ES2752250T3 - 2-Tioimidazolil-carboxamidas sustituidas como pesticidas - Google Patents

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Publication number

ES2752250T3

ES2752250T3 ES16702955T ES16702955T ES2752250T3 ES 2752250 T3 ES2752250 T3 ES 2752250T3 ES 16702955 T ES16702955 T ES 16702955T ES 16702955 T ES16702955 T ES 16702955T ES 2752250 T3 ES2752250 T3 ES 2752250T3

Authority

ES

Spain

Prior art keywords

methyl

spp

cyano

ethyl

alkyl

Prior art date

2015-02-09

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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• 239000000575 pesticide Substances 0.000 title description 28
• -1 hetarylalkyl Chemical group 0.000 claims abstract description 431
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 159
• 150000001875 compounds Chemical class 0.000 claims abstract description 156
• 239000001257 hydrogen Substances 0.000 claims abstract description 103
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 103
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 91
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 75
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 54
• 150000002367 halogens Chemical class 0.000 claims abstract description 54
• 229910052717 sulfur Chemical group 0.000 claims abstract description 53
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 21
• 239000001301 oxygen Substances 0.000 claims abstract description 21
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 16
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 15
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 13
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
• 239000011593 sulfur Chemical group 0.000 claims abstract description 7
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 6
• 125000000753 cycloalkyl group Chemical class 0.000 claims abstract description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 147
• 229910052731 fluorine Inorganic materials 0.000 claims description 129
• 239000011737 fluorine Substances 0.000 claims description 129
• 239000000460 chlorine Substances 0.000 claims description 126
• 229910052801 chlorine Inorganic materials 0.000 claims description 126
• 150000003254 radicals Chemical class 0.000 claims description 121
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 117
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 108
• 241000196324 Embryophyta Species 0.000 claims description 104
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 95
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 94
• 229910052794 bromium Inorganic materials 0.000 claims description 94
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 94
• 238000000034 method Methods 0.000 claims description 67
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 66
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 51
• 239000000203 mixture Substances 0.000 claims description 48
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 46
• 241001465754 Metazoa Species 0.000 claims description 45
• UQZPGHOJMQTOHB-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-ethylethanamine Chemical compound ClCCN(CC)CCCl UQZPGHOJMQTOHB-UHFFFAOYSA-N 0.000 claims description 38
• 238000009472 formulation Methods 0.000 claims description 33
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 32
• 125000001153 fluoro group Chemical group F* 0.000 claims description 30
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 28
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 23
• 241000607479 Yersinia pestis Species 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 12
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 12
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000002883 imidazolyl group Chemical group 0.000 claims description 10
• 239000000463 material 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
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 239000004606 Fillers/Extenders Substances 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 239000003905 agrochemical Substances 0.000 claims description 8
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 8
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 6
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 6
• 101150047265 COR2 gene Proteins 0.000 claims description 6
• 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 6
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 6
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 239000004094 surface-active agent Substances 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 239000012868 active agrochemical ingredient Substances 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 2
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
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• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
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