| (11) | EP 3 353 171 B1 |
(12) | EUROPEAN PATENT SPECIFICATION |
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(54) | ISOXAZOLINE-SUBSTITUTED BENZAMIDES AND ANALOGUES AS INSECTICIDES ISOXAZOLIN-SUBSTITUIERTE BENZAMIDE UND ANALOGE ALS INSEKTIZIDE BENZAMIDES ET ANALOGUES SUBSTITUÉS PAR UNE ISOXAZOLINE EN TANT QU'INSECTICIDES |
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Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). |
A1, A2, A3 and A4 are independently of one another C-H, C-R5, or nitrogen;
R1 is hydrogen, C1-C8alkyl, C1-C8alkylcarbonyl-, C1-C8alkoxy, C1-C8alkoxy-C1-C8alkyl or C1-C8alkoxycarbonyl-;
R2 is C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl, C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl, C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl, C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl, C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, 5-6 membered heteroaryl-C1-C4alkyl, 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7, -N(R8)(R9), -OR10 or halogen;
R3 is C1-C8haloalkyl;
R4 is aryl, aryl substituted by one to three R7, heteroaryl or heteroaryl substituted by one to three R7;
R5 is independently halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, C1-C8alkoxy, C1-C8haloalkoxy, or C1-C8alkoxycarbonyl-, or two R5 on adjacent carbon atoms together form a -CH=CH-CH=CH- bridge or a -N=CH-CH=CH- bridge;
R6a is independently cyano, nitro, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, hydroxy, C1-C8alkoxy, or C1-C8haloalkoxy;
R6b is independently halogen, cyano, nitro, oxo, C1-C8alkyl, C1-C8haloalkyl, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, hydroxyl, C1-C8alkoxy, C1-C8haloalkoxy, phenyl, phenyl substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7;
R7 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy" C1-C8haloalkoxy;
R8 and R9 are independently hydrogen, cyano, cyano-C1-C8alkyl, C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C2-C8alkenyl, C2-C8alkenyl substituted by one to three R6a, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8haloalkoxy substituted by one to three R6a, C1-C8alkoxy substituted by one to three R6a,C1-C8haloalkyl, C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl, C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl, C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl, C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, 5-6 membered heteroaryl-C1-C4alkyl, 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7, -S(O)R10, -S(O)2R10, COR10, COOR10, or R8 and R9 together with the nitrogen atom can be linked through a C3-C8alkylene chain, a C3-C8alkylene chain substituted by one to three R6b or a C3-C8alkylene chain, where one carbon atom is replaced by O, S, S(O) or SO2;
R10 is hydrogen, cyano-C1-C8alkyl, C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl, C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl, C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl, C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl, C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7;
n is 2;
or a tautomer, enantiomer, salt or N-oxide thereof.In an embodiment E1 of formula (I), independent of other embodiments, A1 is CR5 and A2, A3 and A4 are each CH, wherein R5 is as defined in the first aspect of the invention.
In an embodiment E2 of formula (I), independent of other embodiments, R1 is hydrogen, C1-C8alkyl, C1-C8alkylcarbonyl- or C1-C8alkoxycarbonyl-.
In an embodiment E3 of formula (I), independent of other embodiments, R2 is C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C1-C8haloalkyl, di-C1-C8alkylamino, -N(R8)(R9), aryl, aryl substituted by one to three R6b, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R6b, wherein R6a and R6b are as defined in the first aspect of the invention or halogen.
In an embodiment E4 of formula (I), independent of other embodiments, R3 is C1-C4haloalkyl.
In an embodiment E5 of formula (I), independent of other embodiments, R4 is aryl, aryl substituted by one to three R7, 5-6 membered heteroaryl or 5-6 membered heteroaryl substituted by one to three R7, wherein R7 is as defined in the first aspect of the invention.
Embodiment E6 of formula (I) provides compounds of formula (I) wherein A1 is CR5 and A2, A3 and A4 are each CH; R1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl; R2 is C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C1-C8haloalkyl, di-C1-C8alkylamino, aryl, aryl substituted by one to three R6b, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R6b or fluoro; R3 is C1-C4haloalkyl; R4 is aryl or aryl substituted by one to three R7; and n is 2; wherein R5 is halogen or C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, or C2-C8alkenyl; R6a is independently cyano, halogen, nitro, C1-C4alkoxy, or C1-C4haloalkoxy; and R6b is independently halogen, cyano, nitro, C1-C4alkyl, or C1-C4haloalkyl, C1-C4alkoxy, or C1-C4haloalkoxy.
Embodiment E7 of formula (I) provides compounds of formula (I) wherein A1 is CR5 and A2, A3 and A4 are each CH; R1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl; R2 is C1-C4alkyl, C1-C4alkyl substituted by one to three R6a, C2-C4alkenyl, C2-C4alkynyl, C3-C5cycloalkyl, C1-C4haloalkyl, di-C1-C4alkylamino, -NH(C1-C4alkyl), fluoro, phenyl, or 5-6 membered heteroaryl; R3 is C1-C4haloalkyl; R4 is aryl or aryl substituted by one to three R7; and n is 2; wherein R5 is halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl; R6a is independently fluoro, cyano, nitro, methoxy, difluoromethoxy or trifluoromethoxy; and R7 is independently bromo, chloro, fluoro, cyano, nitro methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy.
Embodiment E8 of formula (I) provides compounds of formula (I) wherein A1 is CR5 and A2, A3 and A4 are each CH; R1 is hydrogen; R2 is C1-C4alkyl, C1-C4alkyl substituted by one to three R6a, C2-C4alkenyl, C2-C4alkynyl, C3-C5cycloalkyl, C1-C4haloalkyl, di-C1-C4alkylamino, -NH(C1-C4alkyl), fluoro, 1-3 halo-substituted phenyl, or 5-6 membered heteroaryl; R3 is chlorodifluoromethyl or trifluoromethyl; R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; and n is 2; wherein R5 is bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, or vinyl; R6a is independently fluoro, cyano, nitro, methoxy, difluoromethoxy or trifluoromethoxy; and R6b is independently bromo, chloro, fluoro, cyano, nitro methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy.
Embodiment E9 of formula (I) provides compounds of formula (I) wherein A1 is CR5 and A2, A3 and A4 are each CH; R1 is hydrogen; R2 is C1-C4alkyl, C1-C4alkyl substituted by one to three R6a, C2-C4alkenyl, C2-C4alkynyl, C3-C5cycloalkyl, C1-C4haloalkyl, di-C1-C4alkylamino, -NH(C1-C4alkyl), fluoro or 5-6 membered heteroaryl; R3 is chlorodifluoromethyl or trifluoromethyl; R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluorophenyl or 3,4,5-trichloro-phenyl; and n is 2; wherein R5 is bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, or vinyl; R6a is independently fluoro, cyano, nitro, methoxy, difluoromethoxy or trifluoromethoxy; and R6b is independently bromo, chloro, fluoro, cyano, nitro methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy.
Embodiment E10 of formula (I) provides compounds of formula (I) wherein A1 is CR5 and A2, A3 and A4 are each CH; R1 is hydrogen; R2 is methyl, ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, oxetanyl, thietanyl, chloromethyl, fluoromethyl, difluoromethyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, dimethylamino, methylamino or fluoro; R3 is chlorodifluoromethyl or trifluoromethyl; R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; and n is 2; wherein R5 is bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, or vinyl; R6a is independently fluoro, cyano, nitro, methoxy, difluoromethoxy or trifluoromethoxy; and R6b is independently bromo, chloro, fluoro, cyano, nitro methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy.
Embodiment E11 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is chloro, bromo, trifluoromethyl, fluoro, or methyl; R2 is methyl, ethyl, cyclopropyl, chloromethyl, fluoromethyl, difluoromethyl, iso-propyl, methylamino, dimethlyamino, fluoro, cyclobutyl, 3,3,3,-trifluoropropyl or 2,2,2-trifluoroethyl, or methoxyethyl; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E12 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is chloro or methyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E13 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is chloro, bromo, trifluoromethyl, fluoro, or methyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is phenyl, pyridyl, mono-, di- or tri-substituted phenyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl, or mono- or di-substituted pyridyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl.
Embodiment E14 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is chloro or methyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-dichloro-4-fluorophenyl, 3,4,5-trichloro-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3-chloro-5-trifluoromethyl-phenyl.
Embodiment E15 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is chloro; R2 is methyl, ethyl, cyclopropyl, chloromethyl, fluoromethyl, difluoromethyl, iso-propyl, methylamino, dimethlyamino, fluoro, cyclobutyl, 3,3,3,-trifluoropropyl or 2,2,2-trifluoroethyl, or methoxyethyl; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E16 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is chloro; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E17 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is chloro; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is phenyl, pyridyl, mono-, di- or tri-substituted phenyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl, or mono- or di-substituted pyridyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl.
Embodiment E18 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is chloro; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-dichloro-4-fluorophenyl, 3,4,5-trichloro-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3-chloro-5-trifluoromethyl-phenyl.
Embodiment E19 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is bromo; R2 is methyl, ethyl, cyclopropyl, chloromethyl, fluoromethyl, difluoromethyl, iso-propyl, methylamino, dimethlyamino, fluoro, cyclobutyl, 3,3,3,-trifluoropropyl or 2,2,2-trifluoroethyl, or methoxyethyl; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E20 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is bromo; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E21 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is bromo; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is phenyl, pyridyl, mono-, di- or tri-substituted phenyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl, or mono- or di-substituted pyridyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl.
Embodiment E22 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is bromo; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-dichloro-4-fluorophenyl, 3,4,5-trichloro-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3-chloro-5-trifluoromethyl-phenyl.
Embodiment E23 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is methyl; R2 is methyl, ethyl, cyclopropyl, chloromethyl, fluoromethyl, difluoromethyl, iso-propyl, methylamino, dimethlyamino, fluoro, cyclobutyl, 3,3,3,-trifluoropropyl or 2,2,2-trifluoroethyl, or methoxyethyl; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E24 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is methyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E25 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is methyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is phenyl, pyridyl, mono-, di- or tri-substituted phenyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl, or mono- or di-substituted pyridyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl.
Embodiment E26 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is methyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-dichloro-4-fluorophenyl, 3,4,5-trichloro-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3-chloro-5-trifluoromethyl-phenyl.
Embodiment E27 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is trifluoromethyl; R2 is methyl, ethyl, cyclopropyl, chloromethyl, fluoromethyl, difluoromethyl, iso-propyl, methylamino, dimethlyamino, fluoro, cyclobutyl, 3,3,3,-trifluoropropyl or 2,2,2-trifluoroethyl, or methoxyethyl; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E28 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is trifluoromethyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; especially R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl, pyridyl, or 3-5-substituted pyridyl wherein the substituents are selected from bromo, chloro, fluoro or trifluoro; more preferably R4 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl, 4-bromo-3,5-dichlorophenyl, 3,4,5-trichloro-phenyl, 3,5-dichloro-4-fluorophenyl.
Embodiment E29 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is chlorodifluoromethyl or trifluoromethyl; n is 2; A1 is CR5, wherein R5 is trifluoromethyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is phenyl, pyridyl, mono-, di- or tri-substituted phenyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl, or mono- or di-substituted pyridyl where the substituents are independently selected from chloro, bromo, fluoro, or trifluoromethyl.
Embodiment E30 of formula (I) provides compounds of formula (I) wherein A2, A3 and A4 are each CH; R1 is hydrogen; R3 is trifluoromethyl; n is 2; A1 is CR5, wherein R5 is trifluoromethyl; R2 is methyl, ethyl, cyclopropyl, methylamino, dimethlyamino, chloromethyl, fluoromethyl, difluoromethyl or fluoro; and R4 is 3,5-dichloro-4-fluorophenyl, 3,4,5-trichloro-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3-chloro-5-trifluoromethyl-phenyl.
A1, A2, A3 and A4 are independently of one another C-H, C-R5, or nitrogen;
R1 is hydrogen;
R2 is C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C3cycloalkyl or C3-C3cycloalkyl substituted by one to three R6b, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, -N(R8)(R9) or fluoro;
R3 is C1-C8haloalkyl;
R4 is phenyl or phenyl substituted by one to three R7;
R5 is independently halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl;
R6a is independently C1-C8alkoxy, or C1-C8haloalkoxy;
R6b is independently oxo, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, C1-C8alkoxy, C1-C8haloalkoxy, phenyl, phenyl substituted by one to three R7, 5-6 membered heteroaryl or 5-6 membered heteroaryl substituted by one to three R7;
R7 is independently halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy, or C1-C8haloalkoxy;
R8 and R9 are independently hydrogen, cyano-C1-C8alkyl, C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, -S(O)2R10;
R10 is hydrogen, cyano-C1-C8alkyl, C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, phenyl, phenyl substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7;
n is 2;
or a tautomer, enantiomer, salt or N-oxide thereof.Ra is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C1-C8haloalkoxy;
Rb is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C1-C8haloalkoxy;
Rc is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C1-C8haloalkoxy;
R5 is halogen, cyano, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl;
Rd is S(O)2-R2;
R2 is C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, -N(R8)(R9), halogen;
R5 is independently halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl;
R6a is independently C1-C8alkoxy, or C1-C8haloalkoxy;
R6b is independently oxo, amino, C1-C8alkylamin8, N,N-C1-C8dialkylamino, C1-C8alkoxy, C1-C8haloalkoxy, phenyl, phenyl substituted by one to three R7, 5-6 membered heteroaryl or 5-6 membered heteroaryl substituted by one to three R7;
R7 is independently halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy, or C1-C8haloalkoxy;
R8 and R9 are independently hydrogen, cyano-C1-C8alkyl, C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, -S(O)2R10;
R10 is hydrogen, cyano-C1-C8alkyl, C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, phenyl, phenyl substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7. Preferably at least one of the Ra, Rb and Rc is not hydrogen.
