AU601734B2 – Bactericidal compositions based on phosphorous acid derivatives
– Google Patents
AU601734B2 – Bactericidal compositions based on phosphorous acid derivatives
– Google Patents
Bactericidal compositions based on phosphorous acid derivatives
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Publication number
AU601734B2
AU601734B2
AU72530/87A
AU7253087A
AU601734B2
AU 601734 B2
AU601734 B2
AU 601734B2
AU 72530/87 A
AU72530/87 A
AU 72530/87A
AU 7253087 A
AU7253087 A
AU 7253087A
AU 601734 B2
AU601734 B2
AU 601734B2
Authority
AU
Australia
Prior art keywords
xanthomonas
plants
formula
bacterial disease
erwinia
Prior art date
1986-05-09
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
Application number
AU72530/87A
Other versions
AU7253087A
(en
Inventor
Brian L. Tepper
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience SA
Original Assignee
Rhone Poulenc Agrochimie SA
Priority date (The priority date 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 date listed.)
1986-05-09
Filing date
1987-05-06
Publication date
1990-09-20
1987-05-06
Application filed by Rhone Poulenc Agrochimie SA
filed
Critical
Rhone Poulenc Agrochimie SA
1987-11-12
Publication of AU7253087A
publication
Critical
patent/AU7253087A/en
1990-09-20
Application granted
granted
Critical
1990-09-20
Publication of AU601734B2
publication
Critical
patent/AU601734B2/en
1999-12-16
Assigned to RHONE-POULENC AGRO
reassignment
RHONE-POULENC AGRO
Request to Amend Deed and Register
Assignors: RHONE-POULENC AGROCHIMIE
2007-05-06
Anticipated expiration
legal-status
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Status
Expired
legal-status
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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
A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
A01N59/26—Phosphorus; Compounds thereof
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
Abstract
Bactericidal compositions contain, as active substance, a derivative of the formula
Description
601734 FORM COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952-1973 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE: Class Int Class Application Number: 7 2 Lodged: Complete Specification Lodged: Accepted: Published: Priority: Related Art: F’ 7 «alc~idiel)tS linau- Ur’, j. L s. cr et fo r, sning Name of Applicant: Address of Applicant: Actual Inventor(s): RHONE POULENC AGROCHIMIE 14-20, Rue Pierre Baizet, 69009 LYON, France.
BRIAN L. TEPPER 2 Address for Service: Davies and Collison, 1 Little Collins Street, Melbourne, Victoria 3000, Australia.
Complete Specification for the invention entitled: «BACTERICIDAL COMPOSITIONS BASED ON PHOSPHOROUS ACID
DERIVATIVES»
The following statement is a full description of this invention, including the best method of performing it known to us:- Li la- The present invention relates to new bactericidal compositions based on phosphorous acid derivatives and a method of treatment of plants with these derivatives to control bacterial diseases.
It is known to use phosphorous acid, its salts and salts of some of its monoesters, namely aluminium tris-0-ethylphosphonate, as an active ingredient effective against plant fungal diseases. These compounds have, however, not heretofore been known to possess bactericidal properties and in particular it has not been known or suggested that the compounds might possess utility in the o 00* treatment of bacterial diseases of plants.
O B 0 The present invention provides a bactericidal composition comprising as active ingredient a compound of 00oo 15 the formula:
H
00n+ S(R P 0 M (I) o. II n 0 0 a 00 0 1 in which: i h R is hydroxy, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms, M is an alkali metal, alkaline earth metal or aluminium atom, or, when R is hydroxy, M may represent hydrogen, and n is an integer from 1 to 3, M being the same or different when n is more than 1, in association with an agriculturally acceptable carrier 2 or diluent and/or an agriculturally acceptable I surface-active agent.
Amongst the compounds of formula monosodium or monopotassium and disodium or dipotassium phosphites and sodium, potassium, calcium and aluminium O-ethyl-phosphites are preferred. Aluminium tris-O-ethyl-phosphonate is especially preferred.
