2-(3-nitrophenoxy)-2-thio-3-isopropyl-1,3,2 - oxazaphosphorinane showing nematocidal activity against root-knot nematodes


A01N57/36 - having phosphorus as a ring member

 

(57) Abstract:

Usage: in agriculture as nematocides of the drug. The inventive product: 2-(3 - nitro-phenoxy) -2-thio-3-isopropyl-1,3,2-oxazaphosphorinane

< / BR>
BF Cl2H17N2O4PS, so pl. 45 - 46oC. Reagent 1:

< / BR>
Reagent 2: HOCH2CH2CH2NH(C3H7-out. Reaction conditions: in the environment of methylene chloride at room temperature in the presence of triethylamine. table 2.

The invention relates to new chemical compounds, specifically to 2-(3'-nitrophenoxy)-2-thio-3-isopropyl-1,3,2-oxaze - phosphorinane formula

< / BR>
The specified connection manifests nematocidal activity against root-knot nematodes in the soil, rice aphelenchoidea, rot nematode of potatoes and alfalfa cyst nematodes. The proposed connection, its properties are not described in literature: the synthesis was carried out by a known method.

Known application of chemical compounds of different classes as nematicides. Closest to the proposed connection are nemacur, heteropus and atafo. The last two are used as standards of comparison when testing nematocides asset is cicnet for warm-blooded animals and beneficial insects. So LD50namakura (rats) of 15.3 mg/kg, heterophase 30-70 mg/kg and atafona 250-300 mg/kg

The aim of the invention is the synthesis of new nematocide with along with high nematocidal activity against root-knot nematodes sufficiently low toxicity to warm-blooded animals and beneficial insects.

The objective is achieved by obtaining 2-(3'-nitrophenoxy)-2-thio-3-isopropyl-1,3,2-oxa-Savostina (MHC-69) interaction of N-isopropylidenediphenol with dichlorohydrin m-nitrophenylphosphate acid, the compound obtained is an amorphous powder, insoluble in water, ether, hexane and soluble in acetone, chloroform. The purity and structure of matter confirmed by the data of elemental analysis and thin-layer chromatography (system of hexane:acetone 3:2, Rf0,48).

P R I m e R 1. Getting 2-(3'-nitrophenoxy)-2-thio-3-isopropyl - 1,3,2-oxazaphosphorinane.

To a solution of 1.45 g of dichlorohydrin m-nitrophenylphosphate acid in 10 ml of methylene chloride under stirring and cooling (-10 to -15aboutSince in the reaction mass) is added slowly dropwise a solution of a mixture of 0.7 g of N-isopropylidenediphenol and 1.08 g of triethylamine (1.1 ml methylene chloride and leave for the night, in libraries sodium, remove the solvent in a water jet vacuum pump, then the oil pump, the obtained orange oil when standing zakristallizuetsya. It is recrystallized from ethanol, receiving the target substance in the form of a white amorphous powder with so pl. 45-46aboutWith (yield 0.73 g, 45% of theory. 1.7 g).

Found, C 45,33, 45,26; H 5,55, 5,67; N 8,65, 8,63.

C12H17N2O4PS.

Calculated C 45,56; H 5,42; N 8,86.

P R I m m e R 2. Methodology for processing plants.

Laboratory experience. The toxicity of the substance in relation, for example, to stem nematode of potatoes is determined by immersing the suspension of nematodes in the working solutions of the compounds. Efficiency record spend on a percentage of the death of nematodes by counting under a stereomicroscope living and dead animals within 7 days. (PL.1).

Growing experience. When studying the contact activity of the drug applied to the soil in a uniform mixing for 5 days before sowing seeds. Estimation of technical efficiency 25 days after sowing to reduce galloroman on the roots of plants compared to the control (table.2).

The test results show that technical efficiency against root-knot >/P>2-( 3-Nitrophenoxy)-2-thio-3-isopropyl-1,3,2-oxazaphosphorinane formula

< / BR>
showing nematocidal activity against root-knot nematodes.

 

Same patents:

The invention relates to the class of phosphorus - organic compounds, in particular N, N-dialkylamides-0-(TRANS-2-substituted cycloalkyl)phosphates, and can be used as selective specific inhibitors of cholinesterase, namely butyrylcholinesterase (pixel CEB)

The invention relates to the field of organic chemistry, in particular, butyl ether, 4-isopropyl-4-diethylthiophosphoryl acid formula

(C2H5O)NH-OC4H9-H , (1) with insecticide and acaricide activity

The invention relates to the chemistry of organophosphorus compounds, in particular, to the synthesis of new chemical compounds - 2-dioctyldiphenylamine formula

(C8H17)N, (1) exhibiting fungicidal activity

The invention relates to the field of organic chemistry, in particular 4-phenyl-4-diisopropylphenyl-3-diisopropylamino - fan formula

(i-C3H70)OC3H7-i , (1) with astragalina activity on the sunflower

FIELD: chemistry.

