WO2024028243A1 - Composés pesticides pyrazolo - Google Patents

Composés pesticides pyrazolo Download PDF

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Publication number
WO2024028243A1
WO2024028243A1 PCT/EP2023/071106 EP2023071106W WO2024028243A1 WO 2024028243 A1 WO2024028243 A1 WO 2024028243A1 EP 2023071106 W EP2023071106 W EP 2023071106W WO 2024028243 A1 WO2024028243 A1 WO 2024028243A1
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Prior art keywords
alkyl
cycloalkyl
compounds
spp
halogen
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PCT/EP2023/071106
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English (en)
Inventor
Rupsha Chaudhuri
Pulakesh MAITY
Christian Defieber
Ashokkumar Adisechan
Christian Harald Winter
Kishor Handore
Karsten Koerber
Matthew Charles Linford WAKEHAM
Devendra VYAS
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Basf Se
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Publication of WO2024028243A1 publication Critical patent/WO2024028243A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/32—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • Invertebrate pests and in particular insects, arachnids and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby causing large economic loss to the food supply and to property. Accordingly, there is an ongoing need for new agents for combating invertebrate pests.
  • Carbamoylated and thiocarbamoylated oxime derivatives are known for pesticidal use, for example, in patent publications WO 2016/156076, semi-carbazones and thiosemicarbazones derivatives are known for pesticidal use in patent publication WO 2016/116445 and pyrazolo pesticidal compounds are known for pesticidal use in patent publication WO2021/013561.
  • substituted bicyclic compounds of formula I as depicted and defined below, including their stereoisomers, their salts, in particular their agriculturally or veterinarily acceptable salts, their tautomers and their N-oxides.
  • the present invention relates to the Compounds of the formula I
  • R 5 is H, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, Ci-C6-alkyl-Ci-C 6 -alkoxy or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, phenyl, 5- or 6- membered heteroaryl, -CH 2 -phenyl, -CH 2 -5- or 6- membered heteroaryl, 1 ,3-dioxolan-2-ylmethyl, or halogen, wherein the alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen or CN;
  • R 1 is H, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, halogen, or NR 6 R 7 , wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 2 is H, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, or halogen, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 -cyclo- alkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • D is the moiety DA or DB
  • R 3 is H, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • B is a 5- or 6-membered carbocyclic group, wherein 1 or 2 CH 2 moieties of the carbocyclic group may be replaced by a carbonyl group, O, or S, wherein the carbocyclic group is unsubstituted or substituted with R h ;
  • Ar 1 is phenyl or 5- or 6-membered heteroaryl, which are unsubstituted or substituted with R Ar1 , wherein
  • R Ar1 is halogen, SF 5 , NO 2 , OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocy- clyl, C 3 -C 6 -cycloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl wherein the alkyl, alkoxy, alkenyl, al- kynyl, cycloalkyl, C 3 -C 6 -heterocyclyl, and cycloalkoxy moieties are unsubstituted or substituted with R f ;
  • R 6 and R 7 are, identical or different, H, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, phenyl, -CH 2 -phenyl, 5- or 6- membered heteroaryl, -CH 2 -5- or 6- membered heteroaryl, 1 ,3-dioxolan-2-ylmethyl, or 2- (methylamino)-2-oxo-ethyl, wherein the alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN, Ci-C 6 -alkyl or Ci-C 6 -alkoxy;
  • Ar 2 is phenyl or 5- or 6-membered heteroaryl, which are unsubstituted or substituted with R Ar2 , wherein
  • R Ar2 is halogen, CN, -SCN, -SF 5 , Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 - alkoxy-Ci-C 4 -alkyl, Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 - cycloalkyl-Ci-C 4 -alkyl, C 3 -C 6 -cycloalkoxy-Ci-C 4 -alkyl, wherein the alkyl, alkoxy, alkenyl, al- kynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;
  • R d is H, Ci-C 6 -alkyl
  • R e is Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 4 -alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • R f is halogen, OH, CN, SCN, -SF 5 , Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci- C 6 -alkoxy-Ci-C 4 -alkyl, Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 - C 6 -cycloalkyl-Ci-C 4 -alkyl, C 3 -C 6 -cycloalkoxy-Ci-C 4 -alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;
  • R h is halogen, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy; m is 0, 1 , or 2. and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
  • the present invention also relates to processes and intermediates for preparing compounds of formula I and to active compound combinations comprising them.
  • the present invention relates to agricultural or veterinary compositions comprising the compounds of formula I, and to the use of the compounds of formula I or compositions comprising them for combating or controlling invertebrate pests and/or for protecting crops, plants, plant propagation material and/or growing plants from attack and/or infestation by invertebrate pests.
  • the present invention also relates to methods of applying the compounds of formula I.
  • the present invention also relates to method for protecting crops, plants, plant propagation material and/or growing plants from attack or infestation by invertebrate pests comprising contacting or treating the crops, plants, plant propagation material and growing plants, or soil, material, surface, space, area or water in which the crops, plants, plant propagation material is stored or the plant is growing, with a pesticidally effective amount of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);
  • the present invention relates to seed comprising compounds of formula I.
  • the compounds of formula I includes N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
  • the compounds of formula I can be prepared by procedures as given in below schemes.
  • the compounds of the formula (I) can be prepared by methods of organic chemistry, e.g, by the methods described herein after in schemes 1 to 19 in the synthesis description of the examples.
  • the radicals Ar 1 , B 1 , B 2 , B 3 , B 4 , Q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R h and Ar 2 are as defined above for formula (I), unless otherwise specified.
  • compounds of formula (la-2) are reacted directly with a compound of formula (E1) in the presence of an inorganic base to form a compound of formula (la).
  • An isocyanate compound of formula (la-2) can be generated in situ from either an amine of the formula (la-1) by using one of the common reagents such as phosgene, diphosgene, triphosgene or carbonyldiimidazole (Step I) in a mixed solvent system and in the presence of a base as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • an isocyanate compound of formula (la-2) is generated via a Curtius rearrangement of an acyl azide (la-4), e.g. by analogy to the method described in WO 2014/204622.
  • the acyl azide of the formula (la-4) can be prepared from the corresponding carboxylic acid precursor of formula (la-3) by treatment with ethyl chloroformate and sodium azide in the presence of an amine base such as triethylamine, or with diphenylphosphoryl azide in the presence of an amine base such as triethylamine.
  • amine of formula (la-1) can be treated with an activating agent such as 4-nitrophenyl chloroformate in the presence of a polar aprotic solvent preferably tetrahydrofuran to generate an activated amine (la-1 ’), which in turn is reacted with the compound of formula (E1), in the presence of organic base such as N,N-diisopropylethylamine to form compound of formula (la).
  • an activating agent such as 4-nitrophenyl chloroformate
  • a polar aprotic solvent preferably tetrahydrofuran
  • organic base such as N,N-diisopropylethylamine
  • compound of formula (E1) can be treated with an activating agent such as 4-nitrophenyl chloroformate in the presence of a polar aprotic solvent preferably tetrahydrofuran and an inorganic base such as cesium carbonate or potassium carbonate to generate an activated carbamate intermediate (E1-1), which in turn is reacted with amine of formula (la-1) in the presence of an inorganic base such as cesium carbonate or potassium carbonate to form compound of formula (la).
  • an activating agent such as 4-nitrophenyl chloroformate
  • a polar aprotic solvent preferably tetrahydrofuran
  • an inorganic base such as cesium carbonate or potassium carbonate
  • compounds of the formula (la’) can be prepared by treating aryl thiourea of formula (E1’) with the isocyanate of formula (la-2) in the presence of inorganic bases such as cesium carbonate or sodium hydride in an aprotic solvent.
  • inorganic bases such as cesium carbonate or sodium hydride in an aprotic solvent.
  • compounds of formula (E1’) can be prepared by analogy to the methods described in WO 2021/011722.
  • compounds of formula (E1 -la) can be converted into a variety of cyclized analogs of formula (E1-I), (E1-II), (E1-III) and (E1-IV).
  • Compounds of formula (E1-I) and (E1-II) can be prepared by treatment of compounds of formula (E1 -la) with unsubstituted or mono- or disubstituted 2-chloroacetylchloride and 3-chloropropanoylchloride in two steps as depicted in J. of Med. Chem. 2010, 53(10), 4198-4211.
  • Compounds of formula (E1-llla) and (E1-IVa) can be prepared by treatment of compounds of formula (E1-la) with unsubstituted or mono- or disubstituted 2-chloroactaldehyde and 3-chloro-propanal in 2 steps as mentioned in J. of Het. Chem. 2006, 43(6), 1523-1531.
  • Compounds of formula (E1-III) and (E1-IV) can be prepared by treatment of compounds of formula (E1 -I I la) and (E1-IVa) with potassium thiocyanate in presence of inorganic bases such as cesium carbonate in an aprotic solvent such as acetone.
