IL45768A - 1,3-disubstituted-3-(5-substituted-1,3,4-thiadiazol-2-yl)-ureas with selective herbicidal action - Google Patents

Abstract

The novel urea derivatives of the formula (I) <IMAGE> are employed as active ingredient in selective herbicides. In the urea derivatives of the formula (I) the substituents have the meanings given in Patent Claim 1, and n is 1 or 2. Processes for the preparation of the novel urea derivatives of the formula (I) are also described. The novel selective herbicides have a good activity against weeds and can be used for controlling the latter in a range of crops of useful plants, for example crops of groundnuts, potatoes, maize and peas. [GB1488817A]

Description

adi selective action The 1s concerned new a process for their and rations containing these compounds as active azolyl having a herbicidal action are already known Of f enl egungsschri f ten 16 696 and 20 44 these agents have an insufficient sel The problem of the to provide an agent having a good weeding action and sel dal action towards economic plant The problem of the invention is solved by a which is characterised by a content of at least one compound of the general formula in which represents methyl or ethyl represents hydrogen or methyl and represents or In 1 and German 1 described 1 and 2 there are compounds similar to whose general formula includes the compounds of the present However none of said patents disclose compounds bearing allyl or methoxy as ami or suggest the unexpected superiority of such compounds as demonstrated in comparative example 3 hereinafter with reference to the closest compounds disclosed in 1 The compounds of the invention are thus by their structure and dal and can be used for combating edonous and dicotyledonous weeds in economic plant As such economic plant crops there may be for maize and The compounds of the Invention are used to for weeds In arable such as Stellarla Matricaria Lam um a plexl caule Galium apar Chrysanthemum Ipomea S1nap1s Solanum Setar a Setarla faberl and Poa Depending on the compound used and the region of use there are generally required for combating weeds quantities of about to 5 kg of active substance per the use being either by the method or by the The active substances of the Invention may be used either singly or as mixtures of several active If there may be added other plant protection or pest combating agents for nematoddes or other depending on the purpose An addition of for 1s also When t 1s intended to widen the spectrum of action or to destroy waste land other herbicides may be For there are suitable as herblcldally active components to be added active substances of the groups of an dlaz aliphatic carboxyl c and 1c halogenated benzoic adds and c 1c esters of such carboxyllc carbamlc add thlocarbamlc add add and agents and Among other additions there are to be for also additions that give with herb cides a synergistic Increase 1n such as wetting solvents and oily The active substances are advantageously used the form of such as scattering emulsions or suspensions the addition of liquid solid carriers or and optionally emulsifying dispersing Suitable liquid carriers for aliphatic and aromatic hydrocarbons such as cycl ohexanone and also mineral As solid carriers there are suitable mineral for tonsil silica gel silicic acid and vegetable for As substances there may be for calcium nsul phonate polyoxyethyl ene phenol naphthal enesul c formaldehyde fatty alcohol sulphates and alkali and alkaline earth metal salts of fatty The proportion of active substance or substances 1n the preparations may vary within wide For the preparations may contain about 20 to 80 per cent by weight of active substances about 80 to 20 per cent by weight of or solid and optionally up to 20 per cent by weight of The starting products for carrying out the process descrl are known or can be made by methods 1n themselves The following Examples the preparation of the compounds of the 5 thy 1 sul To a mixture of grams of hydroxyl ne 25 ml of water and ml of are added 14 ml of tr1 ethyl ami ne are added while stirring at grams of chloride melting at The reaction mixture is allowed to stand and then methylene chloride and water are the organic phase is separated dried with magnesium and the solvent is distilled The residue is recrystall sed from isopropyl grams of of 1 1 melting at n The chloride 1s prepared by reacting e with grams of 1 azol are dissolved 1n 100 ml of glacial acetic and 40 ml of Into this mixture are Introduced while stirring at 40eC 15 grams of finely pulverised potassium whereupon the temperature rises to The whole 1s stirred for a further 30 the precipitated pyroluslte 1s reduced at by the dropwise addition of a solution of 9 grams of sodium metabl te 1n 100 ml of and the reaction product 1s precipitated with 400 ml of The Isolated 1 after recrystallisatlon from propanol grams of melts at In the following Table are given further