PL99516B1 - METHOD OF MAKING SUBSTITUTED ORGANOCIN DERIVATIVES - Google Patents

Description

The present invention relates to a process for the preparation of substituted organocin derivatives. Certain substituted tin organic compounds are known. For example, UK Patent No. 966,813 describes the preparation of substituted tin organic compounds useful as polymers, but gives no suggestions on the use of these compounds for controlling insects or other pests, or herbicidal and fungicidal properties. substituted organic tin compounds used as pesticidal, acaricidal, bactericidal, fungicidal and herbicidal or protective film-forming substances. For example, U.S. Patent No. 364-845 describes a bis-tripalkyltin compound of formula (R) 3 SNR'Sn (R) 3, wherein R is an alkyl group and R 'is a dihydrocarbyl having a minimum of 8 carbon atoms. These compounds have a systemic pesticidal activity especially against larvae of lepidopteran insects such as pests of arable crops in South America. Another example is U.S. Patent No. 3,206,489, which shows substituted tin compounds of general formula 6, wherein Ri, R2, R3 and R4 are They may be alkyl radicals of 1-12 carbon atoms, aromatic hydrocarbon radicals, at least one of the R substituents being an alkyl radical present at the end of the lower aliphatic acid group which is characterized by the presence of a thiocarboxylic function. These compounds are used as herbicides. In addition, U.S. Patent 3,591,614 relates to compounds of formula 7 wherein R is 2-cyanoethyl, 2-carboxyl, or 2-carboxyl lower alkoxyethyl. These substituted ethyl derivatives of triclohexy - locins are used as acaricides for the control of mites and ticks. In addition, U.S. Patent 3,641,097 relates to compounds of formula 7 in which R is 2-furyl, 2-pyridyl, 3-pyridyl, 1-indenyl or 2- (2-pyridyl) ethyl. These compounds are used as pesticides, in particular for the control of mites and ticks. Another example is German Patent No. 2,231,814, which relates to compounds of formula (R) 3SnCH2, in which X is an alkyl or arylsulfonyl, alkyl or arylthio group. or di-alkylamino, R is an alkyl group with 1-14 carbon atoms. These compounds are used to protect surfaces from bacteria, fungi, termites and vasopods. U.S. Patent No. 3,725,466 claims the same group of a compound of the formula RS-CH2-SnR'3, wherein R is an alkyl group. having 1-14 carbon atoms, aryl or 9991691511 substituted aryl and R 'is an alkyl group of 1-14 carbon atoms. These compounds show herbicidal activity both before and after emergence of the plants. German Patent No. 2,106,040 corresponding to US Patent No. 3,784,580 also applies to compounds of formula (R) 3SnCHz-X, where X is the group alkylsulfonyl, arylsulfonyl, or dialkylsulfamoyl. These compounds are used as pesticides and acaricides. The compounds described in the two mentioned German patents differ from the compounds produced according to the invention in that the residue X is linearly attached to the tin atom by a single methyl diradical instead of at least 2 carbon atoms. Peterspn is the author of "Preparation and Reactions of some Sulfur-Substitue Tetroarganotion Compounds" J. Organometal Chem. 26, 215-223 (1971). See page 213: "[ (phenylsulfonyl) methyl] -tributyltin (IV) is not reactive towards carbon dioxide and oxygen at room temperature, whereby placing it (IV) on a thin layer in the air causes 50% decomposition to phenylmethylsulfone and tributyltin oxide within four days. This statement is dependent on the combination compatible with the hydrolysis which takes place due to the sensitivity of compound (IV) in air, \ P eterson, in US Pat. No. 3,794,670, describes the preparation of (organosulfonylmethyl) triorganotin derivatives by reacting a triorganotinamine and an organosulfonylmethyl derivative. Ayrey et al. have published in J. Organometal Chem. 35, 105-109 (1972) for the preparation of 3- (trialkylstannyl) propyl aryl sulfides of the formula R3SnCH2CH2CH2SR '. However, no application of these compounds is shown. Coopmans, in his US patent specification, describes the structure of compounds of Formula 8, wherein R 1, R 2 and R 3 are the same or different and represent alkyl groups of 1-12 carbon atoms, phenyl or halophenyl and Q represents the group of formula 9. These compounds have fungicidal and bactericidal properties. The present invention produces four-substituted tin derivatives of formula I, in which R 'is hydrogen, hydroxyl, methoxy or ethoxy. and if R 'represents a hydrogen atom, X represents: (a) a group of the formula -SO2R1, in which R1 is a straight or branched alkyl group having 1-18 carbon atoms, cyclohexyl, benzyl, phenylic optionally substituted with at least one group or with various straight or branched groups b 1 to 20 carbon atoms, cycloaliphatic with 4 to 6 carbon atoms, straight or branched alkene, 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms, and lkylthio with 1-8 carbon atoms, halogen atom, nitro, acetyl, acetamide, carboxyl, alkoxycarbonyl, carbamoyl, cyano, hydroxyl, trifluoromethyl, benzyl, naphthyl or norbornyl group, naphthyl group, diphenyl group, diphenyl group - peridineethylmethiodine, a group of the formula -R2Sn (CH3) 3 in which R2 is a polymethylene group of 2-11 carbon atoms or a group of the formula -R4SO2R5Sn (CH3) 3 in which R4 is an ethylene group and Rs is the meaning given for R2,. (b) a group of the formula -OR7, in which R7 is a straight or branched alkyl group of 8-16 carbon atoms, aryl, alkoxyaryl, alkylaryl, haloalkyl, N, N-dialkylaminoalkyl, a group of the formula -RsSn (CH3) 3, where R8 is an alkylene group of 2-11 carbon atoms, cycloaliphatic of 4-6 carbon atoms, tetrahydro-1,1-dice-3-thienyl; a group of the formula -SR10, in which R10 is a straight or branched alkyl group of 1-16 carbon atoms, phenyl, chlorophenyl, tertiary-butylphenyl or a group of formula -R2Sn (CH3) 3j (d) group of formula -COR11 in which Rn is a group of the formula -NHR12 in which R12 is a straight or branched alkyl group of 1-12 carbon atoms or an aryl group; a group of formula -NHCH2OH, a group of formula -NHNH2; a group of the formula -NHCH2NHCOR2Sn (CH3) 3; a group of the formula -OR13 in which R13 is a straight or branched alkyl group of 8-15 carbon atoms, a group of the formula - (CH2) mOH in which m is a number 2-4; a so group of the formula - (CHi) pN (R14) 2, wherein p is a number 2-4 and R14 is a straight or branched alkyl group with 1-5 carbon atoms; a group of formula - (CH2) qOCOR2Sn (CH3) 3, wherein q is as defined for p; a group of formula - (CH2) sN + (CHi) 31-, wherein s is as defined for p; (e) a group of the formula -NHCONH2; (f) a group of the formula -NHCSNH2; (g) a 1-imidazolyl group; (h) N-2-ketopyrrolidinyl; (I) a group of the formula -OCOR17, in which Rn is a group of the formula -NHRib, in which Ri is a straight or branched alkyl group having 1-5 carbon atoms; a 2-furyl group; and a group of formula -O (CH2) tSn (CH3) 3, in which t is a number 2-11, if R 'is a hydrogen atom or an ethoxy group, X is (j) a group of formula -PO (OR2o) 2 wherein R20 is a straight or branched alkyl group with 1-5 carbon atoms when R 'is hydroxyl X is (k) tetrahydro-1,1-dice-2-thienyl when R' is hydrogen that X is (1) a group of the formula -Si (OR2i) 3, where K21 is a straight or branched alkyl group of 1-5 55 carbon atoms, if R 'is a methyl group X is (m) a group of formula II ; and when R 'is a hydrogen atom, X is a (n) group of formula 3, 6e (o) 2-pyridyl group, (p) 4-pyridyl group or (q) 2-alkyl-5-pyridyl group, and n is the number 1-10. The term "aryl group" includes a phenyl group and a substituted phenyl group, for example a phenyl group substituted with a halogen atom or atoms, or an alkyl group or groups with 1-4 carbon atoms, X may also represent a group with The formula * S (O) R28, in which R28 is a straight or branched alkyl group of 1-18 carbon atoms, cyclohexyl, benzyl, phenyl, tert-butylphenyl or chlorophenyl. If X is a group of the formula -SO2R1, co- a preferred group of compounds is that where R 1 represents a straight or branched alkyl group of 1-18 carbon atoms, cyclopentyl, cyclohexyl, dicyclo- (2.2,1) -heptyl, benzyl, phenyl, alkoxyphenyl with 1-3 carbon atoms. in the alkoxy, halophenyl, piperidine ethylmethiodide, group of formula R2Sn (CH3) l in which R2 is a group of imethylene with 2-11 carbon atoms or R4SO2RsSn (CH3) 3, where R * is ethylene and R5 is as defined above. It has now been found that the new organotin derivatives have a wide range of activities, e.g. they have been found useful as insecticides, acaricides and herbicides. It has been found that the insecticidal, herbicidal and herbicidal properties of the compounds according to the invention depend on the system of the trimethyltin molecule, ie (CH3) jSn-. The degree and nature of the action of these compounds is also dependent on the part of the molecule containing the group of formula 5, such as phytotoxicity to crops, herbicide against harmful plants, absorption and distribution in plants, staying in the ground, oral or dermal toxicity to mammals, physical properties such as volatility, solubility, hydrolytic and / or oxidative stability, sensitivity to ultraviolet sunlight, ease of entry into the nutrient chain , degradation by microorganisms and / or higher forms of organisms, practicality and ease of use. In general, these compounds can be obtained following one reaction step described by R. Sommer and HGKuivil in J. Org. Chem. 33, 802 (1968), which includes the reaction of a compound containing an olefinic residue with trimethyltin hydride according to the reaction shown in Scheme 1. In the compounds shown in this scheme, X has the meaning given above, R 'is a hydrogen atom, a straight or branched alkyl group of 1 -5 carbon atoms or alkoxy group with 1-5 carbon atoms, R "is hydrogen, hydroxy or alkyl group with 1-5 carbon atoms, and m is 0-9. In this synthesis, substituted olefinic derivatives and an equivalent amount of organocin hydride The reaction mixture is introduced into a conventional glass reaction vessel under an inert gas in the presence of a suitable solvent and optionally stirred. The reaction mixture is illuminated with a mercury lamp until organocin hydride is absent, the presence of which is determined by spectrum analysis confirming no positive Sn-H absorption The reaction time depends on the olefinic derivative used and is about 4 to 48 hours, but 1 A * 6 if n is a number 3 or greater, it may be so long that it is 232 hours. The reaction mixture is usually kept at a temperature of about 0 ° C to 5 ° C. When the reactants form heterogeneous phases I and / or when the substrate is in solid form, ether solvents such as benzene and toluene, ester and nitrile solvents such as ethyl acetate and acetonitrile, alcohol such as methanol and alcohol are used to mix the reactants. ethanol, amides such as dimethylformamide and the like. One mole of unsaturated sulfone is prepared by adding one mole of organocin hydride to one mole of a sulfone containing two unsaturated groups (—C = C). For example, according to Scheme 1, divinyl sulfone is reacted with reagents such as mercaptins, amines, alcohols, and phenols. Using essentially the same method as described above to obtain the organocin derivative of Scheme 1, two equivalents of the organocin hydride can be reacted with which produces an adduct containing two organic residues. These reactions are shown in Scheme 2. In the formulas in this scheme, R ', R "and the meanings given above. W is a sulfonyl diradical (-SO2-) analogous to compounds Nos. 1 and 2 shown below in Table 9, diradical oxy (-0-) as in Compounds Nos. 25 and 26 of Table 9, 3 below (J diradical Thio (-S-) as in Compound No. 36 shown below in Table 9, diradical N, N'-methyl- lenobiscarbamoyl (-C) O (-NHCH2NHC) 0 (-) as in Compound No. 41 below in Table 9, 1,2-ethylenedioxydicarbonyl diradical (-C) = 0 (-Q-CH2CH2-O-C) = 0 (-) as in Compound No. 45 shown below in Table 9, Carbonyldioxy (-O-C) = C (-O-) diradical as in Compound No. 52 shown below in Tab. 9, Phenylene diradical of Formula 10 as in Compound No. 60, shown below in Table IX, and the diradical 2,4,8,10-tetraoxaspiro [5.5] undecylene-3.9 of the formula 1 as in Compound No. 63 shown below in Table 9. This method of production is the same as shown in Scheme 1.45, except that two equivalents of organocin hydride are used and the remaining reagent contains two olefinic residues. Alternatively, purification of the organocin compounds can be performed using standard methods such as distillation, chromatography - column graphing or recrystallization. Alternatively, these compounds can be prepared by the method set forth in Karl Zieglei's British Patent No. 966,813 using free-radical generating compounds such as azobisisobutyronitrile, nitriphenylmethane, etc. A variety of substituted derivatives may be used in the preparation of compounds falling within the scope of the invention. Examples of these compounds are set forth below and grouped according to their primary function. Certain compounds are numbered. These compounds are representative and are also shown in more detail below in Table IX.t Sulfones - - divinylsulfone, methylvinylb-ethylvinylsulfone n-propylvinylsulfone isopropylvinylsulfone n-butylvinylsulfone butylvinyl-sulfone T-butylvinyl-sulfone n-pentylvinyl-sulfone isopentylvinyl-sulfone II-pentylvinyl-sulfone T-pentylvinyl-sulfone n-hexylvinyl-sulfone cyclohexylvinyl-sulfone 4-methylcyclohexylvinylvinylvinyl-sulfone-metallovinylvinyl-sulfone Tert.