Granted Patent B2

US 9,138,002 · App. 14/182,793 · Granted Sep 22, 2015

Abstract

Claims (30)

1. A method of using a compound against pathogens affecting meats, plants, or plant parts, comprising contacting the meats, plants, or plant parts with an effective amount of a compound having a structure of formula (A):

R A -L A -G-L B -R B   (A)

wherein

each of R A and R B is independently an oxaborole moiety;

each of L A and L B is independently —O—,

each of R and R′ is independently hydrogen, unsubstituted or substituted C 1-18 -alkyl, arylalkyl, aryl, or heterocyclic moiety; and

G is a substituted or unsubstituted C 1-18 -alkylene, arylalkylene, arylene, or heterocyclic moiety;

and agriculturally acceptable salts thereof.

2. The method of claim 1 , wherein

each of R A and R B is independently derived from a member selected from the group consisting of 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole; 5-chloro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole; 1,3-dihydro-1-hydroxy-2,1-benzoxaborole; and combinations thereof;

the -L A -G-L B - portion of formula (A) is derived from a diol or diamine compound; the diol compound is selected from the group consisting of 1,2-ethylene glycol; 1,2-propylene glycol; 1,3-propylene glycol; 1,1,2,2-tetramethyl-1,2-ethylene glycol; 2,2-dimethyl-1,3-propylene glycol; 1,6-hexanediol; 1,10-decanediol; and combinations thereof; and the diamine compound is 1,2-ethylene diamine; 1,3-propylene diamine; or combinations thereof;

G is a substituted or unsubstituted C 1-8 -alkylene;

and agriculturally acceptable salts thereof.

3. The method of claim 1 , wherein the compound is volatile.

4. The method of claim 1 , wherein the compound is a fungicide.

5. The method of claim 1 , wherein G is selected from —CH 2 —, —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —, —CH(CH 3 )—CH 2 —, —C(CH 3 ) 2 —C(CH 3 ) 2 , and —CH 2 —C(CH 3 ) 2 —CH 2 —.

6. The method of claim 1 , wherein each of R A and R B is independently

7. The method of claim 1 , wherein the compound has the structure of

8. The method of claim 1 , wherein the meats, plants, or plant parts are selected from the group consisting of barley, camphor tree, canola, castor-oil plant, cinnamon, cocoa, coffee, corn, cotton, flax, grapevine, hemp, hops, jute, maize, mustard, nuts, oat, poppy, rape, rice, rubber plant, rye, sunflower, sorghum, soybean, sugar cane, tea, tobacco, and wheat.

9. The method of claim 1 , wherein the plants are selected from the group consisting of banana, pineapple, citrus, grapes, watermelon, cantaloupe, muskmelon, and other melons, apple, peach, pear, cherry, kiwifruit, mango, nectarine, guava, papaya, persimmon, pomegranate, avocado, fig, citrus, and berries.

10. The method of claim 1 , wherein the compound has a structure of formula (A1) or (A2):

wherein each of A 1 , A 2 , D 1 , and D 2 is independently hydrogen, substituted or unsubstituted C 1-18 -alkyl, arylalkyl, aryl, or heterocyclic; or A 1 and D 1 , or A 2 and D 2 together form a 5, 6, or 7-membered fused ring which is substituted or unsubstituted;

each of R 16 , R 17 , R 18 , and R 19 is independently hydrogen, substituted or unsubstituted C 1-6 -alkyl, nitrile, nitro, aryl or aryl alkyl; or R 16 and R 17 , or R 18 and R 19 together form an alicyclic ring which is substituted or unsubstituted;

B is boron; and

G is a substituted or unsubstituted C 1-18 -alkylene, arylalkylene, arylene, or heterocyclic moiety;

and agriculturally acceptable salts thereof.

11. The method of claim 1 , wherein each of R A and R B is independently derived from the group consisting of 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole; 5-chloro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole; 1,3-dihydro-1-hydroxy-2,1-benzoxaborole; and combinations thereof.

12. The method of claim 1 , wherein the -L A -G-L B - portion of formula (A) is derived from a diol or diamine compound.

13. The method of claim 12 , wherein the diol compound is selected from the group consisting of 1,2-ethylene glycol; 1,2-propylene glycol; 1,3-propylene glycol; 1,1,2,2-tetramethyl-1,2-ethylene glycol; 2,2-dimethyl-1,3-propylene glycol; 1,6-hexanediol; 1,10-decanediol; and combinations thereof.

14. The method of claim 12 , wherein the diamine compound is 1,2-ethylene diamine; 1,3-propylene diamine; or combinations thereof.

Assignments (8)