GB2136433A - Phosphonium Salt of N-Formyl-N-Hydroxy-Alanine - Google Patents
Phosphonium Salt of N-Formyl-N-Hydroxy-Alanine Download PDFInfo
- Publication number
- GB2136433A GB2136433A GB08306784A GB8306784A GB2136433A GB 2136433 A GB2136433 A GB 2136433A GB 08306784 A GB08306784 A GB 08306784A GB 8306784 A GB8306784 A GB 8306784A GB 2136433 A GB2136433 A GB 2136433A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphonium salt
- formyl
- alanine
- salt
- hydroxy
- 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- Withdrawn
Links
- XSGZBEAQSXKYJO-VKHMYHEASA-N (2s)-2-[formyl(hydroxy)amino]propanoic acid Chemical compound OC(=O)[C@H](C)N(O)C=O XSGZBEAQSXKYJO-VKHMYHEASA-N 0.000 title claims abstract description 16
- 150000004714 phosphonium salts Chemical class 0.000 title claims abstract description 15
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 241000233866 Fungi Species 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 239000000417 fungicide Substances 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- -1 phosphonium compound Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- VQNQTIUCMJTZGX-UHFFFAOYSA-N 2-hydroxyethyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCO)C1=CC=CC=C1 VQNQTIUCMJTZGX-UHFFFAOYSA-N 0.000 claims description 3
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 claims description 3
- NIWTURHDMVXESD-UHFFFAOYSA-N 7,7,7-triphenylheptylphosphane Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(CCCCCCP)C1=CC=CC=C1 NIWTURHDMVXESD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000209219 Hordeum Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005496 phosphonium group Chemical group 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000028070 sporulation Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 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
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/34—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-halogen bonds; Phosphonium salts
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Phosphonium salt of N-formyl-N-hydroxy-alanine of general formula (I) is disclosed <IMAGE> where each of R<1>, R<2>, R<3> and R<4> represent H, or an optionally substituted alkyl, cycloalkyl or aryl group having up to 12 carbon atoms. 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 also described.
Description
SPECIFICATION
Phosphonium Salt of N-Formyl-N-Hydroxy-Alanine
The present invention relates to certain phosphonium 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 phosphonium 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 phosphonium salt of N-formyl-N-hydroxy-alanine of general formula I
in which each of R', R2, R3 and R4 independently represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl or aryl group having up to 12 carbon atoms.
PreferablyR1, R2, R3 and R4 independently represents alkyl having 1-7 carbon atoms and phenyl.
Most preferred phosphonium salts are selected from the tetraphenylphosphonium, the (2 methyl)propylenetriphenylphosphonium, the 2-hydroxyethyltriphenylphosphonium and the triphenylheptylphosphonium salt of N-formyl-N-hydroxy-alanine.
The present invention also provides a fungicidal composition which comprises a carrier and a phosphonium 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 a 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 18 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 wili be illustrated by the following Examples.
EXAMPLE 1
Preparation of the (2-Methyl)propylenetriphenylphosphonium Salt of N-formyl-N-hydroxy-alanine.
(2-methyl)propylenetriphenylphosphonium chloride (1 mole) in water (1 I.) was treated with damp silver oxide (2mole) and mixture stirred at R.T. for 2 hours. The silver salts were filtered off and the aqueous filtrate treated with N-formyl-N-hydroxyalanine (1 mole) in water (1 I.). Removal of water resulted in a yellow, viscous, hygroscopic oil.
Yield quantitative
anal. Calc.: C 64.9%; H 6.7%, N 2.9%; P 6.45%
Found: C 65.0%; H 7.0%; N 2.8%; P 6.5%
EXAMPLE 2
Preparation of the Tetraphenylphosphonium Salt of N-formyl-N-hydroxy-alanine.
Tetraphenylphosphoniumbromide (1 mole) in water/ethanol (11. 50% soln.) was stirred at room temperature with moist silver oxide (2moles) for 2 hours. The silver salts were filtered off and the aqueous filtrate treated with N-formyl-N-hydroxy-alanine (1 mole) in water (1 I.). Removal of water resulted in a white solid which was triturated under ether.
Yield: 70%.
m.p.: 6668 anal. Calc.: C 661.1% H 5.9% N 2.8%
Found: C 65.3%; H 5.9%; N 3.1%
Further examples of salts of N-formyl-N-hydroxy-alanine according to the present invention are shown in Table I. Of the salts only the phosphonium part is given.
TABLE I Example Phosphonium part C H N
3 triphenylmethylphosphonium anal. Calc. 64.4% 6.1% 3.3%
Found 64.9% 6.1% 3.4%
4 2-hydroxyethyltriphenylphosphonium anal. Calc. 61.9% 5.8% 2.9%
Found 62.6% 6.1% 3.3%
5 triphenylheptyiphosphonium anal. Calc. 68.1% 7.45% 2.7% Found 67.4% 7.8% 2.5%
The present invention will be further described with reference to the following Example.
EXAMPLE 6
Glasshouse Fungicide Evaluation
The following tests which have been described in European patent application 57027 have been carried out.
(a) Antisporulent activity against vine downy mildew (Plasmopara viticola; P.v.a.).
(b) Translaminar activity against vine downy mildew (Plasmopara viticola; P.v.t.).
(c) Activity against apple powdery mildew (Podosphaera leucotricha; P.l.).
A test which has not been described in European patent application 57027 but which has been carried out in connection with the present invention is:
(d) Activity against barley powdery mildew FErysiphe graminis f.sp. horde) Eg.
