- Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)
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Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.
- Chien, Wei-Jynn,Gupta, Sachin,Liu, Bin,Lou, Da Wei,Shen, Yu-Jhe,Syu, Kun-Jie,Tseng, Jui-Chang,Zhang, Yuan-Xin
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- N-Acylated amino acid methyl esters from marine Roseobacter group bacteria
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Bacteria of the Roseobacter group (Rhodobacteraceae) are important members of many marine ecosystems. Similar to other Gram-negative bacteria many roseobacters produce N-acylhomoserine lactones (AHLs) for communication by quorum sensing systems. AHLs regulate different traits like cell differentiation or antibiotic production. Related N-acylalanine methyl esters (NAMEs) have been reported as well, but so far only from Roseovarius tolerans EL-164. While screening various roseobacters isolated from macroalgae we encountered four strains, Roseovarius sp. D12_1.68, Loktanella sp. F13, F14 and D3 that produced new derivatives and analogs of NAMEs, namely N-acyl-2-aminobutyric acid methyl esters (NABME), N-acylglycine methyl esters (NAGME), N-acylvaline methyl esters (NAVME), as well as for the first time a methyl-branched NAME, N-(13-methyltetradecanoyl)alanine methyl ester. These compounds were detected by GC–MS analysis, and structural proposals were derived from the mass spectra and by derivatization. Verification of compound structures was performed by synthesis. NABMEs, NAVMEs and NAGMEs are produced in low amounts only, making mass spectrometry the method of choice for their detection. The analysis of both EI and ESI mass spectra revealed fragmentation patterns helpful for the detection of similar compounds derived from other amino acids. Some of these compounds showed antimicrobial activity. The structural similarity of N-acylated amino acid methyl esters and similar lipophilicity to AHLs might indicate a yet unknown function as signalling compounds in the ecology of these bacteria, although their singular occurrence is in strong contrast to the common occurrence of AHLs. Obviously the structural motif is not restricted to Roseovarius spp. and occurs also in other genera.
- Bruns, Hilke,Ziesche, Lisa,Taniwal, Nargis Khakin,Wolter, Laura,Brinkhoff, Thorsten,Herrmann, Jennifer,Müller, Rolf,Schulz, Stefan
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supporting information
p. 2964 - 2973
(2018/12/13)
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- PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS
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In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.
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- SYNTHETIC SALT COMPLEXES FOR IMPROVEMENT OF PLANT GROWTH AND YIELD
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The disclosure provides agricultural compositions comprising oligoglucosamine salt complexes and methods for improving plant growth and crop yield. These compositions may be applied to plant propagating materials, including seeds and other regenerable plant parts, including cuttings, bulbs, rhizomes and tubers. They may also be applied to foliage, or soil either prior to or following planting of plant propagating materials. Such applications may be made alone or in combination with fungicides, insecticides, nematicides and other agricultural agents used to improve plant growth and crop yield.
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Page/Page column 68; 69
(2015/10/05)
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- SYNTHETIC LIPOAMINO ACID GLUCOSAMINE DERIVATIVES FOR IMPROVEMENT OF PLANT GROWTH AND YIELD
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The invention provides compounds, formulations and methods for improving plant emergence, growth and yield. More specifically, the present invention relates to compositions comprising the synthetic lipoamino acid glucosamine compounds of Formula 1 below wherein the substituents are as defined in the claims. These compounds may be applied to plant propagating materials, including seeds and other regenerable plant parts, including cuttings, bulbs, rhizomes and tubers. They may also be applied to foliage, or soil either prior to or following planting of plant propagating materials. Such applications may be made alone or in combination with fungicides, insecticides, nematicides and other agricultural agents used to improve plant growth and crop yield. The compounds of Formula I can improve the agronomic performance of a variety of crops including barley, canola, corn, potato, soybean and wheat.
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Page/Page column 30; 31
(2014/09/29)
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- A novel synthesis of Z-(9)-hexadecenal in improved yields, from aleuritic acid
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Z-(9)-Hexadecenal, an important pheromonal component, was synthesised from ulcuritic acid, using novel procedure, resulting in improved yields. Microwave-assisted technique was also applied in the esterification of aleuritic acid, leading to shorter reaction times and 98% yield of methyl aleuritate.
- Sarkar,Prasad,Nandy, Sonia
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p. 475 - 476
(2007/10/03)
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- Use of enyne compounds in the synthesis of insect pheromones
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A new approach has been developed to the synthesis of monogenic insect pheromones with acetogenin and macrolide structures, using the low reactivity of ozone and of 9-borabicyclo[3.3.1]nonane towards an acetylenic function as compared with a vinyl function.
- Ishmuratov,Ishmuratova,Odinokov,Tolstikov
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- Stereoselective hydrogenation in synthesis of components or component precursors of pest insect pheromones
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A study is made of stereoselective hydrogenation of high-molecular-weight acetylenic carbinols on supported copper catalysts in ethanol to form cis-olefinic alcohols, components or intermediates of components of pheromones of pest insects: cotton and gray grain cutworm moths.
