SK65896A3 - Derivatives of 2,3,5,6-tetrafluorobenzoic acid and their use in combating pests - Google Patents
Derivatives of 2,3,5,6-tetrafluorobenzoic acid and their use in combating pests Download PDFInfo
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Abstract
Description
Oblasť technikyTechnical field
Vynález sa týka derivátov kyseliny 2,3,5,6-tetrafluórbenzoovej, spôsobu ich výroby, ako i ich použitia na kynoženie škodcov.The present invention relates to 2,3,5,6-tetrafluorobenzoic acid derivatives, to a process for their preparation, and to their use for pest control.
Podstata vynálezuSUMMARY OF THE INVENTION
Predmetom predloženého vynálezu sú deriváty kyselinyThe present invention relates to acid derivatives
2,3,5,6-tetrafluórbenzoovej všeobecného vzorca I2,3,5,6-tetrafluorobenzoic acid of formula I
0) v ktorom0) in which
Y znamená kyslíkový atóm alebo atóm síry aY is an oxygen or sulfur atom; and
X znamená skupinu -0-N=CR1R2, -OR3, -OCHR4-CO-NR5R6 aleboX is -O-N = CR 1 R 2 , -OR 3 , -OCHR 4 -CO-NR 5 R 6, or
-NR7R8, pričom-NR 7 R 8 , wherein
R1 a R2 znamenajú nezávisle od seba prípadne substituovanú alkylovú skupinu, cykloalkylovú skupinu a arylovú skupinu,R 1 and R 2 are each independently an optionally substituted alkyl, cycloalkyl and aryl group,
OABOUT
R znamená alkylovú skupinu s aspoň dvoma uhlíkovými atómami, substituovanú alkylovú skupinu a prípadne substituovanú cykloalkylovú, arylovú a aralkylovú skupinu,R represents an alkyl group with at least two carbon atoms, a substituted alkyl group and an optionally substituted cycloalkyl, aryl and aralkyl group,
R4, R5 a R6 znamenajú nezávisle od seba vodíkový atóm a prípadne substituovanú alkylovú, arylovú a aralkylovú skupinu, aleboR 4 , R 5 and R 6 independently represent a hydrogen atom and an optionally substituted alkyl, aryl and aralkyl group, or
R5 a R6 znamenajú spoločne s dusíkovým atómom, na ktorý sú viazané, prípadne substituovaný kruh aleboR 5 and R 6 together with the nitrogen atom to which they are attached represent an optionally substituted ring or ring
R a R° znamenajú nezávisle od seba vodíkový atóm a pripadne substituovanú alkylovú, cykloalkylovú, arylovú, aralkylovú, alkylheteroarylovú a heteroarylovú skupinu, alebo skupiny -CHR4-COOH a -CHR4-COOCH3, pričom R7 a R8 neznamenajú súčasne vodíkový atóm, aleboR and R ° are each independently hydrogen and optionally substituted alkyl, cycloalkyl, aryl, aralkyl, alkylheteroaryl and heteroaryl, or -CHR 4 -COOH and -CHR 4 -COOCH 3 groups, wherein R 7 and R 8 are not simultaneously hydrogen atom, or
R7 a R8 tvoria spoločne s dusíkovým atómom, na ktorý sú viazané, prípadne substituovaný kruh, ako i ich adičné soli s kyselinami a komplexy kovových solí.R 7 and R 8 together with the nitrogen atom to which they are attached form an optionally substituted ring, as well as their acid addition salts and metal salt complexes.
Ďalej bolo zistené, že sa deriváty kyseliny 2,3,5,6-tetrafluórbenzoovej všeobecného vzorca I získajú tak, že sa 2,3,5,6tetrafluórbenzoylchlorid alebo anhydrid kyseliny 2,3,5,6-tetrafluórbenzoovej nechá reagovať so zodpovedajúcim oximom, alkoholom alebo amínom, prípadne za prítomnosti rozpúšťadla alebo bázy.It has further been found that the 2,3,5,6-tetrafluorobenzoic acid derivatives of the formula I are obtained by reacting 2,3,5,6-tetrafluorobenzoyl chloride or 2,3,5,6-tetrafluorobenzoic anhydride with the corresponding oxime, an alcohol or an amine, optionally in the presence of a solvent or a base.
Konečne bolo zistené, že nové deriváty kyseliny 2,3,5,6tetrafluórbenzoovej všeobecného vzorca I majú výraznú mikrobicídnu účinnosť, najmä proti voči rastlinám patogénnym mikroorganizmom. Okrem toho majú účinné látky podía predloženého vynálezu výrazný rezistenciu indukujúci účinok u rastlín proti napadnutiu nežiaducimi mikroorganizmami.Finally, it has been found that the novel 2,3,5,6-tetrafluorobenzoic acid derivatives of the formula I exhibit significant microbicidal activity, in particular against plants pathogenic microorganisms. In addition, the active compounds according to the invention have a marked resistance-inducing effect in plants against attack by unwanted microorganisms.
V nasledujúcom sú kvôli jednoduchosti uvádzané zlúčeniny všeobecného vzorca I, hoci sú tým mienené ako tieto čisté zlúčeniny, tak tiež zmesi s rôznymi podielmi izomérnych, enantiomérnych a diastereomérnych zlúčenín.In the following, for the sake of simplicity, the compounds of the formula I are mentioned, although they are meant to mean both these pure compounds and mixtures with different proportions of isomeric, enantiomeric and diastereomeric compounds.
Deriváty kyseliny 2,3,5,6-tetrafluórbenzoovej podlá predloženého vynálezu sú definované všeobecným vzorcom I.The 2,3,5,6-tetrafluorobenzoic acid derivatives of the present invention are defined by Formula I.
Vo všeobecnom vzorci I znamená výhodne, ak nie je uvedené inak alkylová skupina, jednotlivo alebo v príbuzných zvyškochIn formula I, preferably unless otherwise indicated, alkyl is singly or in related moieties
- priamu alebo rozvetvenú alkylovú skupinu s 1 až 8 uhlíkovými atómami, obzvlášť s 1 až 4 uhlíkovými atómami. Príkladovo a výhodne je možné uviesť metylovú skupinu, etylovú skupinu, n-propylovú skupinu, i-propylovú skupinu, n-butylovú skupinu, i-butylovú skupinu, sek.-butylovú skupinu a terc.-butylovú skupinu, cykloalkylová skupinaa straight or branched alkyl group having 1 to 8 carbon atoms, in particular 1 to 4 carbon atoms. By way of example and preferably, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl and tert-butyl, cycloalkyl are mentioned.
- trojčlenný až sedemčlenný kruh, obzvlášť kruh s 3, 5 alebo 6 uhlíkovými atómami. Príkladovo a výhodne je možné uviesť cyklopropylovú skupinu, cyklobutylovú skupinu, cyklopentylovú skupinu, cyklohexylovú skupinu a cykloheptylovú skupinu, arylová skupina nesubstituovanú alebo substituovanú arylovú skupinu so 6 až 10 uhlíkovými atómami. Príkladovo a výhodne je možné uviesť nesubstituovanú alebo substituovanú fenylovú a naftylovú skupinu, obzvlášť nesubstituovanú alebo substituovanú fenylovú skupinu, aralkylová skupina nesubstituovanú alebo substituovanú aralkylovú skupinu s 1 až 4 uhlíkovými atómami, obzvlášť s 1 až 2 uhlíkovými atómami v priamej alebo rozvetvenej alkylovej časti a so 6 až 10 uhlíkovými atómami v arylovej časti, obzvlášť vo fenylovej skupine. Príkladovo a výhodne je možné uviesť benzylovú skupinu, 1,1- fenetylovú skupinu, 1,2-fenetylovú skupinu, 1,l-fenylpropylovú skupinu, 1,2- fenylpropylovú skupinu, 1,3-fenylpropylovú skupinu a 2,2- fenylpropylovú skupinu, heteroarylová skupina nesubstituovaný alebo substituovaný päťčlenný až deväťčlenný kruh, obzvlášť päťčlenný až sedemčlenný kruh, ktorý obsahuje 1 až 4, výhodne 1 až 3, rovnaké alebo rôzne heteroatómy. Ako heteroatómy je možné uviesť výhodne kyslík, síru a dusík. Príkladovo a výhodne je možné menovať pyrimidinylovú skupinu, pyrolylovú skupinu, izotiazolylovú skupinu, oxazolylovú skupinu, tienylovú skupinu, furylovú skupinu, pyridazinylovú skupinu, pyrazinylovú skupinu, izoxazolylovú skupinu, tiazolylovú skupinu a obzvlášť pyridylovú skupinu, a heteroarylalkylová skupina- a 3- to 7-membered ring, in particular a ring having 3, 5 or 6 carbon atoms. By way of example and preferably, mention may be made of a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cycloheptyl group, an aryl group which is unsubstituted or substituted by an aryl group having 6 to 10 carbon atoms. Examples which may be mentioned are, for example, unsubstituted or substituted phenyl and naphthyl, especially unsubstituted or substituted phenyl, unsubstituted or substituted aralkyl having 1 to 4 carbon atoms, in particular 1 to 2 carbon atoms in the straight or branched alkyl moiety and 6 to 10 carbon atoms in the aryl moiety, especially in the phenyl group. Examples which may be mentioned are benzyl, 1,1-phenethyl, 1,2-phenethyl, 1,1-phenylpropyl, 1,2-phenylpropyl, 1,3-phenylpropyl and 2,2-phenylpropyl. , a heteroaryl group, an unsubstituted or substituted 5- to 9-membered ring, especially a 5- to 7-membered ring, which contains 1 to 4, preferably 1 to 3, identical or different heteroatoms. The heteroatoms are preferably oxygen, sulfur and nitrogen. Examples which may be mentioned are pyrimidinyl, pyrrolyl, isothiazolyl, oxazolyl, thienyl, furyl, pyridazinyl, pyrazinyl, isoxazolyl, thiazolyl and especially pyridyl, and heteroarylalkyl.