  • compounds of formula (la’) can be converted into a variety of cyclized analogs of formula (la-l), (la-ll), (la-lll) and (la-IV). Cyclization can be achieved by treatment of compounds of formula (la’) with o-halo esters such as methyl bromoacetate or methyl bromo propanoate to form compounds of formula (la-l) and (la-ll) unsubstituted or mono- or disubstituted with R h .
  • Compounds of formula (la-lll) and (la-IV) unsubstituted or mono- or disubstituted with R h can be prepared by treatment of compounds of formula (la’) with vicinal dihalides.
  • steps XVIII and XIX use of sodium acetate in a protic solvent such as Ethanol, at temperatures ranging from about 20°C to about 70°C is preferred.
  • steps XX and XXI use of an inorganic base such as potassium carbonate in a solvent such as acetonitrile or 2-butanone, at a temperature between about 0°C and about 80°C, is preferred. All the above reactions can be performed by analogy to the methods described in WO 2021/011722.
  • Step XXII can be performed via Chan-Lam coupling reaction starting from an aryl boronic acid precursor (1) as described in Chem. A Eur. J., 2017, 23(14), 3285-3290.
  • compounds of formula (la-1) can be prepared by reduction of nitro compounds of formula (llla-1) using reducing agents such as SnCI 2 in acid medium as shown in step XXIII.
  • compounds of formula (la-1) can also be prepared by reacting compounds of the formula (IVa-1) with ammonia in the presence of a metal catalyst or its salts, preferably copper or its salts as described in Chem. Commun., 2009, 3035-3037.
  • compounds of formula (la-1) can also be prepared in two steps from compounds of the formula (IVa-1). Treatment of compounds of formula (IVa-1) with tert-butyl carbamate in the presence of metal catalyst or its salts, preferably palladium or its salts to form compounds of formula (IVa-2) in step XXV, followed by Boc-deprotection using trifluoroacetic acid or diluted hydrochloric acid to form the desired compound in step XXVI. All these reactions are performed as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • Step XXVII involves SNAr reaction between pyrazole (Ila) and p-fluoro nitroarene (2) as described in WO 2017/139274.
  • Step XXVIII can be performed via Chan-Lam coupling reaction starting from an aryl boronic acid precursor (3) as described in Chem. A Eur. J., 2017, 23(14), 3285-3290.
  • Step XXIX can be performed via Chan-Lam coupling reaction starting from an aryl boronic acid precursor (4) as described in Chem. A Eur. J., 2017, 23(14), 3285-3290. Hal as bromide is preferrable.
  • compounds of formula (IVa-1-1a) can be prepared from a commercially available 1 ,3 diketone derivative (5) by reacting it with substituted aryl hydrazines (ArNHNH 2 , 6) as described in WO 2016/044666. Then nitration of compounds of formula (IVa-1- 1a) using a mixture of nitric acid and sulfuric acid in an aprotic solvent such as dichloroethane can produce compounds of formula (IVa-1-1 b).
  • Compounds of formula (IVa-1-1 b) can undergo reduction to compounds of formula (IVa-1-1c) using reducing agents such as SnCI 2 in acid medium or Fe with NH 4 CI in a mixture of Ethanol and water as shown in step XXXII. Then amide coupling reactions of compounds of formula (IVa-1-1c) with the derivatives of benzoic acids can form the compounds of formula (IVa-1-1) using suitable coupling reagents such as HATU or T 3 P and bases like DIPEA, as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • suitable coupling reagents such as HATU or T 3 P and bases like DIPEA
  • the compounds of formula (IVa-1-1) can also be synthesized by treating compounds of formula (IVa-1 -1c) with commercially available benzoyl chlorides in presence of base, as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • the compounds of formula (IVa-1-1) can also be synthesized by in-situ generation of benzoyl chlorides from the corresponding benzoic acids with POCI 3 or SOCI 2 then followed by treatment with the compounds of formula (IVa-1-1c) in presence of base as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • Step XXXV involves pyrazole synthesis as described in Angew., Chem., Int. Ed., 2010, 49(42), 7790-7794.
  • Step XXXVI involves hydrolysis of ester using suitable bases like LiOH, NaOH, as mentioned in WO 2011/050245.
  • Step XXXVII involves amide coupling reactions with aniline derivatives using suitable coupling reagents such as HATU or T 3 P and bases like DIPEA, analogous to as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • Compounds of formula (IVa-1 -3a) can be prepared from a commercially available beta keto ester derivative (7’) by reacting it with substituted aryl hydrazines (ArNHNH 2 , 6) as described in J. of Het. Chem. 1984, 21(6), 1747-52.
  • Compounds of formula (IVa-1-3b) can be prepared from compounds of formula (IVa-1-3a) by treating with POCI 3 . Thenitration of compounds of formula (IVa-1-3b) can be done as described in Bioorg. and Med. Chem. 2014, 22(9), 2739-2752 to produce compounds of formula (IVa-1-3c).
  • the compounds of formula (IVa-1-3) can also be synthesized by treating compounds of formula (IVa-1-3e) with commercially available benzoyl chlorides in presence of base, as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • the compounds of formula (IVa- 1-3) can also be synthesized by in-situ generation of benzoyl chlorides from the corresponding benzoic acids with POCI 3 or SOCI 2 then followed by treatment with the compounds of formula (IVa-1-3e) in presence of base as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • Step XLVIII involves reduction of nitro compounds of formula (lla- 1-1 a) using reducing agents such as SnCI 2 in acid medium or Fe with NH 4 CI in a mixture of Ethanol and water
  • step XLIX involves amide coupling reactions analogous with the derivatives of benzoic acids using suitable coupling reagents such as HATU or T 3 P and bases like DIPEA, as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • Step L involves hydrolysis of ester using suitable base like LiOH, NaOH, as mentioned in WO 2011/050245.
  • Step LI involves amide coupling reactions with aniline derivatives using suitable coupling reagents such as HATU or T 3 P and bases like DIPEA, analogous to as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • Compounds of formula (la-1-1) can be prepared from compounds of formula (la-1-1 a) with R 5 as Ci-C 6 -alkyl or C 3 -C 6 -cycloalkyl or -CH 2 -phenyl or -CH 2 -5- or 6- membered hetaryl or 1 ,3- dioxolan-2-ylmethyl, by reacting with corresponding commercially available alkyl halides or benzyl halides preferably iodides or bromides in presence of bases like cesium carbonate and polar aprotic solvent like DMF, analogous to as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • compounds of formula (la-1-1) with R 5 as phenyl or 5- or 6- membered hetaryl can be prepared from compounds of formula (la-1 -1a) by metal catalyzed reaction with corresponding aryl halides or 5- or 6- membered hetaryl halide preferably iodides or bromides as describe in Chinese J. of Chem. 2012, 30(10), 2356-2362.
  • compounds of formula (la-1-1) can be prepared from compounds of formula (llla-1-1a) in two steps.
  • Step LIII can be performed similarly to step LIL
  • Step LIV involves reduction using reducing agents such as SnCI 2 in acid medium or Fe with NH 4 CI in a mixture of Ethanol.
  • Compounds of formula (la-1-2) can be prepared from compounds of formula (la-1-2a) or from compounds of formula (llla-1 -2a) using the reaction conditions discussed under scheme 16.
  • Compounds of formula (la-1) where in R 1 is Ci-C 6 -alkyl or C 3 -C 6 -cycloalkyl and B 2 or B 3 is CR B2 or CR B3 where in R B2 or R B3 is Hal, are the compounds of formula (la-1-3) can be prepared by analogy to the methods described in scheme 18.
  • Compounds of formula (la-1-3) can be prepared by treating compounds of formula (la-1-3a) with electrophilic halogenating agent such as NCS in a polar aprotic solvent like ACN analogous to as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • electrophilic halogenating agent such as NCS in a polar aprotic solvent like ACN analogous to as described in March’s Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March.
  • Compounds of formula (la-1-1) can be prepared by treating compounds of formula (la-l) with electrophilic halogenating agent such as Palau’Chlor in a non-polar aprotic solvent like chloroform analogous to as described in J. Am. Chem. Soc. 2014, 136, 6908-6911 .
  • electrophilic halogenating agent such as Palau’Chlor in a non-polar aprotic solvent like chloroform analogous to as described in J. Am. Chem. Soc. 2014, 136, 6908-6911 .
  • Individual compounds of formula I can also be prepared by derivatisation of other compounds of formula I or the intermediates thereof.
  • composition(s) according to the invention or “compounds of formula I” comprises the compound(s) as defined herein as well as a stereoisomer, salt, tautomer or N-oxide thereof.
  • compound(s) of the present invention is to be understood as equivalent to the term “compound(s) according to the invention”, therefore also comprising a stereoisomer, salt, tautomer or N-oxide thereof.
  • composition(s) according to the invention” or “composition(s) of the present invention” encompasses composition(s) comprising at least one compound of formula I according to the invention as defined above.
  • the compositions of the invention are preferably agricultural or veterinary compositions.
  • the compounds according to the invention may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the single pure enantiomers or pure diastereomers of the compounds according to the invention, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds according to the invention or their mixtures.
