SI9300611A - Fungicidal 2-alcoxy-2-imidazolin-5-one derivatives - Google Patents
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- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
Description
RHONE-POULENC AGROCHIMIERHONE-POULENC AGROCHIMIE
Fungicidni derivati 2-alkoksi-2-imidazolin-5-onovFungicidal derivatives of 2-alkoxy-2-imidazolin-5-ones
Pričujoči izum se nanaša na nove spojine 2-alkoksi-2-imidazolin-5-one za fitosanitarno uporabo. Nanaša se tudi na postopke za pripravo teh spojin in na produkte, ki so v danem primeru uporabni kot intermediati v postopkih za njihovo pripravo. Nadalje se nanaša na uporabo teh spojin kot fungicidov, na fungicidne pripravke na osnovi teh spojin in na postopke za boj proti glivičnim boleznim v kulturah ob uporabi teh spojin.The present invention relates to novel 2-alkoxy-2-imidazolin-5-one compounds for phytosanitary use. It also relates to processes for the preparation of these compounds and to products which, if appropriate, are useful as intermediates in the processes for their preparation. It further relates to the use of these compounds as fungicides, to fungicidal preparations based on these compounds, and to methods for combating fungal diseases in cultures using these compounds.
En smoter pričujočega izuma je predlagati spojine, ki kažejo izboljšane lastnosti pri zdravljenju glivičnih bolezni.One object of the present invention is to propose compounds that exhibit improved properties in the treatment of fungal diseases.
Drugi smoter pričujočega izuma je predlagati spojine, ki kažejo spekter, ki je tudi izboljšan na področju glivičnih bolezni.Another object of the present invention is to propose compounds that exhibit a spectrum that is also improved in the field of fungal diseases.
Sedaj smo ugotovili, da lahko te smotre dosežemo v celoti ali deloma s pomočjo produktov v smislu izuma, ki so derivati 2-alkoksi-2-imidazolin-5-onov s splošno formulo (I):We have now found that these purposes can be achieved in whole or in part by the products of the invention which are derivatives of 2-alkoxy-2-imidazolin-5-ones of the general formula (I):
v kateriin which
- R1 predstavlja arilni radikal, ki obsega fenil, naftil, tienil, furil, piridil, benzotienil, benzofuril, kinolinil, izokinolinil ali metilen dioksifenil, pri čemer je vsak od teh radikalov v danem primeru substituiran z 1 do 3 skupinami, izbranimi izmed pomenov za R6;- R 1 represents an aryl radical comprising phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolinyl, isoquinolinyl or methylene dioxyphenyl, each of these radicals being optionally substituted by 1 to 3 groups selected from the meanings for R 6 ;
- R2 predstavlja alkilni ali haloalkilni radikal z 1 do 3 atomi ogljika,- R 2 represents an alkyl or haloalkyl radical having 1 to 3 carbon atoms,
- R1 in R2 lahko poleg tega tvorita z ogljikom, na katerega sta vezana na obroču, karbocikel ali heterocikel, ki ima 5 do 7 atomov, pri čemer so lahko ti cikli kondenzirani s fenilom, pri čemer je lahko vsak od teh radikalov v danem primeru substituiran z 1 do 3 skupinami, izbranimi izmed pomenov za R6;- R 1 and R 2 may further form with the ring-attached carbon a carbocyclic or heterocycle having 5 to 7 atoms, these cycles may be fused with phenyl, each of these radicals in optionally substituted by 1 to 3 groups selected from the meanings for R 6 ;
- R3 predstavlja alkilno ali haloalkilno skupino z 1 do 3 atomi ogljika;- R 3 represents an alkyl or haloalkyl group having 1 to 3 carbon atoms;
- R4 predstavlja arilni radikal ki obsega fenil, naftil, piridil, pirimidil, piridazinil, pirazinil, benzotienil, benzofuril, kinolinil, izokinolinil ali metilen dioksifenil, pri čemer je vsak od teh radikalov v danem primeru substituiran z 1 do 3 skupinami, izbranimi izmed pomenov za R6;- R 4 represents an aryl radical comprising phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, quinolinyl, isoquinolinyl or methylene dioxyphenyl, each of these radicals being optionally substituted by 1 to 3 groups selected from meanings for R 6 ;
- R5 predstavlja atom vodika ali formilni ali acilni radikal z 2 do 6 atomi ogljika, aroilni ali alkoksikarbonilni radikal z 2 do 6 atomi ogljika, ariloksikarbonil, alkilsulfonil, arilsulfonil;- R 5 represents a hydrogen atom or a formyl or acyl radical of 2 to 6 carbon atoms, an aroyl or alkoxycarbonyl radical of 2 to 6 carbon atoms, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl;
- R6 predstavlja- R 6 represents
- atom halogena ali- a halogen atom or
- alkilni, haloalkilni, cianoalkilni, alkoksi, haloalkoksi, cianoalkoksi, alkiltio, haloalkiltio, cianoalkiltio ali alkilsulfonilni radikal z 1 do 6 atomi ogljika ali- alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, cyanoalkoxy, alkylthio, haloalkylthio, cyanoalkylthio or alkylsulfonyl radical having from 1 to 6 carbon atoms, or
- cikloalkilni, halocikloalkilni, alkenilni, alkinilni, alkeniloksi, alkiniloksi, alkeniltio, alkiniltio radikal s 3 do 6 atomi ogljika ali- cycloalkyl, halocycloalkyl, alkenyl, alkynyl, alkenyloxy, alkinyloxy, alkenylthio, alkynylthio radicals having 3 to 6 carbon atoms, or
- nitro ali ciano ali tiocianato skupino ali- a nitro or cyano or thiocyanate group, or
- amino radikal, ki je v danem primeru mono ali disubstituiran z alkilnim ali acilnim radikalom z 1 do 6 atomi ogljika ali alkoksikarbonilnim radikalom z 2 do 6 atomi ogljika,- an amino radical optionally mono or substituted by an alkyl or acyl radical having from 1 to 6 carbon atoms or an alkoxycarbonyl radical having from 2 to 6 carbon atoms,
- fenilni, fenoksi, feniltio, fenilsulfonilni ali piridiloksi radikal, pri čemer so ti radikali v danem primeru substituirani z eno ali več naslednjimi skupinami:- phenyl, phenoxy, phenylthio, phenylsulfonyl or pyridyloxy radicals, optionally substituted by one or more of the following groups:
- atom halogena ali- a halogen atom or
- alkilni, haloalkilni, cianoalkilni, alkoksi, haloalkoksi, alkiltio, haloalkiltio ali alkilsulfonilni radikal z 1 do 6 atomi ogljika ali- an alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or alkylsulfonyl radical having 1 to 6 carbon atoms, or
- cikloalkilni, halocikloalkilni, alkenilni, alkinilni, alkeniloksi, alkiniloksi, alkeniltio, alkiniltio s 3 do 6 atomi ogljika ali- cycloalkyl, halocycloalkyl, alkenyl, alkynyl, alkenyloxy, alkinyloxy, alkenylthio, alkynylthio having 3 to 6 carbon atoms, or
- nitro ali ciano ali tiocianato skupina alia nitro or cyano or thiocyanato group, or
- amino radikal, ki je v danem primeru mono- ali disubstituiran z alkilnim ali acilnim radikalom z 1 do 6 atomi ogljika ali alkoksikarbonilnim radikalom z 2 do 6 atomi ogljika,- an amino radical optionally mono- or disubstituted by an alkyl or acyl radical having 1 to 6 carbon atoms or an alkoxycarbonyl radical having 2 to 6 carbon atoms,
- fenilni, fenoksi, feniltio, fenilsulfonilni ali piridiloksi radikal, pri čemer so ti radikali v danem primeru substituirani z eno ali več naslednjimi skupinami: -atom halogena ali- a phenyl, phenoxy, phenylthio, phenylsulfonyl or pyridyloxy radical, these radicals being optionally substituted by one or more of the following groups: -halogen halogen, or
- alkilni, haloalkilni, cianoalkilni, alkoksi, haloalkoksi, alkiltio, haloalkiltio ah alkilsulfonilni radikal z 1 do 6 atomi ogljika ah- alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or alkylsulfonyl radical having 1 to 6 carbon atoms ah
- cikloalkilni, halocikloalkilni, alkenilni, alkinilni, alkeniloksi, alkiniloksi, alkeniltio ali alkiniltio radikal s 3 do 6 atomi ogljika ah- cycloalkyl, halocycloalkyl, alkenyl, alkynyl, alkenyloxy, alkinyloxy, alkenylthio or alkynylthio radicals having 3 to 6 carbon atoms ah
- nitro ali ciano ali tiocianato skupina alia nitro or cyano or thiocyanato group, or
- amino radikal, ki je v danem primeru mono- ali disubstituiran z alkilnim ali acilnim radikalom z 1 do 6 atomi ogljika ali alkoksikarbonilnim radikalom z 2 do 6 atomi ogljika,- an amino radical optionally mono- or disubstituted by an alkyl or acyl radical having 1 to 6 carbon atoms or an alkoxycarbonyl radical having 2 to 6 carbon atoms,
- fenilni, fenoksi, feniltio, fenilsulfonilni ali piridiloksi radikal, in njihove v sol pretvorjene oblike.- phenyl, phenoxy, phenylthio, phenylsulfonyl or pyridyloxy radicals and their salt-converted forms.
