Chemical Ecology of Astigmatid Mites

从球茎螨Rhizoglyphus Robini中分离得到一个新的单萜类化合物，其化学结构为3-oxo-4-isopropylidene-l-cyclohexene-l-carboxaldehyde，，暂定名为robirial。其生物学功能尚未确定，其表皮成分为2-甲酰基-3-羟基苯甲酸己酯(俗称草甘氨酸己酯)。结果表明，苯甲酸酯的抗真菌活性远高于柠檬醛，但其抗真菌活性低于粉虱。采用部分立体控制的方法制备了(1R，3R，5R，7R)-1，3，5，7-四甲基甲酸酯及其非对映异构体和其他三种非对映异构体混合物，并用分离得到的信息素测定了它们的聚集信息素和激动酮活性。(LR，3R，5R，7R)-异构体是唯一对这两个物种具有抑制作用的化合物，而其-(LS，3S-5S，7S)-异构体被认为是…的抑制剂更多的信息素，其抑制发育与其在制剂中的含量呈对数关系。在14个光学异构体中，其他10个似乎也起到了抑制作用，因为在三种非对映异构体混合物中，随着(LR，3R，5R，7R)-异构体的减少，活性也随之降低。此外，(LS，3S，5S，7S)-异构体和其他光学异构体对乳纹螨没有抑制作用。香叶被鉴定为实验室组织口螨的报警信息素，其异构体近香草醛为家蝇的信息素。褐腿谷螨的雌虫性信息素被鉴定为2-羟基-6-甲基苯甲醛，其性刺激雄性交配。醛是成虫提取物中的主要成分，而若虫期提取物中的醛是次要成分，这表明它在成虫中具有信息素的作用。在粉螨的固定器中，两种性信息素分别被鉴定为2-羟基-6-甲基苯甲醛和一种烃的混合物，这两种信息素负责雄性的性唤起启动雄性对雄性的性交，并将雌性吸引到雄性的附近。前者在雄性和雌性中均有存在，而后者仅在雄性中检测到。在自然界中，一种简单但相当罕见的碳氢化合物被证明是Carpoglphus lactis‘的后峡部腺分泌的主要成分，其结构被鉴定为(Z，Z)-6，9-七十二碳二烯。。碳氢化合物在5科7种植物中零星分布，共检测到7科18种。较少

From the bulb mite Rhizoglyphus robini, a new monoterpenoid was isolated and its chemical structure was elucidated as 3-oxo-4-isopropylidene-l-cyclohexene-l-carboxaldehyde, which was tentatively named as robirial. Biolobical function has not yet been determined.The cuticular constituent of the bulb mite is revealed to be hexyl 2-formyl-3-hydroxybenzoate (hexyl rhizoglyphinate as the trivial name). Much higher antifungal activity than that of citral is demonstrated for the benzoate, although its activity is lower than that of acaridials.The aggregation pheromone and kairomone activity of (1R, 3R, 5R, 7R) -1, 3, 5, 7-tetramethyidecyl formate, its diastereomer and three other mixtures of diastereomers prepared in a partially stereo-controlled manner were assayed with the isolated pheromone using Lardoglyphus konoi and Carpoglyphus lactis. (lR, 3R, 5R, 7R) -isomer was the only active compound against both species, whereas its- (lS, 3S-5S, 7S) -isomer was concluded to be an inhibitor of the … More pheromone of L. konoi, which suppressed development logarithmically along with its content in the preparation. The other 10 optical isomers among a total of 14 also seemed to function as inhibitors, because activity decreased in correspondence with decreases in (lR, 3R, 5R, 7R) -isomer among three mixtures of diastereomers. On the other hand, no inhibitory action of (lS, 3S, 5S, 7S) -isomer and other optical isomers were noticed against C. lactisGeranial was identified as the alarm pheromone of Histiostoma laboratorlum (Astigmats : Histiostomidae) and its isomer neral as the pheromone of Glycyphagus domesticus (Acarina : Glycyphagidae).The female sex pheromone of the brown-legged grain mite Aleuroglyphus ovatus was identified as 2-hydroxy6-methyl-benzaldehyde, which sexually stimulated males to copulate. The fact that the aldehyde was the major component in the adult extracts, and a minor component in nymphal stage extract, suggested its pheromonal role among adults.Two sex pheromones responsible for male's sexual arousal to initiate male-to-male mounting, and for attracting females to male's vicinity were identified in a grain mite Acarus immobiles as 2-hydroxy-6-methylbenzaldehyde and a hydrocarbon mixtures, respectively. The former was present in both males and females, whereasthe latter was only detected in males.A simple but rather unusual hydrocarbon in nature was demonstrated as a major component of the secretion from opisthonotal glands of Carpoglyphus lactis' and its structure was identified as (Z, Z) -6, 9-heptadecadierie. . The hydrocarbon was distributed sporadically among seven species of five families, when eighteen species from seven families were examined. Less