Ra is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C1-C8haloalkoxy;
Rb is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C1-C8haloalkoxy;
Rc is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C1-C8haloalkoxy;
R5 is halogen, cyano, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl;
Rd is SO2-CH3, SO2-4-chlorophenyl, SO2-propyl, SO2-CH2Cl, SO2-CH2F, SO2-CHF2, SO2-cyclopropyl, SO2-CH2CH2-Cl, SO2-CH2CF3, SO2-2-thienyl, SO2-N(CH3)2, SO2-CH2CH2CF3, SO2-cyclobutyl, SO2-2-propyl, SO2-CH2CH2-O-CH3, SO2CH2CH3, SO2F, SO2-NH2, SO2-NH(CH3), SO2-N(CH3)(CH2CH3), SO2-N(CH3)(C(=O)CH3), SO2-N(CH3)C(=O)N(CH3)2, SO2-N(CH3)C(=O)OCH2CH3, SO2-N(CH3)C(=O)OCH3, SO2-N(CH3)C(=O)(3-pyridyl), SO2-N(CH3)SO2N(CH3)2, SO2-N(CH3)C(=O)Ph, SO2-N(CH3)CN, SO2-N(CH3)CH2CHCH2, SO2-N(CH3)CH2COCH2, SO2-N(CH3)CH2CH2CH3, SO2-N(CH3)CH2CH2CH2CH3, SO2-N(CH3)CH2Ph, SO2-N(CH3)CH2CN, SO2-N(CH3)CH2CO2CH2CH3, SO2-N(CH3)CH2CH2OCH3, SO2-N(CH2CH3)CO2C(CH3)3, SO2-N(CH3)SO2CH3, SO2-NHCH2CH3, SO2-N(CH3)CH2OCH3, SO2-NHC(CH3)3, SO2-N(CH2CH3)2, SO2-N(CH2)4, SO2-N(CH3)C(CH3)3, SO2-NHCH(CH3)2, SO2-NHC(=O)CH3, SO2-NHSO2CH3, SO2-N(CH3)CH(CH3)2, SO2-N(CH2CH3)CH(CH3)2 or SO2-NHCH2CHCH2. Preferably at least one of the Ra, Rb and Rc is not hydrogen. More preferably at least two of the Ra, Rb and Rc are not hydrogen.
Ra is H, Cl, Br, F, CF3, CH3 or OCF3;
Rb is H, Cl, Br, F, CF3, CH3 or OCF3;
Rc is H, Cl, Br, F, CF3, CH3 or OCF3;
R5 is CH3, Cl, Br, CN, cyclopropyl, CF3, CHCH2;
Rd is SO2-CH3, SO2-4-chlorophenyl, SO2-propyl, SO2-CH2Cl, SO2-CH2F, SO2-CHF2, SO2-cyclopropyl, SO2-CH2CH2-Cl, SO2-CH2CF3, SO2-2-thienyl, SO2-N(CH3)2, SO2-CH2CH2CF3, SO2-cyclobutyl, SO2-2-propyl, SO2-CH2CH2-O-CH3, SO2CH2CH3, SO2F, SO2-NH2, SO2-NH(CH3), SO2-N(CH3)(CH2CH3), SO2-N(CH3)(C(=O)CH3), SO2-N(CH3)C(=O)N(CH3)2, SO2-N(CH3)C(=O)OCH2CH3, SO2-N(CH3)C(=O)OCH3, SO2-N(CH3)C(=O)(3-pyridyl), SO2-N(CH3)SO2N(CH3)2, SO2-N(CH3)C(=O)Ph, SO2-N(CH3)CN, SO2-N(CH3)CH2CHCH2, SO2-N(CH3)CH2COCH2, SO2-N(CH3)CH2CH2CH3, SO2-N(CH3)CH2CH2CH2CH3, SO2-N(CH3)CH2Ph, SO2-N(CH3)CH2CN, SO2-N(CH3)CH2CO2CH2CH3, SO2-N(CH3)CH2CH2OCH3, SO2-N(CH2CH3)CO2C(CH3)3, SO2-N(CH3)SO2CH3, SO2-NHCH2CH3, SO2-N(CH3)CH2OCH3, SO2-NHC(CH3)3, SO2-N(CH2CH3)2, SO2-N(CH2)4, SO2-N(CH3)C(CH3)3, SO2-NHCH(CH3)2, SO2-NHC(=O)CH3, SO2-NHSO2CH3, SO2-N(CH3)CH(CH3)2, SO2-N(CH2CH3)CH(CH3)2 or SO2-NHCH2CHCH2. Preferably at least one of the Ra, Rb and Rc is not hydrogen. More preferably at least two of the Ra, Rb and Rc are not hydrogen.
Tables 1 to 96: Compounds of formula (Ia)
Table 1
Table 1 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is Me, and X3, R3, X1, R5 are as defined in Table P.
Table 2
Table 2 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is Me, and X3, R3, X1, R5 are as defined in Table P.
Table 3
Table 3 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is Me, and X3, R3, X1, R5 are as defined in Table P.
Table 4
Table 4 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is Me, and X3, R3, X1, R5 are as defined in Table P.
Table 5
Table 5 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is Me, and X3, R3, X1, R5 are as defined in Table P.
Table 6
Table 6 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is Me, and X3, R3, X1, R5 are as defined in Table P.
Table 7
Table 7 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is Et, and X3, R3, X1, R5 are as defined in Table P.
Table 8
Table 8 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is Et, and X3, R3, X1, R5 are as defined in Table P.
Table 9
Table 9 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is Et, and X3, R3, X1, R5 are as defined in Table P.
Table 10
Table 10 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is Et, and X3, R3, X1, R5 are as defined in Table P.
Table 11
Table 11 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is Et, and X3, R3, X1, R5 are as defined in Table P.
Table 12
Table 12 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is Et, and X3, R3, X1, R5 are as defined in Table P.
Table 13
Table 13 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is Pr, and X3, R3, X1, R5 are as defined in Table P.
Table 14
Table 14 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is Pr, and X3, R3, X1, R5 are as defined in Table P.
Table 15
Table 15 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is Pr, and X3, R3, X1, R5 are as defined in Table P.
Table 16
Table 16 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is Pr, and X3, R3, X1, R5 are as defined in Table P.
Table 17
Table 17 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is Pr, and X3, R3, X1, R5 are as defined in Table P.
Table 18
Table 18 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is Pr, and X3, R3, X1, R5 are as defined in Table P.
Table 19
Table 19 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is N(Et)2, and X3, R3, X1, R5 are as defined in Table P.
Table 20
Table 20 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is N(Et)2, and X3, R3, X1, R5 are as defined in Table P.
Table 21
Table 21 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is N(Et)2, and X3, R3, X1, R5 are as defined in Table P.
Table 22
Table 22 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is N(Et)2, and X3, R3, X1, R5 are as defined in Table P.
Table 23
Table 23 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is N(Et)2, and X3, R3, X1, R5 are as defined in Table P.
Table 24
Table 24 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is N(Et)2, and X3, R3, X1, R5 are as defined in Table P.
Table 25
Table 25 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is iPr, and X3, R3, X1, R5 are as defined in Table P.
Table 26
Table 26 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is iPr, and X3, R3, X1, R5 are as defined in Table P.
Table 27
Table 27 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is iPr, and X3, R3, X1, R5 are as defined in Table P.
Table 28
Table 28 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is iPr, and X3, R3, X1, R5 are as defined in Table P.
Table 29
Table 29 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is iPr, and X3, R3, X1, R5 are as defined in Table P.
Table 30
Table 30 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is iPr, and X3, R3, X1, R5 are as defined in Table P.
Table 31
Table 31 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is N(Me)2, and X3, R3, X1, R5 are as defined in Table P.
Table 32
Table 32 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is N(Me)2, and X3, R3, X1, R5 are as defined in Table P.
Table 33
Table 33 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is N(Me)2, and X3, R3, X1, R5 are as defined in Table P.
Table 34
Table 34 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is N(Me)2, and X3, R3, X1, R5 are as defined in Table P.
Table 35
Table 35 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is N(Me)2, and X3, R3, X1, R5 are as defined in Table P.
Table 36
Table 36 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is N(Me)2, and X3, R3, X1, R5 are as defined in Table P.
Table 37
Table 37 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is cBu, and X3, R3, X1, R5 are as defined in Table P.
Table 38
Table 38 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is cBu, and X3, R3, X1, R5 are as defined in Table P.
Table 39
Table 39 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is cBu, and X3, R3, X1, R5 are as defined in Table P.
Table 40
Table 40 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is cBu, and X3, R3, X1, R5 are as defined in Table P.
Table 41
Table 41 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is cBu, and X3, R3, X1, R5 are as defined in Table P.
Table 42
Table 42 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is cBu, and X3, R3, X1, R5 are as defined in Table P.
Table 43
Table 43 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is NHEt, and X3, R3, X1, R5 are as defined in Table P.
Table 44
Table 44 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is NHEt, and X3, R3, X1, R5 are as defined in Table P.
Table 45
Table 45 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is NHEt, and X3, R3, X1, R5 are as defined in Table P.
Table 46
Table 46 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is NHEt, and X3, R3, X1, R5 are as defined in Table P.
Table 47
Table 47 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is NHEt, and X3, R3, X1, R5 are as defined in Table P.
Table 48
Table 48 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is NHEt, and X3, R3, X1, R5 are as defined in Table P.
Table 49
Table 49 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is CH2CF3, and X3, R3, X1, R5 are as defined in Table P.
Table 50
Table 50 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is CH2CF3, and X3, R3, X1, R5 are as defined in Table P.
Table 51
Table 51 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is CH2CF3, and X3, R3, X1, R5 are as defined in Table P.
Table 52
Table 52 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is CH2CF3, and X3, R3, X1, R5 are as defined in Table P.
Table 53
Table 53 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is CH2CF3, and X3, R3, X1, R5 are as defined in Table P.
Table 54
Table 54 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is CH2CF3, and X3, R3, X1, R5 are as defined in Table P.
Table 55
Table 55 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is NHMe, and X3, R3, X1, R5 are as defined in Table P.
Table 56
Table 56 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is NHMe, and X3, R3, X1, R5 are as defined in Table P.
Table 57
Table 57 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is NHMe, and X3, R3, X1, R5 are as defined in Table P.
Table 58
Table 58 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is NHMe, and X3, R3, X1, R5 are as defined in Table P.
Table 59
Table 59 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is NHMe, and X3, R3, X1, R5 are as defined in Table P.
Table 60
Table 60 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is NHMe, and X3, R3, X1, R5 are as defined in Table P.
Table 61
Table 61 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is NMeEt, and X3, R3, X1, R5 are as defined in Table P.
Table 62
Table 62 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is NMeEt, and X3, R3, X1, R5 are as defined in Table P.
Table 63
Table 63 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is NMeEt, and X3, R3, X1, R5 are as defined in Table P.
Table 64
Table 64 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is NMeEt, and X3, R3, X1, R5 are as defined in Table P.
Table 65
Table 65 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is NMeEt, and X3, R3, X1, R5 are as defined in Table P.
Table 66
Table 66 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is NMeEt, and X3, R3, X1, R5 are as defined in Table P.
Table 67
Table 67 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is cPr, and X3, R3, X1, R5 are as defined in Table P.
Table 68
Table 68 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is cPr, and X3, R3, X1, R5 are as defined in Table P.
Table 69
Table 69 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is cPr, and X3, R3, X1, R5 are as defined in Table P.
Table 70
Table 70 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is cPr, and X3, R3, X1, R5 are as defined in Table P.
Table 71
Table 71 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is cPr, and X3, R3, X1, R5 are as defined in Table P.
Table 72
Table 72 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is cPr, and X3, R3, X1, R5 are as defined in Table P.
Table 73
Table 73 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is CH2Cl, and X3, R3, X1, R5 are as defined in Table P.
Table 74
Table 74 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is CH2Cl, and X3, R3, X1, R5 are as defined in Table P.
Table 75
Table 75 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is CH2Cl, and X3, R3, X1, R5 are as defined in Table P.
Table 76
Table 76 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is CH2Cl, and X3, R3, X1, R5 are as defined in Table P.
Table 77
Table 77 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is CH2Cl, and X3, R3, X1, R5 are as defined in Table P.
Table 78
Table 78 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is CH2Cl, and X3, R3, X1, R5 are as defined in Table P.
Table 79
Table 79 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is CH2F, and X3, R3, X1, R5 are as defined in Table P.
Table 80
Table 80 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is CH2F, and X3, R3, X1, R5 are as defined in Table P.
Table 81
Table 81 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is CH2F, and X3, R3, X1, R5 are as defined in Table P.
