N-CYCLYLAMIDS AS NEMATICIDES, PESTICIDE AND PHARMACEUTICAL COMPOSITIONS UNDERSTANDING THEM AND THEIR

专利摘要:
n-cyclylamides as nematicides. the present invention relates to compounds of the formula (i), in which the substituents are as defined in claim 1, and are suitable for use as nematicides. the present invention also relates to compositions comprising said compound, a process for the preparation of said compound, a control method and a method of protecting plant propagating material from damage and / or loss of yield caused by a pest and / or fungi (particularly nematodes), to a method of controlling and preventing infestations and infections of endo- and ectoparasitic nematodes in warm-blooded animals. the present invention also relates to a plant propagation material treated with said compound and, further, to compounds of the formula (xixa).
公开号:BR112014023769B1
申请号:R112014023769-7
申请日:2013-03-06
公开日:2021-04-13
发明作者:Olivier Loiseleur；Torsten Luksch；Anthony Cornelius O'sullivan；Roman Staiger；Thomas Pitterna
申请人:Syngenta Participations Ag；
IPC主号:

专利说明:

[001] The present invention relates to the new cyclo-butylcarboxamide compounds, a process for the preparation of these compounds and their use as nematicides.
[002] Cycloalkylcarboxamides are described, for example, in WO 09/043784, WO06 / 122952, WO06 / 122955, WO05 / 103006, WO05 / 103004 and WO04 / 014842.
[003] New cyclobutylcarboxamides characterized by a cis-substituted cyclobutyl ring have now been discovered, which exhibit good nematicidal activity.
[004] The present invention thus relates to compounds of the formula I

[005] where
[006] Y is O, C = O, or CR12R13;
[007] A is a 5- or 6-membered heteroaromatic ring containing 1 to 3 heteroatoms, each independently selected from oxygen, nitrogen and sulfur, or a phenyl ring, in which the heteroaromatic ring or the phenyl ring is optionally substituted with one or more R6;
[008] R6 is independently halogen, cyano, C1- C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkyl, C1-C4-alkoxy- C1-C4-alkyl or C1-C4-haloalkoxy-C1-C4-alkyl;
[009] R1, R2, R3, R4, R12 and R13, independently of each other, are hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1- C4-haloalkyl;
[0010] R5 is hydrogen, methoxy or hydroxyl;
[0011] B is phenyl substituted with one or more R8;
[0012] R8 is, independently of one another, halogen, cyano or a -L-R9 group, where each L is, independently of each other, a bond, -O-, -OC (O) -, -NR7-, - NR7CO-, -NR7S (O) n-, -S (O) n-, -S (O) nNR7-, -COO- or CONR7-;
[0013] n is 0, 1 or 2;
[0014] R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, where benzyl and phenyl are not substituted or are substituted with halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl ;
[0015] R9 is, independently of one another, C1-C6-alkyl, which is not substituted or substituted with one or more R10, C3-C6-cycloalkyl, which is not substituted or is substituted with one or more R10, C6- C14-bicycloalkyl, which is not substituted or substituted with one or more R10, C2-C6-alkenyl, which is not substituted or substituted with one or more R10, C2-C6-alkynyl, which is not substituted or is substituted with one or more R10, phenyl, which is not substituted or substituted with R10, or heteroaryl, which is not substituted or substituted with one or more R10;
[0016] R10 is independently halogen, cyano, C1- C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-alkenyloxy, or C3-C6-alkynyloxy;
[0017] where B and A-CO-NR5 are cis to each other in the four-membered ring,
[0018] and tautomers / isomers / enantiomers of these compounds.
[0019] The compounds of the formula (I) and, where appropriate, their tautomers, in each case in free form or in the form of salt, may be present in the form of one of the isomers that are possible or as a mixture of these, for example example in the form of pure isomers, such as antipodes and / or diastereomers, or as mixtures of isomers, such as mixtures of enantiomers, for example racemates, mixtures of diastereomers or mixtures of racemates, depending on the number, absolute and relative configuration of the asymmetric carbon atoms that occur in the molecule and / or depending on the configuration of the non-aromatic double bonds that occur in the molecule; the invention relates to pure isomers and also to all mixtures of isomers that are possible and is to be understood in each case in this sense here above and here below, even when the stereochemical details are not specifically mentioned in each case. This invention accordingly covers all such isomers and tautomers and their mixtures in all proportions as well as isotopic forms such as deuterated compounds. As an example, the compounds of the invention may contain one or more asymmetric carbon atoms, for example, in the group -CR3R4or Y in - CR12CR13- or their substituents, and the compounds of the formula (I) can exist as enantiomers (or as pairs of diastereoisomers) or as mixtures thereof.
[0020] The invention also encompasses salts and N-oxides of each compound of the formula (I).
[0021] The person skilled in the art also recognizes that, because in the environment and under physiological conditions salts of chemical compounds are in balance with their corresponding non-salt forms, the salts share the biological utility of non-salt forms.
[0022] Thus, a wide variety of salts of compounds of the invention (and active ingredients used in combination with the active ingredients of the invention) can be useful for the control of invertebrate pests and parasites of animals. Salts between agriculturally and / or physiologically tolerable salts include acid addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric.
[0023] Among the suitable agriculturally and / or physiologically tolerable salts can also be the salts of those cations that do not adversely affect the pesticidal and / or parasiticidal action of the compounds of formula (I). Thus, especially suitable cations are the ions of alkali metals including sodium, potassium and lithium, alkaline earth metals including calcium and magnesium, and transition metals including manganese, copper, iron, zinc, cobalt, lead, silver, nickel, and also ammonium or organic ammonium including monoalkylammonium, dialkylammonium, trialkylammonium, tetraalkylammonium, monoalkenylammonium, dialkenylammonium, trialkylenylammonium, monoalquinylammonium, dialkynylammonium, monoalkylammonium, dialkylamino, cycloalkyl, pyridyl, pyridyl, pyridyl benzylammonium, in addition to more phosphonium ions, sulfonium ions, preferably tri (C1-C4-alkyl) sulfonium and sulfoxonium ions, preferably tri (C1-C4-alkyl) sulfoxonium.
The alkyl groups (either alone or as part of a larger group, such as alkoxy-, alkylsulfanyl-, alkylsulfinyl-, alkylsulfonyl-, alkylcarbonyl- or alkoxycarbonyl-) can be in the form of a linear or branched chain and they are, for example, methyl, ethyl, 1-propyl, prop-2-yl, 1-butyl, but-2-yl, or 2-methyl-prop-2-yl. The alkyl group (either alone or as part of a larger group, such as alkoxy-, alkylsulfanyl-, alkylsulfinyl-, alkylsulfonyl-, alkylcarbonyl- or alkoxycarbonyl-), in each embodiment of the invention, is preferably alkyl -C1-C3, more preferably C1-C2-alkyl, especially methyl group. In the case of alkoxy, examples are methoxy, ethoxy, propoxy, n-butoxy, isobutoxy and also their isomeric groups; preferably, independently of other embodiments, methoxy and ethoxy, especially methoxy.
[0025] Alkenyl groups may be in the form of straight or branched chains, and may have, where appropriate, the (E) or (Z) configuration. Examples are vinyl and ally. The alkenyl group, in each embodiment of the invention, is preferably a C2-C3 alkenyl group, more preferably a vinyl or allyl group.
[0026] Alquinyl groups can be in the form of straight or branched chains. Examples are ethinyl and propargyl. The alkynyl group, in each embodiment of the invention, is preferably a C2-C3 alkynyl group, more preferably a propargyl group.
[0027] Halogen is fluorine, chlorine, bromine or iodine; halogen, in each embodiment of the invention, is fluorine, chlorine, or bromine; especially fluorine or chlorine.
[0028] Haloalkyl groups (either alone or as part of a larger group, such as haloalkoxy-, haloalkylsulfanyl-, haloalkylsulfinyl- or haloalkylsulfonyl-) are alkyl groups that are substituted with one or more of the same or different halogen atoms and are, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl and 2,2,2-trifluoroethyl. The haloalkyl group (either alone or as part of a larger group, such as haloalkoxy-, haloalkylsulfanyl-, haloalkylsulfinyl- or haloalkylsulfonyl-), in each embodiment of the invention, is preferably trifluoromethyl. In the case of haloalkoxy, examples are fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2 -trichloroethoxy; preferably difluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy and trifluoromethoxy.
[0029] Cycloalkyl groups are monocyclic and are, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The C3-C6 cycloalkyl group, in each embodiment of the invention, is preferably a C3-C5 cycloalkyl group, more preferably a C3-C4 cycloalkyl group, especially a C3 cycloalkyl group. Where a cycloalkyl moiety is said to be substituted, the cycloalkyl moiety is preferably substituted with one to four substituents, more preferably with one to three substituents, such as one or two substituents, especially with one substituent.
[0030] Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl and tert-butoxycarbonyl; preferred are methoxycarbonyl, ethoxycarbonyl and isopropoxycarbonyl.
[0031] Alkylsulfanyl group is, for example, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, isobutylsulfanyl, sec-butylsulfanyl and tert-butylsulfanyl. Examples of haloalkylsulfanyl are its halogenated substituents with chlorine and / or fluorine, such as difluoromethylsulfanyl, trifluoromethylsulfanyl, chlorodifluoromethylsulfanyl and 2,2,2-trifluoroethylsulfanyl.
[0032] Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, and tert-butylsulfinyl. Examples of haloalkylsulfinyl are its chloro- and / or fluorohalogen substituents, such as difluoro-methylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl and 2,2,2-trifluoro-ethylsulfinyl.
The alkylsulfonyl group is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl. Examples of haloalkylsulfonyl are its chloro- and / or fluorohalogen substituents, such as difluoro-romethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl and 2,2,2-trifluoro-ethylsulfonyl.
[0034] Alkoxyalkyl is, for example, methoxymethyl, 2-methoxyethyl, ethoxymethyl, 2-ethoxyethyl, n-propoxymethyl, n-propoxy-2-ethyl, isopropoxymethyl and 1-isopropoxyethyl. The alkoxyalkyl group, in each embodiment of the invention, is preferably a C1-C4-C1-C4-alkoxy, more preferably a C1-C2-methyl-alkoxy, such as methoxymethyl and ethoxymethyl groups.
[0035] Aryl groups (either alone or as part of a larger group, such as arylalkylene-) are aromatic ring systems that can be mono-, bi- or tricyclic. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, with phenyl being the most preferred.
[0036] Examples of cycloalkylcarbonyl are cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl and cyclohexylcarbonyl; preferred are cyclopropylcarbonyl and cyclobutylcarbonyl.
[0037] Examples of cycloalkoxycarbonyl are cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl and cyclohexyloxycarbonyl; preferred are cyclopropyloxycarbonyl and cyclobutyloxycarbonyl.
[0038] The term "heteroaryl" refers to aromatic ring systems containing at least one heteroatom and consisting of a single ring or two fused rings. Preferably, single rings will contain up to 3 and bicyclic systems up to 5 heteroatoms, which will preferably be chosen from nitrogen, oxygen and sulfur. Examples of such groups include furyl, thienyl, 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, pyridine , pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzothiazolyl, benzisotiazolyl, benzisotiazolyl - zolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthy ridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl
[0039] It is possible that compounds of formula I have additional stereochemical centers, in the carbon carrying R3 and R4, or when Y is CR12R13, or in one of the substituents. Additional isomers are then possible. The invention encompasses all of these isomers and their mixtures.
[0040] The compounds of formula I can occur in different tautomeric forms. The invention encompasses all of these tautomeric forms and mixtures thereof.
[0041] Preferably, A is an optionally substituted 5- or 6-membered heteroaromatic ring, which preferably contains an oxygen atom or one or two nitrogen atoms, such as furyl, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl in particular pyridyl, or A is preferably an optionally substituted phenyl. In an embodiment of any embodiment of A, there are 1 to 3, preferably 1 or 2, R6 substituents on A.
[0042] More preferably, A is an optionally substituted 6-membered heteroaromatic ring, containing 1 or 2 nitrogen atoms (eg, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl, in particular pyridyl) or A is preferably a phenyl optionally replaced.
[0043] Preferred substituents (R6), independently of each other, and regardless of the type of ring, are selected from C1-C4-alkyl, C1-C4-haloalkyl (in particular di- and trifluoromethyl), C1-C4-haloalkoxy, cyan and halogen, in particular trifluoromethyl, fluorine and chlorine.
[0044] Most preferably, A, regardless of other embodiments, is pyridyl, pyrimidinyl, pyrazinyl, or phenyl, which can be unsubstituted or substituted with one or two R6 substituents, which can be independently selected from chlorine, fluorine, trifluoromethyl, methyl, bromine, and cyan.
[0045] The preferred connection point or points of these substitutes is ortho in relation to the connection point from A to C (O) NR5.
Preferred examples of A, regardless of other embodiments, are 2,6-difluorophenyl (A1); 3-chloro-2-pyrazinyl (A2); 3-trifluoromethyl-2-pyridyl (A3); 2-trifluoromethyl-3-pyridyl (A5); 2- trifluoromethyl-phenyl (A6); 2-chloro-3-pyridyl (A7); 3-methyl-2-pyridyl (A11); 2-methyl-3-pyridyl (A22); 3-methyl-2-pyrazinyl (A24); 3-bromo-2-pyrazinyl (A25); 3-trifluoromethyl-2-pyrazinyl (A26); and 2-cyanophenyl (A29).
[0047] The particularly preferred, regardless of other embodiments, is selected from 3-chloro-2-pyrazinyl (A2); 3-trifluoromethyl-2-pyridyl (A3); 2-trifluoromethyl-3-pyridyl (A5); 2- trifluoromethyl-phenyl (A6); 2-chloro-3-pyridyl (A7); 3-methyl-2-pyrazinyl (A24); 3-bromo-2-pyrazinyl (A25); and 3-trifluoromethyl-2-pyrazinyl (A26).
[0048] The especially preferred, regardless of other embodiments, is selected from 3-chloro-2-pyrazinyl (A2); 3-trifluoromethyl-2-pyridyl (A3); 2-trifluoromethyl-3-pyridyl (A5); 2- trifluoromethyl-phenyl (A6); 2-chloro-3-pyridyl (A7); and 3-trifluoromethyl-2-pyrazinyl (A26); advantageously 3-chloro-2-pyrazinyl (A2); 2-trifluoromethyl-3-pyridyl (A5); 2-trifluoromethyl-phenyl (A6); and 3-trifluoromethyl-2-pyrazinyl (A26).
[0049] Preferably, Y is O or CR12R13, where R12 and R13 are, independently of each other, hydrogen, halogen, cyano, C1- C4-alkyl or C1-C4-haloalkyl. In one embodiment, regardless of other embodiments, R12 and R13 are both hydrogen.
[0050] Preferably, R1, R2, R3 and R4 are, independently of each other, hydrogen, halogen, C1-C4-alkyl or halo-C1-C4-haloalkyl. In one embodiment, independent of other embodiments, R1, R2, R3 and R4 are each hydrogen.
[0051] In one embodiment, when Y is CR12R13, five or six of R1, R2, R3, R4, R12 and R13 are hydrogen. In a preferred embodiment, Y is CR12R13, so R1, R3, R4, R12 and R13 are each hydrogen, and R2 is cyano or C1-C4-alkoxy, as methoxy.
[0052] In one embodiment, when Y is O, each of R1, R2, R3 and R4 is hydrogen.
[0053] Preferably, R5 is hydrogen.
[0054] B is phenyl substituted with substituents (R8). In one case, there are 1 to 3 R8 substituents on B. Preferably, the R8 substituent, independently of each other, is selected from halogen, cyano, C1- C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1- C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, cyclopropyl, cyclobutyl, cyclopentyl, C1- C4-haloalkyl-C3-C6-cycloalkyl, phenyl, phenoxy, cyclopentyloxy, ally, propylene, propylene, allyloxy C1-C4-alkylsulfoxide, C1-C4-haloalkylsulfoxide, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylsulfonylamino, propargylsulfonylamino, cyclopropylsulfonamino, cyclobutylsulfonyl, pyridylamino, pyridyl, pyridyl, pyridine pyridyloxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, pyridylcarbonyl, pyridyloxycarbonyl, pyridylcarbonyloxy, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyloxy, cyclopentyloxycarbonyl, alkyloxycarbonyl, alkyloxycarbonyl, propyloxycarbonyl, propyloxycarbonyl, propyloxycarbonyl, propyloxycarbonyl, propyl ci clopentilamino, fenilaminossulfonila, C1-C4-alquilaminossulfonila, ciclopentilaminossulfonila, piridilaminos- sulfonyl, alilaminossulfonila, propargilaminossulfonila, phenylamino, dilamino piri-, allylamino, propargylamino, fenilaminocarbonila, carbonyl piridilamino-, ciclopentilaminocarbonila, phenylcarbonylamino, alkylamino piridilcarboni-, alilcarbonilamino propargilcarbonilamino and wherein these substituents, independently of each other, may not be substituted, or, when possible, may be additionally substituted with one or more substituents (R10). The substituent R10, independently selected from each other, is preferably selected from C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-alkylthio and halogen.
[0055] In one embodiment, regardless of other embodiments, B is a phenyl group substituted with 1 to 3 substituents, independently selected from halogen, cyano, C1-C4-haloalkyl, C1-C4-haloalkoxy, and C3- C6-cycloalkyl. In a preferred embodiment, the substituents are independently selected from bromine, chlorine, fluorine, trifluoromethyl, difluoromethoxy, trifluoromethoxy and cyclopropyl.
[0056] In a group of preferred compounds of formula I, B is a phenyl group, substituted with 1 to 3 substituents, independently selected from halogen, cyclopropyl, C1-C4-haloalkylcyclopropyl, C1-C4-haloalkyl and C1-C4-haloalkoxy , A is a phenyl, furyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl group, whose rings, independently of each other, are not substituted or are substituted with 1 to 3 substituents, independently selected from C1-C4-alkyl, C1-C4-haloalkyl , C1-C4-alkoxy, C1-C4-haloalkoxy, cyano and halogen, Y is O or CH2, and R1, R2, R3, R4 and R5 are hydrogen. In this group of compounds of formula I, B is especially a phenyl substituted with 1 to 3 substituents, independently selected from fluorine, chlorine, bromine, trifluoromethyl and trifluoromethoxy. In that group of compounds of formula I, A is especially a phenyl, pyridyl, pyrazinyl or pyrimidinyl group, whose rings, independently of each other, are not substituted or are substituted with 1 to 3 substituents, independently selected from fluoro, methyl and trifluoromethyl.
[0057] In another group of preferred compounds of formula I, B is a phenyl group substituted with 1 to 3 substituents, independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, trifluoromethylcyclopropyl, difluoromethoxy or trifluoromethoxy, A is a phenyl group, pyridyl or pyrazinyl, whose rings, independently of each other, are not substituted or are substituted with 1 to 3 substituents, independently selected from chlorine, bromine, fluoro, methyl, cyano, and trifluoromethyl, Y is O or CH2, and R1, R2, R3, R4 and R5 are hydrogen. More preferably, in this group of compounds of formula I, B is especially a phenyl group substituted with 1 to 3 substitutents, independently selected from fluoro, chloro, difluoromeotoxy or trifluoromethoxy, A is especially a phenyl, pyrazinyl or pyridyl group, whose rings, independently of each other, are substituted with 1 to 3 substituents, independently selected from chlorine, fluoro, methyl and trifluoromethyl.
[0058] In an especially preferred group of compounds of formula I, B is a phenyl group substituted with 1 to 3 substituents, independently selected from halogen, C1-C4-haloalkyl, and C1-C4-haloalkoxy; A is phenyl, pyridyl or pyrazinyl, whose rings, independently of each other, are monosubstituted with a halogen or C1-C4-haloalkyl; Y is O or CH2; and R1, R2, R3, R4 and R5 are hydrogen. More preferably, in that group of compounds of formula I, B is especially a phenyl group substituted with 1 to 2 substituents, independently selected from fluoro, chloro, trifluoromethyl, difluoromethoxy and trifluoromethoxy; A is especially a phenyl, pyrazinyl or pyridyl group, whose rings are monosubstituted with chlorine, fluoro or trifluoromethyl substituents.
[0059] In a particularly preferred embodiment, a compound of formula I is such that Y is CH2; B is phenyl substituted with mono- or dihalogen; R1 to R5 are each hydrogen and A is selected from phenyl, pyrazinyl or pyridyl, each of which is mono- or disubstituted, independently of each other, with substitutes independently selected from halogen and C1-C4-haloalkyl, preferably A is monosubstituted.
[0060] Compounds of formula I can be prepared by reacting a compound of formula II

