Cyclopentanedione compounds and their use as insecticides and acaricides

The present invention relates to cyclopentanedione compounds and their derivatives as insecticides, acaricides and / or antifungal agents.

Cyclopentanedione compounds having herbicidal activity are described, for example, in WO01 / 74770, WO96 / 03366 and WO2009 / 019015.

Cyclopentanedione compounds with insecticidal and / or acaricidal and / or antifungal properties are currently being found.

<p num="0004"><patcit num="1"><text>International Publication No. 01/74770</text></patcit><patcit num="2"><text>International Publication No. 96/03366</text></patcit><patcit num="3"><text>International Publication No. 2009/019015</text></patcit></p>

Accordingly, the present invention is the use of compounds of formula I as insecticides, acaricides and / or antifungal agents.

<chemistry num="1"><img id="000002" he="44" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /></chemistry> During the ceremony R¹Is methyl, ethyl, n-propyl, isopropyl, halomethyl, haloethyl, halogen, vinyl, ethynyl, methoxy, ethoxy, halomethoxy, haloethoxy, or cyclopropyl. R²And R³Are independent of each other, hydrogen, halogen, C₁-C₆Alkyl, C₁-C₆Haloalkyl, C₁-C₆Alkoxy, C₁-C₆Haloalkoxy, C₂-C₆Alkenyl, C₂-C₆Haloalkenyl, C₂-C₆Alkyne, C₃-C₆Alkenyloxy, C₃-C₆Haloalkenyloxy, C₃-C₆Alkynyloxy, C₃-C₆Cycloalkyl, C₁-C₆Alkylthio, C₁-C₆Alkyl sulfinyl, C₁-C₆Alkylsulfonyl, C₁-C₆Alkoxysulfonyl, C₁-C₆Haloalkoxysulfonyl, cyano, nitro, optionally substituted aryl or optionally substituted heteroaryl, where R²And R³At least one of the optionally substituted aryl or optionally substituted heteroaryl, R⁴Is hydrogen, methyl, ethyl, n-propyl, isopropyl, halomethyl, haloethyl, halogen, vinyl, ethynyl, methoxy, ethoxy, halomethoxy or haloethoxy. R⁵And R¹²Are independent of hydrogen, C₁-C₃Alkyl, C₁-C₃Haloalkyl, C₁-C₃Alkoxy, C₁-C₃Alkylthio, halogen or C₁-C₆Alkoxycarbonyl or R⁵And R¹²Together form a 3- to 7-membered carbocycle, optionally containing oxygen or sulfur, as well as R⁶, R⁷, R⁸, R⁹, R¹⁰And R¹¹Are independently hydrogen or substituents, or R⁷And R⁸Or R⁹And R¹⁰Together with the carbon atoms to which they bind form keto, or optionally substituted imines, or optionally substituted alkenyl units, or R⁷, R⁸, R⁹And R¹⁰Any two of them may together form a 3- to 8-membered carbocycle, optionally containing a heteroatom selected from O, S or N, and optionally substituted. Or R⁷And R¹⁰Together to form a bond, as well as G is hydrogen (a) or is one of the following groups

<chemistry num="2"><img id="000003" he="52" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /></chemistry> During the ceremony E is a metal ion or ammonium ion, L is oxygen or sulfur, and M is oxygen or sulfur, R¹¹In each case, optionally halogen-or cyano-substituted C₁-C₂₀-Alkyl, C₂-C₂₀-Alkenyl, C₁-C₈-Alkoxy-C₁-C₈-Alkyl, C₁-C₈-Alkylthio-C₁-C₈-Alkyl or Poly-C₁-C₈-Alkoxy-C₁-C₈-Alkyl or optionally halogen-, C₁-C₆-Alkyl- or C₁-C₆-Alkoxy-Substitution C₃-C₈-Cycloalkyl, where one or two non-adjacent methylene groups are optionally replaced by oxygen and / or sulfur, In some cases halogen-, cyano-, nitro-, C₁-C₆-Alkyl-, C₁-C₆-Alkoxy-, C₁-C₆-Haloalkyl-, C₁-C₆-Halo Alkoxy-, C₁-C₆-Alkylthio- or C₁-C₆-Alkylsulfonyl-substituted phenyl or In some cases halogen-, nitro-, cyano-, C₁-C₆-Alkyl-, C₁-C₆-Alkoxy-, C₁-C₆-Haloalkyl- or C₁-C₆-Haloalkoxy-Substituted Phenyl-C₁-C₆-Alkyl or Halogen-or C in some cases₁-C₆A 5- or 6-membered heteroatom of the -alkyl-substituted, having one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, or Halogen-or C in some cases₁-C₆-Alkyl-substituted phenoxy-C₁-C₆-Alkyl or In some cases halogen-, amino- or C₁-C₆-Alkyl-substituted 5- or 6-membered hetaryloxy-C₁-C₆-Alkyl, having one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen R²²Is, in each case, a halogen-or cyano-substituted C₁-C₂₀-Alkyl, C₂-C₂₀-Alkenyl, C₁-C₈-Alkoxy-C₂-C₈-Alkyl or Poly-C₁-C₈-Alkoxy-C₂-C₈-Alkyl or In some cases halogen-, C₁-C₆-Alkyl- or C₁-C₆-Alkoxy-Substitution C₃-C₈-Cycloalkyl or Halogen-, cyano-, nitro-, C, respectively, as the case may be₁-C₆-Alkyl-, C₁-C₆-Alkoxy-, C₁-C₆-Haloalkyl- or C₁-C₆-Haloalkoxy-substituted phenyl or benzyl, R³³Is, in some cases, halogen-substituted C₁-C₈-Alkyl or, respectively, optionally halogen-, C₁-C₆-Alkyl-, C₁-C₆-Alkoxy-, C₁-C₄-Haloalkyl-, C₁-C₄-Haloalkoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴⁴And R⁵⁵Are independent of each other and, in some cases, halogen-substituted C₁-C₈-Alkyl, C₁-C₈-Alkoxy, C₁-C₈-Alkylamino, di (C)₁-C₈-Alkyl) amino, C₁-C₈-Alkylthio or C₃-C₈-Alkenylthio or, respectively, optionally halogen-, nitro-, cyano-, C₁-C₄-Alkoxy-, C₁-C₄-Halo Alkoxy-, C₁-C₄-Alkylthio-, C₁-C₄-Halo-alkylthio-, C₁-C₄-Alkyl- or C₁-C₄-Haloalkyl-Substituted phenyl, phenoxy or phenylthio, R⁶⁶And R⁷⁷Are independent of each other, hydrogen, or optionally halogen- or cyano-substituted C, respectively.₁-C₈-Alkyl, C₃-C₈-Cycloalkyl, C₁-C₈-Alkoxy, C₃-C₈-Alkenyl or C₁-C₈-Alkoxy-C₂-C₈-Alkyl or, respectively, optionally halogen-, C₁-C₈-Alkyl-, C₁-C₈-Haloalkyl- or C₁-C₈-Alkoxy-substituted phenyl or benzyl, or together, optionally C₁-C₆-Alkylation-Substitution C₃-C₆-The alkylene group, where one methylene group is optionally replaced by oxygen or sulfur.

In an alternative definition of a compound of formula I, each alkyl moiety is either alone or part of a larger group (eg, alkoxy, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl). , Linear or branched, and, for example, in methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or neopentyl. is there. Alkyl groups are properly C₁From C₆Alkyl group, but preferably C₁-C₄Alkyl, more preferably C₁-C₂It is an alkyl group.

The alkenyl and alkynyl moieties may be in the form of straight chains or branched chains, which may be in (E) -configuration or (Z) -configuration, as required. May be. Examples are vinyl, allyl and propargyl. The alkenyl and alkynyl moieties may contain one or more double and / or triple bonds in any combination. Alenyl and alkylinyl alkenyl are understood to be included in these terms.

Halogen is fluorine, chlorine, bromine or iodine.

A haloalkyl group is an alkyl group substituted with one or more of the same or different halogen atoms, and, for example, CF.₃, CF₂CI, CF₂H, CCI₂H, FCH₂, CICH₂, BrCH₂, CH₃CHF, (CH₃)₂CF, CF₃CH₂Or CHF₂CH₂Is.

In the context of this specification, the term "aryl" preferably refers to phenyl and naphthyl. The term "heteroaryl" refers to an aromatic ring system containing at least one heteroatom and consisting of either a single ring or two or more fused rings. Preferably, the monocycle contains up to 3 heteroatoms preferably selected from nitrogen, oxygen and sulfur, and up to 4 bicyclic systems. Examples of such groups are frills, thienyl, pyrrolyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4. -Oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl , Pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzoisofuryl, benzothienyl, benzoisothienyl, indrill, isoindrill, Indazolyl, benzothiazolyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, benzoimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthylidine, benzotriazil Nyl, prynyl, pteridinyl and indolidinyl can be mentioned. Preferred examples of complex aromatic groups include pyridyl, pyrimidinyl, triazinyl, thienyl, frills, oxazolyl, isooxazolyl, 2,1,3-benzoxadiazolyl and thiazolyl.

Preferred cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Cycloalkylalkyl is preferably cyclopropylmethyl. Cycloalkenyl includes cyclopentenyl and cyclohexenyl.

Carbon ring, eg R⁷, R⁸, R⁹And R¹⁰The ring formed with any two of the two is selected from O, S and N, which results in heterocycles such as 1,3-dioxolane, oxetane, tetrahydrofuran, morpholine, thiomorpholine and piperazine. Examples thereof include cycloalkyl and cycloalkenyl having up to 7 atoms, preferably containing 1 or 2 heteroatoms as described above.

Any substituent on aryl, heteroaryl, cycloalkyl or heterocyclyl, if present, is independent of halogen, nitro, cyano, rhodano, isothiocyanato, C._1-6Alkyl, C_1-6Haloalkyl, C_1-6Alkoxy-(C_1-6) Alkyl, C_2-6Alkenyl, C_2-6Haloalkenyl, C_2-6Alkyne, C_3-7Cycloalkyl (which itself may be C_1-6Substituted with alkyl or halogen. ), C_5-7Cycloalkenyl (which itself may be C_1-6Substituted with alkyl or halogen. ), Hydroxy, C_1-10Alkoxy, C_1-10Alkoxy (C_1-10) Alkoxy, tri (C)_1-4) Alkylsilyl (C_1-6) Alkoxy, C_1-8Alkoxycarbonyl (C_1-10) Alkoxy, C_1-10Haloalkoxy, aryl (C_1-4) Alkoxy (where this aryl group is optionally halogen or C_1-6Substituted with alkyl. ), C_3-7Cycloalkyloxy (where this cycloalkyl group is optionally C_1-6Substituted with alkyl or halogen. ), C_3-10Alkenyloxy, C_3-10Alkynyloxy, Mercapto, C_1-10Alkylthio, C_1-10Haloalkylthio, aryl (C_1-4) Alkylthio, C_3-7Cycloalkylthio (where this cycloalkyl group is optionally C_1-6Substituted with alkyl or halogen. ), Tori (C_1-4)-Alkylsilyl (C_1-6)-Alkylthio, arylthio, C_1-6Alkylsulfonyl, C_1-6Haloalkylsulfonyl, C_1-6Alkyl sulfinyl, C_1-6Haloalkylsulfinyl, arylsulfonyl, tri (C)_1-4) Alkylsilyl, aryldi (C)_1-4)-Alkylsilyl, (C_1-4) Alkyldiarylsilyl, triarylsilyl, C_1-10Alkylcarbonyl, HO₂C, C_1-10Alkoxycarbonyl, aminocarbonyl, C_1-6Alkylaminocarbonyl, di (C_1-6Alkyl) -aminocarbonyl, N- (C_1-3Alkyl) -N- (C_1-3Alkoxy) aminocarbonyl, C_1-6Alkylcarbonyloxy, arylcarbonyloxy, di (C)_1-6) Alkylamino-carbonyloxy, aryl (which itself may be C)_1-6Substituted with alkyl or halogen. ), Heteroaryl (which itself may be C_1-6Substituted with alkyl or halogen. ), Heterocyclyl (which itself may be C)_1-6Substituted with alkyl or halogen. ), Aryloxy (where this aryl group is optionally C_1-6Substituted with alkyl or halogen. ), Heteroaryloxy (where this heteroaryl group is optionally C_1-6Substituted with alkyl or halogen. ), Heterocyclyloxy (where this heterocyclyl group is optionally C_1-6Substituted with alkyl or halogen. ), Amino, C_1-6Alkylamino, di (C_1-6) Alkylamino, C_1-6Alkylcarbonylamino, N- (C_1-6) Alkylcarbonyl-N- (C_1-6) Alkylamino, arylcarbonyl, (where this aryl group is itself optionally halogen or C_1-6Substituted with alkyl. ), Or two adjacent positions on an aryl or heteroaryl system are cyclized and are themselves halogen or C._1-6It can form 5-membered, 6- or 7-membered carbocycles or heterocycles, optionally substituted with alkyl. As a further substituent of aryl or heteroaryl, arylcarbonylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ), (C_1-6) Alkoxycarbonylamino (C)_1-6) Alkoxycarbonyl-N- (C_1-6) Alkylamino, aryloxycarbonylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ), Aryloxycarbonyl-N- (C_1-6) Alkylamino, (where this aryl group is C_1-6Substituted with alkyl or halogen. ), Arylsulfonylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ), Arylsulfonyl-N- (C_1-6) Alkylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ), Aryl-N- (C_1-6) Alkylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ), Arylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ), Heteroarylamino (where this heteroaryl group is C_1-6Substituted with alkyl or halogen. ), Heterocyclylamino (where this heterocyclyl group is C_1-6Substituted with alkyl or halogen. ), Aminocarbonylamino, C_1-6Alkylaminocarbonylamino, di (C)_1-6) Alkylaminocarbonylamino, arylaminocarbonylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ), Aryl-N- (C_1-6) Alkylamino-carbonylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ), C_1-6Alkylaminocarbonyl-N- (C_1-6) Alkylamino, di (C)_1-6) Alkylaminocarbonyl-N- (C_1-6) Alkylamino, arylaminocarbonyl-N- (C_1-6) Alkylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ) And aryl-N- (C_1-6) Alkylaminocarbonyl-N- (C_1-6) Alkylamino (where this aryl group is C_1-6Substituted with alkyl or halogen. ).

