TRIGLYCERIDE BASED SURFACTANTS, PROCESS FOR THE PREPARATION THEREOF AND PLANT PROTECTING COMPOSITIONS CONTAING THE SAME

Abstract: Stabilised liquid plant protecting compositions comprising as main component 5-55 % by weight of an active ingredient, 20-90 % by weight of one or more carrier(s) and other auxiliary agents and 5-25 % by weight of a surfactant of the general Formula I <IMAGE> (wherein R<1> and R<2> together stand for a hydrocarbon chain which when completed by a group of the general Formula -(CH=CH)q- corresponds to the alkyl chain of soya fatty acid; Q is -(CH2)p-, -CH=CH- or phenylene; A is -(CH2CH2O)n- or -[CH(CH3)CH2O]n-; R<3> and R<4> may be the same or different and stand for hydrogen, C1-12 alkyl, benzyl, phenyl or alkylaryl; n is an integral in the range of 3-70; p is an integral number between 0 and 6; q is a number of 1.0-1.5). The compounds of the general Formulae I and II are novel.

Description: TRIGLYCERIDE BASED SURFACTANTS, PROCESS FOR THE PREPARATION' THEREOF AND PLANT PROTECTING COMPOSITIONS CONTAINING THE SAME TECHNICAL FIELD The present invention relates to triglyceride bas surfactants, a process for the preparation thereof and plant protecting compositions comprising the same. According to an aspect of the present invention there are provided surfactants of the non-ionic and anionic type of the general formula I 0=C-Q-COO-A-H and/o r II 0 ! 0=C-Q-COO-A-H (wherein OMP - 2 - R 1 and R2 together stand for a hydrocarbon chain which when completed by a group of the general Formula -(CH=CH) - corresponds to the alkyl chain of soya fatty acid, 5 Q is - (CH ) . m . -CH=CH- o r phenylenβ ; A is - (CH 2 CH 2 0 ) n - o r - [CH (CH 3 )CH 2 03 n - ; R and R may be the same or different and stand for hydrogen, C,_ 1 alkyl, benzyl, phenyl or alkylaryl; n is an integral in the range of 3-70; 10 p is an integral number between 0 and S; q is a number of 1.0-1.5). Acco.rding to other aspect of the present invention there is provided a process for the preparation of the said compounds of the general Formulae I and II. 15 According to a still further aspect of the present invention there are provided plant protecting compositio comprising as surface active agent a surfactant of the gene ral Fo rmula I and/o r II . Surfactants of the non-ionic type are mainly 20 alkylene oxide adducts. The alkylene side chain constitutes the hydrophilic part of the molecule while the mostly water non-soluble moiety attached thereto is the hydrophobic part. The most well-known representativ of the said non-ionic surfactants are the ethylene oxide 25 adducts which can be prepared by subjecting reactive ethylene oxide to a polycondsnsation reaction with a compound containing hydrogen of acidic character. As compounds containing hydrogen of acidic characte alkyl phenols, fatty alcohols, fatty acids, fatty acid 30 amices, amiπo compounds prepared frcr. fatty acids and πercaptans can be used. Thus by changing the polar and/or apolar part(s) various types of surfactants can be prepared, and the properties thereof can be varied between wide ranges and 35 and modified deliberately. 3ACKGRC ..D ART The first basic types o .atεc noπ-ionxc ' j i< £- - surfactants - ethoxylated fatty alcohols and fatty acids - appeared on the market in 1932 as detergents. Later alkyl phenols were used as hydrophobic part of the surfactants. These compounds were wide-spreadly used in all branches of industry using surfactants du to their very advantageous properties (first of all becaus.e they are not sensitive to hard water). In th mean time in certain branches of industry more specif surfactants having higher activity were developped by chemical modification of the basic types. Thus by using fatty acid amides and alkyl amide oxides as hydrophobic part in the said basic types surfactants having excellent foaming capacity and foam