DD256447A1

DD256447A1 - AKARICIDAL AGENTS

Info

Publication number: DD256447A1
Application number: DD29940087A
Authority: DD
Inventors: Sabine Kuehne; Gerd Kaestner; Joachim Mueller; Elke Borgmann
Original assignee: Fahlberg List Veb
Priority date: 1987-01-22
Filing date: 1987-01-22
Publication date: 1988-05-11

Abstract

Die Erfindung betrifft neue akarizide Mittel zur Bekaempfung von pflanzenschaedigenden Milben in Kulturpflanzenbestaenden, die dadurch gekennzeichnet sind, dass sie als wirksame Komponente mindestens ein Pyrazol-1-carbonsaeureamid der allgemeinen Formel I enthalten, in der R1, R2 und R3 unabhaengig voneinander H oder Halogenatome, ggf. substituierte Alkyl- oder Arylreste oder die Nitrogruppe; X ein O- oder S-Atom, R4 ein H-Atom oder eine Methylgruppe und R5 eine ggf. substituierte Aryl-, Methyl-, Cyclohexyl- oder Aralkylgruppe bedeuten. Formel IThe invention relates to novel acaricidal agents for combating plant-causing mites in cultivated plant stocks, which are characterized in that they contain as active component at least one pyrazole-1-carboxylic acid amide of the general formula I in which R 1, R 2 and R 3 independently of one another have H or halogen atoms, optionally substituted alkyl or aryl radicals or the nitro group; X is an O or S atom, R 4 is an H atom or a methyl group and R 5 is an optionally substituted aryl, methyl, cyclohexyl or aralkyl group. Formula I

Description

(I)(I)

in der R¹, R² und R³ unabhängig voneinander Wasserstoff-, o. Halogenatome, ggf. substituierte Alkyl-, ο. Arylreste oder die Nitrogruppe, X ein Sauerstoff- oder Schwefelatom, R⁴ ein Wasserstoff oder eine Methylgruppe und R⁵ eine ggf. substituierte Aryl-, Methyl-, Cyclohexyl- oder Aralkylgruppe bedeuten, als akariziden Wirkstoffe Verwendung finden, die gleiche oder bessere Wirksamkeit als die in der PS-DD 154799 als akarizide Mittel beschriebenen Pyridincarbonsäureanilide aufwiesen.in the R ¹ , R ² and R ^{3 are} independently hydrogen, o. Halogen atoms, optionally substituted alkyl, ο. Aryl radicals or the nitro group, X is an oxygen or sulfur atom, R ^{4 is} a hydrogen or a methyl group and R ^{5 is} an optionally substituted aryl, methyl, cyclohexyl or aralkyl group, are used as acaricidal agents, the same or better activity than have the Pyridincarbonsäureanilide described in PS-DD 154799 as acaricidal agents.

Die erfindungsgemäßen Verbindungen sind z. Teil bekannt. Sie können nach relativ einfachen Syntheseverfahren hergestellt werden. Die in Tab. 1 zusammengestellten Substanzen wurden z. B. durch Umsetzung entsprechend substituierter Pyrazole mit Carbamoylhalogeniden, Isocyanaten bzw. Isothiocyanaten oder mit Phosgen und nachfolgender Reaktion mit Ammoniak oder Aminen hergestellt.The compounds of the invention are for. Part known. They can be prepared by relatively simple synthesis methods. The compiled in Tab. 1 substances were z. B. prepared by reacting appropriately substituted pyrazoles with carbamoyl halides, isocyanates or isothiocyanates or with phosgene and subsequent reaction with ammonia or amines.

Die Verbindungen der Formel I können als solche oder in Kombination mit einem geeigneten Zusatz als akarizide Mittel verwendet werden. Geeignete Zusätze sind beispielsweise Lösungs-, Verdünnungs-, Emulgier-, Verdickungs- und Haftmittel sowie weitere Pflanzenschutz-und Schädlingsbekämpfungsmittel.The compounds of the formula I can be used as such or in combination with a suitable additive as acaricidal agents. Suitable additives are, for example, solvents, diluents, emulsifiers, thickeners and adhesives, as well as other crop protection and pesticides.

