US2104316A - Composition for treatment of seeds - Google Patents
Composition for treatment of seeds Download PDFInfo
- Publication number
- US2104316A US2104316A US59550A US5955036A US2104316A US 2104316 A US2104316 A US 2104316A US 59550 A US59550 A US 59550A US 5955036 A US5955036 A US 5955036A US 2104316 A US2104316 A US 2104316A
- Authority
- US
- United States
- Prior art keywords
- seeds
- composition
- compounds
- mercury
- radical
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title description 13
- 229940100892 mercury compound Drugs 0.000 description 12
- 150000002731 mercury compounds Chemical class 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 208000031888 Mycoses Diseases 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 alkyl mercury nitrogen Chemical compound 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108090001069 Chymopapain Proteins 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HYQZWFWJRVCZLL-UHFFFAOYSA-L S(=O)(=O)([O-])[O-].C[Hg+2] Chemical compound S(=O)(=O)([O-])[O-].C[Hg+2] HYQZWFWJRVCZLL-UHFFFAOYSA-L 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003672 ureas 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
Definitions
- i'his invention relates to seed disinfectants, more particularly to the eradication or control of fungus diseases of seeds.
- the present invention is intended and adapted to overcome the disadvantages of the priorknown compounds, it being among'the objects thereof to provide a method of and a composition for .the treatment of seeds, which will be highly effective, relatively non-toxic, non-odorous, and non-vesi cant.
- R is a carbon containing radical in which the carbon is directly attached to the nitrogen 55 and said radical may contain nitrogen and oxymembers of the group of organic mercury com-' (Ci. Edi-38) gen as well as hydrogen; such as CN and --CONH2.
- the toxic and other objectionable properties of the. preparations containing the previously proposed organic compounds of mercury in the form in which they are normally applied 5 to seeds are substantially reduced by virtue of the use according to the invention as the active princ ple of mercury compounds of the type RHg-NHR'.
- Compounds of the type R-Hg-NI-i-R' are to be distinguished from compounds of the type R-Hg-X where X is an acidic radical, in that the former are derived from organic nitrogen compounds of the type HzN-R which are not acids, and therefore the compounds R--HgNH--R are not salts.
- type compounds included in the present invention are those of the type where R is a divalent radical which is that of the di-aryl and di-alkylsubstituted guanidines.
- the amount of mercury compound in the composition mayvary within wide limits and is dependent on anumber of factors, such as the char- 25 acter of the seeds, the type of disease to be controlled, the nature of the diluent, the particle size, and the like. In general, it may be said that the amount of mercury compound varies from 0.1% to 3.0% of the diluent or filler used.
- the amount of composition used on the seeds also varies with anumber of factors, but usually from 1 to 8.ounces are used per bushel of seeds.
- Example 1 A solution of calcium cyanamide'is added to a suitable amount of precipitated calcium sulphate and thoroughly mixed therewith. To the mixture is then added with stirring a solution of methyl mercury sulphate at ordinary room temperature. A reaction occurs resulting in the formation of the mercury compound in situ according to the following equation:
- the mixture of inert diluent and mercury compound is dried in a rotary drier and ground to a suitable degree of fineness.
- a composition for controlling fungus diseases of seeds comprising a mercury compound having the general formula wherein R is an unsubstituted aliphatic hydrocarbon radical and R is a radical consisting of carbon and nitrogen atoms and in which carbon is directly attached to nitrogen.
- composition for controlling fungus diseases of seeds comprising an alkyl mercury nitrogen compound having the formula CzHsHgNHCONHz 3.
- a composition for controlling fungus diseases of seeds comprising an alkyl mercury nitrogen compound having the formula CHaHgNl-ICN CHaHgNHCONHz.
- a composition for controlling fungus discases of seeds comprising a mercury compound taken from the class consisting of RHgNHCONHz, RHgNI-ICSNI-Iz, RHgNI-ICN, RHgNH aryl, RHgNH alkyl, RI-IgNC(NH aryl)z, RHgNC(NH a1ky1)2, wherein R is an unsubstituted aliphatic hydrocarbon radical.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Patented Jan. 4, 1938 4 uuirsu stares COMPOSITION FOR TEEA'EMENT (NF SEEDS .lloscph Roy Boner, Addiscombe-Surrey, England, and Gustav Kossel, Hackensack, N. .l.
No Drawing. Application January lit i936, Serial No. 59,55@
6 Claims.
i'his invention relates to seed disinfectants, more particularly to the eradication or control of fungus diseases of seeds.
The use of organic mercury compounds for the control of such diseases has been practiced for some years more or less successfully. Many suchv compounds have been described in the literature, and they have been used in the form of solutions and emulsions, and mixed with solid inert diluents in the form of dusts. However,'many of these prior art compounds did not prove successful for the control oi the disease or resulted in injury to the seeds. Other compounds which gave good results in disease control, had certain 15 collateral disadvantages.
It has recently been demonstated (Dillon Weston in Booer-Journal of Agricultural Science. Vol. XXV Part IV, Oct. 1935) that highly eihcient organic mercury compounds for this pur- 21) pose are those of the type R,Hg-X in which R is an unsubstituted hydrocarbon radical and X is an acid radical. These compounds are in principle the salts produced by the neutralization of the alkali RHg-OH with an acid. While'these 25 compounds gave excellent results in seed disease control, being highlyeffective in small amounts, they, possessed the disadvantage that they have a disagreeable odor in some cases, are somewhat toxic and in certain circumstances have a vesi- 39 cant action. r
The present invention is intended and adapted to overcome the disadvantages of the priorknown compounds, it being among'the objects thereof to provide a method of and a composition for .the treatment of seeds, which will be highly effective, relatively non-toxic, non-odorous, and non-vesi cant.
