DD146242A5 - SCHAEDLINGSBEKAEMPFUNGSMITTEL - Google Patents
SCHAEDLINGSBEKAEMPFUNGSMITTEL Download PDFInfo
- Publication number
- DD146242A5 DD146242A5 DD79216031A DD21603179A DD146242A5 DD 146242 A5 DD146242 A5 DD 146242A5 DD 79216031 A DD79216031 A DD 79216031A DD 21603179 A DD21603179 A DD 21603179A DD 146242 A5 DD146242 A5 DD 146242A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- spp
- methyl
- iso
- dihydro
- propyl
- Prior art date
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- 235000013447 Xanthosoma atrovirens Nutrition 0.000 description 1
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- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 241001414985 Zygentoma Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
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- 239000010941 cobalt Substances 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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- 230000001418 larval effect Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
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- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
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- 239000001007 phthalocyanine dye Substances 0.000 description 1
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- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
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- 239000011435 rock Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Die Erfindung betrifft Schaedlingsbekaempfungsmittel fuer die Anwendung in der Land- und Forstwirtschaft, im Material- und Vorratsschutz, auf dem Hygienesektor sowie in der Veterinaermedizin. Ziel der Erfindung sind Schaedlingsbekaempfungsmittel mit verbesserter insektizider, akarizider und nematizider Wirkung. Erfindungsgemaesz werden als Wirkstoffe in den neuen Schaedlingsbekaempfungsmitteln N-iso-Propyl-S-(1,6-dihydro-6-(thi)oxo-pyridazin(1)yl-methyl)-thiol-phosphorsaeureesteramide der Formel I angewendet, in welcher R fuer Alkyl mit 1 bis 6 Kohlenstoffatomen und X fuer Sauerstoff oder Schwefel steht.The invention relates to Schaedlingsbekaempfungsmittel for use in agriculture and forestry, in material and storage protection, in the hygiene sector and in veterinary medicine. The aim of the invention are pesticides with improved insecticidal, acaricidal and nematicidal activity. According to the invention, N-iso-propyl-S- (1,6-dihydro-6- (thi) oxopyridazine (1) yl-methyl) thiol-phosphoric acid ester amides of the formula I are used as active ingredients in the new pest control agents, in which R is alkyl of 1 to 6 carbon atoms and X is oxygen or sulfur.
Description
Berlin, den 28.2.1980Berlin, 28.2.1980
AP C 07 F/216 031 56 229/12AP C 07 F / 216 031 56 229/12
Schädlingsbekämpfungsmittel Anwendungsgebiet der Erfindung Pesticides Field of application of the invention
Die Erfindung betrifft Schädlingsbekämpfungsmittel mit einem Gehalt an neuen N-iso-Propyl-S~(l,6-dihydro~6-(thio)oxopyridazin(l)yl-methyl)-thiolphosphorsäureesteramiden, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Schädlingsbekämpfungsmittel, insbesondere als Insektizide, Akarizide und Nematizide.The invention relates to pesticides containing novel N-iso-Propyl-S ~ (l, 6-dihydro ~ 6- (thio) oxopyridazin (l) yl-methyl) -thiolphosphorsäureesteramiden, a process for their preparation and their use as pesticides , in particular as insecticides, acaricides and nematicides.
Es ist bekannt, daß bestimmte S-(I,6-Dihydro-6-(thio)-oxopyridazin(l)yl~methyl)-(thiono)thiol-phosphorsäureester-. amide wie z. B. N-Allyl-0-äthyl-S-(l,6-dihydro~3-methyl-6-oxo-pyridazin(l)yl-methyl)-thionothiol-phosphorsäureesteramid, N,N-Dimethyl-O-äthyl-S-(1,ö-dihydro-S-methyl-öoxo-pyridazin(l)yl-methyl)-thiolphosphorsäureesteramid und N-iso-Propyl-0-n-propyl-S-(l,6-dihydro-3-methyl-6-thioxopyridazin(l)yl-methyl)-thionοthiol-phosphorsäure-esteramid, insektizide, akarizide und nematizide Eigenschaften aufweisen (vgl. DE-OS 2 348 736 und 2 603 052). Die Wirkung dieser Verbindung ist jedoch, insbesondere bei niedrigen Wirkstoffkonzentrationen und Aufwandmengen, nicht immer zufriedenstellend.It is known that certain S- (I, 6-dihydro-6- (thio) -oxopyridazine (1) yl-methyl) - (thiono) thiol-phosphoric acid ester-. amides such as B. N-allyl-O-ethyl-S- (1,6-dihydro-3-methyl-6-oxopyridazine (1) yl-methyl) -thionothiol-phosphoric acid ester amide, N, N-dimethyl-O-ethyl- S- (1, O-dihydro-S-methyl-δ-oxopyridazine (1) yl-methyl) -thiol phosphoric acid ester amide and N-isopropyl-0-n-propyl-S- (1,6-dihydro-3-methyl 6-thioxopyridazine (I) yl-methyl) -thionothiol-phosphoric acid ester-amide, insecticidal, acaricidal and nematicidal properties (compare German Offenlegungsschriften Nos. 2,348,736 and 2,603,052). However, the effect of this compound, especially at low drug concentrations and application rates, is not always satisfactory.