Spojine s formulo II tu spodaj predstavljajo prednostne spojineThe compounds of formula II below are preferred compounds
v kateri imajo R1 do R6 iste pomene kot prej.in which R 1 to R 6 have the same meanings as before.
Še bolj prednostno predstavlja R4 fenil, substituiran fenil, piridil ali substituiran piridil, in R5 predstavlja atom vodika ali acilni (npr. acetilni) radikal.Even more preferably, R 4 is phenyl, substituted phenyl, pyridyl or substituted pyridyl, and R 5 represents a hydrogen atom or an acyl (e.g. acetyl) radical.
Spojine s formulo I dobimo tako, da presnovimo 2-alkiltio-2-imidazolin-5-one s formulo (III) z alkoholom R3OH v prisotnosti močne baze po shemi:The compounds of formula I are obtained by reacting 2-alkylthio-2-imidazolin-5-ones of formula (III) with an alcohol R 3 OH in the presence of a strong base according to the scheme:
+ R3OH baza + R 3 OH base
->.->.
topilosolvent
OOh
O —R3 O —R 3
NR4 NR 4
II
R5 pri čemer imajo R1, R2, R3 in R4 isti pomen kot za formulo I in R’3 predstavlja alkilno skupino z 1 do 3 atomi ogljika.R 5 wherein R 1 , R 2 , R 3 and R 4 have the same meaning as for Formula I and R ' 3 represents an alkyl group of 1 to 3 carbon atoms.
Kot močno bazo lahko uporabimo alkalijski alkoholat R3O'M+, alkalijski hidroksid ali močno organsko bazo. Presnovo izvedemo prednostno v alkoholu R3OH kot topilu ob uporabi ustreznega natrijevega alkohola ta R3ONa+ kot baze. Presnovo izvedemo pri temperaturi med 20 in 80 °C. 2-alkiltio-2-imidazolin-5-one s formulo (III) dobimo po postopkih, opisanih v evropski patentni prijavi EP 0 551 048. Aciliranje spojin s formulo I, v kateri je R5 atom vodika, se vrši po klasičnih metodah.The alkali alcoholate R 3 O'M + , alkali hydroxide or a strong organic base may be used as the strong base. The metabolism is preferably carried out in alcohol R 3 OH as solvent using the corresponding sodium alcohol, this R 3 ONa + as base. The reaction is carried out at a temperature between 20 and 80 ° C. The 2-alkylthio-2-imidazolin-5-one of formula (III) is obtained according to the procedures described in European patent application EP 0 551 048. The acylation of compounds of formula I in which R 5 is a hydrogen atom is carried out by conventional methods.
Soli spojin s formulo I lahko pripravimo po samih po sebi znanih metodah.Salts of the compounds of formula I can be prepared by methods known per se.
Sledeče primere navajamo za ilustracijo spoj n v smislu izuma, postopkov za njihovo pripravo in njihovih protiglivičnih lastnosti.The following examples are given to illustrate the compounds of the invention, the processes for their preparation and their antifungal properties.
Strukture vseh produktov smo ugotovili z najmanj eno od teh-le spektralnih tehnik: protonska RMN spektrometrija, RMN spektrometrija ogljika 13, infrardeča spektrometrija in masna spektrometrija.The structures of all the products were determined by at least one of these spectral techniques: proton RMN spectrometry, carbon RMN spectrometry 13, infrared spectrometry and mass spectrometry.
V tabeli dalje spodaj predstavljajo metilni, etilni, propilni, piridilni, acetilni in fenilni radikal simboli Me, Et, Pr, Py, Ac oz. Ph, in tal. pomeni tališče (tal.).In the table below, the methyl, ethyl, propyl, pyridyl, acetyl and phenyl radicals are represented by the symbols Me, Et, Pr, Py, Ac or. Ph, and soil. means melting point.
PRIMER 1: Priprava spojine štev. 2EXAMPLE 1: Preparation of Compound Nr. 2
V 100 ml-ski bučki s tremi vratovi presnovimo pod atmosfero suhega dušika 1,4 g (1,74 mmola) natrija v 60 ml etanola. Nato dodamo 4 g (1,28 mmola) 4-metil-2metiltio-4-fenil-l-fenilamino-2-imidazolin-5-ona. Ob refluksu segrevamo 6 h. Medij ohladimo na okolno temperaturo in ga nakisamo z 0,4 ml ocetne kisline. Medij razredčimo s 300 ml etil acetata. Organsko raztopino speremo z vodo, jo nato posušimo na magnezijevem sulfatu in nato koncentriramo pod zmanjšanim tlakom. Dobimo ijavo rdeč sirup. Produkt očistimo s kolonsko kromatografijo na kremeniti. Dobimo 1,25 g (dobitek 31 %) spojine štev. 2 v obliki rahlo rožnatega praška, ki se tali pri 106 °C.In a 100 ml three-necked flask, metabolize 1.4 g (1.74 mmol) of sodium into 60 ml of ethanol under a dry nitrogen atmosphere. Then 4 g (1.28 mmol) of 4-methyl-2methylthio-4-phenyl-1-phenylamino-2-imidazolin-5-one are added. Reflux was heated for 6 h. The medium was cooled to ambient temperature and acidified with 0.4 ml of acetic acid. The medium was diluted with 300 ml of ethyl acetate. The organic solution was washed with water, then dried over magnesium sulfate and then concentrated under reduced pressure. We get red syrup. The product was purified by silica column chromatography. 1.25 g (31% yield) of compound no. 2 in the form of a slightly pink powder, melting at 106 ° C.
Na enak način smo pripravili spojine, opisane dalje spodaj:In the same manner, the following compounds were prepared:
Spojina štev. 7 :Compound no. 7:
Tal. = 73 °CTal. = 73 ° C
Spojina štev.10 :Compound No.10:
Tal. = 86°CTal. = 86 ° C
Spojina štev.22 :Compound No.22:
Tal. = 71°CTal. = 71 ° C
Spojina štev. 86 :Compound no. 86:
PRIMER 2: Test in vivo na Plasmopara viticola (trtna peronospora):EXAMPLE 2 Plasmopara viticola (Vine Peronospora) In Vivo Test:
S finim mletjem pripravimo vodno suspenzijo testne učinkovine s tole sestavo:By fine grinding, prepare the aqueous suspension of the test substance with the following composition:
- učinkovina: 60 mg- active ingredient: 60 mg
- površinsko aktivno sredstvo Tween 80 (oleat polioksietiliranega derivata sorbitana), razredčen na 10 % v vodi: 0,3 ml- Tween 80 surfactant (oleate polyoxyethylated sorbitan derivative) diluted to 10% in water: 0.3 ml
- dopolnimo z vodo do 60 ml.- Make up to 60 ml with water.