-octylvinylsulfone benzylvinylsulfone | 4-chlorobenzylvinylsulfone p-tolylvinylsulfone p-tolylvinylsulfone o-ethylphenylsulfone p-ethylphenylvinylsulfone p-propylphenylvinylsulfone p-iso-propylphenylvinylsulfone p-butylphenylvinylsulfone p-tinylphenylsulfone T-butylphenylvinylsulfone p-iso-butylphenylvinylsulfone p-n-amylphenylvinyl-sulfone p-n-amylphenylvinylsulfone p-n-hexylphenylvinyl-3-sulfone p-n-heptylphenylvinyl-sulfone pn-octylphenyl-III-vinyl sulfone .-octylphenylvinylsulfone p-nonylphenylvinylsulfone p-decylphenylvinylsulfone p-dodecylphenylvinylsulfone p-dodecylphenylvinylsulfone p-trimecylphenylvinylsulfone p-cyclopentylphenylvinylsulfone p-cyclohexylphenylvinylsulfone p-cyclohexylphenylvinylsulfone hept-2-ylphenylvinylsulfone 1 3,4-dimethylphenylvinylsulfone 2,4-dimethylphenylvinylsulfone 2,5-dimethylphenylvinylsulfone 2,4-diethylphenylvinylsulfone 2,5-diethylphenylvinylsulfone 2,4-diisopropylphenylvinylsulfone - -sulfone | 2,5-diisopropylphenylvinylsulfone and 2,4,6-triethylphenylvinylsulfone, 2,5-diisopropylphenylvinylsulfone, 2,4,6-triethylphenylvinylsulfone, 2,5-dicyclohexylphenylvinylsulfone | Union number 2 1, 2, 16 ¦ 3 4 '6 7 11 8 .12 13' 66 67 68 1 - 14 69 70 1 71 72 73 74 79 80 81 75. 76 77 78 | ¦¦ * - ,. Sulfones 1 and 2,4,6-triisopropylphenylvinylsulfone 2,3,5,6-tetramethylphenylvinylsulfone • 2,3,4,5,6-pentomethylphenylvinylsulfone p-allylphenylvinylsulfone p-propenylphenylvinylsulfone p-crotylphenylvinylsulfone p-metallylphenylvinylsulfone p-4-pentenylphenylvinylsulfone p-3-methylcrotylphenylvinylsulfone p-oleylphenylvinylsulfone p-methoxyphenylvinyloxyphenylphenylphenylphenylphenylphenylphenylphenylsulfone p-octoxyphenylvinylsulfone 2,4-dimethoxyphenylvinylsulfone | 2,5-dimethoxyphenylvinylsulfone 1 3,4-dimethoxyphenylvinylsulfone p-methylthiophenylvinylsulfone p-butylthiophenylvinylsulfone p-octylthiophenylvinylsulfone-chloro-2-methoxyphenylvinylsulfone 2-chloro-4-methoxyphenylvinylsulfone 2-chloro-4-methoxyphenylvinylsulfone -chloro-4-methoxyphenylvinylsulfone-bromo-2-methoxyphenylvinylsulfone 2-bromo-4-metho, xyphenylvinylsulfone 3-bromo-4-methoxyphenylvinylsulfone 3-acetamido-4-methoxyphenylvinylsulfone -acetamido-2-methoxyphenylvinylsulfone-nitro-2-methoxyphenylvinylsulfone 2-nitro-4-methoxyphenylvinylsulfone 1 3-nitro-4-methoxyphenylvinylsulfone 2-methyl-4-methoxyphenylvinylsulfone 2-methyl-5-methoxyphenylvinylsulfone 2-methyl-5-chlorophenylvinylsulfone 2-methyl-5-bromophenylvinylsulfone p-fluorophenylvinylsulfone p-bromophenylvinylsulfone p-chlorophenylvinylsullon 2,5-dichlorophenylvinylsulfone -sulfone 3,4-d Dichlorophenylvinylsulfone 2,4,5-trichlorophenylvinylsulfone trifluoromethylphenylvinylsulfone 1 Compound number 1 1 2 "82 84 83 85fttttt 4-chloro-3-nitrophenylvinylsulfone 3-nitrophenylvinylsulfone 2-nitrophenylvinylsulfone 3,5-dichloro-2-hydroxyphenylvinylsulfone p-acetamidophenylvinylsulfone pI: arboxyphenylvinylsulfone phenylvinylcarbonylphenyloxycarbone - -sulfone p-carbamoylphenylvinylsulfone p-cyanophenylvinylsulfone p-acetylphenylvinylsulfone 2-naphthylvinylsulfone 4-bifsnylvinyl-sulfone * sullon n-dodecylvinylsulfone n-octadecylvinylsulfone 1,2-ethylenebis (1,2-ethylenebis) ethyl-1,2-ethylenebis (vinylsulfone) 1,4-tetramethylenebis (vinyl * ^ ullan) 1,6-s'Bciomethylenebis (vinylsulfone) 1,1,8-olstamethyllenbis (vinylsulfone); 2.2 -pipylidenebis (vinylsulfone) 1,1'-methylenebismethylvinylsitilphon) 2- (trimethyltinyl-ethyl-tetryl-diphone methyl-3-butenylsulfone ethyl-4-pentenylsulfone n-propyl-5-hexenylsulfone isopropyl -6-h-cptenyl- * 3-phthono-n-butyl-7-octene-4-phthylate tert-butyl + 8-tetraenyl-s * i Kon IIIrzv ** butyl-9-decenylsulfone n-pentyl-10-undecenylsulfone isopentyl-3-but enyl-sulfone IIrz.-pentenyl-4-pentenyiOrSUlphone III-pentenyl-5-heHsB-methylsulfone n-hexyl-6-heptenylsulfan cyclohexyl-7-octenylsulfan 4-methylcyclohexyl-8-sulfonyl-9-sulfonyl- -decenylsulfone n-octyl-10-undecenylsulfone tertiary-octyI-3-butenylsulfone benzyl-4-pentenylsulfone 4-chlorobenzyl-5-helium-1-sulfone 6-hexenylphenylsulfone 3-butenyl- fp-tolyl-fp-t-butylphenylsulfone 4-pentenyl-p-ethylphenylsulfone-1Suifon S-hexenyl-p-tolH-e ^ nsrlcMsu ^ oii 6-heptenyl-p-propylphenylsulfone 7- octenenyl-p-isopropyl | en-rl-sulfone 8-nonenyl-pn-butylphenyl 9-decenyl-1β-IIrz-butylaphenyl-sulfon-undecenyl-p-tolyl-sulfone 4-peritenyl-p-iso-butylphone sulfon-hexenyl-pn-amylphenylsulfone 6-heptenyl-t-amylphenylsulfone 86 9 17 87 88 89 K ^ 40 * 5 7-octenyl-pn-hexylphenylsulfone 8-nonenyl-pn-heptylphenylsulfone 9 -decenyl-p-octylphenyl-sulfon-undecenyl-t-octylphenyl-sulfone 3-butenyl-p-nonylphenyl-sulfone 4-pentenyl-p-decyl phenylsulfone-hexenyl-pn-dodecylphenylsulfone 6-heptenyl-p-dodecylphenylsulfone 7-octenyl-p-tridecylphenylsulfone 8-inonenyl-p-cyclopentylphenylsulfone 9-decenyl-p-cyclohexylphenyl -sulfon-undecenyl-bicyclo (2.2,1) hept--2-ylphenylsulfone 3-butenyl-3,4-dimethylphenylsulfone 4-pentyl-2,4-dimethylphenyl -sulfone-hexenyl-2, 5-dimethylphenyl • sulfone 6-heptenyl-2,4 ~ dimethylphenylsulfone 7-octenyl-2,5 * diethylphenylsulfone 8-nonenyl-2,4-diisopropylphenylsulfone 9-decenyl-2,5 -diisopropylphenylsulfone-undecenyl-2,5-di-tert -butylphenylsulfone 3-butenylbicyclohexylphenylsulfone 4-pentenyl ^ 2,4,6-trimethylphenylsulfone -hexenyl-2,4,6-triethylphenyl- -sulfone 6-heptenyl-2,4,6-triisopropyl-phenyl-sulfone 7-octenyl-2,3,5 * 6-tetramethyl-phenyl-sulfone 8-nonenyl T 2,3,4,5,6-pentamethyl-phenyl- 9-decenyl-rp-methoxyphenyl-sulfone-undecenyl-p-ethoxyphenyl-sulfone 3-butenyl-^ p-butoxyphenyl-sulfone 4-pentenyl-p-octoxy sulfone enyl-sulfon-hexenyl-2,4-dimethok3yphenylsulfone 6-heptenyl-2,5-dimethoxyphenylsulfone *. ¦ 7-octenyl-3,4-dimethoxyphenylsulfone 8-nonenyl-p-methylthiophenylsulfone 9-deoenyl-p-butylthiophenylsulfone11 99 SIS 12-undecenyl-p-octylthiophenylsulfone 3-butenyl-5 -chloro-2-methoxy-phenyl-sulfone 4-pentenyl-2-chloro-4-methoxy-phenyl-sulfone -he :: senyl-3-chloro-4-methoxy-phenyl-sulfone 6-heptenyl-5-bromo -2-methoxy-phenyl-sulfone 7-oclenyl-2-bromo-4-methoxy-fcnylsulfone 8-nitenyIo-3-bromo-4-methoxyienylsulfone 9-decenyl-3-acetamido-4-methoxy- phenylsulfone-undecenyl-5-acetamido-2-methoxyphenylsulfone 3-butenyl-2-nitro-4-methoxyphenylsulfone 4-pentenyl-3-nitro-4-methoxyphenylsulfone-hexenyl-2 methyl-4-methoxy-phenyl-sulfone 6-heptenyl-2-methyl-5-methoxy-phenyl-sulfone 7-octenyl-2-methyl-5-chlorophenylsulfone 8-nonenyl-2-methyl-5-bromophenyl- -sulfone 9-decenyl-p-fluorophenyl-sulfone-undecenyl-p-bromophenyl-sulfone 3-butenyl-p-chlorophenyl-sulfone 4-pentenyl-2,5-dichlorophenylsulfone-hexenyl-3,4-dichlorophenyl- - 6-heptenyl-2,4,5 sulfone -trichlorophenylsulfone 7-octenyl-trifluoromethylphenylsulfone 8-nonenyl-4-chloro-3-nitrophenylsulfone 9-decenyl-3-nitrophenylsulfon-undecenyl-2-nitrophenes; o-3-butenyl-sulfone 3,5-dichloro-2-hydro-xyphenylsulfone 4-pentenyl-p-acetamidophenylsulfone-hexenyl-p-carboxyphenylsulfone 6-heptenylalkoxycarbonylphenylsulfone 7-octenylcarbamoylphenylsulfone 8-nonenylcyanophenyl sulfone 9-decenyl-p-acetylphenylsulfone-undecenyl-2-naphthylsulfone 3-butenyl-4-biphenylsulfone 4-pentenyl-n-dodecylsulfone-hexenyl-n-octadecylsulfone Ethers divinyl ether ethylvinyl ether 18 - 40 50 * 0 65 n-propyl vinyl ether isopropyl vinyl ether n-butyl vinyl ether isobutyl vinyl ether n-pentyl vinyl ether n-hexyl vinyl ether cyclohexyl vinyl ether n-octyl vinyl ether isooctyl vinyl ether isooctyl ethyl ether, hexyvinyl ethyl vinyl ether, n-hexyl vinyl ethyl ether 2-trifluoroethylvinyl phenyl vinyl ether p-chlorophenyl ether o-tolyl vinyl ether p-methoxyphenyl vinyl ether 2,6,8-trimethyl-4-nonyl vinyl ether N, N-dimethylaminoethyl vinyl ether diallyl ether allyl glycidyl ether allyl phenyl ether allyl p-tert-allyl phenyl ether methoxyphenyl ether allyl-p-chlorophenyl ether allyl (tetrahydro-1,1-diketo-3-thienyl) 1,4-divinyloxybutane 3-vinyl-7-oxabicyclo (4,1) heptane 3.9- divalin-2,4,8-tetraoxaspiro (5,5) undenecene 3-butenylvinyl ether di (3-butenyl) ether 4-pentenylethyl ether 5-hexenyl-n-propyl ether 6-heptenyl-isopropyl ether 7-octenyl ether -n-butyl ether 8 nonenyl isobutyl ether 9-decenyl n-pentyl ether 10-undecenyl n-hexyl ether 3-butenyl cyclohexyl ether 4-pentenyl n-octyl ether 5-hexenyl isooctyl ether 6-n-heptenyl-n-heptenyl nonyl 7-octenyl n-decyl ether 8-nonenyl-n-dodecyl ether 9-decenylhexadecyl ether 10-undecenylbenzyl ether 3-butenyl-2,2,2-trifluoroethyl ether 4-pentenylphenyl ether 5-hexenyl-p-chlorophenyl ether 6-heptenyl-o-tolyl ether 7-octenyl-p-methoxy 8-nonenyl-2,6,8-trimethyl-4-nonyl ether 9-decenyl-N, N-dimethyl - 3-butenyl-N, N-dimethylaminoethyl-aminoethyl ether »$ t4 1 1 n .- .. .. • 3-butenylallyl ether 4-pentenylglycidyl ether 5-hexenylphthite ether e-heptdnyl-p-t-tephthyl ether octenyl p-tert-butyl phenyl ether 8-nonenyl-p-metholfyphenyl phenyl ether 9-decenyl p-chlorophthyl ether 10-undecenyl p-bronlphenyl ether 3-butenyl-p-trifluoromethylphenyl ether 4-pentenyl ether -p-methoxin phenyl ether 5-hexenyl ether (Tetrahydro-1, i-dWuk ^ to-3-thienylthj ^ y). Thioethers diallyl sulphide allylmethyl sulphide allylethyl sulphide allyl-n-propyl sulphide allylisopropyl sulphide-butylsulphide-n allyl-iao-butite 1 altflo-n-pentyl sulfide alUl-n-hexyl sulfide alltlcyclohexyl sulfide allyl-n-octyl sulfide allyl sulfideCOoctyl sulfide allyl decyl sulfide s allylhexadecyl sulphide allylbenzyl sulphide allylphenyl sulphide allyl phenyl sulphide methylvinyl sulphide ethylvinyl sulphide n-propylvinyl sulphide n-butylvinyl sulphide n-hexylvinyl sulphide cyclohexylvinyl sulphide cyclohexylvinyl sulphide hexylvinyl phenyl sulphide phenyvinyl sulphide n-phenyvinyl sulphide n-phenyvinyl sulphide vinyl o-tolylvinyl sulphide p-chlorophenylvinyl sulphide 3-butenylvinyl sulphide 4-pentenylethyl sulphide 5-hexaenyl <-n-propyl sulphide 6-heptenylisopropyl sulphide 7-octenyl n-butyl sulphide 8-butyl isobutyl sulphide -decenyl-n-pentyl sulphide 10-undecenyl-n-hepesyl sulphide 3-butenyl-cyclehexyl sulphide 4-pentenyl-n-ktyl sulphide 5-hexenyl-isooclyl sulphide 6-heptenyl-decyl sulphide 7-octenyl-2'36 * xadeeyl sulphide 7 40 50 8-nonenylbenzyl sulphide 9-decenylphenyl sulphide 10-und sulphide ecenyl-p-chlorophenyl sulphide 3-butenylbenzyl sulphide 4-pentenyl-p-tert-butylphenyl sulphide 5-hexenyl-o-tolyl sulphide 6-heptenyl-p-bromo-phenyl sulphide di / 3-butenyl ester carbonate Allyl-N-methyl divinyl carbonate dimethyl carbonate allyl-N-methyl carbonate allyl-N-ethyl carbonate allyl-N-propyl carbonate allyl-Nn-butyl carbonate allyl-Nn-octyl carbonate allyl-N-dodecyl carbonate-phenyl carbonate 2-N-dodecyl carbonate allyl methyl acrylate ethyl acrylate n-propyl acrylate isopropyl acrylate n-butyl acrylate n-iientyl acrylate n-hexyl acrylate cyclohexyl acrylate n-octyl acrylate • n-decyl acrylate n-dodecyl acrylate phenyl acrylate phenyl acrylate phenyl acrylate phenyl acrylate 1,2-ethylene diacrylate 1,4-tetramethylene diacrylate 1,6-hexamethylene diacrylate 1,8-octamethylene diacrylate 1,10-decamethylene diacrylate 1,12-dodecamethylene diacrylate methyl methacrylate ethyl methacrylate propyl methacrylate isopropyl butyrate methacrylate Hexyl methacrylate cyclohexyl methacrylate n-octyl methacrylate n-decyl methacrylate n-dodecyl methacrylate hydroxyethyl methacrylate benzyl methacrylate allyl methacrylate p-chlorophenyl methacrylate p-chlorophenyl methacrylate 1,2-di-butylamethylenemethylacrylate N-methylacrylate N-methylacrylate methacrylate 53 42, 43 44 4515 1,4-tetramethylene dimethacrylate 1,6-hexomethylene dimethacrylate 3-butenylvinyl carbonate 4-pentenylallyl carbonate | 5-hexenylmethyl carbonate and 6-heptenyl-N-methyl carbonate 7-octenyl-N-ethyl carbonate 8-nonenyl-N-propyl carbonate 9-decenyl-Nn-butyl carbonate 10-undecenyl-Nn-octyl carbonate 3-butenyl carbonate -N-dodecyl carbonate 4-pentenyl-N-phenyl fluoro-25-hexenyl 6-heptene-carboxylic acid methyl ester 7-octene-carboxylic acid ethyl ester 8-nonene-carboxylic acid n-propyl ester 9-docene isopropyl ester - carboxylic acid ". 