PLANT PROTECTING PREPARATIONS, VETERINARY AND ADDITIVE PREPARATIONS

Abstract: The invention relates to a plant protecting or veterinary or additive composition, containing beside the active ingredient and other usually applied auxiliaries, such as solid and liquid carrier(s), surface active agent(s) and further additive(s), one or more surface active agent(s) of general formulae (I) or (II), or a mixture thereof, wherein R, R<2>, R<3> and R<4> are independently from each other hydrogen atom, an organic or inorganic cation or a group of the general formula -(CH2-CH2-O)nR<1>, wherein R<1> is a C10-20 alkyl group and n is an integer from 4 to 20, with the proviso that from among the substituents R, R<2> and R<3> at least one is a group of the general formula (CH2-CH2O)nR<1>.

Description: PLANT PROTECTING PREPARATIONS, VETERINARY AND ADDITIVE PREPARATIONS The invention relates to plant protecting prepara¬ tions, veterinary preparations and additive preparations 5 admixable to plant protecting and veterinary preparations containing as surface active agents compounds of the general formulae (I) CH 2 - COOR 0 H0-C-C00R z (i) CH 2 -C00R and (II) COOR 4 0 further to the prepation thereof. Meaning of the substituents in the general formulae (I) and (II) are as follows: 2 3 4 R, R , R and R are independently hydrogen atom, an organic or inorganic cation, or a group of the 5 general formula -(CHLChL-O) R , wherein n is an integer from 4 to 20, and R is a C,η_2η alkyl group. The inorganic cation is advantageously a sodium-, potassium-, calcium- or magnesium-cation. The organic cation is advantageously a cation deriving from an amiπe, such as triethanolamine or diethaπolamine. The surface active agents of the general formulae (I) and (II) applied in the preparations according to the invention and their use in the cosmetic and detergent therapeutical preparations is disclosed in the published Hungarian Patent specification T/40994. The compounds of the general formulae (I) and (II) can be prepared in such way, that a fatty alcohol corres¬ ponding to R is ethoxylated (mean ethyleneoxide number is n), whereafter it is condensed with citric or tartaric acid and finally a salt is formed as acquired with an alkaline component supplying the suitable cation (pub¬ lished Hungarian Patent Specification T/40994). We have found that the surface active agents of the general formulae (I) and (II) can be advantageously applied in plant protecting and veterinary preparations, respectively. According to the invention from the surface active agents of the formulae (I) and (II) also additive prepa¬ rations without any active ingredient can be prepared, which can be admixed at the time of application with the plant protecting or veterinary preparation to be applied. The surface active agents of the general formulae (I) and (II) exert in the preparations according to the invention the following positive effects: - they are slowing down the chemical decomposition of the active ingredient, this way they are exerting a stabilizing effect; - they are influencing the formation of the adsorptive layer (building up; structure modification); - they are optimalizing the reological properties of the preparations, they are increasing the stability of the dispersion; - in some cases they are founding a liquid crystalline structure, advantageous from the view-point of the dispersion of active ingredient and stability of the preparation; - they are exerting a wetting, solubilizing, penetra¬ tion increasing effect; - they are modifying the transport character (diffu¬ sion, etc.), this way they are suitable for the penetration of capsules; - they are increasing the chemical and physical compatibility of the active ingredients, etc.; - from toxicologie point of view they are very favour¬ able, they have no poisonous effect, biologically they are totally decomposable (a biodegradation of 100 _). The preparations according to the invention contain the surface active agents of the general formulae (I) and (II) in the following amounts: plant protecting preparations 0.1 - 10 mass. veterinary preparations 0.1 - 10 mass. additive preparations 0.1 - 50 mass. The plant protecting preparations according to the invention may contain as active ingredient some fungicide, herbicide, insecticide, nematocide, acaricide or plant growth regulating agents, such as: Maneb: /manganese-ethylene-bis(dithiocarbamate)-polymer7 Zineb: /zinc-ethylene-bis(dithiocarbamate)-polymer7 -~ Manozeb: /complex of manganese-ethylene-bis(dithiocar- bamate-polymer formed with zinc salt7 Metiram: zinc-polyethyleπe-thiuram-disulfide complex Propineb: /zinc-propylene-bis(dithiocarbamate)-polymer7 Kaptan: /ϊ,2,3,6-tetrahydro-N-(trichloromethy1-thio)- 1 -phtalimid§7 Procimidon: /N-(3,5-dichlorophenyl)-l,2-dimethyl-cyclo- -propane-1,2-dicarboximide7 Kaptafol: N-(l,1,2,2-tetrachloro-ethylthio)-tetrahydro- -phtali ide -- Folpet: N-(trichloro-methyl-thio)-phtalimide Anilazin: /2,4-dichloro-6-(2-chloroanilin)-l,3,5-triazine Flutriafol: (RS)-2,4'-difluoro-σ_-(lH-l,2,4-triazole- -l-yl-methyl)-benzhydrile-alcohol Diklofluanid: N,N-dimethyl-N'-phenyl-N'-(fluoro-dichloro- 25 -methyl-thio)-sulphamide Triforin: N,N'-bis-(l-formamido-2,2,2-trichloro-ethyl)- -piperaziπe Vink lozol in : 3- ( 3 , 5-di chl oro-pheπy l ) -5-methyl -viny 1 -1 , 3 - -oxazolidine-2,4-dion Dodin: dodecyl-guanidine-acetate Pirazofos: 2-(0,0-diethyl-thiophosphoryl)-5-methyl-6- -carbetoxy-pyrazolo-(l,5-a)-pyrimidine Bupiri at: 2-ethyl-amino- -me hy1-5-n-buty1-4-yl-dimethyl- -sulfamate Feπarimol: <.-(2-chloro-phenyl)-..-(4 l -chloro-phenyl)-5"- -pyrimidyl-methaπol Beπomyl: l-butyl-carbamoyl-benzimidazole-2-methyl-carba- mate Fuberidazol: 2-(2-furyl)-benzimidazole Thiabendazol: 4-(4-thiazolyl)-lH-benzimidazole Propiconazol: l-/5-(2,4-dichlorophenyl)-4-propyl-l,3- -dioxolane-2-yl-methyl7-lH-l,2,4-triazole Triadimephon: l-(4-chloro-phenoxy)-l-(lH-l,2,4-triazole- -l-yl)-3,3-dimethyl-2-butanoπ Triadimenol: l-(4-chloro-pheπoxy)-l-(lH-l,2,4-triazole-l- -yl)-3,3-dimethyl-2-butanol Bitartanol: (3-(l,1'-biphenyl-4-yl-oxy)- β -(1 ,1-dimethyl- -ethyl)-lH-triazole-l-ethanol Dichlorobutrazol: l-(2,4-dichloro-pheπyl)-4,4-dimethyl- -2-(l,2,4-triazole-l-yl)-pentane-3-ol Thiophaπate-methyl: l,2-bis-(3-methoxy-carbonyl-thio- ureido)-benzene Tridemorph: 4-tridecyl-2,6-dimethyl-morpholiπe Carbendazim: 2-(methoxy-carbonyl-amino)-benzimidazole Phenpropiomorph: 4-(3-/4-(l,l-dimethyl-ethyl)-phenyl7-2- -methyl)-propyl-2,6-cis-dimethylmor- pholine Metalaxyl: D,L-N-(2, -dimethyl-pheπyl)-N-(2'-methoxy- -acetyD-alanine-methyl-ester Prochlorase: N-propyl-N-/2-(2,4,6-trichloro-phenoxy)- -ethyl7-imidazole-l-carboxamide Permetrin: (+_)-cis,traπsz-3-3(2,2-dichloro-vinyl)-2,2- -dimethyl-cyclopropanic acid-3-phenoxy-beπzyl -ester Cipermetrin: 2,2-dimethy1-3-(2,2-dichloro-vinyl)-cyclo¬ propane carboxylic acid-(cC -cyaπo-3-phenoxy- -beπzyD-ester Deltametrin: (IR, 3R)-3-(2,2-dibromo-vinyl)-2,2-dimethyl- -cyclopropane carboxylic acid-(S)-c -cyano-m- -phenoxy-benzyl-ester Biphentrin: (2-methyl)-l,1 '-biphenyl(-3-il)methyl-3-(2- -chloro-3,3,3-trifluoro-l-propenyl)-2,2- -dimethyl-cyclopropane-carboxylate Phenpropatrin: o -cyano-3-phenoxybenzyl-2,2,3,3-tetra- methyl-cyclopropane-carboxylate Malation: 0,0-dimethyl-S-(l,2-dicarbetoxy-ethyl)-dithio- phosphate Chlorphenvinphos: 0,0-diethyl-l-(2,4-dichloro-phenyl)- -2-chloro-vinyl-phosphate Chlorpiriphos: 0,0-diethyl-0-(3,5,6-trichloro-2-pyridyl)- -thiophosphate Dichlorphos: 0,0-di ethyl-2,2-dichloro-viπyl-phosphate Dimetoate: 0,0-dimethyl-S-(N-methyl-carbamoyl-methyl)- -dithiophosphate Phenitrotion: 0,0-dimethyl-0-(3-methyl-4-nitro-phenyl)- -thiophosphate Aldicarb: 2-methyl-2-methylthio-propionaldehyde-0-methyl- -carbamoyl-oxi Carbaryl: N-methyl-1-naphthyl-carbamate Diazinon: 0,0-diethyl-0-(2-isopropyl-4-methyl-pyrimidi- nyl)-thiophosphate Bensultap: S,S '-/2-(dimethyl-a ino)-trimethylen§7- bis-(benzene-thiosulphonate) Endosulphane: l,4,5,6,7,7-hexachloro-bicyclo-(l,l,2)- -5-heptene-2,3-bis-(oxymethyleπe)-sulphite Phenvalerate: p(.-cyano-m-phenoxy-beπzyl-ø.-isopropyl- -p-chloro-phenyl-acetate Metidation: 0,0-dimethyl-S-(2-methoxy-l,3,4-thiadiazole- -5-(4H)-onyl-(4)-methyl)- ithiophosphate Metomyl: S-methyl-l.-(methyl-carbamoyl-oxy)-thioacet- imidate Mevinphos: 0,0-dimethyl-0-(l-methyl-2-carbometoxy)- -viπyl-phosphate Trichlorphon: 0,0-dimethyl-l-hydroxy-2,2,2-trichloro- -ethyl-phosphonate Terbuphos: 0,0-diethyl-S-(terc-butyl-thiomethyl)-phosphor dithioate Quinalphos: 0,0-diethyl-0-/quinoxaliπyl/2/-/thioπphosphate Pyrimiphόs-methyl: 0.0-dimethyl-0-(2-diethyl-amino-4- -methyl-pyrimidine- 6-yl)-thiophos¬ phate Phosalon: 3-0,0-diethyl-dithiophosphoryl-methyl/-6- -chloro-benzoxazolone Chinmix: IRcisS + IScisR and IRtransS+lStransR enantiomer pairs of (RS)-&.