Die Mittel, welche die Wirkstoffe der Formel I enthalten, können in verschiedenster Form appliziert werden, beispielsweise als Emulsionen, Suspensionen, Stäubepulver, Dispersionen, Nebelmittel oder Mikrogranulate. Die Applikationsart richtet sich ausschließlich nach dem Verwendungszweck. Die Herstellung der für die verschiedenen Anwendungsformen geeigneten Wirkstoff-Formulierungen kann nach den in der Formulierungstechnik üblichen Misch- und Mahlverfahren erfolgen.The agents which contain the active compounds of the formula I can be applied in a wide variety of forms, for example as emulsions, suspensions, dusting powders, dispersions, fog agents or microgranules. The type of application depends exclusively on the intended use. The preparation of the active ingredient formulations suitable for the various application forms can be carried out according to the mixing and milling methods customary in formulation technology.

In der Praxis können die Verbindungen der Formel I je nach der Art der durchzuführenden Behandlung, dem Zeitpunkt und dem Entwicklungsstadium der Schädlingspopulation in Konzentrationen von 100 bis 1000 ppm, besonders im Konzentrationsbereich von 200 bis 500 ppm angewendet werden.In practice, the compounds of formula I can be applied in concentrations of 100 to 1000 ppm, especially in the concentration range of 200 to 500 ppm, depending on the type of treatment to be carried out, the time and the stage of development of the pest population.

Die folgenden Beispiele erläutern die Herstellung der erfindungsgemäßen Verbindungen und ihre speziellen akariziden Eigenschaften.The following examples illustrate the preparation of the compounds of the invention and their specific acaricidal properties.

Beispiel 1:?' Example 1 :? '

1-Phenylcarbamoy|-3-(n-butyl)-pyrazol1-Phenylcarbamoy | -3- (n-butyl) pyrazole

6,2g (0,05 Mol) 3-(n-Butyl)-pyrazol werden in 25ml trockenem Benzen gelöst und danach unter Rühren 5,95g Phenylisocyanat, gelöst in 25ml Benzen, zugetropft. Nach beendeter Zugabe wird 2 Stunden bei 60-70⁰C gerührt und dann das Benzen abdestilliert. Der verbleibende Rückstand wird im Ölpumpenvakuum destilliert. Man erhält 8,5g (70,3% d. Th.) einer farblosen, öligen Flüssigkeit, Kp_o,₇122 — 7'⁰C6.2 g (0.05 mol) of 3- (n-butyl) pyrazole are dissolved in 25 ml of dry benzene and then 5.95 g of phenyl isocyanate dissolved in 25 ml of benzene are added dropwise with stirring. After the addition is stirred for 2 hours at 60-70 ⁰ C and then distilled off the benzene. The remaining residue is distilled in an oil pump vacuum. This gives 8.5 g (70.3% of theory) of a colorless, oily liquid, Kp _o , ₇ 122 - 7 ' ⁰ C.

Beispiel 2: eExample 2: e

1-(4-Fluorphenylcarbamoyl)-3-methyl-pyrazol1- (4-fluoro-phenylcarbamoyl) -3-methyl-pyrazole