10-undecanoic acid n-butyl ester n-pentyl ester 3-butene carboxylic acid n-hexyl ester 4-pentene carboxylic acid cyclohexyl ester. 5-hexenecarboxylic acid n-octyl ester 6-heptenecarboxylic acid n-decyl ester 7-octene carboxylic acid n-dodecyl ester 3-none-carboxylic acid n-oceptidecyl ester 9-decenecarboxylic acid benzyl 10-undecenecarboxylic ester phenyl ester 3-butene-carboxylic acid, p-chlorophenyl ester of 4-pentenecarboxylic acid, 1,2-ethylene di (4-pentenecarboxylic acid) ester 1,4-tetramethylene di (5-hexenecarboxylic acid) di (6-hexamethylene) ester heptenecarboxylic acid) 1,8-olitamethylene ester di (7-octene carboxylic acid) 1,10-decamethylene ester di (8-nonenecarboxylic acid) 1,12-dodecamethylene di (9-decenecarboxylic acid) di (2-methyl ester) di ( 10-undecenecarboxylic acid 2-methyl-3-butenecarboxylic acid ethyl ester 2-methyl-4-pentenecarboxylic acid propyl ester 99 516 40 50 55 60 65 2-methyl--5-hexenecarboxylic acid isopropyl ester n-butyl ester sq asu 2-methyl -6-heptenecarboxylic acid hexyl ester 2-methyl-7-octene carboxylic acid cyclohexyl ester ^ 2-methyl-8-nonenecarboxylic acid n-octyl ester 2-methyl-9-decenecarboxylic acid n-decyl ester 2-methyl--10-undecenecarboxylic acid n-dodecyl ester 2-methyl-3-butenecarboxylic acid 2-hydroxyethyl ester 2-methyl-4-pentenecarboxylic acid benzyl ester 2-methyl -5-hexenecarboxylic acid allyl ester 2-methyl -6-hepteriocarboxylic acid phenyl ester 2-methyl-7-octene carboxylic acid p-chlorophenyl ester 2-methyl-8-nonenecarboxylic acid tert-butylaminoethyl ester 2-methyl-9-decenecarboxylic acid ester N 2-Methyl-10-undecene-carboxylic acid, N-dimethylaminoethyl di- (2-methyl-3-butenecarboxylic acid, 1,2-ethylene ester) di (2-methyl acid, 1,4-tert-methylene ester) -4-pentene-carboxylic acid) di (2-methyl-5-hexene-carboxylic acid) 1,6-hexamethylene ester Amides acry N-methylacrylamide N-hydroxymethylacrylamide N-ethylacrylamide N-isopropylacrylamide Nn-butylacrylamide N-tert-butylacrylamide Nn-octylacrylamide N-do * decylacrylamide N, N-methylene bisacrylamide Nmethylene acrylamide Nmethylenebisacrylamide Nmethylenebisacrylamide Nmethylene acrylamide Nmethylene acrylamide -methylmethacrylamide N-ethylmethacrylamide N-isopropylmethacrylamide Nn-butylmethacrylamide N-hexadecylmethacrylamide N-tert-butylmethacrylamide N-octadecylmethacrylamide 38 40 39 41 Lithium 1T ii: i .ii i. 11, i .. 1 i. -phenylmethacrylamide N, N-dimethylmethacrylamide N, N-diethylmethacrylamide N, N-di-n-butylmethacrylamide N, N-di-n-octylmethacrylamide | N-methyl-3-butenamide | N-hydroxy-4-pentenoamide! N-ethyl-5-hexenamide N-isopropyl-6-heptenamide Nn-butyl-7-octeneamide N-tert-butyl-8-nonenoamide Nn-octyl-9-decenoamide N-dodecyl-10-undecenamide N-phenyl- < 3-butenamide N, N'-methylenebis <4 * pentenamide) N-phenyl-5-hexanamide N £ l'-tetramethylenebis (6-heptenamide) N, N'-hexamethylenebis (7-octeneamide) N-allyl -8-nonenoamide 1-methyl-9-decenoamide N-methyl-2-methyl-10-undecenamide ¦¦ .-. ¦ N-ethyl-2-methyl-3-butenamide N-isopropyl ^ -methyl ^ pentenoamide Nn-butyl-2-methyl-5-hexenamide N-hexadecyl-2-methyl-6-heptenamide N-tert-butyl-2-methyl-7-octadecyl-8-octadecyl amide -nonenamide N-phenyl-2-methyl-9-decenoamide N-phenyl-2-methyl-10-undecenylamide N-phenyl-2-methyl-3-butenamide N, N-dimethyl-2-methyl- - 4-pentenamide N, N-diethyl-2-methyl-5-hexenamide N, N-di-n-butyl-2-methyl-6-heptenamide N, N-di-n-octyl-2-methyl- -7-octeneamide Phosphate, diethyl vinylphosphoric acid ester, di-n-butyl vinylphosphoric acid ester, di-n-hexyl ester in vinylphosphoric acid dicyclohexyl ester vinylphosphoric acid di-n-octyl ester vinylphosphoric acid di-dodecyl ester vinylphosphoric acid di-hexadecyl ester vinylphosphoric acid dibenzyl ester vinylphosphoric acid 40 41 50 95 'la diphenyl ester vinylphosphoric acid 2-vinylphosphoric acid vinylphosphate 2-vinylphosphate ester vinylpyridine 3-vinylpyridine 4-vinylpyridine 2-methyl-5-vinylpyridine -methyl-2-vinylpyridine 6-methyl-2-vinylpyridine 6-butyl-2-vinylpyridine 2,6-dimethyl-4-vinylpyridine 4-tert-butyl -2-vinylpyridine 2-allylpyridine 3-allylpyridine 4-allylpyridine 2- (3-butenyl) pyridine 3- (3-butehyl) pyridine 4 - ($ - butenyl) pyridine 3- (4-pentenyl) pyridine 4- (5- hexenyl) pyridine 2-methyl-5 (3-butenyl) pyridine 2-methyl * 5 (7-heptenyl) pyridine 2-methyl-5 (9-nonenyl) pyridine., -methyl <-2 (4-pentenyl) pyridine - methyl-2 (6-hexenyl) pyridine-methyl * 2 (8-octenyl) pyridine-methyl * -2 (10-decenyl) pyridine to 6-methyl-2- (3-butenyl) p iridine 6-butyl-2- (4-pentenyl) pyridine 2,6-dimethyl-2- (3-butenyl) pyridine 2,6-dimethyl-2- (5-hexenyl) pyridine 4-tert. butyl-2- (6-heptenyl) pyridine Other heterocyclic nitrogen compounds N-vinyl N-vinyl-2-methylimidazole N-vinyl-2-phenylimidazole N-vinyl (| -4,5-dimethylimidazole N-vinyl-4, 5-diphenylimidazole N-vintylycarbazole N-vinyl-2-pyrrolidinone N- (3-butenyl) imidazp1 N- (5-helisenyl) imidazole N- (6-hethenyl) -2H-methylimidazole N- (7-octenyl) -2- phenyimidazole N- (8-nonenyl) -4,5-dimethylimidazole Nfi (9-deeenyl) -4,5-diphenylimidazole N- <10-undecenyl) carbazole N- (3-butenyl) -2-pyrrolidinone N - (5-hexenyl) -2-pyrrolidine N- (7-octenyl) -2-pyrroly4inone Ureas allyl-urea N-allyl-N'-phenyl-moss} c N-allyl-N'-benzoyl-urea N- allyl-N'-butyl-unia; . (N-allyl-N'-methyl-urea 55 57 56 50 48 49 4619 - $ 9516 N-allyl-N'-n-octyl-urea N, N'-diallyl-urea N-allyl-N /, N, - dimethyl-urea N-allyl-N /, N, 'dibutyl-urea N-al'yl-N /, N, -diphenyl-urea N- (3-butenyl) urea N- (4-pentenyl) -N'- phenyl-urea NC-hexenyl) -N'-benzyl- -: N- (6-heptenyl) -N'-butyl-urea N- (7-octenyl) -N'-methyl-urea N- (8-nonenyl) ) -N'-n-octyl urea N.N'-di (9-decenyl) urea N- (10-undecenyl) -N ', N'-dimethyl urea N- (3-butenyl) -N ', N'-dibutylurea N- (4-pentenyl) -N', N'-diphenylurea Thioureas allylthiourea N-aHyl-N'-benzoyl-thiourea N-allyl-N'-butyl-thiourea N-allyl -N'-methyl-thiourea N-allyl-N'-n-octyl-thiourea N-allyl-N / -phenyl-thiourea N, N'-diallyl-thiourea N-allyl-N, N'-dimethyl-thiourea N -allyl-N ', N'-dibutyl-thiourea N-allyl-N', N'-diphenyl-thiourea N- (3-butenyl) thiourea N- (4-pentenyl) -N'-benzoyl-thiourea N - (5-hexenyl) -N'-butyl-thiourea N- (6-heptenyl) -N '-methyl-thiourea N- (7-octenyl) -N'-n-octyl-thiourea N- (8-nonenyl) -N'-phenyl-thiourea N, N'-di (9-decenyl) thiourea N- (10-undecenyl) -N ^ N'-dimethyl-thiourea N- (3-butenyl) -N ', N'-dibutyl-thiourea N- (4-pentenyl) -N', N'- diphenyl thiourea silanes vinyltrimethoxysilane winylotrójetoksysilan winylotrójbutoksysilan winylotrójheksyloksysilan winylotrójcykloheksyloksysilan winylotrójoktoksysilan winylotrójfenoksysilan winylotrójbenzyloksysilan dwuwinylodwumetylosilan allilotrójmetoksysilan allilotrójetoksysilan allilotrójbutoksysilan 47 59 50 60 1 1 allilotrój cykloheksylaksysilan allilotrójfenoksysilan (3-butenyl) trójmetoksysilan (4-pentenyl) trójetoksysilan (5- hexenyl) trójbutoksysilan (6-heptenyl) trójheksyloksysilan (7-octenyl) tricyclohexyloxysilane (8-nonenyl) trioctexysilane (9-decenyl) triphenoxysilane (10-undecenyl) tribenzyloxysilane (3-butenyl) trbenzyloxysilane (4-pentenyl) triphenoxysilane (5-hexyctoxysilane) (5-hexyctoxysilane) exyloxy silane (7-octenyIo) trihexyloxysilane Alcohols allyl alcohol metallyl alcohol 3-butenol-1 2-methyl-2-propenol-1 4-penthenol-1 4-penthenol-2 1-penthenol-3 2-methyl-3- butenol-1 3-methyl-3-butenol-1 2-methyl-4-pentenol-2 4-methyl-1-pentenol-3 1,5-hexadienol-3 9-decenol-1 -undecenol-1 1- (tetrahydro -1,1-dicet--2-thienyl) -3-butenol-2-hexenol-1 6-heptenol-1 7-octenol-1 8-nonenol-1 Nitrile acrylonitrile. methacrylonitrile allyl cyanide 3-butenenitrile 4-pentenenitrile-hexenenitrile 6-heptenenitrile 7-octenonitrile 1 8-nonenenitrile 9-decenenitrile -undecenenitrile Benzenes o-vinylbenzene m-vinylbenzene p-divinylisropenebenzene p-methyvinylisropylene-di-benzenepenzenem 2-chlorostyrene 3-chlorostyrene 4-chlorostyrene 4-methylstyrene o-methylstyrene 4-methoxystyrene | 4-ethoxystyrene 2 62 58 6121 1 * 2,5-dimethoxystyrene 1 2,5-dichlorostyrene 1 (3-butenyl) benzene (4-pentenyl) benzene p-di (5-hexenyl) benzene m-di (6-heptenyl) benzene p-DHW (6-heptenyl) benzene 7-octenyl- (3,4-methylenedioxy) -benzene 2-chloro- (7-octenyl) benzene 3-bromo- (8-nonenyl) benzene 4-chloro- (9- decenyl) benzene 4-methyl- (10-undecenyl) benzene 2-methyl- (3-butenyl) benzene 4-methoxy- (4-pentenyl) benzene 4-ethoxy- (5-hexenyl) benzene 2,5-dimethoxy (6 -heptenyl) benzene 2,5-dichloro (7-octenyl) benzene 2-trifluoromethyl- (8-nonenyl) benzene 2,5-dibromQ- (9-decenyl) benzene. 1 2 Trimethyltin hydride used in the process Z5 according to the invention has the formula (CHibSn-H. This hydride is prepared according to known methods as shown, for example, by K. Hayashi, J. Iyod and J. Shiihar in J. Organometal. Chem., 10 , 81 (1967), HG Kuivila W Advan. Organometal Chem., 1, 47 (1964), 30 WP Neumann, Angew. Chem., International Edit., 2, 165 (1965). The compounds falling within the scope of the invention have the properties of insecticides and herbicides and can be used in various ways, in practice they can be used alone, either diluted or suspended in suitable carriers such as water, alcohols, ketones, phenols, toluene or xylene. Optionally one or more active ingredients are used. and / or inert solvents, so they can be used in the form of dusts, granules, wettable powders, pastes, emulsifying concentrates, aerosols, water-soluble concentrates, or in water-soluble solids. For example, to obtain a dust containing as a composition active compound according to the invention. The active ingredient is mixed or absorbed with powdered solid carriers such as various types of mineral silicas, e.g. mica, talcum, pyroflite, and clays in or to obtain a liquid and / or sprayable form. liquids in suitable solvents such as acetone, benzene or kerosene, or in the form of a dispersion in a suitable non-dissolving medium, e.g. water. For plant protection (the term includes crops), it is preferable to use water emulsions containing a surfactant dispersant, which may be a surfactant of the amine, non-ionic or cationic type. Suitable surfactants are known from, for example, US Pat. No. 2,547,724 lines 3 and 4. The active ingredient of the compound according to the invention may be mixed with surfactants with or without the use of a solvent. organic, a concentrate is obtained and the active ingredient is mixed with water to obtain a suspension. The active ingredient can also be mixed with powdered solid carriers such as mineral silicas together with a dispersing surfactant to form a wettable powder that can be used directly or mixed with water to form a suspension. It is suitable for use in water. The composition containing the compound according to the invention may be used in the form of an aerosol. Solutions suitable for use as an aerosol are prepared by dissolving the active ingredient in an aerosol carrier which is liquid under pressure and which is generally gaseous at a temperature of, for example, 20 ° C and atmospheric pressure. An aerosol solution can also be prepared by dissolving the active ingredient in a less volatile solvent and then mixing it with a more volatile liquid aerosol carrier. The active ingredient may be mixed with carriers which are active ingredients themselves, for example other insecticides, acaricides, fungicides and bactericides. The active ingredient is used in amounts appropriate to the desired effect. These amounts can vary and are generally in the range of 1-95% of the carrier. The spray solutions may contain a certain amount of concentrated concentrate per unit area on which the plants grow, and this amount may be about 0.005-5 kg / acre. In principle, the compound of the invention can be used directly. For example, to control aphids on plants they feed on. Spraying is used to efficiently kill aphids adhering to the inner surfaces of curled leaves or aphids living in leaf envelopes, e.g. cereals. Another effective method of applying the compound of the present invention is by introducing it into the ground or other environment. in which plant insects live. The active ingredients affect insects systematically after the compounds have been absorbed by