AP82A - Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines. - Google Patents

Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines. Download PDF

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Publication number
AP82A
AP82A APAP/P/1987/000073A AP8700073A AP82A AP 82 A AP82 A AP 82A AP 8700073 A AP8700073 A AP 8700073A AP 82 A AP82 A AP 82A
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Prior art keywords
compounds
activity
insecticidal
percent
pyrazolines
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APAP/P/1987/000073A
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AP8700073A0 (en
Inventor
Neh Harribet Dr
Buhmann Ulrich Dr
Joppien Hartmut Dr
Giles David Dr
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Schering Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Pyrazolines of

Description

_1.- to new pyrazoline
The present invention relatesderivatives, their preparation and their use as pesticides.
Pyrazolines with insecticidal activity are alreadyknown (see for example DOS 23 04 584 and 25 29 689 as wellas EP 21 506 and 113 213).
This invention relates to pyrazoline derivatives havinginsecticidal and acaricidal activity.
In EP 21506, there are claimed pyrazoline compounds of formula
ap o n 0 0 8 2 wherein is, inter alia, a phenyl group or a halogensubstituted phenyl group, R2 is, inter alia. ahalogenoalkoxy having 1 to 6 carbon atoms and X and Y arehydrogen or halogen. Of the compounds where R^ is aphenyl group, two are described in which R* is a freephenyl group or a p-chlorophenyl group. R2 istrifluoromethoxy and X is chloro. All publishedcompounds, in which R^ is a halo substituted phenylgroup, have only X = chloro as the substituent on the - 1-.- bad original 2 phenyl group in the 3-position.
The object of the present invention is to provide pyrazoline derivatives that have a greater activity andbetter selectivity.
It has now been found that pyrazolines of general formula I„1
(I) 10 .1-5 Λ 15 20 whereinl 2 R and R are the same or different and are hydrogenor fluorine, have improved activity in comparison withknown pyrazolines.
In many cases they also have reduced mammaliantoxicity in comparison with known compounds of closely related structures.
The invention includes all isomeric forms and mixtures of these.
The compound of the invention of formula I can beprepared by reacting a pyrazoline of general formula II 25 - 2 -
BAD ORIGINAL
either
A) with an isocyanate of formula III F 2 C N = C = ( fill) optionally using a solvent, orB) with the reaction product from trichloromethyl
chloroformate and an aniline of formula IV
-NH. (IV) AP000062 optionally using a solvent, in which Rz has themeaning given in formula I.
Suitable solvents are liquids which are inert to thereactants such as aliphatic, alicyclic and aromatichydrocarbons, which can be optionally chlorinated, eghexane, cyclohexane, petroleum ether, benzene, toluene,xylene, dichloroomethane, chloroform, carbontetrachloride, 1,2-dichloroethane, trichloroethylene and - 3 - bad original &amp; 4 chlorobenzene; ethers, such as diethyl ether, methyl ethylether, diisopropyl ether, dibutyl ether, dioxane andtetrahyrofuran; nitriles, such as acetonitrile,propionitrile and benzonitrile; esters, such as ethyl 5 acetate and amyl acetate; amides, such asdimethylformamide, N-methylpyrrolidone orhexamethylphosphoric acid triamide, as well as sulphonesand sulphoxides, such as dimethyl sulphoxide andsulpholane . 10 The reaction variants A) and B) can be carried out over a wide temperature range. Generally, the temperatureis between -20°C and 100°C, preferably at room temperature.
The reaction can be carried out at normal atmosphericpressure but it can also be carried out at higher or 15 reduced pressures.
The compounds of the invention prepared by the aboveprocesses can be isolated from the reaction mixture inconventional mannor, for example by distillation of thesolvent at normal or reduced pressure, by precipitation 20 with water or by extraction. A higher degree of purity canas a general rule be achieved by column chromatography orby recrystallisation.
