Stabilization of aldehydes and / or alcohols

Abstract

The present disclosure relates to a method for protecting aldehydes and / or alcohols from oxidation and / or conversion to acids, comprising contacting the aldehydes and / or alcohols with a protecting agent comprising a sulfur-containing compound.

Description

[Technical field]

[0001] The present disclosure relates to the protection of aldehydes and / or alcohols from oxidation and / or conversion to acids, e.g., during storage or use, as well as compositions comprising such protected aldehydes and / or alcohols and methods for their use. [Background technology]

[0002] Aldehydes and / or alcohols can be generated by, for example, O 2 Aldehydes are vulnerable to oxidation from aldehydes and are converted to carboxylic acids. See, for example, Morrison, RT; Boyd, RN (1992), Organic Chemistry (6th ed.). Aldehydes can also be decomposed by other mechanisms, such as aldol condensation, Tishchenko or Cannizarro reactions. Smith, MB March J. (2001), March Advanced Organic Chemistry (5th ed.). In products that contain aldehydes and / or alcohols as functional and active ingredients, it is necessary to protect these functional ingredients from conversion to the corresponding inactive forms. Summary of the Invention

[0003] The present disclosure describes a method for protecting aldehydes and / or alcohols against oxidation or decomposition to corresponding inactive compounds such as carboxylic acids. Thus, in a first aspect described herein, there is provided a method for protecting aldehydes and / or alcohols against oxidation and / or conversion to acids or other decomposition products, comprising contacting said aldehydes and / or alcohols with a protecting agent comprising a sulfur-containing compound.

[0004] In a further aspect, described herein are compositions comprising an aldehyde and / or alcohol and a protectant comprising a sulfur-containing compound that protects the aldehyde and / or alcohol from oxidation and / or conversion to an acid.

[0005] In a final aspect, described herein are methods of controlling or monitoring pests comprising distributing a composition described herein in a habitat for the pest and allowing the protected aldehydes and / or alcohols to control the pest.

[0006] Citation by reference All publications, patents, and patent applications mentioned in this specification are incorporated by reference to the same extent as if each individual publication, patent, or patent application was specifically and individually indicated to be incorporated by reference. In the event of a conflict between terms in this specification and terms in the incorporated references, the terms in this specification shall take precedence and control. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] The features and advantages of the methods and compositions described herein will become readily apparent to those of ordinary skill in the art from the following detailed description of the embodiments and examples.

[0008] definition The term "pheromone" is used herein to denote a chemical agent that elicits a social response in members of the same species. Pheromones are typically chemicals that can act like hormones outside the body of the secreting individual, influencing the behavior of the receiving individual. Pheromones include alarm pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology. Pheromones are used by many organisms, from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants, and ciliates use pheromones to communicate. The ecological function and evolution of pheromones is a major research topic in the field of chemical ecology.

[0009] The term "accelerated storage test" as used herein refers to a well-known protocol for investigating the stability of a particular composition. This protocol is described, for example, in a memorandum dated November 16, 2012 from the United States Environmental Protection Agency, Washington, DC 20460, with the subject "Accelerated Storage Stability and Corrosion Characteristics Study Protocol." The protocol evaluates product stability at 54°C ± 2°C for 14 days.

[0010] The term "Cannizzaro reaction," as used herein, is well known in the art and refers to an oxidation-reduction reaction involving the transfer of hydride from an aldehyde to another aldehyde: one aldehyde is oxidized to form an acid and the other is reduced to form an alcohol.

[0011] The term "Tishchenko reaction" is used herein to refer to a disproportionation reaction which is well known in the art and which can prepare an ester from two equivalents of an aldehyde.

[0012] Methods for protecting aldehydes and / or alcohols A first aspect described herein is a method for protecting aldehydes and / or alcohols from oxidation and / or conversion to acids with a protecting agent that includes a sulfur-containing protecting compound.

[0013] Aldehydes and / or the corresponding alcohols In the sections below, references to aldehydes apply mutatis mutandis to the corresponding alcohols.

[0014] Aldehydes suitable for protection are especially fatty aldehydes.In one embodiment of the disclosure, fatty aldehyde is a composition that is composed of or comprises a single fatty aldehyde.In another embodiment, such fatty aldehyde composition is composed of, contains, or comprises a small number of fatty aldehydes, for example a mixture of 2 to 5 fatty aldehydes.In yet another embodiment, such fatty aldehyde composition is composed of or comprises several fatty aldehydes, for example 6 or more fatty aldehydes.

[0015] The fatty aldehyde may be a saturated fatty aldehyde, an unsaturated fatty aldehyde. In one embodiment of the disclosure, the fatty aldehyde is a composition that contains only saturated fatty aldehydes. In another embodiment, such fatty aldehyde composition contains only unsaturated fatty aldehydes. In yet another embodiment of the disclosure, the aldehyde composition contains both saturated and unsaturated fatty aldehydes.

[0016] In one embodiment, the fatty aldehyde has a chain length of 8. In another embodiment, the fatty aldehyde has a chain length of 9. In another embodiment, the fatty aldehyde has a chain length of 10. In another embodiment, the fatty aldehyde has a chain length of 11. In another embodiment, the fatty aldehyde has a chain length of 12. In another embodiment, the fatty aldehyde has a chain length of 13. In another embodiment, the fatty aldehyde has a chain length of 14. In another embodiment, the fatty aldehyde has a chain length of 15. In another embodiment, the fatty aldehyde has a chain length of 16. In another embodiment, the fatty aldehyde has a chain length of 17. In another embodiment, the fatty aldehyde has a chain length of 18. In another embodiment, the fatty aldehyde has a chain length of 19. In another embodiment, the fatty aldehyde has a chain length of 20. In another embodiment, the fatty aldehyde has a chain length of 21. In another embodiment, the fatty aldehyde has a chain length of 22.

[0017] The fatty aldehyde may be branched or unbranched (i.e., linear or "straight chain"), In particular embodiments, the fatty aldehyde is unbranched.