- skupina, v ktorej heteroarylová časť zodpovedá vyššie uvedenej definícii a výhodnej oblasti a alkylová časť je priama alebo rozvetvená a obsahuje 1 až 4 uhlíkové atómy, obzvlášť 1 alebo 2 uhlíkové atómy. Príkladovo a výhodne je možné uviesť heteroarylmetylovú skupinu, 1,1-heteroaryletylovú skupinu, 1,2-heteroaryl- etylovú skupinu, 1,1-heteroarylpropylovú skupinu, 1,2-heteroarylpropylovú skupinu,a group in which the heteroaryl moiety is as defined above and in the preferred region and the alkyl moiety is straight or branched and contains 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms. Exemplary and preferably, mention may be made of heteroarylmethyl, 1,1-heteroarylethyl, 1,2-heteroaryl-ethyl, 1,1-heteroarylpropyl, 1,2-heteroarylpropyl,
1,3-heteroarylpropylovú skupinu a 2,2-heteroarylpropylovú skupinu.A 1,3-heteroarylpropyl group and a 2,2-heteroarylpropyl group.
Prípadne substituované zvyšky všeobecného vzorca môžu niesť jeden alebo viacero, výhodne jeden až tri, obzvlášť jeden alebo dva, rovnaké alebo rôzne substituenty. Ako tieto substituenty je možné príkladovo a výhodne uviesť alkylovú skupinu, výhodne s 1 až 4 uhlíkovými atómami, obzvlášť s 1 alebo 2 uhlíkovými atómami, ako je metylová skupina, etylová skupina, n-propylová skupina, i--propylová skupina, n-butylová skupina, i-butylová skupina, sek.-butylová skupina a terc.-butylová skupina; alkoxyskupinu s výhodne 1 až 4 uhlíkovými atómami, obzvlášť 1 alebo 2 uhlíkovými atómami, ako je metoxyskupina, etoxyskupina, npropyloxyskupina, i-propyloxyskupina, n-butyloxyskupina, ibutyloxyskupina, sek.- butyloxyskupina a terc.-butyloxyskupina; alkyltioskupinu s výhodne 1 až 4 uhlíkovými atómami, obzvlášť s 1 alebo 2 uhlíkovými atómami, ako je metyltioskupina, etvltioskupina, n-propyltioskupina, i-propyltioskupina, n-butyltioskupina, i-butyltioskupina, sek.-butyltioskupina a terc.butyltioskupina; halogénalkylovú, halogénalkoxylovú a halogénalkyltio skupinu s výhodne 1 až 4 uhlíkovými atómami, obzvlášť s 1 alebo 2 uhlíkovými atómami a s 1 až 9 obzvlášť s 1 až 5 atómami halogénu, pričom atómy halogénu sú rovnaké alebo rôzne, pričom ako atóm halogénu je možné uviesť výhodne fluór, chlór alebo bróm, obzvlášť fluór, ako je trifluórmetylová skupina, difluórmetylová skupina, pentafluóretylová skupina, tetrafluóretylová skupina, trifluórchlóretylová skupina, trifluóretylová skupina, trifluóretoxyskupina, difluórmetoxyskupina, pentafluóretoxyskupina, tetrafluóretoxyskupina, trifluórchlóretoxyskupina, trifluórmetoxyskupina a trifluórmetyltioskupina; hydroxyskupinu; atóm halogénu, výhodne fluóru, chlóru, brómu a jódu, obzvlášť fluóru, chlóru a brómu; kyanoskupinu; nitroskupinu;, dialkylaminoskupinu s výhodne 1 až 4 uhlíkovým atómami, obzvlášť 1 alebo 2 uhlíkovými atómami v každej alkylovej skupine, ako je dimetylaminoskupina a dietylaminoskupina; karboxyskupinu; alkylalkoxyskupinu s 1 až 4 uhlíkovými atómami, hlavne 1 alebo 2 uhlíkovými atómami v každej alkylovej časti; karbonylalkoxyskupinu s 1 až 4 uhlíkovými atómami, obzvlášť s 1 alebo 2 uhlíkovými atómami v alkylovej časti, ako je karbonylmetoxyskupina a karbonyletoxyskupina; karbonylalkylovú skupinu s 1 až 4 uhlíkovými atómami, obzvlášť s 1 alebo 2 uhlíkovými atómami v alkylovej časti, ako je acetylová skupina a propionylová skupina; formylovú skupinu; karbonylaryloxyskupinu s 5 až 10 uhlíkovými atómami v arylovej časti, ako je karbonylfenoxyskupina; karbonylarylovú skupinu so 6 až 10 uhlíkovými atómami v arylovej časti, ako je benzoylová skupina; oxykarbonylaIkylovú skupinu s 1 až 4 uhlíkovými atómami, obzvlášť s 1 alebo 2 uhlíkovými atómami v alkylovej časti, ako je acetoxyskupinéi; oxykarbonylarylovú skupinu so 6 až 10 uhlíkovými atómami v arylovej časti, ako je benzoyloxyskupina; karboxylamínovú, karbonylaminoalkylovú, karbonylaminodialkylovú, aminokarbonylovú,. alkyloaminokarbonylovú, arainokarbonylalkylovú a alkylaminokarbonylalkylovú skupinu so vždy 1 až 4 uhlíkovými atómami, obzvlášť s 1 alebo 2 uhlíkovými atómami v alkylových častiach; sulfonamidoskupinu; sulfónalkylovú, sulfonylalkylovú a sulfonylalkoxylovú skupinu so vždy 1 až 4 uhlíkovými atómami, obzvlášť s 1 alebo 2 uhlíkovými atómami, alebo fenylovú alebo fenoxylovú skupinu, nesubstituované alebo substituované halogénmi, obzvlášť fluórom, chlórom a/alebo brómom.Optionally substituted radicals of the general formula can carry one or more, preferably one to three, in particular one or two, identical or different substituents. These substituents include, by way of example and preferably, an alkyl group, preferably having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl a group, i-butyl, sec-butyl and tert-butyl; alkoxy having preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms such as methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, ibutyloxy, sec-butyloxy and tert-butyloxy; alkylthio having preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, such as methylthio, ethylthio, n-propylthio, i -propylthio, n-butylthio, i-butylthio, sec-butylthio and tert-butylthio; a haloalkyl, haloalkoxy and haloalkylthio group having preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms and 1 to 9 especially 1 to 5 halogen atoms, the halogen atoms being the same or different, preferably halogen being fluorine , chloro or bromo, especially fluoro such as trifluoromethyl, difluoromethyl, pentafluoroethyl, tetrafluoroethyl, trifluorochloroethyl, trifluoroethyl, trifluoroethoxy, trifluoromethoxy, trifluoromethoxy, pentafluoroethoxy, tetrafluoroethoxy, tetrafluoroethoxy, tetrafluoroethoxy, tetrafluoroethoxy, tetrafluoroethoxy, tetrafluoroethoxy; OH; a halogen atom, preferably fluorine, chlorine, bromine and iodine, especially fluorine, chlorine and bromine; cyano; nitro; dialkylamino having preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms in each alkyl group, such as dimethylamino and diethylamino; carboxy; (C 1 -C 4) alkylalkoxy, in particular 1 or 2 carbon atoms in each alkyl moiety; carbonylalkoxy having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms in the alkyl moiety, such as carbonylmethoxy and carbonylethoxy; carbonylalkyl having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms in the alkyl moiety, such as acetyl and propionyl; a formyl group; carbonylaryloxy of 5 to 10 carbon atoms in the aryl moiety, such as carbonylphenoxy; carbonylaryl having 6 to 10 carbon atoms in the aryl moiety, such as benzoyl; oxycarbonylalkyl having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms in the alkyl moiety, such as acetoxy; a (C 6 -C 10) oxycarbonylaryl group such as a benzoyloxy group; carboxylamine, carbonylaminoalkyl, carbonylaminodialkyl, aminocarbonyl ,. alkyloaminocarbonyl, arainocarbonylalkyl and alkylaminocarbonylalkyl having in each case 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms in the alkyl moieties; sulfonamido; sulfonylalkyl, sulfonylalkyl and sulfonylalkoxy having in each case 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, or phenyl or phenoxy, unsubstituted or substituted by halogens, in particular fluorine, chlorine and / or bromine.
Tu uvádzané definície platia zodpovedajúcim spôsobom tiež pre definície v nasledujúcich výhodných kombináciách zvyškov.The definitions herein also apply accordingly to the definitions in the following preferred residue combinations.