stability were prepared. Sulfuric acid esters o ethoxylated fatty alcohols or alkyl phenols (3ritish patent No. 833.14-6) and sulfuric acid esters of ethoxylated fatty acid amides possess good foaming capacity. The said surfactants can be used for the preparation of shampoos and foam baths. In certain cases foaming is an undesired phenomenon. In such instances the desired result can be achieved by proper selection of the structure of both the hydrophobic {US Patent No. 2.859.250) and the hydrophilic parts (US Patent No. 3.022.335). Similarly surfactants having anti-statitizing effect can be obtained by proper selection of the chemical structure, particularly by increasing the length of the ethoxy chain. According to GFR patent No. 1.18^.^-9 - the antistatitiziπg effect can be achieved by modifying the chemical structure of the hydrophobic part of ethoxylated alkylaryl derivatives. In the formulation of biologically active in¬ gredients - e.g. plant protecting compositions - the main role oτ tne surractaπt is to ensure : he spont aneous fo rmation o f a s table e muls ior. o r suspe nsi BAD ORIGINAL having a suitable degree of dispersion. All the other advantageous effects which can be attributed to the presence of the surfactant can be regarded as plus effect, 5 The surfactants can influence the activity of the plant protecting compositions as well. In the case of herbicides, fungicides and insecticides respectively it depends on the surfactant how the composition moistens the plant, fungi and insects 10 respectively. This enables the preparation of surfactants having the most suitable structure to each composition (P 0 3echet: The Ξmulsifisr, Marcel Decker, Inc. 1973, New York). In the above entioned article and also in other 15 patent specifications surfactants are " described which . possess certain plus effects in addition to the typical surface active effect taken in the s-trict sense of the word. The said plus effects can be mainly achieved by chemical modification of the alkyl, aryl or 20 aralkyl adducts regarded as basic types of the ethoxylated non-ionic surfactants. It is known that certain plant protecting compositions - particularly thio-phosphoric acid and thio-phosphonic acid derivatives and pyretrines - 25 decompose in solutions formed with organic solvents under the formation of acidic products. The said decomposition products formed accelerate the de¬ composition. This involves the risk that on storage the active ingredient might decompose in the solution 30 formed with an organic solvent β In such cases the compositions are usually stabilized by adding acid binding agents or other suitable additives. 0,0-diethyl-0-2-σuinoxalinyl-phosρhorothioate is a highly effective contact insecticide and acaricide 35 and is put on the market mainly in the form of a AL liquid emulsion concentrate. According to valid international standards emulsion concentrates must be stable for at least two years. According to GFR patent No. 1.903.228 stability is ensured by adding tertiary amines and/or diprotic apolar solvents; thus dimethyl sulfoxide, N-methyl-pyrrolidone and tetra- ethyl-urea are admixed in an amount of some per cents to the composition. GFR patent No. 2.4-11.764 relates to the stabilization of 0,0-diethyl-0-2-quinoxalinyl-phosphor thioate as well. According to the said patent a compound comprising epoxy group (such as epoxy-cyclo- hexane, epichlorohydrine or dicyclohexyl-carbodiimide) is added to the solution in an amount of some per cent The use of the above stabilizing agents is howeve accompanied by difficulties. The tertiary amines and above mentioned - poxy compounds are volatile and toxic and therefore the compositions involve serious toxicity risks to the operator. The use of epichloro- hydrine is particularly undesired because the carcino¬ genic effect thereof has been recently