the plants. Harmful insects and pests such as mites attack a wide variety of plants, including both ornamental plants and agricultural plants such as chrysanthemums, azaleas, cotton, corn, cereals, apple trees. not and tobacco, and they cause damage by depriving plants of their vital juices, releasing poisonous substances and often by transmitting diseases. The compound of the invention prevents this damage. Methods of using the compounds according to the invention, the selection and concentration of the active ingredient, of course, depend on various factors such as surfaces, climate, type of infection, etc. The known test methods are used. The insecticidal and herbicidal properties of the compound produced are described below. a method according to the invention. * rt & 23 u Test A. Mosquito larvae. mg of the organocin derivative is dissolved in ml of acetone. This solution is diluted with water to 1 ppm. 25 ml aliquots were placed in test tubes to which 10-25 larvae of fourth stage development of Aedes aegypti (linnaneus) yellow fever mosquitoes were introduced. The tubes were kept in the dark for 72 hours. At the end of this period, the percentage of larval control was calculated. Test B. Aphid. In general, 0.6 g of the organocin derivative is dissolved in 10 ml of acetone, 2 drops of Triton - X 100 wetting agent (ctylphenoxypolyethoxyethanol with 9-10 mole percent polyethylene oxide) are added, and suspended in 300 ml of water to obtain a 6,000 ppm. The aliquot was diluted with distilled water to obtain a concentration of 1000 ppm of organocin derivative. Eight to nine-day-old barley seedlings grown in pots were contaminated with Rhopalosiphum maids (Fitch). After two days, each pot was sprayed with the test compound and the plants were rotated. The plants were then kept for 5 days in a greenhouse. At the end of this period, percent control was calculated by comparison with the untreated control plants. Test C. Butterfly pest of tobacco. The form of the test compound was prepared in a manner analogous to that described in Test B for aphids. Two tenths of the preparation was pipetted onto an area of five grams of synthetic food held in partially filled cells in a plastic jelly-like tray. Each dilution was introduced into five cells. The food mixture was modified with a Vanderzant diet, including wheat germ, soybean flour, agar, sugar, salts, vitamins, preservatives and water. The trays had fifty soils on the surface, each with a size of 2.5 X 4.0 X 1.5 cm. The larvae of the tobacco pest Heliothis virescens (Fabricius) at the third or early fourth stage of development were placed in each The trays were covered with a thin plastic film and a sheet of rigid plastic and placed in an incubator at a temperature (80 ° F) of about 21 ° C. At the end of the week, the trays were tested and percent control was calculated by calculating the natural mortality in the controls using the Abbof's formula . After additional processing of the trays for a week, an anomaly in the development of the surviving larvae was observed. Test D. Cotton weevil pest. A preparation containing the test compound at a concentration of 1000 ppm was produced in a manner analogous to that described in test B for aphids. In the test, 12-14 day old cotton seedlings grown in pots were used. Each dilution was applied to two pots using an atomizer spraying with the pots rotated. Five adult weevils, Anthonomus grandis Boheman, were placed in each pot and the pots were covered with small-perforated styrofoam pots at the bottom. After five days in the greenhouse, the percentage of weevils that survived with natural mortality on horse plants was calculated. trolls using the Abbofs formula. The percentage of nutrient reduction was expressed by visual comparison of damaged food with the control plants, i.e. untreated plants. Test E. Roztocze. The preparation containing the test compound at a concentration of 1000 ppm was produced in a manner analogous to that described in the following: cut B in the case of aphids. Second leaf stage cotton grown in pots under greenhouse conditions at a temperature of about 21 ° -24 ° C (70 ° -75 ° F) was used in the test. One plant (two primary leaves) in one pot was used for each replicate and two replicates were used for each organic derivative. Before application of the compound, 25 adult Tetranyus urticae Koch mites were introduced on each plant. The contaminated plants were sprayed with a small atomizer onto the foliage. The plants were then returned to the greenhouse and held there for six days. After this time, the plants were tested calculating adult live mites remaining on the leaves. The percentage of control was calculated by comparison with the number of living mites remaining on the control plants. Test F. Mites - one-day residue. "" The preparation containing the test compound at a concentration of 50% was produced in a manner analogous to that described in test B for aphids. In the test, cotton plants of the second primary leaf stage were grown in pots under greenhouse conditions at a temperature of about 21-24 ° C (70-75 ° F). One plant was used for each replicate (two primary leaves). ) Two replicates were used for each concentration of the organocin derivative tested. Plants were sprayed with a small spray onto the foliage. One day after spraying, live adult Tetrańus urticae Koch mites were placed on top of the leaves. id Six days after contamination. Plants were tested by counting the remaining adult mites. The results were compared with the number of viable mites in the control sample and the percentage of Walczania.Wzór Abbotfsa% mortality = ¦% of gwyeh iv% alive in the test of kem- - kem- troller work of the Kioo center% alive in the control sample The obtained test results are presented in the table x-cnucflCflc^^^ ^^^^^ l ^ l ^ l ^ l ^ uU'CdCdUuuClllCdCJ ^^ MMMlotoMlo ^^ MHHMHHHMHHM ^ 01 ^ 0J (0h-OCDC0 <10) Ul ^ Wb0MOCD00 ^ 0Cfl ^ WMMO (r) C0 <| 0) OOO ^ C0 ^ a ^ W0MOC000 OO ht ~ 0-3 "OOOOOO -o OOO) About OOOOOO ^ OOOOOOOOh ^ OOOCpOOOOO- ^ OO 000) 0 OOOOOOoOOOlOOoOoOoOOOOoOOOOOOOOOOOOOOOOOOOlOOOOlOOOOUlOOOOOO * • * ¦w ooocoooopoo © © o © © © © oo OOOCJlOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOiOOOOlOOOOOOo OOOOOO OO OOOOOOOOO OO "O" "O" O -O "O" O "O -O" O -O -O -O -O -O -® - ^ O - © - © -O OO O OO OOO j © O * OQOOOOO - OOOOOOO OOOOOO .OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO OO OO OOwOOO © OOO o ^ cnoooo; o- ^ boooboo-q- ^ oi * © 01 -q 4 ^ © --0 ^^ © cncoocoooioioorf ^ oooojtOOioo00iooooio ^ oooojtoocnto0ioooioorf ^ oooojto0ioooi0 ^ 0 ^ 00l - '^ (0 ^^ C0O (0 (0C0 (0tb ^ O00 (0 ^ O ^ GS00 "O tD W <1 -O ^ 10CDcpCDOCDOO 1 00 O OOOOOOlCn; OC ^ C ^ OOOOOOOOOOOlOOOOOOOO © C ^ CnOO ^ OOOOOOOOC7 ^^^ 00000, * ll © © ¦ lll 1 lilli 1 iii 1 iiiiiili I illlliiiii .1 iiiuiiii I i 1 iiiilili I © OlOOOCOOOO © OO © © © Ol © © © © © J © CO LO © © © bO 000 (0 ^ 01 (01000 (000 * 0 bOCOOOOOOOO ©###### PT Vo) * A 00 ** N PT Vo fights Mosquito larvae control 1 ppm% aphid control 1000 ppm% total pest control; Density: 1000 ppm% of fleece pest control 1000 ppm% of nutrient reduction on cotton Mite control test 1000 ppm Mites One day residue 500 ppm by 100% ON CO 3 ft3 • a ¦- * N ^ 001 'U 3 N 3 03 ON CO ts W? D • -i N ^ i- »oo * ao 3 13 CD o- & j a» 3 »o? A - * N * <Ol O ow * C 3 'N 3 03 ON CO 13 P? A »- * M ^ h-» OOV • o 3 13 O a- 03 a 03 13 OV? 1 N «<I- * OOO • a 3 * w wo oopo C * 5 r + y & 13 03 3 N 03 s ^ § 13 o% VT o 9 CO 2 3 every 3 RS-o O 00 1 CO 03 v co ar ¦ «| 3 | 3 O) 03 IO PT IN o 3. to oooooooooooooooooo oo oo co what ooo OOOOOlOOl-jOOO OO Ol OO ooooooooooooooo ooooooooo ooooooooo oo - ^ -oo what oooooooo «J what what what 00 oo what about Ol O) oo 00 Ol is fcO 00 what -a I-- Ol Oi 00 what what ooo what O Ol OOOO _. _. O CO OOOOO Ol OOIIIIIIIIIIIIIII 1 II 1 1 III 1 II 1 II lilii OOOOOOOOOO OOOOOOOOOOOOOOOOOOO ooooooooioo ^ eo I oo OOOOOOOOOOOOOOO O. w'O O "o J9 03 &» «*. Z9 * Compound described by Stammf and colleagues, whose data shown at the end of Table III was prepared by the method described in Example 1 of Stamm and associates. The compound described by Kopmans et al., the data of which is similarly illustrated, was prepared by the method described below. A solution of 5.95 g (0.033 mol) of the compound of formula 66 in 50 ml of H 2 O is introduced into a 250 ml Erlenmeyer flask. Then 6.6 g (0.033 mol) of (CH 3) 3SnCl in 100 ml of acetone is added dropwise. The reaction mixture is heated to 60 ° C in 20 minutes. After stirring overnight, the acetone is removed by evaporation and a sticky white residue is formed. The water is decanted. 50 ml are added to the viscous residue. petroleum ether. The solidified product, weighing 8.1 g, has a melting point of -102 ° C. Peter M. Slegan of the University of North Carolina, Ph.D. thesis 1967 determined a melting point of 98-102 ° C for the trimethyltin salt of p-tolueosulfinic acid. The IR spectrum showed strong absorption at 955 cm-Vi 990 cm-1. The results shown in Table 1 show that the decay of the invention will cure good to exceptionally high insecticidal activity against a variety of insects, especially compared to bad ones of this type. The numbers of the compounds in the tests and examples correspond to the data presented in Table IX.Test II. Testing acaricidal organic compounds at various concentrations. In this test, preparations with various concentrations of the tested compound, ie a representative organocin compound, were used; The tests were carried out as described below. The study used second-leaf stage wool grown in pots under greenhouse conditions at 70-75 ° F. One plant in one pot was used for the seventh replicate, and two replicates were used for each test compound concentration, organocin. Preparation i was prepared by dissolving 50 mg of organocin compound in 1 ml of acetone dropwise Emulfor9 * !. 719 (epoxyethylated vegetable oil) ™ of a known dispersive surfactant, and by slurrying in 50 ml of water, the active ingredient concentration is 1000 ppm. Subartrophages of this solution were obtained by further diluting with distilled water to a concentration of 10% and 20 and 5 ppm. ^ Plants - ulisfcf not sprayed with a small spray agent pomttoa. One day after spraying, the mature Tetnai urticas Koch was placed on the upper surface of the leaves. The number of mites was calculated immediately after insertion and again after six days. The AbbotFs formula was used to calculate the mortality and percent pest control. The results obtained are presented in Table II. 3 Table II 40 45 S5 Compound No. i 14 23 41 66 67 68 1 75 80 One-day mite test 100 ppm 100 100 94 100 100 100 IDO 100 78 ppm 99 68 45 87 79 93 100 95 6 ppm 63 49 44. 