- Kartonozhkina,Pak,Slepov,Izdebskaya
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p. 1013 - 1015
(2007/10/03)
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- A new method for the synthesis of (Z)-9-hexadecen-1-al, an importannt pheromone component of Heliothis armigera and many other pests
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A simple and convenient synthesis of (Z)-9-hexadecen-1-al (1), an important sex pheromone component of 1-Heliothis armigera, has been achieved from the cheap and readily available 10-undecenoic acid (2).
- Narasimhan, S.,Mohan, H.
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p. 950 - 953
(2007/10/03)
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- SYNTHESIS OF HEXADEC-9Z-ENAL - ONE OF THE COMPONENTS OF THE SEX PHEROMONE OF Heliothis armigera
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Hexadec-9Z-enal - a component of the sex pheromone of the cotton bollworm Heliothis armigera - has been obtained by a three-stage synthesis from 9-acetoxynonanal and n-heptyltriphenylphosphonium bromide followed by reduction and oxidation.
- Dzhumakulov, T.,Kadyrova, M. M.
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p. 240 - 241
(2007/10/02)
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- OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XLII. SYNTHESIS OF (9Z)-TETRADECENYL ACETATE AND (9Z)-HEXADECENAL FROM (Z,Z)-1,5-CYCLOOCTADIENE
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A stereocontrolled synthesis of (9Z)-tetradecenyl acetate and (9Z)-hexadecenal, which are components of the sex pheromones of the pine (Panolis flammea) and cotton (Heliothis armigera) moths respectively, was realized on the basis of the partial ozonolysis of (Z,Z)-1,5-cyclooctadiene.
- Odinokov, V. N.,Galeeva, R. I.,Ishmuratov, G. Yu.,Kargapol'tseva, T. A.,Sokol'skaya, O. V.,et al.
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p. 1986 - 1989
(2007/10/02)
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- A facile synthesis of cotton bollworm (Heliothis armigera) pheromone components: (Z)-11-Hexadecenal and (Z)-9-hexadecenal
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(Z)-Hexadecenal (1) and (Z)-9-hexadecenal (2) have been synthesised starting from easily accessible propargyl alcohol.Alkylation of propargyl alcohol yields 3 and 4, which on acetylene-zipper reaction give terminal acetylenes (5 and 6, R'=H).Alkylation of 5 and 6 followed by depyranylation afford 7 and 8.Partial cis-hydrogenation of these with P2Ni followed by PCC oxidation give compounds 1 and 2.
- Mithran, S.,Mamdapur, V. R.
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p. 755 - 756
(2007/10/02)
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- INSECT PHEROMONES AND THEIR ANALOGUES. XVI. PRACTICAL SYNTHESIS OF HEXADEC-9Z-ENAL - A COMPONENT OF THE SEX PHEROMONE OF THE COTTON BOLLWORM Heliothis armigera
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A synthesis of hexadec-9Z-enal - a component of the sex pheromone of the cotton bollworm Heliothis armigera (Huebner) - based on cyclooctene (I) is proposed.Through a solution of 22 g of (I), 250 ml of cyclohexane, and 40 ml of MeOH is passed (at 5 deg C) 0.2 M O3/O2, the solution is decanted off, and the precipitated ozonide is dissolved in 200 ml of MeOH and is reduced with 19 g of NaBH4 (40 deg C) with the isolation, after the usual working up, of 23.4 g of octane-1,8-diol (II).From 0.5 mole of (II) and 0.6 mole of 45percent HBr 8-bromooctan-1-ol (III) is obtained and this is converted into 1-(2-(THPL)oxy)-8-bromooctane (IV).The condensation of (IV) with oct-1-yne (Ar, LiNH2, HMPTA, 10 deg C, 1 h, and then 55 deg C, 10 h) leads to 1-(2-THPL-oxy)hexadec-9-yne (V) the hydrolysis of which (MeOH, H2O, p-TsOH, 20 deg C for 20 h) yields hexadec-9-yn-ol (VI).The reduction of (VI) (Et2O, iso-BuMgBr, Cp2TiCl2, 0 deg C, 15 min, then 20 deg C, 1 h) yields hexadec-9Z-en-1-ol (VII).The oxidation of (VII) (PyHCrO3+ Cl-, CH2Cl2, 20 deg C, 2 h) gives hexadec-9Z-enal (VIII).Characteristics of the compounds (yield (percent), nD20(25): (II) - 80, mp 61-62 deg C; (III) - 75, 1.4807; (IV) - 99, -; (V) - 52, 1,4650; (VI) - 85, 1.4657; (VII) - 99, 1.4650; (VIII) - 98, 1.4600.Characteristics of the IR and PMR spectra of compounds (V-VII) are given.
- Odinolov, V. N.,Dzhemilev, U. M.,Ishmuratov, G. Yu.,Botsman, L. P.,Vostrikova, O. S.,et al.
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p. 242 - 244
(2007/10/02)
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