AP849A - Use of phenylpyrazole derivatives for surface treatment to control cockroaches or ants. - Google Patents

Use of phenylpyrazole derivatives for surface treatment to control cockroaches or ants. Download PDF

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Publication number
AP849A
AP849A APAP/P/1997/001103A AP9701103A AP849A AP 849 A AP849 A AP 849A AP 9701103 A AP9701103 A AP 9701103A AP 849 A AP849 A AP 849A
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Prior art keywords
alkyl
cockroaches
ants
radical
haloalkyl
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APAP/P/1997/001103A
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AP9701103A0 (en
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David Charles Twinn
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Rhone Poulenc Agriculture
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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Diabetes (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Hematology (AREA)
  • Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Use of 1-phenyl pyrazole derivatives for surface treatment to control cockroaches or ants.

Description

NEW METHOD-QF COMBATING, INSECTS
This invention relates to a new method of combating insects such as 5 cockroaches or ants at a locus connected to public health, that is to say at a locus frequented by humans, either private or public.
Many insecticidally active compounds are known, such as the insecticidal pyrazoles described in International Patent Publications No. WO 87/03781,
WO 93/06089 and WO 94/21606, as well as in European Patent Publications
0295117, 0403300, 0385809, and 0679650, German Patent Publication 19511269 and United States Patents 5,232,940 and 5,236,938. The use of such compounds to ΰΣ kill cockroaches or ants has already been contemplated, but such use was essentially m connection with baits or ingested materials or food that the insect is supposed to eat, or also in connection with direct contact application to the said insects.
The use of baits can be problematic because there is a need to place the baits at a proper locus where the cockroaches are supposed to come. Furthermore the baits can become a safety hazard to children, an undesirable situation.
An object of the instant invention is to provide a method of control of 20 cockroaches or ants avoiding the use of baits or ingestible material.
An object of the instant invention is to provide a method of control of cockroaches or ants avoiding the direct application of the active material to the insect itself, as with baits for example.
The object of the instant invention is to provide a simplified and efficient 25 method of control of cockroaches or ants.
The present invention is thus directed to a method of control of cockroaches or ants, preferably cockroaches, or of a population of cockroaches whereby an effective amount of an active ingredient which is a l-phenylpyra2ole derivative is applied to a surface on which the insect makes contact or moves or is moving or is expected to move.
The l-phenylpyrazole derivatives which can be used in the invention are generally compounds of formula (I):
AP/P/ 9 7/01103
APO Ο 0 8 4 s
Rn (I)' wherein :
R| may be CN or methyl;
R-2 may be S(O)nR3 ;
R3 may be alkyl or haloalkyi;
R4 represents a hydrogen or halogen atom; or a NR5R6, S(O)mR7, or C(O)O-R7, alkyl, haloalkyi or QRg radical; or a -N-C(R9)(Rjo) radical;
R5 and Rg, Independently, may be a hydrogen atom or a radical alkyl, haloalkyi, C(O)alkyl or S(O)rCF3; or R5 and Rg may form together a divalent alkylene radical which may be interrupted by one or more divalent heteroatoms such as oxygen or sulfur;
R7 may be an alkyl or haloalkyi radical;
Rg may be an alkyl or haloalkyi radical, or a hydrogen atom ;
R9 may be a hydrogen atom or an alkyl radical;
Rjq may be a phenyl or heteroaryl group, optionally substituted by one or more halogen atoms or group such as OH, -O-alkyl, -S-alkyl, cyano, or alkyl;
Rj (and R12 > independently, represent a hydrogen or halogen atom represent a halogen atom or a haloalkyi, haloalkoxy, S(O)qCF3 or SF5 group;
m,n,q,r may be independently be an integer equal to Ο, 1 or 2 ;
X represent a trivalent nitrogen atom or a C-R|2 radical, the three remaining free bonds of the carbon atom being part of the aromatic ring ;
provided that, when Rj is methyl, then R3 is haloalkyi, R4 is NH2, R11 is Cl
R131SCF3, andXisN.
The alkyl or acyl groups of the formula (I) are preferably lower alkyl or acyl, that is to say radicals having one to four carbon atoms.
AP/P/ 9 7/01103
APO Ο Ο 8 4 9
A preferred class of compounds of formula (Γ) comprises the compounds of formula (I) wherein Rj may be CN, and/or R3 may be haloalkyl, and/or R4 may be NH2, and/or Rj j and R 12 are independently a halogen atom, and Rj3 may be haloalkyl.
Still further preferred active ingredients which may be used in the . invention are those of formula (I) wherein Rj j and Rj2 are chlorine ; R3 and Rj3 are trifluoromethyl; R5 is amino.
Such most preferred insecticides are 5-amino-3-cyano-1-(2,6 dichloro-410 trifluoromethyl)phenyl-4-trifluoromethylsulfinylpyrazoIe (hereafter referred to as compound A), 5-amino-3-cyano-l -(2,6 dichloro-4-trifluoromethyl)phenyl-4trifluoromethylthiopyrazole pyrazole (hereafter referred to as compound B), 5amino-3-cyano-l -(2,6 dichloro-4-trifluoromethyl)phenyI-4trifluoromethylsulfonylpyrazole (hereafter referred to as compound C).
