Classifications

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  • C07C205/32—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to acyclic carbon atoms and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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  • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
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  • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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  • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
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  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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  • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
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  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
  • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
  • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
  • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
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  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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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
  • C07D213/24—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
  • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/57—Nitriles
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  • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
  • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
  • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
  • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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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  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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  • 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
  • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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  • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
  • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
  • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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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
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  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

• the present invention relates (1 ) to compounds of formula
• a ⁇ and A 2 are each independently of the other a bond or a d-C 6 alkylene bridge which is unsubstituted or substituted by from one to six identical or different substituents selected from halogen and C 3 -C 8 cycloalkyl;
• a 3 is a C ⁇ -C 6 alkylene bridge which is unsubstituted or substituted by from one to six identical or different substituents selected from halogen and C 3 -C 8 cycloalkyl;
• Y is O, NR 7 , S, SO or SO 2 ;
• X-i and X 2 are each independently of the other fluorine, chlorine or bromine;
• Q is O, NR 5 , S, SO or SO 2 ;
• D is CH or N
• R 5 , R 6 and R 7 are each independently of the others H, d-C 6 alkyl, d-C 3 haloalkyl, d-C 3 haloalkylcarbonyl, d-C 6 alkoxyalkyl, C ⁇ -C 6 alkylcarbonyl, d-C 6 alkoxycarbonyl, C 3 -C 8 - cycloalkyl, C3-C 8 cycloaIkyl-d-C 6 alkyl, C 3 -C 8 cycloalkylcarbonyl; k is 1 , 2 or 3 when D is nitrogen; or is 1 , 2, 3 or 4 when D is CH; m is 1 or 2;
• R 10 is any radical which comprises from one to three hetero atoms selected from O, N and S; and which may be connected to R 12 via a d-C 6 alkylene bridge;
• the compounds of formula (I) and, where applicable, their tautomers are able to form salts, e.g. acid addition salts.
• the latter are formed, for example, with strong inorganic acids, such as mineral acids, e.g. sulfuric acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, e.g. halo-substituted, C C 4 alkanecarboxylic acids, for example acetic acid, saturated or unsat ⁇ rated dicarboxylic acids, e.g. oxalic, malonic, maleic, fumaric or phthalic acid, hydroxycarboxylic acids, e.g.
• compounds of formula (I) having at least one acid group are able to form salts with bases.
• Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, e.g.
• sodium, potassium or magnesium salts or salts with ammonia or an organic amine, such as morph- oline, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine. It may also be possible for corresponding internal salts to be formed. The free form is preferred. Of the salts of compounds of formula (I), preference is given to agro- chemically advantageous salts.
• any reference to the free compounds of formula (I) or to their salts is to be understood as including, where appropriate, also the corresponding salts or the free compounds of formula (I), respectively.
• Halogen as a group perse and as a structural element of other groups and compounds, such as haloalkyl, halocycloalkyl, haloalkenyl, haloalkynyl and haloalkoxy, is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, more especially fluorine or chlorine, especially chlorine.
• carbon-containing groups and compounds each contain from 1 up to and including 20, preferably from 1 up to and including 18, especially from 1 up to and including 10, more especially from 1 up to and including 6, especially from 1 up to and 70194A
• Alkylene is a straight-chain or branched bridging member and is especially -CH 2 -, -CH2CH2-, -CH2-CH2-CH2-, -CH2-CH -CH2-CH2-, -CH2-CH2-CH2-CH2-, -CH(CH 3 )-, -CH 2 (CH 3 )CH 2 -CH 2 -, -CH(C 2 H 5 )-, -C(CH 3 ) 2 -, -CH(CH 3 )CH 2 -, -CH(CH 3 )CH(CH 3 )- or
• Alkyl as a group perse and as a structural element of other groups and compounds, such as haloalkyl, alkoxy, alkoxyalkyl, haloalkoxy, alkoxycarbonyl, alkylthio, haloalkylthio, alkylsulfonyl and alkylsulfonyloxy, is - in each case giving due consideration to the number of carbon atoms contained in the group or compound in question - either straight-chain, e.g.
• Alkenyl and alkynyl - as groups perse and as structural elements of other groups and compounds, such as haloalkenyl, haloalkynyl, alkenyloxy, haloalkenyloxy, alkynyloxy or halo- alkynyloxy - are straight-chain or branched and each contains two or preferably one unsat- urated carbon-carbon bond(s).
• haloalkenyl, haloalkynyl, alkenyloxy, haloalkenyloxy, alkynyloxy or halo- alkynyloxy - are straight-chain or branched and each contains two or preferably one unsat- urated carbon-carbon bond(s).
• Cycloalkyl - as a group perse and as a structural element of other groups and compounds, such as alkyl - is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Cyclopentyl and cyclohexyl, and especially cyclopropyl, are preferred.
• Halo-substituted carbon-containing groups and compounds such as haloalkyl and haloalkoxy, may be partially halogenated or perhalogenated, the halogen substituents in the case of polyhaiogenation being the same or different.
• haloalkyl - as a group per se and as a structural element of other groups and compounds, such as haloalkoxy - are methyl substituted from one to three times by fluorine, chlorine and/or bromine, such as CHF 2 , CF 3 or CH 2 CI; ethyl substituted from one to five times by fluorine, chlorine and/or bromine, such as CH 2 CF 3) CF 2 CF 3 , CF 2 CCI 3 , CF 2 CHCI 2 , CF 2 CHF 2 , CF 2 CFCI 2 , CH 2 CH 2 CI, CF 2 CHBr 2 , CFgCHCIF, CF 2 CHBrF or CCIFCHCIF; propyl or isopropyl each substituted from one to seven times by fluorine, chlorine and/or bromine, such as CH 2 CHBrCH 2 Br, CF 2 CHFCF 3 , CH 2 CF 2 CF 3 , CF 2 CF 2 CF 3 CF
• fluorine, chlorine and/or bromine such as CF(CF 3 )CHFCF 3 , CF 2 (CF 2 ) 2 CF3 or CH 2 (CF 2 ) 2 CF 3 .