57 1 4 1 0 1 2 4.0. The results show that the representative organocin compounds produced by the process of the invention show a high degree of activity at various concentrations of the agent. Test III. Cotton toast - butterfly pest of tobacco. The test was carried out as described below. The preparation was prepared by dissolving CO ml of organocin compound in 1 ml of acetone, dropwise addition of Emuifbr 719, which is a known dispersing agent. the surface-active agent and preparation of a suspension in 50 ml of water. An active ingredient concentration of 1000 ppm was obtained. Subvalues for this solution were obtained by further diluting with distilled water to concentrations of 100, 20 and 5 ppm. Two-week-old cotton seedlings were used. Plants were grown in pots of two plants in each pot. The diluted solution was applied to the plants with a small atomizer and allowed to dry. Three pots were used for each dilution. Tobacco pest larvae. Third stage Heliothis virescens (Fabficius) were placed in a pot and covered with a polystyrene pot of the same size with a perforated bottom. The percentage of pest control was calculated after two weeks of keeping in a greenhouse. The obtained results are presented in Table of the Jagiellonian University. Table III Butterfly pest of tobacco plants on cotton growing in a greenhouse Compound No. 1 14 W m 41 45 52 * ¦ «100 ppm 100 ioa 6 * 100 100 100 109 'm / o combating ppm 100 100 50 33 100 100 0 33 ppm 100 50 0 06 0 0 0 0 | The results presented in Table III show that the Organocin compounds have excellent properties in combating this type of insect. Tesi fV. This test, similarly to tests II and III, concerns the action of various concentrations of: 'representative organocin compounds. The test was performed as described below. The test preparation was prepared by dissolving 1.0 mg of the organocin compound in 1 ml of acetone, adding one drop (about 30 mg) of Emulfor 719 as a surfactant and diluting it with 100 mg. ml of water to obtain a concentration of 100 ppm of organocin compound in water. A further dilution with water was carried out to obtain a concentration of ppm and 1 ppm. The study used eight-day-old barley seedlings grown in pots. Ten plants were used per pot. The pot together with the soil weighed about 440 g. Seedlings infected with Rhopalosidium maidis (Fitch) corn leaves one day before treatment. Twenty-two ml of the diluted compound was applied to the pot surface, not to the contaminated plant parts. The dose per kg / acre was 440 g / pot and totaled per acre of soil 7 inches deep weighing approximately 1 million kg. The percentage of control was determined by observations made one week after compound application. The results obtained are shown in Table IV. Table IV Compound No. 1 14 23 45 52 56 Test of performance on soil% aphid control = A 100 86 95 100 100 100 1 = A 93 86 99 80 97 0.1 = A | 86 0 78 0 40 70-5. This study has shown that the compounds of the invention are effective as systems. highly effective insecticides of barley plants, which absorb the right amount of organocin for effective control of aphids. Test. V. Organocin compounds as herbicides before plant emergence. This test illustrates the action of the compounds as herbicides before plant emergence. The compound is used by dissolving 600 mg of the organocin compound in 10 ml of an organic solvent, e.g. acetone to which is added the known emulsifiable substances, e.g. isooctyl polyethoxyethanol, "TritonX 100". The solution is diluted to 100 ml with distilled water. Ten milliliters of this 6000 ppm solution is diluted with distilled water to obtain 250 ppm of active ingredient. The solution is used in 5 kg / acre by draining 46 ml of solution with an active ingredient concentration of 250 ppm onto the ground surface of a 4 - whole plastic pot in which the following weeds and grasses grew: Amaranthus retroflexus L; Portulaca oleracea L; Datura Dziedzierzawa Datura Stramonium L .; Ipomea pur- purea (L.) Roth; Datura isch Digitaria isch a-emum (Schreb) Muhl; unilateral weed Echinochloa crusgalli (L.) Beauv; setaria faberi Herm; and Cyperius Rotundus L. The percentage of weed control was compared with that of the untreated plants and calculated two weeks after treatment. Table V shows the indicator of the herbicidal action before emergence of plants. Table V Herbicidal properties of organocin compounds before emergence of plants Compound number 1 1 3 4 6 1 '7 f 8 9 11 12 13 "14 16 17 18 19 .. 21 22 23 Dose kg / acre 2 <Grass weeds 3 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 ioo 100 100 Vareweed 4 lOOp 100 100 100 100 100 100 100 100 lOOp 100 lOOp 100 100 100 100 100 100 100 100 95 50p Jmpomea purpurea 100 100 100 ioo 100 100 100 100 100 100 98 100 100 50 100 100 100 95 50 65 Blood torch g 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 85 95 70 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 every 80 90 One-sided weed 8 lo0 100 100 100 100 1C0 100 100 100 100 100 80 100 100 100 100 100 100 100 100 80non »34 Table V (continued) 1 -24 '25 '26 <27 r28 ** 0 '30 '31 '32 33 34 '36 <«6 37 '98" 39 U40 <41 -42 043, 0.44 045 'J46 U47 t48 ^ 49 -50 / §1 •• 52 -53 84 -55 56 * 57 59 - * r -61 -62 | '63 2 S "5 *: 5 6 f ^ B: 5 8; 5 f5 -: 5 f5? 5 ¦ * 5 1 f5 'L« ~ 5 ~ * - • 5 l5 * V * "5 • UJ ¦r -5 * 5 ~ 5 5 5 3 160 190 190 90 0 100 190 100 100 100 100 100 45 100 100 190 190 S5 1 ^ 0 i * 190 190 190 199 Im KK) 140 100 100 WO 100 100 100 100 100 100 100 100 ^ 95 4 100 100 98 80 • 0 100 0 0 100 100 lOOp 80 0 100 100 196 196 <0 i nO 9 & 90 lOOp 19 »199 109 100 199 100 100 100 100 100 100 109p 100: 0 100 100 100 0 90 0 100 i # o 80 100 100 98 100 190 95 0. a & 100 90 (O 190 190 90 95 n98 80 ieo 80 100 90 100 100 85: 0 ~ 6 '100 100 50 100 0 65 0 90 100 65 100 90 60 100 100 100 100 80 95 00 90 75 190 38 190 © 100 140 100 IW 100 100 100 100 100 100 95 # 5 9 7 100 100 95 100 0 98 98 100 100 98 100 100 60 100 100 100 100 0 100 0 90, 0 100 65 1/90 100 100 1 * 0 m 100 100 100 100 100 MO 100 ^ 0 85 0 8 100 100 0 0 I 100 100 90 10Q 100 100 60 40 100 100 100 100 0 1.00 99 $ 0 $ 8 1O0 $ 5 45 W 100 160 IOO 100 W 100 100 400 100 WQ & 8 M o The data presented in Table V show that the compounds prepared by the method according to the invention u • remove overall, excellent herbicidal action pmsed the emergence of plants with respect to different types of weeds. These * VI. The herbicidal action of the compounds after emergence of the plants. This test illustrates the herbicidal effectiveness of the tested compounds after the emergence of the plants. The compound was applied analogously to the description. The plant was tested in test V, six days after emergence of the plants, and applied to the foliage with a conventional De Vilbiss sprayer. The degree of control was calculated two weeks after the application of the compound. Table VI shows the results obtained. Table VI Post-emergence herbicidal action rpslm Compound, no. 1 l 1 1 3 1 4 Dose in ppm 2 iii Grass weeds 3 100 100 100 Datura and bushes 4 UOOp 90 100 Ipomea purpurea 50 100 100 Stalker 6 50 100 100 Trichomoniasis 7 so 100 73 Unilateral weeds ¦-8 100 100 [WtO ^ OCOC »^ <^ Cn4 ^ WtO ^ O« OC0 ^ 05Cn ^ 05fcOl ^ O 0) 0) OiO) QQO) 0) 0) 0) OV O) O) O) O) a) a) O) O) O) O) O) O} O) O) O) OO) O) O) O) O) O) O} O) OO) O) OtO) O) OOiO) 0) O} O} AO) O) O) O) O) O) OO) O) O) O) OOO, O OOlOOO'0 0100 010 000 000 0'OOIO'OOOlOO'iOOOOOiOOOOOOOOOOOOOOOOOOOO 'OOOO OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO OC0OCDC0OOOOOOC0OOOOOOOC005C0O, COOOOOCOOOO 0Ofc0Oh OC0OC0h ^ ^ l- ^ FC0 "aOOOC0OOO <0OOOOO OOOOOOOOOOOOOOOOOOOOOCnOlCnOOOOOOOlOOOPOlOOlOCnOOOOOCnOOlOOOOOOOOCOOOOOO of 00-and lh ^ - ^ OO O; D h-" OOO Ol O to bO CO OO tO ts9 O | -i hi d fc * KO hh- ^ OOOiSO O hL OOO CO oooooi ^ oooioaioioooooooiooioooooooi ^ PooooioooaiOcnoooociiaic ^ oo ^ Ooocncnoooo 7j 73 aj what - * j this is oo o what cp oooolo, whato ^ this »-» 1 OOOLOC ^ WOOOOOOOCLOOOOClOlOClOOCLOOOOCLOOOOCLOOOOCLOOOOCLOOOOCLOOOOTHOOTHOOT - »1- * (-» I- * h- * h ^ h ^ 'h- »l-» h- »¦ l-» M h- »h ^ 1 CO H OOOOl-'OCOI-'OlCOO CJ1 CO tO tO Ol CJlCOOO ^ adOCOOd fcO CO C71 -a h- »bO I- * h- * hi Oi CJi 00 h- OOO h- * OOOO [OOlOC ^ C ^ OOOOOC ^ OOCDOC ^ OOOlOOOOOCJlOOQOOCJlC7lC ^ CJlC ^ C7lC ^ C7lC ^ C ^ O) O) O (O CO CO h- »O CO O CO CO -J tO 00 00 OO Ol -q O CO CO MO) ht H- tO CO 00 OOO rf * c © ® © O OlOlOOlOOO» OOOOOOOlOOOlOOOOOOl0000000010lOOlOlOlOOOOOlOOOlOOlOOlOOlOOlOOlOOlOOl © © l- »| - * hp *» - * hi h- »(- * | _» I-1 - »I— h-» h- »h- * OOMmmm ^ O © W {DCOMOOOM ^ CO <1M cbMCOMOOC »00 to? - -» • OOl © 00 © © OOOIOOO © © © © Ol © OlOlOl © © Ol © OI © © © 0 © Ol © © OlOlOO © © © OlOl © © OI01 © OOOl © © © © 0 © all-in-one I- * 1 that is 1 * Ol O) ¦ ^ 00 en KIO * ot a # - »N37 The results presented in Table VI indicate that organocin compounds also show in the east lin has excellent herbicidal properties against various types of weeds. As has been shown in the prior art, the sulfonyl compounds described by Peterson are hydrolyzed under the influence of air. The following experiences confirm this statement. The vessel with a capacity of 3.785 liters was placed on a wooden support containing a wire mesh to support the samples in the test over a mixture of 152 g (NHO2SO4 in 168 g H2O. Excess (NH4) 2SCh was contacted with a saturated aqueous solution (NH4): S04, resulting in 81% closed moisture (Handbook of Chemistry and Physics.Chem. Rubber Pub. Co., p. 2500 (1960). The following samples of Peterson's compound were weighed in petri dishes OD 40 mm (minus the coverage) 8 mm deep and the plates were placed in a moistened chamber and then The plate was closed: 15 plates 0.2186 g; 34 plates 0.2006 g. Previously, the samples were equilibrated, a solid shell began to form on the surface of the liquid and within 10 myrtles covered the entire liquid surface. The smell of volatile trimethyltin was noted. In the finished sample chamber, all surfaces on the outside of the plates were coated. A 3,785-liter vessel was placed on the lava under normal laboratory conditions. chamber was 24.5 ° C. After four days, the temperature was lowered to 18 ° C. After 4 days, a = 15 sample was isolated. An oily solid formed beneath the surface of the crust. The sample was scraped with a spatula into 2 g vials. The residual oily matter was weighed in vials containing chlorophore (about 0.5-1 ml). Chloroform was removed under a stream of nitrogen. Sample = 34 was withdrawn from the chamber after 7 days. The sample was completely solidified and scraped into vials. The NMR spectrum of both samples showed that the additional aromatic absorption corresponding to the singlet of the CH3 group of the hydrolyzed product (Formula 69) took place at 307 Hz and the wider singlet flanked by the satellites took place at 36.5 Hz for the (CHa) 3 group and extended singlet at 191 Hz for the OH group. The results obtained indicate the preparation of a mixture of trimethyl tin hydroxide and methyl phenyl sulfone. There was no unreacted original Peterson relationship. A corresponding compound falling within the scope of the invention, i.e. a phenylsulfonylethyltrimethylstinate of the formula 71, was tested in an analogous apparatus and under the same conditions. The following tests of the said compound purified on a chromatographic column were weighed on small lids of petri plates and placed in a 81% humidity chamber. at 27 ° C. Plate = 15-0.2426 g. Plate = 34-0.2020 g. The test duration is as stated above. Maintain room temperature .... Sample = 34 was taken from the chamber after 4 days and the infrared spectrum was examined within a few minutes. No additional absorption bands were found from the original sample. Sample 15 was selected with 99 * 1638 from the chamber after 2 weeks. The infrared spectrum of this test was exactly in line with that of the starting material. No additional absorption steps were present. The NMR spectrum of both samples was identical to the starting material. Thus, it was confirmed that the test compound within the scope of the invention is not hydrolyzed under the specified conditions. The following is a general method of producing a compound of the formula 72 falling within the scope of the invention, that is, according to Peterson's patent specification No. 3,794,670. 2- [p-Tert-butylphenylsulfonyl] ethyltrimethyltinate. However, the resulting compound indicates that it is 1- [p-tert-butylphenylsulfonyl] Gtylotrimethyltinate of formula 73. These losses due to hydrolysis alone weaken the effect of the Peterson compound. round bottom 500 ml 3-necked flask equipped with a mechanical stirrer, Y inlet with N 'tube, additional 125 ml funnel (flame dried and filled with N2) and ice water bath, then a simple distiller, thermometer and oil bath. The materials used were: 1) 140.0 ml (total volume of benzene reagent distilled to remove azeotroup from water, 2) 18.5 ml (13.1 g, 0.13 mol) of diethylamine (dried), 3) 94.0 ml (0.15 mol) 1.6 molar of n-butyllithium and n-hexane, 4) 29.8 gm (0.15 mol) of trimethyltin chloride,) 33.9 gm (0.15 mol) of p-tert-butylphenyl styrene - sulfone (mole by weight 226.3). All syringes were first dried at 110 ° C. and cooled under nitrogen. A syringe of diethylamyrie and 50 ml of benzene was placed in the flask 40. Butyllithium was placed in an additional funnel with a syringe. The reaction flask was cooled with mechanical agitation in a water - ice bath and butyllithium was added dropwise over 33 minutes. The reaction solution turned a milky white color. An additional funnel was introduced with 10 ml of benzene by means of a syringe and the reaction flask was dried. Trinetyltin chloride dissolved in 50 ml of benzene was introduced in a syringe into a N2-purged 125 ml Erlenmeyer flask and poured into an additional funnel using a syringe. An additional 25 mL of benzene was used to rinse the flask and the water was poured into an additional funnel. The temperature of the reaction mixture was kept in the range of 0 ° -5 ° C. with an ice bath. The tin chloride solution was added dropwise to the mixture over an hour. The reaction mixture was then allowed to warm to room temperature while stirring for 1 hour and 10 minutes. The sulfone was weighed and added directly as a solid and dissolved easily. The mixture was stirred for 1 hour at room temperature and kept under nitrogen overnight. The reaction mixture turned a light milky color. In the morning a distillation apparatus with an embedded thermometer, a reflux thermometer, a silica gel TLC (Eastman) thin-layer chromatography was used with 9- ( 1-cyclohexane) EtOAc showed two large spots. Table VII. Start time min. 22 min. min. min. 46 min. 1 hour 5 min. 1 hour 45 min. 2 hours. 