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    • 94. 发明授权
      US3689574A 3,4,5-trimethylcyclohexanol 失效
    • 3,4,5-trimethylcyclohexanol
    • 3,4,5-三甲基环己烷
    • US3689574A
    • 1972-09-05
    • US3689574D
    • 1970-04-28
    • EXXON RESEARCH ENGINEERING CO
    • ENGELHART JOHN E
    • A01N31/06 , A01P3/00 , C07C20060101 , C07C35/00 , C07C35/08 , C07C35/18 , A01N9/24
    • C07C2601/14
    • 3,4,5-TRIALKYLCYCLOHEXANOLS CHARACTERIZED BY THE FOLLOWING STRUCTURAL FORMULA:

      This invention relates to a class of novel compounds. In one aspect this invention relates to new compositions of matter, namely, 3,4,5-trialkylcyclohexanols, wherein R1, R2 and R3 may be the same or different C1-C3 alkyl groups. In another aspect this invention relates to the employment of 3,4,5trialkylcyclohexanols as broad spectrum fungicides. Although substituted cyclohexanols have long been known to the art, the specific compounds of this invention, 3,4,5trialkylcyclohexanols, have never been prepared. These novel compositions can be characterized by the following general formula:

      sieving, purification, and/or other treatments - including, for example, gypsum; tripolite; diatomaceous earth; mineral silicates such as mica, vermiculite, talc, and pyrophyllite; clays of the montmorillonite, kaolinite, or attapulgite groups; calcium or magnesium limes, or calcite and dolomite; etc. Carriers produced synthetically, as for example, synthetic hydrated silica oxides and synthetic calcium silicates can also be used, and many proprietary products of this type are available commercially. The carrier can also be an elemental substance such as sulfur or carbon, preferably an activated carbon. If the carrier possesses intrinsic catalytic activity such that it would decompose the active ingredient, it is advantageous to incorporate a stabilizing agent, as for example, polyglycols such as diethylene glycol, to neutralize this activity. For some purposes, a resinuous or waxy carrier can be used, preferably one which is solvent soluble or thermoplastic, including fusible materials. Examples of such carriers are natural or synthetic resins such as a coumarone resin, rosin, copal, shellac, dammar, polyvinyl chloride, styrene polymers and copolymers, a solid grade of polychlorophenol such as is available under the registered trademark ''''Arochlor'''', a bitumen, an asphaltite, a wax for example, beeswax or a mineral wax such as paraffin wax or montan wax, or a chlorinated mineral wax, or a microcrystalline wax such as those available under the registered trademark ''''Mikrovan Wax. '''' COmpositions comprising such resinous or waxy carriers are preferably in granular or pelleted form. Fluid carriers can be liquids, as for example, water or an organic fluid, including a liquefied normally vaporous or gaseous material, or a vaporous or gaseous material, and can be solvents or nonsolvents for the active material. For example, the horticultural petroleum spray oils boiling in the range of from about 275* to about 575* F., or boiling in the range of about 575* to about 1,000*F. and having an unsulfonatable residue of at
      Specific examples of compounds of this invention are the following: Compound Name 1 3,4,5-trimethylcyclohexanol 2 3,4,5triethylcyclohexanol 3 3,4,5-tripropylcyclohexanol 4 3,5dimethyl-4-ethylcyclohexanol 5 3,5-dimethyl-4-propylcyclohexanol 6 3,4-diethyl-5-methylcyclohexanol 7 3,4-dimethyl-5ethylcyclohexanol 8 3,5-dipropyl-4-methylcyclohexanol 9 3,5dimethyl-4-isopropylcyclohexanol 10 3,5-diisopropyl-4methylcyclohexanol 11 3-methyl-4-propyl-5-ethylcyclohexanol 12 3-ethyl-4-propyl-5-isopropylcyclohexanol 3,4,5-TRIALKYLCYCLOHEXANOLS CAN BE PREPARED BY REDUCING 3,4,5TRIALKYLPHENOLS. This reduction can occur at a temperature ranging from 50* to 300* C., preferably 100* C. to 200*C. under a hydrogen pressure of 500 psi to 5,000 psi, preferably from 1,000 psi to 2,500 psi. Suitable solvents for this reaction are as follows: lower alkanols, saturated hydrocarbon solvents, acetic acid, water and alcohol-water combinations. Suitable hydrogenation catalysts for this reduction are RaneyNickel, ruthenium, rhodium, rhenium, platinum oxide, each of which may be on a suitable support such as alumina, charcoal, kieselguhr, silica gel, barium or calcium carbonates. One pertinent starting reactant, 3,4,5-trimethylphenol, is a commercially available material and its preparation is described in U.S. Pat. Nos. 3,385,902 and 3,385,903. A typical method of synthesis of 3,4,5-trimethyl-cyclohexanol is given in Example I. 3,4,5-trialkylcyclohexanols have been found to possess fungicidal properties. A 3,4,5-trialkylcyclohexanol can be made into a fungicidal compositiOn by admixing one or more of the active ingredients with a conditioning agent of the kind used and referred to in the art as a pest control modifier to provide formulations adapted for ready and efficient application to soil or foliage using conventional applicator equipment. The compounds of the invention have general fungicidal properties. They are especially useful in certain types of foliar fungus control such as, for example, in application to crop lands to give control of the common pathogens, without harming the crop plants. Fungicidal compositions of the invention are prepared by admixing one or more of the active ingredients defined heretofore, in fungicidally effective amounts with a conditioning agent of the kind used and referred to in the art as a pest control adjuvant or modifier to provide formulations adapted for ready and efficient application to soil or foliage using conventional applicator equipment. Thus, the fungicidal compositions or formulations are prepared in the form of solids or liquids. Solid compositions are preferably in the form of granulars or dusts. The compositions can be compounded to give homogeneous freeflowing dusts by admixing the active compound or compounds with finely divided solids preferably talc, natural clays, pyrophyllite, diatomaceous earth, or flours such as walnut shell, wheat, redwood, soya bean, and cottonseed flours. Other inert solid conditioning agents or carriers of the kind conventionally employed in preparing pest control compositions in powdered form can be used. Granulars can be compounded by absorbing the compound in liquid form onto a preformed granular diluent. Such diluents as natural clays, pyrophyllite, diatomaceous earth, flours such as walnut shell, as well as granular sand can be employed. In addition, granulars can also be compounded by admixing the active ingredient with one of the powered diluents described hereinabove, followed by the step of either pelleting or extruding the mixture. Liquid compositions of the invention are prepared in the usual way by admixing one or more of the active ingredients with a suitable liquid diluent medium. In the cases where the compounds are liquids, they may be sprayed in ultra low volume as such. With many solvents, such as alkylated naphthalene or other aromatic petroleum solvents, dimethyl formamide, cycloalkanones, relatively high up to about 50 percent by weight or more concentration of the active ingredient can be obtained in solution. The fungicidal compositions of the invention whether in the form of dust or liquids, preferably also include a surface-active agent sometimes referred to in the art as a wetting, dispersing, or emulsifying agent. These agents, which will be referred to hereinafter more simply as surface-active dispersing agents, cause the compositions to be easily dispersed in water to give aqueous sprays which, for the most part, constitute a desirable composition for application. The surface-active dispersing agents employed can be of the anionic, cationic, or nonionic type and include, for example, sodium and potassium oleate, the amine salts of oleic acid, such as morpholine and dimethylamine oleates, the sulfonated animal and vegetable oils, such as sulfonated fish and castor oils, sulfonated petroleum oils, sulfonated acyclic hydrocarbons, sodium salt of lignin sulfonic acid (goulac), alkylnaphthalene sodium sulfonate, sodium salts of sulfonated condensation products of naphthalene and formaldehyde, sodium lauryl sulfate, disodium monolauryl phosphate, sorbitol laurate, pentaerythritol monostearate, glycerol monostearate, diglycol oleate, polyethylene oxides, ethylene oxide condensation products with stearyl alcohol and alkylphenol, polyvinyl alcohols, salts, such as the acetate of polyamines from reductive amination