Ziel der ErfindungObject of the invention
Ziel der Erfindung ist die Bereitstellung von neuen Schädlingsbekämpfungsmitteln mit verbesserter insektizider, nematizider und akarizider Wirkung, breitem IVirkungsspektrumThe aim of the invention is the provision of new pesticides with improved insecticidal, nematicidal and acaricidal activity, broad spectrum of treatment
£ I O U O, I£ I O U O, I
28.2.1980 AP C 07 F/216 - 2 - 56 229/1228.2.1980 AP C 07 F / 216 - 2 - 56 229/12
und günstiger Pflanzen- und Warmblütertoxizität. Darlegung des Wesens der Erfindung and favorable plant and warm-blooded toxicity. Explanation of the essence of the invention
Der Erfindung liegt die Aufgabe zugrunde, Verbindungen aufzufinden, die die gewünschten Eigenschaften besitzen und die als Wirkstoff in Schädlingsbekämpfungsmitteln geeignet sind.The invention has for its object to find compounds which have the desired properties and which are suitable as active ingredient in pesticides.
Es wurden nun neue N-iso-Propyl-S-(l,6-dihydro-6-(thi )-oxo-pyridazin(l)yl-methyl)-thiolphosphorsäureesteramide der FormelThere are now novel N-iso-propyl-S- (l, 6-dihydro-6- (thi) -oxo-pyridazine (l) yl-methyl) -thiolphosphorsäureesteramide the formula
0 OR N-CH-S-P (I)0 OR N-CH-S-P (I)
NH-C3H7-ISONH-C 3 H 7 -ISO
gefunden, in welcherfound in which
R für Alkyl mit 1 bis 6 Kohlenstoffatomen und X für Sauerstoff oder Schwefel steht.R is alkyl of 1 to 6 carbon atoms and X is oxygen or sulfur.
Man erhält Verbindungen der Formel (I), wenn man 1,6-Dihydro-l-chloromethyl-3-methyl-6-(thi )oxo-pyridazine der FormelCompounds of the formula (I) are obtained when 1,6-dihydro-1-chloromethyl-3-methyl-6- (thi) oxopyridazines of the formula
(II)(II)
in welcher X die oben angegebene Bedeutung hat, mit Salzen von N-iso-Propyl-thiolphosphorsäure-esteramiden der Formelin which X has the meaning given above, with salts of N-iso-propyl-thiolphosphorsäure-esteramides of the formula
28.2.1980 AP C 07 F/216 - 3 - 56 229/1228.2.1980 AP C 07 F / 216 - 3 - 56 229/12
0 Il y 0 Il y
M-S-P · (III)M-S-P (III)
NH-C3H7.isoNH-C 3 H 7 .iso
in welcher R die oben angegebene Bedeutung hat und M für ein Alkalimetall-, Erdalkalimetall- oder Ammoniumäquivalent steht,in which R has the abovementioned meaning and M is an alkali metal, alkaline earth metal or ammonium equivalent,
gegebenenfalls unter Verwendung eines Verdünnungsmittels umsetzt.optionally reacted using a diluent.
Die neuen Verbindungen (I) zeichnen sich durch hohe Wirksamkeit als Schädlingsbekämpfungsmittel, insbesondere durch hervorragende insektizide, akarizide und nematizide Eigenschaften aus.The new compounds (I) are distinguished by high activity as pesticides, in particular by excellent insecticidal, acaricidal and nematicidal properties.
Überraschenderweise zeigen die erfindungsgemäßen M-iso-Propyl· S-(l,5-dihydro-6-(thi)oxo-pyridazin(l)-yl-methyl)~thiolphosphorsäure-esteramide (I) erheblich höhere insektizide, akarizide und nematizide Wirkung als aus dem Stand der Technik bekannte Verbindungen analoger Konstitution und gleicher Wirkungsrichtung.Surprisingly, the M-iso-propyl · S- (l, 5-dihydro-6- (thi) oxopyridazine (l) -yl-methyl) -thiolphosphoric acid esteramides (I) according to the invention exhibit considerably higher insecticidal, acaricidal and nematicidal activity as known from the prior art compounds analogous constitution and the same direction of action.
Die Erfindung betrifft insbesondere Verbindungen der Formel (I), in welcherThe invention particularly relates to compounds of the formula (I) in which
R für geradkettiges Alkyl mit 1 bis 3 KohlenstoffatomenR is straight-chain alkyl having 1 to 3 carbon atoms
und X für Sauerstoff oder Schwefel steht.and X is oxygen or sulfur.
216 03216 03
. 28.2.1980, 02/28/1980
AP C 07 F/216 031 - 4 - 56 229/12AP C 07 F / 216 031 - 4 - 56 229/12
Verwendet man beispielsweise !,ö-Dihydro-l-chlormethyl-S-methyl-6-thioxo-pyridazin und das Natriumsalz von N-iso-Propyl-O-methyl-thiolphosphorsäure-esteramid als Ausgangsstoffe, so kann die Reaktion dieser Verbindungen durch folgendes Formelschema skizziert werden:If, for example, .alpha., .Alpha.-dihydro-1-chloromethyl-S-methyl-6-thioxopyridazine and the sodium salt of N-isopropyl-O-methylthiolphosphoric acid ester-amide are used as starting materials, the reaction of these compounds can be effected by the following Outlined formula scheme:
M °CH3M ° CH 3
. .NaC1 , , NaC1
NH-C H7-XSONH-C H 7 -XSO
NH-C3H7-ISONH-C 3 H 7 -ISO
Die als Ausgangsstoffe zu verwendenden 1,6-Dihydro-lchloromethyl~3-methyl-5-öthi)oxo-pyridazine sind durch die Formel (II), in welcher X für Sauerstoff oder Schwefel steht, definiert.The starting materials to be used 1,6-dihydro-lchloromethyl ~ 3-methyl-5-öthi) oxo-pyridazines are defined by the formula (II) in which X is oxygen or sulfur.