• Aryl is especially phenyl or naphthyl, preferably phenyl.
• Heterocyclyl is to be understood as meaning a five- to seven-membered monocyclic ring which is aromatic or nonaromatic and which contains from one to three hetero atoms selected from the group consisting of N, O and S, especially N and S; or a bicyclic ring system which is aromatic or nonaromatic and which may contain, either in one ring only - as in quinolyl, quinoxalinyl, indolinyl, benzothiophenyl or benzofuranyl, for example - or in both rings - as in pteridinyl or purinyl, for example - one or more hetero atoms selected independently of one another from N, O and S.
• R 13 is C C 12 alkyl, d-C 6 haloalkyl, C 3 -C 6 cycloalkyl, C C 6 alkoxy, d-C 3 haloalkoxy, C C 6 - alkylamino, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl; or R 13 together with Rn is a C C 6 alkylene bridge; or R 13 together with R 12 a C 3 -C 6 alkylene bridge; preferably wherein R 1 3 is C C 12 alkyl, C C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkenyl or C 2 -C 6 haloalkynyl;
• R 14 is H, C C 6 alkyl, C 3 -C 6 cycloalkyl-C C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
• R 15 is H, OH, d-d 2 alkyl, C C 6 alkoxy, d-C 12 haloalkyl, C r C 6 haloalkoxy, C 3 -C 6 alkenyl- oxy, C 3 -C 6 haloalkenyloxy, -N(R 18 ) 2 , C 3 -C 6 cycloalkyl, aryl, aryloxy, benzyloxy or heterocyclyl; or R 15 together with R 1 is an C 1 -C 6 alkylene bridge; and
• R 16 is H, C C 6 alkyl, d-C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-d-C 6 alkyl, C r C 6 alkoxy-C ⁇ -C 6 alkyI, C C 6 haloalkoxy- C C 6 alkyl, d-Cealkoxy-d-Cealkoxy-d-Cealkyi, d-Cehaloalkoxy-d-Cealkoxy-d-Cealkyl, 70194A
• R 17 is H, d-C 6 alkyl, C C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-d-C 6 alkyl, d-Cealkoxy-d-Cealkyl or benzyl; the two substituents R 18 are each independently of the other d-C 12 alkyl or benzyl or together are a C 2 -C 6 alkylene bridge;
• a 3 is a straight-chain alkylene bridge; especially ethylene, propylene or butylenes; more especially propylene;
• the invention relates also to a process for the preparation of a compound of formula (I), or a salt thereof, wherein
• G-Z 2b (1Mb), wherein G denotes the part of the formula in brackets designated G in formula (II), Z 2 is a radical of formula -Y-C( O)R 2 ., Y is as defined for formula (I) under (1) and R 2 ⁇ is d-Cealkyl unsubstituted or substituted by from one to three identical or different halogen substituents, or is phenyl unsubstituted or substituted by from one to three identical or different substituents selected from halogen, CN, nitro, d-C 6 alkyl, d-C 6 haloalkyl, d-C 6 - alkylcarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, d-C 6 haloalkoxy, d-C 6 alkoxycarbonyl and C 3 -C 6 haloalkenyloxy, is converted by hydrolytic cleavage into a compound of formula
• G-Z 3 (IV) wherein G denotes the part of the formula in brackets designated G in formula (II), Z 3 is YH and Y is as defined for formula (I) under (1); or
• Hal is halogen, preferably bromine or chlorine, and alkyl is d-C 6 alkyl, or the two alkyl radicals together form a C 2 -C 8 alkylene bridge, to form a compound of formula
• alkyl and Y are as defined above;
• G-Z 6 (VII), wherein Z 6 is a group -Y-CH 2 -C( O)H, G is as defined above for the compound of formula (II) and Y is as defined for formula (I) under (1 ), either
• L 3 is a leaving group, preferably chlorine or bromine, and Hal is chlorine or bromine;
• Hal is halogen and X is chlorine or bromine.
• the invention relates also to
• R-,, R 2 , R 3 and m are as defined for formula (I) under (1 ), Q is O, NR 5 or S and Z is one of the radicals Z 1 to Z 6 as defined for the above formulae (II) to (VII), and R 5 is as defined for formula (I) under (1), and the resulting compound of formula
• A-,, A 2 , A 3 , D, W, Q, T, R 1 ( R 2 , R 3 , R 4 , R 10 , Rn, R 12 , m and k are as defined for formula (I) under (1) and Z is one of the radicals Z to Z 6 as defined for formulae (II) to (VII) indicated above, is, as necessary, that is to say according to the meaning of the radical Z, reacted further analogously to one or more of process steps (a) to (g).
• Z in compound X a has the same meanings as ⁇ in the compound of formula (II), and Z in compound X/b has the same meanings as Z 2 as defined for formula (III), and so on.
• the invention relates also to
• the radicals Z are as defined above for the compounds X/a to X/f; that is to say, for example, Z in the compound of formula Xll/a has the same meanings as Z 1 in the compound of formula (II), and Z in compound Xll/b has the same meanings as Z 2 as defined for formula (III), and so on.
• the invention relates also to
• the invention relates also to
• R 3 , Q, Y and m are as defined for formula (I) under (1) and R and R 2 are halogen, analogously to Process (k).
