- Insecticidal and neuroblocking potencies of variants of the imidazoline moiety of imidacloprid-related neonicotinoids and the relationship to partition coefficient and charge density on the pharmacophore
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The pharmacophore of the neonicotinoid insecticide imidacloprid, nitroiminoimidazolidine, was modified to heterocycles such as thiazolidine, pyrrolidine, dihydroimidazole, dihydrothiazole, and pyridone conjugated to nitroimine (=NNO2) or nitromethylene (=CHNO2). Their 6-chloro-3-pyridylmethyl or 5-chloro-3-thiazolylmethyl derivatives were examined for insecticidal activity against the American cockroach by injection and for neuroblocking activity using the cockroach ganglion. Most of the compounds having the neonicotinoidal pharmacophore exhibited insecticidal activity at the nanomolar level, which was enhanced in the presence of synergists, and high neuroblocking activity at the micromolar level. Quantitative analysis for the compounds showed that the neuroblocking potency is proportional both to the Mulliken charge on the nitro oxygen atom and to the partition coefficient log P value. The equation for the insecticidal versus neuroblocking potencies indicated that both potencies are related proportionally with each other when the other factors are the same.
- Kagabu, Shinzo,Ishihara, Rika,Hieda, Yosuke,Nishimura, Keiichiro,Naruse, Yuji
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- Synthesis and Insecticidal Evaluation of N-Substituted 2-Nitroiminoimidazolidines
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N-substituted and N,N'-disubstituted 2-nitroiminoimidazolidines were prepared from 2-nitroiminoimidazoline. The feeding-contact and systemic activities as insecticides of some of these new compounds have been evaluated.
- Boelle, Jerome,Schneider, Raphael,Gerardin, Philippe,Loubinoux, Bernard
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Read Online
- Method for synthesizing imidacloprid at high yield
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The invention provides a method for synthesizing imidacloprid at a high yield. 2-chloro-5-chloromethylpyridine, ethylenediamine and cyanogen halide, which are used as raw materials, are aminated, cyclized and nitrified to synthesize the imidacloprid. The method has the advantages of high safety in the production process, good purity and high yield of the product, and easiness in industrializationrealization.
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- Synthetic method of imidacloprid
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The invention provides a synthetic method of imidacloprid, which comprises the following steps: by using 2-chloro-5-chloromethylpyridine, ethylenediamine and guanidine nitrate as raw materials, carrying out aminating, cyclizing, dehydrating and the like to synthesize imidacloprid. According to the method, the safety problem caused by generation of unstable nitroguanidine in the reaction process isavoided, the production process is high in safety, the product purity is good, the yield is high, and industrialization is easy to realize.
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Paragraph 0017; 0020; 0030-0032
(2020/03/02)
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- A MANUFACTURING PROCESS FOR 2-NITROIMINO HETEROCYCLIC COMPOUNDS
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The present invention relates to a process for manufacture of 2-nitroimino heterocyclic compounds and intermediates thereof. More particularly, the present invention relates to a convenient manufacturing process for preparation of 2-nitroimino imidazolidine compounds.
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Paragraph 26
(2020/04/25)
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- Novel nicotinoid structures for covalent modification of wood: An environmentally friendly way for its protection against insects
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Timber is constantly exposed to environmental influences under outdoor conditions which limits its lifetime and usability. In order to counteract the damaging processes caused by insects, we have developed a novel and more environmentally friendly method to protect wood materials via covalent modification by organic insecticides. Starting with an important class of synthetic insecticides which are derived from the natural insecticide nicotine, various new carboxylic acid derivatives of imidacloprid were made accessible. These activated neonicotinoids were utilized for the chemical modification of wood hydroxy groups. In contrast to conventional wood preservation methods in which biocides are only physically bound to the surface for a limited time, the covalent fixation of the preservative guarantees a permanent effect against wood pests, demonstrated in standardized biological tests. Additionally, the environmental interaction caused by non-bound neonicotinoids is significantly reduced, since both, a smaller application rate is required and leaching of the active ingredient is prevented. By minimizing the pest infestation, the lifetime of the material increases while preserving the natural appearance of the material.