The pyrazoline derivitives of the invention arecolourless and odourless and in most cases, crystalline 25 compounds. They are highly insoluble in water and toluene.
BAD ORIGINAL slightly more soluble in ethyl acetate and highly solublein dimethylformamide.
The pyrazolines of formula II used as startingmaterials of are either known or can be prepared accordingto known processes.
The isocyanates of formula III used as startingmaterial in reaction variant A are either known or can beprepared according to known processes.
The anilines of formula IV used as starting materialin reaction variant B are either known or can be preparedaccording to known processes.
The compounds of the invention have insecticidal andacaricidal activity and are particularly useful incombating a variety of economically important insects, andacarids including animal ectoparasites. Examples includeLepidoptera, such as Plutella xylostella. Spodopteralittoralis, Heliothis armigera and Pieris brassicae;Diptera, such as Musca domestica. Ceratitis capitata,Erioischia brassicae, Luci1ia sericata and Aedes aeqypti;Homoptera, including aphids such as Megoura viciae andNilaparvata luqens; Coleoptera, such as Phaedoncochleariae, Anthonomus qrandis and Epilachna varivestisand corn rootworms (Diabrotica spp., e.g. Diabroticaundecimpunctata); Orthoptera, such as cockroaches e.g.Blattella qermanica: Hymenoptera, such as ants e.g. AP 0 0 0 0 8 2 5 - bad original 6 or
Monomorium pharaonis; mange mites, e.g. Sarcoptes spp.;ticks, such as Boophilus microplus and lice, such asDamalinia bovis and Linoqnathus vituli; as well as spider mites such as Tetranychus urticae and Panonychus ulmi. . 5 The compounds of the invention are distinguished by a surprisingly high level of activity against important pestspecies, especially pest insects, which represents avaluable improvement in the art.
The compounds according to the invention can be used10 at a concentration of 0.0005 to 5%, preferably from 0.001 to 1%, calculated as gram active material per 100 ml ofthe composition.
The compounds of the invention can be used eitheralone or in mixture with each other or another 15 insecticide. Optionally other plant protection or pesticidal compositions, such as for example insecticides,acaricides or fungicides can be added depending on the desired result.
An improvement in the intensity and speed of action 20 can be obtained, for example, by addition of suitable adjuvants, such as organic solvents, wetting agents andoils. Such additives may allow a decrease in the dose.
Suitable mixture partners may include phospholipids,e.g. phosphatidylcholine, hydrated phosphatidylcholines. 25 phosphatidylethanolamine, N-acyl-phosphatidylethanol- - 6 - BAD ORIGINAL &amp; 7 amines, phosphatidylinositol, phosphatidylserine,lysolecithin or phosphatidyiglycerol.
The designated active ingredients or their mixturescan suitably be used, for example, as powders, dusts, 5 granules, solutions, emulsions or suspensions, with theaddition of liquid and/or solid carriers and/or diluentsand, optionally, binding, wetting, emulsifying and/ordispersing adjuvants.
Suitable liquid carriers are, for example, water, 10 aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, cyclohexanone. isophorone, dimethylsulphoxide, dimethylformamide, other mineral-oil fractionsand plant oils.
Suitable solid carriers include mineral earths, e.g. 15 bentonite, silica gel, talcum, kaolin, attapulgite. limestone, silicic acid and plant products, e.g. flours.
As surface-active agents there can be used for example calcium 1ignosulphonate, polyoxyethylenealkylphenyl ether,naphthalenesulphonic acids and their salts, 20 phenolsulphonic acids and their salts, formaldehydecondensates, fatty alcohol sulphates, as well assubstituted benzenesulphonic acids and their salts.
The level of the respective active ingredients in thevarious preparations can vary over wide ranges. For 25 example the composition may contain about 10 to 90 percent AP 0 0 0 0 8 2 - 7 -
original 8 by weight of active ingredient, about 90 to 10 percentliquid or dry carriers, as well as optionally up to 20percent by weight of surfactant.