• the invention relates also to a process
• Hal is a halogen atom, preferably bromine or iodine
• a ⁇ , A 2 , A 3 , D, W, Q, T, Ri, R 2 , R 3 , R 4 , m and k are as defined for formula (I) under (1 ), is reacted in the presence of a heavy metal catalyst and, where appropriate, of a phosphine with a compound of formula
• R 0 is as defined for formula (I), and the resulting compound of formula (I) is, if desired, reacted further to form a different compound of formula (I); by, for example,
• the invention relates also to a process for the preparation of a compound of formula (I) as defined above, wherein
• R 10 (Rn)P( O)(O-alkyl) 2 (XXIVb), which are known or can be prepared by processes known perse and wherein R ⁇ 0 and Rn are as defined for formula (I) under (1); or
• R 10 (Rn)C CH 2 (XXV), which is known or can be prepared by processes known perse and wherein R 10 and Rn are as defined for formula (I) under (1); or
• Processes (n) to (t) according to the invention may also be carried out on any desired precursor, and those precursors can then be processed according to Processes (a) to (m) to form the compounds of formula (I).
• the invention relates also to corresponding intermediates.
• Such intermediates, where novel, are the compounds of formulae (II) to (XXVI), in free form or in salt form, and compounds of formulae
• reaction mixture preferably from approximately -20°C to approximately +150°C
• a closed vessel under pressure, under an inert gas atmosphere and/or under anhydrous conditions.
• Especially advantageous reaction conditions can be found in the Examples.
• Especially preferred as leaving group are chlorine, bromine, mesy
• oxidising agents there are used, for example, hydrogen peroxide, a peracid, such as peracetic acid, trifluoroperacetic acid or 3-chloroperbenzoic acid, or a mixture thereof, such as sodium perborate in acetic acid.
• an inorganic base such as NaOH or KOH
• aminolysis with a primary amine, such as n-butylamine can be carried out in a hydrocarbon, such as toluene or benzene, at temperatures of from 0°C to 150°C, preferably at from 20°C to 80°C.
• the preferred reaction temperature is from 0°C to 120°C, especially from 20°C to 80°C.
• a strong mineral acid for example hydrochloric acid, sulfuric acid or 4- toluenesulfonic acid.
• reaction is carried out in an inert solvent, for example benzene or toluene, or an ether, such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran, at temperatures of from 0°C to 150°C, preferably at from 20°C to 80°C.
• an inert solvent for example benzene or toluene
• an ether such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran
• dichlorovinyl compounds it is also possible for the process to be carried out in dimethylformamide, benzene, toluene, or in an ether, at temperatures of from 0°C to 120°C, preferably at from 20°C to 80°C, and in the presence of trichloroacetic acid/sodium trichloroacetate, then by addition of acetic anhydride, optionally with the addition of base, for example triethylamine, and finally by addition of zinc and acetic acid.
• dimethylformamide, benzene, toluene, or in an ether at temperatures of from 0°C to 120°C, preferably at from 20°C to 80°C, and in the presence of trichloroacetic acid/sodium trichloroacetate, then by addition of acetic anhydride, optionally with the addition of base, for example triethylamine, and finally by addition of zinc and acetic acid.
• a coupling reagent for example azodicarboxylic acid diethyl or diisopropyl ester and triphenylphosphine, can be used.
• the process can be carried out in an inert solvent, such as in an ether or in toluene, at from 0°C to 80°C, and in the presence of a suitable base, for example a trialkylamine.
• the reaction is preferably carried out in a solvent, such as dioxane, dichloromethane, acetonitrile or toluene, at from 0 to 100°C, and in the presence of a base.
• a solvent such as dioxane, dichloromethane, acetonitrile or toluene
• the reaction is preferably carried out in water or a chlorinated hydrocarbon and using a halogenating agent, such as chlorine, bromine, NaOCI or tert-butyl hypochlorite.
• a halogenating agent such as chlorine, bromine, NaOCI or tert-butyl hypochlorite.
• the reaction is preferably carried out in dimethylformamide, dimethylacetamide, N- methylpyrrolidone, dioxane, tetrahydrofuran, dimethoxyethane or acetonitrile at from 0 to 200°C, preferably at from 50 to 120°C.
• Suitable catalysts are, for example, Pd(OAc) 2 , PdCI 2 , PdCI 2 (PPh 3 ) and Pd(PPh 3 ) 4 ; a phosphine, for example a triaryl- or trialkyl-phosphine, may be added where appropriate.
• the reaction is preferably carried out in an amide, such as dimethylformamide, dimethylacetamide or N-methylpyrrolidone, in dioxane, dimethoxyethane, acetonitrile, tetrahydrofuran, using an alkyl halide at from 0°C to 120°C, preferably at from 20° to 80°C.
• an amide such as dimethylformamide, dimethylacetamide or N-methylpyrrolidone
• dioxane dimethoxyethane
• acetonitrile acetonitrile
• tetrahydrofuran using an alkyl halide at from 0°C to 120°C, preferably at from 20° to 80°C.
• Suitable bases are, for example, potassium carbonate, sodium carbonate and sodium hydride.
• a phase transfer catalyst for example a tetraalkylammonium salt, is added where appropriate.
• oxidising agent for example, sodium bichromate or chromium trioxide in aqueous sulfuric acid, with a solvent such as acetone; at a working temperature of from 0°C to about 60°C; or with pyridinium dichromate in dichloromethane at -40°C.
• a solvent such as acetone
• pyridinium dichromate in dichloromethane at -40°C.
• a mixture of dimethyl sulfoxide and oxalyl chloride in dichloromethane as solvent and in the presence of a base, for example triethylamine, preferably at a working temperature of from -70°C to +40°C.
