- Conventional chiralpak ID vs. capillary chiralpak ID-3 amylose tris-(3-chlorophenylcarbamate)-based chiral stationary phase columns for the enantioselective HPLC separation of pharmaceutical racemates
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A comparative enantioselective analysis using immobilized amylose tris-(3-chlorophenylcarbamate) as chiral stationary phase in conventional high-performance liquid chromatography (HPLC) with Chiralpak ID (4.6mm ID×250mm, 5μm silica gel) and micro-HPLC with Chiralpak ID-3 (0.30mm ID×150mm, 3μm silica gel) was conducted. Pharmaceutical racemates of 12 pharmacological classes, namely, α- and β-blockers, anti-inflammatory drugs, antifungal drugs, dopamine antagonists, norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, diuretics, antihistaminics, anticancer drugs, and antiarrhythmic drugs were screened under normal phase conditions. The effect of an organic modifier on the analyte retentions and enantiomer recognition was investigated. Baseline separation was achieved for 1-acenaphthenol, carprofen, celiprolol, cizolirtine carbinol, miconazole, tebuconazole, 4-hydroxy-3-methoxymandelic acid, 1-indanol, 1-(2-chlorophenyl)ethanol, 1-phenyl-2-propanol, flavanone, 6-hydroxyflavanone, 4-bromogluthethimide, and pentobarbital on the 4.6mm ID packed with a 5μm silica column using conventional HPLC. Nonetheless, baseline separation was achieved for aminoglutethimide, naftopidil, and thalidomide on the 0.3mm ID packed with a 3μm silica capillary column. Chirality 26:677-682, 2014.
- Ahmed, Marwa,Gwairgi, Marina,Ghanem, Ashraf
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Read Online
- Preparation of a novel bridged bis(β-cyclodextrin) chiral stationary phase by thiol-ene click chemistry for enhanced enantioseparation in HPLC
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A bridged bis(β-cyclodextrin) ligand was firstly synthesized via a thiol-ene click chemistry reaction between allyl-ureido-β-cyclodextrin and 4-4′-thiobisthiophenol, which was then bonded onto a 5 μm spherical silica gel to obtain a novel bridged bis(β-cyclodextrin) chiral stationary phase (HTCDP). The structures of HTCDP and the bridged bis(β-cyclodextrin) ligand were characterized by the 1H nuclear magnetic resonance (1H NMR), solid state 13C nuclear magnetic resonance (13C NMR) spectra spectrum, scanning electron microscope, elemental analysis, mass spectrometry, infrared spectrometry and thermogravimetric analysis. The performance of HTCDP in enantioseparation was systematically examined by separating 21 chiral compounds, including 8 flavanones, 8 triazole pesticides and 5 other common chiral drugs (benzoin, praziquantel, 1-1′-bi-2-naphthol, Tr?ger's base and bicalutamide) in the reversed-phase chromatographic mode. By optimizing the chromatographic conditions such as formic acid content, mobile phase composition, pH values and column temperature, 19 analytes were completely separated with high resolution (1.50-4.48), in which the enantiomeric resolution of silymarin, 4-hydroxyflavanone, 2-hydroxyflavanone and flavanone were up to 4.34, 4.48, 3.89 and 3.06 within 35 min, respectively. Compared to the native β-CD chiral stationary phase (CDCSP), HTCDP had superior enantiomer separation and chiral recognition abilities. For example, HTCDP completely separated 5 other common chiral drugs, 2 flavanones and 3 triazole pesticides that CDCSP failed to separate. Unlike CDCSP, which has a small cavity (0.65 nm), the two cavities in HTCDP joined by the aryl connector could synergistically accommodate relatively bulky chiral analytes. Thus, HTCDP may have a broader prospect in enantiomeric separation, analysis and detection. This journal is
- Gong, Bolin,Guo, Siyu,Zhang, Ning
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p. 35754 - 35764
(2021/12/02)
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- Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC
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A triazole-bridged bis(β-cyclodextrin) was synthesized via a high-yield Click Chemistry reaction between 6-azido-β-cyclodextrin and 6-propynylamino-β-cyclodextrin, and then it was bonded onto ordered silica gel SBA-15 to obtain a novel triazole-bridged bis (β-cyclodextrin)–bonded chiral stationary phase (TBCDP). The structures of the bridged cyclodextrin and TBCDP were characterized by the infrared spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β-blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and eight dansyl amino acids were successfully resolved on TBCDP under the reversed phase with the resolutions of hexaconazole, 2′-hydroxyflavanone, and dansyl-DL-tyrosine, which were 2.49, 5.40, and 3.25 within 30 minutes, respectively. The ten β-blockers were also separated under the polar organic mode with the resolution of arotinolol reached 1.71. Some related separation mechanisms were discussed preliminary. Compared with the native cyclodextrin stationary phase (CDSP), TBCDP has higher enantioselectivity to separate more analytes, which benefited from the synergistic inclusion ability of the two adjacent cavities and bridging linker of TBCDP, thereby enabling it a promising prospect in chiral drugs and food analysis.
- Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng
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p. 168 - 184
(2019/11/25)
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- A class of compounds and its preparation method (by machine translation)
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The invention provides a class of compounds and its preparation method, by chlorine and alcohol compound the formula (I) shown in pesticide compound or its pharmaceutically acceptable salt, by the structural formula (III) as shown by a aryl (heteroaryl) [...][...] reagent with the structural formula (II) shown on the phenyl ethyl ketone nucleophilic addition reaction: (by machine translation)
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Paragraph 0054-0056
(2019/05/16)
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- Preparation method of tebuconazole midbody and preparation method of tebuconazole
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The invention relates to a preparation method of a tebuconazole midbody and a preparation method of tebuconazole. The preparation method of the tebuconazole midbody comprises the following steps of: adding 1-(4-chlorophenyl)-4,4-dimethyl-3-pentanone, trimethylthion chloride or trimethylsulfoxonium bromide, a base and a solvent into a reactor, and carrying out stirring reaction to obtain the tebuconazole midbody; the structural formula of the tebuconazole midbody is as shown in the specification; and the preparation method of the tebuconazole comprises the following steps of: adding triazole salt into the reaction system prepared by the preparation method of the tebuconazole midbody, and carrying out reaction at 110 to 130 DEG C to obtain the tebuconazole. The preparation methods are new routes for synthesizing tebuconazole, are relatively simple in process, easy to get raw materials, relatively low in toxicity of reagents and drugs used in the operation process, mild in reaction conditions and short in time; and compared with conventional methods, the preparation methods are simpler to operate and higher in total yield, so that the synthesis cost is greatly reduced, the three wastes are less, the target products are high in content, and the preparation methods are very suitable for industrial production.
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Paragraph 0026-0027; 0028-0029; 0030-0031; 0032-0039
(2019/02/26)
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- Method for reducing 1,3,4-triazole substituent in 1,2,4-triazole alkylation reaction process
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The invention relates to a method for reducing a 1,3,4-triazole substituent in 1,2,4-triazole alkylation reaction process. The method comprises the steps that 1, 2, 4-triazole and an alkylation reagent are subjected to an alkylation reaction in the presence of an alkali and a catalyst, after the reaction is finished, 1, 2, 4-triazole substituent is obtained through aftertreatment, and the catalystis one or a combination of more of polyether, cyclic crown ether, quaternary ammonium salt, quaternary phosphorus salt, quaternary ammonium base and tertiary amine. The method is simple to operate; the method is wide in application range, the content of the 1, 3, 4-triazole substituent in the alkylation reaction process can be reduced, the yield of the 1, 2, 4-triazole substituent is increased, the reaction time is shortened, the reaction temperature is reduced, solvent use is reduced or avoided, the resource utilization rate is increased, three wastes are reduced, the production cost is reduced, and the method meets the requirements of a green and environment-friendly process.
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Paragraph 0023-0026
(2019/12/25)
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- Clean preparation method of tebuconazole
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The invention belongs to the technical field of organic synthesis and specifically relates to a clean preparation method of tebuconazole. The clean preparation method comprises the following steps: S1: adding 1,2,4-triazole, inorganic alkali and diethylene glycol monomethyl ether serving as a solvent into a reaction vessel, carrying out heating, slowly and dropwise adding a reaction raw material A, and then, carrying out a heat preservation reaction; S2, carrying out a complete reaction, then, carrying out standing and cooling, and then, carrying out aftertreatment to obtain tebuconazole serving as a target product. In the clean preparation method of tebuconazole, a mother solution obtained by aftertreatment can be further applied to the next batch of reaction solution, but the reaction yield and the conversion rate of the reaction raw material A are not affected; and therefore, the solvent is not needed to be recovered, and the aftertreatment is simple and easy. In addition, the totalyield of the clean preparation method of tebuconazole reaches 91% or above, and the purity of a tebuconazole product reaches 98%, and therefore, tebuconazole shows a relatively high industrial application value.