To vodno suspenzijo nato razredčimo z vodo, da dobimo želeno koncentracijo učinkovine.This aqueous suspension is then diluted with water to obtain the desired concentration of the active ingredient.
Sadike i le (Vitis vinifera), sorte Chardonnay, gojimo v loncih. Ko so rastline tare 2 meseca (stadij 8 do 10 listov, višina 10 do 15 cm), jih s škropljenjem obdelamo z gornjo vodno suspenzijo.Seedlings i le (Vitis vinifera), Chardonnay varieties, are grown in pots. When the tare plants are 2 months old (stage 8 to 10 leaves, height 10 to 15 cm), they are sprayed with the above aqueous suspension.
Rastline, ki jih uporabimo kot kontrole, obdelamo z vodno raztopino, ki ne vsebuje učinkovine.The plants used as controls are treated with an aqueous solution containing no active ingredient.
Po 24-urnem sušenju okužimo vsako rastlino s škropljenjem vodne suspenzije spor Plasmopara viticola, dobljene iz 4- do 5-dnevne kulture, ki jo nato suspendiramo s 100 000 enotami na cm3.After drying for 24 hours, each plant was infected by spraying an aqueous suspension of Plasmopara viticol spores obtained from a 4- to 5-day culture, which was then suspended with 100,000 units per cm 3 .
Okužene rastline nato inkubiramo 2 dni pri okoli 18 °C v atmosferi, nasičeni z vlago, nato pa 5 dni pri okoli 20 do 22 °C pri 90 do 100 %-ni relativni vlažnosti.The infected plants are then incubated for 2 days at about 18 ° C in an atmosphere saturated with moisture, and then for 5 days at about 20 to 22 ° C at 90 to 100% relative humidity.
Ocenjevanje se vrši 7 dni po okuženju v primerjavi s kontrolnimi rastlinami.Evaluation is performed 7 days after infection compared with control plants.
V teh pogojih opazimo pri dozi 1 g/1 dobro (najmanj 75 %-no) ali popolno zaščito s temile spojinami: 1, 3 do 21,23 do 25, 27 do 81, 83, 84 in 86.Under these conditions, a good (at least 75%) or complete protection with temile compounds is observed at a dose of 1 g / l: 1, 3 to 21,23 to 25, 27 to 81, 83, 84 and 86.
PRIMER 3: Test in vivo na Puccinia recondita (žitna rja):EXAMPLE 3 In vivo test on Puccinia recondita (cereal rust):
S finim mletjem pripravimo vodno suspenzijo testne učinkovine s tole sestavo:By fine grinding, prepare the aqueous suspension of the test substance with the following composition:
- učinkovina: 60 mg- active ingredient: 60 mg
- površinsko aktivno sredstvo Tween 80 (oleat polioksietiliranega derivata sorbitana), razredčen na 10 % v vodi: 0,3 ml- Tween 80 surfactant (oleate polyoxyethylated sorbitan derivative) diluted to 10% in water: 0.3 ml
- dopolnimo z vodo do 60 ml.- Make up to 60 ml with water.
To vodno suspenzijo nato razredčimo z vodo, da dobimo želeno koncentracijo učinkovine.This aqueous suspension is then diluted with water to obtain the desired concentration of the active ingredient.
Žito v lončkih, posejano na substrat iz šote in pucolanske zemlje 50/50, obdelamo v stadiju z višino 10 cm s škropljenjem z gornjo vodno suspenzijo.The cereal in pots, sown on a 50/50 peat and ground soil substrate, is treated in a 10 cm height by spraying with the above aqueous suspension.
Čez 24 ur poškropimo po žitu vodno suspenzijo spor (100 000 spor/cm3). To suspenzijo smo dobili od okuženih rastlin. Žito damo nato za 24 ur v inkubacijsko celico z okoli 20 °C in 100 %-r»n relativno vlažnostjo, nato pa za 7 do 14 dni s 60 %-no relativno vlažnostjo.Spray the spores (100,000 spores / cm 3 ) over a grain of 24 hours. This suspension was obtained from infected plants. The cereals were then placed in an incubation cell at about 20 ° C and 100% -r »n relative humidity for 24 hours, and then for 7-14 days at 60% relative humidity.
Kontrola stanja rastlin se vrši med 8. in 15. dnevom po okuženju s primerjavo z neobdelano kontrolo.Plant control is performed between days 8 and 15 after infection by comparison with the untreated control.
V teh pogojih opazimo pri dozi 1 g/1 dobro (najmanj 75 %-no) ali popolno zaščito s temile spojinami: 1,4 do 10,14,15,19 do 21, 23,25, 27 do 29, 31 do 33,36, 37, 39,40 do 48, 50 do 55, 57,58, 60,61, 63 do 67, 69,71 do 80, 82 do 84 in 86.Under these conditions, good (at least 75%) or complete protection with temile compounds is observed at a dose of 1 g / l: 1,4 to 10,14,15,19 to 21, 23,25, 27 to 29, 31 to 33 , 36, 37, 39,40 to 48, 50 to 55, 57,58, 60,61, 63 to 67, 69,71 to 80, 82 to 84 and 86.
PRIMER 4: Test in vivo na Phytophthora infestans (paradižnikova plesen):EXAMPLE 4: In vivo test for Phytophthora infestans (tomato mold):
S finim mletjem pripravimo vodno suspenzijo testne učinkovine s tole sestavo:By fine grinding, prepare the aqueous suspension of the test substance with the following composition:
- učinkovina: 60 mg- active ingredient: 60 mg
- površinsko aktivno sredstvo Tween 80 (oleat polioksietiliranega derivata sorbitana), razredčen na 10 % v vodi: 0,3 ml- Tween 80 surfactant (oleate polyoxyethylated sorbitan derivative) diluted to 10% in water: 0.3 ml
- dopolnimo z vodo do 60 ml.- Make up to 60 ml with water.
To vodno suspenzijo nato razredčimo z vodo, da dobimo želeno koncentracijo učinkovine.This aqueous suspension is then diluted with water to obtain the desired concentration of the active ingredient.
Rastline paradižinika (sorta Marmande) gojimo v lončkih. Ko so rastline stare 1 mesec (stadij 5 do 6 listov, višina 12 do 15 cm), jih obdelamo s škropljenjem gornje vodne suspenzije z različnimi koncentracijami testne spojine.Tomato plants (Marmande variety) are grown in pots. When the plants are 1 month old (stage 5 to 6 leaves, height 12 to 15 cm), they are treated by spraying the upper aqueous suspension with different concentrations of the test compound.
Po 24 urah okužimo vsako rastlino s škropljenjem z vodno suspenzijo spor (30 000 spor/cm3) Phytophthora infestans.After 24 hours, infect each plant by spraying with an aqueous suspension of the spores (30,000 spores / cm 3 ) of Phytophthora infestans.
Po tem okuženju damo rastline paradižnika v inkubacijo za 7 dni pri okoli 20 °C v atmosferi, nasičeni z vlago.Following this infection, the tomato plants are incubated for 7 days at about 20 ° C in an atmosphere saturated with moisture.
dni po okuženju primerjamo rezultate, dobljene v primeru rastlin, obdelanih s testno učinkovino, z rezultati, dobljenimi v primeru rastlin, ki smo jih uporabili kot kontrole. V teh pogojih opazimo pri dozi 1 g/1 dobro (najmanj 75 %-no) ali popolno zaščito s temile spojinami: 1, 4 do 10, 15,18 do 21, 23, 28, 29, 31 do 33, 36, 37, 39, 42 do 4^ 46 do 55, 57, 58, 60 do 67, 72 do 74,81,84 in 86.days after infection, the results obtained in the case of plants treated with the test substance are compared with those obtained in the case of the plants used as controls. Under these conditions, a good (at least 75%) or complete protection with temile compounds is observed at a dose of 1 g / l: 1, 4 to 10, 15,18 to 21, 23, 28, 29, 31 to 33, 36, 37 , 39, 42 to 4 ^ 46 to 55, 57, 58, 60 to 67, 72 to 74,81,84 and 86.
PRIMER 5: Test in vivo na Pyricularia oryzae (siva riževa pegavost):EXAMPLE 5 In vivo test for Pyricularia oryzae (gray rice freckles):
S finim mletjem pripravimo vodno suspenzijo testne učinkovine s tole sestavo:By fine grinding, prepare the aqueous suspension of the test substance with the following composition:
- učinkovina: 60 mg- active ingredient: 60 mg
- površšinsko aktivno sredstvo Tween 80 (oleat polioksietiliranega derivata sorbitana), razredčen na 10 % v vodi: 0,3 ml- Tween 80 surfactant (oleate polyoxyethylated sorbitan derivative) diluted to 10% in water: 0.3 ml
- dopolnimo z vodo do 60 ml.- Make up to 60 ml with water.
To vodno suspenzijo nato razredčimo z vodo, da dobimo želeno koncentracijo učinkovine.This aqueous suspension is then diluted with water to obtain the desired concentration of the active ingredient.
Riž, posejan v lončke v mešanici obogatene šote in pucolana 50/50, obdelamo v stadiju z višino okoli 10 cm (kar ustreza stadiju 2 do 3 listov) s škropljenjem z gornjo vodno suspenzijo.The rice, sown in pots in a mixture of fortified peat and 50/50 pucola, is treated at a stage height of about 10 cm (corresponding to stage 2 to 3 leaves) by spraying with the above aqueous suspension.
Po 24 urah nanesemo na liste vodno suspenzijo spor Pyricularia oryzae, dobljeno iz 15-dnevne kulture, ki smo jo nato suspendirali s 100 000 enotami/cm3.After 24 hours, an aqueous suspension of Pyricularia oryzae spores obtained from a 15-day culture was applied to the leaves, which was then suspended with 100,000 units / cm 3 .
Riževe rastline damo za 24 ur v inkubacijo (25 °C, 100 %-na relativna vlažnost), nato pa v opazovalno celico v istih pogojih za 5 dni.Rice plants were incubated for 24 hours (25 ° C, 100% relative humidity) and then in the observation cell under the same conditions for 5 days.
Ocenjevanje se vrši 6 dni po okuženju.Assessment is performed 6 days after infection.
V teh pogojih opazimo pri dozi 1 g/1 dobro (najmanj 75 %-no) ali popolno zaščito s temi-le spojinami: 1, 4 do 7,17,19, 20,23,25,29,31 do 33, 35, 40 do 43,46, 47, 50, 52, 54,55, 57, 59, 61,63 do 67,71, 72, 74, 78,82,84 in 85.Under these conditions, good (at least 75%) or complete protection with these compounds is observed at a dose of 1 g / l: 1, 4 to 7,17,19, 20,23,25,29,31 to 33, 35 , 40 to 43,46, 47, 50, 52, 54,55, 57, 59, 61,63 to 67,71, 72, 74, 78,82,84 and 85.
PRIMER 6: Test in vivc na Septoria tritici (listna pegavost pšenice):EXAMPLE 6 Test in vivc on Septoria tritica (wheat leaf blight):
Vodno suspenzijo s koncentracijo 1 g/1 testirane učinkovine dobimo z mletjem 60 mg učinkovine v tej-le mešanici:An aqueous suspension with a concentration of 1 g / l of the test substance is obtained by grinding 60 mg of the active ingredient in this mixture only:
- aceton: 5 ml- acetone: 5 ml
- površinsko aktivno sredstvo (oleat policksietiliranega derivata sorbitana), razredčen na 10 %: 0;3 ml, nato naravnamo volumer z vodo na 60 ml.- surfactant (oleate of polycycethylated sorbitan derivative) diluted to 10%: 0 ; 3 ml, then adjust the volumer with water to 60 ml.
To vodno suspenzijo nato razredčimo z vodo, da dobimo želeno koncentracijo učinkovine.This aqueous suspension is then diluted with water to obtain the desired concentration of the active ingredient.
Rastline žita (sorta Darius), posejane na substrat iz šote in pucolana 50/50, in gojene v rastlinjaku pri temperaturi 10 do 12 °C, obdelamo v stadiju 1 lista (višina okoli 10 cm) s škropljenjem z zgoraj opisano suspenzijo učinkovine.Cereal plants (Darius variety), sown on a peat and pozzolan 50/50 substrate and grown in a greenhouse at 10 to 12 ° C, are treated in stage 1 leaf (about 10 cm high) by spraying with the active substance suspension described above.
Rastline, uporabljene kot kontrola, obdelamo s škropljenjem z vodno raztopino, ki ne vsebuje učinkovine.The plants used as controls were treated by spraying with an aqueous solution containing no active substance.
ur po obdelavi okužimo rastline s škropljenjem z vodno suspenzijo spor (500 000 spor/ml), dobljenih iz 7 dni stare kulture.hours after treatment, the plants were infected by spraying with an aqueous spore suspension (500,000 spores / ml) obtained from 7 days old culture.
Po okuženju postavimo rastline v vlažno atmosfero z 18 °C. Ocenjevanje se vrši 20 dni po okuženju v primerjavi s kontrolnimi rastlinami.After infection, place the plants in a humid atmosphere at 18 ° C. Evaluation is performed 20 days after infection compared with control plants.
V teh pogojih opazimo pri dozi 1 g/1 dobro (najmanj 75 %-no) ali popolno zaščito s spojinami 1, 4 do 6, 9,19, 20, 23, 32, 33, 35 do 37, 40, 42 do 45, 47, 48, 50, 52, 54, 55, 57,58,60,62 do 64,66,67,71 do 80,83,84 in 86.Under these conditions, good (at least 75%) or complete protection with compounds 1, 4 to 6, 9,19, 20, 23, 32, 33, 35 to 37, 40, 42 to 45 is observed at a dose of 1 g / l , 47, 48, 50, 52, 54, 55, 57,58,60,62 to 64,66,67,71 to 80,83,84 and 86.
Ti rezultati jasno kažejo dobre fungicidne lastnosti derivatov v smislu izuma proti rastlinskim glivičnim boleznim, ki jih povzročajo glivice, ki spadajo v najrazličnejše družine, kot so Phycomycetes, Basidiomycetes, Ascomycetes, Adelomycetes ali Fungi imperfecti, zlasti trtna peronospora, paradižnikova plesen, žitne rje in listne pegavosti pšenice kot tudi siva riževa pegavost.These results clearly demonstrate the good fungicidal properties of the derivatives of the invention against plant fungal diseases caused by fungi belonging to a wide variety of families, such as Phycomycetes, Basidiomycetes, Ascomycetes, Adelomycetes or Fungi imperfecti, in particular vine feathers, tomatoes, and tomato rhizomes wheat leaf freckles as well as gray rice freckles.
Za njihovo praktično uporabo uporabljamo spojine v smislu izuma redko same. Najpogosteje so te spojine del pripravkov. Ti pripravki, ki so uporabni kot fungicidna sredstva, vsebujejo kot učinkovino spojino v smislu izuma, kot je že. opisana, v mešanici s trdnimi ali tekočimi nosilci, sprejemljivimi v poljedelstvu, in/ali površinsko aktivnimi sredstvi, ki so tudi sprejemljiva v poljedeljstvu. Zlasti uporabni so inertni in običajni nosilci in običajna površinsko aktivna sredstva. Ti pripravki so tudi del izuma.For their practical use, the compounds of the invention are rarely used alone. Most often, these compounds are part of the preparations. These preparations, which are useful as fungicidal agents, contain as active ingredient a compound of the invention, as is already the case. described, in admixture with solid or liquid carriers acceptable in agriculture and / or surfactants which are also acceptable in agriculture. Particularly useful are inert and conventional carriers and conventional surfactants. These preparations are also part of the invention.