For substituted aryl moieties, heterocyclyls and heteroaryl groups, one or more substituents are independent, halogen, specifically chloro, cyano, C._1-6Alkyl, C_1-6Haloalkyl, C_1-6Alkoxy, C_1-6Haloalkoxy, C_1-6Alkylthio, C_1-6Alkyl sulfinyl, C_1-6It is particularly preferred to be selected from alkylsulfonyls, nitros and cyanos. Dialkyl substituents include dialkyl groups that together with the bonded N atom form a 5-, 6- or 7-membered heterocycle, which ring is selected from O, N or S1 It may contain one or two additional heteroatoms, and one or two are independently selected (C)._1-6) It is optionally substituted with an alkyl group. If a heterocycle is formed by linking two groups on an N atom, the resulting rings are appropriately pyrrolidine, piperidine, thiomorpholine and morpholine, each of which is one or two independent. Is selected (C_1-6) It may be substituted with an alkyl group.

The present invention also relates to salts in which a compound of formula I can be formed with amines, alkali metals and alkaline earth metal bases or quaternary ammonium bases.

Of the alkali metal and alkaline earth metal hydroxides as salt formations, hydroxides of lithium, sodium, potassium, magnesium and calcium should be mentioned in particular, but sodium hydroxide and potassium hydroxide in particular. Is. The compounds of formula I according to the invention also include hydrates that can be formed during salt formation.

Examples of amines suitable for ammonium salt formation are ammonia and primary, secondary and tertiary C.₁-C₁₈Alkylamine, C₁-C₄Hydroxyalkylamine and C₂-C₄Alkoxyalkylamines such as methylamine, ethylamine, n-propylamine, isopropylamine, four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecyl. Amine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctyl. Amines, dimethylamines, diethylamines, di-n-propylamines, diisopropylamines, di-n-butylamines, di-n-amylamines, diisoamylamines, dihexylamines, diheptylamines, dioctylamines, ethanolamines, n-propanolamines. , Isopropanolamine, N, N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-but-2-enylamine, n-pent-2-enylamine, 2,3-dimethylbut-2-enylamine , Dibut-2-enylamine, n-hex-2-enylamine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri -n-Amilamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indolin, quinuclidine and azepine; primary arylamines such as aniline, methoxyaniline, ethoxyaniline, o-, m- and p-toluidine, phenylenediamine, benzidine, naphthylamine and o-, m- and p-chloroaniline;However, in particular, triethylamine, isopropylamine and diisopropylamine can be mentioned.

A preferred quaternary ammonium base suitable for salt formation is, for example, the formula [N (R)._aR_{b b}R_cR_d)] OH (R here_a, R_{b b}, R_cAnd R_dEach other C₁-C₄Corresponds to alkyl. ) Corresponds to. More suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reaction.

The protecting group G has been selected so that it can be removed by one or a combination of biochemical, chemical or physical processes to give the compound of formula I, where G is. H before, during or after application to the treated area or plant. Examples of these processes include enzymatic cleavage, chemical hydrolysis and photolysis. Compounds carrying such a group G have certain advantages, such as improved permeation of cuticles in treated plants, increased crop resistance, other herbicides, herbicide palliatives, plant growth regulators, fungicides. Alternatively, it may result in improved compatibility or stability in a formulated mixture containing an insecticide, or reduced leachate in the soil.

Substituents G, R¹R², R³, R⁴, R⁵, R⁶, R⁷And R⁸Depending on the nature of, the compounds of formula I may exist in different isomer forms. If G is hydrogen, for example, the compounds of formula I may exist in different tautomeric forms. Also, if the substituent contains a double bond, cis and trans isomers may be present. The present invention includes all such isomers and tautomers and mixtures thereof in all and / or proportions. These isomers are also within the claims of Formula I.

The preferred group of compounds of formula I is R¹Is methyl, ethyl, vinyl, ethynyl, cyclopropyl, difluoromethoxy or trifluoromethoxy. More preferably, R¹Is methyl or ethyl.

Preferably R²And R³Are independent of each other, hydrogen, optionally substituted phenyl, optionally substituted naphthyl or optionally substituted heteroaryl. More preferably, R²And R³Are independent of each other, hydrogen, phenyl or phenyl (C)₁-C₂Alkyl, C₁-C₂Haloalkyl, C₁-C₂Alkoxy, C₁-C₂Substituted with haloalkoxy, fluoro, chloro, bromo or cyano. ), Heteroaryl or Heteroaryl (C₁-C₂Alkyl, C₁-C₂Haloalkyl, C₁-C₂Alkoxy, C₁-C₂Substituted with haloalkoxy, fluoro, chloro, bromo or cyano. ).

Especially R²Is hydrogen, and R³Is phenyl or phenyl (C₁-C₂Alkyl, C₁-C₂Haloalkyl, C₁-C₂Alkoxy, C₁-C₂Substituted with haloalkoxy, fluoro, chloro, bromo or cyano. ) Or R²Is phenyl or phenyl (C₁-C₂Alkyl, C₁-C₂Haloalkyl, C₁-C₂Alkoxy, C₁-C₂Substituted with haloalkoxy, fluoro, chloro, bromo or cyano), and R³Is preferably hydrogen.

Phenyl group R is preferred²And R³It is a group substituted with fluoro, chloro, bromo at the 4-position, particularly with fluoro or chloro.

Preferably R⁴Is hydrogen, methyl, ethyl, vinyl or ethynyl. More preferably, R⁴Is hydrogen, methyl or ethyl.

In the preferred compound of formula I, R⁵And R¹²Are independent of each other, hydrogen or C₁-C₃Alkyl, more preferably R⁵And R¹²Is hydrogen.

Preferably, in the compound of formula I, R⁶And R¹¹Are independent of each other, hydrogen, halogen, formyl, cyano or nitro, or R⁶And R¹¹Are independent of each other, C₁-C₆Alkyl, C₂-C₆Alkenyl, C₂-C₆Alkyne, C₁-C₆Alkoxy, C₃-C₇Cycloalkyl, C₃-C₇Cycloalkenyl, phenyl, heteroaryl or 3- to 7-membered heterocyclyl, all of which are optionally substituted or substituted. R⁶And R¹¹Are independent of each other, the base COR¹³, CO₂R¹⁴Or CONR¹⁵R¹⁸, CR¹⁷= NOR¹⁸, CR¹⁸= NNR²⁰R²¹, NHR²², NR²²R²³Or OR²⁴And here R¹³Is C₁-C₆Alkyl, C₂-C₆Alkenyl, C₂-C₆Alkyne, C₃-C₇Cycloalkyl, C₅-C₇Cycloalkenyl, phenyl, heteroaryl or 3- to 7-membered heterocyclyls, where all of these substituents are optionally substituted. R¹⁴Is hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₅-C₇Cycloalkenyl, phenyl, heteroaryl, or 3- to 7-membered heterocyclyl, where all of these substituents are optionally substituted. R¹⁵Is hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₅-C₇Cycloalkenyl, phenyl, heteroaryl or 3- to 7-membered heterocyclyls, where all of these substituents are optionally substituted. R¹⁶Is hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₁-C₆Alkoxy, C₁-C₆Haloalkoxy, C₃-C₇Cycloalkyl, C₅-C₇Cycloalkenyl, C₁-C₆Alkylsulfonyl, Phenylsulfonyl, Heteroarylsulfonyl, Amino, C₁-C₆Alkylamino, di C₁-C₆Alkylamino, phenyl, heteroaryl or 3- to 7-membered heterocyclyls, where all of these substituents are optionally substituted or R¹⁵And R¹⁶May together form a optionally substituted 3- to 7-membered ring containing oxygen, sulfur or nitrogen atoms. R¹⁷And R¹⁹Are independent of each other, hydrogen, C₁-C₃Alkyl or C₃-C₆Cycloalkyl, R¹⁸, R²⁰And R²¹Are independent of each other, hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₁-C₆Alkylcarbonyl, C₁-C₆Alkoxycarbonyl, C₁-C₆Alkylthiocarbonyl, aminocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, phenyl or heteroaryl, where all of these substituents are optionally substituted, R²²Is C₁-C₆Alkylcarbonyl, C₁-C₆Alkoxycarbonyl, C₁-C₆Alkylthiocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, C₁-C₆Alkylsulfonyl, phenylcarbonyl, phenoxycarbonyl, phenylaminocarbonyl, phenylthiocarbonyl, phenylsulfonyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl, heteroarylthiocarbonyl or heteroarylsulfonyl, where these are substituted. All of the groups have been optionally replaced and R²³Is C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₁-C₆Alkylcarbonyl, C₁-C₈Alkoxycarbonyl, C₁-C₆Alkylthiocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, C₁-C₆Alkylsulfonyl, phenyl or heteroaryl, where all of these substituents are optionally substituted or R²²And R²³Together form a optionally substituted 3- to 7-membered ring containing an oxygen, sulfur or nitrogen atom, where all of these substituents are optionally substituted, as well as R²⁴Is C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₁-C₆Alkylcarbonyl, C₁-C₆Alkoxycarbonyl, C₁-C₆Alkylthiocarbonyl, aminocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, C₁-C₆Alkylsulfonyl, tri (C₁-C₆Alkyl) silyl, phenyl or heteroaryl, where all of these substituents are optionally substituted.

More preferably, R⁶And R¹¹Are independent of each other, hydrogen, halogen, cyano, and optionally substituted C₁-C₆Alkyl or group COR¹³, CO₂R¹⁴Or CONR¹⁵R¹⁶, CR¹⁷= NOR¹⁸Or CR¹⁹= NNR²⁰R²¹And here R¹³, R¹⁴, R¹⁵And R¹⁶Is C₁-C₆Alkyl R¹⁷And R¹⁹Is hydrogen or C₁-C₃Alkyl R¹⁸Is C₁-C₃Alkyl and as well R²⁰And R²¹Are independent of each other, hydrogen or C₁-C₃Alkyl and here R⁶And R¹¹Are independent of each other, hydrogen, methyl or methyl (C)₁-C₃Replaced by alkoxy. ) Is particularly preferable.

A compound of formula I, R⁷, R⁸, R⁹And R¹⁰Are independent of each other, hydrogen, halogen, hydroxyl, formyl, amino, cyano or nitro, or R⁷, R⁸, R⁹And R¹⁰Are independent of each other, C₁-C₆Alkyl, C₂-C₆Alkenyl, C₂-C₆Alkyne, C₁-C₆Alkoxy, C₁-C₆Alkylthio, C₁-C₆Alkyl sulfinyl, C₁-C₆Alkylsulfonyl, C₃-C₇Cycloalkyl, C₄-C₇Cycloalkenyl, tri (C₁-C₆Alkyl) silyl, phenyl, heteroaryl or 3- to 7-membered heterocyclyls, where all of these substituents are optionally substituted or R⁷, R⁸, R⁹And R¹⁰Are independent of each other, and the base COR¹³, CO₂R¹⁴Or CONR¹⁵R¹⁶, CR¹⁷= NOR¹⁸, CR¹⁹= NNR²⁰R²¹, NR²²R²³Or OR²⁴And here R¹³Is C₁-C₆Alkyl, C₂-C₆Alkenyl, C₂-C₆Alkyne, C₃-C₇Cycloalkyl, C₅-C₇Cycloalkenyl, phenyl, heteroaryl or 3- to 7-membered heterocyclyls, where all of these substituents are optionally substituted, R¹⁴Is hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₅-C₇Cycloalkenyl, phenyl, heteroaryl, or 3- to 7-membered heterocyclyl, where all of these substituents are optionally substituted. R¹⁵Is hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₁-C₆Alkoxy, C₁-C₆Alkoxy, C₁-C₆Haloalkoxy, C₃-C₇Cycloalkyl, C₅-C₇Cycloalkenyl, phenyl, heteroaryl or 3- to 7-membered heterocyclyls, where all of these substituents are optionally substituted, R¹⁶Is hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₁-C₆Alkoxy, C₁-C₆Haloalkoxy, C₃-C₇Cycloalkyl, C₅-C₇Cycloalkenyl, C₁-C₆Alkylsulfonyl, amino, C₁-C₆Alkylamino, di C₁-C₆Alkylamino, phenyl, heteroaryl or 3- to 7-membered heterocyclyls, where all of these substituents are optionally substituted or R¹⁵And R¹⁶May together form a optionally substituted 3- to 7-membered ring containing oxygen, sulfur or nitrogen atoms. R¹⁷And R¹⁹Are independent of each other, hydrogen, C₁-C₃Alkyl or C₃-C₆Cycloalkyl, R¹⁸, R²⁰And R²¹Are independent of each other, hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₁-C₆Alkylcarbonyl, C₁-C₆Alkoxycarbonyl, C₁-C₆Alkylthiocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, phenyl or heteroaryl, where all of these substituents are optionally substituted, R²²And R²³Are independent of each other, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₁-C₆Alkylcarbonyl, C₁-C₆Alkoxycarbonyl, C₁-C₆Alkylthiocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, C₁-C₆Alkylsulfonyl, phenyl or heteroaryl, or R²²And R²³Together, they may form optionally substituted 3- to 7-membered rings, optionally containing oxygen, sulfur or nitrogen atoms, where all of these substituents are optionally substituted. , And R²⁴Is C₃-C₆Alkenyl, C₃-C₆Alkyne, C₃-C₇Cycloalkyl, C₁-C₆Alkylcarbonyl, C₁-C₆Alkoxycarbonyl, C₁-C₆Alkylthiocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, C₁-C₆Alkylsulfonyl, tri (C₁-C₆Compounds such as alkyl) silyl, phenyl or heteroaryl, wherein all of these substituents are optionally substituted, are preferred.

More preferably, R⁷, R⁸, R⁹And R¹⁰Are independent of each other, hydrogen, cyano, C₁-C₆Alkyl, C₂-C₆Alkenyl, C₁-C₆Alkoxy, C₁-C₆Alkoxy C₁-C₆Alkyl, 3-7 member heterocyclyl or CR¹⁷= NOR¹⁸And here R¹⁷Is hydrogen or C₁-C₃Alkyl and as well R¹⁸Is C₁-C₃It is alkyl.

R⁷, R⁸, R⁹And R¹⁰Are independent of each other, hydrogen, C₁-C₆Alkyl, C₂-C₆Alkenyl, C₁-C₆Alkoxy or C₁-C₆Alkoxy C₁-C₆Alkyl is particularly preferred.

