- Novel nitenpyram analogues with tetrahydropyridone-fixed cis-configuration: Synthesis, insecticidal activities, and molecular docking studies
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To make further researches on the diversity of nitenpyram analogues with a cis-nitromethylene configuration, a series of cis-nitenpyram analogues (3a-q) with tetrahydropyridone-fixed cis-configuration were designed and synthesized. Preliminary bioassays showed that most of the designed nitenpyram analogues exhibited good insecticidal activity at 100 mg/L against Nilaparvata lugens and Myzus persicae, while analogues 3n afforded the best in vitro activity. Modeling the ligand-receptor complexes by molecular docking study revealed the analogues 3 with various substituents on phenyl show their different binding affinities to the insect nAChR, which also explained the structure-activity relationships observed in vitro. The Japan Institute of Heterocyclic Chemistry.
- Sun, Chuan-Wen,Wang, Jing,Wu, Ying,Nan, Shi-Bin,Zhang, Wang-Geng
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Read Online
- Preparation method of nitenpyram
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The invention discloses a preparation method of nitenpyram. The method comprises the steps: carrying out a catalytic reaction in a low-grade chlorinated hydrocarbon solvent by taking N-ethyl-2-chloro-5-pyridinemethylamine and 1,1-dichloro-2-nitroethylene as starting raw materials and anion exchange resin as an acid binding catalyst, ending the reaction, and carrying out filtration to remove the anion exchange resin to obtain a solution of an intermediate compound (II); introducing methylamine gases to the solution of the intermediate compound (II), ending the reaction, and carrying out filtration; and concentrating a filtrate, and separating out a crystal to obtain a target compound (I). The invention provides the preparation method of a synthesis process of nitenpyram, the preparation method is few in reaction steps, simple in process as well as green and environment-friendly in process, and nitenpyram is high in yield and quality. Compared with an existing technical process, the preparation method is simple and convenient in process operation, low in operation cost, free of wastewater discharge, capable of realizing recycle of the catalyst, green and environment-friendly in process, high in product quality and yield, low in cost, very suitable for industrial production and extremely high in industrial application value.
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Paragraph 0014; 0029-0034
(2018/11/27)
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- NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND
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An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.
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- Nitrogenous heterocyclic compound and use thereof
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The invention relates to a nitrogenous heterocyclic compound with a novel structure and use thereof. The nitrogenous heterocyclic compound is a compound represented by a formula I (shown in the description) or a salt thereof acceptable in pesticide science. The nitrogenous heterocyclic compound provided by the invention can serve as a pesticide. Compared with the existing pesticides, the pesticide provided by the invention has the advantages that the chemical stability is better, and meanwhile, the killing activity to resistant insects is better.
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- Improved preparation method of nitenpyram
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The invention relates to an improved preparation method of nitenpyram. The method comprises steps as follows: firstly, 1,1-dichloroethylene has a reaction with a nitration agent comprising hydrochloric acid and sodium nitrate to generate 1,1,1-trichlorine-2-nitroethane, and the 1,1,1-trichlorine-2-nitroethane has an elimination reaction with NaHCO3 to generate a 1,1-dichlorine-2-nitroethylene intermediate; secondly, 2-chlorine-5-chloromethylpyridine has a reaction with ethylamine, and an ethylamine intermediate is prepared; thirdly, the ethylamine intermediate has a reaction with 1,1-dichlorine-2-nitroethylene intermediate and monomethylamine, and the final product nitenpyram is generated. NaNO3 is used to replace traditional nitric acid to serve as a target phase transfer catalyst, the reaction selectivity is improved, the yield is higher, and the operation is safer.