The composition can be applied in conventional manner.5 for example using water as the carrier in spray amounts of about 100 to 3000 litres/ha. Application in so called lowvolume or ultra-low-volume proceeses is possible as wellas by so-called microgranules.
Formulations can be prepared, for example, from the10 following ingredients.
A WETTABLE POWDER 20 percent by weight active ingredient35 percent by weight bentonite8 percent by weight calcium lignosulphonate15 2 percent by weight of the sodium salt of N-methyl-N-oleyltaurine35 percent by weight silicic acid
B PASTE 45 percent by weight active ingredient20 5 percent by weight sodium aluminium silicate 15 percent by weight cetylpolyglycol ether with 8moles ethylene oxide 2 percent by weight spindle oil10 percent by weight polyethylene glycol 25 23 parts water - 8 - BAD ORIGINAL Ά 9
C EMULSIFIABLE CONCENTRATE 20 percent by weight active ingredient75 percent by weight isophorone 5 percent by weight of an emulsifier mixture of calcium phenylsulphonate and fatty alcohol polyglycol ether
The following examples illustrate the preparation ofcompounds according to the invention.
Example 1 N- (4-Di fluoromethoxyphenyl]-3,4-bis-(4-fluorophenyl) - 4.5- dihydropyrazole-l-carboxamide 9.85 g (0.038 mol) 3.4-bis-(4-fluorophenyl)- 4.5- dihydropyrazole in 80 ml dichloromethane was treatedwith 7.03 g (0.038 mol) 4-difluoromethoxyphenylisocyanate, with stirring at room temperature and stirredfor an hour at room temperature. The reaction mixture wasfiltered through silica gel and the filtrate was concentrated. The residue was treated with 100 mldiisopropyl ether. The precipitated crystals wereseparated and dried in vacuo (100 Torr).
Yield: 14.7 g (87% of theory) M.p.: 144°C.
In a similar manner the following compounds wereobtained, in which the substitutents R1 and R2 havethe meanings given in formula I. AP 0 0 0 0 8 2 9
BAD ORIGINAL 10
Example
No . m.p. (°C)
2 F F 5
3 H F 135 145 140 10 <£» The following Examples illustrate the biological activity of the compounds of the invention,ζ" ** o
Jj Test Example A 15 Activity in curative treatment of broad beans (Vicia fabae L.) against black bean aphids (Aphis fabae scop.1
In a heated greenhouse, broad bean (Vicia fabae)seedlings (one plant per pot) were grown until about 6 cmhigh. The plants were then treated with cultures of black 20 bean aphids (Aphis fabae). After the plants had been colonised with 100 to 200 adults, they were sprayed untildripping wet with aqueous preparations of each activematerial containing 0.1% of active material and put in agreenhouse at about 24°C. After 2 days, the amount of 25 dead aphids was determined. The activity was calculated 10 BAU ORIGINAL 0 11 according to Abbott in comparison with several untreated
V control pots.
With the compounds of the invention of Examples l and4 an activity of more than 75¾ was achieved.
5 Test Example B
Activity in prophylactic treatment of leaves againstbrown rice-hoppers (Niliparvata luqens Stal)
In a heated greenhouse, rice seedlings (about 15 perpot) were grown until formation of the third leaf and then 10 sprayed until dripping wet with an aqueous preparationcontaining 0.1% of active material. After drying thesprayed leaves, a transparent cylinder was placed overeach pot. 30 Adult brown rice-hoppers (Niliparvata luqens)were introduced into each pot. After 2 days at 26°C in the 15 greenhouse, the amount of dead hoppers was determined.
The activity was calculated according to Abbott incomparison with several untreated control pots.
For the compounds of Examples 1-4 the activity reached ΔΡ 0 0 0 0 8 2 75-100%.
20 Test Example C
Activity against larvae of diamond-backed moth(Plutella xylostella).
Formulations of compounds of the invention were madeup with an active ingredient content of 0.0064%. The 25 desired concentration was achieved by diluting solutions
12 f >7.
;V -••Μ» in acetone or emulsifiable concentrates with water.