-cyano-3-phenoxybenzyl(lRS)- -cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethyl- -cyclopropane-carboxylate Transmetrin: IRtransS and lStraπsR enantiomer pairs of (RS)-^ -cyano-3-phenoxybenzyl(lRS)cis- -trans-3-(2,2-dichlorovinyl)-2,2-dimethyl- -cyclopropane-carboxylate. The plant protecting preparations according to the invention can be formulated in the following forms: emulsion forming preparation (EC): wettable powders (WP); dispersible granulate (WG) ; suspension concentrate (SC) ULV preparation; concentrated aqueous solution (SL); microemulsion (EW); capsule-suspension (CS). The veterinary preparations according to the inven¬ tion can be formulated advantageously in the following forms: injection solutions, solutions suitable for oral dosage, concentrate-preparations, emulsions, suspensions, powders, granulates, pilules, tablets, boles, aerosols, pour-on and spot-on preparations. The additive preparations according to the inventio can be formulated advantageously in the following forms: aqueous solutions (SL), anhydrous concentrates (mixture with other surface active ageπt(s) and/or with components of other function, e.g. with a diluting component, a solvent, a filling agent.) In the course of the preparation of compositions according to the invention technologies generally used for the preparation of said formulations can be applied. The preparations according to the invention are contain¬ ing or can contain beside the surface active agents of the general formulae (I) and (II) other generally used additives, such as solid or liquid carrier(s), surface active agent(s) and other additive(s). The surface active agents of the general formulae (I) and (II) may be - depending on the meaning of _. "_. substituents R, R and R - of anionic or nonionic type. The surface active agents of the general formula (I) are of anionic type, in which one or two of the substituents R, R 2 and R3 are a hydrogen atom, or they represent an organic or inorganic cation. Those compounds of the general formula (II) are of anionic type, in which R represents a hydrogen atom or an organic or inorganic cation. The solubility of the surface active agents of the general formulae (I) and (II) depends on the quality of the cations taking part in the salt formation. In the course of the preparation of compositions according to the invention the compounds of the general formulae (I) and/or (II) can be applied without dilution or diluted, in the last case in the form of aqueous solutions. In an aqueous medium it is possible even in a relatively low concentration to form solutions of a mean viscosity. One of the advantages of the new tenzides is that their solutions are barely foaming. In the case using the compounds of the general formulae (I) and (II) in an aqeuous medium, it is prefer¬ able to adjust the pH between 5 and 7, but a more acidic medium (pH 2-5) is also suitable. (Naturally the pH must be choosen in a way, that it must be tolerable to the active ingredient, too.) The compounds of the general formulae (I) and (II) have very different properties depending on the meaning of R, R 1, R2, R3 and n, so they can be applied widely. In Table I the properties of two, in water excellent¬ ly soluble types are summarized: Table I disodium- sodium monolaureate-7- dilaureate-7- -citrate -citrate Cation Na Na E0 7 7 + 7 type of ester mono di Table I (contd. ) disodium- sodium monolaureate-7- dilaureate-7- -citrate -citrate solvent water water dry substance % 25 + 1 25 + 1 (50 °C, 16 h ) water _ 75 ± 1 75 __ 1 viscosity 20 °C P about 30 about 700 pH (1 . of active ingredient in water) 6.5 + 0.3 6.5 + 0.3 surface tension at 20 C (dyn/cm) 0.25 g/1 active ingredient 33.2 31.5 1.0 g/1 active ingredient 32.3 31.0 In Table II some compounds of the general formulae (I) and (II) are described suitable for application in the preparations according to the invention. Table II Component Ester Type R l n Starting Surface Solvent , (code) M=mono acide = = H alkyl acid active carrier D=di salt agent quantity T=tri quantity mass _ mass% A M H lauryl 7 citric acid 100 - C 12 M Na lauryl 8 citric acid 25 water C 12 M Na lauryl 20 citric acid 100 C 12 M TEA lauryl 10 citric acid 100 C 12 M TEA lauryl 4 citric acid 60 Vessalon C 12 -16 7+7 citric acid 100 Table II (contd. ) Component Ester Type R l n Starting Surface Solvent, (code) M=mono acide : = H alkyl acid active carrier D=di salt agent