Table 82
Table 82 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is CH2F, and X3, R3, X1, R5 are as defined in Table P.
Table 83
Table 83 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is CH2F, and X3, R3, X1, R5 are as defined in Table P.
Table 84
Table 84 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is CH2F, and X3, R3, X1, R5 are as defined in Table P.
Table 85
Table 85 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is CHF2, and X3, R3, X1, R5 are as defined in Table P.
Table 86
Table 86 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is CHF2, and X3, R3, X1, R5 are as defined in Table P.
Table 87
Table 87 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is CHF2, and X3, R3, X1, R5 are as defined in Table P.
Table 88
Table 88 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is CHF2, and X3, R3, X1, R5 are as defined in Table P.
Table 89
Table 89 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is CHF2, and X3, R3, X1, R5 are as defined in Table P.
Table 90
Table 90 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is CHF2, and X3, R3, X1, R5 are as defined in Table P.
Table 91
Table 91 provides 250 compounds of formula (Ia) wherein X2 is N, R2 is F, and X3, R3, X1, R5 are as defined in Table P.
Table 92
Table 92 provides 250 compounds of formula (Ia) wherein X2 is CH, R2 is F, and X3, R3, X1, R5 are as defined in Table P.
Table 93
Table 93 provides 250 compounds of formula (Ia) wherein X2 is C-F, R2 is F, and X3, R3, X1, R5 are as defined in Table P.
Table 94
Table 94 provides 250 compounds of formula (Ia) wherein X2 is C-Br, R2 is F, and X3, R3, X1, R5 are as defined in Table P.
Table 95
Table 95 provides 250 compounds of formula (Ia) wherein X2 is C-CI, R2 is F, and X3, R3, X1, R5 are as defined in Table P.
Table 96
Table 96 provides 250 compounds of formula (Ia) wherein X2 is C-CF3, R2 is F, and X3, R3, X1, R5 are as defined in Table P.
from the order Acarina, for example,
Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp, Hyalomma spp., Ixodes spp., Olygonychus spp, Ornithodoros spp., Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp, Polyphagotarsonemus spp, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp, Tarsonemus spp. and Tetranychus spp.;
from the order Anoplura, for example,
Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;
from the order Coleoptera, for example,
Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp, Maladera castanea, Megascelis spp, Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp, Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp, Sphenophorus spp, Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp.;
from the order Diptera, for example,
Aedes spp., Anopheles spp, Antherigona soccata,Bactrocea oleae, Bibio hortulanus, Bradysia spp, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp, Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis spp, Rivelia quadrifasciata, Scatella spp, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;
from the order Hemiptera, for example,
Acanthocoris scabrator, Acrosternum spp, Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp., Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp, Euchistus spp., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic, Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp., Piezodorus spp, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotino-phara spp. , Thyanta spp , Triatoma spp., Vatiga illudens;
Acyrthosium pisum, Adalges spp, Agalliana ensigera, Agonoscena targionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cavariella aegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp, Cofana spectra, Cryptomyzus spp, Cicadulina spp, Coccus hesperidum, Dalbulus maidis, Dialeurodes spp, Diaphorina citri, Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp, Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp, Trialeurodes spp, Tridiscus sporoboli, Trionymus spp, Trioza erytreae , Unaspis citri, Zygina flammigera, Zyginidia scutellaris, ;
from the order Hymenoptera, for example,
Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp. and Vespa spp.;
from the order Isoptera, for example,
Coptotermes spp, Corniternes cumulans, Incisitermes spp, Macrotermes spp, Mastotermes spp, Microtermes spp, Reticulitermes spp.; Solenopsis geminate
from the order Lepidoptera, for example,
Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp, Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp, Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp, Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp, Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Papaipema nebris, Pectinophora gossypiela, Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta, and Yponomeuta spp.;
from the order Mallophaga, for example,
Damalinea spp. and Trichodectes spp.;
from the order Orthoptera, for example,
Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp. , Scapteriscus spp, and Schistocerca spp.;
from the order Psocoptera, for example,
Liposcelis spp.;
from the order Siphonaptera, for example,
Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis;
from the order Thysanoptera, for example,
Calliothrips phaseoli, Frankliniella spp., Heliothrips spp, Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp;
from the order Thysanura, for example, Lepisma saccharina.
Family | Species | Host or Crop Infested |
Buprestidae | Agrilus planipennis | Ash |
Cerambycidae | Anoplura glabripennis | Hardwoods |
Scolytidae | Xylosandrus crassiusculus | Hardwoods |
X. mutilatus | Hardwoods | |
Tomicus piniperda | Conifers |
Family | Species | Host or Crop Infested |
Buprestidae | Agrilus anxius | Birch |
Agrilus politus | Willow, Maple | |
Agrilus sayi | Bayberry, Sweetfern | |
Agrilus vittaticolllis | Apple, Pear, Cranberry, Serviceberry, Hawthorn | |
Chrysobothris femorata | Apple, Apricot, Beech, Boxelder, Cherry, Chestnut, Currant, Elm, Hawthorn, Hackberry, Hickory, Horsechestnut, Linden, Maple, Mountain-ash, Oak, Pecan, Pear, Peach, Persimmon, Plum, Poplar, Quince, Redbud, Serviceberry, Sycamore, Walnut, Willow | |
Texania campestris | Basswood, Beech, Maple, Oak, Sycamore, Willow, Yellow-poplar | |
Cerambycidae | Goes pulverulentus | Beech, Elm, Nuttall, Willow, Black oak, Cherrybark oak, Water oak, Sycamore |
Goes tigrinus | Oak | |
Neoclytus acuminatus | Ash, Hickory, Oak, Walnut, Birch, Beech, Maple, Eastern hophornbeam, Dogwood, | |
Persimmon, Redbud, Holly, Hackberry, Black locust, Honeylocust, Yellow-poplar, Chestnut, Osage-orange, Sassafras, Lilac, Mountain-mahogany, Pear, Cherry, Plum, Peach, Apple, Elm, Basswood, Sweetgum | ||
Neoptychodes trilineatus | Fig, Alder, Mulberry, Willow, Netleaf hackberry | |
Oberea ocellata | Sumac, Apple, Peach, Plum, Pear, Currant, Blackberry | |
Oberea tripunctata | Dogwood, Viburnum, Elm, Sourwood, Blueberry, Rhododendron, Azalea, Laurel, Poplar, Willow, Mulberry | |
Oncideres cingulata | Hickory, Pecan, Persimmon, Elm, Sourwood, Basswood, Honeylocust, Dogwood, Eucalyptus, Oak, Hackberry, Maple, Fruit trees | |
Saperda calcarata | Poplar | |
Strophiona nitens | Chestnut, Oak, Hickory, Walnut, Beech, Maple | |
Scolytidae | Corthylus columbianus | Maple, Oak, Yellow-poplar, Beech, Boxelder, Sycamore, Birch, Basswood, Chestnut, Elm |
Dendroctonus frontalis | Pine | |
Dryocoetes betulae | Birch, Sweetgum, Wild cherry, Beech, Pear | |
Monarthrum fasciatum | Oak, Maple, Birch, Chestnut, Sweetgum, Blackgum, Poplar, Hickory, Mimosa, Apple, Peach, Pine | |
Phloeotribus liminaris | Peach, Cherry, Plum, Black cherry, Elm, Mulberry, Mountain-ash | |
Pseudopityophthorus pruinosus | Oak, American beech, Black cherry, Chickasaw plum, Chestnut, Maple, Hickory, Hornbeam, Hophornbeam | |
Sesiidae | Paranthrene simulans | Oak, American chestnut |
Sannina uroceriformis | Persimmon | |
Synanthedon exitiosa | Peach, Plum, Nectarine, Cherry, | |
Apricot, Almond, Black cherry | ||
Synanthedon pictipes | Peach, Plum, Cherry, Beach, Black Cherry | |
Synanthedon rubrofascia | Tupelo | |
Synanthedon scitula | Dogwood, Pecan, Hickory, Oak, Chestnut, Beech, Birch, Black cherry, Elm, Mountain-ash, Viburnum, Willow, Apple, Loquat, Ninebark, Bayberry | |
Vitacea polistiformis | Grape |
Emulsifiable concentrates:
active ingredient: | 1 to 95 %, preferably 60 to 90 % |
surface-active agent: | 1 to 30 %, preferably 5 to 20 % |
liquid carrier: | 1 to 80 %, preferably 1 to 35 % |
Dusts:
active ingredient: | 0.1 to 10 %, preferably 0.1 to 5 % |
solid carrier: | 99.9 to 90 %, preferably 99.9 to 99 % |
Suspension concentrates:
active ingredient: | 5 to 75 %, preferably 10 to 50 % |
water: | 94 to 24 %, preferably 88 to 30 % |
surface-active agent: | 1 to 40 %, preferably 2 to 30 % |
Wettable powders:
active ingredient: | 0.5 to 90 %, preferably 1 to 80 % |
surface-active agent: | 0.5 to 20 %, preferably 1 to 15 % |
solid carrier: | 5 to 95 %, preferably 15 to 90 % |
Granules:
active ingredient: | 0.1 to 30 %, preferably 0.1 to 15 % |
solid carrier: | 99.5 to 70 %, preferably 97 to 85 % |
Wettable powders | a) | b) | c) |
active ingredients | 25 % | 50 % | 75 % |
sodium lignosulfonate | 5 % | 5 % | - |
sodium lauryl sulfate | 3 % | - | 5 % |
sodium diisobutylnaphthalenesulfonate | - | 6 % | 10 % |
phenol polyethylene glycol ether (7-8 mol of ethylene oxide) | - | 2 % | - |
highly dispersed silicic acid | 5 % | 10 % | 10 % |
Kaolin | 62 % | 27 % | - |
Powders for dry seed treatment | a) | b) | c) |
active ingredients | 25 % | 50 % | 75 % |
light mineral oil | 5 % | 5 % | 5 % |
highly dispersed silicic acid | 5 % | 5 % | - |
Kaolin | 65 % | 40 % | - |
Talcum | - | 20 % |
Emulsifiable concentrate | |
active ingredients | 10 % |
octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) | 3 % |
calcium dodecylbenzenesulfonate | 3 % |
castor oil polyglycol ether (35 mol of ethylene oxide) | 4 % |
Cyclohexanone | 30 % |
xylene mixture | 50 % |
Dusts | a) | b) | c) |
Active ingredients | 5 % | 6 % | 4 % |
Talcum | 95 % | - | - |
Kaolin | - | 94 % | - |
mineral filler | - | - | 96 % |
Extruder granules | |
Active ingredients | 15 % |
sodium lignosulfonate | 2 % |
carboxymethylcellulose | 1 % |
Kaolin | 82 % |
Coated granules | |
Active ingredients | 8 % |
polyethylene glycol (mol. wt. 200) | 3 % |
Kaolin | 89 % |
Suspension concentrate
active ingredients | 40 % |
propylene glycol | 10 % |
nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) | 6 % |
Sodium lignosulfonate | 10 % |
carboxymethylcellulose | 1 % |
silicone oil (in the form of a 75 % emulsion in water) | 1 % |
Water | 32 % |
Flowable concentrate for seed treatment
active ingredients | 40 % |
propylene glycol | 5 % |
copolymer butanol PO/EO | 2 % |
Tristyrenephenole with 10-20 moles EO | 2 % |
1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) | 0.5 % |
monoazo-pigment calcium salt | 5 % |
Silicone oil (in the form of a 75 % emulsion in water) | 0.2 % |
Water | 45.3 % |
Slow Release Capsule Suspension
an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
an acaricide selected from the group of substances consisting of 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithion (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenous oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotin (46) + TX, azothoate (889) + TX, benomyl (62) + TX, benoxafos (alternative name) [CCN] + TX, benzoximate (71) + TX, benzyl benzoate (IUPAC name) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromocyclen (918) + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothion (947) + TX, CGA 50'439 (development code) (125) + TX, chinomethionat (126) + TX, chlorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorfenethol (968) + TX, chlorfenson (970) + TX, chlorfensulfide (971) + TX, chlorfenvinphos (131) + TX, chlorobenzilate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumaphos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, cufraneb (1013) + TX, cyanthoate (1020) + TX, cyflumetofen (CAS Reg. No.: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demephion (1037) + TX, demephion-O (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diazinon (227) + TX, dichlofluanid (230) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimethoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinobuton (269) + TX, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, dinocton (1090) + TX, dinopenton (1092) + TX, dinosulfon (1097) + TX, dinoterbon (1098) + TX, dioxathion (1102) + TX, diphenyl sulfone (IUPAC name) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapyn (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothion (1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, ethoate-methyl (1134) + TX, etoxazole (320) + TX, etrimfos (1142) + TX, fenazaflor (1147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX, fenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, fenson (1157) + TX, fentrifanil (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacrypyrim (360) + TX, fluazuron (1166) + TX, flubenzimine (1167) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1192) + TX, formparanate (1193) + TX, gamma-HCH (430) + TX, glyodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (IUPAC/Chemical Abstracts name) (1216) + TX, hexythiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malathion (492) + TX, malonoben (1254) + TX, mecarbam (502) + TX, mephosfolan (1261) + TX, mesulfen (alternative name) [CCN] + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methidathion (529) + TX, methiocarb (530) + TX, methomyl (531) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naled (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluridide (1309) + TX, nikkomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phenkapton (1330) + TX, phenthoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosphamidon (639) + TX, phoxim (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridaphenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalphos (711) + TX, quintiofos (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sophamide (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, thiafenox (alternative name) + TX, thiocarboxime (1431) + TX, thiofanox (800) + TX, thiometon (801) + TX, thioquinox (1436) + TX, thuringiensin (alternative name) [CCN] + TX, triamiphos (1441) + TX, triarathene (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trifenofos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX,
an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX,
an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,
an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX,
a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodicin (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargaphen (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX, and thiomersal (alternative name) [CCN] + TX,
a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151) + TX, Cryptolaemus montrouzieri (alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX, Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp. (alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX,
a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX,
a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,