Ti pripravki lahko vsebujejo tudi vsakokvrstne druge sestavine, koi npr. zaščitne ko; ide, adhezive, zagostila, tiksotropna sredstva, penetracijska srečava, stabilizatorje, sekvestracijska sredstva itd. Bolj splošno lahko spojine, ki jih uporabljamo v izumu, kombiniramo z vsemi trdnimi ali tekočimi dodatki, ki ustrezajo običajnim tehnikam izdelovanja pripravkov.These preparations may also contain all kinds of other ingredients, such as e.g. protective skin; ide, adhesives, thickeners, thixotropic agents, penetration encounters, stabilizers, sequestration agents, etc. More generally, the compounds used in the invention can be combined with any solid or liquid additives that conform to conventional preparation techniques.
Če ni navedeno drugače, so odstotki, navedeni v pričujočem opisu, izraženi kot masni.Unless otherwise stated, the percentages given in the present description are expressed as mass.
Na splošno vsebujejo pripravki v smislu izuma običajno od 0,05 do okoli 95 (mas.) % spojine v smislu izuma (imenovane v nadaljevanju učinkovina), enega ali več trdnih ali tekočih nosilcev in v danem primeru eno ali več površinsko aktivnih sredstev.Generally, the compositions of the invention typically contain from 0.05 to about 95% by weight of the compound of the invention (hereinafter referred to as the active ingredient), one or more solid or liquid carriers, and optionally one or more surfactants.
Z izrazom nosilec označujemo v pričujočem opisu organsko ali mineralno snov, naravno ali sintetično, s katero kombiniramo spojino, da olajšamo njeno uporabo na rastlini, na zrnih ali na tleh. Ta nosilec je torej na splošno inerten in mora biti sprejemljiv v poljedelstvu, zlasti na obdelani rastlini. Nosilec je lahko trden (gline, naravni ali sintetični silikati, kremenica, smole, voski, trdna gnojila itd.) ali tekoč (voda, alkoholi, zlasti butanol, itd.).The term carrier is used herein to describe an organic or mineral substance, natural or synthetic, with which a compound is combined to facilitate its use on a plant, on grains or on the ground. This carrier is therefore generally inert and must be acceptable in agriculture, in particular on the treated plant. The carrier may be solid (clay, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.) or liquid (water, alcohols, especially butanol, etc.).
Površinsko aktivno sredstvo je lahko emulzijsko, disperzijso ali omočilno sredstvo ionske ali neionske vrste ali mešanica takih površinsko aktivnih sredstev. Za primer lahko navedemo soli poliakrilnih kislin, soli lignosulfonskih kislin, soli fenolsulfonskih kislin ali naftalensulfonskih kislin, polikondenzate etilen oksida na maščobnih alkoholih ali na maščobnih kislinah ali na maščobnih aminih, substituirane fenole (zlasti alkilfenole ali arilfenole), soli estrov sulfojantamih kislin, tavrinove derivate (zlasti alkiltavrate), estre fosforjeve kisline z alkoholi ali polioksietiliranimi fenoli, estre maščobnih kislin in poliolov, derivate prednjih spojin s sulfatnimi, sulfonatnimi in fosfatnimi funkcijami. Prisotnost vsaj enega površinsko aktivnega sredstva je na splošno neobhodno potrebna, če spojina in/ali inertni nosilec nista topna v vodi in če je nosilno sredstvo za uporabo voda.The surfactant may be an emulsion, dispersion or wetting agent of the ionic or non-ionic species or a mixture of such surfactants. For example, salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulfonic acids or naphthalenesulfonic acids, polycondensates of ethylene oxide on fatty alcohols or on fatty acids or on fatty amines, substituted phenols (especially alkylphenols, or aryl sulfenate derivatives) (especially alkyl esters), phosphoric acid esters of alcohols or polyoxyethylated phenols, fatty acid and polyol esters, derivatives of fore-compounds with sulfate, sulfonate and phosphate functions. The presence of at least one surfactant is generally essential if the compound and / or inert carrier is insoluble in water and if the carrier is water.
Tako lahko pripravki za poljedelsko uporabo v smislu izuma vsebujejo učinkovine v smislu izuma v zelo širokih mejah, ki znašajo od 0,05 do 95 (mas.) %. Njihova vsebnost površinsko aktivnega sredstva znaša s pridom med 5 in 40 mas. %.Thus, the preparations for agricultural use of the invention may contain the active ingredients of the invention within very wide limits, ranging from 0.05 to 95% by weight. Their surfactant content is preferably between 5 and 40% by weight. %.
Ti pripravki v smislu izuma so sami po sebi v zelo različnih, trdnih ali tekočih oblikah.These compositions according to the invention are inherently in very different, solid or liquid forms.
Kot oblike trdnih priprs. -'kov lahko navedemo praške za zapraševanje (z vsebnostjo spojine, ki lahko znaša do 100 %) in granulate, zlasti tiste, dobljene z ekstruzijo, s kompaktiranjem, z impregniranjem granuliranega nosilca, z granuliranjem iz prahu (v teh zadnjih primerih je vsebnost spojine v teh granulatih med 0,5 in 80 %), efervescentne komprimate ali tablete.As forms of solid breasts. - Powders (containing up to 100% compound) and granules, in particular those obtained by extrusion, by compacting, by impregnation of a granular carrier, by powder granulation (in these latter cases, the content of the compound may be mentioned in these granules between 0.5 and 80%), effervescent compresses or tablets.
Spojine s formulo (I) lahko uporabimo tudi v obliki prahov za zapraševanje. Uporabimo lahko tudi pripravek, ki vsebuje 50 g učinkovine in 950 g smukca. Uporabimo lahko tudi pripravek, ki vsebuje 20 g učinkovine, 10 g fino porazdeljene kremenice in 970 g smukca. Te sestavine zmešamo in zmeljemo in mešanico nanašamo z zapraševanjem.The compounds of formula (I) may also be used in powder form. A preparation containing 50 g of active ingredient and 950 g of talc may also be used. A preparation containing 20 g of active ingredient, 10 g of finely divided quartz and 970 g of talc may also be used. These ingredients are mixed and ground and the mixture is dusted.
Kot oblike tekočih pripravkov ali oblike, ki so namenjene za to, da tvorijo pri uporabi tekoče pripravke, lahko navedemo raztopine, zlasti v vodi topne koncentrate, emulzibilne koncentrate, emulzije, koncentrirane suspenzije, aerosole, omočljive praške (ali praške za škropljenje), paste in gele.Solution forms, in particular water-soluble concentrates, emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, wettable powders (or spraying powders), pastes, may be mentioned as forms of liquid preparations or forms intended to form a liquid preparation when used. and gels.
Emulzibilni ali topni koncentrati obsegajo najpogosteje 10 do 80 % učinkovine, medtem ko vsebujejo emulzije ali raztopine, pripravljene za uporabo, 0,001 do 20 % učinkovine.Emulsifiable or soluble concentrates most commonly comprise 10 to 80% of the active ingredient, while containing emulsions or ready-to-use solutions, 0.001 to 20% of the active substance.
Poleg topila lahko vsebujejo emulzibilni koncentrati, če je potrebno, 2 do 20 % primernih dodatkov, kot prej navedenih stabilizatorjev, površinsko aktivnih sredstev, penetracijskih sredstev, korozijskih inhibitorjev, barvil ali adhezivov.In addition to the solvent, the emulsifiable concentrates may, if necessary, contain 2 to 20% of suitable additives such as the stabilizers, surfactants, penetration agents, corrosion inhibitors, colorants or adhesives mentioned above.