Die Verbindungen der Formel (II) sind bereits bekannt (vgl. DE-OS 2 348 736 und 2 603 052).The compounds of the formula (II) are already known (cf., DE-OSs 2,348,736 and 2,603,052).
Als Beispiele seien genannt:Examples include:
l.e-Dihydro-l-chloromethyl-S-methyl-ö-oxo-pyridazin und 1,e-Dihydro-l-chloromethyl-S-methyl-ö-thioxo-pyridazin.l.e-dihydro-1-chloromethyl-S-methyl-6-oxopyridazine and 1, e-dihydro-1-chloromethyl-S-methyl-6-thioxo-pyridazine.
216216
28.2.1980 AP C 07 F/216 - 5 - 56 229/12 28.2.1980 AP C 07 F / 216 - 5 - 56 229/12
Die als weitere Ausgangsstoffe einzusetzenden Salze von N-iso-Propyl-thiolphosphorsäure-esteramiden sind durch die Formel (III) definiert. Vorzugsweise stehen darinThe salts of N-iso-propyl-thiolphosphoric acid esteramides to be used as further starting materials are defined by the formula (III). Preferably stand in it
R für geradkettiges Alkyl mit 1 bis 3 KohlenstoffatomenR is straight-chain alkyl having 1 to 3 carbon atoms
und M für Natrium oder Kalium.and M for sodium or potassium.
Als Beispiele seien genannt:Examples include:
Natriumsalz und Kaliumsalz von O-Methyl-N-iso-propyl-thiolphosphorsäure-esteramid, Natriumsalz und Kaliumsalz von O-Äthyl-N-iso-propyl-thiolphosphorsäure-esteramid sowie Natriumsalz und Kaliumsalz von O-n-Propyl-N-iso-propylthiolphosphorsäure-esteramid.Sodium salt and potassium salt of O-methyl-N-isopropyl-thiophosphoric acid ester-amide, sodium salt and potassium salt of O-ethyl-N-isopropyl-thiophosphoric acid-esteramide and sodium salt and potassium salt of on-propyl-N-isopropyl-propylphosphoric acid ester-amide.
Die Ausgangsverbindungen der Formel (III) sind neu. Man erhält diese Verbindungen (III), wenn man N-iso-Propylthionophosphorsäure-esterchloride der FormelThe starting compounds of the formula (III) are new. These compounds (III) are obtained when N-iso-Propylthionophosphorsäure-ester chlorides of the formula
H OR Cl-P-^ (IV)H OR Cl-P- (IV)
V NH-C3H7-XSO V NH-C 3 H 7 -XSO
in welcher R die oben angegebene Bedeutung hat (vorzugsweise geradkettiges Alkyl mit 1 bis 3 Kohlenstoffatomen) mit wenigstens zwei Äquivalenten einer Hydroxyverbindung der Formelin which R has the meaning given above (preferably straight-chain alkyl having 1 to 3 carbon atoms) with at least two equivalents of a hydroxy compound of the formula
M-OH ; (V)M-OH; (V)
216 031216 031
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in welcher M die oben angegebene Bedeutung hat (vorzugsweise Natrium oder Kalium), gegebenenfalls unter Verwondung von Verdünnungsmitteln wie z. B. Wasser und Methanol, bei Temperaturen zwischen 0 und 100 C, vorzugsweise bei 20 bis 80 C, umsetzt. Die Reaktionsprodukte erhält man dann beispielsweise durch Extraktion mit Toluol und Eindampfen der wäßrigen Phase im Vakuum. -in which M has the meaning indicated above (preferably sodium or potassium), optionally with the dilution of diluents such. As water and methanol, at temperatures between 0 and 100 C, preferably at 20 to 80 C, is reacted. The reaction products are then obtained, for example, by extraction with toluene and evaporation of the aqueous phase in vacuo. -
Die Vorprodukte der Formel (IV) sind bekannt oder können analog bekannten Verfahren hergestellt werden (vgl. DE-OS 2 348 736).The precursors of the formula (IV) are known or can be prepared analogously to known processes (cf DE-OS 2 348 736).
Als Beispiele hierfür seien genannt: O-Methyl-, O-Äthyl~ und O-n-Propyl-N-iso-propyl-thionophosphorsäure-esterchlorid.Examples include: O-methyl, O-ethyl and O-n-propyl-N-iso-propyl-thionophosphorsäure ester chloride.
Als Beispiele für die Hydroxyverbindungen der Formel (V) seien Natriumhydroxid und Kaliumhydroxid genannt.As examples of the hydroxy compounds of formula (V) may be mentioned sodium hydroxide and potassium hydroxide.
