AU622292B2 - Heteroaryl-aryl-butene and -butane derivatives, process for their preparation, agents containig them, and their use as pesticides - Google Patents

Heteroaryl-aryl-butene and -butane derivatives, process for their preparation, agents containig them, and their use as pesticides Download PDF

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AU622292B2
AU622292B2 AU51180/90A AU5118090A AU622292B2 AU 622292 B2 AU622292 B2 AU 622292B2 AU 51180/90 A AU51180/90 A AU 51180/90A AU 5118090 A AU5118090 A AU 5118090A AU 622292 B2 AU622292 B2 AU 622292B2
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Manfred Kern
Werner Knauf
Gerhard Salbeck
Stefan Schnatterer
Hans Herbert Schubert
Anna Waltersdorfer
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
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    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P33/10—Anthelmintics
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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    • C07D333/32—Oxygen atoms

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract

The compounds of the formulae I and II, their stereoisomers and the mixtures of these <IMAGE> in which R<1> represents pyridyl, pyrimidyl, thienyl, thiazolyl, furanyl, pyrazolyl, 1,3-oxazolyl or imidazolyl, each of which can be substituted, R<2> represents H, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C3-C6)cycloalkyl, -CH=CH2 or -C IDENTICAL CH, R<3> represents H or (C1-C4)alkyl, R<4> represents H, (C1-C4)alkyl, -CN or -C IDENTICAL CH, A represents CH2, O or S, B represents CH, N or C(CH3), R<5> represents H or halogen and R<6> represents phenyl, phenoxy or benzyl, each of which can be monosubstituted to pentasubstituted by halogen or (C1-C3)haloalkyl, have advantageous insecticidal or acaricidal properties.

Description

I- .i i 11 1111---- COMMONWEALTH OF AUS RLI PATENTS ACT 1952-69 292 Form COMPLETE SPECIFICATION
(ORIGINAL)
Class Int. Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: 4 t s Priority: Related Art t Related Art L Name of Applicant Address of Applicant Actual Inventor Address for Service HOECHST AKTIENGESELLSCHAFT D-6230 Frankfurt am Main 80, Federal Republic of Germany STEFAN SCHNATTERER, HANS HERBERT SCHUBERT, GERHARD GERHARD SALBECK, WERNER KNAUF, ANNA WALTERSDORFER and MANFRED KERN.
WATERMARK PATENT TRADEMARK ATTORNEYS.
LOCKED BAG NO. 5, HAWTHORN, VICTORIA 3122, AUSTRALIA Complete Specification for the invention entitled: HETEROARYL-ARYL-BUTENE AND -BUTANE DERIVATIVES, PROCESS FOR THEIR PREPARATION, AGENTS CONTAINING THEM, AND THEIR USE AS PESTICIDES.
The following statement is a full description of this invention, including the best method of performing it known to US 1.
I-
HOECHST AKTIENGESELLSCHAFT HOE 89/F082 Dr.LO/PP Description i Heteroaryl-aryl-butene and -butane derivatives, process for their preparation, agents containing them, and their use as pesticides It is known that certain 1,4-diarylbutane and 1,4-diarylbutene compounds have insecticidal or acaricidal properties (GB 2,187,452 A or Chem. Abstr. Vol. 109,73119z).
However, the activities of these compounds are insufficient in some cases.
i By introducing heteroaryl groups into the arylbutene and arylbutane structure, it was possible to prepare novel arylbutene and arylbutane derivatives having advantageous pesticidal, in particular insecticidal and/or acaricidal properties.
The present invention therefore relates to the compounds of the formulae I and II, the stereoisomers thereof, and: the mixtures of the latter R1 H C C- A H R R3 R4V( (I) R6 .1 H I R (II) CH CH A R2 3 q
R
6 where
R
1 is pyridyl, pyrimidyl, thienyl, thiazolyl, furanyl, pyrazolyl, 1,3-oxazolyl or imidazolyl, all of which can be substituted,
R
2 is H, (C 1 -C)alkyl, (C-C 4 )haloalkyl, (Ci-C,)alkoxy,
(C
3
-C
6 )cycloalkyl, -CH=CH 2 or -CiCH, '7 i
R
3
R
4
A
B
R
5
R
6 -2 is H or (Ci-C 4 )alkyl, is H, (C 1
-C
4 )alkyl, -CN or -C-CH, is CH 2 O or S, is CH, N or C(CH 3 is H or halogen and is phenyl, phenoxy or benzyl, all of which can be monosubstituted to pentasubstituted by halogen or
(C
1 -C)haloalkyl.