  • Suitable compounds according to the invention also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond or amide group.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • the present invention relates to every possible stereoisomer of the compounds of formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
  • the compounds according to the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention relates to amorphous and crystalline compounds according to the invention, mixtures of different crystalline states of the respective compounds according to the invention, as well as amorphous or crystalline salts thereof.
  • tautomers encompasses isomers, which are derived from the compounds of formula I by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom.
  • tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.
  • stereoisomers encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • One center of chirality is the carbon ring atom of the isothiazoline ring carrying radical R 1 .
  • the invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures.
  • Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
  • N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO). To be more precise, it relates to any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N- oxides of compounds I can in particular be prepared by oxidizing e.g. the ring nitrogen atom of an N-heterocycle, e.g. a pyridine or pyrimidine ring present in Ar or R 11 , or an imino-nitrogen present in central tricyclic core, with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides.
  • a suitable oxidizing agent such as peroxo carboxylic acids or other peroxides.
  • Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
  • Suitable agriculturally or veterinarily acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, which are known and accepted in the art for the formation of salts for agricultural or veterinary use respectively, and do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH 4+ ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C 4 -alkyl, C1-C4- hydroxyalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, hydroxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or -CH 2 -phenyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2- (2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C 4 -alkyl)sulfoxonium.
  • Suitable acid addition veterinarily acceptable salts e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group
  • Suitable acid addition veterinarily acceptable salts include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • invertebrate pest encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
  • the plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting. Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • plants comprises any types of plants including “modified plants” and in particular "cultivated plants”.
  • modified plants refers to any wild type species or related species or related genera of a cultivated plant.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://www.bio.org/speeches/pubs/er/agri_products.asp).
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
  • auxin herbicides such as
  • herbicides e. bromoxynil or ioxynil herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • ALS inhibitors e.g. described in Pest Managem. Sci.
  • cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as 6-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or IP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • VIP1 , VIP2, VIP3 or IP3A vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP- glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium or calcium channels
  • these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g.
  • insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coelop- tera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cryl F toxin and PAT enzyme).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called “pathogenesis- related proteins” (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis- related proteins
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum
  • T4-lysozym e. g. potato cultiv
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
  • a modified amount of substances of content or new substances of content specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual members.
  • the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each case F, Br, Cl or I, in particular F, Cl or Br.
  • alkyl as used herein and in the alkyl moieties of alkoxy, alkylthio, and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 (“Ci-C 2 -alkyl"), 1 to 3 (“Ci-C 3 -alkyl"),1 to 4 (“Ci-C 4 -alkyl”) or 1 to 6 (“Ci-C 6 -alkyl”) carbon atoms.
  • Ci-C 2 -Alkyl is CH 3 or C 2 H 5 .
  • Ci-C 3 -Alkyl is additionally propyl and isopropyl.
  • Ci-C 4 -Alkyl is additionally butyl, 1- methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1 ,1 -dimethylethyl (tert-butyl).
  • Ci-C 6 -Alkyl is additionally also, for example, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1 -ethylpropyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -
  • haloalkyl refers to straight-chain or branched alkyl groups having 1 to 2 (“Ci-C 2 - haloalkyl”), 1 to 3 (“Ci-C 3 -haloalkyl”), 1 to 4 (“Ci-C 4 -haloalkyl”) or 1 to 6 (“Ci-C 6 -haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1- bromoethyl, 1
  • Ci-C 3 -haloalkyl is additionally, for example, 1 -fluoropropyl, 2-fluoropropyl, 3- fluoropropyl, 1 ,1 -difluoropropyl, 2,2-difluoropropyl, 1 ,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3- trifluoropropyl, heptafluoropropyl, 1 , 1 , 1 -trifluoroprop-2-yl, 3-chloropropyl and the like.
  • Examples for Ci-C 4 -haloalkyl are, apart those mentioned for Ci-C 3 -haloalkyl, 4-chlorobutyl and the like.
  • alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • Alkylene has preferably 1 to 6 carbon atoms (Ci-C 6 -alkylene), 2 to 6 carbon atoms (C 2 -C 6 -alkylene), in particular 1 to 4 carbon atoms (Ci-C 4 -alkylene) or 2 to 4 carbon atoms (C 2 -C 4 -alkylene).
  • alkylene examples include methylene (CH2), 1 , 1 -ethandiyl, 1 ,2-ethandiyl, 1 ,3-propandiyl, 1 ,2-propandiyl, 2,2-propandiyl, 1 ,4-butandiyl,
  • alkenyl refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C 2 -C 3 -alkenyl"), 2 to 4 (“C 2 -C 4 -alkenyl") or 2 to 6 (“C 2 -C 6 - alkenyl) carbon atoms and a double bond in any position, for example C 2 -C 3 -alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl or 1 -methylethenyl; C 2 -C 4 -alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1- propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; C 2 -C 6 -
  • alkynyl refers to straight-chain or branched hydrocarbon groups having 2 to 3 (“C 2 -C 3 -alkynyl”), 2 to 4 (“C 2 -C 4 -alkynyl”) or 2 to 6 (“C 2 -C 6 -alkynyl”) carbon atoms and one or two triple bonds in any position, for example C 2 -C 3 -alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; C 2 -C 4 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3- butynyl, 1-methyl-2-propynyl and the like, C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-
  • cycloalkyl refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having in particular 3 to 6 (“C 3 -C6-cycloalkyl") or 3 to 5 (“C 3 -C 5 -cycloalkyl”) or 3 to 4 (“C 3 -C 4 -cycloalkyl”) carbon atoms.
  • monocyclic radicals having 3 to 4 carbon atoms comprise cyclopropyl and cyclobutyl.
  • monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl.
  • Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • cycloalkoxy refers to a cycloalkyl radical, in particular a monocyclic cycloalkyl radical, as defined above having in particular 3 to 6 (“C 3 -C 6 -cycloalkoxy”) or 3 to 5 (“C 3 -C 5 -cycloalkoxy”) or 3 to 4 (“C 3 -C 4 -cycloalkoxy”) carbon atoms, which is bound via an oxygen atom to the remainder of the molecule.
  • cycloalkyl-Ci-C 4 -alkyl refers to a C 3 -C 8 -cycloalkyl ("C 3 -C 8 -cycloalkyl-Ci-C 4 - alkyl”), preferably a C 3 -C 6 -cycloalkyl ("C 3 -C 6 -cycloalkyl-Ci-C 4 -alkyl”), more preferably a C 3 -C 4 - cycloalkyl ("C 3 -C 4 -cycloalkyl-Ci-C 4 -alkyl") as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C 4 -alkyl group, as defined above.
  • Examples for C 3 -C 4 -cycloalkyl-Ci-C 4 -alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl
  • Examples for C 3 -C 6 - cycloalkyl-Ci-C 4 -alkyl, apart those mentioned for C 3 -C 4 -cycloalkyl-Ci-C 4 -alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
  • Ci-C 2 -alkoxy is a Ci-C 2 -alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 3 -alkoxy is a Ci-C 3 -alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 4 -alkoxy is a Ci-C 4 -alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 6 -alkoxy is a Ci-C 6 -alkyl group, as defined above, attached via an oxygen atom.
  • Ci-Cio-alkoxy is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 2 -Alkoxy is OCH 3 or OC 2 H 5 .
  • Ci-C 3 -Alkoxy is additionally, for example, n-propoxy and 1 -methylethoxy (isopropoxy).
  • Ci-C 4 -Alkoxy is additionally, for example, butoxy, 1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert- butoxy).
  • Ci-C 6 -Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1- dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1- methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2- dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1-ethyl-1- methylpropoxy or 1-ethyl-2-methylpropoxy.
  • Ci-C 8 -Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethy I hexyloxy and positional isomers thereof.
  • Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
  • Ci-C 2 -haloalkoxy is a Ci-C 2 -haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 3 -haloalkoxy is a Ci-C 3 -haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 4 -haloalkoxy is a Ci-C 4 -haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 6 -haloalkoxy is a Ci-C 6 -haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 2 -Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHCI 2 , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC 2 F 5 .
  • Ci-C 3 -Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3- fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3- dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3- trichloropropoxy, OCH 2 -C 2 F 5 , OCF 2 -C 2 F 5 , 1-(CH 2 F)-2-fluoroethoxy, 1-(CH 2 CI)-2-chloroethoxy or
  • Ci-C 4 -Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4- chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • Ci-C 6 -Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6- fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
  • Ci-C 6 -alkoxy-Ci-C 4 -alkyl refers to a straight-chain or branched alkyl having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C 6 -alkoxy group, as defined above.
  • Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tertbutoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl, 1 -isopropoxyethyl, 1-n- butoxyethyl, 1-sec-butoxyethyl, 1 -isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2- ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2- isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1-ethoxypropyl, 1 -propoxypropyl, 1- isopropoxypropyl, 1-n-but
  • alkoxyalkoxy refers to an alkoxyalkyl radical, in particular a C1- C 6 -alkoxy-Ci-C 4 -alkyl radical, as defined above, which is bound via an oxygen atom to the remainder of the molecule.