compounds of the 1 nventlon Namessof the compounds Physical constants ad1 166eC 1 1 The compounds of the are colourless and oily or crystalline substances that are only somewhat soluble 1n but dissolve well 1n organic solvents such as methylene tetrahydrof hexanone and following Examples Illustrate the and properties of the compounds of the Invention as compared with known Example In a greenhouse experiment the plants mentioned were treated before emergence with the agents at the rate of kg of active substance per For this purpose the agents were sprayed uniformly over the in the form of aqueous suspension 1n 500 litres of water per The results 3 weeks after the treatment show that the agents of the while having a good action against the were tolerated by crop plants treated 1n the same On the other hand the agent used for comparison damaged the ly honyl th i adi 1 10 10 10 0 2 1 1 3 urea 10 10 10 10 methyl s rea 10 10 Agent for comparison sul phonyl 5 4 2 4 2 0 0 0 0 Untreated 10 10 10 10 10 10 10 10 0 totally 10 not Example 2 In a greenhouse the plants mentioned were treated after emergence with the agents at the rate of 3 kg of active substance per For this purpose the agents were sprayed uniformly over the plants 1n the form of aqueous suspensions In 500 litres of water per As 1s seen from the the agents of the Invention had a better selectivity than the agent used for J Agents of the invention sul 10 10 10 0 0 1 th1 adi azol 10 10 10 0 0 0 0 sulphonyl 8 8 10 0 0 0 3 sulphonyl 10 8 8 0 1 0 Agent for comparison 4 2 2 3 1 0 0 0 0 Untreated 10 10 10 10 10 10 0 Totally destroyed 10 not damaged Comparative Example 3 and herbicide tests Method of propagating test species sanguinalis Setaria glauca Sorgum halapense Echinochloa Amarantus retroflexus Brassi ca spp G Zea Mays Phaseolus vulgaris All crop and weed species were planted individually in containing potting Six each of and snapbeans were seeded to a depth equal to the diameter of the All other species were on the surface and sprinkled with screened soil in an amount sufficient to cover the Immediately after all pots were watered by in green Pots for the phase were seeded one day before Planting dates for the phase were varied so that all seedlings would reach the desired stage of development The proper stage of seedling development for treatment in the phase is as Grasses height gweed 1 or 2 true leaves above visible cotyledons Cotton first true leave 1n expanded cotyledons corn 1n height Beans Primary leaves growing point at primary leaf Method of treatment Compounds were tested at rates of application 3 of actual compound per acre 1n a spray volume of 500 1 per ha Spray hood constants required to deliver the above volume are as Nozzle speed pressure atu Nozzle type to provide uniform flat spray nozzle output 100 ml 1n Formulations for spray applications were prepared the following two 600 mg of compound g Both components are triturated by They were suspended 1n 100 ml Spray applications were made 1n a hood containing a removable One pot of each specie was placed on a wooden Treatments were removed to the greenOhouse after Watering during the observation period was done only by Method of recording results Three weeks after and or control was visually and the results were as shown 1n the following data are provided 1n table II and data are provided 1n table for compounds having the formula in table Table 1 a 1 CH3S02 CH30 3 H Related comparative compounds Patent R R2 12 H H 31 CH3 S H H 33 CS H H Table II control O CO ro co X 3 C co CO 3 3 3 O CO ro c 0 CO 3 ro CO 3 O t cn 3 t ro ε u υ 3 Compounds of 3 0 ro O c co the present 0 10 0 0 i nventi on c O S 50 20 70 70 100 100 0 100 2 50 50 70 70 100 0 100 3 50 50 50 50 100 100 100 20 100 Related comparative compounds Patent 12 0 0 0 0 0 0 0 0 0 40 40 20 15 20 20 0 30 Table III control Compounds of the present nventi on 1 0 20 0 0 100 100 20 100 2 20 100 10 50 100 100 100 0 100 3 30 50 80 30 100 100 0 100 related rative compounds Patent 12 30 40 30 40 60 60 80 30 90 31 30 30 30 20 90 50 40 20 100 33 90 70 80 70 50 90 40 20 100 a insufficientOCRQuality

Claims (5)

45768/2 CI aims :

1. 1 ,3,4-thiadiazol-2-yl-ureas of the general formula 1n which R.J represents methyl or ethyl , R2 represents hydrogen or methyl , and 3 represents allyl or methoxy.

2. 1 ,3-D1methyl -1 -methoxy-3- (5-ethylsul phonyl -1 ,3 ,4-thl ad1 azol 2-yl ) -urea .

3. l-Allyl-3-methyl-3-(5-ethylsulphonyl-l ,3 ,4-thtad1 azol -2-yl )-urea.

4. A herblddal preparation which comprises at least one compound of the general formula 1n which R represents methyl or ethyl 1 R., represents hydrogen or methyl , and R~ represents allyl or methoxy 1n admixture or conjunction with a suitable carrier. ^ ,

5. A method of protecting a living plant against weeds, vhere-1n the area 1n the vicinity of the living plant 1s treated, with a compound as claimed 1n claim 1. For the Applicants Wolff, Bregman and Goller