[0061] where B, Y, R1, R2, R3, R4 and R5 are as defined in formula I; with an acylating agent of the formula III A-C (= O) -R * (III),
[0062] where A is as defined under formula I, and R * is halogen, hydroxy or C1-6 alkoxy, preferably chlorine, in the presence of a base, such as triethylamine, Hunig's base, sodium bicarbonate, sodium carbonate , potassium carbonate, pyridine or quinoline, but preferably triethylamine, and generally in a solvent, such as diethyl ether, TBME, THF, dichloromethane, chloroform, DMF or NMP, for between 10 minutes and 48 hours, preferably 12 to 24 hours , and between 0 o C and reflux, preferably 20 to 25 o C.
[0063] When R * is hydroxyl, an coupling agent, such as benzotriazol-1-yloxitris (dimethylamino) phosphonium hexafluorophosphate, bis- (2-oxo-3-oxazolidinyl) -phosphinic acid (BOP) -Cl), N, N'-dicyclohexylcarbodiimide (DCC) or 1,1'-carbonyl-diimidazole (CDI).
[0064] Compounds of formula IIc where B is as defined in formula I, Y is CH2 and R1, R2, R3 and R4 are H can be prepared from ketone XVIII. This can be accomplished by conversion to the XIX oxime and reduction. DE Nichols et al. (J. Med. Chem 1984, 27, 1108-11) describe methods for this reduction. Certain methods can give rise to trans isomers as by-products.

[0065] Compounds of formula 1e can be prepared by cycloaddition 2 + 2 of aldehydes of formula (VIII) and enamides of formula (Va). This can be done with the aid of UV radiation as described by Bach et al. (Journal of Organic Chemistry (1999), 64 (4), 12651273). They can be accompanied by their trans isomers.

[0066] For the preparation of all additional compounds of formula I functionalized according to the definitions of A, B, R1, R2, R3, R4, R5 and R12 and R13 there are a large number of suitable known standard methods, such as alkylation, halogenation, acylation, amidation, oxidation, oxidation and reduction. The choice of preparation methods that are suitable depends on the properties (reactivity) of the substituents on the intermediates.
[0067] These reactions can be conveniently carried out in a solvent.
[0068] These reactions can be conveniently carried out at various temperatures.
[0069] These reactions can be conveniently carried out in an inert atmosphere.
[0070] Reagents can react in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, metal carbonates alkali or alkaline earth metals, dialkylamides of alkali metals or alkaline earth metals or alkylsilylamides of alkali metals or alkaline earth metals, alkylamines, alkylene diamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbonic hydroxides. Examples that can be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, di- lithium isopropylamide, potassium bis (trimethylsilyl) amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N, N-dimethylamine, N, N-diethylaniline, pyridine, 4- (N, N-dimethylamino) pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).
The reagents can react with each other as such, i.e., without adding a solvent or diluent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. If the reaction is carried out in the presence of a base, bases that can be used in excess, such as triethylamine, pyridine, N-methylmorpholine or N, N-diethylaniline, can also act as solvents or diluents.
[0072] The reaction is advantageously carried out in a temperature range from approximately -80 ° C to approximately +140 ° C, preferably from approximately -30 ° C to approximately +100 ° C, and in many cases in the range between at room temperature and approximately +80 ° C.
[0073] A compound of the formula (I) can be converted in a manner known per se to another compound of the formula (I) by substituting one or more substituents of the starting compound of the formula (I) in the usual way for another (s) ) substituent (s) according to the invention.
[0074] Depending on the conditions of the reactions and starting materials chosen, which are appropriate for each case, it is possible, for example, in a reaction step to substitute only one substitute for another substituent according to the invention, or a plurality of substituents can be replaced by other substituents according to the invention in the same step of the reaction.
[0075] The salts of the compounds of the formula (I) can be prepared in a manner known per se. Thus, for example, acid addition salts of the compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion exchange reagent and salts with bases are obtained by treatment with a suitable base or an ion exchange reagent adequate. A salt is chosen depending on your tolerances regarding the use of the compost, such as agricultural or physiological tolerance.
[0076] The salts of the compounds of the formula (I) can be converted in the usual way to the free compounds I, the acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchange reagent and the base salts, for example, by treatment with a suitable acid or a suitable ion exchange reagent.
[0077] The salts of the compounds of the formula (I) can be converted in a manner known per se to other salts of the compounds of the formula (I), the acid addition salts, for example, in other acid addition salts, for example, by treating an inorganic acid salt such as hydrochloride with an appropriate metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which a salt inorganic form, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.
[0078] Depending on the procedure or the conditions of the reactions, the compounds of formula (I), which have salt-forming properties, can be obtained in free form or in the form of salts.
[0079] Mixtures of diastereomers or mixtures of racemates of the compounds of formula (I), in free form or in salt form, which can be obtained depending on which starting materials and procedures were chosen, can be separated in a different way known in pure diastereomers or racemates based on the physicochemical differences of the components, for example by fractional crystallization, distillation and / or chromatography.
[0080] Mixtures of enantiomers, such as racemates, which can be obtained in a similar way, can be resolved in optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents , for example high performance liquid chromatography (HPLC) in acetylcellulose, with the aid of suitable microorganisms, by cleavage with specific immobilized enzymes, through the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer forms a complex, or by conversion to diastereomeric salts, for example by reaction of a basic final product racemate with an optically active acid such as a carboxylic acid, for example camphoric, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid , and separation of the mixture of diastereomers that can be obtained in this way, for example by fractional crystallization based on their s different solubilities, to give the diastereomers, from which the desired enantiomer can be released by the action of suitable agents, for example basic agents.
[0081] Diastereomers or pure enantiomers can be obtained according to the invention not only by separating appropriate mixtures of isomers, but also by methods known in general of diastereoselective or enantioselective synthesis, for example, when carrying out the process according to the invention with starting materials showing appropriate stereochemistry.
[0082] N-oxides can be prepared by reacting a compound of formula (I) with a suitable oxidizing agent, for example the adduct of H2O2 / urea in the presence of an acid anhydride, eg trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem., 32 (12), 2561-73, 1989 or WO 00/15615 or C. White, Science, vol 318, p.783, 2007.
[0083] It may be advantageous to isolate or synthesize the isomer in each case, for example enantiomer or diastereomer, or mixture of isomers, for example mixture of enantiomers or mixture of diastereomers, biologically more effective, if the individual components have a different biological activity.
[0084] The compounds of formula (I) and, where appropriate, their tautomers, in each case in free form or in salt form, may, if appropriate, also be obtained in the form of hydrates and / or include other solvents, for example those that may have been used for the crystallization of compounds that are present in solid form.
[0085] The invention is additionally directed to intermediate compounds having the formulas (II), and (XIXa), which can be used in the preparation of the compounds of the formula (I).
Accordingly, the present invention makes available a compound of the formula (II)

[0087] where
[0088] Y is O, C = O, or CR12R13;
[0089] R1, R2, R3, R4, R12 and R13, independently of each other, are hydrogen, halogen, cyan, C1-C4-alkyl or C1-C4-haloalkyl,
[0090] R5 is hydrogen, methoxy or hydroxyl,
[0091] B is phenyl substituted with one or more R8,
[0092] R8 is, independently of one another, halogen, cyano or a -L-R9 group, where each L is, independently of each other, a bond, -O-, -OC (O) -, -NR7-, - NR7CO-, -NR7S (O) n-, -S (O) n-, -S (O) nNR7-, -COO- or CONR7-,
[0093] n is 0, 1 or 2,
[0094] R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, where benzyl and phenyl are not substituted or are substituted with halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl ,
[0095] R9 is, independently of one another, C1-C6-alkyl, which is not substituted or is substituted with one or more R10, C3-C6-cycloalkyl, which is not substituted or is substituted with one or more R10, C6- C14-bicycloalkyl, which is not substituted or substituted with one or more R10, C2-C6-alkenyl, which is not substituted or substituted with one or more R10, C2-C6-alkynyl, which is not substituted or is substituted with one or more R10, phenyl, which is not substituted or substituted with R10, or heteroaryl, which is not substituted or substituted with one or more R10,
[0096] R10 is, independently of one another, halogen, cyano, C1- C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-alkenyloxy, or C3-C6-alkynyloxy, provided that B and A-CO-NR5 are cis to each other in the four-membered ring, where the compound of the formula

[0097] is excluded.
[0098] In a preferred embodiment, any preferred substitute of formula (I) in connection with each of B, Y, R1, R2, R3, R4, and R5 is also a preferred substituent, regardless of the formula ( I), for formula (II) in the context of B, Y, R1, R2, R3, R4, and R5, respectively.
[0099] In particular, Y is CH2, R1 to R5 are each hydrogen and B is a phenyl group, substituted with 1 to 3 substituents, independently selected from halogen, cyclopropyl, C1-C4-haloalkylcyclopropyl, C1-C4- haloalkyl and C1-C4-haloalkoxy.
[00100] In a particular embodiment, Y is CH2, R1 to R5 are each hydrogen and B is a phenyl group substituted with 1 to 3 substituents, independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, trifluoromethylcyclopropyl and trifluoromethoxy.
[00101] In a particularly preferred embodiment, Y is CH2, R1 through R5 are each hydrogen and B is a mono or dihalogen-substituted phenyl group.
[00102] The present invention also makes available a compound of the formula (XIXa)

[00103] where
[00104] Y is O, C = O, or CR12R13;
[00105] R1, R3, and R4 independently of each other, are hydrogen, halogen, cyan, C1-C4-alkyl or C1-C4-haloalkyl,
[00106] B is phenyl substituted with one or more R8,
[00107] R8 is, independently of one another, halogen, cyano or a -L-R9 group, where each L is, independently of each other, a bond, -O-, -OC (O) -, -NR7-, - NR7CO-, -NR7S (O) n-, -S (O) n-, -S (O) nNR7-, -COO- or CONR7-,
[00108] n is 0, 1 or 2,
[00109] R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, where benzyl and phenyl are not substituted or are substituted with halogen, cyan, C1-C4-alkyl or C1-C4-haloalkyl ,
[00110] R9 is, independently of one another, C1-C6-alkyl, which is not substituted or substituted with one or more R10, C3 – C6- cycloalkyl, which is not substituted or is substituted with one or more R10, C6– C14-bicycloalkyl, which is not substituted or substituted with one or more R10, C2-C6-alkenyl, which is not substituted or substituted with one or more R10, C2-C6-alkynyl, which is not substituted or is substituted with one or more R10, phenyl, which is not substituted or substituted with R10, or heteroaryl, which is not substituted or substituted with one or more R10,
[00111] R10 is independently halogen, cyano, C1- C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C3-C6-alkenyloxy, or C3-C6-alkynyloxy, provided that B and A-CO-NR5 are cis to each other in the four-membered ring; in which the compounds of the formulas

[00112] are excluded.
[00113] In a preferred embodiment, any preferred substitute of formula (I) in connection with each of B, Y, R1, R3, and R4, is also a preferred substituent, regardless of formula (I), for formula (XIXa) in the context of B, Y, R1, R3, and R4, respectively.
[00114] In particular, Y is CH2, R1 R3 and R4 are each hydrogen and B is a phenyl group, substituted with 1 to 3 substituents, independently selected from halogen, cyclopropyl, C1-C4-haloalkylcyclopropyl, C1-C4 -haloalkyl and C1-C4-haloalkoxy.
[00115] In a particular embodiment, Y is CH2, R1, R3 and R4 are each hydrogen and B is a phenyl group substituted with 1 to 3 substituents, independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, trifluoromethylcyclopropyl and trifluoromethoxy.
[00116] In a particularly preferred embodiment, Y is CH2, R1, R3 and R4 are each hydrogen and B is a mono or dihalogen-substituted phenyl group. TABLES 1 TO 33: COMPOUNDS OF FORMULA IA
[00117] The invention is further illustrated by making available the following individual compounds of the formula (IA) listed below in Tables 1 to 33.

[00118] Each of Tables 1 to 33, following Table Y below, makes available 163 compounds of the formula (IA) in which Y, R1, R2, R3, R4, R9a, R9b and R9c are the defined substituents in Table Y and A is the relevant substituent defined in Table 1 to 33. Thus, Table 1 individualizes 163 compounds of the formula (IA) in which, for each row in Table Y, the substituent A is as defined in Table 1; similarly, Table 2 individualizes 163 compounds of the formula (IA) in which, for each row in Table Y, substituent A is as defined in Table 2; and so on for Tables 3 through 33. TABLE Y







[00119] Table 1 provides 163 compounds of the formula (IA), where A is

[00120] (2,6-difluorophenyl) where the dashed line indicates the point of attachment of the group A to the amide group, and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each line of the Table Y. For example, compound 1.001 has the following structure:

[00121] Table 2 provides 163 compounds of the formula (IA), where A is 3-chloro-2-pyrazinyl (A2) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00122] Table 3 provides 163 compounds of the formula (IA), where A is 3-trifluoromethyl-2-pyridyl (A3) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00123] Table 4 provides 163 compounds of the formula (IA), where A is 3-chloro-2-pyridyl (A4) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00124] Table 5 provides 163 compounds of the formula (IA), where A is 2-trifluoromethyl-3-pyridyl (A5) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00125] Table 6 provides 163 compounds of the formula (IA), where A is 2-trifluoromethyl-phenyl (A6) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00126] Table 7 provides 163 compounds of the formula (IA), where A is 2-chloro-3-pyridyl (A7) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00127] Table 8 provides 163 compounds of the formula (IA), where A is 2-fluoro-6-trifluoromethyl-phenyl (A8) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00128] Table 9 provides 163 compounds of the formula (IA), where A is 2-tolyl (A9) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y .

[00129] Table 10 provides 163 compounds of the formula (IA), where A is 2-pyrimidinyl (A10) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y .

[00130] Table 11 provides 163 compounds of the formula (IA), where A is 3-methyl-2-pyridyl (A11) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00131] Table 12 provides 163 compounds of the formula (IA), where A is 2-fluorophenyl (A12) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y .

[00132] Table 13 provides 163 compounds of the formula (IA), where A is 2-chlorophenyl (A13) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y .

[00133] Table 14 provides 163 compounds of the formula (IA), where A is 2-bromophenyl (A14) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y .

[00134] Table 15 provides 163 compounds of the formula (IA), where A is 2-iodophenyl (A15) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y .

