Pesticidal compositions and related methods

Patent metadata

Field	Value
Publication number	US-9549560-B2
Application number	US-201414517442-A
Country	US
Kind code	B2
Filing date	Oct 17, 2014
Priority date	Oct 22, 2013
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

A pesticidal composition comprises at least one compound selected from a 1-(3-pyridyl-N-oxide) pyrazole compound of formula I, II, or III, or any agriculturally acceptable salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 12 , R 13 , Y, 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 1-(3-pyridyl-N-oxide)pyrazole compound of formula I 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 11 ;
(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 11 , C(═X 1 )R 11 , C(═X 1 )OR 11 , C(═X 1 )N(R 11 ) 2 , N(R 11 ) 2 , N(R 11 )C(═X 1 )R 11 , SR 11 , S(O) n OR 11 , or R 11 S(O) n R 11 ,
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 3 -C 10 halocycloalkenyl, OR 11 , S(O) n OR 11 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, each of which is substituted, unsubstituted, or substituted with R 11 ;
(c) R 5 is 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 11 , C(═X 1 )R 11 , C(═X 1 )OR 11 , C(═X 1 )N(R 11 ) 2 , N(R 11 ) 2 , N(R 11 )C(═X 1 )R 11 , SR 11 , S(O) n OR 11 , or R 11 S(O) n R 11 ,
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 11 , S(O) n OR 11 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, each of which is substituted, unsubstituted, or substituted with R 11 ;
(d) R 6 is H, F, Cl, Br, I, substituted or unsubstituted C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl,
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 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, or C 3 -C 10 halocycloalkenyl;
(e) R 7 is selected from 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 1 -C 6 alkoxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, 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, C 1 -C 6 alkyl-(C 3 -C 10 cycloalkyl) wherein the alkyl and cycloalkyl is independently substituted or unsubstituted,
wherein each said R 7 , 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 11 , S(O) n OR 11 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, or R 11 aryl, each of which is substituted, unsubstituted, or substituted with R 11 ;
(f) R 8 is R 9 S(O) n R 10 or R 9 S(O) n H;
(g) R 9 is substituted or unsubstituted C 2 -C 12 alkenyl, substituted or unsubstituted C 1 -C 12 alkyl, or substituted or unsubstituted C 3 -C 10 cycloalkyl,
wherein each said R 9 , 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 3 -C 10 cycloalkyl, C 3 -C 10 halocycloalkyl, OR 11 , S(O) n R 11 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, each of which is substituted, unsubstituted, or substituted with R 11 ;
(h) R 10 is selected from 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 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 cycloalkenyl, C 3 -C 10 halocycloalkyl, C 3 -C 10 halocycloalkenyl, oxo, OR 11 , S(O) n R 11 , C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl, each of which is substituted, unsubstituted, or substituted with R 11 ;
(i) R 11 is, each independently, selected from H, R 8 , 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 11 , 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, OC 1 -C 6 alkyl, OC 1 -C 6 haloalkyl, S(O) n C 1 -C 6 alkyl, S(O) n OC 1 -C 6 alkyl, C 6 -C 20 aryl, or C 1 -C 20 heterocyclyl;
(j) Q is O, S or S(═O) n ;
(k) X 1 is O or S; and
(l) n is 0, 1 or 2.

2. The composition of claim 1 , wherein R 1 , R 2 , and R 4 are H.

3. The composition of claim 1 , wherein R 3 is selected from H, F, Cl, Br, or I.

4. The composition of claim 1 , wherein R 3 is H or F.

5. The composition of claim 1 , wherein R 5 is selected from F, Cl, Br, I, or unsubstituted C 1 -C 6 alkyl.

6. The composition of claim 1 , wherein R 5 is Cl or CH 3 .

7. The composition of claim 1 , wherein R 6 is H.

8. The composition of claim 1 , wherein R 7 is selected from H, CH 3 , CH 2 CH 3 CH 2 C≡CH, or CH(CH 3 )C≡CH.

9. The composition of claim 1 , wherein R 8 is selected from C 1 -C 6 alkyl-S(O) n CH 2 (uns

Assignees

• Dow Agrosciences Llc

Inventors

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

Classifications

• C05G3/60

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

• A01N25/26

  in coated particulate form · CPC title

• A01N43/56 Primary

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• A01N47/20 Primary

  N-Aryl derivatives thereof · CPC title

• Y10S424/10

  Insect repellent · CPC title