EXTENDED AND CONTINUOUS RELEASE COMPOSITIONS FOR PLANT HEALTH AND METHOD OF USE
The subject matter described herein relates generally to compositions comprising an agriculturally active compound having at least one carboxylic acid moiety or salt thereof in combination with a corresponding ester of the acid for continuous and sustained release of the compound, and methods of using the compositions for improving plant properties.
1 . A composition comprising:
i. an agriculturally active compound having at least one carboxylic acid moiety and having a formula:
or salts thereof,
wherein
e and f are independently an integer from 1 to 4, and
Z and Z′ are a portion of the agriculturally active compound;
ii. one or more ester(s) of the agriculturally active compound selected from the group consisting of:
wherein,
O-A-O is a residue of a first polyol;
e and f are independently an integer from 1 to 4; and
Z and Z′ are a portion of the agriculturally active compound;
wherein,
O-A-O is the residue of a first polyol; and
Z and Z′ are a portion of the agriculturally active compound;
wherein,
A-O is a residue of a first polyol;
A′-O is a residue of a second polyol or a hydroxyl group;
x is an integer from 0 to 3; and
Z is a portion of an agriculturally active compound;
wherein,
O-A-OH is a residue of a first polyol;
y is an integer from 1 to 50; and
Z is a portion of the agriculturally active compound; and
wherein,
O-A-O is a residue of a polyol;
Z is a portion of the agriculturally active compound; and
R 1 is absent or is selected from hydrogen and Q, wherein Q is Z′; and
iii. an agriculturally acceptable carrier.
2 . The composition of claim 1 , wherein the agriculturally active compound is a monocarboxylic acid or dicarboxylic acid and the ester of said agriculturally active compound is a monoester or a diester.
3 . (canceled)
4 . (canceled)
5 . (canceled)
6 . The composition of claim 1 , wherein said first polyol is polyethylene glycol or a copolymer thereof, and said second polyol is polyethylene glycol or a copolymer thereof or is a hydroxyl group, wherein said polyethylene glycol has a weight averaged molecular weight of about 150 D to about 10,000 D.
7 . (canceled)
8 . The composition of claim 6 , further comprising:
a second ester of said agriculturally active compound, said second ester having the formula:
wherein, O-A″-O, A″-O and A′″-O are each a residue of a polyalkylene glycol other than polyethylene glycol (PEG);”
x′ is 0 or 1; and
Z and Z′ are a portion of the agriculturally active compound.
9 . (canceled)
10 . (canceled)
11 . The composition of claim 1 , wherein said first polyol and said second polyol are different types of polyol.
12 . The composition of claim 1 , wherein the ratio of said agriculturally active compound to said ester of said agriculturally active compound is about 0.01:1 to about 0.5:1.
13 . The composition of claim 1 , wherein said agriculturally active compound I′ or I″ is selected from the group consisting of
a. carboxylic acid containing herbicides;
b. carboxylic acid containing fungicides;
c. pyroglutamic acid;
d. levulinic acid;
e. pamoic acid;
f. ketosuccinamide; and
g. a dicarboxylic acid having the structure:
wherein, D is a linear C 1-5 alkyl group having at least one carbonyl embedded in the alkyl group.
14 . The composition of claim 13 comprising:
i. an agriculturally active compound I′, wherein the agriculturally active compounds is pyroglutamic acid having the structure:
or salts thereof, and
ii. said ester of said agriculturally active compound, wherein the ester is one or more esters of Formula IV:
wherein,
O-A-O is a residue of a first polyol;
Z is a
and
R 1 is absent or is selected from hydrogen and Q;
wherein, Q is Q 1 and has the structure:
wherein,
is the point of attachment; or
i. an agriculturally active compound I′, wherein the agriculturally active compounds is levulinic acid having the structure:
or salts thereof, and
ii. said ester of said agriculturally active compound, wherein the ester is an ester of Formula IV:
wherein,
O-A-O is a residue of a first polyol;
Z is
and
R 1 is absent or is selected from hydrogen and Q;
wherein, Q is Q 2 and has the structure:
wherein,
is the point of attachment;
or
i. an agriculturally active compound I′, wherein the agriculturally active compounds is ketosuccinimate having the structure:
or salts thereof, and
ii. said ester of said agriculturally active compound, wherein the ester is an ester of Formula IV:
wherein,
O-A-O is a residue of a first polyol;
Z is
R 1 is absent or is selected from hydrogen and Q;
wherein, Q is Q 3 and has the structure:
wherein,
is the point of attachment; and
an agriculturally acceptable carrier.