In the preferred compound group of the compound of formula I, R⁷And R⁸Together to form the unit = O, or the unit = CR²⁵R²⁶Or unit = NR²⁷Or together with the carbon atoms to which they bond to form a 3- to 8-membered ring, optionally containing a heteroatom selected from O, S or N, and optionally C₁-C₃Alkyl, C₁-C₃Alkoxy, C₁-C₃Alkylthio, C₁-C₃Alkyl sulfinyl, C₁-C₃Alkylsulfonyl, C₁-C₃Haloalkyl, halogen, phenyl, phenyl (C₁-C₄Alkyl, C₁-C₄Haloalkyl, C₁-C₄Alkoxy, C₁-C₄Haloalkoxy, C₁-C₄Alkylthio, C₁-C₄Alkyl sulfinyl, C₁-C₄Alkylsulfonyl, C₁-C₄Alkylcarbonyl, C₁-C₄Alkoxycarbonyl, aminocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Substituted by alkylaminocarbonyl, halogen, cyano. ) Or by nitro, heteroaryl or heteroaryl (C)₁-C₄Alkyl, C₁-C₄Haloalkyl, C₁-C₄Alkoxy, C₁-C₄Haloalkoxy, C₁-C₄Alkylthio, C₁-C₄Alkyl sulfinyl, C_1-C₄Alkylsulfonyl, C₁-C₄Substituted by alkylcarbonyl, halogen, cyano. ) Or by nitro, where R²⁵And R²⁶Are independent of each other, hydrogen, halogen, cyano or nitro, or R²⁵And R²⁶Are independent of each other, C₁-C₆Alkyl, C_1-C₆Alkoxy, C₁-C₆Alkylamino, di C₁-C₆Alkylamino, C₁-C₆Alkylcarbonyl, C₁-C₆Alkoxycarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, N-Phenyl-NC₁-C₆Alkylaminocarbonyl, N-Phenyl C₁-C₆Alkyl-NC_1-C₆Alkylaminocarbonyl, N-heteroaryl-NC₁-C₆Alkylaminocarbonyl, N-heteroaryl C₁-C₆Alkyl-NC₁-C₆Alkylaminocarbonyl, phenyl, heteroaryl, C₃-C₈Cycloalkyl or 3- to 7-membered heterocyclyl, where all of these substituents are optionally substituted or R²⁵And R²⁶Can together form a 5- to 8-membered ring, optionally containing a heteroatom selected from O, S or N, and optionally C₁-C₂Alkyl or C₁-C₂Substituted with alkoxy, R²⁷Is nitro or cyano, or R²⁷Is C₁-C₆Alkylamino, di C₁-C₆Alkylamino, C₁-C₆Alkoxy, C₃-C₆Alkenyloxy, C₃-C₆Alkynyloxy, phenoxy, phenylamino, N-phenyl-NC₁-C₆Alkylamino, N-Phenyl C₁-C₆Alkyl-NC₁-C₆Alkylamino heteroaryloxy, heteroarylamino, N-heteroaryl-NC₁-C₆Alkylamino or N-heteroaryl C₁-C₆Alkyl-NC₁-C₆Alkylamino, here All of these substituents are optionally substituted, where R⁷And R⁸Together unit = O or = NR²⁷Form and here R²⁷Is C_1-3Alkoxy is particularly preferable.

A compound of formula I, R in the formula⁷And R¹⁰Together with the carbon atom to which it is bonded forms a saturated 3- to 4-membered ring, optionally O, S or NR.²⁸Contains heteroatoms or groups selected from, and optionally C₁-C₄Alkyl, C₁-C₄Alkoxy, C₁-C₄Alkylthio, halogen, C₁-C₄Alkylcarbonyl or C₁-C₄Alkoxycarbonyl substituted or R⁷And R¹⁰Together with the carbon atoms to which they are bonded form a 5- to 8-membered ring, optionally containing a heteroatom selected from O, S or N, and optionally C.₁-C₃Alkyl, C₁-C₃Alkoxy, C₁-C₃Alkylthio, C₁-C₃Alkyl sulfinyl, C₁-C₃Alkylsulfonyl, C₁-C₃Haloalkyl, halogen, phenyl, phenyl (C₁-C₄Alkyl, C₁-C₄Haloalkyl, C₁-C₄Alkoxy, C₁-C₄Haloalkoxy, C₁-C₄Alkylthio, C₁-C₄Alkyl sulfinyl, C₁-C₄Alkylsulfonyl, C₁-C₄Alkylcarbonyl, C₁-C₄Alkoxycarbonyl, aminocarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Substituted by alkylaminocarbonyl, halogen, cyano. ) Or nitro, heteroaryl or heteroaryl (C)₁-C₄Alkyl, C₁-C₄Haloalkyl, C₁-C₄Alkoxy, C₁-C₄Haloalkoxy, C₁-C₄Alkylthio, C₁-C₄Alkyl sulfinyl, C₁-C₄Alkylsulfonyl, C₁-C₄Substituted by alkylcarbonyl, halogen, cyano. ) Or replaced by nitro, or R⁷And R¹⁰Together to form a bond, where R²⁸Is hydrogen, C₁-C₆Alkyl, C₃-C₆Alkenyl, C₃-C₆Alkyne, C₁-C₆Alkoxy, C₁-C₆Alkylcarbonyl, C₁-C₆Alkoxycarbonyl, C₁-C₆Alkylaminocarbonyl, di C₁-C₆Alkylaminocarbonyl, Phenoxycarbonyl C₁-C₆Alkylsulfonyl, phenylsulfonyl or heteroaryloxycarbonyl, where all of these substituents are optionally substituted.

More preferably, R⁷And R¹⁰Together form a bond.

The compound of formula (I) is a known compound (see references cited on page 1). The process of preparation is described in this reference.

The following compounds are preferred compounds:

<chemistry num="3"><img id="000004" he="128" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /></chemistry><img id="000005" he="158" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" />

<tables num="1"><img id="000006" he="203" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /></tables><img id="000007" he="213" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000008" he="197" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000009" he="204" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000010" he="204" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000011" he="204" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000012" he="213" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000013" he="147" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" />

The compounds in Tables 1-192 below can be obtained in a similar manner.

Table 1 includes 378 T-1 type compounds.

<chemistry num="4"><img id="000014" he="40" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /></chemistry> In the formula, R¹Is methyl and R⁴Is hydrogen, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is specified in Table 1.

<tables num="2"><img id="000015" he="224" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /></tables><img id="000016" he="221" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000017" he="224" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000018" he="225" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000019" he="226" wi="158" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000020" he="231" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000021" he="227" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000022" he="228" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /><img id="000023" he="77" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" />

Table 2 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 3 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 4 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 5 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 6 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 7 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 8 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 9 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 10 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 11 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 12 contains 378 T-1 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 13 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 14 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 15 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 16 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 17 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 18 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 19 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 20 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 21 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 22 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 23 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 24 contains 378 T-1 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 25 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 26 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 27 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is ethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 28 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 29 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 30 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 31 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 32 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 33 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 34 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 35 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 36 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 37 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 38 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 39 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is ethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 40 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 41 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 42 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 43 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 44 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 45 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 46 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 47 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 48 contains 378 T-1 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 49 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 50 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 51 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 52 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 53 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 54 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 55 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 56 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 57 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 58 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 59 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 60 contains 378 T-1 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 61 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 62 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 63 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 64 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 65 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 66 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 67 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 68 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 69 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵, R⁸And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 70 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 71 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 72 contains 378 T-1 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 73 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 74 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 75 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 76 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 77 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 78 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 79 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 80 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 81 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 82 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 83 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 84 contains 378 T-1 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 85 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 86 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 87 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 88 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 89 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 90 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 91 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 92 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 93 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 94 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 95 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵, R⁶And R⁷Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 96 contains 378 T-1 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷, R⁸, R⁹, R¹⁰Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 97 includes 378 T-2 type compounds.

<chemistry num="5"><img id="000024" he="33" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

R in T-2¹Is methyl and R⁴Is hydrogen and R⁵, R⁶, R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 98 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 99 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 100 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 101 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 102 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 103 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 104 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 105 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 106 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 107 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 108 contains 378 T-2 type compounds, R in the formula.¹Is methyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸And R⁹Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 109 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵, R⁶, R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 110 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 111 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 112 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 113 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 114 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 115 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 116 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 117 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 118 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 119 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 120 contains 378 T-2 type compounds, R in the formula.¹Is ethyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁷And R⁹Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 121 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵, R⁶, R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 122 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is methyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 123 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is ethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 124 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 125 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁷, R⁸, R⁹, R¹⁰, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 126 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 127 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵And R⁶Is hydrogen and R⁸Is methyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 128 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵And R⁶Is hydrogen and R⁸Is ethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 129 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵And R⁶Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 130 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵And R⁶Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 131 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵And R⁶Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 132 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is methyl and R⁵Is hydrogen and R⁶Is methyl and R⁸And R⁹Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 133 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵, R⁶, R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 134 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is methyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 135 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is ethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 136 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 137 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 138 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 139 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵And R⁶Is hydrogen and R⁸Is methyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 140 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵And R⁶Is hydrogen and R⁸Is ethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 141 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵And R⁶Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 142 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵And R⁶Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 143 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵And R⁶And are hydrogen, R⁸Is methoxyethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 144 contains 378 T-2 type compounds, R in the formula.¹And R⁴Is ethyl and R⁵Is hydrogen and R⁶Is methyl and R⁸And R⁹Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 145 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵, R⁶, R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 146 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 147 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 148 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 149 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 150 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 151 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 152 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 153 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 154 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 155 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 156 contains 378 T-2 type compounds, R in the formula.¹Is difluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸And R⁹Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 157 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵, R⁶, R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1 .

Table 158 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 159 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 160 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 161 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 162 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 163 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 164 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 165 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 166 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 167 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 168 contains 378 T-2 type compounds, R in the formula.¹Is trifluoromethoxy and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸And R⁹Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 169 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵, R⁶, R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 170 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 171 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 172 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 173 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 174 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 175 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 176 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 177 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 178 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 179 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 180 contains 378 T-2 type compounds, R in the formula.¹Is cyclopropyl and R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸And R⁹Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 181 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵, R⁶, R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 182 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 183 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 184 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 185 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is ethoxymethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 186 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methoxyethyl and R⁸, R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 187 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 188 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 189 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 190 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is ethoxymethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 191 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵And R⁶Is hydrogen and R⁸Is methoxyethyl and R⁹, R¹¹And R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

Table 192 contains 378 T-2 type compounds, R in the formula.¹Is chlorine, R⁴Is hydrogen and R⁵Is hydrogen and R⁶Is methyl and R⁸And R⁹Is hydrogen and R¹¹Is methyl and R¹²Is hydrogen, as well as R²And R³Is as specified in Table 1.

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Preparation of P12 300 mg of Example T1 was introduced into 10 ml of dichloromethane, 0.34 ml of triethylamine was added, and then 0.09 ml of ethyl chloroformate was added dropwise. The mixture is stirred at room temperature for 30 minutes, then concentrated and the residue is chromatographed on silica gel using 7: 3 heptane / ethyl acetate as a solvent system. This yields 272 mg of product (75% of theoretical value).

The active compounds of the present invention, in combination with good plant resistance and favorable toxicity to warm-blooded animals, as well as being sufficiently resistant to the environment, to increase yields to protect plants and plant organs. In order to improve the quality of harvested materials, and in the protection of animal plagues (insects), specifically agriculture, gardening, livestock, forests, gardens and leisure facilities, stored products and materials, and sanitary areas. Suitable for managing insects, arachnids, parasitic worms, nematodes and soft animals encountered in. These can preferably be used as plant protection (epidemic prevention) agents. They are normally active against sensitive and resistant species, as well as against all or some stages of development. The above-mentioned plagues (pests) include: From the phylum Mollusk, for example, Lamellibranchiata, for example, Dreissena spp. (Dreissena spp.).

From the gastropod (class of the Gastropoda), for example, Arion spp., Biomphalaria spp., Bulinus spp., Deloceras spp., Galva spp. (Galba spp.), Limnaea spp. (Lymnaea spp.), Oncomelania spp. (Oncomelania spp.), Pomacea spp. (Pomacea spp.), Succinea spp. (Succinea spp.).

From the phylum Arthropoda, for example, Isopoda, such as Armadillidium vulgare, Oniscus asellus, Porcellio scaber.

From the arachnids (Arachnida), for example, Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp. .), Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Centruroy Death spp. (Centruroides spp), Corioptes spp. (Chorioptes spp.), Dermanyssus gallinae, Dermatophagoides pteronyssius, Dermatophagoides pteronyssius farinae), Dermacentor spp., Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp. .), Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus spp., Latrodectus spp. . (Loxosceles spp.), Metatetranychus spp. (Metatetranychus spp.), Nuhersa spp. (Nuphersa spp.), Oligonicus spp. (Oligonychus spp.), Ornithodoros spp. spp.), Ornithonyssus spp. (Ornithonyssus spp.), Panonychus spp. (Panonychus spp.), Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp. Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp. Tarsonemus spp.), Tetranychus spp. (Tetranychus spp.), Bayovis spp. (Vaejovis spp.), Vasates lycopersici.

From Symphyla, for example, Scutigerella spp.

From the order Centipede (Chilopoda), for example, Geophilus spp. (Geophilus spp.), Scutigera spp. (Scutigera spp.).

From Collembola, for example, Onychiurus armatus.

From the millipede (Diplopoda), for example, Blaniulus guttulatus.

From the order Zygentoma, for example, Lepisma saccharina, Thermobia domestica.

From Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Dichroplus spp., Glylotalpa spp. (Gryllotalpa spp.), Leucophaea maderae, Roxta spp. (Locusta spp.), Melanoplus spp., Periplaneta spp. -Gregaria (Schistocerca gregaria), Spella longipalpa (Supella longipalpa).

From termites (Dictyoptera), for example, Coptotermes spp. (Coptotermes spp.), Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Mirco Termes obesi, Odontotermes spp., Reticulitermes spp. (Reticulitermes spp.).

Heteroptera, such as Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Simex spp., Collaria spp., Clariades diltus. Creontiades dilutus), Dasynus piperis, Dicherops furcatus, Diconocoris hewetti, Disdercus spp. (Dysdercus spp.), Eusdercus spp. (Eurygaster spp.), Heliopeltis spp. (Heliopeltis spp.), Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Leptoglossus phyllopus, Riggs spp. Macropes excavatus, Milidae, Monalonion atratum, Nezara spp., Oebalus spp., Pentomidae, Pentomidae Quadrats (Piesma quadrats), Piezodorus spp. (Piezodorus spp.), Psallus spp. (Psallus spp.), Pseudacysta persea, Rodnius spp. singularis), Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.

From Psocodea (Anoplura (Phthiraptera)), for example, Damalinia spp., Haematopinus spp., Linognatus spp., Pediculus spp. (Pediculus spp.) spp.), Ptirus pubis, Trichodectes spp.