• the process is preferably carried out in an alcohol, for example methanol, ethanol or isopropanol, in an amide, such as dimethylformamide, dimethylacetamide, N-methylpyrroIi- done, in an ether, such as dioxane or dimethoxyethane, in pyridine or in acetonitrile; at from 0 to 120°C, preferably at from 20 to 80°C.
• an alcohol for example methanol, ethanol or isopropanol
• an amide such as dimethylformamide, dimethylacetamide, N-methylpyrroIi- done
• an ether such as dioxane or dimethoxyethane
• a base for example potassium carbonate, sodium carbonate, sodium acetate, potassium acetate, triethylamine, ethyldiisopropylamine or sodium hydride, is preferably used.
• phase transfer catalyst for example a tetraalkylammonium salt, is used where appropriate.
• the reaction is preferably carried out in toluene, tetrahydrofuran, dioxane, dimethoxyethane, dimethylformamide or dichloromethane at from -60 to 150°C, preferably at from 20°C to 80°C, and in the presence of a base.
• the base for example, potassium tert-butoxide, sodium tert-butoxide, butyllithium, sodium hydride, lithium diisopropylamine, sodium methoxide or an organic base, such as triethylamine, ethyldiisopropylamine, 1 ,8-diazabicyclo[5.4.0]undec-7-ene, in the presence of lithium chloride or lithium bromide.
• reaction is preferably carried out using compounds of formula (XX) wherein Hal is chlorine, bromine or iodine.
• Suitable solvents are amides, such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, ethers, for example dioxane or dimethoxy- 70194A
• reaction is carried out at from 0°C to 200°C, preferably at from 50°C to 120°C.
• the reaction is carried out with the use of a palladium catalyst, such as Pd(OAc) 2 , PdCI 2 or PdCI 2 (PPh 3 ), where appropriate in the presence of a triaryl- or trialkyl-phosphine, and of a base, such as triethylamine, lithium diisopropylamide, sodium carbonate, potassium carbonate, caesium carbonate or sodium hydride.
• a palladium catalyst such as Pd(OAc) 2 , PdCI 2 or PdCI 2 (PPh 3 )
• a base such as triethylamine, lithium diisopropylamide, sodium carbonate, potassium carbonate, caesium carbonate or sodium hydride.
• the reaction can be carried out on the one hand in an alcohol, for example methanol or ethanol, in dimethylformamide, N-methylpyrrolidone or tetrahydrofuran as solvent, in the presence of a base, for example diethylamine, diisopropylamine, piperidine, KOH, NaOH or sodium methoxide, at a temperature of from -70°C to the boiling temperature of the solvent; on the other hand it can also be carried out, for example, in acetic acid at from 20°C to 120°C in the presence of ammonium acetate.
• a base for example diethylamine, diisopropylamine, piperidine, KOH, NaOH or sodium methoxide
• the invention relates especially to the preparation processes described in Examples P1 to P11.
• Salts of compounds of formula (I) can be prepared in a manner known perse.
• salts of compounds of formula (I) with bases are obtained by treatment of the free compounds with a suitable base or with a suitable ion exchange reagent.
• Salts of compounds of formula (I) can be converted into the free compounds of formula (I) in customary manner, for example by treatment with a suitable acid or with a suitable ion exchange reagent. 70194A
• Salts of compounds of formula (I) can be converted in a manner known per se into other salts of a compound of formula (I).
• the compounds of formula (I), in free form or in salt form, may be in the form of one of the possible isomers or in the form of a mixture thereof, for example, depending upon the number of asymmetric carbon atoms occurring in the molecule and their absolute and relative configuration, and/or depending upon the configuration of non-aromatic double bonds occurring in the molecule, in the form of pure isomers, such as antipodes and/or diastereoisomers, or in the form of mixtures of isomers, such as mixtures of enantiomers, for example racemates, mixtures of diastereoisomers or mixtures of racemates.
• the invention relates both to the pure isomers and to all possible mixtures of isomers and is to be interpreted as such hereinbefore and hereinafter, even if stereochemical details are not mentioned specifically in every case.
• enantiomers such as racemates
• Mixtures of enantiomers, such as racemates, that are obtainable in a corresponding manner can be resolved into the enantiomers by known methods, for example by recrystal- lisation from an optically active solvent, by chromatography on chiral adsorbents, for example high pressure liquid chromatography (HPLC) on acetylcellulose, with the aid of suitable microorganisms, by cleavage with specific, immobilised enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, only one enantiomer being complexed, or by conversion into diastereoisomeric salts and separation of the mixture of diastereoisomers so obtained, for example on the basis of their different solubilities by fractional crystallisation, into the diastereoisomers, from which the desired enantiomer can be freed by the action of suitable agents.
• HPLC high pressure liquid chromatography
• the compounds of formula (I), in free form or in salt form, can also be obtained in the form of their hydrates and/or may include other solvents, for example solvents which may have been used for the crystallisation of compounds in solid form.
• the invention relates to all those embodiments of the process according to which a compound obtainable as starting material or intermediate at any stage of the process is used as starting material and some or all of the remaining steps are carried out or a starting material is used in the form of a derivative or salt and/or its racemates or antipodes or, especially, is formed under the reaction conditions.
• the compounds of formula (I) according to the invention are active ingredients exhibiting valuable preventive and/or curative activity with a very advantageous biocidal spectrum and a very broad spectrum, even at low rates of concentration, while being well tolerated by warm-blooded animals, fish and plants. They are, surprisingly, equally suitable for controlling both plant pests and ecto- and endo-parasites in humans and more especially in productive livestock, domestic animals and pets. They are effective against all or individual development stages of normally sensitive animal pests, but also of resistant animal pests, such as insects and representatives of the order Acarina, nematodes, cestodes and trematodes, while at the same time protecting useful organisms.