[0018] In particular embodiments of the disclosure, the fatty aldehyde has a chain length of 12 to 16. In further embodiments of the disclosure, the fatty aldehyde is unbranched and has a chain length of 12 to 16. In even more particular embodiments of the disclosure, the fatty aldehyde is unbranched and has a chain length of 12. In another even more particular embodiment, the fatty aldehyde is unbranched and has a chain length of 14. In another even more particular embodiment, the fatty aldehyde is unbranched and has a chain length of 16.

[0019] In one embodiment of the present disclosure, the fatty aldehyde is a saturated fatty aldehyde.

[0020] In one embodiment of the disclosure, the fatty aldehyde is a saturated fatty aldehyde having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22.

[0021] In one embodiment of the disclosure, the fatty aldehyde is an unsaturated fatty aldehyde. The double bond of the unsaturated fatty aldehyde can have either E or Z configuration, except when the double bond is a terminal double bond. In one embodiment of the disclosure, the fatty aldehyde comprises one or more E-configuration double bonds. In one embodiment of the disclosure, the fatty aldehyde comprises one or more Z-configuration double bonds. In yet another embodiment, the fatty aldehyde comprises one or more E-configuration double bonds and one or more Z-configuration double bonds.

[0022] In some embodiments, the fatty aldehyde is an unsaturated fatty aldehyde. The unsaturated fatty aldehyde may be: (Z)-Δ3 unsaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(E)-Δ3 unsaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ5 unsaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ5 unsaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ6 unsaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(E)-Δ6 unsaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ7 unsaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(E)-Δ7 unsaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(Z)-Δ8 unsaturated fatty aldehydes having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(E)-Δ8 unsaturated fatty aldehydes having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ9 unsaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ9 unsaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ10 unsaturated fatty aldehydes having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ10 unsaturated fatty aldehydes having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ11 unsaturated fatty aldehydes having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(E)-Δ11 unsaturated fatty aldehydes having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(Z)-Δ12 unsaturated fatty aldehydes having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(E)-Δ12 unsaturated fatty aldehydes having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; -(Z)-Δ13 unsaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22; and -(E)-Δ13 unsaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0023] In some embodiments, the fatty aldehyde is an unsaturated fatty aldehyde having a carbon chain length of 12, for example: (Z)-Δ5 unsaturated fatty aldehydes with a carbon chain length of -12; (E)-Δ5 unsaturated fatty aldehydes with a carbon chain length of -12; (Z)-Δ6 unsaturated fatty aldehydes with a carbon chain length of -12; (E)-Δ6 unsaturated fatty aldehydes with a carbon chain length of -12; (Z)-Δ7 unsaturated fatty aldehydes with a carbon chain length of -12; (E)-Δ7 unsaturated fatty aldehydes with a carbon chain length of -12; (Z)-Δ8 unsaturated fatty aldehydes with a carbon chain length of -12; (E)-Δ8 unsaturated fatty aldehydes with a carbon chain length of -12; (Z)-Δ9 unsaturated fatty aldehydes with a carbon chain length of -12; (E)-Δ9 unsaturated fatty aldehydes with a carbon chain length of -12; (Z)-Δ10 unsaturated fatty aldehydes with a carbon chain length of -12; (E)-Δ10 unsaturated fatty aldehydes with a carbon chain length of -12; (Z)-Δ11 unsaturated fatty aldehydes having a carbon chain length of -12; and An (E)-Δ11 unsaturated fatty aldehyde having a carbon chain length of -12.

[0024] In some embodiments, the fatty aldehyde is an unsaturated fatty aldehyde having a carbon chain length of 14, for example: (Z)-Δ5 unsaturated fatty aldehydes with a carbon chain length of -14; (E)-Δ5 unsaturated fatty aldehydes with a carbon chain length of -14; (Z)-Δ6 unsaturated fatty aldehydes with a carbon chain length of -14; (E)-Δ6 unsaturated fatty aldehydes with a carbon chain length of -14; (Z)-Δ7 unsaturated fatty aldehydes with a carbon chain length of -14; (E)-Δ7 unsaturated fatty aldehydes with a carbon chain length of -14; (Z)-Δ8 unsaturated fatty aldehydes with a carbon chain length of -14; (E)-Δ8 unsaturated fatty aldehydes with a carbon chain length of -14; (Z)-Δ9 unsaturated fatty aldehydes with a carbon chain length of -14; (E)-Δ9 unsaturated fatty aldehydes with a carbon chain length of -14; (Z)-Δ10 unsaturated fatty aldehydes with a carbon chain length of -14; (E)-Δ10 unsaturated fatty aldehydes with a carbon chain length of -14; (Z)-Δ11 unsaturated fatty aldehydes with a carbon chain length of -14; (E)-Δ11 unsaturated fatty aldehydes with a carbon chain length of -14; (Z)-Δ12 unsaturated fatty aldehydes with a carbon chain length of -14; (E)-Δ12 unsaturated fatty aldehydes with a carbon chain length of -14; (Z)-Δ13 unsaturated fatty aldehydes having a carbon chain length of -14; and An (E)-Δ13 unsaturated fatty aldehyde with a carbon chain length of -14.