Preferred compounds of the formulae I and II are those lQ in which
R
1 is a radical of the formulae A, B, C, D, E or F r t Sf t t i t t StI I (C(g R7)m
N
R
7 )m
S
N (R 7 -0N y ^Y
R
7 (7)m ~-cy
(F)
::i t :j 1 r: i i, sS ii i;: in which R 7 is H, halogen, (C 1
-C
4 )alkyl, (C 1
-C
4 alkoxy, (C 1
-C
4 )haloalkyl, (C 1
-C
4 )haloalkoxy and m is 15 1 or 2,
R
2 is (Ci-C 3 )alkyl, cyclopropyl or CF 3
R
3 is H or methyl, B is CH,
R
4 is H, methyl, -CN or -CiCH and
R
6 is phenoxy which can be substituted in the 4-position by Cl, Br or CF 3 Particularly preferred compounds of the formulae I and II are those in which
R
7 is Cl, Br, (C 1
-C
3 )alkoxy, -OCF 3
-OCH
2
CF
3 or -OCF 2
CF
2
H.
The substituent R 1 is preferably the radicals of the -3formulae A, B or C, in particular A.
The invention embraces all stereoisomers which can occur in the formulae I and II, in particular the Z- and Ei diastereomers of the olefin function in formula I and their mixtures, furthermore the individual enantiomers as well as pairs of enantiomers of the formulae I and II.
Alkyl is both straight-chain and branched alkyl.
The present invention furthermore relates to a process for the preparation of compounds of the formulae I and II, which comprises a) for compounds of the formula I, reacting a compound S.of the formula III
R
1
(III)
C 0 R2' where R 1 and R 2 are as defined in formula I, with a compound of the formula IV
R
6 H A C P(R)3 14 P 3 (IV) where R 3
R
4
R
5
R
6 A and B are as defined in formula I and R 8 is phenyl, cyclohexyl or butyl, and b) for compounds of the formula II, catalytically hydrogenating the olefin function of the corresponding compound of the formula I with hydrogen or a hydrogen-liberating compound.
The process described under a) is known as a Wittig reaction. The procedure and the reaction parameters are described in the literature Bestmann, Topics in Current Chemistry 109 (1983); Houben-Weyl, Methoden der -i let rt.
4 organ. Chemie [Methods of Organic Chemistry], Vol. El and The carbonyl function of the compound III can be exchanged for the radical =P(R 8 3 of the compound IV, and vice versa.
Furthermore, the radical R 1 can be converted into a corresponding carbonyl compound via an organometal compound. The compound of the formula I then originates by elimination of water from the tertiary alcohol which has formed (Houben-Weyl Vol. 6/la/2).
The ketones III which are used as starting materials for the Wittig reaction a) are obtained by Friedel-Crafts acylation of aromatic compounds containing sufficient electrons (Houben-Weyl, Vol. 7/2a, 39, 83), or, alternatively, by synthesizing the carbon structure by reacting arylmetal compounds with suitable carboxylic acid derivatives, such as carboxylic acid halides, anhydrides, esters or nitriles (Houben-Weyl 7/2a, 548-621; X. Creary, J. Org. Chem. 52, 5026-30 (1987)).
The ylide compounds IV are formed from the corresponding phosphonium salts or phosphonic esters by deprotonation with strong bases, such as alkali metal hydrides, organolithium compounds, alkali metal amides and alkali metal alcoholates in ethers or aromatic hydrocarbons as the solvent, either before the addition of ketone or in the presence of the ketone III, at temperatures of from to +100°C (Houben-Weyl, Vol. El and The phosphonium salts V are obtained by ;i i
N
'i: alkylating triphenylphosphane or trialkylphosphane with arylalkyl halides of the formula VI under reaction
'I
5 conditions known from the literature (Houben-Weyl Vol.
El, 495-515, and 12/1, 79-124).
R
6 B CH A CH X X Cl, Br, J (VI) R4 R3 The alkylating agents VI are formed on the one hand, when A CH 2 from the corresponding 3-arylpropanols VII and hydrogen halide or inorganic acid halides, for example thionyl chloride, on the other hand, if A 0 or S, they are prepared from the corresponding benzyl alcohol and iiformaldehyde and hydrogen halide (Houben-Weyl Vol. 5/3 i and 5/4, DE-A-3,125,338). The 3-arylpropanols VII can be prepared by reducing cinnamic acids and their esters VIII $til# with aluminum hydrogen compounds, for example lithium alanate (Houben-Weyl, Vol. 4/ld, 190-216).
4 SR6 CH 2
CH
2
CH
2 0H
(VII)
R6 B CH CH COOR' R' H, Alkyl (VIII) The arylbutane compounds of the formula II are synthesized by hydrogenating the olefin function in an arylbutene of the formula I with hydrogen or a hydrogenliberating compound, for example hydrazine, cyclohexene or formic acid derivatives, under the catalytic influence of compounds of palladium, platinum, nickel or rhodium, under reaction conditions known from the literature (Houben-Weyl, Vol. 4/Ic).
-Fn -6- The compounds II can furthermore be prepared by an addition reaction of diboranes, borane adducts or alkylsubstituted boranes with the C,C double bond of I, followed by hydrolysis of the boron/carbon bond using water or alcohols (Houben-Weyl, Vol. 4/id, p. 49-59).