It should be understood that in the instant invention, the active ingredient is rather in the form of a thin layer or imbedded in a thin layer, and that this layer is covering totally or partially the surface where the insect is making contact or is moving or walking or going to walk or expected to be walking or supposed to be walking. Due to this thin layer the insect is not able to seize or bite or eat directly a discrete volume of composition comprising the ingredient of formula (I). This is connected with the unobviousness of the invention.
-According to a further aspect of the invention, it provides a method of control of a population of cockroaches or ants able to walk or travel in public or private housing or building or household or home, whereby a non seizable, but insecticidally effective, amount of active ingredient is lying on a surface located in the area to be treated.
According to a further aspect of the invention, it provides a method of control of a population of cockroaches or ants able to walk or travel in public or private housing or building or household or home, whereby a thin layer is covering the surface where the cockroaches or ants are supposed to walk.
According to a further aspect of the invention, it provides a method of control of a population of cockroaches or ants that are able to walk or travel in public or private housing or building or household or home, whereby the said . AP/P/ 9 7/01103
AP Ο Ο Ο 8 4 9 cockroaches or ants are caused to walk on a thin layer covering a surface in or near the area where the said insects are to be killed.
According to a preferred and most efficient embodiment, the invention is applied specifically to cockroaches.
The method of the invention is especially advantageous because it is very easy to apply the active ingredient, preferably by mean of spraying a liquid formulation to the appropriate surface.
The surface which is treated according to the invention.may be smooth or rough or rugged. Smooth surfaces are more effective. Various kinds of surface may be used such as glass, ceramics, concrete ; plastics surface such as vinyl plastics, melamine, linoleum ; metallic or wooden surface such as furniture ; textiles such as clothes.
The deposited layer of active ingredient according to the invention may be wet just after application, or may be dried or dry sometime after. The creation of this layer may be made by all known methods of covering, for example as a spray coat, paint, dip, wash, soak, lacquer, foam, dust, powder, aqueous suspension, paste, cream, wettable powder, aerosol, emulsifiable concentrate, concentrated suspension, flowable suspension, aqueous suspension, oil suspension, oil solution, pressure pack, or other standard formulation well known by those skilled in the art.
Compositions comprising an active ingredient of formula (I), especially liquid compositions, have already been described in the here above cited prior art.
Treatment of cockroaches in public health in public housing or building for the control of so-called American cockroaches fPeriplaneta americana). but also of other cockroaches like German cockroaches (BIatelia germanica). is a preferred feature of the instant invention,
The invention accordingly provides a method for controlling cockroaches or ants which comprises applying to a surface with which the cockroaches or ants make contact or are to make contact a compound of formula 1. The compound is preferably applied as a thin layer.
The preparation of compounds of formula (I) may be performed according to any process described in the here above cited patent applications, or other process according to the knowledge of a person skilled in the art of chemical synthesis.
AP/P/97/0 1 10 3
APO Ο Ο 8 4 8
The effective compositions which may be used in the invention may be offered or presented in different amounts. Usually, it is advantageous to offer the active compositions comprising the compound of formula (I) in an amount between 0.0001 g to 20 g per 100 square meters, preferably between 0.01 g and 10 g/100 m2.
The compositions which are useful in the invention (and which are to be spread on surfaces to control cockroaches or ants) comprise generally 0.0001 up to
15 % w/w of active ingredient, preferably from 0.1 to 6 w/w? They may be in the form of a liquid before application, especially in the form of an emulsifiable concentrate, aqueous emulsion, concentrated suspension or flowable suspension. But after drying of the liquid in the form of a thin layer.
The insecticidal compositions may also contain all kind of compatible surface active agent and/or carrier. Adjuvants may also be used, such as sticking agents, dyestuffs, film forming agent or the like, The carrier itself may be solid or liquid.
The compounds of formula (I) may be used in sequence or admixture, particularly admixtures with another pesticide e.g. an insecticide, acaricide or fungicide.
The compositions may be prepared by admixing the ingredients.
The invention is illustrated by the following examples which should not be considered as limiting or restricting the invention.
AP/P/ 9 7/01 103
EXAMPLE 1 30
