Alkaloid-containing compositions and uses thereof
AssigneeBiotelliga Holdings Limited
InventorsStephen FORD, Emilie GALAND, Bernard Cecil KIMBLE, Alan James ROBINSON, Roelof VAN GINKEL
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Abstract
The present invention provides compositions comprising loline alkaloids including pesticidal compositions, methods of producing the compositions and uses of the compositions including uses as control agents. Methods for the control of pests, including plant or animal pests, for the enhancement of plant growth or reproduction, and treatment and prevention of insect infection and infestation, for example in plants or animals, are also provided.
Claims26
A composition comprising at least about 10 g/L of one or more loline alkaloids having the structure of Formula [I]:
- wherein R═H or CH3 and R′═H, CH3, CHO or COCH3, the one or more loline alkaloids comprising N-formylloline having the structure of Formula [II]:
- and one or more solvents;
- wherein
- a) the molar ratio of total hydroxyl groups and nitrogen-containing groups to N-formylloline of the composition is less than about 20, or
- b) the molar ratio of total hydroxyl groups and nitrogen-containing groups to N-formylloline of the composition is greater than about 20, and wherein the nucleophilicity coefficients of the hydroxyl groups or nitrogen-containing groups of the composition are less than about 0.6 eV;
- wherein the nitrogen-containing groups are selected from ammonia, a primary amine group, a secondary amine group, or mixtures thereof.
The composition of claim wherein the N-formylloline having the structure of Formula [II] is at least partially purified or isolated.
The composition of claim wherein the concentration of N-formylloline present in the composition is reduced by less than about 10% when stored at 54° C. (at 1 atm) for at least two weeks.
A composition comprising at least about 10 g/L of one or more loline alkaloids having the structure of Formula [I]:
- wherein R═H or CH3 and R′═H, CH3, CHO or COCH3, the one or more loline alkaloids comprising at least partially purified or isolated N-formylloline having the structure of Formula [II]:
- and one or more solvents,
- wherein the concentration of N-formylloline present in the composition is reduced by less than about 10% when stored at 54° C. (at 1 atm) for at least two weeks.
The composition of claim wherein
- a) the molar ratio of total hydroxyl groups and nitrogen-containing groups to N-formylloline of the composition is less than about 20, or
- b) the molar ratio of total hydroxyl groups and nitrogen-containing groups to N-formylloline of the composition is greater than 20, and wherein the nucleophilicity coefficients of the hydroxyl groups or nitrogen-containing groups of the composition are less than 0.6 eV;
- wherein the nitrogen-containing groups are selected from ammonia, a primary amine group, a secondary amine group, or mixtures thereof.
The composition of claim, wherein the nucleophilicity coefficients of the hydroxyl or nitrogen-containing groups of the one or more solvents are less than 0.5 eV.
The composition of claim, wherein the composition further comprises one or more loline alkaloids selected from the group comprising loline, norloline, N-acetylloline (NAL), N-acetylnorloline (NANL), and N-methylloline (NML), N-formylnorloline, or a combination of any two or more thereof.
The composition of claim, wherein the composition comprises N-formylloline (NFL), N-acetylloline (NAL), and N-acetylnorloline (NANL).
The composition of claim, wherein the weight ratio of [NANL]:[NFL]:[NAL] is from about 1:12:1 to about 2:5:3.
The composition of claim, wherein the composition comprises at least about 5 g/L of N-formylloline having the structure of Formula [II].
The composition of claim, wherein the composition comprises at least about 50 g/L of loline alkaloids having the structure of Formula [I].
The composition of claim, wherein the N-formylloline having the structure of Formula [II] and/or the one or more loline alkaloids having the structure of Formula [I] are substantially pure.
The composition of claim, wherein the composition is substantially free of non-loline plant derived alkaloids or material.
The composition of claim, consisting essentially of N-formylloline, optionally together with one or more loline alkaloids of Formula [I], and one or more solvents.
The composition of claim, wherein the molar ratio of total hydroxyl groups and nitrogen-containing groups to N-formylloline of the composition is less than about 10;
- wherein the nitrogen-containing groups are selected from ammonia, a primary amine group, a secondary amine group, or mixtures thereof.
The composition of claim, wherein the one or more solvents comprises at least about 10% w/w of the composition.
The composition of claim, wherein the one or more solvents are selected from the group comprising alcohols, ketones, esters, ethers, carbonates, amines, amides, nitriles, sulfoxides, and sulfones.