[0025] In some embodiments, the fatty aldehyde is an unsaturated fatty aldehyde having a carbon chain length of 16, for example: (Z)-Δ5 unsaturated fatty aldehydes with a carbon chain length of -16; (E)-Δ5 unsaturated fatty aldehydes with a carbon chain length of -16; (Z)-Δ6 unsaturated fatty aldehydes with a carbon chain length of -16; (E)-Δ6 unsaturated fatty aldehydes with a carbon chain length of -16; (Z)-Δ7 unsaturated fatty aldehydes with a carbon chain length of -16; (E)-Δ7 unsaturated fatty aldehydes with a carbon chain length of -16; (Z)-Δ8 unsaturated fatty aldehydes with a carbon chain length of -16; (E)-Δ8 unsaturated fatty aldehydes with a carbon chain length of -16; (Z)-Δ9 unsaturated fatty aldehydes with a carbon chain length of -16; (E)-Δ9 unsaturated fatty aldehydes with a carbon chain length of -16; (Z)-Δ10 unsaturated fatty aldehydes with a carbon chain length of -16; (E)-Δ10 unsaturated fatty aldehydes with a carbon chain length of -16; (Z)-Δ11 unsaturated fatty aldehydes with a carbon chain length of -16; (E)-Δ11 unsaturated fatty aldehydes with a carbon chain length of -16; (Z)-Δ12 unsaturated fatty aldehydes with a carbon chain length of -16; (E)-Δ12 unsaturated fatty aldehydes with a carbon chain length of -16; (Z)-Δ13 unsaturated fatty aldehydes having a carbon chain length of -16; and An (E)-Δ13 unsaturated fatty aldehyde with a carbon chain length of -16.

[0026] For example, the fatty aldehyde is an (E)7, (Z)9 unsaturated fatty aldehyde having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22. In some embodiments, the fatty aldehyde is an (E)3, (Z)8, (Z)11 unsaturated fatty aldehyde having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22, such as 14. In some embodiments, the fatty aldehyde is an (Z)9, (E)11, (E)13 unsaturated fatty aldehyde having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21, or 22. In some embodiments, the fatty aldehyde is a (Z)11,(Z)13 unsaturated fatty aldehyde having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21, or 22. In some embodiments, the fatty aldehyde is a (Z)9,(E)12 unsaturated fatty aldehyde having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22. In some embodiments, the fatty aldehyde is an (E)7,(E)9 unsaturated fatty aldehyde having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22. In some embodiments, the fatty aldehyde is an (E)8, (E)10 unsaturated fatty aldehyde having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22.

[0027] In another embodiment, the fatty aldehyde is an (E)7, (Z)9 unsaturated fatty aldehyde having a carbon chain length of 14. In another embodiment, the unsaturated fatty aldehyde is an (E)3, (Z)8, (Z)11 unsaturated fatty aldehyde having a carbon chain length of 14. In another embodiment, the unsaturated fatty aldehyde is a (Z)9, (E)11, (E)13 unsaturated fatty aldehyde having a carbon chain length of 14. For example, the fatty aldehyde is an (E)7, (Z)9 unsaturated fatty aldehyde having a carbon chain length of 12. In another embodiment, the unsaturated fatty aldehyde is an (E)3, (Z)8, (Z)11 unsaturated fatty aldehyde having a carbon chain length of 12. In another embodiment, the unsaturated fatty aldehyde is a (Z)9, (E)11, (E)13 unsaturated fatty aldehyde having a carbon chain length of 12. In another embodiment, the unsaturated fatty aldehyde is an (E)8, (E)10 unsaturated fatty aldehyde having a carbon chain length of 12. In another embodiment, the unsaturated fatty aldehyde is an (E)7, (E)9 unsaturated fatty aldehyde having a carbon chain length of 11. In another embodiment, the unsaturated fatty aldehyde is a (Z)11, (Z)13 unsaturated fatty aldehyde having a carbon chain length of 16. In another embodiment, the unsaturated fatty aldehyde is a (Z)9, (E)12 unsaturated fatty aldehyde having a carbon chain length of 14.

[0028] In some embodiments, the fatty aldehyde is (Z9,E12)-tetradecadien-1-al. Microbial cell factories and methods for obtaining the corresponding alcohol (Z9,E12)-tetradecadien-1-ol from yeast cells are described in detail in application EP21183447.8, entitled "Methods and yeast cells for production of desaturated compounds", filed on July 2, 2021 by the same applicant.

[0029] In some embodiments, the fatty aldehyde is (Z11,Z13)-hexadecadien-1-al. Microbial cell factories and methods for obtaining the corresponding alcohol (Z11,Z13)-hexadecadien-1-ol from yeast cells are described in detail in application EP21183459.3 entitled "Methods and yeast cells for production of desaturated compounds", filed on July 2, 2021 by the same applicant.

[0030] In some embodiments, the fatty aldehyde is (E8,E10)-dodecadien-1-al. Microbial cell factories and methods for obtaining the corresponding alcohol (E8,E10)-hexadecadien-1-ol from yeast cells are described in detail in application WO2021 / 123128.

[0031] In some embodiments, the fatty aldehyde is (Z11)-hexadecen-1-al. Microbial cell factories and methods for obtaining the corresponding alcohol (Z11)-hexadecen-1-ol from yeast cells are described in detail in application WO2016 / 207339. This alcohol can be converted to (Z11)-hexadecen-1-al using the methods disclosed herein.

[0032] In particular embodiments of the disclosure, the fatty aldehyde has a double bond at the 9, 11 or 13 positions, or at the 9 and 11 positions, or at the 11 and 13 positions; or at the 9 or 12 positions, or at the 9 and 12 positions. In even more particular embodiments of the disclosure, the fatty aldehyde has a chain length of 12 and a double bond at the 9 or 11 positions, or at the 9 and 11 positions; or at the 9 or 12 positions; or at the 9 and 12 positions; or at the 9 and 12 positions. In another more particular embodiment of the disclosure, the fatty aldehyde has a chain length of 14 and a double bond at positions 9 or 11, or a double bond at positions 9 and 11. In another more particular embodiment of the disclosure, the fatty aldehyde has a chain length of 16 and a double bond at positions 9 or 11, or a double bond at positions 9 and 11. In another embodiment, the fatty aldehyde has a chain length of 16 and a double bond at positions 11 or 13, or a double bond at positions 11 and 13. In another embodiment, the fatty aldehyde has a chain length of 12 and a double bond at positions 8 or 10, or a double bond at positions 8 and 10.