[00135] Table 16 provides 163 compounds of the formula (IA), where A is 2,6-dichlorophenyl (A16) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each line of the Table Y.

[00136] Table 17 provides 163 compounds of the formula (IA), where A is 2-chloro-6-fluoro-phenyl (A17) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00137] Table 18 provides 163 compounds of the formula (IA), where A is 2,4,6-trifluorophenyl (A18) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00138] Table 19 provides 163 compounds of the formula (IA), where A is 2-trifluoromethoxy-phenyl (A19) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00139] Table 20 provides 163 compounds of the formula (IA), where A is 2-fluoro-6-methyl-phenyl (A20) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00140] Table 21 provides 163 compounds of the formula (IA), where A is 2-fluoro-6-methoxy-phenyl (A21) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00141] Table 22 provides 163 compounds of the formula (IA), where A is 2-methyl-3-pyridyl (A22) and R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00142] Table 23 provides 163 compounds of the formula (IA), where A is 3-fluoro-2-pyridyl (A23) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00143] Table 24 provides 163 compounds of the formula (IA), where A is 3-methyl-2-pyrazinyl (A24) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00144] Table 25 provides 163 compounds of the formula (IA), where A is 3-bromo-2-pyrazinyl (A25) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00145] Table 26 provides 163 compounds of the formula (IA), where A is 3-trifluoromethyl-2-pyrazinyl (A26) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00146] Table 27 provides 163 compounds of the formula (IA), where A is 2-methyl-3-furyl (A27) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00147] Table 28 provides 163 compounds of the formula (IA), where A is 5-chloro-4-pyrimidinyl (A28) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00148] Table 29 provides 163 compounds of the formula (IA), where A is 2-cyanophenyl (A29) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y .

[00149] Table 30 provides 163 compounds of the formula (IA), where A is 2-trifluoromethylthio-phenyl (A30) and Y, R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00150] Table 31 provides 163 compounds of the formula (IA), where A is 2-fluoro-3-pyridyl (A31) and Y, RI, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00151] Table 32 provides 163 compounds of the formula (IA), where A is 3- (difluoromethyl) -1-methyl-pyrazol-4-yl (A32) and R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00152] Table 33 provides 163 compounds of the formula (IA), where A is 3- (trifluoromethyl) -1-methyl-pyrazol-4-yl (A33) and R1, R2, R3, R4, R9a, R9b and R9c are as defined in each row of Table Y.