Zu 0,1 Mol 1,1'-Carbonyl-bis-3-methyl-pyrazol in absolutem Toluen (erhalten durch Umsetzen von 0,1 Mol Phosgen mit 0,4 Mol 3-Methylpyrazol in absolutem Toluol und Abtrennen des ausgefallenen 3-Methyl-pyrazolhydrochlorids) wird unter Rühren bei Raumtemperatur 0,1 Mol4-Fluoranilin in absolutem Toluol langsam zugetropft. Nach beendeter Zugabe wird das Reaktionsgemisch noch 4 Stunden bei 6O⁰C gerührt. Nach Abkühlen wird der ausgefallene Feststoff abgesaugt und aus Cyclohexan umkristallisiert. Man erhält 12,7g (58,1 % d. Th.) weiße, glänzende Kristalle, F. 103,5-105⁰C.To 0.1 mol of 1,1'-carbonyl-bis-3-methyl-pyrazole in absolute toluene (obtained by reacting 0.1 mol of phosgene with 0.4 mol of 3-methylpyrazole in absolute toluene and separating the precipitated 3-methyl pyrazole hydrochloride) is slowly added dropwise while stirring at room temperature 0.1 mol of 4-fluoroaniline in absolute toluene. After completion of the addition, the reaction mixture is stirred for 4 hours at 6O ⁰ C again. After cooling, the precipitated solid is filtered off and recrystallized from cyclohexane. This gives 12.7 g (58.1% of theory) of white, lustrous crystals, mp 103.5-105 ⁰ C.

Beispiel 3: _.....'Example 3: _..... '

Ovizidwirkung gegenüber Tetranychus ürticae Koch.Ovicidal activity against Tetranychus urticae Koch.

Blattscheiben von Phaseolus vulgaris wurden mit Sommereiern von Tetranychus urticae belegt und mit einer wäßrigen Suspension bzw. Emulsion verschiedener Konzentrationen des zu testenden Wirkstoffes besprüht. Nach vollzähligem Larvenschlupf in derunbehandelten Kontrolle wurde die Anzahl der geschlüpften Larven in den behandelten Prüfgliedern festgestellt.Leaf discs of Phaseolus vulgaris were coated with summer eggs of Tetranychus urticae and sprayed with an aqueous suspension or emulsion of various concentrations of the drug to be tested. After complete larval hatching in the untreated control, the number of hatched larvae in the treated test members was determined.

Die als prozentuale Mortalitätsraten errechneten Resultate sind den Tabellen 2 und 3 zu entnehmen.The results calculated as percentage mortality rates are shown in Tables 2 and 3.

Example 4:

Adultiiridwirkung gegenüber Weibchen von Tetranychus urticae Koch.Adultiiridwirkung against females of Tetranychus urticae Koch.

Je 1 Blatt von Phaseolus vulgaris wurde mit 25 Weibchen von Tetranychus urticae besetzt.One leaf of Phaseolus vulgaris was occupied by 25 females of Tetranychus urticae.

Je 2 Blätter pro Prüfglied wurden mit wäßrigen Suspensionen verschiedener Konzentration des zu prüfenden Wirkstoffes besprüht. Nach 48Std. wurde die Anzahl der getöteten Weibchen ermittelt. Die als prozentuale Mortalitätsrate errechneten Resultate sind der Tab. 2 zu entnehmen.2 leaves per test member were sprayed with aqueous suspensions of various concentrations of the test compound. After 48h. the number of females killed was determined. The results calculated as the percentage mortality rate are shown in Tab. 2.

Example 5:

Herstellung eines Spritzpulvers für die Zubereitung von SuspensionenPreparation of a wettable powder for the preparation of suspensions

Folgende Komponenten werden vermischt und anschließend fein vermählen. The following components are mixed and then finely ground.

— Erfindungsgemäßer Wirkstoff 20Ma.-%- active ingredient 20Ma .-% according to the invention

— Inertstoff 45Ma.-%- inert material 45Ma .-%

— Mahlhilfsmittel 25Ma.-%- grinding aid 25Ma .-%

— Mischung aus nichtionogenen u. anionenaktivenTensiden 10Ma.-%- Mixture of nonionic u. anion-active surfactants 10Ma .-%

Example 6:

Herstellung eines Emulsionskonzentrates für die Zubereitung von Emulsionen Nachfolgend aufgeführte Komponenten werden vermischt:Preparation of an emulsion concentrate for the preparation of emulsions The following components are mixed:

— ErfindungsgemäßerWirkstoff ' 20Ma.-%Inventive active substance 20% by mass

— Mischung aus nichtionogenen u. anionenaktivenTensiden 30Ma.-%- Mixture of nonionic u. anion-active surfactants 30Ma .-%

— Alkohol in mittlerer Kettenlänge 50Ma.-%- medium chain alcohol 50Ma .-%

Example 7:

, Bestimmung der Pflanzenverträglichkeit, Determination of plant tolerance

Als Testpflanzen dienten Tomate (1), Sellerie (2) und Ackerbohne (3). Sie wurden tropfnaß mit wäßrigen Suspensionen der formulierten Wirkstoffe gespritzt. Nach 3 bis 14 Tagen erfolgte die visuelle Einschätzung des Schädigungsgrades der Pflanzen nach folgendem Boniturschema:Tomatoes (1), celery (2) and field bean (3) were used as test plants. They were sprayed dripping wet with aqueous suspensions of the formulated active ingredients. After 3 to 14 days, the visual assessment of the degree of damage of the plants was carried out according to the following rating scheme:

BoniturnoteBoniturnote Schädigung der Pflanzen in %Damage to plants in% 00 00 11 bis 25to 25 22 26 bis 7526 to 75 33 > 75> 75

Die Ergebnisse sind in der Tab.4 zusammengestellt.The results are summarized in Tab.4.

Table 1

ιι R¹ R ¹ R² R ² R³ R ³ R⁴ R ⁴ R⁵ R ⁵ XX Fp/Kp(°C)Mp / bp (° C) CX-NCX-N HH HH HH HH C₆H₅ C ₆ H ₅ 00 71-7371-73 Lfd. Nr.Ser. No. CH₃ CH ₃ HH HH HH C₆H₅ C ₆ H ₅ 00 73-7673-76 1.1. CH₃ CH ₃ CH₃ CH ₃ . H, H HH C₆H₅ C ₆ H ₅ 00 110-112110-112 2.Second CH₃ CH ₃ HH ⁵CH₃ ⁵ CH ₃ HH C₆H₅ C ₆ H ₅ 00 64-6664-66 3.Third CH₃ CH ₃ ClCl HH HH C₆H₅ C ₆ H ₅ 00 94-9694-96 4.4th CH₃ CH ₃ Brbr HH HH C₆H₅ C ₆ H ₅ 00 93-9693-96 5.5th CH₃ CH ₃ CICI CH₃ CH ₃ HH C₆H₆ C ₆ H ₆ 00 88-9088-90 6.6th C₂H₅ C ₂ H ₅ HH HH HH C₆H₅ C ₆ H ₅ 00 34,5-3634.5 to 36 7.7th n-C₃H₇ nC ₃ H ₇ HH HH HH C₆H₆ C ₆ H ₆ 00 40-4140-41 8.8th. i-C₃H₇ iC ₃ H ₇ HH HH HH C₆H₅ C ₆ H ₅ 00 31,5-3331.5 to 33 9.9th n-C₄H₉ nC ₄ H ₉ HH HH HH C₆H₅ C ₆ H ₅ 0 Kp_o,₇ 0 kp _o , ₇ 125-127125-127 10.10th J-C₄H₉ JC ₄ H ₉ HH HH HH C₆H₅ C ₆ H ₅ 0 Kpo,₆ 0 Kpo, ₆ 115-120115-120 11.11th C₅H11C ₅ H11 HH HH HH C₆H₅ C ₆ H ₅ 00 41-4241-42 12.12th C₇Hi₅ C ₇ Hi ₅ HH HH HH C₆H₅ C ₆ H ₅ 00 29-3129-31 13.13th C₂H₅ C ₂ H ₅ CH₃ CH ₃ CH₃ CH ₃ HH C₆H₅ C ₆ H ₅ 00 65-66,565 to 66.5 14.14th CH₃ CH ₃ CH₃ CH ₃ CH₃ CH ₃ HH C₆H₅ C ₆ H ₅ 00 88-9188-91 15.15th CH₃ CH ₃ NO₂ NO ₂ HH HH C₆H₅ C ₆ H ₅ 00 143-146143-146 16.16th CH₃ CH ₃ CH₃ CH ₃ NO₂ NO ₂ HH C₆H₅ C ₆ H ₅ 00 134-38134-38 17.17th 4-CI-C₆H₄ 4-CI-C ₆ H ₄ HH HH HH C₆H₅ C ₆ H ₅ 00 124-125,5124 to 125.5 18.18th C₆H₅ C ₆ H ₅ HH HH HH C₆H₅ C ₆ H ₅ 00 117,5-118,5117.5 to 118.5 19.19th HH CH₃ CH ₃ HH HH - C₆H₅ - C ₆ H ₅ 00 98-10198-101 20.20th HH HH HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 115-124115-124 21.21st CH₃ CH ₃ CH₃ CH ₃ HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 114-117114-117 22.22nd C₂H₅ C ₂ H ₅ HH HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 75-77,575 to 77.5 23.23rd n-C₃H₇ nC ₃ H ₇ HH HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 64-66,564 to 66.5 24.24th J-C₃H₇ JC ₃ H ₇ HH HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 50-5250-52 25.25th n-C₄H₉ nC ₄ H ₉ HH HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 36-4036-40 26.26th i-C₄H₉ iC ₄ H ₉ HH HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 50-5550-55 27.27th i-C₄H₉ iC ₄ H ₉ HH HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 69-7269-72 28.28th C₆HnC ₆ Hn HH HH HH 4-Cl-C₆H₄ 4-Cl-C ₆ H ₄ 00 49-50,5 .49-50.5. 29.29th C₂H₅ C ₂ H ₅ CH₃ CH ₃ HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 83-84,583 to 84.5 30.30th C₉Hi₉ C ₉ Hi ₉ HH HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 40-4340-43 31.31st HH Brbr HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 157,5-158,5157.5 to 158.5 32.32nd 33.33rd