an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z)-hexadec-11-enal (IUPAC name) (436) + TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437) + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438) + TX, (Z)-icos-13-en-10-one (IUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (IUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, brevicomin (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemone (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (IUPAC name) (286) + TX, dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, gossyplure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, octadeca-3,13-dien-1-yl acetate (IUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, oryctalure (alternative name) (317) + TX, ostramone (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidin (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN] + TX,
an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX,
an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058) + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), + TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (IUPAC name) (1066) + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate (IUPAC/ Chemical Abstracts name) (1109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts name) (935) + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283) + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamiprid (4) + TX, acethion (alternative name) [CCN] + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, acrylonitrile (IUPAC name) (861) + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, allosamidin (alternative name) [CCN] + TX, allyxycarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminium phosphide (640) + TX, amidithion (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, athidathion (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (41) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azothoate (889) + TX, Bacillus thuringiensis delta endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (IUPAC/Chemical Abstracts name) (892) + TX, barthrin [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultap (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioallethrin (78) + TX, bioallethrin S-cyclopentenyl isomer (alternative name) (79) + TX, bioethanomethrin [CCN] + TX, biopermethrin (908) + TX, bioresmethrin (80) + TX, bis(2-chloroethyl) ether (IUPAC name) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromfenvinfos (914) + TX, bromocyclen (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butathiofos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbophenothion (947) + TX, carbosulfan (119) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorbicyclen (960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyfos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinphos (131) + TX, chlorfluazuron (132) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorphoxim (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cismethrin (80) + TX, clocythrin (alternative name) + TX, cloethocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumithoate (1006) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, crufomate (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanofenphos (1019) + TX, cyanophos (184) + TX, cyanthoate (1020) + TX, cyclethrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cythioate (alternative name) [CCN] + TX, d-limonene (alternative name) [CCN] + TX, d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomet (216) + TX, DDT(219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demephion (1037) + TX, demephion-O (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulphon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapthon (1050) + TX, dichlofenthion (1051) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081) + TX, dimetan (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimetilan (1086) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271) + TX, diofenolan (1099) + TX, dioxabenzofos (1100) + TX, dioxacarb (1101) + TX, dioxathion (1102) + TX, disulfoton (278) + TX, dithicrofos (1108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1115) + TX, ecdysterone (alternative name) [CCN] + TX, EI 1642 (development code) (1118) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empenthrin (292) + TX, endosulfan (294) + TX, endothion (1121) + TX, endrin (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epofenonane (1124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, etaphos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethion (309) + TX, ethiprole (310) + TX, ethoate-methyl (1134) + TX, ethoprophos (312) + TX, ethyl formate (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimfos (1142) + TX, EXD (1143) + TX, famphur (323) + TX, fenamiphos (326) + TX, fenazaflor (1147) + TX, fenchlorphos (1148) + TX, fenethacarb (1149) + TX, fenfluthrin (1150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1153) + TX, fenoxycarb (340) + TX, fenpirithrin (1155) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fensulfothion (1158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (CAS. Reg. No.: 272451-65-7) + TX, flucofuron (1168) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1169) + TX, flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, fonofos (1191) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1192) + TX, formparanate (1193) + TX, fosmethilan (1194) + TX, fospirate (1195) + TX, fosthiazate (408) + TX, fosthietan (1196) + TX, furathiocarb (412) + TX, furethrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (1211) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hyquincarb (1223) + TX, imidacloprid (458) + TX, imiprothrin (460) + TX, indoxacarb (465) + TX, iodomethane (IUPAC name) (542) + TX, IPSP (1229) + TX, isazofos (1231) + TX, isobenzan (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrin (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, kelevan (1249) + TX, kinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lirimfos (1251) + TX, lufenuron (490) + TX, lythidathion (1253) + TX, m-cumenyl methylcarbamate (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malathion (492) + TX, malonoben (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarphon (1258) + TX, menazon (1260) + TX, mephosfolan (1261) + TX, mercurous chloride (513) + TX, mesulfenfos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts name) (1268) + TX, methidathion (529) + TX, methiocarb (530) + TX, methocrotophos (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methoquin-butyl (1276) + TX, methothrin (alternative name) (533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metofluthrin [CCN] + TX, metolcarb (550) + TX, metoxadiazone (1288) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naftalofos (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (IUPAC/Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyram (579) + TX, nithiazine (1311) + TX, nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, 0-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC name) (1057) + TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name) (1074) + TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075) + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathion (615) + TX, parathion-methyl (616) + TX, penfluron (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-38 (development code) (1328) + TX, phenkapton (1330) + TX, phenothrin (630) + TX, phenthoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosnichlor (1339) + TX, phosphamidon (639) + TX, phosphine (IUPAC name) (640) + TX, phoxim (642) + TX, phoxim-methyl (1340) + TX, pirimetaphos (1344) + TX, pirimicarb (651) + TX, pirimiphos-ethyl (1345) + TX, pirimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, prallethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidophos (1349) + TX, profenofos (662) + TX, profluthrin [CCN] + TX, promacyl (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothiofos (686) + TX, prothoate (1362) + TX, protrifenbute [CCN] + TX, pymetrozine (688) + TX, pyraclofos (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, pyridaphenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, pyriproxyfen (708) + TX, quassia (alternative name) [CCN] + TX, quinalphos (711) + TX, quinalphos-methyl (1376) + TX, quinothion (1380) + TX, quintiofos (1381) + TX, R-1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryania (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, sophamide (1402) + TX, spinosad (737) + TX, spiromesifen (739) + TX, spirotetrmat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, terallethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid (791) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, thicrofos (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiofanox (800) + TX, thiometon (801) + TX, thionazin (1434) + TX, thiosultap (803) + TX, thiosultap-sodium (803) + TX, thuringiensin (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin (1440) + TX, triamiphos (1441) + TX, triazamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronat (1452) + TX, trifenofos (1455) + TX, triflumuron (835) + TX, trimethacarb (840) + TX, triprene (1459) + TX, vamidothion (847) + TX, vaniliprole [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994-63-19 + TX, chlorantraniliprole [500008-45-7] + TX, cyenopyrafen [560121-52-0] + TX, cyflumetofen [400882-07-7] + TX, pyrifluquinazon [337458-27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprole [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-2] + TX, triflumezopyrim (disclosed in WO 2012/092115) + TX, fluxametamide (WO 2007/026965) + TX, epsilon-metofluthrin [240494-71-7] + TX, epsilon-momfluorothrin [1065124-65-3] + TX, fluazaindolizine [1254304-22-7] + TX, chloroprallethrin [399572-87-3] + TX, fluxametamide [928783-29-3] + TX, cyhalodiamide [1262605-53-7] + TX, tioxazafen [330459-31-9] + TX, broflanilide [1207727-04-5] + TX, flufiprole [704886-18-0] + TX, cyclaniliprole [1031756-98-5] + TX, tetraniliprole [1229654-66-3] + TX, guadipyr (described in WO2010/060231) + TX, cycloxaprid (described in WO2005/077934) + TX,
a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, trifenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [394730-71-3] + TX,
a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC/Chemical Abstracts name) (1045) + TX, 1,2-dichloropropane (IUPAC/ Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, dichlofenthion (1051) + TX, dicliphos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ethoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothion (1158) + TX, fosthiazate (408) + TX, fosthietan (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidofos (1230) + TX, isazofos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphon (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, Myrothecium verrucaria composition (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazin (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX,
a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,
a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,
a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadine (1183) + TX, flupropadine hydrochloride (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, phosacetim (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, scilliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX,
a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,
an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,
a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX,
and biologically active compounds selected from the group consisting of azaconazole (60207-31-0] + TX, bitertanol [70585-36-3] + TX, bromuconazole [116255-48-2] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [114369-43-6] + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674-21-0] + TX, hexaconazole [79983-71-4] + TX, imazalil [35554-44-0] + TX, imibenconazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0] + TX, pefurazoate [101903-30-4] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [112281-77-3] + TX, triadimefon [43121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [131983-72-7] + TX, ancymidol [12771-68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [41483-43-6] + TX, dimethirimol [5221-53-4] + TX, ethirimol [23947-60-6] + TX, dodemorph [1593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61-2] + TX, mepanipyrim [110235-47-7] + TX, pyrimethanil [53112-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [131341-86-1] + TX, benalaxyl [71626-11-4] + TX, furalaxyl [57646-30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX, chlozolinate [84332-86-5] + TX, dichlozoline [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471-44-8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fenfuram [24691-80-3] + TX, flutolanil [66332-96-5] + TX, mepronil [55814-41-0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [112-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961-52-4] + TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, kresoxim-methyl [143390-89-0] + TX, metominostrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, orysastrobin [248593-16-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, ferbam [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, metiram [9006-42-2] + TX, propineb [12071-83-9] + TX, thiram [137-26-8] + TX, zineb [12122-67-7] + TX, ziram [137-30-4] + TX, captafol [2425-06-1] + TX, captan [133-06-2] + TX, dichlofluanid [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-07-3] + TX, tolylfluanid [731-27-1] + TX, bordeaux mixture [8011-63-0] + TX, copperhydroxid [20427-59-2] + TX, copperoxychlorid [1332-40-7] + TX, coppersulfat [7758-98-7] + TX, copperoxid [1317-39-1] + TX, mancopper [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap [131-72-6] + TX, nitrothal-isopropyl [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenphos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, benthiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamid [180409-60-3] + TX, cymoxanil [57966-95-7] + TX, dichlone [117-80-6] + TX, diclocymet [139920-32-4] + TX, diclomezine [62865-36-5] + TX, dicloran [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP-L190 (Flumorph) [211867-47-9] + TX, dithianon [3347-22-6] + TX, ethaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, fenamidone [161326-34-7] + TX, fenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferimzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [239110-15-7] + TX, flusulfamide [106917-52-6] + TX, fenhexamid [126833-17-8] + TX, fosetyl-aluminium [39148-24-8] + TX, hymexazol [10004-44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (Cyazofamid) [120116-88-3] + TX, kasugamycin [6980-18-3] + TX, methasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencycuron [66063-05-6] + TX, phthalide [27355-22-2] + TX, polyoxins [11113-80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazid [189278-12-4] + TX, pyroquilon [57369-32-1] + TX, quinoxyfen [124495-18-7] + TX, quintozene [82-68-8] + TX, sulfur [7704-34-9] + TX, tiadinil [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [41814-78-2] + TX, triforine [26644-46-2] + TX, validamycin [37248-47-8] + TX, zoxamide (RH7281) [156052-68-5] + TX, mandipropamid [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, sedaxane [874967-67-6] + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide (dislosed in WO 2007/048556) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide (disclosed in WO 2006/087343) + TX, [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate [915972-17-7] + TX, 1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide [926914-55-8] + TX; lancotrione [1486617-21-3] + TX; florpyrauxifen [943832-81-3] + TX;, ipfentrifluconazole[1417782-08-1] + TX;, mefentrifluconazole [1417782-03-6] + TX; quinofumelin [861647-84-9] + TX;, chloroprallethrin [399572-87-3] + TX; cyhalodiamide [1262605-53-7] + TX;, fluazaindolizine [1254304-22-7] + TX; fluxametamide [928783-29-3] + TX; epsilon-metofluthrin [240494-71-7] + TX; epsilon-momfluorothrin [1065124-65-3] + TX; pydiflumetofen [1228284-64-7] + TX; kappa-bifenthrin [439680-76-9] + TX; broflanilide [1207727-04-5] + TX; dicloromezotiaz [1263629-39-5] + TX; dipymetitrone [16114-35-5] + TX; pyraziflumid [942515-63-1] + TX; and kappa-tefluthrin [391634-71-2] + TX; and