[0033] In certain embodiments, the fatty aldehyde is selected from the group consisting of tetradecane-1-al, pentadecane-1-al, hexadecan-1-al, pentadecen-1-al, (Z)-9-hexadecen-1-al, (Z)-11-hexadecen-1-al, (7E,9E)-undeca-7,9-dien-1-al, (11Z,13Z)-hexadecadien-1-al, (9Z,12E)-tetradecadien-1-al, and (8E,10E)-dodecadien-1-al.

[0034] In certain embodiments, the fatty aldehyde is (Z)-11-hexadecenal or (Z)-9-tetradecenal.

[0035] The fatty aldehydes can be present in a composition consisting solely of fatty aldehydes, or it can include fatty aldehydes and other compounds. In one embodiment of the disclosure, such a fatty aldehyde composition comprises 5-10 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises 10-20 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises 20-30 wt% of one or more fatty aldehydes.

[0036] In another embodiment, the fatty aldehyde composition comprises 30-40 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises 40-50 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises 50-60 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises 60-70 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises 70-80 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises 80-90 wt% of one or more fatty aldehydes.

[0037] In another embodiment, the fatty aldehyde composition comprises 90-100 wt% of one or more fatty aldehydes. In particular embodiments of the disclosure, the fatty aldehyde composition comprises in the range of 50-100% of one or more fatty aldehydes. In even more particular embodiments, the fatty aldehyde composition comprises in the range of 60-100% of one or more fatty aldehydes.

[0038] In one embodiment of the disclosure, the fatty aldehyde composition comprises at least 30 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises at least 35 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises at least 40 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises at least 45 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises at least 50 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises at least 55 wt% of one or more fatty aldehydes. In another embodiment, the fatty aldehyde composition comprises at least 60 wt% of one or more fatty aldehydes. In a particular embodiment, the fatty aldehyde composition comprises at least 70 wt% of one or more fatty aldehydes. In another particular embodiment, the fatty aldehyde composition comprises at least 80 wt% of one or more fatty aldehydes. In another particular embodiment, the fatty aldehyde composition comprises at least 90 wt% of one or more fatty aldehydes.

[0039] In additional or alternative embodiments, the fatty aldehyde is an aliphatic fatty aldehyde. Such fatty aldehydes and / or alcohols can contain 5-20 carbons, such as 9-18 carbons, such as 12-18 carbons. In particularly attractive embodiments, the number of carbons in the aliphatic aldehydes and / or alcohols is 12, 14, 16, or 18 carbons. The aldehyde group is suitably located at C1 in the aldehyde. In other embodiments, the aldehydic group is unsaturated and contains one or more double bonds. Particularly attractive aldehydes have a double bond at the 9-position ((Z)-9) and / or at the 11-position ((Z)-11). Particular aldehydes of interest contain 12, 14, 16, or 18 carbons and have a double bond at the 9-position and / or at the 11-position, which are of particular interest. Such aldehydes may have pheromone properties and may provide a non-toxic means for monitoring, regulating and / or controlling pests in crop fields that are sensitive to such pheromones. In further additional or alternative embodiments, the aldehyde comprises two or three or more different aldehydes. In particular, the aldehyde is a pheromone, e.g., an insect pheromone.

[0040] In some embodiments, the aldehyde and / or alcohol contains 16 carbons and has a double bond at the 9-position and / or the 11-position. In some embodiments, the method includes protecting a plurality of fatty aldehydes, a plurality of fatty alcohols, and / or combinations thereof. In some embodiments, the plurality of fatty aldehydes and / or alcohols includes two or three or more different aldehydes and / or alcohols. In some embodiments, the fatty aldehyde and / or fatty alcohol is a pheromone.

[0041] Protective Agent The protective agent described herein comprises a sulfur-containing compound. The sulfur in the protective agent may be conjugated or unconjugated, for example, the sulfur in the protective agent may be conjugated sulfur. In some embodiments, the protective agent comprises a thiol, which may be a heterocyclic thiol and / or an aromatic thiol. In more specific embodiments, the protective agent comprises a compound selected from zinc pyrithione, 5-amino-1,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, 2-mercapto-benzimidazole, 2-mercapto-1-methylimidazole, and sodium pyrithione.

[0042] The aldehyde and / or alcohol are suitably contacted with the protectant by mixing the aldehyde and / or alcohol with the protectant to form a composition.

[0043] In some embodiments, the protective agent is a corrosion inhibitor. In some embodiments, the corrosion inhibitor indirectly helps stabilize the aldehyde, for example by preventing metal ions from catalyzing the decomposition of the aldehyde. In some embodiments, the protective agent comprises a sulfur-containing compound and is a corrosion inhibitor. In some embodiments, the corrosion inhibitor is a compound selected from zinc pyrithione, 5-amino-1,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, 2-mercapto-benzimidazole, 2-mercapto-1-methylimidazole, and sodium pyrithione.

[0044] Stabilizers In some embodiments, the protectants described herein are used in combination with one or more stabilizers, for example, the stabilizers are selected from the group consisting of: antioxidants, radical scavengers, pH adjusters, buffers, UV stabilizers, chelators, and any combination thereof. In some embodiments, the stabilizer is selected from the group consisting of Sumisorb (CAS 3896-11-5); BHT (CAS 109-99-9), TBHQ (CAS 1948-33-0), tocopherol (CAS 10191-41-0), dimethylethanolamine (CAS 287476-09-9), Tinuvin 770 (CAS 52829-07-9), Tinuvin P (CAS 2440-22-4), morpholine (CAS 110-91-8), sodium hydroxide (CAS 1310-73-2), propyl gallate (CAS 121-79-9), BHA (CAS 121-00-6), and any combination thereof. Thus, in some embodiments, the protectant is sodium pyrithione used in combination with the stabilizers disclosed herein.

[0045] Stabilizers that can be used in combination with the protectants of the present disclosure can stabilize using one or more mechanisms, for example, by acting as antioxidants, radical scavengers, pH adjusters, buffers, UV stabilizers, chelators, or any combination thereof.