R¹ R ¹ R² R ² R³ R ³ R⁴ R ⁴ R⁵ R ⁵ XX -4- 256 447-4- 256 447 Lfd. Nr.Ser. No. HH ClCl HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 Fp/KpfC)Fp / KPFC) 34.34th CH₃ CH ₃ HH NO₂ NO ₂ HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 148-149,5148 to 149.5 35.35th CH₃ CH ₃ JJ CH₃ CH ₃ HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 146-150146-150 36.36th CH₃ CH ₃ JJ HH HH 4-CI-C₆H₄ 4-CI-C ₆ H ₄ 00 128-130128-130 37.37th CH₃ CH ₃ HH HH HH 3-CI-C₆H₄ 3-CI-C ₆ H ₄ 00 129-130,5129 to 130.5 38.38th CH₃ CH ₃ CH₃-CH ₃ - HH HH 3-CI-C₆H₄ 3-CI-C ₆ H ₄ 00 91-9491-94 39.39th C₂H₆ C ₂ H ₆ HH HH HH 3-CI-C₆H₄ 3-CI-C ₆ H ₄ 00 107-110107-110 40.40th n-C₃H₇ nC ₃ H ₇ HH HH HH 3-CI-C₆H₄ 3-CI-C ₆ H ₄ 00 37-4037-40 41.41st CH₃ CH ₃ HH HH HH 3—CH3—Cg H43-CH3-Cg H4 00 52-5452-54 42.42nd CH₃ CH ₃ CH₃ CH ₃ HH HH 3—CH3—CgH43-CH3 CgH4 00 70-7270-72 43.43rd CH₃ CH ₃ HH CH₃ CH ₃ HH 3—CH3—CeH43-CH3 CeH4 00 86-8986-89 44.44th CH₃ CH ₃ HH HH HH 4-nC₃H₇O-C₆H₄ 4-nC ₃ H ₇ OC ₆ H ₄ 00 44-4644-46 45.45th C₆H₅ C ₆ H ₅ HH HH HH CH₃ CH ₃ 00 65-6765-67 46.46th CH₃ CH ₃ Brbr HH HH C₆H11C ₆ H11 00 107-111107-111 47.47th CH₃ CH ₃ HH HH HH CH₂-C₆H₅ CH ₂ -C ₆ H ₅ 00 62-6562-65 48.48th CH₃ CH ₃ ClCl HH HH C₆HnC ₆ Hn 0 Kpo,₅ 0 Kpo, ₅ 51-5551-55 49.49th HH HH HH HH 3,4-CI₂-C₆H₃ 3,4-CI ₂ -C ₆ H ₃ 00 130-140130-140 50.50th C₂H₅ C ₂ H ₅ HH HH C4H9C4H9 C₄M₉ C ₄ M ₉ 0 Kp_o,₆ 0 kp _o , ₆ 123-124,5123 to 124.5 51.51st CH₃ CH ₃ CH₃ CH ₃ HH HH C₆HnC ₆ Hn 0 Kpo,₃ 0 Kpo, ₃ 119-121119-121 52.52nd CH₃ CH ₃ HH HH CH₃ CH ₃ CH₃ CH ₃ 00 100-106100-106 53.53rd CH₃ CH ₃ NO₃ NO ₃ HH CH₃ CH ₃ CH₃ CH ₃ 00 80-8980-89 54.54th CH₃ CH ₃ NO₂ NO ₂ HH HH C₆HnC ₆ Hn 00 87,5-9087.5 to 90 55.55th CH₃ CH ₃ HH HH HH (CH₂)J-C₆Hs(CH ₂ ) JC ₆ Hs 00 83-8683-86 56.56th CH₃ CH ₃ HH HH HH HH 00 78,5-8178.5 to 81 57.57th CH₃ CH ₃ ClCl HH HH HH 00 127-29127-29 58.58th HH HH HH HH HH 00 142-144142-144 59.59th CH₃ CH ₃ HH HH HH 4-F-C₆H₄ 4-FC ₆ H ₄ 00 141-141,5141 to 141.5 60.60th CH₃ CH ₃ ClCl HH HH 3—CH₃C₆H₄ 3-CH ₃ C ₆ H ₄ 00 103,5-105103.5 to 105 61.61st CH₃ CH ₃ Brbr HH HH 3—CH₃C₆H₄ 3-CH ₃ C ₆ H ₄ 00 95-9795-97 62.62nd CH₃ CH ₃ Brbr HH HH CH₃ CH ₃ SS 90-9390-93 63.63rd CH₃ CH ₃ HH HH HH C₆H₅ C ₆ H ₅ SS 86-88,586 to 88.5 64.64th C₂H₅ C ₂ H ₅ CH₃ CH ₃ HH HH C₆H₅ C ₆ H ₅ SS 77-9,577-9.5 65.65th Öl, nichtOil, not CH₃ CH ₃ HH HH HH CrH 11CrH 11 SS destillierbardestillierbar 66.66th 52-5452-54