It has now been found and the present invention is based, on this discovery, that certain pounds designated by the general, formula RHg--NH--R' where Ris an unsubstituted hyf drocarbon radical such as methyl, ethyl, phenyl, and tolyl, and the group NH- -R' is the radical of any organic nitrogen compound in which one or more hydrogen atoms are dlrectlyattached to a nitrogen atom, retain the strong fungicidal propcities of the group RHg, and can be used for the control of seed borne fungus diseases by applying them to seeds in appropriate quantities either in solutions,. emulsions, or as dry dusts after intimate incorporation with an inert diluent. R is a carbon containing radical in which the carbon is directly attached to the nitrogen 55 and said radical may contain nitrogen and oxymembers of the group of organic mercury com-' (Ci. Edi-38) gen as well as hydrogen; such as CN and --CONH2. The toxic and other objectionable properties of the. preparations containing the previously proposed organic compounds of mercury in the form in which they are normally applied 5 to seeds are substantially reduced by virtue of the use according to the invention as the active princ ple of mercury compounds of the type RHg-NHR'.
Compounds of the type R-Hg-NI-i-R' are to be distinguished from compounds of the type R-Hg-X where X is an acidic radical, in that the former are derived from organic nitrogen compounds of the type HzN-R which are not acids, and therefore the compounds R--HgNH--R are not salts.
Among the type compounds included in the present invention are those of the type where R is a divalent radical which is that of the di-aryl and di-alkylsubstituted guanidines.
The amount of mercury compound in the composition mayvary within wide limits and is dependent on anumber of factors, such as the char- 25 acter of the seeds, the type of disease to be controlled, the nature of the diluent, the particle size, and the like. In general, it may be said that the amount of mercury compound varies from 0.1% to 3.0% of the diluent or filler used. The amount of composition used on the seeds also varies with anumber of factors, but usually from 1 to 8.ounces are used per bushel of seeds.
The following examples will serve to illustrate the invention:
35 Example 1 Example 2 A solution of calcium cyanamide'is added to a suitable amount of precipitated calcium sulphate and thoroughly mixed therewith. To the mixture is then added with stirring a solution of methyl mercury sulphate at ordinary room temperature. A reaction occurs resulting in the formation of the mercury compound in situ according to the following equation:
The mixture of inert diluent and mercury compound is dried in a rotary drier and ground to a suitable degree of fineness.
The above cited examples are for the purpose of illustrating the invention and are not to be construed as limiting the same. Various modifications may be made within the spirit of the invention. For example, other diluents may be used in place of those mentioned above. Other nitrogen compounds may be used in place of urea and cyanamide, as the aryl and alkyl disubstituted guanidines, aryl and alkyl amines, thioureas, substituted ureas, and the like. While certain proportions of mercury compound in the composition have been specifically set forth, the invention is not limited thereto and the proportion of mercury compound may vary within considerably wide limits. Less than 0.1% or more than 3.0%, even up to 6.0% or 8.0% of mercury compound may be used in the composition, depending upon the circumstances and the character of the application. These and other changes may be made in the present invention, the scope of which is set forth in theclaims appended hereto.
What We claim is:
1. A composition for controlling fungus diseases of seeds comprising a mercury compound having the general formula wherein R is an unsubstituted aliphatic hydrocarbon radical and R is a radical consisting of carbon and nitrogen atoms and in which carbon is directly attached to nitrogen.
2. A composition for controlling fungus diseases of seeds comprising an alkyl mercury nitrogen compound having the formula CzHsHgNHCONHz 3. A composition for controlling fungus diseases of seeds comprising an alkyl mercury nitrogen compound having the formula CHaHgNl-ICN CHaHgNHCONHz.
6. A composition for controlling fungus discases of seeds comprising a mercury compound taken from the class consisting of RHgNHCONHz, RHgNI-ICSNI-Iz, RHgNI-ICN, RHgNH aryl, RHgNH alkyl, RI-IgNC(NH aryl)z, RHgNC(NH a1ky1)2, wherein R is an unsubstituted aliphatic hydrocarbon radical.
JOSEPH ROY BOOER. GUSTAV KOSSEL.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59550A US2104316A (en) | 1936-01-17 | 1936-01-17 | Composition for treatment of seeds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59550A US2104316A (en) | 1936-01-17 | 1936-01-17 | Composition for treatment of seeds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2104316A true US2104316A (en) | 1938-01-04 |
Family
ID=22023695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US59550A Expired - Lifetime US2104316A (en) | 1936-01-17 | 1936-01-17 | Composition for treatment of seeds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2104316A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2524547A (en) * | 1947-06-28 | 1950-10-03 | Frank J Sowa | Fungicidal mercury compounds and methods of making same |
| US3461147A (en) * | 1965-01-14 | 1969-08-12 | Int Lead Zinc Res | Organo-zinc compounds and processes of making same |
-
1936
- 1936-01-17 US US59550A patent/US2104316A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2524547A (en) * | 1947-06-28 | 1950-10-03 | Frank J Sowa | Fungicidal mercury compounds and methods of making same |
| US3461147A (en) * | 1965-01-14 | 1969-08-12 | Int Lead Zinc Res | Organo-zinc compounds and processes of making same |
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