[0046] The protectants disclosed herein can be used in combination with one or more of the following stabilizers, the effects of which are outlined in the table below: [Table 1]

[0047] composition Further aspects described herein are compositions comprising an aldehyde and / or alcohol and a protecting agent as described above, where the protecting agent protects the aldehyde and / or alcohol from oxidation and / or conversion to an acid. In some embodiments, the protecting agent protects the aldehyde and / or alcohol of the present disclosure from degradation.

[0048] In some embodiments, the decomposition occurs by one or more processes selected from the following: oxidation, aldol reaction, aldol condensation, hemiacetal, acetal formation, Cannizarro reaction, and Tishchenko reaction.

[0049] In some embodiments, the degradation occurs by oxidation.

[0050] In some embodiments, the degradation occurs by oxidation of the fatty aldehydes and / or fatty alcohols of the present disclosure to acids.

[0051] Such compositions can further comprise one or more additional carriers, agents, additives and / or excipients.In some embodiments, the composition comprises 10mg or more of protective agent / gram aldehyde and / or alcohol, such as 20mg or more, such as 30mg or more, such as 50mg or more, such as 100mg or more.In addition or alternatively, the composition can comprise at least 0.5wt% aldehyde and / or alcohol, such as at least 1.0wt%, such as at least 1.5wt%, such as at least 3.0wt%, such as at least 5.0wt%, such as at least 10.0wt%, such as at least 25.0wt%.

[0052] Additionally, such compositions can include compounds, such as oxidizing agents, catalysts, ligands and / or bases or combinations thereof that promote oxidation. Such compounds may be residues from processes in which aldehydes and / or alcohols are produced.

[0053] In some embodiments, the catalyst is an aminoxyl radical compound, i.e., NO · In a further embodiment of the present disclosure, the aminoxyl radical compound is a dialkylaminoxyl radical compound. In a further embodiment, the aminoxyl radical compound is a piperidine N-oxide or a derivative thereof. In yet another embodiment, the aminoxyl radical compound is a substituted piperidine N-oxide. In yet another embodiment, the aminoxyl radical compound is (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) or a derivative thereof. In some embodiments, the aminoxyl radical compound is selected from the group consisting of TEMPO, (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxyl (4-OH-TEMPO), 4-acetamido-TEMPO, 4-hydroxy-TEMPO benzoate, 4-amino-TEMPO, 2-azaadamantane-N-oxyl, 9-azabicyclo[3.3.1]nonane-N-oxyl, 4-carboxy-TEMPO, 4-maleimido-TEMPO, 4-methoxy-TEMPO, 1-methyl-2-azaadamantane-N-oxyl, 4-oxo-TEMPO, and polymers functionalized with any of the aminoxyl radical compounds. In particular embodiments of the present disclosure, the aminoxyl radical compound is selected from the group consisting of TEMPO or (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxyl (4-OH-TEMPO). It is contemplated that the aminoxyl radical compounds are part of a catalytic cycle that affects the oxidation of the fatty alcohol compositions of the present disclosure. TEMPO and its derivatives described herein act as a catalyst for the oxidation, while the oxidizing agent is O 2 However, as used herein, TEMPO and derivatives can also be considered to be "oxidizing agents."

[0054] In additional or alternative embodiments, the catalyst comprises a copper(I) source, such as, for example, a copper(I) salt. The copper(I) source can be a material or mixture of materials that includes a copper(I) compound. Examples include, among others, copper(I) chloride, copper(I) bromide, copper(I) iodide, copper(I) cyanide, copper(I) oxide, copper(I) trifluoromethanesulfonate, tetrakis(acetonitrile)copper(I) tetrafluoroborate, tetrakis(acetonitrile)copper(I) tetraphenylborate, tetrakis(acetonitrile)copper(I) hexafluorophosphate, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, copper(I) sulfide, copper(I) thiocyanate, Cu[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]Cl, Cu[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]Br, CuBr(1,10-phenanthroline). 2 , CuCl(1,10-phenanthroline)] 2 , CuI(1,10-phenanthroline) 2 , copper(I) trifluoroacetate, [Cu(PPh 3 ) 3 ]Br, [Cu(PPh 3 ) 3 ]F, [Cu(PPh 3 ) 3 ]Cl, Cu(OCOR 2 ), Cu(SR 2 ), Cu(SR 2 2 )Br, Cu(SR 2 2 )Cl, Cu(SR 2 2 )I, Cu(OSO 2 R 2 ), CuOR 2 , where R 2 is alkyl, preferably C 1 -C 20 Alkyl (optionally substituted with one or more aryl, alkoxy and aryloxy) and aryl, preferably C 5 -C 7aryl (optionally substituted with one or more alkyl, aryl, alkoxy and aryloxy) and mixtures thereof. In addition, the copper(I) source can be a substance or mixture of substances containing copper in any other oxidation state, provided that it can be converted by reduction or oxidation means, chemically or electrochemically, to copper in the +1 oxidation state. In a particular embodiment, the copper(I) source comprises copper present in the +1 oxidation state.

[0055] In particular embodiments, the composition also includes a counterion of the copper(I) source, i.e., a negatively charged ion such as triflate, tetrafluoroborate, hexafluorophosphate, or a halide.

[0056] The composition may further comprise a ligand coordinated to the copper catalyst, including, but not limited to, tetrakisacetonitrile copper(I) triflate, tetrakisacetonitrile copper(I) tetrafluoroborate, tetrakisacetonitrile copper(I) hexafluorophosphate, tetrakisacetonitrile copper(I) halide, CuBr(1,10-phenanthroline). 2 , CuCl(1,10-phenanthroline)] 2 , and CuCl(1,10-phenanthroline) 2 In some embodiments, the catalyst is from the group of tetrakisacetonitrile copper(I) triflate, tetrakisacetonitrile copper(I) tetrafluoroborate, tetrakisacetonitrile copper(I) hexafluorophosphate, and tetrakisacetonitrile copper(I) halide.