The invention relates also to the control of bacterial disease in plants by applying the above-mentioned compounds of formula i The bactericidal properties of the compounds of formula I and of the compositions containing them are Sillustrated in the following Examples.
Example 1 Tomato plants, arranged in groups of three per pot (diameter 15 cm), were contaminated by Xanthomonas l campestris and incubated at 28 C during 24 hours in polyethylene bags. Then the plants were sprayed to run-off with an aqueous dispersion of a commercially available wettable powder (ALIETTE 80 WP) containing 80% by weight of aluminium tris-0-ethylphosphonate fosethyl-Al).
The activity was observed by counting the leaf spots on all plants by choosing the most infested leaf.
In these conditions it was observed that whcreas on the control (contaminated and not treated) 281 leaf spots can be counted, only 45 can be counted on plants treated with fosethyl Al at a rate of 2.2 kg/ha of active i L 3- 3 ingredient. The efficacy was comparable to that obtained with the commercial standard based on copper hydroxide.
This test shows the excellent bactericidal properties of the compounds used according to the invention.
Example 2 Test in vitro on phytopathogenic bacteria The activity of the compounds according to the invention is tested on the following phytopathogenic bacteria: Xanthomonas campestris campestris Xanthomonas campestris citri Xanthomonas campestris malvacearum i Xanthomonas campestris oryzae i Erwinia amylovora Erwinia carotovora atroseptica Erwinia carotovora carotovora Erwinia chrysanthemi Pseudomonas syringae persicae Pseudomonas syringae lachrymans Pseudomonas syringae tomato Corynebacterium michiganense For each test, the procedure is as follows: a nutrient medium (Sahouraud medium) consisting of peptone (10 glucose (20 g/l) and agar (15 g/1) is introduced a 4 Ssupercooled into a series of Petri dishes (20 cc per dish) 1after sterilization in an autoclave at 120 C.
SDuring the filling of dishes, an aqueous solution i of phosethyl-Al is injected into the supercooled medium, to obtain the desired concentration.
Petri dishes similar to the above, into which are poured similar quantities of a nutrient medium which does not contain the active substance, are taken as control.
After 24 or 48 h each dish is seeded by depositing a bacteria-containing aqueous suspension obtained by 100-fold dilution of a suspension having an optical density equal to 1.
The dishes are stored for 2 to 10 days (depending on the bacteria being tested) at 22 0 C, and the growth of the bacteria in the dishes containing the active substance to be tested is compared with that of the control.
Under these conditions, for each bacteria tested, a complete (100 inhibition of the bacteria is observed, Sat a dose of 100 ppm.
Thus, the compounds and compositions of the Spresent invention may be used for the control of bacterial diseases in plants, such as those caused by Xanthomonas spp., especially Xanthomonas campestris pv, for example Xanthomonas campestris campestris, Xanthomonas campestris citri, Xanthomonas campestris malvacearum, Xanthomonas campestris oryzae or Xanthomonas geranii, or by Erwinia spp., especially Erwinia amylovora, Erwinia carotovora I- 5 -5atroseptica, Erwinia carotovora carotovora, Erwinia chrysanthemi, or by Pseudomonas spp., especially Pseudomonas syringae pv. for example Pseudomonas syringae morsprunorum subsp. persicae, Pseudomonas syringae lachrymans or Pseudomonas syringae tomato, or Pseudomonas solanacearum, or by Corynebacterium spp., especially Corynebacterium michiganense.
The composition and method of the invention are of particular interest in combating bacterial disease caused by Xanthomonas campestris or Xanthomonas citri.
Thus these diseases can be cured on various plants such as vegetables e.g. cabbage, radish, turnip, celery, potato, tomato, carrot, endive, bean, cucurbits, cereals e.g. small grains (such as wheat or rice), maize, fruit trees or plants e.g. pear, apple, peach, non-food crops such as tobacco and cotton, ornamentals and turf.