Výhodné sú zlúčeniny všeobecného vzorca I, v ktoromPreferred are compounds of formula I wherein:
R' a R2 sú rovnaké alebo rôzne a znamenajú nesubstituovanú alebo substituovanú alkylovú skupinu s 1 až 4 uhlíkovými atómami, cykloalkylovú skupinu s 3 až 7 uhlíkovými atómami alebo fenylovú skupinu,R 1 and R 2 are the same or different and are unsubstituted or substituted C 1 -C 4 alkyl, C 3 -C 7 cycloalkyl or phenyl,
R' znamená alkylovú skupinu s 2 až 8 uhlíkovými atómami, substituovanú alkylovú skupinu s 1 až 8’uhlíkovými atómami, nesubstituovanú alebo substituovanú cykloalkylovú skupinu s 3 až 7 uhlíkovými atómami, fenylovú skupinu alebo fenylalkylovú skupinu s 1 až 4 uhlíkovými atómami v alkylovej časti,R 'represents an alkyl group having 2 to 8 carbon atoms, a substituted alkyl group having 1 to 8 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 7 carbon atoms, a phenyl group or a phenylalkyl group having 1 to 4 carbon atoms in the alkyl moiety,
R* , R5, R6, R7 a R8 sú rovnaké alebo rôzne a znamenajú vodíkový atóm, nesubstituovanú alebo substituovanú alkylovú skupinu s 1 až 8 uhlíkovými atómami, fenylalkylovú skupinu s 1 až v alkylovej časti, pričom R7 a vodíkový atóm, alebo fenylovú skupinu alebo uhlíkovými atómamiR 7, R 5 , R 6 , R 7 and R 8 are the same or different and represent a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms, a phenylalkyl group having 1 to an alkyl moiety, wherein R 7 and a hydrogen atom , or a phenyl group or carbon atoms
R8 neznamenajú súčasne znamenajú nezávisle od seba dodatočne tiež nesubstituovanú alebo s 3 až 7 uhlíkovými heteroarylovú skupinu, rôzne neteroatómy, ako je kyslík, dusík a síra, alebo zodpovedajúcu heteroarylalkylovú skupinu s 1 až 4 uhlíkovýmiR 8 do not simultaneously represent independently of one another additionally unsubstituted or 3 to 7 carbon heteroaryl, various non-heteroatoms such as oxygen, nitrogen and sulfur, or the corresponding 1 to 4 carbon heteroarylalkyl
substituovanú cykloalkylovú skupinu atómami, päťčlennú až deväťčlennú ktorá obsahuje 1 až 4 rovnaké alebo atómami v alkylovej časti alebosubstituted cycloalkyl group by atoms of five to nine members containing 1 to 4 identical or atoms in the alkyl moiety; or
Rb znamená skupiny -CHR4-COOH a -CHR4-COOCH3, aleboR b is -CHR 4 -COOH and -CHR 4 -COOCH 3 , or
R- a R spoločne s dusíkovým atomom, na ktorý su viazané, tvoria nesubstituovaný alebo substituovaný päťčlenný až sedemčlenný kruh, ktorý dodatočne môže obsahovať 1 alebo 2 rovnaké alebo rôzne heteroatómy, ako je kyslík, dusík a síra, aleboR 1 and R 2 together with the nitrogen atom to which they are attached form an unsubstituted or substituted 5- to 7-membered ring, which may additionally contain 1 or 2 identical or different heteroatoms such as oxygen, nitrogen and sulfur, or
R' a R spoločne s dusíkovým atomom, na ktorý su viazane, tvoria nesubstituovaný alebo substituovaný päťčlenný až sedemčlenný kruh, ktorý dodatočne môže obsahovať 1 alebo 2 rovnaké alebo rôzne heteroatómy, ako je kyslík, dusík a síra.R 1 and R 2 together with the nitrogen atom to which they are attached form an unsubstituted or substituted 5- to 7-membered ring, which additionally may contain 1 or 2 identical or different heteroatoms such as oxygen, nitrogen and sulfur.
Obzvlášť výhodné sú zlúčeniny všeobecného vzorca I, v ktorom ί nParticularly preferred are compounds of formula I wherein n is n
R a R su rovnaké alebo rôzne a znamenajú nesubstituovanu rozvetvenú alkylovú skupinu so 4 až 6 uhlíkovými atómami, substituovanú alkylovú skupinu s 1 až 6 uhlíkovými atómami, nesubstituovanú alebo substituovanú cyklopropylovú, cyklobutvlovú, cyklopéntylovú, cyklohexylovú alebo fenylovú skupinu,R and R are the same or different and are unsubstituted branched alkyl of 4 to 6 carbon atoms, substituted alkyl of 1 to 6 carbon atoms, unsubstituted or substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl,
RJ znamená alkylovú skupinu s 2 až 6 uhlíkovými atómami, substituovanú alkylovú skupinu s 1 až 6 uhlíkovými atómami, nesubstituovanú alebo substituovanú cyklopropylovú, cyklobutylovú, cyklopéntylovú, cyklohexylovú, fenylovú alebo benzylovú skupinu,R < 2 > is alkyl of 2 to 6 carbon atoms, substituted alkyl of 1 to 6 carbon atoms, unsubstituted or substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
R4 znamená vodíkový atóm alebo alkylovú skupinu s 1 až 4 uhlíkovými atómami alebo prípadne substituovanú fenylovú alebo benzylovú skupinu, c: 6R 4 represents a hydrogen atom or a C 1 -C 4 alkyl group or an optionally substituted phenyl or benzyl group, c: 6
R a R su rovnaké alebo rôzne a znamenajú vodíkový atóm, alkylovú skupinu sl až 8 uhlíkovými atómami, alebo nesubstituovanú alebo substituovanú fenylovú skupinu, pričom ako substituenty je možné uviesť výhodne atómy halogénu, alkylovú skupinu, alkoxyskupinu, alkyltioskupinu, halogénalkylovú skupinu, halogénalkoxyskupinu a halogénalkyltioskupinu,R and R are the same or different and are hydrogen, alkyl of 1 to 8 carbon atoms, or unsubstituted or substituted phenyl, preferably halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy and haloalkoxy; .
R7 a R8 sú rovnaké alebo rôzne a znamenajú vodíkový atóm, substituovanú alebo nesubstituovanú alkylovú skupinu s 1 až 6 uhlíkovými atómami, cyklopropylovú, cyklobutylovú, cyklopentylovú, cyklohexylovú, fenylovú a benzylovú skupinu, pričom ako substituenty je možné uviesť výhodne atóm halogénu, alkylovú skupinu, alkoxyskupinu, alkyltioskupinu, halogénalkylovú skupinu, halogénalkoxyskupinu, halogénalkyl tioskupinu a dialkylaminoskupinu, pričom všakR7 and R8 they are the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl and benzyl groups, the substituents being preferably a halogen atom, an alkyl group, an alkoxy group, , haloalkyl, haloalkoxy, haloalkyl thio and dialkylamino, however,
PP
R a R neznamenajú súčasne vodíkový atómR and R do not simultaneously represent a hydrogen atom
R3 znamená skupiny -CHR4-COOH a -CHR4-COOCH3, aleboR 3 is -CHR 4 -COOH and -CHR 4 -COOCH 3 , or
R a R spoločne s dusíkovým atómom, na ktorý sú viazané, tvoria nesubstituovaný alebo substituovaný piperidínový, morfolínový, hexahydroazepínový alebo piperazínový kruh, pričom ako substituenty je možné uviesť výhodne alkylovú skupinu a hydroxyalkylovú skupinu, alebo,R and R together with the nitrogen atom to which they are attached form an unsubstituted or substituted piperidine, morpholine, hexahydroazepine or piperazine ring, the substituents being preferably an alkyl group and a hydroxyalkyl group, or,
R a R° spoločne s dusíkovým atómom, na ktorý sú viazané, tvoria nesubstituovaný alebo substituovaný piperidínový, morfolínový, hexahydroazepínový alebo piperazínový kruh, pričom ako substituenty je možné uviesť výhodne alkylovú skupinu a hydroxyalkylovú skupinu.R and R ° together with the nitrogen atom to which they are attached form an unsubstituted or substituted piperidine, morpholine, hexahydroazepine or piperazine ring, preferably alkyl and hydroxyalkyl being substituents.