made probable. A further drawback is that some of the above additives are very reactive compounds which is a rather undesired property of a stabilizer. Moreover the above additives are rather expensive even when used in a small amount. A further disadvantage is that the said additives might disturb the complicated analysis of the composition comprising a large number of components. DISCLOSURE OF THE INVENTION It has been found in a surprising manner that the above drawbacks can be eliminated by preparing emulsion concentrates comprising the above mentioned active ingredients and surfactants of the general Formula I and/or II. BAD ORIGINAL _ 6 - The present invention relates to new triglyceride based surfactants of the general Formulae I and II, a process for the preparation thereof and plant protecting compositions comprising the same. The molecules of the surfactants of the general Formulae I and II contain epoxy and/or amino groups and play a double role in the plant protecting compositions On the one hand they provide the suitable ready-for-use disperse system and on the other due tb the epoxy and 10 amino groups they inhibit the decomposition of the acti ingredient in the composition. In Table I the important properties of some representatives of the compounds of the general Formula I and II are summarised (q = 1.25). ^ O IGI AL 1 -(CH 2 CH 2 0)n- -CH 2 CH 2 - 34- yellowish 55-60 1000 12,5 brown paste 2 -(CII 2 CH 2 0) n - Phonylone 34- brownish 60-65 1000 12.5 paβta 3 -{cw 2 cι-ι 2 o) n - -Cl CII- - - 34- rown 55-60 1000 12.5 pαsto 4- -(CM 2 CII 2 0) n - -CH 2 CII 2 - 23 brownish 55-60 000 11 paste 5 ~(CH 2 CH 2 0) n - -CH 2 CH 2 4-5 white 60-65 1200 14- paste 6 -(CH 2 CH 2 0) n - ~CH ? CII ? ~ 7 viscous - 550 5.5 liquid 7 * -(cιι 2 cιι 2 o) n - -CH 2 CH 2 - n- -C-.IL- n-C -L. 34- brown 55-60 - / 3 / 13.5 paste 0 .(cιι 2 cιι 2 o) n - -CH 2 CH 2 . n- own 4-0-51 - - C 3 M 7 n - C 3 7 ' 7 7 pas e 0 -(CII 2 CH 2 0) n _ -cι. 2 cι. 2 - (n- -C^ll 9 ) 2 (n-C^lg^ 1 13.5 Ό 34- 50-55 ~ rown O no α G> 10 ~tcι-ι(cιι 3 )cιι 2 c 26 white 60-65 - 10.5 z n -CH 2 CH 2 - > poote - 8 - The compounds of the general Formulae I and II are readily soluble in usual organic solvent and mixtures . 100 C. In .the second step the carboxy group of the ha ester obtained is reacted with the epoxy group of an epoxidized triglyceride, preferably epoxidized soya oi The second addition reaction can be carried out at 5 150-200 °C, preferably at 150-170 °C. The progress of the reaction can be checked by measuring the acid nu ber. The advantage of the above process is that no by¬ products are formed, and both steps can be carried out lθ in the same apparatus by using readily available starting materials. The anionic type surfactants of the general Formula II can be prepared from the surfactants of the general Formula I by reacting the epoxy groups of the 5 compounds of the general Formula I with suitable amino compounds (e.g. di-n-butyl a ine , di-isopropyl-a ine) in the presence or absence of a solvent. The reaction can be preferably ca ' rried out at 20-80 C. The surfactants of the general Formulae I and II 0 can be preferably used for the preparation of stable, particularly liquid plant protecting compositions. According to the present invention there are also provided compositions comprising 5-55 ;j by weight of a plant protecting active ingredient, 5-25 % by weight 5 of a surfactant of the general Formula I and/or II and 20-30 % by weight of one or more a carrier(s). The surfactants of the present invention are particularly suitable for the stabilisation of emulsion concentrates comprising 25 % of 0,0-diethyl-0-2- 0 cuinoxalinyl-phosphorcthioate. The stability of the compositions of the present invention - emulsion concentrates containing 25 % of the active ingredient - is completely equivalent to that of the re fe rence