The composition of claim, wherein the one or more solvents are selected from the group comprising
- a) polyalkylene glycols, or ethers or esters thereof, preferably polyalkylene glycols, or ethers or esters thereof, of the formula R10O—[(C1-6alkylene)O]x—R1, wherein R1 and R10 are each independently selected from hydrogen, aliphatic, cycloaliphatic, acyl, aryl, or arylaliphatic, and x is an integer from 2 to 140;
- b) monoalkylene glycols, or ethers or esters thereof, preferably monoalkylene glycols, or ethers or esters thereof of the formula R20O—(C1-6alkylene)O—R2, wherein R20 and R2 are each independently selected from hydrogen, aliphatic, cycloaliphatic, acyl, aryl, or arylaliphatic;
- c) amines of the formula R25R26R27N, wherein R25, R26, and R27 are each independently selected from hydrogen or aliphatic, or R26 and R27 together with the nitrogen atom to which they are attached form a 5 to 8 membered heterocyclyl ring, which optionally comprises an additional heteroatom;
- d) monoalkylene diamines, preferably monoalkylene diamines of the formula R31NH—(C1-6alkylene)NR30—R32, wherein R31 and R32 are each independently selected from hydrogen, aliphatic, cycloaliphatic, acyl, aryl, or arylaliphatic, and R30 is selected from hydrogen or aliphatic;
- e) amides of the formula CH3CH(OH)C(═O)NR3R4, wherein R3 and R4 are each independently selected from hydrogen, C1-6alkyl, C2-6alkenyl, or C3-6cycloalkyl, each of which is optionally substituted by up to three substituents independently selected from phenyl, hydroxyl, C1-5alkoxy, morpholinyl and NR5R6 where R5 and R6 are each independently selected from C1-3alkyl, or phenyl optionally substituted by up to three substituents independently selected from C1-3alkyl;
- or R3 and R4 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, each of which is optionally substituted by up to three substituents each independently selected from C1-3alkyl;
- f) ketones, preferably ketones of the formula R7C(═O)R8, wherein R7 and R8 are each independently selected from aliphatic, cycloaliphatic, aryl, or arylaliphatic;
- g) aliphatic alcohols, preferably aliphatic alcohols of the formula R40OR41, wherein R40 is aliphatic, preferably C1-6alkyl, and R41 is hydrogen, aliphatic, preferably C1-6alkyl, or acyl;
- h) cycloaliphatic alcohols, preferably a C5-8cycloalkyl alcohol;
- i) aromatic alcohols, preferably an arylaliphatic-OH;
- j) triols or ethers, esters, or carbonates thereof, preferably triols or ethers, esters, or carbonates thereof, of the formula R70OCH2CH(OR71)CH2OR72, wherein R70, R71, and R72 are each independently selected from hydrogen, aliphatic, cycloaliphatic, aryl, arylaliphatic, acyl, or R71 and R72 together with the oxygens to which they are attached form a 5 membered ring;
- k) mono-esters, preferably mono-esters of the formula R77C(O)OR17, wherein R77 and R17 are each independently selected from an aliphatic, cycloaliphatic, aryl, or arylaliphatic group, each of which is optionally substituted with one or more hydroxyl groups;
- l) di-esters, preferably di-esters of the formula R19OC(O)C1-6alkylC(O)OR18, wherein R19 and R18 are each independently selected from an aliphatic, cycloaliphatic, aryl, or arylaliphatic group;
- m) tri-esters, preferably tri-esters of the formula
- wherein R10, R11 and R22 are each independently an aliphatic cycloaliphatic, aryl, or arylaliphatic group, and R21 is hydrogen or hydroxyl;
- n) nitriles, preferably nitriles of the formula R12—CN, wherein R12 is an aliphatic, cycloaliphatic, aryl, or arylaliphatic group;
- o) sulfoxides, preferably sulfoxides of the formula R13S(O)R14, wherein R13 and R14 are each independently selected from aliphatic, cycloaliphatic, aryl, arylaliphatic;
- and
- p) sulfones, preferably sulfones of the formula R15SO2R16, wherein R15 and R16 are each independently selected from aliphatic, cycloaliphatic, aryl, arylaliphatic.
The composition of claim, wherein the one or more solvents are selected from the group comprising dimethyllactamide, dipropylene glycol methyl ether, ethylene glycol phenyl ether, acetophenone, cyclohexanol, polyethylene glycol, polyethylene glycol methyl ether, dimethylsuccinate, dimethylglutarate, dimethyl adapate, butyl benzoate, triethylcitrate, glycerine carbonate, ethylene glycol, propylene glycol, 2-ethylhexyl lactate and benzyl alcohol.
The composition of claim, wherein the one or more solvents are selected from the group comprising dimethyllactamide, ethylene glycol phenyl ether, polyethylene glycol having a molecular weight of from 100 to 6000, a polyethylene glycol methyl ether having a molecular weight of from 100 to 1000, dimethylsuccinate, dimethylglutarate, dimethyl adapate, butyl benzoate, triethylcitrate, glycerine carbonate, 2-ethylhexyl lactate and benzyl alcohol.
The composition of claim, wherein one of the one or more solvents is dimethyllactamide.
The composition of claim, wherein the nucleophilicity coefficients of the hydroxyl groups or nitrogen-containing groups of the one or more solvents are less than 0.3 eV;
- wherein the nitrogen-containing groups are selected from ammonia, a primary amine group, a secondary amine group, or mixtures thereof.
The composition of claim, wherein the one or more solvents comprise a solvent system that is substantially non-aqueous.
The composition of claim, wherein the one or more solvents comprise a solvent system that comprises less than 5% w/w water.
The composition of claim, wherein when the molar ratio of total hydroxyl groups and nitrogen-containing groups to N-formylloline of the composition is less than about 10, and the nucleophilicity coefficients of the hydroxyl or nitrogen-containing groups of the composition are less than 0.6 eV, preferably 0.5 eV;
- wherein the nitrogen-containing groups are selected from ammonia, a primary amine group, a secondary amine group, or mixtures thereof.
A method for controlling one or more insect pests, the method comprising applying to a plant or its surroundings a composition as claimed in claim.
Dependencies are inferred from the claim text.