Celkom obzvlášť výhodné sú zlúčeniny všeobecného vzorca I, v ktorom tVery particularly preferred are compounds of formula I wherein t
RL znamená metyltriazolylovú skupinu, znamená prípadne nesubstituovanú alebo halogénom substituovanú fenoxyskupinu, substituovanú butylovú, pentylovú, hexylovú a heptylovú skupinu, alebo prípadne raz až trikrát fluórom, chlórom, brómom, metylovou skupinou, etylovou skupinou, metoxyskupinou, etoxyskupinou, trifluórmetylovou skupinou alebo trifluórmetoxyskupinou substituovanú fenylovú alebo cyklopropylovú skupinu,R 1 is methyltriazolyl, optionally unsubstituted or halo substituted phenoxy, substituted butyl, pentyl, hexyl and heptyl, or optionally one to three times fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, phenyl or cyclopropyl group,
R·, znamená etylovú skupinu, n-propylovu skupinu, i-propylovú skupinu, n-butylovú skupinu, i-butylovú skupinu, sek.-butylovú skupinu a terc.-butylovú skupinu alebo dimetylaminoskupinou, dietylaminoskupinou, metoxykarbonylovou skupinou alebo etoxykarbonylovou skupinou substituovanú etylovú, n-propylovú, i-propylovú, nbutylovú. i-butylovú, sek.-butylovú a terc.-butylovú skupinu, alebo prípadne fluórom, chlórom, brómom, metylovou skupinou, etylovou skupinou, metoxyskupinou, etoxyskupinou, trifluórmetylovou skupinou alebo trifluórmetoxyskupinou substituovanú fenylovú, benzylovú alebo cyklopropylovú, cyklobutylovú, cyklopentylovú alebo cyklohexylovú skupinuR 6 represents ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl and tert-butyl or dimethylamino, diethylamino, methoxycarbonyl or ethyl-substituted ethoxycarbonyl , n-propyl, i-propyl, n-butyl. i-butyl, sec-butyl and tert-butyl, or optionally fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy substituted phenyl, benzyl or cyclopropyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl, cyclobutyl,
R1' znamená vodíkový atóm, n-propylovú skupinu, skupinu. i-butylovú a terc.-butylovú skupinuR 1 'represents a hydrogen atom, an n-propyl group, a group. i-butyl and tert-butyl
R·' znamená vodíkový atóm, n-propylovú skupinu, skupinu, i-butylovú a terc.-butylovú skupinuR 4 'represents a hydrogen atom, an n-propyl group, an i-butyl group and a tert-butyl group
R6 znamená vodíkový atóm, n-propylovú skupinu, skupinu, i-butylovú a terc.-butylovú skupinu metylovu skupinu, etylovú skupinu, i-propylovú skupinu, n-butylovú skupinu, sek.-butylovú skupinu metylovú skupinu, etylovú skupinu, i-propylovú skupinu, n-butylovú skupinu, sek.-butylovú skupinu metylovú skupinu, etylovú skupinu, i-propylovú skupinu, n-butylovú skupinu, sek.-butylovú skupinu aleboR 6 represents a hydrogen atom, an n-propyl group, an i-butyl group and a tert-butyl group a methyl group, an ethyl group, an i-propyl group, a n-butyl group, a sec-butyl group a methyl group, an ethyl group, i -propyl, n -butyl, sec -butyl, methyl, ethyl, i -propyl, n -butyl, sec -butyl, or
R° a R6 spoločne s dusíkovým atómom, na ktorý sú viazané, tvoria piperidínový, morfolínový, hexahydroazepinový alebo piperazínový kruh,R 0 and R 6 together with the nitrogen atom to which they are attached form a piperidine, morpholine, hexahydroazepine or piperazine ring,
R' znamená vodíkový atóm, metylovú skupinu, etylovú skupinu, n-propylovú skupinu, i-propylovú skupinu, n-butylovú skupinu, i-butylovú skupinu, sek.-butylovú skupinu a terc.-butylovú skupinu,R 'represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group and a tert-butyl group,
Rc znamená prípadne dimetylaminoskupinou, dietylaminoskupinou, metoxykarbonylovou skupinou alebo etoxykarbonylovou skupinou substituovanú metylovú, etylovú, n-propylovú, i-propylovú, n-butylovú, i-butylovú, sek.-butylovú a terc.-butylovú skupinu. alebo prípadne raz až trikrát fluórom, chlórom, brómom, metylovou skupinou, etylovou skupinou, metoxyskupinou, etoxyskupinou, trifluórmetylovou skupinou alebo trifluórmetoxyskupinou substituovanú fenylovú, benzylovú, cyklopropylovú, cyklobutylovú, cyklopentylovú alebo cyklohexylovú skupinu, alebo znamená skupiny -CHR4 -COOH alebo -CHR4 -COOCHg, pričomR c is optionally dimethylamino, diethylamino, methoxycarbonyl or ethoxycarbonyl substituted by methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl and tert-butyl. or optionally mono- to trisubstituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy-substituted phenyl, benzyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or represents the group -CHR 4 -COOH or -CHR 4 -COOCHg, wherein
R4' znamená vodíkový atóm, metylovú skupinu, etylovú skupinu, n-propylovú skupinu, i-propylovú skupinu, n-butylovú skupinu, i-butylovú skupinu, sek.-butylovú skupinu, terc.-butylovú skupinu, fenylovú skupinu, bifenylovú skupinu, hydroxyfenylovú skupinu a benzylovú skupinu, aleboR 4 'represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a biphenyl group , hydroxyphenyl and benzyl, or
R' a R8 spoločne s dusíkovým atómom, na ktorý sú viazané, tvoria prípadne raz alebo dvakrát skupinou, hydroxymetylovou skupinou substituovaný metylovou skupinou, etylovou skupinou a hydroxyetylovou piperidínový, morfolínový, piperazínový alebo pyrolidínový kruh.R 1 and R 8 together with the nitrogen atom to which they are attached optionally form once or twice a group, a hydroxymethyl group substituted with a methyl group, an ethyl group and a hydroxyethyl piperidine, morpholine, piperazine or pyrrolidine ring.
Výhodné zlúčeniny sú tiež adičné produkty z kyselín a ich deriváty všeobecného vzorca I, v ktorých majú substituenty R1 a R8 významy, uvádzané už vyššie ako výhodné.Preferred compounds are also acid addition products and derivatives thereof of the general formula I, in which the substituents R 1 and R 8 have the meanings indicated above as being preferred.
Ku kyselinám, ktoré sa môžu adovať, patria výhodne halogénvodíkové kyseliny, ako je napríklad kyselina chlorovodíková a kyselina bromovodíková, obzvlášť kyselina chlorovodíková, ďalej kyselina fosforečná, kyselina dusičná, kyselina sírová, monofunkčné, difunkčné a trifunkčné karboxylové a hydroxykarboxylové kyseliny, ako je napríklad kyselina octová, kyselina rvaleinová, kyselina jantárová, kyselina fumarová, kyselina vínna, kyselina citrónová, kyselina salicylová, kyselina sorbová a kyselina mliečna, sulfónové kyseliny, ako je napríklad kyselina p-toluén-sulfónová a kyselina 1,5-naftaléndisulfónová, ako i sacharín alebo tiosacharín.Acids which can be added preferably include hydrohalic acids such as hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, monofunctional, difunctional and trifunctional carboxylic and hydroxycarboxylic acids, such as acetic acid, raleinic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, sulfonic acids such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid as well as saccharin or thiosaccharin.
Okrem toho výhodné zlúčeniny sú tiež adičné produkty zo solí a kovov II. až IV. hlavnej a I. a II., ako i IV. až VIII. vediajšej skupiny periodického systému prvkov a ich deriváty fi všeobecného vzorca I, . v ktorých majú substituentý R az R° významy, uvádzané už vyššie ako výhodné.In addition, salt and metal addition products II are also preferred. to IV. the main and I. and II., and IV. to VIII. the sub - group of the Periodic System of the Elements and their derivatives of formula (I),. in which the substituents R and R 0 have the meanings given above as being preferred.
Pritom sú obzvlášť výhodné soli medi, zinku, mangánu, horčíka, cínu, železa a niklu. Ako anióny týchto solí prichádzajú do úvahy také, ktoré sú odvodené od takých kyselín, ktoré vedú k adičným produktom, prijatelným pre životné prostredie. Ako obzvlášť výhodné kyseliny je možné v tejto súvislosti uviesť halogénvodíkové kyseliny, ako je napríklad kyselina chlorovodíková a kyselina bromovodíková, alebo kyselinu dusičnú a kyselinu sírovú.The salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred. Possible anions of these salts are those derived from acids which lead to environmentally acceptable addition products. Particularly preferred acids in this context are hydrohalogenic acids such as, for example, hydrochloric acid and hydrobromic acid, or nitric acid and sulfuric acid.
Nové deriváty tetrafluórbenzoovej kyseliny všeobecného vzorca I sa dajú vyrobiť spôsobmi analogickými spôsobom známym. Východiskové zlúčeniny potrebné na výrobu zlúčenín všeobecného vzorca I, sú známe, prípadne sa môžu vyrobiť pomocou všeobecne známych metód.The novel tetrafluorobenzoic acid derivatives of the formula I can be prepared by methods analogous to those known in the art. The starting compounds required for the preparation of the compounds of the formula I are known or can be prepared by methods known per se.
Reakcia východiskových zlúčenín sa vykonáva výhodne v inertných, s vodou nemiešatelných zrieďovadlách, ako sú napríklad aromatické, nearomatické alebo“halogénované uhlovodíky, ako sú napr.vklad chlórované uhlovodíky, napríklad dichlórmetán a trichlórme.tán, aromáty, napríklad toluén, alebo cyklohexán prípadne ich zmesi, alebo estery, napríklad etylester kyseliny octovej a/alebo za prítomnosti látok viažucich kyseliny, napríklad uhličitanu draselného, trietylamínu, pyridínu,The reaction of the starting compounds is preferably carried out in inert, water-immiscible diluents such as aromatic, non-aromatic or halogenated hydrocarbons such as chlorinated hydrocarbons such as dichloromethane and trichloromethane, aromatics such as toluene or cyclohexane or mixtures thereof or esters such as ethyl acetate and / or in the presence of acid binders such as potassium carbonate, triethylamine, pyridine,
N-metylpiperidinu, hydroxidu draselného alebo hydroxidu sodného, pri teplote v rozmedzí 0 C až 100 °C, výhodne 20 “C až 40 °C a za normálneho tlaku. Pri reakcii s aminokyselinami sa pracuje vo vodnom roztoku, výhodne s hydroxidom sodným ako pomocnou bázou, pri teplote v rozmedzí 0 °C až 20 °C.N-methylpiperidine, potassium hydroxide or sodium hydroxide, at a temperature in the range of 0 ° C to 100 ° C, preferably 20 ° C to 40 ° C and under normal pressure. The reaction with the amino acids is carried out in aqueous solution, preferably with sodium hydroxide as an auxiliary base, at a temperature in the range of 0 ° C to 20 ° C.
Predložený vynález zahrňuje ako čisté izoméry, tak tiež zmesi. Tieto zmesi sa môžu pomocou použiteľných metód, napríklad selektívnou kryštalizáciou z vhodných rozpúšťadiel alebo chromatografiou na silikagéli alebo oxide hlinitom rozdeliť na svoje komponenty. Racemáty sa môžu rozdeliť na jednotlivé enantioméry pomocou bežných metód, napríklad tvorbou solí s opticky aktívnymi kyselinami, ako je kyselina gáforsulfónová alebo kyselina dibenzoylvínna a ďalej selektívnou kryštalizáciou alebo derivatizáciou s vhodnými opticky aktívnymi reagenciami, oddelením diastereomérnych derivátov a spätným štiepením alebo delením na opticky aktívnom materiáli stĺpca.The present invention includes both pure isomers and mixtures. These mixtures can be separated into their components using suitable methods, for example by selective crystallization from suitable solvents or by chromatography on silica gel or alumina. The racemates can be separated into the individual enantiomers by conventional methods, for example by forming salts with optically active acids, such as camphorsulfonic acid or dibenzoyltartaric acid, and further by selective crystallization or derivatization with suitable optically active reagents, separation of diastereomeric derivatives and reverse resolution or optically active resolution. column.