microbials including: Acinetobacter lwoffii + TX, Acremonium alternatum + TX + TX, Acremonium cephalosporium + TX + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternate + TX, Alternaria cassia + TX, Alternaria destruens (Smolder®) + TX, Ampelomyces quisqualis (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL 21882 (Aflaguard®) + TX, Aspergillus spp. + TX, Aureobasidium pullulans + TX, Azospirillum + TX, (MicroAZ® + TX, TAZO B®) + TX, Azotobacter + TX, Azotobacter chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus licheniformis strain HB-2 (Biostart™ Rhizoboost®) + TX, Bacillus licheniformis strain 3086 (EcoGuard® + TX, Green Releaf®) + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe® + TX, BioNem-WP® + TX, VOTiVO®) + TX, Bacillus firmus strain I-1582 + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides strain AQ726 + TX, Bacillus papillae (Milky Spore Powder®) + TX, Bacillus pumilus spp. + TX, Bacillus pumilus strain GB34 (Yield Shield®) + TX, Bacillus pumilus strain AQ717 + TX, Bacillus pumilus strain QST 2808 (Sonata® + TX, Ballad Plus®) + TX, Bacillus spahericus (VectoLex®) + TX, Bacillus spp. + TX, Bacillus spp. strain AQ175 + TX, Bacillus spp. strain AQ177 + TX, Bacillus spp. strain AQ178 + TX, Bacillus subtilis strain QST 713 (CEASE® + TX, Serenade® + TX, Rhapsody®) + TX, Bacillus subtilis strain QST 714 (JAZZ®) + TX, Bacillus subtilis strain AQ153 + TX, Bacillus subtilis strain AQ743 + TX, Bacillus subtilis strain QST3002 + TX, Bacillus subtilis strain QST3004 + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (Taegro® + TX, Rhizopro®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1Ab + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis israelensis (BMP123® + TX, Aquabac® + TX, VectoBac®) + TX, Bacillus thuringiensis kurstaki (Javelin® + TX, Deliver® + TX, CryMax® + TX, Bonide® + TX, Scutella WP® + TX, Turilav WP ® + TX, Astuto® + TX, Dipel WP® + TX, Biobit® + TX, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis var. aizawai (XenTari® + TX, DiPel®) + TX, bacteria spp. (GROWMEND® + TX, GROWSWEET® + TX, Shootup®) + TX, bacteriophage of Clavipacter michiganensis (AgriPhage®) + TX, Bakflor® + TX, Beauveria bassiana (Beaugenic® + TX, Brocaril WP®) + TX, Beauveria bassiana GHA (Mycotrol ES® + TX, Mycotrol O® + TX, BotaniGuard®) + TX, Beauveria brongniartii (Engerlingspilz® + TX, Schweizer Beauveria® + TX, Melocont®) + TX, Beauveria spp. + TX, Botrytis cineria + TX, Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis (Novodor®) + TX, BtBooster + TX, Burkholderia cepacia (Deny® + TX, Intercept® + TX, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp. + TX, Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida saitoana (Bio-Coat® + TX, Biocure®) + TX, Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cedecea dravisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium chlorocephalum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp. + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX, Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus (Cryptex®) + TX, Cupriavidus campinensis + TX, Cydia pomonella granulovirus (CYD-X®) + TX, Cydia pomonella granulovirus (Madex® + TX, Madex Plus® + TX, Madex Max/ Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp. + TX, Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean® / Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop® + TX, Prestop®) + TX, Gliocladium roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulovirus (Granupom®) + TX, Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi + TX, Halomonas spp. + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®) + TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar®) + TX, Isoflavone - formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp. + TX, Lagenidium giganteum (Laginex®) + TX, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Met52®) + TX, Metarhizium anisopliae (Destruxin WP®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®) + TX, Muscodor roseus strain A3-5 + TX, Mycorrhizae spp. (AMykor® + TX, Root Maximizer®) + TX, Myrothecium verrucaria strain AARC-0255 (DiTera®) + TX, BROS PLUS® + TX, Ophiostoma piliferum strain D97 (Sylvanex®) + TX, Paecilomyces farinosus + TX, Paecilomyces fumosoroseus (PFR-97® + TX, PreFeRal®) + TX, Paecilomyces linacinus (Biostat WP®) + TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1®) + TX, Pantoea spp. + TX, Pasteuria spp. (Econem®) + TX, Pasteuria nishizawae + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart® + TX, TagTeam®) + TX, Penicillium brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp. + TX, Penicillium viridicatum + TX, Phlebiopsis gigantean (Rotstop®) + TX, phosphate solubilizing bacteria (Phosphomeal®) + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp. + TX, Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava + TX, Pseudomons fluorescens (Zequanox®) + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®) + TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium paroecandrum + TX, Pythium oligandrum (Polygandron® + TX, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia (Dormal® + TX, Vault®) + TX, Rhizoctonia + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula spp. + TX, Rhodotorula glutinis + TX, Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorula rubra + TX, Saccharomyces cerevisiae + TX, Salinococcus roseus + TX, Sclerotinia minor + TX, Sclerotinia minor (SARRITOR®) + TX, Scytalidium spp. + TX, Scytalidium uredinicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X® + TX, Spexit®) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp. + TX, Sordaria fimicola + TX, Spodoptera littoralis nucleopolyhedrovirus (Littovir®) + TX, Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus + TX, Streptomyces griseoviridis (Mycostop®) + TX, Streptomyces lydicus (Actinovate®) + TX, Streptomyces lydicus WYEC-108 (ActinoGrow®) + TX, Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp. + TX, Trichoderma asperellum (T34 Biocontrol®) + TX, Trichoderma gamsii (Tenet®) + TX, Trichoderma atroviride (Plantmate®) + TX, Trichoderma hamatum TH 382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum-P® + TX, PlantShield HC® + TX, RootShield® + TX, Trianum-G®) + TX, Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp. LC 52 (Sentinel®) + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX, Trichothecium spp. + TX, Trichothecium roseum + TX, Typhula phacorrhiza strain 94670 + TX, Typhula phacorrhiza strain 94671 + TX, Ulocladium atrum + TX, Ulocladium oudemansii (Botry-Zen®) + TX, Ustilago maydis + TX, various bacteria and supplementary micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Verticillium lecanii (Mycotal® + TX, Vertalec®) + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Xenorhabdus bovienii + TX, Xenorhabdus nematophilus; and
Plant extracts including: pine oil (Retenol®) + TX, azadirachtin (Plasma Neem Oil® + TX, AzaGuard® + TX, MeemAzal® + TX, Molt-X® + TX, Botanical IGR (Neemazad® + TX, Neemix®) + TX, canola oil (Lilly Miller Vegol®) + TX, Chenopodium ambrosioides near ambrosioides (Requiem®) + TX, Chrysanthemum extract (Crisant®) + TX, extract of neem oil (Trilogy®) + TX, essentials oils of Labiatae (Botania®) + TX, extracts of clove rosemary peppermint and thyme oil (Garden insect killer®) + TX, Glycinebetaine (Greenstim®) + TX, garlic + TX, lemongrass oil (GreenMatch®) + TX, neem oil + TX, Nepeta cataria (Catnip oil) + TX, Nepeta catarina + TX, nicotine + TX, oregano oil (MossBuster®) + TX, Pedaliaceae oil (Nematon®) + TX, pyrethrum + TX, Quillaja saponaria (NemaQ®) + TX, Reynoutria sachalinensis (Regalia® + TX, Sakalia®) + TX, rotenone (Eco Roten®) + TX, Rutaceae plant extract (Soleo®) + TX, soybean oil (Ortho ecosense®) + TX, tea tree oil (Timorex Gold®) + TX, thymus oil + TX, AGNIQUE® MMF + TX, BugOil® + TX, mixture of rosemary sesame pepermint thyme and cinnamon extracts (EF 300®) + TX, mixture of clove rosemary and peppermint extract (EF 400®) + TX, mixture of clove pepermint garlic oil and mint (Soil Shot®) + TX, kaolin (Screen®) + TX, storage glucam of brown algae (Laminarin®); and
pheromones including: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Codling Moth Pheromone (Paramount dispenser-(CM)/ Isomate C-Plus®) + TX, Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone®) + TX, Leafroller pheromone (3M MEC - LR Sprayable Pheromone®) + TX, Muscamone (Snip7 Fly Bait® + TX, Starbar Premium Fly Bait®) + TX, Oriental Fruit Moth Pheromone (3M oriental fruit moth sprayable pheromone®) + TX, Peachtree Borer Pheromone (Isomate-P®) + TX, Tomato Pinworm Pheromone (3M Sprayable pheromone®) + TX, Entostat powder (extract from palm tree) (Exosex CM®) + TX, (E + TX,Z + TX,Z)-3 + TX,8 + TX,11 Tetradecatrienyl acetate + TX, (Z + TX,Z + TX,E)-7 + TX,11 + TX,13-Hexadecatrienal + TX, (E + TX,Z)-7 + TX,9-Dodecadien-1-yl acetate + TX, 2-Methyl-1-butanol + TX, Calcium acetate + TX, Scenturion® + TX, Biolure® + TX, Check-Mate® + TX, Lavandulyl senecioate; and
Macrobials including: Aphelinus abdominalis + TX, Aphidius ervi (Aphelinus-System®) + TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline® + TX, Andersoni-System®) + TX, Amblyseius californicus (Amblyline® + TX, Spical®) + TX, Amblyseius cucumeris (Thripex® + TX, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii® + TX, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus loecki + TX, Anagyrus pseudococci (Citripar®) + TX, Anicetus benefices + TX, Anisopteromalus calandrae + TX, Anthocoris nemoralis (Anthocoris-System®) + TX, Aphelinus abdominalis (Apheline® + TX, Aphiline®) + TX, Aphelinus asychis + TX, Aphidius colemani (Aphipar®) + TX, Aphidius ervi (Ervipar®) + TX, Aphidius gifuensis + TX, Aphidius matricariae (Aphipar-M®) + TX, Aphidoletes aphidimyza (Aphidend®) + TX, Aphidoletes aphidimyza (Aphidoline®) + TX, Aphytis lingnanensis + TX, Aphytis melinus + TX, Aprostocetus hagenowii + TX, Atheta coriaria (Staphyline®) + TX, Bombus spp. + TX, Bombus terrestris (Natupol Beehive®) + TX, Bombus terrestris (Beeline® + TX, Tripol®) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperla carnea (Chrysoline®) + TX, Chrysoperla carnea (Chrysopa®) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus chamaeleon + TX, Closterocerus spp. + TX, Coccidoxenoides perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug® + TX, Cryptoline®) + TX, Cybocephalus nipponicus + TX, Dacnusa sibirica + TX, Dacnusa sibirica (Minusa®) + TX, Diglyphus isaea (Diminex®) + TX, Delphastus catalinae (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsis jucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea + TX, Diglyphus isaea (Miglyphus® + TX, Digline®) + TX, Dacnusa sibirica (DacDigline® + TX, Minex®) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max® + TX, Encarline® + TX, En-Strip®) + TX, Eretmocerus eremicus (Enermix®) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend®) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus + TX, Eretmocerus eremicus (Ercal® + TX, Eretline e®) + TX, Eretmocerus eremicus (Bemimix®) + TX, Eretmocerus hayati + TX, Eretmocerus mundus (Bemipar® + TX, Eretline m®) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiella acarisuga (Spidend®) + TX, Feltiella acarisuga (Feltiline®) + TX, Fopius arisanus + TX, Fopius ceratitivorus + TX, Formononetin (Wirless Beehome®) + TX, Franklinothrips vespiformis (Vespop®) + TX, Galendromus occidentalis + TX, Goniozus legneri + TX, Habrobracon hebetor + TX, Harmonia axyridis (HarmoBeetle®) + TX, Heterorhabditis spp. (Lawn Patrol®) + TX, Heterorhabditis bacteriophora (NemaShield HB® + TX, Nemaseek® + TX, Terranem-Nam® + TX, Terranem® + TX, Larvanem® + TX, B-Green® + TX, NemAttack ® + TX, Nematop®) + TX, Heterorhabditis megidis (Nemasys H® + TX, BioNem H® + TX, Exhibitline hm® + TX, Larvanem-M®) + TX, Hippodamia convergens + TX, Hypoaspis aculeifer (Aculeifer-System® + TX, Entomite-A®) + TX, Hypoaspis miles (Hypoline m® + TX, Entomite-M®) + TX, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar (Natufly®) + TX, Lysiphlebus testaceipes + TX, Macrolophus caliginosus (Mirical-N® + TX, Macroline c® + TX, Mirical®) + TX, Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus lounsburyi + TX, Micromus angulatus (Milacewing®) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar@) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumeris (THRYPEX®) + TX, Neoseiulus fallacis + TX, Nesideocoris tenuis (NesidioBug® + TX, Nesibug®) + TX, Ophyra aenescens (Biofly®) + TX, Orius insidiosus (Thripor-I® + TX, Oriline i®) + TX, Orius laevigatus (Thripor-L® + TX, Oriline I®) + TX, Orius majusculus (Oriline m®) + TX, Orius strigicollis (Thripor-S®) + TX, Pauesia juniperorum + TX, Pediobius foveolatus + TX, Phasmarhabditis hermaphrodita (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex® + TX, Phytoline p®) + TX, Podisus maculiventris (Podisus®) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Psyllaephagus pilosus + TX, Psyttalia concolor (complex) + TX, Quadrastichus spp. + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C® + TX, Millenium® + TX, BioNem C® + TX, NemAttack® + TX, Nemastar® + TX, Capsanem®) + TX, Steinernema feltiae (NemaShield® + TX, Nemasys F® + TX, BioNem F® + TX, Steinernema-System® + TX, NemAttack® + TX, Nemaplus® + TX, Exhibitline sf® + TX, Scia-rid® + TX, Entonem®) + TX, Steinernema kraussei (Nemasys L® + TX, BioNem L® + TX, Exhibitline srb®) + TX, Steinernema riobrave (BioVector® + TX, BioVektor®) + TX, Steinernema scapterisci (Nematac S®) + TX, Steinernema spp. + TX, Steinernematid spp. (Guardian Nematodes®) + TX, Stethorus punctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b®) + TX, Trichogramma brassicae (Tricho-Strip®) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae + TX, Trichogramma platneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator; and
other biologicals including: abscisic acid + TX, bioSea® + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper Octanoate (Cueva®) + TX, Delta traps (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct® + TX, Ni-HIBIT Gold CST®) + TX, Ferri-phosphate (Ferramol®) + TX, Funnel traps (Trapline y®) + TX, Gallex® + TX, Grower's Secret® + TX, Homo-brassonolide + TX, Iron Phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait®) + TX, MCP hail trap (Trapline f®) + TX, Microctonus hyperodae + TX, Mycoleptodiscus terrestris (Des-X®) + TX, BioGain® + TX, Aminomite® + TX, Zenox® + TX, Pheromone trap (Thripline ams®) + TX, potassium bicarbonate (MilStop®) + TX, potassium salts of fatty acids (Sanova®) + TX, potassium silicate solution (Sil-Matrix®) + TX, potassium iodide + potassiumthiocyanate (Enzicur®) + TX, SuffOil-X® + TX, Spider venom + TX, Nosema locustae (Semaspore Organic Grasshopper Control®) + TX, Sticky traps (Trapline YF® + TX, Rebell Amarillo®) + TX and Traps (Takitrapline y + b®) + TX.