Table 2

Akarizide Wirkung gegenüber Tetranychus urticaeAcaricidal activity against Tetranychus urticae

Wirkungeffect ovizidovicidal Mortalitätsrate [%]Mortality rate [%] adultizidadulticide lfd. Nr. nach Tab. 1No. according to Tab. 1 100,0100.0 2,02.0 1 000 ppm AS1 000 ppm AS 100,0100.0 15,215.2 1.1. 90,790.7 6,46.4 2.Second 97,897.8 18,418.4 3.Third 98,598.5 14,614.6 4.4th 99,299.2 17,317.3 5.5th 100,0100.0 15,815.8 6.6th 86,686.6 25,025.0 7.7th 100,0100.0 21,921.9 8.8th. 100,0100.0 16,216.2 9.9th 100,0100.0 31,831.8 10.10th 91,891.8 13,613.6 11.11th 100,0100.0 17,917.9 12.12th 100,0100.0 37,537.5 13.13th 100,0100.0 9,89.8 14.14th 100,0100.0 0,00.0 15.15th 100,0100.0 14,614.6 16.16th 86,786.7 2,42.4 21.21st 98,398.3 17,017.0 22.22nd 100,0100.0 23,923.9 25.25th 99,699.6 6,76.7 27.27th 99,499.4 13,513.5 28.28th 94,094.0 6,16.1 30.30th 95,595.5 0,00.0 31.31st 94,494.4 15,815.8 38.38th 100,0100.0 8,18.1 39.39th 40.40th