The active compounds are suitable for combating animal pests, in particular insects, arachnida, Helminthes and mollusks, very particularly preferably for combating insects and arachnida, encountered in agriculture, in animal husbandry, in forestry, in the protection of stored products and of materials, and in the hygiene field, and have good plant tolerance and favorable toxicity to warm-blooded animals. They are active S' against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include: ,tlftt
I
From the order of the Acarina, for example Acarus siro, Agras spp., Ornithrodoros app., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp. From the order of the Isopoda, for example, Oniscus asellus, Armadium vulgare and Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera 3po.
From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example, Lepisma saccharina. From the order of the Collembola, for example, Onychiurus armatus. From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. From the order of the Dermaptera, for example, Forficula auricularia. From the order of
'V
V
-7 I t the Isoptera, for example, Reticulitermes Opp.. From the order of the Anoplura, for example, Phylloxera vastatrix, Pemphigus app., Pediculus humanus corporis, Haematopinus spp. and Linognathus Opp. From the order of the Mallophaga, for example, Trichodectes Opp. and Damalinea Opp.
From the order of the Thysanoptera, for example, Hercinothxips femoralis and Thrips tabaci. From the order of the Heteroptera, for example, Eurygaster app., Dysdercus intermedius, Piesma quadzata, Cimex lectularius, Rhodnius prolixus and Triatoma Opp. From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporarium, Aphis gossypii, Brevicornyne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus app., Phorodon humuli, Rhopalosiphum padi, Empoasca app., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, t I Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantli, Aspidiotus hederae, Pseudococcus app. and Paylla Opp. From the order of the Lepidoptera, for example, Pectinophora gosaypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctia chrysorrhoea, Lymantria app., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis app., Euxoa app., Feltia app., Earias insulana, Heliothis app., Laphygma exigua, Mamestra brasaicae, Panolis flammea, Prodenia litura, Spodoptera app., Trichoplusia ni, Carpocapsa pomonella, Pieris app., Chilo app., Pyrausta nubilalis, Ephestia kuehuiella, Gallericmellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana. From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica Opp.W Psylliodes chrysocephala, Epilachna variveatia, Atomaria app., Oryzaephilus surinamensis, Anthonomus Opp., Sitophilus Opp., -7 3 -8- I. I i j i i '3 i;i i i i Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera poatica, Dernestes app., Trogoderma Bpp., Anthrenus app., Attagenus spp., Lyctus app., Meligethes aeneus, Ptinus app., Niptus hololeucus, Gibbium paylloides, Tribolium app., Tenebrio molitor, Agriotes app., Conoderus app., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica. From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa app., Lasus app., Monomorium pharaonis and Vespa app. From the order of the Diptera, for example, Aedes app., Anopheles app., Culex app., Drosophila melanogaster, Musca app., Fannia app., Calliphora erythrocephala, Lucilia app., Chrysomyia app., Cuterebra app., Gastrophilus app., Hyppobosca app., Stomoxys app., 1 i5 Oestrus app., Hypoderma spp., Tabanus app., Tannia app., Bibio hortulanus, Oscinella frit, Phorbia app., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. From the order of the Siphonaptera, for example, Xenopsylla cheopia and 'Ceratophyllus spp. From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. From the class of the Helminthes, for example Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Qesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola and phytopathogenic nematodes, for example those of the genera Meloidogyne, Heterodera, Ditylenchus, Aphelenchoides, Radopholus, Globodera, Pratylenchus, Longidorus and Xiphinema. From the class of the Gastropoda, for example, Deroceras app., 30 Arion app., Lymnaea app., Galba app.,Succinea app., Biophalaria app., Bulinus app. and Oncomelania app.. From the class of the Bivalva, for example, Dreissena app..
The invention also relates to agenta which contain the compounds of the formulae I and II, besides suitable formulation auxiliaries.
The agents according to the invention generally contain the active compounds of the formulae I and II to the -9extent of 1 to 95% by weight.
They can be formulated in a variety of ways, as predetermined by the biological and/or chemicophysical parameters. The following possibilities are therefore suitable for formulation: wettable powders emulsifiable concentrates aqueous solutions emulsions, sprayable solutions, dispersions on an oil or water base suspo-emulsions dusting agents seeddressing agents, granules in the form of microgranules, spray granules, coated granules and adsorption granules, 1 water-dispersible granules ULV formulations, microcapsules, waxes or baits.
These individual formulation types are known in principle and are described, for example, in: Winnacker-Kiichler, "Chemische Technologie [Chemical S Technology]", Volume 7, C. Hauser Verlag Munich, 4th Ed., 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker 2nd Ed. 1972-73; K. Martens, "Spray Drying j Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.
i 20 The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are i likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; S 25 H.v.Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley Sons, Marschen, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp.
Ridgewood Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schbnfeldt, "Grenzfl&chenaktive Xthylenoxidaddukte" [Surface-active Ethylene Oxide Adducts]", Wiss.
Verlagsgesell., Stuttgart 1976; Winnacker-Kichler, "Chemische Technologie [Chemical Technology]", Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986.
