IL27724A - Thiaimidazolidines and their preparation - Google Patents

Description

and their preparation FARBENPABRI BAYER A 26269 2 The present invention relates to new which have properties and to their paration and It is already known that imidazolidines as the of the formula have a herbicidal activity Patent Specification The invention provides new thiaimidazolidines of the general formula in which is alkoxy lmercapto having 2 or 3 carbon or and where there are 2 or substituents they may be the same or is hydrogen or an alkyl radical having 1 4 carbon and n is 2 or These compounds exhibit a strong herbicidal activity which is particularly Both this activity and selectivity are surprisingly much better than the properties of those known imidazolidines of similar chemical structure which are most closel related to compounds according to the invention as regards structure and type of The invention also consists in a process for the preparation of of formula I wherein a urea derivative of the in which and n have the same meaning as is reacted with optionally in the presence of a When chloride and are used as the course o C HOI Examples of urea derivatives of formula II are The reaction is preferably carried out in the presence a When working with those are preferably used which do not or react only with As such solvents there are mentioned for carbons as chlorinated hydrocarbons as methylene carbon chlor ethers as dibutyl any tures of these The reaction temperature may be varied within a wide In is carried out at 20 to preferably 50 to In the reactants are used in approximately eq The reaction can be carried out for example in such a way that chloride is added dropwise at 60 to a solution or suspension of the urea and kept at this perature until the splitting off of hydrogen chloride has After completion of the evaporation in a vacuum is The residue in most cases is is stirred together with warm methanol and the solid substance filtered The thia midazolidine is thus obtained in pure The of the invention exhibit strong herbicidal They can therefore be used for the destruction of unwanted Since their herbicidal effectiveness varies greatly in respect of different they can also be used as selective they can be used for weed control in agricultural cultivations such as To be deemed weeds in the broadest sense are plants which grow in cultivations or in places where they are not Especially well capable of being controlled The active compounds of the invention may be converted into pastes and These may be prepared in known for example by mixing the active compounds with that solid or liquid diluents or optionally with the use of that emulsifying agents dispersing In the case of the use of water as organic solvents may for example also be used as auxiliary As liauid diluents or there are preferably used aromatic such as xylenes or chlorinated aromatic such as chlorobenzenes such as mineral oil such as methanol or and strongly polar such as dimethyl formamide or dimethyl as well as As solid diluents or carriers there are preferably used ground natural such as talc or or ground synthetic such as highly dispersed acid or cates Preferred examples of emulsifying agents include and anionic such as polyoxyethylene fatty acid polyoxyethylene fatty alcohol for example alkylaryl glycol alkyl sulphonates and preferred examples of dispersing agents include sulphite waste liquors and methyl The active compounds of the invention may be present in the formulations in admixture with known active such as phenoxycarb nitrated triazines or The formulations in between and preferably between and by weight of active The active compounds may be used as or in the form of their formulations or of special application preparations made therefr m such as read solutions emulsions s s e ons Application may be effected in customary for example by scattering or The active compounds can be used according to the gence but are particularly effective when they are used according to the The concentration of active compound may vary within wide It is dependent on the weather on the purpose for which the active compound is and on the plants which are to be controlled or When the active compounds are used as total the content of active compound in the composition actually applied in between and 2 per cent by preferably between and per cent by When the active compounds are used as selective the content of active in between and per cent by preferably between and per cent by The invention also nrovides a herbicidal composition ing as active ingredient a thiaimidazolidine as described herein in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a The invention also a method of combating weeds which comnrises anplying to the weeds or a weed habitat a dine as described herein alone or in the form of a composition taining as active ingredient a thiaimidazolidine as described herein in admixture with a solid or liauid diluent or The following Examples A and B the herbicidal activity of the active compounds of the Example A test 5 parts by weight acetone 1 part by weight alkylaryl polyglycol ether by weight of active is mixed with the stated amount of the stated amount of emulsifier is added and the trate is then diluted with water to the desired Test plants which have a height of about 5 15 are sprayed with the preparation of the active compound until just dew After three the degree of dama e to the plants is determined and by the value 0 which have following 0 no 1 a few slightly burnt spots 2 marked damage to leaves 3 some leaves and parts of stalks partially dead 4 plant partially destroyed 5 plant completel The active their concentrations and the results obtained can be see from the following TABLE o CD Table teat Active compound tration podium pis soga laria of chloa ive There act the same manner ample test 5 parte by weight acetone 1 part by weight arylalkyl polyglycol ether To produce a suitable preparation of active 1 part by weight of active compound is mixed with the stated amount of the stated amount of emulsifier is added and the trate is then diluted with water to the desired Seeds of the test plants are sown in normal soil after 24 with the preparation of the active It is expedient to keep constant the amount of water per unit The concentration of the active compound the preparation is of no only the amount of active compound applied per unit area being After three the degree of damage to the test plants is determined and characterised by the values 0 5 whic have the following 0 no effect 1 slight damage or delay in growth 2 marked damage or of growth 3 heavy damage and only deficient development or only 0 emerged 4 partially destroyed after germination or only emerged 5 plants completely dead or not The active the amounts applied and the results obtained can seen from the following Table test Ο Ο Active compound Active compound Ohenopodium used Table test Active compound Active compound Chenopodium used The following Examples 1 and 2 Illustrate the process of the 1 22 g are pended in 150 cc 14 g chloride are added dropwise at 70 and the mixture is left at this temperature until the evolution of hydrogen chloride has Concentration is then effected in a vacuum and the product which precipitates is filtered off with suction after ether has been added to the After from warm 20 g 158 are The chlorcarbonylsulphen chloride used for the reaction is obtainable as 210 ml 18 g water and 186 g 1 chloride are heated to 45 with vigorous 1 to nearly 2 mole split off and the evolution of HC1 The two layers of the reaction material are separated in a separating The light nhase is crude chloride which ready possesses It can be further purified by mm The following compounds are prepared in the same manner as stated 0 106 2 The follovlng compounds also prepared in the same manner as in 148 Example 3 g are suspended in 300 cc chlorbenzene and heated under reflux together with 21 g c lorcax ony su p en chloride until the evolution of hydrogen chloride has ended 4 Cooling is then followed by filtration from undissolved matter and tration in a The residue is stirred together with warm the undissolved product is filtered off with suction and washed with 8 g insufficientOCRQuality