  • Examples thereof are OCH 2 -OCH 3 , OCH 2 -OC 2 H 5 , n-propoxymethoxy, OCH 2 -OCH(CH 3 ) 2 , n-butoxymethoxy, (1 -methylpropoxy) methoxy, (2-methylpropoxy)methoxy, OCH 2 -OC(CH 3 ) 3 , 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1- methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2- methylpropoxy)ethoxy, 2-(1 ,1-dimethylethoxy)ethoxy, etc.
  • aryl relates to phenyl and bi- or polycyclic carbocycles having at least one fused phenylene ring, which is bound to the remainder of the molecule.
  • bi- or polycyclic carbocycles having at least one phenylene ring include naphthyl, tetrahydronaphthyl, indanyl, indenyl, anthracenyl, fluorenyl etc.
  • aryl-Ci-C 4 -alkyl relates to Ci-C 4 -alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryl radical, in particular a phenyl radical.
  • aryl-Ci-C 4 -alkyl include -CH 2 -phenyl, 1-phenethyl, 2-phenetyl, 1 -phenylpropyl, 2-phenylpropyl, 3- phenyl-1 -propyl and 2-phenyl-2-propyl.
  • aryloxy-Ci-C 4 -alkyl relates to Ci-C 4 -alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryloxy radical, in particular a phenoxy radical.
  • aryloxy-Ci-C 4 -alkyl include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyetyl, 1- phenoxypropyl, 2-phenoxypropyl, 3-phenoxy-1 -propyl and 2-phenoxy-2-propyl.
  • aryl-Ci-C 4 -carbonyl relates to aryl as defined above, , in particular a phenyl radical, which is bound by a carbonyl to the remainder of the molecule.
  • arylcarbonyl include benzoyl, 1 -naphthoyl and 2-naphthoyl.
  • heteroaryl relates to aromatic heterocyclyl or heterocycles having either 5 or 6 ring atoms (5- or 6-membered hetaryl) and being monocyclic or 8, 9 or 10 ring atoms and bing bicyclic. Hetaryl will generally have at least one ring atom selected from O, S and N, which in case of N may be an imino-nitrogen or an amino-nitrogen, which carries hydrogen or a radical different from hydrogen. Hetaryl may have 1 , 2, 3 or 4 further nitrogen atoms as ring members, which are imino nitrogens.
  • Examples of 5- or 6-membered hetaryl include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1- pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4- oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1-yl, 1 ,3,4-triazol-2-yl, 1 ,3,4-oxadiazolyl-2-yl, 1 ,3,4-thiadiazol-2-yl, 2-pyridinyl, 3- pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl
  • Examples of 8-, 9- or 10-membered hetaryl include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizynyl, isoindolyl, indazolyl, benzofuryl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzimidazolyl, imidazo[1 ,2- a]pyridine-2-yl, thieno[3,2-b]pyridine-5-yl, imidazo-[2,1-b]-thiazol-6-yl and 1 ,2,4-triazolo[1 ,5- a]pyridine-2-yl.
  • N-bound 5-, 6-, 7 or 8-membered saturated heterocyclyl or heterocycles include: pyrrolidin-1 -yl, pyrazolidin-1 -yl, imidazolidin-1 -yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4- yl, 1-oxothiomorpholin-4-yl, 1 ,1-dioxothiomorpholin-4-yl, azepan-1-yl and the like.
  • hetaryl-Ci-C 4 -alkyl relates to Ci-C 4 -alkyl, as defined above, wherein one hydrogen atom has been replaced by a hetaryl radical, in particular a pyridyl radical.
  • hetaryl-Ci-C 4 -alkyl include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1-(2- pyridyl)ethyl, 2-(2-pyridyl)ethyl, 1-(3-pyridyl)ethyl, 2-(3-pyridyl)ethyl, 1-(4-pyridyl)ethyl, 2-(4- pyridyl)ethyl etc.
  • hetaryloxy-Ci-C 4 -alkyl relates to Ci-C 4 -alkyl, as defined above, wherein one hydrogen atom has been replaced by an hetaryloxy radical, in particular a pyridyloxy radical.
  • hetaryloxy-Ci-C 4 -alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl, 4- pyridyloxymethyl, 1-(2-pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl, 1-(3-pyridyloxy)ethyl, 2-(3- pyridyloxy)ethyl, 1-(4-pyridyloxy)ethyl, 2-(4-pyridyloxy)ethyl etc.
  • hetaryl-Ci-C 4 -carbonyl relates to hetaryl as defined above, in particular a C- bound hetaryl radical, e.g. 2-, 3-or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl radical, which is bound by a carbonyl to the remainder of the molecule.
  • a C- bound hetaryl radical e.g. 2-, 3-or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl radical, which is bound by a carbonyl to the remainder of the molecule.
  • substituted if not specified otherwise refers to substituted with 1 , 2, or up to maximum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not mentioned otherwise.
  • maximum two of B 1 , B, 2 and B 3 can be N;
  • B 1 is CR B1
  • B 2 is CR B2
  • B 3 is CR B3 ;
  • B 1 is N
  • B 2 is CR B2
  • B 3 is CR B3 ;
  • B 1 is CR B1
  • B 2 is N
  • B 3 is CR B3 ;
  • B 1 is CR B1 , B 2 is N, and B 3 is N;
  • B 1 is N
  • B 2 is N
  • B 3 is CR B3 ;
  • B 1 is CR B1
  • B 2 is N or CR B2
  • B 3 is N or CR B3 ;
  • B 3 is CR B3
  • B 1 is N or CR B2
  • B 2 is N or CR B3 .
  • R 1 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 1 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R 1 is H, halogen, or Ci-C 6 -alkyl, wherein the alkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 1 is H or Ci-C 6 -alkyl, wherein the alkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 1 is Ci-C 6 -alkyl, which is unsubstituted or substituted with halogen or CN;
  • R 1 is Ci-C 6 -alkyl, which is unsubstituted
  • R 1 is Ci-C 6 -alkyl, which is substituted with halogen or CN;
  • R 1 is C 3 -C 6 -cycloalkyl, which is unsubstituted or substituted with halogen or CN;
  • R 1 is C 3 -C 6 -cycloalkyl, which is unsubstituted
  • R 1 is C 3 -C 6 -cycloalkyl, which is substituted with halogen or CN;
  • R 1 is H or halogen
  • R 1 is H
  • R 1 is halogen
  • R 1 is H, Cl, CH 3 , or cyclopropyl
  • R 1 is H or NR 6 R 7 ;
  • R 1 is NR 6 R 7 .
  • R 6 and R 7 are, identical or different, H, Ci-C 6 -alkyl, phenyl, -CH 2 - phenyl, 5- or 6- membered heteroaryl, -CH 2 -5- or 6- membered heteroaryl, 1 ,3-dioxolan-2- ylmethyl, or 2-(methylamino)-2-oxo-ethyl, wherein the alkyl, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN, or Ci-C 6 -alkyl.
  • R 6 and R 7 are, identical or different, H, phenyl, -CH 2 -phenyl, 5- or 6- membered heteroaryl, -CH 2 -5- or 6- membered heteroaryl, 1 ,3-dioxolan-2-ylmethyl, or 2- (methylamino)-2-oxo-ethyl, wherein the, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen or CN,
  • R 6 and R 7 are, identical or different, H, phenyl, -CH 2 -phenyl, 5- or 6- membered heteroaryl, -CH 2 -5- or 6- membered heteroaryl, 1 ,3-dioxolan-2-ylmethyl, or 2- (methylamino)-2-oxo-ethyl, wherein the, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN, or Ci-C 6 -alkyl;
  • R 6 and R 7 are, identical or different, H, -CH 2 -5- or 6- membered heteroaryl, 1 ,3-dioxolan-2-ylmethyl, or 2-(methylamino)-2-oxo-ethyl, wherein the, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN, or Ci-C 6 -alkyl;
  • R 6 is H and R 7 is -CH 2 -5- or 6- membered heteroaryl, 1 ,3- dioxolan-2-ylmethyl, or 2-(methylamino)-2-oxo-ethyl, wherein the alkyl, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN, or Ci-C 6 -alkyl;
  • R 6 and R 7 independantly of each other are selected from Rx- 1 to Rx-7 as shown in table Rx.
  • R 6 and R 7 independantly of each other are selected from Rx- 1 , Rx-2, Rx-7, and Rx-8, more preferably from Rx-1 and Rx-7.
  • R 2 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 2 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R 2 is H, halogen, or Ci-C 6 -alkyl, wherein the alkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 2 is H or Ci-C 6 -alkyl, wherein the alkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 2 is Ci-C 6 -alkyl, which is unsubstituted or substituted with halogen or CN;
  • R 2 is Ci-C 6 -alkyl, which is unsubstituted
  • R 2 is Ci-C 6 -alkyl, which is substituted with halogen or CN;
  • R 2 is C 3 -C 6 -cycloalkyl, which is unsubstituted or substituted with halogen or CN;
  • R 2 is C 3 -C 6 -cycloalkyl, which is unsubstituted
  • R 2 is C 3 -C 6 -cycloalkyl, which is substituted with halogen or CN;
  • R 2 is H or halogen
  • R 2 is H
  • R 2 is halogen
  • R 2 is H, Cl, Br, F, CH 3 , C 2 H 5 , n-C 3 H 7 , isopropyl, cyclopropyl, CH 2 F, CHF 2 , or CF 3 .
