IL43282A - N,n,n'-trimethyl-n'-(5-substituted-1,3,4-thiadiazol-2-yl)-ureas having selective herbicidal activity - Google Patents
N,n,n'-trimethyl-n'-(5-substituted-1,3,4-thiadiazol-2-yl)-ureas having selective herbicidal activityInfo
- Publication number
- IL43282A IL43282A IL43282A IL4328273A IL43282A IL 43282 A IL43282 A IL 43282A IL 43282 A IL43282 A IL 43282A IL 4328273 A IL4328273 A IL 4328273A IL 43282 A IL43282 A IL 43282A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- general formula
- urea
- tr1methyl
- th1ad1azol
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
ureas having selective herbicidal activity The present Invention 1s concerned with new sulphon and processes for their and also with preparations containing these ureas have already been described as active The best known compound 1s f 1 oromethyl German This active substance however of use as a selective combating agent because has ty towards cultivated German the action of which contain an group containing to 3 carbon These compounds do exhibit satisfactory tivity towards cultivated Similarly Israel Specification 33499 and the corresponding German specification as well as German specification and specifically teach compounds similar to those of the present formulas which formally their broad scope the novel compounds of the present however publications do not teach or suggest the specific compounds claimed or the surprising superior herblddal and selective action of the compounds of the present Invention as demonstrated 1n examples 8 and 9 There been a need for an which avoids the advantages of the aforesaid known agents and 1n addition to a good action against a better towards cultivated plants than do the aforesaid known This need 1s satisfied in accordance the present by an agent containing at least one compound of the general formulae as defined The present accordingly provides compounds of the general formula I which represents an al kyl group containing 4 to 8 carbon atoms and represents or As al kyl groups represented by 1n the general formula there may be mentioned for example the form of mixtures of several active If there may be added other plant protection agents of pest combating for example nematicides or other depending on the result 1s also for to add When ed to widen the spectrum of action or to destroy flora on waste other herbicides may be For there are suitable as dally active of mixtures active substances belonging to the groups of aliphatic carboxylic and halogenated benzoic acids and phenyl esters of such carboxylic add esters and acid agents and Among other additives there are to be for which exert a synergistic 1n action upon for example wetting solvents and oily The compounds of the present are advantageously used 1n the form of herblcidal for example spraying or dusting emulsions or the addition of liquid solid vehicles or 1f of for example adherent dispersing Suitable carriers for aliphatic and aromatic for example cycl ohexanone and an also mineral oil As solid carriers there are suitable mineral for example ica gel limestone and silicic and vegetable for example As agents there may be for calcium phenol naphthalene sulphonlc phonic formaldehyde fatty sulphates and alkali and alkaline earth metal salts of fatty The total amount of the active compounds or compounds of the present invention 1n the herbiddal preparations may vary within For the preparations may contain about 20 to 80 per cent by weight of active about 80 to 20 per cent by weight of liquid or solid 1f up to 20 per cent by weight of The present invention further provides a process for the ture of a compound of the general formula wherein a compound of the formula II 1n which has the meaning given is treated in a solvent an oxidizing For the preparation of compounds of the general formula there may be when 1 as oxidizing agents preferably organic for example or for example or acid for example or inorganic oxidizing for example hydrogen peroxide or purpose there are advantageously used two oxidation equivalents of the oxidizing agent or a excess per one mole of the at temperatures of about 0 For the preparation of compounds of the general formula I 1n which n 1s 2 there are addition to the oxidizing agents already inorganic for example chlorine or potassium chromic or salts or nitric in a temperature range from about 0 to For each of the there are advantageously used