- Acker, Sophie,Kaufmann, Dieter E.,Namyslo, Jan C.,Plarre, Rudy,S?ftje, Martin
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p. 15726 - 15733
(2020/05/13)
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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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- Cascade reaction synthesis method of the Imidacloprid
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The invention discloses a method for synthesizing imidacloprid employing cascade reaction. The method comprises the following steps: with 2-chlorine-5-chloromethyl pyridine, ethidene diamine and guanidine nitrate as raw materials, mixing 2-chlorine-5-chloromethyl pyridine, ethidene diamine and guanidine nitrate with a certain amount of solvent ethanol; adding a little of ionic liquid as a catalyst, controlling the pH value of the reaction process to be about 6 with a little of hydrochloric acid; heating, warming, and slowly dropwise adding a certain amount of ethidene diamine, reacting, heating for a certain period of time, stopping heating, and cooling to a room temperature; and purifying and drying to obtain an imidacloprid product. Due to adoption of one-pot cascade reaction, an intermediate product 2-degree amine is high in activity, and easily forms a heterocyclic ring together with nitroguanidine; byproducts can be prevented; and the high-purity imidacloprid is synthesized. Compared with an original two-step technology, the method for preparing the imidacloprid disclosed by the invention is simple in reaction step; the yield and the purity of the product are greatly improved; the yield reaches more than or equal to 95%; the purity of a reaction product through gas chromatography reaches more than or equal to 90%.
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Paragraph 0024; 0025; 0026; 0027; 0028; 0029; 0030; 0031
(2017/10/20)
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- Method for synthesizing imidacloprid
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The invention relates to the chemical field, and discloses a method for synthesizing imidacloprid. The method comprises the following steps: enabling nitroguanidine, 70% sulfuric acid, ethanediamine, 2-cholo-5-chloromethyl pyridine to react, wherein the reaction steps comprise the following steps: adopting nitroguanidine and 70% sulfuric acid, dropwise adding ethanediamine, and heating to a temperature being 80 DEG C to synthesize an intermediate imidazolidine; adding acetonitrile, the imidazolidine, potassium carbonate and CsCl to mix, dropwise adding an acetonitrile solution dissolved with 2-cholo-5-chloromethyl pyridine, heating and refluxing to react for 5 hours, and filtering to obtain the imidacloprid. According to the method, the product imidacloprid can be obtained by virtue of two-step reaction; and the preparation method is safe, environmentally friendly, suitable for industrial production, and has a wide application prospect.
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Paragraph 0004; 0005; 0016; 0017; 0018
(2017/01/02)
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- Process for the preparation of polymorphs of imidacloprid
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A process for the preparation of a Form I crystalline polymorph of imidacloprid, including: (i) dissolving imidacloprid in an appropriate amount of aqueous solvent or mixture of solvents to obtain an aqueous solution; (ii) cooling the aqueous solution slowly, thereby forming crystals of polymorph Form I of imidacloprid; (iii) isolating the crystals. A process for the preparation of a Form II crystalline polymorph of imidacloprid, comprising: dissolving imidacloprid in an appropriate amount of non-aqueous solvent or mixture of non-aqueous solvents to obtain a non-aqueous solution; (ii) cooling the solution rapidly, thereby forming crystals of polymorph Form II of imidacloprid; (iii) isolating the crystals.
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Page/Page column 7
(2016/01/09)
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- Process for the preparation of the insecticide imidacloprid
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A process for the preparation of the insecticide imidacloprid includes the reaction of 2-chloro-5-chloromethyl pyridine with 2-nitroiminoimidazolidine, carried out in the molar ratio of 1:1 to 1:1.2, in the presence of an alkali metal hydroxide in an aprotic solvent at 45 to 60° C. under stirring.