Wirkstoffactive substance ovizidovicidal Moralitätsrate [%]Morality rate [%] adultizidadulticide lfd. Nr. nach Tab. 1No. according to Tab. 1 99,399.3 11,511.5 1 000 ppm AS1 000 ppm AS 96,496.4 15,615.6 41. .41.. 85,385.3 9,39.3 42.42nd ' 100,0'100.0 16,716.7 43.43rd 96,796.7 2,12.1 44.44th 79,879.8 12,012.0 45.45th 97,997.9 15,215.2 46.46th 95,295.2 9,19.1 47.47th 100,0100.0 0,00.0 48.48th 89,189.1 10,910.9 60.60th 98,998.9 6,16.1 63.63rd 100,0100.0 13,613.6 65.65th 66.66th

Table 3

Akarizide Wirkung gegenüber Eiern von Tetranychus urticae Koch nach Applikation verschiedener AS-KonzentrationenAcaricidal activity against eggs of Tetranychus urticae Koch after administration of various AS concentrations

Wirkstoff Formul.Active ingredient Formul. 10Wp10Wp Mortalitätsratemortality rate 800800 ovizidovicidal [%][%] bei der Konzentration [ppm]at the concentration [ppm] 2020 1010 Lfd. Nr.Ser. No. 20Wp20Wp 10001000 100100 400400 200200 100100 —- —- 1.1. 20Wp20Wp 100100 97,697.6 94,994.9 74,474.4 —- 0,80.8 6,76.7 6.6th 20EC20EC 99,299.2 100100 97,497.4 63,663.6 6,46.4 65,465.4 32,732.7 7.7th 20Wp20Wp 100100 100100 93,193.1 80,280.2 93,993.9 —- —- 9.9th 20EC20EC 100100 100100 84,284.2 36,136.1 —- 39,639.6 10,210.2 11.11th 20Wp20Wp 100100 100100 100100 99,199.1 100100 1,01.0 00 13.13th 20Wp20Wp 100100 100100 99,499.4 83,7 ·83.7 · 65,565.5 —- —- 14.14th 20EC20EC 100100 100100 100100 42,442.4 —- 3,63.6 3,93.9 15..15 .. 20WP20Wp 100100 100100 99,199.1 . 96,9, 96.9 84^284 ^ 2 91,291.2 43,543.5 21.21st 20EC20EC 100100 100100 99,199.1 100100 100100 —- —- 27.27th 20EC20EC 100100 100100 100100 96,896.8 . —, - —- ¹ — ¹ - 28.28th 20EC20EC 99,699.6 99,599.5 84,484.4 45,445.4 —- 6,26.2 0,80.8 30.30th 20EC20EC 99,499.4 75,775.7 99,799.7 89,389.3 71,171.1 —- —- 41.41st 20EC20EC 99,399.3 46,246.2 37,937.9 16,516.5 —- 24,324.3 40,140.1 45.45th 20EC20EC 96,796.7 99,499.4 33,333.3 31,331.3 60,160.1 27,627.6 13,113.1 60.60th 20Wp20Wp 100100 100100 97,797.7 73,073.0 67,867.8 —- —- 66.66th 20Wp20Wp 100100 100100 98,598.5 56,856.8 24,124.1 —- —- AA 100100 —- 100100 9696 6464 —- —- BB 6,56.5 —- —- —-

