Abstract: An efficient process for preparing (9E,11Z)-9,11-hexadecadienal of formula (4) is provided. The process includes at least steps of: conducting a nucleophilic substitution reaction between an (8E,10Z)-8,10-pentadecadienyl magnesium halide derived from an (8E,10Z)-1-halo-8,10-pentadecadiene of (1): and an orthoformate ester (2) to thereby prepare a (9E, 11Z)-1,1-dialkoxy-9, 11-hexadecadiene (3): and hydrolyzing the (9E, 11Z)-1,1-dialkoxy-9,11-hexadecadiene (3) to obtain (9E, 11Z)-9,11-hexadecadienal (4).

Abstract: A halide compound having one or more carbon-carbon unsaturated bonds is catalytically reduced with substantially no dehalogenation to produce a reduced halide compound in which at least one of the one or more unsaturated bonds is reduced. Specifically provided is a method for producing a reduced halide compound including steps of: reacting a nickel compound, a zinc compound, and a borohydride compound in a solvent to obtain a reduction catalyst; and subjecting a halide compound having one or more carbon-carbon unsaturated bonds to catalytic reduction in the presence of the reduction catalyst to reduce at least one of the one or more carbon-carbon unsaturated bonds to thereby obtain a reduced halide compound.

Abstract: One object of the invention is to provide a method for preparing a 9,9-dialkoxy-7-nonynoate ester and (7E)-7,9-decadienoate ester, which are valuable as intermediates. The method for preparing a (7E)-7,9-decadienoate ester (5) comprises at least steps of: hydrolyzing a 9,9-dialkoxy-7-nonenoate ester (2), R3O(R2O)CHCH?CH(CH2)5CO2R1, to form a (7E)-9-oxo-7-nonenoate ester (3); and subjecting the (7E)-9-oxo-7-nonenoate ester (3) to a Wittig reaction with a triarylphosphonium methylide (4), Ar3P?CH2, to form the (7E)-7,9-decadienoate ester (5). The 9,9-dialkoxy-7-nonenoate ester may be prepared by, for example, reducing a 9,9-dialkoxy-7-nonynoate ester (1).

Abstract: A composition containing a substance having sex pheromone activity on San Jose scale (SJS) after finding the substance. More specifically, there are provided a composition having sex pheromone activity on SJS, the composition containing 3,7-dimethyl-7-octenyl propionate as a substance having sex pheromone activity on SJS; an attractant for SJS, the attractant containing the composition and a support for supporting the composition in such a manner as to allow the substance to be released; a mating disruptant for SJS, the disruptant containing the composition and a container for storing the composition in such a manner as to allow the substance to be released; and a method for attracting SJS or disrupting mating of SJS, the method including a step of installing the attractant or the mating disruptant for SJS in a field to release the substance from the attractant or the mating disruptant into the field.

Abstract: Methods selectively and efficiently produce 3,7-dimethyl-7-octenol and a carboxylic acid ester thereof. More specifically, a method produces 3,7-dimethyl-7-octenol, including steps of: subjecting a 3-methyl-3-butenyl nucleophilic reagent (2) and a 1,3-dihalo-2-methylpropane compound (3) to a coupling reaction to obtain a 2,6-dimethyl-6-heptenyl halide compound (4); converting the compound (4) into a 2,6-dimethyl-6-heptenyl nucleophilic reagent (5); and subjecting the nucleophilic reagent (5) to an addition reaction with at least one electrophilic reagent selected from the group made of formaldehyde, paraformaldehyde and 1,3,5-trioxane, followed by a hydrolysis reaction to obtain 3,7-dimethyl-7-octenol (6); and the other method.

Abstract: One object of the invention is to provide a method for preparing a 9,9-dialkoxy-7-nonynoate ester and (7E)-7,9-decadienoate ester, which are valuable as intermediates. The method for preparing a (7E)-7,9-decadienoate ester (5) comprises at least steps of: hydrolyzing a 9,9-dialkoxy-7-nonenoate ester (2), R3O(R2O)CHCH?CH(CH2)5CO2R1, to form a (7E)-9-oxo-7-nonenoate ester (3); and subjecting the (7E)-9-oxo-7-nonenoate ester (3) to a Wittig reaction with a triarylphosphonium methylide (4), Ar3P?CH2, to form the (7E)-7,9-decadienoate ester (5). The 9,9-dialkoxy-7-nonenoate ester may be prepared by, for example, reducing a 9,9-dialkoxy-7-nonynoate ester (1).

Abstract: A high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process including at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.

Abstract: A high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process including at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.

Abstract: Provided are a sustained release pheromone preparation capable of maintaining a high amount of pheromone release throughout a control period of vine mealybug (VMB) having lavandulyl senecioate (LVSN) as a pheromone substance; and a control method with the preparation. More specifically, provided are a sustained release pheromone preparation comprising a first pheromone substance, and a first container having the first pheromone substance sealed therein and comprising a first polymer membrane made of an ethylene vinyl acetate copolymer containing vinyl acetate units of from 0.5 to 10% by weight, wherein the first pheromone substance is lavandulyl senecioate, which is a pheromone substance of vine mealybug, and the lavandulyl senecioate can be released into the air through the first polymer membrane for 150 days or more; and others.