Účinné látky podľa predloženého vynálezu všeobecného vzorca I vykazujú silný účinok voči škodcom a môžu sa prakticky použiť na kynoženie škodlivých organizmov. Tieto účinné látky sú vhodné na použitie ako ochranné prostriedky pre rastliny, hlavne ako fungicídy.The active compounds according to the invention of the general formula (I) show a strong action against pests and can be used in practice for the control of harmful organisms. These active compounds are suitable for use as plant protection agents, in particular as fungicides.
Fungicídne prostriedky v ochrane rastlín sa používajú na kynoženie Plasmodiophoromycet, Oomycet, Chytridiomycet,Fungicidal agents in plant protection are used for the proofing of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes,
Zygomycet, Ascomycet, Basidiomycet a Deuteromycet.Zygomycet, Ascomycet, Basidiomycet and Deuteromycet.
Príklade zo, ale nie obmedzujúcim spôsobom, je možné uviesť niektorých pôvodcov hubových ochorení, ktorí spadajú pod vyššie uvedené.Examples of, but not limited to, some agents of fungal diseases that fall under the above.
Druhy Pythium, ako je napríklad Pythium ultimum.Pythium species, such as Pythium ultimum.
Druhy Phytophzhora, ako je napríklad Phytophthora infestans.Phytophzhora species, such as, for example, Phytophthora infestans.
Druhy Pseudoperonospora, ako je napríklad Pseudoperonospora humuli alebo Pseudoperonospora cubensis.Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis.
Druhy Plasmopara, ako je napríklad Plasmopara viticola.Plasmopara species, such as, for example, Plasmopara viticola.
Druhy Peronospora, ako je napríklad Peronospora pisi alebo Peronospora brassicae.Peronospora species, such as Peronospora pisi or Peronospora brassicae.
Druhy Ervsiphe, ako je napríklad Erysiphe graminis.Ervsiphe species, such as Erysiphe graminis.
Druhy Sphaerotheca, ako je napríklad Sphaerotheca fuliginea.Sphaerotheca species, such as Sphaerotheca fuliginea.
Druhy Podosphaera, ako je napríklad Podosphaera leucotricha.Podosphaera species, such as, for example, Podosphaera leucotricha.
Druhy Venturia, ako je napríklad Venturia inaequalis.Venturia species, such as Venturia inaequalis.
Druhy Pyrenophora, ako je napríklad Pyrenophora teres alebo Pyrenophora graminea (konídiová forma: Drechslera, Synonymum: Helminthosportum).Pyrenophora species, such as Pyrenophora teres or Pyrenophora graminea (conidia form: Drechslera, Synonym: Helminthosportum).
Druhy Cochliobolus, ako je napríklad Cochliobolus sativus (konídiová forma: Drechslera, Synonymum: Helminthosporium).Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, Synonym: Helminthosporium).
Druhy Uromyces, ako je napríklad Uromyces appendiculatus.Uromyces species, such as Uromyces appendiculatus.
Druhy Pucciniu, ako je napríklad Puccinia recondita.Puccinia species, such as Puccinia recondita.
Druhy Tilletia, ako je napríklad Tilletia caries.Tilletia species, such as Tilletia caries.
Druhy Ustilago, ako je napríklad Ustilago nuda alebo Ustilago avenae.Ustilago species, such as Ustilago nuda or Ustilago avenae.
Druhy Pellicularia, ako je napríklad Pellicularia sasakii.Pellicularia species, such as Pellicularia sasakii.
Druhy Pyricularia, ako je napríklad Pyricularia oryzae.Pyricularia species, such as Pyricularia oryzae.
Druhy Leptosphaeria, ako je napríklad Leptosphaeria nodorum.Leptosphaeria species, such as Leptosphaeria nodorum.
Druhy Cercospora, ako je napríklad Cercospora canescens.Cercospora species, such as Cercospora canescens.
Druhy Alternácia, ako je napríklad Alternaria brassicae.Alternative species, such as Alternaria brassicae.
Druhy Pseudocercosporella, ako je napríklad Pseudocercosporella herpotrichoides.Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.
Dobrá prijateľnosť účinných látok pre rastliny v koncentráciách nevyhnutných na kynoženie ochorení rastlín dovoľuje ošetrenie nadzemných častí rastlín, sadeníc rastlín, osiva a pôdy.The good acceptability of the active ingredients for plants at the concentrations necessary for the propagation of plant diseases permits the treatment of above-ground parts of plants, plant seedlings, seeds and soil.
Účinné látky podľa predloženého vynálezu sa pritom dajú použiť s obzvlášť dobrým úspechom na kynoženie druhu Pyricularia na ryžu.The active compounds according to the invention can in this case be used with a particularly good success for the proofing of Pyricularia on rice.
Účinné látky podľa predloženého vynálezu majú ďalej silný rezistenciu indikujúci účinok u rastlín. Sú teda vhodné na vypestovanie rezistencie u rastlín proti napadnutiu nežiaducimi mikroorganizmami.Furthermore, the active compounds according to the invention have a strong resistance indicating activity in plants. They are therefore suitable for growing resistance in plants to attack by unwanted microorganisms.
Pod pojmom rezistenciu indukujúce látky sa v danej súvislosti chápu také látky, ktoré jednak pri priamom pôsobení na nežiaduce mikroorganizmy vykazujú iba nepatrnú aktivitu, na druhej strane ale sú schopné stimulovať obranný systém rastlín tak, že ošetrené rastliny pri nasledujúcej inokulácii nežiaducimi mikroorganizmami majú vyvinutú vysokú rezistenciu voči týmto mikroorganizmom.Resistance-inducing substances in this context are understood to be those which, by acting directly on undesirable microorganisms, exhibit only slight activity but, on the other hand, are capable of stimulating the plant defense system so that the treated plants have a high resistance when subsequently inoculated with undesirable microorganisms. against these microorganisms.
Pod pojmom nežiaduce mikroorganizmy sa v uvedenom prípade chápu fytopatogénne huby, baktérie a vírusy. Látky podlá predloženého vynálezu sa môžu teda použiť tak, aby rastliny v priebehu určitého časového úseku po ošetrení získali rezistenciu proti napadnutiu uvedenými pôvodcami poškodenia.The term undesirable microorganisms in this case refers to phytopathogenic fungi, bacteria and viruses. Thus, the compounds of the present invention can be used so that the plants acquire resistance to attack by said causative agents over a period of time after treatment.
Časový úsek, počas ktorého sa dosiahne rezistencia, je všeobecne 1 až 10 dní, výhodne 1 až 7 dní, po ošetrení rastlín účínnými látkami.The time period during which resistance is achieved is generally 1 to 10 days, preferably 1 to 7 days, after treatment of the plants with the active substances.
K nežiaducim mikroorganizmom v ochrane rastlín patria huby z tried Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes a Deuteromycetes.Undesirable microorganisms in plant protection include fungi of the classes Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Účinné látky sa môžu v závislosti od svojich fyzikálnych a/alebo chemických vlastností previesť na bežné prípravky, ako sú roztoky, emulzie, suspenzie, prášky, peny, pasty, granuláty, aerosóly, jemné kapsule v polymérnych látkach a zapuzdrovacie h roty pre os i/o, ako i prípravky na hmlenie za studená a za tepla (ULV-pŕípravky).The active substances can, depending on their physical and / or chemical properties, be converted into conventional preparations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, fine capsules in polymeric substances and encapsulating tips for axes. as well as cold and hot milling preparations (ULV preparations).
Tieto prípravky sa vyrábajú pomocou známych spôsobov, napríklad zmiešaním účinnej látky s plnidlom, teda kvapalným rozpúšťadlom, za tlaku skvapalneným plynom a/alebo pevným nosičom, prípadne za použitia povrchovo aktívnych činidiel, teda emulgačných činidiel a/alebo dispergačných činidiel a/alebo penotvorných činidiel. V prípade použitia vody ako zrieďovacieho činidla sa môžu tiež ako pomocné rozpúšťacie prostriedky použiť napríklad organické rozpúšťadlá.These preparations are prepared by known methods, for example by mixing the active ingredient with a filler, i.e. a liquid solvent, under pressure with a liquefied gas and / or a solid carrier, optionally using surfactants, i.e. emulsifying agents and / or dispersing agents and / or foaming agents. If water is used as a diluent, for example, organic solvents can also be used as solubilizers.
Ako kvapalné rozpúšťadlá prichádzajú v podstate do úvahy: aromáty, akc. je napríklad xylén, toluén a alkylnaftalény, cí;.órované aromáty alebo chlórované alifatické uhľovodíky, ako sú napríklad chlórbenzény, chlóretylény alebo metylénchlorid, alifatické uhľovodíky, ako je cyklohexán alebo parafíny, napríklad ropné frakcie, ďalej alkoholy, ako je butylalkohol alebo glykoly. ako i ich étery a estery, ketóny, ako je acetón, m·..-tyletylketó:i, metylizobutylketón alebo cyklohexanón, silne polárne rozpúšťadlá, ako je dimetylformamid alebo ó; iietylsulfox i.d, ako i voda. Pod pojmom skvapalnené zried'ovadlá a obo nosiče sa chápu také kvapaliny, ktoré sú pri normálnej teplote a pri normálnom tlaku plynné, napríklad aerosólové nosné piyny ako je bután, propán, dusík a oxid uhličitý.Basically suitable liquid solvents are: aromatics, ac. is, for example, xylene, toluene and alkylnaphthalenes, fluorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins such as petroleum fractions, alcohols such as butyl alcohol or glycols. as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or δ; ethylsulfox i.d as well as water. Liquid diluents and both carriers are understood to be those liquids which are gaseous at normal temperature and pressure, for example aerosolized carrier gases such as butane, propane, nitrogen and carbon dioxide.