• the insecti- cidal or acaricidal activity of the active ingredients according to the invention may manifest itself directly, i.e. in the mortality of the pests, which occurs immediately or only after some time, for example during moulting, or indirectly, for example in reduced oviposition and/or hatching rate.
• Good activity corresponds to a mortality of at least 50 to 60 %.
• Diptera Siphonaptera, Thysanura and Acarina, mainly Acarina, Diptera, Thysanoptera, Lepidoptera and Coleoptera. Very especially good control is possible of the following pests:
• Abagrotis spp. Abraxas spp., Acantholeucania spp., Acanthoplusia spp., Acarus spp., Acarus siro, Aceria spp., Aceria sheldoni, Acleris spp., Acoloithus spp., Acompsia spp., Acossus spp., Acria spp., Acrobasis spp., Acrocercops spp., Acrolepia spp., Acrolepiopsis spp., Acronicta spp., Acropolitis spp., Actebia spp., Aculus spp., Aculus pointedendali, Adoxophyes spp., Adoxophyes reticulana, Aedes spp., Aegeria spp., Aethes spp., Agapeta spp., Agon
• spp . Olindia spp., Olygonychus spp., Olygonychus gallinae, Oncocnemis spp., Operophtera spp F ., Ophisma spp., Opogona spp., Oraesia spp., Omiodoros spp., Orgyia spp., Oria spp., Orseolia spp., Orthodes spp., Orthogonia spp., Orthosia spp., Oryzaephilus spp., Oscinella spp., Oscinella frit, Osminia spp., Ostrinia spp., Ostrinia nubilalis, Otiorhynchus spp., Ourap- teryx spp., Pachetra spp., Pachysphinx spp., Pagyda s
• Scrobipalpopsis spp. Semiothisa spp., Sereda spp., Sesamia spp., Sesia spp., Sicya spp., Sideridis spp., Simyra spp., Sineugraphe spp., Sitochroa spp., Sitobion spp., Sitophilus spp., Sitotroga spp., Solenopsis spp., Smerinthus spp., Sophronia spp., Spaelotis spp., Spar- galoma spp., Sparganothis spp., Spatalistis spp., Sperchia spp., Sphecia spp., Sphinx spp., Spilonota spp., Spodoptera spp., Spodoptera littoralis, Stagmatophora spp., Staphylino-
• pests of the class Nematoda include, for example, root knot nematodes, cyst-forming nematodes and also stem and leaf nematodes; especially of Heterodera spp., e.g. Heterodera schachtii, Heterodora avenae and Heterodora trifolii; Globodera spp., e.g. Globodera rostochiensis; Meloidogyne spp., e.g. Meloidogyne incognita and Meloidogyne javanica; Radopholus spp., e.g.
• An especially important aspect of the present invention is the use of the compounds of formula (I) according to the invention in the protection of plants against parasitic feeding pests.
• Suitable additives include, for example, representatives of the following classes of active ingredient: organophosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carba- mates, pyrethroids, chlorinated hydrocarbons, neonicotinoids and Bacillus thuringiensis preparations.
• Examples of especially suitable mixing partners include: azamethiphos; chlorfenvin- phos; cypermethrin, cypermethrin high-cis; cyromazine; diafenthiuron; diazinon; dichlorvos; dicrotophos; dicyclanil; fenoxycarb; fluazuron; furathiocarb; isazofos; iodfenphos; kinoprene; lufenuron; methacriphos; methidathion; monocrotophos; phosphamidon; profenofos; dio- fenolan; a compound obtainable from the Bacillus thuringiensis strain GC91 or from strain NCTC11821 ; pymetrozine; bromopropylate; methoprene; disulfoton; quinalphos; tau- fluvalinate; thiocyclam; thiometon; aldicarb; azin
• ethofenprox ethoprophos; etrimphos; fenamiphos; fenbutatin oxide; fenothiocarb; fenpropathrin; fenpyrad; fenthion; fluazinam; flucycloxuron; flucythrinate; flufenoxuron; flufenprox; fonophos; fosthiazate; fubfenprox; HCH; hexaflumuron; hexythiazox; flonicamid; iprobenfos; isofenphos; isoxathion; ivermectin; malathion; mecarbam; mesulfenphos; metaldehyde; metolcarb; milbemectin; moxidectin; naled; NC 184; nithiazine; omethoate; oxamyl; oxydemethon M; oxy
• the compounds according to the invention can be used to control, i.e. to inhibit or destroy, pests of the mentioned type occurring on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forestry, or on parts of such plants, such as the fruits, blossoms, leaves, stems, tubers or roots, while in some cases plant parts that grow later are still protected against those pests.
• Target crops include especially cereals, such as wheat, barley, rye, oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet; fruit, e.g. pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, e.g.
• strawberries, raspberries and blackberries leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil, cocoa and groundnuts; cucurbitaceae, such as marrows, cucumbers and melons; fibre plants, such as cotton, flax, hemp and jute; citrus fruits, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocado, cinnamon and camphor; and tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants and ornamentals.
• the invention therefore relates also to pesticidal compositions, such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules and encapsulations of polymer substances, that comprise at least one of the compounds according to the invention, the choice of formulation being made in accordance with the intended objectives and the prevailing circumstances.
• pesticidal compositions such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules and encapsulations of polymer substances, that comprise at least one of the compounds according to the invention, the choice of formulation being made in accordance with the intended objectives and the prevailing circumstances.
• the active ingredient is used in those compositions in pure form, a solid active ingredient, for example, in a specific particle size, or preferably together with at least one of the adjuvants customary in formulation technology, such as extenders, e.g. solvents or solid carriers, or surface-active compounds (surfactants).