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Paragraph 0043-0048
(2019/05/15)
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- Synthesis of magnetic multiwall carbon nanotubes for enantioseparation of three pesticide residues in fruits and vegetables by chiral liquid chromatography
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In this study, magnetic multiwalled carbon nanotubes (MMWCNTs) were synthesized and used as adsorbent for preconcentration of chiral pesticide residues (including epoxiconazole, tebuconazole, and metalaxyl) in lettuce, cabbage, and apple. Several parameters affecting the treatment efficiency were investigated, including extraction solvent and absorption solvent. Under the optimal conditions, all three chiral pesticides showed decent enantiomeric separation (Rs?>?1.48). The linearity of each target was good with the correlation coefficient (r2) being greater than 0.9923. The average recoveries of the three spiked levels were 73.4% to 110.9% with repeatability (RSDr) less than 7.6%, and the limit of quantification of the method was 0.10 to 0.25?mg·kg?1. The results indicated that MMWCNTs had a good purifying effect, which can be applied as an effective pretreatment tool for the determination of residual chiral pesticides in fruits and vegetables.
- Lei, Shuo,Li, Xianhui,Wang, Yang,Sun, Lirong,Liu, Hao,Zhao, Longshan
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p. 1321 - 1329
(2018/11/03)
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- Method for effectively preparing high-purity 1H-tebuconazole
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The invention discloses a method for effectively preparing high-purity 1H-tebuconazole. The method comprises the following steps: putting penta-epoxide(2-(4-chlorophenyl ethyl)-2-tert-butyl epoxyethane), triazole, caustic soda flake, polyethyleneglycol (PEG) and a crown ether catalyst into a reaction kettle and uniformly stirring; heating the system to 105 to 108 DEG C, and dropwise adding the penta-epoxide in a high-level groove into the reaction kettle; heating twice and carrying out heat preservation twice after dropwise addition is completed until the penta-epoxide is completely reacted; cooling the system to a room temperature, adding water and crystallization solvents; standing and layering; cooling and crystallizing an organic layer and separating out 1H-tebuconazole; washing the 1H-tebuconazole with water until pH reaches 7 to 8 to obtain the 1H-tebuconazole; cooling and crystallizing a water layer and separating out the PEG, and recycling the PEG to be applied. According to the method disclosed by the invention, the PEG and the crown ether catalyst are combined and applied to the synthesis of the 1H-tebuconazole, and the obtained 1H-tebuconazole is high in yield and high in purity; moreover, the content of a byproduct is low, and the quality of the 1H-tebuconazole prepared by adopting the method is much higher than that of a product prepared by adopting an existing process.
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Paragraph 0024; 0025; 0026; 0027; 0028; 0029; 0030-0040
(2017/09/29)
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- Novel technology for synthesizing bactericide tebuconazole without solvent
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The invention discloses a novel technology for preparing a bactericide tebuconazole through a solvent-free method. The technology comprises the steps that 2-tertiary butyl-2-(4-chlorphenyl ethyl)ethylene oxide and 1,2,4-triazole are taken as raw materials and react under the catalytic action of an alkaline catalyst and a phase transfer catalyst, and aftertreatment is conduced on a reaction product to obtain the product tebuconazole. According to the technology, no solvent is used in the synthesizing reaction process, and therefore the solvent cost input is reduced; in addition, due to the fact that the reaction concentration is high, the reaction speed is greatly increased, the product yield is significantly increased, a separation method is easy and convenient to operate, and industrialized production is easy.
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Paragraph 0041; 0042
(2017/08/28)
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- Preparation method of converting tebuconazole isomer into tebuconazole
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The invention relates to the field of organic synthesis, in particular to a preparation method of converting a tebuconazole isomer into tebuconazole. The tebuconazole is mainly used for preventing and controlling various fungal diseases of crops such as wheat, peanuts, bananas and apples, and is broad in fungicide spectrum, high in activity and long in lasting time. In a tebuconazole production process, a large amount of tebuconazole isomer waste solids are generated by side reaction, so that enormous pressure is brought to environmental protection, the utilization rate of a raw material is reduced, and the yield of a product is further reduced. According to the preparation method, the separated tebuconazole isomer is efficiently converted into a target product, i.e. the tebuconazole, under the reaction conditions of high temperature, a strong base and a catalyst, the content reaches over 98 percent, and the conversion yield is over 95 percent.