Das Verfahren zur Herstellung der erfindungsgemäßen N-iso-Pröpyl-S-(1,6-dihydro-5-(thi)oxo-pyridazin(l)yl-methyl)-thiolphosphorsäure-esteramide wird bevorzugt unter Verwendung geeigneter Lösungs- oder Verdünnungsmittel durchgeführt. Als solche kommen praktisch alle inerten organischen Solventien in Frage. Hierzu gehören insbesondere aliphatische und aromatische, gegebenenfalls chlorierte Kohlenwasserstoffe, wie Benzin, Benzol, Toluol, Xylol, Methylenchlorid, Chloroform, Tetrachlorkohlenstoff, Chlorbenzol und o-Dichlorbenzol, Äther wie Diäthyl- und Dibutyläther, Tetrahydrofuran und Dioxan, Ketone wie Aceton, Methyläthyl-, Methylisopropyl- und Methylisobutylketon sowie Nitrile wie Acetonitril und Propionitril.The process for preparing the N-iso-propyl-S- (1,6-dihydro-5- (thi) oxopyridazine (1) -yl) -thiol phosphoric acid ester-amides according to the invention is preferably carried out using suitable solvents or diluents , As such, virtually all inert organic solvents come into question. These include in particular aliphatic and aromatic, optionally chlorinated hydrocarbons, such as benzine, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, Methyl isopropyl and methyl isobutyl ketone and nitriles such as acetonitrile and propionitrile.
11 6 U 3 1 1 1 6 U 3 1
. 28.2.1980, 02/28/1980
AP C 07 F/216 ' - 7 - 56 229/12AP C 07 F / 216 '- 7 - 56 229/12
Die Reaktionstemperatur kann innerhalb eines größeren Bereichs variiert werden. Im allgemeinen arbeitet man zwischen O und 100 0C, vorzugsweise bei 20 bis 80 0C.The reaction temperature can be varied within a wider range. In general, one works between O and 100 0 C, preferably at 20 to 80 0 C.
Das erfindungsgemäße Verfahren wird im allgemeinen bei Normaldruck durchgeführt.The process of the invention is generally carried out at atmospheric pressure.
Auf 1 Mol der l,6-Dihydro-l-chloromethyl-3-methyl-6-(thi) oxo-pyridazine (II) setzt man im allgemeinen zwischen 1,0 und 1,2 Mol, vorzugsweise zwischen 1,05 und 1,15 Hol der Salze von N-iso-Propyl-thiolphosphorsäureesteramiden (III) ein.On 1 mol of l, 6-dihydro-l-chloro-methyl-3-methyl-6- (thi) oxo-pyridazines (II) is generally used between 1.0 and 1.2 mol, preferably between 1.05 and 1 15 of the salts of N-iso-propyl-thiol phosphoric ester amides (III).
Die Umsetzung wird im allgemeinen in einem der oben angegebenen Verdünnungsmittel durchgeführt, und das Reaktionsgemisch wird mehrere Stunden bei der erforderlichen Temperatur gerührt. Danach wird mit einem organischen Lösungsmittel wie z. B. Toluol verdünnt und die organische Phase wie üblich durch V.'aschen, Trocknen und Abdestillieren des Lösungsmittels aufgearbeitet. Zur Charakterisierung der Produkte, welche im allcpneinen in öliger Form anfallen dient der Brechungsindex.The reaction is generally carried out in one of the above diluents, and the reaction mixture is stirred for several hours at the required temperature. Thereafter, with an organic solvent such. B. toluene and the organic phase worked up as usual by V.'aschen, drying and distilling off the solvent. The refractive index serves to characterize the products which are generally obtained in oily form.
Die neuen N~iso-Propyl-S-(l,6-dihydro-6~(thi)oxo-pyridazin-(l)yl-methyl)-thlolphosphorsäure-esteramide (I) zeichnen sich, wie bereits erwähnt, durch hervorragende insektizide, akarizide und nematozide Wirksamkeit aus. Sie besitzen bei geringer Phytotoxizität eine gute Wirkung gegen saugende und fressende Insekten, wie auch gegen Spinnmilben und Nematoden.The new N-iso-propyl-S- (1,6-dihydro-6- (thi) oxopyridazine- (1) -yl-methyl) -thol phosphoric acid ester amides (I) are characterized, as already mentioned, by excellent insecticidal agents , acaricidal and nematocidal activity. With low phytotoxicity, they have a good action against sucking and eating insects, as well as against spider mites and nematodes.
2t 6 03 i2t 6 03 i
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Daher können die erfindungsgemäßen Verbindungen (I) mit Erfolg im Pflanzenschutz als Schädlingsbekämpfungsmittel eingesetzt werden.Therefore, the compounds (I) of the present invention can be successfully used in crop protection as a pesticide.
Die Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit und günstiger Warmblütertoxizität zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:The active compounds are suitable for good plant tolerance and favorable toxicity to warm-blooded animals for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored products and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
Aus der Ordnung der Isopoda z. B. Oniscue asellus, Armadillidium vulgäre, Porcellio scaber.From the order of Isopoda z. B. Oniscue asellus, Armadillidium vulgaris, Porcellio scaber.
Aus der Ordnung der Diplopoda z. B. Blaniulus guttulatus.From the order of Diplopoda z. B. Blaniulus guttulatus.
Aus der Ordnung der Chilopoda z. B. Geophilus carpophagus, Scutigera spec.From the order of Chilopoda z. Geophilus carpophagus, Scutigera spec.
Aus der Ordnung der Symphyla z. B. Scutigerella immaculata.From the order of Symphyla z. B. Scutigerella immaculata.