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Paragraph 0058-0066
(2016/10/07)
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- Design, synthesis, insecticidal evaluation and molecular docking studies of cis-nitenpyram analogues bearing diglycine esters
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Based on the strategies of receptor structure-guided neonicotinoid design, a series of novel cis-nitenpyram analogues bearing diglycine esters were designed and synthesized. Preliminary bioassays indicated that the insecticidal spectra of the target compounds were expanded compared with our previous work, while all the target compounds presented excellent insecticidal activities against Nilaparvata lugens and Aphis medicagini at 100 mg/L. Among these analogues, 6b showed 100% mortality against Nilaparvata lugens (LC50 = 0.163 mg/L) and 90% against Aphis medicagini at 4 mg/L. SARs suggested that the insecticidal potency of our designed cis-nitenpyram analogues was dual-controlled by the size and species of the ester groups. The molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique molecular recognition and binding mode compared with the previously designed compounds. Introduction of the peptide bond gave rise to more significant hydrogen bonds between the nitenpyram analogues bonding with the amino acid residues of insect nAChRs. The docking results explained the SARs observed in vitro, and shed light on the novel insecticidal mechanism of these cis-nitenpyram analogues.
- Chen, Yanxia,Sun, Chuanwen,Wen, Xiaxia,Zhang, Wanggeng
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p. 159 - 168
(2013/07/26)
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- Cis-nitenpyram analogues containing 1,4-dihydropyridine: Synthesis, insecticidal activities, and molecular docking studies
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A novel series of cis-nitenpyram analogues (2a-2p) were designed and prepared by introducing the 1,4-dihydropyridine, with their cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed that most compounds exhibited good insecticidal activities at 20 mg/L against Aphis medicagini, and analogues 2a and 2d afforded the best activity, and both of them had 100% mortality at 4 mg/L. In addition, molecular docking studies were also performed to model the ligand-receptor complexes, and the results explained the structure-activity relationships observed in vitro, which may provide some useful information for future design of new insecticides. Copyright
- Sun, Chuanwen,Chen, Yanxia,Liu, Tianyan,Wu, Ying,Fang, Ting,Wang, Jing,Xing, Jiahua
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scheme or table
p. 1415 - 1422
(2012/09/07)
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- Design, synthesis, and particular biological behaviors of chain-opening nitromethylene neonicotinoids with cis configuration
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On the basis of the structure of heterocyclic-fused cis configuration derivatives and chain-opening neonicotinoids, two series of novel chain-opening tetrahydropyridine analogues were designed and synthesized. The preliminary bioassay tests were determined on cowpea aphid (Aphis craccivora) and armyworm (Pseudaletia separata Walker). The results showed that some of the target compounds exhibited repellent effects, whereas others showed good insecticidal activities.
- Lu, Siyuan,Shao, Xusheng,Li, Zhong,Xu, Zhiping,Zhao, Shishuai,Wu, Yinli,Xu, Xiaoyong
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experimental part
p. 322 - 330
(2012/04/04)
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- Synthesis, insecticidal activity, crystal structure, and molecular docking studies of nitenpyram analogues with an ω-hydroxyalkyl ester arm anchored on the tetrahydropyrimidine ring
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On the basis of the research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a new series of nitenpyram analogues with an ω-hydroxyalkyl ester arm anchored on the tetrahydropyrimidine ring was designed and synthesized to further enhance the strength of the hydrogen-bonding action they display in binding with the nAChR. The structures of the target compounds were characterized by 1H NMR, IR, and elemental analysis, and the cis configuration was confirmed by X-ray diffraction. Preliminary bioassays indicated that all of the nitenpyram analogues exhibited good insecticidal activity against Nilaparvata lugens and Myzus persicae at 100 mg/L, whereas analogues 4d and 6a afforded the best in vitro activity that had ≥95% mortality at 4 mg/L; the LC50 values of the analogues 4d and 6a were 0.170 and 0.154 mg/L, respectively. Structure-activity relationship (SAR) studies suggested that their insecticidal potency was also dual-controlled by the flexibility and size of the molecule. In addition, molecular docking simulations revealed that analogues 4d and 6a displayed stronger hydrogen-bonding action in binding with the nAChR, which explained the SARs observed in vitro and implied that the designed nitenpyram analogues are both practical and feasible.