10 Combinations with other pesticidally active substances, ifertilizers and/or growth regulators may also be prepared on the basis of these formulations, for example in the form of a readymix or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and I which, besides the active substance, also contain wetting i agents, for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkylsulfonates or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'i disulfonate, sodium dibutylnaphthalenesulfonate, or alternatively sodium oleylmethyltaurinate, in addition to a diluent or inert substance. Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene and also higher-boiling aromatic compounds or hydrocarbons, with the addition of S one or more emulsifiers. Examples of emulsifiers which S. can be used are: calcium salts of an alkylarylsulfonic S 20 acid such as Ca-dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol Sethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
Dusting agents can be obtained by grinding the active j substance with finely divided solid substances, for example talc or natural clays, such as kaolin, bentonite, i 30 pyrophillite, or diatomaceous earth. Granules can be produced either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of carriers, such as sand, kaolinites or granulated inert material, by means of binders, for example polyvinyl alcohol, sodium polyacrylate or, alternatively, mineral oils. Suitable active substances can also be granulated in the manner which is conventional for the production of S11- Sfertilizer granules, if desired in a mixture with fertilizers.
The concentration of active substance in wettable powders is, for example, about 10 to 90% by weight; the remainder to 100% by weight is composed of conventional formulation I components. In the case of emulsifiable concentrates, the concentration of active substance can be about 5 to by weight. Formulations in the form of dusts usually contain 5 to 20% by weight of active substance, sprayable solutions about 2 to 20% by weight. In the case of granules, the active substance content depends partly on Iwhether the active compound is liquid or solid and on which granulation auxiliaries, fillers etc. are used.
In addition, the active substance formulations mentioned contain, if appropriate, the adhesives, wetting agents, dispersing agents, emulsifiers, penetrants, solvents, I fillers or carriers which are conventional in each case.
For use, the concentrates, present in commercially available form, are diluted, if appropriate, in a customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases, also in the case of microgranules.
I Preparations in the form of dusts or granulated preparations and also sprayable solutions are usually not further diluted with other inert substances before use.
The application rate required varies with the external conditions, such as, inter alia, temperature, humidity, etcetera. It can vary within wide limits, for example between 0.005 and 10.0 kg/ha or more of active substance; preferably, however, it is between 0.01 and 5 kg/ha.
The active substances according to the invention may be present in their commercially available formulations, and in the application forms prepared from these formulations, as a mixture with other active compounds, such _f -12as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth regulators or herbicides.
The insecticides include, for example, phosphoric esters, carbamates, carboxylic esters, formamidines, tin compounds and substances produced by micro-organisms, inter alia.
Preferred mixture components are 1. from the group comprising the phosphorus compounds acephate, azamethiphos, azinphos-ethyl, azinphos its. methyl, bromophos, bromophos-ethyl, chlorfenvinphos, C, chiormephos, chlorpyriphos-methyl, demeton, demeton- T r 4 :S-methyl, demeton-S-methylsulfone, dialifos, diazinon, 9 t dichlorvos, dicrotophos, 0,0-1,2,2, 2-tetrachloroethyl phosphothioate (SD 208,304) diinethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, fainphur, fenamiphos, fenitrothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isazophos, isothioate, isoxathion., malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, pirimophosethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, pzothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion; 2. from the group comprising the carbamates aldicarb, 2-sec-butylphenyl methylcarbamate
(BPMC),
carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb methomyl, 5-methyl-m-cumenylbutyryl (methyl )carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6, 9-triaza-4-benzyl-6, l0-dimethyl-8-oxa-7-oxo- I13 11-dithia-9-dodecenoate (OK 135), 1-methylthio- (ethylideneamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717); 3. from the group comprising the carboxylic esters allethrin, aiphametrin, 5-benzyl-3-furylmethyl (iR) cis-2, 2-dimethyl-3- (2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bioallethrin, bloallethrin ((S)cyclopentyl isomer), bioresmethrin, biphenate (RS) -1-cyano-1- (6-phenoxy-2-pyridyl )methyl (iRS) -trans-3- (4-tert .butylphenyl 2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthxin, II fenpropathzin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D-isomer), permethrin, pheothrin ((R)-isomer), d-pralethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, tralomethrin; 4. from the group comprising the amidines amitraz, chiordimeform; from the group comprising the tin compounds cyhexatin, fenbutatin oxide; 6. others abamectin, Bacillus thuringiensis, bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzialate, chlorfluazuron, 2-(4-chlorophenyl) 5-diphenylthiophene (UBI-T 930), clofentezine, 2-naphthylauethyl cyclopropanecarboxylate (Ro 12-0470), cyromazin, ethyl N-(3,5-dichloro-4l,2,3,3,3,-hexafluoro-1-propyloxy)phenylcarbamoyl- 2-chlorobenzocarboximidate, DDT, dicofol, dichloro-4- 2-tetraf luoroethoxy) phenylamino) carbonyl)-2,6-difluorobenzamide (IRD 473), diflubenzuron, N-(2 ,3-dihydro-3-methyl-1, 3-thiazol-2ylidene) 4-zylidine, dinobuton, dinocap, endosulfan, S- 14 14 ethofenprox, (4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)propyl)silane, (4-ethoxyphenyl)(3-(4-fluoro-3phenoxyphenyl)propyl)dimethylsilane, fenoxycarb, 2fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-l-pentyl) diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-NCH, hexythiazox, hydramethylnon (AC 217300), ivermectin, 2-nitromethyl- 4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl-3,4dihydrothiazole (SD 35651), 2-nitromethylene-l,2thiazinan-3-ylcarbamaldehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, triflumuron.
