ES2747810T3 - Compuestos bicíclicos como agentes para combatir parásitos - Google Patents

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Publication number

ES2747810T3

ES2747810T3 ES15724728T ES15724728T ES2747810T3 ES 2747810 T3 ES2747810 T3 ES 2747810T3 ES 15724728 T ES15724728 T ES 15724728T ES 15724728 T ES15724728 T ES 15724728T ES 2747810 T3 ES2747810 T3 ES 2747810T3

Authority

ES

Spain

Prior art keywords

alkyl

halogen

cycloalkyl

alkoxy

cyano

Prior art date

2014-06-05

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 244000045947 parasite Species 0.000 title claims description 28
• 125000002619 bicyclic group Chemical group 0.000 title description 3
• -1 alkylskylaryl Chemical group 0.000 claims abstract description 474
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 222
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 166
• 150000002367 halogens Chemical class 0.000 claims abstract description 156
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 137
• 150000001875 compounds Chemical class 0.000 claims abstract description 127
• 239000001257 hydrogen Substances 0.000 claims abstract description 106
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 106
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 91
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 84
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 73
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 63
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 62
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 61
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 58
• 239000001301 oxygen Substances 0.000 claims abstract description 58
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 55
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 46
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 26
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 24
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
• 125000003118 aryl group Chemical group 0.000 claims abstract description 20
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 17
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 16
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 16
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 16
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 15
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 15
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 14
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 14
• 150000001721 carbon Chemical group 0.000 claims abstract description 14
• 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 13
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 13
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims abstract description 12
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims abstract description 10
• 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 7
• 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 5
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 5
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 5
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims abstract description 5
• 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 5
• 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims abstract description 4
• 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 4
• 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims abstract description 3
• 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims abstract description 3
• 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims abstract description 3
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims abstract description 3
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 99
• 239000011737 fluorine Substances 0.000 claims description 99
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 91
• 239000000460 chlorine Substances 0.000 claims description 91
• 229910052801 chlorine Inorganic materials 0.000 claims description 91
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 79
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 65
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 65
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 64
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 62
• 229910052794 bromium Inorganic materials 0.000 claims description 62
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 58
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 52
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 42
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 39
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 37
• 239000011575 calcium Substances 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical class [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 29
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 29
• 125000001153 fluoro group Chemical group F* 0.000 claims description 28
• 239000003795 chemical substances by application Substances 0.000 claims description 26
• 125000004076 pyridyl group Chemical group 0.000 claims description 24
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
• 239000011593 sulfur Chemical group 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 150000002500 ions Chemical class 0.000 claims description 20
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 20
• 125000000335 thiazolyl group Chemical group 0.000 claims description 20
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 17
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 17
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 13
• 125000002971 oxazolyl group Chemical group 0.000 claims description 12
• 239000011734 sodium Substances 0.000 claims description 12
• 229910052708 sodium Inorganic materials 0.000 claims description 12
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
• 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 claims description 11
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 10
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 229910052791 calcium Inorganic materials 0.000 claims description 10
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
• 229910052744 lithium Inorganic materials 0.000 claims description 10
• 229910052749 magnesium Inorganic materials 0.000 claims description 10
• 239000011777 magnesium Substances 0.000 claims description 10
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
• 229910052700 potassium Inorganic materials 0.000 claims description 9
• 239000011591 potassium Substances 0.000 claims description 9
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
• 125000005002 aryl methyl group Chemical group 0.000 claims description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 229910052790 beryllium Inorganic materials 0.000 claims description 7
• ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 7
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 229910052701 rubidium Inorganic materials 0.000 claims description 7
• IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 7
• 229910052712 strontium Inorganic materials 0.000 claims description 7
• CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 7
• 239000004094 surface-active agent Substances 0.000 claims description 7
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
• TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 4
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 4
• 125000006426 1-chlorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(Cl)* 0.000 claims description 4
• 125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 claims description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
• 125000002393 azetidinyl group Chemical group 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 4
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
• 239000011630 iodine Chemical group 0.000 claims description 4
• 229910052740 iodine Chemical group 0.000 claims description 4
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 3
• 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
• 229910052792 caesium Inorganic materials 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000005458 thianyl group Chemical group 0.000 claims description 3
• 125000001166 thiolanyl group Chemical group 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
• 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 2
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 2
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• GGFNXKFGVQQNRV-UHFFFAOYSA-N Ethyl 4-phenylbutanoate Chemical class CCOC(=O)CCCC1=CC=CC=C1 GGFNXKFGVQQNRV-UHFFFAOYSA-N 0.000 claims description 2
• 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004439 haloalkylsulfanyl group Chemical group 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• 229910021645 metal ion Inorganic materials 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 125000005475 oxolanyl group Chemical group 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
• 239000003513 alkali Substances 0.000 claims 5
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 5
• 229910052788 barium Inorganic materials 0.000 claims 4
• DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 4
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 2
• AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims 1
• HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 125000002098 pyridazinyl group Chemical group 0.000 claims 1
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract description 2
• 125000005103 alkyl silyl group Chemical group 0.000 abstract 10
• 241000196324 Embryophyta Species 0.000 description 94
• 125000005843 halogen group Chemical group 0.000 description 67
• 239000000203 mixture Substances 0.000 description 62
• 238000000034 method Methods 0.000 description 50
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 48
• 238000009472 formulation Methods 0.000 description 43
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 30
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 29
• 239000003112 inhibitor Substances 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• 241001465754 Metazoa Species 0.000 description 21
• 239000002904 solvent Substances 0.000 description 19
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 15
• 108090000623 proteins and genes Proteins 0.000 description 15
• 241000238631 Hexapoda Species 0.000 description 14
• 239000002671 adjuvant Substances 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 239000000645 desinfectant Substances 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 235000019441 ethanol Nutrition 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 230000009261 transgenic effect Effects 0.000 description 12
• 239000002270 dispersing agent Substances 0.000 description 11
• 238000002156 mixing Methods 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 10
• 241000894006 Bacteria Species 0.000 description 10
• 244000000054 animal parasite Species 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 239000008187 granular material Substances 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 150000003839 salts Chemical class 0.000 description 10
• 125000001424 substituent group Chemical group 0.000 description 10
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 241000255925 Diptera Species 0.000 description 9
• 238000003306 harvesting Methods 0.000 description 9
• 239000013598 vector Substances 0.000 description 9
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 8
• 241000238876 Acari Species 0.000 description 8
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