Compounds A and B were dissolved in an acetone/water mixture and deposited on glass and left overnight to dry. The following results were observed :
COMPOUND DOSELEVEL mg/100 m2 Mortality % 90 min. after introduction of the cockroaches Mortality % 18 h. after introduction of the cockroaches
B 125 ioo 100
B 31 100 100
SUBSTITUTE SHEET {RULE 26)
APOΟ Ο 8 4 9
A
B 10 0 91
A 125 100 100
A 31 100 100
A 10 5 100
Example 2
Compound A was formulated as a 12.5 grams per liter liquid formulation in three compositions; (i) an emulsifiable concentrate (EC-wetting agent and an organic solvent); (ii) an aqueous emulsion (EW- wetting agent plus water plus an organic solvent); and (iii) a concentrated suspension (SC- dispersing agent and water). Each formulation was dissolved in water and deposited on samples of painted cement and plastic flooring (as described in Methode C.E.B, n° 159
Chapitre 11 / § 1, Methode d'essai d'efficacite practique de specialties insecticides destinees a la destruction des blattes dans les locaux Novembre 1992,” paragraph 2.6.) co provide deposits of 125 mg/100 nN 500 mg/100 m2, and 1250 mg/100 m2, Blattella germanica (German cockroaches) between 2 and 15 days old were placed on the surfaces for four hours and then removed, put in an untreated jar and observed after 96 hours from the beginning of the exposure. Each treatment was replicated 3 times. The following results were observed. Mortalities are reported as percentages of dead insects among living ones.
Formulation / Dose Mortality % on Plastic Mortality % on Cement
EC /125 mg/100 m2 10.2 100
EC/500 mg/100 m2 ., 100 100
EC / 1250 mg/100 m2 100 100
EW / 125 mg/100 m2 93.3 100
EW/500 mg/100 m2 88 95,7
EW / 1250 mg/100 m2 . 100 100
SC/125 mg/100m1 93.3 100
AP/P/ 9 7 / 0 1 1 0 3
-SUBSTITUTE SHEET .(RULE 26)
APOΟ 0 8 4 9
Ί
Γ--- SC/500 mg/100 m2 67.7 100
SC / 1250 mg/l00m2 100 100
Example 3
The samples of plastic flooring and cement of Example 2 were held at 25°C 5 in the dark for 24 hours. The infestation and observations of Example 2 were repeated. The following results were observed:
Formulation / Dose Mortality % on Plastic Mortality % on Cement
EC /125 mg/100 m2 14 100
EC/500 mg/100 m2 100 100
EC / 1250 mg/100 m2 100 100
EW /125 mg/100 m2 49 100
EW /500 mg/100 m2 74 100
EW / 1250 mg/100 m2 100 100
SC /125 mg/100 m2 43 100
SC/500 mg/100 m2 100 100
SC/ 1250 mg/100 m2 100 100
AP/P/ 9 7/01103
Example 4
The samples of plastic flooring and cement of Example 2 were held at 25°C in the dark for 14 days. The infestation and observations of Example 2 were repeated. The following results were observed:
Formulation 1 Dose Mortality % on Plastic Mortality % on Cement
EC/125 mg/100 m2 13.6 100
EC/500 mg/100 m2 100 100
EC/1250 mg/100 m2 100 100
EW / 125 mg/100 m2 37.7 100
EW / 500 mg/100 m2 77.7 100
EW / 1250 mg/100 m2 100 100
SC / 125 mg/100 m2 · 44.3 100
SC/500 mg/100 m2 100 100
SC / 1250 mg/100 m2 100 100
Example 5
The samples of plastic flooring and cement of Example 2 were held at 25°C 5 in the dark for 30 days. The infestation and observations of Example 2 were repeated. The following results were observed:
Formulation / Dose Mortality % on Plastic Mortality % on Cement
EC /125 mg/100 m2 6.7 72.3
EC/500 mg/100 m2 100 100
EC / 1250 mg/100 m2 100 100
EW / 125 mg/100 m2 53.3 100
EW / 500 mg/100 m2 S2.3 100
EW / 1250 mg/100 m2 100 100
SC/125 mg/100 m2 51 100
SC / 500 mg/100 m2 100 100
SC / 1250 mg/100 m2 100 100
AP/P/ 9 7/ 01103
Example 6
The samples of plastic flooring and cement of Example 2 were held at 25°C in the dark for 90 days. The infestation and observations of Example 2 were repeated. The following results were observed:
A»0 0 ο 8 4 9
Formulation I Dose Mortality % on Plastic Mortality % on Cement
EC /125 mg/100 m2 8.9 24.3
EC / 500 mg/100 m2 95,7 100
EC /1250 mg/100 m2 100 100
EW / 125 mg/100 m2 69 100
EW /500 mg/100 m2 95.7 100
EW / 1250 mg/100 m2 100 100
SC 1125 mg/100 m2 84.3 100
SC/500 mg/100 m2 100 100
SC / 1250 mg/100 m2 100 100
. . ,ν — .(Ο-* • '?
Example 7
The samples of plastic flooring and cement of Example 2 were held at 25°C 5 in the dark for 120 days. The infestation and observations of Example 2 were repeated. The following results were observed:
Formulation / Dose Mortality % on Plastic Mortality % on Cement
EC /125 mg/100 m2 4.3 8.8
EC/500 mg/100 m2 95.7 97.7
EC /1250 mg/100 m2 100 100
EW /125 mg/100 m2 69 100
EW / 500 mg/100 m2 88.7 100
EW / 1250 mg/100 m2 100 100
SC / 125 mg/100 m2 86.7 100
SC/500 mg/100 m2 100 100
SC / 1250 mg/100 m2 100 100
. AP/P/ 9 7/01103
Examples
APOΟ Ο 8 4 9
Μ.
The samples of plastic flooring and cement of Example 2 were held at 25°C in the dark for 180 days. The infestation and observations of Example 2 were repeated. The following results were observed:
Formulation / Dose Mortality % on Plastic Mortality % on Cement
EC / 125 mg/lOOm2 O O
EC/500mg/100m2 100 100
EC / 1250 mg/100 m2 100 100
EW /125 mg/100m2 60 100
EW/500 mg/100 m2 93.3 100
EW / 1250 mg/10Qm2 100 100
SC /125 mg/100 m2 24.4 75.5
SC / 500 mg/100 m2 100 100
SC /1250 mg/100 m2 100 100
Example 9
Porous concrete is impregnated with a 20 ppm solution acetone/water solution of Compound B and cockroaches (Blattella germanica) were permitted to walk on the surface. One day after treatment, the insects were observed. 50% of the insects had died.