  • R 2 is H, CH 3 , C 2 H 5 , isopropyl, or cyclopropyl;
  • R 2 is H
  • R 2 is CH 3 ;
  • R 2 is C 2 H 5 ;
  • R 2 is isopropyl
  • R 2 is cyclopropyl
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, or Ci-C 6 -alkyl, wherein the alkyl moieties are unsubstituted or substituted with halogen;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, Cl, Br, F, CN, CH 3 , C 2 H 5 , n-C 3 H 7 , isopropyl, cyclopropyl, CF 3 , CH 2 F, OCH 3 , or OCHF 2 .
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, Cl, Br, F, CN, CH 3 , isopropyl, OCH 3 , or OCHF 2 .
  • R B1 and R B4 independently of each other are H, Cl, or CH 3 .
  • R B2 and R B3 independently of each other are H, Cl, Br, F, CN, CH 3 , isopropyl, cyclopropyl, OCH 3 , or OCHF 2 .
  • R B2 and R B3 independently of each other are H, Cl, F, CN, CH 3 , or OCH 3 ;
  • R B2 and R B3 independently of each other are H or Cl.
  • R 5 is H, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, or Ci-C 6 -alkyl-C 3 -C 6 - cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are substituted with halogen or CN;
  • R 5 is H, CH 3 , C 2 H 5 , or -CH 2 -cyclopropyl
  • D is DA
  • R 3 is H, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 3 is H or Ci-C 6 -alkyl, wherein the alkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 3 is H or C 3 -C 6 -cycloalkyl, wherein the cycloalkyl moieties are unsubstituted or substituted with halogen or CN; In another preferred embodiment, R 3 is H;
  • R 3 is H and DA exists in any of below tautomeric forms D3 and D4;
  • R 4 is H or C 3 -C 6 -cycloalkyl, wherein the cycloalkyl moieties are unsubstituted or substituted with halogen or CN;
  • R 4 is H
  • R 4 is H and DA exists in any of below tautomeric forms D1 D2
  • D is DB wherein B is a 5- or 6-membered carbocyclic group, wherein 1 or 2 CH 2 moieties of the carbocyclic group may be replaced by a carbonyl group, wherein the carbocyclic group is unsubstituted or substituted with R h ;
  • D is DB wherein B is a 5- or 6-membered carbocyclic group, wherein one CH 2 moiety of the carbocyclic group may be replaced by a carbonyl group, wherein the carbocyclic group is unsubstituted or substituted with R h ;
  • D is DB wherein B is a 5- or 6-membered carbocyclic group, wherein one CH 2 moiety of the carbocyclic group may be replaced by a carbonyl group;
  • D is DB wherein B is a 5- or 6-membered carbocyclic group, wherein one CH 2 moiety of the carbocyclic group is replaced by a carbonyl group;
  • D is DB which is selected from D5 to D7, and wherein the carbocyclic group of D5 to D7 moeities are unsubstituted or substituted with 1 or 2 substituents R h ,
  • D is a group selected from of D5 to D7 moeities, which are unsubstituted or substituted with 1 or 2 substituents R h ,
  • D is DB which is selected from D5 to D7, and wherein the carbocyclic group of D5 to D7 moeities are unsubstituted;
  • D is DB which is selected from D5 to D7, and wherein wherein the carbocyclic group of D5 to D7 moeities are substituted with 1 or 2 substituents R h ;
  • D is selected from DA, D5, D6, and D7 as defined herein;
  • D is selected from DA, D5, D6, and D7, wherein the carbocyclic group of D5, D6, and D7 moeities are unsubstituted or substituted with 1 or 2 substituents R h ;
  • D is DA or D5, wherein D5 is unsubstituted or substituted with 1 substituent R h ;
  • D is selected from DA or D5, wherein the carbocyclic group of D5 is substituted with 1 substituent R h ;
  • D is selected from DA or D5, wherein the carbocyclic group of D5 is unsubstituted;
  • D is D5, wherein the carbocyclic group of D5 is unsubstituted or substituted with 1 substituent R h ;
  • Ar 1 is phenyl which is unsubstituted or substituted with R Ar1 .
  • Ar 1 is 5- or 6-membered hetaryl, which is unsubstituted or substituted with R Ar1 ;
  • Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, which are unsubstituted or substituted with R Ar1 .
  • R Ar1 is halogen, SF 5 , NO 2 , OH, CN, Ci-C 6 -alkyl, Ci-C 6 - alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocyclyl, C 3 -C 6 -cycloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C 3 -C 6 -heterocyclyl, and cycloalkoxy moieties are unsubstituted or substituted with R f
  • Ar 1 is 5- or 6- membered hetaryl, which is unsubstituted or substituted with R Ar1 ;
  • R Ar1 is halogen, SF 5 , NO 2 , CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 - C 6 -cycloalkyl, C 3 -C 6 -heterocyclyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C 3 -C 6 -heterocyclyl, and cycloalkoxy moieties are unsubstituted or substituted with R f ;
  • R Ar1 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, wherein the alkyl and alkoxy moieties are unsubstituted or substituted with R f ,
  • Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, which are unsubstituted or substituted with R Ar1 ;
  • R Ar1 is halogen, SF 5 , NO 2 , OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 - heterocyclyl, C 3 -C 6 -cycloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C 3 -C 6 -heterocyclyl, and cycloalkoxy moieties are unsubstituted or substituted with R f ;
  • R a , R b and R c identical or different, are H, Ci-C 6 -alkyl, which are unsubstituted or substituted with halogen;
  • R d is H or Ci-C 6 -alkyl
  • R e is Ci-C 6 -alkyl or Ci-C 6 -haloalkyl
  • R f is halogen, OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 -cycloalkoxy, which are unsubstituted or substituted with halogen; m is 0, 1 ,or 2.
  • Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, which are unsubstituted or substituted with R Ar1 ;
  • R Ar1 is halogen, NO 2 , CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocyclyl, C 2 - C 6 -alkenyl, C 2 -C 6 -alkynyl wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C 3 -C 6 - heterocyclyl moieties are unsubstituted or substituted with R f ;
  • R a , R b and R c identical or different, are H, Ci-C 6 -alkyl, which are unsubstituted or substituted with halogen;
  • R d is H or Ci-C 6 -alkyl
  • R e is Ci-C 6 -alkyl or Ci-C 6 -haloalkyl
  • R f is halogen, OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 -cycloalkoxy, which are unsubstituted or substituted with halogen; m is 0, 1 ,or 2.
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -26 as shown in Table Ar1 ,
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -9;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -8; In another preferred embodiment, Ar 1 is selected from Ar 1 -1 to Ar 1 -3;
  • Ar 2 is phenyl which is unsubstituted or substituted with R Ar2 ;
  • Ar 2 is 5- or 6-membered hetaryl, which is unsubstituted or substituted with R Ar2 ;
  • Ar 2 is phenyl, pyrimidinyl, thiophenyl, thiazolyl, or pyridyl, which are unsubstituted or substituted with R Ar2 .
  • R Ar2 is halogen, CN, -SCN, -SF 5 , Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 - C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 -alkoxy-Ci-C 4 -alkyl, Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkyl-Ci-C 4 -alkyl, C 3 -C 6 -cycloalkoxy-Ci-C 4 -alkyl, wherein the
  • R Ar2 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkoxy- Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; or NR b R c ;
  • R Ar2 is halogen, CN, NR b R c , Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci- C 6 -alkoxy-Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R Ar2 is NR b R c ;
  • R Ar2 is halogen, CN, Ci-C 6 -alkyl, wherein the alkyl, moieties are unsubstituted or substituted with halogen;
  • R Ar2 is halogen or Ci-C 6 -alkyl, wherein the alkyl moieties are unsubstituted or substituted with halogen;
  • R Ar2 is halogen or Ci-C 6 -alkyl
  • R Ar2 is halogen
  • R Ar2 is halogen or CN
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -20 as shown in Table Ar2,
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -3;
  • R a , R b and R c identical or different, are H, Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, which are unsubstituted or substituted with halogen;
  • R a , R b and R c identical or different are H, Ci-C 6 -alkyl which is unsubstituted or substituted with halogen;
  • R d is H; In another preferred embodiment, R d is Ci-C 6 -alkyl.
  • R e is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, or C 3 -C 6 - halocycloalkyl;
  • R e is Ci-C 6 -alkyl or Ci-C 6 -haloalkyl
  • R f is halogen, OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, or C 3 -C 6 -cycloalkoxy, which are unsubstituted or substituted with halogen;
  • R f is halogen, OH, CN, or Ci-C 6 -alkyl.
