Composition of chemicals for manipulating the behavior of the orange wheat blossom midge, sitodiplosis mosellana (Géhin)

A method of preventing male Sitodiplosis mosellana from locating, and mating with female S. mosellana comprising deploying in a wheat field a pheromone containing release device, or micro-encapsulated pheromone, said pheromone being a chemical selected from one or more of the group consisting of (2S,7S)-2,7-nonanediyl dibutyrate, (2S,7R)-2,7-nonanediyl dibutyrate, (2R,7S)-2,7-nonanediyl dibutyrate and (2R,7R)-2,7-nonanediyl dibutyrate.

A synthetic process for preparing a mixture containing the four stereoisomers of 2,7-nonanediyl dibutyrate which comprises benzylating racemic 4-pentyne-2-ol to yield 2-O-benzyl-4-pentyne, treating 2-O-benzyl-4-pentyne with butyl lithium and butylene epoxide to yield 2-O-benzyl-4-nonyne-2,7-diol, hydrogenating 2-O-benzyl-4-nonyne-2,7-diol to yield 2,7-nonanediol and esterifying 2,7-nonanediol to yield 2,7-nonanediyl dibutyrate.

A synthetic process for preparing four optically active stereoisomers of 2,7-nonanediol dibutyrate comprising:

• (a) coupling S-propylene oxide with Grignard reagent derived from 5-bromo-1-pentene to yield (2S)-8-octen-2-ol, oxidizing (2S)-8-octen-2-ol with m-chloroperoxybenzoic acid to yield (7S)-1,2-epoxy-7-hydroxyoctane, kinetically resolving (7S)-1,2-epoxy-7-hydroxyoctane with (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt (II) and water to yield (2R,7S)-1,2-epoxy-7-hydroxyoctane, opening the epoxy ring of (2R,7S)-1,2-epoxy-7-hydroxyoctane with methylmagnesium bromide in the presence of CuI to yield (2S,7S)-2,7-nonanediol, esterifying (2S,7S)-2,7-nonanediol to yield (2S,7S)-2,7-nonanediyl dibutyrate;
• and
• (b) when either of the remaining three stereoisomers is desired, synthesizing respective epoxy intermediates from (S)- or (R)-propylene oxide and 5-bromo 1-pentene, kinetically resolving these intermediates, opening their epoxy rings and esterifying the diols.

A method of alleviating wheat damage in a wheat field caused by Sitodiplosis mosellana which comprises deploying in the field release devices or micro-encapsulation containing a chemical selected from one or more of the group consisting of:

• (2S,7S)-2,7-nonanediyl dibutyrate, (2S,7R)-2,7-nonanediyl dibutyrate, (2R,7S)-2,7-nonanediyl dibutyrate and (2R,7R)-2,7-nonanediyl dibutyrate.

A method of diagnosing the population density of Sitodiplosis mosellana in a wheat field which comprises deploying in the field traps baited with a release device containing a chemical selected from one or more of the group consisting of:

• (2S,7S)-2,7-nonanediyl dibutyrate, (2S,7R)-2,7-nonanediyl dibutyrate, (2R,7S)-2,7-nonanediyl dibutyrate and (2R,7R)-2,7-nonanediyl dibutyrate.