IL45479A - Herbicidally active 1,3-dimethyl-3-(5-alkylthio-1,3,4-thiadiazol-2-yl) urea derivatives - Google Patents

Description

Herbicidally active derivatives The present Invention 1s concerned with new and herblcldal preparations containing these compounds as active Thladlazolyl having a herblcldal action have been known and These have Insufficient action against monocotyledonous and dicotyledonous and also their selectivity 1s unsatisfactory when used in agricultural the problem upon which present 1s based has been to provide an agent having an action against monocotyledonous and dnous plants and selective properties towards agricultural problem 1s now sol ed accordance the present invention by using of the general formula as defined The present accordingly provides compounds of the general formula which represents isopentyl propyl n represents 1 or 2 and represents a hydrogen atom when represents also represents a methyl While in Israel Patent 32 German Of 1 816 2 028 778 and 1 936 241 and 1 195 there are described compounds similar to whose general formula includes the compounds of the present none of said patents disclose the specific compounds of the present invention or suggest the unexpected of such compounds as demonstrated 1n comparative example 7 hereinafter reference to the closest disclosed 1n German Of 1 816 The compounds of the present Invention are thus distinguished by their structure and by a and and can used for combating monocotyledonous and dicotyledonous weeds in As such agricultural crops there may be for cereals potatoes seed shrubs frui t peas and other leguminous plants and Weeds that can be combated for a vulgaris Matricaria Lamlum Galium Chrysanthemum Ipomea Slnapls Chenopodaceae Allium Avena a Alopecurus myosuroldes Echlnochloa crus galll Seterla Setarla Poa annua and urn Depending on the compound the region of use there are generally required for combating seed weeds applications of approximately to 5 kg of active substance per either the or method being when two or mope compounds of the general formula I are i used the range of approximately to 5 kg refers of course to the total amount applied of The present Invention accordingly also provides a paration which comprises a compound of the general formula In admixture or conjunction wit a suitable The preparation may of course contain one or more compounds of the general formula The present Invention further provides a method protecting a living plant against wherein the area n the vicinity of a s treated a compound of the general formula The present Invention further provides a method of protecting a crop area against wherein a crop area 1s treated with a compound of the general formula The present Invention further provides a pack which comprises a compound of the general formula I together with Instructions for use as a The new active compounds may be used either singly or as a mixture of two or several active If other protecting or for example nematfcldes or other may be added depending on the purpose It 1s also possible to for fert If t Is ntended to widen the spectrum of action or to destroy a waste land flora there may be added other For there are suitable as active to be added active stances of the groups of tr am1 otr1azoles anll des d azlnes uracils aliphatic 1c adds and adds genated benzoic adds carbam c acid esters and thlocarbanrfc acid esters and agents and other additions there are to be for also toxic additions that give with herbicides a synergistic crease In for example wetting agents sifters solvents and oily The active compounds of the general formula I are advantageously used 1n the form of herblcldal preparations for example powders strewable granules solutions emulsions or suspensions with the addition of liquid solid vehicles or diluents f of agents for example emulsifying dispersing Sui able carriers for example and aromatic hydrocarbons for example xylene cyclohexanone and also mineral oil As solid carriers there are suitable mineral earths for example tonsil silica gel limestone and silicic and vegetable products for example As agents there may be for calcium phenol naphthalene sulphonlc adds pheno ul honic adds formaldehyde condensates fatty alcohol sulphates and alkali metal and alkaline earth metal salts of fatty total amount of the active compound or compounds of the present Invention the herblcldal preparations may vary within wide The preparations nay for approximately 20 to 80S by weight of active approximately 80 to 20X by weight of liquid or solid If up to 202 by weight of Some compounds of the present Invention are listed the followng Name of the compound Physical constant 1 th 1 1 1 thad thad 1 rop l The compounds of the present Invention of the general formula I are colourless and or crystalline substances that dissolve only to some extent 1n but readily 1n organic for example methylene hexanone and The following Examples Illustrate the Examples 1 to 4 the manufacture of compounds of the present Examples 5 to 7 Illustrate the herblcldal and selective properties of the compounds of the present Invention as compared the known active substances the results given In Examples 5 to 7 are expressed by a numerical scale extending from 0 to the value 0 being equivalent to total destruction and the value 10 being equivalent to no Example 1 of were d ssolved In 200 of To the so ution were added dropwlse while stirring grams of methyl After allowing the mixture to stand t was poured Into litres of and the substance that was filtered off with suction and recrystaii zed from There were obtained 187 grams of the product of the theoretical Melting 20 The used as starting compound was obtained by reacting Isobutyl bromide with ami 3 1 1 th one Examp e 2 l To a solution of 52 grams of th1 ad1 In 160 of glacial acetic were added while grams of perhydrol of After standing for 6 days the solution was concentrated In The solid residue was recrystaiilzed from methanol The yield of the product was 53 grams of the theoretical Melting Example 3 1 Into a mixture of grams of l 200 ml of glacial acetic and 60 ml of water were slowly between and while stirring grams of finely powdered potassium The nate the reaction the mixture was stirred for a further 30 minutes at 300 ml of was were and the precipitated manganese dioxide was reduced with 19 grams of sodium dissolved in 70 ml of water until product was 23 of the theoretical Melting Example 4 1 From bromide and thione was obtained melting at torr which was reacted th methyl isocyanate to form melting at Example 5 In a series of tests carried out in a greenhouse the plants listed 1n the fol lowing Table were treated by the pre method with parations used in such amounts that 1 kg of the active substance being tested was per For purpose the active substances were in each uniformly sprayed over the 1n the form of an aqueous pension using 500 of water per The results given 1n the following Table show that 3 weeks after the treatment the compounds of the present invention while having a good action against the weeds were tolerated by the crop plants In contradistinction thereto the comparison agents used for damaged the crops o o Poiyctonum ny 1 1 azol 1 0 0 1 propy 1 o 0 2 2 2 3 2 0 0 0 Untreated 10 10 10 10 10 10 10 Agent used for compar son thl azol phony adi Example 6 In a series of tests carried out 1n a greenhouse the types of plants listed 1n the following Table were treated by the method with preparations used n such amounts that the specified amount of the active substance being tested was appl ed per For this purpose the active substances were 1n each case sprayed uniformly over the plants 1n the form of an aqueous suspension using 500 litres of water per The obtained 3 weeks after the treatment show that the compounds of the present nvention did not damage the potatoes even at the rate of 8 kg of active substance per while the weeds even at the rate of 3 kg of active sbstance per hectare were completely In contradistinction thereto the agents used for comparison caused damage to the crops even at the rate of 3 kg of active substance per I I I Potatoes media vulgaris Matricaria Example 7 In a series of tests carried out 1n a greenhouse the plants l isted 1n the following Table were treated after emergence parations used 1n such amounts that 1 kg of the active substance being tested was appl ied per For this purpose the active substances were 1n each case uniformly sprayed over the plants n the form of an aqueous suspension using 500 l itres of water per As be seen from the better selectivity was achieved with the compounds of the present Invention than wi th the agents used for 0 totally destroyed 10 not damaged Compounds of the present 1 1 propyl phi nyl ad1 azol 1 propyl th1 ad1 azol 1 th1 th1 ad1 azol thy purea 1 1 Agent used for comparison to 1 1 1 Compounds of the present Invention sdpentyl sul phony 1 1 1 propyl th1ada1zol adiazol 1 propyl phonyl 3 1 1 1 Agent used for comparison nq to 816 l thladlazol kilift Rtgonca app oea ssanveu ac o insufficientOCRQuality