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Page/Page column 2
(2008/06/13)
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- Active agent combinations
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The novel active compound combinations of extracts from seeds of the neem tree and the active compounds of groups (B) to (F) listed in the description have very good insecticidal and acaricidal properties.
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- PROCESS FOR THE PREPARATION OF DIAMINE SINGLE-SIDED CONDENSATION PRODUCTS
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Disclosed is a preferred process for preparation of diamine single-sided condensation products. The preferred process involves gradually co-feeding stoichiometric amounts of a heterocyclic compound and a diamine compound into an organic solvent in the presence of an alkali carbonate while heating at ≧60° C. This preferred process can increase the reaction rate, improve yield, minimize double-sided condensation byproduct, and produce a high-quality product.
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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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- Preparation of new imidacloprid analogues
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A 3-step synthesis of the biologically active metabolites (2 and 3) of imidacloprid from aminoacetaldehyde diethyl acetal or ethylenediamine was developed. A series of new imidacloprid analogues were also prepared.
- Novak, Lajos,Hornyanszky, Gabor,Kiraly, Imre,Rohaly, Janos,Kolonits, Pal,Szantay, Csaba
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- Agents for preserving technical materials against insects
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The use of the compounds of the formula (I) as agents for preserving technical materials against insects.
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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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- Capsule preparations for plant treatment
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Novel capsule preparations for the treatment of plants, which preparations are composed of A) a capsule shell comprising water-soluble polyoxyethylene having a number average molecular weight of 100,000 or more, at least one plasticizer and optionally, one or more additives, and B) a filling comprising at least one biologically active compound and optionally, one or more auxiliaries, and a method for administering biologically active compounds to plants, such as trees and shrubs, by inserting the novel capsule preparations into the plants.
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- Fungicidal active compound combinations
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The present application relates to new active compound combinations composed, on the one hand, of prior art compounds metaconazole, 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl-methyl)cyclopentanol and imidacloprid, 1-[(6-chloro-3-pyridinyl)-methyl]-4,5-dihydro-N-nitro-1H-imidazole-2-amine, and, on the other hand, of other prior-art active compounds, the combinations being extremely suitable for the protection of wood products.
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- Anti-fouling compositions
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An anti-fouling composition comprising a carrier, and a binder, the improvement which comprises an effective amount of at least one insecticide. The composition is applied to the surfaces of articles which come into contact with seawater or brackish water, especially wood. Other conventional anti-fouling agents may also be present.
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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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- Agrochemical formulations for water surface application
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New agrochemical formulations for application to the water of paddy fields, which formulations comprise A) at least one solid core material having an apparent specific density of less than 1 and a particle diameter within the range from about 300 μm to about 1,400 μm, and B) a coating layer comprising at least one biologically active compound, at least one substance having the ability to reduce the interfacial tension between water and air, at least one oily substance and, if appropriate, one or more additives, and the use of such agrochemical formulations for applying biologically active compounds to the water of paddy fields.
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- Nitroimino compound as intermediate for insecticides and pharmaceuticals
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Nitroinimo compound as intermediate for insecticides and pharmaceauticals of the formula I STR1 wherein R1 and R2 are the same or different from each other and denote lower alkyl of 1 to 4 carbon atoms.
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- PROCESS FOR PRODUCING NITROGENOUS HETEROCYCLE
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A process for producing a nitrogenous heterocycle represented by general formula (III) by the reaction of an N-nitroimidodithiocarbonate represented by general formula (I) with a diamine represented by general formula (II), wherein R1 and R2 represent each alkyl; R3 and R4 represent each hydrogen or alkyl which may be substituted with a heterocycle; R5 represents hydrogen or alkyl; and n represents 2 to 4.
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- Heterocyclic compounds
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Novel insecticides of the formula STR1 in which n is 0 or 1, X is S, O, STR2 Y is N or STR3 Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R9 variously represent hydrogen or specified organic radicals.
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