Homoptera, for example, Acyrthosipon spp., Acrogonia spp., Aeneolamia spp., Agonoscena spp., Agonoscena spp. spp. (Aleurodes spp.), Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Anuraphis cardui, Aoniziera spp. .), Aphanostigma piri, Aphis spp. (Aphis spp.), Arboridia apicalis, Aspidiella spp. (Aspidiella spp.), Aspidiotus spp. Atanus spp.), Aulacorthum solani, Bemisia spp. (Bemisia spp.), Brachycaudus helichrysii, Brachycolus spp. Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp. Chlorita onukii, Chromaphis juglandicola), Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp. (Coccus spp.), Cryptomyzus ribis Dalbulus spp.), Dialeurodes spp., Diaphorina spp., Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp. Dismicoccus spp. (Dysmicoccus spp.), Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus), Felicia spp. (Ferrisia spp.), Geococcus coffeae, Hieroglyphus, Homalodisca coagulata, Hyalopterus arunginis (Hyalopterus) spp.), Idiocerus spp. (Idiocerus spp.), Idioscopus spp. (Idioscopus spp.), Laodelphax striatellus, Lecanium spp. (Lecanium spp.), Lepidosaphes spp. Erisimi (Lipaphis erysimi), Macrosiphum spp. (Macrosiphum spp.), Mahanarva spp. (Mahanarva spp.), Melanaphis sacchari), Metcalfiella spp. (Metcalfiella spp.), Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Monelliopsis pecanis, Mizus spp. ribisnigri), Nephotettix spp. (Nephotettix spp.), Nilaparvata lugens, Oncometopia spp. spp.), Parlatoria spp. (Parlatoria spp.), Pemphigus spp. (Pemphigus spp.), Peregrinus maidis), Phenacoccus spp. (Phenacoccus spp.), Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. (Phylloxera spp.), Phylloxera spp. (Planococcus spp.), Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Pseudococcus spp., Psylla spp. (Pteromalus spp.), Pyrilla spp. (Pyrilla spp.), Quadraspidiotus spp., Quesada gigas, Rastrococcus spp. (Rastrococcus) spp.), Rhopalosiphum spp. (Rhopalosiphum spp.), Saissetia spp., Scaphoides titanus, Schizaphis graminum, Serena spidus ulticulatus art . (Sogata spp.), Sogatalla furcifera, Sogatodes spp. (Sogatodes spp.), Stictocephala festina, Tenalaphara malayensis, Tenalaphara malayensis, Tinalaphara malayensis ), Tomaspis spp. (Tomaspis spp.), Toxoptera spp. (Toxoptera spp.), Trialeurodes spp. (Trialeurodes spp.), Triosa spp. (Trioza) spp.), Tifrosiba spp. (Typhlocyba spp.), Unaspis spp. (Unaspis spp.), Viteus vitifolii, Zygina spp. (Zygina spp.).

From Coleoptera, for example, Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agelastica alni. (Agriotes spp.), Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp. (Anoplophora spp.), Ant spp.), Anthrenus spp. (Anthrenus spp.), Apion spp. (Apion spp.), Apogonia spp. spp.), Bruchidius obtectus, Bruchus spp., Cassida spp., Cerotoma trifurcata, Ceutorhynchus spp., Ceuthorhynchus spp. . (Chaetocnerna spp.), Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelitra zealandica, Setenicera spp. Curculio spp., Cryptorhynchus lapathi, Cylindrocopturus spp., Dermestes spp., Diabrotica spp. (Diabrotica spp.), Cryptorhynchus lapathi. spp.), Dichrocrocis spp. (Dichrocrocis spp.), Diloboderus spp. (Diloboderus spp.), Epilacuna spp. (Epilachna spp.), Epitrix spp. (Epitrix spp.), Faustinus spp. Gibbium psylloides, Hella undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes, Hylotrupes. Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Lema spp. (Lema spp.), Leptinotarsa decemlineata), Leucoptera spp. (Leucoptera spp.), Lissorhoptrus oryzophilus, Lixus spp. (Lixus spp.), Luperodes spp. (Megascelis spp.), Melanotus spp. (Melanotus spp.), Meligethes aeneus, Melolontha spp. (Melolontha spp.), Migdolus spp. (Migdolus spp.), Monocamus spp. (Monochamus spp.), Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis), Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetonia jucunda, Phaedon cochleariae, Phyadon cochleariae, phylofaga spp. spp.), Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., Psylliodes spp., Ptinus spp. Bentralis (Rhizobius ventralis), Rhizopertha dominica, Sitophilus spp. (Sitophilus spp.), Sphenophorus spp. (Sphenophorus) spp.), Stegobium paniceum, Sternechus spp., Symphyletes spp., Tanimecus spp., Tenebrio molitor, Tenebrio molitor (Tribolium spp.), Trogoderma spp. (Trogoderma spp.), Tychius spp. (Tychius spp.), Xylotrechus spp. (Xylotrechus spp.), Zabrus spp. (Zabrus spp.).

From Hymenoptera, for example, Acromyrmex spp., Atalia spp., Atta spp., Diprion spp. ), Hoplocampa spp., Lasius spp., Monomorium pharaonis, Solenopsis invicta, Tapinoma spp. (Tapinoma spp.), Vespa spp. spp.).

From Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp. (Alabama spp.), Amyelois transitella, Anarsia spp. (Anarsia spp.), Anticarsia spp. (Anticarsia spp.), Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Cacoecia spp. theivora), Capua reticulana, Carpocapsa pomonella, Carposina niponesis, Cheimatobia brumata, Kilo spp. (Chilo spp.), Codling moth spp. .), Clysia ambiguella, Cnaphalocerus spp., Cnaphalocerus spp., Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Conotrachelus spp. (Copitarsia spp.), Sidia spp. (Cydia spp.), Dalaca noctuides, Diaphania spp. (Diaphania spp.), Diatraea saccharalis), Aeris spp. (Earias spp.), Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Eldana saccharina, Efestia spp. Epinotia spp.), Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Eupoecilia ambiguella, Euproctis spp. . (Euxoa spp.), Feltia spp. (Feltia spp.), Galleria mellonella, Gracilaria spp. (Gracillaria spp.), Grapholitha spp. spp. (Hedylepta spp.), Helicoverpa spp. (Helicoverpa spp.), Heliothis spp. (Heliothis spp.), Hofmannophila pseudospretella, Homoeosoma spp. (Homoeosoma spp.), Homona spp. spp.), Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Laphygma spp. (Leucoptera spp.), Lithocolletis spp., Lithocolletis antennata, Lobesia spp., Loxagrotis albicosta), Lymantria spp. (Lymantria spp.), Lyonetia spp. (Lyonetia spp.), Malakosoma neustria, Maruca testulalis, Mamestra brassicae, Mamestra brassicae. Mocis spp.), Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrial spp. spp. (Ostrinia spp.), Oulema oryzae, Panoris flammea, Parnara spp. (Parnara spp.), Pectinophora spp. (Pectinophora spp.), Perileucoptera spp.), Phthorimaea spp. (Phthorimaea spp.), Phyllocnistis citrella, Phyllonorycter spp., Pieris spp. -Intel punk terra (Plodia interpunctella), Prucia spp. (Plusia spp.), Plutella xylotella, Price spp. (Prays spp.), Prodenia spp. (Prodenia spp.), Protoparce spp. .), Psedaletia spp. (Psedaletia spp.), Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp.), Scirpophaga spp. (Scirpophaga spp.), Scotia segetum, Sesamia spp. (Sesamia spp.), Sparganothis spp. Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Thermesia gemmatalis , Tineola bisselliella, Trichoplusia spp. (Tortrix spp.), Trichophaga tapetzella, Trichoplusia spp., Tuta absoluta), Virachola spp. (Virachola spp.).

From Diptera, for example, Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp., Asphondylia spp. .), Bactrocera spp. (Bactrocera spp.), Bibio hortulanus, Calliphora erythrocephala, Cerattis capitata, Cerattis capitata, Kironomas spp. (Chironomus spp.) spp.), Chrysops spp., Cochliomyia spp., Contalinia spp., Cordylobia anthropphaga, Crex spp. (Culex) spp.), Culicoides spp. (Culicoides spp.), Culicoides spp. (Culiseta spp.), Cuterebra spp., Dacus oleae, Decineura spp. (Dasyneura spp.), Delia spp. (Delia spp.), Dermatobia hominis, Drosphila spp., Echinocnemus spp., Fannia spp., Gasterophilus spp. ), Grossina spp., Haematopota spp., Hydrellia spp., Hylemyia spp., Hylemyia spp., Hypovosca spp. (Hypoderma spp.), Liriomyza spp. (Liriomyza) spp.), Lucilia spp. (Lucilia spp.), Lutzomia spp. (Lutzomia spp.), Mansonia spp. (Mansonia spp.), Musca spp. (Musca spp.), Nezara spp. spp. (Oestrus spp.), Ocinella frit, Pegomyia spp. (Pegomyia spp.), Frebotos spp. (Phlebotomus spp.), Forbia spp. (Phorbia spp.), Formia spp. (Phormia spp.) .), Prodiplosis spp. (Prodiplosis spp.), Psila rosae, Rogoletis spp. (Rhagoletis spp.), Sarcophaga spp. (Sarcophaga spp.), Simulium spp. (Stomoxys spp.), Tabanus spp. (Tabanus spp.), Tania spp. (Tannia) spp.), Tetanops spp. (Tetanops spp.), Tipula spp. (Tipula spp.).

From the order Thrips (Thysanoptera), for example, Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneotrips flavens flavens. (Frankliniella spp.), Heliotrips spp. (Heliothrips spp.), Hercinothrips femoralis, Ripiphorothrips cruentatus, Silttrips spp. (Scirtothrips spp.) . (Thrips spp.).

From Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp., Tunga penetrans, Xenopsylla cheop. ..

From the phylum phylums Plathelminthes and the phylum Nematoda as animal parasites, for example, Ancylostoma (Helminths), for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acrostoma Acylostoma braziliensis, Ancylostoma spp. (Ancylostoma spp.), Ascaris spp. (Ascaris spp.), Brugia malayi, Brugia timori, Bunostomum spp. spp.), Cabertia spp. (Chabertia spp.), Clonorchis spp. (Clonorchis spp.), Cooperia spp. (Cooperia spp.), Dicrocoelium spp. filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus granulosus, Echinococcus multilocularis, enterococcus vermicularis, enterococcus multilocularis Faciola spp. (Faciola spp.), Hemonchus spp. (Haemonchus spp.), Heterakis spp. (Heterakis spp.), Hymeno lepis nana, Histrongrass spp. (Loa Loa), Nematodirus spp. (Nematodirus spp.), Oesophagostomum spp. (Oesophagostomum spp.), Opisthorchis spp.), Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides fuelleborni Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis, Trichinella spiralis Trichinella britovi, Trichinella nelsoni, Trichinella Pseudospiralis pseudopsiralis), Trichostrongulus spp. (Trichostrongulus spp.), Trichuris trichuria, Wuchereria bancrofti.

From ascaris (phylum Nematoda) as plant pests, for example, Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp. (Ditylenchus spp.), Potato cyst nematode. spp. (Globodera spp.), Heterodera spp. (Heterodera spp.), Longidorus spp. (Longidorus spp.), Meloidogyne spp. ), Trichodoras spp. (Trichodorus spp.), Tylenchulus semipenetrans, Kiphenema spp. (Xiphinema spp.).

From the Protozoa submon, for example, Eimeria.

If desired, the compounds of the invention can be used at specific concentrations or rates, as herbicides, palliatives, growth regulators or agents to improve plant properties, or as fungicides (microbicides), for example. , As antifungals, fungicides, fungicides, herbicides (including agents against viroids), or as MLOs (Mycoplasma-like organisms) and RLOs (Rickettsia) -like organisms)) can be used as an agent. If desired, these compounds may also be used as intermediates or precursors for the synthesis of other active compounds.

All plants and parts of plants can be processed according to the present invention. Plants should be understood in the context of the present invention to mean all plants and plant populations, such as desired and undesired wild plants or crops, including naturally occurring crops. A crop is a plant that can be obtained by conventional plant breeding and optimal methods, or by biotechnology and genetic manipulation, or by a combination of these methods, including transgenic plants, and plant breeders. It may be a plant containing a plant-grown variety that can or cannot be protected by the rights of. The plant part should be understood to mean all parts and organs above and below the ground, such as buds, leaves, flowers and roots, for example leaves, needles. , Stalks, stems, flowers, seedlings, fruits, seeds, roots, lumps and rhizomes (underground stems). Plant parts also include harvests, as well as asexual and fertile growths, such as cut parts, tubers, rhizomes (rhizomes), side branches and seeds.

Treatment of plants and plant parts with active compounds according to the invention can be performed directly or by routine treatment methods of the compounds, eg, dipping, spraing, evaporation, fogging, scattering, painting, injecting. By, and in the case of breeds, specifically in the case of seeds, and also by applying one or more coatings, to be able to act on the surroundings, habitat or storage space. Do by.

Active compounds are conventional formulations such as solutions, emulsions, wettable powders, water and oil-based suspensions, powders, dust, pastes, soluble powders, soluble granules, powders for spraying, suspension-emulsion concentrates. , Natural products impregnated with active compounds, synthetics impregnated with active compounds, fertilizers and microcapsules in polymer materials.

These formulations are prepared in a known manner, for example, with an active compound and a bulking agent (which is a liquid solvent and / or a solid carrier), and optionally a surfactant (emulsifier and / or dispersant and / or foaming agent). Is produced by mixing by the use of.). This formulation is prepared in a suitable plant, or otherwise before or during application.

Suitable for use as an adjunct are certain properties of the composition itself and / or the preparations derived from it (eg, sprays, seed powder coatings), such as certain technical properties and / or certain organisms. It is a suitable substance to impart scientific properties as well. Typical suitable adjuncts are: bulking agents, solvents and carriers.

Suitable bulking agents are, for example, water, polar and non-polar organic chemical liquids, such as hydrocarbons in the aromatic and non-aromatic classifications (eg, paraffin, alkylbenzene, alkylnaphthalene, chlorobenzene), alcohols and polyols (eg, paraffin, alkylbenzene, alkylnaphthalene, chlorobenzene). It may be substituted, etherified and / or esterified, as required), ketones (eg, acetone, cyclohexanones), esters (including fats and oils) and (. Poly) ethers, unsubstituted and substituted amines, amides, lactams (eg, N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (eg, dimethylsulfoxides).

When the bulking agent used is water, for example, an organic solvent can be used as the bulking solvent. In essence, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalene, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons. Hydrogens such as cyclohexane or paraffins such as petroleum fractions, mineral oils and vegetable oils, alcohols such as butanol or glycols, and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, potent Also polar solvents such as dimethylsulfoxides, as well as water.

