GB2136416A - Fungicidal sulphur containing salt of N-formyl-N-hydroxy-alanine - Google Patents
Fungicidal sulphur containing salt of N-formyl-N-hydroxy-alanine Download PDFInfo
- Publication number
- GB2136416A GB2136416A GB08306782A GB8306782A GB2136416A GB 2136416 A GB2136416 A GB 2136416A GB 08306782 A GB08306782 A GB 08306782A GB 8306782 A GB8306782 A GB 8306782A GB 2136416 A GB2136416 A GB 2136416A
- Authority
- GB
- United Kingdom
- Prior art keywords
- salt
- formyl
- alanine
- hydroxy
- plants
- 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.)
- Withdrawn
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A new sulphur containing salt of N-formyl-N-hydroxy-alanine, having the formula <IMAGE> a fungicidal composition comprising a carrier and the above salt, a method for combating fungus, the use of the salt as fungicide and a process for preparing the salt are described.
Description
SPECIFICATION
Sulphur containing salt of N-formyl-N-hydroxy-alanine
The present invention relates to certain sulphur containing salts of N-formyl-N-hydroxy-alanine.
European patent application 57027 in the name of Applicant describes the fungicidally active compound N-formyl-N-hydroxy-alanine and a variety of derivatives showing fungicidal activity as well.
It has now been found that certain sulphur containing salts of N-formyl-N-hydroxy-alanine which are not known from European patent application 57027 appear to show very suitable fungicidal activities.
The present invention therefore provides a salt of N-formyl-N-hydroxy-alanine of general formula I
in which each of R', R2 and R3 independently represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl or aryl group having up to 12 carbon atoms and n=1 or 0.
Preferably R', R2 and R3 independently represents methyl or ethyl.
Preferred salts are the trimethyl and triethyl sulphonium salt and the trimethylsulphoxonium salt of
N-formyl-N-hydroxy-alanine.
The present invention also provides a fungicidal composition which comprises a carrier and a sulphur containing salt as hereinbefore described.
A carrier in a composition according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed or soil, or to facilitate storage, transport or handling. A carrier may be solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid, and any of the carriers normally used in formulating fungicidal compositions may be used.
Suitable carriers have been described in European patent application 57027 on page 4, line 1 8 until page 6, line 4.
Further reference is made to European patent application 57027, on page 6, line 5 until page 7, line 9, with respect to what kind of formulations are suitable in connection with the present invention.
In another aspect, the invention also provides a method for combating fungus as described in
European Patent Application 57027 on page 3, last paragraph until page 4, first paragraph.
The present invention will be further described with reference to the following Examples.
EXAMPLE I
Preparation of the trimethyl sulphonium salt of N-formyl-N-hydroxy-alanine.
Trimethylsulphoniumiodide (1 mole) in water (11.) and ethanol (100ml) was treated with damp silver oxide (2moles) and the reaction mixture stirred at room temperature for 2 hours. The silver salts were filtered off and the aqueous filtrate was treated with N-formyl-N-hydroxy alanine (1 mole) in water (1 1.). The solution was evaporated to dryness and the crystals obtained washed with acetone.
Yield: 80% m.p.: 106--1100 (dec.)
anal. calc: 040.1%; H 7.2%; N 6.7%
found: C 39.9%; H 7.6%; N 6.7%
EXAMPLE II
Preparation of trieth ylsulphonium salt of N-form yl-N-h ydroxy-alanine.
Triethylsulphoniumiodide (1 mole) in water (11.) and ethanol (100ml) was treated with damp silver oxide (2moles) and the reaction mixture stirred at room temperature for 2 hours. The silver salts were filtered off and the aqueous filtrate was treated with N-formyl-N-hydroxyalanine (1 mole) in water (11.). The solution was evaporated to dryness to yield a dark yellow oil.
Yield: quantitative
anal. calc: 044.6%; H 8.6%; N 5.3%
found: 044.3%; H 9.4%; N 5.1 % EXAMPLE Ill
Preparation of the trimethyl suiphoxonium salt ofN-formyl-N-hydroxy-alanine Trimethylsulphoxoniumiodide (1 mole) in water (2 1.) passed down IRA- 410 0 (OHe) ion exchange column and eluted with water. The eluant was treated with N-formyl-N-hydroxy alanine (1 mole) in water (1 1.). The solution was evaporated to dryness and the white crystals obtained were reprecipitated from ethanol/ether.
Yield: 70% m.p.: 102-1050C anal. calc: C 37.4%; H 6.7%; N 6.2%
found: C 36.4%; H 6.8%; N 6.3%
The present invention will be further described with reference to the following Example.
EXAMPLE 4
Glasshouse Fungicide Evaluation
The following tests which have been described in European patent application 57027 have been carried out.
a) Antisporulant activity against vine downy mildew (Plasmopara viticola; P.v.a.) and (b) Translaminar activity against vine downy mildew (Plasmopara viticola; P.v.t)
The extent of disease control in the above tests is expressed as a rating compared with a diluent sprayed control according to the criteria: 0 = less than 50% disease control
1 = about 5080% disease control
2 = greater than 80% disease control
In Table 1 the results of the above test are shown.
Table 1
Fungicidal
Activity Compound of Example n R1 R2 R3 P.v.a. P.v.t.
0 methyl methyl methyl 2 0 II 0 ethyl ethyl ethyl 2 1 1 1 methyl methyl methyl 2 1
Claims (11)
1. A salt of N-formyl-N-hydroxy-alanine of general formula I
in which each of Rt, R2 and R3 independently represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl or aryl group having up to 12 carbon atoms and n = 1 or 0.
2. A salt as claimed in claim 1 in which each of R, R2 and R3 independently represents methyl or ethyl.
3. A salt of as claimed in claim 2 in which Rt=R2=R3= methyl or ethyl and n=O.
4. A salt as claimed in claim 1 in which R,=R2=R3= methyl and n=1.
5. A fungicidal composition which comprises a carrier and a salt as claimed in any one of the claims 1-4.
6. A method for combating fungus at a locus which comprises treating the locus with a fungicidally effective amount of a salt as defined in any one of the claims 1 4.
7. A method as claimed in claim 6 in which the locus comprises plants subject or subjected to fungal attack, seeds of such plants or the medium in which the plants are growing or are to be grown.
8. A method as claimed in claim 7 in which said plants are vines.
9. The use as a fungicide of a salt as claimed in any one of claims 1-4.
10. A process for the preparation of a salt as claimed in any one of the claims 1-4 according to methods known in the art.
11. A process for the preparation of a salt as claimed in any one of the claims 1-4 using a process as hereinbefore described with particular reference to the Examples.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08306782A GB2136416A (en) | 1983-03-11 | 1983-03-11 | Fungicidal sulphur containing salt of N-formyl-N-hydroxy-alanine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08306782A GB2136416A (en) | 1983-03-11 | 1983-03-11 | Fungicidal sulphur containing salt of N-formyl-N-hydroxy-alanine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8306782D0 GB8306782D0 (en) | 1983-04-20 |
| GB2136416A true GB2136416A (en) | 1984-09-19 |
Family
ID=10539408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08306782A Withdrawn GB2136416A (en) | 1983-03-11 | 1983-03-11 | Fungicidal sulphur containing salt of N-formyl-N-hydroxy-alanine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2136416A (en) |
-
1983
- 1983-03-11 GB GB08306782A patent/GB2136416A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB8306782D0 (en) | 1983-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |