US3298819A - Method of controlling weeds - Google Patents
Method of controlling weeds Download PDFInfo
- Publication number
- US3298819A US3298819A US484498A US48449865A US3298819A US 3298819 A US3298819 A US 3298819A US 484498 A US484498 A US 484498A US 48449865 A US48449865 A US 48449865A US 3298819 A US3298819 A US 3298819A
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- United States
- Prior art keywords
- controlling weeds
- beta
- soil
- compound
- applying
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000000034 method Methods 0.000 title claims description 13
- 241000196324 Embryophyta Species 0.000 title description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000002689 soil Substances 0.000 claims description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000025670 Eleusine indica Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 244000236458 Panicum colonum Species 0.000 description 2
- 235000015225 Panicum colonum Nutrition 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 244000152045 Themeda triandra Species 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000055702 Amaranthus viridis Species 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FXJJRTVXGFTULP-UHFFFAOYSA-N n-(2-chloroethyl)benzenesulfonamide Chemical compound ClCCNS(=O)(=O)C1=CC=CC=C1 FXJJRTVXGFTULP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BPLJLGTYWGSFCL-UHFFFAOYSA-M potassium;oxido-propan-2-yloxy-propan-2-ylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound [K+].CC(C)OP([O-])(=S)SC(C)C BPLJLGTYWGSFCL-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
Definitions
- polar solvents are better than non-polar solvents and certain catalysts such as tertiary amines and dimethyl formamide aid in bringing the reaction to completion.
- seeds of the test weed species are planted in individual rows one-half inch deep in Santa Cruz sandy loam soil contained in '8" x 12" metal flats. Enough seeds are planted to give about 30 to .50 plants of each weed species in each fiat.
- the flats are watered after planting and the following day each fiat is sprayed at a rate of 5 pounds of the compound under test in gallons of solution per The spraying is conducted as the flat is carried by a moving belt under a sprayer to simulate field spraying conditions. Two weeks later the degree of weed control is' determined by comparing the amount of germination and growth of each weed in the treated flats with the weeds in several untreated control flats.
- the ether solution was dried Inn 100 1m 0 0 over anhydrous magnesium sulfate, filtered and the ether g2; igg 8 ii if? removed on the steam bath with an air jet.
- the viscous gm; 100 10 50 2mg 30 1115 product weighed 170 g. of theory).
- Example 2-N-(beta-0,a-diisopropyldithiophosphoryl)- benzene sulfonamide By an analogous procedure as for Example 1, a mixture of 13.2 g. (0.06 M) of N-(beta-chloroethyl)-benzenesulfonamide, 25.2 g. (0.1 M) of potassium-diisopropyl dithiophosphate and 100 ml. of methyl ethyl ketone Patented Jan. 17, 1967 3,2es,s 19
- the flats are watered after planting and the following day each flat is sprayed at a rate of 20 pound s of the com-v pound under test in 80 gallons of solution per acre.
- a No. 152 DeVilbiss atomizer is used to spray the solution on the soil surface. Two weeks later the degree of weed control is determined by comparing the amount of germination and growth of each weed in the treated flats with the weeds in several control flats.
- R and R are lower alkyl radicals and X is .lower alkyl and nitro.
- the method of controlling weeds comprising applying to the soil a herbicidally effective amount of the compound N- (beta-o,o-diethyldithiophosphorylethyl) -benzene sulfonamide.
- the method of controlling weeds comprising applying to the soil a herbicidally eiTective amount of the compound N- beta-o,o-diisopropyldithiophosphorylethyl) -2,5- dichlorobenzene sulfonamide.
- the method of controlling weeds comprising applying to the soil a herbicidally eifective amount of the compound N (beta 0,0 di-n-propyldithiophosphorylethyl)- benzene sulfonamide.
- the method of controlling weeds comprising applying to the soil a herbicidally effective amount of the compound N- (beta-o,o-di-n-propyldithiophosphorylethyl -2,5- dichlorobenzene sulfonamide.
- the method of controlling weeds comprising applying to the soil a herbicidally effective amount of the compound N- (beta-o-ethyl-o-isopropy1dithiophosphorylethyl) benzene sulfonamide.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
United States PatentO 3,298,819 METHOD OF CONTROLLING WEEDS Llewellyn W. Fancher, Lafayette, Calif., and Chester L. Dewald, Houston, Tex., assignors to Staufier Chemical Company, New York, N.Y., a corporation of Delaware No Drawing. Original application May 28, 1963, Ser. No. 283,709, now Patent No. 3,205,253, dated Sept. 7,
1965. Divided and this application July 16, 1965, Ser.
8 Claims. (Cl. 71-2.6)
(NHrCl) NaGl The beta-chloro intermediates only have been indicated in the above reaction merely for economic reasons. However, the beta-bromo and beta-iodo intermediates will also yield the equivalent phosphate derivatives.
The Completeness of the above reaction is dependent upon the type of solvent used. In general, polar solvents are better than non-polar solvents and certain catalysts such as tertiary amines and dimethyl formamide aid in bringing the reaction to completion.
