GB2163652A - Fungicidal composition based on aluminium tris-(ethyl-phosphonate) - Google Patents
Fungicidal composition based on aluminium tris-(ethyl-phosphonate) Download PDFInfo
- Publication number
- GB2163652A GB2163652A GB08521365A GB8521365A GB2163652A GB 2163652 A GB2163652 A GB 2163652A GB 08521365 A GB08521365 A GB 08521365A GB 8521365 A GB8521365 A GB 8521365A GB 2163652 A GB2163652 A GB 2163652A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- phosethyl
- composition according
- aqueous solution
- composition
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 239000003381 stabilizer Substances 0.000 claims abstract description 8
- 241000233866 Fungi Species 0.000 claims abstract description 7
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003751 zinc Chemical class 0.000 claims abstract description 5
- 239000004246 zinc acetate Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- 235000001014 amino acid Nutrition 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 229960001484 edetic acid Drugs 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 244000038559 crop plants Species 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 6
- 239000007924 injection Substances 0.000 abstract description 6
- 239000000243 solution Substances 0.000 description 14
- 238000011282 treatment Methods 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 2
- 244000025272 Persea americana Species 0.000 description 2
- 235000008673 Persea americana Nutrition 0.000 description 2
- 241000233614 Phytophthora Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 241000233618 Phytophthora cinnamomi Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- XRBGEQKKQIRUOE-UHFFFAOYSA-N dialuminum ethyl phosphite Chemical compound [Al+3].[Al+3].CCOP([O-])[O-].CCOP([O-])[O-].CCOP([O-])[O-] XRBGEQKKQIRUOE-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- -1 phosphorous acid ester Chemical class 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000037921 secondary disease Diseases 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The fungicidal compositions of the invention comprise, in aqueous solution, phosethyl A1 (aluminium tris-(ethyl phosphonate)) and, as stabilising agent, a water-soluble zinc salt of a weak acid (e.g. zinc acetate), and are especially suitable for injection into the trunks of crop trees or shrubs to combat attack by phytophagous fungi.
Description
SPECIFICATION
Fungicidal composition based on aluminium tris-(ethyl phosphonate)
The present invention relates to new fungicidal compositions based on a phosphorous acid ester, and to a method of combating fungal disease of plants using such compositions.
French Patent 2,254,276 describes compositions for combating fungal diseases of plants, which contain, as the active ingredient, at least one salt of an alkyl-phosphorous acid. These compositions are effective against many phytophagous fungi, such as Phycomycetes, in particular
Plasmopara viticola and various Phytophthora. In practice, aluminium ethyl phosphite (otherwise known as aluminium tris-(ethyl phosphonate) and hereinafter identified as "phosethyl Al") is used commercially, in the form of a wettable powder, for treatment by spraying the leaves. Although this formulation is quite effective when used in this manner, in particular for protecting vines, its effectiveness takes longer to appear when it is applied curatively to tropical crops attacked, aften heavily, by fungi of the Phytophthora type, such as Phytophthora cinnamoni which cause avocado rot or rot of citrus fruits.
In fact, the amounts absorbed by a foliage of low absorbency are relatively small, and are insufficient if trees which have already been attacked are treated curatively. This necessitates more applications, rendering the treatment prohibitive, slow in all respects and even inadequate against severe attacks by the fungi.
It has now been found that these diseases can be effectively comabated by application, in particular by injection into the trunks of crop trees or shrubs, of a stabilised aqueous solution of phosethyl Al. However, this poses a problem inasmuch as this active ingredient is susceptible to hydrolysis in an aqueous medium, which substantially and progressively decreases its concentration, making it impossible to obtain concentrated aqueous compositions which are stable over a period of time.
The present inventon provides a fungicidal composition which comprises, in aqueous solution, phosethyl Al and, as a stabilising agent, a water soluble zinc salt of a weak acid.
The invention also relates to a process for stabilising aqueous solutions of phosethyl Al, which comprises adding a water-soluble zinc salt of a weak acid, as a stabiliser, to the aqueous solution of phosethyl Al. The term "weak acid" is to be understood as meaning a mineral acid or preferably an organic acid, such as an aliphatic acid for example a lower aliphatic acid containing 1 to 6 carbon atoms such as acetic acid, propionic acid, butyric acid, lactic acid or citric acid, or an aminoacid, such as ethylene-diaminetetracetic acid.