Ako pevné nosiče prichádzajú do úvahy napríklad prírodné präškovité horniny ako je kaolín, íl, mastenec, krieda, kremeň, a- ’.pulgiť., montmorillonit alebo kremelina a syntetické múčky, ako sá vysoko disperzná kyselina kremičitá, oxid hlinitý a silikáty. Ako pevné nosiče pre granuláty prichádzajú do úvahy napríklad drvené a frakcionované prírodné horniny, ako je kalcit, mramor, popaza, sepiolit, dolomit, ako i syntetické granuláty z anorganických a organických múčok a granuláty z organických materiálov, ako sú piliny, škrupiny kokosových orechov, kukuričné tyče a tabakové stonky.Suitable solid carriers are, for example, natural powdery rocks such as kaolin, clay, talc, chalk, quartz, and pulp, montmorillonite or diatomaceous earth and synthetic flours such as highly disperse silica, alumina and silicates. Suitable solid carriers for granulates are, for example, crushed and fractionated natural rocks such as calcite, marble, popaz, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours and granules of organic materials such as sawdust, coconut shells, corn bars and tobacco stems.
Ako emuigátory a/alebo speňovacie prostriedky prichádzajú do úvahy napríklad neionogénne a anionické emulgátory, ako sú estery po ..yoxyetylén-mastných kyselín a étery polyoxyetylén-mastných alkoholov, napríklad alkylarylpolyglykolétery, alkylsulfonáty, a jkylsulfáty, arylsulfonáty, ako i bielkovinové hydrolyzáty. Ako dispergačné činidlá prichádzajú napríklad do úvahy lignínsulfitové výluhy a metylcelulóza.Suitable emulsifiers and / or foaming agents are, for example, non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters and polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, and alkylsulfates, arylsulfonates, as well as protein sulfonates. Suitable dispersing agents are, for example, lignosulphite leachates and methylcellulose.
V prípravkoch sa môžu tiež použiť prostriedky na zvýšenie priľnavosti, ako je karboxymetylcelulóza, prírodné a syntetické, p, iškovité, zrnité alebo latexovité polyméry, ako arabská guma, p .· i.yvinylalkc-hol aAdhesion enhancers such as carboxymethylcellulose, natural and synthetic, β, clinker, granular or latex polymers such as acacia, p.
n.viríklad kefalíny polyvinylacetát, ako i prírodné fosfolipidy, a lecitíny a syntetické fosfolipidy. Ďalšími .:·< r.ivami môžu byť minerálne a rastlinné oleje.n, for example, polyvinyl acetate cephalins, as well as natural phospholipids, and lecithins and synthetic phospholipids. Other ingredients may be mineral and vegetable oils.
Môžu sa tiež použiť farbivá, ako sú anorganické pigmenty, .v oriklad oxidy železa, oxid titaničitý, ferokyanátová modrá a organické ľarbivá, ako sú alizarínové farbivá, azofarbivá kovové fta locyanínové farbivá a stopové živné látky, ako sú j L i železa, nangánu, boru, medi, kobaltu, molybdénu a zinku.Dyes such as inorganic pigments, such as iron oxides, titanium dioxide, ferrocyanate blue and organic colorants such as alizarin dyes, azo dyes metal phthalocyanine dyes and trace nutrients such as iron, nangan, boron, copper, cobalt, molybdenum and zinc.
Prípravky obsahujú všeobecne 0,1 až 95 % hmotnostných hc.nnej látky. výhodne 0,5 až 90 % hmotnostných.The formulations generally contain from 0.1 to 95% by weight of the active substance. preferably 0.5 to 90% by weight.
Účinné 1itky podlá predloženého vynálezu sa môžu vyskytovať -·· ' prípravkoch v zmesi s inými známymi účinným látkami, ako sú x iigicídy, insekticídy, akaracídy, nematocídy a herbicídy, ako ·. '' zmesi s hnojivami a rastovými regulátormi.The active ingredients of the present invention may be present in the formulations in admixture with other known active ingredients such as xigicides, insecticides, acaracids, nematicides and herbicides, such as. Mixtures with fertilizers and growth regulators.
Účinné látky podlá predloženého vynálezu sa môžu používať vo svojich prípravkoch tiež v zmesi so známymi fungicídmi, baktericídmi, insekticídmi, akaracídmi, nematocídmi a herbicídmi, aby sa tak rozšírilo ich spektrum účinku alebo sa zamedzilo vzniku rezistencie. V mnohých prípadoch sa pritom dosiahne synergický efekt, to znamená, že účinok zmesi je vyšší ako účinok j ·..-inot 1 ivých komponentov.The active compounds according to the invention can also be used in their formulations in admixture with known fungicides, bactericides, insecticides, acaracides, nematicides and herbicides in order to broaden their spectrum of action or to prevent resistance. In many cases, a synergistic effect is achieved, i.e. the effect of the mixture is higher than that of the individual components.
Ako zložky týchto zmesí je možné uviesť nasledujúce látky:The components of these mixtures include:
'<·' i.-igicídy:'<·' I.-igicides:
2-aminobután 2-anilino-4-metyl-6-cyklopropyl-pyrimidín, 2',6'd.i :)romo-2-mer.yl-4 * -trifluórometoxy-4 ' -trif luóro-metyl-1,3-tiazol2-Aminobutane 2-anilino-4-methyl-6-cyclopropyl-pyrimidine, 2 ', 6'-dihydro-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3- thiazole
--carboxani Ϊ Ld, 2,6-dichlóro-N- ( 4-trif luórometylbenzyl) -benzamid, (E)-2~metoxyimino-N-metyl-2-(2-fenoxyfenyl)-acetamid, 8-hydroxyquinolínsulfát, metyl-(E)-2-{2-[6-(2-kyanofenoxy)-pyrimidín4 -yloxy]f eny11-3-metoxyakrylát, metyl-(E)-metoximino-[a-(o-to1vLoxy)-o-tol/1Jacetát, 2-fenylfenol (OPP),- carboxanil, 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide, (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide, 8-hydroxyquinoline sulphate, methyl - (E) -2- {2- [6- (2-cyanophenoxy) -pyrimidin-4-yloxy] -phenyl-3-methoxyacrylate, methyl (E) -methoxyimino- [α- (o-tolyl) oxy] -o-tol / 1 Acetate, 2-phenylphenol (OPP),
AJ.dimorph, Amoropylfos, Anilazin, Azaconazol,AJ.dimorph, Amoropylfos, Anilazine, Azaconazole,
Eiiaiaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Betertanol, nl isticidin··.:·, Bromuconazole, Bupirimate, Buthiobate, ··. :.ciumpoly:i·;··!;.fid, Captafol, Captan, Cardendazim, Carboxin,Eiiaiaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Betertanol, nl isticidin: ·, Bromuconazole, Bupirimate, Buthiobate, ··. : .ciumpoly: i ·; ··!; .fid, Captafol, Captan, Cardendazim, Carboxin,
C.;, .nomethiona- (Quinomethionat) , Chloroneb, Chloropicrin,C.;, .Nomethiona- (Quinomethionat), Chloroneb, Chloropicrin,
Ch i.orothaloni L, Chlozolinat, Cufraneb, Cymaxanil, Cyproconazole, Cyprofurán,Ch i.orothaloni L, Chlozolinate, Cufraneb, Cymaxanil, Cyproconazole, Cyprofuran,
D i.--.hlorophen .. Diclobutrazol, Diclof luanid , Diclomezin, Dicloran,D i .--. Hlorophen .. Diclobutrazole, Diclof luanide, Diclomezin, Dicloran,
Dlethofencar:? Difenocanazol, Dimethirimol, Dimethomorph, D.i.niconazol , Dinocap, Diphenylamin, Dipyrithion, Ditalimfos, Dithianon, Dedine, Drazoxolon,Dlethofencar :? Difenocanazole, Dimethirimol, Dimethomorph, D.I.niconazole, Dinocap, Diphenylamine, Dipyrithion, Ditalimfos, Dithianon, Dedine, Drazoxolone,
Ed .fenphoEd .fenpho
Γ cf \arimol , npropidin. rbam , F r iquincona /Im cf \ arimol, npropidine. rbam, F iquincona /
Flutriafo).,Flutriafol).
Fv.ralaxyl, i'iF. lalaxyl, i'i
TJTJ
t.; Λt .; Λ
Fpoxyconazole, enbuconazole,Fpoxyconazole, enbuconazole,
Fenpropimorph, rimzone, Fluazinam,Fenpropimorph, rimzone, Fluazinam,
Le, Flusilazole, folpet, Fosetyl-Aluminium, rmecyclox,Le, Flusilazole, Folpet, Fosetyl-Aluminum, rmecyclox,
Ethirimol, Etridiazol,Ethirimol, Etridiazole,
Fenfuram, Fenitropan, Fenpiclonil, Fentinacetat, Fentrinhydroxyd, Fluoromide, Flutolanil, Fuberidazol,Fenfuram, Fenitropan, Fenpiclonil, Fentinacetate, Fentrinhydroxyd, Fluoromide, Flutolanil, Fuberidazole,
Fludioxonil,fludioxonil
Flusulfamide,flusulfamide.
Fthalide,Fthalide.
Guazatine,guazatine;
Heachlorobenzol, Hexaconazol, Hymexazol,Heachlorobenzole, Hexaconazole, Hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobenfos (IBP), Iprodion,Imazalil, Imibenconazole, Iminoctadine, Iprobenphos (IBP), Iprodion,
Tsoprot-hiolan .Tsoprot-hiolan.