Claims (20)

45479/2 / What we claim 1s:

1. A 1 ,3,4-th1adiazol-2-yl -urea of the general formula I * In which 1 - R-j represents isobutyl , isopentyl or/methyl propyl n represents 0, 1 or 2 and f*2 represents a hydrogen atom and, when n_ represents 0, al so represents a methyl group.

2. 1 ,3-D1methyl-l-(5-1sobutylsulphonyl-l ,3,4-th1ad1azol-2-yl )-urea.

3. 1 ,3-D1methyl-l-(5-1sobutylsulph1nyl-l ,3,4-thiad1azol-2-yl )-urea.

4. 1 ,3-D1methyl-l-(5-1sopentylsulphonyl-l ,3,4-thiad1azol-2-yl )-urea.

5. 1 ,3-Dimethyl-l-(5-1sopentylsulphinyl-l ,3,4-th1adiazol-2-yl )-urea.

6. 1 ,3-Diraethyl-l-[5-(l-methylpropyl ) sulphon l-! ,3,4-th1adiazol-2-yl]urea.

7. 1 ,3-Dimethyl-l -[5- (1 -methyl propyl )sulph1nyl-l ,3,4-th1adiazol-2-yl]urea.

8. 1 ,3-D1methyl-l-(5-1sobutylth1o-l ,3,4-thiadiazol-2-yl )-urea.

9. 1 ,3-D1methyl -1 - (5-i sopentyl th1 o-l ,3 ,4-th1 adlazol -2-yl )-urea .

10. l -(5-Isobutylth1o-l ,3,4-th1ad1azol-2-yl )-l ,3,3-tr1methyl-urea.

11. U* l-[5-(l-Methylpropyl )th1o-l ,3,4-thiadiazol-2-yl]-l ,3,3-tr1methyl-urea.

12. A herbicidal preparation which comprises a compound of the general formula I given in claim 1 , 1n which n and R2 have the meaning given In claim 1 , 1n admixture or conjunction with a suitable carrier.

13. A herbicidal preparation which comprises the compound claimed 1n any one of claims 2 to 11 , in admixture or conjunction wi th a suitable carrier.

14. A herbicidal preparation which comprises the compound claimed in any one of claims 12-13 in admixture or conjunction with a suitable carrier which is In the form of a powder, a strewable preparation , granules , a solution , an emulsion or a suspension.

15. A preparation as claimed in any one of claims 12-14 containing a single compound of the general formula I in an amount of approximately 20 45479/2

16. A preparation as claimed n any one of claims 12-15, containing two or more compounds of the general foraula I In a total amount of approximately 20 to 80% by weight.

17. A preparation as claimed In any one of claims 12-16, containing a single surface-active agent 1n an amount of up to 20% by weight.

18. A preparation as claimed 1n any one of claims 12-16, containing two or more surface-active agents In a total amount of up to 20% by weight.

19. Any one of the herblddal preparations as claimed In claim 12 and substantially as described in Examples 5 and 7 herein.

20. Any one of the herblddal preparations as claimed n claim 12 and substantially as described in Example 6 herein. For the Applicants Wolff, Bregman and Goller By: ~¾Λ¾