The amount of stabiliser depends on the nature thereof and the concentration of phosethyl Al in the aqueous compositions. In fact, if the stabiliser is present either in too small an amount or, on the other hand, in too large an amount, the solution is not clear which signifies that solubilisation of the active ingredient is insufficient, with the result that the effectiveness is correspondingly limited. Surprisingly, it has moreover been found that the most suitable amount is not that corresponding to the stoichiometric amount relative to phosethyl Al. Generally amounts from 30 to 80% of the stoichiometric amount are suitable. For example, in the case of zinc acetate, about half the stoichiometric amount gives a stable clear solution, whilst twice this amount gives rise to a precipitate.
The aqueous composition according to the invention may also contain other water-soluble adjuvants, such as surface-active agents, although this is not necessary for injectable solutions.
It may also contain certain oligo-elements which promote growth of the plants, eg. crop trees or shrubs or are advantageous in combating deficiencies, in suitable amounts.
The phosethyl Al is generally present in the compositions according to the invention in a concentration of between 1 and 120 g/litre, preferably between 10 and 110 g/litre.
This solution can be applied to plants to combat attacks by phytophagous fungi by any suitable treatment, such as spraying of the leaves or soaking of the roots. Excellent results have been obtained by injection into the trunk of diseased crop trees, e.g., avocado trees, and the process can also be applied to other trees, such as citrus fruit trees, or hevea or cocoa trees.
The treatment is carried out by first making holes distributed around the trunk of the tree.
In a second stage, a defined amount of the aqueous phosethyl Al solution employed, which may vary from 0.1 to 5 g/m2 of soil covered by the foliage, is injected into the holes with any appropriate device, with or without using pressure.
The liquid is absorbed slowly and is preferably kept under pressure in the injection apparatus.
When the injection has ended, it may be desirable to block the hole or holes with the aid of a material which is non-aggressive towards the plant tissue, e.g., a wax, which may contain adjuvants, such as disinfectants, in order to reduce the risk of introducing secondary diseases.
The number of treatments is very small, especially with respect to the number of interventions necessary when the leaves are sprayed. For example, on a severely attacked crop tree or shrub, effective curative treatment is obtained in the first year with two injections, and in the following years treatment once per year is sufficient to keep the crop tree or shrub healthy or on the way to recovery. The effectiveness of the treatment is remarkable, heavily attacked crop trees or shrubs being cured within 2 years, which is surprising since other systemic fungicides which are usually active on these fungi are ineffective when injected under the same conditions.
The Examples which follow illustrate the invention.
Example 1:
The three following compositions, in which amounts are by weight, are prepared by dissolving successively phosethyl Al and, where appropriate, zinc acetate in water:
Composition of the
invention
Control
Composition 1 2
Technical grade 98 % pure
Phosethyl Al ....... 102 102 102
Zinc acetate dihydrate - 47 70
Water qsp 1 litre .... 948 916 898
The amounts of acetate in Compositions 1 and 2 correspond respectively to half the stoichiometric amount of phosethyl Al, for composition 1, and to three quarters of this stoichiometric amount, for composition 2.
The three solutions are subjected to a stability test at 500C for 1 month, after which the relative degradation of phosethyl Al and the appearance of the solution are evaluated. The results are shown in the following table:
I Evaluation criterion : Invention after 1 month at 500C : Control I 1 2 I I I I ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ I ~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~ I Relative degradation I of phosethyl Al l 100 % : 13 16 I I I ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ I ~~~~~~~~~~~~~~~~ I ~~~~~~~~~~~~~~~~~~~~~ I Appearance of the I I I solution (initially : Precipitate : Clear Slightly clear) l I cloudy I I I I I I I ~~~~~~~~~~~~~~~~ I ~~~~~~~~~~~~~~~~~~~~~ This table clearly shows that after 1 month at 50 C: -in the control solution, the phosethyl Al is completely degraded and a precipitate forms in the solution. This solution is thus neither stable nor clear; -in solutions 1 and 2 according to the invention, the degradation of phosethyl Al is limited in an acceptable manner; it will be seen that the decomposition of phosethyl Al is less in solution 1 than in solution 2.
Example 2:
Two compositions are prepared by diluting composition 1, obtained in Example 1, once and, respectively, twice. Compositions containing, respectively, 51 and 25.5 grams of 98% pure phosethyl Al and 23.5 and 11.75 grams of zinc acetate per litre are thus obtained.