[0057] In other embodiments, the catalyst can include a copper(II) compound and a reducing agent capable of reducing copper(ii) to copper(I). In addition, the composition can include a counterion of Cu(II). Thus, in some embodiments, the catalyst is selected from the group of copper(II) triflate, copper(II) tetrafluoroborate, copper(II) hexafluorophosphate, copper(II) bromide, copper(II) chloride, copper(II) iodide, and copper(II) perchlorate. The reducing agent can reduce copper(II) to copper(I) and can be either an organic or inorganic reducing agent. In one embodiment, the reducing agent is selected from the group consisting of copper metal, zinc metal, aluminum metal, sodium bisulfite, formic acid, salts of formic acid, oxalic acid, and salts of oxalic acid. The metal-based reducing agent can conveniently be in powder, pellets, shavings, or otherwise finely divided form.

[0058] When the compositions described herein include a ligand coordinated to copper(I), such ligand can be coordinated to Cu(I) through nitrogen, oxygen, phosphorus, or other atoms having lone pairs, for example, through a moiety selected from the group consisting of pyridine, triarylphosphine, diarylphosphine, amine, imidazole, pyrazole, pyrrole, triazole, tetrazole, imine, enamine, phenol. Additionally or alternatively, the ligand can be monodentate, bidentate, or polydentate, for example, a polydentate ligand coordinated with three or more atoms. The ligand can include a single type of ligand, a mixture of two or more types of ligand. More particularly, the ligand can be selected from the group consisting of DETA, PMDETA, TETA, HMTETA, Me 6 TREN, Cyclam, Me 6The ligand may be from the group of cyclam, DMCBCy, bpy, dNbpy, 1,10-Phen, tpy, tNtpy, BPMPrA, BPMOA, BPMODA, TPMA, and TPEA. In other embodiments, the ligand is a secondary amine, for example, a secondary amine with a bulky substituent (i.e., reducing the nucleophilicity of the amine). In one embodiment of the present disclosure, the ligand is a bidentate nitrogen ligand. In one embodiment, the ligand comprises a 2,2'-bipyridine moiety or a 2,2'-bipyrimidine moiety. Additionally or alternatively, the ligand may be from the group of 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dimethyl-2,2'-bipyridine 2,2'-bipyrimidine, 2,2'-bipyridine-4,4'-dicarboxylic acid or ester thereof, 2,2'-bipyridine-5,5'-dicarboxylic acid or ester thereof.

[0059] Additionally or alternatively, the composition may also include a base, such as a nitrogen base, for example, a Schiff base or an oxygen base. Such bases include those selected from the following. In one embodiment of the present disclosure, the base is selected from the group consisting of 1-methylimidazole, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,1,3,3-tetramethylguanidine, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, and potassium t-butoxide. In one embodiment of the present disclosure, the base is selected from the group consisting of 1-methylimidazole, potassium tert-butoxide, or 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU).

[0060] In yet another embodiment, the compositions described herein can include a carrier that promotes the controlled, slow and / or delayed release of aldehydes and / or alcohols.Such carriers can suitably be polymeric substrates or microporous solids.Suitable polymeric substrates include one or more materials selected from plastics, wax emulsions, oil emulsions, microcapsules or microparticles.Interesting microparticles for this purpose are described, for example, in US10,271,547, while other interesting polymeric substrates are described in US2008 / 0254083.Suitable microporous solids include zeolites, as described in Munoz-Pallares et al; J. Agric. Food Chem. 2001, 49, 4801-4807.

[0061] In some embodiments, the compositions provided include copper (Cu), e.g., Cu + and / or Cu 2+ In some embodiments, the composition comprises 40 ppm or less Cu. In some embodiments, the composition comprises 10 ppm to 40 ppm Cu, such as 10 ppm to 30 ppm, such as 10 ppm to 20 ppm, such as 10 ppm Cu.

[0062] How to use A further embodiment described herein is a method for controlling or monitoring pests, in which the composition described herein is distributed in the habitat of the pest (infested by the pest) and allows the protected aldehyde and / or alcohol to control the pest.Such habitat (infested by the pest) is preferably a field or forest or any habitat that is infested by the pest or susceptible to becoming infested by the pest.The susceptible pests controlled or monitored by said method are typically arthropods, such as insects, or other animals that use aldehyde and / or alcohol to induce a social response in members of the same or similar species.