H The active substance content of the use forms prepared j 15 from the commercially available formulations can be from S0.00000001 to 100% by weight of active substance, preferably between 0.00001 and 1% by weight.
SApplication is effected in a conventional fashion, i matched to the use forms.
S 20 The active substances according to the invention are also suitable for combating endo- and ecto-parasites, preferably in the veterinary medicine area or in the area of animal husbandry.
The active substances according to the invention are i 5 applied in a known fashion, such as by oral application in the form of, for example, tablets, capsules, potions or granules, by dermal application in the form of, for example, dipping, spraying, pouring-on and spotting-on and powdering, and also by parenteral application in the form of, for example, injection.
The novel compounds, according to the invention, of the formula I can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese 15 etc.). In a preferred embodiment of the invention, the novel compounds, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since excretion in the droppings occurs in an effective I ffashion, the development of insects in the animal j droppings can be prevented very simply in this fashion.
SThe dosages and formulations suitable in each case are particularly dependent on the type and stage of development of the productive animals and also on the degree of infestation of the insects, and can easily be determined and fixed by conventional methods. In the case of cattle, the novel compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight.
The following examples serve to illustrate the invention.
A. Formulation Examples a) A dusting agent is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as inert material and comminuting the mixture in I 20 a hammer mill.
j b) A wettable powder which is easily dispersible in water |I is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of kaolin-containing -t quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of j sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding the mixture in a pin disk mill.
c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water, and grinding the mixture in a ball mill to a fineness of below 5 microns.
16 d) An emulsifiable concentrate can be prepared from Sparts by weight of active substance, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol (10 EO) as emulsifier.
j e) Granules can be prepared from 2 to 15 parts by weight Sof active substance and an inert granule carrier I material such as attapulgite, granulated pumice and/or I quartz sand.
Advantageously, a suspension of the wettable powder from i Example b) having a solids content of 30 is used, and tic" this is sprayed onto the surface of attapulgite granules, iwhich are dried and mixed intimately. The proportion by weight of the wettable powder is about 5 and that of S 1 .5 the inert carrier material about 95 of the finished granules.
B. Chemical examples i 1,1,1-Trifluoro-2-(2-ethoxy-5-pyridyl)-5-(3-phenoxyi phenyl)-2-pentene (No. 1, example of formula I) 2.5 g (11.4 mmol) of i 6.0 g (10.8 mmol) of 3-(3-phenoxyphenyl)-propyltriphenylphosphonium bromide and 1.3 g (12.0 mmol) of potassium tert.-butoxide are mixed in 50 ml of toluene under a protective gas atmosphere, and the mixture is stirred for 6 hours at 20"C. The potassium bromide is then removed by Swashing with water, the toluene phase is concentrated, MR and the toluene extract is separated by column chromatography (eluent: ethyl acetate:heptane 2:8; stationary phase: silica gel). This gives 3.50 g (75 of the olefin product as colorless liquid. Solubility: readily soluble in heptane and toluene; insoluble in water. The 1 H-NMR and GC measurements confirm that a mixture of diastereomers (Z and E isomers) is present in the ratio 2.3:1, b.p.
1013 :386 and 395"C (GC measurement).
-17- 1,1,1-Trifluoro-2-(2-ethoxy-5-pyridyl)-5-(3-phenoxyphenyl)-pentane (No. 61, example of formula II) g of platinum on active carbon (10 is initially introduced into 100 ml of ethanol under an atmosphere of hydrogen, and 5.0 g (12.1 mmol) of olefin are added.
After 4 hours at 1013 mbar, the reaction mixture is filtered through silica gel and concentrated. This gives the compound No. 61 as a colorless liquid, the yield is 4.9 g (97 The compounds of the formulae I and II, which are listed below, may be prepared in accordance with these procen dures.
Abbreviations: Me CH 3 Et C 2
H
5 Ph C 8
H
5 iPr CH(CH 3 2 0 t C t I ~Table 1I18 R2 7 3 B4 QB R 6
(I)
Ex.
No.