Kasugamycin. meďnaté prípravky, ako hydroxid meďnatý, naftenát meďnatý, oxychlorid meďnatý, síran meďnatý, oxid meďnatý, Oxin-meď a Bordeaux-zmes, ľ'bancopper, ilancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Meeconazol, ?le thysulf ocarb, Methfuroxam, Metiram, Metsulfovax,Kasugamycin. copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxin-copper and Bordeaux-blend, bancopper, ilancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Meeconazole, le thysox ocarb, Methfuroxam Metiram, Metsulfovax,
Mvclobutanil, rĽekel-dimet rditiocarbamat, Nitrothyl-izopropyl, Naurimol,Mycobutanil, rekel-dimethyl rdithiocarbamat, Nitrothyl-isopropyl, Naurimol,
Oí'arace, Oxadixyl, Oxamocarb, Oxycarboxin,Irradiation, Oxadixyl, Oxamocarb, Oxycarboxin,
Peťurazoat, Penconazol, Pencycuron, Phosdiphen, Phthalid, P.i.maricin, Fiperalin, Polycarbamate, Polyoxin, Probenazol, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb, Pyrazophos, žyrifenox, Pyrimethynil, Pyroquilon,Peturazoate, Penconazole, Pencycuron, Phosdiphen, Phthalid, P.i.maricin, Fiperalin, Polycarbamate, Polyoxin, Probenazole, Prochloraz, Procymidone, Propamocarb, Propiconazole, Propineb, Pyrazophos, Žyrifenox, Pyrimethynil, Pyroquilon,
Quintozen (PCNB), síra a sírne prípravky,Quintozene (PCNB), sulfur and sulfur preparations,
Tí· buconazol, Tecloftalam, Tacnazen, Tetraconazol, Thiabendazol, Ti: Lcyofen, Thiophanat-metyl, Thiram, Tolclophos-metylTolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, '?: .cyclazol.. Tridemorph, Triflumizol, Triforin, Triticonazol, v a1 idamycin A Vinclozolin.T-buconazole, Tecloftalam, Tacnazen, Tetraconazole, Thiabendazole, Ti: Lcyofen, Thiophanate-methyl, Thiram, Tolclophos-methylTolylfluanid, Triadimefon, Triadimenol, Triazoxide, Trichlamide, Tricylamide, Triforol, Triforol, Triforol, Triforol, Triforol, α1 idamycin A Vinclozolin.
Zrneb, ZiramZrneb, Ziram
B Z.·tericidy i< :>nopol, Dí.chlorophen, Nitrapyrin, Nickel-Dimethyldithio -bamat, Kasugamycin, Octhilinon, kyselina furánkarboxylová, t 'tetracycj ta, Probenazol, Streptomycín, Tecloftalam, síranB. Z. tericides i <:> nopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithio-bamat, Kasugamycin, Octhilinone, furancarboxylic acid, tetracyclic, Probenazole, Streptomycin, Tecloftalam, sulphate
ľ.-·· ífnatý a d’cJ. áie prípravky medi :· ;ekticídy/.->:<aricídy/NematicídyI '. - ·· Phosphate and d'cJ. ecticides /.->: <aricides / Nematicides
AB.imectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, ä ·. íhamethrin.. Amitraz, Avermectin AZ 60541, Azadirachtin, Azi.nphos A, A?,inphos M, Azocyclotin,AB.imectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, and. Amitraz, Avermectin AZ 60541, Azadirachtin, Azi.nphos A, A? inphos M, Azocyclotin,
Bacilus tturingiensis, Bendiocarb, Benfuracarb, Bensultap, Beaacyluthrin .· Bifentrin, BPMC, Brofenprox, Bromophos A, Eufencarb, Buprofezin, Butocarboxin, Butylpyridaben,Bacilus tturingiensis, Bendiocarb, Benfuracarb, Bensultap, Beaacyluthrin · Bifentrin, BPMC, Brofenprox, Bromophos A, Eufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran,Cadusafos, Carbaryl, Carbofuran,
C:ta p , CGA 157 419, CGA 184699,C: ta p, CGA 157 419, CGA 184699
C 'i lorfenviphcs, Chlorfl.uazuron,C 'i lorfenviphcs, Chlorfl.uazuron,
Carbophenothion, Carbosulfan, Chloethocarb, Chorethoxyfos, chlormephos, Chlorpyrifos,Carbophenothion, Carbosulfan, Chloethocarb, Chorethoxyfos, Chlorormephos, Chlorpyrifos,
C··, i.orpyrif os M,C ··, i.orpyrif axis M,
Cis-Resmethrin, Clocythrin, Clofentezin, č/anophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin,Cis-Resmethrin, Clocythrin, Clofentezin, b / anophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin,
D?, ľtainethrin. Demeton M, Demeton S, Demeton-S-methyl, i;...ifenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, .rotophos. Biethion, Diflubenzuron, Dimethoat, Dimethylvinphos,D ?, lethethrin. Demeton M, Demeton S, Demeton-S-methyl, ... ifenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, .rotophos. Biethion, Diflubenzuron, Dimethoat, Dimethylvinphos,
D..oxathion, Disulfoton,D. oxathion, Disulfoton,
FenothiocarbFenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, r’Aiithion, kanva lerate, Fipronil, Fluazinam, Flucycloxuron, ľ'ixythrinat. Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, šaľ'mathion, Fosthiazat, Fubfenprox, Furathiocarb,FenothiocarbFenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, r'Aiithion, lerate can, Fipronil, Fluazinam, Flucycloxuron, l'ixythrinat. Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, salmion, Fosthiazat, Fubfenprox, Furathiocarb,
H. í, Heptenc'ť ios , Hexaf lumuron, Hexythiazox,H., Heptosios, Hexaf lumuron, Hexythiazox,
IÍdacloprid, Ibrobenfos, Isazophos, Isofenphos, Isoprocarb, . >->xathion, ve.rmectin, Lambda-cyhalothrin, Lufenuron,Idacloprid, Ibrobenfos, Isazophos, Isofenphos, Isoprocarb,. > -> xathion, ve.rmectin, Lambda-cyhalothrin, Lufenuron,
1' .athion, íecarbam, Mervinphos, Mesulfenphos, Metaldehyd, íhacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, ii·· rolcarb, Milbemectin, Monocrotophos, Moxidectin,1 '.athion, Iecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Alacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, ii ·· rolcarb, Milbemectin, Monocrotophos, Moxidectin,
’.ed, NC 182 , NI 25, Nitenpyram, ithoat, Oxamyl, Oxydemethon M, Oxydeprofos,Ed .ed, NC 182, NI 25, Nitenpyram, ithoat, Oxamyl, Oxydemethone M, Oxydeprofos,
·.-athion A, Parathion M, Permethrin, Phenthoat, Phorat, ’ .salón, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos 1; Pirimipho s A, Profenofos, Promecarb, Propaphos, Propoxur, : -athiofos , Prothoat, Pymetrozin, Pyrachlophos , Pyradaphenthion, P.·-esmethrin , Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Q· i .nalphos, λ ·. 5992 ,· Athion A, Parathion M, Permethrin, Phenthoat, Phorat, 'saloon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos 1; Pirimipho s A, Profenofos, Promecarb, Propaphos, Propoxur, -athiophos, Prothoat, Pymetrozine, Pyrachlophos, Pyradaphenthion, P. · esmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Q · inalphos, λ ·. 5992,
3· ·. ..ithion, Sebufos, Silafluofen, Sulfotep, Sulfprofos, ··.?. rufenozid , Tebufenpyrad, Tebupirimphos, Teflubenzuron, ,;luthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Th.afenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Th iringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, < chlorfon, Triflumuron, Trimethacarb,3 · ·. ..ithion, Sebufos, Silafluofen, Sulfotep, Sulfprofos, ··. rufenozide, Tebufenpyrad, Tebupirimphos, Teflubenzuron,, ; luthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Th.afenox, Thiodicarb, Thiofanox, Thiomethon, Thionazine, Th iringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, <chlorphon, Triflumuron, Trimethacarb,
v.aiidothion,v.aiidothion.
i.·':;, Xylylcarb,i. · ': Xylylcarb
5301/5302, .! '.amethrin.5301/5303,.! '.Amethrin.
Možné sú tiež zmesi s inými známymi účinnými látkami, ako sú iio -bicidy, alebo s hnojivami a rastovými regulátormi.Mixtures with other known active substances such as iobicides or with fertilizers and growth regulators are also possible.
Účinné Latky sa môžu používať ako také, vo forme svojich P r ^pravkov, alebo z nich pripravených aplikačných foriem, ako sú • .ikačné roztoky, suspenzie, postrekové prášky, pasty, rozpustné prášky, postreky a granuláty. Aplikácia sa vykonáva bežnými spôsobmi, napríklad polievaním, postrekovaním rozstrekovaním, Poprašovaním, rozprašovaním, napeňovaním, natieraním a podobne. D- ..ej je tiež možné použiť postup Ultra-Low-Volume alebo . .šikovať próoravok účinnej látky alebo účinnú látku samotnú do ;.> ·!y. Môže sa tiež spracovávať osivo rastlín.The active ingredients can be used as such, in the form of their formulations, or from their application forms, such as solution solutions, suspensions, spray powders, pastes, soluble powders, sprays and granules. The application is carried out by conventional means, for example by watering, spraying, spraying, spraying, foaming, coating and the like. It is also possible to use the Ultra-Low-Volume method. bias the pro-drug of the active substance or the active substance itself into;. Plant seed may also be processed.