6 For their use in practice, the compounds used according to the invention are not generally employed by themselves.
Most frequently, they are used in compositions which generally comprise, in addition to the active ingredient, an inert carrier (or diluent) and/or a surface-active agent which are compatible with the active ingredient.
The compositions usually contain from 0.001 to 95% by weight of active ingredient. They generally contain between 0.1% and 20% by weight of surface-active agent.
In the present account, the term «carrier» denotes an organic or inorganic, natural or synthetic material with which the active ingredient is combined in order to facilitate its application to the plant, to seeds or to the soil. This carrier is therefore generally inert and it must be acceptable in agriculture, in particular on the plant treated. The carrier can be solid (clays, natural or synthetic silicates, silica, chalks, resins, waxes, solid fertilisers, etc.) or Liquid (water, alcohols, ketones, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorohydrocarbons, Liquefied gases, etc.).
The surface-active agent can be an emulsifying, dispersing or wetting agent of ionic or non-ionic type.
Examples which may be mentioned are polyacrylic acid salts, LignosuLphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide with fatty alcohols, fatty acids, fatty amines or substituted phenols (in particular alkylphenols, arylphenols -7 or styrylphenol), salts of sulphosuccinic acid esters, taurine derivatives (in particular alkyLtaurates) and phosphoric acid esters of condensates of ethylene oxide with alcohols or phenoLs. The presence of at least one surface-active agent is generally essential, especially if the inert carrier is not soluble in water and if the vehicle of application is water.
The compositions used in the invention can be in a fairly wide variety of solid or liquid forms.
As forms of solid compositions there may be mentioned dusting powders or sprinkling powders (with an active ingredient content which can range up to 100%).
As forms of liquid compositions or compositions which-are to be made up into liquid compositions on applithere may be mentioned solutions, in particular water-soluble concentrates, emulsifiable concentrates, emulsions, suspension concentrates, aerosols, wettable powders (or spraying powders) and pastes.
The emulsifiable or soluble concentrates most comprise 10 to 90% of active ingredient, and the emulsions or solutions which are ready for application contain 0.001 to 20% of active ingredient. In addition to the solvent, and where necessary, the emulsifiable concentrates can contain 2 to 20% of suitable additives such as stabilisers, surface-active agents, penetrating agents, corrosion inhibitors, dyestuffs and adhesives.
Starting from these concentrates, emulsions of any desired 8 concentration, which are particuLarly suitable for application to the Leaves, can be obtained by dilution with water.
The suspension concentrates, which can also be applied by spraying, are prepared so as to give a stable fluid product which does not form a deposit, and they Susually contain from 10 to 75% of active ingredients, from i 0.5 to 15% of surface-active agents, from 0.1 to 10% of thixotropic agents, from 0 to 10% of suitable additives such as anti-foam agents, corrosion inhibitors, stabil- Sisers, penetrating agents and adhesives, and, as the carrier, water or an organic liquid in which the active ingredient is sparingly soluble or insoluble; certain organic solids, or inorganic salts, can be dissolved in the carrier in order to assist in preventing sedimentation or to act as anti-freeze agents for the water.
The wettaL.e powders (or spraying powders) are usually prepared so as to contain 20 to 95% of active ingredients, and they usually contain, in addition to the carrier, from 0 to 5% of a wetting agent, from 3 i to 10% of a dispersing agent and, where necessary, from 0 to 10% of one or more stabilisers and/or other additives such as penetrating agents, adhesives, anti-caking agents, dyestuffs, etc.