Ri R' R' A R4 B R 5 R 6 Physical data OC, GC) 1013 mbar 0000 0 0 0009 0 Ot 0 0 0 0 00 0*0000 0 0 0 001000 0 4 04 O 4 0 #4 0 1 CF 3
H
2 I CF' 3
H
3 CF 3
H
14 CF 3
H
5 CF 3
H
TI CH 3
H
7 CH 3
H
8 CH 3
H
9 II H H 0 it H H 1 ff iPr H 2 'I iPr H 3 Cf1 3
H
14 CH 3
H
o H S H CH2 H O H CH2
H
o H S H CH2 H o H CH2 H o H CH2 H o H
HH
CHi H CH F CH F CH H CH H CH H CH H CHi H CH H CH H CH F CH F OPh 393, 1401 OPh OPh OPh 389, 397 OPh 401, 1410 OPh 405, 415 OPh OPh OPh OPh 405, 1409 OPh OPh ONh CH2 H CH- H OPh 386, 395 -t 0.:
CH
2
CF
3
CF
3 H CH 2 H CH H OPh 372, 382
TICF
3
H
TiCF 3
H
'ICF
3
H
'I H 3
H
Ti Cl 3
H
H H 0 H CH2 H 0 H CH2 H o H CH2j CHi H CH F CH- F CH- H Cli H OPh 377, 387 OPh 374, 385 OPh 381, 390 OPh OPh 392, 398 CHi H OPh 19 Table 1 continuation Ex. R1 R 2
A
3 A R 4 B R5~ R' Physical No. data OC, GC) 1013 abar 22 j.O Pr H M2 H CH H OPh
CH
2
CF
3 23 iPr H 0 H CHI H OPh 241 H H 0 H CH H OPh C H2 H CH H OPh S 26 H CF 3 H 0 H CH H OPh C t t rMeOC; 27 CF 3 H 0A H CI H OPh 29 C1,2 CF 3 H 0H H CH H OPh 290 L CF 3 H 0H H CH H OPh 31 CF 3 H CH2 H CH H OPh 32 CF 3 H 0 H CH H OPh 33 CF 3 H CH 2 H CH F OPh 341 CF 3 H 0 H CH F OPh iPr H H 2 H CH H Oft 36 O~rH 0 H CH H OPh
A
20 Table 1 continuation Ex.
No.
R 1 R2 R 3 A R 4 B R5 R 6 Physical data OC, GC) 1013 mbar EtON
QCF
3
H
CR
2 H CH H OPh I .1
CF
3 H 0 H Q CF 3 H CH 2
H
CF
3 H 0 H EtQ-
CF
3 Cf1 3
CH
2
H
it Cl1 3
CH
3
CH
2
H
it CF 3
CR
3 Cf1 2
H
it CF 3 H 0 CN GC17>CF3 H
CH
2
H
CF
3 H 0 H
CH
3 H CH 2
H
CR
3 H 0 H EtQt:
CF
3 H
CH
2
H
CF
3 H 0 H CH H CH H CR H CR H CH H CR F di,-H CH H CH H CH H CH H CH H CH H OPh OPh OPh OPh OPh OPh OPh OPh OPh OPh OPh OPh OPh 1~j 51 1/ CRH3 H 52
CH
3
H
e0
CR
2 H CH H OPh 364I, 372 0 H CR H OPh 371, 376 7V I- r r- re i -I I I -I 21 Table 1 continuation Ex.
No.
R rR 2
R
3 A R" B R' R' Physical data OC, GC) 1013 mbar
NCF
CH2 H CH H OPh
CF
3 H 0 H CH H OPh CH2 H CH H OPh
CF
3 H 0 H CH H OPh 1 4 t *I I .1 57 CF 3
H
58 11 CF 3
H
59 or CF 3
H
C
2 0
CF
3
CF
3
H
CH2 H N H OPh O H N H OPh CH2 H N H OPh 0 H N H OPh i :i t i i 1H-NMR data (eluent: CDC131, standard: TMS, 6(H) [ppm]) 4 E-Olefin: 1,39, t (3H, 0QH 2
CH
3 7.3 Hz); 2,30, m (2H,
CH
2 CH2CH); 2,61, t (2H, krHc2H 2 7.0 Hz); 4,36, q, (2H, OCH2CH 3 7.3 Hz); 6,42 tq (1H, C=CHCH 2 1.7 Hz, 7.5 Hz); 6,68-7,35, m (10H, Aryl-H); 7,86, d (1H, 6-yridyl-H, 2.5 Hz).
Z-Olefin: 1,38, t (3H, 0CH2CH 3 7.3 Hz); 2,73, m (4H, ArCH 2
CH
2 CH); 4,36, q (2H, QCH 2
CH
3 7.3 Hz); 5,95, tq (1H, C=CHCH 2 6,9 Hz); 6,65, d (1H, 3-Pyridyl-H, 8.8 Hz); 6,85-7,48, m (10H, Aryl-H); 7,99, d (1H, 6-?yridyl-H, Hz).
641s 4
LI
A,
.I
22 Table 2 R1 CH ?i A R R2"I 3 t R
(II)
Ex.
No.
Ri R2 R3 A R 4B R R1 Physical data C, GC) 1013 mbar
I
61 EtO NY
CF
3 H CH2 H CH H OPh 392 I,.1
CF
3 H 0 H
CF
3 H 0 H
CF
3 H CH 2
H
CH
3 H CH 2
H
CH
3 H 0 H H H CE 2
H
H H 0 H iPr H 0 H iPr H CH 2
H
CF
3
CH
3
CH
2
H
CH
3
CH
3
CH
2
H
CF
3
CM
3
CH
2
H
CF
3 H 0 CN CH H CH F CH F CH H CH H CH H CH H CH H CH H CH H CM H CH F CH H OPh 390 OPh 385 OPh 3941 OPh 405 OPh 411 OPh OPh OPh OPh UPh OPh OPh OPh i-; i:i i i re 75 CF 3
H
1.