quantity T=tri quantity mass _ mass . G D TEA C 14 4+4 citric acid 100 - H D TEA ' C 18 6+6 citric acid 80 xylene I D Ca C 12 7+7 citric acid 70 butyl digylcol 3 T - C 12 6+6+6 citric acid 100 - K M H C 12 6 tartaric acid 100 - M D - C 12 5+5 tartaric acid 100 - N D - C 10 8+8 tartaric acid 100 - Table II (contd . ) Component Ester Type R l n Starting Surface Solvent, (code) M=mono acide = H alkyl acid active carrier D=di salt agent quantity T=tri quantity mass% mass% P D - C 12 7+7 tartaric acid 70 xylene R M Na C 12 6 citric acid 80 DMA 0 M Na C 12 6 tartaric acid 25 water S D Na C 12 6 + 6 citric acid 25 water T D Na C 12 6+6 citric acid 100 - X M K C 12 9+9 tartaric acid 40 water Y T - C 12 4+4+4 citric acϊd 50 Vessalon Table II (contd. ) Component Ester Type R l n Starting Surface Solven , (code) M=mono acide = = H alkyl acid active carrier D=di salt agent quantity T=tri quantity mass . mass% Z M Ca C 12 7 citric acid 100 - V D TEA C 12 5+5 citric acid 100 - W D MEA C 12 5+5 citric acid 50 water The surface activity of compounds of the general formulae (I) and (II) is excellent, that is they are decreasing suitably the water/air interfacial tension even in a low concentration. This is illustrated in Table III. Table III Surface tension dyn/cm 0.25 g/1 1 g/1 Compound of the general formula (I) code S 31.5 31.0 B 33.2 32.3 0 34.0 33.6 Sodium-dodecyl- -beπzene-sulphonate 41.2 34.2 Sodium-laury/.-stπer- -sulphate (E0:2) 35.0 31.8 The preparations according to the invention are illustrated by the following examples, without any limitation as to the scope of invention. l.) Emulsion forming agents (In the following preparations the components according to the invention (A, F, K) are increasing the chemical stability of the active ingredients.) a.) Dichlorvos (96 %) 20.85 mass_ Component A 2 mass _ Emulson AG/CAL 3 mass% Emulsoπ AG/EL 4 mass . Xylene ad 100 mass% where Emulson AG/CAL = calcium-dodecyl-benzeπe- -sulphoπate (a 60% active ingredient solution), b.) Cypermethrin (90%) 11.1 mass. Component F 1.5 mass% Emulson AG/CAL 2.5 mass% Emulson AG/C0H 2.5 mass% Solvesso 150 ad 100 mass% where Emulson AG/C0H = ethoxylated E0:25 hydrogeπated (saturated) castor oil derivative. Solvesso 150 = aromatic solvent. c.) Phenmedipham (97%) 16.1 mass% Component K 2.0 mass% Emulsogen AG/CAL 5.0 mass . Emulson AG/2B 4.0 mass% Emulson AG/7B 9.0 mass% Isophoron ad 100 mass% where Emulson AG/2B = ethoxylated nonylphenol, E0 : 2 Emulson AG/9B = ethoxylated nonylphenol, E0 : 9 2. Emulsion forming agents (EC) (In the following preparations the components according to the invention (G, Z, H, 3 , P, M) are possess- sing an e ulsing activity.) a.) Metolachcor (96%) 75 mass% 5 mass% Component G 6 mass% 3 mass% Emulson AG/CAL 2 mass% Emulson AG/PE 4 mass% Emulson AG/EL - 5 mass% Xylene ad 100 mass% where Emulson AG/PE = an E0 + PrO condensate b.) Cypermethrin (90 %)11. mass% 20.8 mass% Component Z 5 mass% 5 mass% Emulson AG/CAL 1 mass% 2.5 mass% Emulson AG/EL 2 mass% 2.5 mass% Solvesso 150 ad 100 mass% Xylene ad 100 mass% Cyclohexanon - 10 mass% c.) Quinalphos (in 50 % xylene) 50 mass% 50 mass% Component H 6 mass% 4 mass% Component 3 2 mass% 2 mass% Component P 2 mass% Component M - 4 mass ?- Xylene ad 100 mass% ad 100 mass 5 3. Aqueous solutions (SL) Foliage wetting increasing activity (promotion of biological activity) MCPA K - salt (97 %) 412 g/1 Dichloroprop K-salt (95%) - 526 g/1 Component B 20 g/1 Component S - 25 g/1 Water ad 1 litre 4. Water soluble powder concentrate (SP) Wetting agent, drop-spreading increasing effect. Cartapchloride (95 %) 42.1 mass% Component M 3 mass% Powdered sugar ad 100 mass%. Component M is advantageously moderating the clott¬ ing inclination of the preparation formed with water soluble sugar due to its hygroscopic property, that is it ensures better storage. 