Suitable solid carriers include: For example, ammonium salts and soil natural minerals such as kaolin, clay, talc, chalk, quartz, attapulsite, montmorillonite, or diatomaceous soil, and soil synthetic minerals such as ultrafine silica, alumina and silicate; granules. Suitable solid carriers for are: for example, ground and split natural stones such as calcite (sulfates), marbles, pebbles, sea sulphates and dolomites (white cloud stones), and also the synthesis of inorganic and organic meals. Granules, as well as organic granules such as paper, litter, coconut shells, corn stalks and tobacco stems; suitable emulsifiers and / or foaming agents are: eg, nonionic and anionic emulsifiers, eg poly Oxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulfates, aryl sulfonic acids and also protein hydrolysates; suitable dispersants are, for example, alcohol-POE-. And / or-POP-ethers, acids and / or POP-POE esters, alkylaryls and / or POP-POE ethers, fats-and / or POP-POE adducts, POE- and / or POP-polyol derivatives, POE- And / or nonionic and / from the classification of POP-sorbitan-or-sugar adducts, alkyl or aryl sulfates, alkyl- or aryl sulfonates, and alkyl or aryl phosphates or corresponding PO ether adducts. Or it is an ionic substance. In addition, suitable oligo-or polymers such as those derived from vinyl monomers, acrylic acids, EO and / or PO can be used alone or in combination with, for example, (poly) alcohols or (poly) amines. It is also possible to use lignin and its sulfonic acid derivatives, unmodified and modified cellulose, aromatic and / or aliphatic sulfonic acids and their adducts with formaldehyde.

Adhesive agents such as carboxymethyl cellulose and natural and synthetic polymers are in the form of powders, granules or latexes such as Arabic rubber, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin. Also synthetic phospholipids can be used in this formulation.

Colorants such as inorganic dyes such as iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes, and metallic phthalocyanine dyes, and micronutrients such as iron, magnesium, It is possible to use salts of boron, copper, cobalt molybdenum and zinc.

Other possible additives are perfumes, mineral oils or vegetable oils, optionally modified oils, waxes and nutrients (including micronutrients), such as iron, magnesium, boron, copper, cobalt molybdenum and zinc salts. Is.

Stabilizers, such as cold stabilizers, preservatives, antioxidants, light stabilizers, or other agents that improve chemical and / or physical stability may also be present.

This formulation generally contains 0.01% to 98% by weight of active compound, preferably 0.5% to 90%.

The active compounds according to the present invention are in this commercially available formulation and in the form of use prepared from these formulations, other active compounds such as insecticides, attractants, fungicides, bactericides, acaricides. It may be used as an agent, an anti-nematode agent, an antifungal agent, a growth regulator, a herbicide, a toxicity mitigating agent, a fertilizer or a mixture with an information substance.

Mixtures with other known active compounds such as herbicides, fertilizers, growth regulators, toxicity mitigators, semiochemicals and otherwise agents that improve plant properties can also be used.

When used as an insecticide, the active compound according to the invention may also be present in commercial formulations and in the form of use prepared from these formulations as a mixture with synergists. The synergistic agent is a compound that increases the action of the active compound, and the synergistic agent to be added does not have to be active in itself.

When used as an insecticide, the active compounds according to the invention are further in use in commercial formulations and in the form prepared from these formulations, in the plant environment, on the surface of plant parts, or in plant tissues. It may be present as a mixture with an inhibitor that reduces the degradation of this active compound after use in.

The content of this active compound in use, prepared from a commercially available formulation, can vary over a wide range. The active compound concentration of this use type can be 0.00000001% by weight to 95% by weight, preferably 0.00001% by weight to 1% by weight of the active compound.

The active compound is used in a conventional manner suitable for the type of use.

The active compounds according to the invention are not only against plant, hygiene and storage pests, but also animal pests (ectoparasites and endoparasites), such as caterpillars, soft mites, mange mites, leaves. It is also useful in the veterinary department for mites (leaf mites), flies (biting and licking), parasitic fly larvae, squirrels, hair blemishes, feather lice and fleas. These parasites include: From the louse (Anoplurida), for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp. Solenopotes spp.).

From Mallophagida and Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Torrington spp. ), Bovicola spp., Verneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. (Felicola spp.).

From Diptera and Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp. , Simulium spp. (Simulium spp.), Eusimulium spp. (Eusimulium spp.), Ferrebotomus spp. (Phlebotomus spp.), Lutzomyia spp. (Lutzomyia spp.), Culicoides spp. (Chrysops spp.), Hibomitra spp. (Hybomitra spp.), Atylotus spp. (Atylotus spp.), Tabanas spp. (Tabanus spp.), Haematopota spp. , Braula spp. (Braula spp.), Musca spp. (Musca) spp.), Hydrotaea spp. (Hydrotaea spp.), Stomoxys spp. (Stomoxys spp.), Haematobia spp. (Haematobia spp.), Morellia spp. (Morellia spp.), Fannia spp. spp. (Glossina spp.), Caliphora spp. (Calliphora spp.), Lucilia spp. (Lucilia spp.), Chrysomyia spp. Sarcophaga spp.), Oestrus spp. (Oestrus spp.), Hippoderma spp. (Hypoderma spp.), Gasterophilus spp. , Melophagus spp. (Melophagus spp.).

From the flea eyes (Siphonapterida), for example, Plex spp. (Pulex spp.), St. cephalides spp. (Ctenocephalides spp.), Xenopsylla spp. (Xenopsylla spp.), Seratophyllus spp. (Ceratophyllus spp.).

From the order Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the cockroaches (Blattarida), for example, Blatta orientalis, Periplaneta americana, Blattela germanica, Spella spp. (Supella spp.).

From the suborders Acari (Acarina), as well as the suborders Metastigmata and Mesostigmata, for example, Argas spp., Ornithodorus spp., Ornithodorus spp. ( Otobius spp.), Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp. .), Hyaloma spp. (Hyalomma spp.), Lipicephalus spp. (Rhipicephalus spp), Dermanyssus spp., Raillietia spp., Pneumonyssus spp. (Sternostoma spp.), Baroa spp. (Varroa) spp.).

From Actinedida (Prostigmata) and Astigmatina (Acaridida (Astigmata)), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp. , Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. . (Acarus spp.), Tyrophagus spp. (Tyrophagus spp.), Caloglyphus spp., Hypodectes spp., Pterolichus spp. ), Corioptes spp. (Chorioptes) spp.), Otodectes spp. (Otodectes spp.), Sarcoptes spp. (Sarcoptes spp.), Notoe dress spp. (Notoedres spp.), Knemidocoptes spp. spp. (Laminosioptes spp.).

The active compound of formula (I) according to the invention also comprises other pets such as agricultural livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens, beetles, ducks, geese and bees. Suitable for controlling, for example, dogs, cats, pet birds and aquarium fish, and also phalanx animals that flock to so-called research animals such as hamsters, guinea pigs, rats and mice. By managing these arthropods, reductions in deaths and production (eg meat, milk, wool, leather, eggs, honey, etc.) should be reduced, resulting in more economic and easier Animal husbandry is possible by the use of active compounds according to the invention.

The active compounds according to the invention are in the form of tablets, capsules, potions, drenchs, granules, pastes, boluses, feed-through processes and suppositories in known methods by intestinal administration in the veterinary department and in animal livestock. By parenteral administration, eg, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), by implant, nasal administration, eg, transdermal use, spray, pouring in the form of immersion or basing. And used by spotting, cleaning and powdering, and also as an aid to moldings containing active compounds, such as collars, ear tags, tail markers, leg bands, end ropes, marking instruments, etc.

When used in cattle, poultry, pets, etc., the compound of formula (I) may be directly or from 100 as a formulation containing the active compound in an amount of 1-80% by weight (eg, powder, emulsion, free-flowing composition). It may be used as a 10000-fold dilution, or it may be used as a medicinal bath.

The compounds according to the invention have also been further found to have strong insecticidal activity against insects that destroy industrial materials.

The following insects are, but are not limited to, examples and preferred: Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Xestobium rufovillosum, Petitrinus petilius pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus planicollis, Lyctus planicollis ), Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis), Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sino Sinoxylon spec.), Dinoderus minutus; Hymenopterons, such as Sileks juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur; Termites, such as Karotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes flavipes, santonensis), Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; Bristletails, such as Lepisma saccharina.

Industrial materials in the present invention mean non-living materials such as plastics, adhesives, glue sizes, paper and cardboard, leather, wood and processed wood products and coating compositions. It should be understood to do.

Ready-to-use compositions may optionally include additional pesticides and optionally one or more antifungal agents.

For possible additional additives, the pesticides and antifungal agents mentioned above can be referred to.

The compounds according to the invention may also be used to protect objects that come into contact with seawater or brackish water, such as hulls, shields, nets, buildings, mooring rigging and signaling systems, against deposits. Good.

In addition, the compounds according to the invention may be used alone or in combination with other active compounds as antifouling (adhesion-preventing) agents.

In home, hygiene and storage protection, active compounds are also found in animal pests, specifically in enclosed spaces such as homes, factory halls, offices, vehicle cabins, etc. , Suitable for managing arachnids and mites. They may be used alone or in combination with other active compounds and auxiliaries in household insecticide products for controlling these pests. They are active against sensitive and resistant species, as well as against all stages of development. These pests include: From the Scorpion idea, for example, Buthus occitanus.

From the ticks (Acarina), for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus. , Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula alfreddugesi, Neutrombicula autumnalis, Neutrombicula autumnalis (Dermatophagoides forinae).

From the spider order (Araneae), for example, Aviculariidae, Araneidae.

From the order Harvestmen (Opiliones), for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiriones phalangium.

From the Isopoda, for example, Oniscus asellus, Porcellio scaber.

From the millipede (Diplopoda), for example, Blaniulus guttulatus, Polydesmus spp. (Polydesmus spp.).

From the centipede (Chilopoda), for example, Geophilus spp. (Geophilus spp.).

From the order Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.

From the cockroaches (Blattaria), for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp. , Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Periplaneta fuliginosa (Supella longipalpa).

From the order Orthoptera (Saltatoria), for example, Acheta domesticus.

From Earwigs (Dermaptera), for example, Forficula auricularia.

From the order Dictyoptera (Isoptera), for example, Karotermes spp. (Kalotermes spp.), Reticulitermes spp. (Reticulitermes spp.).

From the order Psocoptera (Psocoptera), for example, Lepinatus spp. (Lepinatus spp.), Liposcelis spp. (Liposcelis spp.).

From Coleoptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp. (Necrobia spp.) .), Petinus spp. (Ptinus spp.), Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Sitophilus zeamais, Sitophilus zeamais ).

From Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp. (Anopheles spp.) -Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Culex tarsalis Drosophila spp.), Fannia canicularis, Musca domestica, Frebotos spp. (Phlebotomus spp.), Sarcophaga carnaria (Sarcophaga) carnaria), Simulium spp. (Simulium spp.), Stomoxys calcitrans, Tipula paludosa.

From Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellion , Tineola bissellielia.

From the flea (Siphonaptera), for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans. penetrans), Xenopsylla cheopis.

Hymenoptera, such as Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Lasius Monombratus, Monomorium s. spp. (Parave spula spp.), Tetramorium caespitum.

From the louse (Anoplura), for example, Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Pemphigus spp., Phylola large -Phthirus pubis.

From Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household pesticides, they may be derived alone or from other suitable active compounds such as phosphate esters, carbamates, pyrethroids, neonicotinoids, growth regulators, or other known pesticides Used in combination with the active compound of.

These are aerosols, non-pressurized spray products, such as pumps and spray sprays, automatic spray systems, foggers, evaporators with foam, gel, cellulose or plastic evaporators, liquid evaporators, gels and membranes. Evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, used in fly paper, fly catchers and fly catch gels, as granules or dust, in wood feeds or in feeding grounds.

The compounds according to the invention exhibit strong antibacterial activity and can be used to combat unwanted microorganisms such as fungi and bacteria in plant protection and in material protection.

Antifungal agents include Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Ascomycetes, and Basidiomycetes. It may be used for plant epidemics in.

Bactericides are used to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae in plant epidemics. It may be used for.

Examples include, but are not limited to, several pathogens of fungal and bacterial diseases that fall under the generic name listed above: For example, the following diseases caused by powdery mildew pathogens, Blumeria species, such as Blumeria graminis; Various species of the genus Podosphaera, such as Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator; For example, diseases caused by the following rust disease pathogens, Gymnosporangium species, such as Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as Puccinia recondita; Uromyces species, such as Uromyces appendiculatus; For example, diseases caused by the following oomycetes pathogens, Bremia species, such as Bremia lactucae; Various species of the genus Peronospora, such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans; Various Plasmopara species, such as Plasmopara viticola; Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis etc .; Pythium species, such as Pythium ultimum; For example, leaf spot diseases and leaf wilts, caused by: Alternaria species, such as Alternaria solani; Various Cercospora species, such as Cercospora beticola; Cladosporium species, such as Cladosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus; (Conidia morphology: Drechslera, nickname: Helminthosporium); Colletotrichum species, such as Colletotrichum lindemuthanium; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Various Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea; Mycosphaerella species, such as Mycosphaerella graminicola and Mycosphaerella fijiensis; Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophora species, such as Pyrenophora teres; Ramularia species, such as Ramularia collo-cygni; Rhynchosporium species, such as Rhynchosporium secalis; Various Septoria species, such as Septoria apii; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis; For example, root and stem diseases caused by: Corticium species, such as Corticium graminearum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Rhizoctonia species, such as Rhizoctonia solani; Various species of the genus Tapesia, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis basicola; For example, ear and panicle diseases (including maize cobs), caused by: Alternaria species, such as Alternaria spp.; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Various Claviceps species, such as Claviceps purpurea; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis; For example, the following diseases caused by smut disease, Various species of the genus Sphacelotheca, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries; Urocystis species, such as Urocystis occulta; Various Ustilago species, such as Ustilago nuda; For example, fruit rot caused by: Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Penicillium species, such as Penicillium expansum and Penicillium purpurogenum; Sclerotinia species, such as Sclerotinia sclerotiorum; Verticilium species, such as Verticilium alboatrum; Seed and soil-borne decay fungi rots and wilts, as well as seedling diseases, caused by, for example: Alternaria species, such as Alternaria brassicicola; Aphanomyces species, such as Aphanomyces euteiches; Ascochyta species, such as Ascochyta lentis; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium herbarum; Cochliobolus species, such as Cochliobolus sativus; (Conidia morphology: Drechslera, Bipolaris nickname: Helminthosporium); Colletotrichum species, such as Colletotrichum coccodes; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Macrophomina species, such as Macrophomina phaseolina; Monographella species, such as Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsi species, such as Phomopsis sojae; Phytophthora species, such as Phytophthora cactorum; Pyrenophora species, such as Pyrenophora graminea; Pyricularia species, such as Pyricularia oryzae; Pythium species, such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani; Rhizopus species, such as Rhizopus oryzae; Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septoria nodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae; For example, ulcer disease (cankers), galls and witches' broom, caused by: Nectria species, such as Nectria galligena; For example, wilts caused by: Various Monilinia species, such as Monilinia laxa; Leaf, flower and fruit malformations caused by, for example: Taphrina species, such as Taphrina deformans; For example, degenerative diseases of woody plants caused by: Esca species, such as Phaeomoniella clamydospora, Phaeoacremonium aleophilum and Fomitiporia mediterranea; For example, flower and seed diseases caused by: Botrytis species, such as Botrytis cinerea; Diseases of plant tubers caused by, for example: Rhizoctonia species, such as Rhizoctonia solani; Helminthosporium species, such as Helminthosporium solani; Diseases caused by, for example, the following bacterial pathogens: Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Various Erwinia species, such as Erwinia amylovora.