Aus der Ordnung der Thysanura z. B. Lepisma saccharina.From the order of Thysanura z. B. Lepisma saccharina.
Aus der Ordnung der Collembola z. B. Onychiurus armatus.From the order of Collembola z. B. Onychiurus armatus.
Aus der Ordnung der Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaca maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.From the order of Orthoptera z. Blatta orientalis, Periplaneta americana, Leucophaca maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
Aus der Ordnung der Dermaptera z. B. Forficula auricularia.From the order of Dermaptera z. B. Forficula auricularia.
Aus der Ordnung der Isoptera z. B. Reticulitermes epp.From the order of Isoptera z. B. Reticulitermes epp.
Aus der Ordnung der Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.From the order of Anoplura z. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
Aus der Ordnung der Mallophaga z. B. Trichodectes spp.From the order of Mallophaga z. B. Trichodectes spp.
Z1.Ö UOiZ1.Ö UOi
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Damalinea spp. 'Damalinea spp. '
Aus der Ordnung der Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.From the order of Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.
Aus der Ordnung der Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.From the order of Heteroptera z. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
Aus der Ordnung der Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorura, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae» Laodelphax striatellus, Nilaparvat'a lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. Aus der Ordnung der Lepidoptera z, B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo epp., Pyrausta nubilalis, Ephöstia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana. « Aus der Ordnung der Coleoptera 2. B. Anobium puncta'tum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaodon cochlearla.e, Diabrotica spp.,From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorura, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae "Laodelphax striatellus, Nilaparvat'a lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. From the order of Lepidoptera z, B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp. , Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo epp., Pyrausta nubilalis, Ephöstia kuehniella, Galleria mellonella , Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana. «From the order of Coleoptera 2. B. Anobium puncta'tum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaodon cochlearla.e, Diabrotica spp.,
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Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethos aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica. Aus der Ordnung der Hymenoptera ζ. B. Diprion spp., Hoplocampa spp., Lasius spp., Monornorium pharaonis, Vespa spp. Aus der Ordnung der Diptera z. 8. Aedes spp.; Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethos aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica. From the order of Hymenoptera ζ. B. Diprion spp., Hoplocampa spp., Lasius spp., Monornorium pharaonis, Vespa spp. From the order of Diptera z. 8. Aedes spp .; Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp. Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
Aus der Ordnung der Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp. . .From the order of Siphonaptera z. Xenopsylla cheopis, Ceratophyllus spp. , ,
Aus der Ordnung der Arachnida z. B. Scorpio maurus, Latrodectus mactans.From the order of Arachnida z. B. Scorpio maurus, Latrodectus mactans.
Aus der Ordnung der Acarina z. B. .Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhlpicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp..From the order of Acarina z. B. acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhlpicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp. , Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.
Zu den pflanzenparasitären Nematoden gehören Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, TylenchulusPlant parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus
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semipenotrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp..semipenotrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.
Dio Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Wirkstoffe imprägnierte Natur- und synthetische Stoffe, Feinstver-r Kapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, ferner in Formulierungen mit Brennsätzeri, wie Räucherpatronen, -dosen, -Spiralen u. ä., sowie ULV-KaIt- und Warmnebel-Formulierungen.Dio active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substances impregnated natural and synthetic substances, ultrafine encapsulations in polymeric substances and in seed coatings, also in Formulations with Brennerineri, such as smoke cartridges, doses, spirals u. Ä., And ULV KaIt and warm mist formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verr flüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe,1 wie Chlorbenzole, Chloräthylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Äther und Ester, Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser; mit verflüssigten gasförmigen Streckmitteln oderThese formulations are prepared in a known manner, for. Example , by mixing the active compounds with extenders, ie liquid solvents, pressurized verr liquid gases and / or solid carriers, optionally with the use of surfactants, emulsifiers and / or dispersants and / or foam-forming agents. In the case of using water as an extender z. As well as organic solvents can be used as auxiliary solvent. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, 1 such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for. As petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water; with liquefied gaseous extenders or
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Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgas, wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid; als feste Trägerstoffe kommen in Frage: z. B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; als feste Trägerstoffe für Granulate kommen in Frage: z. B. gebrochene und fraktionierte natürliche Gesteine, wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengel; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z. B. nichtionogene und anionische Emulgatoren, wie Polyoxyäthylen-Fett säure-Ester, Polyoxyäthylen-Fettalkohol-Äther, z. B. Alkylarylpolyglykol-äther, Alkylsulfonate, Alkylsulfate, Arylsulfate sowie Eiweißhydroiysate; als Dispergiermittel kommen in Frage: z. B. Lignin-Sulfitablaugen und Methylcellulose.Carriers are meant liquids which are gaseous at normal temperature and under normal pressure, eg. B. aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers are: z. Natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as fumed silica, alumina and silicates; As solid carriers for granules are: z. Crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam-producing agents are in question: z. Nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylarylpolyglykol ether, alkyl sulfonates, alkyl sulfates, aryl sulfates and protein hydrosysates; as dispersants in question: z. As lignin-sulphite liquors and methylcellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate may be used in the formulations.
Es können Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azol-Metallphthalocyaninfarbstoffe und Spurennährsalzc wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet'werden.It can dyes such as inorganic pigments, eg. For example, iron oxide, titanium oxide, ferrocyan blue, and organic dyes such as alizarin, azole metal phthalocyanine dyes, and trace nutrient salts such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc are used.