• extenders e.g. solvents or solid carriers
• surfactants surface-active compounds
• Solvents are, for example: non-hydrogenated or partly hydrogenated aromatic hydrocarbons, preferably fractions C 8 to C ⁇ 2 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols, such as ethanol, propanol or butanol, glycols and ethers and esters thereof, such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl or -ethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, non-epoxidized or epoxidized plant oils, such as non-epoxid
• the solid carriers used are as a rule natural rock powders, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly disperse silicic acids or highly disperse absorbent polymers can also be added to improve the physical properties.
• Granular adsorptive granule carriers are porous types, such as pumice, crushed brick, sepiolite or bentonite, and non-sorbent carrier materials are calcite or sand. A large number of granular materials of inorganic or organic nature can furthermore be used, in particular dolomite or comminuted plant residues.
• Surface-active compounds are, depending on the nature of the active compound to be formulated, nonionic, cationic and/or anionic surfactants or surfactant mixtures with good emulsifying, dispersing and wetting properties.
• the surfactants listed below are to be 70194A
• Nonionic surfactants are, in particular, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
• Substances which are furthermore suitable are water-soluble polyethylene oxide adducts, containing 20 to 250 ethylene glycol ether and 10 to 100 propylene glycol ether groups, on propylene glycol, ethylene diaminopolypropylene glycol and alkyl polypropylene glycol having 1 to 10 carbon atoms in the alkyl chain.
• the compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
• examples are nonylphenol-polyethoxyethanols, castor oil polyglycol ethers, polypropylene-polyethylene oxide adducts, tributylphenoxypoly- ethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
• Other substances are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.
• the cationic surfactants are, in particular, quaternary ammonium salts which contain, as substituents, at least one alkyl radical having 8 to 22 C atoms and, as further substituents, lower, non-halogenated or halogenated alkyl, benzyl or lower hydroxyalkyl radicals.
• the salts are preferably in the form of halides, methyl-sulfates or ethyl-sulfates. Examples are stearyl-trimethyl-ammonium chloride and benzyl-di-(2-chloroethyl)-ethyl- ammonium bromide.
• Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds.
• Suitable soaps are the alkali metal, alkaline earth metal and substituted or unsubstituted ammonium salts of higher fatty acids (C ⁇ 0 -C 22 ), such as the sodium or potassium salts of oleic or stearic acid, or of naturally occurring fatty acid mixtures, which can be obtained, for example, from coconut oil or tall oil; and furthermore also the fatty acid methyl-taurine salts.
• synthetic surfactants are more frequently used, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
• the fatty sulfonates and sulfates are as a rule in the form of alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts and in general have an alkyl radical of 8 to 22 C atoms, alkyl also including the alkyl moiety of acyl radicals; examples are the sodium or calcium salt of ligninsulfonic acid, of dodecylsulfuric acid ester or of a fatty alcohol sulfate mixture prepared from naturally occurring fatty acids. These also 70194A
• alkylarylsulfonates are, for example, the sodium, calcium or triethanolammonium salts of dodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic acid-formaldehyde condensation product.
• Corresponding phosphates such as salts of the phosphoric acid ester of a p-nonylphenol-(4-14)-ethylene oxide adduct or phospholipids, can further also be used.
• Emulsifiable concentrates active ingredient 1 to 90%, preferably 5 to 20% surfactant: 1 to 30%, preferably 10 to 20% solvent: 5 to 98%, preferably 70 to 85%
• Dusts active ingredient: 0.1 to 10%, preferably 0.1 to 1 % solid carrier: 99.9 to 90%, preferably 99.9 to 99%
• Suspension concentrates active ingredient: 5 to 75%, preferably 10 to 50% water: 94 to 24%, preferably 88 to 30% surfactant: 1 to 40%, preferably 2 to 30%
• Wettable powders active ingredient: 0.5 to 90%, preferably 1 to 80% surfactant: 0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 99%, preferably 15 to 98% 70194A
• Granules active ingredient: 0.5 to 30%, preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%
• compositions according to the invention may also comprise further solid or liquid adjuvants, such as stabilisers, e.g. vegetable oils or epoxidised vegetable oils (e.g. epoxi- dised coconut oil, rapeseed oil or soybean oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders and/or tackifiers as well as fertilisers or other active ingredients for obtaining special effects, e.g. acaricides, bactericides, fungicides, nematicides, mollus- cicides or selective herbicides.
• stabilisers e.g. vegetable oils or epoxidised vegetable oils (e.g. epoxi- dised coconut oil, rapeseed oil or soybean oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders and/or tackifiers as well as fertilisers or other active ingredients for
• the crop protection products according to the invention are prepared in known manner, in the absence of adjuvants, e.g. by grinding, sieving and/or compressing a solid active ingredient or mixture of active ingredients, for example to a certain particle size, and in the presence of at least one adjuvant, for example by intimately mixing and/or grinding the active ingredient or mixture of active ingredients with the adjuvant(s).
• the invention relates likewise to those processes for the preparation of the compositions according to the invention and to the use of the compounds of formula (I) in the preparation of those compositions.
• the invention relates also to the methods of application of the crop protection products, i.e. the methods of controlling pests of the mentioned type, such as spraying, atomising, dusting, coating, dressing, scattering or pouring, which are selected in accordance with the intended objectives and the prevailing circumstances, and to the use of the compositions for controlling pests of the mentioned type.
• Typical rates of concentration are from 0.1 to 1000 ppm, preferably from 0.1 to 500 ppm, of active ingredient.
• the rates of application per hectare are generally from 1 to 2000 g of active ingredient per hectare, especially from 10 to 1000 g/ha, preferably from 20 to 600 g/ha.