- Sun, Chuan-Wen,Fang, Ting,Wang, Jing,Hao, Zhi-Bing,Nan, Shi-Bing
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p. 9553 - 9561,9
(2012/12/12)
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- METHOD FOR SEPARATING AND PURIFYING alpha- UNSATURATED AMINE COMPOUND
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A method for purifying an α-unsaturated amine compound represented by Formula (1), the method comprising a step of extracting with water the compound of Formula (1) from a crude product of the α-unsaturated amine compound represented by Formula (1), and a step of extracting with a pyridine solvent the α-unsaturated amine compound of Formula (1) from the aqueous solution containing the compound of Formula (1) obtained in the previous step to obtain a pyridine solvent solution of the compound of Formula (1): wherein R1 represents a hydrogen atom, a C1-4 alkyl group, a halo C1-4 alkyl group, a C1-4 alkoxy-C1-4 alkyl group, a C7-9 aralkyl group, or an optionally substituted phenyl group, R2 represents a hydrogen atom, a C1-4 alkyl group, or a C7-9 aralkyl group, and R3 represents a hydrogen atom, a C1-5 alkyl group, a halo C1-4 alkyl group, a hydroxy C1-4 alkyl group, a C1-4 alkoxy-C1-4 alkyl group, C2-4 alkenyl group, or a C7-9 aralkyl group.
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Page/Page column 5
(2011/08/06)
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- Synthesis, insecticidal activity, and molecular docking studies of nitenpyram analogues with a flexible ester arm anchored on tetrahydropyrimidine ring
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To make further researches on the structure-activity relationships (SARs) of our previous synthesized neonicotinoid compounds, a new series of nitenpyam analogues with flexible ester arm were synthesized. Preliminary bioassays indicated that all of our newly designed nitenpyam analogues exhibited good insecticidal activity at 100 mg/L, while analogues 4c and 4d afforded the best in vitro activity, and both of them had 100% mortality at 20 mg/L. The SAR studies suggested that their insecticidal potency was dual-controlled by the length of the ester arm and the size of the ester group. In addition, the molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique molecular recognition and binding mode, which explained the SARs observed in vitro, and shed light on the novel insecticidal mechanism of these novel nitenpyam analogues.
- Sun, Chuanwen,Xu, Xiao,Xu, Yonghua,Yan, Dingrong,Fang, Ting,Liu, Tianyan
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scheme or table
p. 4828 - 4835
(2011/11/29)
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- HETEROCYCLIC NITROGENOUS OR OXYGENOUS COMPOUNDS WITH INSECTICIDAL ACTIVITY FORMED FROM DIALDEHYDES AND THEIR PREPARATION AND USES THEREOF
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The heterocyclic nitrogenous or oxygenous compounds of formula (A), (B), (C) or (D) formed from dialdehydes, their optical isomers, cis- and trans- isomers, or agrochemically acceptable salts, their preparation methods, agrochemical compositions comprising the compounds and the uses thereof are provided. The compounds and their derivatives have high insecticidal activities to several farming and forestry pests including homoptera and lepidoptera pests, such as aphis, fulgorid, whitefly, leafhopper, common thrips, cotton bollworm, cabbage caterpillar, cabbage moth, cotton leafworm, armyworm and so on.
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- HETEROCYCLIC NITROGENOUS OR OXYGENOUS COMPOUNDS WITH INSECTICIDAL ACTIVITY FORMED FROM DIALDEHYDES AND THEIR PREPARATION AND USES THEREOF
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The heterocyclic nitrogenous or oxygenous compounds of formula (A), (B), (C) or (D) formed from dialdehydes, their optical isomers, cis- and trans- isomers, or agrochemically acceptable salts, their preparation methods, agrochemical compositions comprising the compounds and the uses thereof are provided. The compounds and their derivatives have high insecticidal activities to several farming and forestry pests including homoptera and lepidoptera pests, such as aphis, fulgorid, whitefly, leafhopper, common thrips, cotton bollworm, cabbage caterpillar, cabbage moth, cotton leafworm, armyworm and so on.
