IP Library Granted Patent US 8,563,470
Granted Patent B2
US 8,563,470 · App. 13/234,174 · Granted Oct 22, 2013

Anthranilic diamide and cyclodextrin compositions for propagule coating

Inventor: Wilson Tam (Boothwyn, PA)
Assignee: E I du Pont de Nemours and Company
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Quick Facts
Patent No.
US 8,563,470
App. No.
13/234,174
Granted
Oct 22, 2013
Kind
B2
Abstract

Disclosed is an insecticidal composition comprising by weight based on the total weight of the composition: a) from about 9 to about 91% of one or more anthranilic diamide insecticides; and (b) from about 9 to about 91% of a cyclodextrin; wherein the ratio of component (b) to component (a) is about 1:10 to about 10:1 by weight. Also disclosed are inclusion complexes of the anthranilic diamide insecticides with the cyclodextrin. Also disclosed is a geotropic propagule coated with an insecticidally effective amount of the aforedescribed composition. Further disclosed is a liquid composition comprising the insecticidal composition, and a method for protecting a geotropic propagule and plant derived therefrom from a phytophagous insect pest.

Claims (43)

1. An insecticidal composition comprising by weight based on the total weight of the composition:

(a) from about 9 to about 91% of one or more anthranilic diamide insecticides; and

(b) from about 9 to about 91% of a cyclodextrin;

wherein the ratio of component (b) to component (a) is about 1:10 to about 10:1 by weight,

wherein component (a) comprises at least one compound selected from anthranilic diamides of Formula 1, N-oxides, and salts thereof,

wherein

X is N, CF, CCl, CBr or Cl;

R 1 is CH 3 , Cl, Br or F;

R 2 is H, F, Cl, Br or —CN;

R 3 is F, Cl, Br, C 1 -C 4 haloalkyl or C 1 -C 4 haloalkoxy;

R 4a is H, C 1 -C 4 alkyl, cyclopropylmethyl or 1-cyclopropylethyl;

R 4b is H or CH 3 ;

R 5 is H, F, Cl or Br; and

R 6 is H, F, Cl or Br.

2. The composition of claim 1 , wherein component (a) is selected from compounds of Formula 1 wherein X is N; R 1 is CH 3 ; R 2 is Cl or —CN; R 3 is Br; R 4a is CH 3 ; R 4b is H; R 5 is Cl; and R 6 is H; and salts thereof.

3. The composition of claim 2 , wherein component (a) is the compound of Formula 1 wherein R 2 is Cl.

4. The composition of claim 2 , wherein component (a) is the compound of Formula 1 wherein R 2 is —CN.

5. The composition of claim 1 wherein component (b) is at least 15% of the composition by weight.

6. The composition of claim 1 wherein the ratio of component (b) to component (a) is at least 1:5 by weight.

7. The composition of claim 1 wherein component (b) is selected from the group of α-cyclodextrins, β-cyclodextrins and γ-cyclodextrins.

8. The composition of claim 7 wherein component (b) is a β-cyclodextrin.

9. The composition of claim 8 wherein the β-cyclodextrin is 2-hydroxypropyl-β-cyclodextrin.

10. A geotropic propagule coated with an insecticidally effective amount of the composition of claim 1 .

11. The geotropic propagule of claim 10 wherein the geotropic propagule is a seed.

12. The geotropic propagule of claim 11 wherein the seed is a seed of cotton, maize, soybean, rapeseed, rice, wheat or barley.

13. A liquid composition consisting of about 5 to 80 weight % of the composition of claim 1 and about 20 to 95 weight % of a volatile aqueous liquid carrier.

14. A method for protecting a geotropic propagule and plant derived therefrom from a phytophagous insect pest, the method comprising coating the propagule with an insecticidally effective amount of the liquid composition of claim 13 and then evaporating the volatile aqueous liquid carrier of the composition.

15. The method of claim 14 wherein the insect pest is in a taxonomic order selected from Hemiptera and Lepidoptera.

16. An inclusion complex comprising:

(a) an anthranilic diamide of Formula 1, an N-oxide, or a salt thereof,

wherein

X is N, CF, CCl, CBr or Cl;

R 1 is CH 3 , Cl, Br or F;

R 2 is H, F, Cl, Br or —CN;

R 3 is F, Cl, Br, C 1 -C 4 haloalkyl or C 1 -C 4 haloalkoxy;

R 4a is H, C 1 -C 4 alkyl, cyclopropylmethyl or 1-cyclopropylethyl;

R 4b is H or CH 3 ;

R 5 is H, F, Cl or Br; and

R 6 is H, F, Cl or Br; and

(b) a cyclodextrin selected from the group of α-cyclodextrins, β-cyclodextrins and γ-cyclodextrins wherein the ratio range of component (a) to component (b) is from about 1:10 to about 10:1 by weight.

17. The inclusion complex of claim 16 wherein the anthranilic diamide is selected from compounds of Formula 1 wherein X is N; R 1 is CH 3 ; R 2 is Cl or —CN; R 3 is Br; R 4a is CH 3 ; R 4b is H; R 5 is Cl; and R 6 is H; and salts thereof.

18. The inclusion complex of claim 17 wherein the anthranilic diamide is the compound of Formula 1 wherein R 2 is Cl.

19. The inclusion complex of claim 17 wherein the anthranilic diamide is the compound of Formula 1 wherein R 2 is —CN.

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded Nov 29, 2022
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 063141/0155 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2011
From: TAM, WILSON
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 027186/0168 →
Continuity (2)
Provisional Application 61422256 · Dec 13, 2010
Related Publication 20120149564A1 · Jun 14, 2012