SUBSTANCE: in phosphazene, applied on carrier, catalyst for cyclic monomer polymerisation or for substituent substitution in compound or for carrying out reaction with formation of carbon-carbon bond, carrier is insoluble in used solvent and has group, which is able to form bond with group described with general formula (1) where n is integer in interval from 1 to 8 and represents number of phosphazene cations, Zn- is anion of compound, containing atoms of active hydrogen in form obtained as result of release of n protons from compound, which contains atoms of active hydrogen, in which there are , at most, 8 atoms of active hydrogen; each of a, b, c and d represents positive integer equal 3 or less; R represents similar or different hydrocarbon groups, containing from 1 to 10 carbon atoms, and two R, located on each common nitrogen atom, can be bound with each other with formation of ring structure; R1 represents hydrogen atom or hydrocarbon group, containing from 1 to 10 carbon atoms; D represents direct bond or divalent group able to bind N with carrier. Described are phosphazene compound and phosphazene salts and methods of cyclic monomer polymerisation, substitution of substituent in compound and carrying out of reaction with formation of carbon-carbon bond using applied on carrier catalyst. According to invention method polymerisation of cyclic monomers, substitution of substituents, reactions with formation of carbon-carbon bond, etc. can be carried out with extremely high efficiency.

EFFECT: increase of efficiency of carrying out different organic reactions and absence of activity decrease even after removal and re-use of catalyst, economic benefit.

10 cl

FIELD: chemistry.

SUBSTANCE: present invention relates to ionic liquids based on a cation of formula (1): where substituting groups R1-R9 are selected from hydrogen, alkyl; any carbon atom in R1-R9 can be substituted with a -O-, -C(O)-, -C(O)O-, -S-, -S(O)-, -SO2- or -SO3- group; X is S, O or C; R8 and R9 exist only when X is carbon; the anion is selected from [RSO3]-, [RfSO3]-, [(RfSO2)2N]-, [(FSO2)3C]-, [RCH2OSO3]-, [RC(O)O]-, [RfC(O)O]-, [CCl3C(O)O]-, [(CN)3C]-, [(CN)2CR]-, [(RO(O)C)2CR]-, [B(OR)4]-, [N(CF3)2]-, [N(CN)2]-, [AlCl4]-, PF6-, BF4-, SO42-, HSO4-, NO3-; where R is hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, Rf is a fluorine-containing substituting group.

EFFECT: obtaining new ionic liquids with improved electrochemical properties.

15 cl, 18 ex, 2 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to ionic liquid used in electrical energy accumulation devices and as a solvent which contains a cation of general formula where X1, X2 and X3 denote N, O, S or C; R1-R11, X1, R1, R2 and R3, X2, R6, R7 and R8, X3, R9, R10 and R11 can form ring structures; the anion is selected from [RSO3]-, [RfSO3]-, [(RfSO2)2N]-, [(RfSO2)3C]-, [(FSO2)3C]-, [ROSO3]-, [RC(O)O]-, [RfC(O)O]-, [CCl3C(O)O]-, [(CN)3C]-, [(CN)2CR]-, [(RO(O)C)2CR]-, [R2P(O)O]-, [RP(O)O2]2-, [(RO)2P(O)O]-, [(RO)P(O)O2]2-, [(RO)(R)P(O)O]-, [Rf2P(O)O]-, [RfP(O)O2]2-, [B(OR)4]-, [N(CN)2]-, [AlCl4]-, PF6-, [RfPF5]-, BF4-, [RfBF3]-, SO42-, HSO4-, NO3- I-, bis(oxalate)borate; R, R1-R11 are selected from hydrogehn, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl and heterocyclyl, halogen, CN- or NO2-; the carbon in R and R1-R11 can be substituted with O-, -Si(R')2-, -C(O)-, -C(O)O-, -S-, -S(O)-, -SO2-, -SO3-, -N= -N=N-, -NH-, -NR'-, -N(R')2-, -PR'-, -P(O)R4 -P(O)R'-O-, -O-P(O)R'-O- and -P(R')2=N-; where R' denotes alkyl, fluoroalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, phenyl or heterocyclyl; Rf denotes a fluorine-containing substitute.

EFFECT: obtaining novel ionic liquids which are stable in liquid state in a wide temperature range.

