Abstract: Provided are a terminal conjugated trienal acetal compound useful as an intermediate for producing a terminal conjugated trienal compound, and a method for producing a terminal conjugated trienal compound through deprotection of the terminal conjugated trienal acetal compound. More specifically, provided are a terminal conjugated trienal acetal compound represented by General Formula (1); a method for producing a (Z,E)-terminal conjugated trienal acetal compound, the method comprising the step of: reacting a phosphonium salt represented by General Formula (7) with (E)-2,4-pentadienal through Wittig reaction to obtain a (Z,E)-terminal conjugated trienal acetal compound represented by General Formula (3); and a method for producing a terminal conjugated trienal compound, the method comprising the step of: deprotecting the terminal conjugated trienal acetal compound represented by General Formula (1) to obtain a terminal conjugated trienal compound represented by General Formula (2).

Abstract: Provided is a method for industrially producing 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate, which is, for example, a sex pheromone substance of vine mealybug. More specifically, there is provided a method for producing 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate, comprising a step of transesterifying 2-isopropenyl-5-methyl-4-hexen-1-ol represented by Formula (1) with alkyl senecioate represented by General Formula (2) in the presence of a catalyst, while distilling off an alcohol represented by General Formula (4) formed as a by-product, to obtain 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate represented by Formula (3).

Abstract: Provided is a geometrically selective method for producing (±)-(E)-2-isopropyl-5-methyl-3,5-hexadienyl acetate, which is a sex pheromone of grape pineapple mealybug (GPMB). Specifically provided is a method for producing a an (E)-2-isopropyl-5-methyl-3,5-hexadienyl carboxylate compound (4), the method comprising the steps of: dehydrating a 3-hydroxy-2-isopropyl-5-methyl-4-hexenoate compound (1) to obtain an (E)-2-isopropyl-5-methyl-3,5-hexadienoate compound (2); reducing the alkoxycarbonyl group of the compound (2) to obtain (E)-2-isopropyl-5-methyl-3,5-hexadienol (3); and esterifying the compound (3) to obtain the compound (4).

Abstract: Provided is a sustained release pheromone preparation used for the control of insect pest, which can maintain a high release rate of a pheromone substance during the control period of the insect pest which has, as the pheromone substance, a C20-35 aliphatic hydrocarbon compound having such a melting point that the aliphatic hydrocarbon is in a solid form at normal temperature. More specifically, provided is a sustained release pheromone preparation comprising a membrane of an ethylene-vinyl acetate copolymer, and a C20-35 aliphatic hydrocarbon compound which is carried by the membrane, is permeable through the membrane, and has such a melting point that the aliphatic hydrocarbon compound is in a solid form at normal temperature, wherein the preparation targets an insect pest having the aliphatic hydrocarbon compound as a pheromone substance.

Abstract: Target compounds are synthesized simply, efficiently and selectively. More specifically, provided are a method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexenone (1) to obtain a 2,4,4-trimethyl-2-cyclohexenylidenemethyl ether compound (2) and hydrolyzing Compound (2) to obtain the (2,4,4-trimethyl-1-cyclohexene)carbaldehyde (3); a method for producing (2,4,4-trimethyl-1-cyclohexene)methanol, comprising a step of reducing Compound (3) to obtain the (2,4,4-trimethyl-1-cyclohexene)methanol (4); and a method for producing a (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound, comprising a step of esterifying Compound (4) to obtain the (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound (5).

Abstract: Provided is a 1-(2-acyloxyethyl)cyclopropyl sulfonate compound of General Formula (2): wherein R1 is a monovalent hydrocarbon group having 1 to 10 carbon atoms and optionally containing one or more unsaturated bonds and Z is a monovalent hydrocarbon group having 1 to 10 carbon atoms and optionally containing one or more unsaturated bonds.