Preferably, the following soybean diseases can be controlled.

Fungal diseases of leaves, stems, pods and seeds caused by, for example: Alternaria spot disease (Alternaria spec.atrans tenuissima), anthrax (Colletotrichum gloeosporoides dematium var (variant). Colletotrichum gloeosporoides dematium var. , Brown spot disease (Septoria glycines), Sercospora spot disease and leaf blight (Cercospora kikuchii), Koanehora leaf blight (Choanephora infundibulifera trispora) syn.)), Dactuliophora glycines, and Peronospora manshurica), Drechslera glycini (Drechslera glycini), White spot disease (Cercospora sojina), Leptosphaerlina spot disease (Leptosphaerina triholi) fol Spot disease (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), Udonko disease (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight Rhizoctonia solani), rust (Phakopsora pachyrhizi), Fusarium head blight (Sphaceloma glycines), Stemphyllium leaf blight (Stemphylium botryosum), purpura (Purpura) target spot) (Corynespora cassiicola).

Root and stem-based fungal diseases caused by, for example: Black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), Fusarium leaf blight or wilt, root rot, and pod and color rot (Fusarium oxysporum) (Fusarium oxysporum), Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus root rot (Mycolrestodiscus) Cosmospora (Neocosmopspora vasinfecta), sheath and stalk blight (Diaporthe) phaseolorum), Chestnut blight (Diaporthe phaseolorum var.caulivora), Pythium rot (Phytophthora megasperma), Brown stalk rot (Pytophthora megasperma) Phialophora gregata)), Pythium rot (Pythium aphanidermatum), Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium myriotylum )), Rhizoctonia root rot, stem corrosion and seedling blight (Rhizoctonia solani), Sclerotinia stalk corrosion (Sclerotinia) sclerotiorum)), Sclerotinia white silk disease (Sclerotinia rolfsii), Thieraviopsis root rot (Thielaviopsis basicola).

The active compound according to the present invention also exhibits a strong activating effect in plants. Therefore, these compounds are suitable for mobilizing the plant's internal defenses against unwanted microbial attack.

In the context of the present invention, plant-enhancing (resistance-inducing) substances are such that when the plant being treated is continuously inoculated with unwanted microorganisms, it exhibits broad resistance to these microorganisms. It should be understood to mean substances capable of stimulating the plant's defense system.

In the case of the present invention, unwanted microorganisms should be understood to mean phytopathogenic fungi, bacteria and viruses. Therefore, the substances according to the invention may be used to protect plants for a period of time after treatment against attacks by the mentioned harmful pathogens. The period for which this protection is achieved generally extends from 1 to 10 days, preferably 1 to 7 days after treating the plant with this active substance.

Due to the fact that the active substance is well tolerated by the plant at the concentrations required to control the disease of the plant, the treatment of the above-ground parts of the plant, the plant growth material and seeds, and the soil It will be possible.

In the present invention, the active substances according to the present invention are, for example, grain diseases such as Puccinia species, and viticulture such as Botrytis, Venturia or Alternaria species, fruits and. It can be used particularly successfully to control diseases in vegetable cultivation.

The active material according to the invention is also suitable for increasing crop yields. In addition, they show reduced toxicity and are well tolerated by plants.

The active agent according to the invention can also be used, optionally, at specific concentrations and in applied amounts, as a herbicide, to affect plant growth and to control animal pests. They can optionally also be used as intermediates and precursors for the synthesis of additional active substances.

All plants and parts of plants can be treated according to the present invention. In the present invention, plant should be understood to mean all plants and plant populations such as desirable and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants that can be obtained by conventional breeding and optimization methods, by biotechnology and genetic engineering methods, or by a combination of these methods, including transgenic plants. Also included are plant varieties that can or cannot be protected by various certification criteria. The part of a plant must be understood to mean all parts and organs of the plant above and below, such as buds, leaves, flowers and roots, for example leaves, needle-shaped leaves ( Needles), stems, stems, flowers, offspring, fruits and seeds, as well as roots, tubers and substems. Plant parts also include harvested crops and substances that propagate by vegetative propagation and reproduction, such as cuttings, tubers, rhizomes, cuts and seeds.

Treatment of plants and plant parts with active substances according to the invention may be carried out directly or by using conventional treatment methods, for example by dipping, spraying, evaporation, atomizing, scattering, spraying of the growing material. In some cases, especially in the case of seeds, this is done by further applying a single or multi-layer coating to act on their surroundings, habitat or storage location.

In addition, the treatment according to the invention can reduce the content of mycotoxins in harvested crops and foodstuffs as well as foodstuffs prepared from them. In the present invention, the following mycotoxins, although not exclusively, can be mentioned: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2 and HT2 toxins, toxins, fumonicins. , Zearalenone, moniliformin, fusarium, diacetoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferine, fusarenole, ochratoxins, patulin Alkaloids and afratoxins (these can be caused, for example, by the following fungal diseases: Fusarium spec., For example, Fusarium acuminatum, F.avenaceum, F.crookwellense, F.culmorum, F.graminearum (Gibberella) zeae)), F.equiseti, F.fujikoroi, F.musarum, F.oxysporum, F.proliferatum, F.poae, F.pseudograminearum, F.sambucinum, F.scirpi, F.semitectum, Fusarium F.solani, F.sporotrichoides, F.langsethiae, F.subglutinans, F.tricinctum, F.tricinctum, F.tricinctum (F.verticillioides) and also various Aspergillus genus (Aspergillus) Spec.), Penicillium spec., Claviceps purpurea, Stachybotrys spec., Etc.

In material protection, the materials according to the invention may be used to protect industrial materials from unwanted microbial attack and destruction.

Industrial materials should be understood in the present invention to mean non-living materials prepared for industrial use. For example, industrial materials protected by active substances according to the invention from microbial alterations or destruction include adhesives, glues (sizes), paper and cardboard, textiles, leather, wood, paints and plastic products, cooling lubricants. , And other materials that can be attacked or destroyed by microorganisms. In the context of materials to be protected, some of the manufacturing plants, such as cooling water circuits that can be harmed by the growth of microorganisms, can also be mentioned. In the present invention, preferably industrial materials consist of adhesives, glues (sizes), paper and cardboard, leather, wood, paints, cooling lubricants, and heat exchangers, especially wood. Can be mentioned.

Examples of microorganisms that can corrode (decompose) or modify industrial materials include bacteria, fungi, yeasts, algae and slime organisms. The active material according to the invention is preferably active against fungi, especially molds, fungi that discolor or destroy wood (Basidiomycetes), and slime organisms and algae.

Microorganisms of the following genera can be cited as examples: Alternaria, for example Alternaria tenuis, Aspergillus, for example Aspergillus niger, Chaetomium, such as Chaetomium globosum, Wet Rot (Coniophora), for example Coniophora puetana, Lentinus, for example Lentinus tigrinus, The genus Penicillium, for example Penicillium glaucum, Polyporus, for example Polyporus versicolor, Aureobasidium, for example Aureobasidium pullulans, The genus Sclerophoma, for example Sclerophoma pityophila, The genus Trichoderma, for example Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, The genus Staphylococcus (Staphylococcus aureus), for example Staphylococcus aureus.

The present invention relates to compositions for controlling unwanted microorganisms, which comprises at least one of the compounds according to the invention.

The compounds according to the invention are, in this regard, depending on their respective physical and / or chemical properties, standard formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules. It can be converted into microcapsules, in aerosols, in polymer materials and in coating materials, and also in ULV-cold fogging formulations, and ULV-warm fumigants.

These formulations are optionally made by mixing an active substance with a bulking agent (a liquid solvent, a gas liquefied under pressure, and / or a solid carrier) in a known manner, optionally a surfactant ( It is prepared by mixing an emulsifier and / or a dispersant and / or a foaming agent). When water is used as the bulking agent, for example, an organic solvent can also be used as a co-solvent. Possible liquid solvents are essentially: Aromatic hydrocarbons such as xylene, toluene or alkylnaphthalene, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffin, such as petroleum Fractions, alcohols such as butanol or glycols, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, and also water. Liquefied gas bulking agents or carriers are liquids that are gaseous at standard temperatures and pressures, such as aerosol sprays, such as halogenated hydrocarbons, and also butane, propane, nitrogen and dioxide. It should be understood that carbon also means. Potential solid carriers are, for example, natural minerals of the soil, such as kaolin, pottery, talc, chalk, quartz, attapulsite, montmorillonite or diatomaceous earth and soil synthetic minerals, such as ultrafine silica, oxidation. Aluminum and silicate. Potential solid carriers for granules are, for example, ground and split natural stones such as calcite (calcite), dolomite, marble, sea foam or dolomite (white cloud stone), and also inorganic and organic. Synthetic granules formed from dust, as well as granules formed from organic matter such as dolomite, coconut shells, corn stalks and tobacco stems. Potential emulsifiers and / or foaming agents are, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkyl sulfos. Nart, alkyl sulfates, aryl sulfonic acids and also protein hydrolysates. Potential dispersants are, for example, lignosulphite.

Adhesive agents such as carboxymethyl cellulose, natural and synthetic polymers (in the form of powders, granules, or latex), such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalin. , Lecithin, etc., as well as synthetic phospholipids may be utilized in this formulation. Other possible additives are mineral oils and vegetable oils.

Colorants such as inorganic pigments pigments (eg iron oxide, titanium oxide, Prussian blue) and organic dyes (eg alizarin dyes, azo dyes, and metallic phthalocyanine dyes) and trace elements (eg iron, manganese, boron, copper, etc.) Cobalt, molybdenum, and zinc salts) can also be utilized.

This formulation generally contains 0.1 to 95% by weight, preferably 0.5 to 90% of the active substance.

The above-mentioned preparations may be used in the method according to the present invention for exterminating unwanted microorganisms, in which the compounds according to the present invention are given to the microorganisms and / or to this habitat.

Control of phytopathogens by treating plant seeds has long been known and is the subject of sustained improvement. Nevertheless, a series of problems arise in seed processing, which cannot always be satisfactorily solved. Therefore, it is desirable to develop methods for protecting seeds and germinated plants that result in extra or at least significantly reduced application of the plant defense composition after sowing or emergence of the plant. The seeds and germinative plants are given the best possible protection against attack by phytopathogens, but the plant itself can be further optimized for the amount of active material used so that it is not damaged by the active material used. desirable. Specifically, methods for the treatment of seeds also provide the unique antifungal properties of transgenic plants to achieve optimal protection of seeds and germinated plants while minimizing the expenditure of plant defense compositions. Must be included.

Accordingly, the invention also specifically relates to a method for protecting seeds and germinated plants from attack by phytopathogens by treating the seeds with the compositions according to the invention.

The present invention also relates to the use of the compositions according to the invention for the treatment of seeds to protect seeds and germinated plants from phytopathogens.

Furthermore, the present invention relates to seeds treated with the compositions according to the invention to protect against phytopathogens.

One of the advantages of the present invention is that, thanks to the specific permeability properties of the compositions according to the invention, the treatment of seeds with these compositions not only protects the seeds themselves from phytopathogens, but also the resulting plants. Is to protect against phytopathogens even after budding. In this method, immediate treatment of the crop may be given at or immediately after sowing.

Similarly, it is considered an advantage that the mixture according to the invention can be used specifically in transgenic seeds.

The compositions according to the invention are suitable for the protection of seeds of any plant species used in agriculture, greenhouses, forests or horticulture. The seeds according to the present invention specifically include cereals (eg wheat, barley, rye, millet and oats (crow beet)), corn, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, beets (eg, eg). Seeds of sugar beets and feed beets), peanuts, plants (eg, tomatoes, ryes, onions and lettuce), turf and ornamental plants. Cereals (eg wheat, barley, rye and oats (oats)), and corn and rice seeds are of particular importance.

In the present invention, the compositions of the present invention are applied to the seed alone or in a suitable formulation. Preferably, the seeds are treated under adequate conditions so as not to cause damage during the treatment. In general, seed processing can be done at any time between harvesting and sowing. Seeds that have been isolated from the plant and have had their pods, shells, stems, epidermis, hair or pulp removed are usually used. Thus, for example, it is possible to use seeds that have been harvested, cleaned, and dried to a humidity of up to less than 15% by weight. Alternatively, the dried seeds can be treated with, for example, water and then dried again for use.

Generally, in the treatment of seeds, the amount of the composition according to the invention and / or the additional additives applied to the seeds so that the germination of the seeds is not impaired, and the plants obtained from it Care must be taken to choose not to be disturbed. This should be considered, specifically, with active substances that can exhibit phytotoxic effects at specific rates of application.

The compositions according to the invention may be applied immediately and therefore without additional ingredients and without dilution. It is generally preferred to apply the composition to the seeds in the form of a suitable formulation. Suitable formulations and methods for treating seeds are known to those of skill in the art and are described, for example, in the following literature: US4272417A, US4245432A, US4808430A, US5876739A, US2003 / 0176428A1, WO2002 / 080675A1, WO2002 / 028186A2.

Combinations of active substances that can be used in accordance with the present invention are converted into powdered formulations such as solutions, emulsions, suspensions, powders, foams, slurries or other coating agents for seeds, as well as ULV formulations. May also be converted.