Claims (14)
1. A fungicidal composition which comprises, in aqueous solution, phosethyl Al and, as a stabilising agent, a water soluble zinc salt of a weak acid.
2. A composition according to claim 1 in the form of a clear aqueous solution.
3. A composition according to claim 1 or 2 wherein the weak acid is an organic acid.
4. A composition according to claim 1 or 2 wherein the weak acid is an aliphatic acid or an aminoacid.
5. A composition according to claim 1 or 2 wherein the weak acid is acetic acid, propionic acid, butyric acid, lactic acid, citric acid or ethylenediaminetetracetic acid.
6. A composition according to any one of claims 1 to 5, in which the stabilising agent is zinc acetate.
7. A composition according to any one of claims 1 to 6 in which the stabilising agent is present in an amount from 30% to 80% of the stoichiometric amount of phosethyl-Al.
8. A composition according to any one of claims 1 to 7 which comprises from 1 to 120 g/litre of phosethyl Al.
9. A composition according to claim 1 substantially as hereinbefore described in Example 1 or 2.
10. A process for the preparation of a stable aqueous solution comprising phosethyl Al according to any one of claims 1 to 9, which comprises adding a water-soluble zinc salt of a weak acid to an aqueous solution comprising phosethyl Al.
11. A process according to claim 10 substantially as hereinbefore described in Example 1.
12. A method of combating attacks by phytophagous fungi on crop plants which comprises applying to the plants an effective amount of a composition according to any one of claims 1 to 9.
13. A method according to claim 12 in which the composition is injected into the trunk of a crop tree or shrub.
14. A method according to claim 13 substantially as hereinbefore described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MYPI87002815A MY101391A (en) | 1984-08-29 | 1987-10-01 | Fungicidal composition based on aluminium tris - (ethyl phosphonate) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8413557A FR2569530B1 (en) | 1984-08-29 | 1984-08-29 | FUNGICIDAL COMPOSITION BASED ON ALUMINUM TRIS ETHYL PHOSPHONATE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8521365D0 GB8521365D0 (en) | 1985-10-02 |
| GB2163652A true GB2163652A (en) | 1986-03-05 |
| GB2163652B GB2163652B (en) | 1988-04-20 |
Family
ID=9307383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08521365A Expired GB2163652B (en) | 1984-08-29 | 1985-08-28 | Fungicidal composition based on aluminium tris-(ethyl phosphonate) |
Country Status (14)
| Country | Link |
|---|---|
| AU (1) | AU571995B2 (en) |
| BR (1) | BR8503988A (en) |
| EG (1) | EG17846A (en) |
| FR (1) | FR2569530B1 (en) |
| GB (1) | GB2163652B (en) |
| GR (1) | GR852006B (en) |
| HU (1) | HUT38204A (en) |
| IL (1) | IL75942A (en) |
| IT (1) | IT1186526B (en) |
| MA (1) | MA20509A1 (en) |
| MY (1) | MY101391A (en) |
| OA (1) | OA08084A (en) |
| PT (1) | PT81042B (en) |
| ZA (1) | ZA856518B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007878A1 (en) * | 1989-01-23 | 1990-07-26 | Rhone Poulenc Agro Kabushiki Kaisha | Stabilized pesticide composition |
| US5133891A (en) * | 1990-04-27 | 1992-07-28 | Rhone Poulenc Ag Co. | Treatment of plants for frost protection |
| GB2304708A (en) * | 1995-09-05 | 1997-03-26 | Rhone Poulenc Agrochimie | Improving the fruit yields from banana plants |
| US5656281A (en) * | 1989-12-14 | 1997-08-12 | Rhone-Poulenc Agrochimie | Water-dispersible granules of phosphite fungicidal products |
| WO2002102159A1 (en) * | 2001-06-20 | 2002-12-27 | Alastair James Forsyth | Plant treatment composition |