• a preferred method of application in the area of crop protection is application to the foliage of the plants (foliar application), the frequency and the rate of application being dependent upon the risk of infestation by the pest in question.
• the active ingredient can also penetrate the plants through the roots (systemic action) when the locus of the plants is impregnated with a liquid formulation or when the active ingredient is incorporated in solid form into the locus of the plants, for example into the soil, e.g. in granular form (soil application). In the case of paddy rice crops, such granules may be applied in metered amounts to the flooded rice field. 70194A
• the crop protection products according to the invention are also suitable for protecting plant propagation material, e.g. seed, such as fruits, tubers or grains, or plant cuttings, against animal pests.
• the propagation material can be treated with the composition before planting: seed, for example, can be dressed before being sown.
• the active ingredients according to the invention can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation.
• the composition can also be applied to the planting site when the propagation material is being planted, for example to the seed furrow during sowing.
• the invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.
• Example P1 Preparation of 3-(4-(3-r2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy1- propoxy)-phenyl)-acrylonitrile
• Example P2 Preparation of 4-(4-(3-r2,6-dichloro-4-(3.3-dichloro-allyloxy)-phenoxy1- propoxy)-phenyl)-but-3-vn-2-ol
• Example P3 Preparation of 1 ,3-dichloro-5-(3,3-dichloro-allyloxy)-2-(3-r4-(3-methoxy- methoxy-but-1-vnyl)-phenoxyl-propoxy)-benzene
• Example P6 Preparation of 1 ,3-dichloro-5-(3,3-dichloro-allyloxy)-2-(3- 4-(2-nitro- vinvD-phenoxyl-propoxyl-benzene
• Example P7 Preparation of 4-(4-(3-r2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy1- propoxy)-phenyl)-but-3-en-2-one
• Example P8 Preparation of 4-(4-(3-f2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy1- propoxy,-phenyl)-but-3-en-2-one O-ethyl-oxime
• Example P10 Preparation of 3-(4-(3-r2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy ,
• Example P11 The Examples of the following Tables can also be prepared in a manner analogous to that described above. Some of the compounds listed in the Tables are obtained in the form of E/Z isomeric mixtures, although only one isomer is indicated in the E column. Mp. is the melting point in °C, n D 20 the refraction index at 20°C and the wavelength of the sodium D-line. The symbol in the formulae signifies the bond of the fragment E to the remainder of the structure. 70194A
• Table 2 A compound of the general formula (Id) wherein X ! and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 3 A compound of the general formula (le) wherein Xi and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 4 A compound of the general formula (If) wherein Xi and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B. 70194A
• Table 5 A compound of the general formula (Ig) wherein Xi and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 6 A compound of the general formula (Ih) wherein X 1 and X 2 are chlorine and n is 2, and the substituent R-
• Table 7 A compound of the general formula (li) wherein i and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 8 A compound of the general formula (Ik) wherein X and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 9 A compound of the general formula (Im) wherein X 1 and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 10 A compound of the general formula (In) wherein Xi and X 2 are chlorine and n is 2, and the substituent R 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 11 A compound of the general formula (lo) wherein X- t and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 12 A compound of the general formula (Ip) wherein X ! and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 13 A compound of the general formula (Iq) wherein X and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 14 A compound of the general formula (Ir) wherein X 1 and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B. 70194A
• Table 15 A compound of the general formula (Is) wherein X and X 2 are chlorine and n is 2, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 16 A compound of the general formula (It) wherein Xi and X 2 are chlorine and n is 2, and the substituent R i0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 17 A compound of the general formula (lu) wherein X 1 and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 18 A compound of the general formula (Iv) wherein X-i and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 19 A compound of the general formula (Iw) wherein X and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 20 A compound of the general formula (Ix) wherein Xi and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 21 A compound of the general formula (ly) wherein Xi and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 22 A compound of the general formula (Iz) wherein X and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 23 A compound of the general formula (laa) wherein X-i and X 2 are chlorine and n is 2, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 24 A compound of the general formula (Ibb) wherein X 1 and X 2 are chlorine and n is 2, and the substituent R 0 for each compound corresponds to a line B.1 to B.191 of Table B. 70194A
• Table 25 A compound of the general formula Ice) wherein Xi and X 2 are chlorine and n is 2, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 26 A compound of the general formula Idd) wherein X 1 and X 2 are chlorine and n is 2, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 27 A compound of the general formula lee) wherein X-i and X 2 are chlorine and n is 2, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 28 A compound of the general formula Iff) wherein Xi and X 2 are chlorine and n is 2, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 29 A compound of the general formula Igg) wherein X and X 2 are chlorine and n is 2, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 30 A compound of the general formula Ihh) wherein X and X 2 are chlorine and n is 2, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 31 A compound of the general formula lii) wherein X and X 2 are chlorine and n is 2, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 32 A compound of the general formula Id) wherein X and X 2 are chlorine and n is 3, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 33 A compound of the general formula le) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound co responds to a line B.1 to B.191 of Table B.
