Pesticidal compositions and processes related thereto
View Patent ↗This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Nematoda, Arthropoda, and/or Mollusca, processes to produce such molecules and intermediates used in such processes, compositions containing such molecules, and processes of using such molecules against such pests. These molecules may be used, for example, as nematicides, acaricides, insecticides, miticides, and/or molluscicides. This document discloses molecules having the following formula (“Formula One”).
1. A molecule having the following formula
wherein:
(a) R1, R2, R3, R4, and R5, are, each independently, H, F, Cl, Br, I, CN, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, or (C 1 -C 6 )haloalkoxy;
(b) R6 is (C 1 -C 6 )haloalkyl;
(c) R7 is H;
(d) R8 is H, (C 1 -C 6 )alkyl, or (C 1 -C 6 )haloalkyl;
(e) R9 is H, F, Cl, Br, I, (C 1 -C 6 )alkyl, or (C 1 -C 6 )haloalkyl;
(f) R10 is F, Cl, Br, I, (C 1 -C 6 )alkyl, or (C 1 -C 6 )haloalkyl;
(g) R11 and R12 are, each independently, H, F, Cl, Br, I, (C 1 -C 6 )alkyl, or (C 1 -C 6 )haloalkyl;
(h) L is
(1) a linker that is a bond connecting the two nitrogen atoms, or
(2) a (C 1 -C 6 )alkyl that is optionally substituted with one or more substituents, wherein each substituent is independently selected from F, Cl, Br, I, CN, OH, oxo, (C 1 -C 6 )alkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 wherein each (C 1 -C 6 )alkyl is independently selected, and wherein each said alkyl or alkoxy has one or more substituents independently selected from H, F, Cl, Br, and I;
(i) R13 is
(1) an H, or
(2) a (C 1 -C 6 )alkyl that is optionally substituted with one or more substituents, wherein each substituent is independently selected from F, Cl, Br, I, CN, OH, oxo, (C 1 -C 6 )alkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 wherein each (C 1 -C 6 )alkyl is independently selected, and wherein each said alkyl or alkoxy has one or more substituents independently selected from H, F, Cl, Br, and I; and
(j) R14 is independently selected from (C 1 -C 8 )alkyl, (C 1 -C 8 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 2 -C 8 )alkenyl, or (C 2 -C 8 )alkynyl, wherein each said alkyl, haloalkyl, cycloalkyl, alkenyl, and alkynyl has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , OH, oxo, (C 1 -C 6 )alkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 wherein each (C 1 -C 6 )alkyl is independently selected, and wherein each said alkyl or alkoxy has one or more substituents independently selected from H, F, Cl, Br, and I.
2. A molecule according to claim 1 wherein:
(a) R1 is H;
(b) R2 is H, F, Cl, or Br;
(c) R3 is H, F, Cl, or Br;
(d) R4 is H, F, Cl, or Br;
(e) R5 is H;
(f) R6 is (C 1 -C 8 )haloalkyl;
(g) R7 is H;
(h) R8 is H;
(i) R9 is H;
(j) R10 is selected from a group consisting of F, Cl, Br, I, (C 1 -C 6 )alkyl, and (C 1 -C 6 )haloalkyl;
(k) R11 is H;
(l) R12 is H;
(m) L is
(1) a linker that is bond connecting the two nitrogen atoms, or
(2) a (C 1 -C 6 )alkyl;
(n) R13 is
(1) an H, or
(2) a (C 1 -C 8 )alkyl;
(o) R14 is independently selected from (C 1 -C 8 )alkyl, (C 1 -C 8 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 2 -C 8 )alkenyl, or (C 2 -C 8 )alkynyl, wherein each said alkyl, haloalkyl, cycloalkyl, alkenyl, and alkynyl has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , OH, oxo, (C 1 -C 6 )alkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 wherein each (C 1 -C 6 )alkyl is independently selected, and wherein each said alkyl or alkoxy has one or more substituents independently selected from H, F, Cl, Br, and I.