Iz teh koncentratov lahko dobimo z razredčenjem z vodo emulzije z vsako želeno koncentracijo, ki so zlasti primerne za uporabo na kulturah.These concentrates can be obtained by diluting with water emulsions at any desired concentration, which are particularly suitable for use on cultures.
Za primer navajamo sestavo nekaterih emulzibilnih koncentratov:For example, the composition of some emulsifiable concentrates is as follows:
Primer CE1:Example CE1:
- učinkovina 400 g/1- active substance 400 g / l
- alkalijski dodecilbenzen sulfonat 24 g/1- Alkali dodecylbenzene sulfonate 24 g / l
- oksietilirani nonilfenol z 10 molekulami etilen oksida 16 g/1- oxyethylated nonylphenol with 10 ethylene oxide molecules 16 g / l
- cikloheksanon 200 g/1- cyclohexanone 200 g / l
- aromatsko topilo q.s. za ί liter- aromatic solvent q.s. for ί liter
Po drugi formuli emulzibilnega koncentrata uporabimo:According to the second formula of emulsifiable concentrate, we use:
Primer CE 2:Example CE 2:
- učinkovina 250 g- active ingredient 250 g
- epoksidirano rastlinsko olje 25 g- epoxidized vegetable oil 25 g
- mešanica alkilarilsulfonata in poliglikoletra in maščobnih alkoholov 100 g- a mixture of alkylarylsulfonate and polyglycol ether and fatty alcohols 100 g
- dimetilformamid 50 g- dimethylformamide 50 g
- ksilen 575 g- xylene 575 g
Koncentrirane suspenzije, ki so uporabne tudi s škropljenjem, pripravimo tako, da dobimo stabilen tekoč produkt, ki se ne useda, in običajno vsebujejo 10 do 75 % učinkovine, 0,5 do 15 % površinsko aktivnih sredstev, 0,1 do 10 % tiksotropnih sredstev, 0 do 10 % primernih dodatkov, kot protipenil, korozijskih inhibitorjev, stabilizatorjev, penetracijskih sredstev in adhezivov, in kot nosilec vodo ali organsko tekočino, v kateri je učinkovina malo topna ali netopna. Določene organske trdne snovi ali mineralne soli lahko raztopimo v nosilcu, da pomagamo preprečiti usedanje, ali kot sredstva proti zmrzovanju za vodo.Concentrated suspensions, also useful by spraying, are prepared to give a stable, non-settling liquid product, typically containing 10 to 75% of the active ingredient, 0.5 to 15% of surfactants, 0.1 to 10% of thixotropic agents, 0 to 10% of suitable additives, such as anti-foaming agents, corrosion inhibitors, stabilizers, penetrating agents and adhesives, and as a carrier water or an organic liquid in which the substance is slightly soluble or insoluble. Certain organic solids or mineral salts can be dissolved in the carrier to help prevent settling, or as freezing agents for water.
Za primer navajamo sestavo koncentrirane suspenzije.For example, the composition of a concentrated suspension.
Primer SC 1:Example SC 1:
- učinkovina 500 g- active ingredient 500 g
- polietoksilirani tristirilfenol fosfat 50 g- polyethoxylated tristyrylphenol phosphate 50 g
- polietoksilirani alkilfenol 50 g- polyethoxylated alkylphenol 50 g
- natrijev polikarboksila20 g- Polycarboxyl sodium20 g
- etilen glikol . 50 g- ethylene glycol. 50 g
- organopolisiloksansko olje (protipenilo) 1 g- Organopolysiloxane oil (antifoam) 1 g
- polisaharid 1,5 g- polysaccharide 1.5 g
-voda 316,5 g-water 316.5 g
Omočjive praške (ali praške za škropljenje) pripravimo običajno tako, da vsebujejo 20 do 95 % učinkovine, in običajno vsebujejo poleg trdnega nosilca 0 do 30 % omočila, in če je potrebno, 0,1 do 10 % enega ali več stabilizatorjev in/ali drugih dodatkov, kot penetracijskih sredstev, adhezivov ali sredstev proti skepljanju, barvil itd. Da dobimo praške za škropljenje ali omočljive praške, temeljito pomešamo učinkovine v primernih mešalnikih z dodatnimi snovmi in zmeljemo z mlini ali drugimi primernimi drobilniki. Tako dobimo praške za škropljenje, katerih omočljivost in suspendimost sta ugodni. Suspendiramo jih lahko z vodo do vsake želene koncentracije in te suspenzije so zelo ugodno uporabne zlasti za nanašanje na liste rastlin. Namesto omočljivih praškov lahko izdelamo paste. Pogoji in načini za izdelavo in uporabo teh past so podobni tistim za omočljive praške ali praške za škropljenje.Moisturizing powders (or spraying powders) are usually prepared to contain from 20 to 95% of the active ingredient, and typically contain from 0 to 30% of a wetting agent in addition to the solid carrier and, if necessary, from 0.1 to 10% of one or more stabilizers and / or other additives such as penetrating agents, adhesives or anti-caking agents, dyes, etc. In order to obtain a spray powder or a wettable powder, thoroughly mix the ingredients in suitable mixers with additional substances and grind with mills or other suitable crushers. Spray powders with a wettability and suspendability are thus obtained. They can be suspended with water to any desired concentration and these suspensions are very advantageous especially for application to plant leaves. Pastes can be made instead of wettable powders. The conditions and methods for making and using these traps are similar to those for wettable or sprayable powders.
Za primer navajamo različne pripravke omočljivih praškov (ali praškov za škropljenje):For example, here are various preparations of wettable powders (or spray powders):
Primer PM 1:Example PM 1:
Primer PM 2:Example PM 2:
- učinkovina 10 %- active ingredient 10%
- sintetičen okso alkohol razvejenega tipa s 13C atomi, etoksiliran z 8 do 10 etilen oksidi (omočilo) 0,75 %- Synthetic branched-type oxo alcohol with 13C atoms, ethoxylated with 8 to 10 ethylene oxides (wetting) 0,75%
- nevtralni kalcijev lignosulfonat (dispergent) 12 %- neutral calcium lignosulfonate (dispersant) 12%
- kalcijev karbonat (inertno polnilo) q.s. za 100 %- calcium carbonate (inert filler) q.s. 100%
Primer PM 3:Example PM 3:
Ta omočljivi prašek vsebuje iste sestavine, kot v prejšnjem primeru, v tehle deležih:This wettable powder contains the same ingredients as in the previous example in the following proportions:
- učinkovina 75 %- active ingredient 75%
- o močilo 1,50 %- o moistener 1.50%
- dispergent 8%- dispersant 8%
- kalcijev karbonat (inertno polnilo) q.s. do 100 %- calcium carbonate (inert filler) q.s. up to 100%
Primer PM 4:Example PM 4:
- učinkovina 90 %- active ingredient 90%
- etoksilirani maščobni alkohol (omočilo) 4 %- ethoxylated fatty alcohol (wetting) 4%
- etoksilirani feniletilfenol (dispergent) 6 %- ethoxylated phenylethylphenol (dispersant) 6%
Primer PM 5:Example PM 5:
- učinkovina 50 %- active ingredient 50%
- mešanica anionskih in neionskih površinsko aktivnih sredstev (omočilo) 2,5 %- Mixture of anionic and nonionic surfactants (wetting agent) 2.5%
- natrijev lignosulfonat (dispergent) 5 %- sodium lignosulfonate (dispersant) 5%
- kaolinska glina (inertni nosilec) 42,5 %- kaolin clay (inert carrier) 42.5%
Vodne disperzije in emulzije, na primer pripravki, dobljeni z razredčenjem omočljivega praška ah emulzibilnega koncentrata v smislu izuma s pomočjo vode, so vključeni v splošni okvir pričujočega izuma. Emulzije so lahko vrste voda-v-olju ah olje-v-vodi in imajo lahko gosto konsistenco, kot je konsistenca majoneze.Aqueous dispersions and emulsions, for example, preparations obtained by diluting the wettable powder ah emulsifiable concentrate of the invention by means of water are included in the general scope of the present invention. Emulsions can be water-in-oil or oil-in-water types and may have a dense consistency, such as mayonnaise consistency.