14 cl, 76 ex, 3 dwg

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of producing ionic liquids with a [(C2F5)2P(O)]2N- anion and a cation selected from cations of formula (2) or (6) [PR24]+ (2), [HetN]+ (6), where R2 denotes C1-20alkyl; HetN+ is selected from imidazolium, pyrazolium, pyrazolinium, dihydroimidazolium, pyrrolidinium, triazolium, pyridinium, pyridazinium, pyrimidinium, piperidinium, morpholinium, pyrazinium, thiazolium, oxazolium, indolium, quinolinium, isoquinilinium, quinoxalinium, indolinium, having substitutes selected from C1-20-alkyl and hydrogen. The disclosed method involves reaction of compounds of formula [(RF)2P(O)]2NY (7), where Y=H, RF=C2F5, in a solvent or mixture of solvents, with K+A- type compounds, where K+ is selected from cations of formula (2) or (6) and A-=Cl-, Br-, I-, BF4-, R'OSO3-, R'SO3- or (R')2P(O)O-, where R'=H, C1-C6-alkyl, C1-C6-fluoroalkyl, C1-C6-perfluoroalkyl, C3-C7-cycloalkyl, unsubstituted or substituted phenyl.

EFFECT: novel method of producing low-viscosity ionic liquids and high electrochemical stability.

4 cl, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to phosphoramidate alkylator prodrugs which can be used to treat cancer separately or combined with other anti-tumour agents, having formula: , where each X4 denotes Cl or Br.

EFFECT: obtaining novel compounds, having antiproliferative activity and pharmaceutical compositions based on said compositions.

9 cl, 7 dwg, 56 ex, 43 tbl

FIELD: chemistry.

SUBSTANCE: disclosed is a method which involves treatment of phosphorus oxychloride with excess dimethylamine in toluene medium, adding the mixture of phosphorus oxychloride and toluene in droplets, raising the reaction temperature, after precipitation of dimethylamine hydrochloride salt, to room temperature and then to 100°C, filtering the salt on a Buchner funnel, distilling toluene from the filtrate in a vacuum, separating hexamethylphosphorotriamide by distillation at pressure of 1.0-1.5 mm Hg, and is characterised by that treatment of phosphorus oxychloride with excess dimethylamine in toluene is carried out in the presence of a catalyst - anhydrous aluminium chloride at temperature of -5…+5°C.

EFFECT: method increases output of pure hexamethylphosphorotriamide and reduces power consumption.

3 ex, 2 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula (3) which can be used in the method for synthesis of precursors to immunological adjuvant E6020. In formula (3), R1, R2, R3 denote a C5-C15 alkyl group, C5-C15 alkenyl group or C5-C15 alkynyl group. The invention also relates to compounds of formula (4), which can also be used in synthesis of precursors to said adjuvant. In formula (4) R4 is a C1-C6 alkyl group, C3-C5 alkenyl group, C3-C5 alkynyl group, cycloalkyl group, ethyl group substituted in position 2, halogen ethyl group, aryl group, benzyl group or silyl group; R5, R6 independently denote a C1-C6 alkyl group, C3-C6 alkenyl group or C3-C6 alkynyl group; or R5 and R6 together a nitrogen atom with which they are bonded form a 5- or 6-member heterocyclic ring.

EFFECT: invention also relates to methods for synthesis of compounds of formulae (3) and (4) and crystalline forms of specific representations thereof.

34 cl, 8 dwg, 2 tbl, 6 ex

FIELD: pharmaceutics.

SUBSTANCE: invention relates to compounds of formula (I) used in oncology, their pharmaceutically acceptable salts and compositions based on:

where Ar is phenyl or naphthyl and optionally substituted with -NO2; R3 is selected from benzyl, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, cyclohexyl, 2-indanyl, 3,3-dimethyl-1-butyl, cyclobutyl, cyclopropylmethyl, cyclopentyl, tetrahydropyranyl and 2,2-dimethylpropyl; R4 is H atom; R1 and R2 are selected from H atom and C1-C16alkyl, optionally substituted with phenyl, or one of R1 and R2 has C3-alkylene link connected to N atom so, that total number of ring atoms, including N and C atoms, is equal to 5 atoms, atom H, connected with N atom, is absent and one from R1 and R2 comprises atom H or C1-C16 alkyl; or pharmaceutically acceptable salt of compound of formula I, if said compound is not compound containing in combination unsubstituted phenyl as Ar, CH3 as R3, H as R4, H as one of R1 and R2 and CH3 as one of R1 and R2.

EFFECT: new effective anticancer agent and method of its production are presented.

67 cl, 11 dwg, 8 tbl, 8 ex

FIELD: chemistry.

SUBSTANCE: description is given of a hetero-aromatic compounds with a phosphonate group with formula (I) and their pharmaceutical salts, radicals of which are given in the formula of invention. The compounds are inhibitors of fructose-1,6-bisphosphotase. Description is also given of pharmaceutical compositions based on compounds with formula (I) and (X) and the method if inhibiting fructose-1,6-bisphosphotase, using the compound with formula (I).

EFFECT: obtaining of new biologically active substances.

184 cl, 52 tbl, 62 ex

Up!