2 hours. 15 min. 3 hours 20 min. 3 hours S5 min. 4 hours 5 min. 4 hours 15 min. 4 hours 50 min. at 5 min. at 15 minutes Oil bath temperature 54 69 84 86 83 95.5 100 110 117 123.5 125 125 125.5 124.5 123 123 123.55 Internal temperature stains 37.5 55.0 64 66 73.5 77 83 95 105 112 115 115 115.5 115.5 113 113 114 Reflux temperature 24 (RT) 24 49 54 61.5 70 72 73 75.5 70 50.5 60 49 44 43 57.5 51 (distillate entering the collector) ¦ «.- ¦ (Schlieren effect present in the collector) (Schlieren effect present in the collector) (reduce leakage) (Cessation. Spot contains haze, brown paste) (reduced mixing, a few drops over) (rare drops) (initially N2 cleans the reaction vessel and collector, reflux temperature up to 66 ° C, spot temperature - 111 ° C and overflow distillate) (thin drops) (rare drops; cooling to RT in N2 atmosphere.) [With an oil bath gauge and condenser, and a 300 mL flat bottom 1-neck flask with contents were kept under a nitrogen atmosphere. The distillation apparatus was disassembled during cooling. The drain was kept under nitrogen and cooled to 0 ° -5 ° C. in an ice bath. A light brown paste was obtained. A solution of 4.0 g, 3.4 cm *, (0.04 mol) HCl in 200 cm * H2O was added to the receiver. The dew point temperature was 30-35 ° C and fell rapidly. The remaining amount of HG1 was added. the ice bath was removed. Two phases were formed. Clear top H2O and light brown sticky oily top layer. The oily substance was dissolved by adding 100 cm of GHCl and all of the 0 was transferred to a 1 L separating funnel. Most of the organic phase was decanted. The remaining organic and aqueous phases were washed twice with CHCl. The resulting organic phase was decanted. The combined organic phases were dried over anhydrous. MgSO 4 overnight. The total was filtered under pressure using a 15 cm Buchner filter to prevent the filter and mixture from coming into contact with air. The pale pulp was treated with Darco G 60 at room temperature for 1.5 hours and drained by gravity. (keeping covered) into a tared 1 liter 1-neck round bottom flask, and the GHCl3 was removed on a Rotovac (Rotovac was kept under N2) to give a clear-brown bright viscous liquid, 46.2 gm. the distance from the original was 25 mm and 37 mm. The shorter distance of spots had the same distance as for the starting ethylsulfone. The spots observed under short UV waves were of almost equal size. iarach and intensity. The oily material was distilled under reduced pressure with brief heating and a single 50 ml receiver. The oily matter was collected at 120 ° -154 ° C and 0.6-0.12 mm Hg pressure. The temperature of the vessel was 150 ° -200 ° C. No separation emerged. The oily distillate formed some solids which were separated by decanting the oily substance and pressing the solid on a filter paper. 3.86 g of a solid was obtained which, after recrystallization from petroleum ether, had a melting point of 43-65 ° C. TLC of this material showed * 2 spots the same as the crude product. The oily distillate was redistilled by a microWar, Vigreaux vacuum column. Harvest = 1 - boiling point 48-12 ° C (2.5-3X10 ~ 3nm). TLC showed a large stain (starting sulfone) and a weak stain in the product. Harvest —2 boiling point 108—136 ° C (2—8X X10-8 mm). TLC showed a large stain of substrate and one smaller product. Harvest = 3 - boiling point 140-145 ° (0.1 mm) indicated as the main ingredient - product and a smaller stain of the sulfone substrate. Harvest 1 and 2 were formed because it contained little MH6 of the product. All three crops were slalic substances. Harvest = 3 weighed 5.6 g. Solids from the harvest were taken into boiling petroleum ether and filtered to remove impurities. The solution was adjusted to approximately 25 ml and cooled in a mixture of ice and water. The solids were filtered under pressure under nitrogen to give 2.73 g of a white solid, mp 78-81 ° C. This material was recrystallized from petroleum ether (about 10-15 ml) and cooled to -15 ° C. The solids were filtered under increased nitrogen pressure to give 2.21 g of a white crystalline solid with a melting point of 79.5-81.5 ° C. The magnetic spectrum of nuclear resonance showed that a 1,4-disubstituted aromatic a pattern with a relative intensity of 4 protons including a center band at 7.75 <3 corresponding to 2 ortho protons to the SO2 group and its mirror image concentrated at 7.47 <5 corresponding to two ortho protons to the tertiary butyl group. The band quartet was concentrated at 2.84 <5, the relative intensity of one proton corresponding to that of the methyl proton. Tertiary butyl and single methyl resonance produce a band of relative intensity, a tertiary resonance appearing as a singlet centered at 1.35? 5 and a methyl resonance appearing as. doublet centered 41 lanes. Plants were kept in a 85 ° F-holding chamber and exposed to high-intensity fluorescent radiation within 3 days after placing the mites on the plants. 3 week old plants covered with gauze were used during the test. Six replications were used for each test compound. The r larvae were observed 3 days after the spraying, and then 6 days after the spraying. In both tests, the solutions were expressed in millimoles / liter, so that the obtained results were exactly comparable, as the compounds differed in molecular weights. The clear superiority of the compounds falling within the scope of the invention over the comparative Peterson compounds and over the hydrolysis products are easily discernible. was used in comparative tests because it was found that Peterson's alkyl-substituted phenyl derivatives could not be obtained by the Peterson method described in U.S. Patent No. 3,794,670. The following are details of the preparation of trimethyl-4-tert-butylphenylsulfonyl-methyltinate. No. 1 of the US patent specification - Table VIII 1 Compound No. 13 with formula 74 Compound with formula 75 (CHabSnOH Mites% 0.6 98.4 44 9 control 0.3 100 14 34 0.15. 73 18 7 Butterfly pest of tobacco% 0 , 6 100 66 66 control 6 / o reduction 0.3 83 0 16 0.15 83 40 16 0.6 98 90 81 0.3 92 52 69 0515 88 73 | 50 | at 1.295. Singlet at 0.37 5 (37 Hz) flanked by two small satellite doublets with an overall relative intensity of 9 protons. This band is suitable for the trimethyltin group. The two satellite doublet sites are suitable for the associated three methyl groups to the two isotopes Sn — Sn117 and Sn119 with a nuclear spindle -. Thus, the structure shown in the preceding paragraph is confirmed by this example. The comparative data in Table VIII was obtained for Compound No. 13 falling within the scope of the invention, trimethylphenylsulfonylmethylstinate (Peterson's compound 55) and the hydrolysis product of Peterson compound designated as trimethyltin hydroxide. The Peterson compound was prepared according to Example 1 of US Patent No. 3,794,670 except that an equivalent amount of trimethyltin chloride was used instead of triethyltin bromide. Trimethyltin hydroxide was prepared by the method described by G.A. Luijten, Rec. Trav. chim 82, 1179 (1963). The one-day test of the American Pat. No. 3,794,670 was used and the procedure described below was used. To a solution of 18.5 ml (0.18 mol) of diethylamine in 50 ml of anhydrous benzene, 94.0 ml (0.15 mol) of 1.6 M n-butyllithium in n-hexane was added dropwise at 0-8 ° C. A solution of 29.8 g (0.15 mol) of trimethyltin chloride in 50 ml of benzene was added to the white suspension at 0-5 ° C. over 40 minutes. The reaction mixture was stirred at room temperature for 1.5 hours. and added to it 3l.8 g (0.15 mol) of 4-tert-butylphenylmethylsulfone. After the reaction mixture was stirred overnight at room temperature, the reaction vessel was heated until diethylamine and benzene had distilled off and then kept at 100-110 ° C for 2 hours. After cooling to room temperature, a solution of 4 g of concentrated hydrochloric acid in 200 ml of water is added rapidly to the reaction mixture within 2 minutes. The mixture obtained is washed quickly in a separate funnel with 200 ml of chloroform. The lower organic phase is separated, dried over MgSO and the solvent is separated, yielding 51.8 g of an amber oily substance. The viscous material is MM 43 separated by vacuum distillation using short-term heating. The following harvest is obtained: = 1, boiling point 26-145 ° C (5 × 10-3 mm) steady, Harvest = 2, boiling point 145-158 ° C (0.014—-0.03 mm) solid Oily, Harvest = 3, boiling point 158— 159 ° C <0.03— -0.48 mm) oily. Cooling residue black glass 16.2 g. The harvest was analyzed by (gpc) gas-liquid phase chromatography using a 6'XI / 8 "column. filled with 10% silicone rubber on silariized-diatomaceous earth at a column temperature of 260 ° C. Major component of the harvest = 1 indicates that it is up to 4-tert-butylphenylmethylsulfone; = 2 is a mixture of the primary sulfone input plus the higher component boiling point = 3 is the same mixture enriched with p component with Wy A very volatile component was also found, the amount of which increased successively with each batch. Further observations were made for the degree of pressure reduction associated with thermal decomposition. Crops 2 and 3 were combined and subjected to a second distillation using a vacuum Vigreaux column. One crop was obtained with a boiling point of 43-125 ° C (0.016-0.025 mm). The solid which was analyzed showed mainly a starting sulfone and a small amount of the higher boiling point component. Analysis of 8 g of the residue showed a mixture close to 1: 1 of the original sulfone and the higher boiling component. The Vigr6aux column was replaced by a third distillation with a short heat supply away the following shots: throw = 1 - boiling point 28-172 ° C (0.002— - ^ - 0.02 mm) about 1 ml of a yellowish liquid; projection = 2 - boiling point 174–1666 ° C (0.025-0.13 mm) constant 1.5 ml. Shot analysis = 1 again showed a mixture of nine of the same components, and projection = 2 only original sulfone. Shot sample = 1 was analyzed by spectrum nuclear magnetic resonance (TNMR). The NMR spectrum shows a 1: 1 molar mixture of the starting sulfone and the expected product, ie 4-tert-butylphenylsulfonylmethyltrimethylethate. In summary, the product could only be obtained as a mixture of the starting sulfone and the three distillations needed to separate the mixture. All indicated the points of thermal stability of the product at the temperature set for the distillation of the starting sulfone. In addition, testing of a cold trap (-70 ° C) (used to prevent the calculation of the vacuum pump) showed that the liquid that volatized at room temperature was causing the decomposition of the product. The method described in example 3 of US Patent No. 3,794 670 was unsuccessful in the preparation and isolation of trimethyl-4-tert-butylphenylsulfonylmethyltinin using the same starting materials. In this case, 53.6 g of an oily substance were obtained. 2 using a vacuum Vigreaux column, and the distillation of this material gave only a small amount of distillate with a boiling point of 70 ° -132 ° C (0.02 ° 0.04 mm), which was found to be the starting sulfone upon analysis. After replacing the column with short-term heating, it was possible to obtain only 11.9 of distillate with a boiling point of 70-150 ° C (0 # 19-0.27 mm) corresponding to the pressure loss. Analysis of the "glpc" distillate showed a starting sulfone in 90% of the distillate. The following examples illustrate the preparation of organocin derivatives and the anti-killing and herbicidal properties of these compounds. Example I. Eighty nil Schenk tube 5 from Pyrex glass by two the necks equipped with a magnetic stirrer are filled with nitrogen and kept in an air-free atmosphere. The tube is then filled with a mixture of 16.5 g (100 mmoles) of trimethyl tin and 5.9 g (50 mmoles) of divinyl sulfone, closed and illuminated. 