[00153] Examples of the formula (II) made available are those where the substituents B, Y, R1, R2, R3, R4 and R5 in the formula (II) correspond to each row in Table Y above in the context of the formula (Ia). Thus, for example, a compound of formula (II) in the context of line Y.001 is such that B is 4-chloro phenyl; Y is CH2; and R1 through R5 are each hydrogen.
[00154] Examples of the formula (XIXa) made available are those where the substituents B, Y, R1, R2, R3, and R4 in the formula (XIXa) correspond to each row in Table Y above in the context of the formula (Ia). Thus, for example, a compound of the formula (XIXa) in the context of the Y.001 line is such that B is 4-chloro phenyl; Y is CH2; and R1 through R4 are each hydrogen.
[00155] A compound of formula (I) has been found to control damage caused by a pest and / or fungi.
[00156] In one embodiment, a compound of the formula (I) can be used in agriculture.
[00157] Accordingly, the invention is furthermore directed to a method of controlling damage and / or loss of yield caused by a pest and / or fungi comprising application to a pest, a locus of a pest, or a plant susceptible to attack by a pest and / or fungi or plant propagating material of an effective amount of a compound of formula (I).
[00158] The compounds according to the invention can be used for control, ie, containment or destruction, of pests and / or fungi that occur in particular on plants, especially useful plants and ornamental plants in agriculture, horticulture and in forests, or on organs, such as fruits, flowers, foliage, stems, tubers, seeds or roots, from such plants, and in some cases even plant organs that are formed at a later time remain protected from these pests.
[00159] The compounds of the formula (I) according to the invention are active ingredients preventively and / or curatively valuable in the area of pest control, even at low rates of application, which can be used against pests and fungi resistant to pesticides, whose compounds of formula (I) have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants.
[00160] The compounds according to the invention can act in all stages of development or in individual stages of development of pests of animals normally sensitive, but also resistant, such as insects or representatives of the order Acari. The insecticidal or acaricidal activity of the compounds according to the invention can manifest itself directly, ie, in the destruction of the pests, which takes place either immediately or only after some time has passed, for example during ecdysis, or indirectly, for example in a reduced oviposition and / or hatching rate, with good activity corresponding to a destruction rate (mortality) of at least 50 to 60%.
[00161] It has now been discovered that the compounds of the formula I according to the invention have, for practical purposes, a very advantageous spectrum of activities for the protection of useful animals and plants against attack and damage by nematodes. Accordingly, the present invention also provides a nematicidal composition comprising compounds of the invention, as of formula (I).
[00162] The compounds of formula (I) are especially useful for the control of nematodes. Thus, in an additional aspect, the invention also relates to a method of controlling damage to plants and their parts by plant parasitic nematodes (Endoparasitic, Semiendoparasitic and Ectoparasitic nematodes), especially plant parasitic nematodes such as nematodes from the root nodule, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other species of Molidogyne; cyst-forming nematodes, Globodera rostochiensis and other species of Globodera; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other species of Heterodera; Nematodes from seed galls, species from Angola; Stem and leaf nematodes, Aphelenchoid species; Nematodes of the roots stylets, Eelonolaimus longicaudatus and other species of Belonolaimus; Nematodes of pine trees, Bur- saphelenchus xylophilus and other species of Bursaphelenchus; Ringed nematodes, species of Criconema, species of Criconemella, species of Criconemoides, species of Mesocriconema; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl-shaped nematodes, Dolichodorus species; Spiraled nematodes, Heliocotylenchus multicinctus and other species of Helicotylenchus; Sheathoid and sheathoid nematodes, species of Hemicycliophora and species of Hemiciconiconides; Hirshmanniella species; Lanceolated nematodes, Hoploaimus species; False nematodes of root galls, Nacobbus species; Needle-shaped nematodes, Longidorus elongatus and other species of Longidorus; Stiletto nematodes, species of Pratylenchus; Lesion-forming nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvita- tus, Pratylenchus goodeyi and other species of Pratylenchus; Cavernous nematodes, Radopholus similis and other species of Radodphus; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other species of Rotylenchus; species of Scutellonema; Root shortening and thickening nematodes, Trichodromus primitivus and other species of Trichodorus, species of Parathorchodorus; Stem nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other species of Tylenchorhynchus; Citrus nematodes, species of Tylenchulus; Dagger-shaped nematodes, Xiphinema species; and other species of plant parasitic nematodes, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quini-sulcius spp ..
[00163] Particularly, the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp. and Pratylenchus spp. can be controlled by compounds of the invention. EXAMPLES OF ANIMAL PESTS ARE: - of the order Acarina, for example,
[00164] Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gall, Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp, Hyalomma spp., Ixodes spp., Olygonychus spp., Ornithodoros spp., Polyphagotarsone latus, Panonychus spp. ., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp, Tarsonemus spp. and Tetranychus spp .; - from the Anoplura order, for example,
[00165] Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp .; - of the order Coleoptera, for example,
[00166] Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp., Curinis nitp. , Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, La- gria vilosa, Leptinotarsa sp. Megascelis spp, Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp, Phlyctinus spp., Popillia spp. spp., Somaticus spp, Sphenophorus spp, Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp .; - of the order Diptera, for example,
[00167] Aedes spp., Anopheles spp, Antherigona soccata, Bactracea oleae, Bibio hortulanus, Bradysia spp, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypoderma spp., Hyp- pobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia ., Oscinella frit, Pegomyia hycoscami, Phorbia spp., Rhagoletis spp, Rivelia quadrifasciata, Scatella spp, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp .; - of the Hemiptera order, for example,
[00168] Acanthocoris scabrator, Acrosternum spp, Adelphocoris liolol, Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp. ., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcías nobilellus, Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic, Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp., Nysius spans. Piezodorus spp, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinaphara spp., Thyanta spp, Triatoma spp., Vatiga illudens; - of the order Homoptera, for example,
[00169] Acyrthosium pisum, Adalges spp, Agalliana ensigera, Agnoscena targionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus spp. ., Aulacorthum solani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cava-riella aegopodi-i Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictypad, Crypuspica, , Coccus hesperidum, Dalbulus mai- dis, Dialeurodes spp, Diaphorina citri, Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp. Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp, Met prude pollen, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myri-cae, Parlatrice, Paratrio, Paratrio, Paratrio spp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp. , Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp, Trialeu- rodes spp, Tridiscus spp. citri, Zygina flammigera, Zyginidia scutellaris; - of the order Hymenoptera, for example,
[00170] Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp, Sle- nopsis invic . and Vespa spp .; - of the order Isoptera, for example,
[00171] Coptotermes spp, Corniternes cumulans, Incisitermes spp, Macrotermes spp, Mastotermes spp, Microtermes spp, Reticulitermes spp .; Solenopsis geminate; - of the order Lepidoptera, for example,
[00172] Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp., Autyrphaenia spp., Autographa spp., Bucculatrix thurberiella, Busse Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp. binotalis, Cryptophlebia leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp. spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp, Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis, Lithocollis sp. botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolism spea. Papaipema nebris, Pectinophora gossypiela, Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaea operculetula, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp. Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta, and Yponomeuta spp .; - of the order Mallophaga, for example,
[00173] Damalinea spp. and Trichodectes spp .; - of the order Orthoptera, for example,
[00174] Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscus spp, and Schistocerca spp .; - of the order Psocoptera, for example,
[00175] Liposcelis spp .; - of the order Siphonaptera, for example,
[00176] Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; - of the order Thysanoptera, for example,
[00177] Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii, Sericcothrips variabilis, Taeniothrips spp., Thrips spp; - of the order Thysanura, for example,
[00178] Lepisma saccharina.
[00179] In an additional aspect, the invention can also relate to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, in which a compound of formula (I) is applied as an active ingredient to plants, to their parts or its locus. The compounds of the formula (I) according to the invention are distinguished by their activity, for being well tolerated by plants and for being environmentally safe. They have very useful healing, preventive and systemic properties and are used to protect numerous useful plants. The compounds of formula (I) can be used to inhibit or destroy diseases that occur in plants or parts of plants (fruit, flowers, leaves, stems, tubers, roots) of different useful plants, while at the same time also protecting those parts of plants that grow later, eg of phytopathogenic microorganisms. It is also possible to use the compounds of the formula (I) as treatment agents for the treatment of plant propagating material, in particular seeds (fruits, tubers, grains) and plant cuttings (eg, rice), for protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
[00180] Examples of fungi include: Fungi imperfecti (for example, Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria); Basidiomycetes (for example, Rhizoctonia, Hemileia, Puccinia); the Ascomycetes classes (for example, Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula); Oomycetes classes (for example, Phytophthora, Pythium, Plasmopara); Zygomycetes (for example, Rhizopus spp.); family Phakopsoraceae, particularly those of the genus Phakopsora, for example, Phakopsora pachyrhizi, which is also referred to as Asian soybean rust, and those of the Pucciniaceae family, particularly those of the genus Puccinia, such as Puccinia graminis, also known as stem rust or rust black, which is a problematic disease in cereal plants, and Puccinia recondita, also known as brown rust.
[00181] Among the plants and the possible diseases of these plants protected by the method according to the present invention, mention may be made of:
[00182] - wheat, with regard to the control of the following seed diseases: Fusarium wilt (Microdochium nivale and Fusarium roseum), smelly pouch (Tilletia caries, Tilletia controversa or Tilletia indica), septoriosis disease (Septoria nodorum) and loose pouch;
[00183] - wheat, with regard to the following diseases of the aerial parts of the plant: cereal bedding (Tapesia yallundae, Tapesia acuformis), rot (Gaeumannomyces graminis), foot plague (F. culmo-rum, F. graminearum), black spot (Rhizoctonia cerealis), powdery mildew (Erysiphe graminis forms specie tritici), rust (Puccinia striiformis and Puccinia recondita) and septoriosis diseases (Septoria tritici and Septoria nodorum);
[00184] - wheat and barley, with regard to the control of bacterial and viral diseases, for example yellow mosaic of barley; - barley, with regard to the control of the following seed diseases: spot-reticular (Pyrenophora graminea, Pyrenophora teres and Cochliobolus sativus), loose pouch (Ustilago nuda) and fusarium wilt (Microdochium nivale and Fusarium roseum);
[00185] - barley, with regard to the control of the following areas of the aerial parts of the plant: cereal bedding (Tapesia yallundae), spot-reticular (Pyrenophora teres and Cochliobolus sati- vus), powdery mildew (Erysiphe graminis forma specie hordei ), forage of dwarf leaves (Puccinia hordei) and leaf spot (Rhynchosporium secalis);
[00186] - potato, with regard to the control of diseases of the tubers (in particular Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fusarium solani), downy mildew (Phytopthora infestans) and certain viruses (Y virus);
[00187] - potato, with regard to the control of the following types of foliage: black spot (Alternaria solani), downy mildew (Phytophthora infestans);
[00188] - cotton, with regard to the control of the following diseases of young plants grown from seeds: tipping and rot (Rhizoctonia solani, Fusarium oxysporum) and black root rot (Thielaviopsis basicola);
[00189] - plants that originate proteins, for example peas, with regard to the control of the following seed diseases: anthracnose (Ascochyta pisi, Mycosphaerella pinodes), fusarium wilt (Fusarium oxysporum), gray mold (Botrytis cinerea) and downy mildew (Peronospora pisi);
[00190] - oilseed plants, for example rapeseed, with regard to the control of the following seed diseases: Phoma lingam, Alternaria brassicae and Sclerotinia sclerotiorum;
[00191] - corn, with regard to the control of diseases of the mind: (Rhizopus sp., Penicillium sp.,
[00192] Trichoderma sp., Aspergillus sp., And Gibber ellafujikuroi);
[00193] - flax, with regard to the control of the disease of minds: Alternaria linicola;
[00194] - forest trees, with regard to the control of tipping (Fusarium oxysporum, Rhizoctonia solani);
[00195] - rice, with regard to the control of the following diseases of the aerial parts: blast (Magnaporthe grisea), mela (Rhizoctonia solani);
[00196] - leguminous plants, with regard to the control of the following diseases of seeds or young plants grown from seeds: tipping and rot (Fusarium oxysporum, Fusarium roseum, Rhizoctonia solani, Pythium sp.);
[00197] - leguminous plants, with regard to the control of the following aerial part diseases: gray mold (Botrytis sp.), Powdery mildew (in particular Erysiphe cichoracearum, Sphaerotheca fuliginea and Leveillula taurica), fusarium wilt (Fusarium oxysporum , Fusarium roseum), leaf spot (Cladosporium sp.), Alternaria leaf spot (Alternaria sp.), Anthracnose (Colletotrichum sp.), Septic leaf spot (Septoria sp.), Black spot (Rhizoctonia solani), downy mildew (for example Bremia lactucae, Peronospora sp., Pseudoperonospora sp., Phytophthora sp.);
[00198] - fruit trees, with respect to diseases of the aerial parts: monilia disease (Monilia fructigenae, M. laxa), scabies (Venturia inaequalis), powdery mildew (Podosphaera leucotricha); - grapevine, with regard to foliage diseases: in particular gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), black rot (Guignardia biwelli) and mildew (Plasmopara viticola);
[00199] - beet root, with respect to the following diseases of the aerial parts: cercospora rust (Cercospora beticola), powdery mildew (Erysiphe beticola), leaf spot (Ramularia beticola).
[00200] The fungicidal composition according to the present invention can also be used against fungal diseases that can grow on or inside wood. The term "wood" means all types of wood species, and all types of work of this wood intended for construction, for example solid wood, high density wood, laminated wood, and plywood. The method for treating wood according to the invention consists mainly of contacting one or more compounds of the present invention, or a composition according to the invention; this includes, for example, direct application, spraying, immersion, injection or any other suitable medium.
[00201] The compounds of this invention are effective for the control of nematodes, insects, mite pests and / or fungal pathogens of agronomic plants, growing and collected, when used alone, they can also be used in combination with other biological active agents used in agriculture, such as one or more nematicides, insecticides, acaricides, fungicides, bactericides, plant activator, molluscicide, and pheromones (chemical or biological). Mixing the compounds of the invention or their compositions in the form of use as pesticides with other pesticides often results in a broader pesticidal spectrum of action. For example, the compounds of the formula (I) of this invention can be effectively used in conjunction or in combination with pyrethroids, neocinotinoids, macrolides, diamides, phosphates, carbamates, cyclodienes, formamidines, phenol and tin compounds, chlorinated hydrocarbons, benzoylphenols , pyrroles and the like.
[00202] The activity of the compositions according to the invention can be increased considerably, and adapted to prevailing circumstances, by adding, for example, one or more other insecticidal, acaricidal, nematicidal and / or fungicidal active ingredients. Combinations of compounds of the formula (I) with other insecticidal, acaricidal, nematicidal and / or fungicidal active ingredients can also have additional surprising advantages, which can also be described, in a broader sense, as synergistic activity. For example, better plant tolerance, reduced phytotoxicity, pests or fungi can be controlled in their different stages of development or better behavior during their production, for example during crushing or mixing, during storage or during use.
[00203] The following list of pesticides in conjunction with which the compounds according to the invention can be used is intended to illustrate possible combinations by way of example.
[00204] The following combinations of the compounds of the formula (I) with other active compounds are preferred (the abbreviation "TX" means "a compound selected from the 163 compounds of each of Tables 1 through 33 of the present invention"):
[00205] an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
[00206] an acaricide selected from the group of substances consisting of 1,1-bis (4-chlorophenyl) -2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC name / from Chemical Abstracts ) (1059) + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocil (3) + TX, acetoprol [CCN] + TX, acrinatrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidition (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amiton (875) + TX, amiton hydrogenoxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, nioso (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotine (46) + TX, nitrogen (889) + TX, benomyl (62) + TX, benoxafos (alternative name) [CCN] + TX, benzoxide (71) + TX, benzyl benzoate (IUPAC name) [CCN] + TX, biphenazate (74) + TX, bifenthrin (76) + TX, bipacril (907) + TX, brofenvalerate (alternative name) + TX, bromocyclic (918) + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxy (103) + TX, butoxycarboxin (104) + TX, butylpyridabene (alternative name ) + TX, calcium polysulfide (IUPAC name) (111) + TX, camfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbofenotion (947) + TX, CGA 50'439 (development code) (125) + TX, quinomethionate (126) + TX, clorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorinaphar (130) + TX, chlorphenethol (968) + TX, chlorfenson (970) + TX, chlorfen sulfide (971) + TX, chlorfenvinfos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX , cinerin I (696) + TX, cinerin II (696) + TX, cinerines (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumafos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxifos (1010) + TX, cufraneb (1013) + TX, cyantoate (1020) + TX, ciflumetofen (CAS No: 400882-07-7) + TX, cyhalothrin ( 196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demefion (1037) + TX, demefion-O (1037) + TX, from - mefion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S ( 1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafentiuron (226) + TX, dialiphos (1042) + TX, diazinon (227) + TX, diclofluanide ( 230) + TX, dichlorvos (236) + TX, diclifos (alternative name) + TX, dicofol (242) + TX, dicrotofos (243) + TX, diene-chlor (1071) + TX, dimefox (1081) + TX, dimetoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinobuton (269) + TX, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, dinocton (1090) + TX, dinopenton ( 1092) + TX, dinosulfon (1097) + TX, dinoterbon (1098) + TX, dioxation (1102) + TX, diphenylsulfone (IUPAC name) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfoton ( 278) + TX, DNOC (282) + TX, dofenapin (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endotion (1121) + TX, EPN (297) + TX , eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, etoato-methyl (1134) + TX, ethoxazole (320) + TX, etrimphos (1142) + TX, fenazaflor (1147) + TX, phenazaquin (328) + TX, fenbutatin oxide (330) + TX, phenothiocarb (337) + TX, fenpropatrin (342) + TX, fenpirad (alternative name) + TX, fenpyroximate (345) + TX, fenson (1157) + TX , fentri-fanyl (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacripimim (360) + TX, fluazuron (1166) + TX, flubenzimine (1167) + TX, flucicloxuron (366 ) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, fluphenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, flupiradifurone + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formethanate (405) + TX, formethanate hydrochloride (405) + TX, formotion (1192) + TX, formparanate (1193) + TX, range-HCH (430) + TX, gliodine (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (IUPAC / Chemical Abstracts name) (1216) + TX, hexithiazox (441) + TX , iodomethane (IUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, O- (methoxyminothiophosphoryl) isopropyl salicylate (in IUPAC me) (473) + TX, ivermectin (alternative name) [CCN] + TX, Jasmine I (696) + TX, Jasmine II (696) + TX, Jodfenfos (1248) + TX, Lindane (430) + TX, Lufenuron (490) + TX, Malation (492) + TX, Maconoben (1254) + TX, mecarbam (502) + TX, mefosfolan (1261) + TX, messulfene (alternative name) [CCN] + TX, metacryphs (12 66) + TX, metamidophos (527) + TX, metidation (529) + TX, metiocarb (530) + TX, methomyl (531) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinfos (556) + TX, mexacarbato (1290) + TX, milbemycine (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, myfox (1293) + TX, monocrotophos (561) + TX, morfotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naled (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluidide (1309) + TX, nicomycins (alternative name) [CCN] + TX, nitrile carb (1313) + TX, nitrilacarb complex 1: 1 zinc chloride (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxideprofos (1324) + TX, oxisulfoton (1325) + TX, pp'-DDT (219) + TX , paration (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, fencapton (1330) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phosfol an (1338) + TX, fosmet (638) + TX, phosphamidon (639) + TX, foxim (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins ( alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacil (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX , protidation (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX, pyridafention (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalfos (711) + TX, quintiofos (1381) + TX, R- 1492 (development code) (1382) + TX, RA-17 (code development) (1383) + TX, rotenone (722) + TX, scradano (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sofamide (1402) + TX, spirodiclofen (738) + TX, spiromesifene (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau- fluvalinate (398) + TX, tebufenpirade (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinfos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425 ) + TX, thiafenox (alternative name) + TX, thiocarboxime (1431) + TX, thio-fanox (800) + TX, thiometon (801) + TX, thioquinox (1436) + TX, turinigensin (alternative name) [ CCN] + TX, triamphos (1441) + TX, triara-teno (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorphon (824) + TX, triphenophos (1455) + TX, trinactin (alternative name) (653) + TX, vamidotion (847) + TX, vaniliprol [CCN] and YI-5302 (compound code) + TX,
[00207] an algaecide selected from the group of substances consisting of betoxazine [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutrin [CCN] + TX, diclone ( 1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, phentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamide ( 1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX,
[00208] an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomato (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, benzoate emamectin (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,
[00209] an avicide selected from the group of substances consisting of chloralose (127) + TX, endrine (1122) + TX, fention (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX,
[00210] a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophene (232) + TX, dipyritinone (1105) + TX, dodicin (1112) + TX, phenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafene (alternative name) [CCN] + TX, ca-sugamycin (483) + TX, hydrated casugamycin hydrochloride (483) + TX, nickel bis (dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapirin (580) + TX, octylinone ( 590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, keyboard software (766) + TX, and timersal (alternative name) [CCN] + TX,
[00211] a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani ( alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide ( scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151) + TX, Cryptolaemus montrouzieri ( alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX , Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp. (alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Pasteuria penetrans + TX, Pasteuria thornei + TX, Pasteuria nishizawae + TX, Pasteuria ramosa + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera requires multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci ( alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX,
[00212] a soil sterilizer selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX,
[00213] a chemosterilizer selected from the group of substances consisting of afolate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif ( alternate name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiote [CCN] + TX, methyl aflate [CCN] + TX, morzid [ CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, tiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,
[00214] an insect pheromone selected from the group of substances consisting of (E) -dec-5-en-1-yl acetate with (E) -dec-5-en-1-ol (IUPAC name) (222) + TX, (E) -tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E) -6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E, Z) -tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779) + TX, (Z) -dodec-7-en-1-yl acetate (IUPAC name) ) (285) + TX, (Z) - hexadec-11-enal (IUPAC name) (436) + TX, (Z) -hexadec- 11-en-1-yl acetate (IUPAC name) (437) + TX , (Z) -hexadec-13-en- 11-in-1-yl acetate (IUPAC name) (438) + TX, (Z) -icos-13-en-10-one (IUPAC name) (448) + TX, (Z) -tetradec-7-en-1-al (IUPAC name) (782) + TX, (Z) -tetradec-9-en-1-ol (IUPAC name) (783) + TX, acetate (Z) - tetradec-9-en-1-yl (IUPAC name) (784) + TX, (7E, 9Z) acetate - dodeca-7,9-dien-1-yl (IUPAC name) (283) + TX, (9Z, 11E) acetate - tetradeca-9,11-dien-1-yl (IUPAC name) (780) + TX, (9Z, 12E) -tetradeca-9,12-dien-1- acetate ila (IUPAC name) (781) + TX, 14- methyloctadec-1- eno (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, brevicomina (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemona (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (IUPAC name) (286) + TX, dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodeca-8 + TX, acetate 10-dien-1-ila (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN ] + TX, front (alternative name) [CCN] + TX, gossiplure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name ) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (name alte alternative) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca acetate-2,13- dien- 1-ila (IUPAC name) (588) + TX, octadeca-3,13-dien-1-yl acetate (IUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, orictalure (name alternative) (317) + TX, ostramona (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, acetate tetradec-11-en- 1-ila (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN] + TX,
[00215] an insect repellent selected from the group of substances consisting of 2- (octylthium) ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy (polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyl toluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and pica- ridina [CCN] + TX,
[00216] an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (IUPAC / Chemical Abstracts name) (1058) + TX, 1,1-dichloro-2,2-bis (4-ethylphenyl) ethane (IUPAC name) (1056), + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX , 1-bromo-2-chloroethane (IUPAC / Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1- (3,4-dichlorophenyl) ethyl acetate (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl phosphate (IUPAC name) (1066) + TX, 2- (1,3-dithiolan-2-yl) phenyl dimethylcarbamate (IUPAC / Chemical Abstracts name) (1109) + TX, 2- (2-butoxyoxy) ethyl thiocyanate (IUPAC / Chemical Abstracts name) (935) + TX, 2- (4,5-dimethyl-1,3-dioxolan-2-yl) phenyl methylcarbamate ( IUPAC / Chemical Abstracts name) (1084) + TX, 2- (4-chloro-3,5-xylyloxy) ethanol (IUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidone (IUP name AC) (1225) + TX, 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 2-methyl (prop-2-inyl) aminophenyl methylcarbamate (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate ( IUPAC name) (1283) + TX, 4-methyl (prop-2-ynyl) amino-3,5-xylyl methylcarbamate (IUPAC name) (1285) + TX, 5,5-dimethyl-3- dimethylcarbamate oxocyclohex-1-enyl (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamipride (4) + TX, acetion (alternative name) [CCN] + TX, acetoprol [CCN ] + TX, acrocrine (9) + TX, acrylonitrile (IUPAC name) (861) + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, aldrin (864) + TX, alethrin (17) + TX, alosamidine (alternative name) [CCN] + TX, alixi- carb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX , aluminum phosphide (640) + TX, amidition (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton hydrogenoxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, atidation (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadiractin (alternative name) (41) + TX, azametiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl ( 45) + TX, nitrogen (889) + TX, delta endotoxins from Bacillus thuringiensis (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (IUPAC / Chemical Abstracts name) ) (892) + TX, bartrina [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarbe (60) + TX, bensultap (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioalethrin (78) + TX, S-cyclopentenyl isomer of bioallethrin (alternative name) (79) + TX, bioethanomethin [CCN] + TX, biopermetrin (908) + TX, bioresmethrin (80) + TX, bis (2-chloroethyl) ether (IUPAC name) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromphenthals ( 914) + TX, bromocyclene (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb (924) + TX, buprofezin ( 99) + TX, butacarb (926) + TX, butathiophos (927) + TX, butocarboxy (103) + TX, butonate (932) + TX, butoxycarboxy (104) + TX, butylpyridabene (alternative name) + TX, cadusafos ( 109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphorlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC / Chemical Abstracts name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbofenotion (947) + TX, carbosulfan (119) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorobicycene (960) + TX , chlordane (128) + TX, chlordecone (963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyphos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinfos (131) + TX, chlorfluazuron (132) + TX, chlorephes (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorfoxin (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX , chlorpyrifos-methyl (146) + TX, chlortiofos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerines (696) + TX, cis-resmethrin (alternative name) + TX, schismetrin (80) + TX, clocitrine (alternative name) + TX, cloetocarbe (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, acetoarsenite copper [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumafos (174) + TX, coumitoate (1006) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, crufomato (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) ( 1012) + TX, cyano-phenphos (1019) + TX, cyanophos (184) + TX, cyantoate (1020) + TX, cycloctrine [CCN] + TX, cycloprotrin (188) + TX, cyfluthrin (193) + TX , cyhalotrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cytate (alternative name) [CCN] + TX, d-limonene (alternative name ) [CCN] + TX, d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomet (216) + TX, DDT (219) + TX, de-carbofuran (1034) + TX, deltamethrin (223) + TX, demefion (1037) + TX, demefion-O (1037) + TX, demefion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton- O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafentiuron (226) + TX, dialects (1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapton (1050) + TX, diclofention (1051) + TX, dichlorvos (236) + TX, di- clifos (alternative name) + TX, dicresil (alternative name) [CCN] + TX, dicrotofos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, 5-methylpyrazol-3-yl diethyl phosphate (IUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimeflutrin [CCN] + TX, dimefox (1081) + TX, dimethane (1085) + TX, dimetoate (262) + TX, dimethrin (1083) + TX, dimethylvinfos (265) + TX, dimethylan (1086) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271) + TX, diophenolan (1099) + TX, dioxabenzofos (1100) + TX, dioxacarb (1101) + TX, dioxation (1102) + TX, disulfoton (278) + TX, dithycrophos (1108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1115) + TX, ecdysterone (alternative name) [CCN] + TX, EI 1642 (development code) (1118) + TX, emamectin ( 291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empentrin (292) + TX, endosulfan (294) + TX, endotion (1121) + TX, endrine (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epophenone (1124) + TX, eprinomectin (alternative name) [CCN] + TX, sphenthalerate (302) + TX, etafos (alternative name) [CCN] + TX, etiofencarbe (308) + TX , etion (309) + TX, etiprol (310) + TX, etoate-methyl (1134) + TX, etoprofos (312) + TX, ethyl format (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name ) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimphos (1142) + TX, EXD (1143) + TX, famfur (323) + TX, fenamiphos (326) + TX, fenazaflor (1147) + TX, phenclorfos (1148) + TX, fenetacarb (1149) + TX, fenflutrina (1150) + TX , fenitrotion (335) + TX, phenobucarb (336) + TX, fenoxacrim (1153) + TX, phenoxycarb (340) + TX, phenpiritrin (1155) + TX, fenpropatrin (342) + TX, fenpirad (alternative name) + TX , fensul-fotion (1158) + TX, fention (346) + TX, fention-ethyl [CCN] + TX, fenfererate (349) + TX, fipronil (354) + TX, flonicamide (358) + TX, flubendi - amide (No. (At the. CAS Reg .: 272451-65-7) + TX, flucofuron (1168) + TX, flucicloxuron (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenerin [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, fonofos (1191) + TX, formethanate (405 ) + TX, formethanate hydrochloride (405) + TX, formotion (1192) + TX, formparanate (1193) + TX, fosmetilan (1194) + TX, phospirate (1195) + TX, fostiazate (408) + TX, fostietan ( 1196) + TX, furatiocarb (412) + TX, furetrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatin (422) + TX, guazatin acetates (422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (1211) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, h iquincarb (1223) + TX, imidacloprid (458) + TX, imiprotrine (460) + TX, indoxa-carb (465) + TX, iodomethane (IUPAC name) (542) + TX, IPSP (1229) + TX, isazophos ( 1231) + TX, isobenzane (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrine (1235) + TX, isofenfos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX , O- (methoxyminothiophosphoryl) isopropyl salicylate (IUPAC name) (473) + TX, isoprothiolan (474) + TX, isothioate (1244) + TX, isoxation (480) + TX, ivermectin (alternative name) [CCN] + TX , Jasmine I (696) + TX, Jasmine II (696) + TX, Jodfenfos (1248) + TX, Youth Hormone I (alternative name) [CCN] + TX, Youth Hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, chelvan (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin [CCN ] + TX, leptophos (1250) + TX, lindane (430) + TX, lirimphos (1251) + TX, lufenuron (490) + TX, litidation (1253) + TX, methyl m-cumenyl carbamate (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malation (492) + TX, malonoben (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarfon (1258) + TX, menazon (1260) + TX, mefosfolan (1261) + TX, mercury chloride (513) + TX, mesulfens (1263) + TX, metaflumizone [CCN] + TX , metam (519) + TX, metha-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, metacryphs (1266) + TX, metamidophos (527) + TX, methane fluoride- sulfonyl (IUPAC / Chemical Abstracts name) (1268) + TX, metidation (529) + TX, metiocarb (530) + TX, metocrotophos (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methoquin-butyl (1276) + TX, methetrine (alternative name) (533) + TX, methoxychloride (534) + TX, methoxyphenid (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methyl-chloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metoflutrin [CCN] + TX, metolcarb (550) + TX, methoxyzone (1288 ) + TX, mevinfos (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX , monocrotofos (561) + TX, morphotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (IUPAC / do name Chemical Abstracts) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpiram (579) + TX, nitiazine (1311) + TX, nitrilacarb (1313) + TX, nitrilacarb complex 1: 1 zinc chloride (1313) + TX, NNI-0101 (compound code ) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novauron (585) + TX, noviflumuron (586) + TX, O-5- dichloro-ethylphosphonothioate 4-iodophenyl O-ethyl (IUPAC name) (1057) + TX, O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate O, O-diethyl (IUPAC name) (1074) + TX, O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate of O, O-diethyl (IUPAC name) (1075) + TX, O, O, O ', O'-tetrapropyl dithiopyrophosphate (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxidemeton-methyl (609) + TX, oxide profos (1324) + TX, oxisulfoton (1325 ) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, paration (615) + TX, paration-methyl (616) + TX, penfluron (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-38 (development code) ( 1328) + TX, phencapton (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, fosmet (638 ) + TX, fosnichlor (1339) + TX, phosphamidon (639) + TX, phosphine (IUPAC name) (640) + TX, foxim (642) + TX, foximmethyl (1340) + TX, pyrimetafos (1344) + TX, pirimicarb (651) + TX, pirimiphos-ethyl a (1345) + TX, pyrimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name ) [CCN] + TX, primidofos (1349) + TX, profenofos (662) + TX, profluentin [CCN] + TX, promacil (1354) + TX, promecarbe (1355) + TX, propafos (1356) + TX, propetamfos (673) + TX, propoxur (678) + TX, protidation (1360) + TX, protiofos (686) + TX, protoate (1362) + TX, proton-fenbute [CCN] + TX, pimetrozina (688) + TX, pyraclofes (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyralidalyl (700) + TX, pyridafention (701) + TX, pyrimidiphene (706) + TX, pyromitate (1370) + TX, pyriproxyphene (708) + TX, quássia (alternative name) [CCN] + TX, quinalfos (711) + TX, quinalfos-methyl (1376) + TX, quinotion (1380) + TX, quintiofos (1381) + TX, R-1492 (development code) (1382 ) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) ( 1386) + TX, riania (alternative name) (1387) + TX, rianodine (traditional name) (1387) + TX, sabadila (alternative name) (725) + TX, scra- damage (1389) + TX, sebufos (name alternative) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI -0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, fluoride sodium (IUPAC / Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623 ) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, sofamide (1402) + TX, spinosad (737) + TX, spiromesifene (739) + TX, spirotetramat [CCN ] + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpirade (763) + TX, tebupirimphos (764) + TX, teflubenzuron (768) + TX, teflutrin (769) + TX, temefos (770) + TX, TEPP (1417) + TX, teralethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiaclopride (791) + TX, tiafenox (alternative name ) + TX, thiamethoxam (792) + TX, ticrophos (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogenoxalate (798) + TX , thio-dicarb (799) + TX, thiophanox (800) + TX, thiometon (801) + TX, thionazine (1434) + TX, thiosultap (803) + TX, thiosultap-sodium (803) + TX, thuringian (alternative name) [CCN] + TX, tolfenpirade (809) + TX, tralometrine (812) + TX, transflutrin (813) + TX, transpermetrin (1440) + TX, triamiphos (1441) + TX, triazamate (818 ) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronat (1452) + TX, triphenophos ( 1455) + TX, triflumuron (835) + TX, trimetacarb (840) + TX, triprene (1459) + TX, vamidotion (847) + TX, vaniliprol [CCN] + TX, veratridine (alternative name) (725) + TX , veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name ) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprol [736994-63-19] + TX, cl o- rantraniliprol [500008-45-7] + TX, cyienopyraphene [560121-52-0] + TX, cyflumetophen [400882-07-7] + TX, pyrifluquinazone [337458-27-2] + TX, espinetoram [187166- 40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprole [70488618-0] + TX, meperflutrin [915288-13- 0] + TX, tetramethylflutrin [8493788-2] + TX,
[00217] a molluscicide selected from the group of substances consisting of bis (tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloro-carb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulphate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, metiocarb (530 ) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodic carb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [394730-71-3] + TX,
[00218] a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC / Chemical Abstracts name) (1045) + TX, 1,2- dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 1,1 -3,4-dichlorotetrahydrothiophene (IUPAC / Chemical Abstracts name) (1065) + TX, 3- (4-chlorophenyl) -5-methylrodanine (IUPAC name) (980) + TX, 5-methyl-6- acid thioxo-1,3,5-thiadiazinan-3-ylacetic (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprol [CCN] + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridabene (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrina (141) + TX, clo rpirifos (145) + TX, cloetocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, diclofention (1051) + TX, diclifos (alternative name) + TX, dimetoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, etoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpirad (alternative name) + TX, fensulfotion ( 1158) + TX, fosthiazate (408) + TX, fosthietan (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX , iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (alternative name) [CCN] + TX, cinnamon (alternative name) (210) + TX, mecarfon (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, is methyl otiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, composition of Myrothecium verrucaria (alternative name) (565) + TX, NC-184 ( compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC / Chemical Abstracts name) (1422) + TX, tiafenox (alternative name) + TX , thiozazine (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX,
[00219] a nitrification inhibitor selected from the group of substances consisting of potassium ethyl xanthate [CCN] and nitrapirin (580) + TX,
[00220] a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and extract of Reynoutria sachalinensis (alternative name) (720) + TX ,
[00221] a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX , alpha-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, antu (880) + TX, arsenious oxide (882) + TX, barium carbonate (891) + TX, bistiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorofacinone (140) + TX, cholecalciferol (alternative name ) (850) + TX, coumaclor (1004) + TX, coumafuril (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, diphthialone (249) + TX, difhacinone (273) + TX, ergocalciferol (301) + TX, flocoumadeno (357) + TX, fluoroacetamide (379) + TX, flupropadine (1183) + TX, flupropadine hydrochloride (1183) + TX, gamma-HCH (430 ) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, phosphor magnesium (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, matt (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN ] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, sciliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX,
[00222] a synergist selected from the group of substances consisting of 2- (2-butoxyethoxy) ethyl piperonylate (IUPAC name) (934) + TX, 5- (1,3-benzodioxol-5-yl) -3-hexylcyclohex -2-enona (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296 ) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolina ( 1394) and sulfoxide (1406) + TX,
[00223] an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatin (422) + TX, guazatin acetates (422) + TX, metiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX , take out (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,
[00224] a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
[00225] a wound protector selected from the group of substances consisting of mercuric oxide (512) + TX, octylinone (590) and thiophanate-methyl (802) + TX,
