HU202365B - Insecticide compositions containing nitro-methylene derivative and process for producing the active component - Google Patents

Insecticide compositions containing nitro-methylene derivative and process for producing the active component Download PDF

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Publication number
HU202365B
HU202365B HU895815A HU581586A HU202365B HU 202365 B HU202365 B HU 202365B HU 895815 A HU895815 A HU 895815A HU 581586 A HU581586 A HU 581586A HU 202365 B HU202365 B HU 202365B
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Hungary
Prior art keywords
formula
producing
compositions containing
active component
compounds
Prior art date
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HU895815A
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English (en)
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HU895815D0 (en
Inventor
Kozo Shiokawa
Shinichi Tsuboi
Shinzo Kagabu
Koichi Moriya
Original Assignee
Nihon Tokushu Noyaku Seizo Kk
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27548804&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HU202365(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from JP60018628A external-priority patent/JPH0649699B2/ja
Priority claimed from JP60018627A external-priority patent/JPH066585B2/ja
Priority claimed from JP60023683A external-priority patent/JPH07613B2/ja
Priority claimed from JP10685385A external-priority patent/JPH0629258B2/ja
Priority claimed from JP60106854A external-priority patent/JPS61267575A/ja
Priority claimed from JP60219082A external-priority patent/JPH0730070B2/ja
Application filed by Nihon Tokushu Noyaku Seizo Kk filed Critical Nihon Tokushu Noyaku Seizo Kk
Publication of HU895815D0 publication Critical patent/HU895815D0/hu
Publication of HU202365B publication Critical patent/HU202365B/hu

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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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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    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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    • A01N47/22—O-Aryl or S-Aryl esters thereof
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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Description

