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EP-4740735-A1 - COMPOSITION CONTAINING NATURAL PYRETHRIN AND ANTIOXIDANT

EP4740735A1EP 4740735 A1EP4740735 A1EP 4740735A1EP-4740735-A1

Abstract

The present invention relates to a composition containing natural pyrethrin and an antioxidant selected from Group P or Group S: Group P is a group consisting of a compound represented by Formula (1) [In the formula, R 1 and R 2 are identical to or different from each other, and each represents a C9-C14 alkyl group.], 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, tris(nonylphenyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphinate, tridodecyl trithiophosphite, and the like; Group S is a group consisting of pentaerythritol tetrakis[3-(dodecylthio)propionate], 2-mercaptobenzimidazole, 2, 4-bis(dodecylthio)methyl]-6-methylphenol, and didodecyl 3,3'-thiodipropionate.

Inventors

  • TOKUNAGA TAKASHI
  • YAMADA NORIKO
  • SONOBE Fuhito

Assignees

  • Sumitomo Chemical Company, Limited

Dates

Publication Date
20260513
Application Date
20240627

Claims (18)

  1. A composition comprising natural pyrethrin and one or more phosphorus-based antioxidants selected from Group P or one or more sulfur-based antioxidant selected from Group S: Group P is a group consisting of a compound represented by Formula (1) [In the formula, R 1 and R 2 are identical to or different from each other, and each represents a C9-C14 alkyl group.], 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, tris(nonylphenyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphinate, tridodecyl trithiophosphite, triisodecyl phosphite, diphenyl isodecyl phosphite, 4,4'-butylidenebis(3-methyl-6-tert-butylphenyl ditridecyl phosphite), and tetra(C12-15 alkyl)-4,4'-isopropylidenediphenyldiphosphite; Group S is a group consisting of pentaerythritol tetrakis[3-(dodecylthio)propionate], 2-mercaptobenzimidazole, 2, 4-bis(dodecylthio)methyl]-6-methylphenol, and didodecyl 3,3'-thiodipropionate.
  2. The composition according to claim 1, wherein Group P is a group consisting of 3,9-bis(isodecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(isotridecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, tris(nonylphenyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphinate, tridodecyl trithiophosphite, triisodecyl phosphite, diphenyl isodecyl phosphite, 4,4'-butylidenebis(3-methyl-6-tert-butylphenyl ditridecyl phosphite), and tetra(C12-15 alkyl)-4,4'-isopropylidenediphenyldiphosphite.
  3. The composition according to claim 1 or 2, comprising a phenolic antioxidant.
  4. The composition according to claim 1, wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are one or more phosphorus-based antioxidants selected from Group P L : Group P L is a group consisting of triisodecyl phosphite, diphenyl isodecyl phosphite, and 4,4'-butylidenebis(3-methyl-6-tert-butylphenyl ditridecyl phosphite).
  5. The composition according to claim 4, comprising a phenolic antioxidant.
  6. An insect pest controlling formulation for heat-transpiration, comprising the composition according to claim 4 and a paraffinic solvent.
  7. A method for controlling mosquitoes, using the composition according to claim 4 or 5 or the insect pest controlling formulation for heat-transpiration according to claim 6.
  8. The composition according to claim 1, wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are one or more phosphorus-based antioxidants selected from Group P M : Group P M is a group consisting of triisodecyl phosphite, diphenyl isodecyl phosphite, 4,4'-butylidenebis(3-methyl-6-tert-butylphenyl ditridecyl phosphite), and tetra(C12-15 alkyl)-4,4'-isopropylidenediphenyldiphosphite.
  9. The composition according to claim 8, comprising a phenolic antioxidant.
  10. The composition according to claim 1, wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are the compound represented by Formula (1).
  11. The composition according to claim 1, wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are 3,9-bis(isodecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane or 3,9-bis(isotridecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane.
  12. The composition according to claim 1, wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are one or more phosphorus-based antioxidants selected from Group P U or one or more sulfur-based antioxidants selected from Group S: Group P U is a group consisting of 3,9-bis(isodecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, tris(nonylphenyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphinate, and tridodecyl trithiophosphite.
  13. The composition according to claim 12, wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are one or more phosphorus-based antioxidants selected from Group P U .
  14. The composition according to claim 12, wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are one or more sulfur-based antioxidants selected from Group S.
  15. The composition according to claim 14, wherein the one or more sulfur-based antioxidants selected from Group S are pentaerythritol tetrakis[3-(dodecylthio)propionate], 2-mercaptobenzimidazole, or 2,4-bis[(dodecylthio)methyl]-6-methylphenol.
  16. The composition according to any one of claims 12 to 15, comprising a phenolic antioxidant.
  17. The composition according to any one of claims 12 to 15, comprising citric acid.
  18. The composition according to claim 16, comprising citric acid.