composition comp rising e pi- 5 chio rohyd riπ e . BAD O IGINAL IJVJRK In field experiments the compositions comprising the surfactants of the present invention proved to have biological activity being completely equivalent to that of the reference composition. The compositions were tested in plough-land cultures on best, potato, tobacco lucerne, pea, maize, sugar beet, autumn wheat, vegetables and fruits (e.g. grape, apple, peach, plum and cherry) against various pests. In various stages of the cultures excellent biological effect was found but no phitotoxicity was observed. BEST HOPE OF CARRYING OUT THE INVENTION Further details of the present invention are to be found in the Examples without limiting the scope of protection to the Examples. Example 1 50- g of succinic anhydride and 750 g of polyethyle glycol (OH number 75 g KOH/g) are reacted at 90 °C. To the half ester thus obtained 4-52 g of epoxidized soya oil(epoxy equivalent 250, iodine number 6) are added and the mixture is reacted at 170-130 C until the acid number becomes smaller than 1 mg KOH/g. On cooling a ' compound of the general Formula I is obtained wherein A is - CH 2 CH 2 0) 3 - Q is -CH^K^ and q = 1.25. Characteristic data: mp. : 55-60 °C, OH number 0.05 mg KOH/g, epoxy equivalent 1000, HLB value 12.5 C Example 2 74-- g of phthalic anhydride and 750 g of polyethylen glycol (OH number 75 g KOH) are reacted at 90 °C. To the half ester- thus obtained 4-52 g of epoxidized soya oil are added (epoxy equivalent 250, icdine number 6) and the mixture is reacted at 170-180 °C until the acid number becomes smaller than 1 mg/KOH/c. On cooling a surfactant of the general Formula I is obtained wherein A is -(CH CH 0) 3Z ,-; Q is phenylene and q is 1.2 Characteristic data: mp. : 60-65 C, OH number 0.05 mg KOH/g, epoxy equivalent 1000, HLB value 12.5. Example 3 50 g of succinic anhydride and 500 g of poly¬ ethylene glycol (OH number 112 mg KOH/g) are reacted at 90 °C. To the half ester thus obtained 4-52 g of epoxidized soya oil are added (epoxy equivalent 250, iodine number 5) and the mixture is reacted at 170-180 C until the acid number becomes lower than 1 mg KOH/g. On cooling a surfactant-of the general Formula I is obtained wherein A is -(CH,-,CH-0)_ 3 -; Q = -CH 2 CH 2 - and q = 1.25. Characteristic data: p. : 55-SO C, OH number 0.06 mg KOH/g, epoxy equivalent SCO, HL3 value 11.0. Example 4- 50 g of succinic anhydride and 1000 g of poly¬ ethylene glycol (OH number 55 mg KOH/g) are reacted at 90 C. To the half ester thus- obtained 4-52 g of epoxidized soya oil are added (epoxy equivalent 250, iodine number 6) and the mixture is reacted at 170-180 C until the acid number becomes smaller than 1 mg KOH/g. On cooling a surfactant-of the general formula I is obtained wherein A s -(CH p CH^O)^ ^ -, Q is -CH 2 CH 2 - ; q = 1.25. Characteristic data: mp. : 50-55 C, OH number 0.04- mg KOH/g, epoxy equivalent = 1200, HLB value 14-.0. Example 5 50 g of succinic anhydride are reacted with 150 g of polyethylene glycol (OH number: 374- mg KOH/g) at 90 C. To the half ester thus obtained 4-52 g of BAD ORIGINAL epoxidized soya oil are added (epoxy equivalent 250, iodine number 6) and the mixture is reacted at 170-180 until the acid value becomes lower than 1 mg KOH/g. On cooling a compound of the general Formula I is obtained wherein A is -(CH 2 CH 2 0) 7 -; Q is -CH 2 CH 2 -; q = 1.25. Characteristic data: OH number 0.1 mg KOH/q, epoxy equivalent 520, HLB value 5.5. Example 6 250 g of a' compound of the general Formula I (wherein -(CH^CH 0) 3 .- and Q = -CH 2 -CH 2 ~) and 20.2 g of di-n-propyl-amine are reacted at SO C for 90 minutes. O cooling a compound of the general Formula II is obtained wherein A is -(CH CH 0) 3i ,-; Q is -CH ~ CH 2~ ' a - ~ 1 » 25 » R and R' = ri-propyl. Characteristic data: OH number 0.1 mg KOH/g, HL3 value 13 Example 7 130 g of a compound of the general Formula I (wherein A is - CH OH 0) -, Q is -CH 2 -CH -) are reacted with 20.2 g of di-n-propyl amiπe at 60 °C for 90 minutes On cooling a compound of the general Formula II is obtained wherein r- A is / -(CH2_CH rZ.0) /-; Q is. -CH--L-CH«£-.