A találmány új nitro-metilén-származékokat tartalmazó inszekticid készítményekre és ilyen vegyületek előállítási eljárására vonatkozik.
Ismert, hogy bizonyos nitro-metilén-származéknak, így például az l-benzil-2-(nitro-metilén)-tetrahidropirimidin-nek (2 514 402 számú német szövetségi köztársaságbeli szabadalmi leírás) inszekticid hatása van, míg bizonyos tri azol in-származékok bélrendszeri daganatokkal szembeni (tumor-ellenes) hatással rendelkeznek (196 877/1984 számú japán nyilvánosságrahozatali irat).
Az l-benzil-2-(nitro-imino)-imidazolidint a Can.
J. Chem. 39, 1878-1796 irodalmi hely ismerteti.
Azt tapasztaltuk, hogy a (I) általános képletnek megfelelő új vegyületeknek inszekticid hatása van. Az (I) általános képletű 3- nitro-3-[l-(piridil-metil)(lH,4H,5H,6H-tetrahidropirimidin-(vagy 2-imidazolin)-2-il)]-akrilsav-származékokban n értéke 0 vagy 1, m értéke 0 vagy 1,
Y jelentése halogénatom.
A találmány szerinti eljárással az (I) általános képletű vegyűleteket úgy állítjuk elő, hogy egy (II) általános képletű l-(piridil-metil)-2-(nitro-metilén)-hexahidropirimidin - vagy -2-imidazolin-vegyületet a képletben n, m, és Y jelentése a fenti - glioxilsavval reagáltatunk.
A találmány szerinti eljárásnál kiindulási vegyületként alkalmazott (II) általános képletű vegyületek szintén új vegyületek, részletesen a jelen bejelentéssel azonos elsőbbségű, 200 654 lajstromszámú magyar szabadalmi leírásban vannak ismertetve.
A találmány szerinti eljárást előnyösen oldószer jelenlétében végezzük, erre a célra bármely ismert szerves oldószer alkalmazható, így például a következők: adott esetben klórozott alifás, aliciklusos vagy aromás szénhidrogének, így például hexán, ciklohexán, petroléter, Ugróin, benzol, toluol, xilol, metilénklorid, kloroform, szén-tetraklorid, etilén-klorid, triklór-etilén, klór-benzol; éterek, így például dietil-éter, metil-etil-éter, diizopropil-éter, dibutil-éter, dipropiléter, dioxán vagy tetrahidrofurán; nitrilek, így például acetonitril, propionitril vagy akrilnitril; alkoholok, így például metanol, etanol, izopropanol, butanol vagy etilénglikol; savamidok, így például dimetil-formamid vagy dimetil-acetamid; szulfonok vagy szulfidok, így például dimetil-szulfoxid vagy szulfolán; valamint bázisok, így például piridin.
A találmány szerinti eljárást széles hőmérséklettartományban végezhetjük, előnyösen 0 °C és 50 ’C közötti hőmérsékletet és normál nyomást alkalmazunk.
A találmány szerinti eljárással előállíthatjuk az (I) általános képletű veggyületek sóit is, így például szervetlen vagy szerves savakkal képzett sóit, továbbá szulfonátjait vagy fémsóit is.
A találmány szerinti eljárással előállított (I) általános képletű vegyületek kiváló inszekticid hatással rendelkeznek és így előnyösen alkalmazhatók a legkülönbözőbb rovarok, így például szívó- és csípőrovarok, valamint egyéb növényparaziták és egészségkárosító és tárolt takarmányokat károsító kártevők pusztítására.
Példaképpen felsoroljuk a következő kártevőket: Coleopterous rovarok: Callosobruchus chinensis, Sitophilus zeamais, Tribolium castaneum, Epilachna 2 vjgjtochtomaculata, Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Monochamus altematus, Lissorhoptrus oryzophilus és Lytus brunneus.
Lepidopterous rovarok: Lymantria dispar, Malacosoma neustrium, Pieris rapae, podoptera litura, Mamestra brassicae, Chilo suppressalis, Pyrausta nubilalis, Ephestia cautella, Adoxophyes orana, Carpocapsa pomonella, Agrotis fucosa, Galleria mellonella, Plutella maculipennis, és Phyllocnistis citrella.
Hemipterous rovarok: Nephotettix cincticeps, Nilaparvata lugens, Pseudococcus comstocki, Unaspis ynonensis, Myzus persicae, Aphis pomi, Aphis gossypii, Rhopalosiphum pseudobrassicas, Stephanitis nashi, Nazara spp., Cimex lectularius, Trialeurodes vaporariorum, és Psylla spp.
Orthopterous rovarok: Blatella germanica, Periplaneta americana, Cryllotalpa africana és Locusta migratoria migratoriodes.