Various compositions of wettable powders are now given as examples: Example 3: *i 9 active ingredient .50 ethyLene oxide/fatty alcohoL condensate (wetting agent) ethylene oxide/styryLphenoL condensate (dispersing agent) 5 chaLk (inert carrier) 42.5% Another example of a wettable powder has the following composition:Example 4: active ingredient phosethyl-AL 88.3% ethylene oxide/fatty alcohol condensate (wetting agent) 5.7% ethylene oxide/styryphenol condensate (dispersing agent) 6 To obtain these spraying powders or wettable powders, the active ingredient is intimately mixed with the additional substances in suitable mixers and the mixture is ground in mills or other suitable grinders. This gives spraying powders of advantageous wettability and suspendability; they can be suspended in water at any desired concentration and this suspension can be used very advantageously, in particular for application to the leaves of the plants.
As already stated, the aqueous dispersions and aqueous emulsions, e.g. compcctions obtained by diluting, U with water, a wettable powder or an emulsifiable concentrate according to the invention, are included within the general scope of the present invention. The emulsions can be of the water-in-oil or oil-in-water type and they can have a thick consistency sucl- aat of a «mayonnaise».
i The granules, which are intended to be placed on the soil, are usually prepared so as to have dimensions of between 0.1 and 2 mm, and they can be manufactured by agglomeration or impregnation. In general, the granules contain 0.5 to 25% of active ingredient and 0 to 10% of additives such as stabilisers, slow release modifiers, binders and solvents.
The compounds of the formula can also be used in the form of dusting powders; thus, it is possible to use a composition comprising 50 g of active ingredient and 950 g of talc; it is also possible to use a composition comprising 20 g of active ingredient, 10 g of finely divided silica and 970 g of talc; these constituents are mixed and ground and the mixture is applied by dusting.
The invention also relates to a method for treating plants against phytopathogenic bacteria which I si method comprises applying to the plants an effective amount of a composition containing a compound according to the formula as the active ingredient. The term «effective amount» is understood as meaning a sufficient amount to enable the bacteria present on these plants to be 11 controlled or destroyed. However, the use doses can vary within wide limits, according to the bacteria to be combated, the type of crop and the climatic conditions. AS will be readily appreciated the method of the invention may be used to combat bacterial diseases of plants which are either not infested with fungus or are not susceptible to fungal infestation.
The invention provides a method for the control of bacterial disease on plants at a locus which comprises applying thereto an effective amount of a compound of formula The invention also provides such a method preceded by the step of determining that the plants are suffering from or subject to bacterial disease.
i |i )j _j
Claims (7)
1.2 12 THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS: 1. A method for the control of bacterial disease on plants at a locus which comprises applying thereto.an effective amount of a bactericidal composition comprising as active ingredient, a compound of the formula: H (R P 0 Mn+ (I) 0 in which: R is hydroxy, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms, M is an alkali metal, alkaline earth metal or aluminium atom, or, when R is hydroxy, M may represent hydrogen, and n is an integer from 1-to 3, M being the same or different, when n is more than 1, in association with an agriculturally acceptable diluent or carrier and/or an agriculturally acceptable surface-active agent.
2. A method according to claim 1 wherein the compound of formula is monosodium, monopotassium, disodium or dipotassium phosphite or sodium, potassium, calcium or aluminium O-ethyl-phosphite. i 3. A method according to claim 1, wherein the compound of the formula is aluminium tris-0-ethyl- phosphonate.
4. A method according to claim 1 substantially as hereinbefore described in Example 3 or 4. A method according to claim 1 in which the S .ASAT.550-.r, ^v~3qC ^Q702o~.PSOT.05l 7508.r 2 13 bacterial disease is caused by Xanthomonas campestris campestris, Xanthomonas campestris citri, Xanthomonas campestris malvacearum, Xanthomonas campestris oryzae, Xanthomonas geranii, Erwinia amylovora, Erwinia carotovora atroseptica, Erwinia carotovora carotovora, Erwinia chrysanthemi, Pseudomonas syringae morsporunorum subsp persicae, Pseudomonas syringae lachrymans, Pseudomonas syringae tomato, Pseudomonas solanacearum or h Corynebacterium michiganense.
