Pesticidal compositions and processes related thereto

• US 9,676,704 B2
• Filed: 06/08/2015
• Issued: 06/13/2017
• Est. Priority Date: 06/09/2014
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Hunter, James E., Watson, Gerald B., Lo, William C., LePlae, Jr., Paul Renee, Herbert, John
• Primary Examiner(s): Haghighatian, Mina
• Assistant Examiner(s): HIRT, ERIN E
• Application Number:
  US14/733,057
• Publication Number:
  US 20150353477A1
• Time in Patent Office: 736 Days
• Field of Search: None
• CPC Class Codes: A01N 33/08 containing oxygen or sulfur
• CPC Class Codes: A01N 37/18 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
• CPC Class Codes: A01N 37/20 containing the group , wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• CPC Class Codes: A01N 37/26 containing the group; Thio analogues thereof
• CPC Class Codes: A01N 37/28 containing the group; Thio analogues thereof
• CPC Class Codes: A01N 37/34 Nitriles
• CPC Class Codes: A01N 37/36 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
• CPC Class Codes: A01N 37/44 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
• CPC Class Codes: A01N 41/10 Sulfones; Sulfoxides
• CPC Class Codes: A01N 53/00 Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• CPC Class Codes: C07B 2200/07 Optical isomers
• CPC Class Codes: C07C 225/16 and containing six-membered aromatic rings
• CPC Class Codes: C07C 233/78 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
• CPC Class Codes: C07C 233/83 of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 243/38 with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 255/19 containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
• CPC Class Codes: C07C 255/46 to carbon atoms of non-condensed rings
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 317/28 with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
• CPC Class Codes: C07C 317/44 having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
• CPC Class Codes: C07C 323/41 : Y being a hydrogen or an acyclic carbon atom
• CPC Class Codes: C07C 323/60 : with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms

Abstract

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”).

Claims

1. A molecule having the following formula

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 (C₁-C₈)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, (C₁-C₆)alkyl, and (C₁-C₆)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 (C₁-C₆)alkyl;

(n) R13 is

(1) an H, or

(2) a (C₁-C₈)alkyl;

(o) R14 is independently selected from (C₁-C₈)alkyl, (C₁-C₈)haloalkyl, (C₃-C₈)cycloalkyl, (C₂-C₈)alkenyl, or (C₂-C₈)alkynyl, wherein each said alkyl, haloalkyl, cycloalkyl, alkenyl, and alkynyl has one or more substituents selected from F, Cl, Br, I, CN, NO₂, OH, oxo, (C₁-C₆)alkoxy, S(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, S(O)₂(C₁-C₆)alkyl, and N((C₁-C₆)alkyl)₂ wherein each (C₁-C₆)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 (C₁-C₈)haloalkyl;

(g) R7 is H;

(h) R8 is H;

(i) R9 is H;

(j) R10 is Br, (C₁-C₈)alkyl, (C₁-C₈)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 (C₁-C₆)alkyl;

(n) R13 is

(1) an H, or

(2) a (C₁-C₈)alkyl;

(o) R14 is (C₁-C₈)alkyl, (C₁-C₈)haloalkyl, (C₃-C₈)cycloalkyl, or (C₂-C₈)alkenyl, wherein each said alkyl or cycloalkyl is substituted with CN, SCH₃, S(O)CH₃, or S(O)₂CH₃.

4. A molecule according to claim 1 wherein said molecule is selected from one of the following molecules

5. A molecule according to claim 1 wherein said molecule is selected from one of the following molecules

6. A molecule according to any one of claims 1, 2, or 3, wherein R14 is (C₁-C₆)alkyl or (C₃-C₆)cycloalkyl that is substituted with one or more substituents selected from CN, S(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, and S(O)₂(C₁-C₆)alkyl.

7. A molecule according to any one of claim 1 or 2 wherein R14 is CF₃, CH₂CF₃, CH₂CH₂CF₃, CH₂CH₂CH₂CF₃, CH₂CH₂CH(CF₃)CH₃, CH(CH₃)CH₂CF₃, C(CH₃)₂CF₃, C(CH₃)₂CH₂CF₃, CH₃, CH₂CH₃, CH₂CH₂CH₃, CH₂CH₂CH₂CH₃, CH₂CH₂CH₂CH₂CH₃, CH(CH₃)₂, CH₂CH(CH₃)₂, CH₂CH₂CH(CH₃)₂, C(CH₃)₃, CH₂C(CH₃)₃, CH₂CH₂C(CH₃)₃, CH₂CH₂CH₂C(CH₃)₃, cyclopropyl, CH═

CH₂, CH═

CH(CH₃), CH═

C(CH₃)₂, CH₂CH═

CH₂, CH₂CH═

CH(CH₃), C(CH₃)═

CH₂, C(CH₃)═

CH(CH₃), C≡

CH, CH₂C≡

CH, CH₂CN, CH₂CH₂CN, CH₂SCH₃, CH₂CH₂SCH₃, CH₂S(O)CH₃, CH₂CH₂S(O)CH₃, CH₂S(O)₂CH₃, and CH₂CH₂S(O)₂CH₃.

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 CF₃.

12. A molecule according to any one of claims 1, 2, or 3, wherein R10 is Br, CH₃, or CF₃.

13. A molecule according to any one of claims 1, 2, or 3, wherein L is —

CH₂—

, —

CH(CH₃)—

, —

CH(CH₂CH₃)—

, or —

CH₂CH₂—

.

14. A molecule according to any one of claims 1, 2, or 3, wherein R13 is H or CH₃.