Preparatory Examples:
MS | Spectra were recorded on a Mass Spectrometer from Waters (SQD or SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30 V, Extractor: 2.00 V, Source Temperature: 150°C, Desolvation Temperature: 350°C, Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da). |
LC | Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 µm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH: gradient: 0 min 0% B, 100%A; 1.2-1.5min 100% B; Flow (ml/min) 0.85. |
MS | Spectra were recorded on a Mass Spectrometer from Waters (SQD or SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 45 V, Extractor: 2.00 V, Source Temperature: 150°C, Desolvation Temperature: 350°C, Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da). |
LC | Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 µm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH: gradient: 0 min 0% B, 100%A; 1.2-1.5min 100% B; Flow (ml/min) 0.85. |
MS | Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 3.00 kV, Cone range: 30V, Extractor: 2.00 V, Source Temperature: 150°C, Desolvation Temperature: 350°C, Cone Gas Flow: 50 l/h, Desolvation Gas Flow: 650 l/h, Mass range: 100 to 900 Da) |
LC | Acquity UPLC from Waters: Binary pump, heated column compartment, diode-array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 µm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH, gradient: 10-100% B in 2.7 min; Flow (ml/min) 0.85 |
MS | Spectra were recorded on a Waters SQD2 Mass Spectrometer (Single quadrupole mass spectrometer) lonisation method: Electrospray, Polarity: positive ions Capillary (kV) 3.50, Cone (V) 30.00, Extractor (V) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 400 Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700, Mass range: 140 to 800 Da; DAD Wavelength range (nm): 210 to 400 | |||
LC | Method Waters ACQUITY UPLC with the following HPLC gradient conditions (Solvent A: Water/Methanol 9:1,0.1 % formic acid and Solvent B: Acetonitrile, 0.1% formic acid) | |||
Time (minutes) | A (%) | B (%) | Flow rate (ml/min) | |
0 | 100 | 0 | 0.75 | |
2.5 | 0 | 100 | 0.75 | |
2.8 | 0 | 100 | 0.75 | |
3.0 | 100 | 0 | 0.75 | |
Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60°C. |
Example 1: N-(2-cyclobutylsulfonylisoxazolidin-4-yl)-4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzamide (example A014 in table A)
Step A: tert-butyl 4-[[4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoyl]amino]isoxazolidine-2-carboxylate
Step B: 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-isoxazolidin-2-ium-4-yl-2-methyl-benzamide; 2,2,2-trifluoroacetate
Step C: N-(2-cyclobutylsulfonylisoxazolidin-4-yl)-4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzamide
Example 2: 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(2-methylsulfonylisoxazolidin-4-yl)benzamide (example A001 in table A)
Step A: tert-butyl4-[[4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoylamino]isoxazolidine-2-carboxylate
Steps B and C: 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(2-methylsulfonylisoxazolidin-4-yl)benzamide
Example 3: Single diastereomers 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-[(4R)-2-methylsulfonylisoxazolidin-4-yl]benzamide (example A013 in Table A) and 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-[(4S)-2-methylsulfonylisoxazolidin-4-yl]benzamide (example A012 in table A)
Analytical HPLC method:
HPLC: Waters UPLC - HClass, DAD Detector Waters UPLC
Column: Daicel CHIRALPAK® IB, 3µm, 0.46cm x 10cm
Mobile phase: Hept/EtOH 90/10
Flow rate: 1.0 ml/min
Detection: 265 nm
Sample concentration: 1mg/mL in DCM/iPrOH 50/50
Injection: 2µl
Preparative HPLC method:
Autopurification System from Waters: 2767 sample Manager, 2489 UV/Visible Detector, 2545 Quaternary Gradient Module.
Column: Daicel CHIRALPAK® IB, 5µm, 1.0 cm x 25cm
Mobile phase: Hept/EtOH 90/10
Flow rate: 10 ml/min
Detection: UV 260 nm
Sample concentration: 50mg/mL in (4ml Heptane/2ml EtOH)
Injection: 250µl - 500µl
Results:
First eluting enantiomer | Second eluting enantiomer |
Retention time (min) ∼ 6.68 | Retention time (min) ∼ 10.79 |
Chemical purity (area% at 265 nm) 99 | Chemical purity (area% at 265 nm) 99 |
Enantiomeric excess (%) > 99 | Enantiomeric excess (%) > 99 |
4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-[(4R)-2-methylsulfonylisoxazolidin-4-yl]benzamide (example A013 in Table A) with a retention time of 21.71 min under the conditions described hereafter
and
4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-[(4S)-2-methylsulfonylisoxazolidin-4-yl]benzamide (example A012 in table A) wit a retention time of 17.61 min under the same conditions.
Analytical method:
HPLC:Waters UPLC - HClass
DAD Detector Waters UPLC
Column: Daicel CHIRALPAK® IB, 3µm, 0.46cm x 10cm
Mobile phase: Heptane/EtOH 90/10
Flow rate: 1.0 ml/min
Detection: 265nm
Sample concentration: 1 mg/mL in DCM/iPr 50/50
Injection: 2µL
Example 4: 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[2-(dimethylsulfamoyl)isoxazolidin-4-yl]-2-methyl-benzamide (example A010 in table A)
Analytical HPLC method:
HPLC: Waters UPLC - HClass, DAD Detector Waters UPLC
Column: Daicel CHIRALPAK® IA, 3µm, 0.46cm x 10cm
Mobile phase: TBME/EtOH 98/02
Flow rate: 1.0 ml/min
Detection: 265 nm
Sample concentration: 1mg/mL in DCM/iPrOH 50/50
Injection: 2µl
Preparative HPLC method:
Autopurification System from Waters: 2767 sample Manager, 2489 UV/Visible Detector, 2545 Quaternary Gradient Module.
Column: Daicel CHIRALPAK® IA, 5µm, 1.0 cm x 25cm
Mobile phase: TBME/EtOH 98/02
Flow rate: 10 ml/min
Detection: UV 260 nm
Sample concentration: 25mg/mL in dichloromethane, filtered
Injection: 100µl - 200µl
First eluting enantiomer (compound A143 in table A) | Second eluting enantiomer (compound A034 in table A) |
Retention time (min) ∼ 3.6 | Retention time (min) ∼ 4.77 |
Chemical purity (area% at 266 nm) 99 | Chemical purity (area% at 266 nm) 99 |
Enantiomeric excess (%) > 99 | Enantiomeric excess (%) > 99 |
Example 5: 2-chloro-N-[(4R)-2-(cyclopropylsulfamoyl)isoxazolidin-4-yl]-4-[(5S)-5-(3.5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzamide (compound A154 in table A)
Step A: methyl 2-[(4S)-4-hydroxyisoxazolidine-2-carbonyl]benzoate
Step B: (4S)-isoxazolidin-2-ium-4-ol chloride
Step C: tert-butyl (4S)-4-hydroxyisoxazolidine-2-carboxylate
Step D: tert-butyl (4S)-4-methylsulfonyloxyisoxazolidine-2-carboxylate
Step E: tert-butyl (4R)-4-azidoisoxazolidine-2-carboxylate
Step F: tert-butyl (4R)-4-aminoisoxazolidine-2-carboxylate
HPLC: Waters UPLC - HClass
DAD Detector Waters UPLC
Column: Daicel CHIRALPAK® IF, 3µm, 0.46cm x 10cm
Mobile phase: Heptane/EtOH/DEA 80/20/0.1%
Flow rate: 1.0 ml/min
Detection: 220 nm
Sample concentration: 1 mg/mL in iPrOH 100%
Injection: 2µL
Under these conditions, the enantiomers have a retention time of 5.99 min and 9.69 min respectively. The product obtained as described above showed only the peak of the short retention time, the other isomer being not detected.Step G: tert-butyl (4R)-4-[[2-chloro-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzoyl]amino]isoxazolidine-2-carboxylate
Step H: 2-chloro-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-isoxazolidin-4-yl]benzamide
Step I: N-[(4R)-2-(dimethylsulfamoyl)isoxazolidin-4-yl]-2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzamide (compound A154 in table A)
Example 6: N-[(4R)-2-(dimethylsulfamoyl)isoxazolidin-4-yl]-2-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzamide (compound A037 in table A)
Step A: [(4S)-2-(dimethylsulfamoyl)isoxazolidin-4-yl]methanesulfonate
Steps B then C: (4R)-4-amino-N,N-dimethyl-isoxazolidine-2-sulfonamide
Step D: N-[(4R)-2-(dimethylsulfamoyl)isoxazolidin-4-yl]-2-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzamide
Example 7: Synthesis of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2 ethylsulfonylisoxazolidin-4-yl]-2-methyl-benzamide (Compound A121 in table A)
Step A: [(4S)-2-ethylsulfonylisoxazolidin-4-yl]ethanesulfonate
Step B: (4R)-4-azido-2-ethylsulfonyl-isoxazolidine
Step C: (4R)-2-ethylsulfonylisoxazolidin-4-amine
Step D: 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethylsulfonylisoxazolidin-4-yl]-2-methyl-benzamide
Example 8 : 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(2-methylsulfonylisoxazolidin-4-yl)benzamide
Step A: tert-butyl 4-[(4-acetyl-2-methyl-benzoyl)amino]isoxazolidine-2-carboxylate
Step B: 4-acetyl-2-methyl-N-(2-methylsulfonylisoxazolidin-4-yl)benzamide
Step C: 4-[(E-Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-N-(2-methylsulfonylisoxazolidin-4-yl)benzamide
Step D : 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(2-methylsulfonylisoxazolidin-4-yl)benzamide
Example 9: Method for preparing compounds of the invention from a carboxylic acid
Example 10: Resolution of 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[2-(dimethylsulfamoyl)isoxazolidin-4-yl]-2-methyl-benzamide (examples A037 and A112 in table A)
Analytical HPLC method:
HPLC: Waters UPLC - HClass, DAD Detector Waters UPLC
Column: Daicel CHIRALPAK® IF, 3µm, 0.46cm x 10cm
Mobile phase: Hept/EtOAc 70/30
Flow rate: 1.0 ml/min
Detection: 265 nm
Sample concentration: 1mg/mL in DCM/iPrOH 50/50
Injection: 2µl
Preparative HPLC method:
Autopurification System from Waters: 2767 sample Manager, 2489 UV/Visible Detector, 2545 Quaternary Gradient Module.