Description

[Technical Field] The present invention relates to a composition containing natural pyrethrin and an antioxidant. This application claims priority to and benefit of Japanese Patent Application No. 2023-109574 filed on July 3, 2023, and Japanese Patent Application No. 2023-143206 filed on September 4, 2023, the entire contents of which are incorporated by reference into this description. [Background Art] Due to the increasing consumer preference for natural products, natural pyrethrin has been attracting attention (for example, Patent Literature 1). Although natural pyrethrin is suitably used for insect pest control and the like, it is known that its insect pest controlling effect or storage stability tends to decrease over time due to the instability of its chemical structure. [Citation List] [Patent Literature] [Patent Literature 1] WO2022/220294 [Summary of the Invention] [Problems to be Solved by the Invention] An object of the present invention is to provide a novel composition containing natural pyrethrin, which has excellent maintenance of insect pest controlling effects or storage stability. [Means for Solving the Problems] The inventors conducted studies to provide a novel composition containing natural pyrethrin. As a result, they found that a composition containing natural pyrethrin and a specific antioxidant has excellent effects, thereby completing the present invention. The present invention includes, but is not limited to, the following embodiments. [1] A composition containing natural pyrethrin and one or more phosphorus-based antioxidants selected from Group P or one or more sulfur-based antioxidants selected from Group S (hereinafter referred to as the composition of the present invention) : Group P is a group consisting of a compound represented by Formula (2) [In the formula, R represents a C9-C14 alkyl group.], 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, tris(nonylphenyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphinate, tridodecyl trithiophosphite, triisodecyl phosphite, diphenyl isodecyl phosphite, 4,4'-butylidenebis(3-methyl-6-tert-butylphenyl ditridecyl phosphite), and tetra(C12-15 alkyl)-4,4'-isopropylidenediphenyldiphosphite;Group S is a group consisting of pentaerythritol tetrakis[3-(dodecylthio)propionate], 2-mercaptobenzimidazole, 2,4-bis[(dodecylthio)methyl]-6-methylphenol, and didodecyl 3,3'-thiodipropionate.[2] The composition according to [1], wherein Group P is a group consisting of 3,9-bis(isodecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(isotridecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, tris(nonylphenyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphinate, tridodecyl trithiophosphite, triisodecyl phosphite, diphenyl isodecyl phosphite, 4,4'-butylidenebis(3-methyl-6-tert-butylphenyl ditridecyl phosphite), and tetra(C12-15 alkyl)-4,4'-isopropylidenediphenyldiphosphite.[3] The composition according to [1] or [2], containing a phenolic antioxidant.[4] The composition according to [1], wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are one or more phosphorus-based antioxidants selected from Group PL : Group PL is a group consisting of triisodecyl phosphite, diphenyl isodecyl phosphite, and 4,4'-butylidenebis(3-methyl-6-tert-butylphenyl ditridecyl phosphite).[5] The composition according to [4], containing a phenolic antioxidant.[6] An insect pest controlling formulation for heat-transpiration, containing the composition according to [4] or [5] and a paraffinic solvent.[7] A method for controlling mosquitoes, using the composition according to any one of [4] or [5] or the insect pest controlling formulation for heat-transpiration according to [6].[8] The composition according to [1], wherein the one or more phosphorus-based antioxidants selected from Group P or the one or more sulfur-based antioxidants selected from Group S are tetra(C12-15 alkyl)-4,4'-isopropylidenediphenyldiphosphite.[9] The composition according to [8], containing a phenolic antioxidant. The present invention further includes, but is not limited to, the following embodiments. <1> A composition containing natural pyrethrin and one or more phosphorus-based antioxidants selected from Group P or one or more sulfur-based antioxidant selected from Group S: Group P is a group consisting of a compound represented by Formula (1) [In the formula, R1 and R2 are identical to or different from each other, and each represents a C9-C14 alkyl group.], 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, tris(nonylphenyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphinate, tridodecyl trithiophosphite, t