[00226] and biologically active compounds selected from the group consisting of azaconazole (60207-31-0] + TX, bitertanol [70585-36-3] + TX, bromuconazole [116255-48-2] + TX, cyproconazole [94361-06 -5] + TX, diphenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [114369-43-6] + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutria-fol [76674-21-0] + TX, hexaconazole [79983-71-4] + TX, imazalil [3555444- 0] + TX, imibenconazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0] + TX, pefurazoate [101903-30-4] + TX, penconazole [66246-88-6] + TX, protoconazole [178928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09 -5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [112281-77-3] + TX, triadimefon [43121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, tritic onazole [13198372-7] + TX, ancimidol [12771-68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [41483-43-6] + TX, dimethyrimol [5221-53-4] + TX, ethirimol [23947-60-6] + TX, dodemorph [1593-77-7] + TX, phenpropidine [67306-00-7] + TX, fenpropimorph [67564 -91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-43-3] + TX, cypridinyl [121552-61-2] + TX, mepanipirim [110235-47-7 ] + TX, pyrimethanil [53112-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [13134186-1] + TX, benalaxyl [71626-11-4] + TX, furalaxil [57646- 30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148 -79-8] + TX, clozolinate [84332-86-5] + TX, diclozoline [24201-58-9] + TX, iprodione [36734-197] + TX, myclozoline [54864-61-8] + TX, procymidone [32809-16-8] + TX, vinclozoline [5 0471-44-8] + TX, boscalide [188425-85-6] + TX, carboxine [5234-68-4] + TX, fenfuram [24691-80-3] + TX, flutolanil [6633296-5] + TX, mepronil [55814-41-0] + TX, oxycarboxine [5259-88-1] + TX, pentiopyrade [183675-82-3] + TX, tifluzamide [130000-40-7] + TX, guazatin [108173 -90-6] + TX, dodine [2439-10-3] [112-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-338] + TX, dimoxystrobin [149961-52-4] + TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, cresoxim-methyl [143390-89-0] + TX, metominostrobin [133408-50- 1] + TX, trifloxystrobin [141517-21-7] + TX, orisotrobin [248593-16-0] + TX, picoxystrobin [117428-22-5] + TX, pi-raclostrobin [175013-18-0] + TX, ferbam [14484-64-1] + TX, manchezebe [8018-01-7] + TX, manebe [12427-38-2] + TX, put [9006-422] + TX, propineb [12071 -83-9] + TX, remove [137-26-8] + TX, zineb [12122-67-7] + TX, remove [137-30-4] + TX, captafol [2425-06-1] + TX, captana [133-06-2] + TX, dichlofluanide [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-07-3] + TX, tolylfluanide [731- 27-1] + TX, bordeaux mixture [8011-63-0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758 -98-7] + TX, copper oxide [1317-39-1] + TX, maneuver [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap [131-72 -6] + TX, nitrotal- isopropyl [10552-74-6] + TX, buildings [17109 -49-8] + TX, iprobenfos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphen [3651900-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, bentiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, quinomethionate [2439-01-2] + TX, chloronebe [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamide [ 180409-60-3] + TX, cymoxanil [57966-95-7] + TX, diclone [117-80-6] + TX, diclocimet [139920-32-4] + TX, diclomezine [62865-36-5] + TX, dichloran [99-30-9] + TX, diethylphenocarb [87130-20-9] + TX, dimetomorph [110488-70-5] + TX, SYP-LI90 (Flumorf) [211867-47-9 ] + TX, dithianon [3347-22-6] + TX, etaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [13180757-3] + TX, phenamidone [161326- 34-7] + TX, phenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferimzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX , fluopicolide [239110-15-7] + TX, flusulfamide [106917-52-6] + TX, phenhexamide [126833-17-8] + TX, fosetyl aluminum [39148-24-8] + TX, himexazole [10004-44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF- 916 (Cyzofamide) [120116-88-3] + TX, casugamycin [6980-18-3] + TX, metasulfocarb [66952-49-6] + TX, methamphenone [220899-03-6] + TX , pencicuron [66063-05-6] + TX, phthalide [27355-22-2] + TX, polyoxins [11113-80-7] + TX, probenazole [2760576-1] + TX, propamocarb [25606-41-1 ] + TX, proquinazide [18927812-4] + TX, piroquilon [57369-32-1] + TX, quinoxyphene [124495-18-7] + TX, quintozene [82-68-8] + TX, sulfur [7704- 34-9] + TX, thiadinyl [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [4181478-2] + TX, triforin [26644-46-2] + TX, validamycin [37248-47-8] + TX, zoxamide (RH7281) [156052-68-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, silkxane [874967- 67-6] + TX, 3-difluoromethyl-1-methyl-1H-pyrazole- (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl) -amide 4- carboxylic (developed in WO 2007/048556) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2- (2,4-dichlorophenyl) - 2-methoxy-1-methyl-ethyl] -amide (disclosed in WO 2008/148570) + TX, 1- [4- [4 - [(5S) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1 , 3-thiazol-2-yl] piperidin-1-yl] -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone + TX, 1- [4- [4- [ 5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl] piperidin-1-yl] -2- [5-methyl -3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone [1003318-67-9], (both disclosed in WO 2010/123791, WO 2008/013925, WO 2008/013622 and WO 2011/051243 page 20) + TX, e 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3 ', 4', 5'-trifluoro-biphenyl-2-yl) (disclosed in WO 2006/087343) + TX.
[00227] References in square brackets behind the active ingredients, for example, [3878-19-1], refer to the Chemical Abstracts Registration number. The mixing partners described above are known. When the active ingredients are included in the "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Publisher: C. D. S. TomLin; The British Crop Protection Council], are described there with the entry number given in curly brackets here above for the particular compound; for example, the compound "abamectin" is described under the entry number (1). Where "[CCN]" is added here above to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the Internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprol" is described with the Internet address: http://www.alanwood.net/pesticides/acetoprole.html.
[00228] In the present document, most of the active ingredients described above are called by a so-called "common name", the relevant "common name ISO" or another "common name" that is used in particular cases. If the designation is not a "common name", the nature of the alternative designation used is given in parentheses for the particular compound; in this case, the IUPAC name, the Chemical Abstracts / IUPAC name, a "chemical name", a "traditional name", a "compound name" or a "development code" are used or, if none of these designations or a "common name" is used, an "alternative name" is used. "CAS Registration No." means the Chemical Abstracts Registration Number.
[00229] The weight ratio of any of the two ingredients in each combination is selected to give, for example, the desired synergistic action. In general, the mass ratio would vary depending on the specific ingredient and how many ingredients are present in the combination. Generally, the weight ratio between any two ingredients in any combination of the present invention, independently of one another, is 100: 1 to 1: 100 including 99: 1, 98: 2, 97: 3, 96: 4, 95 : 5, 94: 6, 93: 7, 92: 8, 91: 9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83:17 , 82:18, 81:19, 80:20, 79:21, 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70 : 30, 69:31, 68:32, 67:33, 66:34, 65:45, 64:46, 63:47, 62:48, 61:49, 60:40, 59:41, 58:42 , 57:43, 56:44, 55:45, 54:46, 53:47, 52:48, 51:49, 50:50, 49:51, 48:52, 47:53, 46:54, 45 : 55, 44:56, 43:57, 42:58, 41:59, 40:60, 39:61, 38:62, 37:63, 36:64, 35:65, 34:66, 33:67 , 32:68, 31:69, 30:70, 29:71, 28:72, 27:73, 26:74, 25:75, 24:76, 23:77, 22:78, 21:79, 20 : 80, 19:81, 18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 11:89, 10:90, 9:91, 8:92 , 7:93, 6:94, 5:95, 4:96, 3:97, 2:98, 1:99. Preferred mass ratios between any two components of the present invention are 75: 1 to 1:75, more preferably, 50: 1 to 1:50, especially 25: 1 to 1:25, advantageously 10: 1 to 1:10, such as 5: 1 to 1: 5, for example 1: 3 to 3: 1. Mixing ratios are understood to include, on the one hand, ratios by mass, and also, on the other hand, molar ratios.
[00230] Examples of application methods for the compounds of the invention and their compositions, that is, the methods of pest / fungus control in agriculture, are spraying, atomization, dusting, brushing in, treatment, dispersion or spillage - which they are to be selected to suit the intended objectives of the prevailing circumstances.
[00231] A preferred method of application in agriculture is application to the foliage of plants (foliar application), being possible to select the frequency and application rate to correspond to the dangers of infestation with the pest / fungus in question. Alternatively, the active ingredient can reach the plants through the root system (systemic action), by applying the compound to the plant's locus, for example by applying a liquid composition of the compound to the soil (by soaking), or by applying a solid form of the compound in the form of granules to the soil (application to the soil). In the case of rice crops in paddy fields, such granules can be dosed in the flooded paddy fields.
[00232] Typical application rates per hectare are generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g / ha, preferably 10 to 600 g / ha, such as 50 to 300 g / ha.
[00233] The compounds of the invention and their compositions are also suitable for the protection of plant propagating material, for example seeds, such as fruit, tubers or grains, or plants in nurseries, against pests of the aforementioned type. The propagation material can be treated with the compost before planting, for example, a seed can be treated before sowing. Alternatively, the compound can be applied to the seed grains (coating), either by soaking the grains in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted at the application site, for example in the seed groove during the process of forming rows. These treatment methods for plant propagation material and plant propagation material treated in this way are still objects of the invention. Typical treatment rates would depend on the plant and the pest / fungus to be controlled and are generally between 1 and 200 grams per 100 kg of seeds, preferably between 5 and 150 grams per 100 kg of seeds, such as between 10 and 100 grams per 100 kg of seeds.
[00234] The term seed covers seeds and plant propagules of all types including but not limited to true seeds, pieces of seeds, sprouts, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cuttings and similar and means, in a preferred embodiment, true seeds.
[00235] The present invention also comprises seeds coated or treated with or containing a compound of formula I. The term "coated or treated with and / or containing" generally means that the active ingredient is mostly on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate the seed material, depending on the method of application. When said seed product is (re) planted, it can absorb the active ingredient. In one embodiment, the present invention makes available a plant propagating material adhered thereto with a compound of the formula (I). In addition, a composition comprising a plant propagating material treated with a compound of formula (I) is hereby made available.
[00236] Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed disinfection, seed coating, seed powdering, seed soaking and seed pelleting. The application of seed treatment of the compound of formula I can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during sowing / planting of seeds.
[00237] Suitable target plants are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar beet or fodder; fruits, for example, peach fruit, stone fruit or sweet fruits, such as apples, pears, plums, peaches, almonds, cherries or berries, for example, strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soybeans; oilseed plants, such as rapeseed, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or peanuts; cucurbits, such as pumpkins, cucumbers or melons; fiber plants, such as cotton, linen, hemp or jute; citrus fruits, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes or peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, the banana family, latex plants and ornamental plants (like flowers, and lawn or peat).
[00238] In one embodiment, the plant is selected from cereals, corn, soybeans, rice, sugar cane, vegetables and oilseeds.
[00239] The term "plant" should be understood to also include plants that have been transformed using DNA-combining techniques so that they are able to synthesize one or more toxins with selective action, such as those known, for example, from bacteria producing toxins, especially those of the Bacillus genus.
[00240] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins of Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, for example, CrylAb, CrylAc, CrylF, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip, "vegetative insecticidal proteins"), for example, Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins from bacteria colonized by nematodes, for example, Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomyces toxins, plant lectins, such as pea lectins, barley lectins, or white bellflower lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactive proteins (RIP), such as ricin, corn RIP, abrina, lufina, saporina or briodina; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA reductase, ion channel blockers, such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.
[00241] In the context of the present invention, they are to be understood by δ-endotoxins, for example, CrylAb, CrylAc, CrylF, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vip1, Vip2, Vip3 or Vip3A, also expressly hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of these proteins (see, for example, WO 02/15701). Truncated toxins, for example a truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid substitutions, preferably non-naturally occurring protease recognition sequences are inserted into the toxin, as, for example, in the case of Cry3A055, a cathepsin G recognition sequence is inserted into a Cry3A toxin (see WO 03/018810 ).
Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP- A-451 878 and WO 03/052073.
[00243] The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Deoxyribonucleic acids of the CryI type and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.
[00244] The toxin contained in transgenic plants provides plants with tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in beetles (Coleoptera), double-winged insects (Diptera) and butterflies (Lepidoptera).
[00245] Transgenic plants that contain one or more genes that encode an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (a corn variety that expresses a Cry1Ab toxin); YieldGard Rootworm® (corn variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (corn variety that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink® (corn variety that expresses a Cry9C toxin); Herculex I® (corn variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricin-N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate-ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a CrylAc and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (tolerant to characteristic GA21 glyphosate), Agrisure® CB Advantage (characteristic Bt11 corn borer (CB)) and Protecta®. ADDITIONAL EXAMPLES OF SUCH TRANSGENIC PLANTS ARE:
[00246] Bt11 corn from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96/05/10. Genetically modified Zea mays that has been made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.
[00247] Bt176 corn from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96/05/10. Genetically modified Zea mays that has been made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.
[00248] MIR604 corn from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96/05/10. Maize that has been made resistant to insects by the transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by inserting a cathepsin-G-protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03/018810.
[00249] MON 863 corn from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02/9. MON 863 expresses a Cry3Bb1 toxin and is resistant to certain Coleoptera insects.
[00250] Cotton IPC 531 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96/02.
[00251] Corn 1507 from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00/10. Maize genetically modified to express the Cry 1F protein to achieve resistance to certain Lepidoptera insects and PAT protein to achieve tolerance to the herbicide glufosinate ammonium.
[00252] Maize NK603 x MON 810 from Monsanto Europe S.A. 270272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It consists of hybrid maize varieties conventionally improved by crossing the genetically modified varieties NK603 and MON 810. Maize NK603 x MON 810 transgenically expresses the CP4 EPSPS protein, obtained from the CP4 strain of Agrobacterium sp., Which provides tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki that provides tolerance to certain Lepidoptera, including the European corn borer.
[00253] Generally, a compound of the present invention is used in the form of a composition (e.g., formulation) containing a carrier. A compound of the invention and its compositions can be used in various forms, such as aerosol dispenser, suspension for capsules, cold fogging concentrate, dustable powder, emulsifiable concentrate, oil-in-water emulsion, water-in-oil emulsion, encapsulated granule, granule fine, flowable concentrate for seed treatment, gas (under pressure), gas-generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil flowable miscible concentrate, liquid miscible in oil, paste, plant sticks, dry seed treatment powder, seed coated with a pesticide, soluble concentrate, soluble powder, seed treatment solution, suspension concentrate (flowable concentrate), ultra low volume (ulv), ultra low volume suspension (ulv), water-dispersible granules or tablets, water-dispersible powder for treating water-soluble pastes, granules or tablets, water-soluble powder for seed treatment and wettable powder.
[00254] A formulation typically comprises a liquid or solid carrier and optionally one or more usual formulation auxiliaries, which can be solid or liquid auxiliaries, for example, non-epoxidized or epoxidized vegetable oils (for example, coconut oil, rapeseed oil or epoxidized soybean oil), defoamers, for example, silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and / or adhesion promoters. The composition may also further comprise a fertilizer, a micronutrient donor or other preparations that influence plant growth, as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematocides, plant activators, acaricides, and insecticides.
Accordingly, the present invention also makes possible a composition comprising a compound of the invention and a carrier agronomically and optionally one or more usual formulation aids.
[00256] The compositions are prepared in a manner known per se, in the absence of auxiliaries, for example, by grinding, sieving and / or compression of a solid compound of the present invention and in the presence of at least one auxiliary, for example , by intimate mixing and / or grinding the compound of the present invention with the auxiliary (auxiliary). In the case of solid compounds of the invention, the grinding / grinding of the compounds is to ensure specific particle size. These processes for the preparation of the compositions and the use of the compounds of the invention for the preparation of these compositions are also an object of the invention.
[00257] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersible, directly sprayable or dilutable solutions, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, powders wettables, dust, granules or encapsulations in polymeric substances, which comprise - at least - a compound according to the invention and the type of composition is to be selected to suit the intended objectives and prevailing circumstances.
[00258] Examples of suitable liquid carriers are non-hydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the C8 to C12 fractions of alkylbenzenes, such as mixtures of xylene, alkylated naphthalenes or tetrahydronaphthalenes, aliphatic or cyclaliphatic hydrocarbons, such such as paraffins or cyclohexane, alcohols such as ethanol, propanol or butanol, glycols and their ethers and esters, such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N, N-dimethylformamide, water, epoxidized or non-epoxidized vegetable oils, such as oil rapeseed, castor, coconut or soy epoxidized or not epoxidized, and silicone oils.
[00259] Examples of solid carriers that are useful for example for dust and dispersible powders are, as a rule, crushed natural minerals such as calcite, talc, kaolin, montmorillonite or atapulgite. To improve physical properties, it is also possible to add highly dispersible silicas or highly dispersible absorbable polymers. Particulate absorbable vehicles suitable for granules are porous types, such as pumice, brick crushed stone, sepolite or bentonite, and appropriate non-absorbable vehicle materials are calcite or sand. In addition, a large number of granulated materials of an organic or inorganic nature can be used, in particular dolomite or comminuted plant residues.
[00260] The compounds with appropriate surface activity are, depending on the type of active ingredient that will be formulated, nonionic, cationic and / or anionic surfactants or mixtures of surfactants with good emulsifying, dispersing and wetting properties . The surfactants mentioned below should be considered as examples only; a large number of additional surfactants which are conventionally used in the formulation technique and which are appropriate according to the invention are described in the relevant literature.
[00261] Suitable nonionic surfactants are especially derived from polyglycolic ether of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids or alkyl phenols which may contain about 3 to about 30 groups of glycolic ether and about 8 to about 20 carbon atoms in the aliphatic hydrocarbon radical (cycle) or about 6 to about 18 carbon atoms in the alkyl fraction of the alkyl phenols. Water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediamine polypropylene glycol or alkyl polypropylene glycol having 1 to approximately 10 carbon atoms in the alkyl chain and approximately 20 to approximately 250 ethylene glycol ether groups and approximately 10 are also suitable to approximately 100 propylene glycol ether groups. Typically, the aforementioned compounds contain 1 to approximately 5 units of ethylene glycol per unit of propylene glycol. Examples that can be mentioned are nonylphenoxypolyetoxyethanol, castor oil polyglycol ether, polypropylene glycol / polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol. Also suitable are esters of polyoxyethylene sorbitan fatty acids, such as polyoxyethylene sorbitan trioleate.
[00262] Cationic surfactants are, especially, quaternary ammonium salts that generally have at least one alkyl radical of about 8 to about 22 C atoms as substituents and alkyl or hydroxyalkyl radicals of short or benzyl chain (non-halogenated) or halogenated) as additional substituents. The salts are preferably in the form of halides, methylsulphates or ethylsulphates. Examples are stearyltrimethylammonium chloride and benzyl-bis (2-chloroethyl) ethylammonium bromide.
[00263] Examples of suitable anionic surfactants are water-soluble soaps or compounds with synthetic water-soluble surface activity. Examples of suitable soaps are the alkaline, alkaline earth or ammonium salts (unsubstituted or substituted) of fatty acids with about 10 to about 22 C atoms, such as the sodium or potassium salts of oleic or stearic acid, or mixtures of natural fatty acids that can be obtained, for example, from coconut oil or liquid resin; mention should also be made of the fatty acid methyl taurates. However, synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, derivatives of sulfonated benzimidazole or alkylaryl sulfonates. As a rule, fatty sulfonates and fatty sulfates are present in the form of alkaline, alkaline earth or ammonium salts (substituted or unsubstituted) and generally have an alkyl radical of approximately 8 to approximately 22 C atoms, alkyl should also be understood as including the alkyl fraction of acyl radicals; examples that can be mentioned are the sodium or calcium salts of lignosulfonic acid, dodecyl sulfuric ester or a mixture of fatty alcohol sulphates prepared from natural fatty acids. This group also includes the salts of sulfuric esters and sulfonic acids in fatty alcohol / ethylene oxide adducts. Sulphonated benzimidazole derivatives preferably contain 2 sulfonyl groups and a fatty acid radical of approximately 8 to approximately 22 C atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a condensate of naphthalenesulfonic acid / formaldehyde. In addition, suitable phosphates are also possible, such as phosphoric ester salts of a p-nonylphenol / (4-14) ethylene oxide adduct, or phospholipids.
[00264] As a rule, the compositions comprise 0.1 to 99%, in particular 0.1 to 95%, of the compound according to the present invention and 1 to 99.9%, in particular 5 to 99.9%, of at least one solid or liquid carrier, it being possible, as a rule, that 0 to 25%, in particular 0.1 to 20%, of the composition consists of surfactants (% in each case meaning weight percentage). While concentrated compositions tend to be preferred for marketed goods, the end consumer usually uses diluted compositions that have significantly lower concentrations of the active ingredient. Preferred compositions are composed particularly as follows (% = weight percentage): Emulsifiable concentrates: Active ingredient: 1 to 95%, preferably 5 to 20% surfactant: 1 to 30%, preferably 10 to 20% solvent: 5 to 98% , preferably 70 to 85% Dust: Active ingredient: 0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99% Concentrates in suspension and concentrates capable of flowing : Active ingredient: 5 to 75%, preferably 10 to 50% water: 94 to 24%, preferably 88 to 30% surfactant: 1 to 40%, preferably 2 to 30% Wettable powders: Active ingredient: 0.5 to 90% , preferably 1 to 80% surfactant: 0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 99%, preferably 15 to 98% Granules: Active ingredient: 0.5 to 30%, preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85% Examples of formulation (% = weight percentage) Example F1: Emulsion concentrates a) b) c) Active ingredient 25% 40% 50% Calcium dodecylbenzenesulfonate 5% 8% 6% Polyethylene glycol castor oil ether (36 mol of EO ) 5% - - Tributylphenoxypolyethylene glycol ether (30 mol of EO) - 12% 4% Cyclohexanone - 15% 20% Mixture of xylenes 65% 25% 20%
[00265] Emulsions of any desired concentration can be prepared from such concentrates by diluting with water. Example F2: Solutions a) b) c) d) Active ingredient 80% 10% 5% 95% Ethylene glycol monomethyl ether 20% - - - Polyethylene glycol PM 400 - 70% - - N-Methylpyrrolid-2-one - 20% - - Epoxidized coconut oil - - 1% 5% Petroleum ether (boiling range: 160-190 °) - - 94% -
[00266] The solutions are suitable for use in the form of microdroplets. Example F3: Granules a) b) c) d) Active ingredient 5% 10% 8% 21% Kaolin 94% - 79% 54% Highly dispersed silica 1% - 13% 7% Atapulgite - 90% - 18%
[00267] The active ingredient is dissolved in dichloromethane, the solution is sprayed on the carrier (s), and the solvent is subsequently evaporated under vacuum. Example F4: Dust a) b) Active ingredient 2% 5% Highly dispersed silica 1% 5% Talc 97% - Kaolin - 90%
[00268] Ready-to-use dust is obtained by intimately mixing the carriers and the active ingredient. Example F5: Wettable powders a) b) c) Active ingredient 25% 50% 75% Sodium lignosulfonate 5% 5% - Sodium lauryl sulfate 3% - 5% Sodium diisobutyl-naphthalenesulfonate - 6% 10% Ether octylphenoxypolyethylene glycol (7-8 mol of EO) - 2% - Highly dispersed silica 5% 10% 10% Kaolin 62% 27% -
[00269] The active ingredient is mixed with the additives and the mixture is thoroughly ground in a suitable mill. This gives rise to wettable powders, which can be diluted with water to provide suspensions of any desired concentration. Example F6: Extruder granules Active ingredient 10% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 87%
[00270] The active ingredient is mixed with the additives, and the mixture is crushed, moistened with water, extruded, granulated and dried in an air stream. Example F7: Coated granules Active ingredient 3% Polyethylene glycol (PM 200) 3% Kaolin 94%
[00271] In a mixer, the finely crushed active ingredient is applied evenly to kaolin, which has been moistened with polyethylene glycol. This provides dust-free coated granules. Example F8: Suspension concentrate Active ingredient 40% Ethylene glycol 10% Nonylphenoxypolyethylene glycol ether (15 mol EO) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% 37% formaldehyde aqueous solution 0.2% Silicone oil (emulsion 75% aqueous) 0.8% Water 32%
[00272] The finely crushed active ingredient is intimately mixed with the additives. Suspensions of any desired concentration can be prepared from the resulting suspension concentrate by dilution with water. Example F9: Dry seed treatment powders a) b) c) active ingredient 25% 50% 75% light mineral oil 5% 5% 5% highly dispersed silicic acid 5% 5% - Kaolin 65% 40% - Talc - - 20%
[00273] The combination is completely mixed with the adjuvants and the mixture is carefully ground in a suitable mill, providing powders that can be used directly for seed treatment. Example F10: Emulsifiable concentrate active ingredient 10% polyethylene glycol octylphenol ether 3% (4-5 mol ethylene oxide) calcium dodecylbenzenesulfonate 3% castor oil polyglycol ether (35 mol ethylene oxide) 4% cyclohexanone 30% mixture of xylenes 50%
[00274] Emulsions of any required dilution, which can be used to protect plants, can be obtained from this concentrate by dilution with water. Example F11: Flowable concentrate for seed treatment active ingredients 40% propylene glycol 5% butanol PO / EO copolymer 2% Triestyrenophenol with 10-20 moles of EO 2% 1,2-benzisothiazolin-3-one (in the form of a 20% solution 0.5% in water) 5% monoazo pigment calcium salt Silicone oil (in the form of a 75% emulsion in 0.2% water) Water 45.3%
[00275] The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by diluting with water. Using these dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, spilling or immersion. Examples of foliar formulation types for premix compositions are: GR: WP granules: wettable powders WG: water dispersible granules (powder) SG: water-soluble granules SL: EC-soluble concentrates: EW emulsifiable concentrate: emulsions, oil in water ME: microemulsion SC: aqueous concentrate in suspension CS: aqueous suspension for capsules OD: concentrate in suspension based on oil, and SE: suspo-emulsion in water. Whereas, examples of formulation types of pre-mix compositions for seed treatment are: WS: wettable powders for seed treatment slurry LS: seed treatment solution ES: seed treatment emulsions FS: concentrate in suspension for treatment of WG seeds: granules dispersible in water, and CS: aqueous suspension of capsules.
[00276] Examples of suitable formulation types for tank mix compositions are solutions, diluted emulsions, suspensions, or a mixture thereof, and dust.
[00277] As with the nature of the formulations, the application methods, such as foliar, submersion, spraying, atomization, sprinkling, spreading, coating or pouring, are chosen according to the intended objectives and the prevailing circumstances.
[00278] Tank mix compositions are generally prepared by diluting with a solvent (e.g., water) one or more premix compositions containing different pesticides, and optionally additional auxiliaries.
[00279] Suitable carriers and adjuvants can be solid or liquid and are the substances commonly used in the formulation technology, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackiness agents, thickeners, binders or fertilizers.
[00280] Generally, a tank mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15%, of the desired ingredients, and 99.9 to 80%, especially 99.9 to 85%, of solid or liquid auxiliaries (including, for example, a solvent, such as water), in which auxiliaries may consist of a surfactant in an amount from 0 to 20%, especially from 0.1 to 15%, based on the tank mix formulation.
[00281] Typically, a premix formulation for foliar application comprises 0.1 to 99.9%, especially 1 to 95%, of the desired ingredients, and 99.9 to 0.1%, especially 99 to 5% , of a solid or liquid adjuvant (including, for example, a solvent, such as water), where auxiliaries may consist of a surfactant in an amount of 0 to 50%, especially 0.5 to 40%, based on the premix formulation.
[00282] Typically, a tank mix formulation for applying a seed treatment comprises 0.25 to 80%, especially 1 to 75%, of the desired ingredients and 99.75 to 20%, especially 99 to 25%, of solid or liquid auxiliaries (including, for example, a solvent, such as water), where auxiliaries may consist of a surfactant in an amount of 0 to 40%, especially 0.5 to 30%, based on the formulation of tank mix.
[00283] Typically, a premix formulation for application in seed treatment comprises 0.5 to 99.9%, especially 1 to 95%, of the desired ingredients, and 99.5 to 0.1%, especially 99 5%, of a solid or liquid adjuvant (including, for example, a solvent, such as water), where auxiliaries may consist of a surfactant in an amount of 0 to 50%, especially 0.5 to 40% , based on the pre-mix formulation.
[00284] Although commercial products are preferably formulated as concentrates (for example, premix composition (formulation)), the end user will normally employ diluted formulations (for example, tank mix composition).
[00285] Preferred premix formulations for seed treatment are concentrated in aqueous suspension. The formulation can be applied to seeds using conventional treatment techniques and machines, such as fluidized bed techniques, the roller mill method, roto-static seed scrubbers, and drum coaters. Other methods, such as gushing beds, may also be useful. The seeds can be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
[00286] In general, the premixed compositions of the invention contain 0.5 to 99.9, especially 1 to 95, advantageously 1 to 50%, by weight, of the desired ingredients, and 99.5 to 0, 1, especially from 99 to 5%, by weight, of a solid or liquid adjuvant (including, for example, a solvent, such as water), where auxiliaries (or adjuvant) may consist of a surfactant in an amount of 0 to 50, especially 0.5 to 40%, by weight, based on the mass of the premix formulation.
[00287] A compound of the formula (I) is in a preferred embodiment, independent of any other embodiments, in the form of a treatment (or protection) composition of plant propagating material, wherein said composition of Protection of plant propagating material further comprises a coloring agent. The protective composition or mixture of plant propagating material may also comprise at least one polymer starting from water-soluble and water-dispersible film-forming polymers that improve the adhesion of the active ingredients to the treated plant propagation material, the polymer of which generally has a average molecular weight of at least 10,000 to about 100,000.
[00288] The combinations of the present invention (i.e., those comprising a compound of the present invention and one or more biological active agents) can be applied simultaneously or sequentially.
[00289] In the event that the ingredients of a combination are applied sequentially (ie, one after the other), the ingredients are applied sequentially within a reasonable period of one another to achieve biological performance, such as within a few hours or days. The order of application of the ingredients in the combination, i.e., whether the compounds of formula (I) are to be applied first or not, is not essential to the work of the present invention.
[00290] If the ingredients of the combinations are applied simultaneously in the present invention, they can be applied as a composition containing the combination, in which case (A) the compound of the formula (I) and the one or more other ingredients in the combinations can be obtained from separate formulation sources and mixed together (known as a ready-to-apply tank mixture, spray broth, or paste), or (B) the compound of formula (I) and one or more others ingredients can be obtained as a single formulation mix source (known as a premix, ready mix, concentrate, or formulated product).
[00291] In one embodiment, independent of other embodiments, a compound according to the present invention is applied as a combination. Accordingly, the present invention also provides a composition comprising a compound according to the invention as described herein and one or more other biological active agents, and optionally one or more usual formulation aids; which can be in the form of a tank mix or premix composition.
[00292] Alternatively to the real synergistic action with regard to biological activity, the combinations according to the invention can also have surprising advantageous properties which can also be described, in a broader sense, as synergistic activity. Examples of such advantageous properties that can be mentioned are the following: advantageous behavior during formulation and / or by application, for example, by grinding, sifting, emulsifying, dissolving or dispensing; greater stability during storage, improved stability to light; more advantageous degradability; improved toxicological and / or ecotoxicological behavior, or any other familiar advantages for one skilled in the art.
[00293] The compounds of the present invention for use in agriculture are preferably a nematicide.
[00294] The compounds of the present invention may also find application in other areas, such as one or more of protection of stored goods and storage chambers, the protection of raw materials (such as wood or textiles), floor coverings and buildings, and in hygiene management - especially the protection of humans, domestic animals and productive livestock against pests. The invention therefore also makes pesticidal compositions available for such uses and the methods for them. The composition would need to be modified for use in a particular use, and a person skilled in the art would be able to make such compositions available for any particular use.
[00295] In the hygiene sector, the compositions according to the invention are active against ectoparasites such as hard ticks, soft ticks, scabies mites, thrombiculous mites, flies (biting and licking), parasitic fly larvae, lice , hair lice, bird lice and fleas. Examples of such parasites are:
[00296] - Of the order Anoplurida: Haematopinus spp., Linognathus spp., Pediculus spp. and Phtirus spp., Solenopotes spp ..
[00297] - Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp ..
[00298] - Of the order Diptera and of the sub-orders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culi- coides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp. ., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. . and Melophagus spp ..
[00299] - Of the order Siphonapterida, for example Pulex spp., Cetocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
[00300] - Of the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..
[00301] - Of the order Blattarida, for example Blatta orientalis, Peri- american planet, Blattela germanica and Supella spp ..
[00302] - From the subclass Acaria (Acarida) and the orders Metastigmata and Mesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp. , Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp ..
[00303] - Of the orders Actinedida (Prostigmata) and Acaridida (Astig-mata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp. ., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocopod spp., Cy and Laminosioptes spp ..
[00304] The compositions according to the invention are also suitable for protection against insect infestations in the case of materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cardboard, leather, floor coverings and buildings. The compositions according to the invention can be used, for example, against the following pests: beetles, such as Hylotrupes baculus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovilloumum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobi- a carpini , Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus species, Tryptodendron species, Apate monachus, Bos- trychus capucins, Heterobostrychus brunneus and mininos, Sino and Dinosaur, Sino such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, and termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Copter- silver, like Lepisma saccharina.
[00305] The application methods for applying a compound or a composition to stored goods, storage chambers, raw materials (such as wood and textiles), floor and building coverings, and in hygiene management are known in the art .
[00306] The invention also provides a method for treating, curing, controlling, preventing and protecting warm-blooded animals, including humans, and fish against infestation and infection by helminths, arachnids and arthropod endo- and ectoparasites that comprise oral, topical administration or parenteral or application to said animals of an anti-helminthic, acaricidal or endo- or ectoparasiticidal amount of the compound of formula (I).
[00307] The above method is particularly useful for the control and prevention of infestations and infections by helminths, nematodes, mites and endo- and arthropod ectoparasites in warm-blooded animals such as cattle, sheep, pigs, camels, deer, horses, birds domestic animals, fish, rabbits, goats, mink, fox, chinchillas, dogs and cats, as well as humans.
[00308] In the context of control and prevention of infestation and infections in warm-blooded animals, the compounds of the invention are especially useful for the control of helminths and nematodes. Examples of helminths are members of the class Trematoda, commonly known as worms or flatworms, especially members of the genera Fasciola, Fascioloides, Paramphistomu, Dichro-coelium, Eurytrema, Ophisthorchis, Fasciolopsis, Echinostoma and Para- gonimus. Nematodes that can be controlled by the compounds of formula (I) include the genera Haemonchus, Ostertagia, Cooperia, Oesphagastomu, Nematodirus, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaria and the like.
[00309] The compound of this invention can also control infestations of arthropod endoparasites, such as cattle worm and stomach larva. Additionally, mite infestations and arthropod ectoparasites in warm-blooded animals and fish, including biting lice, sucking lice, fly larvae, biting flies, muscoid flies, flies, myasitic fly larvae, worms, mosquitoes, fleas, mites, ticks, nasal larvae, flies and maruins can be controlled, prevented or eliminated by the compounds of this invention. Biting lice include members of Mallophaga such as Bovicola bovis, Trichodectes canis and Damilina ovis. Sucking lice include members of Anoplura such as Haematopinus eurysternus, Haematopinus suis, Linognathus vituli and Soilopotes capillatus. Biting flies include members of Haemomatobia. Ticks include Boophilus, Rhipicephalus, Ixodes, Hylomma, Amblyomma and Dermacentor. The compounds of the invention can also be used to control mites that are parasitic in warm-blooded mammals and poultry including mites of the orders Acariformes and Parasitiformes.
[00310] For oral administration to warm-blooded animals, the compounds of the invention can be formulated as animal feed, animal feed premixtures, animal feed concentrates, pills, solutions, pastes, suspensions, potions, gels, pills, boluses and capsules. In addition, the compounds of the invention can be administered to animals in their drinking water. For oral administration, the chosen dosage form should provide the animal with about 0.01 mg / kg to 100 g / kg of animal body weight per day of the compound of the invention.
Alternatively, the compounds of the invention can be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the invention can be dispersed or dissolved in a pharmaceutically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the invention can be formulated into an implant for subcutaneous administration. In addition, the compounds of the invention can be administered transdermally to animals. For parenteral administration, the chosen dosage form should provide the animal with about 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compound of the invention.
[00312] The compounds of the invention can also be applied topically to animals in the form of dips, dust, powders, necklaces, medallions, sprayers and spill formulations. For topical application, dips and sprayers contain about 0.5 ppm to 5,000 ppm and preferably about 1 ppm to 3,000 ppm of the compound of the invention. In addition, the compounds of the invention can be formulated as eartags for animals, particularly quadrupeds, such as cattle and sheep.
[00313] The compounds of the invention can also be used in combination or in conjunction with one or more other parasitized compounds (to broaden the spectrum of activity), including but not limited to anthelmintics, such as benzimidazoles, piperazine, levami - sun, pyrantel, praziquantel and the like; endectocides, such as avermectins, milbemycins and the like; ectoparasiticides, such as arylpyrroles, organophosphates, carbamates, gamma-butyric acid inhibitors, including fipronil, pyrethroids, spinosads, imidacloprid and the like; insect growth regulators, such as pyriproxifen, chiromazine and the like; and chitin synthase inhibitors, such as benzoylurines, including fluphenoxuron.
[00314] The parasiticidal compositions of the present invention include a parasiticidal effective amount of a compound of the invention or its combinations mixed with one or more physiologically tolerable inert, solid or liquid carriers known from veterinary medical practice for oral, percutaneous and topical. Such compositions may comprise additional additives, such as stabilizers, defoamers, viscosity regulators, binders and adhesion promoters, whereas commercial products will preferably be formulated as concentrates, the end consumer will normally employ diluted formulations.
[00315] The compositions according to the present invention can also be used for the preparation of compositions useful for curatively or preventively treating human and animal fungal diseases such as, for example, mycoses, dermatoses, Trichophyton's diseases and candidiasis or diseases caused by Aspergillus spp., For example Aspergillus fumigatus.
[00316] In one embodiment, independent of any other embodiments, a compound of formula (I) is an anthelmintic compound.
[00317] In one embodiment, independent of any other embodiments, a compound of formula (I) is a pesticidal compound, preferably a nematicidal compound.
[00318] In each aspect and embodiment of the invention, "consisting essentially" and its inflections are a preferred embodiment of "comprising" and its inflections, and "consisting of" and its inflections are a preferred embodiment of " consisting essentially of "and its inflections.
[00319] Disclosure in this application makes each and every combination of embodiments disclosed here available.
[00320] The following Examples serve to illustrate the invention. They do not limit the invention. Temperatures are given in degrees Celsius; the solvent mixing ratios are given in parts by volume. EXAMPLES Preparation examples: Example P1: Preparation of N- [cis-2- (4-chlorophenyl) oxetan-3-yl] -2- (trifluoromethyl) benzamide (compound 5710)