5. Sprayable powders (WP) Wetting agent Benomyl (95 %) 52.6 mass% - Carbeπdazim (97 %) - 51.6 Folpet (93 %) - 50 Copperoxychloride (50 % copper) - 30 Permetrin (95 %) - - - 26 Ultrasil VN 3 5 5 5 20 Calciumcarbonate ad 100 Kaolin ad 100% ad 100% ad 1003 Component E 3.5 2 - - Component Y - 2 3 3 Borresperse 3 A 3.5 3 5 4 where Borresperse 3 A =sodium-ligπiπe-sulphonate 6. Suspension concentrates (SC) mass % Flutriafol (98%) 25.5 - - - - Carbendazim (96%) - 20.9 - - - - 5 Carbofuran (93%) - - 43 - - - Atrazine (97%) - 51.5 - Isoproturon (96%) - - - - 47.5 Chloridazon (92%) _ _ _ _ _ 38.9 - Copperoxychloride ig (50% copper) - - - - - - 6 White oil - 20 8 - - - - Component W 0.5 1.5 - 0.4 0.4 - - Component 0 0.5 - - - - 0.8 - Component S - - 1 - 0.2 - 1 15 Propyleneglycol 5 6 6 6 6 6 6 Emulson AG/1314 0.5 0.3 0.5 - 0.5 2 0.5 Emulson AG/6130 1.0 0.75 0.9 1 0.8 - 1.5 Emulson AG/2527 - 1.2 0.9 - - 0.5 - Madeol AG/2376 0.5 0.5 0.2 0.2 0.2 0.15 0.2 20 Product 0.028 0.5 0.4 0.5 0.5 0.5 - 0.5 Water ad ad ad ad ad ad ad 100% 100% 100% 100% 100% 100% 100 where Madeol AG/2376 = xanthane gum + silicic acid Product 0028 = silicon oil emulsion (30%) antifoaming 25 agent Emulson AG/1314 = ethoxylated bisphenol (E0 : 13) Emulson AG/2527 = ethoxylated castor oil (E0 : 25) Emulson AG/6130 = triethanolamine salt of ethoxylated and phosphatized bisphenol (mixture of mono- and diphosphate, ethoxyla- tioπ : 13 EO) 7. Wettable powders (WS) mass% Carbendazim ( 96 ) 52. ,1 - - Folpet (93%) - 53.8 - Copper oxyquinolate (95%) - - 52.6 Ultrasil VN 3 5 5 5 Mowinol 4/88 8 8 8 Madeol AG/OR 95 2. 5 3 3.5 Component T 3 2.5 3.5 Irgalite-blue 1 1 0.8 Kaolin ad 100 where Mowinol 4/88 = polyvinyl-alcohol (Hoechst) Irgalite-blue = colouring agent 8. Suspension dressing agents (FS) mass% Carbendazim (96%) 26.1 Flutriafol (98%) - 12.8 Copper oxyquinolate (95%) - - 21.1 Ethyleπeglycole 7 7 7 Viπavil EVA 06 T 18 18 18 Component K 1 - 0.3 Component S - 0. 8 0.3 Emulson AG/1314 0.2 0. ,5 - Emulson AG/PE 0.3 1. 2 - Emulson AG/6130 0.5 «. 1.5 Continuation of page 21) Madeol AG/2376 0.1 0.2 Basasol ROT 76 L 0.5 0.5 0.8 Silicon SRE 0.7 0.7 0.5 Water ' ad 100 where Vinavil EVA 06 T = a film forming polymer polyvinylacetate derivative (Montedison) Basasol ROT 76 L = a colouring component (BASF) Silisoπ SRE = an antifoaming agent in a silicon oil emulsion of 30 % (Wacker) . 9. Microemulsions (EW) (a good stability between -5 °C and 54 °C) mass% a.)Cypermetrin (90%) 4.5 4.5 Permetrin (95%) - - 10.5 PB0 (90%) 15 Component B 3.0 - 5.0 Component 0 2.0 1.0 Component S - 4.0 Emulson AG/1314 12 15 14 Emulson AG/0600 3 3 6 Water ad 100 where Emulson AG/0600 = Emulson AG/CAL (calcium- -dodecyl-benzosulphonate) PB0 = piperonyl-butoxyde b.) Cypermetrin-isomer (g//ι1) mass _ - lRcisS+lScisR 20 20 - - - IRtransS+lStransR 30 30 50 50 PBO _ 100 — 100 Ethyleneglycol 90 - 90 Propyleπeglycol - 90 - 90 Butanol 50 - 40 30 Ethanol 40 Component B 60 50 40 60 Component 0 - 10 10 90 Component S 5 10 Emulson AG/1314 100 70 50 70 Emulson AG/0600 60 40 50 60 Water ad 1000 ml c. ) mass% Quinalphos 250 250 200 - 200 Cypermetrin isomer - lRcisS+lScisR 20 - lRtraπsS + lStraπsR - - 30 50 50 Tetrametriπ 5 Butyl-hydroxytoluene - - 10 10 10 Solvesso 200 10 Butanol 70 200 50 10 30 Component B 50 - 10 - 25 Component 0 70 - - 100 Component S - 100 30 - 40 (continuation of page 23) Component H 50 - 20 Component I 10 - - 30 Component M - - 50 - 15 Emulson AG/1314 40 10 50 Water ad 1000 ml 10. Granulates dispersable in water (WG) (promoting quick wetting) Carbendazim (96%) 78.1 mass% Atrazine (97%) - 77.3 mass% Component W 3 mass% Component B - 4.5 mass% Emulson AG/0240 0.7 mass% 0.5 mass% Madeol AG/DR95 5 mass% 5 mass% Ultrasil VN 3 5 mass% 5 mass% Kaolin ad 100 % Where Emulson AG/0240 = ethoxylated-bisphenol (E0:24) In the course of the preparation on the powderous mixtures consisting of the component above - after fine grounding - in the form of an aqueous solution the suitable quantity of the surface active ingredient according to the invention is sprayed in a granulating mixer (plate granulator). 11. Ultra ULV preparations (Drop spreading and adhesion improving, active ingredient stabilizing, viscosity adjusting effect) Cypermethrin (90%) 11.1 mass% Phosalome (95%) - 26.3 mass% Solvesso 200 25.0 mass% 35.0 mass . Component I 2.0 mass% 2.0 mass% Sunflower oil ad 100 mass% ad 100 mass% 12. Microcapsule (Control of the active ingredient release, influenc¬ ing the capsule-preparation) mass% a.) Transmetrin 12.62 Tetrametrin 1.24 PBO 86.14 Poly-phenylisocyanate (31%) 3.0 Component I 1.0 Water 32.9 aqueous diluted 1,6-hexamethylene- diamine solution (1,6-HMD aqueous 12.4 % solution) 3.0 Ethyleneglycol 15.7 Component M 1.0 CaCl 2 3.0 b.) Permetriπ 28.6 Aromatol 21.5 Poly-phenylisocyanate 3.5 Component I 1.1 Water 40.8 HMD-diluted 3.5 CaCl 2 1.1 c.) Permetrin 29.0 mass% Solvesso 100 14.6 Component I 1.0 Water 35.6 HMD-diluted 3.0 CaCl 2 5.0 NaCl 1.0 Component M 1.0 d.) Cypermetrin : Aromatol 1:1 47.3 Poly-phenylisocyanate 3.3 Component I 1.0 HMD-diluted 3.3 Ethyleneglycol 4.9 Water 38.8 CaCl 2 0.6 Component P 0.8 e.) Cypermetrin : Aromatol 20: 15 38.6 Poly-phenylisocyanate 2.7 Component I 0.9 Water 31.6 HMD-diluted 2.7 Ethyleneglycol 23.0 CaCl 2 0.5 f.) Cypermetrin : Aromatol 20: 15 48.0 Poly-phenylisocyanate 3.4 Component I 1.1 Water 39.5 ma ss% HMD-diluted 3.4 Ethyleneglycol 2.4 CaCl 2 0.6 Component N 1.2 g.) Transmetrin-Solvesso 100 10:35 37.8 Poly-phenylisocyanate 2.9 Component I 1.6 Water 30.8 HMD-diluted 2.8 Ethyleneglycol 8.1 CaCl 2 12.2 NaCl 3.3 Component M 0.8 h.) Transmetrin : Solvesso 100 : Xylene 10 : 16 : 5 49.3 Poly-phenylisocyanate 3.4 Component I 1.1 Water 40.0 HMD-diluted 3.4 CaCl 2 2.8 i.) Ekalux 50 38.3 Poly-phenylisocyanate 3.4 Water 40.0 HMD-diluted 3.4 CaCl 2 2.8 j.) EPTC 36.3 Poly-phenylisocyanate 2.5 mass% Component I 1.6 Water 29.5 HMD-diluted 3.1 NaCl 1.6 CaCl 2 3.1 Component M 0.8 k.) Permetrin-Aromatol (20 : 15) 47.5 Poly-phenylisocyanate 3.2 Component I 1.0 Water 38.1 HMD-diluted 3.2 CaCl 2 5.0 NaCl 1.0 Component N 1.0 The microcapsules above were prepared by the following steps: a.) the active ingredient and the poly-phenylisocyanate were kneaded to a homogen phase; b.) the surface active agent and the water were mixed to one phase; c.) into the aqueous phase (b) the oily phase (a) was poured slowly, thereafter by turaxing slowly while cooling with water an emulsion was formed; d.) to the emulsion the diluted HMD solution was added drop-by-drop, whereafter while cooling with water the mixture was turaxed; e.) if necessary to the finished formulation ethylene¬ glycol was added and the suitable quantities of CaCl , and NaCl respectively, were added to adjust the viscosity. 13. Preparation for bathing animals Chinmix 250 g/1 Component A 70 g/1 Xylene ad 1000 ml By mixing the mixture above in a ratio of 1:2 - - 1:20 with phenolfree kreoline and diluting the same with a 500-2000 fold quantity of water a good stabilized emulsion for bathing animals is obtained. Kreolin = mixture of coal oil, Na-iktiol, sodium hydroxide and caπifol 14. Additive preparation containing no active ingredient a. Component X Potassium-mono-laurate-ethoxy(9)-tartarate 40 mass% Water 60 mass% b . Component B Sodium-mono-laurate-ethoxy(δ)-citrate 25 mass% Water 75 mass% 15. Preparation of tankmixtures Tankmixtures of the following compositions were prepared in a way, that the combination of a plant protecting agent and/or an artificial chemical fertilizer (from time to time in a prediluted form) is added to the additive preparation. mass% Component X 2.0 1.5 Component B 3.0 1.5 Fundazol 50 WP 1.0 Olitref EC 1.2 Dithiane M-45 1.0 0.7 Carbamide 15.0 Sequestren 138 Fe 1.0 Water ad 100

Claims: What we claim is 1. A plant protecting composition, containing beside the active ingredient and other usually applied auxiliaries, such as solid and liquid carrier(s), surface active agent(s) and further additive(s), one or more surface active agent(s) of the general formulae (I) or ( I I ) HO - CH ( I I ) COOR^ or a mixture thereof, wherein R, R 2 , R3 and R4 are independently from- each other hydrogen atom, an organic or inorganic cation or a froup of the general formula -(CH 2 -CH 2 -0)_R , wherein R is a C 10 _ 20 alkyl group and n is an integer from 4 to 20, with the provisio that from among the substituents R, R 2 and R3 at least one is a group of the general formula CH^CH^^R 1 . 2. Plant protecting composition according to claim 1, character ized by that they are formulated in the form of emulsion forming preparation (EC), spray- able powder (WP), dispersable granulate (WG) , suspension concentrate (SC), ULV preparation, concentrated aqueous solution (SL), icroemulsion (ES), capsule suspension (CS). 3. Plant protecting composition according to claims 1 or 2, characterized by that as active ingredien it contains a fungicide, herbicide, insecticide, nemato- cide, acaricide or plant growth regulating agent . 4. Plant protecting composition according to claims 1 to 3, char acterized by that as a surface active agent it contains compounds of the general formula (I) in which R is a group of the general formula (CH 2 ~ -CH 2 0) R 1, R2 and R3 are hydrogen atoms or organic or inorganic cations and the meanings of R and n are the same as given in claim 1. 