Abstract: Provided is a simple, selective and efficient method for producing 4-alkyl-3-methylenebutyl carboxylates such as 7-methyl-3-methylene-7-octenyl propionate. More specifically, provided is, for example, a method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, comprising an acyloxylation step of subjecting a 1-(2-haloethyl)cyclopropyl sulfonate compound (1) to acyloxylation to obtain a 1-(2-acyloxyethyl)cyclopropyl sulfonate compound (2), a halogenation step of subjecting the compound (2) to halogenation involving cyclopropyl-allyl rearrangement to obtain a 3-halomethyl-3-butenyl carboxylate compound (3), and a coupling step of subjecting the compound (3) to a coupling reaction with an organometallic reagent (4) to obtain the 4-alkyl-3-methylenebutyl carboxylate compound (5).

Abstract: Target compounds are synthesized simply, efficiently and selectively. More specifically, provided are a method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexenone (1) to obtain a 2,4,4-trimethyl-2-cyclohexenylidenemethyl ether compound (2) and hydrolyzing Compound (2) to obtain the (2,4,4-trimethyl-1-cyclohexene)carbaldehyde (3); a method for producing (2,4,4-trimethyl-1-cyclohexene)methanol, comprising a step of reducing Compound (3) to obtain the (2,4,4-trimethyl-1-cyclohexene)methanol (4); and a method for producing a (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound, comprising a step of esterifying Compound (4) to obtain the (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound (5).

Abstract: Provided is a simple, selective and efficient method for producing 4-alkyl-3-methylenebutyl carboxylates such as 7-methyl-3-methylene-7-octenyl propionate. More specifically, provided is, for example, a method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, comprising an acyloxylation step of subjecting a 1-(2-haloethyl)cyclopropyl sulfonate compound (1) to acyloxylation to obtain a 1-(2-acyloxyethyl)cyclopropyl sulfonate compound (2), a halogenation step of subjecting the compound (2) to halogenation involving cyclopropyl-allyl rearrangement to obtain a 3-halomethyl-3-butenyl carboxylate compound (3), and a coupling step of subjecting the compound (3) to a coupling reaction with an organometallic reagent (4) to obtain the 4-alkyl-3-methylenebutyl carboxylate compound (5).

Abstract: Provided is a geometrically selective method for producing (±)-(E)-2-isopropyl-5-methyl-3,5-hexadienyl acetate, which is a sex pheromone of grape pineapple mealybug (GPMB). Specifically provided is a method for producing a an (E)-2-isopropyl-5-methyl-3,5-hexadienyl carboxylate compound (4), the method comprising the steps of: dehydrating a 3-hydroxy-2-isopropyl-5-methyl-4-hexenoate compound (1) to obtain an (E)-2-isopropyl-5-methyl-3,5-hexadienoate compound (2); reducing the alkoxycarbonyl group of the compound (2) to obtain (E)-2-isopropyl-5-methyl-3,5-hexadienol (3); and esterifying the compound (3) to obtain the compound (4).

Abstract: Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ?-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).

Abstract: Provided is a simple, selective and efficient method for producing 4-alkyl-3-methylenebutyl carboxylates such as 7-methyl-3-methylene-7-octenyl propionate. More specifically provided is a method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, the method comprising a diacyloxylation step of subjecting a 4-halo-2-halomethyl-1-butene compound (6) to diacyloxylation to obtain a 3-acyloxymethyl-3-butenyl carboxylate compound (3), and a coupling step of subjecting the 3-acyloxymethyl-3-butenyl carboxylate compound (3) to a coupling reaction with an organometallic reagent (4) to obtain the 4-alkyl-3-methylenebutyl carboxylate compound (5).

Abstract: Provided is a simple, selective and efficient method for producing 7-methyl-3-methylene-7-octenyl propionate and the like. More specifically, provided is, for example, a method for producing 7-methyl-3-methylene-7-octenyl propionate, comprising the steps of: subjecting a nucleophile represented by Formula (1) and an electrophile represented by Formula (2) to a coupling reaction to obtain a 7-methyl-3-methylene-7-octenyl halide represented by Formula (3), and subjecting the 7-methyl-3-methylene-7-octenyl halide (3) to propionyloxylation to obtain the 7-methyl-3-methylene-7-octenyl propionate represented by Formula (4).