Claims (1)

1. CLAIMS 1. I Thiaimidazolidines of the formula in which R is alkyl, alkoxy and/or alkylmercapto (each having 1, 2 or 3 carbon atoms) or halogen, and where there are 2 or 3 R substituents they may be the same or different; R' is hydrogen or an alkyl radical having 1 - 4 carbon atoms, and-n is 0, 1, 2 or 3* 2, I The thiaimidazolidine of the formula The thiaimidazolidine of the formula The thiaimidazolidine of the formula 5. The thiaimidazolidine of the formula The thiaimidazolidine of the formula The thiaimidazolidine of the formula 8. The thiaimidazolidine of the formula 9. The thiaimidazolidine of the formula The thiaimidazolidine of the formula The thiaimidazolidine of the formula 27724/2 17. A process for the production of thiaioidazolid- -fcnea according to Olaim 1, in which an urea derivative of the formula in which R, R* and n have the same meaning as in Olaim 1, is reacted with chlorocarbonylsulphen^ chloride. 18. A process according to Claim 17, in which the reaction Is carried out at 20 to 150°C, preferably at 50 to 80°C. 19· A process according to Claims 17 or 18, in which the reaction is carried out in the presence of a solvent, 20. A process for the production of thiaimidazolid-ines according to Claim 1 substantially as hereinbefore described in any of the Examples/ l to 3. 21. Herbioldal compositions containing as active ingredient a thiaimidazolidine according to any of Claims 1 to 16, in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 22· Compositions according to Claim 21 containing from 0*01 to 95% by weight of the active compound, preferably from 0.1 to 2% or from 0.01 to 0.2 . 23* A method of combating weeds which comprises applying to the weeds or a weed habitat a thiaimidazolidine according to any of Claims 1 to 16, or a composition 27724/2 according to Claims 21 or 22. 24· A nethod according to Claim 23 , being applied to combatting the following weeds, risi- Sinapie, Galineoga, Stellaria, Urtica, Matricaria, Daucus, Pastinaea and/or Echinochlo*. 25· A method according to Claim 24, substantially as described herein with reference to Examples A or fi. For the Applicants DR. HBISHOID COHK AHD PAHTNBRS