IL38183A - Herbicidally active s-methyl n-(carbamoyloxyphenyl)thio carbamates - Google Patents
Herbicidally active s-methyl n-(carbamoyloxyphenyl)thio carbamatesInfo
- Publication number
- IL38183A IL38183A IL38183A IL3818374A IL38183A IL 38183 A IL38183 A IL 38183A IL 38183 A IL38183 A IL 38183A IL 3818374 A IL3818374 A IL 3818374A IL 38183 A IL38183 A IL 38183A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- compound
- methyl
- general formula
- treated
- Prior art date
Links
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 title claims 8
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 48
- 241000196324 Embryophyta Species 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- -1 3-ethyl phenyl Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 238000010531 catalytic reduction reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 244000192528 Chrysanthemum parthenium Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000017945 Matricaria Nutrition 0.000 description 3
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Herblcldally active carbamoyl oxhphenyl thio carbamates invention oonoemed with new substituted and with their manufacture and especially their use as selective veed control agents in cultivated She activity of phenyl for example of has been Israel Patent 26696 known German it has been found that this active substance is not sufficient enough against types of The present invention provides compounds of the general formula I in which represents a lover these new compounds of the present invention are used as herbicides tile disadvantage mentioned above of the aforesaid known tiocarbamates ie overeome since they are especially suitable for the selective control of undesired types of especially among cultivated In combination with an inert vehicle the compounds of the general formula I effectively control types of especially types of for example Setarda Eohinocloa crus and the active compounds of the present invention possess a high selectivity towards cultivated especially towards plants which themselves represent types of Since millet plants often grow as undesired grasses in crops of the use of the compounde of the present invention makes it possible to control types of millet without the cultivated an extraordinary technical The activity of the active compounds of the present invention not limited to the aforesaid types of grasses but extends equally to other for dicotyledonous for example Stellaria Seneoio Matricaria Centaurea Ipomea purpurea and are also controlled by the new used as herbicides the compounds of the present invention are preferably applied at the that is to say after theplants have germinated so that an aqueous preparation of the active substanee attacks them The preparations applied to the water surface of the flooded fields of the growing When the stage is the preferred amount applied ranges from about 1 to kg of active substanee according to the present invention per hectare active substance being made up of one compound of the general formula I or a mixture of two or more compounds of the general formula It also possible to use the active compounds at the but in this case a higher amount in excess of kg of active substance per hectare must be The present invention accordingly also provides a method of protecting a living plant against wherein the area in the vicinity of a living plant is treated with a compound of the general formula The present invention further provides a method of protecting a crop area against wherein a crop area is treated with a compound of the general formula active compounds of the invention be used as preparations which take the form of the conventional herbicidal present invention accordingly further provides a herbicidal preparation which comprises a compound of the general in admixture Or conjunction with a suitable the herbicidal preparations may be in the form for spraying or dusting emulsions or Emulsions appropriate additives are especially suitable as Suitable additives for these preparations are liquid solid vehicles or diluents if for example vetting emulsifiers andor dispersing as veil as fertilizers or other Suitable liquid vehicles for petroleum fractions or other organic for example carbon dimet lformamide or Suitable solid vehicles for attaclay and other As agents there may be for cationic and for example ethoxylated alkylphenol polyglycol tributylphenyl polyglycol polyether isotrideoyl lauryl ether fatty alcohol ethylene oxide ethoxylated castor polyoxyathylene alkyl ethoxylated sorbitol esters and lauryl alcohol polyglycol ether The preparations of the present invention may be in a known for example by mixing or If the individual constituents may be mixed only shortly prior to use as is done in for in the tank mix The content of active substance which may be a single compound of the general formula I or a mixture of two or more of the general formula in a herbieidal preparation ready for use ranges advantageously from about 2 to by preferably from 15 to by referred to the weight of the In addition such preparations contain about 98 to by weight of or solid if up to about by weight of a single agent or a mixture of