6. A method according to claim 5 in which the bacterial disease is caused by Xanthomonas capestris or Xanthomonas citri.
7. A method according to claim 1 preceded by the step of determining that the plants are suffering from or subject to bacterial disease.
8. A method according to any one of claims 5 to 7 ccoo substantially as hereinbefore described. on 0 DATED this 2nd day of July, 1990 0. Sc»‘ RHONE-POULENC AGROCHIMIE by its Patent Attorneys Coo’ DAVIES COLLISON C
900709.PASDAT035.7253Q-87,rs0 13
AU72530/87A
1986-05-09
1987-05-06
Bactericidal compositions based on phosphorous acid derivatives
Expired
AU601734B2
(en)
Applications Claiming Priority (2)
Application Number
Priority Date
Filing Date
Title
US86154386A
1986-05-09
1986-05-09
US861543
1986-05-09
Publications (2)
Publication Number
Publication Date
AU7253087A
AU7253087A
(en)
1987-11-12
AU601734B2
true
AU601734B2
(en)
1990-09-20
Family
ID=25336097
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
AU72530/87A
Expired
AU601734B2
(en)
1986-05-09
1987-05-06
Bactericidal compositions based on phosphorous acid derivatives
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EP
(1)
EP0249566B1
(en)
JP
(1)
JPH0796484B2
(en)
KR
(1)
KR870010782A
(en)
CN
(1)
CN1022160C
(en)
AT
(1)
ATE70160T1
(en)
AU
(1)
AU601734B2
(en)
BR
(1)
BR8702354A
(en)
CS
(1)
CS270564B2
(en)
DD
(1)
DD259562A5
(en)
DE
(1)
DE3775118D1
(en)
DK
(1)
DK234987A
(en)
EG
(1)
EG18317A
(en)
ES
(1)
ES2026935T3
(en)
GR
(1)
GR3003325T3
(en)
HU
(2)
HU205841B
(en)
IL
(1)
IL82311A
(en)
MA
(1)
MA20968A1
(en)
MY
(1)
MY102853A
(en)
NZ
(1)
NZ220216A
(en)
OA
(1)
OA08593A
(en)
PH
(1)
PH22407A
(en)
PT
(1)
PT84845B
(en)
SU
(1)
SU1588265A3
(en)
TR
(1)
TR24619A
(en)
ZA
(1)
ZA873243B
(en)
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Biocidal delivery system of phosphate ester and method of preparation thereof
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1989-01-23
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Stabilized pesticide composition
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1989-12-14
1994-04-29
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DISPERSABLE GRANULES OF FUNGICIDE PRODUCTS.
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*
1990-04-27
1992-07-28
Rhone Poulenc Ag Co.
Treatment of plants for frost protection
US5206228A
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*
1991-10-29
1993-04-27
Rhone-Poulenc Ag Company
Control of arthropod pests with phosphorous acid and mono-esters and salts thereof
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1993-06-05
1998-12-30
杨德山
‘Shuangteling’ bactericide
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1995-04-03
1997-02-04
Rhone-Poulenc, Inc.
Fungicidal compositions for the enhancement of turf quality
FR2738112B1
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*
1995-09-05
1997-09-26
Rhone Poulenc Agrochimie
METHOD FOR IMPROVING BANANA FRUIT YIELDS
AU749429B2
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*
1996-06-19
2002-06-27
Bayer S.A.S.