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Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %. The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90 %.
Die Anwendung der erfindungsgemäßen Wirkstoffe erfolgt in Form ihrer handelsüblichen Formulierungen und/oder den aus diesen Formulierungen bereiteten Anwendungsformen.The application of the active compounds according to the invention takes place in the form of their commercially available formulations and / or the use forms prepared from these formulations.
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoff konzentration der Anwendungsnamen kann von 0,0000001 bis zu 100 Gevu-% Wirkstoff, vorzugsweise zwischen 0,01 und 10 Gew.-% liegen.The active substance content of the application forms prepared from the commercial formulations can vary within wide ranges. The active compound concentration of the application name can be from 0.0000001 to 100% Gevu- active ingredient by weight, preferably between 0.01 and 10 -. Lie%.
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.The application is done in a custom forms adapted to the application.
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnen sich die Wirkstoffe durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekalkten Unterlagen aus.When used against hygiene and storage pests, the active ingredients are characterized by an excellent residual effect on wood and clay and by a good alkali stability on limed substrates.
Ausf ührun.qsbeispiel · Example of embodiment
Die Erfindung wird nachstehend an einigen Ausführungsboispielen näher erläutert.The invention will be explained in more detail below on some Ausführungsboispielen.
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Beispiel A · Example A ·
Grenzkonzentrations-Test / NematodenLimit concentration test / nematodes
Testnematode: Meloidogyne incognita Lösungsmittel: 3 Gewichtsteile Aceton Emulgator: 1 Gewichtsteil AlkylarylpolyglykolätherTest nematode: Meloidogyne incognita Solvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge« Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Die Wirkstoffzubereitung vvird innig mit Boden vermischt, der mit den Testnematoden stark verseucht ist. Dabei spielt die Konzentration des Wirkstoffs in der Zubereitung praktisch keine Rolle, entscheidend ist allein die Wirkstoffmenge pro Volumeneinheit Boden, welche in ppm angegeben wird. Man füllt den behandelten Boden in Töpfe, sät Salat ein und hält die Töpfe bei einer Gewächshaustemperatur von 27 0C.The preparation of active compound is intimately mixed with soil that is heavily contaminated with the test nematodes. In this case, the concentration of the active ingredient in the preparation plays virtually no role, the only decisive factor is the amount of active substance per unit volume of soil, which is stated in ppm. Pour the treated soil into pots, sow lettuce and keep the pots at a greenhouse temperature of 27 ° C.
Nach vier Wochen werden die Salatwurzeln auf Nematodenbefall (Wurzelgallen) untersucht und der Wirkungsgrad des Wirkstoffs in % bestimmt. Der Wirkungsgrad ist 100 %, wenn der Befall vollständig vermieden wird, er ist 0 %, wenn der Befall genau so hoch ist wie bei den Kontrollpflanzen in unbehandeltem, aber in gleicher Weise verseuchtem Boden.After four weeks, the roots of the roots are examined for nematode infestation (root galls) and the efficiency of the active ingredient is determined in % . The efficiency is 100 %, if the infestation is completely avoided, it is 0 %, if the infestation is just as high as in the control plants in untreated, but equally contaminated soil.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: 1, 2, 3 und 4.In this test, z. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: 1, 2, 3, and 4.
28.2.1980 AP C 07 F/216 - 15 - 56 229/1228.2.1980 AP C 07 F / 216 - 15 - 56 229/12
Beispiel B Phaedon-Larven-Test Example B Phaedon larval test
Lösungsmittel: 3 Gewichtsteile Aceton Emulgator: 1 Gewichtsteil AlkylarylpolyglykolätherSolvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angegebenen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound with the stated amount of solvent and the stated amount of emulsifier and the concentrate is diluted with water to the desired concentration.
Kohlblätter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Meerettichblattkäfer-Larven (Phaedon cfeochleariae) besetzt, solange die Blätter noch feucht sind.Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with horseradish beetle larvae (Phaedon cfeochleariae) while the leaves are still moist.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, daß alle Käfer-Larven abgetötet sind; 0 % bedeutet, daß keine Käfer-Larven abgetötet wurden.After the desired time the kill is determined in % . 100 % means that all beetle larvae are killed; 0 % means that no beetle larvae have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: 1, 2, 3 und 4.In this test, z. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: 1, 2, 3, and 4.
216 03 1216 03 1
.28.2.1980 AP C 07 F/216 031 - 16 - 56 229/12.28.2.1980 AP C 07 F / 216 031 - 16 - 56 229/12
Tetranychus-Test (resistent) ·Tetranychus test (resistant) ·
Lösungsmittel: 3 Gewichtsteile Aceton Emulgator: 1 Gevvichtsteil AlkylarylpolyglykolätherSolvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angegebenen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound with the stated amount of solvent and the stated amount of emulsifier and the concentrate is diluted with water to the desired concentration.
Bohnenpflanzen (Phaseolus vulgaris), die.stark von allen Entwicklungsstadien der gemeinen Spinnmilbe oder Bohnenspinnmilbe (Tetranychus urticae) befallen sind, werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt.Bean plants (Phaseolus vulgaris) that are heavily infested with all stages of development of the common spider mite or bean spider mite (Tetranychus urticae) are treated by being dipped into the preparation of active compound of the desired concentration.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, daß alle Spinnmilben abgetötet wurden; 0 % bedeutet,' daß keine Spinnmilben abgetötet wurden.After the desired time the kill is determined in % . 100 % means that all spider mites have been killed; 0 % means' that no spider mites have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: 1, 2, 3 und 4.In this test, z. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: 1, 2, 3, and 4.