four oxidation equivalents if an excess that to at least twice as much as 1s used for the above described da for the preparation of the defined compounds in which n As reaction media there may advantageously be for organic for example for example acetic for example for example acid for example dimethyl for example or either alone or in admixture The present Invention further provides a process for the manufacture of a compound of the general formula wherein a compound of the general formula III which and have the meanings given is reacted a carbamoyl of the general formula IV in which Hal represents a bromine or iodine 1n a solvent and the presence of an or 1n an solvent and 1n the presence of an agent a carbonic ester halide or phosgene and the resulting derivative of 1s then reacted with dimethyl amine of the formula V As carbonic acid ester ldes there are used preferably carbonic acid phenyl ester chloride and ester Whereby there 1s for an sulphonyl which 1s then reacted In processes 1n which a hydrohalic acid 1s there are added to the add organic bases for example tertiary amines for example ethyl amine dimethyl pyridine bases or suitable inorganic bases for example oxides and hydroxides of alkali and alkaline earth The reaction carbonic add chlorides 1s carried out at between about and and the subsequent reaction with d1methylam1ne of the general V 1s carried out at between about and but in general at room As reaction media there are used solvents that are inert to the As such solvents there may be for aliphatic and aromatic hydrocarbons and halogenated hydrocarbons for example toluene methylene carbon chloride and chlorinated ethylenes ketones compounds a Iky ted amides The present further provides a process for the manufacture of the ky falling wi thin the scope of the general formula I 1s those compounds of the general formula I in which n wherein a sulphinic acid or salt of the general formula VI 1 1 20 1 Tri nD sulphonyl L The compounds of the present are colourless and or crystalline which are insoluble for water and benzine and soluble for methylene dimethyl cyclohexanone and The following Examples the While Examples and 2 illustrate the manufacture of compounds of the present Examples 3 to 7 the and selective properties of the compounds of the present as compared those of the known active substances Example 1 To a solution of 300 grams of in litres of glacial acetic were added dropwise 136 grams of perhydrol at room temperature and The temperature rose to After the mixture to stand for 5 the excess of perhydrol was destroyed manganese the glacial acetic was distilled off as far as possible in the residue was taken up in methylene and treated twice active the solvent was led and the oil that remained behind was dried in a high grams of the theoretical 1 5617 Example 2 grams of 1 were dissolved in 150 ml of glacial acetic and 50 ml of grams of finely pulverized potassium permanganate were duced into this solution at between 70 and the mixture was stirred for a further and finally the precipitated manganese dioxide 1n the mixture cooled to 0eC was reduced by the dropwise addition of a solution of 30 grams of sodium metabi in 50 ml of The oil that separated was taken up in methyene chloride the methylene chloride extracted by agitation several times with carbonate solution and and the organic phase was dried wi th magnesium treated active and concentrated in The residue that remained behind was recrystal lized from isopropyl Mel ting gram of the theoretical Example 3 In a test the plants listed 1n the fol lowing Table were treated before their emergence 1n a series of experiments with preparations used in such amounts that the compounds being tested were appl ied at the rates For purpose the compounds being tested were 1n each case uniformly applied to the the form of an aqueous suspension using 500 litres per The results produced three weeks after the treatment show that the compounds of the present invention have a good selectivity as compared with the known compounds The results are expressed by a numerical scale extending from 0 to the value 0 representing total destruction and the value 10 representing no i j ί ΰ γ r i i Γ t Π Γ i J i i l Tri sul phonyl thi adi 10 10 10 0 1 0 Trimethyl phonyl 10 10 10 10 10 0 Trimethyl sulphonyl 0 Trimethy phi nyl 10 10 10 Q sul phi nyl 10 10 10 0 10 10 10 0 totally destroyed not damaged 1 