Column: Daicel CHIRALPAK® IF, 5µm, 1.0 cm x 25cm
Mobile phase: Hept/EtOAc 70/30
Flow rate: 10 ml/min
Detection: UV 260 nm
Sample concentration: 166 mg/mL in EtOAc/Hept, filtered
Injection: 30µl - 150µl
First eluting enantiomer (compound A112 in table A) | Second eluting enantiomer (compound A037 in table A) |
Retention time (min) ∼ 5.45 | Retention time (min) ∼ 8.86 |
Chemical purity (area% at 265 nm) 99 | Chemical purity (area% at 265 nm) 99 |
Enantiomeric excess (%) > 99 | Enantiomeric excess (%) > 99 |
Example 11: (4R)-4-[[4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoyl]amino]isoxazolidine-2-sulfonyl fluoride (compound A198 in table A)
Biological examples
Diabrotica balteata (Corn root worm)
Euschistus heros (Neotropical Brown Stink Bug)
Myzus persicae (Green peach aphid):Feeding/Contact activity
Plutella xylostella (Diamond back moth)
Spodoptera littoralis (Egyptian cotton leaf worm)
Spodoptera littoralis (Egyptian cotton leaf worm)
Tetranychus urticae (Two-spotted spider mite):Feeding/contact activity
Thrips tabaci (Onion thrips) Feeding/Contact activity
A1, A2, A3 and A4 are independently of one another C-H, C-R5, or nitrogen;
R1 is hydrogen, C1-C8alkyl, C1-C8alkylcarbonyl-, C1-C8alkoxy, C1-C8alkoxy-C1-C8alkyl or C1-C8alkoxycarbonyl-;
R2 is C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl, C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl, C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl, C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl, C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, 5-6 membered heteroaryl-C1-C4alkyl, 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7, -N(R8)(R9), halogen or -OR10;
R3 is C1-C8haloalkyl:
R4 is aryl, aryl substituted by one to three R7, heteroaryl or heteroaryl substituted by one to three R7;
R5 is independently halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl. C1-C8haloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, C1-C8alkoxy, C1-C8haloalkoxy, or C1-C8alkoxycarbonyl-, or two R5 on adjacent carbon atoms together form a -CH=CH-CH=CH- bridge or a -N=CH-CH=CH- bridge;
R6a is independently cyano, nitro, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, hydroxy, C1-C8alkoxy, or C1-C8haloalkoxy;
R6b is independently halogen, cyano, nitro, oxo, C1-C8alkyl, C1-C8haloalkyl, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, hydroxyl, C1-C8alkoxy, C1-C8haloalkoxy, phenyl, phenyl substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7;
R7 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy,, C1-C8haloalkoxy;
R8 and R9 are independently hydrogen, cyano, cyano-C1-C8alkyl, C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C2-C8alkenyl, C2-C8alkenyl substituted by one to three R6a, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8haloalkoxy substituted by one to three R6a, C1-C8alkoxy substituted by one to three R6a,C1-C8haloalkyl, C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl, C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl, C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl, C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, 5-6 membered heteroaryl-C1-C4alkyl, 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7, -S(O)R10, -S(O)2R10, COR10, COOR10, or R8 and R9 together with the nitrogen atom can be linked through a C3-C8alkylene chain, a C3-C8alkylene chain substituted by one to three R6b or a C3-C8alkylene chain, where one carbon atom is replaced by O, S, S(O) or SO2;
R10 is hydrogen, cyano-C1-C8alkyl, C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl. C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl, C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2 C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl, C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl, C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkryl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7;
n is 2;
or a tautomer, enantiomer, salt or N-oxide thereofRa is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C1-C8haloalkoxy;
Rb is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8aloalkyl, or C1-C8haloalkoxy;
Rc is hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, or C1-C8haloalkoxy;
R5 is halogen, cyano, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl;
Rd is S(O)2-R2;
R2 is C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, -N(R8)(R9), C1-C4alkylamino, fluoro;
R5 is independently halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl;
R6a is independently C1-C8alkoxy, or C1-C8haloalkoxy;
R6b is independently oxo, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, C1-C8alkoxy, C1-C8haloalkoxy, phenyl, phenyl substituted by one to three R7, 5-6 membered heteroaryl or 5-6 membered heteroaryl substituted by one to three R7;
R7 is independently halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy, or C1-C8haloalkoxy;
R8 and R9 are independently hydrogen, cyano-C1-C8alkyl, C1-C8alkyl, C1-C8alkyl substituted by one to three R6a, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, -S(O)2R10;
R10 is hydrogen, cyano-C1-C8alkyl, C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, phenyl, phenyl substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7.
wherein A1, A2, A3, A4, R1, R2 and n are as defined for a compound of formula (I) according to any one of claims 1 to 9 and XB is a leaving group, or XB is cyano, formyl, CH=N-OH or acetyl; or a tautomer, enantiomer, salt or N-oxide thereof; or
a compound of formula (Int-II)
wherein A1, A2, A3, A4, R1, R2 and n are as defined for a compound of formula (I) according to any one of claims 1 to 9 and XC is CH2-halogen, CH=C(R3)R4, or CH2C(OH)(R3)R4 wherein R3 and R4 are as defined for a compound of formula (I) according to any one of claims 1 to 9; or a tautomer, enantiomer. salt or N-oxide thereof; or a compound of formula (Int-III)
wherein R1, R2 and n are as defined for a compound of formula (I) according to any one of claims 1 to 9; or a tautomer, enantiomer, salt or N-oxide thereof
A1, A2, A3 und A4 unabhängig voneinander für C-H, C-R5 oder Stickstoff stehen,
R1 für Wasserstoff, C1-C8-Alkyl, C1-C8-Alkylcarbonyl-, C1-C8-Alkoxy, C1-C8-Alkoxy-C1-C8-alkyl oder C1-C8-Alkoxycarbonyl- steht,
R2 für C1-C8-Alkyl, durch ein bis drei R6a substituiertes C1-C8-Alkyl, C1-C8-Halogenalkyl, durch ein bis drei R6a substituiertes C1-C8-Halogenalkyl, C3-C8-Cycloalkyl, durch ein bis drei R6b substituiertes C3-C8-Cycloalkyl, C3-C8-Cycloalkyl, bei dem ein Kohlenstoffatom durch O, S, S(O) oder SO2 ersetzt ist, C3-C8-Cycloalkyl-C1-C8-alkyl, C3-C8-Cycloalkyl-C1-C8-alkyl, bei dem ein Kohlenstoffatom in der Cycloalkylgruppe durch O, S, S(O) oder SO2 ersetzt ist, C3-C8-Cycloalkyl-C1-C8-halogenalkyl, C2-C8-Alkenyl, durch ein bis drei R6a substituiertes C2-C8-Alkenyl, C2-C8-Halogenalkenyl, durch ein bis drei R6a substituiertes C2-C8-Halogenalkenyl, C2-C8-Alkinyl, C2-C8-Halogenalkinyl, Phenyl, durch ein bis drei R7 substituiertes Phenyl, Phenyl-C1-C4-alkyl, Phenyl-C1-C4-alkyl, bei dem die Phenylgruppierung durch ein bis drei R7 substituiert ist, 5- oder 6-gliedriges Heteroaryl, durch ein bis drei R7 substituiertes 5- oder 6-gliedriges Heteroaryl, 5- oder 6-gliedriges Heteroaryl-C1-C4-alkyl, 5- oder 6-gliedriges Heteroaryl-C1-C4-alkyl, bei dem die Heteroarylgruppierung durch ein bis drei R7 substituiert ist, -N(R8)(R9), Halogen oder -OR10 steht,
R3 für C1-C8-Halogenalkyl steht,
R4 für Aryl, durch ein bis drei R7 substituiertes Aryl, Heteroaryl oder durch ein bis drei R7 substituiertes Heteroaryl steht,
R5 unabhängig für Halogen, Cyano, Nitro, C1-C8-Alkyl, C3-C8-Cycloalkyl, C1-C8-Halogenalkyl, C2-C8-Alkenyl, C2- C8-Halogenalkenyl, C2-C8-Alkinyl, C2-C8-Halogenalkinyl, C1-C8-Alkoxy, C1-C8-Halogenalkoxy oder C1-C8-Alkoxycarbonyl-, steht oder zwei R5 an benachbarten Kohlenstoffatomen zusammen eine -CH=CH-CH=CH-Brücke oder eine -N=CH-CH=CH-Brücke bilden,
R6a unabhängig für Cyano, Nitro, Amino, C1-C8-Alkylamino, N,N-C1-C8-Dialkylamino, Hydroxy, C1-C8-Alkoxy oder C1-C8-Halogenalkoxy steht,
R6b unabhängig für Halogen, Cyano, Nitro, Oxo, C1-C8-Alkyl, C1-C8-Halogenalkyl, Amino, C1-C8-Alkylamino, N,N-C1-C8-Dialkylamino, Hydroxyl, C1-C8-Alkoxy, C1-C8-Halogenalkoxy, Phenyl, durch ein bis drei R7 substituiertes Phenyl, 5- oder 6-gliedriges Heteroaryl oder durch ein bis drei R7 substituiertes 5- oder 6-gliedriges Heteroaryl steht,
R7 unabhängig für Halogen, Cyano, Nitro, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkoxy steht,
R8 und R9 unabhängig für Wasserstoff, Cyano, Cyano-C1-C8-alkyl, C1-C8-Alkyl, durch ein bis drei R6a substituiertes C1-C8-Alkyl, C2-C8-Alkenyl, durch ein bis drei R6a substituiertes C2-C8-Alkenyl, C1-C8-Alkoxy, C1-C8-Halogenalkoxy, durch ein bis drei R6a substituiertes C1-C8-Halogenalkoxy, durch ein bis drei R6a substituiertes C1-C8-Alkoxy, C1-C8-Halogenalkyl, durch ein bis drei R6a substituiertes C1-C8-Halogenalkyl, C3-C8-Cycloalkyl, durch ein bis drei R6b substituiertes C3-C8-Cycloalkyl, C3-C8-Cycloalkyl, bei dem ein Kohlenstoffatom durch O, S, S(O) oder SO2 ersetzt ist, C3-C8-Cycloalkyl-C1-C8-alkyl, C3-C8-Cycloalkyl-C1-C8-alkyl, bei dem ein Kohlenstoffatom in der Cycloalkylgruppe durch O, S, S(O) oder SO2 ersetzt ist, C3-C8-Cycloalkyl-C1-C8-halogenalkyl, C2-C8-Alkenyl, durch ein bis drei R6a substituiertes C2-C8-Alkenyl, C2-C8-Halogenalkenyl, durch ein bis drei R6a substituiertes C2-C8-Halogenalkenyl, C2-C8-Alkinyl, C2-C8-Halogenalkinyl, Phenyl, durch ein bis drei R7 substituiertes Phenyl, Phenyl-C1-C4-alkyl, Phenyl-C1-C4-alkyl, bei dem die Phenylgruppierung durch ein bis drei R7 substituiert ist, 5- oder 6-gliedriges Heteroaryl, durch ein bis drei R7 substituiertes 5- oder 6-gliedriges Heteroaryl, 5- oder 6-gliedriges Heteroaryl-C1-C4-alkyl, 5- oder 6-gliedriges Heteroaryl-C1-C4-alkyl, bei dem die Heteroarylgruppierung durch ein bis drei R7 substituiert ist, -S(O)R10, -S(O)2R10, COR10 oder COOR10, oder R8 und R9 zusammen mit dem Stickstoffatom über eine C3-C8-Alkylenkette, eine durch ein bis drei R6b substituierte C3- C8-Alkylenkette oder eine C3-C8-Alkylenkette, bei der ein Kohlenstoffatom durch O, S, S(O) oder SO2 ersetzt ist, verbunden sein können,
R10 für Wasserstoff, Cyano-C1-C8-alkyl, C1-C8-Alkyl, durch ein bis drei R6a substituiertes C1-C8-Alkyl, C1-C8-Halogenalkyl, durch ein bis drei R6a substituiertes C1-C8-Halogenalkyl, C3-C8-Cycloalkyl, durch ein bis drei R6b substituiertes C3-C8-Cycloalkyl, C3-C8-Cycloalkyl, bei dem ein Kohlenstoffatom durch O, S, S(O) oder SO2 ersetzt ist, C3-C8-Cycloalkyl-C1-C8-alkyl, C3-C8-Cycloalkyl-C1-C8-alkyl, bei dem ein Kohlenstoffatom in der Cycloalkylgruppe durch O, S, S(O) oder SO2 ersetzt ist, C3-C8-Cycloalkyl-C1-C8-halogenalkyl, C2-C8-Alkenyl, durch ein bis drei R6a substituiertes C2-C8-Alkenyl, C2-C8-Halogenalkenyl, durch ein bis drei R6a substituiertes C2-C8-Halogenalkenyl, C2-C8-Alkinyl, C2-C8-Halogenalkinyl, Phenyl, durch ein bis drei R7 substituiertes Phenyl, Phenyl-C1-C4-alkyl, Phenyl-C1-C4-alkyl, bei dem die Phenylgruppierung durch ein bis drei R7 substituiert ist, 5- oder 6-gliedriges Heteroaryl, durch ein bis drei R7 substituiertes 5- oder 6-gliedriges Heteroaryl, 5- oder 6-gliedriges Heteroaryl-C1-C4-alkyl oder 5- oder 6-gliedriges Heteroaryl-C1-C4-alkyl, bei dem die Heteroarylgruppierung durch ein bis drei R7 substituiert ist, steht,
n für 2 steht,
oder ein Tautomer, ein Enantiomer, ein Salz oder ein N-Oxid davon.Ra für Wasserstoff, Halogen, Cyano, C1-C8-Alkyl, C1-C8-Halogenalkyl oder C1-C8-Halogenalkoxy steht,
Rb für Wasserstoff, Halogen, Cyano, C1-C8-Alkyl, C1-C8-Halogenalkyl oder C1-C8-Halogenalkoxy steht,
Rc für Wasserstoff, Halogen, Cyano, C1-C8-Alkyl, C1-C8-Halogenalkyl oder C1-C8-Halogenalkoxy steht,
R5 für Halogen, Cyano, C1-C8-Alkyl, C3-C8-Cycloalkyl, C1-C8-Halogenalkyl oder C2-C8-Alkenyl steht,
Rd für S(O)2-R2 steht,
R2 für C1-C8-Alkyl oder durch ein bis drei R6a substituiertes C1-C8-Alkyl, C1-C8-Halogenalkyl oder durch ein bis drei R6a substituiertes C1-C8-Halogenalkyl,
C3-C8-Cycloalkyl oder durch ein bis drei R6b substituiertes C3-C8-Cycloalkyl, Phenyl, durch ein bis drei R7 substituiertes Phenyl, Phenyl-C1-C4-alkyl, Phenyl-C1-C4-alkyl, bei dem die Phenylgruppierung durch ein bis drei R7 substituiert ist, 5- oder 6-gliedriges Heteroaryl, durch ein bis drei R7 substituiertes 5- oder 6-gliedriges Heteroaryl, -N(R8) (R9), C1-C4-Alkylamino oder Fluor steht,
R5 unabhängig für Halogen, Cyano, Nitro, C1-C8-Alkyl, C3-C8-Cycloalkyl, C1-C8-Halogenalkyl oder C2-C8-Alkenyl steht,
R6a unabhängig für C1-C8-Alkoxy oder C1-C8-Halogenalkoxy steht,
R6b unabhängig für Oxo, Amino, C1-C8-Alkylamino, N,N-C1-C8-Dialkylamino, C1-C8-Alkoxy, C1-C8-Halogenalkoxy, Phenyl, durch ein bis drei R7 substituiertes Phenyl, 5- oder 6-gliedriges Heteroaryl oder durch ein bis drei R7 substituiertes 5- oder 6-gliedriges Heteroaryl steht,
R7 unabhängig für Halogen, Cyano, C1-C8-Alkyl, C1-C8-Halogenalkyl, C1-C8-Alkoxy oder C1-C8-Halogenalkoxy steht, R8 und R9 unabhängig für Wasserstoff, Cyano-C1-C8-alkyl, C1-C8-Alkyl, durch ein bis drei R6a substituiertes C1-C8-Alkyl, C2-C8-Alkenyl oder durch ein bis drei R6a substituiertes C2-C8-Alkenyl, Phenyl-C1-C4-alkyl, Phenyl-C1-C4-alkyl, bei dem die Phenylgruppierung durch ein bis drei R7 substituiert ist, oder -S(O)2R10 stehen,
R10 für Wasserstoff, Cyano-C1-C8-alkyl, C1-C8-Alkyl oder durch ein bis drei R6a substituiertes C1-C8-Alkyl, Phenyl, durch ein bis drei R7 substituiertes Phenyl, 5- oder 6-gliedriges Heteroaryl oder durch ein bis drei R7 substituiertes 5- oder 6-gliedriges Heteroaryl steht.