CH
2 F3 76 CF 3
H
77 CF 3
H
78 t F 3
H
79 C CM 3
H
iPr H
CM
2 H CM H OPh 380 O H
CH
2
H
O H
CM
2
H
CH2 H CH H CH F CH F CM H CH H OPh 382 OPh 3 84 OPh 378 OPh 386 OPh -23- Table 2 -continuation Ex. RR R A R' B R R 6 Pyia No. data OC, GC) 1013 mbar 81i~ H 0 H CH H OPh H2 CF 3 82 CF 3 H CH2 H CH H OPh 83 CF 3 H 0 H CH H OPh 84 3 CH a H OPh MeJQ' F H
CH
CF
3 H 0 H CH H OPh 86 r CF H CH2 H CH H OPh IV 8 CF 3 HCHH~ H OPh 88 if CF 3 H CH2 H ai F OPh 89 If CF 3 H 0 H CH F OPh EtC
C
3 H CH 2 HF CH H OPh 91 CF 3 H 0 H CH H OPh 92 H CH2 H CH H OPh EtC S 93 H CF 3 H 0 H CH H OPh 94 K1- CF 3 H CH2 H CH H OPh CF3 H 0 H CH H O~h 24 Table 2 continuation Ex.
No.
RI R 2 R' A Ri' B R'
R
6 Physical data
GC)
1013 mbar 96 97 98 99 100 101 102 103 10i4
CF
3
H
I? CF 3 Hi
CF
3
H
CF
3 C)r
CF
3
H
CH
2
CF
3 CH2 H 0 H CR2 H 0 H
CH
2
H
0 H 0 H OPh OPh OPi2 OPh OPh OPh OPh 390 ~Q CF 3 H CR2 H CR F OPh CF 3
~C
3
CF
3 H 0 H CH F OPh I I r 25 Table 2 continuation Ex.
No.
Ri R 2
R
3 A R 4 B R5 R 6 Physical data i(b.p. GC) 1013 mbar 105 106
CR
3
H
CR
3
H
CH2 H 0 H 1 H-NMR data (eluent: CDCl 3 1 standard: TMS, 6(H) (ppm]) Ex.No. 1,4, (2H, CH2); 1,90, mn (2H, CH 2 t (I&rCH2, 2H, 7.3 Hz); 3,19, m (1H, F 3 CCH); 4 73 q (21H, OCH 2
CF
3 8,6 Hz); 6,75-7,36, mn (10H, Aryl-H); 7,51, dd (OH, 4-Pyridyl-H, 8.8 Hz, 2.5 Hz); 7,98, d O1H, 6.-Fyridy1-H, Hz).
26 C. Biological Examples Example 1 The insides of the lid and the bottom of a Petri dish are each uniformly coated with 1 ml of the formulation to be tested, emulsified in water, and a batch of 10 imagines of the common house fly (Musca domestica) are introduced when the coating has dried on. After the dish has been sealed, .t is stored at room temperature, and the mortality of the test animals is determined after 3 hours.
At 250 ppm (relative to the content of active substance, preparations 1, 2, 6, 7, 11, 15, 16, 19, 20, 51, 52, 61, 64, 65, 75 and 79 show a good action (100 mortality) against the common house fly.
Example 2 Batches of 10 larvae (L4) of the German cockroach (Blattella germanica) are introduced into the Petri dish treated as in Example 1, the dishes are sealed, and the mortality of the test animals is determined after 5 days.
4 At 100 ppm (relative to the content of active substance) 20 the preparations 1, 2, 11, 15, 20, 61, 65, 65, 75 and 79 showed a good action (100 mortality) against the German cockroach.
0 Example 3 L One layer of filter paper and on this an amount of 3 5 ml of a semisynthetic diet are applied to the insides of the bottom of a Petri dish. After cooling, decreasing concentrations of the formulation to be tested are sprayed with water onto the surface of the feed and the filter paper, and, when the spray coating has dried on, batches of 10 larvae (L3 L4) of the cotton worm (Prodenia litura) are introduced.
.4
J
-C S-27 The Petri dishes are sealed with lids and stored for 7 I days at room temperature, and the mortality of the test animals is then determined.
At 1000 ppm (relative to the content of active substance), preparations 1, 2, 6, 15, 16, 19, 61, 64, and 79 show a good action against larvae of the cotton worm.
Example 4 {1 Larvae of the Mexican bean beetle (Epilachna varivestis, L III) were treated in a spraying apparatus with a preparation of active substance of the desired concentration. At the same time, leaves of dwarf beans (Phaseolus vulgaris) were dipped into the corresponding solutio of active substance. After the spray coating had dried on, the larvae of the beetle were placed on the bean leaves.