butyl 10 10 10 10 1 10 10 10 10 pentyl 10 methyl propyl 10 10 10 Compound for comparison 1 1 tri 1 uorome th urea 0 0 0 totally destroyed 10 not damaged sul phony 4 0 5 0 0 0 5 2 3 0 0 0 5 4 3 0 0 0 1 2 2 2 0 0 0 1 4 4 7 0 0 0 1 sopropyl 7 2 5 0 0 0 Untreated 10 10 10 10 10 0 total ly destroyed 10 not damaged Example 4 In a greenhouse test the listed 1n the following Table were are expressed by a numerical scale extending from 0 to the value 0 resenting total destruction and the value 10 representing no 5 In an open land which was carried out plots of potatoes were treated with the compound tioned in the Table by the The compound was sprayed over the plots in the form of an aqueous suspension using 500 litres per the rate of being continually reduced from kg of active substance per hectare to kg of active substance per Even 6 weeks after the treatment the plots were practically which were treated with active substance free from the dosage range between 2 kg and kg of active substance per hectare with complete protection of the whereas the untreated control plots were very heavily with Polygonum Thlaspi album and also showed nodora An evaluation after a total of 8 weeks an even better the treated plots being practically free from weeds even down to kg of active substance per In case also the potatoes were not In the following Table are given the average values of the minimum rates of which are required for a very good weeding Compound of the present dose Minimum dose 6 weeks after 8 weeks after treatment treatment kg of kg of active active stance per stance per hectare hectare Example 6 In a further open land experiment out with potatoes on humous sand the compounds mentioned the Table were suspended 1n 500 litres of water per by the emergence method at decreasing rates of At the time of the rst evaluation untreated portions of land were heavily Infested with Chenopodium and Polygonum convol vul covering of Evaluations were Example 7 and trimethyl sul phony were each sprayed onto a potato crop by the method at decreasi ng rates of application suspended 1n 500 li tres of water per used resulted 1n an almost destruction of The Table again gives for each active substance the threshhold value for weeding action and the selectivity Index 4 weeks after appl The compound of the present Invention proved to be selective al though the known compound was no longer selective under these difficult conditions Compound of the present Invention Minimum dose for Selectivity very cjood weeding Index action 1 1 Compound for comparison 1 EXAMPLE 8 In a field test the compounds set forth 1n the following table were applied 1n decreasing amounts to potato plants 1n humus sand while 1n the The field was strongly Infested weeds such as Thlaspl Matricaria and Polygonum area covered About 6 weeks after application threshold values for crop ttSerance and weedlcidal activity were Table below shows the minimum dosage for substantially complete freedom from weeds and the selectivity index Indicating compatibility to crop for a compound of this Invention and a dimethyl T A B L E Minimum dosage for Selectivity complete Index 6 weeks weedlcidal activity 6 after Compound weeks after application application 20 Comparison compound Application 1 816 compound EXAMPLE 9 A potato field was in with as well as sul fonyl suspended 1n 500 litres at a decreasing At the time of treatment the potato plants had developed 6 to The heavy weed contamination consisted mainly of Solanum a Galeopsls and Polygonum which has developed 2 to 10 true The table shows the threshold values for weedlcidal activity and the selectivity Index took place 4 weeks after The compound according to the proved the comparison compound was Minimum dosage Compound according for very good Selectivity to Invention dal activity Index Comparison compound Appl ication 1 816 Compound thladlazol 1 insufficientOCRQuality
Claims (41)
1. What we claim 1s:- 1. A compound of the general formula I
2. l,l,3-Tr1methyl-3- 5-n-butylsulph1nyl-l ,3,4-th1ad1azol-2-yl)-urea.
3. l.l,3-Tr1methyl-3- 5-n-butyl sul phonyl -1 ,3,4-th1ad1azol-2-yl )-urea.
4. , l,l,3-Tr1methyl-3- 5-pentylsulph1nyl-l ,3,4-th1ad1azol-2-yl )-urea.
5. 1 ,1 ,3-Tr1methyl-3- 5-he*ylsulph1ny1-l ,3,4-th1ad1azol-2-yl)-urea.
6. 1 ,1 ,3-Tr1methyl-3- 5-heptylsulphlnyl-l ,3,4-th1ad1azol-2-yl )-urea.
7. l,l,3-Tr1methyl-3- 5-pentylsulphonyl-l ,3,4-th1ad1azol-2-yl )-urea.
