Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
View Patent ↗This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, compositions containing such molecules, and processes of using such molecules and compositions against such pests. These molecules and compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).
1. A molecule having the following formula
wherein:
(A) R 1 , R 5 , R 6 , R 11 , and R 12 are each independently selected from the group consisting of H, F, Cl, Br, I, CN, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 4 )haloalkoxy;
(B) R 2 , R 3 , and R 4 are each independently selected from the group consisting of H, F, Cl, Br, I, CN, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(C) R 7 is (C 1 -C 6 )haloalkyl;
(D) R 9 is selected from the group consisting of (F), H, F, Cl, Br, I, CN, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, and (C 1 -C 4 )haloalkoxy;
(E) R 10 is selected from the group consisting of (F), F, Cl, Br, I, CN, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(F) R 9 and R 10 together can optionally form a 3- to 5-membered saturated or unsaturated, hydrocarbyl link,
wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, OH, and oxo;
(G) Q 1 and Q 2 are each independently O or S;
(H) R 13 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(I) R 14 is selected from the group consisting of (K), (O), H, (C 1 -C 4 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(J) R 15 is selected from the group consisting of (K), H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(K) R 14 and R 15 together can optionally form a 2- to 5-membered saturated, hydrocarbyl link,
wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, and CN;
(L) L is selected from the group consisting of
(1) a bond connecting C(R 14 )(R 15 ) to C(=Q 2 ), and
(2) a (C 1 -C 6 )alkyl wherein said alkyl is optionally substituted with one or more substituents independently selected from the group consisting of F, Cl, CN, OH, and oxo;
(M) X is selected from the group consisting of
(1) a bond connecting C(=Q 2 ) to R 17 , and
(2) a N, O, and S connecting C(=Q 2 ) to R 17 ;
(N) R 16 is selected from the group consisting of (O), H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )haloalkoxy, amino, and NHC(O)O(C 1 -C 6 )alkyl;
(O) R 14 and R 16 together can optionally form a 2- to 4-membered saturated, hydrocarbyl link, which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen,
wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, OH, and oxo;
(P) R 17 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkyl, (C 1 -C 6 )alkoxy, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )haloalkoxy, and (C 1 -C 6 )alkyl(C 3 -C 6 )cycloalkyl;
(Q) R 16 and R 17 together can optionally form a 2- to 6-membered saturated, hydrocarbyl link, which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen,
wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, OH, and oxo; and agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, resolved stereoisomers, and tautomers, of the molecules of Formula One.
2. A molecule according to claim 1 wherein R 1 , R 3 , R 4 , R 5 , R 6 , R 9 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 are H.
3. A molecule according to claim 1 wherein R 2 is F, Cl, Br, or CH 3 .
4. A molecule according to claim 1 wherein R 3 is F, Cl, Br, or CH═CH 2 .
5. A molecule according to claim 1 wherein R 4 is Cl, Br, or CH 3 .
6. A molecule according to claim 1 wherein R 2 , R 3 , and R 4 are C 1 .
7. A molecule according to claim 1 wherein R 7 is (C 1 -C 6 )haloalkyl.
8. A molecule according to claim 1 wherein R 7 is CF 3 , CF 2 CH 3 , or CF 2 CH 2 CH 3 .
9. A molecule according to claim 1 wherein R 10 is Cl, Br, I, CH 3 , or CF 3 .
10. A molecule according to claim 1 wherein Q 1 and Q 2 are O.
11. A molecule according to claim 1 wherein R 13 , R 14 , and R 15 are CH 3 or CH 2 CH 3 .
12. A molecule according to claim 1 wherein R 14 and R 15 together form a 2-membered saturated, hydrocarbyl link.
13. A molecule according to claim 1 wherein L is a bond connecting C(R 14 )(R 15 ) to C(=Q 2 ).
14. A molecule according to claim 1 wherein X is a bond connecting C(=Q 2 ) to R 17 .
15. A molecule according to claim 1 wherein X is N connecting C(=Q 2 ) to R 17 .
16. A molecule according to claim 1 wherein R 16 is CH 3 , CH 2 CH 3 , OCH 3 , OCH 2 CH═CH 2 , NH 2 , or NHC(O)OC(CH 3 ) 3 .
17. A molecule according to claim 1 wherein R 14 and R 16 together form a 2- to 4-membered saturated, hydrocarbyl link, which may contain one or more oxygen heteroatoms.
18. A molecule according to claim 1 wherein R 17 is CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH(CH 3 ) 2 , CH 2 CH═CH 2 , CH 2 C≡CH, CH 2 CHF 2 , CH 2 CF 3 , CH 2 CH 2 CF 3 , CH 2 CF 2 CH 3 , CH(CH 3 )CF 3 , CH 2 CH 2 CH 2 CF 3 , CH═CHCH 2 CF 3 , 3,3-difluorocyclobutyl, CH 2 CH 2 cyclopropyl, and CH 2 cyclobutyl.