28.2.1980 AP C 07 F/216 - 17 - 56 229/1228.2.1980 AP C 07 F / 216 - 17 - 56 229/12
Herstellungsbeispiele ,Beispiel 1: Producible ungsbei games, Example 1:
(D(D
NH-C3H7-ISONH-C 3 H 7 -ISO
Eine Mischung von 15,8 g (0,1 Mol) 1,6-Dihydro-l-chloromethyl-3-methyl-5-oxo-pyridazin und 24,3 g (0,11 Mol) des Kaliumsalzes des O-Athyl-N-iso-propyl-thiolphosphorsäureesteramids wird in 200 ml Acetonitril 13 Stunden auf 50 C erhitzt. Dann wird das Reaktionsgemisch auf 20 C abgekühlt und in 500 ml Toluol gegossen. Die Toluollösung wird mit 50 ml gesättigter Natriumhydrogencarbonatlösung gewaschen, über Natriumsulfat getrocknet und dann eingedampft. Man erhält 25 g (82 % der Theorie) O-Äthyl-N-isopropyl-S-(l,6~dihydro-3-methyl-6-oxo-pyridazin(l)yl-methyl)- thiolphosphorsäureesteramid als gelbes öl mit dem ßrechungs-A mixture of 15.8 g (0.1 mol) of 1,6-dihydro-1-chloromethyl-3-methyl-5-oxopyridazine and 24.3 g (0.11 mol) of the potassium salt of the O-ethyl N-iso-propyl-thiolphosphoric acid ester amide is heated to 50 ° C. in 200 ml of acetonitrile for 13 hours. Then, the reaction mixture is cooled to 20 C and poured into 500 ml of toluene. The toluene solution is washed with 50 ml of saturated sodium bicarbonate solution, dried over sodium sulfate and then evaporated. This gives 25 g (82 % of theory) of O-ethyl-N-isopropyl-S- (l, 6 ~ dihydro-3-methyl-6-oxo-pyridazin (l) yl-methyl) - thiolphosphorsäureesteramid as a yellow oil with the ßrechungs-
00 index n^ : 1,5396. 00 index n ^: 1.5396.
Analog wurden die folgenden aufgeführten Verbindungen hergestellt:Analogously, the following compounds were prepared:
Ausbeute: O oc υ 74 % der Theorie;Yield: O oc υ 74 % of theory;
Brechungsindex: (2) nD : Refractive index: (2) n D :
t %jf W "W t% jf W "W
28.2.198002/28/1980
AP C 07 F/216AP C 07 F / 216
56 229/1256 229/12
CH.CH.
0 Il0 Il
-CH2-S-P-CH 2 -SP
OC3H7-ηOC 3 H 7 -η
Ausbeute: 82 % der Theorie; Brechungsindex: : 1,5280Yield: 82 % of theory; Refractive index:: 1.5280
(3)(3)
OCHOCH
NH-C3H7-ISONH-C 3 H 7 -ISO
Ausbeute:Yield:
89 % der Theorie; Brechungsindex:89 % of theory; Refractive index:
nf : 1,5495nf: 1.5495
(4)(4)
Die als Ausgangsmaterialien einzusetzenden Alkalisalze der Thiolphosphorsäureesteramide können z. B. wie folgt hergestellt werden:The alkali metal salts of the Thiolphosphorsäureesteramide to be used as starting materials can, for. B. be prepared as follows:
KS-PKS-P
0C3H7-n0C 3 H 7 -n
NH-C3H7-ISONH-C 3 H 7 -ISO
(5)(5)
Ein Gemisch aus 150 ml Wasser, 100 ml Methanol, 61,6 g (1,1 Mol) Kaliumhydroxid und 107,8 g (0,5 Mol) Thionophosphorsäure-0-propylester-N-iso-propy1amidchlorid wird 1 Stunde unter Rückfluß gekocht und dann auf Raumtemperatur abgekühlt. Man schüttelt die Lösung mit 200 ml Toluol, trennt die wäßrige Phase ab und dampft sie im Vakuum zur Trockne ein. Der Rückstand wird mit Aceton verrieben, man filtriert vom Ungelösten und destilliert das Lösungsmittel im Vakuum ab. Zurück bleiben 59 g (53 % der Theorie) Kalium-A mixture of 150 ml of water, 100 ml of methanol, 61.6 g (1.1 mol) of potassium hydroxide and 107.8 g (0.5 mol) of thionophosphoric acid 0-propyl ester N-iso-propy1amidchlorid is refluxed for 1 hour and then cooled to room temperature. The solution is shaken with 200 ml of toluene, the aqueous phase is separated off and evaporated to dryness in vacuo. The residue is triturated with acetone, filtered from undissolved and the solvent is distilled off in vacuo. 59 g (53 % of theory) of potassium remain behind
6 ι ο y & ϊ6 ι ο y & ϊ
28.2.1980 AP C 07 F/216 - 19 - 56 229/1228.2.1980 AP C 07 F / 216 - 19 - 56 229/12
salz des O-n-Propyl-N-iso-propyl-thiolphosphorsäureesteramids mit dem Schmelzpunkt 144 0C.salt of the On-propyl-N-iso-propyl-thiolphosphorsäureesteramids with the melting point of 144 0 C.