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Paragraph 0024-0026
(2017/07/21)
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- FUNGICIDAL MIXTURES
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The present invention relates to fungicidal mixtures comprising, as active components, 1) azolylmethyloxiranes of the general formula I wherein the variables have the meanings described in the application, 2) a fungicidal compound II, and 3) optionally a further fungicidal compound II, where the compounds II of components 2 and 3 independently of one another are selected from the group consisting of the compounds described in the application, with the proviso that components 2 and 3 are not identical, and to the use of the fungicidal mixtures for controlling phytopathogenic fungi and to the compositions comprising them.
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- FUNGICIDAL MIXTURES
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The present invention relates to fungicidal mixtures comprising, as active components, 1) azolylmethyloxiranes of the general formula I in which the variables have the meanings described in the application, and 2) a fungicidal compound II, where the compounds II of component 2 are selected from among the compounds described in the application, and to the use of the fungicidal mixtures for controlling phytopathogenic fungi and to the compositions comprising them.
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- Synergistic Active Compound Combinations Comprising Phenyltriazoles
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The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.
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- Synergistic Fungidical Active Substance Combinations
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The present invention relates to novel active substance combinations which contain spiroxamine, which is known, a known azole and a known carboxamide and which are very suitable for controlling undesired phytopathogenic fungi.
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- Fungicidal mixtures
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Fungicidal mixtures comprising a) a benzophenone of the formula I, b) a carbamate of the formula II, and c) an azole derivative of the formula III in a synergistically effective amount, and a method for controlling harmful fungi using mixtures of the compounds I, II and III are described. The active compounds of the formulae I, II and III are defined in the description.
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- Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides
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The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.
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- Wood preservatives
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Wood preservatives having biocidal properties which include quaternary ammonium compounds of general formula (I): wherein R1 is a C8-18-alkyl group or an optionally substituted benzyl group, R2 is a C8-18-alkyl group, R3 is a C1-4-alkyl group or a group of the formula —[CH2—CH2—O]n—H, R4 is a C1-4-alkyl group, n is a number from 0.5 to 8, preferably from 1 to 5, and A?is the anion of an organic carboxylic acid which contains 2 to 12 C atoms and carries at least one hydroxyl, amino or sulfonic acid group. The wood preservatives also penetrate deeply into the wood without the use of pressure, and have only a mild corrosive action on metals. Furthermore, a process for treating timbers with these compositions, concentrates for the preparation thereof, the use of new and known quaternary ammonium compounds in wood preservatives and new quaternary ammonium compounds and their use as biocides.
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- Iminoacetic acid amides and their use as pest control agents
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PCT No. PCT/EP96/04345 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 7, 1996 PCT Pub. No. WO97/14673 PCT Pub. Date Apr. 24, 1997Iminoacetamides of the formula (I) in which A represents a single bond or optionally substituted alkylene, Q represents oxygen or sulphur, R1 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R2 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R3 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, R4 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyl a process for their preparation, pesticidal compositions containing them, and their use for controlling pests.
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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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- 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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- Microbicidal benzotriazoles
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Novel benzotriazoles of the formula STR1 in which R, X1, X2, X3, X4 and Y have the meanings given in the description, and their acid addition salts and metal salt complexes, a process for the preparation of these substances and their use as microbicides in crop protection and in material protection.
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- Halogen alkenyl azolyl microbicides
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Novel halogenoalkenyl-azolyl derivatives of the formula STR1 in which R1 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or represents optionally substituted heteroaryl, R2 represents alkyl, halogenoalkyl, 1-hydroxyalkyl, 2-hydroxyalkyl, 1-hydroxyhalogenalkyl, 1-alkenyl or 2-alkenyl, X1 represents fluorine, chlorine, bromine or iodine, X2 represents fluorine, chlorine, bromine or iodine, and Y represents nitrogen or a CH group, and addition products thereof with acids or metal salts are very active as microbicides in plant protection and in the protection of materials.
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- Acylated 5-aminopyrazoles and the use thereof to combat animal parasites
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The present invention relates to new acylated 5-aminopyrazoles of the formula (I) STR1 in which R1, R2, R3, R4 and R5 have the meaning given in the description, to processes for their preparation and to their use as pesticides.
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- Substituted tetrahydro-5-nitro-pyrimidines
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The present invention relates to novel substituted in that one tetrahydro-5-nitro-pyrimidine of the formula (I), according to claim 1, STR1 in which n, R1, R2 have the meaning given in the description, to a process for its preparation and to its use for combating animal pests, especially insects, arachnids and nematodes, which are encountered in agricultural, in forestry, in the protection of stored products and of materials and, in the hygiene sector.