5. Plant protecting composition according to claims 1 to 3, char acterized by that as surface active agent it contains compounds of the general formula (I) in which R and R are a group of the general formula (CH 2 -CH 2 0 R 1 and R2 is a hydrogen atom or an organic or inorganic cation and the meaning of R and n are the same as given in claim 1. 6. Plant protecting composition according to claims 1 to 3, c h a r a c t er i z e d b y that as surface active ingredient it contains compounds of the general formula (I) in which R and R are a group of the general formula (CH 2 -CH 2 0) R , R is a hydrogen atom or an organic or inorganic cation and the meaning of R and n are the same as given in claim 1. 7. Plant protecting composition according to claims 1 to 3, c h a r a c t er i z e d b y that as surface active agent it contains compounds of the general formula 2 3 (I), in which the meaning of R , R and R is a group of the general formula (CH^CH^^R 1 and that of R 1 and n is the same as given in claim 1. 8. Plant protecting composition according to claims 1 to 3, c h a r a ct er i z e d b y that as surface active agent it contains compounds of the general formula (II) 4 in which R is hydrogen atom, or an organic or inorganic cation and the meaning of R and n is the same as given in claim 1. 9. Plant protecting composition according to claims 1 to 3, c h a r a c t e r i z e d b y that as surface active agent it contains compounds of the general formula (II) in which R is a group of the general formula (CH ? - -CH 2 0) R and the meanings of R and n are the same as given in claim 1. 10. Plant protecting composition according to claims 1 to 6 or 8, c h a r a cter i z e d b y that as surface active agent it contains compounds of the general formula (I) and/or (II) in which the inorganic cation is H and/or Na + and/or K + and/or Ca + and/or Mg + and the organic cation is triethanolamine and/or diethanolamine cation. 11. Plant protecting or veterinary additive composi¬ tion containing beside the in the plant protection usually applied auxiliaries, thus solid or liquid carrier(s), surface active ageπt(s) and other auxiliaries, in a quantity of 0.1 - 99.9 mass% one or more surface actife agent(s) of the general formulae (I) or ( ID I HO - CH COOR^ _? " _. / in which R , R , R and R are independently from each other hydrogen atom, an organic or inorganic cation, or a group of the general formula (CH -CH 2 0) R , wherein R is a C, Q _ 20 alkyl group, n is an integer from 4 to 20, with the provisio that from among the substituents 2 3 R, R and R at least one is a group of the general formula (CH 2 -CH 2 0) n R 1 . 12. An additive composition according to claim 11, c h a r a c t e r i z e d b y that as active ingredient it contains a fungicide, herbicide, insecticide, πemato- cide, acaricide or plant growth regulating agent. 13. An additive composition according to claim 11, c h a r a c t er i z e d b y that as surface active agent it contains compounds of the general formula (I) in which R is a group of the general formula (CH 2 -CH 2 0) R R 2 and R3 mean hydrogen atom or an organic or inorganic cation, the meaning of R and n are given in claim 1. 14. An additive composition according to claim 11, ch ar a ct e r i ze d b y that as surface active agent it contains a compound of the general formula (I) in which R and R mean a group of the general formula (CH 2 -CH 2 0) R 1, R2 means hydrogen atom or an organic or inorganic cation, the meanings of R and n are given in claim 1. 15. An additive composition according to claim 11, c h a r a c t e r i z e d b y that as surface active agent it contains compounds of the general formula (I) in which R and R ^ mean a group of the general formula (CH 2 -CH 2 0) R , R means hydrogen atom or an organic or inorganic cation, the meanings of R and n are given in claim 1. 16. An additive composition according to claim 11, characterized by that as surface active agent it contains compounds of the general formula (I) in which R, R 2 and R3 mean a group of the general formula (CH 2 -CH 2 0) R , the meanings of R and n are given in claim 1. 17. An additive composition according to claim 11, characterized by that as surface active agent it contains compounds of the general formula (II) in which R 4 means a hydrogen atom or an organic or inorganic cation, the meanings of R and n are given in claim 1. 