Method for improving the health of banana plants
IL129528A0
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*
1999-04-20
2000-02-29
Luxembourg Ind Pamol Ltd
Pesticides
US20110052720A1
(en)
*
2007-12-20
2011-03-03
Wim Van Der Krieken
Compositions for the control of plant pathogens and for use as plant fertilizer
US8546360B2
(en)
2008-04-22
2013-10-01
Bayer Cropscience Lp
Method of treating citrus plants to reduce bacterial infections
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MEANS FOR CONTROLLING PHYTOPATHOGENIC MICROORGANISMS
1987
1987-04-23
IL
IL82311A
patent/IL82311A/en
not_active
IP Right Cessation
1987-05-04
DE
DE8787420118T
patent/DE3775118D1/en
not_active
Expired – Lifetime
1987-05-04
AT
AT87420118T
patent/ATE70160T1/en
not_active
IP Right Cessation
1987-05-04
EP
EP87420118A
patent/EP0249566B1/en
not_active
Expired – Lifetime
1987-05-04
ES
ES198787420118T
patent/ES2026935T3/en
not_active
Expired – Lifetime
1987-05-05
CS
CS873156A
patent/CS270564B2/en
not_active
IP Right Cessation
1987-05-06
ZA
ZA873243A
patent/ZA873243B/en
unknown
1987-05-06
AU
AU72530/87A
patent/AU601734B2/en
not_active
Expired
1987-05-06
TR
TR87/0316A
patent/TR24619A/en
unknown
1987-05-06
MY
MYPI87000586A
patent/MY102853A/en
unknown
1987-05-06
MA
MA21206A
patent/MA20968A1/en
unknown
1987-05-06
EG
EG264/87A
patent/EG18317A/en
active
1987-05-06
NZ
NZ220216A
patent/NZ220216A/en
unknown
1987-05-06
JP
JP62110413A
patent/JPH0796484B2/en
not_active
Expired – Lifetime
1987-05-08
PH
PH35234A
patent/PH22407A/en
unknown
1987-05-08
DD
DD87302571A
patent/DD259562A5/en
not_active
IP Right Cessation
1987-05-08
DK
DK234987A
patent/DK234987A/en
not_active
Application Discontinuation
1987-05-08
OA
OA59116A
patent/OA08593A/en
unknown
1987-05-08
PT
PT84845A
patent/PT84845B/en
unknown
1987-05-08
HU
HU901193A
patent/HU205841B/en
unknown
1987-05-08
KR
KR870004532A
patent/KR870010782A/en
not_active
Application Discontinuation
1987-05-08
HU
HU872080A
patent/HU200266B/en
unknown
1987-05-08
CN
CN87103407A
patent/CN1022160C/en
not_active
Expired – Lifetime
1987-05-08
SU
SU874202541A
patent/SU1588265A3/en
active
1987-05-08
BR
BR8702354A
patent/BR8702354A/en
not_active
IP Right Cessation
1991
1991-12-12
GR
GR91401025T
patent/GR3003325T3/en
unknown
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Title
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(en)
*
1984-08-29
1988-04-28
Rhone-Poulenc Agrochimie
Fungicidal composition based on aluminium tris (ethyl phosphonate)
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Publication number
Publication date
PT84845A
(en)
1987-06-01
AU7253087A
(en)
1987-11-12
ES2026935T3
(en)
1992-05-16
HU200266B
(en)
1990-05-28
CN87103407A
(en)
1988-01-20
MY102853A
(en)
1993-03-31
EP0249566B1
(en)
1991-12-11
PH22407A
(en)
1988-08-26
IL82311A0
(en)
1987-10-30
KR870010782A
(en)
1987-12-18
NZ220216A
(en)
1989-10-27
TR24619A
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1991-12-24
GR3003325T3
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1993-02-17
DE3775118D1
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1992-01-23
ATE70160T1
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1991-12-15
EG18317A
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1992-12-30
SU1588265A3
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1990-08-23
ZA873243B
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1987-10-29
JPS62281808A
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1987-12-07
CS270564B2
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1990-07-12
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1989-11-14
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1992-07-28
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1992-06-21
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1989-01-30
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1987-12-16
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1988-08-31
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1988-11-30
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1988-02-17
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1990-05-28
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1995-10-18
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1987-12-31
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1990-02-08
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1987-11-10
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1993-09-22
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1987-05-08
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