3. A molecule according to claim 1 wherein:
(a) R1 is H;
(b) R2 is Cl or Br;
(c) R3 is H, F, Cl, or Br;
(d) R4 is Cl or Br;
(e) R5 is H;
(f) R6 is (C 1 -C 8 )haloalkyl;
(g) R7 is H;
(h) R8 is H;
(i) R9 is H;
(j) R10 is Br, (C 1 -C 8 )alkyl, (C 1 -C 8 )haloalkyl;
(k) R11 is H;
(l) R12 is H;
(m) L is
(1) a linker that is bond connecting the two nitrogen atoms, or
(2) a (C 1 -C 6 )alkyl;
(n) R13 is
(1) an H, or
(2) a (C 1 -C 8 )alkyl;
(o) R14 is (C 1 -C 8 )alkyl, (C 1 -C 8 )haloalkyl, (C 3 -C 8 )cycloalkyl, or (C 2 -C 8 )alkenyl, wherein each said alkyl or cycloalkyl is substituted with CN, SCH 3 , S(O)CH 3 , or S(O) 2 CH 3 .
4. 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
5. 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
P36
P37
P38
P39
P40
P41
P42
P43
P44
P45
P46
P47
P48
P49
P50
P51
P52
P53
P54
6. A molecule according to any one of claims 1 , 2 , or 3 , wherein R14 is (C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl that is substituted with one or more substituents selected from CN, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, and S(O) 2 (C 1 -C 6 )alkyl.
7. A molecule according to any one of claim 1 or 2 wherein R14 is CF 3 , CH 2 CF 3 , CH 2 CH 2 CF 3 , CH 2 CH 2 CH 2 CF 3 , CH 2 CH 2 CH(CF 3 )CH 3 , CH(CH 3 )CH 2 CF 3 , C(CH 3 ) 2 CF 3 , C(CH 3 ) 2 CH 2 CF 3 , CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH 2 CH 2 CH(CH 3 ) 2 , C(CH 3 ) 3 , CH 2 C(CH 3 ) 3 , CH 2 CH 2 C(CH 3 ) 3 , CH 2 CH 2 CH 2 C(CH 3 ) 3 , cyclopropyl, CH═CH 2 , CH═CH(CH 3 ), CH═C(CH 3 ) 2 , CH 2 CH═CH 2 , CH 2 CH═CH(CH 3 ), C(CH 3 )═CH 2 , C(CH 3 )═CH(CH 3 ), C≡CH, CH 2 C≡CH, CH 2 CN, CH 2 CH 2 CN, CH 2 SCH 3 , CH 2 CH 2 SCH 3 , CH 2 S(O)CH 3 , CH 2 CH 2 S(O)CH 3 , CH 2 S(O) 2 CH 3 , and CH 2 CH 2 S(O) 2 CH 3 .
8. A pesticidal composition comprising a molecule according to claim 1 and further comprising one or more compounds having a mode of action selected from: acetylcholinesterase (AChE) inhibitors; GABA-gated chloride channel antagonists; sodium channel modulators; nicotinic acetylcholine (nAChR) agonists; nicotinic acetylcholine receptor (nAChR) allosteric activators; chloride channel activators; juvenile hormone mimics; miscellaneous non-specific (multi-site) inhibitors; selective homopteran feeding blockers; mite growth inhibitors; microbial disruptors of insect midgut membranes; inhibitors of chitin biosynthesis, type 0; inhibitors of chitin biosynthesis, type 1; moulting disrupter, dipteran; ecdysone receptor agonists; octopamine receptor agonists; mitochondrial complex III electron transport inhibitors; mitochondrial complex I electron transport inhibitors; voltage-dependent sodium channel blockers; inhibitors of acetyl CoA carboxylase; mitochondrial complex IV electron transport inhibitors; mitochondrial complex II electron transport inhibitors; and ryanodine receptor modulators.
9. A process of controlling a pest comprising applying a pesticidal composition comprising a molecule according to claim 1 to a locus, in a sufficient amount to control said pest.
10. A molecule according to any one of claims 1 , 2 , or 3 , wherein R2, R3, and R4 are Cl.
11. A molecule according to any one of claims 1 , 2 , or 3 , wherein R6 is CF 3 .
12. A molecule according to any one of claims 1 , 2 , or 3 , wherein R10 is Br, CH 3 , or CF 3 .
13. A molecule according to any one of claims 1 , 2 , or 3 , wherein L is —CH 2 —, —CH(CH 3 )—, —CH(CH 2 CH 3 )—, or —CH 2 CH 2 —.
14. A molecule according to any one of claims 1 , 2 , or 3 , wherein R13 is H or CH 3 .