8. l,l,3-Tr1methyl-3- 5-hex l sulphonyl- 1 ,3,4-th1ad1azol-2-yl )-urea.
9. 1, 1,3-Tr1 methyl -3- 5-heptylsulphonyl-l ,3,4-th1ad1azol-2-yl)-urea.
10. l,l,3-Tr1methyl-3- 5-octyl sul phony 1 -1 ,3 ,4-th1 ad1 azol -2-yl ) -urea .
11. l,l,3-Tr1methyl-3- 5-1 sobuty 1 sul phonyl -1 , 3/l-th1 ad1 azol -2-yl ) -urea. [l -ethyl butyl 1-suTphonvl . .
12. l,l,3-Tr1methyl-3- 5-Sty-T ht-Uu-W^V-l ,3,4-th1ad1azol-2*yl )-urea.
13. 1, 1,3-Tr1 methyl -3- 5-1 sopentyl sul phonyl -1 ,3 ,4- th1 ad1 azol -2-yl )-urea .
14. I,l,3-Tr1 methyl -3- 5- (1 -ethyl pentyl )-sul phonyl -1 ,3 ,4- th1 ad1 azol -2- yl]-urea.
15. 1 ,1 ,3-Tr1methyl-3-[5-(l-methylpropyl )-suiphonyl-l ,3,4-th1ad1azol- 2-yl]-urea.
16. A herblddal pepparatlon which comprises a compound of the general formula I I n which represents an alkyl group contai ni ng 4 to 8 carbon atoms and ji represents 1 or 2 , 1 n admixture or conjunction wi th a suitable carrier.
17. A herblddal preparation which comprises the compound claimed 1n any one of claims 2 to 15 , in admixture or conjunction wi th a suitable carrier.
18. A preparation claimed 1 n claim 16 or 17 , which 1s 1n the form of a powder, a spraying or dusting agent, granules , a solution , an emulsion or a suspension.
19. A preparation as claimed 1n any one of claims 16 to 18, containing a single compound of the general formula I 1n an amount of about 20 to 80% by weight.
20. A preparation as claimed 1n any one of claims 16 to 18, containing two or more compounds of the general formula I 1n a total amount of about 20 to 80% by weight.
21. . A preparati on as claimed 1 n any one of claims 16 to 20, containing a single surface-active agent 1n an amount of up to 20% by weight.
22. A preparation as claimed 1n any one of claims 16 to 20 , containing two or more surface-active agents In a total amount of up to 20% by weight.
23. Any one of the herblddal preparations as claimed 1n claim 16 and 'substantial ly as described 1n Examples 3 to 7 herein.
24. A method of protecti ng a l iving plant against weeds , wherein the area n the vicinity of a l iving plant 1s treated with a compound of the general formula I given 1n claim 1 , 1n which and n have the meanings given i n claim 1 .
25. A method as claimed 1 n claim 24, wherei n the area 1s treated with the compound claimed 1n any one of claims 2 to 15.
26. A method as cl aimed 1n claim 24, wherein, the area 1s treated wi th a herblddal. preparation as claimed 1n any one of claims 16 to 23.
27. A method as claimed 1n any one of claims 24 to 26, wherein a single compound of the general formula I 1s used 1n an amount of from 1 to 5 kg per hectare.
28. A method as claimed 1n any one of claims 24 to 26, wherein two orQ more compounds of the general formula I are used in a total amount of from 1 to 5 kg per hectare.
29. A method as claimed 1n claim 24, conducted substantially as described 1n Example 3 or 4 herein.
30. D . A method of protecting a crop area against weeds , wherein a crop area is treated with a compound of the general formula I given 1n claim 1 , 1n which and n have the meanings given 1n claim 1 ,
31. A method as claimed in claim 30, wherein the crop area 1s treated with the compound claimed 1n any one of claims 2 to 15.
32. A method as claimed 1n claim 30, wherei n the crop area is treated with a herbicidal preparation as claimed in any one of claims 16 to 23.