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- NITROGENOUS HETEROCYCLIC COMPOUND WITH INSECTICIDAL ACTIVITY AND ITS PREPARATION AND USE
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The present invention relates to nitro-containing heterocyclic or ring-opening nitrogenous compounds of formula (A), wherein R1, R2, R3, R4, R5, Y, Z, and W are as defined in the specification. The present invention discloses the preparation and the uses of a novel insecticide. Said compound and the derivatives thereof have high insecticidal activity to farm insects including homoptera and lepidoptera pests, such as aphis, fulgorides, aleyrodids, leafhopper, commom thrips, cotton bollworm, cabbage caterpillar, cabbage moth, cotton leafworm, armywom and so on.
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Page/Page column 13
(2011/02/26)
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- METHOD FOR SEPARATING AND PURIFYING ALPHA -UNSATURATED AMINE COMPOUND
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A method for purifying an α-unsaturated amine compound represented by Formula (1), the method comprising a step of extracting with water the compound of Formula (1) from a crude product of the α-unsaturated amine compound represented by Formula (1), and a step of extracting with a pyridine solvent the α-unsaturated amine compound of Formula (1) from the aqueous solution containing the compound of Formula (1) obtained in the previous step to obtain a pyridine solvent solution of the compound of Formula (1): wherein R1 represents a hydrogen atom, a C1-4 alkyl group, a halo C1-4 alkyl group, a C1-4 alkoxy-C1-4 alkyl group, a C7-9 aralkyl group, or an optionally substituted phenyl group, R2 represents a hydrogen atom, a C1-4 alkyl group, or a C7-9 aralkyl group, and R3 represents a hydrogen atom, a C1-5 alkyl group, a halo C1-4 alkyl group, a hydroxy C1-4 alkyl group, a C1-4 alkoxy-C1-4 alkyl group, C2-4 alkenyl group, or a C7-9 aralkyl group.
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Page/Page column 7
(2010/06/15)
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- NITROGENOUS HETEROCYCLIC COMPOUNDS WITH INSECTICIDAL ACTIVITY, AND THE PREPARATION AND USE THEREOF
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The present invention relates to nitro-containing heterocyclic or ring-opening nitrogenous compounds of formula (A), wherein R1, R2, R3, R4, R5, Y, Z, and W are as defined in the specification. The present invention discloses the preparation and the uses of a novel insecticide. Said compound and the derivatives thereof have high insecticidal activity to farm insects including homoptera and Lepidoptera pests, such as aphis, fulgorides, aleyrodids, leafhopper, commom thrips, cotton bollworm, cabbage caterpillar, cabbage moth, cotton leafworm, armyworn and so on.
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Page/Page column 10
(2010/12/29)
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- Nitromethylene neonicotinoids analogues with tetrahydropyrimidine fixed cis-configuration: Synthesis, lnsecticidal activities, and molecular docking studies
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Two series of new nitromethylene neonicotinoid analogues (2a-2h and 3a-3h) were designed and prepared, with the cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed that most analogues exhibited excellent insectlcidal activities at 500 mg/L, and analogues with optical activity (2c-2g) were highly potent at 100 mg/L, while compound 2d had >90% mortality at 20 mg/L, which suggested that it could be used as a lead for future insecticides development. Modeling the ligand-receptor complexes by molecular docking study explained the structureactivity relationships observed in vitro and revealed an intriguing molecular binding mode at the active site of the nAChR model, thereby possibly providing some useful information for future receptor structure-based designs of novel insecticidal compounds.
- Chuanwen, Sun,Dingrong, Yang,Jiahua, Xing,Haifeng, Wang,Jia, Jin,Jun, Zhu
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scheme or table
p. 3415 - 3421
(2011/07/30)
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- Discovery of bis-aromatic ring neonicotinoid analogues fixed as cis-configuration: Synthesis, insecticidal activities, and molecular docking studies
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A novel series of bis-aromatic ring neonicotinoid analogues (1a-1l, 2a-2c), were designed and prepared by introducing a new substituted aromatic ring into nitenpyram and forming a tetrahydropyrimidine ring, with the cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed most analogues exhibited good insecticidal activities at 100 mg/L, and compound 1d and 2a were highly potent even at 10 mg/L. Modeling the ligand-receptor complexes by molecular docking study explained the structure-activity relationships observed in vitro, which may provide some useful information for future design of new insecticides.