A = Picolinsäure-p-chloranilid (DD 154799)A = picolinic acid p-chloroanilide (DD 154799)

B = TH 60-41 i-fp-ChlorphenylcarbamoyD-S-lp-chlorphenyll^-pyrazolin (DE OS 2304584)B = TH 60-41 i-fp-chlorophenylcarbamoyl-S-lp-chlorophenyl-pyrazoline (DE OS 2304584)

Tabelle 4Table 4 Konz. d.Conc. D. 11 Testpflanzetest plant 33 Bestimmung der PhytotoxizitätDetermination of phytotoxicity Wirkstoffesagent 22 Lfd. Nr.Ser. No. 2 000 ppm2,000 ppm 00 BoniturnoteBoniturnote 00 2 000 ppm2,000 ppm 11 00 11 2 000 ppm2,000 ppm 00 00 00 6.6th 2 000 ppm2,000 ppm 11 . 0, 0 00 11.11th 2 000 ppm2,000 ppm 00 11 00 13.13th 2 000 ppm2,000 ppm 00 00 00 21.21st 2 000 ppm2,000 ppm 11 00 00 27.27th 2 000 ppm2,000 ppm 00 30.30th 31.31st

Claims

Acaricidal agent, characterized in that it contains as active ingredient at least one substituted pyrazole-1-carboxamide of the general formula I in which R ¹ , R ² and R ³ independently of one another are hydrogen or halogen atoms, optionally substituted alkyl or aryl radicals or Nitro group, X is an oxygen or sulfur atom, R ^{4 is} a hydrogen atom or a methyl group and R ^{5 is} an optionally substituted aryl, methyl, cyclohexyl or aralkyl group, in addition to the usual carriers, solvents and / or formulation auxiliaries.

Field of application of the invention

The invention relates to novel acaricidal agents for controlling plant-damaging mites in cultivated plant stands, which are characterized in that they contain as active component at least one pyrazole derivative.

Characteristic of the known state of the art

Plant-damaging mites are widespread worldwide and of great economic importance as direct damage in vegetable growing under glass and plastics as well as in the field, in fruit and hops, in ornamental plants, in cotton, tea and other important crops. For the control of these mites, a number of effective chemical compounds are known, which have more or less economic and / or technical defects. Sorrounding u.a. with repeated use of the same drugs resistance phenomena, which makes their substitution by acaricides with a different chemical structure (rotation of the agent) is required. Hence the need to constantly develop new effective acaricides with the trend towards specialty acacia for certain crops. Substituted pyrazoles and pyrazolines have been proposed in various patents as crop protection and pest control agents as well as biological process control agents. So z. B. 5-amino-1-phenylpyrazol-4-carbonitriles (or carboxylic acid esters) as herbicidal agents (DD 160271, DD 201750), 3-alkoxy (alkylthio) -pyrazolyl- (5) -N, N-dimethylcarbamate as insecticidal agents (DD 133034), 1-acylpyrazoles as nitrification inhibitors (DD 131063, DD 133088), 1-aryloxyalkylcarbonyl-pyrazoles as growth regulators (DAS 1745906) and pyrazoline-1-carboxylic acid amides as insecticides (US 4174393, DD 129396, US 4010271, DE 2304584 ) claimed. Acaricidal pyrazoles or pyrazolines have not previously been described.

Object of the invention

The aim of the invention is the development of new effective means for controlling plant-damaging mites, which are equal to or superior to the previously applied acaricides in their effect on plant pests, do not damage crops and natural enemies of the mites and keep in this way the pest infestation below the economic damage threshold.

Explanation of the essence of the invention

The invention has for its object to develop new acaricidal agents based on new chemical agents to accelerate the currently particularly urgent need for rotation of acaricidal agents to prevent resistance phenomena and thus to avoid loss of yield in crop cultivation by a beneficial control of pests.

According to the invention this object is achieved in that substituted pyrazole-1-carboxamides of the general formula I,