These formulations, in a known manner, combine active substances or combinations of active substances with conventional additives such as conventional bulking agents, as well as solvents or diluents, colorants, moisturizers, dispersants, emulsifiers, It is prepared by mixing with antifoaming agents, preservatives, secondary thickeners, adhesives, diberelin and also water.

Suitable colorants that may be present in the seed powder coating formulation that can be used according to the present invention include all colorants that are convenient for such purposes. In the present invention, both pigments that are sprayed and dissolved in water and pigments that are soluble in water can be utilized. Examples include colorants known from the description of Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1.

Possible moisturizers that may be present in the seed powder coating formulation that can be used according to the present invention include all substances that promote moisturization and are convenient in the formulation of agriculturally effective substances. Preferably, alkylnaphthalene sulfonates, such as diisopropyl- or diisobutylnaphthalene sulfonate, can be utilized.

Suitable dispersants and / or emulsifiers that may be present in the seed powder coating formulation that can be used according to the present invention are all nonionic, anionic and cationic dispersants that are convenient in the formulation of agriculturally effective substances. including. Preferably, a nonionic or anionic dispersant or a mixture of nonionic or anionic dispersants can be utilized. Suitable nonionic dispersants include ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and also tristyrylphenol polyglycol ethers, and phosphate or sulfate derivatives thereof. Suitable anionic dispersants are specifically lignosulphonates, polyacrylates, and arylsulphonates / formaldehyde condensates.

The defoaming agent that may be present in the seed powder coating preparation that can be used according to the present invention includes all foaming inhibitors that are convenient in the preparation of an agriculturally effective substance. Preferably a silicone defoamer and magnesium stearate can be utilized.

Preservatives that may be present in seed powder coating formulations that can be used in accordance with the present invention include all substances that can be used in agricultural compositions for such purposes. Dichlorophen and benzyl alcohol hemiformal can be mentioned.

Possible secondary thickeners that may be present in the seed powder coating formulation that can be used in accordance with the present invention include all substances that can be used in agricultural compositions for such purposes. Preferably suitable are cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly dispersible silica.

Possible adhesives present in the seed powder coating formulation that can be used in accordance with the present invention include all convenient binders that can be used in the seed powder coating. Preferably, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose may be mentioned.

Possible gibberellins that may be present in seed powder coatings that can be used in accordance with the present invention preferably include gibberellins A1, A3 (= gibberellic acid), A4 and A7; particularly preferably gibberellic acid is utilized. Gibberellin is known (reference, R. Wegler, "Chemie der Pflanzenschutz-und Schaedlingsbekaempfungsmittel" [Chemistry of Plant Protection and Pest Control Agents], Volume 2, Springer Verlag, 1970, pp. 401-412).

The seed powder coating formulation that can be used according to the present invention can be used directly or before and after dilution with water for the treatment of seeds of most altered species. Thus, the concentrations or compositions that can then be obtained by diluting with water are cereal seeds such as wheat, barley, rye, oats (crow wheat) and triticale, as well as corn, rice, rapeseed, pea, legume, cotton, sunflower. And can be used for beet seeds, or oats for the seeds of most varied properties of vegetable seeds. The seed dressing preparation or the diluted composition which can be used according to the present invention can also be used for the seed dressing of transgenic plants. In the present invention, additional synergistic effects can also result in interactions with the substances formed by expression.

All mixing devices that can be conveniently used for powder coating are suitable for treatment of seeds with the seed powder coating formulation that can be used according to the present invention, or the composition prepared from it by the addition of water. Specifically, in this powdering procedure, the seeds are introduced into the mixture and the desired amount of seed powder coating is added at each time, either as is or before or after dilution with water, to form the formulation. The procedure is such that mixing is performed until it is evenly distributed on the seeds. If necessary, drying work continues.

The application rate of the seed powder-coated preparation that can be used according to the present invention can be changed in a relatively wide range. This rate depends on the relative content of the active substance in the formulation and on the seeds. The application rate of the active substance combination is generally between 0.01 g and 50 g per kg of seeds, preferably 0.01 g to 15 g per kg.

The compounds according to the invention are, as they are, or in their formulations, and in mixtures with known antifungal agents, fungicides, acaricides, nematodes or insecticides, thus, for example, a spectrum of activity. Can be used to spread or prevent the development of resistance.

It can also be mixed with other known active substances such as herbicides, or with fertilizers and growth regulators, toxicity mitigators or semiochemicals.

In addition, the compounds of formula (I) according to the invention also exhibit very good bactericidal activity. These compounds have an extremely broad spectrum of bactericidal activity, specifically dermatophytons and sprouting fungi, mold and biphasic fungi (eg, Candida species, eg, Candida albicans), Against Candida glabrata, and also Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus. Species such as Trichophyton mentagrophyte, Microsporon species, such as Microsporon Has bactericidal activity against canis) and audouinii. The list of these bacteria by no means limits the spectrum of bacteria that can be included, but is merely an example.

The compounds according to the invention can therefore be used in both medical and non-medical applications.

The active substance, as is, in the form of these formulations or in the form of an application prepared from them, for example in ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dust and granules. It may be applied in the form. Applications are standard methods, such as by pouring, spraying, atomizing, scattering, dusting, foaming, spreading, etc. Do. In addition, it is possible to apply the active substance by the ultra-low volume method or to inject the active substance composition or the active substance itself into the soil.

It is also possible to process the seeds of the plant.

When the compound according to the invention is used as a disinfectant, the rate of application may vary over a fairly large range, depending on the type of application. In the treatment of plant portions, the application rate of the active substance is generally 0.1 to 10,000 g per ha, preferably 10 to 1,000 g per ha. When treating seeds, the application rate of the active substance is generally 0.001 to 50 g per kg of seeds, preferably 0.01 to 10 g per kg of seeds. When treating soil, the application rate of the active substance is generally between 0.1 and 10,000 g per ha, preferably between 1 and 5,000 g per ha.

As already mentioned above, all plants and some of them can be treated according to the present invention. In a preferred embodiment, plant species and plant varieties that appear in the wild or are obtained by conventional biological breeding methods (eg, crosses or protoplast fusions), and some of these are treated. In a further preferred embodiment, genetic engineering methods optionally treat transgenic plants and plant varieties obtained in combination with conventional methods (genetically engineered organisms), and parts thereof. The terms "part" or "part of plant" or "plant part" have been described above.

The method of treatment according to the invention can be used in the treatment of genetically engineered organisms (GMOs), such as plants or seeds. A genetically engineered plant (or transgenic plant) is a plant in which a heterologous gene is stably integrated into the genome. The expression "heterologous gene" is essentially new or improved agronomic to transformed plants when provided or assembled outside the plant and introduced into the nuclear, chloroplast or mitochondrial genome. Or other properties, by expressing the protein or polypeptide of interest, or by down-regulating or silencing other genes (s) present in the plant (eg, antisense techniques, co-suppression techniques). Alternatively, RNA-interfering RNAi technology is used), meaning the gene that results. Heterologous genes located in the genome are also called transgenes. The transgene is defined by this particular location in the plant genome and is referred to as a transformation or transgenic event.

Depending on the plant species or plant cultivar, their location and growth conditions (soil, climate, vegetation period, diet), the treatments according to the invention can also produce hyperadditive (synergistic) effects. Thus, for example, lowering the applicability and / or expanding the activity spectrum, and / or increasing the activity of the active substances and compositions that can be used by the present invention, better plant growth, increased resistance to high or low temperatures , Increased resistance to drought or water or soil salt content, increased flowering capacity, faster harvest, accelerated maturation, higher yield, larger fruits, larger plant heights, darker leaf greens, faster Flowering, higher quality and / or higher nutritional value of the harvested product, higher sugar concentration in the fruit, better storage stability, and / or processability of the harvested product are possible, these are Exceeds the actual expected effect.

At a particular rate of application, the combination of active substances according to the invention may also have a potentiating effect on the plant. Therefore, they are suitable for mobilizing plant defense systems against attacks by unwanted phytopathogens and / or microorganisms and / or viruses. This can be, if desired, one reason for the enhanced activity of the combination according to the invention, eg, on fungi. Plant-enhancing (resistance-inducing) substances are, in the context of the present invention, these undesired phytopathogenic substances if the treated plant is subsequently inoculated with unwanted phytopathogenic fungi and / or microorganisms and / or viruses. It should be understood to mean a substance or combination of substances that can stimulate the plant's defense system in such a way that it exhibits a substantial degree of resistance to fungi and / or microorganisms and / or viruses. In the present invention, the undesired phytopathogenic fungi and / or microorganisms and / or viruses should be understood to mean phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be used to protect plants against attack by the pathogens described above within a specific period of time after treatment. The period for which protection is achieved generally extends from 1 to 10 days, preferably 1 to 7 days after treatment of the plant with the active substance.

Plants and plant cultivars preferably treated according to the present invention include all plants having a genetic material that imparts particularly advantageous and useful properties to these plants (whether obtained by breeding or not). And / or as obtained by biotechnology methods).

Bacteria and plant-grown varieties that are also preferably treated according to the present invention are resistant to one or more biological stresses, i.e. the plant is resistant to animal and microbial pests, eg, viroids. Shows good protection against insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

The plants and plant cultivars that are also preferably treated according to the present invention are plants that are resistant to one or more abiotic stresses. Abiotic stress conditions include, for example, drought, cold exposure, heat exposure, permeable stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, etc. Restrictions on the availability of phosphorus nutrition and shade repellent can be mentioned.

Plants and plant cultivars that are also preferably treated according to the present invention are plants characterized by a characteristic enhancement of yield. Increased yields in this plant include, for example, improved plant physiology, growth and growth, such as water utilization efficiency, water retention efficiency, nitrogen utilization improvement, carbon assimilation improvement, photosynthesis improvement, germination efficiency increase and maturation. It can be the result of acceleration. Yields also include early flowering, flowering control for hybrid seed production, seed vitality, plant size, number and distance between nodes, root growth, seed size, fruit size, sheath size. Affected by plant structure improvements, including, number of pods or ears, number of seeds per pod or ear, seed mass, increased seed enrichment, reduced seed dispersal, reduced pot dehiscence, and lodging resistance. Get (under stressed and unstressed conditions). Further yield characteristics include seed composition, such as hydrocarbon content, protein content, oil content and composition, nutritional value, reduction of non-nutritive compounds, improved processability and improved storage stability.

Plants that can be treated according to the present invention are hybrid plants that have already developed the characteristics of heterosis or hybrid vitality, which generally provide high yield, vitality, health and resistance to biological and abiotic stressors. Occurs. Such plants are typically produced by crossing a homozygous male sterile parent strain (female strain) with another inbreeding male fertile parent strain (male parent). Hybrid seeds are typically collected from male nonflammable parents and sold to growers. Male sterile plants can sometimes be produced by removing bushes (ie, mechanical removal of male reproductive organs or male flowers), but more typically male sterility is , The result of genetic determinants in the plant genome. In that case, and especially if the seed is the desired product to be harvested from the hybrid plant, ensure that male fertility is fully restored in the hybrid plant containing the genetic determinants responsible for male sterility. Is typically useful. This can be achieved by ensuring that the male parent has the appropriate fertility repair gene (including the genetic determinant responsible for male fertility) capable of repairing male fertility in hybrid plants. The genetic determinant of male sterility can be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, in various Brassica species (WO1992 / 005251, WO1995 / 009910, WO1998 / 27806, WO2005 / 002324, WO2006 / 021972 and US6229072). However, the genetic determinants for male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods, such as genetic engineering. A particularly useful means of obtaining male sterile plants is described in WO89 / 10396, where, for example, ribonucleases (eg, barnase) are selectively expressed in stamen tapetum cells. Then fertility is barstar

Plants or plant cultivated varieties that can be treated according to the present invention (obtained by plant biotechnology methods such as genetic engineering) have been made resistant to herbicide-tolerant plants, i.e. one or more predetermined herbicides. It is a plant. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such herbicide resistance.

Herbicide-tolerant plants are, for example, glyphosate-resistant plants, i.e., plants that have been made resistant to the herbicide glyphosate or salts thereof. For example, glyphosate-resistant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyrvir shikimate-3-phosphase synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (variant CT7) of the bacterial Salmonella typhimurium (Comai et al., Science 1983, 221,370-371), the bacterial Agrobacterium. CP4 gene of species (Agrobacterium sp.) (Barry et al., Current Topics Plant Physiology (Curr. Topics Plant) Physiol.) (1992), 7,139-145), Genes Encoding Petunia EPSPS (Shah et al., Science 1986, 233,478-481), Tomato EPSPS (Gasser et al., Journal of Biological Chemistry) Biological Chemistry (J.Biol.Chem.) 1988, 263,4280-4289) or Eleusine EPSPS (WO2001 / 66704). It may also be, for example, the mutated EPSPS described in EP-A0837944, WO2000 / 066746, WO2000 / 066747 or WO2002 / 026995. Glyphosate-tolerant plants can also be obtained by expressing genes encoding glyphosate oxidoreductase as described in US5776760 and US5463175. Glyphosate-resistant plants may also be obtained by expressing genes encoding glyphosate acetyltransferases, such as those described in WO2002 / 036782, WO2003 / 092360, WO2005 / 012515 and WO2007 / 024782. Glyphosate-resistant plants may also be obtained by selecting plants containing naturally occurring variants of the genes described above, for example as described in WO2001 / 024615 or WO2003 / 013226.

Other herbicide-tolerant plants are plants that are resistant to herbicides that inhibit the enzyme glutathione synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme that detoxifies herbicides, or a variant of the glutamine synthetase enzyme that is resistant to inhibition. One such efficient detoxifying enzyme is the enzyme encoding phosphinotricine acetyltransferase, such as the bar or pat protein from various Streptomyces sources. Plants expressing endogenous phosphinotricine acetyltransferase are described, for example, in US5561236; US5648477; US5646024; US5273894; US5637489; US5276268; US5739082; US5908810 and US7112665.

Further herbicide-tolerant plants are also plants that have been made resistant to herbicides that inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). Hydroxyphenylpyruvic acid dioxygenase is an enzyme that catalyzes the conversion of para-hydroxyphenylpyruvic acid (HPP) to homogenticate. Plants resistant to HPPD inhibitors are genes encoding naturally occurring resistant HPPD enzymes, or genes encoding mutated HPPD enzymes, as described in WO1996 / 038567, WO1999 / 024585 and WO1999 / 024586. Can be transformed. Resistance to HPPD inhibitors can also be obtained by transforming the plant with a gene encoding a particular enzyme capable of forming homogenticinates, regardless of the inhibition of the natural HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002 /. Plant resistance to HPPD inhibitors can also be improved by transforming plants with a gene encoding the enzyme prephenate dehydrogenase, in addition to the gene encoding the HPPD resistant enzyme, as described in WO2004 / 024928.

