesticidal effect Effects 0.000 title claims abstract description 18
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title claims description 45
• 150000001875 compounds Chemical class 0.000 claims abstract description 222
• 239000000203 mixture Substances 0.000 claims abstract description 92
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 71
• 238000000034 method Methods 0.000 claims abstract description 55
• 241000238421 Arthropoda Species 0.000 claims abstract description 44
• 150000002367 halogens Chemical group 0.000 claims abstract description 43
• 229910052736 halogen Chemical group 0.000 claims abstract description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
• 241000244206 Nematoda Species 0.000 claims abstract description 34
• 239000001257 hydrogen Substances 0.000 claims abstract description 34
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
• 241001124076 Aphididae Species 0.000 claims abstract description 25
• 241000238631 Hexapoda Species 0.000 claims abstract description 24
• 238000002360 preparation method Methods 0.000 claims abstract description 23
• 244000000013 helminth Species 0.000 claims abstract description 22
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 20
• 150000003217 pyrazoles Chemical class 0.000 claims abstract description 17
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
• 125000005843 halogen group Chemical group 0.000 claims abstract description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
• 238000006467 substitution reaction Methods 0.000 claims abstract description 5
• -1 nitro, thiocyanato Chemical group 0.000 claims description 175
• 239000000460 chlorine Substances 0.000 claims description 146
• 241000196324 Embryophyta Species 0.000 claims description 68
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
• 241000607479 Yersinia pestis Species 0.000 claims description 45
• 241001465754 Metazoa Species 0.000 claims description 32
• 239000002689 soil Substances 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 26
• 239000004480 active ingredient Substances 0.000 claims description 22
• 150000002431 hydrogen Chemical class 0.000 claims description 22
• 241000255925 Diptera Species 0.000 claims description 21
• 239000007787 solid Substances 0.000 claims description 21
• 239000007788 liquid Substances 0.000 claims description 19
• 239000000126 substance Substances 0.000 claims description 19
• 241000254173 Coleoptera Species 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 238000006243 chemical reaction Methods 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 239000011737 fluorine Substances 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 239000000654 additive Substances 0.000 claims description 10
• 238000011161 development Methods 0.000 claims description 10
• 241000238876 Acari Species 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 9
• 239000003456 ion exchange resin Substances 0.000 claims description 8
• 229920003303 ion-exchange polymer Polymers 0.000 claims description 8
• 239000004094 surface-active agent Substances 0.000 claims description 8
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 241000251539 Vertebrata <Metazoa> Species 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 150000002576 ketones Chemical class 0.000 claims description 7
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 239000003054 catalyst Substances 0.000 claims description 6
• 241000255777 Lepidoptera Species 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 241000258937 Hemiptera Species 0.000 claims description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
• 150000002905 orthoesters Chemical class 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 150000001356 alkyl thiols Chemical class 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 239000003729 cation exchange resin Substances 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 150000007522 mineralic acids Chemical class 0.000 claims description 3
• 150000007524 organic acids Chemical class 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 241001414989 Thysanoptera Species 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 2
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
• 125000006371 dihalo methyl group Chemical group 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
• 230000036541 health Effects 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000004951 trihalomethoxy group Chemical group 0.000 claims description 2
• 239000012442 inert solvent Substances 0.000 claims 2
• ZROILLPDIUNLSE-UHFFFAOYSA-N 1-phenyl-1h-pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC=CC=C1 ZROILLPDIUNLSE-UHFFFAOYSA-N 0.000 claims 1
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 125000005265 dialkylamine group Chemical group 0.000 claims 1
• AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims 1
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
• 230000008569 process Effects 0.000 abstract description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
• 239000000243 solution Substances 0.000 description 55
• 239000013543 active substance Substances 0.000 description 43
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• 102100029952 Double-strand-break repair protein rad21 homolog Human genes 0.000 description 16
• 101000584942 Homo sapiens Double-strand-break repair protein rad21 homolog Proteins 0.000 description 16
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