The following non-limiting examples illustrate the preparation of this class of compounds:
Example 1--N-(beta-0,0-diethyldithiophosphorylelhyl)- benzene sulfonamide yielded after a four hour reflux period, 20.8 g. (88% of acre.
theory) of viscous product. n =l.5428.
Analysis Sulfur, Nitrogen, Phosphorus,
Percent Percent Percent Theory 24. 15 3. 54 7.79 Found 25. 42 3. 6.72
By analogous procedures the following additional compounds were prepared:
R and R:
n-Butyl 0 p-Ghlorophenyl 3,4-diehlorophenyl- Ethyl-isopropyl Methyl-isopropyl Ethyl-n-propyl Methyl-ethyl The compounds of the present invention are excellent herbicides as will be indicated by the test results shown hereinafter wherein the compounds of the present invention are used as pre-emergence herbicides.
In making the tests for pre-emergence application, seeds of the test weed species are planted in individual rows one-half inch deep in Santa Cruz sandy loam soil contained in '8" x 12" metal flats. Enough seeds are planted to give about 30 to .50 plants of each weed species in each fiat. The flats are watered after planting and the following day each fiat is sprayed at a rate of 5 pounds of the compound under test in gallons of solution per The spraying is conducted as the flat is carried by a moving belt under a sprayer to simulate field spraying conditions. Two weeks later the degree of weed control is' determined by comparing the amount of germination and growth of each weed in the treated flats with the weeds in several untreated control flats.
The following chart shows the results of such tests.
A mixture Of 116 g. (0.53 M) Of N-(betachloroethyl)- Foxtail Annual Crab Grass Nut Grass benzene sulfonamide, 162.4 g. (0.8 M) of ammonium- 50 Com Bluegrass diethyldithiophosphate and 250 ml. of methyl ethyl ketone pound P P P P er- 81'- 6!- erwas stlrred and refluxed for four hours. The solvent was cent cent Gr Gent Gr cent Gr removed on a steam bath with an air et, and the residue Ge Ge Ge Ge taken up in ethyl ether and washed three times with dilute aqueous sodium chloride. The ether solution was dried Inn 100 1m 0 0 over anhydrous magnesium sulfate, filtered and the ether g2; igg 8 ii if? removed on the steam bath with an air jet. The viscous gm; 100 10 50 2mg 30 1115 product weighed 170 g. of theory). n 1.5468. 5,115 70 7 10 5ms 100 10 100 10 10 100 10 0 Analysis Sulfur, Nitrogen, Phosphorus, 10 30 3 0 10 Percent Percent Percent 0 00 10 50 7 Theory 26.00 3. 79 g, 39 Legends: Gegermination. Gr-growth (on a rating system of 0 to 10; Found 25.69 3.88 7,79 ll death or very severe effects, 10=n0nnal), iii-malformation, ch--- 0 OIOSlS.
Example 2-N-(beta-0,a-diisopropyldithiophosphoryl)- benzene sulfonamide By an analogous procedure as for Example 1, a mixture of 13.2 g. (0.06 M) of N-(beta-chloroethyl)-benzenesulfonamide, 25.2 g. (0.1 M) of potassium-diisopropyl dithiophosphate and 100 ml. of methyl ethyl ketone Patented Jan. 17, 1967 3,2es,s 19
The flats are watered after planting and the following day each flat is sprayed at a rate of 20 pound s of the com-v pound under test in 80 gallons of solution per acre. A No. 152 DeVilbiss atomizer is used to spray the solution on the soil surface. Two weeks later the degree of weed control is determined by comparing the amount of germination and growth of each weed in the treated flats with the weeds in several control flats.
The results of these tests are as follows:
Foxtail Annual Water grass Pigweed Bluegrass C ompound Per- Per- Per- Percent Gr cent Gr cent Gr cent Gr Ge Ge Ge Ge 15 0 20 2:1 0 a. 16 50 5 20 2bz 50 5 I 20 2b;
Legends: Gegerminati0n, Gr-growth (on a0 to scale; 0=deathor very severe effect, 10=n0rmal), bburn, ddesiccation. Compounds 17 through 20 were tested in the same manner as were compounds 15 and 16. The test rate, however, was 2 lbs/acre and the weed' species tested were crab grass, foXtail and water grass. The results were as Legends: Gegermination, Grgrowth (on a rating system of 0 to 10; 0=death or very severe effects, 10=n0rma1).
We claim:
1. The method of controlling weeds comprising applying to the soil a herbicidally effective amount of a compound of the formula:
wherein R and R are lower alkyl radicals and X is .lower alkyl and nitro.
2. The method of controlling weeds comprising applying to the soil a herbicidally effective amount of the compound N- (beta-o,o-diethyldithiophosphorylethyl) -benzene sulfonamide.
3, The method of controlling weeds comprising'applying to the soil at herbicidally effective amount of the compound N-(beta 0,0 diisopropyldithiophosphorylethyl)- benzene sulfonamide.
