- Use of prochloraz for wood protection
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The active compound prochloraz and fungicidal compositions based on prochloraz are highly suitable for protecting wood and timber products against attack and/or destruction by soft-rot fungi.
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- Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively
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We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.
- Nakatsuji, Hidefumi,Morimoto, Mami,Misaki, Tomonori,Tanabe, Yoo
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p. 12071 - 12080
(2008/03/13)
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- Water solvent method for esterification and amide formation between acid chlorides and alcohols promoted by combined catalytic amines: Synergy between N-methylimidazole and N,N,N′,N′-tetramethylethylenediamine (TMEDA)
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An efficient method for esterification between acid chlorides and alcohols in water as solvent has been developed by combining the catalytic amines, N-methylimidazole and N,N,N′,N′-tetramethylethylenediamine (TMEDA). The present Schotten-Baumann-type reaction was performed by maintaining the pH at around 11.5 using a pH controller to prevent the decomposition of acid chlorides and/or esters and to facilitate the condensation. The choice of catalysts (0.1 equiv.) was crucial: the combined use of N-methylimidazole and TMEDA exhibited a dramatic synergistic effect. The catalytic amines have two different roles: (i) N-methylimidazole forms highly reactive ammonium intermediates with acid chlorides and (ii) TMEDA acts as an effective HCl binder. The production of these intermediates was rationally supported by a careful 1H NMR monitoring study. Related amide formation was also achieved between acid chlorides and primary or secondary amines, including less nucleophilic or water-soluble amines such as 2-(or 4-)chloroaniline, the Weinreb N-methoxyamine, and 2,2-dimethoxyethanamine.
- Nakatsuji, Hidefumi,Morita, Jun-Ichi,Misaki, Tomonori,Tanabe, Yoo
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p. 2057 - 2062
(2007/10/03)
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- Method for producing cyclopropanecarboxylates
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There is disclosed a method for producing cyclopropanecarboxylates of the formula (3): by transesterification in the presence of a lanthanoid metal alkoxide
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- Methods for producing cyclopropane carboxylates
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There is provided a method for producing a cyclopropanecarboxylate of formula (3): wherein R1, R2, R3, R4 and R5 each independently represent:a hydrogen atom, halogen atom,an optionally substituted alkyl group and the like; andR7 represents:an optionally substituted alkyl group, and the like,which is characterized byreacting a cyclopropanecarboxylate of the formula (1) wherein R1, R2, R3, R4 and R5 are as defined above, andR6 represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group,with a monohydroxy compound of the formula (2):R7OH ??(2) wherein R7 is the same as defined above,in the presence of an alkali metal hydroxide.
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- Method for producing cyclopropanecarboxylates
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There is provided a method for producing a cyclopropanecarboxylate of formula (1):???which comprises contacting???a cyclopropanecarboxylate of formula (2):???with a monohydroxy compound of formula (3):R7OH???in the presence of a lithium compound of formula (4):R8OLiwherein R1, R2, R3, R4and R5each independently representa hydrogen atom, a halogen atom,a substituted or unsubstituted alkyl group,a substituted or unsubstituted alkenyl group, ora substituted or unsubstituted aryl group;R6represents an alkyl group having 1 to 10 carbon atoms ora substituted or unsubstituted phenyl group;R7and R8do not simultaneously represent the same and each independently representa substituted or unsubstituted alkyl group, ora substituted or unsubstituted aryl group.
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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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- Para-hydroxyphenylacetic acid for reducing the repellency of insecticides
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The present invention relates to the new use of p-hydroxyphenylacetic acid, by itself or in a mixture with other chemical compounds, for reducing the repellency of insecticides in the control of cockroaches, and to cockroach control compositions which comprise these mixtures, details being found in the description.
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- Search for Routes of Synthesis of Permethrin and Chloropermethrin Starting from Halogen-containing Alkenoic Acids
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Promising procedures were developed for the synthesis of permethrin and I-chloropermethrin starting from acid chloride, nitrile, and esters of 3,3-dimethyl-2,2,4,6,6-pentachloro-5-alkenoic acid and 3,3-dimethyl-2,2,6,6-tetrachloro-5-alken-4-olide, which were prepared by adding derivatives of trichloroacetic acid to 1,1-dichloro-4-methyl-1,3-pentadiene in the presence of catalytic amounts of monovalent copper ions and amine.
- Badanyan,Stepanyan,Mikaelyan,Ovivyan,Panosyan
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- A Practical and Efficient Synthesis of Fluorinated Pyrethroids. cis-3-(2-Chloro--3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates
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A practical and efficient route to fluorinated pyrethroids has been developed which involves the selective formation of the cis-cyclopropane ring using intramolecular alkylation of the haloaldehyde and a novel transformation of the aldehydes to the corresponding esters via the cyanohydrins.
- Nishida, Mayumi,Fuchikami, Takamasa,Kondo, Kiyosi
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p. 703 - 706
(2007/10/02)
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- Methods and agents for combating cockroaches
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The present invention relates to the use of compounds of the general formula I STR1 in which R1 represents C1 -C5 -alkyl or hydroxy-C1 -C5 -alkyl; R2 represents C1 -C5 -alkyl; and m represents an integer from 10 to 20, for combating cockroaches.