-; q is 1.25 and R and R' are n-propyl. Characteristic data: OH number 0.2 mg KOH/g, HLB value 7 Example 8 (reference Example) An emulsifiable concentrate (EC) containing 25 % of 0,0-diethyl-G-2-cuiπoxalinyl-phosphorothioate is pre¬ pared by admixing the following components i Component Amount, parts by weight 0,0-diethyl-0-2-quinoxalinyl- phosphorothioate 25.0 Noπylphenol-polyglycoiether, HLB=12.0 3.0 Calcium salt of dodecyl benzene sulfonic acid 1.0 Xylene 25.0 BAD ORIGINAL Shellsol R 4-5.0 Ξpichlorohydrine 1.0 Example 9 Amount, parts by wei Component 0,0-diethy1-0-2-quinoxaliny1- phosphorotioate 25.0 Surfactant of the general Formula I wherein A is -(CH„CH 0)-,-, Q is -CH 2 -CH 2 -, q = 1.25 2.8 Calcium salt of dodecyl benzene sulfonic acid 1.0 Xylene 71.2 ' Example 10 Component Amount, parts by weig 0,0-diethyl-0-2-quinoxalinyl- phosphorothioa e 25.0 Surfactant of the general Formula I [A is -(CH 2 CH 2 0) 3 -, Q = -CH=CH-, q = 1.25] 3.2 Calcium salt of dodecyl benzene sulfonic acid 1.0 Xylene 25.0 Shellsol R 4-5.8 Example 11 Component Amoun t , p a r ts by we ig 0,0-diethy1-0-2-quinoxalinyl- phosphorothioate 55.0 Surfactant of the general Formula I [A is -(CK 2 CH 2 0), 5 - / Q is -CH 2 «CH 2 - q = 1.25] 5. 5 Surfactant of the general Formula I [A is - (CH CH 3 0 ) y - , Q is -CH -CH - , q = 1. 25] 2.0 AD ORIGINA ε- _ l -J- _ Calcium salt of dodecyl benzene sulfonic acid 2.0 Xylene 35.5 Example 12 Component Amount, Darts bv v/eicnt 0,0-diethyl-0-2-quinoxalinyl- phosphorothioate 5.0 Surfactant of the general Formula II [A is -(CH 2 CH 2 0) 3 ^-, Q is -CH 2 -CH 2 -, q = 1.25, R = R *1" = n_ propyl] 2.0 Calcium salt of dodecyl benzene sulfonic acid 0.5 Xylene 4-0.0 Isopropaπol 12.5 Shellsol R 4-0.0 Example 13 In this Example the application of the composition according to Examples 8-12 is described and the testing of the activity thereof is disclosed. The emulsion concentrates according to Examples 8-12 are subjected to the following tests: Emulsion stability: emulsions of a concentration of 5 vol. % are prepared by using standard hard water (about 19 IH ) and standard saft water (about 2 IH ). The emulsions are allowed to stand at a temperature of 30 +1 C and the amount of precipitate is weighed after 2, 24, and 4-S hours respectively. Accelerated testinα of the stability of the emulsion concentrate: the samples (20 ml) are stored for 30 minutes under airtight sealing at 4-0 °C . 50 °C and 60 C respectively. In the heat-treated samples the amount of the decomposition product (2-hydroxy- quinoxaline) is measured by UV spectrophotometrical methods. Thin layer chromatoqraphy : the 0.0-diethyl-0-2-quinoxalinyl-phosphorothioate acti ingredient content is determined with the aid of a Vide o-densi tome ter. Cold resistance of the emulsion concentrate: the samples (100 ml) are stored at -5 °C for 72 hours. Samples which remain as clear solution after this period of time are considered to have adequate cold resistance. The results are summarised in Table III. Table III Sample Emulsion stability; Testing of stability; Col No. amount of supernatant decomposed active resist or precipitate (ml) ingredient [ ) after 2 24- • 4-8 4-0 C 50°C 60°C h o u r s Example 8 (reference) 0.5 1.0 0.5 0.8 1.4- corresp Example 9 - 0.1 0.4- 0.5 0.8 u Example 10 - 0.1 0.2 0.5 0.7 u Example 11 - 0.1 - 0.4- 0.5 Example 12 - — — 0.5 0.7 Example 14- Field tests are carried out by using the emulsion concentrates prepared according to Examples 8-10. The samples are tested against various pests. In order to show the efficiency of the compositions according to the present