Abstract: Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

Abstract: Provided are industrial and economical methods for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate (3), which is, for example, a sex pheromone component of Comstock mealybug, and 2,6-dimethyl-1,5-heptadien-3-ol (2), which is an intermediate of the acetate (3). More specifically, provided are a method for producing 2,6-dimethyl-1,5-heptadien-3-ol comprising a step of subjecting 2-methyl-3-buten-2-yl 2-methyl-2-propenyl ether (1) to a rearrangement reaction in the presence of a base to obtain 2,6-dimethyl-1,5-heptadien-3-ol (2), and a method for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate comprising a step of acetylating the produced 2,6-dimethyl-1,5-heptadien-3-ol (2) to obtain 2,6-dimethyl-1,5-heptadien-3-yl acetate (3).

Abstract: Methods of producing a 2,4-dienal acetal compound and a 2,4-dienal compound useful as synthesis intermediates of a sex pheromone compound having a conjugated diene structure or a conjugated triene structure. More specifically, a method produces a 2,4-dienal acetal compound of Formula (2): R1CH?CH—CH?CH—CH(OR2)(OR3), including a step of subjecting a 2-enal acetal compound having a leaving group X at position C5 and being expressed by Formula (1): R1CHX—CH2—CH?CH—CH(OR2)(OR3) to an elimination reaction in the presence of a base to obtain the 2,4-dienal acetal compound (2); and a method for producing a 2,4-dienal compound of Formula (3): R1CH?CH—CH?CH—CHO, further including a step of deprotecting the 2,4-dienal acetal compound (2) to obtain the 2,4-dienal compound (3).

Abstract: Provided are a 1-halo-6,9-pentadecadiene useful as an intermediate having a skipped diene skeleton and a method for producing (7Z,10Z)-7,10-hexadecadienal. More specifically, provided are a method for producing (7Z,10Z)-7,10-hexadecadienal including steps of subjecting a Grignard reagent formed from a (6Z,9Z)-1-halo-6,9-pentadecadiene to a nucleophilic substitution reaction with an orthoformate ester to obtain a (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene; and hydrolyzing the (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene in the absence of an oxidation reaction to obtain the (7Z,10Z)-7,10-hexadecadienal; and the like.

Abstract: Methods of producing a 2,4-dienal acetal compound and a 2,4-dienal compound useful as synthesis intermediates of a sex pheromone compound having a conjugated diene structure or a conjugated triene structure. More specifically, a method produces a 2,4-dienal acetal compound of Formula (2): R1CH?CH—CH?CH—CH(OR2)(OR3), including a step of subjecting a 2-enal acetal compound having a leaving group X at position C5 and being expressed by Formula (1): R1CHX—CH2—CH?CH—CH(OR2)(OR3) to an elimination reaction in the presence of a base to obtain the 2,4-dienal acetal compound (2); and a method for producing a 2,4-dienal compound of Formula (3): R1CH?CH—CH?CH—CHO, further including a step of deprotecting the 2,4-dienal acetal compound (2) to obtain the 2,4-dienal compound (3).

Abstract: Provided are a 1-halo-6,9-pentadecadiene useful as an intermediate having a skipped diene skeleton and a method for producing (7Z,10Z)-7,10-hexadecadienal. More specifically, provided are a method for producing (7Z,10Z)-7,10-hexadecadienal including steps of subjecting a Grignard reagent formed from a (6Z,9Z)-1-halo-6,9-pentadecadiene to a nucleophilic substitution reaction with an orthoformate ester to obtain a (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene; and hydrolyzing the (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene in the absence of an oxidation reaction to obtain the (7Z,10Z)-7,10-hexadecadienal; and the like.

Abstract: A sustained release pheromone preparation for controlling a pest insect contains, as sex pheromone components, an unsaturated aliphatic acetate and an unsaturated aliphatic alcohol having a structure where the acetyl group of the acetate is replaced with a hydrogen atom, wherein a ratio between the acetate and the alcohol in the mixture solution contained in the sustained release pheromone preparation can be kept constant throughout the effective action period. More specifically, the preparation includes a mixture solution containing the unsaturated aliphatic acetate and the unsaturated aliphatic alcohol in a weight ratio of 10:90 to 99.5 to 0.5 and a container for enclosing the mixture solution, the container containing, as at least a part of the container, a membrane of a polyester corresponding to Formula (I) below, a copolymer thereof, or a polymer blend of the polyester or copolymer with a biodegradable polyester.

Abstract: Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

Abstract: Provided are a method for producing a terminal conjugated dienal compound without an oxidation reaction and a terminal hydroxyacetal compound useful as an intermediate in the method. More specifically, provided are a method for producing an (E)-dienal compound comprising the steps of: a metalation reaction of an alkynal acetal compound (1) to obtain an organic metal compound (2), an addition reaction of (2) to ethylene oxide to obtain a hydroxyalkynal acetal compound (3), a reduction reaction of (3) to obtain an (E)-hydroxyalkenal acetal compound (4), a functional group conversion reaction of (4) to obtain an (E)-alkenal acetal compound (5) having a leaving group X, an elimination reaction of (5) to obtain an (E)-dienal acetal compound (6), and a hydrolysis reaction of (6) to obtain the (E)-dienal compound (7); and others.

Abstract: There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4).

Abstract: There is provided a method for producing ethyl 4-methyloctanoate at a lower cost, by fewer steps, and in higher yield. More specifically, there is provided a method for producing ethyl 4-methyloctanoate comprising the steps of: reacting 1-chloro-2-methylhexane through malonic ester synthesis to obtain diethyl 2-methylhexylmalonate, and subjecting the diethyl 2-methylhexylmalonate to a Krapcho reaction to obtain ethyl 4-methyloctanoate.