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- Pesticidal composition containing a microencapsulated organo-phosphorus or carbamate in a pyrethroid dispersion
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An insecticidal and/or acaricidal and/or nematicidal composition having a rapid efficacy and residual activity which comprises a mixture of a poorly water-soluble organophosphorus insecticide and/or acaricide and/or nematicide and/or a poorly water-soluble carbamate insecticide and/or acaricide which have been microencapsulated in water-insoluble polymer coatings with a dispersing agent used in forming a microcapsule part, with a poorly water-soluble pyrethroid insecticide and/or acaricide emulsified or suspended in water with the above-mentioned dispersing agent used in forming a flowable part.
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- Insecticidal aerosol
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A mono-layer liquid phase type water-based insecticidal aerosol comprises (A) a base liquid for aerosol containing at least one specific pyrethroidal compound, a specific organic solvent and a buffer solution, which base liquid has a pH of from 7.0 to 9.0 and (B) dimethyl ether as a propellant. The aerosol according to the present invention has a long-term storage stability, as well as an excellent insecticidal activity and causes no degradiation of the container.
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- 1,5-Disubstituted imidazoles as inhibitors of juvenile hormone
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The present invention provides a 1,5-disubstituted imidazole represented by the formula (1) STR1 wherein R1 is a lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group, and R2 is a 2,6-dimethyl-1,5-heptadienyl group or a 2,6-dimethylheptyl group, except for a compound wherein R1 is a phenyl lower alkyl group and R2 is a 2,6-dimethyl-1,5-heptadienyl group, and a salt thereof, a process for their preparation and an active agent able to inhibit the activity of the juvenile hormone.
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- Insecticidal resin coating film
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An insecticidal resin coating film comprising a combination of an acrylonitrile and/or methacrylonitrile copolymer resin and an insecticidal component selected from the group consisting of specified compounds exhibits an insecticidal effect, since the compound is kept on the surface of the coating film in a state capable of exhibiting its insecticidal effect for a long period of time.
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- Long-acting pyrethrum/pyrethroid based pesticides with silicone stabilizers
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Pesticidal compositions based on nontoxic, naturally unstable insecticides (pyrethrum, synthetic pyrethroids and mixtures thereof) include a liquid alkyl aryl silicone polymer which stabilizes the insecticide to provide an extended effective killing life. The compositions additionally include a synergist to provide an immediate killing action and an antioxidant to protect the insecticide against destruction by oxygen. Ultraviolet protectants and insect repellents may also be included. Applications include control of insect pests to animals and plants and general purpose insect control. Exemplary formulations are given for compositions to be applied as sprays, dips, powdered or dusts, foggers and shampoos.
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- Process for preparing dihalovinylcyclopropanecarboxylic acids
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A cyclopropanecarboxylic acid of the formula STR1 is prepared by the reaction of a compound of the formula STR2 with an alkali metal hydroxide or alkaline earth metal hydroxide in an ether type solvent. R1, R2, and R4 each independently is hydrogen or a hydrocarbon residue, R3 is hydrogen or lower alkyl, X is halogen, and A is --CH2 --CX, 3 or --CH=CX2.
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- Process for preparing dihalovinylcyclopropanecarboxylates
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Novel syntheses of dihalovinylcyclopropanecarboxylates, including potent insecticides, are described. The processes begin with the reaction between an alkenol and an orthoester to produce a γ-unsaturated carboxylate, followed by the catalyzed addition of a carbon tetrahalide to the double bond and dehydrohalogenation to produce a cyclopropane derivative.
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- Preparation of halogenovinyl-substituted tetra-hydrofuran-2-ones
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Halogenovinyl-substituted tetrahydrofuran-2-ones of the formula STR1 are prepared by reacting a peracid such as peracetic, perpropionic or m-chloroperbenzoic acid with a halogenvinyl-substituted cyclobutanone of the formula STR2 in which R1 to R8 can be hydrogen, halogen, cyano or various organic radicals, or in pairs can make up a ring. Products wherein R3 is not hydrogen or R1 is not halogen are new. The products are useful as intermediates in making insecticides.
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- Process for preparation of substituted cyclopropane carboxylic acids and esters thereof and intermediates of said acids and esters
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When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a γ-halogeno-δ-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.
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- Preparation of esters of m-phenoxybenzyl alcohol and its α-cyano and α-ethinyl derivatives with 2,2-dimethylcyclopropanecarboxylic acids
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Process for the preparation of esters of m-phenoxybenzyl alcohol and its α-cyano and α-ethinyl derivatives with carboxylic acids containing at least 6 carbon atoms by heating together a methyl or ethyl ester of the carboxylic acid, an ester of m-phenoxyphenyl alcohol or its α-cyano or α-ethinyl derivative with an acid of the formula R.CO2 H wherein R is an alkyl group containing not more than 3 carbon atoms, and tetramethyl or tetraethyl titanate at a temperature such that the methyl or ethyl ester of the acid of formula R.CO2 H is removed by distillation as it is formed.
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