SK279252B6 - 1-aryl-5-(substituovaný alkylidénimino)pyrazoly, s - Google Patents

Info

Publication number

SK279252B6

SK279252B6 SK1337-92A SK133792A SK279252B6 SK 279252 B6 SK279252 B6 SK 279252B6 SK 133792 A SK133792 A SK 133792A SK 279252 B6 SK279252 B6 SK 279252B6

Authority

SK

Slovakia

Prior art keywords

group

alkyl

cyano

atom

formula

Prior art date

1991-04-30

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• 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 21
• 150000001875 compounds Chemical class 0.000 claims abstract description 227
• 239000000203 mixture Substances 0.000 claims abstract description 115
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 64
• 238000000034 method Methods 0.000 claims abstract description 44
• 241000238421 Arthropoda Species 0.000 claims abstract description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
• 241000244206 Nematoda Species 0.000 claims abstract description 32
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
• 125000005843 halogen group Chemical group 0.000 claims abstract description 28
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
• 229910052736 halogen Chemical group 0.000 claims abstract description 21
• 150000002367 halogens Chemical group 0.000 claims abstract description 21
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 20
• 125000004414 alkyl thio group Chemical group 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
• 239000001257 hydrogen Substances 0.000 claims abstract description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
• 238000006467 substitution reaction Methods 0.000 claims abstract description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
• 230000008569 process Effects 0.000 claims abstract description 9
• -1 cycloalkylcarbonyl radical Chemical group 0.000 claims description 184
• 239000000460 chlorine Chemical group 0.000 claims description 120
• 241000607479 Yersinia pestis Species 0.000 claims description 62
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 38
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 239000007787 solid Substances 0.000 claims description 26
• 239000013543 active substance Substances 0.000 claims description 23
• 238000002360 preparation method Methods 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 230000000361 pesticidal effect Effects 0.000 claims description 18
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 239000004615 ingredient Substances 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 16
• 239000007788 liquid Substances 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• 239000000654 additive Substances 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 8
• 239000003054 catalyst Substances 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 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
• 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
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
• 239000003456 ion exchange resin Substances 0.000 claims description 6
• 229920003303 ion-exchange polymer Polymers 0.000 claims description 6
• UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 239000000969 carrier Substances 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000005265 dialkylamine group Chemical group 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 150000002905 orthoesters Chemical class 0.000 claims description 4
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
• 230000002378 acidificating effect Effects 0.000 claims description 3
• 150000001356 alkyl thiols Chemical class 0.000 claims description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 239000003729 cation exchange resin Substances 0.000 claims description 3
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
• 125000000168 pyrrolyl group Chemical group 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
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 125000002252 acyl group Chemical group 0.000 claims description 2
• 125000004423 acyloxy group Chemical group 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 125000006371 dihalo methyl group Chemical group 0.000 claims description 2
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
• 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
• 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 2
• 125000004951 trihalomethoxy group Chemical group 0.000 claims description 2
• 239000003701 inert diluent Substances 0.000 claims 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 241000239223 Arachnida Species 0.000 claims 1
• 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims 1
• AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims 1
• 244000000013 helminth Species 0.000 abstract description 15
• 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Chemical group 0.000 abstract 2
• 238000012360 testing method Methods 0.000 description 76
• 241000196324 Embryophyta Species 0.000 description 57
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
• 239000004480 active ingredient Substances 0.000 description 41
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• 239000002689 soil Substances 0.000 description 33
• 239000000243 solution Substances 0.000 description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 241000238631 Hexapoda Species 0.000 description 23
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• 239000000047 product Substances 0.000 description 22
• 239000000126 substance Substances 0.000 description 19
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
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