The active compounds of the present invention of the general formula I may be used either alone or in the form of mixtures containing several active It is possible to incorporate other herbicides with them to broaden the activity to improve the selectivity or the effect on the soil or to improve the stability towards atmospheric Especially suitable additives are those that are capable of causing a synergistic activity for example certain wetting solvents and Preferred substituents represented by in the general formula I given above of the active substances are groups containing 1 to carbon atoms and as the preferred substituents represented by there may be for The hitherto unknown active compounds of the general formula I may be manufactured by known for exmaple from the appropriate acid esters and aniline derivatives or the appropriate phenols or their salts carbamoylohlorides the presence of inorganic or organic bases or from the appropriate by hydrogenation of the nitro group to the amino for example with the use of Eaney nicke in and reactio with thioformic if desired in the presence of an inorganic or tertiary organic The present invention accordingly further provides a process for the manufacture of a compound of the general formula wherein a compound of the general formula reacted in the presence of an inorganic or organic base with an amine of the formula a compound of the general formula or a salt thereof is reacted the presence of an inorganic or organic base with a oarbamoylchloride of the general formula a compound of the general formula is catalytically reduced to the corresponding which is then reacted with a compound the general formula S if desired in the presence of an inorganic or tertiary organic In the above formulae and have the meanings given The manufacture of compounds of the present invention is exemplified in Examples 1 and 2 In a manner similar to that described la Example 1 or 2 below the following compounds of the present invention may be o melting at 104 to melting at 158 to melting at 100 to 10 melting at 114 to melting at 148 to 20 following Examples the Example 1 thiocarbamate A solution of g of ester and g of evaporated the residue was dissolved in methylene chloride and the solution with and washed successively with a dilute sodium hydroxide dilute hydrochloric water and a sodium then dried over sulphate and She initially oily residue furnished from ether 108 of theoretical of a crystalllzate melting at 101 to of While stirring and cooling to 10 to a solution of g of in 50 ml of ethyl there were simultaneously added a solution of g of chloroforoic thio phenyl ester 100 ml of ethyl acetate and a solution of g of potassium in ml of The mixture was stirred for another minutes without and the organic phase was then washed with dilute hydrochloric acid and water with the addition of The solution was dried over magnesium sulphate and filtered in ethyl acetate through neutral alumina and evaporated under g of the theoretical Melting point after recrystallization from 104 to used as one of the starting materials was prepared in the usual manner from the ester and phosgene with the addition of dimethylaniline in ethyl Example In a greenhouse the test plants listed in the Table were treated in the stage in a series of experiments with preparations eontaining compounds of the present the preparations being used such amounts that 1 kg of active substance was applied per The She preparations were evenly sprayed over the soil in the form of aqueous emulsions using 500 litres per Se control compound was likewise sprayed as anaqueous emulsion at a concentration of 1 kg of active substance per hectare using 500 litres per The results show that the preparations containing the compounds of the present invention did not damage the cultivated plants and produced a much better control of the undesired plants than did the preparation containing the known control The results are expressed by numerical scale extending from 0 to the value 0 being equivalent to total destruction and the value 10 being equivalent to no evaluation was carried out 3 weeks after the Active compound in preparation 1 2 3 4 5 6 7 8 1011 121314 invention totally destroyed undamaged 81 seed rice 2 Sinapis 3 4 vulgaris 5 Matricaria 7 evanua 8 Amarantus aparine 0 purpurea 12 Echinoohloa She test plants listed in the Table below treated in a greenhouse as described in Example expressed in the same manner as in Example are shown in the These likeise prove that the preparations containing the compounds of the present invention superio in their effect against undesired plants a compared with the preparation containing the control compound and did not damage the cultivated Active compound in preparation of this i 5 6 7 9 10 11 12 invention 10 0 0 0 0 0 0 0 0 0 0 0 0 ocarbamate 10 0 0 0 0 0 0 0 0 0 1 0 0 Control compound 1 Seed rice 2 Sinapis 3 Stellaria media 4 Senecio vulgaris 5 Matricaria 6 caule Centanrea cvanus 8 Amarantus retroflexus 9 Chrysanthemum insufficientOCRQuality
Claims (24)
1. 38183/2 What we claim 1s:- A compound of the general formula I n which R^ represents a lower alkyl group and R¾ represents a phenyl or al Kyi phenyl group.