Further herbicide-tolerant plants are those that have been made resistant to acetactase synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylureas, imidazolinone, triazolopyrimidine, pyrimidinyoxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. Various variants of the ALS enzyme (acetohydroxy acid synthase, also known as AHAS) include, for example, Tranel and Wright, Weed. It is known to confer resistance to various herbicides and herbicide groups, as described in Science (2002), 50,700-712, but also in US5605011, US5378824, US5141870 and US5013659. The production of sulfonylurea-resistant and imidazolinone-resistant plants is described in US5605011; US5013659; US5141870; US5767361; US5731180; US5304732; US4761373; US5331107; US5928937; and US5378824; and WO 1996/033270. Other imidazolinone resistant plants are also described, for example, in WO2004 / 040012, WO2004 / 106529, WO2005 / 020673, WO2005 / 093093, WO2006 / 007373, WO2006 / 015376, WO2006 / 024351 and WO2006 / 060634. Additional sulfonylurea and imidazolinone resistant plants are also described, for example, in WO 2007/024782.

Other plant resistances to imidazolinone and / or sulfonylureas include, for example, soybeans on US5084082, rice on WO1997 / 41218, sugar beet on US5773702 and WO1999 / 057965, lettuce on US5198599, or sunflower on WO2001 / 065922. Can be obtained by herbicide or mutant going species, induced abrupt changes in cell culture in the presence of herbicides, selection, as described in.

Plants or plant-grown varieties that can be processed according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are insect-tolerant transgenic plants, ie, plants that have been made resistant to attack by specific target insects. Is. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such insect resistance.

"Insect-resistant transgenic plant" as used herein includes any plant containing at least one transgene containing a coding sequence encoding: 1) Bacillus thuringiensis-derived insecticidal crystalline protein or this insecticidal portion, eg http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/) Crickmore et al., Updated by Crickmore et al. (2005) in the toxin nomenclature of Bacillus thuringiensis, Microbiology and Molecular Biology Reviews) 1998, 62, 807-813 listed insecticidal crystal proteins or their insecticidal components, eg, Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Ae or Cry3Bb proteins or their insecticidal portions of the Cry protein classification; Or 2) Bacillus Consists of a second other crystalline protein from thuringiensis) or a crystalline protein from Bacillus thuringiensis that is insecticidal in the presence of this portion, such as Cry34 and Cry35 crystalline proteins. Binary toxins (Moellenbeck et al., Nature Biotechnol. 2001, 19, 668-72; Schnepf et al., Applied and Environmental Microbiology (Applied Environm. Microbiol.) 2006, 71, 1765-1774) or 3) A hybrid insecticidal protein containing parts of two different insecticidal crystalline proteins from Bacillus thuringiensis, eg, a hybrid of the protein of 1) above or a hybrid of the protein of 2) above, eg, a corn event MON98034. Cry1A.105 protein produced by (WO2007 / 027777); or 4) Reasons for changes introduced into the coding DNA to obtain higher insecticidal activity on the target insect species and / or to expand the range of affected target insect species and / or during cloning or transformation. In one of the proteins 1) to 3) above, where some, especially 1 to 10 amino acids, have been replaced with another amino acid, eg, the Cry3Bb1 protein in corn event MON863 or MON88017, or corn. Event Cry3A protein in MIR604; 5) Insecticidal secretory protein from Bacillus thuringiensis or Bacillus cereus, or this insecticidal portion, eg http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore Proteins from the classification of plant insecticidal (VIP) proteins listed in /Bt/vip.html, eg VIP3Aa proteins; or 6) Bacillus thuringiensis or Bacillus cereus (Bacillus thuringiensis) or Bacillus cereus (Bacillus thuringiensis), which is insecticidal in the presence of a second secretory protein from Bacillus thuringiensis or B. cereus. A two-component toxin composed of secretory proteins from Bacillus cereus), such as VIP1A and VIP2A proteins (WO1994 / 21795); 7) A hybrid insecticidal protein containing a portion from a different secretory protein from Bacillus thuringiensis or B. cereus, eg, a hybrid of the protein in 1) above or a protein in 2) above. Hybrid; or 8) Changes introduced into the coding DNA to obtain higher insecticidal activity on the target insect species and / or to expand the range of affected target insect species and / or during cloning or transformation. , Still encoding an insecticidal protein.) Some, especially 1 to 10 amino acids are replaced with another amino acid, any one of the above 1) to 3) proteins, eg , Wata event VIP3Aa protein in COT102.

Of course, the insect-tolerant transgenic plants used herein include any plant that contains a combination of genes encoding any one of the proteins in categories 1-8 above. In one embodiment, insect resistant plants are insecticidal to the same target insect species, but are affected by using different proteins with different modes of action, such as binding to different receptor binding sites of insects. Includes two or more transgenes encoding a protein of any one of the above categories 1-8 to expand the range of target insect species or delay the development of insect resistance to plants.

Plants or plant cultivars that can be processed according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are resistant to abiotic stress. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such stress tolerance. Particularly useful stress-tolerant plants include: Transgenes that can reduce the expression and / or activity of the poly (ADP-ribose) polymerase (PARP) gene in plant cells or plants, as described in WO2000 / 004173 or EP04077984.5 or EP06009836.5. Plants including.

b. Plants containing a stress tolerance-enhancing transgene that can reduce the expression and / or activity of a gene encoding PARG in a plant or plant cell, eg, as described in WO2004 / 090140; c. For example, as described in EP04077624.7 or WO2006 / 133827 or PCT / EP07 / 002433, nicotinamidase, nicotinatophosphoribosyltransferase, nicotinate mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthase or nicotin. A plant containing a stress tolerance enhancing transduction gene encoding a plant functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including amidophosphoribosyltransferase.

Plants or plant cultivated varieties that can be processed according to the present invention (obtained by plant biotechnology methods such as genetic engineering) include varying amounts, quality and / or storage stability and / or storage stability of harvested products such as: Show the altered properties of certain ingredients of the harvested product: 1) In this physicochemical property, in particular, amylase content or amylopectin ratio, degree of branching, average chain length, side chain distribution, viscosity behavior, gel strength, starch particle size and / or starch particle morphology. A transgenic plant that synthesizes modified starch, in which the modified starch has been modified to better match a particular application as compared to starch synthesized in wild-type plant cells or plants. This transgenic plant that synthesizes modified starch is, for example, EP0571427, WO1995 / 004826, EP0719338, WO1996 / 15248, WO1996 / 19581, WO1996 / 27674, WO1997 / 11188, WO1997 / 26362, WO1997 / 32985, WO1997 / 42328. , WO1997 / 44472, WO1997 / 45545, WO1998 / 27212, WO1998 / 40503, WO99 / 58688, WO1999 / 58690, WO1999 / 58654, WO2000 / 008184, WO2000 / 008185, WO2000 / 28052, WO2000 / 72729, WO2001 / 12782, WO2001 / 12826, WO2002 / 101059, WO2003 / 071860, WO2004 / 056999, WO2005 / 030942, WO2005 / 030941, WO2005 / 095632, WO2005 / 095617, WO2005 / 095619, WO2005 / 095618, WO2005 / 123927, WO2006 / 018319, WO2006 / 103107 , WO2006 / 108702, WO2007 / 009823, WO2000 / 22140, WO2006 / 063862, WO2006 / 072603, WO2002 / 034923, EP06090134.5, EP06090228.5, EP06090227.7, EP07090007.1, EP07090009.

2) Transgenic plants that synthesize non-starch carbohydrate polymers or that have altered properties compared to wild plants without the use of genetic modification. Examples include plants that produce inulin and levan-type polyfructose, especially those disclosed in EP0663956, WO1996 / 001904, WO1996 / 021023, WO1998 / 039460 and WO1999 / 024593, WO1995 / 031553, US2002 / 031826, US6284479, US5712107. , WO1997 / 047806, WO1997 / 047807, WO1997 / 047808 and WO2000 / 14249, a plant that produces α-1,4-glucan, WO2000 / 73422, α-1,6 branch α- Plants that produce 1,4-glucan, as well as plants that produce alternan as disclosed in WO2000 / 047727, EP06077301.7, US5908975 and EP0728213.

3) For example, a transgenic plant producing hyaluronan disclosed in WO2006 / 032538, WO2007 / 039314, WO2007 / 039315, WO2007 / 039316, JP2006-304779, and WO2005 / 012529.

Plants or plant cultivated varieties that can be processed according to the present invention (can be obtained by plant biotechnology methods such as genetic engineering) are plants such as cotton plants with altered fibrous properties. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such altered fibrous properties, including: a) Plants such as cotton plants containing altered morphology of the cellulose synthase gene described in WO 1998/000549, b) Plants such as cotton plants containing variants of the rsw2 or rsw3 homologous nucleic acids described in WO2004 / 053219; c) Plants such as cotton plants with increased expression of sucrose phosphate synthase described in WO2001 / 017333, d) Plants such as cotton plants with increased expression of sucrose synthase described in WO 02/45485; e) Plants such as cotton plants whose timing of opening and closing of plasmodesma at the base of fibrous cells is altered, for example, through downregulation of fiber-selective β-1,3-glucanase, as described in WO2005 / 017157; f) Plants such as cotton plants having fibers with altered reactivity through expression of the N-acetylglucosamine transferase gene, including the nodC and chitin synthase genes, as described in WO 2006/136351.

Plants or plant cultivated varieties that can be processed according to the present invention (can be obtained by plant biotechnology methods such as genetic engineering) are plants such as Brassica plants or related Brassica plants with altered oil profile characteristics. Is. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that impart such altered oil characteristics, including: a) Plants such as oilseed rape plants that produce oils with high oleic acid content as described in US5969169, US5840946, US6323392 or US6063947; b) Plants such as oilseed rape plants that produce oils with low linolenic acid content as described in US6270828, US6169190 or US5965755. c) Plants such as oilseed rape plants that produce oils with low levels of saturated fatty acids as described in US 5434283, for example.

Particularly useful transgenic plants that can be processed according to the present invention are plants that contain one or more genes encoding one or more toxins and are transgenic plants sold under the following trade names. YIELD GARD® (eg corn, cotton, soybeans), KnockOut® (eg corn), BiteGard® (eg corn), Bt-Xtra® (eg corn), StarLink® (eg Corn), Bollgard® (Wata), Nucotn® (Wata), Nucotn33B® (Wata), NatureGard® (eg Corn), Protecta (Registered Trademark) and New Leaf® (Potato). Examples of herbicide-tolerant plants that can be mentioned are corn varieties, cotton varieties and soybean varieties, such as: Roundup Ready® (Glyphosate resistance, eg corn, cotton, soybean), Liberty. Sold under Link® (tolerance to phosphinotricin, eg oilseed rape), IMI® (tolerance to imidazolinone strains), and SCS® (tolerance to sulfonylureas) (eg corn). It is a plant that has been used. Examples of herbicide-tolerant plants (plants that have been bred in a conventional manner with respect to herbicide resistance) include varieties sold under the trade name Clearfield® (eg, corn).

Particularly useful transgenic plants that can be processed according to the present invention include transforming events, or combinations of transforming events, such as databases of various national or local authorities (eg, http://gmoinfo.jrc.it/). The plants listed in gmp_browse.aspx and http://www.agbios.com/dbase.php).

<p num="0409"> Phaedon cochleariae-test; (PHAECO spray applied) Solvent: 78.0 parts by weight acetone 1.5 parts by weight dimethylformamide Emulsifier: 0.5 parts by weight alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with a predetermined amount of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing the emulsifier. .. A disc of Chinese cabbage (Brassica pekinesis) leaves is sprayed with a preparation of the active compound at the desired concentration. Once dried, the leaf discs are swarmed with mustard beetle (Phaedon cochleariae) larvae.</p><p num="0410"> Measure mortality (%) after 7 days. 100% means that all beetle larvae have died, and 0% means that no beetle larvae have died.</p>

<p num="0411"> Spodoptera frugiperda-Test (SPODFR spray applied) Solvent: 78.0 parts by weight acetone 1.5 parts by weight dimethylformamide Emulsifier: 0.5 parts by weight alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with a predetermined amount of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing the emulsifier. .. Maize (Zea mais leaf sections are sprayed with the desired concentration of active ingredient preparation. Once dried, the leaf sections are larvae of the fall armyworm (Spodoptera frugiperda). ) Flock.</p><p num="0412"> Measure mortality (%) after 7 days. 100% means that all hornworms have died, and 0% means that no hornworms have died.</p>

<p num="0413"> Myzus persicae test (MYZUPE spray applied) Solvent: 78.0 parts by weight acetone 1.5 parts by weight dimethylformamide Emulsifier: 0.5 parts by weight alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with a predetermined amount of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing the emulsifier. .. Chinese cabbage (Brassica oleracea) leaf discs are infected with all-aged Myzus persicae and sprayed with the desired concentration of active ingredient preparation.</p><p num="0414"> Measure mortality (%) after 6 days. 100% means that all aphids have died, and 0% means that no aphids have died.</p>

<p num="0415"> Root-knot nematode test (MELGIN) Solvent: 80.0 parts by weight of acetone To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with a predetermined amount of solvent and the concentrate is diluted to the desired concentration with water containing an emulsifier.</p><p num="0416"> The container is filled with sand, a solution of the active ingredient, a suspension containing Meloidogyne incognita eggs and larvae, and salad seeds. Salad seeds germinate and seedlings grow. A hump develops in the root.</p><p num="0417"> After 14 days, nematode activity is measured based on the rate of hump formation. 100% meant that no humps were found, and 0% was equal to the number of humps found in the roots of the treated plant as in the untreated control plant. Means that.</p>

<p num="0418"> Tetranychus urticae-Test; OP resistant (TETRUR spray applied) Solvent: 78.0 parts by weight acetone 1.5 parts by weight dimethylformamide Emulsifier: 0.5 parts by weight alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with a predetermined amount of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing the emulsifier. .. The bean (Phaseolus vulgaris) is densely clustered with all-stage spider mite (two spotted spider mite) (Tetranychus urticae) and sprayed with the preparation of the active compound at the desired concentration.</p><p num="0419"> Measure mortality (%) after 6 days. 100% means that all spider mites have died, and 0% means that no spider mites have died at all.</p><p num="0420"><tables num="4"><img id="000029" he="64" wi="159" file="JP5771189B2_D0001.tif" img-format="tif" img-content="drawing" /></tables></p>