• Table 34 A compound of the general formula (If) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B. 70194A
• Table 35 A compound of the general formula (Ig) wherein X and X 2 are chlorine and n is 3, and the substituent R i0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 36 A compound of the general formula (Ih) wherein X and X 2 are chlorine and n is 3, and the substituent R 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 37 A compound of the general formula (li) wherein Xi and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 38 A compound of the general formula (Ik) wherein X 1 and X 2 are chlorine and n is 3, and the substituent R 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 39 A compound of the general formula (Im) wherein X ! and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 40 A compound of the general formula (In) wherein X and X 2 are chlorine and n is 3, and the substituent R 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 41 A compound of the general formula (lo) wherein X 1 and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 42 A compound of the general formula (Ip) wherein X 1 and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 43 A compound of the general formula (Iq) wherein X and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 44 A compound of the general formula (Ir) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B. 70194 A
• Table 45 A compound of the general formula (Is) wherein Xi and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 46 A compound of the general formula (It) wherein X and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 47 A compound of the general formula (lu) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 48 A compound of the general formula (Iv) wherein X and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 49 A compound of the general formula (Iw) wherein Xi and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 50 A compound of the general formula (Ix) wherein Xi and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 51 A compound of the general formula (ly) wherein Xi and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 52 A compound of the general formula (Iz) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 53 A compound of the general formula (laa) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 54 A compound of the general formula (Ibb) wherein Xi and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B. 70194A
• Table 55 A compound of the general formula (Ice) wherein Xi and X 2 are chlorine and n is 3, and the substituent Rio for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 56 A compound of the general formula (Idd) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 57 A compound of the general formula (lee) wherein Xi and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 58 A compound of the general formula (Iff) wherein Xi and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 59 A compound of the general formula (Igg) wherein X 1 and X 2 are chlorine and n is 3, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 60 A compound of the general formula (Ihh) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 61 A compound of the general formula (lii) wherein Xi and X 2 are chlorine and n is 3, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 62 A compound of the general formula (Id) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 63 A compound of the general formula (le) wherein Xi and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 64 A compound of the general formula (If) wherein Xi and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B. 70194A
• Table 65 A compound of the general formula (Ig) wherein Xi and X 2 are chlorine and n is 4, and the substituent R i0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 66 A compound of the general formula (Ih) wherein X and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 67 A compound of the general formula (li) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 68 A compound of the general formula (Ik) wherein Xi and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 69 A compound of the general formula (Im) wherein Xi and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 70 A compound of the general formula (In) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 71 A compound of the general formula (lo) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 72 A compound of the general formula (Ip) wherein X and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 73 A compound of the general formula (Iq) wherein X and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 74 A compound of the general formula (Ir) wherein Xi and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B. 70194A
• Table 75 A compound of the general formula (Is) wherein X and X 2 are chlorine and n is 4, and the substituent R i0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 76 A compound of the general formula (It) wherein Xi and X 2 are chlorine and n is 4, and the substituent Rio for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 77 A compound of the general formula (lu) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 78 A compound of the general formula (Iv) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 79 A compound of the general formula (Iw) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 80 A compound of the general formula (Ix) wherein Xi and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 81 A compound of the general formula (ly) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 82 A compound of the general formula (Iz) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 83 A compound of the general formula (laa) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 84 A compound of the general formula (Ibb) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B. 70194A
• Table 85 A compound of the general formula (Ice) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 86 A compound of the general formula (Idd) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 87 A compound of the general formula (lee) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 88 A compound of the general formula (Iff) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 89 A compound of the general formula (Igg) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 90 A compound of the general formula (Ihh) wherein Xi and X 2 are chlorine and n is 4, and the substituent R 10 for each compound corresponds to a line B.1 to B.191 of Table B.
• Table 91 A compound of the general formula (lii) wherein Xi and X 2 are chlorine and n is 4, and the substituent R ⁇ 0 for each compound corresponds to a line B.1 to B.191 of Table B.
• Example F1 Emulsifiable concentrates a) b) c) active ingredient 25 % 40 % 50 % calcium dodecylbenzenesulfonate 5 % 8 % 6 % castor oil polyethylene glycol ether (36 mol EO) 5 % - - tributylphenol polyethylene glycol ether (30 mol EO) - 12 % 4 % cyclohexanone - 15 % 20 % xylene mixture 65 % 25 % 20 %
• Example F2 Solutions a) b) c) d) active ingredient 80 % 10 % 5 % 95 % ethylene glycol monomethyl ether 20 % - - - polyethylene glycol (MW 400) - 70 % - -
• N-methylpyrrolid-2-one 20 % - - epoxidised coconut oil - - 1 % 5 % benzine (boiling range: 160-190°) - - 94 % .
• Example F3 Granules a) b) c) d) active ingredient 5 % 10 % 8 % 21 % kaolin 94 % - 79 % 54 % highly dispersed silicic acid 1 % - 13 % 7 % attapulgite - 90 % - 18 %
• the active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier mixture and the solvent is evaporated off in vacuo.
• Example B1 Action against Heliothis virescens caterpillars
• the soybean plants are populated with 10 caterpillars of Heliothis virescens in the first stage and placed in a plastics container. Evaluation is made 6 days later. The percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.
• the compounds of the Tables exhibit good activity against Heliothis virescens in this test.
• the compounds 1.1 to 1.13 and 1.15 to 1.27 are more than 80 % effective.
• Example B2 Action against Plutella xylostella caterpillars
• Young cabbage plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient. After the spray-coating has dried, the cabbage plants are populated with 10 caterpillars of Plutella xylostella in the third stage and placed in a plastics container. Evaluation is made 3 days later. The percentage reduction in population and the 70194A
• percentage reduction in feeding damage are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.
• the compounds of the Tables exhibit good activity against Plutella xylostella in this test.
• the compounds 1.1 to 1.13 and 1.15 to 1.27 are more than 80 % effective.
• Example B3 Action against Spodoptera littoralis
• Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient and, after the spray-coating has dried, the plants are populated with 10 caterpillars of Spodoptera littoralis in the first stage and then placed in a plastics container. 3 days later, the percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.
• the compounds of the Tables exhibit good activity against Spodoptera littoralis in this test.
• the compounds 1.1 to 1.13 and 1.15 to 1.27 are more than 80 % effective.

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