2. A compound as claimed In claim 1 · wherein R, represents an alkyl group containing 1 to 3 carbon atoms.
3. A compound as claimed In claim 1 or 2, wherein Rg represents a phenyl , 2-methyl phenyl , 3-methyl phenyl , 3-ethyl phenyl cr4-ethyl phenyl group .
4. S-Methyl -N-[3- (N ' -methyl -N ' -phenyl carbamoyl oxy) -phenyl ]-th1ocarbamate.
5. S-Meth l -N- j 3- [N 1 -methyl -N 1 - { 41 -eth l phenyl )-carbamoyloxy]-phenyl j-t ocarbamate.
6. S-Methyl -N- 13- [ ' -ethyl - 1 - (4 * -methyl phenyl ) -carbamoyl oxy ]-phenyl j-thloearbamate.
7. S-Methyl -H- [3-(N ' -ethyl -N 1 -phenyl carbamoyl oxy )-pheny1 ]-thlocarbamate.
8. S-Methyl -N- j3~[N* -ethyl - ' - { 3 ' -methyl phenyl )-carbamoy1 ox ]-phenyl j-thlocarbamate.
9. S-Methyl -N- J 3- [N ' -eth l -N ' - ( 2 ' -methyl henyl ) -carbamo l oxy ]-phenyl J -thlocarbamate.
10. S-Methyl -N- [3- (N ' - sopropyl -N ' -phen l -carbamoyl oxy ) -phen l ]-thlocarbamate.
11. S-Methyl -N- |3- [N ' -methyl -N · - (3 · -methyl phenyl ) -carbamoyl oxy 3-pheny 1 | -thlocarbamate.
12. A herblcldal preparation which comprises a compound of the general formula I 38183/2 1n which j represents a lower alkyl group and 2 represents a phenyl or alkyl phenyl group* 1n admixture or conjunction with a suitable carrier.
13. A herblddal preparation which comprises a compound as claimed 1n claim 2 or 3, 1n admixture or conjunction with a suitable carrier.
14. A herblddal preparation which comprises the compound claimed 1n any one of claims 4 to 11 , In admixture or conjunction with a suitable carrier.
15. A method of protecting a living plant against weeds , wherein the area In the vicinity of a living plant Is treated with a compound of the general formula I , as defined In claim 1.
16. A method of protecting a living plant against weeds , wherein the area In the vicinity of a living plant 1s treated with a compound as claimed 1n claim 2 or 3. V.
17. A method of protecting a living plant against weeds, wherein the area In the vicinity of a living plant 1s treated with the compound claimed In any one of claims 4 to 11.
18. A method of protecting a crop area against weeds , wherein a crop area 1s treated with a compound of the general formula I , as defined 1n claim 1 .
19. A method of protecting a crop area against weeds , wherein a crop area 1s treated with a compound as claimed In claim 2 or 3.
20. A method of protecting a crop area against weeds , wherein a crop area s treated with the compound claimed In any one of claims 4 to 11.
21. A process for the manufacture of a compound of the general formula I 38183/2 In which represents a lower alk l group and Rg represents a phenyl or al yi phenyl group, wherein a compound of the general formula s Veated In the presence of an Inorganic or organic base with an amine of the formula ^ R, 1 NH 1n which R^ and Rg have the meanings given above, or a compound of the general formula or a salt thereof Is reacted 1n the presence of an Inorganic or organic base with a carbamoyl chloride of the general formula 1n which R^ and R2 have the meanings given above; or a compound of the general formula 38183/2 1n which and Rg have the meanings given above, 1s catalytlcally reduced to the corresponding amine which 1s then reacted with a compound of the formula CH3 - S - CO - CI .