Isopterous rovarok: Deocutermes separatus és Coptotermes formosanus.
Dipterous rovarok: Musca domestica, Aedes aegypti, Hylemia platura, Culex pipiens, Anopheles sinensis és Culex tritaeniorhynchus.
Az állatgyógyászat területén a találmány szerinti eljárással előállított aktív vegyületek a legkülönbözőbb állatparaziták (endo- és ecto-paraziták), így például rovarok és férgek ellen alkalmazhatók. Ilyenek például a következők:
rovarok: Gastrophilus spp., Stomoxys spp., Trichodectes spp., Rhodnium spp. és Ctenocephalides canis.
A találmány szerinti eljárással előállított (I) általános képletű vegyűleteket a szokásos készítmények formájában alkamazzuk, így például oldatok, emulziók, szuszpenziók, porok, habok, paszták, granulátumok, aeroszolok, valamint hatóanyaggal impregnált természetes és mesterséges anyagok, finomkapszulák formájában, továbbá vetőmagokat bevonó készítmények, különböző füstölőkészítmények, valamint ULV hideg és meleg ködkészítmények formájában.
Ezek a készítmények ismert módon állíthatók elő, például úgy, hogy hatóanyagokat a szilárd vagy folyékony, vagy cseppfolyósított gáz hordozó-, illetve szaporítóanyaggal elkeverjük, adott esetben emulgeáló-, diszpergáló és/vagy habképző-hatású felületaktív anyag jelenlétében. Ha hordozóanyagként vizet alkalmazunk, segédoldószerként szerves oldószer is felhasználható.
Folyékony hordozóként például a következő anyagok alkalmazhatók: aromás szénhidrogének, így például xilol, toluol vagy alkil-naftalinok; klórozott aromás vagy alifás szénhidrogének, így például klórbenzol, klór-etilének vagy metilén-klorid; alifás szénhidrogének, így például ciklohexán, vagy paraffinok, így például különböző ásványolajfrakciők; alkoholok, így például butanol vagy glikol, valamint ezek éterei, észterei vagy ketonjai, így például aceton, metil-etilketon, metil-izobutil-keton vagy ciklohexanon; erősen poláros oldószerek, így például dimetil-formamid vagy dimetil-szulfoxid, valamint víz.
Cseppfolyósított gáz hordozóanyagokon olyan anyagokat értünk, amelyek normál nyomáson és hőmérsékleten gázok, ilyenek például az aeroszol vivőanyagok, például a halogén-szénhidrogének, valamint a bután, propán, nitrogén vagy szén-dioxid.
HU 202365 Β
A szilárd hordozóanyagok lehetnek például őrölt, természetes ásványi anyagok, így például kaolin, agyagok, talkum, kréta, kvarc, attapulgit, montmorillonit vagy diatomaföld, továbbá őrölt szintetikus anyagok, így például nagydiszperzitású kovasav alumínium-dioxid vagy szilikátok. Granulátomok esetében a hordozóanyag lehet például aprított és frakcionált természetes kőzet, így például kalcit, márvány, habkő, szepiolit vagy dolomit, továbbá szervetlen és szerves őrlemények granulátumai, valamint különböző szerves anyagok granulátumai, így például fűrészpor, kókuszdióhéj, kukoricaszár és dohányszár granulátum.
Emulgeáló és habképző anyagként alkalmazhatunk különböző nemionos és anionos anyagokat, így például poli(etilén-oxi)-zsírsav-észtereket, poli(etilén-oxi)zsíralkohol-étereket, így például alkil-aril-poliglikolétereket, alkil-szulfonátokat, alkil-szulfátokat, arilszulfátokat, aril-szulfonátokat, valamint albumin-hidrolizátumokat. Diszpergálószerként például ligninszulfitszennylúgot vagy metil-cellulózt alkalmazunk.
Ragasztóanyagként például karboxi-metil-cellulózt vagy természetes vagy mesterséges polimereket alkalmazunk por, granulátum vagy latex formájában, így például poli(vinil-alkohol), poli(vinil-acetát).
A készítményekhez színezőanyagokat is adagolhatunk, ilyenek például: a szervetlen pigmentek, például vas-oxid, titán-oxid vagy berlini kék, továbbá szerves színezékek, így például alizarin-, azo- vagy fém-ftalo-színezékek, így például alizarin-, azo- vagy fémftalo-színezékek. Nyomelemként vas-sókat, mangán, bór, réz, kobalt, molibdén, valamint cinksókat alkalmazunk.
A találmány szerinti készítmények általában 0,1-95 t%, előnyösen 0,5-90 t% hatóanyagot tartalmaznak.