  • R h is halogen or Ci-C 6 -alkyl
  • m is 0;
  • m is 1 ;
  • n 2;
  • m is 0 or 1 ;
  • m is 1 or 2.
  • D is DA, D5, D6, or D7, preferably D5;
  • B 1 is N or CR B1
  • B 2 is CR B2
  • B 3 is CR B3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, or Ci-C 6 - alkoxy, wherein the alkyl and alkoxymoieties are unsubstituted or substituted with halogen;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl;
  • R 1 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R 2 is H or Ci-C 6 -alkyl
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, which are unsubstituted or substituted with R Ar1 ;
  • R a , R b and R c identical or different, are H, Ci-C 6 -alkyl, which are unsubstituted or substituted with halogen;
  • R d is H or Ci-C 6 -alkyl
  • R e is Ci-C 6 -alkyl or Ci-C 6 -haloalkyl
  • R f is halogen, OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 -cycloalkoxy, which are unsubstituted or substituted with halogen; m is 0, 1 , or 2.
  • D is DB, preferably D5;
  • B 1 is N or CR B1
  • B 2 is CR B2
  • B 3 is CR B3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, or Ci-C 6 - alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl;
  • R 1 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R 2 is Ci-C 6 -alkyl
  • Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, which are unsubstituted or substituted with R Ar1 ;
  • R Ar1 is halogen, NO 2 , CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocyclyl, C 2 -C 6 - alkenyl, C 2 -C 6 -alkynyl wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C 3 -C 6 - heterocyclyl moieties are unsubstituted or substituted with R f ;
  • Ar 2 is phenyl which is unsubstituted or substituted with R Ar2 ;
  • R Ar2 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; or NR b R c ;
  • R a , R b and R c identical or different, are H, Ci-C 6 -alkyl, which are unsubstituted or substituted with halogen;
  • R d is H or Ci-C 6 -alkyl
  • R e is Ci-C 6 -alkyl or Ci-C 6 -haloalkyl
  • R f is halogen, OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 -cycloalkoxy, which are unsubstituted or substituted with halogen; m is 0, 1 , or 2.
  • compounds of formula I are selected from compounds of formulae A.1 to A.10,
  • compounds of formula I are selected from compounds of formula A.1 to A.5
  • compounds of formula I are selected from compounds of formula A.6 to A.10 In another preferred embodiment compounds of formula I are selected from compounds of formula A.1 and A.6;
  • compounds of formula I are selected from compounds of formula A.2 and A.7;
  • compounds of formula I are selected from compounds of formula A.3 and A.8;
  • compounds of formula I are selected from compounds of formula A.4 and A.9;
  • compounds of formula I are selected from compounds of formula A.5 and A.10;
  • compounds of formula I are selected from compounds of formula A.1 to A.5, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • compounds of formula I are selected from compounds of formula A.6 to A.10, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • compounds of formula I are selected from compounds of formula A.1 and A.6, Wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • compounds of formula I are selected from compounds of formula A.2 and A.7, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • compounds of formula I are selected from compounds of formula A.3 and A.8, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • compounds of formula I are selected from compounds of formula A.4 and A.9, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • compounds of formula I are selected from compounds of formula A.5 and A.10, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is selected from the compounds of formulae 1.1 to 1.4,
  • the compound of formula I is selected from the compounds of formulae 1.1 and 1.2;
  • the compound of formula I is selected from the compounds of formulae 1.1 and 1.3;
  • the compound of formula I is selected from the compounds of formulae 1.3 and 1.4;
  • the compound of formula I is selected from the compounds of formulae 1.2 and 1.4;
  • the compound of formula I is compound of formula 1.1 ;
  • the compound of formula I is compound of formula 1.2;
  • the compound of formula I is compound of formula 1.3;
  • the compound of formula I is compound of formula 1.4;
  • the compound of formula I is selected from the compounds of formulae 1.1 to 1.4, wherein
  • B 1 is N or CR B1
  • B 2 is CR B2
  • B 3 is CR B3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, or Ci-C 6 - alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl;
  • R 1 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R 2 is Ci-C 6 -alkyl
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, which are unsubstituted or substituted with R Ar1 ;
  • R Ar1 is halogen, NO 2 , CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocyclyl, C 2 -C 6 - alkenyl, C 2 -C 6 -alkynyl wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C 3 -C 6 - heterocyclyl moieties are unsubstituted or substituted with R f ;
  • Ar 2 is phenyl which is unsubstituted or substituted with R Ar2 ;
  • R Ar2 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; or NR b R c ;
  • R a , R b and R c identical or different, are H, Ci-C 6 -alkyl, which are unsubstituted or substituted with halogen;
  • R d is H or Ci-C 6 -alkyl
  • R e is Ci-C 6 -alkyl or Ci-C 6 -haloalkyl
  • R f is halogen, OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 -cycloalkoxy, which are unsubstituted or substituted with halogen; m is 0, 1 , or 2.
  • the compound of formula I is selected from the compounds of formulae 1.1 to 1.4, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 to Ar 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is selected from the compounds of formulae 1.1 to 1.4, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is selected from the compounds of formulae 1.1 and 1.2, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is selected from the compounds of formulae 1.1 and 1.3, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is selected from the compounds of formulae 1.3 and 1.4, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is selected from the compounds of formulae 1.2 and 1.4, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is compound of formula 1.1 , wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is compound of formula 1.2, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 3 is H or Ci-C 6 -alkyl
  • R 4 is H or Ci-C 6 -alkyl
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is compounds of formula 1.3, wherein
  • B 1 is N or CR B1
  • B 2 is CR B2
  • B 3 is CR B3 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, or Ci-C 6 - alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl;
  • R 1 is H, halogen, Ci-C 6 -alkyl, or C 3 -C 6 -cycloalkyl;
  • R 2 is Ci-C 6 -alkyl
  • Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, which are unsubstituted or substituted with R Ar1 ;
  • R Ar1 is halogen, NO 2 , CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocyclyl, C 2 - C 6 -alkenyl, C 2 -C 6 -alkynyl wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C 3 -C 6 - heterocyclyl moieties are unsubstituted or substituted with R f ;
  • Ar 2 is phenyl which is unsubstituted or substituted with R Ar2 ;
  • R Ar2 is halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; or NR b R c ;
  • R a , R b and R c identical or different, are H, Ci-C 6 -alkyl, which are unsubstituted or substituted with halogen;
  • R d is H or Ci-C 6 -alkyl
  • R e is Ci-C 6 -alkyl or Ci-C 6 -haloalkyl
  • R f is halogen, OH, CN, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 -cycloalkoxy, which are unsubstituted or substituted with halogen; m is 0, 1 , or 2.
  • the compound of formula I is compound of formula 1.3, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • the compound of formula I is compound of formula 1.4, wherein
  • R 5 is H, Ci-C 6 -alkyl, or Ci-C6-alkyl-C 3 -C 6 -cycloalkyl, preferably H, CH 3 , C 2 H 5 , or -CH 2 - cyclopropyl, more preferably H or CH 3 ;
  • R 1 is H or Ci-C 6 -alkyl, preferably H or CH 3 ;
  • R 2 is H or Ci-C 6 -alkyl, preferably CH 3 ;
  • B 1 is N or CR B1 ;
  • B 2 is N or CR B2 ;
  • B 3 is N or CR B3 ;
  • B 4 is CR B4 ;
  • R B1 , R B2 , R B3 , and R B4 independently of each other are H, halogen, CN, Ci-C 6 -alkyl, C 3 -C 6 - cycloalkyl, or Ci-C 6 -alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen;
  • Ar 1 is selected from Ar 1 -1 to Ar 1 -17, preferably from Ar 1 -1 to Ar 1 -8, more preferably from Ar 1 -1 toAr 1 -3;
  • Ar 2 is selected from Ar 2 -1 to Ar 2 -13, preferably from Ar 2 -1 to Ar 2 -3;
  • Particular compounds of formula I are the compounds of the formulae 1.1 to 1. 4 that are compiled in the following tables 1 to 48, wherein the combination of variables B 1 , B 2 , B 3 , and B 4 for each compound of tables 1 to 48 corresponds to each line of Table B.
  • Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
  • Table 49 to Table 96 Includes all the compounds as disclosed in Table 1 to Table 48 respectively wherein compound of formula 1.3 is replaced by compound of formula 1.4;
  • the term “compound(s) of the present invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to as “compound(s) of formula I” or“compound(s) I” or “formula I compound(s)”, and includes their salts, tautomers, stereoisomers, and N-oxides.
  • the present invention also relates to a mixture of at least one compound of the invention with at least one mixing partner as defined herein.
  • Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly from 10:1 to 1 :10.
  • components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers.
  • Preferred mixing partners are insecticides, nematicides and fungicides.