Spojine v smislu izuma lahko formuliramo v obliki granulatov, ki se dajo dispergirati v vodi, ki so tudi obseženi v okviru izuma.The compounds of the invention can be formulated in the form of water-dispersible granules that are also present in the scope of the invention.
Ti disperzibilni granulati z navidezno gostoto, ki je na splošno med okoli 0,3 in 0,6, imajo velikost delcev, ki je na splošno med okoli 150 in 2000 in prednostno med 300 in 1500 pm.These dispersible granules with a apparent density, generally between about 0.3 and 0.6, have a particle size of generally between about 150 and 2000 and preferably between 300 and 1500 pm.
Vsebnost učinkovine v teh granulatih je na splošno med okoli 1 % in 90 % in prednostno med 25 % in 90 %.The active substance content of these granules is generally between about 1% and 90% and preferably between 25% and 90%.
Preostanek granulata sestoji v bistvu iz trdnega polnila in v danem primeru površinsko aktivnih pomožnih snovi, ki podele granulatu lastnost disperzibilnosti v vodi. Ti granulati so lahko v bistvu dveh različnih vrst glede na to, ali je preostalo polnilo topno v vodi ali ne. Če je polnilo topno v vodi, je lahko mineralno ali prednostno organsko. Odlične rezulUie smo dosegli s sečnino. V primeru netopnega polnila je le-to prednostno mineramo, kot npr. kaolin ali bentonit. V tem primeru so mu s pridom dodana površinsko aktivna sredstva (v množini od 2 do 20 mas. % granulata), od katerih tvori več kot polovico na primer vsaj en dispergent, v bistvu anionski, kot alkalijski ali zemeljsko alkalijski polinaftalen sulfonat ali alkalijski ali zemeljsko alkalijski lignosulfonat, preostanek pa tvorijo neionska ali anionska omočila, kot alkalijski ali zemeljsko alkalijski alkil naftalen sulfonat.The remainder of the granulate consists essentially of a solid filler and, optionally, of surfactants that give the granulate a water-dispersible property. These granules can be essentially of two different types depending on whether or not the remaining filler is soluble in water. If the filler is soluble in water, it may be mineral or preferably organic. Excellent results were achieved with urea. In the case of insoluble filler, it is a preferred mineral such as e.g. kaolin or bentonite. In this case, surfactants (in an amount of 2 to 20% by weight of granulate) are advantageously added, of which more than half form for example at least one dispersant, substantially anionic, such as alkali or alkaline earth polynaphthalene sulfonate or alkali or terrestrial alkali lignosulfonate and the remainder is formed by non-ionic or anionic wetting agents, such as alkali or terrestrial alkali alkyl naphthalene sulfonate.
Sicer pa lahko, četudi to ni neobhodno, dodamo druga pomožna sredstva, kot protipenila.Otherwise, although not necessary, other auxiliaries may be added, such as antifoams.
Granulat v smislu izuma lahko pripravimo tako, da zmešamo potrebne sestavine in jih nato granuliramo po različnih tehnikah, ki so znane same po sebi (priprava za dražiranje, fluidizirani sloj, atomiziranje, ekstruzija itd.). Na splošno zaključimo z drobljenjem, ki mu sledi sejanje na dimenzijo delcev, ki jo izberemo v zgoraj omenjenih mejah.The granulate of the invention can be prepared by mixing the necessary ingredients and then granulating them according to various techniques known per se (irrigation, fluidized bed, atomizing, extrusion, etc.). Generally, we conclude with crushing followed by sieving to the particle dimension selected within the limits mentioned above.
Prednostno ga dobimo z ekstruzijo, pri čemer delamo tako, kot je navedeno v primerih dalje spodaj.It is preferably obtained by extrusion, doing the same as described in the examples below.
Primer GDI: Disperzibilni granulatGDI example: Dispersible granulate
V mešalniku zmešamo 90 mas. % učinkovine in 10 % sečnine v kroglicah. Mešanico nato meljemo v mlinu na čepe. Dobimo prah, ki ga navlažimo z okoli 8 mas. % vode.In the mixer mix 90 wt. % of the active substance and 10% of the urea in the beads. The mixture is then ground in a mill into plugs. A powder is obtained which is moistened with about 8 wt. % water.
Vlažni prah ekstrudiramo v ekstruderju s perforiranim valjem. Dobimo granulat, ki ga sušimo, nato zdrobimo in presejemo tako, da obdržimo samo granulat z dimenzijami med 150 in 2000 gm.The wet powder is extruded in an extruder with a perforated cylinder. A granulate is obtained which is dried, then crushed and sieved to retain only a granulate with dimensions between 150 and 2000 gm.
Primer GD2: Disperzibilni granulatExample GD2: Dispersible granulate
V mešalniku mešamo tele sestavine:In the mixer mix the following ingredients:
- učinkovina 75 %- active ingredient 75%
- omočilno sredstvo (natrijev alkilnaftalen sulfonat) 2 %- wetting agent (sodium alkylnaphthalene sulfonate) 2%
- dispergent (natrijev polinaftalen sulfonat) 8 %- dispersant (sodium polynaphthalene sulfonate) 8%
- inertno, v vodi netopno polnilo (kaolin) 15 %- inert, water-insoluble filler (kaolin) 15%
To mešanico granuliramo v fluidiziranem sloju v prisotnosti vode, jo bi»to sušimo, zdrobimo in presejemo, da dobimo granule z dimenzijami med 0,15 in 0,80 mm.This mixture was granulated in a fluidized bed in the presence of water, which would be dried, crushed and sieved to give granules with dimensions between 0.15 and 0.80 mm.
Te granule lahko uporabljamo same, raztopljene ali dispergirane v vodi tako, da dobimo zahtevano dozo. Uporabimo jih lahko tudi za pripravo združkov z drugimi učinkovinami, zlasti fungicidi, pri čemer so le-ti lahko v obliki omočljivih praškov ali granul ali vodnih suspenzij.These granules can be used alone, dissolved or dispersed in water to obtain the required dose. They can also be used to prepare compounds with other ingredients, in particular fungicides, in the form of wettable powders or granules or aqueous suspensions.
Kar zadeva pripravke, prilagojene skladiščenju in transportu, vsebujejo bolj s pridom 0,5 do 95 (mas.) % učinkovine.As regards preparations adapted for storage and transport, they contain more than 0.5 to 95% by weight of the active substance.
Predmet izuma je tudi uporaba spojin v smislu izuma za boj proti glivičnim boleznim rastlin s preventivno ali kurativno obdelavo le-teh ali njihovega rastišča.The subject of the invention is also the use of the compounds of the invention for combating fungal diseases of plants by preventive or curative treatment of them or their habitat.
S pridom jih uporabljamo v dozah od 0,005 do 5 kg/ha in podrobneje 0,01 do 1 kg/ha.They are advantageously used in doses from 0.005 to 5 kg / ha and in particular from 0.01 to 1 kg / ha.