| WO2014095366A3 (en) * | 2012-12-18 | 2015-01-29 | Beiersdorf Ag | Improved protection against body odor |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL82311A (en) * | 1986-05-09 | 1992-06-21 | Rhone Poulenc Agrochimie | Bactericidal compositions based on phosphorous acid derivatives |
| CN112544619B (en) * | 2019-09-25 | 2022-04-12 | 沈阳中化农药化工研发有限公司 | Bactericidal composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1389940A (en) * | 1971-05-03 | 1975-04-09 | Rohm & Haas | Metal salt stabilized coating compositions |
| GB2137498A (en) * | 1983-03-31 | 1984-10-10 | Rhone Poulenc Agrochimie | Fungicidal compositions based on aluminium tris-(ethyl phosphonate) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2254276B1 (en) * | 1973-12-14 | 1977-03-04 | Philagro Sa |
-
1984
- 1984-08-29 FR FR8413557A patent/FR2569530B1/en not_active Expired
-
1985
- 1985-07-24 IT IT48404/85A patent/IT1186526B/en active
- 1985-07-29 IL IL75942A patent/IL75942A/en not_active IP Right Cessation
- 1985-08-14 OA OA58665A patent/OA08084A/en unknown
- 1985-08-19 GR GR852006A patent/GR852006B/el unknown
- 1985-08-21 MA MA20735A patent/MA20509A1/en unknown
- 1985-08-21 BR BR8503988A patent/BR8503988A/en unknown
- 1985-08-26 HU HU853228A patent/HUT38204A/en unknown
- 1985-08-27 ZA ZA856518A patent/ZA856518B/en unknown
- 1985-08-27 AU AU46696/85A patent/AU571995B2/en not_active Ceased
- 1985-08-28 PT PT81042A patent/PT81042B/en not_active IP Right Cessation
- 1985-08-28 GB GB08521365A patent/GB2163652B/en not_active Expired
- 1985-09-01 EG EG539/85A patent/EG17846A/en active
-
1987
- 1987-10-01 MY MYPI87002815A patent/MY101391A/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1389940A (en) * | 1971-05-03 | 1975-04-09 | Rohm & Haas | Metal salt stabilized coating compositions |
| GB2137498A (en) * | 1983-03-31 | 1984-10-10 | Rhone Poulenc Agrochimie | Fungicidal compositions based on aluminium tris-(ethyl phosphonate) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007878A1 (en) * | 1989-01-23 | 1990-07-26 | Rhone Poulenc Agro Kabushiki Kaisha | Stabilized pesticide composition |
| US5656281A (en) * | 1989-12-14 | 1997-08-12 | Rhone-Poulenc Agrochimie | Water-dispersible granules of phosphite fungicidal products |
| US5133891A (en) * | 1990-04-27 | 1992-07-28 | Rhone Poulenc Ag Co. | Treatment of plants for frost protection |
| GB2304708A (en) * | 1995-09-05 | 1997-03-26 | Rhone Poulenc Agrochimie | Improving the fruit yields from banana plants |
| GB2304708B (en) * | 1995-09-05 | 1999-03-17 | Rhone Poulenc Agrochimie | Method for improving fruit yields from banana plants |
| WO2002102159A1 (en) * | 2001-06-20 | 2002-12-27 | Alastair James Forsyth | Plant treatment composition |
| WO2014095366A3 (en) * | 2012-12-18 | 2015-01-29 | Beiersdorf Ag | Improved protection against body odor |
| AU2013361865B2 (en) * | 2012-12-18 | 2018-05-10 | Beiersdorf Ag | Improved protection against body odor |
Also Published As
| Publication number | Publication date |
|---|---|
| HUT38204A (en) | 1986-05-28 |
| IL75942A (en) | 1989-05-15 |
| EG17846A (en) | 1991-03-30 |
| PT81042B (en) | 1988-01-22 |
| AU4669685A (en) | 1986-03-06 |
| GR852006B (en) | 1985-12-19 |
| GB2163652B (en) | 1988-04-20 |
| BR8503988A (en) | 1986-06-10 |
| MA20509A1 (en) | 1986-04-01 |
| MY101391A (en) | 1991-10-23 |
| AU571995B2 (en) | 1988-04-28 |
| IT8548404A0 (en) | 1985-07-24 |
| PT81042A (en) | 1985-09-01 |
| IT1186526B (en) | 1987-11-26 |
| IL75942A0 (en) | 1985-12-31 |
| FR2569530B1 (en) | 1986-09-05 |
| GB8521365D0 (en) | 1985-10-02 |
| OA08084A (en) | 1987-03-31 |
| ZA856518B (en) | 1986-04-30 |
| FR2569530A1 (en) | 1986-03-07 |
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| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930828 |