invention the results of the tests carried out against two pests are given below. BAD ORIGINAL a) Protection against apple ermel (Laspeyresia ponomella L). Parcel size: 2.5 ha Sort: Starking Golden delicious Replicate (number of tests): 4- Amouπt of water: 800 1/ha Samples: Control EC according to Example 8 (reference sample EC according to Example 9 and 10 Concentration: 0.15 %, The results obtained are summarised in Table IV. Table IV Sample Effect related to control ' (%) Reference Example 8 81.5 Example 9 • 82.1 Example 10 80.5 b) Protection against Argyresthia coπjugella. The test is carried out on area strongly infected first of all by Lithocolletis Blancardella Forr and to a smaller extent by Nepticula alella. Parcel size: 1.3 ha Replicate number: 2 Sample: control Reference Example 8 Examples 9 and 10 A out of water: 1500 1/ha Concentration: 0.2 %. The results are summarised in Table V. BAD ORIGINAL Table V Sample Ef fe ct relate d to cont {%) Re fe rence Example 8 80.2 Example 9 82.1 Ex ample 10 80.6 Example 15 Component Amount, parts by weight 0 f 0-Dimethyl-(l-hydroxy-2,2,2- trichloro-ethyl)-phosphonate (Trichlorphon) 70 Surfactant of the general Formula I (wherein A is -(CH 2 CH_0) ..-, Q is -CH=CH and q = 1.25) 2 Propylene-glycol-1,2 28 Example 16 Component Amount, parts by weight Trichlorphon 50.0 Xylene 39.5 Propylene-glycol-1,2 8.0 Surfactant of the general Formula I (wherein A is -(CH CK 0) z ,-, Q = -CH 2 -CH - and q = 1.25) 2.0 Calcium salt of dodecyl benzene sulfonic acid 0.5 Example 17 The tests described in Example 13 are carried out by using the compositions prepared according to Example 15 and 16. As standard Dipterex 50 is used in the same active ingredient concentration. According to the application tests the composition according to Examples 15 and 16 proved to be equivalent GINAL -BU E - 18 - to the standard. The activity tests are carried out under laborato conditions. The activity of the compositions accordin to Example 15 and 16 were eσuivalent to that of the standard composition. Example 18 Component " Amount, parts by weight Dichlorphos (OjO-dimethyl-2,2- dichloro-vinyl—phosphate) 50.0 10 Xylene 39.0 Propyleneglycol-1,2 4-.5 Surfactant of the general Formula I [A is -(CH 2 CH 2 0) 3{ -, Q is phenyleπe, σ = 1.25] 4. ..F Z. 15 Calcium salt of dodecyl benzene sulfonic acid 2.0 The application tests were carried out according t Examples 13. As standard Vapona 4-8 ED was used. The composition of the present invention according to 20 Example 18 proved to be equivalent to the standard composition. Example 19 Component Amount, parts by weight Per etrin [3-phenoxybeπ∑yl-3-(2,2- 25 dichlorovinyl)-2,2-dimethyl-cyclo- propane carboxylic acid] 23.0 Tetrametrin (3,4-,5-tetrahydro- phthalimidonethyl-chrysantemate) 2.0 Benzyl alcohol 5.0 30 Butyl-hydroxy-tolueπe 0.1 Propylene-glycol-1,2 1.0 Surfactant of the general Formula I (A=- (CH 2 CH 2 0) 23 - , Q=-CH 2 CH 2 - , σ=1.25] 2.0 BAD ORIGINAL Surfactant of the- general Formula I [wherein A is - (CH 2 CH 2 0)_,- f Q is -CH 2 -CH 2 -, q = 1.25] 3.5 Calcium salt of dodecyl benzene sulfonic acid 4-.0 Xylene 10.0 Sunflower oil 38.6 Example 20 Component Amount, parts by weight Permetrin 23.0 Tetra etrin 2.0 Benzyl alcohol 5.0 3utyl-hydroxy-toluene 0.1 Propyleπeglycol-1,2 5.5 Surfactant of the general Formula I [wherein A is -(CH CH 2 0) -, Q is -CH=CH- and q - 1.25) 5.5 Calcium salt of dodecyl benzene sulfonic acid 4-.0 Xylene 4-.9 Shellsol R 50.0 Example 21 The application tests of the compositions prepared according to Examples 19 and 20 were carried out as described in Example 13. As standard Ambush 25 EC was used. The composition according to Examples 19 and 20 proved to be equivalent to the standard sample. BAD ORIGINAL