A találmány szerinti készítményekeket adott esetben összekeverhetjük más ismert hatóanyaggal is, így például inszekticidekkel, attraktánsokkal, sterilizáló szerekkel, akaricidekkel, nematicidekkel, fungicidekkel, növekedésszabályozó szerekkel, valamint herbicidekkel is. Inszekticidként például a következők alkalmazhatók: hoszfátok, karbamátok, karboxilátok, klórozott szénhidrogének, fenil-karbamidok, vagy mikroorganizmusok által termelt anyagok.
A találmány szerinti készítmények összekeverhetők továbbá aktiváló hatású anyagokkal is, amelyek alatt olyan anyagokat értünk, amelyek növelik a készítmények hatásosságát, anélkül, hogy önmaguk hatásosak lennének.
A felhasználásra kerülő készítmények - amelyek lehetnek kereskedelmi készítmények, vagy ezekből nyert felhasználásra kész készítmények - hatóanyagtartalma 0,0000001 - 90 t% közötti, előnyösen 0,0001 és 1 t% közötti érték.
A készítményeket ismert módon a megfelelő formában alkalmazzuk.
A találmány szerinti eljárással előállított vegyületeket tartalmazó készítményeket egészségkárosító rovarok és tárolt termékek rovarkártevői ellen alkal20 mazva, megállapíthatjuk, hogy kiválóak mind maradék-hatásukat, mind stabilitásukat tekintve meszes anyagokkal szemben.
A következő példákkal a találmányt közelebbről illusztráljuk.
7. példa (l) képletű vegyület
1,2 g finomra porított l-(4-piridil-metil)-2-(nitrometilénj-tetrahidropirimidint 20 ml metanolban ol30 dunk, hozzáadunk 2 csepp koncentrált kénsavat, majd 1,6 g 26 t%-os vizes glioxilsavat, majd a keveréket 3 órán át szobahőmérsékleten keverjük. A pH 7-es értékre való beállítása után a kiváló csapadékot szűrjük, metanollal és éterrel mossuk, szárítjuk. A tennék
1,1 g 3-[l-(4-piridil-metil)-lH,4H,5H,6H-tetrahidropirimidin-2-il]-3-nitro-akrilsav, olvadáspontja 150— 155 ’C (bomlik).
A találmány szerinti eljárással még a következő, (I) általános képletnek megfelelő vegyületeket állí40 tottuk elő:
Vegy. száma Z R R1 R2 R3 R4 R3 R6 n L Hal
2 nv3“ H H H H H 0 Cl Cl
3 α/Λ_ - 1Ψ=7 H H H H H 0 Cl Cl
4 ci/Λ- N~7 H H H H H 0 Br Br op.: 140-143 ’C (bomlik)
5 Cl/Λ N^7 H H H H H 0 Cl Br
6 (2) képletű vegyület op.: 170-175 ’C
Biológiai példák
I. példa 60
Organofoszfor készítményekkel szemben rezisztens
Nephotettix cincticeps kártevő elleni hatás Oldószer 3 tömegrész xilol Emulgeátor: 1 tömegrész poli(oxi-etilén)-alkil-fenil-éter. 65
A vizsgálatokhoz szükséges készítmények előállításához az 1 tömegrész hatóanyagot a fenti oldószerrel és emulteátorral elkevertünk és vízzel a kívánt koncentrációra hígítottuk.
Vizsgálati eljárás:
cm átmérőjű cserepekben termesztett 10 cm magas rizsnövényeket 10-10 ml fenti, meghatározott 3
HU 202365 Β koncentrációjú készítménnyel bepermetezünk, megszárítjuk és 7 cm átmérőjű és 14 cm magas hálóval letakarjuk, majd 30 nőstény imagót helyezünk minden hálóra. A cserepeket ezután konstans hőmérsékleten tartjuk, majd a 2 nap elteltével az elpusztult egyedeket megszámoljuk és a halálozási arányt megállapítjuk.
ppm hatóanyagtartalom esetében a 4. számú vegyület esetében például 100%-os halálozási arányt határoztunk meg.
Az összehasonlító vegyületek esetében a halálozási arány a következő volt:
A-l: 65% 40 ppm hatóanyagmennyiségnél,
A-2: 40% 200 ppm hatóanyagmennyiségnél és
0% 40 ppm hatóanyagmennyiségnél,
A-3: 0% 200 ppm hatóanyagmennyiségnél és
A-4: 30% 200 ppm hatóanyagmennyiségnél.
Készítmény előállítási példák
1. Permetpor készítmény (Diszpergálható por) t% 1. példa szerinti hatóanyagot elkeverünk t% dibutil-naftalinszulfonáttal, 5 t% nátrium-lignoszulfáttal, 2 t% nagydiszperzitású kovasavval és t% természetes kőzetliszttel és finom porrá őröljük. A kapott poranyagot felhasználáshoz annyi vízzel keverjük el, hogy a kívánt koncentrációjú készítményt nyerjük.
2. Emulgeálható koncentrátum t% 4. példa szerinti hatóanyagot feloldunk 55 t% xilol és 10 t% ciklohexanon elegyében és hozzáadunk 10 t% dodecil-benzol-szulfonsav-kalciumsó és nonil-fenol-poliglikol-éter keveréket. A kapott koncentrátumot felhasználás előtt vízzel a kívánt koncentrációra hígítjuk.