Claims (12)

  1. I. Method of control of cockroaches or ants or of a population of cockroaches or ants wherein an effective amount of an active ingredient which is a 15 phenylpyrazole is applied to a surface on which the insect is moving or expected to move, the active ingredient being in the form of a thin layer or embedded in a thin layer, which layer the insect is not able to seize or bite or eat directly and wherein the 1-phenylpyrazole derivatives are compounds of formula (I):
    (I) wherein;
    Rj may be CN;
    R2 may be S(O)nR3;
    R3 may be alkyl or haloalkyl;
    R4 represents a hydrogen or halogen atom; or a NR5R<;, S(O)mR7, or C(O)OR7, alkyl, haloalkyl or ORg radical; or a -N=C(R9)(Ri0) radical;
    R5 and R<;, independently, may be a hydrogen atom or a radical alkyl, haloalkyl, C(O)alkyl or S(O)rCF3; or R5 and R<; may form together a divalent alkylene radical which may be interrupted by one or more divalent heteroatoms such as oxygen or sulfur;
    R7 may be an alkyl or haloalkyl radical;
    R8 may be an alkyl or haloalkyl radical, or a hydrogen atom;
    s 01 I 0 / L 6 /d/dV
    -12R-9 may be a hydrogen atom or an alkyl radical;
    R,„ may be a phenyl or heteroaryl group, optionally substituted by one or more halogen atoms or group such as OH, O-alkyl, -S-alkyl, cyano, or alkyl;
    R,, and RI2, independently, represent a hydrogen or halogen atom ;
    Rl3 represent a halogen atom or a haloalkyl, haloalkoxy, S(0)qCF, or SF5 group;
    m, n, q, r may be independently an integer equal to 0, l or 2;
    X represent a trivalent nitrogen atom or a C-R12 radical, the three remaining free bonds of the carbon atom being part of the aromatic ring;
  2. 2. Method of control according to claim 1 wherein R3 may be haloalkyl, and/or R4 may be NH2, and /or Rn and RI2 are independently a halogen atom, and RI3 may be haloalkyl.
    15
  3. 3. Method of control according to claim 1 or 2 wherein Rn and R12 are chlorine;
    R3 and RI3 are trifluoromethyl; R5 is amino.
  4. 4. Method of control according to any one of the foregoing claims which is a method of control of a population of cockroaches or ants able to walk or travel in
    20 public or private housing or buildings or household or home.
  5. 5. Method of control according to any one of the foregoing claims which is a method of control of a population of cockroaches or ants able to walk or travel in public or private housing or buildings or household or home, wherein the said
    25 cockroaches or ants are caused to walk on a thin layer covering a surface in or near the area where the said insects are to be killed.
  6. 6. Method according to any one of the foregoing claims when applied to cockroaches.
    AP/P/ 97/01103
  7. 7.
    Method according to any one of the foregoing claims wherein the insecticidal
    AP Ο Ο Ο 8 4 9
    -13compositions comprising the compound of formula (I) in an appropriate form are applied in an amount from 0.0001 g to 20 g per 100 square metres.
  8. 8 Method according to any one of the foregoing claims wherein the insecticidal 5 compositions comprising the compound of formula (I) in an appropriate form are applied in an amount from 0.01 g to 10 g per 100 square metres.
  9. 9. Method according to any one of the foregoing claims wherein the insecticidal compositions comprise from 0.0001 to 15% w/w of active ingredient.
  10. 10. Method according to any one of the foregoing claims wherein the insecticidal compositions comprise from 0.1 to 6% w/w of active ingredient.
  11. 11. A composition for the control of cockroaches or ants which comprises from
    15 0.0001 to 15% w/w of active ingredient as defined in any one of claims 1 to 3 in the form of a thin layer as defined in claim 1.
  12. 12. A composition according to claim 1 which comprises from 0.1 to 6% w/w of ' active ingredient.
APAP/P/1997/001103A 1995-04-05 1996-03-27 Use of phenylpyrazole derivatives for surface treatment to control cockroaches or ants. AP849A (en)