Cabbage leaves (Brassica oleracea qonqylodes), placed in polystyrene petri dishes, were sprayed with these2 preparations (4 mg spray/cm ). After the sprayed surface5 had dried. 10 young larvae of the diamond-backed moth (Plutella xylostella) were placed in each petri dish andthereby exposed to the treated food in the closed dishesfor two days. Feeding with untreated cabbage leaves thenfollowed for a further three days. The % mortality of the 10 larvae after five days indicated the level of activity.
Compounds according to Examples 1-4 showed an activity of 80-100%.
Test Example D
Activity against larvae (L 2) of the cotton army worm15 (Spodoptera 1ittoralis)
Formulations of compounds of the invention were madeup with an active ingredient content of 0.0064%. Thedesired concentration was achieved by diluting solutions in acetone or emulsifiable concentrates with water. 20 Leaflet pairs of beans (Vicia fabae) as well as 10 larvae (L 2) of the cotton army worm (Spodoptera littoralis) per2 experiment were sprayed with 4 mg spray/cm of thesepreparations in polystyrene petri dishes. The closed petridishes were left in the laboratory under extended daylight
13 leaves then followed for a further three days. The %mortality of the larvae after 5 days indicated the level of activity.
Compounds according to Examples 1-4 showed an activity 5 Of 80-100%.
Test Example E
Contact activity against larvae (L 2) of the cottonbollworm (Heliothis viriscens)
Formulations of compounds of the invention were made 10 up with an active ingredient content of 0.0064%. The desired concentration was achieved by diluting solutions in acetone or emulsifiable concentrates with water. The inner surface of petri dishes were sprayed with 4 mg2 spray/cm of these preparations. After drying the spray 15 coating, 5 larvae of the cotton bollworm (Heliothis viriscens per petri dish were exposed to the spray coatingfor 24 hours. After this the larvae were placed inuntreated petri dishes and fed with a non toxic artificialdiet for another 4 days. The tests were carried out in the 20 laboratory under extended daylight conditions. The % mortality of the larvae after 5 days indicated the levelof activity.
Compounds according to Examples 1-4 showed an activityof 80-100%. _ " 2 5 AP 0 0 0 0 8 2 bad original - 13 - 14 on •2» Λ >
Test Example F
Soil insecticide activity against eggs/larvae of thecorn rootworm (Diabrotica undecimpunctata)
Formulations of compounds of the invention were made5 up with an active ingredient content of 0.0064%. The desired concentration was achieved by diluting solutionsin acetone or emulsifiable concentrates with water. 20 mlof this preparation was poured into each plastic flowerpot (66 x 66 x 82 mm) each of which was filled with 200 ml 10 earth and ca. 100 eggs of the corn rootworm (Diabrotica undecimpunctata) as well as 2 grains of corn (Zea mays) ata depth of ca 1 cm of soil. The pots were left in theglasshouse under extended daylight conditions and at24-26°C for 14 days. The criterion for judging the 15 activity was the emergence of maize plants in untreatedpots with and without eggs within 14 days.
It was shown that compounds according to Examples 1-4gave undisturbed plant growth.
Test Example G 20 Insecticidal activity against sheep blowfly (Lucilia sericata) 1 ml Aliquots of an acetone solution containing testcompound at various concentrations were applied to cottonwool dental rolls 1 cm x 2 cm, contained in glass vials 25 (2 cm diameter x 5 cm long). After drying, the treated
bad original s 15 10 15 materials were then impregnated with 1 ml of nutrientsolution, infested with first instar larvae of sheepblowfly (Lucilia ser icata). closed by a cotton wool plug and held at 25°C for 24 hours.
At a concentration of 0.1 ppm compounds of Examples 1-3 gave 100¾ mortality. This mortality was reached at 3ppm with the compound of Example 4.
For the purposes of comparison, the compounds of EP21506 having the closest structure were also tested. Theseare compound 2: N-(4-trifluoromethoxyphenyl)-3- (4-chlorophenyl)-4-phenyl-4,5-dihydropyrazole-1-carboxamide,and compound 10: N-(4-trifluoromethoxyphenyl]-3-3,4-bis-(4-chlorophenyl )-4,5-dihydropyrazole-1-carboxamide.At 0.1 ppm, compound 2 gave 70¾ mortality and compound 10gave 20¾ mortality. ΛΡ Q 0 0 0 8 2 20 25 - 15 -
BAD ORIGINAL

