Pesticidal compositions and related methods

Patent metadata

Field	Value
Publication number	US-9445597-B2
Application number	US-201414517353-A
Country	US
Kind code	B2
Filing date	Oct 17, 2014
Priority date	Oct 22, 2013
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

A pesticidal composition comprises one or more of the following compounds: 3-(thiazol-2-yl)pyridine 1-oxide compound of formula I or II, or N-(4-chloro-2-(pyridin-3-yl)thiazol-5-yl)-3-(methylthio)propanamide compound (C3), or any agriculturally acceptable salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and Q, are as described herein. A method of controlling pests comprises applying the pesticidal composition near a population of pests.

First claim

We claim:

1. A pesticidal composition, comprising one or more of the following compounds:
3 (thiazol-2-yl)pyridine 1-oxide compound of formula I or II, or any agriculturally acceptable salt thereof

wherein:
(a) R 1 , R 2 , and R 4 are independently selected from H, F, Cl, Br, I, substituted or unsubstituted C 1 -C 6 alkyl, or substituted or unsubstituted C 1 -C 6 haloalkyl,
wherein each said R 1 , R 2 , and R 4 , when substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 3 -C 10 cycloalkyl, or C 3 -C 10 halocycloalkyl, each of which is substituted, unsubstituted, or substituted with R 10 ;
(b) R 3 is selected from H, F, Cl, Br, I, CN, NO 2 , substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 1 -C 6 haloalkyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, OR 10 , C(═X 1 )R 10 , C(═X 1 )OR 10 , C(═X 1 )N(R 10 ) 2 , N(R 10 ) 2 , N(R 10 )C(═X 1 )R 10 , SR 10 , S(O) n OR 10 , or R 10 S(O) n R 10 ,
wherein each said R 3 , when substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 halocycloalkyl, C 1 -C 10 halocycloalkenyl, OR 10 , S(O) n OR 10 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, each of which is substituted, unsubstituted, or substituted with R 10 ;
(c) R 5 is selected from H, F, Cl, Br, I, CN, NO 2 , substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, OR 10 , C(═X 1 )R 10 , C(═X 1 )OR 10 , C(═X 1 )N(R 10 ) 2 , N(R 10 ) 2 , N(R 10 )C(═X 1 )R 10 , SR 10 , S(O) n OR 10 , or R 10 S(O) n R 10 ,
wherein each said R 5 , when substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 halocycloalkyl, C 3 -C 10 halocycloalkenyl, OR 10 , S(O) n OR 10 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, each of which is substituted, unsubstituted, or substituted with R 10 ;
(d) for the 3-(thiazol-2-yl)pyridine 1-oxide of formula I or any agriculturally acceptable salt thereof, R 6 is substituted or unsubstituted C 2 -C 6 alkynyl, or C 1 -C 6 alkyl C 2 -C 6 alkynyl wherein the alkyl and alkynyl is independently substituted or unsubstituted,
wherein each said R 6 , when substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , 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 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 halocycloalkyl, C 3 -C 10 halocycloalkenyl, OR 10 , S(O) n OR 10 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, R 10 aryl, each of which is substituted, unsubstituted, or substituted with R 10 ;
for the 3-(thiazol-2-yl)pyridine 1-oxide of formula II or any agriculturally acceptable salt thereof, R 6 is H, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 2 -C 6 alkynyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 alkynyl wherein the alkyl and alkynyl is independently substituted or unsubstituted, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, C 1 -C 6 alkyl C 6 -C 20 aryl wherein the alkyl and aryl is independently substituted or unsubstituted, C 1 -C 6 alkyl-(C 3 -C 10 cyclohaloalkyl) wherein the alkyl and cyclohaloalkyl is independently substituted or unsubstituted, or C 1 -C 6 alkyl-(C 3 -C 10 cycloalkyl) wherein the alkyl and cycloalkyl is independently substituted or unsubstituted,
wherein each said R 6 , when substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , 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, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 halocycloalkyl, C 3 -C 10 halocycloalkenyl, OR 10 , S(O) n OR 10 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, R 10 aryl, each of which is substituted, unsubstituted, or substituted with R 10 ;
(e) Y is a bond, or is substituted or unsubstituted C 1 -C 6 alkyl, or substituted or unsubstituted C 2 -C 6 alkenyl,
except where Y is a bond, wherein each said Y, when substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, or C 3 -C 10 cycloalkyl,
optionally Y and R 7 are connected in a cyclic arrangement, where optionally such arrangement have one or more heteroatoms selected from O, S, or N, in the cyclic structure connecting Y and R 7 ;
(f) R 7 is R 8 S(O) n R 9 ;
(g) R 8 is substituted or unsubstituted C 1 -C 12 alkenyl, substituted or unsubstituted C 1 -C 12 alkyl, or substituted or unsubstituted C 3 -C 10 cycloalkyl,
wherein each said R 8 , when substituted, has one or more substituents selected from F, Cl, Br, I, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 1 -C 10 cycloalkyl, C 3 -C 10 halocycloalkyl, OR 10 , S(O) n R 10 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, each of which is substituted, unsubstituted, or substituted with R 10 ;
(h) R 9 is substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 halocycloalkyl substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, or substituted or unsubstituted C 1 -C 20 heterocyclyl,
wherein each said R 9 , when substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 halocycloalkyl, C 3 -C 10 halocycloalkenyl, oxo, OR 10 , S(O) n R 10 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, each of which is substituted, unsubstituted, or substituted with R 10 ;
(i) R 10 is H, CN, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, substituted or unsubstituted S(O) n C 1 -C 6 alkyl, or substituted or unsubstituted N(C 1 -C 6 alkyl) 2 ,
wherein each said R 10 , when substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cyclo

Assignees

• Dow Agrosciences Llc

Inventors

• Garizi Negar
• Walsh Martin J
• Buysse Ann M
• Knueppel Daniel
• Kubota Asako
• Niyaz Noormohamed M
• Zhang Yu
• Hunter Ricky
• Trullinger Tony K

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• C05G3/60

  Biocides or preservatives, e.g. disinfectants, pesticides or herbicides; Pest repellants or attractants · CPC title

• A01N25/08

  containing solids as carriers or diluents · CPC title