of ethylene/carbon monoxide polymers, laurylamine hydrochloride, laurylpyridinium bromide, stearyl trimethylammonium bromide, cetyldimethylbenzYl ammonium chloride, lauryldimethylamine oxide, and the like. Generally, the surface-active agent will not comprise more than about 5 to 15 percent by weight of the composition, and in certain compositions the percentage will be 1 percent or less. Usually, the minimum lower concentration will be 0.1 percent. The fungicidal compositions are applied either as a spray, granular or a dust to the locus or area to be protected from fungal infection. Such application can be made directly upon the locus or area during the period of fungal infestation in order to destroy the fungal pathogen, but preferably, the application is made in advance of an anticipated fungus infestation to prevent such infestation. Thus, the compositions can be applied as aqueous foliar sprays but can also be applied as sprays directly to the surface of the soil. Alternatively, the dry powdered compositions can be dusted directly on the plants or on the soil. The active compound is, of course, applied in an amount sufficient to exert the desired fungicidal action. The amount of the 3,4,5-trialkylcyclohexanol present in the compositions as actually applied for destroying or preventing fungus infections will vary with the manner of application, the particular pathogens for which control is sought, the purpose for which the application is being made, and like variables. In general, the fungicidal compositions as applied in the form of a spray, dust or granular, will contain from about 0.1 to 100 percent by weight of 3,4,5-trialkylcyclohexanol. Fertilizer materials, other fungicidal agents, and other pest control agents such as insecticides and herbicides can be included in the fungicidal compositions of the invention if desired. The term ''''carrier'''' or ''''diluent'''' as used herein means a material, which can be inorganic or organic and synthetic or of natural origin, with which the active ingredient is mixed or formulated to facilitate its storage, transport, and handling and application to the plants to be treated. The carrier is preferably biologically and chemically inert, and as used, can be a solid or fluid. When solid carriers are used, they are preferably particulate, granular, or pelleted; however, other shapes and sizes of solid carrier can be employed as well. Such preferable solid carriers can be natural occuring minerals although subsequently subjected to grinding,
    • 其特征在于以下结构式：其中R 1，R 2和R 3可以是相同或不同的C 1 -C 3烷基。 已经发现这些化合物具有独特的广谱杀真菌活性。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 97. 发明申请
      US20190389793A1 CONTROL AND REPELLENCY OF BED BUGS 审中-公开
    • CONTROL AND REPELLENCY OF BED BUGS
    • US20190389793A1
    • 2019-12-26
    • US16559752
    • 2019-09-04
    • BEDOUKIAN RESEARCH, INC.
    • Robert H. Bedoukian
    • C07C69/675 , A01N31/06 , A01N37/18 , A01N43/08 , A01N43/16 , A01N37/22 , A01N37/36 , A01N37/42 , C07C35/06 , C07C35/18 , C07C59/205 , C07C69/708 , C07C235/74 , C07D307/33 , C07D309/30
    • Control or repellency of bed bugs is accomplished by bringing the bed bugs into contact with at least one of the compounds of the structure (I) Wherein R is selected from —OH, —OC(O)R4, —OR6, —(OR6)2, wherein each R6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R4 is a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms; X is O or CH2, with the proviso that when X is O, R can only be ═O; each Z is independently selected from (CH) and (CH2) y is a numeral selected from 1 and 2; R1 is selected from H or a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms. R2 is selected from H and a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms. R3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, —(CH2)nOH, —C(O)OR5, —CH2C(O)OR7, —CH2C(O)R8, —C(O)NR9R10, —CH2C(O)NR11R12 where each of R5, R7, R8, R9, R10, R11 and R12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is an integer of from 1 to 12; and the bond between the 2 and 3 positions in the ring structure may be a single or a double bond, and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Global Dossier Espacenet 法律信息 同族专利 专利引用
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