100 watt mercury vapor for 4 hours. The reaction mixture is kept at 20 ° C and stirred with a mechanical stirrer. After recrystallization of the solid product from petroleum ether, 15 g of 2,2'-sulfonylbisethyltrimethylcymahu are obtained. mp 78.5—80.5 ° C - Compound No. 1 in Table X. The presence of both sulfonyl and trimethyltin groups indicates salt infrared absorption bands at 1300 cm-i, 1240 cm-*, 1140 cm-1, 1105 cm- * and 765 cm- * using KBr disk. The nuclear magnetic resonance (NMR) spectrum showed the protons at the sulfonyl residue appearing as a complex multiplet centered at 302 Hz (4 protons), the beta protons at the sulfonyl residue appearing as a complex multiplet concentrated at 114.5 Hfc (4 protons), protons of the trimethyltin group at 14.5 Hz, singlet consistent with one satellite band at the other end 40 (9 protons). CHS Sn percent analysis Calculated for OHO SSn: 26.9 5.87% \ T 53 .0 Found 26.9 6.16 6.89. 52.6 Example II. This example illustrates the use of a solvent in the reaction described in Example I. Proceeding in an analogous manner to that described in Example 1 using the same apparatus, 46 g (279 mmol) of trimethyl tin hydride, 16.5 g (139 mmol) of divinylsulfdnum and 30 ml of benzerir are introduced into a glass reaction tube Schenk * a.Tube is irradiated while stirring at temperature. 29 ° C under nitrogen atmosphere for 18 hours After filtration and evaporation of the solvent, the crude product was recrystallized from petroleum ether to give 48.5 g of 2,2'-sulfonylbisethyltrimethylstinate, m.p. 78.3-79.3 ° C, ie compound No. 2 with Table X. The analysis was carried out as described in Example 1. Compounds Nos. 16, 46 and 53 in Table X were prepared using the apparatus described in Example I, following the procedure described below. Example III. A mixture of 4.4 ml (5 g, H 42.4 mmoles) of divinyl sulfone, 5 ml (42.4 mmoles) of MSlt 45 "trimethyltin hydride and S ml of toluene is irradiated for 18 hours. From the liquid residue obtained after filtering The solvent is evaporated off. Five milliliters of piperidine are added to the crude product while stirring and cooling. Stirring is then continued for two hours at room temperature. Excess piperidine is removed under reduced pressure to give 9.2 g of liquid. - an oily state: 1.23 ml of methyl iodide are added to a solution of 5.2 g of the material obtained in 50 ml of benzene, after stirring for 3 days at room temperature, the filtration of 2.3 g of solid is collected; Purification of the solid by precipitation from acetone with diethyl ether gives 2- (2-piperidineethylsulfonyl) -ethyltrimethylstinate methadide, mp 122 ° -124 ° C, i.e. Compound No. 16 of Table X. The presence of sulfonyl residues and trimethyltin is shown to be with the help of absorb bands infrared rays at 1305 cm-1, 1260 cm-1, 1120 cm-1 and 770 cm-1 using KBr disk Percentage analysis: CHN calculated for CiaHsrfNOzSSN: 30.61 5 ^ 3 2.75 Found: 30 , 08 5.87 2.83 Example IV. A mixture of 8 g (30 moles) of 2- (ethoxycarbonyl) ethyltrimethyl cyttism (compound No. 47), ml (150 moles) ^ 95% hydrazine in 10 ml of ethanol is heated under reflux for 2 hours. Volatile substances are separated under reduced pressure. The distillation of the crude product gave 5.6 g of 2- (hydrazinocarbonyl) -ethyltrimethylstinate, boiling at 92-98 ° C (0.07 mm), that is, Compound No. 42 of Table 1. The infrared spectrum of the desylate showed the following absorption characteristics: 3300 cm-1 (NH), 1660 cm-1, 1530 cm-1 (-QO (-N =) and 760 cm-1 (Sn (CHa) 3). The chromatogram of the sample showed a single peak at 6 'X 1/8 "using column chromatography with 10% silicon gum on silanized diatomaceous earth. The NMR spectrum showed the following absorption; proton: wide singlet at 752 Hz (1 proton) transferred to NH, singlet at 3S8 Hz (2 protons) assigned to NH2, triplet at 235 Hz (2 protons) assigned to -C (0) -CH2, triplet at 98 Hz (2 protons) assigned to CH2-Sn and sin glet at 6 Hz (9 protons) assigned to Sn (CH3) 3. Percentage analysis: CHN calculated for CeHieN2 Sn: 28.72 6.43 11.17 Found: 28.08 6.44 10.53 Example V. Two-necked A 60 ml Schlenk reaction tube with a pyrex glass, provided with a magnetic Teflon-coated stirrer, is filled with nitrogen and kept in an air-free atmosphere. The tube is filled with 10.7 g (42.5 mmoles) of 3-butenic-4-tertiary-butylphenylsulfone and 7.0 g (42.5 mmoles) of trimethyltin hydride, closed and placed in a water bath. temperature of 20 ° C. The tube is illuminated within 7tf; § Łódźf 100 watt mercury lamp placed in a large tube and located 5-10 cm from * the reaction tube. After recrystallization of the solid product from petroleum ether, 3.6 g of 4- (4-ft. -Butylphenylsulfon) butyltrimethylstinate, mp 80-81.8 ° C, are obtained. The presence of both sulfonyl and trimethyltin residues shows strong bands of infrared absorption at 1300 cm-1, 1282 cm-1, 1147 cm-1 (-SO2) and 780 cm-1 [(CHOaSn-] using KBr disk. Magnetic spectrum Nuclear resonance (NMR) shows: Aromatic protons appear as two multiplets centered at 777 and 753 Hz (2 protons each); the alpha protons at the sulfonyl residue appear as a complex multiplet centered at 307 Hz (2 protons); methylene protons beta and gamma of the sulfo group appear as a complex multiplet centered at 162 Hz (4 protons); methyl protons of the tertiary-13-butyl group appear as a singlet at 134 Hz (9 protons); methylene protons attached to a tin atom appear as a remainder complex concentrated at 73 Hz (2 protons); the protons of the trimethyltin group appear with the same change as the tetramethylsilane (internal standard) 1 Hz. Percentage analysis: CHS Sn calculated for C17H30O2SSn: 4 8.94 7.25 7.68 28.45 found:, 49.06 7.33 8.19 27.60 Example VI. Proceeding analogously to that described in Example 5, 10.1 g (42.5 mmoles) of 5-hexenyl-p-tolylsulfone and 14.0 g (85 mmoles) of trimethyltin hydride are reacted. 232 h. The excess of trimethyltin hydride is evaporated from the reaction mixture under nitrogen flow. The unreacted 5-hexenyl-p-tolylsulfone is released from the reaction mixture by distillation under 1 × 10 × mm Hg to give 3 , 25 g of crude product From the chromatography column, a distillation residue on silica gel using toluene and 1% acetone in toluene as eluents gives 6- (p-tolylsulfonyl) -hexyl-1-trimethylstinate as an oil. 4 () Presence of sulfonyl and trimethyltin residues indicates strong infrared absorption bands at 1315 cm-1 and 1140 cm-1 (-SO2) and 760 cm-1 [(CIfc) 3JSn-l.NMR showed: aromatic protons appearing as two.multiplets concentrated at 775 45 and 732 Hz ( 2 protons each); alpha protons of the sulfonyl group appearing as a complex multiplet centered at 303 Hz (2 protons); methyl protons of the tolyl group appearing as a singlet at 243 Hz (3 protons); bQ beta methylene protons by with the epsilon sulfonate group appearing as an extended complex multiplet at 147 Hz (8 protons); methylene protons attached to a tin atom appearing as a triplet concentrated at 74 Hz (2 protons); protons 55 of the trimethyltin group appearing as a sinewave at -2 Hz according to the satellite band at one end (9 protons). Percentage analysis: * CH calculated for C16H2aO2SSn:, 47 ^ 7 7.00 60 Found: 47.52 7 , 00 Example VII. Proceeding analogously to the example described, 13.1 g (42.5 mmol) of 10-undecenyl-p-tolylsulfone and 14.0 g (85 mmol) of triethyltin hydride are used in the reaction. The reaction mixture was irradiated for 180 hours. The excess of triethyltin hydride evaporates from the reaction mixture in a nitrogen purge. The remaining oily substance, 5 g. Half of the crude product is chromatographed on a silica gel column using toluene and 2% acetone in toluene as eluents. The product obtained is 11- (p-Tolylsulfonyl) undecyltrimethylstinate as an oil * Obscnofcc; of both sulfonyl and trimethyltin groups showed strong infrared absorption bands at 1315 cm-1, 1300 cm-1, 1285 cm-1, 1140 crrr1 (-SO 2) and 760 cm-1 [(CHaJsSn-]. NMR showed: aromatic protons appearing as two multiplets concentrated at 771 and 728 Hz (2 protons each); alpha protons of a sulfonyl residue consisting of a multiplet positioned at 300 Hz (2 protons); methyl protons - tolyl groups appearing as a singlet at 24 ° C Hz (a-papotons); methylene [(£ Hl) «] p ^ appears as an extended mole * tiplet with a maximum peak * at 161 and 119 Hz (18 tones); alpha methylene protons at the tin atom appearing as a centered triplet at 76 Hz (2 protons); the protons of the trimethyltin group appear as a singlet at 0 Hz according to one satellite band at the opposite end (9 protons). Percentage analysis: GH calculated for l * -C2iH3j} OsSSn: 53.29 8.09 found: 53.81 8.09 Example VIII Proceeding in a manner analogous to that described in Examples I and II, other organocin derivatives are produced using analogous apparatus. These compounds and the products obtained in Examples 1-7 are shown in Table IX. The term "high vacuum" means a pressure of at least 0.1 mm Hg. Table I also indicates the solvent used for polishing orafc the melting point or the boiling point under pressure expressed in mm of mercury. All compounds are identified as cyanates because contain * "cyanate group", i.e. StiH ** Compounds designated with numbers I ^ -1-7, 21 ^ -23, 25 ^ 34, 36, 39-42 44-47, 49-56, 58-60 and 63 The -92 are new and are not yet known. The rest of the compounds are known or close to those known as their varieties. The state of engineering is also shown above for JA Appl. Chem, 9, 106-113 (1353); CA. 68. il $ Ch C106 &); Ayrey and contributors supra; Ziegler British Patent No. 966813; U.S. Patent BublL-tz * a No. 3,591,614; Bublftz, United States Patent No. 3,641,037], German Patent No. 1,198,974; J. Appl. Chem, 9, 176 (1959); J. Appl. Chem. 7, 356 (lf57); Etiss. Abstr. 22, 73 (1961) also relates to the subject matter of the invention. The foregoing description explains in detail the subject matter of the invention and should be understood to mean that various modifications and improvements can be made within the scope of the invention. R "R 'R" (CH3) 3SnH + H2C = C- (CH) m -X —MCH3) 3 SnCH2CH - (CH) m - X FORMULA U SCHEME 1 R 'R "R" R' 2 (CH3) 3SnH + H2C = C - (CH) mW - (CH) m— C = CH, R 'R "R" R' (CH3) 3Sn-CH2-CH- (CH) m —W - (CH) mCHCH2 -Sn (CH3) 3 SCHEME 2 Z.P. Bz-wo, z. MS ("5 + 2") 2.78 Price PLN 45 PL

Claims (1)

1. Claim: a method for the preparation of substituted ornular derivatives of the general formula 1, in which II 'represents a hydrogen atom, a group: hydroxyl, a-phthox, straight or branched. a group, alkyl of 1-5 carbon atoms, X represents (a) a group of the formula -SOeRi, where R 'is an atom. hydrogen and R 1 in the formula —SO 2 R 1 represents a straight or branched alkyl group of 1-18. carbon, cyclohexyl, benzyl, phenyl optionally substituted with one or more of the same void with different groups, such as a straight or branched alkyl group with 1-20 carbon atoms, cycloaliphatic with 4-6 carbon atoms, simple or branched alpha-cenyl group with 2R-20 carbon atoms, alkpxyl group with 1-8 carbon atoms, phenoxy, alkUotip group with 1-8 carbon atoms, halogen, nitrogen, acetyl, acetamide, carboxyl groups , alkoxycarbonyl, carbamoyl, cyano, hydroxy, trifluoronethyl, benzyl, naphthyl or norbonyl; naphthyl, biphenylyl, piperidineethylmethodo, group of formula -R * Sn (CH3) a »in which R2 is polymethylene group with; .2r-11 carbon atoms, -R4SO2RsSn (CH3) 3, where R * is ethyleneovar and Rs has the meaning given to djaiJ &; (b) grupfe. of the formula -OR7, in which R * represents a straight or branched alkyl group with 1-20 carbon atoms, chloo, palkyl, aryl, haloarite, [alpha] alkylaryl, alkoxyaryl, epoxyalkylene groups, in which the alkylene residue contains 2 to 4 carbon atoms * SW-di-alkylaminoalkyl, tetrahydro-l, lydifeeto-S-thienyl, group of formula -R8Sn (CH.i) &lt; RTI ID = 0.0 &gt; where Re is an alkyl group of 2-11 carbon atoms, cycloaliphatic. having 4-6 carbon atoms or aryl; (c) a group of the formula -SRw, wherein R 'is hydrogen and R10 in the formula rSR5 is straight or branched; an alkyl group; with 1-18 carbon atoms, cyclohexyl, benzyl, phenyl, optionally substituted with one or more of the same or different groups, such as a straight or branched alkyl group with 1-20 carbon atoms * cycloaliphatic group with 4R-6 carbon atoms, straight or branched alkenyl group with 2-20 carbon atoms * alkoxy group 1-8 carbon atoms alkylthio group with 1- ^ 8 carbon atoms, halogen atom, nitro, acetamide, carboxyl, alkoxycarbonyl, carbamoyl, cyano, hydroxy, trifluoromethyl, benzyl, naphthyl or norbornyl; naphthyl, biphenylyl, piperidinethylmethylmethyl, group of formula -R2Sn (CH3K where * R2 is polymethylene residue with 2-11 carbon atoms, group {of formula -R4SOdR5Sn (CJ &) 3, where Ba is grape, ethylene *, and Rs has the meaning given for Rz; (d) a group of the formula -COR, in which Rn represents a group of the formula -NH ', -NHNH2, -NHCHsOH, -NIJJta, in which Ri2 subsets to a pro or a branched alkyl group, with W12 a * o «¥ carbon or group, aryIowa: group a Mohrze -NHCH? NHGOR2Sn (Cfrjb, -OR13, where Rw denotes a straight or branched alkyl group with 1 - 15 carbon atoms * group of formula - ( CHAmOHi in which m is a number, ^ 4, a group of the formula - (CHzprf (Ri4) 2, in which p, is a number 2-4, and Rm; is a pro taflul | branched top rupe aU ^ ilOw ^ o 1-5; carbon atoms, group of formula - (Cm) q0C »RjSn {IJb) 3,. In Ittóry, q has the meaning given for- p, gpupe. O elevation ^ CH2) sN7l- (CH3) 3X-r X Compounds of formula 1 Compound number 1 1 2 3 4 5 0 li I 7 1 8 1 9 10 11 1; 12 13 li 14 15 16 tinate% 2,2'-sulfo nylbisethyltrimethyl-2,2'-sulfonylbis-ethyltrimethyltrimethyl-2- (methylsulfonyl) ethyl- 2- (ethylsulfonyl) ethyltrimethyltrimethyl-2- (iso-propylsulfonyl) ethyl-2- (IIC-butylsulfonyl) -trimethyltrimethyl - (tertiary-pentylsulfonyl) ethyl trimethyl-2- (n-octylsulfonyl) ethyl- 2- (n-dodecylsulfonyl) -ethyltrimethyltrimethyl-2- (n-octadecylsulfonyl) ethyl-1- (cyclohexylsulfonyl) -ethyltrimethyl- (benzylsulfonyl) -ethyltrimethyltrimethyl-2- (phenylsulfonyl) ethyl- 1- 2- (p-tert-butylphenylsulfonyl) ethyltrimethyl- I 2- (p-chlorophenylsulfonyl) ethyltrimethyl- 2- (2-piperidineethylsulfonyl) methyltrimethyl -, 1 methadide R '3 HHHHHHHHHHHHHHH n 4 X 5 -SO2CH2CH2Sn (CH3) 3 -SO2CH2CH2Sn (CHi) s -SO2CH3 -SO2-i-CiH7 -SO2CH (CH3) CH2CA -S0.2C (OH3) rCH2CHi -CsHi7 -SO2n-C12H25 -SQ2-n-C13Hj7 formula 12 formula 13 formula 14 formula 15 formula 16 formula 17 Reaction solvent 6 benzene toluene toluene toluene acetonitrile toluene Purification method 7 recrystallization recrystallization recrystallization distillation distillation distillation distillation high vacuum high vacuum recrystallization distillation high vacuum high vacuum recrystallization recrystallization washing with ether Melting or boiling temperature ° C (mm Hg) 8] 78.5-8A, 5J 78 , 3—7-a, 3 51—53 w — m (0l — 2) 90: —9 $ WD 96—99 | (0.06) 97-102 (0.07-0.09) oil oil 55-55.5 140-50 (0.07-0.15) oil and oil 118-20 57-60 122-24 Table X ( continued) 1 1 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 2 2.2 '- (ethylenedisulfonyl) -bisethyltrimethyl-2-ethoxyethyltrimethyl-2-n-butoxyethyltrimethyl-2-iso- butoxyethyltrimethyl-trimethyl-2-iso-octoxyethyl-2-decoxyethyltrimethyl-2-dodecoxyethyltrimethyl- 3- (2,3-epoxypropoxy) -pro- 2,2'-oxybisethyltrimethyl-3,3'-oxybispropyltrimethyltrimethyl-3-phenoxypropyl 3- (p-tert-butylphenoxy) propyltrimethyltrimethyl-3- (p-methoxyphenoxy) propyl- 3- (p-chlorophenoxy) propyltrimethyl- 2- (2,2,2-trifluoroethoxy) ethyltrimethyl- 2- ( N, N-dimethylaminoethoxy) -ethyltrimethyl- 2- (hexadecoxy) ethyltrio- 3 HHHHHHHHHHHHHHHHH 4 2 1 2 2 2 2 1 1 1 5 -SO2 (CH2) 2SO2- - (CH2) 2Sn (CH3) 3 -OC2H5 -O-11-C4H9 -OCH2CH (CHs) 2 -0-i-CsHi7 -OC10H21 -OC12H25 formula 18 -OCH2CH2Sn (CH3) 3 -OCH2CH2CH2Sn (CH3) 3 formula 19 formula 20 formula 21 formula 22 -OCH2CF3 -OCH2CH2N ( CHs) 2 -OC16H33 6 ethyl acetate - ~ "- - ~~ ¦ ~~ - - - ~~ i. - - ~~ "- 7 recrystallization distillation distillation distillation distillation distillation distillation distillation distillation distillation distillation distillation distillation distillation distillation high vacuum 8 141.5 (decomposition) 80-82 (50) 86-91 (15) 95-93 ( 30) 58-62 (0.05) 68-71 (0.03) 113-17 (0.07) 1 100-2 (4.5) 55-58 (0.1) 74-5 (0.07 ) 66—70 (0.025) 98—100 (0.08) 98—100 (0.1) 84—88 (0.07) 81—86 (50) 43—43.5 (0.07—0.03 ) oil | Table X (continued) 1 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 1 2 1 3- (tetrahydro-1,1-dice-3-thienyloxy) propyltrimethyltrimethyl-3 -phenylthiopropyl- 3,3'-thiobispropyltrimethyl- 2- (p-chlorophenylthio) ethyltrimethyl- 2-carbamoylethyltrimethyl- 2- (N-tert -butylcarbamoyl) -ethyl- trimethyl- 2- (N-hydroxymethylcarbamoyl) ethyltrimethyl- , N'-methylenebis (2-carbamoylethyltrimethyl) - 2- (hydrazinocarbonyl) ethyltrimethyl- 2- (ethoxycarbonyl) ethyltrimethyl- 2- (dodecoxycarbonyl) -ethyltrimethyl- 2,2 '- (ethylenedioxydicarbonyl) -bisethyl-trimethyl-trimethyl-3-ureidopropyl-trimethyl-3-thioureidopropyl- 2- (N-carbazoyl) ethyltrimethyl-trimethyl-2- (2-ketopyrrolidinyl) ethyl- 2- (N-imidazolyl) ethyltrimethyl- 1HHHHH 1H 3 HHHH 4 2 2 2 1 V 2 2 1 1, 1 5 pattern 23 pattern 24 -SCH2CH2CH2Sn (CH3) j pattern 25 pattern 26 pattern 27 pattern 28 pattern 29 pattern 30 -COOC2H5 -COO-11-C12H25 -COO (CH2) 2COC ( CH2) 2 -Sn (CH3) 3 -NHCONH2 -NHCSNH2 formula 31 formula 32 formula 33 6 - - - ~~ "tetrahydrate0- furan tetrahydrofuran tetrahydrofuran acetonitrile ethanol - - - tetrahydrofuran tetrahydrofuran toluene ¦ ~ - 7 high vacuum distillation distillation distillation recrystallization recrystallization recrystallization distillation distillation distillation distillation recrystallization recrystallization recrystallization distillation 8 1 oil 82.5-7 (0.06) 94-98 (0.06) 90-92 (0, 07) 69—70.2 74—75.5 79—84 128—8.5 1 92—98 (0.07) 85—6 (10) 116—17 (0.003) 122—30 (0.07—0 , 1) 79.5-82 124.5-125.5 93.5-95.5 69-80 (0.03 ) 85-6 (0,1) 1 Table X; (continued) 1 51 52 53 54 55 56. 57 58 59 60 61 62 63 64 65 2 2- (0.0-diethylphosphono) ethyltrimethyl 3,3'-carbonyldioxy) bispropyltrimethyl- 3- (2-furoyloxy) propyltrimethyl 3- (N-methylcarbamoyloxy) propyltrimethyl- 2- (2-pyridyl) ethyltrimethyl- 2- (2-methyl-5-pyridyl) ethyltrimethyl- 2- (4-pyridyl) ethyltrimethyl- 4- (tetrahydro-1,1-diceto-2-thienyl) - -3- hydroxybutyltrimethyl- 2- (triethoxysilyl) ethyltrimethyl- 2,2'-m-phenylene bispropyltrimethyl 2-cyananoethyltrimethyl- 3- (hydroxypropyl) trimethyl- 2,2 '- [2,4,8,10-tetraoxaspiro (5.5) undec- -3,9-ylene] -bisethyltrimethyl 2-ethoxy-2 (0,0-diethylphosphono) -ethyltrimethyl- 2- (2,6,8-trimethyl-4-methoxy) -ethyltrimethyl-3 | 4 H H H H H H H OH 1 2 2 2 1 1 1 2 -SKOCsHó) * CHa, 1 H H H 1 2 1 OC2H5 1 H 1 5 | 6 -PO (OC2H5) 2 -OCOO (CH?) 3Sn (CH03 pattern 34 -OCONHCHj pattern 35 pattern 36 pattern 37 pattern 38 pattern 39 -CN -OH pattern 40 -PO (C02H5) 2 * pattern 41 rrv "- ~~ m - ~~~ ~~ "- ~~ • - - ~ - ~~~ ~~~ ^ ~ t - ^ ~ 7 [distillation distillation distillation distillation distillation distillation distillation recrystallization distillation distillation distillation distillation distillation distillation 8 49.5— 51 (0.02) 104-108 (0.05) 92-95 (0.1). 78-81 (0.15) 56 (0.1) 72-7 (0.05) 63-66 (0 , 15) 99-103.5 56-7 (0.09) 110-11 (0.1) 87-9 (10) 37-8 (0.1) 144] (0.0025) 79 (0.45 —0.05) 67—71 j (0.003) Table X (continued) 1 66 67 68 69 70 71 72 73 74 75 76 77 1 2 2- (p-tolylsulfonyl) ethyltrimethyl-2- (p-ethylphenylsulfonyl) ethyl - trimethyl 2- (p-isopropylphenylsulfonyl) ethyltrimethyl- 2- (p-pentylphenylsulfonyl) ethyltrimethyl-2- (p- / 1,1-dimethylpropyl (phenylsulfonyl) -ethyltrimethyl- 2- (p-octylphenylsulfonyl) ethyl-trimethyl- 2- (p-dodecylphenylsulfonyl) ethyl-trimethyl- 2- (pn-dodecylphenylsulfonyl) -ethyltrimethyl - 2- (pn-tridecylphenylsulfonyl) ethyl-trimethyl- 2- (2,4-dimethylphenylsulfonyl) - ethyltrimethyl- 2- (2,5-dimethylphenylsulfonyl) - -ethyltrimethyl- 2- (2,4-diethylphenylsulfonyl) - -ethyltrimethyl- 3 HHHNHHHHHHH j, 5 pattern 42 pattern 43 pattern 44 pattern 45 L pattern 46 pattern 47 pattern 48 pattern 49 pattern 50 pattern 51 pattern 53 1 6 tetrahydrofuran tetrahydrofuran 1 furan tetrahydrofuran toluene toluene tetrahydrofuran tetrahydrofuran toluene toluene tetrahydrofuran and tetrahydrofuran tetrahydrofuran | 7 recrystallization recrystallization recrystallization high underpressure recrystallization high underpressure high underpressure recrystallization recrystallization high underpressure high underpressure high underpressure 1 * 1 55.5-58 52-56.5 53-57.5 oil 72-74 oil oil 33-34 43.3 ^ 14.8 oil oil oil 178 79 80 81 82 83 84 KR 86 87 8fl 89 2- (2,5-diisopropylphenylsulfonyl) -ethyltrimethyl-2- (p-cyclopentylphenylsulfonyl) - ethyltrimethyl- 2- (p-cyclohexylphenylsulfonyl) - ethyltrimethyl 2- (p-bicyclo 2,2,1-hept-2-yl-phenyl) - ethyltrimethyl- 2- (p-methoxyphenylsulfonyl) ethyltrimethyl- 2- ( p-bromophenylsulfonyl) ethyltrimethyl- 2- (p-fluorophenylsulfonyl) ethyltrimethyl- 2- (3,4-dichlorophenylsulfonyl) -ethyltrimethyl- 2- (2-naphthylsulfonyl) ethyltrimethyl- 4- [p- (1,1- dimethylethylphenylsulfonyl] - butyltrimethyl- 6- (p-tolylsulfonyl) hexyltrimethyl-11- (p-tolylsulfonyl) undecyltrimethyl 3 1 II HHHHHH 1 H 1 HH II H 4 | 1 1 1 1 1 1 1 1. 1 3 5 10 pattern 54 pattern 55 pattern 56 pattern 57 pattern 58 pattern 59 pattern 60 pattern 61 pattern 62 pattern 63 pattern 64 pattern 65 Table X (continued) 1 tetrahydrofuran tetrahydrofuran tetrahydrofuran tetrahydrofuran tetrahydrofuran tetrahydrofuran tetrahydrofuran toluene tetrahydrofuran - - - 7 high vacuum recrystallization recrystallization recrystallization recrystallization recrystallization recrystallization recrystallization recrystallization recrystallization chromatographic column chromatographic column 8 oil 94-95 116-118 106-110 35.5— 39 84.5-86.5 65-66.5 102.2-103.5 88.5-90.7 80-81.8 oil oil 61 W 516 62 in which s is as defined for p; (e) a group of the formula -NHCONH2; (f) a group of the formula -NHCSNH2; (g) a 2-pyridyl group; (i) 2-alkyl-5-pyridyl; (j) a 9-carbozoyl group; (k) a 1-imidazolyl group; (1) N-2 -ketopyrrolidinyl; (m) a group of the formula -OCORi7 in which Rn is a group of the formula -NHRib in which Ria is a straight or branched alkyl group of 1-5 carbon atoms or an aryl: 2-furyl group; a group of formula -O (CH2) tSn (CHs) i wherein t is a number 2-11; (n) a group of the formula -PO (OR20) 2 in which R20 is a straight or branched alkyl group having 1-5 carbon atoms; (o) tetrahydro-l, l-dio-2-thienyl; (p) a group of the formula -Si (OR2i) a, in which Rn is a straight or branched alkyl group having 1-5 carbon atoms; 4) a group of the formula II; cyano group; (s) OH group; (t) the group of formula III, and n is a number 1-10, characterized in that the trimethylolhydride is reacted with a compound of formula IV containing an olefinic residue, in which X is as defined above, R 'is hydrogen, straight or branched alkyl group of 1-5 carbon atoms or alkoxy of 1-5 carbon atoms, aR "is hydrogen, hydroxy or alkyl of 1-5 carbon atoms, and m is 0-9, the use of which is about an equimolar amount of the compound containing the olefin residue and the mixture is stirred in an inert gas atmosphere by irradiation with a mercury lamp for about 4-232 hours at a temperature of about 0-50 ° C. 1099,516? (CH3) 3Sn (CH2) n — CH — X FORMULA 1 CH3 <^ - C — CH2Sn (CH3) 3 H FORMULA 2 .0- / \ / Ov H \ (O R2Sn (CH3) and FORMAT 3 Ri — Sn— R3 FORMAT 6 '--Sn —R y FORMULA 7 R2 Sn - 0. R3 FORMULA 8 r ¦ (CH2) nCHX FORMULA 5 OT OSC6H4CH3 (p) FORMULA 9 FORMULA 10 ^ 0-CH2- ^ ^ -CH2-0- ^ "^ 0-CH2 ^ CH2 ~ 0 PATTERN 11 - SO2— PATTERN 12 - S02CH2- ^ O) PATTERN 13 -so2— (g) PATTERN U ¦S02— (£)) - C (CH3) PATTERN 15 —s o2— {0) - ci FORMULA 16 S02CH2CH2 — N "MODEL 17 A -OCH2CHCH2 MODEL 1899 51C '- © -O- FORMULA 19 - C— (o) —C (CH3) 3 FORMULA 20 —o— (o) - och3 PATTERN 21 o- (0th PATTERN 22 0- \ y so2 PATTERN 23; - <ó PATTERN 24 S— (O) - Cl PATTERN 25 O II - C — NH2 PATTERN 26 O - C — NHC (CH3) 3 FORMULA 27 O - C —NHCH2OH FORMAT 28 OH HO II II II C — NCH2NC (CH2) 2Sn (CH3) 3 FORMULA 29 - C — NHNH2 FORMAT 30 and FORMAT 31 —OCO O FOR FORMAT 34 O) - CH3 1 N FORMAT 36 - vO, N- PATTERN 35 '- © PATTERN 37 U PATTERN 32 - N PATTERN 33 - CHr-tsJ O2 PATTERN 38WS1 # (ó fH, CHCH2Sn (CH3) 3 FORMULA 39 O HC (CH2) 2Sn (CH3) 3 O MODEL 40 XH2CH (CH3) 2 -OC —- H ^ CH2CH (CH3) CH2CH (CH3) 2 FORMULA 41 —SO2 ^ O / - CH3 FORMULA 42 - SO2 - ((5) -C12H25 FORMULA 48 SO2 - (0) - ( CH2) nCH3 FORMULA 49 —SO2— (0) ~ (CH2) i2CH3 FORMULA 50 - SO2- / O ^ -CH3 CH3 FORMULA 51 CH3 - SO2— (0 CH3 so2— (O) - ch2ch3 FORMULA 43 FORMULA 44 - so2— (5) - (ch2Uch3 FORMULA 45 CH, - SO2 - (O) - CCH2CH3 CH3 FORMULA 46 —SO2— (O) - (CH2) 7CH3 so2 ¦so2 -S0; PATTERN 47 - (Q) —CH2CH3 CH2CH3 PATTERN 53 / CH (CH3) 2 - <£ ¦ CHICH 3) 2 PATTERN 54, - <ó ^ PATTERN 55 PATTERN 52 -so2 ^ 0 ^} PATTERN 56 S02- PATTERN 5799 516 so2 - -so2 • so2- ¦sc2- -so2 io; WZOR - © WZOR - @ WZOR - 0CH3 58) - Br 59) —F 60 r ~ x \ 2 / WZOR 1§ WZOR 1 — Cl 61 o) 62 —so2— (C ^ -c (ch3) 3 WZdR 63 - SO2— (OV-CH, FORM 64 - SO2- ^ Oy-CH3 WZdR 65 O II .'nC4Hj,) 3 SnCH2CH2—5— CCH3 WZdR 66 O (CH3) 3SnOS - (p) —CH3 WZdR 67 CH3— < (V-S02Na WZdR 68 li ^^ (C! L3! 3SnCH2S - (0 /) O FORMULA 69 CH3S02— @ FORMULA 70 (CH3) 3 SnCH2CH2S - {q) O FOR MODEL 7199 516 (CH3) 3SnCH2CH2S— (Q) - C (CH3) 3 O WZdR 72 CH3 OI II (CH3) 3-Sn-CH —S - ^^ - C-lCH -,) - 0 FORMULA 73 U / TA (CH3) 3SnCH2CH2 — S - ('O) 0 MODEL Ik S / TA (CH3) 3SnCH2-S- (2 / O WZdR 75 R * PL