- Sun, Chuanwen,Jin, Jia,Zhu, Jun,Wang, Haifeng,Yang, Dingrong,Xing, Jiahua
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scheme or table
p. 3301 - 3305
(2010/08/06)
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- Method for exterminating termites
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A method for exterminating termites comprising using an entomopathogenic nematode together with an inset-growth regulator or a slow-acting insecticide, wherein insecticidal effects are reinforced compared with the cases using singly the entomopathogenic nematode and the insect-growth regulator or the slow-acting insecticide, respectively, and a bait station for exterminating termites that contains an entomopathogenic nematode with an insect-growth regulator or a slow-acting insecticide. According to the invention, emission of harmful chemicals to environment can be suppressed. The invention is nonpoisonous for human being and livestock, and is useful for indoor or outdoor extermination of termites.
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- PROCESS FOR THE PREPARATION OF RICE SEED FOR SOWING
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A method for preparing rice seed for sowing whereby the seed is pregerminated and thereafter treated with a plant growth regulator and, optionally, a phytoprotection product such as an insecticide.
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- Method for the treatment of plants with agrochemical tablet compositions
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Novel method for applying agrochemicals to plants, which method consists in attaching to the surface of the plants tablets comprising at least one agrochemically active compound and at least one adjuvant, which is solid, liquid of pasty at room temperature, and optionally, one or more excipients optionally in admixture with one or more other additives and/or water.
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- Patch preparations for treating plants
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The following invention introduces a patch preparation for treating plants, whereas the patch preparations comprise a chemical layer composed of at least one agrochemically active compound, at least one adhesive and optionally, one or more additives. The components are dispersed in a matrix state on a substrate which are then introduced on the roots of the plant to be treated.
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- Pesticidal compositions in paste form
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Novel pasty compositions for the control of animal pests and fungal diseases on plants, which compositions comprise at least one pesticidally active or fungicidally active compound and at least one adjuvant, which is solid, liquid or pasty at room temperature and optionally, one or more excipients and water.
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- Poisonous baits for controlling soil-inhabiting pests
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A poisonous bait for controlling soil-inhabiting pests comprising an active compound for controlling a soil-inhabiting pest and, as excipient, an artificial culture medium for mushrooms or the medium obtained after culture of mushrooms.
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- Use of substituted amines for the treatment of brain function disorders
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The invention relates to the use of substituted amines for the treatment and prevention of brain function disorders. The substituted amines are suitable on the basis of their properties as agonistic or antagonistic ligands for nicotinergic receptors, in particular for the treatment and prevention of senile and presenile dementia and dementia of the Alzheimer type, and of depressions.
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- 1,1,1-trichloro-2-nitroethane production
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Methods for the production of 1,1,1-trihalogeno-2-nitroethanes from 1,1-dihalogenoethylene by using nitric acid or its salt and hydrogen chloride or hydrogen bromide or its salt, and for the production of α-unsaturated amines from the 1,1,1-trihalogeno-2-nitroethanes which are useful as insecticides.
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- Formicidal agent for combating termites
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A method of combating termites comprising combating termites and/or their habit with an effective termite combating amount of at least one active compound of the formula (I) STR1 wherein R1 represents hydrogen atom or a C1-4 alkyl group, R2 represents --S--CH3 or STR2 wherein R3 and R4 each represent hydrogen atom or a C1-4 alkyl group, Y represents CH or N, and Z represents a nitro group or a cyano group, provided that where Z represents a cyano group, then Y represents N, either alone or in admixture with an extender and/or a surface active agent.
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- Tetrahydropyrimidines, their production and use
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There is provided a pest control composition containing a compound represented by the formula, STR1 wherein R1, R2, R3 and R4 are the same or different and independently mean a hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted and X means an electron attracting group or a salt thereof. The compounds are of minimal toxicity to man, domestic animals and fish and selectively display remarkable control effect on pests.
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