Abstract: An silicon-containing antireflective coating (SiARC) material is applied on a substrate. The SiARC material which includes a base polymer and may include a boron silicate polymer including silsesquioxane. An etch sequence is utilized, which includes a first wet etch employing a basic solution, a second wet etch employing an acidic solution, and a third wet etch employing another basic solution. The first wet etch can be employed to break up the boron silicate polymer, and the second wet etch can remove the base polymer material, and the third wet etch can remove the residual boron silicate polymer and other residual materials. The SiARC material can be removed from a substrate employing the etch sequence, and the substrate can be reused for monitoring purposes.

Abstract: Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC?C—Z1—Y1 to a coupling reaction with an alkynyl halide (2) Y2—Z2—C?C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y2—Z2—C?C—C?C—Z1—Y1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

Abstract: There is disclosed a method for producing a substrate for making a microarray, the method comprising: at least, a step of forming a monomolecular film having orientated oxysilanyl groups toward an outmost surface on the substrate; and a step of forming a monomolecular film having orientated amino groups toward an outmost surface on the substrate by applying a solution containing a diamine compound to the oxysilanyl groups. There can be provided a method for producing a substrate for making a microarray in which density and orientation of amino groups orientated toward an outmost surface are controllable, and in addition, there is no delamination of a monomolecular film formed on the substrate.

Abstract: Target compounds are synthesized simply, efficiently and selectively. More specifically, provided are a method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexenone (1) to obtain a 2,4,4-trimethyl-2-cyclohexenylidenemethyl ether compound (2) and hydrolyzing Compound (2) to obtain the (2,4,4-trimethyl-1-cyclohexene)carbaldehyde (3); a method for producing (2,4,4-trimethyl-1-cyclohexene)methanol, comprising a step of reducing Compound (3) to obtain the (2,4,4-trimethyl-1-cyclohexene)methanol (4); and a method for producing a (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound, comprising a step of esterifying Compound (4) to obtain the (2,4,4-trimethyl-1-cyclohexenyOmethyl ester compound (5).

Abstract: A targeted compound is produced simply, efficiently and selectively. Specifically provided are a method for producing (2,4,4-trimethyl-2-cyclohexene)methanol, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexenone (1) to obtain 1-methylene-2,4,4-trimethyl-2-cyclohexene (2) and reacting the exocyclic double bond of Compound (2) to obtain the (2,4,4-trimethyl-2-cyclohexene)methanol (3); and a method for producing a (2,4,4-trimethyl-2-cyclohexenyl)methyl ester compound, comprising a step of esterifying Compound (3) to obtain the (2,4,4-trimethyl-2-cyclohexenyl)methyl ester compound (4).

Abstract: Provided is a simple, selective and efficient method for producing 7-methyl-3-methylene-7-octenyl propionate and the like. More specifically, provided is, for example, a method for producing 7-methyl-3-methylene-7-octenyl propionate, comprising the steps of: subjecting a nucleophile represented by Formula (1) and an electrophile represented by Formula (2) to a coupling reaction to obtain a 7-methyl-3-methylene-7-octenyl halide represented by Formula (3), and subjecting the 7-methyl-3-methylene-7-octenyl halide (3) to propionyloxylation to obtain the 7-methyl-3-methylene-7-octenyl propionate represented by Formula (4).

Abstract: Provided is a simple, selective and efficient method for producing 4-alkyl-3-methylenebutyl carboxylates such as 7-methyl-3-methylene-7-octenyl propionate. More specifically, provided is, for example, a method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, comprising an acyloxylation step of subjecting a 1-(2-haloethyl)cyclopropyl sulfonate compound (1) to acyloxylation to obtain a 1-(2-acyloxyethyl)cyclopropyl sulfonate compound (2), a halogenation step of subjecting the compound (2) to halogenation involving cyclopropyl-allyl rearrangement to obtain a 3-halomethyl-3-butenyl carboxylate compound (3), and a coupling step of subjecting the compound (3) to a coupling reaction with an organometallic reagent (4) to obtain the 4-alkyl-3-methylenebutyl carboxylate compound (5).