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GBGB9507073.6A GB9507073D0 (en) 1995-04-05 1995-04-05 New method of combating insects

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AP849A true AP849A (en) 2000-06-13

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JPH0987111A (en) * 1995-09-27 1997-03-31 Sumitomo Chem Co Ltd Poison bait for pest control
EP0845211B1 (en) * 1996-11-29 2003-10-01 Bayer CropScience S.A. Protection of buildings against termites by 1-Arylpyrazoles
US5906983A (en) * 1997-08-20 1999-05-25 The Clorox Company High fructose containing insecticide compositions and methods of using the same
BR9705278A (en) * 1997-10-15 1999-05-25 Rhone Poulenc Agrochimie Composition method to control cut leaf ants and commercial product
EP2424370A2 (en) * 2009-04-28 2012-03-07 BASF Corporation Foamable pesticide compositions
EP3868193A4 (en) 2018-10-18 2022-07-13 Sumitomo Chemical Company, Limited PHENYLPYRAZOLE COMPOUND AND METHOD FOR CONTROLLING PLANT DISEASE

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WO1992013451A1 (en) * 1991-02-11 1992-08-20 Schering Agrochemicals Limited Imidazole pesticides
EP0500209A1 (en) * 1991-01-18 1992-08-26 Rhone-Poulenc Agrochimie Pesticidal 1-(2-pyridyl)pyrazoles

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Publication number Priority date Publication date Assignee Title
EP0295117A1 (en) * 1987-06-12 1988-12-14 Rhone-Poulenc Agriculture Limited Derivatives of N-phenylpyrazoles
EP0500209A1 (en) * 1991-01-18 1992-08-26 Rhone-Poulenc Agrochimie Pesticidal 1-(2-pyridyl)pyrazoles
WO1992013451A1 (en) * 1991-02-11 1992-08-20 Schering Agrochemicals Limited Imidazole pesticides

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HUP9801558A2 (en) 1998-11-30
CZ313997A3 (en) 1998-02-18
EP0818952A1 (en) 1998-01-21
MY117634A (en) 2004-07-31
PL322659A1 (en) 1998-02-16
AU5274396A (en) 1996-10-23
SG40858A1 (en) 1997-06-14
WO1996031123A1 (en) 1996-10-10
ATE306815T1 (en) 2005-11-15
HUP9801558A3 (en) 1999-03-29
ZA962444B (en) 1996-11-18
NZ304867A (en) 1999-11-29
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