Pri ošg 'mrení častí rastlín sa môžu koncentrácie účinnýchConcentrations can be effective in controlling plant parts
..rok v aplikačných formách pohybovať v širokom rozmedzí...year in application forms to move in a wide range.
\ :obecne ’j-? táto koncentrácia 1 až 0,0001 % hmotnostných, ,'iodne 0,5 .ιζ 0,001 % hmotnostných.\: generally ’j-? this concentration is from 1 to 0.0001% by weight, i.e. 0.5 to 0.001% by weight.
Pri ošetrení osiva sú všeobecne potrebné množstvá účinnej .ky 0,001 až 50 g na jeden kilogram osiva, výhodne 0,01 až 10In the treatment of seed, amounts of active compound of from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
Pri ošetrení pôdy sú potrebné koncentrácie účinnej látky 0 :000i až ),1 % hmotnostných, výhodne 0,0001 až 0,02 %In soil treatment, active compound concentrations of 0: 000 to 1% by weight, preferably 0.0001 to 0.02%, are required.
V.. .••tnostných na mieste pôsobenia.In .. •• on site.
Pri po;.ti ako induktorov rezistencie sa môžu koncentrácie >.:·· nnej látky na ošetrenie rastlinných častí pohybovať v iplikačnýcn formách v širokom rozmedzí. Pohybujú sa všeobecne tozmedzí 1 až 0,0001 % hmotnostných, výhodne 0,5 až 0,001 % ia ••.otnostnýchWhen used as resistance inducers, the concentrations of the plant substance treatment agent can vary widely in application forms. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
Príklady vyhotovenia vynálezu výroba a použitie látok podlá predloženého vynálezu sú <f:;;asnené pojwcou nasledujúcich príkladov vyhotovenia.Examples The preparation and use of compounds of the present invention, the <f: ;; simultaneously pojwcou following examples.
Výrobné príkladyProduction examples
Príklaprik
FF
FF
Za miešaaia sa pri teplote 20 “C prikvapká 55 g (0,26 mól) ;,5,6-tetia fluórbenzoylchloridu k roztoku 42,4 g (0,27 mól) · -lydroxyace :/1 -2,3 ,4,5,6,7-hexahydroazepínu a 27 g (0,27 mól) t -.étylámínv; v 500 ml metylénchloridu v priebehu 30 minút. Po :šani cez noc sa reakčná zmes spracuje vodou a dichlórmetánom organická fáza sa oddelí a vo vákuu sa zahustí. Získa sa takto v.:. ;ká olejoviuá kvapalina, ktorá čoskoro kryštalizuje.55 g (0.26 mol) of 5,6-tetrafluorobenzoyl chloride are added dropwise with stirring at 20 DEG C. to a solution of 42.4 g (0.27 mol) of. 5,6,7-hexahydroazepine and 27 g (0.27 mol) of t-ethylamine; in 500 mL of methylene chloride over 30 minutes. After stirring overnight, the reaction mixture is treated with water and the dichloromethane is separated and the organic phase is concentrated in vacuo. It is obtained as follows:. an oily liquid which soon crystallizes.
K roztoku 8,08 g (49 mmól) L-fenylalanínu v 25 ml 2N hároxidu sodného sa prikvapká za chladenia ladom súčasne 10,6g ! mmól) 2.3,5,6-tetrafluórbenzoylchloridu a 25 ml 2N hydroxidu s iného. Po miešaní cez noc sa hodnota pH upraví pomocou :: edene j kyseliny chlorovodíkovej na 2 a vytvorený kryštalizát s· odsaje.To a solution of 8.08 g (49 mmol) of L-phenylalanine in 25 ml of 2N sodium hydroxide was added dropwise simultaneously with ice-cooling 10.6 g. 2.3,5,6-tetrafluorobenzoyl chloride and 25 ml of 2N hydroxide with another. After stirring overnight, the pH was adjusted to 2 with dilute hydrochloric acid and the crystallizate formed was filtered off with suction.
.ažok.: 15, ň g (93,4 % teória) : : 146 až 147 °C.Yield: 15 µg (93.4% of theory): 146-147 ° C.
Zodpovedajúcim spôsobom sa vyrobia nasledujúce zlúčeniny ' robecného /zorca IThe following compounds of general formula (I) are prepared accordingly
F FF F
Príklady použitiaExamples of use
Príklad AExample A
Test na Pyricularia (ryža)/systemickýPyricularia (rice) / systemic test
Rozpúšťadlo: 12,5 hmotnostných dielov acetónu emulgátor: 0,3 hmotnostných dielov alkylarylpolyglykoléteru kSolvent: 12.5 parts by weight of acetone emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether to
Na výrobu účelného prípravku účinnej látky sa zmieša 1 hmotnostný diel účinnej látky s uvedeným množstvom rozpúšťadla a koncentrát sa zriedi vodou a uvedeným množstvom emulgátora na požadovanú koncentráciu.To make a suitable active ingredient preparation, 1 part by weight of the active ingredient is mixed with the stated amount of solvent and the concentrate is diluted with water and the said amount of emulsifier to the desired concentration.
Kvôli skúške systemických vlastností sa naleje 40 ml prípravku účinnej látky na jednotkovú pôdu, v ktorej boli mladé rastliny ryže. 7 dní po ošetrení sa rastliny inokulujú vodnou suspenziou spór Pyricularia oryzae. Rastliny sa potom nechajú pri teplote 25 C a 100 % relatívnej vlhkosti v skleníku.To test the systemic properties, 40 ml of the active ingredient preparation is poured onto the unit soil in which the young rice plants were. 7 days after treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then kept in a greenhouse at 25 ° C and 100% relative humidity.
••
Vyhodnotenie napadnutia chorobou sa vykonáva 4 dni po • inokulácii.Assessment of disease infestation is performed 4 days after inoculation.
Zlúčeniny podlá výrobných príkladov 1, 2,3a 37 vykazujú pri aplikovanom množstve 100 mg účinnej látky pre 100 cm3 100 % stupeň účinku.The compounds according to Production Examples 1, 2, 3 and 37 show a 100% degree of action at an application rate of 100 mg of active ingredient per 100 cm 3 .
Claims (2)
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DE4340180A DE4340180A1 (en) | 1993-11-25 | 1993-11-25 | Derivatives of 2,3,5,6-tetrafluorobenzoic acid |
PCT/EP1994/003775 WO1995014688A1 (en) | 1993-11-25 | 1994-11-14 | Derivatives of 2,3,5,6-tetrafluorobenzoic acid and their use in combating pests |
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JP (1) | JPH09511221A (en) |
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AU (1) | AU1064995A (en) |
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CZ (1) | CZ147396A3 (en) |
DE (1) | DE4340180A1 (en) |
HU (1) | HUT74715A (en) |
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SK (1) | SK65896A3 (en) |
TW (1) | TW258646B (en) |
WO (1) | WO1995014688A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19615452A1 (en) * | 1996-04-19 | 1997-10-23 | Bayer Ag | 2,3,5,6-tetrafluorobenzoic acid amides |
KR100587198B1 (en) * | 1997-08-28 | 2006-10-19 | 신젠타 파티서페이션즈 아게 | Insects or representative ticks |
CN103819408B (en) * | 2014-03-13 | 2015-08-05 | 山东理工大学 | Nitro imidazole derivatives and its production and use |
CN105254577B (en) * | 2015-08-07 | 2017-08-01 | 常州大学 | A kind of pair of triazole substituted benzene diformic ester compound, preparation method and purposes |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1642224B2 (en) * | 1967-04-28 | 1976-04-29 | Basf Ag, 6700 Ludwigshafen | USE OF SUBSTITUTED BENZOIC ANILIDES FOR CONTROL OF FUNGI FROM THE CLASS OF BASIDIOMYCETS |
US4055663A (en) * | 1974-06-27 | 1977-10-25 | National Patent Development Corporation | Halogenated acylamino acids as fungicides |
DE2944446A1 (en) * | 1979-11-03 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | TRISUBSTITUTED BENZYL OXIMETERS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES |
-
1993
- 1993-11-25 DE DE4340180A patent/DE4340180A1/en not_active Withdrawn
-
1994
- 1994-10-26 TW TW083109861A patent/TW258646B/zh active
- 1994-11-14 BR BR9408162A patent/BR9408162A/en not_active Application Discontinuation
- 1994-11-14 WO PCT/EP1994/003775 patent/WO1995014688A1/en not_active Application Discontinuation
- 1994-11-14 EP EP95901380A patent/EP0730592A1/en not_active Withdrawn
- 1994-11-14 SK SK658-96A patent/SK65896A3/en unknown
- 1994-11-14 AU AU10649/95A patent/AU1064995A/en not_active Abandoned
- 1994-11-14 PL PL94314587A patent/PL314587A1/en unknown
- 1994-11-14 JP JP7514796A patent/JPH09511221A/en active Pending
- 1994-11-14 CN CN94194787A patent/CN1141037A/en active Pending
- 1994-11-14 HU HU9601420A patent/HUT74715A/en unknown
- 1994-11-14 CZ CZ961473A patent/CZ147396A3/en unknown
Also Published As
Publication number | Publication date |
---|---|
CN1141037A (en) | 1997-01-22 |
HUT74715A (en) | 1997-02-28 |
WO1995014688A1 (en) | 1995-06-01 |
AU1064995A (en) | 1995-06-13 |
HU9601420D0 (en) | 1996-07-29 |
BR9408162A (en) | 1997-08-05 |
JPH09511221A (en) | 1997-11-11 |
EP0730592A1 (en) | 1996-09-11 |
DE4340180A1 (en) | 1995-06-01 |
PL314587A1 (en) | 1996-09-16 |
CZ147396A3 (en) | 1996-08-14 |
TW258646B (en) | 1995-10-01 |
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