Analog können hergestellt werden:Analog can be produced:
KS-P 06)KS-P 06)
NH-C3H7-IsONH-C 3 H 7 -IsO
KS-P^ (7)KS-P ^ (7)
NH-C3H7-XSONH-C 3 H 7 -XSO
Claims (5)
-CH-S-P^ (I)OR
-CH-SP ^ (I)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19782843823 DE2843823A1 (en) | 1978-10-07 | 1978-10-07 | N-ISO-PROPYL-S- (1,6-DIHYDRO-6- (THI) OXO- PYRIEZIN (1) -YL-METHYL) -THIOLPHOSPHORSAEURE- ESTERAMIDES, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS A PEST CONTROL |
Publications (1)
Publication Number | Publication Date |
---|---|
DD146242A5 true DD146242A5 (en) | 1981-02-04 |
Family
ID=6051660
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD79216031A DD146242A5 (en) | 1978-10-07 | 1979-10-04 | SCHAEDLINGSBEKAEMPFUNGSMITTEL |
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---|---|
EP (1) | EP0010612B1 (en) |
JP (1) | JPS5553296A (en) |
AR (1) | AR222352A1 (en) |
AT (1) | ATE226T1 (en) |
AU (1) | AU5155979A (en) |
BR (1) | BR7906435A (en) |
CA (1) | CA1115275A (en) |
CS (1) | CS208789B2 (en) |
DD (1) | DD146242A5 (en) |
DE (2) | DE2843823A1 (en) |
DK (1) | DK420479A (en) |
ES (1) | ES484785A1 (en) |
IL (1) | IL58392A0 (en) |
PL (1) | PL119128B1 (en) |
PT (1) | PT70254A (en) |
ZA (1) | ZA795331B (en) |
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JP2501245Y2 (en) * | 1992-02-04 | 1996-06-12 | 大昭和精機株式会社 | Tool holder |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2348736A1 (en) | 1973-09-28 | 1975-04-10 | Bayer Ag | S- SQUARE CLIP ON 1,6-DIHYDROPYRIDAZINE- (1) -YLMETHYL SQUARE CLIP FOR -THIOLPHOSPHORIC ACID ESTER- OR. -ESTERAMIDE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS NEMATICIDES |
DE2603052A1 (en) | 1976-01-28 | 1977-08-04 | Bayer Ag | S- SQUARE CLIP ON 1,6-DIHYDRO- 6-THIOXO-PYRIDAZINE- (1) YLMETHYL SQUARE CLIP FOR - (THIONO) - (DI) -THIOL-PHOPSHOR (PHOSPHON) - ACID ESTER- OR. -ESTERAMIDE DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES |
-
1978
- 1978-10-07 DE DE19782843823 patent/DE2843823A1/en not_active Withdrawn
-
1979
- 1979-09-25 EP EP79103633A patent/EP0010612B1/en not_active Expired
- 1979-09-25 DE DE7979103633T patent/DE2960842D1/en not_active Expired
- 1979-09-25 AT AT79103633T patent/ATE226T1/en not_active IP Right Cessation
- 1979-10-01 PT PT70254A patent/PT70254A/en unknown
- 1979-10-04 IL IL58392A patent/IL58392A0/en unknown
- 1979-10-04 DD DD79216031A patent/DD146242A5/en unknown
- 1979-10-05 CS CS796799A patent/CS208789B2/en unknown
- 1979-10-05 PL PL1979218751A patent/PL119128B1/en unknown
- 1979-10-05 DK DK420479A patent/DK420479A/en unknown
- 1979-10-05 ES ES484785A patent/ES484785A1/en not_active Expired
- 1979-10-05 BR BR7906435A patent/BR7906435A/en unknown
- 1979-10-05 CA CA337,076A patent/CA1115275A/en not_active Expired
- 1979-10-05 ZA ZA00795331A patent/ZA795331B/en unknown
- 1979-10-05 AR AR278384A patent/AR222352A1/en active
- 1979-10-06 JP JP12935079A patent/JPS5553296A/en active Pending
- 1979-10-08 AU AU51559/79A patent/AU5155979A/en not_active Abandoned
Also Published As
Publication number | Publication date |
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PT70254A (en) | 1979-11-01 |
CA1115275A (en) | 1981-12-29 |
BR7906435A (en) | 1980-06-17 |
EP0010612A1 (en) | 1980-05-14 |
IL58392A0 (en) | 1980-01-31 |
AU5155979A (en) | 1980-04-17 |
AR222352A1 (en) | 1981-05-15 |
PL119128B1 (en) | 1981-11-30 |
DE2960842D1 (en) | 1981-12-03 |
ATE226T1 (en) | 1981-10-15 |
JPS5553296A (en) | 1980-04-18 |
EP0010612B1 (en) | 1981-09-16 |
ES484785A1 (en) | 1980-06-16 |
DK420479A (en) | 1980-04-08 |
DE2843823A1 (en) | 1980-04-24 |
CS208789B2 (en) | 1981-09-15 |
ZA795331B (en) | 1980-10-29 |
PL218751A1 (en) | 1980-07-28 |
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