The test is a direct antisporulant one, using a foliar spray. Leaves of barley seedlings, cultivar
Golden Promise, are inoculatedby dusting with mildew conidia one day prior to treatment with the test compound. The inoculated plants are kept overnight at glasshouse ambient temperature and humidity prior to treatment. The plants are sprayed at a dosage of 1 kg. of active material per nectare using a track sprayer as described under (a). After drying, plants are returned to a compartment at ambient temperature and humidity for up to 7 days, followed by assessment. Assessment is based on the percentage of leaf area covered by sporulation compared with that on leaves of control plants.
The extent of disease control in all the above tests is expressed as a rating compared with a diluent sprayed control according to the criteria: O=less than 50% disease control
1 =about 5080% disease control
2=greater than 80% disease control
TABLE II
Fungicidal Activity
Compound
of
Example R' R2 R3 R4 P.v.a. P.v.t. P.l. E.g.
3 methyl phenyl phenyl phenyl 2 0 0 0
2 phenyl phenyl phenyl phenyl 2 1 0 2
4 2-hydroxyethyl phenyl phenyl phenyl 2 1 0 1 1 2-methyl-1 -propenyl phenyl phenyl phenyl 1 1 2 0
5 heptyl phenyl phenyl phenyl 2 2 1 0
Claims (9)
1. A phosphonium salt of N-formyl-N-hydroxy-alanine of general formula I
in which each of R', R2, R3 and R4 independently represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl or aryl group having up to 1 2 carbon atoms.
2. A phosphonium salt as claimed in claim 1 in which each of R', R2, R3 and R4 independently represents alkyl having 1-7 carbon atoms or phenyi.
3. A phosphonium salt as claimed in claim 1 or 2 which is selected from the group consisting of the triphenylmethylphosphonium, the tetraphenylphosphonium, the (2methyl)propylenetriphenylphosphonium, the 2-hydroxyethyltriphenylphosphonium and the triphenylheptylphosphonium salt of N-formyl-N-hydroxy-alanine.
4. A fungicidal composition which comprises a carrier and a phosphonium salt as claimed in any one of the claims 1-3.
5. A method for combating fungus at a locus which comprises treating the locus with a fungicidally effective amount of a phosphonium salt as defined in any one of the claims 1-3 or of a fungicidal composition as claimed in claim 4.
6. A method as claimed in claim 5 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.
7. A method as claimed in claim 6 in which said plants are vines.
8. The use as a fungicide of a phosphonium salt as claimed in any one of the claims 1-3.
9. A process for the preparation of a phosphonium salt of general formula I which comprises reacting N-formyl-N-hydroxy-alanine with a phosphonium compound as hereinbefore defined according to known procedures.
1 0. A process for the preparation of a salt of general formula I using a process as hereinbefore described with particular reference to the Examples.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08306784A GB2136433A (en) | 1983-03-11 | 1983-03-11 | Phosphonium Salt of N-Formyl-N-Hydroxy-Alanine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08306784A GB2136433A (en) | 1983-03-11 | 1983-03-11 | Phosphonium Salt of N-Formyl-N-Hydroxy-Alanine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8306784D0 GB8306784D0 (en) | 1983-04-20 |
| GB2136433A true GB2136433A (en) | 1984-09-19 |
Family
ID=10539410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08306784A Withdrawn GB2136433A (en) | 1983-03-11 | 1983-03-11 | Phosphonium Salt of N-Formyl-N-Hydroxy-Alanine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2136433A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223533A1 (en) * | 1985-11-11 | 1987-05-27 | Albright & Wilson Limited | Compounds and methods for control of bryophytes, lichens, algae and fungal and microbial plant pathogens |
| EP0444749A1 (en) * | 1990-03-01 | 1991-09-04 | Shell Internationale Researchmaatschappij B.V. | Fungicidal compositions containing benzyl-tris(aryl) phosphonium salts |
| US5741757A (en) * | 1985-08-06 | 1998-04-21 | Albright & Wilson Limited | Biocidal mixture of tetrakis (hydroxymethyl) phosphonium salt and a surfactant |
-
1983
- 1983-03-11 GB GB08306784A patent/GB2136433A/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741757A (en) * | 1985-08-06 | 1998-04-21 | Albright & Wilson Limited | Biocidal mixture of tetrakis (hydroxymethyl) phosphonium salt and a surfactant |
| EP0223533A1 (en) * | 1985-11-11 | 1987-05-27 | Albright & Wilson Limited | Compounds and methods for control of bryophytes, lichens, algae and fungal and microbial plant pathogens |
| US4775407A (en) * | 1985-11-11 | 1988-10-04 | Albright & Wilson Limited | Method of treating surfaces to control bryophytes or lichens using a water soluble tetrakis (hydroxymethyl) phosphonium salt |
| US5139561A (en) * | 1985-11-11 | 1992-08-18 | Albright & Wilson Limited | Method for protecting growing plants against fungal or microbial path pathogens |
| EP0444749A1 (en) * | 1990-03-01 | 1991-09-04 | Shell Internationale Researchmaatschappij B.V. | Fungicidal compositions containing benzyl-tris(aryl) phosphonium salts |
| WO1991013073A1 (en) * | 1990-03-01 | 1991-09-05 | Shell Internationale Research Maatschappij B.V. | Fungicidal compositions containing benzyl-tris(aryl)phosphonium salts |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8306784D0 (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) |