Claims (9)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9214432A FR2698359B1 (en) | 1992-11-25 | 1992-11-25 | DERIVATIVES OF 2-ALKOXY 2-IMIDAZOLINE-5-ONES FUNGICIDES. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI9300611A true SI9300611A (en) | 1994-06-30 |
Family
ID=9436084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9300611A SI9300611A (en) | 1992-11-25 | 1993-11-25 | Fungicidal 2-alcoxy-2-imidazolin-5-one derivatives |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0599749A1 (en) |
| JP (1) | JPH06211804A (en) |
| KR (1) | KR940011450A (en) |
| CN (1) | CN1111240A (en) |
| AP (1) | AP446A (en) |
| AU (1) | AU666783B2 (en) |
| BG (1) | BG98239A (en) |
| BR (1) | BR9304573A (en) |
| CA (1) | CA2103192A1 (en) |
| CZ (1) | CZ253393A3 (en) |
| FI (1) | FI935228A (en) |
| FR (1) | FR2698359B1 (en) |
| HR (1) | HRP931431A2 (en) |
| HU (1) | HUT65906A (en) |
| IL (1) | IL107706A0 (en) |
| MA (1) | MA23032A1 (en) |
| MX (1) | MX9307271A (en) |
| MY (1) | MY109069A (en) |
| NZ (1) | NZ250216A (en) |
| PL (1) | PL301187A1 (en) |
| SI (1) | SI9300611A (en) |
| SK (1) | SK130793A3 (en) |
| TR (1) | TR28264A (en) |
| ZW (1) | ZW15993A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3931907A1 (en) * | 1989-09-25 | 1991-04-04 | Henkel Kgaa | AQUEOUS LACQUER SPRAY PROTECTIVE COATING FOR SPRAY CABINS AND METHOD FOR THE PRODUCTION THEREOF |
| FR2706456B1 (en) * | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Optically active derivatives of 2-imidazoline-5-ones and 2-imidazoline-5-thiones fungicides. |
| US6002016A (en) * | 1991-12-20 | 1999-12-14 | Rhone-Poulenc Agrochimie | Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones |
| US6008370A (en) * | 1992-11-25 | 1999-12-28 | Rhone-Poulenc Agrochimie | Fungicidal-2-alkoxy/haloalkoxy-1-(mono- or disubstituted)amino-4,4-disubstituted-2-imidazolin-5-ones |
| AU1892495A (en) * | 1994-03-09 | 1995-09-25 | Rhone-Poulenc Agrochimie | Pesticide substituted 2-imidazolinones |
| FR2721022B1 (en) * | 1994-06-10 | 1996-07-19 | Rhone Poulenc Agrochimie | Derivatives of 5-imino 2-imidazolines fungicides. |
| FR2722499B1 (en) * | 1994-07-13 | 1996-08-23 | Rhone Poulenc Agrochimie | NEW 2-IMIDAZOLINE-5-ONES FUNGICIDE DERIVATIVES |
| FR2722652B1 (en) | 1994-07-22 | 1997-12-19 | Rhone Poulenc Agrochimie | FUNGICIDE COMPOSITION COMPRISING A 2-IMIDAZOLINE-5-ONE |
| FR2751327A1 (en) | 1996-07-22 | 1998-01-23 | Rhone Poulenc Agrochimie | INTERMEDIATES FOR THE PREPARATION OF 2-IMIDAZOLINE-5-ONES |
| CA2294549A1 (en) * | 1997-06-18 | 1998-12-23 | Synaptic Pharmaceutical Corporation | Heterocyclic substituted piperidines and uses thereof |
| US6159990A (en) | 1997-06-18 | 2000-12-12 | Synaptic Pharmaceutical Corporation | Oxazolidinones as α1A receptor antagonists |
| CN111848521A (en) * | 2020-08-26 | 2020-10-30 | 韶远科技（上海)有限公司 | Preparation method of 2-substituted-4-alkoxy imidazole compound |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB967167A (en) * | 1960-10-31 | 1964-08-19 | Ici Ltd | N-trichloromethylmercaptohydantoins and fungicidal compositions containing them |
| NL257812A (en) * | 1959-11-10 | |||
| FR2706456B1 (en) * | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Optically active derivatives of 2-imidazoline-5-ones and 2-imidazoline-5-thiones fungicides. |
| FR2685328B1 (en) * | 1991-12-20 | 1995-12-01 | Rhone Poulenc Agrochimie | DERIVATIVES OF 2-IMIDAZOLINE-5-ONES AND 2-IMIDAZOLINE-5-THIONES FUNGICIDES. |
| FR2693192B1 (en) * | 1992-07-02 | 1994-08-12 | Rhone Poulenc Agrochimie | Derivatives of 2-imidazoline-5-ones and 2-imidazoline-5-thiones fungicides. |
-
1992
- 1992-11-25 FR FR9214432A patent/FR2698359B1/en not_active Expired - Fee Related
-
1993
- 1993-11-16 CA CA002103192A patent/CA2103192A1/en not_active Abandoned
- 1993-11-17 NZ NZ250216A patent/NZ250216A/en unknown
- 1993-11-17 MA MA23338A patent/MA23032A1/en unknown
- 1993-11-18 AP APAP/P/1993/000591A patent/AP446A/en active
- 1993-11-22 JP JP5292012A patent/JPH06211804A/en active Pending
- 1993-11-22 MX MX9307271A patent/MX9307271A/en unknown
- 1993-11-22 EP EP93420462A patent/EP0599749A1/en not_active Ceased
- 1993-11-22 IL IL10770693A patent/IL107706A0/en unknown
- 1993-11-23 TR TR01108/93A patent/TR28264A/en unknown
- 1993-11-23 ZW ZW15993A patent/ZW15993A1/en unknown
- 1993-11-23 SK SK1307-93A patent/SK130793A3/en unknown
- 1993-11-24 FI FI935228A patent/FI935228A/en not_active Application Discontinuation
- 1993-11-24 PL PL93301187A patent/PL301187A1/en unknown
- 1993-11-24 AU AU51880/93A patent/AU666783B2/en not_active Ceased
- 1993-11-24 CZ CZ932533A patent/CZ253393A3/en unknown
- 1993-11-24 HU HU9303342A patent/HUT65906A/en unknown
- 1993-11-24 BR BR9304573A patent/BR9304573A/en not_active Application Discontinuation
- 1993-11-24 HR HR9214432A patent/HRP931431A2/en not_active Application Discontinuation
- 1993-11-24 BG BG98239A patent/BG98239A/en unknown
- 1993-11-24 MY MYPI93002465A patent/MY109069A/en unknown
- 1993-11-25 CN CN93120371A patent/CN1111240A/en active Pending
- 1993-11-25 KR KR1019930025288A patent/KR940011450A/en not_active Application Discontinuation
- 1993-11-25 SI SI9300611A patent/SI9300611A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL107706A0 (en) | 1994-02-27 |
| ZW15993A1 (en) | 1994-04-27 |
| BR9304573A (en) | 1994-06-14 |
| HRP931431A2 (en) | 1996-12-31 |
| TR28264A (en) | 1996-04-17 |
| AU5188093A (en) | 1994-06-09 |
| HUT65906A (en) | 1994-07-28 |
| CZ253393A3 (en) | 1994-06-15 |
| EP0599749A1 (en) | 1994-06-01 |
| CN1111240A (en) | 1995-11-08 |
| CA2103192A1 (en) | 1994-05-26 |
| FI935228A (en) | 1994-05-26 |
| MX9307271A (en) | 1994-07-29 |
| FR2698359B1 (en) | 1995-10-27 |
| MA23032A1 (en) | 1994-07-01 |
| FI935228A0 (en) | 1993-11-24 |
| NZ250216A (en) | 1995-07-26 |
| HU9303342D0 (en) | 1994-03-28 |
| AP9300591A0 (en) | 1994-01-31 |
| MY109069A (en) | 1996-11-30 |
| FR2698359A1 (en) | 1994-05-27 |
| AU666783B2 (en) | 1996-02-22 |
| AP446A (en) | 1996-01-17 |
| JPH06211804A (en) | 1994-08-02 |
| SK130793A3 (en) | 1994-11-09 |
| PL301187A1 (en) | 1994-05-30 |
| KR940011450A (en) | 1994-06-21 |
| BG98239A (en) | 1994-07-15 |
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