IP Library Granted Patent US 9,661,850
Granted Patent B2
US 9,661,850 · App. 14/423,177 · Granted May 30, 2017

Methods of soil pest control

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Quick Facts
Patent No.
US 9,661,850
App. No.
14/423,177
Granted
May 30, 2017
Kind
B2
Abstract

The present invention relates to methods of controlling and/or preventing soil-dwelling pests in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof with a compound of formula (I) wherein —B 1 —B 2 —B 3 — is —C═N—O—, —C═N—CH 2 —, —C═CH 2 —O— or —N—CH 2 —CH 2 —; L is a direct bond or methylene; A 1 and A 2 are C—H, or one of A 1 and A 2 is C—H and the other is N; X 1 is group X, formula (X) R 1 is C 1 -C 4 alkyl, C 1 -C 4 aloalkyl or C 3 -C 6 cycloalkyl; R 2 is chlorodifluoromethyl or trifluoromethyl; each R 3 is independently bromo, chloro, fluoro or trifluoromethyl; R 4 is hydrogen, halogen, methyl, halomethyl or cyano; R 5 is hydrogen; or R 4 and R 5 together form a bridging 1,3-butadiene group; p is 2 or 3. Preferably the soil-dwelling pest is selected from corn rootworm, wireworms, grubs, in particular white grubs (e.g. Phyllophaga sp., Diloboderus sp., Popillia japonica ), termites (in particular for sugar cane), subterraneous stinkbugs (e.g. Scaptocoris sp.), cutworms (e.g. agrotis sp.), millipedes (e.g. Julus sp.) and broca gigante (e.g. Telchin licus ).

Claims (30)

1. A method of controlling and/or preventing soil-dwelling pests in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof with a compound of formula I

wherein

—B 1 —B 2 —B 3 — is —C═N—O—, —C═N—CH 2 —, —C═CH 2 —O— or —N—CH 2 —CH 2 —;

L is a direct bond or methylene;

A 1 and A 2 are C—H, or one of A 1 and A 2 is C—H and the other is N;

X 1 is group X

R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl;

R 2 is chlorodifluoromethyl or trifluoromethyl;

each R 3 is independently bromo, chloro, fluoro or trifluoromethyl;

R 4 is hydrogen, halogen, methyl, halomethyl or cyano;

R 5 is hydrogen;

or R 4 and R 5 together form a bridging 1,3-butadiene group;

p is 2 or 3,

and where the soil-dwelling pest includes at least one pest chosen from a wireworm; a grub; a white grub; a termite; a subterraneous stinkbug; a cutworm; a millipede; and a broca gigante.

2. A method according to claim 1 , wherein the compound of formula I is applied directly to soil.

3. A method according to claim 1 wherein the compound of formula I is applied to soil by treatment of a seed with a compound of formula I.

4. A method comprising applying a compound of formula I as defined in claim 1 to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I directly to soil.

5. A method according to claim 3 , wherein the compound of formula I is applied in-furrow.

6. A method according to claim 1 , wherein A 1 and A 2 are C—H, R 2 is trifluoromethyl, and R 5 is hydrogen, wherein the soil-dwelling pests are optionally wireworms.

7. A method according to claim 1 , wherein A 1 and A 2 are C—H, R 2 is trifluoromethyl, R 4 is methyl, R 5 is hydrogen, each R 3 is chlorine, p is 2, wherein the soil-dwelling pests are optionally wireworms.

8. A method according to claim 1 , wherein R 1 is methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, trifluoroethyl, difluoroethyl, wherein the soil-dwelling pests are optionally wireworms.

9. A method according to claim 1 , wherein R 1 is ethyl or trifluoroethyl, wherein the soil-dwelling pests are optionally wireworms.

10. A method according to claim 1 , wherein X 1 is 3,5-dichloro-phenyl, 3,5-dichloro-4-fluorophenyl-, 3,4,5-trichlorophenyl-, or 3,5-bis(trifluoromethyl)phenyl, wherein the soil-dwelling pests are optionally wireworms.

11. A method according to claim 1 , wherein —B 1 —B 2 —B 3 — is —C═N—O—, wherein the soil-dwelling pests are optionally wireworms.

12. A method according to claim 1 , wherein the compound of formula I is a mixture of compounds I* and I**

wherein the molar proportion of compound I** compared to the total amount of both enantiomers is greater than 50%, wherein the soil-dwelling pests are optionally wireworms.

13. A method according to claim 1 , wherein the compound of formula I is a mixture of compounds I′ and I″

(S═S stereochemistry, R═R stereochemistry)

wherein the molar proportion of compound I″ compared to the total amount of both enantiomers is greater than 50%, preferably wherein the soil-dwelling pests are wireworms.

14. A method for obtaining regulatory approval for the use of one or more of a compound of formula I as defined in claim 1 to control a pest selected from wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Mar 14, 2025
From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 070517/0654 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2016
From: EL QACEMI, MYRIEM; CASSAYRE, JEROME YVES; KURTZ, BENEDIKT
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 037733/0956 →