4. The method of controlling weeds comprising applying to the soil a herbicidally eiTective amount of the compound N- beta-o,o-diisopropyldithiophosphorylethyl) -2,5- dichlorobenzene sulfonamide.
5. The method of controlling weeds comprising applying to the soil a herbicidally eifective amount of the compound N (beta 0,0 di-n-propyldithiophosphorylethyl)- benzene sulfonamide.
6. The method of controlling weeds comprising applying to the soil a herbicidally effective amount of the compound N- (beta-o,o-di-n-propyldithiophosphorylethyl -2,5- dichlorobenzene sulfonamide.
7. The method of controlling weeds comprising applying to the soil a herbicidally effective amount of the compound N- (beta-o-ethyl-o-isopropy1dithiophosphorylethyl) benzene sulfonamide.
8. The method of controlling weeds comprising applying to the soil a herbicidally effective amount of the compound N-(beta-o-methyl-o-isopropyldithiophosphorylethyl)-benzene sulfonamide.
References Cited by the Examiner UNITED STATES PATENTS 2,705,195 3/1955 Cupery et a1 71-2.6 2,744,819 5/1956 Toorman 712.6 2,803,580 8/1957 Metivier 260461 2,862,019 11/1958 Schrader 260-461 2,865,801 12/1958 Baker et al 260461 X 2,894,017 7/1959 Schegk et a1 260461 3,005,004 10/ 1961 Berkelhammer 260461 FOREIGN PATENTS 927,092 4/ 1955 Germany.
LEWIS GOTTS, Primary Examiner.
J. O. THOMAS, JR., Examiner.
Claims (1)
1. THE METHOD OF CONTROLLING WEEDS COMPRISING APPLYING TO THE SOIL A HERBICIDALLY EFFECTIVE AMOUNT OF A COMPOUND OF THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US484498A US3298819A (en) | 1963-05-28 | 1965-07-16 | Method of controlling weeds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US283709A US3205253A (en) | 1963-05-28 | 1963-05-28 | Nu-(beta-omicron-dialkyldithiophosphoryl)-arylsulfonamides |
| US484498A US3298819A (en) | 1963-05-28 | 1965-07-16 | Method of controlling weeds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3298819A true US3298819A (en) | 1967-01-17 |
Family
ID=26962191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US484498A Expired - Lifetime US3298819A (en) | 1963-05-28 | 1965-07-16 | Method of controlling weeds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3298819A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059432A (en) * | 1974-05-27 | 1977-11-22 | Mitsubishi Petrochemical Co., Ltd. | Plant growth regulator |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2705195A (en) * | 1951-09-27 | 1955-03-29 | Du Pont | Herbicidal compositions and methods employing solutions of substituted ureas in monohydric phenols |
| DE927092C (en) * | 1953-01-08 | 1955-04-28 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
| US2744819A (en) * | 1954-10-13 | 1956-05-08 | Dow Chemical Co | Method for the control of undesired grasses |
| US2803580A (en) * | 1955-03-05 | 1957-08-20 | Rhone Poulenc Sa | Phosphorus derivatives, process for their preparation and compositions containing same |
| US2862019A (en) * | 1956-03-12 | 1958-11-25 | Fabrenfabriken Bayer Ag | Thiophosphoric acid esters and their production |
| US2865801A (en) * | 1956-04-06 | 1958-12-23 | Monsanto Chemicals | Propargyl phosphorothioates |
| US2894017A (en) * | 1956-04-26 | 1959-07-07 | Bayer Ag | Thiophosphoric acid esters and their production |
| US3005004A (en) * | 1959-06-01 | 1961-10-17 | American Cyanamid Co | Sulfamoylphenyl esters of organic phosphorothioates |
-
1965
- 1965-07-16 US US484498A patent/US3298819A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2705195A (en) * | 1951-09-27 | 1955-03-29 | Du Pont | Herbicidal compositions and methods employing solutions of substituted ureas in monohydric phenols |
| DE927092C (en) * | 1953-01-08 | 1955-04-28 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
| US2744819A (en) * | 1954-10-13 | 1956-05-08 | Dow Chemical Co | Method for the control of undesired grasses |
| US2803580A (en) * | 1955-03-05 | 1957-08-20 | Rhone Poulenc Sa | Phosphorus derivatives, process for their preparation and compositions containing same |
| US2862019A (en) * | 1956-03-12 | 1958-11-25 | Fabrenfabriken Bayer Ag | Thiophosphoric acid esters and their production |
| US2865801A (en) * | 1956-04-06 | 1958-12-23 | Monsanto Chemicals | Propargyl phosphorothioates |
| US2894017A (en) * | 1956-04-26 | 1959-07-07 | Bayer Ag | Thiophosphoric acid esters and their production |
| US3005004A (en) * | 1959-06-01 | 1961-10-17 | American Cyanamid Co | Sulfamoylphenyl esters of organic phosphorothioates |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059432A (en) * | 1974-05-27 | 1977-11-22 | Mitsubishi Petrochemical Co., Ltd. | Plant growth regulator |
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