AP82A - Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines. - Google Patents
Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines. Download PDFInfo
- 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
- Authority
- AP
- ARIPO
- Prior art keywords
- compounds
- activity
- insecticidal
- percent
- pyrazolines
- Prior art date
Links
- 230000000749 insecticidal effect Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 14
- 241000238631 Hexapoda Species 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000003219 pyrazolines Chemical class 0.000 abstract description 8
- 230000000694 effects Effects 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
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- 239000004480 active ingredient Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 238000009472 formulation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
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- 238000007865 diluting Methods 0.000 description 4
- 235000021186 dishes Nutrition 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 240000007124 Brassica oleracea Species 0.000 description 3
- 241000489973 Diabrotica undecimpunctata Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- -1 dichloroomethane Chemical compound 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
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- 239000002917 insecticide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 239000012948 isocyanate Substances 0.000 description 2
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- 239000008096 xylene Substances 0.000 description 2
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XLUSNOUGZQJPRN-UHFFFAOYSA-N 1-(difluoromethoxy)-4-isocyanatobenzene Chemical compound FC(F)OC1=CC=C(N=C=O)C=C1 XLUSNOUGZQJPRN-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
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- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
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- 235000019738 Limestone Nutrition 0.000 description 1
- 241000171293 Megoura viciae Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 241000952627 Monomorium pharaonis Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
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- 241001454295 Tetranychidae Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
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- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
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- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 235000021405 artificial diet Nutrition 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VJOCYCQXNTWNGC-UHFFFAOYSA-L calcium;benzenesulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1 VJOCYCQXNTWNGC-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
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- 201000002266 mite infestation Diseases 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
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- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
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- 239000010773 plant oil Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
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- 238000011321 prophylaxis Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
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- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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Classifications
-
- 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 & 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 & 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 £
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 |
Publications (2)
Publication Number | Publication Date |
---|---|
AP8700073A0 AP8700073A0 (en) | 1987-11-01 |
AP82A true AP82A (en) | 1990-05-30 |
Family
ID=6313772
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
APAP/P/1987/000073A AP82A (en) | 1986-11-11 | 1987-11-09 | Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines. |
Country Status (26)
Country | Link |
---|---|
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) |
TR (1) | TR23185A (en) |
ZA (1) | ZA878479B (en) |
Families Citing this family (4)
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
-
1986
- 1986-11-11 DE DE19863638631 patent/DE3638631A1/en not_active Withdrawn
-
1987
- 1987-11-02 IL IL84330A patent/IL84330A/en not_active IP Right Cessation
- 1987-11-06 NZ NZ222468A patent/NZ222468A/en unknown
- 1987-11-09 AP APAP/P/1987/000073A patent/AP82A/en active
- 1987-11-09 DD DD87308850A patent/DD265783A5/en not_active IP Right Cessation
- 1987-11-09 JP JP62281179A patent/JPS63135373A/en active Pending
- 1987-11-10 EP EP87730141A patent/EP0267869B1/en not_active Expired - Lifetime
- 1987-11-10 CA CA000551554A patent/CA1266674A/en not_active Expired - Lifetime
- 1987-11-10 US US07/119,191 patent/US4837220A/en not_active Expired - Fee Related
- 1987-11-10 IE IE301387A patent/IE59525B1/en not_active IP Right Cessation
- 1987-11-10 HU HU875003A patent/HU204791B/en not_active IP Right Cessation
- 1987-11-10 DE DE8787730141T patent/DE3780574T2/en not_active Expired - Fee Related
- 1987-11-10 KR KR870012625A patent/KR880006201A/en not_active Ceased
- 1987-11-10 TR TR774/87A patent/TR23185A/en unknown
- 1987-11-10 ES ES87730141T patent/ES2043684T3/en not_active Expired - Lifetime
- 1987-11-10 BR BR8706059A patent/BR8706059A/en not_active Application Discontinuation
- 1987-11-10 CS CS878056A patent/CS264299B2/en unknown
- 1987-11-10 AT AT87730141T patent/ATE78468T1/en not_active IP Right Cessation
- 1987-11-10 PT PT86104A patent/PT86104B/en not_active IP Right Cessation
- 1987-11-11 OA OA59223A patent/OA08774A/en unknown
- 1987-11-11 DK DK591687A patent/DK167012B1/en not_active IP Right Cessation
- 1987-11-11 FI FI874976A patent/FI874976A7/en not_active Application Discontinuation
- 1987-11-11 PH PH36055A patent/PH25609A/en unknown
- 1987-11-11 AU AU80990/87A patent/AU602367B2/en not_active Ceased
- 1987-11-11 ZA ZA878479A patent/ZA878479B/en unknown
- 1987-11-11 CN CN87107752A patent/CN1016168B/en not_active Expired
-
1992
- 1992-10-08 GR GR920402128T patent/GR3005908T3/el unknown
Patent Citations (3)
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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