22. A process as claimed 1n claim 21 , wherein the catalytic reduction Is carried out with the use of Raney nickel 1n methanol .
23. A process as claimed In claim 21 or 22, wherein the reaction with the compound of the formula Is carried out In the presence of an Inorganic or tertiary organic base.
24. A process as claimed In claim 21 , conducted substantially as described 1n Example 1 or 2 herein. For the Applicants Wolff, Bregman and Goller By: -¾ , J^
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702059309 DE2059309A1 (en) | 1970-11-24 | 1970-11-24 | Selective herbicidal agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL38183A true IL38183A (en) | 1974-12-31 |
Family
ID=5789776
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38183A IL38183A0 (en) | 1970-11-24 | 1971-11-19 | Herbicidally-active substituted phenylthiocarbamates and their manufacture and use |
| IL38183A IL38183A (en) | 1970-11-24 | 1974-11-19 | Herbicidally active s-methyl n-(carbamoyloxyphenyl)thio carbamates |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38183A IL38183A0 (en) | 1970-11-24 | 1971-11-19 | Herbicidally-active substituted phenylthiocarbamates and their manufacture and use |
Country Status (29)
| Country | Link |
|---|---|
| JP (1) | JPS5015847B1 (en) |
| AT (1) | AT311717B (en) |
| AU (1) | AU461419B2 (en) |
| BE (1) | BE775754A (en) |
| BG (1) | BG20071A3 (en) |
| BR (1) | BR7105564D0 (en) |
| CA (1) | CA946408A (en) |
| CH (1) | CH561009A5 (en) |
| CS (1) | CS167323B2 (en) |
| DE (1) | DE2059309A1 (en) |
| DK (1) | DK128552B (en) |
| EG (1) | EG10238A (en) |
| ES (1) | ES393926A1 (en) |
| FI (1) | FI54219C (en) |
| FR (1) | FR2115339B1 (en) |
| GB (1) | GB1369491A (en) |
| HU (1) | HU163629B (en) |
| IE (1) | IE35674B1 (en) |
| IL (2) | IL38183A0 (en) |
| IT (1) | IT941776B (en) |
| LU (1) | LU64313A1 (en) |
| NL (1) | NL7116114A (en) |
| NO (1) | NO131151C (en) |
| OA (1) | OA03840A (en) |
| PH (1) | PH11826A (en) |
| PL (1) | PL81438B1 (en) |
| RO (2) | RO62289A2 (en) |
| YU (1) | YU35351B (en) |
| ZA (1) | ZA715706B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2310649C3 (en) * | 1973-03-01 | 1982-05-06 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethanes and selective herbicidal agents containing them |
-
1970
- 1970-11-24 DE DE19702059309 patent/DE2059309A1/en not_active Withdrawn
-
1971
- 1971-06-18 DK DK301571AA patent/DK128552B/en not_active IP Right Cessation
- 1971-06-25 YU YU1660/71A patent/YU35351B/en unknown
- 1971-07-20 FI FI2057/71A patent/FI54219C/en active
- 1971-07-28 CS CS5527A patent/CS167323B2/cs unknown
- 1971-08-05 ES ES393926A patent/ES393926A1/en not_active Expired
- 1971-08-11 PH PH12743A patent/PH11826A/en unknown
- 1971-08-16 BG BG018353A patent/BG20071A3/en unknown
- 1971-08-25 BR BR5564/71A patent/BR7105564D0/en unknown
- 1971-08-26 ZA ZA715706A patent/ZA715706B/en unknown
- 1971-09-27 GB GB4494571A patent/GB1369491A/en not_active Expired
- 1971-09-28 IE IE1210/71A patent/IE35674B1/en unknown
- 1971-09-30 CA CA124,101A patent/CA946408A/en not_active Expired
- 1971-10-01 RO RO68336A patent/RO62289A2/en unknown
- 1971-10-01 RO RO76243A patent/RO62664A2/en unknown
- 1971-11-15 EG EG498/71A patent/EG10238A/en active
- 1971-11-15 AU AU35714/71A patent/AU461419B2/en not_active Expired
- 1971-11-19 IL IL38183A patent/IL38183A0/en unknown