18. An additive composition according to claim 11, characterized by that as surface active agent it contains compounds of the general formula (II), in which R means a group of the general formula (CH 2 -CH 2 0) R and the meanings of R and n are given in claim 1. 19. An additive composition according to claim 11, characterized by that as surface active agent it contains compounds of the general formula (I) and/or (II) in which the inorganic cation is H and/or Na + and/or K + and/or Ca + and/or Mg , the organic cation is triethanolamine and/or diethanolamine cation. 20. Veterinary preparation, containing beside the active ingredient and auxiliaries applied usually in the veterinary therapy, thus solid or liquid carrier(s) surface active agent(s) and other additives, 0.1-10 mass% of one or two surface active agents of the general formulae (I) CH 2 ~COOR HO-C-COOR d ) CH 2 -C00R 3 or (II), COθ / CH 2 - CH 2 θ / n R 1 I HO - CH HO - CH " ( I I ) l , COOR 4 or their mixture, in which R, R , R and R are indepen¬ dently from each other hydrogen atom, an organic or inorganic cation, or a group of the general formula (CH 2 -CH 2 0) r) R 1 , R 1 is a C 1Q _ 20 alkyl group, n is an integer from 4 to 20 with the provisio that at least one of the substituents R, R 2 and R3 is a group of the general formula (CH^CH^^R 1 . - 38 - 21. A veterinary preparation according to claim 20, c h a r a c t er i z e d b y that as active ingredient it contains fungicide, insecticide, nematocide or acari- cide. 22. A veterinary preparation according to claim 20, c h a r a cter i ze d b y that as surface active agent it contains a compound of the general formula (I), in which R means a group of the general formula (CH 2 -CH 2 0) R 1 , R2 and R3 represent hydrogen atom, or an organic or inorganic cation, R and n are the same as given in claim 1. 23. A veterinary preparation according to claim 20, c h ar a cter i ze d b y that as surface active agent it contains a compound of the general formula (I), in which R and R represent a group of the general formula (CH 2 -CH 2 0) R 1, R2 is a hydrogen atom, or an organic or inorganic cation, R and n are the same as given in claim 1. 24. A veterinary preparation according to claim 20, c h a r a c ter i ze d b y that as surface active agent it contains a compound of the general formula 2 (I), in which R and R represent a group of the general formula (CH 2 ~CH 2 ) R , R is hydrogen atom, or an organic or inorganic cation, R and n are the same as given in claim 1. 25. A veterinary preparation according to claim 20, character ized by that as surface active agent it contains a compound, in which R, R2 and R3 represent a group of the general formula (CH„-CH 2 0) R , R and n are the same as given in claim 1. 26. A veterinary preparation according to claim 20, c h a r a c t e r i z e d b y that as surface active agent it contains a compound of the general formula (II), in which R represents hydrogen atom, or an or¬ ganic or inorganic cation, R and n are the same as given in claim 1. 27. A veterinary preparation according to claim 20, c h a r a c t e r i z e d b y that as surface active agent it contains a compound of the general formula (II), in which R represents a group of the general formula (CH 2 -CH 2 0) R , R and n are the same as given in claim 1. 28. A veterinary preparation according to claim 20, c h a r a c t e r i z e d b y that it contains surface active agents of the general formula (I) and/or (II) in which the inorganic cation is H and/or Na and/or K + and/or Ca2+ and/or Mg2+ and the organic cation is triethanolamine and/or diethanolamine cation. 29. Process for the preparation of the veterinary preparation according to claim 20, c h a r a c t e r i z e d b y that the active ingredient and other usually applied auxiliaries, thus solid or liquid carrier(s), other auxiliaries are admixed with one or two surface active agent(s) of the general formula (I) or (II) or with the mixture thereof, where the meaning of R , R 1 , R2 and R and n is given in claim 20 - and the mixture obtained is formulated in the usually applied form.

Inventors: BOHUS PETER, MARMAROSI TAMASNE, NAGY LAJOS, PAP LASZLO, SZEGOE ANDRAS, SZEKELY ISTVAN, BOHUS, PETER, MARMAROSI, TAMASNE, NAGY, LAJOS, PAP, LASZLO, SZEGOE, ANDRAS, SZEKELY, ISTVAN
Applicants: CHINOIN GYOGYSZER ES VEGYESZET, CHINOIN GYOGYSZER ES VEGYESZETI TERMEKEK GYARA RT
Application year: 1990
Main classification: A01N25
IPC codes: A01N25, A61K9, A61K47