Claims (3)

16 Cla ims 10
(I • .C !> 15 wherein1
2 R and R are the same or different and are hydrogen or fluorine. An insecticidal or acaricidal composition whichcomprises a compound claimed in claim 1, in admixturewith an agriculturally acceptable diluent or carrier.
3. A method for combating insects or acarids which20 comprises applying to the insect, acarid or their locus an effective amount of a compound claimed in claim 1. DATED this ^th day of November 1987· 25 Τ' - 16 - BAD ORIGINAL £
APAP/P/1987/000073A 1986-11-11 1987-11-09 Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines. AP82A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19863638631 DE3638631A1 (en) 1986-11-11 1986-11-11 PYRAZOLINE, THEIR PRODUCTION AND USE AS A MEDICINE WITH INSECTICIDAL AND ACARICIDAL EFFECT

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AP8700073A0 AP8700073A0 (en) 1987-11-01
AP82A true AP82A (en) 1990-05-30

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APAP/P/1987/000073A AP82A (en) 1986-11-11 1987-11-09 Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines.

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US (1) US4837220A (en)
EP (1) EP0267869B1 (en)
JP (1) JPS63135373A (en)
KR (1) KR880006201A (en)
CN (1) CN1016168B (en)
AP (1) AP82A (en)
AT (1) ATE78468T1 (en)
AU (1) AU602367B2 (en)
BR (1) BR8706059A (en)
CA (1) CA1266674A (en)
CS (1) CS264299B2 (en)
DD (1) DD265783A5 (en)
DE (2) DE3638631A1 (en)
DK (1) DK167012B1 (en)
ES (1) ES2043684T3 (en)
FI (1) FI874976A7 (en)
GR (1) GR3005908T3 (en)
HU (1) HU204791B (en)
IE (1) IE59525B1 (en)
IL (1) IL84330A (en)
NZ (1) NZ222468A (en)
OA (1) OA08774A (en)
PH (1) PH25609A (en)
PT (1) PT86104B (en)
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Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5116850A (en) * 1987-11-30 1992-05-26 E. I. Du Pont De Nemours And Co. Heterocyclic pyrazoline carboxanilides
DE3924112A1 (en) * 1989-07-20 1991-01-31 Bayer Ag FUNGICIDES BASED ON 1,3,5-TRIARYL-2-PYRAZOLINE DERIVATIVES, NEW 1,3,5-TRIARYL-2-PYRAZOLINES AND A METHOD FOR THE PRODUCTION THEREOF
AU7145591A (en) * 1990-01-31 1991-08-21 E.I. Du Pont De Nemours And Company Arthropodicidal pyrazolines, pyrazolidines and hydrazines
WO1993005024A1 (en) * 1991-08-28 1993-03-18 E.I. Du Pont De Nemours And Company Arthropodicidal anilides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1108154A (en) * 1979-07-03 1981-09-01 Roelof Van Hes Pyrazoline derivatives as insecticides
CA1111048A (en) * 1976-01-09 1981-10-20 Jan J. Van Daalen 1,3,4 substituted pyrazoline derivatives
CA1212118A (en) * 1982-12-30 1986-09-30 Fbc Limited Pyrazoline insecticides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4663341A (en) * 1984-02-16 1987-05-05 Rohm And Haas Company Insecticidal n-aryl-3-aryl-4,5-dihydro-1h-pyrazole-1-carboxamides
DE3545786A1 (en) * 1985-12-21 1987-06-25 Schering Ag Pyrazoline derivatives, their preparation, and their use as insecticides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1111048A (en) * 1976-01-09 1981-10-20 Jan J. Van Daalen 1,3,4 substituted pyrazoline derivatives
CA1108154A (en) * 1979-07-03 1981-09-01 Roelof Van Hes Pyrazoline derivatives as insecticides
CA1212118A (en) * 1982-12-30 1986-09-30 Fbc Limited Pyrazoline insecticides

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IL84330A0 (en) 1988-04-29
CS805687A2 (en) 1988-09-16
EP0267869B1 (en) 1992-07-22
IL84330A (en) 1991-08-16
IE59525B1 (en) 1994-03-09
CS264299B2 (en) 1989-06-13
BR8706059A (en) 1988-06-14
DK591687D0 (en) 1987-11-11
TR23185A (en) 1989-09-23
HU204791B (en) 1992-02-28
CA1266674A (en) 1990-03-13
HUT45020A (en) 1988-05-30
ES2043684T3 (en) 1994-01-01
US4837220A (en) 1989-06-06
DK591687A (en) 1988-05-12
OA08774A (en) 1989-03-31
CN1016168B (en) 1992-04-08
AU8099087A (en) 1988-05-12
PT86104A (en) 1987-12-01
FI874976A0 (en) 1987-11-11
KR880006201A (en) 1988-07-22
PT86104B (en) 1990-08-31
AU602367B2 (en) 1990-10-11
DE3780574D1 (en) 1992-08-27
GR3005908T3 (en) 1993-06-07
DE3638631A1 (en) 1988-05-26
DK167012B1 (en) 1993-08-16
PH25609A (en) 1991-08-08
CN87107752A (en) 1988-05-25
DE3780574T2 (en) 1993-01-21
DD265783A5 (en) 1989-03-15
JPS63135373A (en) 1988-06-07
IE873013L (en) 1988-05-11
EP0267869A1 (en) 1988-05-18
NZ222468A (en) 1990-10-26
FI874976A7 (en) 1988-05-12
AP8700073A0 (en) 1987-11-01
ZA878479B (en) 1988-05-09
ATE78468T1 (en) 1992-08-15

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