33. A method as claimed 1n any one of claims 30 to 32, wherein a single compound of the general formula I is used in an amount of from 1 to 5 kg per hectare.
34. A method as claimed in any one of claims 30 to 32, wherein two or more compounds of the general formula I are used in a total amount of from 1 to 5 kg per hectare.
35. A method as claimed in claim 30, conducted substantial ly as described in any one of Examples 5 to 7 herein.
36. A process for the manufacture of a compound as claimed 1n claim 1 , wherein a compound of the general formula II 1n which R, has the meaning given in claim 1 , is treated 1n a solvent
37. A process as claimed in claim 36, wherein the oxidizing agent 1s an organic hydroperoxide, a per-ac1d or an Inorganic oxidizing agent.
38. A process as claimed in claim 36, conducted substantially as described in Example 1 or 2 herein.
39. A process for the manufacture of a compound as claimed in claim 1, wherein a compound of the general formula III in which and have the meanings given in claim 1, is reacted (a) with a carbamoyl halide of the general formula IV in which Hal represents a chlorine, bromine or Iodine atom, 1n a solvent and in the presence of an add-bind1ng agent, or (b) in an Inert solvent and in the presence of an add-binding agent with a carbonic acid ester halide or with phosgene and the resulting product is then reacted with dimethyl amine of the formula V
40. A process as claimed in claim 39, wherein the carbonic add ester halide is carbonic add phenyl ester chloride or thiocarbonic add-S-phenyl ester chloride.
41. A process for the manufacture of a compound of the general formula I given in claim 1, in which represents an alkyl group containing 4 to 8 carbon atoms, and jn represents 2, wherein a compound of the general formula VI 1n which B represents a hydrogen atom, a monovalent metal equivalent or a tertiary organic base, 1s treated with an alkylating agent of the general formula VII Hal-^ (VII), 1n which j has the meaning given above and Hal represents a chlorine, bromine or Iodine atom, or with an appropriate ester of sulphuric add or an appropriate ester of an aromatic sul phonic add. For the Applicants Wolff, Bregman and Gol§¾r by: , . J ^
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2246461A DE2246461C2 (en) | 1972-09-21 | 1972-09-21 | 1,1,3-Trimethyl-3- (5-butylsulfonyl-1,3,4-thiadiazol-2-yl) urea and herbicidal agents containing this compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43282A0 IL43282A0 (en) | 1973-11-28 |
| IL43282A true IL43282A (en) | 1976-07-30 |
Family
ID=5857018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43282A IL43282A (en) | 1972-09-21 | 1973-09-21 | N,n,n'-trimethyl-n'-(5-substituted-1,3,4-thiadiazol-2-yl)-ureas having selective herbicidal activity |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS565722B2 (en) |
| AT (1) | AT326945B (en) |
| BE (1) | BE805165A (en) |
| BG (2) | BG22783A3 (en) |
| CA (1) | CA1008454A (en) |
| CH (1) | CH586009A5 (en) |
| CS (1) | CS169847B2 (en) |
| DD (1) | DD105111A5 (en) |
| DE (1) | DE2246461C2 (en) |
| DK (1) | DK132024C (en) |
| ES (1) | ES418476A1 (en) |
| FI (1) | FI56177C (en) |
| FR (1) | FR2200272B1 (en) |
| GB (1) | GB1454796A (en) |
| HU (1) | HU167875B (en) |