Claims: WHAT WE CLAIM IS: 1. Stabilized liquid plant protecting composition comprising as main component 5-55 % by weight of an active ingredient, 20-90 % by weight of one or more carrier(s) and other auxiliary agents and 5-25 % by weight of a surfactant of the general Formula I 0 0=C-Q-C00-A-H and/or II (wherein R 1 and R 2 together stand for a hydrocarbon chain which when completed by a group of the general Formula -(CH=CH) - corresponds to the alkyl chain of soya fatty acid; Q is -( CH 2) D ~' -CH=CH- or phenylene; A is -(CH 2 CH 2 0) n - or - [CH(CH 3 )CH 2 0 n - ; BAD ORIGINAL R3 and R4- may be the same or different and stand for hydrogen, C-, -,-, alkyl, benzyl, phenyl, or alkylar n is an integral in the range of 3-70; . ; p is an integral number between 0 and 6; q is a number of 1.0-1.5). 2. Composition according to claim 1, comprising O j O-diethyl-O-(2-quinoxalinyl)-phosphorothioate as acti ingredient. 3. Composition according to Claim 1 comprising 0,0-dimethyl-(l-hydroxy-2,2,2-trichloroethyl)-phosphona as active ingredient. 4-. Composition according to Claim 1 comprising 0,0-dimethyl-2,2-dichloro-vinyl-phosphate as active ingredient. 5. Composition according to Claim 1 comprising 3-phenoxy-benzyl-3-(2,2-dichloro-vinyl)-2,2-dimethyl- cyclopropane carboxylic acid and/or 3,4-,5-tetrahydro- phthalimido-methyl-chrysantenate as active ingredient. 6. Composition according t o Claim 1 comprising as main component 25 % by weight of 0,0-diethyl-O-(2- quinoχalinyl)-phosphorothioate , 30-70 % by weight of an aromatic hydrocarbon and/or alcohol, 1-5 % by weight of a surfactant of the general Formula I or II (wherein , R ~ ' , R2, R3, R4-, Q, A, n, p and q are as stated in Claim 1 and 0,5-4- % by weight of a surfactant comprisin a sulfonic acid calcium salt as hydrophilic part. 7. Composition according to Claim 1 comprising as surfactant a compound of the general Formula I wherein A is -(CH 2 CH 2 0) 3j _- is -CH 2 -CH 2 - and q is 1.25. 8. Composition according to claim 1 comprising as surfactant a compound of the general Formula I, wherein A is -(CH 2 CH 2 0 23 -; Q is -CH 2 -CH 2 -; q is 1.25. 9. Composition according to Claim 1 comprising as surfactant a compound of the general Formula I wherein A is -(CH 2 CH 2 0 7 - Q is -CH -CH - and q is 1.25. 10. Composition according to Claim 1 comprising as surfactant a compound of the general Formula II wherein Q is -CH -CH - and q is 1.25. 11. Composition according to Claim 1 comprising, as surfactant a compound of the general Formula II wherein A is -(CH 2 CH 2 0) 7 -; . Q is -CH 2 -CH 2 - and q is 1.25. 12. Process for the preparation of surfactants of the general Formulae I 0 0=C-Q-C00-A-H and II . BAD ORIGINAL ' 0=C-Q-COO-A-H (wherein R , R , Q, A, R , R ,4-, n, p and q are as stated in Claim 1) which comprises a) for the preparation of compounds of the general Formu I, reacting epoxidized soya oil with a half ester of dicarboxylic acid formed with a polyalkylene glycol having a molecular weight of from 2000 to 3000 in the presence or absence of a solvent at a temperature of 100-200 °C, preferably between 150 °C and 180 °C; or b) for the preparation of compounds of the general Formula II, reacting a compound of the general Formul I (wherein 1, R2, Q, A, n, p and q are as stated in Claim 1) with ammonia or a primary or secondary amino compound in the presence or absence of a solvent. 13. Process according to method a) of Claim 12 which comprises using maleic acid, phtnalic acid, adipic acid or succinic acid as dicarboxylic acid. 14-, Surfactants of the general Formula I (wherein R , R , Q, A, n, p and q are as stated in Claim 1). 15. Surfactants of the general Formula II (wherein R 1, R2, R3, R4-, Q, A, n, p and q are as stated in Claim 1). BAD ORIGINAL

Inventors: CSERMELY GYOERGY, LANYI GYOERGY, MEZES FERENC, MOLNAR ATTILA, RACZ ISTVAN
Applicants: CHINOIN GYOGYSZER ES VEGYESZET
Application year: 1982
Main classification: C08G63
IPC codes: A01N25, C07D303