  • M.1 Acetylcholine esterase (AChE) inhibitors M.1A carbamates, e.g. aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
  • GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S- cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esf
  • Nicotinic acetylcholine receptor agonists MAA neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.1 4,5-Dihydro-N-nitro-1-(2-oxiranylmethyl)-1 H-imidazol-2-amine, M.4A.2: (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7- hexahydroimidazo[1 ,2-a]pyridine; or M.4B nicotine
  • Nicotinic acetylcholine receptor allosteric activators e.g. spinosad orspinetoram;
  • M.6 Chloride channel activators from the class of avermectins and milbemycins e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;
  • M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, kino- prene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;
  • M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic;
  • M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon;
  • M.10 Mite growth inhibitors e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole
  • M.11 Microbial disruptors of insect midgut membranes e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry 1 Ab, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miticides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetradifon;
  • Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues bensultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
  • M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
  • benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;
  • Octopamin receptor agonists e.g. amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;
  • M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A METI acaricides and insecticides such as fenazaquin, fen pyroxi mate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B metaflumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4- chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;
  • M.23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion;
  • M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
  • Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;
  • M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N1- ⁇ 2-methyl-4-[1 ,2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid, M.28.2: (S)-3-Chloro-N1- ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1- methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5- dibromo-2-( ⁇ [3-bro
  • M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
  • M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afidopyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chino- methionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metaldehyde, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, M.UN.3: 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9- azadispiro[4.2.4.2]-tetradec-11-en-10-one,
  • M.UN.5 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-
  • M.UN.8 fluazaindolizine
  • M.UN.10 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;
  • M.UN.11 .m N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11 .n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11 .o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl- benzamide; M.
  • M.UN.12. a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.UN.12.b) 2-[6-[2-(5- Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12. c) 2-[6-[2-(3-Pyridinyl)-5- thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.
  • M.UN.14a 1-[(6-Chloro-3-pyridinyl)methyl]- 1 ,2, 3,5,6, 7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M.UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; M. UN.16a) 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.
  • UN.16b 1- (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
  • M. UN.16c N,5- dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide;
  • M.UN.16d 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
  • M.UN.16e N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.UN.16f 1-(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M .UN.16g 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
  • M.UN.16h N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide
  • M.UN.16i 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-
  • M. UN.17a N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
  • M. UN.17b N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
  • M.UN.17c N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide
  • M.UN.17d 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4- carboxamide
  • M.UN.17e 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5- carboxamide
  • M.UN.17f methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydr
  • M.UN.21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide;
  • M. UN.22a 2-(3-ethylsulfonyl-2- pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine;
  • M.4 cycloxaprid is known from W02010/069266 and WO2011/069456.
  • M.4A.1 is known from CN 103814937; CN105367557, CN 105481839.
  • M.4A.2, guadipyr is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO 2007/101369.
  • MAE.1a) to M.4E.1f) are known from WO2018177970.
  • M.22B.1 is described in CN10171577 and M.22B.2 in CN102126994.
  • Spiropidion M.23.1 is known from WO 2014/191271.
  • M.28.1 and M.28.2 are known from W02007/101540.
  • M.28.3 is described in W02005/077934.
  • M.28.4 is described in W02007/043677.
  • M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO 2013/024010,
  • M.28.5i) is described in WO2011/085575
  • M.28.6 can be found in WO2012/034472.
  • M.UN.3 is known from W02006/089633 and M.UN.4 from W02008/067911 .
  • M.UN.5 is described in W02006/043635, and biological control agents on the basis of bacillus firmus are described in W02009/124707. Flupyrimin is described in WO2012/029672.
  • M.UN.8 is known from WO2013/055584.
  • M.UN.9.a) is described in WO2013/050317.
  • M.UN.9.b) is described in WO2014/126208.
  • M.UN.10 is known from WO2010/060379.
  • M.UN.H .b) to M.UN.H .h) are described in W02010/018714, and M.UN.H i) to M.UN.H .p) in WO 2010/127926.
  • M.UN.12.a) to M.UN.12.C) are known from WO2010/006713, M.UN.12.d) and M.UN.12.e) are known from WO2012/000896.
  • M. UN.14a) and M. UN.14b) are known from W02007/101369.
  • M.UN.16.a) to M.UN.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497.
  • M. UN.17a) to M.UN.17J) are described in WO2015/038503.
  • M.UN.18 Tycloprazoflor is described in US2014/0213448.
  • M.UN.19 is described in WO2014/036056.
  • M.UN.20 is known from WO2014/090918.
  • M.UN.21 is known from EP2910126. M.
  • M.UN.22a and M.UN.22b are known from W02015/059039 and W02015/190316.
  • M.UN.23a and M. UN.23b are known from WO2013/050302.
  • M.UN.24a) and M.UN.24b) are known from WO2012/126766.
  • Acynonapyr M.UN.25 is known from WO 2011/105506.
  • Benzpyrimoxan M.UN.26 is known from W02016/104516.
  • M.UN.27 is known from WO2016/174049.
  • M.UN.28 Oxazosulfyl is known from WO2017/104592.
  • M. UN.29a) to M.UN.29f) are known from W02009/102736 or WO2013116053.
  • M.UN.30 is known from WO2013/050302.
  • M.UN.30a) to M. UN.30k) are known from WO2018/052136.
  • Inhibitors of complex III at Q o site azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-
  • C14 demethylase inhibitors triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1 A), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21), propiconazole (B.1.2
  • Delta14-reductase inhibitors aldimorph (B.2.1), dodemorph (B.2.2), dodemorph- acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);
  • Nucleic acid synthesis inhibitors phenylamides or acyl amino acid fungicides benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7); other nucleic acid synthesis inhibitors: hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p- tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4
  • MAP I histidine kinase inhibitors fluoroimid (F.1 .1), iprodione (F.1 .2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);
  • G protein inhibitors quinoxyfen (F.2.1);
  • Phospholipid biosynthesis inhibitors edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4); lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7); phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7); compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1); inhibitors of oxysterol binding protein: oxa
  • component 2 The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci.
  • WO 10/069882 WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 , WO 13/162072, WO 13/092224, WO 11/135833, ON 1907024, ON 1456054, ON 103387541 , ON 1309897, WO 12/84812, ON 1907024, WO 09094442, WO 14/60177, WO 13/116251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511 , WO 11/081174, WO 13/47441).
  • Some compounds are identified by their CAS Registry Number which is separated by hyphens into three parts, the first consisting from two up to seven digits, the second
  • Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides fall into two major classes, microbial and biochemical pesticides:
  • Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.
  • Biochemical pesticides are naturally occurring substances or or structurally-similar and functionally identical to a naturally-occurring substance and extracts from biological sources that control pests or provide other crop protection uses as defined below, but have non-toxic mode of actions (such as growth or developmental regulation, attractents, repellents or defence activators (e.g. induced resistance) and are relatively non-toxic to mammals.
  • Biopesticides for use against crop diseases have already established themselves on a variety of crops. For example, biopesticides already play an important role in controlling downy mildew diseases. Their benefits include: a 0-Day Pre-Harvest Interval, the ability to use under moderate to severe disease pressure, and the ability to use in mixture or in a rotational program with other registered pesticides.
  • Biopesticidal seed treatments are e.g. used to control soil borne fungal pathogens that cause seed rots, damping-off, root rot and seedling blights. They can also be used to control internal seed borne fungal pathogens as well as fungal pathogens that are on the surface of the seed.
  • Many biopesticidal products also show capacities to stimulate plant host defenses and other physiological processes that can make treated crops more resistant to a variety of biotic and abiotic stresses or can regulate plant growth. Many biopesticidal products also show capacities to stimulate plant health, plant growth and/or yield enhancing activity.
  • biopesticides in conjunction with which the compounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them:
  • Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens ssp. plantarum (also referred to as B. velezensis), B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, B.
  • violaceusniger Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, zucchini yellow mosaic virus (avirulent strain);
  • Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity harpin protein, Reynoutria sachalinensis extract;
  • Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beauveria bassiana, B.
  • brongniartii Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L.
  • HearNPV Helicoverpa armigera nucleopolyhedrovirus
  • HzNPV Helicoverpa zea nucleopolyhedrovirus
  • HzSNPV Helicoverpa zea single capsid nucleopolyhe
  • Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity Azospirillum amazonense, A. brasilense, A. lipoferum,
  • the biopesticides from group L1) and/or L2) may also have insecticidal, acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity.
  • the biopesticides from group L3) and/or L4) may also have fungicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity.
  • the biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity.
  • velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181 — 197, 1998; e. g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. a. ssp. plantarum or B. velezensis MBI600 isolated from faba bean in Sutton Bonington, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B-50595; US 2012/0149571 A1 ; e. g. Integral® from BASF Corp., USA), B. a. ssp. plantarum or B.
  • velezensis QST-713 isolated from peach orchard in 1995 in California, U.S.A. (NRRL B-21661 ; e. g. Serenade® MAX from Bayer Crop Science LP, USA), B. a. ssp. plantarum or B. velezensis TJ1000 isolated in 1992 in South Dakoda, U.S.A, (also called 1 BE; ATCC BAA-390; CA 2471555 A1 ; e. g. QuickRootsTM from TJ Technologies, Watertown, SD, USA); B.
