Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto

Patent metadata

Field	Value
Publication number	US-9249133-B2
Application number	US-201414208394-A
Country	US
Kind code	B2
Filing date	Mar 13, 2014
Priority date	Mar 14, 2013
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

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”).

First claim

We claim:

1. A process comprising reacting 2-iminolthiazolidin-4-one (3-1a) with an isocyanate (1-2) to produce thiobiuret (3-1′)

wherein
(A) Ar 1 is selected from
(1) phenyl, pyridazinyl, pyridyl, pyrimidinyl, or
(2) substituted phenyl, substituted pyridazinyl, substituted pyridyl, or substituted pyrimidinyl,
wherein said substituted phenyl, substituted pyridazinyl, substituted pyridyl, and substituted pyrimidinyl, have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, substituted phenyl and substituted phenoxy
wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, and phenoxy;

(B) Het is a 5- or 6-membered, saturated or unsaturated, heterocyclic ring, containing one or more heteroatoms independently selected from nitrogen, sulfur, or oxygen, and where Ar 1 and Ar 2 are not ortho to each other (but may be meta or para, such as, for a five-membered ring they are 1, 3 and for a 6-membered ring they are either 1, 3 or 1, 4) and where said heterocyclic ring may also be substituted with one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , OXO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, substituted phenyl and substituted phenoxy
wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), phenyl, and phenoxy;

(C) Ar 2 is selected from
(1) phenyl, pyridazinyl, pyridyl, pyrimidinyl, or
(2) substituted phenyl, substituted pyridazinyl, substituted pyridyl, or substituted pyrimidinyl,
wherein said substituted phenyl, substituted pyridazinyl, substituted pyridyl, and substituted pyrimidinyl, have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, substituted phenyl and substituted phenoxy
wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, and phenoxy;

(D) R 1 is selected from H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)O(C 1 -C 6 alkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)OC(═O)(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), and (C 1 -C 6 alkyl)OC(═O)O(C 1 -C 6 alkyl),
wherein each alkyl, cycloalkyl, cycloalkoxy, alkoxy, alkenyl, and alkynyl are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , OXO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, and phenoxy;

(E) R 2 is selected from (J), H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(═O)(C 1 -C 6 alkyl), (C 1 -C 6 alky

Assignees

• Dow Agrosciences Llc

Inventors

• Fischer Lindsey G
• Ward Andrew L
• Ross Jr Ronald
• Giampietro Natalie C
• Deamicis Carl
• Hao Yan
• Crouse Gary D
• Sparks Thomas C
• Baum Erich W
• Petkus Jeff

Classifications

• A01N25/00

  Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests · CPC title

• A01N43/653 Primary

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C07D417/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title

• A01N47/42

  containing —N=CX2 groups, e.g. isothiourea · CPC title