- 1971-11-22 LU LU64313D patent/LU64313A1/xx unknown
- 1971-11-22 PL PL1971151698A patent/PL81438B1/pl unknown
- 1971-11-22 CH CH1697271A patent/CH561009A5/xx not_active IP Right Cessation
- 1971-11-23 NL NL7116114A patent/NL7116114A/xx not_active Application Discontinuation
- 1971-11-23 NO NO4303/71A patent/NO131151C/no unknown
- 1971-11-23 HU HUSCHE364*1A patent/HU163629B/hu unknown
- 1971-11-23 FR FR7141818A patent/FR2115339B1/fr not_active Expired
- 1971-11-23 AT AT1007871A patent/AT311717B/en not_active IP Right Cessation
- 1971-11-23 OA OA54416A patent/OA03840A/en unknown
- 1971-11-24 BE BE775754A patent/BE775754A/en not_active IP Right Cessation
- 1971-11-24 JP JP46094400A patent/JPS5015847B1/ja active Pending
- 1971-11-24 IT IT31542/71A patent/IT941776B/en active
-
1974
- 1974-11-19 IL IL38183A patent/IL38183A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2515091C2 (en) | N-acyl-N-phenyl-alanine derivatives and -glycine derivatives, processes for their preparation and fungicidal agents containing these compounds | |
| US3063823A (en) | Method of killing weeds and influencing plant growth | |
| EP0388873B1 (en) | [[1,3,5-Triazin-2-yl)aminocarbonyl]aminsulfonyl] benzoic acid esters as herbicides, their preparation and their use | |
| EP0332009A1 (en) | N-aryl-tetrahydrophthalimide compounds | |
| US3535101A (en) | Herbicide and algicide means | |
| US3377375A (en) | N-aralkylsulfonyl carbamates | |
| DE2543888B2 (en) | l-Phenyl-S-alkyl-S-benzylureas, process for their preparation and their use as fungicides | |
| JPS584757A (en) | Substituted cyclopropylmethoxyurea, herbicidal composition and weeding method | |
| IL38183A (en) | Herbicidally active s-methyl n-(carbamoyloxyphenyl)thio carbamates | |
| DE2824126C2 (en) | Tetrahydro-1,3,5-thiadiazin-4-one compounds | |
| US3583987A (en) | Herbicidal azido-s-triazine derivatives | |
| EP0062254A1 (en) | Substituted acetanilides, process for their preparation and their use as herbicides | |
| US3241942A (en) | Method for combating weeds | |
| CS195717B2 (en) | Herbicide and method of producing the same | |
| EP0084673A1 (en) | Aminothiadiazoles, process for their preparation and their use in combating unwanted plant growth | |
| EP0144052A2 (en) | Quinolinoxyphenyl ureas, process for their preparation and their use to combat unwanted plant growth | |
| US3137562A (en) | Herbicidal compositions and methods | |
| EP0107123B1 (en) | Aniline derivatives, process for their preparation and their use in combating undesired plant growth | |
| US3705914A (en) | Pesticidal carbamate derivatives of naphthaquinones | |
| EP0476403B1 (en) | Herbicidal(((1,3,5-triazine-2-yl)aminocarbonyl)aminosulfonyl)benzoeacidesters, method for their preparation and their use | |
| EP0022750A1 (en) | 1,3,4-Thiadiazolyloxy-phenyl ureas, their preparation and herbicides containing them | |
| CH645883A5 (en) | Nitrogen-containing carbonic acid derivatives, a process for their preparation and pesticides containing them | |
| EP0040310A2 (en) | Fungicidal heterocyclic substituted thioglycolic acid-anilides, their preparation and pesticides containing them | |
| US3644112A (en) | Method of controlling unwanted plants | |
| EP0092632B1 (en) | New benzonitrile derivatives, method for their preparation and herbicidal compositions |