wobei A1, A2, A3, A4, R1, R2 und n wie für eine Verbindung der Formel (I) nach einem der Ansprüche 1 bis 9 definiert sind und XB für eine Abgangsgruppe steht oder XB für Cyano, Formyl, CH=N-OH oder Acetyl steht, oder ein Tautomer, ein Enantiomer, ein Salz oder ein N-Oxid davon, oder
Verbindung der Formel (Int-II)
wobei A1, A2, A3, A4, R1, R2 und n wie für eine Verbindung der Formel (I) nach einem der Ansprüche 1 bis 9 definiert sind und Xc für CH2-Halogen, CH=C(R3)R4 oder CH2C(OH) (R3)R4 steht, wobei R3 und R4 wie für eine Verbindung der Formel (I) nach einem der Ansprüche 1 bis 9 definiert sind, oder ein Tautomer, ein Enantiomer, ein Salz oder ein N-Oxid davon, oder Verbindung der Formel (Int-III)
wobei R1, R2 und n wie für eine Verbindung der Formel (I) nach einem der Ansprüche 1 bis 9 definiert sind, oder ein Tautomer, ein Enantiomer, ein Salz oder ein N-Oxid davon.
A1, A2, A3 et A4 étant indépendamment les uns des autres C-H, C-R5, ou azote ;
R1 étant hydrogène, C1-C8alkyle, C1-C8alkylcarbonyle-, C1-C8alcoxy, C1-C8alcoxy-C1-C8alkyle ou C1-C8alcoxycarbonyle- ;
R2 étant C1-C8alkyle, C1-C8alkyle substitué par un à trois R6a, C1-C8halogénoalkyle, C1-C8halogénoalkyle substitué par un à trois R6a, C3-C8cycloalkyle, C3-C8cycloalkyle substitué par un à trois R6b, C3-C8cycloalkyle où un atome de carbone est remplacé par O, S, S(O) ou SO2, C3-C8cycloalkyl-C1-C8alkyle, C3-C8cycloalkyl-C1-C8alkyle où un atome de carbone dans le groupe cycloalkyle est remplacé par O, S, S(O) ou SO2, C3-C8cycloalkyl-C1-C8halogénoalkyle, C2-C8alcényle, C2-C8alcényle substitué par un à trois R6a, C2-C8halogénoalcényle, C2-C8halogénoalcényle substitué par un à trois R6a, C2-C8alcynyle, C2-C8halogénoalcynyle, phényle, phényle substitué par un à trois R7, phényl-C1-C4alkyle, phényl-C1-C4alkyle, le fragment phényle étant substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons, hétéroaryle à 5 à 6 chaînons substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons-C1-C4alkyle, hétéroaryle à 5 à 6 chaînons-C1-C4alkyle, le fragment hétéroaryle étant substitué par un à trois R7,-N(R8) (R9), halogène ou -OR10 ;
R3 étant C1-C8halogénoalkyle ;
R4 étant aryle, aryle substitué par un à trois R7, hétéroaryle ou hétéroaryle substitué par un à trois R7 ;
R5 étant indépendamment halogène, cyano, nitro, C1-C8alkyle, C3-C8cycloalkyle, C1-C8halogénoalkyle, C2-C8alcényle, C2-C8halogénoalcényle, C2-C8alcynyle, C2-C8halogénoalcynyle, C1-C8alcoxy, C1-C8halogénoalcoxy, ou C1-C8alcoxycarbonyle-, ou deux R5 sur des atomes de carbone adjacents formant ensemble un pont -CH=CH-CH=CH- ou un pont -N=CH-CH=CH- ;
R6a étant indépendamment cyano, nitro, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, hydroxy, C1-C8alcoxy, ou C1-C8halogénoalcoxy ;
R6b étant indépendamment halogène, cyano, nitro, oxo, C1-C8alkyle, C1-C8halogénoalkyle, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, hydroxyle, C1-C8alcoxy, C1-C8halogénoalcoxy, phényle, phényle substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons, hétéroaryle à 5 à 6 chaînons substitué par un à trois R7;
R7 étant indépendamment halogène, cyano, nitro, C1-C8alkyle, C1-C8halogénoalkyle, C1-C8alcoxy, C1-Cshalogénoalcoxy ;
R8 et R9 étant indépendamment hydrogène, cyano, cyano-C1-C8alkyle, C1-C8alkyle, C1-C8alkyle substitué par un à trois R6a, C2-C8alcényle, C2-C8alcényle substitué par un à trois R6a, C1-C8alcoxy, C1-C8halogénoalcoxy, C1-C8halogénoalcoxy substitué par un à trois R6a, C1-C8alcoxy substitué par un à trois R6a, C1-C8halogénoalkyle, C1-C8halogénoalkyle substitué par un à trois R6a, C3-C8cycloalkyle, C3-C8cycloalkyle substitué par un à trois R6b, C3-C8cycloalkyle où un atome de carbone est remplacé par O, S, S(O) ou SO2, C3-C8cycloalkyl-C1-C8alkyle, C3-C8cycloalkyl-C1-C8alkyle où un atome de carbone dans le groupe cycloalkyle est remplacé par O, S, S(O) ou SO2, C3-C8cycloalkyl-C1-C8halogénoalkyle, C2-C8alcényle, C2-C8alcényle substitué par un à trois R6a, C2-C8halogénoalcényle, C2-C8halogénoalcényle substitué par un à trois R6a, C2-C8alcynyle, C2-C8halogénoalcynyle, phényle, phényle substitué par un à trois R7, phényl-C1-C4alkyle, phényl-C1-C4alkyl, le fragment phényle étant substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons, hétéroaryle à 5 à 6 chaînons substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons-C1-C4alkyle, hétéroaryle à 5 à 6 chaînons-C1-C4alkyle le fragment hétéroaryle étant substitué par un à trois R7, -S(O)R10, -S(O)2R10, COR10, COOR10, ou R8 et R9, conjointement avec l'atome d'azote pouvant être liés par l'intermédiaire d'une chaîne C3-C8alkylène, d'une chaîne C3-C8alkylène substituée par un à trois R6b ou d'une chaîne C3-C8alkylène, où un atome de carbone est remplacé par O, S, S(O) ou SO2 ;
R10 étant hydrogène, cyano-C1-C8alkyle, C1-C8alkyle, C1-Csalkyle substitué par un à trois R6a, C1-C8halogénoalkyle, C1-C8halogénoalkyle substitué par un à trois R6a, C3-C8cycloalkyle, C3-C8cycloalkyle substitué par un à trois R6b, C3-C8cycloalkyle où un atome de carbone est remplacé par O, S, S(O) ou SO2, C3-C8cycloalkyl-C1-C8alkyle, C3-C8cycloalkyl-C1-C8alkyle où un atome de carbone dans le groupe cycloalkyle est remplacé par O, S, S(O) ou SO2, C3-C8cycloalkyl-C1-C8halogénoalkyle, C2-C8alcényle, C2-C8alcényle substitué par un à trois R6a, C2-C8halogénoalcényle, C2-C8halogénoalcényle substitué par un à trois R6a, C2-C8alcynyle, C2-C8halogénoalcynyle, phényle, phényle substitué par un à trois R7, phényl-C1-C4alkyle, phényl-C1-C4alkyle, le fragment phényle étant substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons, hétéroaryle à 5 à 6 chaînons substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons-C1-C4alkyle ou hétéroaryle à 5 à 6 chaînons-C1-C4alkyle le fragment hétéroaryle étant substitué par un à trois R7 ;
n étant 2 ;
ou forme tautomère, énantiomère, sel ou N-oxyde correspondant(e).Ra étant hydrogène, halogène, cyano, C1-C8alkyle, C1-C8halogénoalkyle, ou C1-C8halogénoalcoxy ;
Rb étant hydrogène, halogène, cyano, C1-C8alkyle, C1-C8halogénoalkyle, ou C1-C8halogénoalcoxy ;
Rc étant hydrogène, halogène, cyano, C1-C8alkyle, C1-C8halogénoalkyle, ou C1-C8halogénoalcoxy ;
R5 étant halogène, cyano, C1-C8alkyle, C3-C8cycloalkyle, C1-C8halogénoalkyle, C2-C8alcényle ;
Rd étant S(O)2-R2;
R2 étant C1-C8alkyle ou C1-C8alkyle substitué par un à trois R6a, C1-C8halogénoalkyle ou C1-C8halogénoalkyle substitué par un à trois R6a, C3-C8cycloalkyle ou C3-C8cycloalkyle substitué par un à trois R6b, phényle, phényle substitué par un à trois R7, phényl-C1-C4alkyle, phényl-C1-C4alkyle le fragment phényle étant substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons, hétéroaryle à 5 à 6 chaînons substitué par un à trois R7, -N(R8) (R9), C1-C4alkylamino, fluoro ;
R5 étant indépendamment halogène, cyano, nitro, C1-C8alkyle, C3-C8cycloalkyle, C1-C8halogénoalkyle, C2-C8alcényle ;
R6a étant indépendamment C1-C8alcoxy, ou C1-C8halogénoalcoxy ;
R6b étant indépendamment oxo, amino, C1-C8alkylamino, N,N-C1-C8dialkylamino, C1-C8alcoxy, C1-C8halogénoalcoxy, phényle, phényle substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons ou hétéroaryle à 5 à 6 chaînons substitué par un à trois R7;
R7 étant indépendamment halogène, cyano, C1-C8alkyle, C1-C8halogénoalkyle, C1-C8alcoxy, ou C1-C8halogénoalcoxy ;
R8 et R9 étant indépendamment hydrogène, cyano-C1-C8alkyle, C1-C8alkyle, C1-C8alkyle substitué par un à trois R6a, C2-C8alcényle ou C2-C8alcényle substitué par un à trois R6a, phényl-C1-C4alkyle, phényl-C1-C4alkyle le fragment phényle étant substitué par un à trois R7,-S(O)2R10 ;
R10 étant hydrogène, cyano-C1-C8alkyle, C1-C8alkyle ou C1-C8alkyle substitué par un à trois R6a, phényle, phényle substitué par un à trois R7, hétéroaryle à 5 à 6 chaînons, hétéroaryle à 5 à 6 chaînons substitué par un à trois R7.
A1, A2, A3, A4, R1, R2 et n étant tels que définis pour un composé de formule (I) selon l'une quelconque des revendications 1 à 9 et XB étant un groupe partant, ou XB étant cyano, formyle, CH=N-OH ou acétyle ; ou forme tautomère, énantiomère, sel ou N-oxyde correspondant(e) ; ou
un composé de formule (Int-II)
A1, A2, A3, A4, R1, R2 et n étant tels que définis pour un composé de formule (I) selon l'une quelconque des revendications 1 à 9 et Xc étant CH2-halogène, CH=C(R3)R4, ou CH2C(OH)(R3)R4, R3 et R4 étant tels que définis pour un composé de formule (I) selon l'une quelconque des revendications 1 à 9 ; ou forme tautomère, énantiomère, sel ou N-oxyde correspondant(e) ;
ou un composé de formule (Int-III)
R1, R2 et n étant tels que définis pour un composé de formule (I) selon l'une quelconque des revendications 1 à 9 ; ou forme tautomère, énantiomère, sel ou N-oxyde correspondant(e).
REFERENCES CITED IN THE DESCRIPTION
Patent documents cited in the description
Non-patent literature cited in the description