  • CNCM 1-1582 a variant of parental strain EIP-N1 (CNCM 1-1556) isolated from soil of central plain area of Israel (WO 2009/126473, US 6,406,690; e. g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizosphere in Mexico (IDAC 260707-01 ; e. g. PRO-MIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to as BU-F22 and BU-F33 isolated at least before 1993 from cucumber infested by Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), B.
  • pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014/029697; e. g. BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B-30087; e. g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; US 8,445,255), B.
  • subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US 2010/0260735; WO 2011/109395); B. thuringiensis ssp. aizawai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG-6346; ATCC SD-1372; e. g. XenTari® from BioFa AG, Munsingen, Germany), B. t. ssp.
  • israeltaki ABTS-351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e. g. Dipel® DF from Valent BioSciences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B-50753; e. g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp.
  • tenebrionis NB-176-1 a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585 215 B1 ; e. g. Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e. g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e. g. Naturalis® from CBC (Europe) S.r.l . , Italy), B.
  • DSM 5480 Tenebrio molitor
  • EP 585 215 B1 e. g. Novodor® from Valent BioSciences, Switzerland
  • Beauveria bassiana GHA ATCC 74250; e. g. BotaniGard® 22WGP from Laverlam Int. Corp., USA
  • bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e. g. BroadBand® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e. g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B.
  • japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e. g. in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); B. japonicum strains deposited at SEMIA known from Appl. Environ. Microbiol.
  • SEMIA 5079 isolated from soil in Cerrados region, Brazil by Embrapa- Cerrados used in commercial inoculants since 1992 (CPAC 15; e. g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under lab condtions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, being a natural variant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e. g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp.
  • HSSNPV single capsid nucleopolyhedrovirus
  • ABA-NPV-U e. g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia
  • Heterorhabditis bacteriophora e. g.
  • Met52® Novozymes Biologicals BioAg Group, Canada Metschnikowia fructicola 277 isolated from grapes in the central part of Israel (US 6,994,849; NRRL Y-30752; e. g. formerly Shemer® from Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89/030550; WO1991/02051 ; Crop Protection 27, 352-361 , 2008; e. g.
  • Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014/029697; NRRL B-50755; e.g. BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa), Paenibacillus strains isolated from soil samples from a variety of European locations including Germany: P. epiphyticus Lu17015 (WO 2016/020371 ; DSM 26971), P. polymyxa ssp. plantarum Lu16774 (WO 2016/020371 ; DSM 26969), P. p. ssp.
  • the solid material (dry matter) of the biopesticides (with the exception of oils such as Neem oil) are considered as active components (e.g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).
  • the weight ratios and percentages used herein for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).
  • the total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms can be determined using the amount of CFU of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1 x 10 10 CFU equals one gram of total weight of the respective active component.
  • Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells.
  • CFU may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, such as Steinernema feltiae.
  • the application rates preferably range from about 1 x 10 6 to 5 x 10 15 (or more) CFU/ha, preferably from about 1 x 10 8 to about 1 x 10 13 CFU/ha, and even more preferably from about 1 x 10 9 to about 1 x 10 12 CFU/ha.
  • the application rates preferably range inform about 1 x 10 5 to 1 x 10 12 (or more), more preferably from 1 x 10 8 to 1 x 10 11 , even more preferably from 5 x 10 8 to 1 x 10 10 individuals (e. g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.
  • the application rates with respect to plant propagation material preferably range from about 1 x 10 6 to 1 x 10 12 (or more) CFU/seed.
  • the concentration is about 1 x 10 6 to about 1 x 10 9 CFU/seed.
  • the application rates with respect to plant propagation material also preferably range from about 1 x 10 7 to 1 x 10 14 (or more) CFU per 100 kg of seed, preferably from 1 x 10 9 to about 1 x 10 12 CFU per 100 kg of seed.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.
  • An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof.
  • the term "pesticidally effective amount” is defined below.
  • compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
  • compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
  • the compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi-ers and binders.
  • suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants,
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, alkylated
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose, starch
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul-fates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl-sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters. Exam-pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth-oxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli-nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are: i) Water-soluble concentrates (SL, LS)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a compound I according to the invention 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active sub-stance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1-2 wt% thickener e.g. xanthan gum
  • up to 100 wt% water 100 wt% water
  • Dilution with water gives a stable suspension of the active sub-stance.
  • binder e.g. polyvinylalcohol
  • wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • WP, SP, WS Water-dispersible powders and water-soluble powders
  • wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
  • wt% dispersants e.g. sodium lignosulfonate
  • wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a compound I according to the invention In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active sub-stance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1-5 wt% thickener e.g. carboxymethylcellulose
  • a compound I according to the invention 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alkohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g.
  • a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • solid carrier e.g. silicate
  • 1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • organic solvent e.g. aromatic hydrocarbon.
  • compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • auxiliaries such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 : 100 to 100: 1 , preferably 1 : 10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components e. g. components comprising compounds of the present invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
  • the compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the present invention.
  • the compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the present invention.
  • the compounds of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
  • the compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above.
  • the components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture “in situ” on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
  • Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application.
  • Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection.
  • Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting.
  • furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow.
  • Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment.
  • pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.
  • the term "contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
  • animal pest includes arthropods, gastropods, and nematodes.
  • Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
  • Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
  • crop refers to both, growing and harvested crops.
  • plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • iceberg lettuce chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g. carnation, petunias, geranium/pelargoniums, pansies and impatiens), shrubs, broadleaved trees (e.g.
  • poplar or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses.
  • Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • cultiva plants is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome.
  • Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
  • Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
  • one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
  • the process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
  • Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. However, most of the herbicide tolerance traits have been created via the use of transgenes.
  • ALS acetolactate synthase
  • Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
  • HPPD 4- hydroxyphenylpyruvate dioxygenase
  • Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
  • T ransgenic corn events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHGOJG, HCEM485, VCO-01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.
  • Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211 , BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
  • Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1 , HCN10, HCN28, HCN92, MS1 , MS8, PHYU, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.
  • Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants.
  • Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1A, crylAb, cry1 Ab-Ac, crylAc, cry1A.1O5, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20.
  • genes of plant origin have been transferred to other plants.
  • genes coding for protease inhibitors like CpTI and pinll.
  • a further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes.
  • An example for such a transgene is dvsnf7.
  • Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt 10, Bt 11 , Bt 176, MON801 , MON802, MON809, MON810, MON863, MON87411 , MON88017, MON89034, 33121 , 4114, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.
  • Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701 , MON87751 and DAS-81419.
  • Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321. Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
  • Cultivated plants comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
  • Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IND-00410-5.
  • Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process.
  • Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.
  • Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art.
  • ISAAA International Service for the Acquisition of Agri-biotech Applications
  • CERA Center for Environmental Risk Assessment
  • compositions according to the invention on cultivated plants may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
  • the pesticidal activity of the compounds of the present invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.
  • plant propagation material refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 .
  • the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
  • the compounds of the invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects.
  • the invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermination with a compound of the invention.
  • the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking insects, chewing insects and nematodes.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods.
  • seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the invention also comprises seeds coated with or containing the active compound.
  • coated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
  • Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize I sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
  • Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included.
  • the active substance concentrations in ready-to-use formulations are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Especially preferred FS formulations of the compounds of the invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.
  • a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like
  • the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
  • the invention therefore also relates to seed comprising a compound of the invention, or an agriculturally useful salt thereof, as defined herein.
  • the amount of the compound of the invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
  • the compounds of the invention may also be used for improving the health of a plant. Therefore, the invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the invention.
  • an effective and non-phytotoxic amount means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.
  • plant and “plant propagation material” are defined above.
  • Plant health is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves (“greening effect”), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).
  • yield for example increased biomass and/or increased content of valuable ingredients
  • quality for example improved content or composition of certain ingredients or shelf life
  • plant vigour for example improved plant growth and/or greener leaves (“greening effect”)
  • tolerance to abiotic for example drought
  • biotic stress for example disease
  • production efficiency for example, harvesting efficiency, processability

Abstract

La présente invention concerne les composés de formule (I), et les N-oxydes, stéréoisomères, tautomères et sels acceptables sur le plan agricole ou vétérinaire de ceux-ci, les variables étant définies selon la description, la formule (I), (I). Les composés de formule (I), ainsi que les N-oxydes, stéréoisomères, tautomères et sels acceptables sur le plan agricole ou vétérinaire de ceux-ci, sont utiles pour combattre ou lutter contre les invertébrés nuisibles, en particulier les arthropodes nuisibles et les nématodes. L'invention concerne également un procédé de lutte contre les invertébrés nuisibles faisant appel à ces composés ainsi qu'un matériel de propagation des végétaux et une composition agricole et vétérinaire comprenant lesdits composés.
PCT/EP2023/071106 2022-08-02 2023-07-31 Composés pesticides pyrazolo WO2024028243A1 (fr)

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