After 3 days, the destruction of the larvae was determined as a percentage. At 1000 ppm (relative to the active substance), the preparations 1, 2, 6, 7, 15, 16, 19, 20, 51, 52, 61, 64, 65, 75 and 79 showed a good action against the Mexican bean beetle.
i Example 11 Larvae of the last larval stage of the brown plant hopper (Nilaparvata lugens) are placed in Petri dishes where a Ji treated, absorbent piece of paper has been placed on the i| 25 bottom. Before the animals are introduced, each filter paper is moistened with 2 ml of distilled water and subsequently sprayed with decreasing dosages of the test preparation, emulsified in water corresponding to 600 1 of water/ha. After the animals have been introduced into the dishes, the latter are sealed immediately and stored for 24 hours under laboratory conditions until they are evaluated. After this, the action mortality) is evaluated. At a concentration of active substance in the spray liquor of 125 ppm, the preparations 1, 6, 51, 64, j v r i
E
-1 ill 1 ,u 28 and 79 show 100 action against brown plant hoppers.
xample 6 Field beans (Vicia faba) which are heavily infested with a cow pea aphid (Aphis craccivora) are sprayed with aqueous dilutions of concentrations of wettable powders with an active substance content of 100 ppm until the runoff point is reached. The mortality of the aphids is determined after 3 days. 100 destruction can be achieved with the compounds of Examples 1, 15, 16, 19, 61, 64, 65, 75 and 79.
t t I Ittltl t It

Claims (5)

1. A compound of the formulae I and II, the stereo- isomers thereof, and the mixtures of the latter C=C A C R R 6 CH-A-R R6 (I) (II) t 11th A A where Ri is pyridyl, pyrimidyl, thienyl, thiazolyl, furanyl, pyrazolyl, 1,3-oxazolyl or imid- azolyl, all of which can be substituted, R 2 is H, alkyl, (Cl-C) haloalkyl, alkoxy, (C 3 -C 6 cycloalkyl, -CH=CH 2 or -C-CH, R 3 is H or (Cl-C 4 )alkyl, R4 is H, (Cl-CA)alkyl, -CN or -CinCH, A is CH 2 0 or S, B is CHI, N or C (CHA) is H or halogen and R 6 is phenyl, phenoxy or benzyl, all of which can be monosubstituted to pentasubstituted by halogen or (Cl-CA)haloalkyl. A compound of the formulae I and II of claim 1, in which Ri is a radical of the formulae A, B, C, D, E or F (R7)m yt7)mCR 7 )m R 7 m I) 30 HOE 89/F 082 (7)m N (R7)m N 0 (F) in which R 7 is H, halogen, (Ci-C 4 )alkyl, (Ci-C 4 )alkoxy, (Ci-C 4 haloalkyl, (Cl-C4)halo- alkoxy and m is 1 or 2, ,a R 2 is (Ci-C 3 )alkyl, cyclopropyl or CF 3 R 3 is H or methyl, SB is CH, i R is H, methyl, -CN or -C-CH and R 6 is phenoxy which can be substituted in the i 4-position by Cl, Br or CF 3
3. A compound of the formulae I and II of claim 2, where R 7 is Cl, Br, (C 1 -C 3 )alkoxy, -OC, -H 2 CF 3 Sor -OCF 2 CF 2 H.
4. A compound as claimed in one or more of claims 1 to 3, wherein R 1 is a radical of the formula A, B or C. A compound as claimed in one or more of claims 1 Sto 4, wherein R I is a radical of the formula A. S6. A process for the preparation of a compound of formulae I and II as claimed in one or more of claims 1 to 5, which comprises a) for compounds of the formula I, reacting a compound of the formula III (III) N C 0 IR2 where R 1 and R 2 are as defined in formula C Ui 31 I, with a compound of the formula IV R 6 B CH A -C P(R R 4 R 3 where R3, R 4 R5, R 6 A and B are as defined in formula cyclohexyl or butyl, and (IV) I and R8 is phenyl, for compounds of the formula II, catalytically hydrogenating the olefin the corresponding compound of the formula I with hydrogen or a liberating compound. function of hydrogen- rrre r t I Ittr rr i Is t r i trir ri E Il I I r Il L (I I I I I i I(I t It( PI
7. A insecticidal or acaricidal composition comprising an effective amount of a compound of the formulae I and/or II in adjunct with insecticidally or acaricidaily effective carriers or excipients.
8. A method of controlling insect pests or acarids, which comprises applying an effective amount of a compound of the formulae I and/or II to these insect pests or acarids, or the plants, areas or substrates infested with them. DATED. this 20th day of January, 1992 HOECHST AKTIENGESELLSCHAFT WATERMARK PATENT TRADEMARK ATTORNEYS THE ATRIUM 290 BURWOOD ROAD HAWTHORN VICTORIA 3122 AUSTRAUA DBM/KJS:JJC AU5118090.WPC (DOC.07)
AU51180/90A 1989-03-10 1990-03-09 Heteroaryl-aryl-butene and -butane derivatives, process for their preparation, agents containig them, and their use as pesticides Ceased AU622292B2 (en)

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