15 . The composition of claim 14 , wherein the agriculturally active compound is pyroglutamic acid, and said ester of pyroglutamic acid comprises one or more esters of pyroglutamic acid esters selected from the group consisting of Formulae V-VII:
or salts thereof, wherein
O-A-O is a residue of a linear or branched polyalkylene glycol or oligomer or dendrimer thereof, and R 1 is absent or is selected from the group consisting of hydrogen and Q 1 ;
or salts thereof, wherein,
R 2 , R 3 and R 4 , in each instance, is independently selected from the group consisting of hydrogen and Q 1 ;
or salts thereof, wherein,
R 3 and R 4 , in each instance, is independently selected from the group consisting of hydrogen and Q 1 .
16 . (canceled)
17 . The composition of claim 15 , wherein the residue of a linear or branched polyalkylene glycol or oligomer or dendrimer thereof is a residue of PEG or PPG.
18 . The composition of claim 14 , wherein the ester is of Formula Va:
wherein, O-PEG-O is a residue of PEG; R 1 is selected from hydrogen and Q.
19 . (canceled)
20 . The composition of claim 18 , wherein about 10% to about 90% of R 1 is Q and the remainder of R 1 is hydrogen.
21 . The composition of claim 15 , comprising a mixture of esters of pyroglutamic acid, the mixture comprising Formulae V and VI; Formulae V and VII; Formulae VI and VII; and Formula V, VI and VII.
22 . (canceled)
23 . (canceled)
24 . The composition of claim 13 , wherein said agriculturally active compound I or I′ is:
g. a dicarboxylic acid having the structure:
wherein D is
25 . The composition of claim 24 , wherein the ester of said agriculturally active compound has the Formula IIa′:
wherein, D is
26 . The composition of claim 25 , wherein O-A and O-A-OH, in each instance, is: a residue of a polyalkylene glycol; and/or
residue of a different polyalkylene glycol; and/or
a residue of tetraethylene glycol; and/or
a residue of tetraethylene glycol having the structure:
27 . The composition of claim 1 , wherein from about 50% to about 100% of the ester of said agriculturally active compound is hydrolyzed and/or released over a period of about 50 days or less after the composition is contacted with the plant or area adjacent to the plant.
28 . (canceled)
29 . The composition of claim 1 , wherein said agriculturally active compound I′ or I″ is a herbicide selected from the group consisting of cambendichlor, chloramben, dicamba, 2,3,6-TBA, tricamba and carboxylic acid analogs thereof, byspyribac and pyriminobac and carboxylic acid analogs thereof, aminopyralid, clopyralid, florpyrauxifen, halauxifen and picloram, quinclorac, quinmerac, clacyfos, 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, and 2,4,5-T, cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, and mecoprop-P, chlorazifop, clodinafop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiafop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, kuicaoxi, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, and endothal.
30 . (canceled)
31 . The composition of claim 1 , wherein said agriculturally active compound I′ or I″ is a fungicide selected from the group consisting of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, pefurazoate, valifenalate and carboxylic acid analogs thereof, blasticidin-S, kasugamycin, natamycin, polyoxorim, azoxystrobin, bifujunzhi, coumoxystrobin, enoxastrobin, flufenoxystrobin, jiaxiangjunzhi, picoxystrobin, pyraoxystrobin, cloquintocet, fenchlorazole, isoxadifen, mefenpyr, megatomoic acid and carboxylic acid analogs thereof and salts thereof.
32 . An article comprising a composition of claim 1 having an engineered three-dimensional shape, wherein the shape is selected from the group consisting of a rod, a spike, a block, and an orb.
33 . (canceled)
34 . A method for improving plant properties comprising:
contacting the plant or area adjacent to the plant with an effective amount of a composition of claim 1 ,
wherein improving plant properties comprises one or more of: increasing growth rate, increasing nodulation, increasing the percent dry weight of the plant, and/or increasing fresh weight.
35 . (canceled)
36 . (canceled)
37 . (canceled)
38 . (canceled)
39 . (canceled)
40 . (canceled)
41 . (canceled)
42 . (canceled)
43 . (canceled)
44 . A method for improving resistance to pests comprising contacting the area adjacent to the plant with a composition of claim 1 .
45 .- 48 . (canceled)