[00321] A solution of 4-fluorobenzaldehyde (288 mg, 2.32 mmol) and 2-trifluoromethyl-N-vinyl-benzamide (example P8b) (1 g, 4.65 mmol) in acetonitrile (15 ml) was irradiated with a sodium vapor lamp through a quartz filter for 7 days. The cloudy reaction mixture was evaporated and the crude semi-solid (1.6 g) was chromatographed on silica with EtOAc / cyclohexane, then again with MeOH / dichloromethane and again with EtOAc / cyclohexane, giving rise to 43 mg (3%) of N- [cis-2- (4-chlorophenyl) oxetan-3-yl] -2- (trifluoromethyl) benzamide.
[00322] 1H-NMR (CDCl3) 4.51 (1H, t); 5.17 (1H, t); 5.48 (1H, M); 5.71 (1H, broad d); 6.08 (1H, d); 6.93 (1H, d); 7.12 (2H, t); 7.38 (2H, m); 7.47 (2H, m); 7.63 (1H, d). Example P2: Preparation of cis N- [2- (4-chlorophenyl) cyclobutyl] -2- (trifluoromethyl) benzamide (compound 57.006):
The. Preparation of 2- (4-chlorophenyl) cyclobutanone
[00323] To a stirred solution of 4-chloro-benzaldehyde (142 mg, 1 mmol) and cyclopropyl diphenylsulfonium tetrafluoroborate (317 mg, 1 mmol) in 10 mL of dry THF, cooled to 0 ° C, was added dropwise, with agitation, a tert paste. potassium butoxide (1.4 mL, 1 M). After the addition was complete, the reaction was stirred for 30 minutes and 1 M tetrafluoroboric acid (10% in THF) (10 ml) was added. The mixture was allowed to warm to room temperature and was collected in ether and the ether solution was washed with saturated NaHCO3, brine and water and was dried. Filtration and concentration by rotary evaporation gave rise to an oil. Chromatography on silica gel and elution with i-Hx: ether 5: 1 gave 2- (4-chlorophenyl) cyclobutanone as an oil (180 mg, 83%).
[00324] 1H-NMR (CDCl3) 2.20 (1H, m); 2.57 (1H, m); 3.06 (1H, m); 3.23 (1H, m); 4.51 (1H, m); 7.20 (2H, m); 7.29 (3H, m). B. Preparation of 2- (4-chlorophenyl) cyclobutanone oxime
[00325] A solution of 2- (4-chlorophenyl) cyclobutanone (1,122 g, 6.09 mmol), hydroxylamine hydrochloride (3.541 g, 8.2 eq.) And 36 ml of 5% NaOH in 30 ml of EtOH heated to reflux for 2 hours. The solution was cooled, adjusted to pH 6, and extracted with CHCl3. The organic extract was washed with brine and was dried. Filtration and concentration gave 2- (4-chlorophenyl) cyclobutanone oxime as an oil. 1 g (84%).
[00326] 1H-NMR (CDCl3) 2.13 (1H, m); 2.53 (1H, m); 3.01 (2H, m); 4.40 (1H, m); 7.27 (5H, m). ç. Preparation of 2- (4-chlorophenyl) cyclobutanamine
[00327] To a solution of 2- (4-chlorophenyl) cyclobutanone oxime (200 mg, 1 mmol) in methanol (5 mL) was added MoO3 (205 mg, 1.4 eq.) And sodium borohydride (394 mg, 10 eq) at 0 ° C. After stirring at rt for 2 hours, the solvent was evaporated. A mixture of H2O and CH2Cl2 was added. The organic phase was separated, washed with brine, dried and concentrated in vacuo. 120 mg of product-amine was isolated in the form of a mixture of cis and trans isomers 2: 1. The crude product without purification was used for the next reaction. d. Preparation of N- [2- (4-chlorophenyl) cyclobutyl] -2- (trifluoromethyl) benzamide: To a solution of 2- (4-chlorophenyl) cyclobutanamine (105 mg, 0.55 mmol) and triethylamine (140 mg, 2 , 5 eq.) In THF 2-trifluoromethyl-benzoyl chloride (127.46 mg, 1.1 eq.) Was added at 0 ° C. The MR was stirred at rt for 2 h. Et3N.HCl was removed by filtration and the THF was evaporated. The residue - mixture of two cis and trans isomers (2: 1) was purified and separated with chromatography on silica gel, eluent i-Hx: diethyl ether 1: 1 (KMnO4 stain). N- [cis-2- (4-chlorophenyl) cyclobutyl] -2- (trifluoromethyl) benzamide (cis) (33 mg, mp 147-9 ° C) and its trans isomer (17 mg, mp 117-9 ° C) were isolated in the form of crystalline products. Example P3: Preparation of 2- (4-chlorophenyl) cyclobutanone (alternative)
The. Preparation of 1-chloro-4- (cyclopropylidenomethyl) benzene To a suspension of (4-bromopropyl) triphenylphosphonium bromide (29.3 g) in anhydrous THF (200 mL) was added, in 5 separate portions with intervals of 15 minutes, tert. potassium butoxide (14.19 g, 2.2 eq.), giving rise to a yellow suspension. The mixture was heated to reflux for 10 minutes and 4-dichlorobenzaldehyde (8.08 g, 56.9 mmol) was added, giving rise to an orange suspension. The reaction mixture was stirred and then heated to reflux for 4 hours. The MR was then cooled to room temperature, and was filtered on a Celite pad. The solvent was removed in vacuo, and the resulting crude material (9 g) was subjected to flash chromatography with i-hexane as the eluent, yielding 1-chloro-4- (cyclopropylidenomethyl) benzene (5 g, 53%) .
[00328] 1H-NMR (CDCl3) 1.19 (2H, m); 1.41 (2H, m); 6.70 (1H, m); 7.27 (2H, m); 7.46 (2H, m). B. Preparation of 2- (4-chlorophenyl) cyclobutanone
[00329] To a solution of 1-chloro-4- (cyclopropylidenomethyl) benzene (5 g, 30 mmol) in CH2Cl2 (80 mL) was added, in 5 separate portions, m-chloroperbenzoic acid (5.3 g, 30 mmol) at 0 ° C. After stirring at 0 ° C for 3 hours, the reaction mixture was washed with saturated aqueous NaHCO3 solution and brine, dried over Na2SO4 and concentrated. To the crude product in CH2Cl2 (40 ml) was added 10% HBF4 (11.6 ml, 48% HBF4 and 46 ml H2O). After stirring at r.t. for 17 hours, the mixture was extracted with CH2Cl2, washed with saturated aqueous NaHCO3 solution and brine. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel (eluent i-hexane, KMnO4 stain), yielding 2- (4-chlorophenyl) cyclobutanone (3.470 g, 64%). TABLES 57: CHARACTERIZING DATA
[00330] Table 57 shows data for selected melting points, selected HPLM-MS, and selected NMR for compounds of the present invention. CDCl3 was used as a solvent for NMR measurements, unless otherwise indicated. No attempts are made to list all characterizing data in all cases.
[00331] In Table 57 and throughout the following description, temperatures are presented in degrees Celsius; "NMR" means nuclear magnetic resonance spectrum; HPLC is high pressure liquid chromatography; MS designates mass spectrum; "%" is percent by weight, unless corresponding concentrations are indicated in other units. The following abbreviations are used throughout this description: mp = melting point [° C] p.e. = boiling point. S = wide singlet = wide d = doublet dd = doublet of doublets t = triplet q = quartet m = multiplet ppm = parts per million
[00332] Table 57 below is a list of compounds characterized by the formula Id. This represents formula I, where Y is O or CH2 and R1, R2, R3, R4, and R5 are H.