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- P-hydroxyaniline derivatives, their preparation and their use
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p-Hydroxyaniline derivatives of the formula I STR1 where the substituents have the following meanings: R1 is unsubstituted or substituted bicycloalkyl or bicycloalkenyl; R2 and R3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; R4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, OR5 or NR5 R6, where R5 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, and R6 is hydrogen or alkyl, and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests are described.
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- Fungicide compositions
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Compositions of azole fungicides exhibiting reduced eye irritation are prepared by replacing a significant portion of the hydrocarbon solvent with a combination of propylene glycol and a long chain fatty alcohol.
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- Process for the preparation of oxiranes
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A process for the preparation of an oxirane of the formula STR1 in which X is 4-chlorobenzyl, 4-phenylphenoxy or 1H-(1,2,4)-triazolyl, comprising reacting dimethyl sulphate with an excess of dimethyl sulphide thereby to form trimethylsulphonium methyl-sulphate of the formula and without prior isolation reacting the trimethylsulphonium methyl-sulphate with a keytone of the formula STR2 in the presence of solid potassium hydroxide or sodium hydroxide in dimethyl sulphide at a temperature between 0° C. and 50° C.
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- Fungicide compositions
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A fungicide composition having reduced eye irritation comprising in percent by weight based on the weight of the composition 5-50% of an azole fungicide which irritates the eye in combination with an aromatic hydrocarbon, 20-40% propylene glycol, 1-20% fatty alcohol having at least 10 carbon atoms, 10-40% surfactant and less than about 20% aromatic hydrocarbon.
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- Antiviral agents
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The invention relates to hydroxyethylazolyl derivatives, defined herein by formula (I) and particularly to the use of said derivatives for the treatment of viral infections.
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- Process for the preparation of β-hydroxyethyl-(1,2,4-triazole) derivatives
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The known β-hydroxyethyl-(1,2,4-triazole) derivatives of the formula STR1 in which R1 represents alkyl, halogenoalkyl, alkenyl, alkinyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl or an optionally substituted heterocyclic radical and R2 represents hydrogen, alkyl, halogenoalkyl, alkenyl, alkinyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl or an optionally substituted heterocyclic radical, are prepared by a new process, which comprises stirring a β-hydroxyethyl-(1,3,4-triazole) derivative of the formula STR2 in which R1 and R2 have the abovementioned meanings, in the presence of a base and in the presence of an aprotic, dipolar diluent.
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- Process for the preparation of beta-hydroxyethyl-(1,2,4-triazole) derivatives
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Known β-hydroxyethyl-(1,2,4-triazole) derivatives of the formula STR1 in which R represents alkyl, halogenoalkyl, optionally substituted cycloalkyl or optionally substituted phenyl, Z represents halogen, alkyl, cycloalkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylalkyl or optionally substituted phenylalkoxy and m represents the number 0, 1, 2 or 3, are prepared by a new process, which comprises reacting oxiranes of the formula STR2 in which R, Z and m have the abovementioned meaning, with 1,2,4-triazole of the formula STR3 in the presence of a cylcic amid of the formula STR4 in which R1 represents alkyl with 1 to 4 carbon atoms and n represents the number 3, 4 or 5, as diluent, and in the presence of a base.
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- Oxirane compounds
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Oxirane compounds of the formula STR1 in which R represents tert-butyl, iso-propyl radical, cyclopropyl, substituted cyclopropyl, cyclopentyl or substituted cyclopentyl, cyclohexyl or substituted cyclohexyl, in each case the substituent being selected from methyl, or phenyl which is optionally mono or di-substituted by identical or different substituents selected from fluorine, chlorine, methyl and trifluoromethyl, Y represents a grouping --OCH2 --, each Z is individually selected from the group consisting of a fluorine, chlorine or bromine atom, methyl, tert-butyl, cyclohexyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, phenyl, phenoxy, benzyl and benzyloxy, said phenyl, phenoxy, benzyl and benzyloxy being optionally mono or di-substituted by identical or different substituents selected from fluorine, chlorine and methyl, m is 0, 1, 2 or 3; these compounds are particularly useful as intermediates for compounds used in agricultural compositions as plant growth regulants.
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- Synergistic compositions for inhibiting plant growth
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A plant growth-inhibiting composition comprising STR1 wherein the various radicals are as defined.
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