[0063] Further itemized embodiments The following sub-embodiments are further described herein: Item 1. A method for protecting an aldehyde and / or alcohol from oxidation and / or conversion to an acid, comprising contacting the aldehyde and / or alcohol with a protecting agent comprising a sulfur-containing compound. Item 2. The method of item 1, wherein the aldehyde and / or alcohol is a fatty aldehyde and / or alcohol. Item 3. The method of any preceding item, wherein the fatty aldehyde and / or alcohol is an aliphatic fatty aldehyde and / or alcohol. Item 4. The method of items 2-3, wherein the fatty aldehyde and / or alcohol contains 5-20 carbons, such as 9-18 carbons, such as 12-18 carbons, such as 12, 14, 16, or 18 carbons. Item 5. The method of any preceding item, wherein the aldehyde and / or alcohol groups are C1 aldehydes and / or C1 alcohols. Item 6. The method of any preceding item, wherein the aldehyde and / or alcohol are unsaturated and contain one or more double bonds. Item 7. The method of any preceding item, wherein the aldehyde and / or alcohol has a double bond at the 9-position ((Z)-9) and / or at the 11-position ((Z)-11). Item 8. The method of any preceding item, wherein the aldehyde and / or alcohol contains 16 carbons and has a double bond at the 9-position and / or the 11-position. Item 9. The method of any preceding item, wherein the aldehyde and / or alcohol comprises two or three or more different aldehydes and / or alcohols. Item 10. The method of any preceding item, wherein the aldehyde and / or alcohol is a pheromone. Item 11. The method of item 10, wherein the pheromone is an arthropod pheromone, optionally an insect pheromone. Item 12. The method of any preceding item, wherein the sulfur in the protective agent is conjugated sulfur. Item 13. The method of any preceding item, wherein the protecting agent comprises a thiol. Item 14. The method of item 13, wherein the thiol is a heterocyclic thiol. Item 15. The method of Item 13, wherein the thiol is an aromatic thiol. Item 16. The method of any preceding item, wherein the protecting agent comprises a compound selected from zinc pyrithione, 5-amino-1,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, 2-mercapto-benzimidazole, 2-mercapto-1-methylimidazole and sodium pyrithione. Item 17. The method of any preceding item, wherein the aldehyde and / or alcohol is contacted with the protectant by mixing the aldehyde and / or alcohol with the protectant to form the composition. Item 18. A composition comprising an aldehyde and / or alcohol and a protecting agent comprising a sulfur-containing compound that protects the aldehyde and / or alcohol from oxidation and / or conversion to an acid. Item 19. The composition of item 18, further comprising one or more additional carriers, agents, additives and / or excipients. Item 20. The composition according to items 18 to 19, wherein the aldehyde and / or alcohol is the aldehyde and / or alcohol of items 5 to 11. Item 21. The composition according to Items 18 to 20, wherein the protective agent is the protective agent according to Items 12 to 16. Item 22. The composition of items 18 to 21, comprising at least 10 mg of a protective agent / gram aldehyde and / or alcohol. Item 23. The composition of items 18 to 22, comprising at least 0.5 wt% of an aldehyde and / or alcohol. Item 24. The composition of items 18 to 23, further comprising an oxidizing agent or a catalyst that promotes oxidation. Item 25. The composition of item 24, wherein the oxidizing agent is 4-hydroxy-TEMPO. Item 26. The composition of item 24, wherein the catalyst comprises Cu. Item 27. The composition of items 18 to 26, further comprising a carrier that promotes the slow release of the aldehyde and / or alcohol. Item 28. The composition of item 27, wherein the carrier is a polymeric matrix or a microporous solid. Item 29. The composition of item 28, wherein the polymeric substrate is one or more materials selected from a plastic, a wax emulsion, an oil emulsion, or a microcapsule. Item 30. The composition of item 28, wherein the microporous solid is a zeolite. Item 31. A method for controlling or monitoring pests, comprising distributing the composition of items 18 to 30 in a habitat for the pests and allowing the protected aldehyde and / or alcohol to control the pests. Item 32. The method of item 31, wherein the habitat is a field and the pest is an insect.

[0064] Working Example Example 1 A mixture of aldehydes containing: (Z)-9-hexadecenal, (Z)-11-hexadecenal, hexadecanal, (Z)-11-hexadecen-1-ol, (Z)-11-hexadecenoic acid, and 40 ppm Cu, was added with the additives shown in Table 1 below. The mixture was thoroughly mixed and heated uncapped in an oven at 55° C. for 14 days as an accelerated storage test. As can be seen in Table 1, the concentration of aldehydes was significantly reduced in the sample without additive, while the concentration of (Z)-11-hexadecenoic acid increased. Surprisingly, many of the compounds, especially sodium pyrithione, were particularly efficient at inhibiting decomposition. [Table 2]

[0065] Example 2 To a mixture of aldehydes containing: (Z)-9-hexadecenal, (Z)-11-hexadecenal, hexadecanal, (Z)-11-hexadecen-1-ol, (Z)-11-hexadecenoic acid and 10 ppm Cu, in the composition listed in Table 2 below, were added the additives listed in the table below. The mixture was thoroughly mixed and heated in an oven at 55°C for 14 days, uncapped, as an accelerated storage test. As can be seen in the table, the concentration of aldehydes was significantly reduced in the sample without additive, while the concentration of (Z)-11-hexadecenoic acid increased. Surprisingly, many of the compounds, especially sodium pyrithione, were very efficient at inhibiting the decomposition. [Table 3]

[0066] Example 3 To a mixture of aldehydes containing: 4-hydroxy-TEMPO (4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl), (Z)-10-pentenal, (Z)-9-hexadecenal, (Z)-11-hexadecenal, hexadecanal, (Z)-11-hexadecen-1-ol, (Z)-11-hexadecenoic acid and 10 ppm copper, in the compositions listed in Table 3 below, the additives in the table below were added to 1%. The mixtures were mixed thoroughly and heated in an oven at 55° C. for 14 days, uncapped. As can be seen in the table, the concentration of aldehydes was significantly reduced in the sample without additive, while the concentration of (Z)-11-hexadecenoic acid was increased. Surprisingly, a number of compounds are particularly effective at inhibiting acid formation and the decomposition of aldehydes, in particular: zinc pyrithione, 5-amino-1,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 2-thiazoline-2-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, 2-mercapto-benzimidazole, 2-mercapto-1-methylimidazole and sodium pyrithione. [Table 4]

[0067] Example 4 To a mixture of aldehydes containing: 4-hydroxy-TEMPO (4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl), (Z)-10-pentenal, (Z)-9-hexadecenal, (Z)-11-hexadecenal, hexadecanal, (Z)-11-hexadecen-1-ol, and (Z)-11-hexadecenoic acid, in the compositions listed in Table 4 below, the additives in the table below were added to 1%. The mixtures were mixed thoroughly and heated in an oven at 55° C. for 14 days, uncapped. As can be seen in the table, the concentration of aldehydes was significantly reduced in the sample without additive, while the concentration of (Z)-11-hexadecenoic acid was increased. Surprisingly, a number of compounds are particularly effective at inhibiting acid formation and decomposition of aldehydes, namely; zinc pyrithione, 5-amino-1,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 2-thiazoline-2-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, 2-mercapto-1-methylimidazole and sodium pyrithione. [Table 5]

[0068] Example 5 (Stability test at 5°C and 54°C) Two standard samples of 14 g of the pheromone mixture containing the compositions listed in Table 5 were sealed in 25 ml HDPE vials. Two additional samples containing 14 g of the pheromone mixture and doped with the protectant sodium pyrithione (NaPyr) 0.2 wt % (Sigma Aldrich CAS No.: 3811-73-2 95% purity) were similarly prepared.