19. A molecule according to claim 1 wherein
(A) R 1 , R 5 , R 6 , R 11 , and R 12 are H;
(B) R 2 , R 3 , and R 4 are each independently selected from the group consisting of H, F, Cl, Br, (C 1 -C 6 )alkyl, and (C 2 -C 6 )alkenyl;
(C) R 7 is (C 1 -C 6 )haloalkyl;
(D) R 9 is H;
(E) R 10 is selected from the group consisting of Cl, Br, I, (C 1 -C 6 )alkyl, and (C 1 -C 6 )haloalkyl;
(G) Q 1 and Q 2 are O;
(H) R 13 is selected from the group consisting of H and (C 1 -C 6 )alkyl;
(I) R 14 is selected from the group consisting of (K), (O), H, and (C 1 -C 4 )alkyl;
(J) R 15 is selected from the group consisting of (K), H, and (C 1 -C 6 )alkyl;
(K) R 14 and R 15 together can optionally form a 2- to 5-membered saturated, hydrocarbyl link;
(L) L is a bond connecting C(R 14 )(R 15 ) to C=Q 2 ;
(M) X is selected from the group consisting of
(1) a bond connecting C(=Q 2 ) to R 17 , and
(2) a N, O, and S connecting C(=Q 2 ) to R 17 ;
(N) R 16 is selected from the group consisting of (O), H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 2 -C 6 )alkenyloxy, amino, and NHC(O)O(C 1 -C 6 )alkyl;
(O) R 14 and R 16 together can optionally form a 2- to 4-membered saturated, hydrocarbyl link, which may contain one or more oxygen heteroatoms;
(P) R 17 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkyl, and (C 1 -C 6 )alkyl(C 3 -C 6 )cycloalkyl.
20. A pesticidal composition comprising a molecule according to claim 1 further comprising one or more active ingredients.
21. A pesticidal composition according to claim 20 wherein said active ingredient is from AIGA.
22. A pesticidal composition comprising a molecule according to claim 1 further comprising one or more MoA Materials.
23. A pesticidal composition according to claim 22 wherein said MoA Material is from MoAMGA.
24. A pesticidal composition comprising a molecule according to claim 1 and a seed.
25. A process to control a pest said process comprising applying to a locus, a pesticidally effective amount of a pesticidal composition wherein said pesticidal composition comprises a molecule according to claim 1 .
26. A molecule according to claim 1 wherein said molecule is selected from one of the following molecules
No.
Structure
F1
F2
F3
F4
F5
F6
F7
F8
F9
F10
F11
F12
F13
F14
F15
F16
F17
F18
F19
F20
F21
F22
F23
F24
F25
F26
F27
F28
F29
F30
F31
F32
F33
F34
F35
F36
F37
F38
F39
F40
F41
F42
F43
F44
F45
F46
F47
F48
F49
F50
F51
F52
F53
F54
F55
F56
F57
F58
F59
F60
F61
F62
F63
F64
F65
F66
F67
F68
F69
F70
F71
F72
F73
F74
F75
F76
F77
F78
F79
F80
F81
F82
F83
F84
F85
F86
F87
F88
F89
F90
F91
F92
F93
F94
F95
F96
F97
F98
F99
F100
F101
F102
F103
F104
F105
F106
F107
F108
F109
F110
F111
F112
F113
F114
F115
F116
F117
F118
F119
F120
F121
F122
F123
F124
F125
F126
F127
F128
F129
F130
F131
F132
F133
F134
F135
F136
F137
F138
F139
F140
F141
F142
F143
F144
F145
F146
F147
F148
F150
F153
F154
F155
F157
F158
F159
F160
F161
F162
F163
F164
F165
F166
F167
F168
F169
F170
F171
F172
F173
F174
F175
F176
F177
F178
F180
F181
F182
F183
F184
F185
F186
F187
F188
F189
F190
F191
F192
F193
F194
F195
F196
F197
F198
F199
F200
F201
F202
F203
F204
F205
F206
F207
F208
F209
F210
F211
F212
F213
F214
F215
F216
F217
27. A molecule according to claim 1 wherein said molecule is selected from one of the following molecules
No.
Structure
P1
P2
P3
P4
P5
P6
P7
P8
P9
P10
P11
P12
P13
P14
P15
P16
P17
P18
P19
P20
P21
P22
P23
P24
P25
P26
P27
P28
P29
P30
P31
P32
P33
P34
P35
P37
P39
P40
P41
P42
P43
P44
P45
P46
P47
P48
P49
P50
P51
P52
P53
P54
P55
P56
P57
P58
P59
P60
P61
P62
P63
P64
P65
P66
P67
P68
P69
P70
P71
P72
P73
P74
P75
P76
P77
P78
P79
P80
P81
P82
P83
P84
P85
P86
P87
P88
P89
P90
P91
P92
P93
P94
P95
P96
P97
P98
P99
P100
P101
P102
P103
P104
28. A pesticidal composition according to claim 20 wherein said active ingredient is selected from the group consisting of chlorpyrifos, chlorpyrifos-methyl, methoxyfenozide, spinetoram, spinosad, and sulfoxaflor.