Claims (2)

  1. SZABADALMI IGÉNYPONTOK
    1. Inszekticid készítmény, azzal jellemezve, hogy hatóanyagként 0,1-95 tömeg% mennyiségben valamely (I) általános képletű 3-nitro-3-[l-(piridiImetil)-(lH,4H,5H,6H-tetrahidropirimidin(vagy -2imidazolin)-2-il)]-akrilsav-származékot vagy annak sóját - a képletben n értéke 0 vagy 1, m értéke 0 vagy 1, és
    Y jelentése halogénatom tartalmazza szilárd hordozóanyaggal, előnyösen természetes kőzetliszttel vagy ezek összetételének megfelelő szintetikus úton előállított őrleményekkel, folyékony hordozóanyaggal, előnyösen szerves vagy szervetlen oldószerekkel és/vagy egyéb segédanyaggal, előnyösen anionos vagy nemionos felületaktív anyaggal elkeverve.
  2. 2. Eljárás (I) általános képletű vegyületek és sóik előállítására - a képletben n értéke 0 vagy 1, m értéke 0 vagy 1,
    Y jelentése halogénatom, azzal jellemezve, hogy egy (II) általános képletű l-(piridil-metil)-2-(nitro-metiIén)- hexahidropirimidint vagy -2-imidazolint - a képletben n, m és
    Y jelentése a fenti - glioxilsavval reagáltatunk és kívánt esetben a kapott vegyületet sóvá alakítjuk.
HU895815A 1985-02-04 1986-02-03 Insecticide compositions containing nitro-methylene derivative and process for producing the active component HU202365B (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP60018628A JPH0649699B2 (ja) 1985-02-04 1985-02-04 ニトロメチレン誘導体、その製法及び殺虫剤
JP60018627A JPH066585B2 (ja) 1985-02-04 1985-02-04 ニトロメチレン誘導体、その製法及び殺虫剤
JP60023683A JPH07613B2 (ja) 1985-02-12 1985-02-12 ニトロメチレン誘導体、その製法及び殺虫剤
JP10685385A JPH0629258B2 (ja) 1985-05-21 1985-05-21 殺虫性ニトロメチレン誘導体
JP60106854A JPS61267575A (ja) 1985-05-21 1985-05-21 ニトロイミノ誘導体、その製法及び殺虫剤
JP60219082A JPH0730070B2 (ja) 1985-10-03 1985-10-03 新規複素環式化合物

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HU86466A HU200651B (en) 1985-02-04 1986-02-03 Insecticide comprising nitromethylene or nitroimino derivative and process for producing such compounds

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HUT41954A (en) 1987-06-29
DK51986A (da) 1986-08-05
PH30435A (en) 1997-05-09
DK172805B1 (da) 1999-08-02
US5580889A (en) 1996-12-03
AU5286686A (en) 1986-08-07
CA1276018C (en) 1990-11-06
US4742060A (en) 1988-05-03
DK104292D0 (da) 1992-08-21
US5750704A (en) 1998-05-12
NL971014I1 (nl) 1997-09-01
ATE67493T1 (de) 1991-10-15

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