[00333] Either of R9a, R9b, and R9c is hydrogen depending on the substituents defined in each line
[00334] + NMR data:
[00335] 57,011:
[00336] 2.08 (1H, m); 2.37 (2H, m); 2.62 (1H, m); 4.26 (1H, m); 5.05 (1H, m); 5.42 (1H, m); 7.32 (2H, m); 7.41 (1H, s); 7.49 (1H, m); 7.65 (1H, m); 8.69 (1H, d).
[00337] 57,012:
[00338] 2.13 (IH, m); 2.39 (2H, m); 2.62 (IH, m); 4.28 (IH, m); 5.17 (IH, m); 7.33 (3H, m); 7.42 (IH, d); 7.75 (1H, broad d); 8.76 (1H, d).
[00339] 57,013:
[00340] 2.18 (IH, m); 2.35 (2H, m); 2.62 (IH, m); 3.39 (IH, m); 5.07 (IH, m); 7.20 (2H, d); 7.27 (2H, d); 7.38 (1H, t); 7.75 (IH, broad d); 8.75 (2H, d).
[00341] 57,015:
[00342] 2.11 (IH, m); 2.30 (2H, m); 2.61 (IH, m); 4.15 (IH, m); 5.02 (IH, m); 5.53 (1H, broad d); 4.10 (1H, d); 7.10 (IH, m); 7.17 (2H, m); 7.27 (1H, m); 7.47 (2H, m); 7.61 (IH, d).
[00343] 57,004:
[00344] 4.51 (1H, dd); 5.18 (1H, dd); 5.50 (1H, ddd); 5.69 (1H, dollar); 6.08 (1H, d); 6.90 (1H, d); 7.35 - 7.77 (7H, m).
[00345] HPLC-MS method for 57.047 and 57.070 to 57.111
[00346] The spectra were recorded on a Waters Mass Spectrometer (SQD or ZQ single quadripole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150 ° C, Desolvation Temperature: 350 ° C, Cone Gas Flow: 0 L / Hour, Desolvation Gas Flow: 650 L / Hour, Mass range: 100 to 900 Da) and an UPLC Acquity from Waters: Binary pump, heated column compartment and diode array detector. Solvent degasser, binary pump, heated column compartment and diode array detector. Column: UPLC HSS T3 from Waters, 1.8 mm, 30 x 2.1 mm, Temp: 60 ° C; DAD wavelength range (nm): 210 to 500, Solvent Gradient: A = water + 5% MeOH + 0.05% HCO-OH, B = Acetonitrile + 05% HCOOH: gradient: 0 minutes B 0% , 100%; 1.2-1.5 minutes B 100%; Flow (mL / minute) 0.85.
[00347] Table 58 below is a list of characterized compounds of the formula Ie. This represents formula I, where B is 4-chlorophenyl, A is A6, Y is CH2 and R1, R3, R4, and R5 are H.