| IE (1) | IE39006B1 (en) |
| IL (1) | IL43282A (en) |
| IT (1) | IT995462B (en) |
| LU (1) | LU68455A1 (en) |
| NL (1) | NL7313046A (en) |
| NO (1) | NO139605C (en) |
| PL (1) | PL84425B1 (en) |
| RO (1) | RO78370A (en) |
| SE (1) | SE396384B (en) |
| SU (2) | SU559616A3 (en) |
| TR (1) | TR18582A (en) |
| YU (1) | YU34885B (en) |
| ZA (1) | ZA737492B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607481A1 (en) * | 1976-02-20 | 1977-08-25 | Schering Ag | 2-DIMETHYLCARBAMOYLIMINO-1,3,4-THIADIAZOLIN-3-ID DERIVATIVES, PROCESS FOR THE PREPARATION OF THESE COMPOUNDS AND HERBICIDAL AGENTS THESE CONTAINED |
| ZA775225B (en) * | 1977-08-29 | 1978-03-29 | Lilly Co Eli | Herbicidal combinations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1195672A (en) * | 1968-02-01 | 1970-06-17 | Mobil Oil Corp | Novel Urea Derivatives and Herbicides containing the same |
| CH513585A (en) * | 1969-07-18 | 1971-10-15 | Agripat Sa | Thiadiazolyl (2)- ureas prodn |
| DE2028778A1 (en) * | 1970-06-06 | 1971-12-23 | Thiadiazolyl-urea herbicides - 5 - substd by sulphinyl or sulphonyl | |
| ES393478A1 (en) * | 1970-09-03 | 1974-10-01 | Schering Ag | Herbicidally active thiadiazolylureas and their manufacture and u se |
| DE2044442C2 (en) * | 1970-09-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3 - (- 5-Ethylsulfonyl-1,3,4-Thiadiazol-2-yl) -urea with herbicidal action |
-
1972
- 1972-09-21 DE DE2246461A patent/DE2246461C2/en not_active Expired
-
1973
- 1973-07-19 TR TR18582A patent/TR18582A/en unknown
- 1973-08-06 DD DD172728A patent/DD105111A5/xx unknown
- 1973-08-08 CS CS5617A patent/CS169847B2/cs unknown
- 1973-08-20 GB GB3928973A patent/GB1454796A/en not_active Expired
- 1973-08-21 DK DK461073A patent/DK132024C/en not_active IP Right Cessation
- 1973-08-27 YU YU2283/73A patent/YU34885B/en unknown
- 1973-08-29 BG BG25350A patent/BG22783A3/xx unknown
- 1973-08-29 BG BG24413A patent/BG22780A3/xx unknown
- 1973-08-30 IE IE01539/73A patent/IE39006B1/en unknown
- 1973-09-03 HU HUSE000442 patent/HU167875B/en unknown
- 1973-09-04 ES ES418476A patent/ES418476A1/en not_active Expired
- 1973-09-17 FI FI2891/73A patent/FI56177C/en active
- 1973-09-19 CA CA181,436A patent/CA1008454A/en not_active Expired
- 1973-09-19 LU LU68455A patent/LU68455A1/xx unknown
- 1973-09-20 PL PL1973165325A patent/PL84425B1/pl unknown
- 1973-09-20 NO NO3685/73A patent/NO139605C/en unknown
- 1973-09-20 SU SU1961452A patent/SU559616A3/en active
- 1973-09-20 FR FR7333734A patent/FR2200272B1/fr not_active Expired
- 1973-09-20 SE SE7312828A patent/SE396384B/en unknown
- 1973-09-21 IT IT29215/73A patent/IT995462B/en active
- 1973-09-21 ZA ZA737492*A patent/ZA737492B/en unknown
- 1973-09-21 AT AT815073A patent/AT326945B/en not_active IP Right Cessation
- 1973-09-21 NL NL7313046A patent/NL7313046A/xx not_active Application Discontinuation
- 1973-09-21 BE BE135913A patent/BE805165A/en not_active IP Right Cessation
- 1973-09-21 JP JP10682073A patent/JPS565722B2/ja not_active Expired
- 1973-09-21 RO RO7376133A patent/RO78370A/en unknown
- 1973-09-21 IL IL43282A patent/IL43282A/en unknown
- 1973-09-21 CH CH1361673A patent/CH586009A5/xx not_active IP Right Cessation
-
1974
- 1974-05-07 SU SU2021991A patent/SU559645A3/en active
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