[0069] One standard sample (sample 1) and one stabilized sample (sample 2) were placed in an oven and kept at 54° C. for 14 days.

[0070] Another standard sample (sample 3) and a stabilized sample (sample 4) were placed in a refrigerator at 5° C. for 17 days.

[0071] The composition of the pheromone mixture was investigated by gas chromatography after the aging experiment and the results are listed in Table 5. [Table 6]

[0072] conclusion This example demonstrates that pheromone samples containing a protectant, e.g., sodium pyrithione (2 and 4), resulted in less aldehyde decomposition than corresponding samples without such a protectant (1 and 3). Furthermore, this example demonstrates that this effect was observed in both cold (5°C) and warm (54°C) environments, demonstrating that the protectant is effective regardless of temperature.

Claims

1. A method for protecting fatty aldehydes and / or fatty alcohols from decomposition, comprising contacting the aldehyde and / or alcohol with a protective agent comprising a sulfur-containing compound, wherein the fatty aldehyde and / or fatty alcohol comprises 12 to 18 carbon atoms and one or more double bonds at position 9 ((Z)-9) and / or position 11 ((Z)-11), and the protective agent comprises conjugated sulfur. Optionally, the decomposition may occur by one or more processes selected from oxidation, aldol reaction, aldol condensation, hemiacetal formation, acetal formation, Cannizerro reaction, or Tishchenko reaction. For example, the decomposition occurs by the oxidation of the fatty aldehyde and / or fatty alcohol to an acid. method.

2. (a) The aldehyde and / or alcohol comprises 16 carbon atoms and has a double bond at the 9th and / or 11th positions, or (b) The aldehyde and / or alcohol is a pheromone. The method according to claim 1.

3. The method described above includes protecting multiple fatty aldehydes, multiple fatty alcohols, and / or combinations thereof. Optionally, the plurality of fatty aldehydes and / or alcohols include two or three or more different aldehydes and / or alcohols. The method according to claim 1 or 2.

4. The method according to any one of claims 1 to 3, wherein the fat aldehyde is an arthropod pheromone.

5. The protective agent is a corrosion inhibitor, and / or The protective agent comprises a thiol, wherein the thiol is a heterocyclic thiol or an aromatic thiol. The method according to any one of claims 1 to 4.

6. The method according to claim 5, wherein the thiol is a heterocyclic thiol or an aromatic thiol.

7. The method according to any one of claims 1 to 6, wherein the protective agent comprises a compound selected from zinc pyrithione, 5-amino-1,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, 2-mercapto-benzimidazole, 2-mercapto-1-methylimidazole, and sodium pyrithione.

8. The method according to any one of claims 1 to 7, wherein the aldehyde is brought into contact with the protective agent by mixing the aldehyde with the protective agent to form a composition.

9. A composition comprising a fatty aldehyde, optionally a pheromone, and a protective agent comprising a sulfur-containing compound to protect the aldehyde from decomposition, wherein the fatty aldehyde comprises 12 to 18 carbon atoms and has one or more double bonds at position 9 ((Z)-9) and / or position 11 ((Z)-11), and the protective agent comprises conjugated sulfur. Optionally, the decomposition may occur by one or more processes selected from oxidation, aldol reaction, aldol condensation, hemiacetal formation, acetal formation, Cannizerro reaction, or Tishchenko reaction. For example, the decomposition occurs by the oxidation of the fatty aldehyde and / or fatty alcohol to an acid. Further comprising one or more additional carriers, active substances, additives and / or excipients, composition.

10. (a) comprising at least 10 mg of the protective agent / gram aldehyde and / or alcohol, and / or (b) containing at least 0.5 wt% aldehyde and / or alcohol, The composition according to claim 9.

11. Further comprising an oxidizing agent or a catalyst that promotes oxidation, For example, containing Cu in amounts of 40 ppm or less, 10 ppm to 40 ppm, for example 10 ppm to 30 ppm, for example 10 ppm to 20 ppm, for example 10 ppm. The composition according to claim 9 or 10.

12. The composition according to claim 11, wherein the oxidizing agent is 4-hydroxy-TEMPO.

13. The composition according to claim 11, wherein the catalyst comprises Cu.

14. The composition according to claim 13, wherein the composition contains Cu in an amount of 40 ppm or less, 10 ppm to 40 ppm, for example, 10 ppm to 30 ppm, for example, 10 ppm to 20 ppm.

15. The composition according to any one of claims 9 to 11, further comprising a stabilizer selected from the group consisting of: antioxidants, radical scavengers, pH adjusters, buffers, UV stabilizers, chelators, and any combination thereof.

16. The composition according to any one of claims 9 to 15, further comprising a stabilizer selected from the group consisting of: Sumisorb (CAS 3896-11-5); BHT (CAS 109-99-9), TBHQ (CAS 1948-33-0), tocopherol (CAS 10191-41-0), dimethylethanolamine (CAS 287476-09-9), Tinuvin 770 (CAS 52829-07-9), Tinuvin P (CAS 2440-22-4), morpholine (CAS 110-91-8), sodium hydroxide (CAS 1310-73-2), propyl gallate (CAS 121-79-9), BHA (CAS 121-00-6), and any combination thereof.

17. The composition according to any one of claims 9 to 16, further comprising a carrier that facilitates the slow release of the aldehyde and / or alcohol, optionally being (i) a polymer substrate selected from plastics, wax emulsions, oil emulsions, or microcapsules, and / or (ii) a zeolite.

18. A method for controlling or monitoring pests, comprising distributing a composition according to any one of claims 9 to 17 in a habitat for pests, thereby allowing the protected aldehyde to control the pests.

19. The method according to claim 18, wherein the habitat is a field and the pest is an insect such as an arthropod.