[00348] LC-MS method:
[00349] Waters ACQUITY SQD Mass Spectrometer (Single Quadripole Mass Spectrometer)
[00350] Ionization method: Electrospray
[00351] Polarity: positive ions
[00352] Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, Source Temperature (° C) 150, Desolvation Temperature (° C) 400, Gas Flow no Cone (L / Hr) 60, Desolvation Gas Flow (L / Hr) 700
[00353] Mass range: 100 to 800 Da
[00354] DAD wavelength range (nm): 210 to 400
[00355] Waters UPLC ACQUITY method with the following HPLC gradient conditions
[00356] (Solvent A: Water / Methanol 9: 1, 0.1% formic acid and Solvent B: Acetonitrile, 0.1% formic acid)

[00357] Column type: UPLC ACQUITY HSS T3 by Waters; Column length: 30 mm; Column internal diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60 ° C. BIOLOGICAL EXAMPLES:
[00358] Contact activity of Meloidogyne spp. (Root nodule nematode), preventive. Purse test.
[00359] Filter papers (9 cm x 4.5 cm) with a small pocket were placed in plastic bags (12 cm x 6 cm). A seed of cv. Cucumber toshka was placed in the center of the filter paper pocket of all the bags needed for a test. The cucumber seeds in the bags were treated with 200 ppm test solutions by pipetting the solution directly onto the cucumber seed in the filter paper pocket in the bag. Before application, the compost solution was prepared at twice the required concentration and the egg suspension is prepared with 3000 eggs / 0.5 mL FORL nutrient solution. After application of all treatments, 3000 eggs (in 0.5 mL of FORL nutrient solution) were pipetted into the bags. The bags were incubated in a humidity chamber for twelve days and were watered regularly to maintain good moisture in the filter paper, essential for the growth of the root system of the cucumber. After this period, the filter paper containing the germinated cucumber seedlings was removed from the plastic bag to assess the number of tumors caused by Meloidogyne spp. by root system.
[00360] The following compounds showed a greater than 80% reduction in tumors compared to the untreated control: 57,009, 57,010, 57,011, 57,017, 57,012, 57,015, 57,014, 57,006, 57,016, 57,018, 57,020, 57,021, 57,022, 57.023, 57.024, 57.025, 57.028, 57.029, 57.030, 57.031, 57.033, 57.035, 57.036, 57.037, 57.039, 57.047, 57.048, 57.051, 57.052, 57.054, 57.055, 57.056, 57.057.
[00361] Contact activity of Meloidogyne spp. (Root nodule nematode), preventive, waterlogging test.
[00362] Seeds of cv. Cucumber toshka were sown directly in pots filled with a sandy substrate. Six days later, each vessel was treated with 5 ml of a 20 ppm WP10 suspension of the test compound. Then, the pots were incubated with 3000 eggs of M. incognita. The assay was collected fourteen days after application and inoculation of the assay. Root tumors were evaluated according to the Zeck tumor index (Zeck, 1971).
[00363] The following compounds showed a greater than 80% reduction in tumors compared to the untreated control: 57,001, 57,002, 57,003, 57,004, 57,005, 57,006, 57,007, 57,008, 57,010, 57,011, 57,014, 57,015, 57,016, 57.017, 57.018, 57.020, 57.021, 57.022, 57.023, 57.024, 57.025, 57.026, 57.028, 57.029, 57.031, 57.032, 57.033, 57.034, 57.035, 57.036, 57.037, 57.039, 57.040, 57.041, 57.042, 57.047, 57.048, 57.047, 57.048, 57.047, 57.048, 57.047, 57.048, 57.047, 57.048, 57.047, 57.048, 57.047, 57.048, 57.047, 57.048, 57.047, 57.048, 57.047, 57.042, 57.047, 57.042, 57.047 and 57.042, 57.047, 57.042 and 57.07, 577.07.0.0.0 and 57.07, 57.207.07.07.07.07.07.07.07.07.07.07.07.07.07.07ofnastunia's 57.07 and 577.07.07.07's Toshino said, `` the team has been working with the company for over 20 years. 57.052, 57.054, 57.055, 57.056, 57.057. Heterodera schachtii
[00364] The volume of 0.5 mL of an aqueous solution of the test compound (200 ppm or 20 ppm) is pipetted into each of the three wells. To each well, 0.5 ml of a suspension of nematodes containing approximately 200-500 J2 larvae of Heterodera schachtii are added. After storage in the dark at 25 ° C for 48 hours, the larvae mobility was evaluated and the average of the three wells was averaged.
[00365] Nematodes were 0 to 40% active in wells treated with 20 ppm of compounds 57,033, 57,035, 57,036, 57,037, 57,040, 57,041, 57,043, 5744, 57,055, 5756, 57,057.
[00366] Nematodes were 0 to 40% active in wells treated with 200 ppm of compounds 57,007, 57,008, 57,009, 57,010, 57,011, 57,017, 57,018, 5720, 57,022, 57,023, 57,024, 57,025, 57,028, 57,029, 57,030, 57,031 , 57,039, 57,047, 57,048.
[00367] Table 59 below shows the comparison of the nematicidal activity of cis isomers, which are the object of this invention with their corresponding trans isomers. The trans isomers were obtained using the P2 method above and separated from their cis isomers as described in the P2d method. In the table they are numbered according to their cis isomers with the suffix "trans" as shown in this example of 57-009 and 57-009trans


[00368] - Biological Screening Neither 1. Contact activity of Meloi- dogyne spp. (Root nodule nematode), preventive. Purse test. Values are given in% of tumors.
[00369] - Biological Screening Neither 2. Contact activity of Meloi- dogyne spp. (Nematode of the root nodule), preventive, quenching test. Values are given in% of tumors.
[00370] - nt means not tested.

权利要求:
Claims (20)
[0001]
1. Compound characterized by presenting formula I,
[0002]
2. Compound according to claim 1, characterized by the fact that A is a 6-membered heteroaromatic ring containing 1 to 2 nitrogen atoms and with 1 to 3 substituents selected from R6, or a phenyl ring with 1 or 3 substituents selected from R6.
[0003]
Compound according to claim 1 or 2, characterized in that B is a phenyl group substituted with 1 to 3 substituents R8.
[0004]
A compound according to any one of claims 1 to 3, characterized in that B is a phenyl group substituted with 1 to 3 substituents, independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, difluoromethoxy and trifluoromethoxy; A is a phenyl, pyridyl or pyrazinyl group, whose rings, independently of each other, are not substituted or are substituted with 1 to 3 substituents, independently selected from chlorine, bromine, fluorine, methyl, cyano, and trifluoromethyl, Y is O or CH2 , and R1, R2, R3, R4 and R5 are each hydrogen.
[0005]
Compound according to any one of claims 1 to 4, characterized in that Y is CH2; B is a mono or di-substituted phenyl with halogen; A is selected from phenyl, pyrazinyl and pyridyl, each of which is mono or di-substituted with substituents independently selected from halogen and C1-C4-haloalkyl; R1, R2, R3, R4 and R5 are each hydrogen.
[0006]
6. Compound according to claim 1, characterized by the fact that the compound is selected from any of the compounds 1 to 118 of formula (Id)
[0007]
7. Compound, or a salt or N-oxide thereof, according to claim 1, characterized in that it is selected from N - [(1,2 cis) -2- (4-chlorophenyl) cyclobutyl] -2- (trifluormethyl) pyridine-3-carboxamide; N - [(1,2 cis) -2- (2,4-dichlorophenyl) cyclobutyl] -2,6-difluorobenzamide; N - [(1,2 cis) -2- (2,4-dichlorophenyl) cyclobutyl] -2- (trifluoromethyl) benzamide; N - [(1,2 cis) -2- (2,4-dichlorophenyl) cyclobutyl] -2- (trifluoromethyl) pyridine-3-carboxamide; N - [(1,2 cis) -2- (2,4-difluorophenyl) cyclobutyl] -2- (trifluormethyl) benzamide; N - [(1,2 cis) -2- (2,4-difluorophenyl) cyclobutyl] -2- (trifluormethyl) pyridine-3-carboxamide; N - [(1,2 cis) -2- (2,4-difluorophenyl) cyclobutyl] -3- (trifluormethyl) pyrazine-2-carboxamide; N - [(1,2 cis) -2- [2-chloro-4- (trifluormethyl) phenyl] cyclobutyl] -3-trifluormethyl) pyridine-2-carboxamide; N - [(1,2 cis) -2- [2-chloro-4- (trifluormethyl) phenyl] cyclobutyl] -2-trifluormethyl) pyridine-3-carboxamide; N - [(1,2 cis) -2- [2-chloro-4- (trifluormethyl) phenyl] cyclobutyl] -3- (trifluormethyl) pyrazine-2-carboxamide; N - [(1,2 cis) -2- [2-fluor-4- (trifluoromethyl) phenyl] cyclobutyl] -2-trifluoromethyl) benzamide; N - [(1,2 cis) -2- [2-fluor-4- (trifluormethyl) phenyl] cyclobutyl] -3- (trifluormethyl) pyridine-2-carboxamide; N - [(1,2 cis) -2- [2-fluor-4- (trifluoromethyl) phenyl] cyclobutyl] -2- (trifluormethyl) pyridine-3-carboxamide; N - [(1,2 cis) -2- [2-fluor-4- (trifluormethyl) phenyl] cyclobutyl] -3- (trifluormethyl) pyrazine-2-carboxamide; 2- (trifluormethyl) -N - [(2,3 cis) -2- (2,4,6-trifluorphenyl) oxetan-3-yl] benzamide; 2,6-difluor-N - [(2,3 cis) -2- (2,4,6-trifluorophenyl) oxetan-3-yl] benzamide; N - [(2,3 cis) -2- (2,4-difluorfenyl) oxetan-3-yl] -2- (trifluoromethyl) benzamide; N - [(2,3 cis) -2- (2,4-difluorfenyl) oxetan-3-yl] -2- (trifluormethyl) pyridine-3-carboxamide; 3-chloro-N - [(1,2 cis) -2- (2,4-dichlorophenyl) cyclobutyl] pyrazine-2-carboxamide; N - [(1,2 cis) -2- (2,4-dichlorophenyl) cyclobutyl] -3- (trifluormethyl) pyridine-2-carboxamide; 3-chloro-N - [(1,2 cis) -2- (2,4-dichlorophenyl) cyclobutyl] pyridine-2-carboxamide; N - [(1,2 cis) -2- (2,4-dichlorophenyl) cyclobutyl] -2-methylpyridine-3-carboxamide; N - [(1,2 cis) -2- (2,4-dichlorophenyl) cyclobutyl] -3-methylpyridine-2-carboxamide; N - [(1,2 cis) -2- (2,4-difluorfenyl) cyclobutyl] -2- (trifluormethyl) pyridine-3-carboxamide; 2-Chlorine-N - [(1,2 cis) -2- (2,4-dichloro-phenyl) -cyclobutyl] -nicotinamide; N - [(1,2 cis) -2- (2-chloro-4-fluorophenyl) cyclobutyl] -2- (trifluormethyl) pyridine-3-carboxamide; N - [(1,2 cis) -2- (2-chloro-4-fluorophenyl) cyclobutyl] -3- (trifluormethyl) pyridine-2-carboxamide; N - [(1,2 cis) -2- (4-bromo-2-chloro-phenyl) cyclobutyl] -3- (trifluormethyl) pyridine-2-carboxamide; N - [(1,2 cis) -2- (2,4-difluorfenyl) cyclobutyl] -3- (trifluormethyl) pyridine-2-carboxamide; N - [(1,2 cis) -2- (4-methoxyphenyl) cyclobutyl] -3- (trifluoromethyl) pyridine-2-carboxamide; N - [(1,2 cis) -2- (4-chloro-2-fluorophenyl) cyclobutyl] -3- (trifluormethyl) pyridine-2-carboxamide; and N - [(1.2 cis) -2- (2-chloro-4-fluor-phenyl) cyclobutyl] -2- (trifluoromethyl) benzamide.
[0008]
8. Pesticidal composition, characterized in that, in addition to comprising adjuvants to the formulation, it comprises an effective pesticidal amount of a compound of formula I as defined in any one of claims 1 to 8.
[0009]
Composition according to Claim 8, characterized in that it further comprises one or more other agents insecticide, caress, nematicically and / or fungally active.
[0010]
10. A method of controlling damage and / or loss of yield caused by a pest and / or fungi characterized by application to a pest, or a plant susceptible to attack by a pest and / or fungi or a locus thereof, or to a plant propagating material of an effective amount of a compound, as defined in any one of claims 1 to 7, or a composition as defined in claim 8 or 9.
[0011]
11. Method for the protection of plant propagating material against damage and / or loss of yield caused by a pest and / or fungi characterized by the fact that it comprises application to the propagating material or to the place where the propagating material is planted in an effective amount of a compound as defined in any one of claims 1 to 7, or a composition as defined in claim 8 or 9.
[0012]
12. Method according to claim 10 or 11, characterized in that the damage or loss is caused by a nematode plague.
[0013]
13. Coated plant propagation material, characterized in that the coating of plant propagation material comprises a compound, as defined in any one of claims 1 to 7.
[0014]
14. Use of a compound, as defined in any one of claims 1 to 7, characterized in that it is in the preparation of a composition for the control of helminths, arachnids or arthropod endo- or ectoparasites that comprises a conforming compound, defined in any of the claims 1 to 7, a physiologically tolerable vehicle and optionally one or more usual formulation aids.
[0015]
15. Pharmaceutical composition characterized by comprising a compound, as defined in any one of claims 1 to 8, a physiologically tolerable vehicle and optionally one or more usual formulation aids for preventing infection with diseases transmitted through helminths, arachnids or endo- or arthropod ectoparasites.
[0016]
16. Composition according to claim 14 or 15, characterized in that it further comprises one or more other biologically active compounds.
[0017]
17. Use of a composition, as defined in claim 15, characterized in that it is in the preparation of a medication for the control and prevention of endo- and ectoparasitic nematode infestations and infections in warm-blooded animals, in which the medication is injected, applied topically or administered orally.
[0018]
18. Process for the preparation of compounds of formula I, characterized in that it comprises reacting a compound of formula II
[0019]
19. Compounds characterized by having the formula (XIXa)
[0020]
20. Compounds characterized by the formula (II), where B, Y, R1, R2, R3, R4 and R5 are as defined in where the compound of the formula is excluded.

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法律状态:
2018-03-13| B06T| Formal requirements before examination [chapter 6.20 patent gazette]|

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2018-03-27| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|

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2020-05-05| B07D| Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]|Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS. |

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2020-07-21| B07G| Grant request does not fulfill article 229-c lpi (prior consent of anvisa) [chapter 7.7 patent gazette]|

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2020-09-01| B07A| Technical examination (opinion): publication of technical examination (opinion) [chapter 7.1 patent gazette]|

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2021-02-02| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2021-04-13| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 06/03/2013, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

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申请号 | 申请日 | 专利标题

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EP12161190.9A|EP2644595A1|2012-03-26|2012-03-26|N-Cyclylamides as nematicides|

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EP12161190.9|2012-03-26|

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PCT/EP2013/054461|WO2013143811A1|2012-03-26|2013-03-06|N-cyclylamides as nematicides|

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